EP0328024A1

Tetramethylpiperidino-s triazines.

Abstract

Compounds which contain at least one group of the formula Iwhere X is a group that complements the ring to a piperidine ring, are effective stabilizers for organic materials against damage by light, oxygen and heat.

EP0328024A1, drawing sheet 1 — Sheet 1 of 278

Term

Term ended

Projected expiry passed 6 February 2009, 17.6 years ago.

27 claims: 27 independent, 0 dependent

1
A compound which contains at least one group of the formula Iwhere X is a group that complements the ring to a piperidine ring, except for 2- (2,2,6,6-tetramethyl-1-piperidino) -4,6-bis (2,4,4-trimethyl-2 -pentylamino) triazine and 2,4-Dichtor-6- (2,2,6,6-tetramethyl-1-piperidino) triazine. 1. Eine Verbindung, die mindestens eine Gruppe der Formel I enthält, wobei X einer Gruppe ist, die den Ring zu einem Piperidinring ergänzt, mit Ausnahme von 2-(2,2,6,6-Tetramethyl-1-piperidino)-4,6-bis(2,4,4-trimethyl-2-pentylamino)-triazin und 2,4-Dichtor-6-(2,2,6,6-tetramethyl-1-piperidino)-triazin. 1. Organisches Material, enthaltend als Stabilisator mindestens eine Verbindung, die mindestens eine Gruppe der Formel I enthält, wobei X eine Gruppe ist, die den Ring zu einem Piperidinring ergänzt.
2
Eine Verbindung gemäss Anspruch 1 der Formel II, worin n eine ganze Zahl von 1 bis 6 bedeutet, R1 einen Rest der Formel oder Cl, OH, -OR3, -SR3 oder -NR4R5 bedeutet, wobei R3 C1-C18-Alkyl, Allyl, Cyclohexyl, Benzyl, Phenyl oder eine Gruppe der Formel A bedeutet, R4 Wasserstoff, C1-C12-Alkyl, 2-Hydroxyethyl, Allyl, Cyclohexyl, Benzyl oder eine Gruppe der Formel A bedeutet,R5 C1-C12-Alkyl, 2-Hydroxyethyl, Allyl, Cyclohexyl, Benzyl, Phenyl, durch Halogen, C1-C4-Alkyl oder C1-C4-Alkoxy substituiertes Phenyl, eine Gruppe der Formel A oder eine Gruppe der Formel C bedeutet, worin D durch unterbrochenes C2-C20-Alkylen bedeutet, Ra und Rb C1-C12-Alkyl, Cs-C6-Cycloalkyl, C6-C10-Aryl oder C7-C9-Phenylalkyl bedeuten und Ra auch Wasserstoff bedeutet oderR4 und R5 zusammen C4-C8-Alkylen bedeuten, das durch -0- oder -N(R8)-unterbrochen sein kann und worin R8 Wasserstoff, C1-C4-Alkyl oder Acetyl bedeutet,R6 Wasserstoff, C1-C12-Alkyl, C7-C9-Phenylalkyl, C3-C5-Alkenyl, C2-C4-Alkanoyl, C3-C5-Alkenoyl, -O°, -OH oder -OR7 bedeutet undR7 C1-C18-Alkyl, C5-C8Cycloalkyl, C7-C9-Phenylalkyl, Phenyl, C2-C18-Alkanoyl oder Benzyl bedeutet,R2, wenn n = 1 ist, Cl, OH, -OR3, -SR3 oder -NR4R5 bedeutet,wenn n = 2 ist, eine Gruppe -O-R9-O-, -S-R9-S-, -N(R10)-R9-N(R10)-, -O-R9-N(R10)-, oder -NH-NH- bedeutet, wobeiR9 C2-C2o-Alkylen, das durch ein oder mehrere -O-, -N(R8)- oder -OOC-R17-COO- unterbrochen sein kann, C4-C8-Cycloalkylen, Xylylen, Phenylen oder Tolylen bedeutet,R10 Wasserstoff, C1-C12-Alkyl, Allyl, 2-Hydroxyethyl, Benzyl, Phenyl oder eine Gruppe der Formel A bedeutet,wenn n = 3 ist, eine Gruppe -NH-(CH2) -(CH2) NH- oder bedeutet, worin a 2 oder 3 ist, Q -O-, -S- oder -N(R10)- ist und T C3-C20-Alkantriyl oder eine Gruppe bedeutet, worin Alk eine C2-C12-Alkylengruppe ist,wenn n = 4 ist, Gruppe C(CH2O-)4 oder bedeutet, worina 2 oder 3 ist und b 2-12 ist,wenn n = 5 ist, eine Gruppe -NH(CH2CH2 N )3CH2CH2NH- bedeutet, und wenn n = 6 ist, eine Gruppe -NH(CH2CH2 N )4CH2CH2NH- bedeutet,Y eine Gruppe bedeutet, worin m 0, 1 oder 2 ist, q eine ganze Zahl von 5 - 11 ist,R11 Wasserstoff, C1-C12-Alkyl, C3-C7-Alkenyl, C5-C8-Cycloalkyl, C7-C11Aralkyl oder eine Gruppe -CO-R18 bedeutet,R12 Wasserstoff, C1-C18-Alkyl, C3-C7-Alkenyl, C5-C8-Cycloalkyl, C7-C11-Aralkyl, C2-C4-Hydroxyalkyl, C3-C8-Alkoxyalkyl, C4-C20-Dialkylaminoalkyl, C3-C14-Alkoxyoarbonylalkyl oder eine Gruppe der Formel A bedeutet,R13 C1C12-Alkyl, C2-C4-Hydroxyalkyl, C3-C7-Alkenyl, Cs-Cs-Cycloalkyl, Phenyl, durch Halogen, C1-C4-Alkyl oder C1-C4-Alkoxy substituiertes Phenyl, C2-C20-Alkanoyl, C3-C8-Alkenoyl, Benzoyl, Phenylacetyl oder einen Triazinylrest der Formel B bedeutet, oderR12 und R13 zusammen C4-C8-Alkylen bedeuten, das durch -O- oder -N(R8)-unterbrochen sein kann oder R12 und R13 zusammen einen Rest der Formel bedeuten, worin R21 C1-C18-Alkyl bedeutet,R14 C1-C18-Alkyl, C5-C8-Cycloalkyl oder C7-C9-Phenylalkyl bedeutet oder beide Gruppen R14 zusammen C2-C6-Alkylen, o-Phenylen oder o-Xycylen bedeuten,R15 Wasserstoff, C1-C12-Alkyl, Cs-Cs-Alkenyl, C7-C9-Phenylalkyl, C2-C4-Hydroxyalkyl, C3-C8-Alkoxyalkyl oder C3-C14-Alkoxycarbonylalkyl bedeutet,R16 Wasserstoff, C1-C12-Alkyl, Allyl oder Benzyl bedeutet,R17 C1-C12-Alkylen, Vinylen, Cyclohexylen, Xylylen oder C6-C12-Arylen bedeutet,R18 C1-C18-Alkyl, C2-C6-Alkenyl, C5-C8-Cycloalkyl, C7-C9-Phenylalkyl, Phenyl oder durch Halogen, Nitro, C1-C4-Alkyl, Hydroxy oder C1-C4-Alkoxy substituiertes Phenyl oder durch Hydroxy und C1-C4-Alkyl substituiertes C7-C9-Phenylalkyl bedeutet,R19 eine der für R1 gegebenen Bedeutungen hat, undR20 Cl, -OH, OR3, -SR3 oder -NR4Rs bedeutet. 2. Organisches Material gemäss Anspruch 1, enthaltend mindestens eine Verbindung der Formel II worin n eine ganze Zahl von 1 bis 6 bedeutet, R1 einen Rest der Formel oder Cl, OH, -OR3, -SR3 oder -NR4R5 bedeutet, wobei R3 C1-C18-Alkyl, Allyl, Cyclohexyl, Benzyl, Phenyl oder eine Gruppe der Formel A bedeutet, R4 Wasserstoff, C1-C12-Alkyl, 2-Hydroxyethyl, Allyl, Cyclohexyl, Benzyl oder eine Gruppe der Formel A bedeutet,R5 C1-C12-Alkyl, 2-Hydroxyethyl, Allyl, Cyclohexyl, Benzyl, Phenyl, durch Halogen, C1-C4Alkyl oder C1-C4-Alkoxy substituiertes Phenyl, eine Gruppe der Formel A oder eine Gruppe der Formel C bedeutet, worin D durch unterbrochenes C2-C20-Alkylen bedeutet, Ra und Rb C1-C12-Alkyl, C5-C6-Cycloalkyl, C5-C10-Aryl oder C7-C9-Phenylalkyl bedeuten und Ra auch Wasserstoff bedeutet, oderR4 und R5 zusammen C4-C8-Alkylen bedeuten, das durch -0- oder -N(R8)-unterbrochen sein kann und worin R8 Wasserstoff, C1-C4-Alkyl oder Acetyl bedeutet,R6 Wasserstoff, Cl-C12-Alkyl, C7-C9-Phenylalkyl, C3-C5-Alkenyl, C2-C4-Alkanoyl, C3-C5-Alkenoyl, -O°, -OH oder -OR7 bedeutet undR7 C1-C18-Alkyl, Cs-Cs-Cycloalkyl, C7-C9-Phenylalkyl, Phenyl, C2-C18-Alkanoyl oder Benzoyl bedeutet,R2, wenn n = 1 ist, CI, OH, -OR3, -SR3 oder -NR4R5 bedeutet,wenn n = 2 ist, eine Gruppe -O-R9-O-, -S-R9-S-, -N(R10)-R9-N(R10)-, -O-R9-N(R10-, oder -NH-NH- bedeutet, wobeiR9 C2-C20-Alkylen, das durch ein oder mehrere -O-, -N(R8)- oder -OOC-R17-COO- unterbrochen sein kann, C4-C8-Alkenylen, C5-C8-Cycloalkylen, Xylylen, Phenylen oder Tolylen bedeutet,R10 Wasserstoff, C1-C12-Alkyl, Allyl, 2-Hydroxyethyl, Benzyl, Phenyl oder eine Gruppe der Formel A bedeutet,wenn n = 3 ist, eine Gruppe -NH-)CH2) -(CH2) NH- oder bedeutet, worin a 2 oder 3, ist, Q -O-, -S- oder -N(R10)- ist und T C3-C20-Alkantriyl oder eine Gruppe bedeutet, worin Alk eine C2-C12-Alkylengruppe ist,wenn n = 4 ist, eine Gruppe C(CH2O-)4 oder bedeutet, worina 2 oder 3 ist und b 2-12 ist, wenn n = 5 ist, eine Gruppe -NH(CH2CH2 N )3CH2CH2NH- bedeutet, und wenn n = 6 ist, eine Gruppe -NH(CH2CH2 N )4CH2CH2NH- bedeutet,Y eine Gruppe bedeutet, worin m 0, 1 oder 2 ist, q eine ganze Zahl von 5-11 ist,R11 Wasserstoff, C1-C18-Alkyl, C3-C7-Alkenyl, C5-C8-Cycloalkyl, C7-C11-Aralkyl oder eine Gruppe -CO-R18 bedeutet,R12 Wasserstoff, C1-C12-Alkyl, C3-C7-Alkenyl, C5-C8-Cycloalkyl, C7-C11-Aralkyl, C2-C4-Hydroxyalkyl, C3-C8-Alkoxyalkyl, C4-C20-Dialkylaminoalkyl, C3-C14-Alkoxycarbonylalkyl oder eine Gruppe der Formel A bedeutet,R13 C1-C12-Alkyl, C2-C4-Hydroxyalkyl, C3-C7-Alkenyl, C5-C8-Cycloalkyl, Phenyl, durch Halogen, C1-C4-Alkyl oder C1-C4-Alkoxy substituiertes Phenyl, C2-C20-Alkanoyl, C3-C8-Alkenoyl, Benzoyl, Phenylacetyl oder einen Triazinylrest der Formel B bedeutet, oderR12 und R13 zusammen C4-C8-Alkylen bedeuten, das durch -O- oder -N(R8)-unterbrochen sein kann oder R12 und R13 zusammen einen Rest der Formel bedeuten, worin R21 C1-C18-Alkyl bedeutet,R14 C1-C18-Alkyl, Cs-Cs-Cycloalkyl oder C7-C9-Phenylalkyl bedeutet oder beide Gruppen R14 zusammen C2-C6-Alkylen, o-Phenylen oder o-Xylylen bedeuten,R15 Wasserstoff, C1-C12-Alkyl, C3-C5-Alkenyl, C7-C9-Phenylalkyl, C2-C4-Hydroxyalkyl, C3-C8-Alkoxyalkyl oder C3-C14-Alkoxycarbonylalkyl bedeutet,R16 Wasserstoff, C1-C12-Alkyl, Allyl oder Benzyl bedeutet,R17 C1-C12-Alkylen, Vinylen, Cyclohexylen, Xylylen oder C6-C12-Arylen bedeutet,R18 C1-C18-Alkyl, C2-C6-Alkenyl, Cs-Cs-Cycloalkyl, C7-C9-Phenylalkyl, Phenyl oder durch Halogen, Nitro, C1-C4-Alkyl, Hydroxy oder C1-C4-Alkoxy substituiertes Phenyl oder durch Hydroxy und C1-C4-Alkyl substituiertes C7-C9-Phenylalkyl bedeutet,R19 eine der für R1 gegebenen Bedeutungen hat, undR20 CI, -OH, -OR3, -SR3 oder -NR4Rs bedeutet. 2nd A compound according to claim 1 of formula II,where n is an integer from 1 to 6,R1 a remainder of the formulaor Cl, OH, -OR3, -SR3 or -NR4R5 means, where R3 C.1-C18Alkyl, allyl, cyclohexyl, benzyl, phenyl or a group of the formula A,R4 Hydrogen, C1-C12Alkyl, 2-hydroxyethyl, allyl, cyclohexyl, benzyl or a group of the formula A,R5 C.1-C12-Alkyl, 2-hydroxyethyl, allyl, cyclohexyl, benzyl, phenyl, by halogen, C1-C4-Alkyl or C1-C4Alkoxy-substituted phenyl, a group of the formula A or a group of the formula C, where D bybroken C2-C20-Alkylene means Ra and Rb C.1-C12-Alkyl, Cs-C6Cycloalkyl, C6-C10-Aryl or C7-C9-Phenylalkyl and Ra also means hydrogen orR4 and R5 together C4-C8-Alkylene mean that by -0- or -N (R8) -interrupted and in which R8 Hydrogen, C1-C4-Alkyl or acetyl meansR6 Hydrogen, C1-C12-Alkyl, C7-C9-Phenylalkyl, C3-C5Alkenyl, C2-C4-Alkanoyl, C3-C5-Alkenoyl, -O °, -OH or -OR7 means andR7 C.1-C18-Alkyl, C5-C8Cycloalkyl, C7-C9-Phenylalkyl, phenyl, C2-C18-Alkanoyl or benzyl meansR2if n = 1, Cl, OH, -OR3, -SR3 or -NR4R5 meansif n = 2, a group -OR9-O-, -SR9-S-, -N (R10) -R9-NO10) -, -OR9-NO10)-, or -NH-NH- means, whereinR9 C.2-C2o-Alkylene, which is replaced by one or more -O-, -N (R8) - or -OOC-R17-COO- can be interrupted, C4-C8Cycloalkylene, xylylene, phenylene or tolylene,R10 Hydrogen, C1-C12Alkyl, allyl, 2-hydroxyethyl, benzyl, phenyl or a group of the formula A,if n = 3, a group -NH- (CH2) - (CH2) NH- ormeans what a is 2 or 3, Q is -O-, -S- or -N (R10) - is and TC3-C20Alkanetriyl or a groupmeans, where Alk is a C2-C12-Alkylene group,if n = 4, group C (CH2O-)4 ormeans whata is 2 or 3 and b is 2-12,if n = 5, a group -NH (CH2CH2 N)3CH2CH2NH- means, and if n = 6, a group -NH (CH2CH2 N)4CH2CH2NH- meansY a groupmeans where m is 0, 1 or 2, q is an integer from 5 to 11,R11 Hydrogen, C1-C12-Alkyl, C3-C7Alkenyl, C5-C8Cycloalkyl, C7-C11Aralkyl or a group -CO-R18 meansR12 Hydrogen, C1-C18-Alkyl, C3-C7Alkenyl, C5-C8Cycloalkyl, C7-C11Aralkyl, C2-C4-Hydroxyalkyl, C3-C8Alkoxyalkyl, C4-C20Dialkylaminoalkyl, C3-C14-Alkoxyoarbonylalkyl or a group of the formula A,R13 C.1C.12-Alkyl, C2-C4-Hydroxyalkyl, C3-C7Alkenyl, Cs-Cs-Cycloalkyl, phenyl, by halogen, C1-C4-Alkyl or C1-C4-Alkoxy substituted phenyl, C2-C20-Alkanoyl, C3-C8-Alkenoyl, benzoyl, phenylacetyl or a triazinyl radical of the formula B.means orR12 and R13 together C4-C8-Alkylene mean that by -O- or -N (R8) -interrupted or R12 and R13 together a remainder of the formulamean, where R21 C.1-C18-Alkyl meansR14 C.1-C18-Alkyl, C5-C8Cycloalkyl or C7-C9-Phenylalkyl means or both groups R14 together C2-C6Alkylene, o-phenylene or o-xycylene,R15 Hydrogen, C1-C12-Alkyl, Cs-CsAlkenyl, C7-C9-Phenylalkyl, C2-C4-Hydroxyalkyl, C3-C8-Alkoxyalkyl or C3-C14-Alkoxycarbonylalkyl meansR16 Hydrogen, C1-C12-Alkyl, allyl or benzyl meansR17 C.1-C12-Alkylene, vinylene, cyclohexylene, xylylene or C6-C12-Arrylen meansR18 C.1-C18-Alkyl, C2-C6Alkenyl, C5-C8Cycloalkyl, C7-C9-Phenylalkyl, phenyl or by halogen, nitro, C1-C4-Alkyl, hydroxy or C1-C4-Alkoxy substituted phenyl or by hydroxy and C1-C4Alkyl substituted C7-C9-Phenylalkyl meansR19 one of the for R1 has given meanings, andR20 Cl, -OH, OR3, -SR3 or -NR4Rs means.
3
Eine Verbindung gemäss Anspruch 1 der Formel III, worin p 2, 3 oder 4 ist, R19 und R20 die in Anspruch 2 gegebenen Bedeutungen haben und Z, wenn p = 2 ist, eine der Gruppen bedeutet, worinR22 C2-C12-Alkylen, C4-C8-Alkenylen, Xylylen oder -CO- bedeutet,R23 C1-C12-Alkylen, Vinylen, Cyclohexylen, Xylylen, C6-C12-Arylen oder durch Halogen, Nitro oder C1-C4-Alkyl substituiertes Phenylen oder eine direkte Bindung bedeutet,R24 Wasserstoff, C1-C12-Alkyl, C5-C8-Cycloalkyl, C7-C9-Phenylalkyl, C3-C7-Alkenyl, C2-C18-Alkanoyl, C3-C7-Alkenoyl, oder Benzoyl bedeutet,R25 C2-C12-Alkylen, durch NH oder 0 unterbrochenes C4-C16-Alkylen, C4-C8-Alkenylen, Xylylen oder Cyclohexylen bedeutetR26 Wasserstoff, C1-C12-Alkyl, Cs-C8-Cycloalkyl oder eine Gruppe der Formel A bedeutet,R27 eine der für R23 gegebenen Bedeutungen hat oder eine Gruppe -NH-R28-NH ist,R28 C2-C12-Alkylen oder C6-C12-Arylen bedeutet, das durch C1-C4-Alkyl substituiert sein kann,R29 Wasserstoff, C1-C12-Alkyl, C2-C18-Alkanoyl oder einen Triazinylrest der Formel B bedeutet, und R1, A und B die in Anspruch 2 gegebenen Bedeutungen haben,und wenn p = 3 ist, eine der Gruppen bedeutet, worin R30 C3-C18-Alkantriyl oder C6-C12-Arentriyl bedeutet, und wenn p = 4 ist, eine Gruppe bedeutet, worin R31 C4-C16-Alkantetrayl oder C6-C12-Arentetrayl bedeutet. 3. Organisches Material gemäss Anspruch 1, enthaltend mindestens eine Verbindung der Formel III, worin p 2, 3 oder 4 ist, R19 und R20 die in Anspruch 2 gegebenen Bedeutungen haben undZ, wenn p = 2 ist, eine der Gruppen bedeutet, worinR22 C2-C12-Alkylen, C4-C8-Alkenylen, Xylylen oder -CO- bedeutet,R23 C1-C12-Alkylen, Vinylen, Cyclohexylen, Xylylen, C6-C12-Arylen oder durch Halogen, Nitro oder C1-C4-Alkyl substituiertes Phenylen oder eine direkte Bindung bedeutet,R24 Wasserstoff, C1-C12-Alkyl, Cs-Cs-Cycloalkyl, C7-C9-Phenylalkyl, C3-C7-Alkenyl, C2-C18-Alkanoyl, C3-C7-Alkenoyl, oder Benzoyl bedeutet,R25 C2-C12-Alkylen, durch NH oder 0 unterbrochenes C4-C16-Alkylen, C4-C8-Alkenylen, Xylylen oder Cyclohexylen bedeutetR26 Wasserstoff, C1-C12-Alkyl, C5-C8-Cycloalkyl oder eine Gruppe der Formel A bedeutet,R27 eine der für R23 gegebenen Bedeutungen hat oder eine Gruppe -NH-R2s-NH ist,R28 C2-C12-Alkylen oder C6-C12-Arylen bedeutet, das durch C1-C4-Alkyl substituiert sein kann,R29 Wasserstoff, C1-C12-Alkyl, C2-C18-Alkanoyl oder einen Triazinylrest der Formel B bedeutet, und R1, A und B die in Anspruch 2 gegebenen Bedeutungen haben,und wenn p = 3 ist, eine der Gruppen bedeutet, worin R30 C3-C18-Alkantriyl oder C6-C12-Arentriyl bedeutet, undwenn p = 4 ist, eine Gruppe bedeutet, worin R31 C4-C16-Alkantetrayl oder C6-C12-Arentetrayl bedeutet. 3rd A compound according to claim 1 of formula III,where p is 2, 3 or 4,R19 and R20 have the meanings given in claim 2 and, if p = 2, Z is one of the groupsmeans whatR22 C.2-C12Alkylene, C4-C8-Alkenylene, xylylene or -CO- meansR23 C.1-C12-Alkylene, vinylene, cyclohexylene, xylylene, C6-C12Aryls or by halogen, nitro or C.1-C4-Alkyl substituted phenylene or a direct bond,R24 Hydrogen, C1-C12-Alkyl, C5-C8Cycloalkyl, C7-C9-Phenylalkyl, C3-C7Alkenyl, C2-C18-Alkanoyl, C3-C7-Alkenoyl, or benzoyl meansR25 C.2-C12-Alkylene, C interrupted by NH or 04-C16Alkylene, C4-C8-Alkenylene, xylylene or cyclohexyleneR26 Hydrogen, C1-C12-Alkyl, Cs-C8Cycloalkyl or a group of the formula A,R27 one of the for R23 has given meanings or a group -NH-R28-NH isR28 C.2-C12-Alkylene or C6-C12-Arylene means that by C1-C4-Alkyl can be substituted,R29 Hydrogen, C1-C12-Alkyl, C2-C18-Alkanoyl or a triazinyl radical of the formula B, and R1, A and B have the meanings given in claim 2,and if p = 3, one of the groupsmeans, where R30 C.3-C18Alkanetriyl or C6-C12-Arentriyl means, and if p = 4, a groupmeans, where R31 C.4-C16-Alkantetrayl or C6-C12-Arentetrayl means.
4
Eine Verbindung gemäss Anspruch 1 der Formel IV, worin r ein Wert von 3 bis 50 ist, Q und Q' unabhängig voneinander -0-, -S- oder -N(R10)- bedeuten und Y, R9 und R10 die in Anspruch 2 gegebenen Bedeutungen haben, oder worin -Q-R9-Q'- eine Gruppe -NHNH-, ist. 4. Organisches Material gemäss Anspruch 1, enthaltend mindestens eine Verbindung der Formel IV, worin r ein Wert von 3 bis 50 ist, Q und Q' unabhängig voneinander -O-, -S- oder -N(R10)- bedeuten und Y, R9 und R10 die in Anspruch 2 gegebenen Bedeutungen haben, oder worin -Q-R9-Q'- eine Gruppe -NHNH-, ist. 4th A compound according to claim 1 of formula IV,where r is a value from 3 to 50, Q and Q 'independently of one another -0-, -S- or -N (R10) - mean and Y, R9 and R10 have the meanings given in claim 2, or in which -QR9-Q'- a group -NHNH-,is.
5
