Piperidine derivatives
1 claim: 1 independent, 0 dependent
- 1Prooeldeu pentru prepararea unor derivați ai pipenidiiuei cu structura chatmică conform formulei generale I :~ r, O--r 3 \/ /\ • c \l l/ CH · ω _ te _η. în care simbolul n reprezintă cifrele 1, 2, 3 sau 4, siimiboluli Rt reprezintă o grupă alchii ou 1 .. . 20 (atomi de carbon, de preferință eu 1 ... 12 atomi idie caiibon, o grapă alchenil saiu alchiniiil cu 3 ... 20 aitomi de oarbon, die preferință cu 3...12 atomi de dartîou, o gnuipă ariailichil cu 7 ... 12 atomi de carbon sau o grupă eu formula —(CHs)™—CH—Xt sau eu formula Rî —CH—X2 în oare simbolul m este egal I R4 cu 1, 2 sau 3, isimboiluil R4 reprezintă un atom de hidrogen, o gnupă metil sau fenil, simbolul X? reprezintă un aitom de halogen, o grapă oan sau o grupă ou formula —CH— CHs, —CORs, —CO—ORs, \ / O —CO- SR5 sau —CO—NRsRu, tar simbolul X, reprezintă o grupă hiildeoxill, un atotn de halogen, o grapă olan sau una dintre grupele : —OCR5, —OCR 5 , —OR 5 , II II O s y to j to —OCNf , —OCN ζ , il te ft X to O S , —ORj, - -COR 5i —CSR s , li II , II 000 t II II o s în cape simbolul Rs reprezintă· o gnupă alchiiil cu 1 ... 20 atomi ide loairibioia, o grapă ailcheniil cu 2 .., 20 latomi de carbon, o grupa dîcfciailchiitl ou 5 ... 12 aitomi de carbon o grupă arii ou 6...11 ,atomi de carbon sau o grupă araichil cu 7... 14 latomi de carbon, simbolul Rs pultînid reprezenta', de asemenea, ,un aibom de hidrogen ciunti cînid ©site legat, de un atom dc azot, simbolul R« reprezintă un altora de hidrogen sau o gnupă islchil cu 1... 4 attomi de carbon saiu simbcilunille Rs și Rs ipoit forma împreună ou atomul de azot de care sînt ilegalte un iiinial cu 5 saiu 6 membri, care nu conțin nici un alt heteroatom sau care mai conțin unul sau mai mulți biți hetetraatomi, sau simbolul Ri reprezintă o grupă acd.l —CO—R?, în oare simbolul R7 reprezintă un atom de hidrogen,, un rest alifatic, eventual subsliltiutit, cu 1 ... 20 atomi de carbon, o grupă alchenil sau alchimii qu 2 ... 20 atomi die carbon·, o grupă ciicjloialifătâcă cu 5... 12 (atomi de carbon, un rest alifaftfc cu 7 ... 14 laitomi de carbon, un rest anomialtliic ou 6 .. . 20 atomi die carbon, de preferință ou 6...12 atomi de oairiboni sau un rest heterorioliic, s.au simbolul Ri reprezintă o grapă carbamoill sau itiodarbamoil ra formiuila : to N—C— în Oare slmbOilul X3 reprezintă un altom die oxigen sau un atom. de sulf, simbolul Rs reprezintă un atom de hidrogen sau o grupă alchil cu 1 ... 4 atomi de oarbon, ilar simbolul R? reprezintă un atom ide hidrogen, o grupă ailchiil cu 1 ... 20 aitomi de icarbon, o .grapă alchenil cu 3 ... 20 aitomi de oarbon, o grapă olcloallchtil au 5 ... 42 laitomi d'e oarbon sau o grupă sirii nesuibsitîlfauÎită sau substituită ou 6 ... 12 atomi de carbon, simbolul R2 reprezintă o grupă ailchil cu 4 .. .-4 atomi de carbon, o grupă ălohen'il sau alchimii ou 3 ... 20 atomi de oarbon, de preferință ra 3 sau 4 atomii de carbon, o grupă ciclOalchil eu 5 ... 12 atomi de oarbon, o grapă anii cu 6... 11 atomii de o'airfbon, 0 grapă arailchiil cu 7...9 aitomi ide oarbon, sau, de preferință, un atom de hidrogen, și, .dtumed cînid simbolul n este egal cu 1, simbolul Rs reprezintă un radical monovaienit ou semnificații ideirâce ou 'acelea sie simboilului R1, sau reprezintă un rest mlonioviaienit obținui· prin înldiepădtadea unei grupe hidroxil dintr-un acid sulifiinto, dintr-un 'aciid stuifcnic, dintr-un aicsild care conține fosfor sau (din acidul buric, sau (reprezintă o grupă lattiil, o grapă catetoailchiil ra 5
463 paragraphs in 19 sections, as filed
© Process for the preparation of piperidine derivatives
The present invention relates to a process for the preparation of some piperidine derivatives with the chemical structure according to the general formula;
4¾ \ / θ
-Rs .mula —CH — CH2, —CORs, - CO — OR :, \ /
O -CO-SRs or -CO-NRsRf, and symbol 5, XI represents a hydroxyl group, a halogen atom, a cyano group or one of the groups:
(1)
H<sub>3</sub>C<sub>X</sub>| |<sub>z</sub>CH<sub>3</sub> h<sub>3</sub>c<sup>/ x</sup>n<sup>/</sup>^ ch<sub>3</sub>
I _ <sup>R</sup>, in which the symbol n represents the digits I, 2, <sub>I5 </sub>3 or 4, the symbol R 1 represents an allyl group with 1 to 20 carbon atoms, preferably 1 to 12 carbon atoms, an alkenyl or alkenynyl group with 3 to 20 carbon atoms, preferably egg 3 ... 12 carbon atoms, an aralkyl group with 7 20
... 12 carbon atoms or a group of formula - (CH2) <sub>m</sub>—CH — Xi or forcibly the mule —CH — X2 in which the symbol m is m I
Rt equal to 1, 2 or 3, the symbol Rj represents a hydrogen atom, a methyl or phenyl group, the symbol X? represents a halogen atom, a cyano group or a 10-OR group<sub>5</sub>, —OCR,
II o
/ 5
-OCR ,, -OCN <
II 11 <sup>x</sup> Ri so / R5 —OCN (, -cr „--COR ,, -CSR<sub>5</sub>, // II II lî s 000
CN
R, to —CNif II <sup>X </sup>S
R<sub>5</sub>
R 1 wherein the symbol Rs represents an alkyl group of 1 ... 20 carbon atoms, an alkenyl group with 2 ... 20 carbon atoms, a cycloalkyl group of 5 ... 12 carbon atoms, an aryl egg group 6 ... 11 carbon atoms or an aralkyl group with 7 ... 14 carbon atoms, the symbol Rs being also able to represent a hydrogen atom when cinnamon is linked to an atom of
PRICE LEI 12.75 nitrogen, the symbol Re represents a hydrogen atom or an alkyl group egg 1 ... 4 carbon atoms or the symbols Rs and R «can form, together with the nitrogen atom to which they are linked, a ring with 5 or 6 members, which does not contain any other heteroatoms or c. which contains one or more other heteroatoms or the symbol R 1 represents an allyl group - CO - R 7, wherein the symbol R 7 represents a hydrogen atom, an unsubstituted aliphatic moiety, or substituted by 1 ... 20 carbon atoms, an alkenyl or alkynyl moiety with 2 to 20 carbon atoms, a cycloaliphatic group of 5. 12 carbon atoms, one. aralifa't'ite residue with 7 ... 14 carbon atoms, an aromatic residue with 6 ... 20 carbon atoms, preferably with 6 ... 12 carbon atoms, or a heterocyclic residue or the symbol R 1 represents carbamoyl or thiocarbamoyl group of formula:
wherein the symbol Xn represents an oxygen atom, or a sulfur atom, the symbol Rs represents a hydrogen atom or an alkyl group with 1-4 carbon atoms, and the symbol Rs represents a hydrogen atom, a C 1-4 alkyl group. , u 1 ... 20 carbon atoms, an alkenyl group with 3 ... 20 carbon atoms, an eialalkyl group with
5. .12 carbon atoms or an aryl group unsubstituted or substituted with 6. 12 carbon atoms, the symbol R 1 represents an alkyl group with 1-4 carbon atoms, an alkenenyl or alkynyl group with
3.. . 20 carbon atoms, preferably egg 3 or 4 carbon atoms, a cycloalkyl group with 5, 12 carbon atoms, an aryl group with 6 ... 11 carbon atoms, an aryl group with 7, 9 atoms. carbon or, preferably, a hydrogen atom, and then, when the symbol n is equal to 1, the symbol R 1 represents a monovalent radical with meanings identical to those of the symbol R 1 or represents a monovalent residue obtained by removing a hydroxy group from a sulfinie acid, of a sulfonic acid, of an acid containing phosphorus, or of boric acid or representing an aryl group), a group of 5 to 12 carbon atoms, or a residue of the formula:
CH<sub>3</sub>CH<sub>3</sub> \/ \
XN-R<sub>10</sub>
R / \ "/ / \ ch<sub>3</sub>ch<sub>3</sub> wherein the symbol Rw represents a hydrogen atom or has meanings identical to the symbol Ri, when the symbol n equals 2, the symbol Rs represents a bivalent residue, namely an alkylene group with 1 ... 20 carbon atoms, an alkenylene group with 2 ... 20 carbon atoms, preferably 3,. 20 carbon atoms, an alkynylene group with 2 ... 20 carbon atoms, preferably with 3 ... 20 carbon atoms, a cycloalkyl group. with 5. . . 12 carbon atoms, one aryl group with 6 ... 14 carbon atoms, an aralkylene egg group 8 ... 14 carbon atoms, an aliphatic, aromatic or hexagonal clicker group, a -CO-, a -CO-CO-, a dicarbamoyl or an aliphatic or aromatic dithiocarbamoyl group , a sulfindyl group), a sulfonyl group, or a bivalent residue obtained by removing two hydroxyl groups from a disulfonic acid, from a phosphorus-containing acid, or from a boric acid, when the symbol n is equal to 3 , the symbol R 1 represents a trivalent residue, namely a group of alcantries, an arenifcryl group or a group of triacyl arsenic, a triac group. aliphatic or aromatic, or a triac group originating from orthophosphoric, or, tofoisfocos or orthoboric acid and, when the symbol n is equal to 4, the R symbol represents a tetravalent residue, namely an alkantetrail residue, a t & tracil residue derived from a tetraearboxylic acid. aliphatic or aromatic or orthosilicic acid, compounds used as stabilizers for polymers.