A compound according to claim 1 of formula V, where r is a value from 3 to 50, Y and R1 have the meanings given in claim 2, to a C2-C4Is alkylene group and R23 has the meaning given in claim 3. 5. Eine Verbindung gemäss Anspruch 1 der Formel V, worin r ein Wert von 3 bis 50 ist, Y und R1 die in Anspruch 2 gegebenen Bedeutungen haben, An eine C2-C4-Alkylengruppe ist und R23 die in Anspruch 3 gegebene Bedeutung hat. 5. Organisches Material gemäss Anspruch 1, enthaltend mindestens eine Verbindung gemäss Anspruch 1 der Formel V, worin r ein Wert von 3 bis 50 ist, Y und R1 die in Anspruch 2 gegebenen Bedeutungen haben, An eine C2-C4-Alkylengruppe ist und R23 die in Anspruch 3 gegebene Bedeutung hat.
6
A compound according to claim 1 of formula VI,where r is a value from 3 to 50, R20 has the meaning given in claim 2 and Z'-R32-Z ' means one of the following groupswherein R22, R23, R24, R25, R26, R27 and R29 have the meaning given in claim 3 and q and R16 has the meaning given in claim 2. 6. Eine Verbindung gemäss Anspruch 1 der Formel VI, worin r ein Wert von 3 bis 50 ist, R20 die in Anspruch 2 gegebene Bedeutung hat und Z'-R32-Z' eine der folgenden Gruppen bedeutet worin R22, R23, R24, R25, R26, R27 und R29 die in Anspruch 3 gegebene Bedeutung haben und q und R16 die in Anspruch 2 gegebene Bedeutung hat. 6. Organisches Material gemäss Anspruch 1, enthaltend mindestens eine Verbindung der Formel VI, worin r ein Wert von 3 bis 50 ist, R20 die in Anspruch 2 gegebene Bedeutung hat und Z'-R32-Z' eine der folgenden Gruppen bedeutet worin R22, R23, R24, R25, R26, R27 und R29 die in Anspruch 3 gegebene Bedeutung haben und q und R16 die in Anspruch 2 gegebene Bedeutung hat.
7
A compound according to claim 1 of formula VII,wherein s is 0 or 1, t 0 or 2 and u is a value from 5 to 100,Q "-O-, -NH- or -N (C1-C4-Alkyl) - meansR34 Is hydrogen or methyl,R35 and R36 independently of one another -OR3, -SR3 or -NR4R5 mean whatR3, R4 and R5 have the meanings given in claim 2,and copolymers of such a compound with (meth) acrylic acid, alkyl (meth) acrylates, hydroxyalkyl (meth) acrylates or maleic anhydride. 7. Eine Verbindung gemäss Anspruch 1 der Formel VII, worin s 0 oder 1, t 0 oder 2 und u einen Wert von 5 bis 100 bedeutet, Q" -O-, -NH- oder -N(C1-C4-Alkyl)- bedeutet,R34 Wasserstoff oder Methyl ist,R35 und R36 unabhängig voneinander -OR3, -SR3 oder -NR4R5 bedeuten, worinR3, R4 und R5 die in Anspruch 2 gegebenen Bedeutungen haben, sowie Copolymere einer solchen Verbindung mit (Meth)acrylsäure, Alkyl(meth)acrylaten, Hydroxyalkyl-(meth)acrylaten oder Maleinsäureanhydrid. 7. Organisches Material gemäss Anspruch 1, enthaltend mindestens eine Verbindung der Formel VII, worin s 0 oder 1, t 0 oder 2 und u einen Wert von 5 bis 100 bedeutet, Q" -O-, -NH- oder -N(C1-C4-Alkyl)- bedeutet,R34 Wasserstoff oder Methyl ist,R35 und R36 unabhängig voneinander -OR3, -SR3 oder -NR4R5 bedeuten, worin R3, R4 und RS die in Anspruch 2 gegebenen Bedeutungen haben, sowie Copolymere einer solchen Verbindung mit (Meth)acrylsäure, Alkyl(meth)acrylaten, Hydroxyalkyl-(meth)acrylaten oder Maleinsäureanhydrid.
8
Eine Verbindung gemäss Anspruch 1 der Formel VIII, worin r ein Wert von 3 bis 50 ist, t 0 oder 2 ist, R9, Q und Q' die in Anspruch 4 gegebenen Bedeutungen haben,Q" -O-, -NH oder -N(C1-C4-Alkyl)- bedeutet undR35 und R36 die in Anspruch 7 gegebenen Bedeutungen haben. 8. Organisches Material gemäss Anspruch 1, enthaltend mindestens eine Verbindung der Formel VIII, worin r ein Wert von 3 bis 50 ist, t 0 oder 2 ist, R9, Q und Q die in Anspruch 4 gegebenen Bedeutungen haben,Q" -0-, -NH- oder -N(C1-C4-Alkyl)- bedeutet undR35 und R36 die in Anspruch 7 gegebenen Bedeutungen haben. 8th. A compound according to claim 1 of formula VIII,where r is a value from 3 to 50, t is 0 or 2,R9"Q and Q" have the meanings given in claim 4,Q "-O-, -NH or -N (C1-C4-Alkyl) - means andR35 and R36 have the meanings given in claim 7.
9
A compound according to claim 1 of formula IX,wherein v is a value from 2 to 30, t is 0 or 2, R35 and R36 have the meanings given in claim 7,R37 C.2C.8Alkylene, C4-C8-Alkenylene, xylylene, -CH2-CH (OH) -CH2-or -CH2CH (OH) CH2-OR39-O-CH2CH- (CH) CH2- meansR38 one of the for R37 has given meanings orisR38 C.2-C8-Alkylene, phenylene ormeans andR27 has the meaning given in claim 3. 9. Eine Verbindung gemäss Anspruch 1 der Formel IX, worin v ein Wert von 2 bis 30 ist, t 0 oder 2 ist, R35 und R36 die in Anspruch 7 gegebenen Bedeutungen haben, R37 C2C8-Alkylen, C4-C8-Alkenylen, Xylylen, -CH2-CH(OH)-CH2-oder -CH2CH(OH)CH2-O-R39-O-CH2CH-(CH)CH2- bedeutet,R38 eine der für R37 gegebenen Bedeutungen hat oder ist,R38 C2-C8-Alkylen, Phenylen oder bedeutet undR27 die im Anspruch 3 genannte Bedeutung hat. 9. Organisches Material gemäss Anspruch 1, enthaltend mindestens eine Verbindung der Formel IX, worin v ein Wert von 2 bis 30 ist, t 0 oder 2 ist, R35 und R36 die in Anspruch 7 gegebenen Bedeutungen haben, R37 C2-C8-Alkylen, C4-C8-Alkenylen, Xylylen, -CH2-CH(OH)-CH2-oder -CH2CH(OH)CH2-0-R39-0-CH2CH-(CH)CH2- bedeutet,R38 eine der für R37 gegebenen Bedeutungen hat oder ist,R39 C2-C8-Alkylen, Phenylen oder bedeutet undR27 die im Anspruch 3 genannte Bedeutung hat.
10
Eine Verbindung gemäss Anspruch 1 der Formel X, worin t 0 oder 2 ist, v ein Wert von 2 bis 30 ist, An C2-C4-Alkylen bedeutet, R35 und R36 die in Anspruch 7 gegebenen Bedeutungen haben und R23 die in Anspruch 3 gegebene Bedeutung hat. 10. Organisches Material gemäss Anspruch 1, enthaltend mindestens eine Verbindung der Formel X, worin t 0 oder 2 ist, v ein Wert von 2 bis 30 ist, An C2-C4-Alkylen bedeutet, R35 und R36 die in Anspruch 7 gegebenen Bedeutungen haben und R23 die in Anspruch 3 gegebene Bedeutung hat. 10th A compound according to claim 1 of formula X,where t is 0 or 2, v is a value from 2 to 30, At C2-C4-Alkylene means R35 and R36 have the meanings given in claim 7 and R23 has the meaning given in claim 3.
11
A compound according to claim 1 of formula XI,wherein n is an integer from 1 to 6, t is 0 or 2, R2 has the meaning given in claim 2, Q ", R35 and R36 have the meanings given in claim 7 and R40 either one of the for R1 has the meanings given in claim 2 or a groupmeans. 11. Eine Verbindung gemäss Anspruch 1 der Formel XI, worin n eine ganze Zahl von 1 bis 6 bedeutet, t 0 oder 2 ist, R2 die in Anspruch 2 gegebene Bedeutung hat, Q", R35 und R36 die in Anspruch 7 gegebenen Bedeutungen haben und R40 entweder eine der für R1 in Anspruche 2 gegebenen Bedeutungen hat oder eine Gruppe bedeutet. 11. Organisches Material gemäss Anspruch 1, enthaltend mindestens eine Verbindung der Formel XI, worin n eine ganze Zahl von 1 bis 6 bedeutet, t 0 oder 2 ist, R2 die in Anspruch 2 gegebene Bedeutung hat, Q", R35 und R36 die in Anspruch 7 gegebenen Bedeutungen haben und R40 entweder eine der für R1 in Anspruch 2 gegebenen Bedeutungen hat oder eine Gruppe bedeutet.
12
Eine Verbindung gemäss Anspruch 1 der Formel XII, worin r ein Wert von 3 bis 50 ist, R9 die in Anspruch 2 gegebene Bedeutung hat, die Gruppe Z'-R32-Z' eine der in Anspruch 6 gegebenen Bedeutungen hat, Q und Q' unabhängig voneinander -0-, -S- oder -N-(R10)- bedeuten und R35 die in Anspruch 7 gegebene Bedeutung hat. 12. Organisches Material gemäss Anspruch 1, enthaltend mindestens eine Verbindung der Formel XII, worin r ein Wert von 3 bis 50 ist, R9 die in Anspruch 2 gegebene Bedeutung hat, die Gruppe Z'-R32-Z eine der in Anspruch 6 gegebenen Bedeutungen hat, Q und Q unabhängig voneinander -0-, -S- oder -N-(R10)- bedeuten und R35 die in Anspruch 7 gegebene Bedeutung hat. 12th A compound according to claim 1 of formula XII,where r is a value from 3 to 50, R9 has the meaning given in claim 2, the group Z'-R32-Z ' has one of the meanings given in claim 6, Q and Q 'independently of one another -0-, -S- or -N- (R10) - mean and R35 has the meaning given in claim 7.
13
A compound according to claim 2 of formula II, where n is an integer from 1-4,R1 a residue Cl, -OR3 or -NR4R5 is whatR3, R4 and R5 have the meanings given in claim 2, R2if n = 1, CL, -OR3 or -NR4R5 meansif n = 2, a group -N (R10) -R9-NO10) - ormeans, where R9 and R10 have the meanings given in claim 2,if n = 3, a groupmeans andif n = 4, a groupmeans where a is 2 or 3 and b is 2 to 8 and Y is a groupiswhere R11, R12, R13 and R14 the meanings given in claim 2 13. Eine Verbindung gemäss Anspruch 2 der Formel II, worin n eine ganze Zahl von 1-4 ist, R1 ein Rest Cl, -OR3 oder -NR4R5 ist, worinR3, R4 und R5 die in Anspruch 2 gegebenen Bedeutungen haben, R2, wenn n = 1 ist, CL, -OR3 oder -NR4R5 bedeutet,wenn n = 2 ist, eine Gruppe -N(R10)-R9-N(R10)- oder bedeutet, worin R9 und R10 die in Anspruch 2 gegebenen Bedeutungen haben,wenn n = 3 ist, eine Gruppe bedeutet undwenn n = 4 ist, eine Gruppe bedeutet, worin a 2 oder 3 und b 2 bis 8 bedeuten und Y eine Gruppe ist, worin R11, R12, R13 und R14 die in Anspruch 2 gegebenen Bedeutungen 13. Organisches Material gemäss Anspruch 1;das ein organisches Polymer ist.
14
A compound according to claim 2 of formula II, wherein n is 1 or 2, R1 a remainder of the formulaor Cl, -OR3 or -NR4R5 means, where R3 C.1-C12Is alkyl, allyl or a group of formula A, R4 Hydrogen, C1-C8Represents alkyl, 2-hydroxyalkyl or a group of the formula A,R5 C.1-C8-Alkyl, 2-hydroxyethyl, a group of formula A or a group of formulameans, where Ra and Rb C.1-C4-Alkyl mean, or R4 and R5 together mean 3-oxapentamethylene,R2 at n = 1 Cl, -OR3 or -NR4R5 means, where R3, R4 and R5 have the meanings above, and when n = 2 -NH (CH2)6-NH- meansY one of the groupsiswherein R "is hydrogen, C1-C6-Alkyl, acetyl, acryloyl, benzyl or a group of the formulaisR12 Hydrogen or C1-C4-Alkyl isR13 C.1-C4-Alkyl or a radical of formula B in whichR19 and R20 CI or NO4R5 are, and R15 C.1-C12-Alkyl is. 14. Eine Verbindung gemäss Anspruch 2 der Formel II, worin n 1 oder 2 ist, R1 einen Rest der Formel oder Cl, -OR3 oder -NR4R5 bedeutet, wobei R3 C1-C12-Alkyl, Allyl oder eine Gruppe der Formel A ist, R4 Wasserstoff, C1-C8-Alkyl, 2-Hydroxyalkyl oder eine Gruppe der Formel A bedeutet, R5 C1-C8-Alkyl, 2-Hydroxyethyl, eine Gruppe der Formel A oder eine Gruppe der Formel bedeutet, worin Ra und Rb C1-C4-Alkyl bedeuten, oder R4 und R5 zusammen 3-Oxapentamethylen bedeuten,R2 bei n = 1 Cl, -OR3 oder -NR4R5 bedeutet, worin R3, R4 und R5 die obigen Bedeutungen haben, und bei n = 2 -NH(CH2)6-NH- bedeutet,Y eine der Gruppen ist,worin R" Wasserstoff, C1-C6-Alkyl, Acetyl, Acryloyl, Benzyl oder eine Gruppe der Formel ist,R12 Wasserstoff oder C1-C4-Alkyl ist,R13 C1-C4-Alkyl oder ein Rest der Formel B ist, in derR19 und R20 CI oder-NR4R5 sind, und R15 C1-C12-Alkyl ist. 14. Organisches Material gemäss Anspruch 1, das ein Anstrichstoff ist.
15
A compound according to claim 3 of formula III, wherein p is 2, 3 or 4, R19 and R20 independently of one another -OR3 or -NR4R5 mean whatR3, R4 and R5 have the meanings given in claim 2,Z if p = 2, one of the groupsmeans, where R23, R24, R25 and R26 have the meanings given in claim 3,if p = 3, one of the groupsmeans, where R30 C.3-C8Alkanetriyl or C6-C12-Arentriyl means and R26 has the meaning given in claim 3, andif p = 4, a groupis where R31 C.4-C12-Alkantetrayl or C6-C12-Arentetrayl mean. 15. Eine Verbindung gemäss Anspruch 3 der Formel III, worin p 2, 3 oder 4 ist, R19 und R20 unabhängig voneinander -OR3 oder -NR4R5 bedeuten, worin R3, R4 und R5 die in Anspruch 2 gegebenen Bedeutungen haben,Z, wenn p = 2 ist, eine der Gruppen bedeutet, worin R23, R24, R25 und R26 die in Anspruch 3 gegebenen Bedeutungen haben,wenn p = 3 ist, eine der Gruppen bedeutet, worin R30 C3-C8-Alkantriyl oder C6-C12-Arentriyl bedeutet und R26 die in Anspruch 3 gegebene Bedeutung hat, undwenn p = 4 ist, eine Gruppe ist, worin R31 C4-C12-Alkantetrayl oder C6-C12-Arentetrayl bedeuten. 15. Organisches Material gemäss Anspruch 1, das eine photographische Schicht ist.
16
A compound according to claim 3 of formula III, wherein p is 2, R19 and R20 CI or NR4R5 mean, where R4 and R5 C.1-C4-Alkyl, and Z one of the groupsmeans where R23 C.2-CsIs alkylene or phenylene and R25 - (CH2)6- means. 16. Eine Verbindung gemäss Anspruch 3 der Formel III, worin p 2 ist, R19 und R20 CI oder -NR4R5 bedeuten, worin R4 und R5 C1-C4-Alkyl sind, und Z eine der Gruppen bedeutet, worin R23 C2-Cs-Alkylen oder Phenylen ist und R25 -(CH2)6- bedeutet. 19. Photographische Schicht gemäss Anspruch 15, enthaltend zusätzlich ein sterisch gehindertes Phenol.
17
Eine Verbindung gemäss Anspruch 4 der Formel IV, worin r ein Wert von 3 bis 25 ist, Q und Q' -O-oder -N(R10)- bedeuten und Y, R9 und R10 die in Anspruch 2 gegebenen Bedeutungen haben. 17th A compound according to claim 4 of formula IV, wherein r is a value from 3 to 25, Q and Q '-O-or -N (R10) - mean and Y, R9 and R10 have the meanings given in claim 2.
18
Eine Verbindung gemäss Anspruch 4 der Formel IV, worin r ein Wert von 3 bis 50 ist, Y eine Gruppe oder CH-OC1-C8-Alkyl ist, Q und Q' -NH- bedeuten und R9 -(CH2)6- bedeutet. 18th A compound according to claim 4 of formula IV, wherein r is a value from 3 to 50, Y is a groupor CH-OC1-C8Is alkyl, Q and Q 'are -NH- and R is9 - (CH2)6- means.
19
Eine Verbindung gemäss Anspruch 5 der Formel V, worin r ein Wert von 3 bis 50 ist, Y eine Gruppe der Formel bedeutet, An -CH2-CH2- ist und R23 C2-C8-Alkylen ist. 19th A compound according to claim 5 of the formula V, wherein r is a value from 3 to 50, Y is a group of the formulameans to -CH2-CH2- is and R23 C.2-C8-Alkylene is.
20
Organisches Material, enthaltend als Stabilisator mindestens eine Verbindung, die mindestens eine Gruppe der Formel I enthält, wobei X eine Gruppe ist, die den Ring zu einem Piperidinring ergänzt. 20th Organic material containing, as a stabilizer, at least one compound which contains at least one group of the formula I,where X is a group that complements the ring to a piperidine ring.
21
Organic material according to claim 20, which contains at least one compound of the formula II of claim 2, the formula III of claim 3, the formula IV of claim 4, the formula V of claim 5, the formula VI of claim 6, the formula VII of claim 7, formula VIII of claim 8, formula IX of claim 9, formula X of claim 10, formula XI of claim 11 or formula XII of claim 12. 21. Organisches Material gemäss Anspruch 20, das als Stabilisator mindestens eine Verbindung der Formel II des Anspruches 2, der Formel III des Anspruches 3, der Formel IV des Anspruches 4, der Formel V des Anspruches 5, der Formel VI des Anspruches 6, der Formel VII des Anspruches 7, der Formel VIII des Anspruches 8, der Formel IX des Anspruches 9, der Formel X des Anspruches 10, der Formel XI des Anspruches 11 oder der Formel XII des Anspruches 12 enthält.
22
An organic material according to claim 20 which is an organic polymer. 22. Organisches Material gemäss Anspruch 20, das ein organisches Polymer ist.
23
An organic material according to claim 20 which is a paint. 23. Organisches Material gemäss Anspruch 20, das ein Anstrichstoff ist.
24
Organisches Material gemäss Anspruch 20, das eine photographische Schicht ist. 24th An organic material according to claim 20 which is a photographic layer.
25
Photographische Schicht gemäss Anspruch 24, enthaltend zusätzlich ein sterisch gehindertes Phenol. 25th The photographic layer according to claim 24, additionally containing a sterically hindered phenol.
26
Use of a compound which contains at least one group of the formula Iwhere X is a group that complements the ring to a piperidine ring, as a stabilizer for organic materials against damage by light, oxygen and heat. 26. Verwendung einer Verbindung, die mindestens eine Gruppe-der Formel I enthält, worin X eine Gruppe ist, die den Ring zu einem Piperidinring ergänzt, als Stabilisator für organische Materialien gegen Schädigung durch Licht, Sauerstoff und Hitze.
27
27 Use according to claim 26 of a compound of the formulawhere X is a group that complements the ring to a piperidine ring, D a byinterrupted C2-C2oAlkylene radical, Ra and Rb C.1-C12-Alkyl, Cs-C6Cycloalkyl, C6-C10-Aryl or C7-C9-Phenylalkyl and Ra also means hydrogen, as stabilizers for photographic dyes. 27. Verwendung gemäss Anspruch 26 einer Verbindung der Formel worin X eine Gruppe ist, die den Ring zu einem Piperidinring ergänzt, D ein durch unterbrochener C2-C2o-Alkylenrest ist, Ra und Rb C1-C12-Alkyl, Cs-C6-Cycloalkyl, C6-C10-Aryl oder C7-C9-Phenylalkyl bedeuten und Ra auch Wasserstoff bedeutet, als Stabilisatoren für photographische Farbstoffe.