There are known compounds that have the general formula:
~ <sub>0</sub>--r-<sub>3</sub> /\
Hi <\ | | / R '
H<sub>3</sub>C<sup>/ X</sup>'N<sup>/</sup>'<sup>7</sup>R '<sub>2</sub> _ II _ n 'wherein the symbols R'i and R'2 are the same or different and each represent an alkyl group or form together with the carbon atom to which an allyl, saturated click or group of the formula are linked:
CH<sub>3</sub> ch<sub>3</sub> \ / ch<sub>3</sub> ch<sub>3</sub> symbol n<sup>r</sup> represents an integer between 1 and 3, when the symbol n<sup>r</sup> is equal to 1, the symbol Rb represents 64573 targets an acyl group from an aliphatic, alicolic or heterocyclic monocarboxylic acid, an N-substituted carbamoyl group from an N-substituted carbamic acid, an unsubstituted thiocarbamoyl group from a thiocarbamic acid Non-substituted, a monovalent group obtained by removing a hydroxyl radical from an oxoacid, an alkyl group, a cycloalkyl group, an aralkyl group, an aryl group or a group of the formula:
ch<sub>3</sub> ch<sub>3 </sub>\/
X NH / / \
R'i R '<sub>2</sub> in which the symbols R'i and R'î have the meanings above; when the symbol r 1 is equal to 2, the symbol R b represents a diacyl group derived from an aliphatic, alicyclic, aromatic or heterocyclic dicarboxylic acid, a dicarbamoyl group from a diicarbamic acid, a bis-thioicarbamoyl group from a bis-thiocanbaimic acid, a carbon group !!, a bivalent group obtained by removing two hydroxyl radicals from an oxoacid, a<sub>35 </sub>alkylene group, an arylene group or an arylendialalkylene group; when the symbol r 1 is equal to 3, the symbol R b represents a triacyl group originating from an aliphatic, alicyclic, aromatic or heterocyclic tricaPboxylic acid, a trccanamoyl group from a tricarbamic acid, a tris-tionba / moyl group from - a tris-thiocarbamic acid, a trivalent group<sub>45 </sub>obtained by removing three hydroxyl radicals from an oxoacid, an alkanitriyl group, an arentriyl group or an arentriyl trialalkylene group.
The process according to the invention extends the range of piperidine derivatives by treating a piperidinol of general formula II:
z \
ΟΗ<sub>3χ</sub>| |<sub>z</sub>ch<sub>3</sub>
I
Ri where Ri and R2 have the meanings of may <sup>(I1</sup>) 60 above, with a compound of general formula III:
R<sub>3</sub>- (OH) n · (ΠΙ) where Rr and n have the above meanings, the reaction takes place at reflux temperature, in benzene, toluene or anhydrous xylene as an inert solvent, in the presence of a lower tetraalkyl titamate as catalyst , after which the product is separated from the reaction mixture in a self-known manner.
39 Examples of carrying out the process according to the invention are given below.
Example 1. A mixture consisting of 10.26 parts by weight 1,2,2,6,6-pentamethylpiperidin-4-ol, 6.06 parts by weight sebacic acid, 1.0 parts by weight titanium tetra-n- butyl and 100 parts by weight xylene is heated under reflux for a period of 60 hours. After removal of xylene by distillation under reduced pressure, an oily substance is obtained, which is treated with 0.5 parts by weight sodium carbonate, 0.5 parts by weight coal and 25 parts by weight water, the resulting mixture being then boiled under reflux over a period of one hour. After removal of the water by distillation under reduced pressure, a black residue is obtained, which is extracted several times with ether.
The ethereal extracts are combined and dehydrated, and the eiter is removed by distillation under reduced pressure, to obtain a yellow oil, which is distilled under reduced pressure, to give 5.0 parts sebacate bis (l, 2,2,6,6-pentamethyl-4-piperiidinyl) as an oil. colorless with a boiling point of 220 ... 222 ° C, under a vacuum of 0.2 mm Hg and with the following elemental analysis (¼ mass):
Penitentiary analysis. C30H55N2O1:
- calculated: C = 70.82; H, 11.10; N, 5.51;
- Found: C, 70.60; H = 11.00; N, = 4.81.
Instead of xylene, benzene or toluene can be used as a solvent.
Table 1 presents a series of esters which are prepared by the process described in Example 1.
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All compounds of general formula I can be prepared by working in the manner described in example l
Then the symbol n is equal to 1, the symbol R1 and / or its symbol R1 may represent an aitohyl group with 1 ... 20 carbon atoms and preferably egg 1 ... 18 carbon atoms; Examples may include methyl, eethyl, n-propyl, n-butyl, socbutyl, tert-butyl, n-hexyl, n-ioctyl, 2-atylhenryl, n-nomyl, n-decyl, n-unidecyl, n-docicoil. , n-trideicyl, n-tetradecyl, n-hexadecyl, n-odsaidoyl and eiioosyl. However, in terms of optimum compatibility with polycdefinitive substrates, it is preferred for the symbols R1 and / or R1 alkyl groups with 5 ... 20 carbon atoms and preferably 5 ... 12 carbon atoms. A subgroup of R 1 alkyl radicals is represented by those radifiers containing 1 ... 4 carbon atoms and preferably the methyl radical, in cases where R 1 and / or the R 1 symbol represents an 3-alkenyl group. 20 carbon atoms may be mentioned as examples allyl, metalyl, 3-hexenyl, 4-octenyl, 6-deicenyl, 10-unideeeml and 8oethaddcenyl, but the preferred substituents in this hinge feel represented by the allyl group and the meltalyl group. In cases where the symbol R1 and / or the symbol R1 represents alkynyl groups, propargyl butyn-1-yl, bi-2-yl, pentin-d-yl, hexin-1-yl, octyl-1yl groups may be mentioned as examples. ten-il, twelve-4-il, tetradeicin-il and ootaidepinHl. However, the preferred alkynyl groups include propargyl and methyl propargyl. if the symbol R1 and / or the symbol R1 represents an arachyl group, the examples may be mentioned as the groups benzyl, beta-phenylelthyl, alpha-rnetylbenzyl, alpha, ^ lifa'-dimethylbenzyl, alpha-tnaffilme, til and ptnetyl-alpha-methylbenzyl . Of these groups, the band is preferred.
Another subgroup of substituents R1 and / or R1 is constituted by the alkyl radicals substituted by the formula:
- (CH <sub>m</sub> —CH — X, or —CH — X<sub>2 </sub>R4 IX i wherein R 1, X t and X 2 have the above meanings, but R t is preferably a hydrogen atom, and m is preferably equal to egg 1.
Dondi dud Xi represents a hydroxyl group, examples of Rt and / or Fea-u may be mentioned as 2-hydroxyethyl, 2-hydroxyethyl, 3-hydroxyl, oxypropyl, 3-hydroxy-bifyl, 4-hydroxybibyl, 4-hydroxypentyl and 2-hydroxy-2-phenylethyl, preferring the groups 2-hydroxyethyl 2-hydroxyprotyl and 2h | droxte2-lpheniieitifl.
Then canidine X1 and / or Xz represent halogen atoms, as examples, of α and / or R2 aufoatitiators, mention may be made of the 2-chloroethyl, 2-hromethyl, 2-chloropropyl, 3-chloropropyl, 2-bramprapil, 3-bromopropyl, 3- groups. chlorobutyl, 4-chloro-butyl, 2-chloro-2-phenylethyl, preferring the groups 2-doroethyl, 2-thiol'propyl and 2-chloro-, 2-phenylethyl.
in the case of the XI and / Bau X2 pathways, they represent cyan groups, as substitutes represented by R1 and / or Rî, the groups ciaumethyl, 1-cyanlbutdl, 2.cyanbutyl 4-cyanbutyl, 2-cyan-2- may be mentioned. phenyl> til, preferably 2eciaindtil group. in the oasis in which X2 represents a group
1.2- epoxy, R1 and / R8 represents the group
2,3-epoxyl-n-propyl or 2,3-epoxymethyl-propyl, if Xt represents a group - OR - OCORs - OOSRs, -OCONRJb, -CSNRsRî or when X1 and / or X2 represents a group - CORs, —COORs, —COSRs or —CONRsRs, and R1 represents an alkyl group, the preferred group having 1 ... 12 carbon atoms and in particular 1 or 2 carbon atoms; then kinnid represents an alkenyl group, the substituent R1 preferably contains 2 ... 4 carbon atoms; then cinnid represents a • cidloalkyl group, Rs preferably has 6 carbon atoms; If it represents an aryl group, Rs preferably contains 6 or 7 carbon atoms, and when it represents an arachyl group, Rs preferably contains 7 or 8 carbon atoms. The symbols Rs and Ri, taken together with the nitrogen atom to which they are linked, can form a 5- or 6-membered ring, such as, for example, the pyrrolidinyl, imidazolandinyl, pyrazolidim, piperidim, piperasinyl or morpholind group.
As examples of substituents R1 and / or R1 in this subgroup, mention may be made of the 2-methoxyethyl, 2-ethoxyfenyl, 2-proxyopethyl, 2-butoxyethyl, 2-methoxypropyl, 2-ethoxypropyl, 3-eethoxypropyl, 2n-butoxypropyl, 3-n-butoxypropyl, 3-methoxybutyl, 4-methoxybutyl, 3-ethoxybutyl, 4-ethoxybutyl, 3-ibutoxybutyl, 4-butoxybutyl / 4-methoxypentyl, 4-ethoxypenyl, 4-n-butoxypentyl, 2-methoxy-2- ifenylethyl, 2-ethoxy-2-phenylethyl, 2-alethoxyethyl, 2-n-propyl: nooxyethyl, 2-benzoyloxyethyl, 2-acetoxypropyl, 2-n-propionoxypropyl, 4-acetoxybutyl, 4-n-tpropionoxybutyl, 4-, aiceitoxipenityl, 4-n-propionoxypentyl, 2-phtemyl) -2-acetoxy<sup>it</sup>eitil<sub>it</sub> 2- (metiLcaubamoiloxi) -ethyl<sub>(</sub> 2- (ethylcarbamoyloxy) -ethyl, 2 (phenylcarbamoyloxy) - © til, 2 -. (M<sup>:</sup>ethylcarbatmohyloxy) -piqpil, 2- (eitilcarbam<sup>|</sup>oxyloxy) -propyl, 2-phenyl-2- (carhamthyloxy) -ethyl, 2- (9-yltylarycarbamoyloxy) -ethyl, 2-phenyl-2 - (methitoarbamoyloxy) -ethyl, mefiicarbonylmethyl, 2- (methylearbonylj-ethyl, 2- (ethylcarbondyl) ) -atyl, 2- (methylcarbonyl-1-propyl and 2- (matylcarbonyl) -2-phenylethyl; methoxycarbonylmethyl, 2- (ethoxyarbondyl) -ethyl, 2- (methoxycarbonyl) -p (ropyl, 2-
<img file="RO64573A_D0003.tif" />
»7 (methoxycarbonyl) - 2-phenylethyl, 2- {ethylthiocarbonyl-ethyl, 2- (methylthiocarbonyl) -piOpyl and 2 (methylthiocarbyl) -2-phenylethyl, carbamoylmethyl, 2-canbamethylethyl, 2- methylcarbam.oilefil, 2-ethylearbamethyl, dimethylcarbamoylmethyl, 2-άί6ϋ1ϋ9ΛααηοϊΐΘϋ1, 2- (itioca'rbamoil) -atil, 2-m ethyl thio cai'bam oii eti 1, dime ti 1 ti ocarbam οι Im ethyl, 2- enilcarbaamoil) -eti 1.
When n equals egg 1, and R1 and / or R3 represents a crane, for acyl -COR7, in which R7 represents an aliphatic residue unsubstituted or substituted by 1 ... 20 carbon atoms, this symbol may represent one of the methyl, ethyl, propyl, butyl, hexyl, n-octyl, 2-ethylhexdl, n-decyl, nundecyl, n-tridecyl, n-tetradecyl, n-hexadecyl, n groups -heptadecyl, eicosil, chloroethyl, chlorhexyl, methylthioethyl, ethylthioethyl, octylthioethyl or dodecylthioethyl; the alkenyl groups representing the symbol R7 have 2. .. 20 carbon atoms, preferably 2, 6 carbon atoms, such as, for example, vinyl, allyl, metalyl, isobutenyl or hexenyl groups; the alkynyl groups .pe representing R7 have 2. . . 20 carbon atoms, preferably 2 ... 6 carbon atoms, such as, for example, the propargyl group; the cycloaliphatic residues representing the symbol R7 have 5. . . 12 carbon atoms and in particular 6 carbon atoms such as cyclopentyl or cyclohexyl; the araliphatic residues represented by the symbol R7 have 7 ... 14 carbon atoms, preferably 7 ... 9 carbon atoms, such as, for example, the benzyl group, beta-phenylethyl, diphenylmethyl, or news; when it represents unsubstituted aromatic residues, the symbol R7 has 6 ... 14 carbon atoms and preferably 6 ... 10 carbon atoms, such as phenyl or naphthyl group aryl; when it represents a substituted aromatic residue, the symbol R7 is substituted by an alkyl group having 1-4 carbon atoms, such as, for example, the tolyl group or the p-tert -butylphenyl group; heterocyclic radicals R7 may be represented by furan or thiophene residues. As compounds wherein R1 and / or R3 are acyl unsaturated groups, those compounds in which mimim one of them is assigned an unsaturated acyl group are preferred.
As examples of acyl groups, represented by R1 and / or R3, mention may be made of the groups formyl, acetyl, propionyl, n-butyryl, hexane-oil, hept-anoyl, octanoyl, 2-eethylhexanoyl, 2,2, 4-trimeti.lpentanoi.1, n-decan-oil, n-d'odecan.oil, n-tetradeeanoil, n-hexadecanoyl, n-octadecanoyl, nylooyl, acryloyl, alpha-methacryloyl, cr-otonoyl, umdecan-10- oil, o.ctaidecan-9-oil, beta-methylthiopropio-nll, methylthioacetyl, betaoctilithiopropionyl, beta-dodecylthioipropionyl, cyclopentanoyl, cyclohexanoyl, benzoyl, a-lfanaphthoyl, beta-naphthyl, cyclopemethylacetyl, cyclohexylacetyl, phenylacetyl, beta-femipro18 prionyl, diphenylacetyl, beta-phenylacryloyl, 0toloyl, m-to-lOoyl, p-toluoyl, meth-yloxy, meth-yloxy, methyl , o-elorbenzoyl, m-chlorobenzoyl, p-chlorobenzoyl, 2-furoyl and 2-pycolinoyl.
When the symbol n is equal to 1, R 1 and / or R <may represent a carbaanoyl group or a thiocarbamoyl group having a 10-mule:
wherein X 3 represents an oxygen or sulfur atom, Re represents a hydrogen atom or an alkyl group egg 1 ... 4 carbon atoms, and R? represents a hydrogen atom, an alkyl group of 1 to 20 carbon atoms, alkenyl of 3 to 20 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aryl unsubstituted or substituted, for example, by alkyl or halogen atoms, this aryl group having 6 ... 12 carbon atoms, preferably 6 ... 10 carbon atoms, As examples of such substituents, the radicals may also be mentioned: carbamoyl, N-methylarbamoyl, N-ethylcarbamoyl, N-npropylcarbamoyl, N-isopropylcarbathoyl, Nn-butylcarbamoyl, Nn-pentyl-cai-bamoyl, Nn-octyl carbamoyl, Nn-sdecylcarbamoyl,
N-dodecylcarbamoyl, N-ootadecylcarbamoyl, Nn-eicoBilcarbamoyl, N-allylcarbamoyl, N -methylcarbamoyl, N-undecenylcarbamoyl, N-cyclopentylcarbamoyl, N-cyclohexylcarbamoyl, N-methylcycloalkyl - (2-perhydronaphthyl) -arbamoyl, N-adamantylearbamoyl, N-oyclopentylmethylcarbamoyl, N-benzylcarbamoyl, N- (beta-phenylethyl-earbamoyl, N-tert-naphthylmethyl) earbaimoyl, N- (2-naphthylmethyl) ^ carbamoyl,<sup>45</sup> phenylcarbamoyl, N- (o-tolyl) -carbamoyl, N (m-tolyl) -carbamoyl, N- (p-tolyl) -carbamoyl, N- (2,4-xylyl) -carbamoyl, N- (2,6- xylyl) -carbamoyl, N- (alpha-naphthyl) -carbamoyl, N- (betanaftllj-ca-rbamoyl, N, N - dimethylcarbamoyl, 50 N -nethyl-N-ethylcarbamoyl, NN-diethylcarbamoyl, Ν, Ν-diisopropylcarbamyl , N, N -di-npr a pilearbamoyl, N, N -di-n-butylcarbamoyl, Ν, Ν-diisobutylcarbamoyl, as well as the corresponding thiocarbamoyl radicals.
When R 2 represents an alkyl group, it may be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, preferably methyl; as alkenyl group, R? represents, for example, the allyl, metalyl, 3-hexenyl, 4-octanyl, 6-decenyl, 10-undecenyl or 8-octadecenyl groups and preferably allyl or m-ethyl; As an alkynyl radical, R 2 may, for example, represent a propargyl group, butynyl-1-yl, butyn-2-yl, pentin-1-11, hexin-1-yl, octin'ί
1, ten, 1, dodeein, 1, tetradecin-1yl and octadccin-1 and preferably propargyl; as a cycloalkyl group,
R 1 represents, for example, cyclopentyl, eiclohexyl, ethyl cyclone, cyclododecyl; In the aryl radical category, R 2 represents, for example, the phenyl, p-tolyl, berthyl-butylphenyl, naphthyl groups; as aralkyl radical, R? represents, for example, the groups of the benzyl, alpha-mefcilbenzyl, alpha-dimethyl-benzyl.
if the symbol n is equal to 1, R3 may have meanings identical to R 1. When representing an alkyl group, Ra has 3 ... 18 carbon atoms. As an aryl radical, R 3 represents, for example, an aromatic residue with 6 ... 20 carbon atoms and preferably an aryl group with 6 ... 12 carbon atoms. As a cycloalkyl radical, R3 represents 20 cyclopentyl, eiclohexyl, cyclooctyl, or cyclopododecane groups.
When the symbol n is equal to 2,
R1 represents, for example, an alkylene group with 1, 20 carbon atoms and preferably 2 to 6 carbon atoms, such as methylene, ethylene, polymethylene, tetramethylene or hexamethylene. As alkynylene radicals, R 3 preferably contains 3 ... 20 carbon atoms and 30 in particular 3 or 4 carbon atoms and may represent, for example, the 1,3-propen-2-en or 1,4-butene group. 2-ene. As alkynylene residues, R3 preferably contains 3 ... 20 carbon atoms and more<sub>33 </sub>selected 4 carbon atoms and represents, for example, 1, 4-butyn-2-ylene. When it is a cycloalkylidene residue, R3 preferably contains 7 or 8 carbon atoms, such as, for example, the cyclohexycetidymethylene group. if repre-<sup>40 </sup>targeting an arylene group, R 3 preferably contains 6 ... 12 carbon atoms, for example, the 1,3-phenylene or 4,4'-diphenylene group. As an aralkylene group, R 3 may, for example, be the alpha, aifa-p-xiiylene group. As diacyl radicals, R 3 represents diacyl residues from an aliphatic, aromatic or heterocyclic dicarboxylic acid. As aliphatic dicarboxylic acids may be mentioned acids with 2 ... 20 carbon atoms, preferably 6-alkanidicarboxylic acids. . .
carbon atoms, such as, for example, malonic, succinic, glutaric, adipic, pimelic, suberic, aceiac, ssbacic, 1,12-dodeicandioic, 1,18-octadeicandioic, 1, 20-dacoeanidioic and N-methyl acids] imino diacetic. As examples of aromatic diacyl residues, one may mention the radicals pro-<sup>6C </sup>come from phthalic acid, isophthalic acid and terephthalic acid, these residues possibly being substituted in the ring with halogen atoms, with an alkyl or alkoxy group <sup>61</sup> with 1 ... 20 carbon atoms, with a hydroxy group or with a tertiary amino group.