Independent claims27

282 paragraphs, as filed

The invention relates to new triazine derivatives which contain at least one tetramethylpiperidino group and to their use as stabilizers for organic materials.

Compounds which contain at least one triazine group and a 2,2,6,6-tetramethyl-4-piperidinyl group in their molecule are known as stabilizers for organic materials. Such compounds either contain only one triazine group, such as the compounds described in US Pat. No. 3,925,376, or they contain several triazine groups, such as the compounds described in US Pat. No. 4,108,829. They can also be oligomers or polymers with a recurring triazine group, such as, for example, the compounds described in US Pat. No. 4,086,204. In all of these known compounds, the piperidine residue is linked to the triazine ring via its 4-position.

Compounds have now been found in which the 2,2,6,6-tetramethylpiperidine residue is bonded to the triazine ring via its 1-position (the nitrogen atom) . Two such compounds are described in DE-A-2,025,080 and were proposed there as medicaments. Use as stabilizers is not mentioned.

The invention relates to compounds which contain at least one group of the formula I<chemistry id="chem0001" num="0001"><img file="EP0328024A1_D0001.tif" /></chemistry>where X is a group that complements the ring to a piperidine ring, with the exception of 2- (2,2,6,6-tetramethyl-1-piperidino) -4,6-bis (2,4,4-tri methyl- 2-pentylamino) triazine and 2,4-dichloro-6- (2,2,6,6-tetramethyl-1-piperidino) triazine.

Preference is given to compounds which contain at least one group of the formula I in which X is not CH2 is.

Such groups can exist in a wide variety of classes of compounds. The most important classes of compounds according to the invention are the following<ul id="ul0001" list-style="none"><li>1) compounds of the formula II,<chemistry id="chem0002" num="0002"><img file="EP0328024A1_D0002.tif" /></chemistry>where n is an integer from 1 to 6, R1 a remainder of the formula<chemistry id="chem0003" num="0003"><img file="EP0328024A1_D0003.tif" /></chemistry>or Cl, OH, -OR3, -SR3 or -NR4R5 R means where R3 C.1-C18Alkyl, allyl, cyclohexyl, benzyl, phenyl or a group of the formula A,<chemistry id="chem0004" num="0004"><img file="EP0328024A1_D0004.tif" /></chemistry><ul id="ul0002" list-style="none"><li>R4 Hydrogen, C1-C12-Alkyl, 2-hydroxyethyl, allyl, cyclohexyl, benzyl or a group of the formula A,</li><li>R5 C.1-C12-Alkyl, 2-hydroxyethyl, allyl, cyclohexyl, benzyl, phenyl, by halogen, C1-C4-Alkyl or C1-C4Alkoxy-substituted phenyl, a group of the formula A or a group of the formula C,<chemistry id="chem0005" num="0005"><img file="EP0328024A1_D0005.tif" /></chemistry>where D by<chemistry id="chem0006" num="0006"><img file="EP0328024A1_D0006.tif" /></chemistry>interrupted C2-C20-Alkylene means Ra and Rb C.1-C12-Alkyl, Cs-C6-cycloalkyl, C6-C10-Aryl or C7-C9-Phenylalkyl and Ra also means hydrogen, or</li><li>R4 and R5 together C4-C8-Alkylene mean that by -0- or -N (RS) -interrupted and in which R8 Hydrogen, C1-C4-Alkyl or acetyl means</li><li>R6 Hydrogen, C1-C12-Alkyl, C7-C9-Phenylalkyl, C3-C5Alkenyl, C2-C4-Alkanoyl, C3-C5-Alkenoyl, -O. -OH or -OR7 means and</li><li>R7 C.1-C18-Alkyl, Cs-Cs cycloalkyl, C7-C9-Phenylalkyl, phenyl, C2-C18-Alkanoyl or benzoyl means</li><li>R2if n = 1, CI, OH, -OR3, -SR3 or -NR4R5 means if n = 2, a group -0-R9-0-, -SR9-S-, -N (R10) -R9-NO10) -, -OR9-NO10)-, <chemistry id="chem0007" num="0007"><img file="EP0328024A1_D0007.tif" /></chemistry>or -NH-NH- means, wherein</li><li>R9 C.2-C20-Alkylene, which is replaced by one or more -0-, -N (R8) - or -OOC-R17-COO- can be interrupted, C4-C8Alkenylene, C5-C8Cycloalkylene, xylylene, phenylene or tolylene,</li><li>R10 Hydrogen, C1-C12Denotes alkyl, allyl, 2-hydroxyethyl, benzyl, phenyl or a group of the formula A, if n = 3, a group -NH- (CH2) a N- (CH2) a NH- or<chemistry id="chem0008" num="0008"><img file="EP0328024A1_D0008.tif" /></chemistry>means what a is 2 or 3, Q is -O-, -S- or -N (R10) - is and TC3-C20Alkanetriyl or a group<chemistry id="chem0009" num="0009"><img file="EP0328024A1_D0009.tif" /></chemistry>means, where Alk is a C2-C12-Alkylene group, when n = 4, is a group C (CH20-)4 or<chemistry id="chem0010" num="0010"><img file="EP0328024A1_D0010.tif" /></chemistry>means what</li><li>a is 2 or 3 and b is 2-12,</li><li>if n = 5, a group -NH (CH2CH2 N)3CH2CH2NH- means, and if n = 6, a group -NH (CH2CH2 N)4CH2CH2NH- means</li><li>Y a group<chemistry id="chem0011" num="0011"><img file="EP0328024A1_D0011.tif" /></chemistry><chemistry id="chem0012" num="0012"><img file="EP0328024A1_D0012.tif" /></chemistry>means where m is 0, 1 or 2, q is an integer from 5 to 11,</li><li>R "hydrogen, C1-C18-Alkyl, C3-C7Alkenyl, C5-C8Cycloalkyl, C7-C11Aralkyl or a group -CO-R18 means</li><li>R12 Hydrogen, C1-C12-Alkyl, C3-C.7Alkenyl, C5-C8Cycloalkyl, C7-C11Aralkyl, C2-C4-Hydroxyalkyl, C3-C8Alkoxyalkyl, C4-C20Dialkylaminoalkyl, C3-C14Alkoxycarbonylalkyl or a group of the formula A,</li><li>R13 C.1-C12-Alkyl, C2-C4-Hydroxyalkyl, C3-C7-Alkenyl, Cs-Cs-cycloalkyl, phenyl, by halogen, C1-C4-Alkyl or C1-C4-Alkoxy substituted phenyl, C2-C20-Alkanoyl, C3-C8-Alkenoyl, benzoyl, phenylacetyl or a triazinyl radical of the formula B.<chemistry id="chem0013" num="0013"><img file="EP0328024A1_D0013.tif" /></chemistry>means or</li><li>R12 and R13 together C4-C8-Alkylene mean that by -0- or -N (R8) -interrupted or R12 and R13 together a remainder of the formula<chemistry id="chem0014" num="0014"><img file="EP0328024A1_D0014.tif" /></chemistry>mean, where R21 C.1-C18-Alkyl means</li><li>R14 C.1-C18-Alkyl, Cs-Cs cycloalkyl or C7-C9-Phenylalkyl means or both groups R14 together C2-C6Alkylene, o-phenylene or o-xylylene,</li><li>R15 Hydrogen, C1-C12-Alkyl, C3-C5Alkenyl, C7-C9-Phenylalkyl, C2-C4-Hydroxyalkyl, C3-C8-Alkoxyalkyl or C3-C14-Alkoxycarbonylalkyl means</li><li>R16 Hydrogen, Cl-C12-Alkyl, allyl or benzyl means</li><li>R17, C1-C12-Alkylene, vinylene, cyclohexylene, xylylene or C6-C12-Arrylen means</li><li>R18 C.1-C18-Alkyl, C2-C6Alkenyl, C5-C8Cycloalkyl, C7-C9-Phenylalkyl, phenyl or by halogen, nitro, C1-C4-Alkyl, hydroxy or C1-C4-Alkoxy substituted phenyl or by hydroxy and C1-C4Alkyl substituted C7-C9-Phenylalkyl means</li><li>R19 one of the for R1 has given meanings, and</li><li>R20 CI, -OH, -OR3, -SR3 or -NR4R5 means.</li></ul></li></ul>

If any substituents are alkyl, this can be straight or branched chain alkyl. Examples include methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, tert-butyl, iso-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, iso-decyl , n-dodecyl, n-hexadecyl or n-octadecyl. R12, R13 and R15 in the meaning of hydroxyalkyl can be, for example, 2-hydroxypropyl, 3-hydroxypropyl or 2-hydroxybutyl, but in particular 2-hydroxyethyl.

R12 and R15 as alkoxyalkyl there can be, for example, 2-methoxyethyl, 2-ethoxyethyl, 2-methoxypropyl, 2-butoxypropyl or 2-hexyloxyethyl. R12 as dialkylaminoalkyl can be, for example, 2-dimethylaminoethyl, 2-dibutylaminoethyl, 2-diethylaminopropyl or 2-dihexylaminoethyl.

R18 as C2-Cs-Alkenyl can in particular be vinyl or 2-propenyl. R6, R11, R12, R13 and R15 as alkenyl in particular can be allyl or methallyl.

R6, R7, R4 , R15, R17, and R18 as C7-C9Phenylalkyl can in particular be benzyl or phenylethyl. R12 as C7-C11Aralkyl can be, for example, benzyl, phenylethyl or naphthylmethyl.

R7, R", R12, R13, R14 and R18 cyclohexyl may in particular be cycloalkyl.

R6, R7, R13 and R17 as alkanoyl can be straight or branched. Examples include acetyl, propionyl, isobutyryl. Hexanoyl, octanoyl, lauroyl or stearoyl. R6 Alkenoyl can be, in particular, acryloyl or methacryloyl.

R9 as alkylene can be straight or branched or interrupted by heteroatoms. Examples include di-, tri-, tetra-, hexa-, octa-, deca- or dodecamethylene, 2,2-dimethyltrimethylene or 2,2,4-trimethyltetramethylene, 3-oxapentamethylene, 3-azapentamethylene, 3-methylazapentamethylene, 4 -Butylazaheptamethylene or 3,6-Dioxaoctamethylene.

R4 and R5 together as well as R12 and R13 together C4-C8-Alkylene, which can be replaced by -O- or -N (R8) - can be interrupted. In this case, together with the N atom to which they are attached, they form a heterocyclic ring, which is preferably 5- or 6-membered. Examples include pyrrolidine, piperidine, 2,6-dimethylpiperidine, morpholine, piperazine, 4-methylpiperazine or 4-acetylpiperazine.

R9 in particular 2-butenylene-1,4-alkenylene may be used. R9 cycloalkylene can be, in particular, 1,4-cyclohexylene.

If R2 C.3-C20-Alkanetriyl, this radical can be straight or branched. Examples include propane-1,2,3-triyl, butane-1,3,4-triyl, pentane-1,3,5-triyl or 2-methylpentane-1,3,5-triyl.

Preferred compounds of the formula II are those in which n is an integer from 1-4<ul id="ul0003" list-style="none"><li>R1 a residue Cl, -OR3 or -NR4R5 is what</li><li>R3, R4 and R5 have the meanings given above,</li><li>R2if n = 1, CI, -OR3 or -NR4R5 means</li><li>if n = 2, a group -N (R10) -R9-NO10) - or<chemistry id="chem0015" num="0015"><img file="EP0328024A1_D0015.tif" /></chemistry>means, where R9 and R10 have the meanings given above,</li><li>if n = 3, a group<chemistry id="chem0016" num="0016"><img file="EP0328024A1_D0016.tif" /></chemistry></li><li>means and if n = 4, a group<chemistry id="chem0017" num="0017"><img file="EP0328024A1_D0017.tif" /></chemistry>means where a is 2 or 3 and b is 2 to 8 and</li><li>Y a group<chemistry id="chem0018" num="0018"><img file="EP0328024A1_D0018.tif" /></chemistry>is</li><li>where R11, R12, R13 and R14 have the meanings given above.</li></ul>

Preferred among these are those of the formula II in which n = 1 and R1 and R2 are identical.

Compounds of the formula II in which n = 1 are particularly preferred, R1 and R2 independently of one another CI or -NR4R5 mean R4 Hydrogen or C1-C12-Alkyl means R5 C.1-C12-Alkyl means or R4 and R5 together represent pentamethylene or 3-oxapentamethylene, and Y is a group<chemistry id="chem0019" num="0019"><img file="EP0328024A1_D0019.tif" /></chemistry><chemistry id="chem0020" num="0020"><img file="EP0328024A1_D0020.tif" /></chemistry>means where R11 Hydrogen, C1-C12-Alkyl or -CO-R18 means and R18 C.1-C18Is alkyl or phenyl, R14 C.1-C4Is alkyl and R15 Hydrogen or C1 -C1 2-Alkyl means.

To prepare the compounds of the formula II, it is advantageous to start from cyanuric acid chloride and react this with one equivalent of a tetramethylpiperidine of the formula XIII.<chemistry id="chem0021" num="0021"><img file="EP0328024A1_D0021.tif" /></chemistry>

The dichlorotriazine XIV obtained can in a second reaction stage with one mole of a compound R1N are reacted to give a monochlorotriazine XV.<chemistry id="chem0022" num="0022"><img file="EP0328024A1_D0022.tif" /></chemistry>

By reacting n equivalents XV with a compound R2-(H)" the desired compound of formula II is obtained in a third reaction stage.

The individual reaction stages can be carried out without isolating the intermediates XIV and XV. All three reaction stages are preferably carried out in an inert solvent with the addition of bases as HCI scavengers.

Examples of suitable solvents are benzene, toluene or xylene. Examples of suitable bases are tertiary amines such as tributylamine or dimethylaniline or alkali metal hydroxides such as NaOH or KOH or alkali metal carbonates such as Na2C03 or K2C03. Excess piperidine XIII can also be used as an HCI scavenger.

The reactions are preferably carried out by heating the reaction mixtures. The base is preferably added successively as the reaction proceeds. The progress of the reaction can be monitored, for example, by analyzing the bound and / or the ionized chlorine. Another possibility of the reaction control is a chromatographic analysis of the reaction mixture.

To isolate the product, the base salts are expediently filtered off or extracted with water and the organic solution is evaporated. If one wants to isolate the intermediate products, one proceeds in the same way.

Alternatively, the intermediate XIV can first with R2(H)n and then with RI.H can be implemented. If R1 and. R2 are identical, the second and third reaction stages can be combined by XIV with 2 equivalents of R1H implements.