As hetero dicarboxylic acids, cyclic may be referred to as 2,5-thiopenedarboxylic acid or 2,5-furanidicarboxylic acid. As an aliphatic or aromatic dicarbamoyl radical, R 3 may represent a bivalent alkyldicarbamoyl moiety, such as, for example, butane-1,4-dicarbamoyl or hexane-1,6-dicarbamoyl; As a bivalent residue of the years Micarbamoyl, R3 represents the bivalent group phenyl-1,4-dIicarbamoll. as a rest. Goose, ailiphatic or aromatic moiety, R 3 represents a bivalent alkenithiocarbamoyl moiety such as, for example, butane-1, 4-dithiocarbamoyl or hexane-1, 6-dithioarybamoyl; As bivalent aryldithiocarbamoyl residue, R3 represents the phenyl-1,4-dithiocarbamoyl group.
When the symbol n is 3, R 3 represents a triacyl residue from an aliphatic tricarboxylic acid, such as nitrilotriacetic acid, tricarbalyl acid, or a triacyl residue from an aromatic tricarboxylic acid, such as benzentricarboxylic acid, or a triacyl residue from an inorganic acid, such as, for example, orthophosphoric, orthophosphoric or orthoboric acid, or a triacyl residue from oxyacids such as benzene, 3,5-triS'UlfcnLc.
When the symbol n is equal to 4, R 3 represents, for example, a tetraaeyl group derived from tetracarboxylic acid and ethylenediammotetracarboxylic acid, 1,2,4,5-benzentetracarboxylic acid or o-eilic acid.
The symbol R3 preferably represents an acyl, N-substituted carbamoyl, alkyd, optionally substituted group or an aralkyl group. The symbol R1 preferably represents an alkyl, alkenyl, substituted alkyl group such as, for example, hydroalkyl, alkylcarbonyloxy or aralkyl.
as compounds of general formula I in which n is 1, the substances may be mentioned: 4-methoxy-1, 2,2,6,6-pentamethylipiperiidine, 4-n-butoxy-1, 2,2,6,6-pentamethib piperidine, 4-nd; odecik> xi-l, 2,2,6 , 6-pentamethylpiperldine, 4-n-oiotadecyloxy-d, 2,2,6,6pentamethylpiparidine, 4- (2'-cyanethoxy) -1,2,2,6,6-pentamethylpiperidine, 4- (2 '- toxic hydroxy) -1,2,2,6,6-penile ti.lpiperi.dina, 1-npropyl-4-ffnetoxy - 2,2,6,6-tetramethylpiper.idine, ln-propyl-4- n-dodium oxy-2,2,6,6-tetraimethylpipemidine, ln-prapil-4-n-actadecyloxy-2,2,6,6nthin-methylpiperide, 1-secbutyl-4-n-dodeeyloxy - 2,2,6,6-tetramethylpiperidine, 1-oethyl-4-methoxy-2,2,6,6-tetramethylpiperidine ·, n-dodecyl-4-n-dodeeyloxy-2 , 2,6,6-tetramethylpiperiidine, 1-n-octadecyl-4-methoxy - 2,2,6,6-tefcramethylpiperidine, 1-n-octadecyl-4-n-o'ctadicyloxy-2,2 , 6.6 tetra amethylpiperidin, ln - and icosii-4-.metox i6457.3
2,2.6.6-tetramethylpipei'idine, 1-allyl-4-methoxy-2,2,6,6-tetramethylpyridine, 1-allyl-4-allyloxy-2,2,6,6-tetramethylipylpiperidine, 1- (1-) undec-1'-enylj-dn-hutoxy - 2,2,6,6-tetyramethylpiperiidine, 1- (l'-undec-10'-enii) -4- (eleven-lO'-enyloxy) - 2, 2,6,6-tetramethylpiperiidine, l-oleyl-4-imethoxy-2,2,6,6-tetrame-tilpilperidine, l-oleyl-4-oilyi-oxy-2,2,6,6-tetramethylpiperidine, propargyl-4-ethoxy-2,2,6, 6-tebramethylpiperiide, l-propargyl-4-propargyloxy - 2,2,6,6-tetraimethylpiperidine, 1-bandsM-n-xtadecyloxy - 2,2,6,6-tetramethylpiperidine, l-benzyl-4-allyloxy-2,2,6,6-te, tramethylpiperiidine, l-benzyl-4-ylOpargyloxy 2,2,6, 6-tetramethylpiperidine, benzyl-4-benz; loxy-2,2,6,6-tetramethylpi'peridine, 1 (2'-hi <d, roxietyl) -4-, melOxi-2,2,6,6-tel .ramethylpiperidine, 1- (2'-hydroxypraipyl) -4-allyloxy2.2.6.6- tetra, methyl, piperidine, 1- (2'-hydroxyethyl) -4-proipargiioxy - 2,2,6,6-tetramethylpyridine , (2'-hydroxyproipyl) -4-benzyloxy2.2.6.6- tetramethylpiperidine, (2'-hydroxyethyl) -4- {2'-hihydroxyethoxy) - 2,2,6,6-Letramethylpiperidine, 1 -. (2<sup>,</sup>-ΜιάΓ0ΧΐρΓορί1) -4- (2'-ΜΐΌxijprop oxy) - 2,2,6, e ^ tetram ethylipiperidine, 1 (2'-hydroxy.-2'-femletyl) - 4-n-butoxy-2,2,6 , 6-tetramethylpiperidine, 1- (2'-hfdroxy-2'-phenylethyl) -4- (2'-hiidiOxi-2b-phenylethoxy) - 2,2,6,6-tetraimethylpiperidine, 1- (2'-ethyl) - 4-Node, loxy-212,6,6-tetramethylpiperidine, 1 (2'-chlolpropyl) -4-bands<sup>1</sup>loxi -2,2,6,6-tetramethylpiperiidine, 1- (2'-bromethyl) -4- (2'-hromethoxy-1'-.e ^ -tetrame'tilpiiperidine, 1- (2'-cl, or 2'Hphemtebil) ) -4-n-O'Ctyloxy - 2,2,6,6-tetraimethipiperidine, 1- (2'-cyanethyl) -4-phenoxy-2, -2.61 6-tetra-amethylthiperidine, (2'-cyanethyl) -4-benzyloxy-2,2,6,6-tetramethyl, lipiperiidine, 1 {2'-cyanethyl) -4- (2 '-' cyanethoxy) - 2,2,6,6 -tetramebilpiiperijdine, (2'-cyanpro! fur) -4-imethoxy-2,2,6,6-tetramethers<sup>,</sup>lpi | peridine, l (2 ', 3'-epoxypropyl) -4-n-butoxy - 2,2,6,6-' tetrameliylpiper iidine, 1 - (2 ', 3' -epoxypril) - 4-benz il oxy2.2.6.6- tetramethylpiperperidine, (2 ', 3'-epoxypiproipyl) -4- (2', 3'-eipoxy, propoxy) -2,2,6,6-ietramethylpiperidine, 1 - (2 ' -methoxyethyl) -4-ethoxy2.2.6.6- tetrah, methyl'piperidine, 1- (2'-methoxyethyl) -4- (2'4-methoxyethyl) - 2,2,6,6-t & tramethylpiperidine, ( 2'-etoxipro / PIL) -4-2,2-aIilcxi,
6,6-tetraimethylpiperidine, 1- (2'-ethoxy-2'-phenylethyl) -4-benzyloxy - 2,2,6,6-tetramethylpiperidine, 1- (2'-acetoxy & lt) -4-n-butoxy-2,2 , 6,6-tetramethylpiperidine, 1- (2'-benzoyloxyethyl} 4- (2'-benzyloxyethoxy) -2,2,6,6-tetramethylpiper, riidine, 1- (2'-prepionoxypiipyl) -4-allyloxy2.2.6.6 - tetnameti: lpiţperÎdina, 1 - [2 '- (methylcarbamoyloxy) -ethyl] - 4doenzyloxy-2,2,6,6-<sup>!</sup>tetramethylpiperidine, l - [. 2 '- (methylcarbamoyloxy) -ethyl] -4- [2' - (me tilcanbamo i.ioxi) -ethoxl] 2.2.6.6- tebram'etiipiperidine, l [2 '- (femlcairbamoyloxy) - ethyl] -4- (2'-Jianyanoxy) -2,2,6,6-tet amethylipiperyldine, 1- [2 '- (ethylthiocarbamoyloxy) -ethyl] 4- [i2<sup>,</sup>- (ethylOarbamyloxy) -ethoxy] 2.2.6.6-tetramethylpiperidine, 1-methylcarbonylmethyl-4-methoxy - 2,2,6,6-tetra methylipiiphydine, l - [(methylcarbons: l) -ethyl .L] -4-n-octilo.xi22
2.2.6.6- tetra-methylpiperidine, 1-imethylcarbonylmethyl-d-imethylcarbonylmethoxy -2,2,6,6-tetramethylpiperidine, 1- (2'-methoxycarbonylethyl) -4- (2'-methoxycarbonylethoxy) - 2,2,6, 6-.tetramethylipiperidine, 1- (2'-imetoxycarbonylethyl) -4-ethoxy-2,2,6,6-tetramethylpiperildine, 1 [2 '- (ethoxycarbonyl) -ethyl] -4- (2'-hydroxyethoxy) 2.2. 6,6-tetramethylpiperidine, 1- [2 '- (thioethoxy, carbonyl) -ethyl] -4-imethoxy-2,2,6,6- - tetraimethylpiperidine, l-carbamoylmethyl-4-benzyloxy-2,2,6,6- tebraimetilpiJperidina, 1- (2 '-: carbamoylethyl-4-: dod.ecyloxy-2,2,6,6-tetramethylpiperidine, 1- [2' - (methicarbamoyl) -ethyl] -4 (2 '-, methylcarbaimoethoxy) -2, 2,6,6-tet amethylpiperidine, 1- [2 '- (diethylcarbaimOil) -ethyl] -4-methoxy-2,2,6,6-tetramethylpiperidine, 1-thiocarbamoylmethyl-4-allyloxy-2,2,6, 6 - tetramethylpiperidine, 1- (di, methyl, thiocairbainiooyl-methyl-4-benzyl-Ioxl-2,2,6,6-tetramethylpiperidine, l-acetyl-4-benzyloxy - 2,2,6,6-tet.ramethylipiperidine, l -lau, roil-4- (2'-hydroxyethoxy) -2.2, 6, B-tetraimethyllylpiperiidine, i-stearyl-4-anethoxy-2,2,6, 6-tetramethyridine peridine, 1-benzoyl-4-n-butoxy-2,2,6,6-tetraimethylphiperidine, 1ca<sup>,</sup>rbamoyl-4-n-octadecyloxy - 2,2,6,6-tetramethyl, piperidine, 1-methylchanbaimoyl-4- <bands] oxy-2,2,6,6-tetramethylipiperidine, 1-phenylcarbamoyloxy-4- (2 ' -hydroxyethoxy) - 2,2,6,6-tetramethylpiperidine, 1-phenylthiocarbamoyl 4- (cyclohexyloxy) - 2,2,6,6-tetramethylpiperidine, dimethylcarbamyl M-imethoxy-J, 2,6,6-tetramethylpiperidine, l-methylthiocarban- Octiloxy-2,2,6,6-tetramethyl] piiperidine, 1-phenylthiocarbamoyl-4-imethoxy-2,2,6,6-tetramethylpiperidine, 1,2,2,6,6-pentamethylpiperidinyl- (4) formate, 1,2,2,6,6pentamethylpiperidine acetate: iI- (4), isobutyrate
1.2.2.6.6- ^ pen taine tiilip i, for idi nil- (4), n-oc ta noatul of 1,2,2,6,6-pentamethylpyridiml- (4), pivalate of 1,2,2, 6,6-pentamethylpiperidinyl- (4), 1,2,2,6,6-pentamide stearate, tilpiperidinyl- (4), 1,2,2,6,6-pentametiipiperidinyl- (4) cyclosenoate , 2'-ethylhexanoate of
1.2.2.6.6- pentamethylpiperidyl nyl- (4), 1,2,2,6,6-pentamethylpiperidinyl- (4) acrylate, 1,2,2,6,6-pentamethylpiperidinyl- (4) oleate, cyolohexancarboxylate of 1,2,2,6,6-pentamethylpiperidinyl- (4), addntan -1-like rboxi to l, 2,2,6,6-pentamethylpiperidinyl- (4), benzoate of 1,2,2 , 6,6-pentamethylpiperiidinyl (4), p-fco'luate of 1,2,2,6,6-pentamefcilLpiperidini] - (4), p-tert-butylbenzoate of 1,2,2,
6,6-pentamethyl: 1,2,2,6,6-pentamethylipiperidyl- (4), 1,2,2,6,6-pentamethylpiperidinyl alpha-naphthoate piipe.ridin.yl- (4), - (4), phenylacetate of 1.2,
2,6.6-pentamethylpiper; perdindin (4), 1,2,2,6,6-pentamethylpiperidinyl- (4), 1,2,2,6,6-hypentamethylpiperidinyl- (4) cinnamyl, (diphenylacetate) of 1,2,2,6,6-ipentamethylipip er 1- (4), n-dodecylthioacetate of 1,2,2,6,6-pentamethylpiperidinyl- (4), furan-2'-ca, rboxylate : 1,2,2,6,6-pentamethylpiperidinyl- (4), 1,2,2 dimethyltrimethyl,
6.6- Jpentamethylipiperidines, 1- (4), acetate
643713
Ι-η, -ipropyl -2,2,6,6-tetramethyltylpiperiidinyl- (4), ln-propyl-2,2,6,6-tetraimethylpiipeirijdiniI- (4) octane, ln-propit stearate2.2.6 .6- tetramethyl) piperidinyl- (4), 1-n-acti-1-2,2,6,6-telamide di-nyl (4) benzoate, n-dodecyl-2 n-octanoate , 2,6,6-tetramethylpipe. 1-diminyl- (4), 1-dodojoyl p-chlorobenzoate - 2,2,6,6-tetramethylpiperidinyl (4), 1-octadecyl-2 benzoate, 2,6,6-tetramethylpiperidinyl- (4), 1-allyl 2,2,6,6-tetraimethylpiperidinyl- (4) n-octanoate, 1-allyl-2,2,6,6-tetramethylpiperidine-1-cyclohexanecanboxylate (4), 1-allyl-2,2-benzoate, eG-tetramethylpiperidinyl-L), 1-alpha-metalyl-2-acetate 2,6,6-tetraanetylpiperidyl (4), l-.oleyl-2,2-cialohexancarboxylate,
6,6-tetramethylpiperiidinyl- (4), 1-propargyl p-methoxybenzoate-2,2,6,6-4eta.-ametipiperiidinyl- (4), 1-benzyl-2,2-octanoate,
6-Aenzyl-2,2,6,6- tetramethylpiperidinyl- (4), 2'-ethylhexanoate<sup>it</sup>tetramethylβiperidyl (4), 1-benzyl-2,2,6,6-tetramethylpiperildinyl- (4) stearate, 1-benzyl benzoate2,2, 6,6-tetramethylpiperidinyl- (4), acetate 1- (2'-hydroxy.ethyl) -2,2,6,6-tetramethylpiperidinyl- (4), la (1'-hydroxyethyl) laurate -2,2, 6,6-tetraimethylpiperi dimers- (4), 1- (2'-hydroxyatyl) - 2,2,6,6-tetramethylpiperidinyl- (4) stearate, (2'-hi (droxiethyl) -2,2) benzoate,
6,6-tetramethylpiperes from 1- (4), eleate, 1- (Z-hydroxypipyl) - 2,2,6,6-tetramethylpiperidinyl- (4), phenylacetate of 1- (2'-hydroxy-2'-phenylethyl) - 2,2,6,6-letramethylpiperidinyl (4), (2'-clarethyl) -2,2,6,6t n-octanoate tr-methylpiperidinyl- (4), eiclobexancaib or (2 ') xylate -br'm (prppil) -2,2,6,6-tetramethylpiperidinyl- (4), 1- (2'-chloro-2'-phenylethyl) - 2,2,6,6-teteaimethylpiperidinyl- (2'-chloro-2'-phenylethyl) (4), (2'-cyan.piOpil) -2,2,6,6-tetraimethylpip.eridinyl- (4) benzoate (4)<sub>></sub> acetate from {2<sup>r</sup>, 3'-epoxypropyl) -2,2,6,6-tetramethylpiperiidinyl- (4), 2'-ethylhexane. 1 (2'-ethoxypropyl) - 2,2,6,6-tetramethylpiperidinyl (4) oat, diphenylacetate of 1- (2'-ethoxy-2'-phenylethyl) -2,2,6,6-tetra methylpiperijdin.ii- (4), laurate of 1- (2 '-' acetoxyethyl) -2,2, 6,6-tetramethylpiperijdinyl- (4), [2 '- (methylcarbaimoyloxy) -ethyl] -12,2,6,6-tetraimethylpi'peridinyl- (4) benzoate, [2' - ( phenylcarbamoyloxy) -ethyl] -2,2, 6,6-tetramethylpiiparidinyl- (4), 1- [2 '- (ethylthiocarbamoyloxy) - © tyl] -2,2,6,6-tetramethylpiperidinyl (4), methylcarboniylimethyl phenylacetate 2,2,6,6-tetramethylpiperidines: 1 (4), acetate of [2 '- (methylicartionyl) -ethyl] -2,' 2,6<sub>!</sub>6-Phtetramethylpiperidinyl- (4), p-methoxybenzoate of ethoxybiomethylnethnyl-2,2,6,6-tetramethylpiperi-diinyl- (4), p-toiluate of [2 '- (methoxicanbonyl) -ethyl] - 2,2,6,6-tetramethylpiperidinyl- (4), 1-carbamoylmethyl pumethoxybenzoate-2,2,6,6-tetramethylpiperidinyl- (4), 1- (2'-carbamollethyl) stearate -2.2, 6,6-tetramethylpipe, redini- (4), (imetillcairbam oxyl) -ethyl} -2,2,6,6-tetramethylpiperidinyl- (4) octanoate, 1- (Dimethyl24 thiocarbamoyl) -anethyl-2,2,6,6-tetramethylpiperidinyl- (4) isobutyrate, (1,2-acetyl-2,2,6,6-tetramethylpiperidinyl-id), 2'-ethylhexanoatyl acetate tert-2,2,6,6-tetranethyl] ipiiperidini- (4), l-acetyl-2,2,6,6-tetramethylpiperidinyl- (4), n-octanoate of isobutyryl-2,
2,6.6- tetraimethylpiperidi nil- (4), cyclo-ring 1 of 1 -lauroyl-2,2,6,6-ftetramethylpiperidinyl- (4), 1-stearyl acetate-Oil-2,2,6,6-tetramethylpiperiinyl- (( 4), 1-benzoyl-2,2,6, 6-tetr ame tiiljp ip & ridinil- (4), 1'-naphthyl thalamus and 1-carb amoyl-2,2,6, 6-tetramethyl ether ridinyl- (4), 1-methylca.bramoyl 2, 2,6,6-tetramethylpipyridinyl- (4) n-octanoate, 1-enylcarbamoyl-2,2,6,6-tetraimethylpiperidine phenylacetate (4) ) laurate of 1-diyl thiylearbamoyl-2,2,6,6 - tetramethylpiperidinyl- (4), pterty-butylbenzoate of 1-phenylthioarbaimoyl2.2.6.6-tetramethyltipi eriidinyl- (4), 4-c -aramailloxy-l , 2,2,6,6Hpentamethylpiperidine, 4, methylcaiibamoyloxy-1,1,2,2,6,6-pentamethylpiperidine, 4-dimethylcarbamoyloxy-1,2,2,6,6pentam and tllpiperiid in a, 4-isopropylcarbamoyloxy- , 1,2,2,6,6-ipentamethylpiperidine, 4-tert-butylcarbamoyloxy - 1,2,2,6,6-pentameethylpiperidine, 4-n-hexylcanbamoyloxy-1,2,2,6,6-pentamethylpiperidine, 4- (2'-ethylhexylica'bbaimoyloxy) -l, 2,2,6,6-pentamethylpiperifdma, 4n-dodecylcarbiunooyloxy-1,2,2,6,6-pentamethylipiperiidine, 4-no, ctadeicylcar, 'bam.oÎ' alkyloxy it,