It goes without saying that a compound XIII is used in the first stage, the group Y of which is inert to cyarauroyl chloride under the reaction conditions. Above all, Y should not contain any free OH, NH or SH groups. Following the three-stage synthesis of II, the original (inert) group Y can be exchanged for another group Y in a further reaction or reaction sequence. For example, an original ketal group<chemistry id="chem0023" num="0023"><img file="EP0328024A1_D0023.tif" /></chemistry>to the keto group <img file="EP0328024A1_D0024.tif" />C = O can be hydrolyzed. The keto group can be reduced to the group -CH-OH, which in turn can be etherified or esterified to form<img file="EP0328024A1_D0024.tif" />CHOIR11. The keto group <img file="EP0328024A1_D0024.tif" />C = O can be reductively aminated into an amino group <img file="EP0328024A1_D0024.tif" />CH-NHR12 be converted into a group by appropriate N substitution <img file="EP0328024A1_D0024.tif" />CH-NO12R13 can be transferred.

The keto group: C = 0 can be converted into the corresponding a-hydroxy- or a-aminonitriles, which in turn can be converted into the corresponding spirohydantoins and spirooxazolidones by addition of isocyanates or ketones.

Similarly, other known group Y conversion reactions can be used.

Examples of individual compounds of formula II are the following compounds.

2) compounds of the formula III,<chemistry id="chem0024" num="0024"><img file="EP0328024A1_D0030.tif" /></chemistry>where p is 2, 3 or 4,<ul id="ul0004" list-style="none"><li>R19 and R20 have the meanings given above and Z, if p = 2, one of the groups<chemistry id="chem0025" num="0025"><img file="EP0328024A1_D0031.tif" /></chemistry><chemistry id="chem0026" num="0026"><img file="EP0328024A1_D0032.tif" /></chemistry><chemistry id="chem0027" num="0027"><img file="EP0328024A1_D0033.tif" /></chemistry><chemistry id="chem0028" num="0028"><img file="EP0328024A1_D0034.tif" /></chemistry>means what</li><li>R22 C.2-C12 alkylene, C4-C8-Alkenylene, xylylene or -CO- means R23 C.1-C12-Alkylene, vinylene, cyclohexylene, xylylene, C6-C12Aryls or by halogen, nitro or C.1-C4-Alkyl substituted phenylene or a direct bond,</li><li>R24 Hydrogen, C1-C12-Alkyl, Cs-CsCycloalkyl, C7-C9-Phenylalkyl, C3-C7Alkenyl, C2-C18-Alkanoyf, C3-C7-Alkenyl, or benzoyl means</li><li>R25 C.2-C12-Alkylene, C interrupted by NH or 04-C16Alkenylene, C4-C8-Alkylene, xylylene or cyclohexylene,</li><li>R26 Hydrogen, C1-C12-Alkyl, C5-C8Cycloalkyl or a group of the formula A,</li><li>R27 one of the for R23 has given meanings or a group -NH-R2s-NH- is</li><li>R28 C.2-C12-Alkylene or C6-C12-Arylene means that by C1-C4-Alkyl can be substituted,</li><li>R29 Hydrogen, C1-C12-Alkyl, C2-C18-Alkanoyl or a triazinyl radical of the formula B, and R1 has the meaning given above,</li><li>and if p = 3, one of the groups<chemistry id="chem0029" num="0029"><img file="EP0328024A1_D0035.tif" /></chemistry><chemistry id="chem0030" num="0030"><img file="EP0328024A1_D0036.tif" /></chemistry>means, where R30 C.3-C18Alkanetriyl or C6-C12-Arentriyl means</li><li>and if p = 4, one of the groups<chemistry id="chem0031" num="0031"><img file="EP0328024A1_D0037.tif" /></chemistry>means, where R31 C.4-C16-Alkantetrayl or C6-C12-Arentetrayl means.</li></ul>

If R24, R26 or R29 C.1-C12-Alkyl means, this can be straight or branched chain alkyl, such as methyl, ethyl, iso-propyl, n-butyl, sec-butyl, iso-amyl, n-hexyl, n-octyl, 2-ethylhexyl, n- Decyl or n-dodecyl. R24 as C3-C7-Alkenyl can in particular be allyl.

R24 and R29 as C5-C8Cycloalkyl can in particular be cyclohexyl. R24 as C7-C9Phenylalkyl can in particular be benzyl.

R24 and R28 as C2-C18-Alkanoyl can be straight or branched. Examples of these are acetyl, propionyl, eutyroy, octanoyl, lauroyl or stearoyl. R24 as C3-C7-Alkenoyl can in particular be acryloyl or methacryloyl.

R22, R25 and R28 as C2-C12-Alkyls can be straight or branched. Examples include di-, tri-, tetra-, hexa-, octa-, deca- or dodecamethylene, 2,2-dimethyltrimethylene, diethylmethylene or 2,2,4-trimethyl-tetramethylene. R23 as C1-C14-Alkylene can also be, for example, methylene or tetradecamethylene. R25 as interrupted alkylene can be, for example, 3-oxapentamethylene, 3-azapentamethylene, 3-methylazapentamethylene or 4-oxaheptamethylene. R22 as C4-C8-Alkenylene can in particular be 2-butenylene-1,4.

R23 and R28 as C3-C12Aryls can be, for example, phenylene, diphenylene or naphthylene.

R30 the trivalent radical can be, for example, propane-1,2,3-triyl, butane-1,2,4-triyl, benzene-1,2,4-triyl or naphthalene-1,4,6-triyl.

R31 the tetravalent radical can be, for example, butane-1,2,3,4-tetrayl, benzene-1,2,4,5-tetrayl or naphthalene-1,4,5,8-tetrayl.

Compounds of the formula III in which p is 2, 3 or 4 are preferred, R19 and R20 independently of one another, -OR3 or -NR4 R5 mean, where R3, R4 and R5 have the meanings given above, Z, if p = 2, one of the groups<chemistry id="chem0032" num="0032"><img file="EP0328024A1_D0038.tif" /></chemistry><chemistry id="chem0033" num="0033"><img file="EP0328024A1_D0039.tif" /></chemistry><chemistry id="chem0034" num="0034"><img file="EP0328024A1_D0040.tif" /></chemistry>means, where R23, R24, R25 and R26 have the meanings given above, if p = 3, one of the groups<chemistry id="chem0035" num="0035"><img file="EP0328024A1_D0041.tif" /></chemistry>means, where R30 C.3-C8Alkanetriyl or C6-C12-Arentriyl means and R26 has the meaning given above, and if p = 4, a group<chemistry id="chem0036" num="0036"><img file="EP0328024A1_D0042.tif" /></chemistry>is where R31 C.4-C12-Alkantetrayl or C6-C12-Arentetrayl mean.

Preferred among these are those compounds of the formula III in which R19 and R20 are identical.

To prepare the compounds of the formula III, p equivalents of cyanuric acid chloride can be reacted with a bis-, tris- or tetrakispiperidine compound XVI in a first step.<chemistry id="chem0037" num="0037"><img file="EP0328024A1_D0043.tif" /></chemistry>

The intermediate XVII can then in two further reaction steps with R19H and R20H can be implemented. Are R19 and R20 identical, they can be introduced in one step.

The individual reaction steps mean a gradual substitution of the three chlorine atoms on the triazine ring. They can be carried out as previously described for the synthesis of II.

Alternatively, you can first prepare a compound of formula XVIII, as described for the preparation of II, and react it with di-, tri- or tetravalent reagents XIX.<chemistry id="chem0038" num="0038"><img file="EP0328024A1_D0044.tif" /></chemistry>

For example, Y is a group <img file="EP0328024A1_D0024.tif" />CH-OH, a compound Hal-R22-Hal, CICO-R23- COCI, AIkOOC-R23-COOAlk, or<chemistry id="chem0039" num="0039"><img file="EP0328024A1_D0045.tif" /></chemistry>be used. As a trivalent reagent XIX, a compound (CICO)3R30, (AlKOOC)3R30 or cyanuric chloride can be used as tetravalent XIX a compound (ClCO)4 R31 or (AIKOOC)4 R31. Herein shark means a halogen atom and Alk a C1-C4-Alkyl group.

Y is a group <img file="EP0328024A1_D0024.tif" />CH-NHR26, you can proceed analogously. Y is a group<img file="EP0328024A1_D0024.tif" />C = 0, this can be reacted, for example, with a tetraol to form a bis-ketal.

Examples of compounds of the formula III are the following compounds:<tables id="tabl0006" num="0006"><img file="EP0328024A1_D0046.tif" /></tables><tables id="tabl0007" num="0007"><img file="EP0328024A1_D0047.tif" /></tables>

3) compounds of the formula IV,<chemistry id="chem0040" num="0040"><img file="EP0328024A1_D0048.tif" /></chemistry>where r is a value from 3 to 50, Q and Q 'independently of one another -O-, -S- or -N (R10) - mean and Y, R9 and R10 have the meanings given above, or in which -QR9-Q'- a group -NHNH-,<chemistry id="chem0041" num="0041"><img file="EP0328024A1_D0049.tif" /></chemistry>is. R is preferably a value from 3 to 25 and Q and Q '-0- or -N (R10).

These compounds can be prepared by reacting a dichlorotriazine XIV with a compound HQ-R9-Q'H. The latter compound can be, for example, a diol, a dithiol, a diamine or a hydroxyamine. Depending on the molar ratio of the two starting materials, products with a high or low degree of polycondensation r are obtained. The polycondensation is carried out in the presence of bases which bind the HCI formed.

Examples of compounds of the formula IV are the following compounds:<tables id="tabl0008" num="0008"><img file="EP0328024A1_D0050.tif" /></tables>

4) compounds of the formula V,<chemistry id="chem0042" num="0042"><img file="EP0328024A1_D0051.tif" /></chemistry>where r is a value from 3 to 50, Y and R1 have the meanings given earlier, To a C2-C4Is alkylene group and R23 has the meaning given above.

These compounds can be prepared from a monochlorotriazine of the formula XV by reaction with a compound HN (AnOH)2 and subsequent polycondensation with a dicarboxylic acid dialkyl ester<chemistry id="chem0043" num="0043"><img file="EP0328024A1_D0052.tif" /></chemistry>Herein Alk means C1-C4-Alkyi. An is preferably -CH2-CH2-. Here, too, the degree of polycondensation r can be varied by varying the molar ratio of the starting materials. Examples of dicarboxylic acid dialkyl esters which can be used are dimethyl succinate, diethyl adipate, dimethyl sebacate, dimethyl terephthalate or diethyl isophthalate.

Examples of compounds of formula V are the following compounds:<tables id="tabl0009" num="0009"><img file="EP0328024A1_D0053.tif" /></tables>

5) compounds of the formula VI,<chemistry id="chem0044" num="0044"><img file="EP0328024A1_D0054.tif" /></chemistry>where r is a value from 3 to 50, R20 has the meaning given above and <img file="EP0328024A1_D0024.tif" />Z'-R32-Z '<img file="EP0328024A1_D0055.tif" /> means one of the following groups<chemistry id="chem0045" num="0045"><img file="EP0328024A1_D0056.tif" /></chemistry><chemistry id="chem0046" num="0046"><img file="EP0328024A1_D0057.tif" /></chemistry><chemistry id="chem0047" num="0047"><img file="EP0328024A1_D0058.tif" /></chemistry><chemistry id="chem0048" num="0048"><img file="EP0328024A1_D0059.tif" /></chemistry><chemistry id="chem0049" num="0049"><img file="EP0328024A1_D0060.tif" /></chemistry><chemistry id="chem0050" num="0050"><img file="EP0328024A1_D0061.tif" /></chemistry>where q, R16, R22, R23, R24, R25, R26, R27 and R29 have the meaning given earlier.

These compounds can be prepared by first preparing a compound of the formula XX in which Y contains an OH or NH group by stepwise substitution of cyanuric acid chloride as described in (1),<chemistry id="chem0051" num="0051"><img file="EP0328024A1_D0062.tif" /></chemistry>and reacted this with a difunctional reagent. If, for example, Y is a group<img file="EP0328024A1_D0024.tif" />Is CH-OH, a compound Hal-R22-Hal or AIKOOC-R23-COOAIk can be used.

Alternatively, a bis-piperidine compound of the formula XXI<chemistry id="chem0052" num="0052"><img file="EP0328024A1_D0063.tif" /></chemistry>with a compound of formula XXII<chemistry id="chem0053" num="0053"><img file="EP0328024A1_D0064.tif" /></chemistry>implement. Or you can react a compound XXI with an equivalent of cyanuric acid chloride and finally leads R20 by implementation with R2° H on.

Examples of compounds of the formula VI are<tables id="tabl0010" num="0010"><img file="EP0328024A1_D0065.tif" /></tables>6) Compounds of formula VII<chemistry id="chem0054" num="0054"><img file="EP0328024A1_D0066.tif" /></chemistry>wherein s is 0 or 1, t 0 or 2 and u is a value from 5 to 100, Q "-O-, -NH- or -N (C1-C4Alkyl) means R34 Is hydrogen or methyl, R35 and R36 independently of one another -OR3, -SR3 or -NR4R5 mean, and copolymers of such a compound with (meth) acrylic acid, alkyl (meth) acrylates, hydroxyalkyl (meth) acrylates or maleic anhydride.

Such compounds can be obtained by polymerizing a monomer of the formula XXIII<chemistry id="chem0055" num="0055"><img file="EP0328024A1_D0067.tif" /></chemistry>or by copolymerization of XXIII with (meth) acrylic acid, an alkyl (meth) acrylate, a hydroxyalkyl (meth) acrylate or maleic anhydride. The polymerization takes place using .radical polymerization initiators such as organo-peroxides or azo compounds. The monomers XXIII can be prepared by stepwise substituents on cyanuric chloride as described in (1).

Preferred compounds of the formula VII are those in which s = 1, t = 0 and Q "-O-.

Examples of compounds of the formula VII are:<chemistry id="chem0056" num="0056"><img file="EP0328024A1_D0068.tif" /></chemistry>and its 1: 1 copolymer with methyl acrylate,<chemistry id="chem0057" num="0057"><img file="EP0328024A1_D0069.tif" /></chemistry>and its 1: 1 copolymer with butyl acrylate<chemistry id="chem0058" num="0058"><img file="EP0328024A1_D0070.tif" /></chemistry>and its 1: 1 copolymer with methyl methacrylate,<chemistry id="chem0059" num="0059"><img file="EP0328024A1_D0071.tif" /></chemistry>and its 1: 1 copolymer with hydroxyethyl acrylate. 7) compounds of the formula VIII,<chemistry id="chem0060" num="0060"><img file="EP0328024A1_D0072.tif" /></chemistry>where r is a value from 3 to 50, t is 0 or 2,<ul id="ul0005" list-style="none"><li>Q and Q 'have the meanings given,</li><li>Q "-O- -NH- or -N (C1-C4-Alkyl) - means and</li><li>R9, R35 and R36 have the meanings given above.</li></ul>

These compounds can be prepared by polycondensation of a compound of the formula XXIV,<chemistry id="chem0061" num="0061"><img file="EP0328024A1_D0073.tif" /></chemistry>with a difunctional compound HQ-R9-Q'H in the presence of two equivalents of a base. The starting materials XXIV can be prepared by stepwise substitution of cyanuric chloride as described under (1).

Compounds of the formula VIII in which t = 0 are preferred.

Examples of compounds of formula VIII are the following compounds:<chemistry id="chem0062" num="0062"><img file="EP0328024A1_D0074.tif" /></chemistry>8) compounds of the formula IX,<chemistry id="chem0063" num="0063"><img file="EP0328024A1_D0075.tif" /></chemistry> where v is a value from 2 to 30, t is 0 or 2, R35 and R36 have the meanings given above, R37 C.2-C8-Alkylene, C4-Ca-alkylene, xylylene, -CH2-CH (OH) -CH2-or -CH2CH (OH) CH20OR39-O-CH2(CH) CH2- means R38 one of the for R37 has given meanings or<chemistry id="chem0064" num="0064"><img file="EP0328024A1_D0076.tif" /></chemistry>-is, R39 C.2-C8-Alkylene, phenylene or<chemistry id="chem0065" num="0065"><img file="EP0328024A1_D0077.tif" /></chemistry>means and R27 has the meaning given above.

These compounds can be prepared from a compound of formula XXV<chemistry id="chem0066" num="0066"><img file="EP0328024A1_D0078.tif" /></chemistry>by reaction with a difunctional compound whose functional groups can react with secondary amines. Examples include the Hal-R dihalides38-Hal or epichlorohydrin or diglycidyl ether of the formula XXVa<chemistry id="chem0067" num="0067"><img file="EP0328024A1_D0079.tif" /></chemistry>

If R38 equal to R37 is, the compounds of formula IX from a primary amine of formula XXVI<chemistry id="chem0068" num="0068"><img file="EP0328024A1_D0080.tif" /></chemistry>by implementation with Hal-R37Hal, with epichlorohydrin or with a diglycidyl ether XXVa. The starting materials XXV and XXVI can be prepared by stepwise substitution of cyanuric chloride as described under (1) or (2).

Examples of compounds of the formula IX are:<chemistry id="chem0069" num="0069"><img file="EP0328024A1_D0081.tif" /></chemistry>9) compounds of the formula X,<chemistry id="chem0070" num="0070"><img file="EP0328024A1_D0082.tif" /></chemistry> where t is 0 or 2, v is a value from 2 to 30,

At C2-C4-Alkylene means R19, R20 and R23 have the meanings given above.

These compounds can be obtained by polycondensation of compounds of the formula XXVII<chemistry id="chem0071" num="0071"><img file="EP0328024A1_D0083.tif" /></chemistry>with dicarboxylic acid dialkyl esters AIKOOC-R23-COOAlk can be produced. Preference is given to the compounds of the formula X in which t is zero and An -CH2CH2- is. The starting materials XXVII can be prepared by stepwise substitution of cyanuric chloride as described in (1).

Examples of compounds of the formula X are<chemistry id="chem0072" num="0072"><img file="EP0328024A1_D0084.tif" /></chemistry>10) compounds of the formula XI,<chemistry id="chem0073" num="0073"><img file="EP0328024A1_D0085.tif" /></chemistry>wherein n is an integer from 1 to 6, t is 0 or 2, R2"Q", R35 and R36 have the meanings given above and R40 either one of the for R1 has given meanings or a group<chemistry id="chem0074" num="0074"><img file="EP0328024A1_D0086.tif" /></chemistry>mean.

To prepare these compounds, n equivalents of a compound of the formula XXVIII<chemistry id="chem0075" num="0075"><img file="EP0328024A1_D0087.tif" /></chemistry>with one equivalent of a compound of the formula<chemistry id="chem0076" num="0076"><img file="EP0328024A1_D0088.tif" /></chemistry>react in the presence of n equivalents of a base.

But you can also first a compound of formula XXVllla<chemistry id="chem0077" num="0077"><img file="EP0328024A1_D0089.tif" /></chemistry>and then n equivalents of XXVllla with one equivalent of R2(H)n implement.

The starting materials XXVIII and XXVllla can be prepared by stepwise substitution of cyanuric chloride as described under (1).

Examples of compounds of the formula XI are the following compounds:<chemistry id="chem0078" num="0078"><img file="EP0328024A1_D0090.tif" /></chemistry>11) compounds of the formula XII,<chemistry id="chem0079" num="0079"><img file="EP0328024A1_D0091.tif" /></chemistry>wherein r is a value from 3 to 50, R9 and R35 have the meanings given above, the group <img file="EP0328024A1_D0024.tif" />Z'-R23-Z<img file="EP0328024A1_D0055.tif" /> has one of the meanings given for class 5 and Q and Q 'independently of one another -0-, -S- or -N- (R10) mean.

To prepare these compounds, a bis-piperidine compound of the formula XXIX is first used<chemistry id="chem0080" num="0080"><img file="EP0328024A1_D0092.tif" /></chemistry> with 2 equivalents of cyanuric acid chloride, then leads the residue R35 by reaction with 2 equivalents of R35H and uses the product with a difunctional compound HQ-R9-0'H around. This can be, for example, a diol, a dithiol, a diamine or a hydroxyamine.