2.2.6.6-, pen tylenipidide and na, 4-allylcarbamoyl Ioxi-1,2,2,6,6-peppermint tilpiiperi dina, 4 • oleilca! Pbaimoi<sup>and</sup>oxy-1, 2,2,6,6-pentamethylpiperidine, 4-cyclohexylcarbamoyloxy-1,2,2,6, 6-pentamethylpiperiidine, 4- (3'-n-ethylcyclohexylcarbamoyloxy) -l, 2,2,6 , 6- pentamethylpiperidine, 4 "(4'-rie<sup>!</sup>cLo'hc: xyl.rEi.î'b.aini'Oil oxii) 4l, 2,2,6,6-pentamethylpiperaboration, 4-cyclohexylimethylcarbamoyloxy-1,2,2,6,6-penfamethylpiperidine, 4-benzyl earbam: oiloxy-l, 2,<sup>!</sup>2,6, e-ip.entamietylpiperidine, 4-phenylcarbamoyloxy-1, 2,2,6,6-hypentamethyltype; redine, 4-phenylcarbimoyloxy-1,2,2,6,6-pentamethylpiperidine, 4Hm-ltolylcarbamoyloxy-1,2,2,6,6-pentamethylpiperiidine, 4-p-dlorfen, ilcarbamodloxy-1,2,2,6,6-pentamethylipiperidine, 4-pter-butylAllenylcarbaryloxyix-1,2,2,6, 6-pentanethylpiperpi'dine, 4-alpha-naphthylcarbaimoyl, oxy-1,2,2,6,6-pentamethylpiper.i'dina, 4-cyclohexylcarbamoyloxy-1-ethyl-2,2,6,6-tetramethylpiperidine, d-Tmethylcarbamoyloxy-1-n-ipropiyl-2,2,6,6-tetramethylpiperidine, 4-tethylcarbamoyloxy-1-isec-butyl-2,2,6,6-tetramethylpiperidine a, 4-n-octadecylcarbamoyloxy-1 n- bu.ttl-2,2,6,6-tetramethylpdipe (redine, 4-anethylcarbamoyloxy-1-octyl-2,2,6,6-tetramethylpiperi'd, 4-rethylethylearbamoyl-1-n- oc 1 ad ecyl-2,2,6,6-tetramethylpyridine, 4-phenylcarbamoyloxy-1-allyl 1-2,2,6,6-tetramethylpylpiperine, 4-p-tolylcarbaimoyloxy-l-oleyl-2,2 , 6.6t efe · aimetilpip eriidine, 4-methylcarb-amyloxy-1-protargill-2,2,6,6-terephenylmethylpiperidine, 4-phenylcarbineyloxy.-1-ihen.zi.l - 2,2,6,6-tetramethylpiperidine, Ί-methylicaibaimoyloxy-1 - (2-hydroxyethyl) - 2,2,6,6-tetramethylpi; peridine, 4 I cyclohexylcarbaimoyloxy - 1- (2'-chlorproipyl) 2.2.6.6-tetramethylipiper.idine, 4-phenylicarbamoyloxy-1 (2'-Jhydroxy-2<sup>,</sup>-phenyls, thiyl) - 2,2,6,6-fold tilpiperidine α, 4-methylcarbam or iloxyl- (2 ', 3'-epoxypropyl) - 2,2,6,6-tetramethylpi-5-peridine, 4-carbamoyloxy- 1- (2'-imethoxyethyl) 2.2.6.6- with amine ethylpler, 4-dian and tilcarbaanoyloxy-1 (2<sup>,</sup>-acetoxieti<sup>:</sup>l) - 2,2,6,6-tetramethylpiperi / dina, 4-n-hexylcarbamoyloxy-1 [2 '- (methylcarbamoyloxy) -ethyl] -2,2,6,6 - tetra-10 methylpiperiiddna, 4-mefileai' bamoyloxy - 1methylcarbonylmethyl-2,2,6,6 - tetramethylpiperr idina, 4- nifcarbaimoyloxy -1 fa '-mylcarbonylethyl) - 2,2,6,6-teiramL + HeparinIldine, 4-benzylcarbaimioyloxy-l-carbamoylmethyl - 2.2, 15
6,6- tetramethylpiperiidine, 4-n-dodecycarbamoyloxy-1- (2 '-earbamoylethyl) -2,2,6,6- -tetramethylipiperiidine, 4 ^ βηοΗτ63ΐηιοϊ1οχί-1- (2Γ thiobabaimylethyl) - 2,2,6,6-tetyramine , 4-methylbaryloxyloxy-1-acetyl-2,2,6,6- 20 tetramethylpiperidine, 4-phenylca, residue: loxy1-stearoyl-2,2,6,6- tetra amethylpip idine, 4-methylthiocarbamoyloxy-1-lauroyl - 2,2,6,6-tetramethylpiperyrene, 4- (2'-ethylhexylcarbamoyloxy) -l-benzoyl-2,2,6,6-tetramethylpip.eriidi-25 na, 4-icarbamoyloxy-1-carbamoyl-2,2,6,6-by-tramethylpipeyrildin, 4-<sup>,</sup>metitcairbamoyloxy-lι · η6ΐΐ'ΐΌ3ΐ + 9ίΓΏΌί; 1-2,2,6,6 - tetramethylpiperidine a, 4-if and niihcarbamOyloxy -1 - fe nil carb am-oi l2,2, 6,6-tetramethylpiperidine, 4-methyl a carboxyloxy-methylcarbaryl-2,2,6,6-tetramethylpiperidine, 4-phenylthio-thamooyloxy-1,4-enithiocarbamyl-2,2,6,6-tetraethylpiperiidine, 4-diamethyl<sup>it</sup>caj<sup>J</sup>bamoyloxy-1-dimethylcarbamoyl-2,2,6,6-tetramethylpiperidine, 4- 35 stearyloxy-1,2,2,6,6-hexamethylpiperidine, n-4-phenyl-1-tanoate, 2,2,6, 6-pentametilpiperi! dlinill- (4).
if the symbol n is equal to, the following substances can be given as examples: 1,2- 49a<sup>r</sup>, 2 ', 6', 6'-pentaanetyl - 4Apiperidyloxy) -and, 1,4-biis - (1 '-n -proipiyl-2', 2<sup>1</sup>, 6 ', 6 tetramethyl-T-piperidyloxy-butene, 1,6-bis {1-n-octadeicyl - 2<sup>,</sup>, 2 ', 6', 6'-tetraimethyl-4'Hpi ~ peiridyloxy-hexaneU, l, 4-ibis - (. L'-ali: l-2 ', 2', 6 ', <sub>4g </sub>6Metramethyl-4 + peppers: diyloxy) -cyclohexane,
1,4- Ibis - ('l'-pyropargyl - 2', 2 ', 6', 6'-tetraimethyl4'-piiperyldiyl'0XL) -hut-2-ena, alpha, alpha-bis- (lbenzyl-2,2, 6,6-tetramethyl-4-peppers! Diloxy) -, pxilen, l, 3-bis- [l '- (2'-hi'droxyethyl) -2', 2 '<sub>)</sub>6' <sub>50</sub>
6 '-, tet amethyl-4' -piperiidyloxy] -benzene, 1,2bis- [r- (2-cyanethyl) -2 ', 2', 6 ', 6'-tetramethyl-4'-piperidyloxyJ-ethane, 1,4-bis - (l -acetyl-2 ', 2<sup>r</sup>, (^ e'-tetraimethyl - ^ '- ppiperidiil'OxÎ) - but-2-ina,
4,4- bis- (1-methylcarbamoyl) - 2,2,6,6-te- <sub>gg</sub> tr amet-4-piperidyloxy) - diphenylmethane-1, bile- (1,2,2,6,0-pentamethyl-4Hpiperidiniyl) caronate, bis-1,2,2,6,6-pemtaimotyl-4-piperidine oxalate. il), bis- (il, 2, 2, 6,6-pen'taimethyl-4-! pIipei'idÎmil) malonate, a- <sub>60 </sub>bis- (1,2,2,6,6-pentaimethyl-4-piperidiniyl) diabate, bis- (1,2,2,6,6-pentamethyl-4-ipiperildinyl) sebacate, bis- (1) fuimarate ,2,
2,6,6 Hpemtaim ethyl-4- pipe.ridm.il), isophthalate bis- (1,2,2,6,6-) pentamethyl-4-pi, peridinyl), <sup>65</sup> cyblohexane-1,4'-di.carboxi] atulul bis- (1,2,
2.6.6- pentamethyl-4-piperidines), bis - (], 2,2,6,6-pentamethyl-4-pipe <redine) thiopropionate, bis- (1,2,6,6,6) methyl brimesate - β-pentamethyl-4-piperidinyl), bis (1-n-prapyl-2,2,6,6-tetramethyl-4-piperidinyl) adipate, bis- (1-eec-bulyl-2,2) succinate, 6,6-tetramethyl-4-piperidinyl), b (s) (ln-octyl-2,2,6,6-tetramethyl-lspiperidiniyl), bis- (ln-dadecyl-2,2,6,6-tetraimethyl) adipate -4-piperi) dinyl), bis- (1-noctadecyl-2,2,6,6-tetramethyl M-piperidiml) sebacate, bis- (1-allyl-2,2,6,6-letramelyl-4-piperidinyl) adipate, thiophan-2 ', 5'-bis-(1-allyl-2,2,6,6-tetramethyl) dicarboxylate -I-piperldinyl), bis- (1-ol-2,2,6,6-letramethyl-4-pi'peridinyl) thiothiylpropionab, bis- (lpropargiyl-2,2,6,6-tetramethyl-4) sebacate -piperidinyl), bi'S- (i-ben.zyl) 2,2,6,6-tefcyla-4-piperildiniyl sebacate, bis- [1- (2-hydroxyethyl) adipate - 2,2,6,6-tetramethyl; 4-pi> peridiin] nyl], bis- [1- (2'-chloropO; pil) -2,]
2.6.6-tetramethyl-4-pi<sup>|</sup>peri-dinyl), bis-[1- (2'-dia, netyl) - 2,2,6,6-tetramethyl-4- I piperidinyl] sebacate, biiS- [1- (2 ') acetate , 3'-eipoxypropyl) -2,2,6,6 - tetramethyl-4-piperidinyl], pimelate of bis- [1 (2)<sup>T</sup>-methoxyethyl) -2,2,6,6-tetramethyl-4-piperidinyl], bis-glutarate, [1- (2'-acetoxyethi, 1) -2,2,6,6-tetramethyl-4- pi- '1 peridinyl], bis-] 1- (2'-methyl-? caiibampiyloxyethyl) -2,2,6,6-tetramethyl-4-pi- 1 peridinyl] malonate, biis- [-1- ( methylcar- j.