Examples of compounds of the formula XII are:<chemistry id="chem0081" num="0081"><img file="EP0328024A1_D0093.tif" /></chemistry>

The compounds of the formulas IV to X and XII are polymeric compounds, the formula representing the repeating molecular unit. The end groups of these polymeric products can be corresponding groups of the starting materials or of the polymerization catalyst. A desired limitation of the molecular weight of the polymeric products can be achieved by adding monofunctional compounds or chain terminators during production (polymerization). In this case, end groups are also created that correspond to these additions.

The compounds according to the invention can be used as stabilizers for organic materials against damage by light, oxygen and heat. Such materials to be stabilized can be, for example, oils, fats, waxes, cosmetics, biocides or photographic or reprographic materials. Of particular interest is the use in polymeric materials, such as those found in plastics, rubbers, paints or adhesives. Examples of polymers that can be stabilized in this way are the following:<ul id="ul0006" list-style="none"><li>1. Polymers of mono- and diolefins, for example polypropylene, polyisobutylene, polybutene-1, polymethylpentene-1, polyisoprene or polybutadiene and polymers of cycloolefins such as cyclopentene or norbornene; also polyethylene (which may or may not be crosslinked), for example high density polyethylene (HDPE), low density polyethylene (LDPE), linear low density polyethylene (LLDPE).</li><li>2nd Mixtures of the polymers mentioned under 1), for example mixtures of polypropylene with polyisobutylene, polypropylene with polyethylene (for example PP / HDPE, PP / LDPE) and mixtures of different types of polyethylene (for example LDPE / HDPE).</li><li>3rd Copolymers of mono- and diolefins with one another or with other vinyl monomers, such as, for example Ethylene-propylene copolymers, linear low-density polyethylene (LLDPE) and mixtures thereof with low-density polyethylene (LDPE), propylene-butene-1 copolymers, propylene-isobutylene copolymers, ethylene-butene-1 copolymers, ethylene-hexene Copolymers, ethylene-methylpentene copolymers, ethylene-heptene copolymers, ethylene-octene copolymers, propylene-butadiene copolymers, isobutylene-isoprene copolymers, ethylene-alkyl acrylate copolymers, ethylene-alkyl methacrylate copolymers, Ethylene-vinyl acetate copolymers or ethylene-acrylic acid copolymers and their salts (ionomers), as well as terpolymers of ethylene with propylene and a diene, such as hexadiene, dicyclopentadiene or ethylidene norbornene; furthermore mixtures of such copolymers with one another and with polymers mentioned under 1), for example polypropylene / ethylene-propylene copolymers, LDPEl ethylene-vinyl acetate copolymers, LDPE / ethylene-acrylic acid copolymers, LLDPE / ethylene-vinyl acetate copolymers and LLDPE / ethylene-acrylic acid Copolymers.</li><li>3a. Hydrocarbon resins (e.g. Cs-C9) including hydrogenated modifications thereof (e.g. tackifier resins).</li><li>4th Polystyrene, poly- (p-methylstyrene), poly- (ci-methylstyroi).</li><li>5. Copolymers of styrene or a-methylstyrene with dienes or acrylic derivatives, such as styrene-butadiene, styrene-acrylonitrile, styrene-alkyl methacrylate, styrene-butadiene-alkyl acrylate, styrene-maleic anhydride, styrene-acrylonitrile-methyl acrylate; Mixtures of high impact strength from styrene copolymers and another polymer, such as, for example, a polyacrylate, a diene polymer or an ethylene-propylene-diene terpolymer; and block copolymers of styrene, such as Styrene-butadiene-styrene, styrene-isoprene-styrene, styrene-ethylene / butylene-styrene or styrene-ethylene / propylene-styrene.</li><li>6. Graft copolymers of styrene or o-methylstyrene, such as styrene on polybutadiene, styrene on polybutadiene-styrene or polybutadiene-acrylonitrile copolymers, styrene and acrylonitrile (or methacrylonitrile) on polybutadiene; Styrene, acrylonitrile and methyl methacrylate on polybutadiene; Styrene and maleic anhydride on polybutadiene; Styrene, acrylonitrile and maleic anhydride or maleimide on polybutadiene; Styrene and maleimide on polybutadiene, styrene and alkyl acrylates or Alkyl methacrylates on polybutadiene, styrene and acrylonitrile on ethylene-propylene-diene terpolymers, styrene and acrylonitrile on polyalkylacrylates or polyalkyl methacrylates, styrene and acrylonitrile on acrylate-butadiene copolymers, as well as their mixtures with the copolymers mentioned under 5), as described, for example, as so-called ABS, MBS, ASA or AES polymers are known.</li><li>7. Halogen-containing polymers, such as polychloroprene, chlorinated rubber, chlorinated or chlorosulfonated polyethylene, epichlorohydrin homo- and copolymers, in particular polymers made from halogen-containing vinyl compounds, such as polyvinyl chloride, polyvinylidene chloride, polyvinyl fluoride, polyvinylidene fluoride; and their copolymers, such as vinyl chloride-vinylidene chloride, vinyl chloride-vinyl acetate or vinylidene chloride-vinyl acetate.</li><li>8th. Polymers derived from α, 8-unsaturated acids and their derivatives, such as polyacrylates and polymethacrylates, polyacrylamides and polyacrylonitriles.</li><li>9. Copolymers of the monomers mentioned under 8) with one another or with other unsaturated monomers, such as, for example, acrylonitrile-butadiene copolymers, acrylonitrile-alkyl acrylate copolymers, acrylonitrile-alkoxyalkyl acrylate copolymers, acrylonitrile-vinyl halide copolymers or acrylonitrile-alkyl methacrylate-butadiene-butadiene.</li><li>10th Polymers derived from unsaturated alcohols and amines or their acyl derivatives or acetals, such as polyvinyl alcohol, polyvinyl acetate, stearate, benzoate, maleate, polyvinyl butyral, polyallylphthalate, polyallylmelamine; as well as their copolymers with olefins mentioned in point 1.</li><li>11. Homopolymers and copolymers of cyclic ethers, such as polyalkylene glycols, polyethylene oxide, polypropylene oxide or their copolymers with bisglycidyl ethers.</li><li>12th Polyacetals, such as polyoxymethylene, and also those polyoxymethylenes which contain comonomers, such as, for example, ethylene oxide; Polyacetals modified with thermoplastic polyurethanes, acrylates or MBS.</li><li>13. Polyphenylene oxides and sulfides and their mixtures with styrene polymers or polyamides.</li><li>14. Polyurethanes derived from polyethers, polyesters and polybutadienes with terminal hydroxyl groups on the one hand and aliphatic or aromatic polyisocyanates on the other hand, and their precursors.</li><li>15. Polyamides and copolyamides derived from diamines and dicarboxylic acids and / or from aminocarboxylic acids or the corresponding lactams, such as polyamide 4, polyamide 6, polyamide 6,6, 6/10, 6/9, 6/12, 4/6, polyamide 11, polyamide 12, aromatic polyamides starting from m-xylene, diamine and adipic acid; Polyamides made from hexamethylenediamine and iso- and / or terephthalic acid and optionally an elastomer as a modifier, for example Poly-2,4,4-trimethylhexamethylene terephthalamide, poly-m-phenylene-isophthalamide. Block copolymers of the aforementioned polyamides with polyolefins, olefin copolymers, ionomeric or chemically bonded or grafted elastomers; or with polyethers, such as with polyethylene glycol, polypropylene glycol or polytetramethylene glycol. Furthermore, polyamides or copolyamides modified with EPDM or ABS; as well as polyamides condensed during processing ("RIM polyamide systems").</li><li>16. Polyureas, polyimides, polyamide-imides and polybenzimidazoles.</li><li>17th Polyesters which are derived from dicarboxylic acids and dialcohols and / or from hydroxycarboxylic acids or the corresponding lactones, such as polyethylene terephthalate, polybutylene terephthalate, poly-1,4-dimethylolcyclohexane terephthalate, polyhydroxybenzoates, and also block polyether esters which are derived from polyethers having hydroxyl end groups; furthermore polyesters modified with polycarbonates or MBS.</li><li>18th Polycarbonates and polyester carbonates.</li><li>19th Polysulfones, polyether sulfones and polyether ketones.</li><li>20th Crosslinked polymers derived from aldehydes on the one hand and phenols, urea or melamine on the other hand, such as phenol-formaldehyde, urea-formaldehyde and melamine-formaldehyde resins.</li><li>21. Drying and non-drying alkyd resins.</li><li>22. Unsaturated polyester resins derived from copolyesters of saturated and unsaturated dicarboxylic acids with polyhydric alcohols, as well as vinyl compounds as crosslinking agents, as well as their halogen-containing, flame-retardant modifications.</li><li>23. Crosslinkable acrylic resins derived from substituted acrylic esters, such as epoxy acrylates, urethane acrylates or polyester acrylates.</li><li>24th Alkyd resins, polyester resins and acrylate resins which are crosslinked with melamine resins, urea resins, polyisocyanates or epoxy resins.</li><li>25th Crosslinked epoxy resins derived from polyepoxides, for example from bis-glycidyl ethers or from cycloaliphatic diepoxides.</li><li>26. Natural polymers, such as cellulose, natural rubber, gelatin, and their polymer-homologously chemically modified derivatives, such as cellulose acetates, propionates and butyrates, or the cellulose ethers, such as methyl cellulose; as well as rosins and derivatives.</li><li>27 Mixtures (polyblends) of the aforementioned polymers, such as PP / EPDM, polyamide / EPDM or ABS, PVC / EVA, PVC / ABS, PVC / MBS, PC / ABS, PBTP / ABS, PC / ASA, PC / PBT, PVC / CPE, PVC / acrylates, POM / thermoplastic PUR, PC / thermoplastic PUR, POM / acrylate, POM / MBS, PPO / HIPS, PPO / PA 6.6 and copolymers, PA / HDPE, PA / PP, PA / PPO.</li></ul>

The stabilization of polyolefins and binders for paints is of particular importance.

The stabilizers are expediently added to the organic materials in an amount of 0.01 to 5% by weight, calculated on the material to be stabilized. 0.1 to 2% by weight is preferably used. Polymeric materials can be added as early as their manufacture (polymerization). It is preferably carried out before or during the shaping of the polymer.

In certain cases it may be advantageous to use mixtures of two or more of the stabilizers according to the invention.

Together with the stabilizers according to the invention, other stabilizers or other customary additives can be added to the organic material. Examples of this are the following additions:

1. Antioxidants

1.1. Alkylated monophenols, for example 2,6-di-tert-butyl-4-methylphenol. 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert. butyl-4-i-butylphenol, 2,6-di-cyclopentyl-4-methylphenol, 2- (a-methylcyclohexyl) -4,6-dimethylphenol, 2,6-di-octadecyl-4-methylphenol, 2,4, 6-tri-cyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, 2,6-di-nonyl-4-methylphenol.

1.2. Alkylated hydroquinones, e.g. 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butyl-hydroquinone, 2,5-di-tert-amyl-hydroquinone, 2,6-diphenyl-4- octadecyloxyphenol.

1.3. Hydroxylated thiodiphenyl ethers, for example 2,2-thio-bis- (6-tert-butyl-4-methylphenol), 2,2-thio-bis- (4-octylphenol), 4,4-thio-bis- (6-tert .butyi-3-methyl! phenol), 4,4-thio-bis- (6-tert.butyl-2-methylphenol).

1.4. Alkylidene bisphenols, e.g. 2,2-methylene-bis- (6-tert-butyl-4-methylphenol), 2,2-methylene-bis- (6-tert-butyl-4-ethylphenol), 2,2-methylene-bis- [4th -methyl-6- (a-methylcyclohexyi) phenol], 2,2'-methyl-bis- (4-methyl-6-cyclohexylphenol), 2,2-methylene-bis- (6-nonyl-4-methylphenol) , 2,2-methylene-bis- (4,6-di-tert-butylphenol), 2,2-ethylidene-bis- (4,6-di-tert-butylphenol), 2,2-ethylidene-bis- (6- tert-butyl-4-isobutylphenol), 2,2-methylene-bis- [6- (α-methylbenzyl) -4-nonylphenol], 2,2-methylene-bis- [6- (α, α-dimethylbenzyl) - 4-nonylphenolj, 4,4-methylene-bis- (2,6-di-tert-butylphenol), 4,4-methylene-bis- (6-tert-butyl-2-methylphenol), 1,1-bis- (5-tert .butyl-4-hydroxy-2-methylphenyl) butane, 2,6-bis (3-tert-buti-5-methyl-2-hydroxybenzyl) -4-methylphenol, 1,1,3-tris (5th tert-butyl-4-hydroxy-2-methylphenyl) butane, 1,1-bis (5-tert-butyl-4-hydroxy-2-methylphenyl) -3-n-dodecyl mercaptobutane, ethylene glycol bis [3 , 3-bis (3-tert-butyl-4-hydroxyphenyl) -butyrate], bis- (3-tert-butyl-4-hydroxy-5-methylphenyl) -dicyclopentadiene, Bis- [2- {3-tert-butyl-2-hydroxy-5-methyl-benzyl) -6-tert-butyl-4-methyl-phenyl] terephthalate.

1.5 benzyl compounds, e.g. 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) -2,4,6-trimethylbenzene, bis- (3,5-di-tert-butyl-4-hydroxybenzyl) - sulfide, 3,5-di-tert-butyl-4-hydroxybenzyl-mercaptoacetic acid isooctyl ester, bis- (4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) dithiol terephthalate, 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, 1,3,5-tris (4-tert.butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate, 3.5- Di-tert-butyl-4-hydroxybenzylphosphonic acid dioctadecyl ester, Ca salt of monoethyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate, 1,3,5-tris (3,5-dicyclohexyl-4-hydroxybenzyl) isocyanurate.

1.6. Acylaminophenols, e.g. 4-hydroxy-lauric anilide, 4-hydroxy-stearic anilide, 2,4-bis (octylmercapto) -6- (3,5-di-tert-butyl-4-hydroxyanilino) -s-triazine, N- ( 3,5-di-tert-butyl-4-hydroxyphenyl) carbamic acid octyl ester.

1.7. Esters of β- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid with mono- or polyhydric alcohols, such as with methanol, octadecanol, 1,6-hexanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol , Tris (hydroxyethyl) isocyanurate, N, N-bis (hydroxyethyl) oxalic acid diamide. 1.8. Esters of β- (5-tert.8utyl-4-hydroxy-3-methylpheny!) Propionic acid with mono- or polyhydric alcohols, such as with methanol, octadecanol, 1,6-hexanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxy) ethyl isocyanurate, N, N-bis (hydroxyethyl) oxalic acid diamide. 1.9. Esters of β- (3,5-dicyclohexyl-4-hydroxyphenyl) propionic acid with mono- or polyhydric alcohols, such as, for example with methanol, octadecanol, 1,6-hexanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxy) ethyl isocyanurate, N, N-bis (hydroxyethyi) oxalic acid diamide. 1.10. Amides of β- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid, such as, for example, N, N-bis (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) hexamethylene diamine, N, N -Bis- (3,5-di-tert.buty) -4-hydroxypheny! Propionyt) -tr! Methylenediamine, N, N-bis- (3,5-di-tert.butyl-4-hydroxyphenylpropionyl) -hydrazine.

2nd UV absorbers and light stabilizers

2.1. 2- (2-Hydroxyphenyl) benzotriazoles, such as 5'-methyl-, 3 ', 5'-di-tert-butyl-, 5'-tert-butyl-, 5' - (1,1,3, 3-Tetramethylbutyl) -, 5-chloro-3, 5-di-tert.butyt-, 5-Ch! Or-3'-tert.buty) -5'-methyt-, 3'-sec.Buty! -5 '-tert.butyl, 4'-octoxy, 3,5-di-tert.amyl, 3,5-bis (α, α-dimethylbenzyl) derivative.

2.2. 2-hydroxybenzophenones, such as, for example, 4-hydroxy, 4-methoxy, 4-octoxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy, 4,2, 4-trihydroxy, 2-hydroxy- 4,4-dimethoxy derivative.

2.3. Esters of optionally substituted benzoic acids, such as 4-tert-butylphenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoylresorcinol, bis- (4-tert.butylbenzoyl) resorcinol, benzoylresorcinol, 3,5-di-tert.butyl-4- 2,4-di-tert-butylphenyl hydroxybenzoate, hexadecyl 3,5-di-tert-butyl-4-hydroxybenzoate.

2.4. Acrylates, such as, for example, o-cyano-ß, ß-diphenylacrylic acid ethyl ester or isooctyl ester, α-carbomethoxy-cinnamic acid methyl ester, α-cyano-β-methyl-p-methoxy-cinnamic acid methyl ester or -butyl ester, a-carbomethoxy-p- methoxycinnamic acid methyl ester, N- (ß-carbomethoxy-ß-cyanovinyl) -2-methyl-indoline.

2.5. Nickel compounds, such as Nickel complexes of 2,2-thio-bis- [4- (1,1,3,3-tetramethylbutyl) phenol], such as the 1: 1 or the 1: 2 complex, optionally with additional ligands, such as n- Butylamine, triethanolamine or N-cyclohexyl-diethanolamine, nickel dibutyldithiocarbamate, nickel salts of 4-hydroxy-3,5-di-tert-butylbenzylphosphonic acid monoalkyl esters, such as methyl or ethyl ester, nickel complexes of ketoximes, such as 2-hydroxy-4-methyl -phenyl-undecylketoxime, nickel complexes of 1-phenyl-4-lauroyl-5-hydroxy-pyrazole, optionally with additional ligands.

2.6. Sterically hindered amines, such as Bis (2,2,6,6-tetramethylpiperidyl) sebacate, bis (1,2,2,6,6-pentame-thyipiperidyl) sebacate, n-butyl-3,5-di-tert.butyl- 4-hydroxybenzylmalonic acid bis (1,2,2,6,6-pentamethylpiperidyl) ester, condensation product from 1-hydroxyethyl-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid, condensation product from N, N '-Bis- (2,2,6,6-tetramethyl-4-piperidyl) hexamethylenediamine and 4-tert-octylamino-2,6-dichloro-1,3,5-s-triazine, tris- (2.2 , 6,6-tetramethyl-4-piperidyl) nitrite lotriacetate, Tetrakis (2,2,6,6-tetramethyl-4-piperidyl) -1,2,3,4-butanetetraoate, 1,1- (1,2-ethanediyl) -bis- (3,3,5,5 -tetramethyl-piperazinone).

2.7. Oxalic acid diamides, such as 4,4-di-octyloxy-oxanilide, 2,2-dioctyloxy-5,5-di-tert-butyl-oxanilide, 2,2'-didodecytoxy-5,5 di-tert.buty! -Oxani ! id, 2-ethoxy-2-ethyl-oxaniiide. N, N-bis (3-dimethy! Aminopropyi) oxaiamide. 2-ethoxy-5-tert-butyl-2-ethyloxanilide and its mixture with 2-ethoxy-2-ethyl-5,4-di-tert.butyl-oxanilide, mixtures of o- and p-methoxy- and of o- and p-ethoxy-di-substituted oxanilides.

2.8. 2- (2-hydroxyphenyl) -1,3,5-triazines such as 2,4,6-tris (2-hydroxy-4-octyloxyphenyl) -1,3,5-triazine, 2- (2-hydroxy- 4-octyloxyphenyl) -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2- (2,4-dihydroxyphenyl) -4,6-bis (2,4-dimethylphenyl) -1 , 3,5-triazine, 2,4-bis (2-hydroxy-4-propyloxyphenyl) -6- (2,4-dimethylphenyi) -1,3,5-triazine, 2- (2-hydroxy-4-octyloxyphenyl ) -4,6-bis (4-methylphenyl) -1,3,5-triazine, 2- (2-hydroxy-4-dod®cyloxyphenyl) -4,6-bis- (2,4-dimethylphenyl) -1 , 3,5-triazine.

3rd Metal deactivators such as N, N-diphenyloxalic acid diamide, N-salicylal-N-salicyloylhydrazine, N, N-bis- (salicyloyl) hydrazine, N, N-bis (3,5-di-tert-butyl-4-hydroxyphenylpropionyi ) -hydrazine, 3-salicyloylamino-1,2,4 = triazole, bis (benzylidene) oxalic acid dihydrazide.