bonylmethyl) -2,2,6,6 - tetramethyl-4-ipiiperiid.
nyl], bis- (1-carbamoyloxymethyl-2,2,6,6-tetramethyl-4-piperidinyl) cyclohexane-1'-dicarboxylate, bis- [1- (methylicarbamoylethyl) -2-thiopropionate)<sub>(</sub>6,6-tetylamethyl-4-piperidyl], bis- (1-acetyl-2,2) sebacate
6.6- tetraimethyl-4-pilperidintl), the swine <sup>;</sup> bis - '(star! roil-2,2,6,6 - teitramethyl-1-pipe-) ridinyl), dodecanidiioab of bis- (l-benzoyl2.2.6.6- tetra, methyl-i-! piperidinyl) , the adipate of bie- (1-methyl-blyl-2,2,6,6-tetramcyl.piperidime), bis-1-phenylthio isophthalate. carbamoyl-2,2,6,6-tetramethyl-4-piperidyl), ethan-Γ, 2'-bis ~ (4-carbamoyloxy-1,2,2,6,6-pentamethylpiperi'dine), hexane-l ', 6 '-bi »s- (4-carbamoyloxy'yl, 2,2,6,6-pentamethylpiperidine, 2', 4<sup>,</sup>, 4'-trImethylhexan-r, 6 '- bi's- (4'carbam.oiloxb-1,2,2,6,6-pentamethylipiperidine), cyclohoxane-1'-3'-bis- (eai'baimoyloxy-1,
2.2.6.6-ipentamethylpiperidine), benzene-1 ', 4'-bis-1-carbamoyloxy - 1,2,2,6,6-dpentamethyl] pipcridine), toluene-2', 4'-bis- (4-carbamoyloxy) 1,2,2,6,6-pentamethylpiperidine), toluene 2 ', 4'-bis- (4-iiocarbamoyloxy - 1,2,2,6,6-ipen- and tamethylpiperidine), nasal acid - Γ, 5Ά> ιβ- (4-carbamoyl-OXI-1,2,2,6,6 - «pentamethylpiperidine), toluene-2 ', 4'-bis- (4-4-carbaim.olloxi-1-ipr-oipyl-2, .2,6 , 6-itetrame'thiylpiperidine), hexam-r, 6 '- .bîs - ^ - carbamorloxy-ln-butyl · ^,
2,6,6 - tetramethylpiperiidine), hexane-Γ, 6'- <sup>:</sup> bis- (4-carba.moyloxy-4-n-Cyctyl-2,2,6,6-tetramethylpiperdiidine), 2 ', 4<sup>it</sup>, 4'-trim.eitilhexan-.r,, |
6'-bis - (4-Ca''bamoyl-oxy-1-octadecyl-2,2)<sub>J</sub>6,
6457,3
6, -teteame'tiilplperidine), cyclohexane-Γ, 4'bis- (4-carbamoyloxy- 1-ayl., 2, 2, 2, 6, 6-fold tilpdlpenidyl), 2 ', 4', 4 '-trimethylhexane - Γ, 6 bis- (4-yl-arbaimoyloxy-1,1-allyl-2,2,6,6-tetraimethylplperidene), benzene-1 ', 4'-bis- (4-carbamoyloxy-1-propargyl-2,2) , 6,6-tet-tramethylpiperidine), tol'uen-2 ', 4'-bis - (4-: carbamoyl-alkoxy-2-yl2-2)<sub>f</sub>2,6,6-tetraimeti4piperÎidin, a), to'luen2 '', 4- [4-carbamoyloxy - 1- (2'-h5droxy; il) - 2,
2.6.6- tetramethylpiperidine], dilfeniijmethane ', 4-bliis - [4- oairbamoyloxy -1 - (2' - ci'ane til) 2,2,6,
6-tetraimethylpiperiddiine], toluene-2 ', 4' '- bi8 [4-caibyloxyoxy-1- (2' '- acetoxyethyl) - 2,2,6,6-tetramethylpiperiperidine, ethane-1', 2'-bis (4-way · Ββιιηο-ίΙιΟχΙ-.Ι-ηΐθΐίΙεβΛοηΐιΙηΐΐίΙίίΙ - 2,2,6,6-ii.etrameMpiiperidine '), hexane-l', 6-biK- [4-icarbamoyloxy-1 (2'-melylOairbarooiil ) - 2,2,6,6tetramethylpipei'idinate, naphthalene-1 ', 5<sup>r</sup>-his- (4cai'bamoiloxj-l-nce! sl - 2,2,6,6-tetramefiljpjperiidine), 2 ', 4'; 4 '-! triimeti'Ihex-an-l<sup>,</sup>, 6'-bi8- (4-carbamoyloxy-1-searoyl - 2,2,6,6-leitramethylpiperadine), hexane-1 ', 6' -bis- (4-'caa'baimoiL · oxy-l-meÎ.iilic : ai'bamoyl-2,2,6,6 - tetr-ametUpiperiidine) and bis- (1,2,2,6,6-pentaime, till-4-pipedidinyl) - ether.
if the symbol is not equal to the following examples of substances are given: nitrilotriiacetate of trils- (1,2,2,6,6-penitamebil-4-ipiperidinyl), trils- triearbailylate- (1,2,2,6,6-pentaan.ethyl-4-, pcip ss i'dinyl) , The tnis- (1,2,6,6,6Hp. Embamethyl-4-piperidinyl) mesylate, the t> ris- (1,2,2,6,6pentarnebil-d-piperidinyl) mesylate, the triphyrite ( 1,2,2,6,6-pentamethyl-1-piperidiinyl), triis- (1,2,2,6,6-pentamethyl-4-piperidine), tris-borate, 2 2,6,6-pentamethyl-4-piperidinyl) trimisab-tris- (ln-ocbaidecyl) 2,2,6,6-ite tramethyl-4-iplperldinyl), f osfitui. of trife- (1-allyl-2,2,6,6-tetyramethyl-4-pipeylidyryl-1), borate of triB- (1-ipyropargyl-2,2,6,6-tetr, amdtil-4-piperidines! i), tris (trimethyl-2,2,6,6-tetramethyl-4-piperidinyl) trimethylate of tris- [1- (2'-hydroxyethyl) -2,2,6,6-tetramethyl-4-pipeniidinyl trimethylate ), the phosphorus-of the tunnels [1- (2'-cyanethyl-1) - 2,2,6,6-tetrames: til-4-piperidini'l], the borate of tris- (1-acetates, l-2,2 , 6,6-tetramethyl-4-piperine) and tris- (1H-methylcarbamoyl-2,2,6,6-tetramelyl-4-piperate, idinyl) trimates.
In this case, the symbol is not equal to the following examples of substances: tetra-cis- (1,2,6,6-peatametiM-pipecidinill) ethylene, tetra-cis-carboxylate, tetra-cis- pyromelite, il, 2,2,6,6-pentamethyl-4-piperidinyl), o-ish / tetracis- (1, 2,2,6,6-pentamethyl)<sup>and</sup>l-4-piper'idinyl), tetra-cyB- (ln-oethyl-2,2,6,6-tetranethyl-4-, pi) pyridinyl) pyrrole-eylatate, tetra-cis-1-allyl hyperamelity ^^ Ae - tetramethyl ether (piperidi iniyl), tetra-α-ae- (1-propargyl-2,2,6,6-tetramethyl-4-piperiidinyl), ethyl-end-iaminotetracarboxylaib tet-a-siliicate eits- (lbenzyl-2,2,6,6-tetramethyl-4-piperidinyl), tetra-oxylylate, α-cis- [1- (2'-hydroxy, rcipoxy) 2.2.6.6-ietramatyl-4-piperiddinyl, tetraHtis- (ls-tearoi-l-2,2,6,6-tetra28 methyl-4-piper®dmil) pyrethrinelite and tetracis- (l-phenylcarbamoyl-2,2) o-silicate<sub>)</sub>6<sub>)</sub>6-tetr.ameiJil-4-piperidinyl).
From the compounds of the general formula I, salts can be prepared, for example, salts with inorganic acids - o phosphates, carbonates, sulphates and chlorides, as well as salts with organic acids such as acetates, stearates, maleats, olites, tartarates, oxalates, benzoates and salts of substituted cairbami acids.
Examples of salts include: mono- (4-n-butoxy-1-phosphate),
2.2.6.6- pen.taim & fcpperpyridine), hydrochloride hydrochloride, 2,2,6,6-pentamethylpiip'eridine, sebaioato-sulphate of biis- (1,2,2,6,6 pentamethyl-piperidiin yl) , beta- (3 ', 5' - d-iterert-buttl-4 '_ hiidr-oxifeml) - 1,2,2,6,6-pentameidyl-4-piperiidiniyl acetate, 4-methylicairbaim acetate -oiiioxi-1,
2.2.6.6- ipentamethylpiperidine-, the sitate aerate
1,6- ibffs- (4'-caribamoyloxy - Ι '^' ^ ', δ', β'-ρεηtamethylip-iperiidin) -hexane, 4-phenyl-carbamoyl benzoate-xi-1,2,2,6,6 - pentaimethylp- hyperidine, 1,2,2,6,6-penta n-oiotanoa-bul • methyl-4-piperiidinyl, 3 ', 5' - di-tert-butyl-4 '-hydroxybenzoyl 1,2,2 , 6,6-pen, tamatil-4pipeiiidini-l, 1,4-bis- (l ', - 2', 2 ', 6 acid oxalate)<sup>[</sup>, 6'-penitamethyl-4'-piperIdyloxy) - butane, the burning compound of 4 - (2'-eianetQ 'i) -l, 2,2,6,6pentaimieiti-ipiiperiides, the titrate of 4-stearylcarbamoyloxy-1 , 2, -2,6,6 - pentamefcilipiperiidine, n-octane-Oiatottai'tratull of (2'-hydroxyethyl) -2,2,6,6-itetrameethyl-4-piipeyridinyl, d-ylbutylcarbamate benzoate of 1, 2,2,6,6-ipent dizziness- 4-piperidine 1.