4th Phosphites and phosphonites, such as Triphenylphosphite, diphenylalkylphosphite, phenyldialkylphosphite, tris- (nonylphenyl) -phosphite, trilaurylphosphite, trioctadecylphosphite, distearyl-pentaerythritol-diphosphite, tris- (2,4-di-tert.butylphenyl) -phosphite, diisodhritol-bisditodite-bis-ditodite-bisphosphite -tert.butylphenyl) pentaerythritol diphosphite, tristearyl sorbitol triphosphite, tetrakis (2,4-di-tert.butylphenyl) -4,4 -biphenylene diphosphonite, 3,9-bis- (2,4-di-tert .butylphenoxy) -2,4,8,10-tetraoxa-3,9-diphosphaspiro [5.5] undecane.

5. Peroxide-destroying compounds, such as, for example, esters of β-thio-dipropionic acid, for example the lauryl, stearyl, myristyl or tridecyl ester, mercaptobenzimidazole, the zinc salt of 2-mercaptobenzimidazole, zinc dibutyl dithiocarbamate, dioctadecyl disulfite tetrakis (pentaerythracetate) dodecylmercapto) propionate.

6. Polyamide stabilizers, such as copper salts in combination with iodides and / or phosphorus compounds and salts of divalent manganese.

7. Basic co-stabilizers, such as melamine, polyvinylpyrrolidone, dicyandiamide, triallyl cyanurate, urea derivatives, hydrazine derivatives, amines, polyamides, polyurethanes, alkali and alkaline earth metal salts of higher fatty acids, for example Ca stearate, Zn stearate, Mg stearate, Na -Ricinoleate, K-palmitate, antimony catecholate or tin catecholate.

8th. Nucleating agents, such as 4-tert-butylbenzoic acid, adipic acid, diphenylacetic acid.

9. Fillers and reinforcing agents such as calcium carbonate, silicates, glass fibers, asbestos, talc, kaolin, mica, barium sulfate, metal oxides and hydroxides, carbon black, graphite.

10th Other additives, such as plasticizers, lubricants, emulsifiers, pigments, optical brighteners, flame retardants, antistatic agents, blowing agents.

When such costabilizers are also used, synergistic effects can occur, which is particularly the case when UV absorbers are also used.

When the compounds according to the invention are used as stabilizers for photographic materials, use in photographic layers, for example on films or photographic papers, is of particular interest.

Some of the compounds according to the invention can also be used as an intermediate in the production of other compounds according to the invention. This is especially true for compounds bearing chlorine atoms on the triazine ring. Preferred stabilizers are those compounds which contain no chlorine atoms on the triazine radicals.

The following examples illustrate the preparation and use of the compounds according to the invention in more detail. Parts and% mean parts by weight and% by weight. The temperatures are given in degrees Celsius.

Example 1: 2,4-dichloro-6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine.

92.2 g of cyanuric chloride and 142.6 g of 2,2,6,6-tetramethylpiperidine are stirred in 400 ml of xylene at 120 ° for 10 hours. After cooling to room temperature, the 2,2,6,6-tetramethylpiperidine hydrochloride formed is filtered off and washed with 100 ml of xylene. The yellow to brownish xylene solution is washed three times with 100 ml of water, dried over sodium sulfate, stirred with 5 g Tonsil optimum (bleaching earth) and 5 g animal charcoal for 10 minutes, clarified and evaporated in vacuo. The residue obtained is recrystallized from 300 ml of hexane with the addition of 3 g of Tonsil optimum. The 2,4-dichloro-6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine is obtained as colorless crystals with a melting point of 129..

Example 2: 2,4-dichloro-6- (2,2,6,6-tetramethyl-4-benzoyloxypiperidin-1-yl) -1,3,5-triazine.

46.1 g of cyanuric chloride and 136.0 g of 2,2,6,6-tetramethyl-4-benzoyloxypiperidine are reacted and worked up in 300 ml of xylene as described in Example 1. After recrystallization from isopropanol, 2,4-dichloro-6- (2,2,6,6-tetramethyl-4-benzoyloxy-piperidin-1-yl) -1,3,5-triazine is obtained as colorless crystals with a Melting point of 145 °.

Example 3: 2-Chloro-4-ethylamino-6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine.

28.9 g of 2,4-dichloro-6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine (prepared according to Example 1) in 250 ml of ethanol at room temperature with 15 g of a 70% aqueous ethylamine solution are added. The temperature rises quickly to about 35*. Then 12 hours at 55* stirred, 25 ml of water added and on 5. cooled down. The resulting precipitate is filtered off, washed with 200 ml of water and dried. Crystallization from acetonitrile gives the 2-chloro-4-ethylamino-6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine as colorless crystals with a melting point of 148 °.

Example 4: 2-chloro-4-diethylamino-6- (2,2,6,6-tetramethylpiperidin-1-yl) 1,3,5-triazine.

If 15 g of diethylamine are used instead of the ethylamine solution and the procedure is otherwise as described in Example 3, 2-chloro-4-diethylamino-6- (2,2,6,6-tetramethylpiperidin-1-yl) -1 is obtained , 3,5-triazine as a colorless substance with a melting point of 77 °.

Example 5: 2,4-bis-isopropylamino-6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine.

43.4 g of 2,4-dichloro-6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine are combined with 39.0 g of isopropylamine in 200 ml of xylene for 8 hours in one Autoclave heated to 160 °. After cooling to room temperature, the contents of the autoclave are washed three times with 100 ml of water each time, the yellowish xylene solution is dried over sodium sulfate, stirred for 10 minutes with 5 g of Tonsil optimum (bleaching earth), filtered and evaporated. The 2,4-bis-isopropylamino-6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine obtained is a slightly yellowish resin which could not be crystallized.

Example 6: 2,4-bis-dibutylamino-6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine.

57.8 g of 2,4-dichloro-6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine are suspended in 200 ml of xylene at room temperature. 25.8 g of dibutylamine are added dropwise in the course of 15 minutes, the temperature rising to 40 °. A solution of 8.8 g of sodium hydroxide in 40 ml of water is added to the reaction mixture in about 15 minutes and the mixture is then stirred at 60 'for 2 hours. The aqueous phase is now separated off and 28.4 g of dibutyiamine and a solution of 9.6 g of sodium hydroxide in 20 ml of water are added to the clear, organic phase. It is now heated on a water separator until an internal temperature of approx. 135 ° is reached and then stirred at this temperature for 12 hours. The contents of the flask are cooled to 90 °, a solution of 3 g of sodium hydroxide in 100 ml of water is added and the mixture is stirred vigorously at 90 for 30 minutes. The aqueous phase is now separated off, the xylene solution is washed five times with 100 ml of water each time and evaporated in vacuo. The yellowish oily residue is distilled in a high vacuum. 2,4-Bis-dibutylamino-6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine is obtained as a colorless oil with a boiling point of 173 ° at 6.5 Pa.

Example 7: 2,4-Dimorpholino-6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine.

If 36.6 g of morpholine (1st portion: 17.4 g; 2nd portion: 19.2 g) are used instead of dibutylamine and the procedure is otherwise as described in Example 6, after crystallization from ethanol, the 2,4-Dimorpholino-6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine with a melting point of 147-48 °.

Example 8: 2,4-bis-butylamino-6- (2,2,6,6-tetramethyl-4-benzoyloxypiperidin-1-yl) -1,3,5-triazine.

20.5 g of 2,4-dichloro-6- (2,2,6,6-tetramethyl-4-benzoyloxypip®ridin-1-yl) -1,3,5-triazine (prepared according to Example 2) are made in 200 ml of xylene with 8.0 g of n-butylamine was stirred under reflux for 4 hours. 4.4 g of powdered sodium hydroxide are added to the reaction mixture and the mixture is stirred under reflux for a further 15 hours. The contents of the flask are cooled to room temperature and, after adding 100 ml of water, stirred vigorously until the precipitated salt has completely dissolved. The aqueous phase is separated off, the xylene solution is washed three times with 100 ml of water and evaporated in vacuo. The oily residue becomes 100. and 13 Pa. dried. 2,4-Bis-butylamino-6- (2,2,6,6-tetramethyl-4 = benzoylpiperidin-1-yl) -1,3,5-triazine is obtained as a yellowish viscous mass.

Example 9: 2,4-bis-butylamino-6- (2,2,6,6-tetramethyl-4-hydroxypiperidin-1-yl) -1,3,5-triazine.

10th g 2,4-bis-butylamino-6- (2,2,6,6-tetramethyl-4-benzoyloxypiperidin-1-yl) -1,3,5-triazine (prepared according to Example 8) are mixed with 50 ml of methanol and 50 ml of 20 percent sodium hydroxide solution heated under reflux for 6 hours. The methanol is distilled off in vacuo from the reaction mixture. 100 ml of toluene and 50 ml of water are added to the residue, the mixture is shaken vigorously, the aqueous phase is separated off and the toluene solution is washed three times with 50 ml of water each time. After evaporation of the toluene solution, 2,4-bis-butylamino-6- (2,2,6,6-tetramethyl-4-hydroxypiperidin-1-yl) -1,3,5-triazine is obtained as a yellowish viscous mass. Crystallization from acetonitrile gives colorless crystals, which at 90. C melt.

Example 10: 2,4-dichloro-6- (2,2,6,6-tetramethyl-4-hexyloxypiperidin-1-yl) -1,3,5-triazine.

62.7 g of 4-hexyloxy-2,2,6,6-tetramethylpiperidine are added to a solution of 23.9 g of cyanuric chloride in 100 ml of toluene with stirring. The mixture is then heated to 80 ° for 24 hours. A white precipitate of the piperidine hydrochloride is formed. After cooling, the precipitate is filtered off, the toluene solution is washed several times with 2N hydrochloric acid and dried over Na2S04 and evaporate it. The residue is recrystallized from acetonitrile. The product obtained melts at 49-51 °.

Example 11: 2,4-Dimorpholino-6- (2,2,6,6-tetramethyl-4-hexyloxypiperidin-1-yl) -1,3,5-triazine.

9.7 g of the product from Example 10 are heated under reflux with 50 ml of morpholine for 3 hours. The orange reaction mixture is poured onto water. The resulting crude product is dissolved in ethyl acetate and on a Si02Column cleaned chromatographically. The cleaned product is a viscous mass.

Example 12: If diisobutylamine is used instead of morpholine in example 11 and the procedure is otherwise the same as in example 11, 2,4-bis (diisobutylamino) -6- (2,2,6,6-tetramethyl-4-hexyloxypiperidine) is obtained -1-yl) -1,3,5-triazine as a viscous liquid.<tables id="tabl0012" num="0012"><img file="EP0328024A1_D0095.tif" /></tables>

Example 13: If dibutylamine is used instead of morpholine in Example 11 and the procedure is otherwise as described in Example 11, 2,4-bis (dibutylamino) -6- (2,2,6,6-tetramethyl-4-hexyloxypiperidine) is obtained -1-yl) -1,3,5-triazine as a viscous mass.<tables id="tabl0013" num="0013"><img file="EP0328024A1_D0096.tif" /></tables>

Example 14: Polycondensate of 2,4-dichloro-6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine and hexamethylene diamine.

A solution of 12.4 g (43 mmol) of 2,4-dichfor-6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine in 50 ml of xylene is added at 100 ° a solution of 10.5 g (90 mmol) of hexamethylenediamine in 50 ml of xylene is slowly added dropwise, and the reaction mixture is stirred under reflux for 22 hours. After cooling, the mixture is filtered, the filtrate is washed twice with 50 ml of water and the amount of hexane is added until no more precipitation occurs. The precipitate is filtered off, the filtrate washed three times with 50 ml of water, over Na2SO4 dried and evaporated. The residue is dried in vacuo at 50 °. A resin-like polymer with a molecular weight M is obtainedn = 1029 / m w = 1545 (Ge! Permeation chromatography).

Example 15: 2,4-dichloro-6- (1,3,8-triaza-2,4-dioxo-3,7,7,9,9-pentamethyl-spiro [4,5] dec-1-yl) -1,3,5-triazine.

To a solution of 90.9 g (0.38 moi) 1,3,8-triaza-2,4-dioxo-3,7,7,9,9-pentamethyl-spiro [4,5] decane in 500 ml A solution of 35.1 g (0.19 mol) of cyanuric chloride in 200 ml of xylene is added dropwise at 0-5 with stirring. The mixture is then heated to reflux for 24 hours. After cooling, the precipitate is filtered off and the filtrate is washed first with water which has been adjusted to pH 5 with acetic acid, then with a Na2C03 solution and finally with water. The xylene solution is filtered, over Na2S04. dried and evaporated in vacuo. The residue is recrystallized from 70 ml of acetonitrile. A brownish powder is obtained which melts at 237-242 °.<tables id="tabl0014" num="0014"><img file="EP0328024A1_D0097.tif" /></tables>

Example 16: 2,4-Dimorpholino-6- (1,3,8-triaza-2,4-dioxo-3,7,7,9,9-pentamethyl-spiro [4, 5] dec-1-yl) -1,3,5-triazine.

5.4 g of morpholine are slowly added to 6 g of the product from Example 15 with ice cooling. Then another 30 ml of morpholine are added and the reaction mixture is heated to reflux. After refluxing for 38 hours, the mixture is cooled and 50 ml of water are added. The precipitate is filtered off, washed with water and dried. The product is recrystallized from methylene chloride / hexane. A white powder is obtained which melts at 319-321 ° with decomposition.<tables id="tabl0015" num="0015"><img file="EP0328024A1_D0098.tif" /></tables>

Example 17: 2,4-dichloro-6- (4,4-eth ylenedioxy-2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine.

A solution of 55.3 is added to a solution of 119.6 g (0.6 m ° 1) of 4,4-ethylenedioxy-2,2,6,6-tetramethylpiperidine in 100 ml of xylene with stirring and cooling to 0-5 ° g (0.3 mol) of cyanuric chloride in 300 ml of xylene were added dropwise. The mixture is then heated to reflux and kept at the boil for 26 hours. After adding 150 ml of xylene, the mixture is allowed to cool and the precipitate is filtered off. The filtrate is evaporated in vacuo. The residue is recrystallized from 300 ml of acetonitrile. The product obtained is a brownish powder that melts at 169-172 °.<tables id="tabl0016" num="0016"><img file="EP0328024A1_D0099.tif" /></tables>

Example 18: 2-Chloro-4-diisopropylamino-6- (4,4-ethylenedioxy-2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine.

26.1 g (258 mmol) of diisopropylamine are added to a solution of 29.9 g (86 mmol) of the product from Example 17 in 100 ml of toluene with stirring. The mixture is heated to reflux and kept at this temperature for 24 hours. After cooling, a solution of 4.1 g of NaOH in 21 ml of water is added. The solid product is filtered off and recrystallized from 25 ml of toluene. A yellowish powder is obtained which melts at 179-184 °.<tables id="tabl0017" num="0017"><img file="EP0328024A1_D0100.tif" /></tables>

Example 19: 2-Octyiamino-4-diisopropylamino-6- (4,4-ethylenedioxy-2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine.

15 g (36.4 mmol) of the product from Example 18 are heated together with 30 ml of octylamine at 120 ° for 3 hours. After cooling, 40 ml of water are added and extracted three times with 30 ml of methylene chloride. The CH2Cl2Solution is washed with water, over Na2S04 dried and evaporated. The oily residue is dissolved in hexane / acetone and on a Si02Column cleaned chromatographically. The main fraction is a viscous mass.<tables id="tabl0018" num="0018"><img file="EP0328024A1_D0101.tif" /></tables>

Example 20: 2,4-Dimorpholino-6- (4,4-ethylenedioxy-2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine.

40 g of morpholine are added to 40 g of the product from Example 17 with ice cooling. After adding a further 100 g of morpholine, the mixture is slowly heated to 130 ° with stirring and boiled under reflux for 6 hours. After cooling to room temperature, 150 ml of water are added. The precipitate formed is filtered off, washed with water and recrystallized from acetonitrile. The product obtained melts at 216-221<tables id="tabl0019" num="0019"><img file="EP0328024A1_D0102.tif" /></tables>

Example 21: 2,4-Dimorpholino-6- (4-oxo-2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine.

29.6 g of the product from Example 20 in 200 ml of a solution of 1.26 g of p-toluenesulfonic acid in a 1: 1 mixture of tetrahydrofuran and water are introduced with stirring. After adding a further 60 ml of tetrahydrofuran, the mixture is heated to 50 'for 5 hours. Then another 1.26 g of toluenesulfonic acid are added and the mixture is stirred at 50 'for a further 14 hours. After cooling, it is extracted five times with 50 ml of methylene chloride. The united CH2Cl2- Solutions are washed with water, over Na2S04. dried and evaporated. The residue is recrystallized from 80 ml of acetonitrile. The white crystals obtained melt at 188-192 °.<tables id="tabl0020" num="0020"><img file="EP0328024A1_D0103.tif" /></tables>

Example 22: 2,4-dichloro-6- (2,2,6,6-tetramethyl-4-dodecyloxypiperidin-1-yl) -1,3,5-triazine.

If, instead of the 4-hexyloxy-2,2,6,6-tetramethylpiperidine described in Example 10, the same molar equivalent amount of 4-dodecyloxy-2,2,6,6-tetramethylpiperidine is used and the procedure is exactly the same as in Example 10 described, the above compound is obtained as a slightly yellowish oil<tables id="tabl0021" num="0021"><img file="EP0328024A1_D0104.tif" /></tables>

Example 23: 2,4-dichloro-6- (2,2,6,6-tetramethyl-4-allyloxypiperidin-1-yl) -1,3,5-triazine.

If the 4-hexyloxy-2,2,6,6-tetramethylpiperidine described in Example 10 is used, the same molar equivalent amount of 4-allyloxy-2,2,6,6-tetramethylpiperidine is used and the procedure is exactly the same as in Example 10 described, the above compound is obtained as a crystalline product which can be recrystallized from ethanol. The product obtained melts at 53-55 'C.

Example 24: If di (-2-ethyl-hexyl) amine is used instead of the morpholine in Example 11 and the procedure is exactly the same as described in Example 11, 2,4-bis [di (-2-ethyl- hexyl) amino] -6- (2,2,6,6-tetramethyl-4-hexyloxypiperidin-1-yl) -1,3,5-triazine as a yellowish oil.<tables id="tabl0022" num="0022"><img file="EP0328024A1_D0105.tif" /></tables>

Example 25: If 4-butylamino-2,2,6,6-tetramethylpiperidine is used instead of the morpholine in Example 11 and the procedure is exactly the same as that described in Example 11, 2,4-bis- [N- ( 2,2,6,6-tetramethylpiperidin-4-yl) butylamino] -6- (2,2,6,6-tetramethyl-4-hexyloxypiperidin-1-yl) -1,3,5-triazine as white crystals which can be recrystallized from acetonitrile. M.p .: 135-137 ° C.

Example 26: 2-Chloro-4-diisopropylamino-6- (2,2,6,6-tetramethylpiperidin-4-hexyloxypiperidin-1-yl) -1,3,5-triazine

In Example 3, instead of 2,4-dichloro-6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine, the same molar equivalent amount of the compound prepared in Example 10 is used and instead an ethylamine solution, a molar equivalent amount of diisopropylamine and otherwise exactly the same as described in Example 3, the above compound is obtained as a colorless oil.<tables id="tabl0023" num="0023"><img file="EP0328024A1_D0106.tif" /></tables>

Example 27: N, N-bis- [4-diisopropylamino-6- (4,4-ethylenedioxy-2,2,6,6-t®tramethylpiperidin-1-yl) triazin-2-yl] hexamethylene diamine

2.07 g (17 mmol) of 1,6-diamino-hexane and a solution of 1.36 g (34 mmol) of sodium hydroxide in 4 are added to 14 mg (34 mmol) of the product from Example 18 in 40 ml of xylene at 100 ° ml of water added. While distilling off water, the internal temperature is raised to 135 ° C. After 21 hours, 0.1 g of 1,6-diamino-hexane is added and the reaction is continued for 6 hours at the same temperature. The mixture is allowed to cool to 70 ° C., 0.26 g of sodium hydroxide, dissolved in 7.4 ml of water, is added, the mixture is stirred for 30 minutes and the two phases are separated. The organic phase is washed three times with water, over Na2SO4. dried and evaporated. The residue is dissolved in chloroform and on an Si02-Litches cleaned chromatographically. The main fraction obtained is the above product, which melts at 145-147 ° after drying well.<tables id="tabl0024" num="0024"><img file="EP0328024A1_D0107.tif" /></tables>

Example 28: 2,4-dichloro-6- (1,3,8-triaza-2,4-dioxo-3-dodecyl-7,7,9,9-tetramethyl-spiro [4,5] dec-1- yl) -1,3,5-triazine

Instead of the 1,3,8-triaza-2,4-dioxo-3,7,7,9,9-pentamethyl-spiro [4,5] decane described in Example 1.5, a molar equivalent amount of 1,3,8 is used -Triaza-2,4-dioxo-3-dodecyl-7,7,9,9-tetramethyl-spiro [4,5] decane and otherwise operates in the same way as described in Example 15, the result is obtained after the product obtained in Hexane / acetone dissolved and on a Si02Column had been purified by chromatography, the above product, which melts at 109-115`.

Example 29: 2,4-Dimorpholino-6- (1,3,8-triaza-2,4-dioxo-3-dodecyl-7,7,9,9-tetramethyl-spiro [4,5] dec-1- yl) -1,3,5-triazine

If, instead of the 2,4-dichloro-6- (1,3,8-triaza-2,4-dioxo-3,7,7,9,9-pentamethyl-spiro [4,5] described in Example 15, dec-1-yl) -1,3,5-triazine a molar equivalent amount of the 2,4-dichloro-6- (1,3,8-triaza-2,4-dioxo-3-dodecyl-7) described in Example 28 , 7,9,9-tetramethytspiro [4,5] dec-1-yl) -1,3,5-triazine and the procedure is otherwise the same as that given in Example 16, the above product is obtained, which is 185-188 melts.<tables id="tabl0025" num="0025"><img file="EP0328024A1_D0108.tif" /></tables>

Example 30: 2,4-bis-N-butylmethylamino-6- (1,3,8-triaza-2,4-dioxo-3-dodecyl-7,7,9,9-tetramethyl-spiro [4,5] -dec-1-yl) -1,3,5-triazine

If the procedure is the same as that given in Example 29, but a molar equivalent amount of N-butylmethylamine is used instead of morpholine, the above compound is obtained and melts at 93-96 °.<tables id="tabl0026" num="0026"><img file="EP0328024A1_D0109.tif" /></tables>

Example 31: 2,4-bis-N-butylmethylamino-6- (4,4-ethylenedioxy-2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine

24 ml of N-butylmethylamine are added to 15 g of the product from Example 17 with ice cooling. After adding a further 50 ml of N-butylmethylamine, the mixture is slowly heated to 88 'with stirring and boiled under reflux for 24 hours. After cooling to room temperature, 150 ml of water are added and a little HCl to pH 2. Then it is shaken out with methylene chloride; the organic phase is over Na2SO4 dried, evaporated and dried. The product of the above formula is obtained as a slightly yellow oil.<tables id="tabl0027" num="0027"><img file="EP0328024A1_D0110.tif" /></tables>

Example 32: 2,4-bis-dibutylamino-6- (4,4-ethylenedioxy-2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine

If, instead of the N-butylmethylamine described in Example 31, a molar equivalent amount of dibutylamine is used, the procedure is otherwise the same as that given in Example 32, the product finally being dissolved in toluene / hexane and on an SiO 22Acid is purified chromatographically, the above product is obtained as a colorless oil.<tables id="tabl0028" num="0028"><img file="EP0328024A1_D0111.tif" /></tables>

Example 33: 2,4-bis-N-butylmethylamino-6- (4-oxo-2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine

If, instead of the 2,4-dimorpholino-6- (4,4-ethylenedioxy-2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine described in Example 21, a molar equivalent amount of that in the example is used 31 described 2,4-bis-N-butylmethylamino-6- (4,4-ethylenedioxy-2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine and otherwise operates in the same way as in Example 21 given, the product finally dissolved in hexane / acetone and on a Si02Column is purified chromatographically, the above product is obtained as a colorless oil.<tables id="tabl0029" num="0029"><img file="EP0328024A1_D0112.tif" /></tables>

Example 34: 2,4-Dimorpholino-6- (4-hydroxy-2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine

5 g 2,4-Dimorpholino-6- (4-oxo-2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine (product from Example 21) are dissolved in 100 ml tetrahydrofuran at 60 ' and a pressure of 100 bar with Raney nickel as a catalyst until the reaction has stopped. The reaction mixture is filtered, evaporated and recrystallized from 20 ml of toluene. The above substance is obtained as white crystals that melt at 202-204 '.<tables id="tabl0030" num="0030"><img file="EP0328024A1_D0113.tif" /></tables>

Example 35: 2-Chloro-4- (1-acetyl-2,2,6,6-tetramethylpiperidin-4-oxy) -6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3 , 5-triazine

43.4 g of 2,4-dichloro-6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine (product from Example 1) are dissolved in 175 ml of toluene, whereupon 42 , 1 g of powdered KOH, 1 g of potassium carbonate and 3.4 g of tetrabutylammonium hydrogen sulfate are added. A solution of 29.9 g of 1-acetyl-2,2,6,6-tetramethyl-4-hydroxy-piperidine in 110 ml of toluene is then added dropwise, the internal temperature being kept at 10 ° with an ice bath. After stirring for 3.5 hours, 100 ml of water are added. The phases are separated, the organic phase is washed with water, over Na2S04 dried and evaporated. After recrystallization from hexane, the above product is obtained as a white powder which melts at 114-116 ° C.<tables id="tabl0031" num="0031"><img file="EP0328024A1_D0114.tif" /></tables>

Example 36: 2-Chloro-4- (1-oxyl-2,2,6,6-tetramethylpiperidin-4-oxy) -6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3 , 5-triazine

Instead of the 1-acetyl-2,2,6,6-tetramethyl-4-hydroxy-piperidine described in Example 35, a molar equivalent amount of 1-oxyl-2,2,6,6-tetramethyl-4-hydroxy-piperidine is used and otherwise operates as described in Example 35, the product being finally recrystallized from acetonitrile, the above product is obtained as a reddish powder which melts at 152-1530.<tables id="tabl0032" num="0032"><img file="EP0328024A1_D0115.tif" /></tables>

Example 37: N, N'-bis- [4- (1-acetyl-2,2,6,6-tetramethylpiperidin-4-oxy) -6- (2,2,6,6-tetramethylpiperidin-1-yl) -triazin-2-yl] hexamethylene diamine

To 20 g of 2-chloro-4- (1-acetyl-2,2,6,6-tetramethylpiperidin-4-oxy) -6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3 , 5-triazine (product from Example 35), 60 ml of xylene, 2.6 g of 1,6-diaminohexane and a solution of 1.8 g of sodium hydroxide in 5 ml of water. The mixture is then heated, the water being distilled off. If the temperature remains constant, the mixture is stirred at reflux for 24 hours. After cooling, a little sodium hydroxide solution is added and the phases are separated. The organic phase is over Na2SO4 dried and evaporated. After recrystallization from chloroform / hexane, dissolving the product in chloroform / methanol and chromatographic purification on a Si02Column, the above product is obtained as a white powder that melts at 201-202 °.<tables id="tabl0033" num="0033"><img file="EP0328024A1_D0116.tif" /></tables>

Example 38: 2-Morpholino-4- (1-oxyl-2,2,6,6-tetramethylpiperidin-4-oxy) -6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3 , 5-triazine

5 g 2-Chloro-4- (1-oxyl-2,2,6,6-tetramethylpiperidin-4-oxy) -6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5 triazine (product from Example 36) are stirred with 50 ml of morpholine for 3 hours under reflux. After cooling to 20 °, 200 ml of water are added and the precipitate is filtered off. After recrystallization from petroleum ether, the above product is obtained as reddish crystals which melt at 153-157 °.<tables id="tabl0034" num="0034"><img file="EP0328024A1_D0117.tif" /></tables>

Example 39: 2- (1-acetyl-2,2,6,6-tetramethylpiperidine-4-oxy) -4- (1-oxyl-2,2,6,6-tetramethylpiperidine-4-oxy) -6- ( 2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine

4th g 2-Chloro-4- (1-oxyl-2,2,6,6-tetramethylpiperidin-4-oxy) -6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5 triazine (product from Example 36) are dissolved in 30 ml of toluene, whereupon 2.6 g of powdered KOH, 1 g of potassium carbonate and 0.15 g of tetrabutylammonium hydrogen sulfate are added. 1.95 g of 1-acetyl-2,2,6,6-tetramethyl-4-hydroxypiperidine are added with stirring. The mixture is heated to 60 ° over 17 hours. After cooling, 30 ml of water are added. The phases are separated. The organic phase is over Na2SO4. dried and evaporated. After recrystallization from methylene chloride / hexane, dissolution of the product in hexane / acetic acid and chromatographic purification on a Si02Column gives the above product, which melts at 175-176.<tables id="tabl0035" num="0035"><img file="EP0328024A1_D0118.tif" /></tables>

Example 40: 2-Chloro-4- [N-bis (2,2,6,6-tetramethylpiperidin-4-yl) amino] -6- (2,2,6,6-tetramethylpiperidin-1-yl) -

, 3,5-triazine

To 28.9 g of 2,4-dichloro-6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine (product from Example 1), dissolved in 130 ml of toluene 29.5 g of bis (2,2,6,6-tetramethylpiperidin-4-yl) amine, dissolved in 60 ml of toluene, are added. After stirring at reflux for 26 hours and allowing to cool, 5.6 g of powdered KOH and 30 m! Water is added and the phases are separated. The organic phase is over Na2SO4. dried and evaporated. After recrystallization from acetonitrile, the above product is obtained as a white powder which melts at 240-242 '.<tables id="tabl0036" num="0036"><img file="EP0328024A1_D0119.tif" /></tables>

Example 41: N, N'-bis- {4- [N-bis (2,2,6,6-tetramethylpiperidin-4-yl) amino] -6- (2,2,6,6-tetramethylpiperidin-1 -yl) -triazin-2-yl} hexamethylene diamine

Instead of the 2-chloro-4- (1-acetyl-2,2,6,6-tetramethylpiperidine-4-oxy) -6- (2,2,6,6-tetramethylpiperidine-1-) described in Example 37 yl) -1,3,5-triazine, a molar equivalent amount of the product described in Example 40 and otherwise proceeding as described in Example 37, the product obtained above is obtained as a white powder which melts at 216-218 °.<tables id="tabl0037" num="0037"><img file="EP0328024A1_D0120.tif" /></tables>

Example 42: Compound of Formula

To 150 g of 2,2,4,4,14,14,16,16-octamethyl-7.11,18.21-tetraoxa-3.15-diaza-trispiro [5.2, 2.5.2.2] heneicosane. suspended in 300 ml of xylene. are added at 0 66 g of cyanuric chloride, dissolved in 500 ml of xylene. After stirring at reflux for 51 hours, the mixture is allowed to cool slightly, filtered and the liquid phase is evaporated. After solution in acetone / chloroform / methylene chloride, chromatographic purification on an SiO2Column and recrystallization from toluene gives the compound of the above structure, which melts at 277-278 °.<tables id="tabl0038" num="0038"><img file="EP0328024A1_D0122.tif" /></tables>

Example 43: Compound of Formula

If, instead of the 2,4-dichloro-6- (4,4-ethylenedioxy-2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine used in Example 31, a molar equivalent amount of Tetrachloro compound described in Example 42 and otherwise follows the same procedure as in Example 31, the compound of the above structure is obtained after recrystallization from acetone, which melts at 141-143 '.<tables id="tabl0039" num="0039"><img file="EP0328024A1_D0124.tif" /></tables>

Example 44: 2-Chloro-4-morpholino-6- (4,4-ethylenedioxy-2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine

To a solution of 30 g of 2,4-dichloro-6- (4,4-ethylenedioxy-2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine (product from Example 17) in 100 ml of toluene are added to 3.8 g of morpholine and 15 minutes later a solution of 1.7 g of NaOH in 5 ml of water. Now it is heated to 60 ° and after 45 minutes a further 3.8 g of morpholine and 1.7 g of NaOH in 5 ml of water are added. The reaction is complete after a further 1.5 hours. After cooling and adding 200 ml of toluene, the phases are separated. The organic phase is over Na2SO4 dried and evaporated. Recrystallization from acetonitrile leads to the connection of the above structure, which melts at 154-156 ° (white powder).<tables id="tabl0040" num="0040"><img file="EP0328024A1_D0125.tif" /></tables>

Example 45: 2- [bis- (2-hydroxyethyl) amino] -4-morpholino-6- (4,4-ethylenedioxy-2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5 -triazine

To a solution of 20 g of 2-chloro-4-morpholino-6- (4,4-ethylenedioxy-2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine (product from Example 44) in 50 ml of xylene are added to 5.3 g of diethanolamine and a solution of 1 g of NaOH in 3 ml of water. After stirring under reflux, a further 1 g of NaOH in 3 ml of water is added after 1.75 hours. After 14 hours, 7.9 g of diethanolamine are added, followed by stirring under reflux for 28 hours. It is allowed to cool, washed with water and the organic phase is separated off. After drying over Na2S04Evaporation and recrystallization twice from toluene give the above product as a white powder which melts at 135-140 °.<tables id="tabl0041" num="0041"><img file="EP0328024A1_D0126.tif" /></tables>

Example 46: Polycondensate from 2- [bis- (2-hydroxyethyl) amino] -4-morpholino-6- (4,4-ethylenedioxy-2,2,6,6-tetramethylpiperidin-1-yl) -1,3 , 5-triazine and diethyl succinate

To a solution of 9.8 g of 2- [bis- (2-hydroxyethyl) amino] -4-morpholino-6- (4,4-ethylenedioxy-2,2,6,6-tetramethylpiperidin-1-yl) - 1,3,5-triazine (product from Example 45) in 50 ml of toluene, 3.5 ml of diethyl succinate and 0.4 g of tetrabutyl orthotitanate (monomer) are added. The mixture is heated for 24 hours so that toluene distills off very slowly. After cooling slightly, filter through bleaching earth and evaporate. The residue is dried in vacuo at 80 °. A resin-like polymer with a molecular weight of Mn = 966 / Mw = 1409 is obtained (gel permeation chromatography).

Example 47: 2,4-bis-morpholino-6- (4-butylamino-2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine

12th g of 2,4-bis-morpholino-6- (4-oxo-2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine (product from Example 21) are in 120 ml of methanol and 60 ml of ethyl acetate at 40 ° and a pressure of 80 bar with 5% platinum on carbon as a catalyst in the presence of 6 g of butylamine and 0.25 g of p-toluenesulfonic acid until the reaction has stopped. The reaction mixture is filtered and evaporated. After dissolving in methylene chloride and washing with water, the organic phase is washed over Na2SO4 dried and evaporated. The residue is dissolved in toluene / acetone and on a Si02Column cleaned chromatographically. The oily product crystallizes after a few days and melts at 82-87 °.<tables id="tabl0042" num="0042"><img file="EP0328024A1_D0127.tif" /></tables>

Example 48: Compound of Formula

8 g of 2,4-bismorpholino-6- (4-butylamino-2,2,6,6-tetramethylpiperidin-1-yl) are added to a solution of 3.2 g of cyanuric chloride in 40 ml of acetone while cooling to 0 °. -1,3,5-triazine (product from Example 47) added dropwise in 30 ml of acetone. After adding 0.8 g of NaOH in 2 ml of water, the mixture is stirred at 0 for 3 hours, after which 60 ml of water are added. The product thus precipitated is filtered off and recrystallized from acetonitrile. The white crystals of the above structure thus obtained melt at 198-203 C.<tables id="tabl0043" num="0043"><img file="EP0328024A1_D0129.tif" /></tables>

Example 49: Compound of Formula

<chemistry id="chem0085" num="0085"><img file="EP0328024A1_D0130.tif" /></chemistry>Polycondensate from the compound from Example 48 and hexamethylene diamine

Instead of the 2,4-dichloro-6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine described in Example 14, the dichloro compound described in Example 48 is used in a molar equivalent amount and If the procedure is otherwise the same as that described in Example 14, a pulverizable polymer of molecular weight M is obtainedn = 1520 / Mw = 1985 (gel permeation chromatography).

Example 50: 2,4-bis-morpholino-6- (4-methacryloyloxy-2,2,6,6-tetramethylplperidin-1-yl) -1,3,5-triazine

10.2 g of 2,4-dimorpholino-6- (4-hydroxy-2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine (product from Example 34) together with 6, 9 ml of methacrylic acid ethyl ester, 0.04 g of 2,6-bis-tert-butyl-p-cresol and 0.04 ml of tetrabutyl orthotitanate (monomer) are heated to 120, some liquid being slowly distilled off. The mixture is left to react for 50 hours, with some methyl methacrylate and catalyst being temporarily added. After the reaction has ended, the mixture is filtered through bleaching earth and evaporated. The residue is dissolved in toluene / acetone and on an SiO2Column cleaned chromatographically, the above product being obtained as a colorless resin.<tables id="tabl0044" num="0044"><img file="EP0328024A1_D0131.tif" /></tables>

Example 51: Homopolymer of 2,4-bis-morpholino-6- (4-methacryloyloxy-2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine

6 g 2,4-bis-morpholino-6- (4-methacryloyloxy-2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine (product from Example 50) together with 0.13 g of dodecyl mercaptan and 0.1 g of α, α'-azo-isobutyronitrile in 25 ml of isopropyl methyl ketone under nitrogen over a period of 12 hours to 75. heated. After evaporation and drying for 72 hours at 60 ° under vacuum, a white, pulverizable polymer of molecular weight M is obtainedn = 3188 / mw = 12064 (gel permeation chromatography).

Example 52: N, N'-Bis [1- (2,4-dimorpholino-1,3,5-triazin-6-yl) -2,2,6,6-tetramethylpiperidin-4-yl] hexamethylene diamine

If, instead of the butylamine used in Example 47, a molar equivalent amount of 1.6-

Diaminohexane and otherwise the same procedure as given in Example 47, the above compound is obtained as a white powder which melts at 161-163 °.<tables id="tabl0045" num="0045"><img file="EP0328024A1_D0132.tif" /></tables>

Example 53: 2-chloro-4,6-bis (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine

18.4 g of cyanuric chloride and 113 g of 2,2,6,6-tetramethylpiperidine are heated in a 300 ml autoclave at 180 ° for 10 hours and then at 210 ° for 10 hours. The contents of the autoclave are taken up in 500 ml of water, the insoluble residue is filtered off with suction, washed with water and dried. The brownish residue is crystallized from ligroin. The 2-chloro-4,6-bis (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine is obtained as colorless crystals with a melting point of 188 °.

Example 54: 2,4-dichloro-6- [2,2,6,6-tetramethyl-4- (N-acetylbutylamino) piperidin-1-yl) -1,3,5-triazine

9.2 g of cyanuric chloride and 26.7 g of 2,2,6,6-tetramethyl-4- (N-acetyl-butylamino) piperidine are reacted and worked up in 100 ml of xylene as described in Example 1. 2,4-Dichloro-6- [2,2,6,6-tetramethyl-4- (N-acetyl-butylamino) piperidin-1-yl) -1,3,5-triazine is obtained as colorless crystals with a melting point of 131-133 °.

Example 55: 2-Chloro-4-isopropyloxy-6- (2,2,6,6-tetrarnethylpiperidin-1-yl) -1,3,5-triazine

104.0 g of 2,4-dichloro-6-isopropyloxy-1,3,5-triazine and 148.3 g of 2,2,6,6-tetramethylpiperidine are reacted and worked up in 300 ml of xylene as described in Example 1. Crystallization from hexane gives the 2-chloro-4-isopropyloxy-6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine as colorless crystals with a melting point of 111-112 °.

Example 56: 2,4-bis-isopropyloxy-6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine

12.5 g of 2-chloro-4-isoproplyoxy-6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine (product from Example 55) 11.2 g of finely powdered potassium hydroxide and 0.7 g of tetrabutylammonium hydrogen sulfate are placed in 60 ml of toluene. 2.6 g of isopropanol are added dropwise to this orange-colored suspension in 15 minutes: weak exotherm to about 30 °. The light brown flask contents are stirred at 60 ° for 8 hours, cooled to 0-5 °, diluted with 80 ml of water and then with 40 ml of toluene. The brown, aqueous phase is separated from the colorless, organic phase and washed four times with 80 ml of water each time, dried over sodium sulfate and completely evaporated in vacuo. A slightly yellowish oil is obtained which solidifies after a short time to give 2,4-bis-isopropyloxy-6- (2,2,6,6tetramethylpiperidin-1-yl) -1,3,5-triazine with a melting range of 70-98 ° .

Example 57: 2-isopropyloxy-4-n-octoxy-6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine

If 5.7 g of 1-octanoi are used instead of isopropanol and the procedure is as described in Example 56, 2-isopropyloxy-4-n-octoxy-6- (2,2,6,6-tetramethylpiperidine-1- yl) -1,3,5-triazine as a pale yellowish resin Analysis: Calculated: 13.78% N, found. 13.87% N

Example 58: 2-isopropyloxy-4-dibutylamino-6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine

12.5 g of 2-chloro-4-isopropyloxy-6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine and 5.5 g of dibutylamine are dissolved in 100 ml of xylene. After adding a solution of 1.8 g of sodium hydroxide in 10 ml of water, the water is slowly distilled off on a water separator under a weak stream of nitrogen. The contents of the flask are then stirred at 135 ° for about 16 hours. Allow to cool slightly, add 50 ml of water to the flask contents and stir vigorously for 10 minutes. The aqueous phase is separated off and the organic layer is washed four times with 50 ml of water each time, dried over sodium sulfate and completely evaporated in vacuo. The 2-isopropyloxy-4-dibutylamino-6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine obtained is a slightly yellowish resin. Analysis N: calc. 17.27%, found. 17.29%

Example 59: Compound of Formula

<chemistry id="chem0086" num="0086"><img file="EP0328024A1_D0133.tif" /></chemistry>18.8 g of 2-chloro-4-isopropyloxy-6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine, 3.6 g of 1,6-diaminohexane and a solution 2.6 g of sodium hydroxide in 10 ml of water are reacted in 100 ml of xylene as described in Example 58. Crystallization from xylene gives the compound of the above formula as colorless crystals with a melting point of 224-226 °.

Example 60: 2,4-bis (2-hydroxyethylamino) -6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine

If 26.9 g of ethanolamine (1st portion: 12.2 g; 2nd portion: 14.7 g) are used instead of dibutylamine and the procedure is otherwise as described in Example 6, the product obtained after crystallization from toluene is 2,4-bis (2-hydroxyethylamino) -6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine with a melting point of 147-148 °.

Example 61: Polymer of the formula

<chemistry id="chem0087" num="0087"><img file="EP0328024A1_D0134.tif" /></chemistry>23.1 g 2,4-dichloro-6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine and 31.4 g 1,6-bis- (2.2 , 6,6-tetramethyl-4-piperidylamino) hexane are reacted in the presence of 6.8 g of sodium hydroxide in 200 ml of xylene as described in Example 6. The slightly yellowish resin obtained has a molecular weight of 1330.

Example 62: Compound of Formula

<chemistry id="chem0088" num="0088"><img file="EP0328024A1_D0135.tif" /></chemistry>57.8 g of 2,4-dichloro-6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine are placed in 200 ml of xylene. 17.4 g of N-methylbutylamine are added dropwise in 15 minutes. The temperature rises to 50 °. A solution of 8.8 g of sodium hydroxide in 30 ml of water is then added dropwise to the reaction mixture in 10 minutes and the mixture is stirred at 60 ° for 2 hours. The aqueous phase is then separated off, 41.4 g of 1,6-bis (2,2,6,6-tetramethyl-4-piperidylamino) hexane are added, the mixture is warmed to 90 and then a solution of 9 is added. Add 6 g sodium hydroxide in 30 ml water. The water is then slowly distilled off on a water separator under a weak stream of nitrogen and the contents of the flask are then stirred at 135 ° for 18 hours. Allow to cool slightly, add 100 ml of water to the reaction mixture and stir vigorously for 10 minutes. The aqueous phase is separated off and the organic solution is washed three times with 50 ml of water each time, dried over sodium sulfate and evaporated in vacuo. Crystallization of the residue from methyl ethyl ketone gives the compound of the above formula as colorless crystals with a melting point of 137-138 °.

Example 63: Compound of Formula

28.9 g of 2,4-dichloro-6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine are added with 12.9 g of dibutylamine and then with 1.6 g Diaminohexane as described in Example 62, the compound of the above formula is obtained after crystallization from acetonitrile as colorless crystals with a melting point of 93-94 °.

Example 64: Compound of Formula

<chemistry id="chem0090" num="0090"><img file="EP0328024A1_D0137.tif" /></chemistry>19.0 g of 2,4-bis-butylamino-6- (2,2,6,6-tetramethyl-4-hydroxypiperidin-1-yl) -1,3,5-triazine (prepared according to Example 9) are mixed with 5 , 8 g of dimethyl sebacate in 150 ml of xylene after the addition of 0.2 g of lithium amide under a weak stream of nitrogen and distilling off the methanol formed, heated under reflux for 12 hours. The reaction mixture is allowed to cool to about 100 °, 5 g of Tonsil optimum (bleaching earth) are added, the mixture is stirred for 5 minutes and filtered. Evaporation of the solvent gives the compound of the above formula as a slightly yellow resin. Analysis: calc. 18.20% N, found 18.51% N

Example 65: Compound of Formula

If, instead of dimethyl sebacate, 3.6 g of dimethyl succinate is used and the procedure described in Example 64 is followed, the compound of the above formula is obtained after crystallization from acetonitrile as colorless crystals with a melting point of 131 °.

Example 66: Compound of Formula

If, instead of dimethyl sebacate, 4.8 g of dimethyl terephthalate are used and the procedure described in Example 64 is followed, the compound of the above formula is obtained after crystallization from xylene as colorless crystals with a melting point of 181 °.

Example 67: 2,4-bis-butylamino-6- {2,2,6,6-tetramethyl-4- [2- (3,5-di-tert-butyl-4-hydroxyphenyl) propionyloxy] piperidine -1-yl} -1,3,5-triazine

If, instead of dimethyl sebacate, 14.6 g of methyl 2- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate are used and the procedure is as described in Example 64, 2,4-bis-butylamino is obtained -6- {2,2,6,6-tetramethyl-4- [2- (3,5-di-tert-butyl-4-hydroxyphenyl) propionyloxy] piperidin-1-yl} -1,3, 5-triazine as a pale yellowish resin. Analysis: calc. 13.15% N, found 13.36% N

Example 68: Compound of Formula

<chemistry id="chem0093" num="0093"><img file="EP0328024A1_D0140.tif" /></chemistry>16.9 g of 2,4-bis (2-hydroxyethylamino) -6- (2,2,6,6-tetramethylpiperidin-1-yl) -1,3,5-triazine (prepared according to Example 60) are mixed with 29 , 2 g of β- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid methyl ester in 100 ml of xylene after the addition of 0.2 g of lithium amide under a weak stream of nitrogen and distilling off the methanol formed, heated under reflux for 12 hours. The reaction mixture is allowed to cool to about 100 °, mixed with5 g Tonsil Optimum (bleaching earth), stirred for 5 minutes and filtered. After evaporation of the solvent, the compound of the above formula is obtained as a yellowish resin Analysis: calc. 9.78% N, found 9.67% N.

Example 69: Compound of Formula

If, instead of β- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid methyl ester, 25.0 g of β- (3-methyl-4-hydroxy-5-tert.butyl-phenyl) propionic acid methyl ester and If the procedure is as described in Example 68, the compound of the above formula is obtained as a yellowish, pulverizable resin. Analysis: calc. 10.84% N, found 10.57% N.

Example 70: 2-chloro-4- [N- (2,2,6,6-tetramethyl-4-piperidyl) -n-butylamino] -6- (2,2,6,6-tetramethyl-4-hexyloxypiperidine- 1-yl) -1,3,5-triazine

If the dichloro derivative from Example 10 is reacted with an equivalent of 4-butylamino-2,2,6,6-tetramethylpiperidine and the procedure described in Example 26 is followed, the title compound is obtained as a colorless oil. Analysis: calc. 14.87% N, found 14.74% N.

Example 71: N, N ', N' '- Tris {2- (2,2,6,6-tetramethyl-4-hexyloxypiperidin-1-yl) -4- [N- (2,2,6,6- tetramethylpiperidin-4-yl) -butylamino) -1,3,5-triazin-6-yl} -diethylenetriamine

0.71 ml of diethylenetriamine and 0.9 g of NaOH, dissolved in 3 ml of water, are added to 10.6 g of the monochloro derivative from Example 70, dissolved in 50 ml of toluene. After heating to 100 °, the solvent begins to distill off. A further 50 ml of toluene and 1 g of polyethylene glycol 1000 and 0.9 g of NaOH are added and the mixture is heated under reflux with stirring for 14 h. After cooling, the reaction mixture is diluted with 100 ml of ethyl acetate and the solution is washed four times with water. The organic solution is over Na2S04 dried and evaporated. The residue is dissolved in 50 ml of methanol, filtered through 200 g of silica gel and washed with 500 ml of methanol. The methanol solution is evaporated, the residue is an almost colorless resin. Analysis: calc. 17.4% N, found 17.4% N.

Example 72: Stabilization of a two-layer lacquer

A clear varnish is prepared by mixing the following components:<ul id="ul0007" list-style="none"><li>58.3 parts of an acrylic resin (Viacryl®VC 373, Vianova AG)</li><li>27.3 parts of a melamine resin (MaprenalMFf 590, Hoechst AG)</li><li>4.0 parts of an aromatic solvent mixture (Solvesso®150)</li><li>5.4 parts of xylene</li><li>4.0 parts of butyl glycol acetate</li><li>1.0 part of a leveling aid (Baysilon @ A, Bayer AG)</li></ul>

The light stabilizers listed in Table 1 are added to this lacquer. The paint is diluted with a 1: 1: 1 mixture of butyl acetate and xylene to make it sprayable and sprayed onto an aluminum sheet coated with a silver metallic basecoat. The samples are then cured at 130 C for 30 minutes. The clearcoat has a layer thickness of 40-45 µm.

The samples prepared in this way are weathered in a UVCON® exposure device (Atlas Corp.) with a cycle of 8 h of UV radiation at 70 ° C. and 4 h of condensation at 50 ° C.

After 400 h of weathering, the 20 gloss of the samples is measured in accordance with DIN 67530. The results are shown in Table 1.<tables id="tabl0046" num="0046"><img file="EP0328024A1_D0142.tif" /></tables>

Example 73: - Outdoor exposure of a two-layer lacquer

Two-coat lacquers are prepared as described in Example 70. The samples are exposed to 54 months outdoor exposure in Florida. The 20 ° gloss is measured every 12 months in accordance with DIN 67530. The results are shown in Table 2.<tables id="tabl0047" num="0047"><img file="EP0328024A1_D0143.tif" /></tables>

Example 74:

0.087 g of the yellow coupler of the formula<chemistry id="chem0095" num="0095"><img file="EP0328024A1_D0144.tif" /></chemistry>are dissolved in 2.0 ml of a solution of the stabilizer listed in Table 3 in ethyl acetate (2.25 g / 100 ml). To 1.0 ml of this solution are added 9.0 ml of a 2.3% aqueous gelatin solution, which is adjusted to a pH of 6.5, and 1.744 gil of the wetting agent of the formula<chemistry id="chem0096" num="0096"><img file="EP0328024A1_D0145.tif" /></chemistry>contains.

2 ml of a silver bromide emulsion with a silver content of 6.0 g / l and 1.0 ml of a 0.7% aqueous solution of the hardener of the formula are added to 5.0 ml of the coupling emulsion thus obtained<chemistry id="chem0097" num="0097"><img file="EP0328024A1_D0146.tif" /></chemistry>and poured it onto a 13 x 18 cm plastic-coated paper. After a curing time of 7 days, the samples are exposed behind a silver step wedge with 125 lux's and then processed in the Ektaprint 2 @ process from Kodak.

The yellow wedges obtained are placed in an Atlas Weather-Ometer with a 2500 W xenon lamp behind a UV filter (Kodak 2C) with a total of 60 k joules / cm2 irradiated.

A sample without stabilizer runs as standard.

The following Table 3 shows the loss of color density which occurred during the irradiation at the absorption maximum of the yellow dye, measured with a TR 924A densitometer from Macbeth.

The light protection effect can be seen from the loss of color density. The smaller the density loss, the higher the light protection effectiveness.<tables id="tabl0048" num="0048"><img file="EP0328024A1_D0147.tif" /></tables>

Example 75:

0.033 g each of the cyan coupler of the formula<chemistry id="chem0098" num="0098"><img file="EP0328024A1_D0148.tif" /></chemistry>and the stabilizer shown in Table 4 are dissolved in 2.0 ml of a mixture of dibutyl phthalate / ethyl acetate (0.8 g / 100 ml).

To 1.0 ml of this solution are added 9.0 ml of a 2.3% aqueous gelatin solution which is adjusted to a pH of 6.5 and contains 0.872 g / l of the wetting agent sodium dibutylnaphthalenesulfonate.

The emulsion is then used as described in Example 72, but with the difference that the silver bromide emulsion has a silver content of 3 g / l.

The color step wedges obtained are placed in an Atlas Weather-Ometer with a 2500 W xenon lamp behind a UV filter (Kodak 2c) with a total of 60 k joules / cm2 irradiated and then the loss of color density, as described in Example 72, determined.

The results are summarized in Table 4 below.<tables id="tabl0049" num="0049"><img file="EP0328024A1_D0149.tif" /></tables>

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Every citation, both waysCites: the store holds 14 of 15

Citations
Document	Relation	Office	Cited during
US5457199A	Cited by	United States of America	Search report
EP0634412A1	Cited by	European Patent Office (EPO)	Search report
EP0165608A2	Cites	European Patent Office (EPO)	Search report
EP0165608A2	Cites	European Patent Office (EPO)	Search report
DE2025080A1	Cites	Germany	Search report
DE2025080A1	Cites	Germany	Search report
DE2456735A1	Cites	Germany	Search report
DE2456735A1	Cites	Germany	Search report
DE3208570A1	Cites	Germany	Search report
DE3208570A1	Cites	Germany	Search report
US3382221A	Cites	United States of America	Search report
US3382221A	Cites	United States of America	Search report
US4629752A	Cites	United States of America	Search report
US4629752A	Cites	United States of America	Search report
US4722806A	Cites	United States of America	Search report
US4722806A	Cites	United States of America	Search report

16 members in 12 offices

This recordMember, by publication datePriority claim2 more offices are in the list below

Priority claims5

Priority claims
Document	Office	Kind	Date
44088	Switzerland	–	1988-02-08
44088	Switzerland	A	1988-02-08
44088	Switzerland	A	1988-02-08
44088	–	–	–
CH19880000440	–	–	–

Members16

Family members, oldest first
Document	Office	Kind
EP0328024A1This record	European Patent Office (EPO)	A1	1989-08-16
AU2877489A	Australia	A	1989-09-14
KR890012997A	Republic of Korea	A	1989-09-20
BR8900532A	Brazil	A	1989-10-03
ZA89928B	South Africa	B	1989-10-25
CN1036760A	China	A	1989-11-01
JPH01294672A	Japan	A	1989-11-28
DD283411A5	German Democratic Republic (until 1990)	A5	1990-10-10
US5059689A	United States of America	A	1991-10-22
AU621082B2	Australia	B2	1992-03-05
EP0328024B1	European Patent Office (EPO)	B1	1994-12-28
AT116311T	Austria	T	1995-01-15
ATE116311T1	Austria	T1	1995-01-15
DE58908808D1	Germany	D1	1995-02-09
CA1339783C	Canada	C	1998-03-31
JP2782449B2	Japan	B2	1998-07-30

38 legal events, as 3 offices reported them to INPADOC

Over the term

Point at a mark for the event

Events

Legal events, newest first
	Event	Code	Office
2005-02-06	Lapsed in a contracting state [announced via postgrant information from national office to epo]LapsedPG25	PG25	EP
2001-12-01	Lapsed in a contracting state [announced via postgrant information from national office to epo]LapsedPG25	PG25	EP
2001-11-30	Notification of lapseLapsedST	ST	FR
2001-10-31	Lapsed in a contracting state [announced via postgrant information from national office to epo]LapsedPG25	PG25	EP
2001-09-26	Gb: european patent ceased through non-payment of renewal feeCeasedGBPC	GBPC	EP
2001-08-31	Be: lapsedLapsedBERE	BERE	EP
2001-02-28	Lapsed in a contracting state [announced via postgrant information from national office to epo]LapsedPG25	PG25	EP
2001-02-06	Lapsed in a contracting state [announced via postgrant information from national office to epo]LapsedPG25	PG25	EP
2000-07-28	Annual fee paid to national office [announced via postgrant information from national office to epo]GrantedPGFP	PGFP	EP
2000-04-12	Annual fee paid to national office [announced via postgrant information from national office to epo]GrantedPGFP	PGFP	EP
2000-01-25	Annual fee paid to national office [announced via postgrant information from national office to epo]GrantedPGFP	PGFP	EP
1999-12-20	Annual fee paid to national office [announced via postgrant information from national office to epo]GrantedPGFP	PGFP	EP
1999-09-01	Lapsed in a contracting state [announced via postgrant information from national office to epo]LapsedPG25	PG25	EP
1998-04-17	Transmission of propertyTP	TP	FR
1997-12-31	Annual fee paid to national office [announced via postgrant information from national office to epo]GrantedPGFP	PGFP	EP
1997-06-02	Nl: modifications of names registered in virtue of documents presented to the patent office pursuant to art. 16 a, paragraph 1NLT1	NLT1	EP
1997-05-21	Amendments to the register in respect of changes of name or changes affecting rights (sect. 32/1977)732E	732E	GB
1997-03-03	Nl: assignments of ep-patentsNLS	NLS	EP
1996-12-31	Be: change of holder's nameBECN	BECN	EP
1995-12-20	No opposition filedOpposition26N	26N	EP
1995-11-01	No opposition filed within time limitOppositionORIGINAL CODE: 0009261PLBE	PLBE	EP
1995-11-01	Information on the status of an ep patent application or granted ep patentGrantedSTATUS: NO OPPOSITION FILED WITHIN TIME LIMITSTAA	STAA	EP
1995-04-21	Fr: translation filedET	ET	EP
1995-03-28	Lapsed in a contracting state [announced via postgrant information from national office to epo]LapsedPG25	PG25	EP
1995-03-15	Gb: translation of ep patent filed (gb section 77(6)(a)/1977)GBT	GBT	EP
1995-02-28	Lapsed in a contracting state [announced via postgrant information from national office to epo]LapsedPG25	PG25	EP
1995-02-28	Lapsed in a contracting state [announced via postgrant information from national office to epo]LapsedPG25	PG25	EP
1995-02-09	Corresponds to:REF	REF	EP
1995-02-06	Lapsed in a contracting state [announced via postgrant information from national office to epo]LapsedPG25	PG25	EP
1995-02-03	It: translation for a ep patent filedITF	ITF	EP
1995-02-03	It: translation for a ep patent filedITF	ITF	EP
1994-12-28	Designated contracting statesAK	AK	EP
1994-12-28	Corresponds to:REF	REF	EP
1994-11-11	(expected) grantORIGINAL CODE: 0009210GRAA	GRAA	EP
1992-10-28	First examination report despatched17Q	17Q	EP
1989-08-16	Request for examination filed17P	17P	EP
1989-08-16	Designated contracting statesAK	AK	EP
1989-07-01	Public reference made under article 153(3) epc to a published international application that has entered the european phaseORIGINAL CODE: 0009012PUAI	PUAI	EP

Tetramethylpiperidino-s triazines.

Abstract

Term

Priority claims5

Members16

Over the term

Events

Numbers

Titles3

Classification

Designated states10