The symbol R, or the symbol R 1 may be represented by a monovalent, bivalent or trivalent radcal obtained by removing a number of from 1 to 3 hydroxy groups from a sulphonic, sulphine, disulfonic acid, from an ati (d which contains phosphorus or boron-ilc acid.
Examples of such compounds in which n is 1 are: benzenesulfonate of 1,2,2,
6.6- (tethamethylipipeTidinyl- (4), benzene hydrochloride 1,2,2,6,6-hypentaimethylpiperiyliniyl X4), methylsulfate I, 2,2,6,6Hpenitaimebilpi (peri<sup>:</sup>din- (4), the 1,2,2,6,6-per-methyl ethylpiipetidine I- (4), phenylphosphonite of 1,
2.2.6.6- pentamethylpiperiidinyl- (4), 1,2,2,6,6-pentamethylpiipetridiiniyl diphenyl (4), 1,2,2,6,6-hypentamephiolipipiidinyl (4) diphosphate.
Compounds in which n is 2 are: bisis- (1,2,2,6,6-p entamethyl-4-piip ertdin.il) sulphate, bisis phosphonalt- (1,2,2,6,6-penit .methyl-4'-piperidiinjil), bis- (1,2,2,6,6pentam phenylphosphate, ethyl-4-pipeyl), benzene-1,3-di9-bisulfinate (1,2) 2,6, G-pentametiil-d-piperidinyl).
Also, compounds of this genus in which n is 3 are: be-nzen-1, 3,5-trisulfo-natu-i of -tr.is- (1,2,2,6,6-pentamethyl-4-piperidinyl) and benzene, 3,5-tniis<sup>and</sup>ulcerated yeast (1,2,6,6,6-pentamethyl-4-piperidinyl).
6457®
A preferred subgroup of compounds of general formula I comprises those compounds of formula Ia:
4-dithyl-1-naphthyl, 4-igopropylH-naphthyl, 4-tert-butyl-1-yl or a group of the formula:
CHj CH<sub>3</sub> \ dd
Y — N \ __
Z \ _CII, CH.,
H
O- C (Ia) —Oiz \
\ z
N-CHj _Z Z \ ni wherein Y represents an alkyl group egg 1. 20 carbon atoms and preferably with 1 ... 4 carbon atoms, an ischemic group with 3 ... 20 carbon atoms or an aralkyl group, which preferably has 7 ... 9 carbon atoms, and m has the value 1 or 2, when m is equal to egg 1, R represents a hydrogen atom, a monovalent aliphatic residue and 1 to 20 carbon atoms, a monovalent other residue and 5 to 12 carbon atoms or one east. monovalent aromatic with 6 ... 20 carbon atoms or a group egg formula:
Particularly preferred substituents for the R symbol sine above groups with 6 ... 20 carbon atoms, as well as the group;
Rn —O— ch<sub>3</sub> ch<sub>3 </sub>\/
------.<sub>x</sub>
N — Y ___Z z \
CH<sub>3</sub> CHj and when equals egg 2, R represents a bivalent aliphatic residue I 1. .. 35 carbon atoms, a bivalent alicyclic residue with 5 ... 12 carbon atoms or a bivalent aromatic residue with 6 ... 14 carbon atoms,
When m is equal to 1, R can 40-spray a hydrogen atom or one of the methyl, ethyl, η-propyl, isoproipyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, 2- groups. eiti) llproipdl, 2-methylbutyl, n-hexyl, 2-methylpenityl, n-heptyl, 2-ethyl lpenitSl, π-ofctil, 45 2,2,4-thyrilmyl |<sup>,</sup>l, n-deciyl, n-undec.il, ntradecâl, n-pe> ffitaidecil, n-heptadecyl, n-eicosiil, vinyl, allfa-meitilvlnal, beta-methylvlmil, deoen-9-il, heptedecen-8-il, betta-methylthioelthyl, beta-oictiylthioethyl, beta-dodecalltio- 50 ethyl, oiclopentyl, oiiclohexyl, cyclohexen-3-yl, meithylohexyl, teiȚ-tultiMelohexyl, cyclododeicil, l-perhydronephtyl, 2-penylethyl, , (perhddronfialtil) - 55 methyl, 2- (perhydronaphthyl) methyl, beta- (1-pyrrhionyl) - ethyl, beita- (2-hyperhydroxy.aftyl) - 'ethylphenyl, benzyl, batanfemyls til, heta-phenylvinyl, l-Ulyphtylimieityl, 2-naphthylimates<sup>it</sup>1, beta- (1-methyl) ethyl, beta- (2-natal) -ethyl, phenyl, o-tolyl, p-to- <sup>60 </sup>lil, o-ethylphenyl, -m-elyl-phenyl, p-eite, l-phenyl, 0-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, o-tert-butylphenyl, m-tert-butylphentyl, p-tert-butylphenyl, p-tert-butylphenyl, -1-naphthyl, 65
R11 wherein R10 and Rn are the same or different and each represents an alkyl group of egg 1 ... 6 carbon atoms, such as methyl, eiti.1, n-; proptl, isopropyl, sec-butyl, tert-bubyl groups , tert-pentyl, (1,1-dime.thalpropyl), tert-hexiyl, (l, l-idiim'ethyl! butyl) and preferably the methyl, iso-propyl or tert-butyl groups, the symbol A represents a group - CH2 -, a group — CH<sub>2</sub>----- CH2-, again
I
That the symbol m is 0 or 1.
Atone when we are equal to 2, R can represent one of the methylene, 1,2-ethylene, 1,4-n-buitylene, 1,8-n-ootylene, 2,2,4-trimelthiyl-1,4-biu groups thalen, l, 10-n-so, len, 1,2-eicosylene, vinylene, propenylene, 1,2-oiclohexylene, 1,3-cyclohexd.lane, 1,4-cfclohexylene, cyclohexyl-3-en, 1 , 2-phenylene, 1,3-phenylene, 1,4-phenylene, p-xithylien, 1,4-n-typhon, 1,5-naphthylene, diphenylene or diphenylmethylem.
Another preferred subgroup of compounds of general formula I comprises compounds of formula lb:
CHj CH, \ Z_
Υ, -Ν <sub>/ χ</sub> > - fe _ CH<sub>3</sub> CH, O _ <sub>q</sub> wherein Y 1 represents an alkyl group with 1 ... 12 carbon atoms, an alchemyl group with 3 ... 12 carbon atoms, or an aralkyl group with 7 ... 9 carbon atoms, and Ria represents an atoms of hydrogen, an alkyl or alkylene ring having a maximum of 20 carbon atoms, an alkyl group substituted by the formula:
- (CH?) M —CH — X<sub>3</sub> or —CH — X.,
II
R'4 R4 \ z<sup>H</sup>
645 713 wherein m is equal to 1, 2 or 3, RJ represents a hydrogen atom or a group (methyl, Xi represents a halogen atom or a methoxy group, and X2 a haloogen moiety, an alkenyl or alkenylene group with a maximum of 20. carbon atoms, a cycloalkyl or etholohealkyl group having 5 to 12 carbonyl amides or an aryl or anylene group having 6 to 12 carbon atoms, q being 1 or 2.
When q is equal to 1, R12 may represent a hydrogen atom or one of the groups meltil, ethyl, nspropyl, isopropyl, n-butyl, sec-buitdll, tert-butyl, n-pentdl, 2-ethylpropll, 2 -methylbutyl, n-hexyl, 2-methylpenityl, n4-ethyl, 2-ylethylipentyl, n-octyl, Sseitiihexyl, 2,2,4-trlmeJtitlpentyl, n-decyl, ndoldecti, n-tetrahydrecyl, n-odtaldehyde, eicosil , mesothiol, allyl, olail, aylcopeinyl, cyclohexyl, meUMtlohexyl, tertri-tertoylidlohexyl, tertoctilcylcyclohexyl, cyclodadecyl, l-perhydronaphthyl, 2-pihyldihydronaphthyl, adaimantyl, eielopentylmethyl, cyclohexiflmel'l, beta-eielhexylethyl, benzyl, belta-phenylethyl, l-nalEthyymethyl, 2-naphthylimeifyl, belta-lithium-naphthyl-beethyl,<sup>!</sup>ta- (2-naphtha ·!) ethyl, phenyl, o-tolyl, m-tolyl, p-toli'l, 2,4-xylyl, 2,6-xylyl, ρ-chlorophenyl, 3-clnrHp-tolyl, 0-ethylphemyl ], p-tert-buJIi''ifen <i. '!, 2,3 ^ dichlorfeml, SS ^ dUdlor'îenyl, alfamafitil, beta-naphthyl, phenylenyl.
Then, when q is equal to 2, R12 may represent one of the methylene groups,
1,2-ethylene, 1,4-n-butylene, 1,6-, n-bexylene, 1,8ntectylene, 2,4,4-trimethyl-1,6-hexylene, 1,10n-decylene, 1,2-eicolsylene , 1,2-eicoseniien,
1,3-Cidlohexilein, 1,4-Cidto'hexylene, 1,3-Phenylene, 1,4-Fetylene, 2,4-Foluylene, 1,5-Naphthylene, 4,4'ediylpheinrlen, 4,4'- <Uphenylimfiibiylene, 3,3'-dimiefcil-4,4 '-difernl! in, 3.3 '-dilm ethyl-4.4'<sup>J</sup>diff and niimeftiten.
As examples of Yi substituents of formula Ib, mention should be made of the groups meltil, ethyl, 11-propyl, isopropyl, n-butyl, sec-butyl, η-hexiyl, n-octyl, n-dodecyl, allyl, alpha-. metalill, 10 units, eoeinyl, benzyl, α-methylbenzenyl, p-imethylbenzene 1, pam-eethyl-alpha a-methyl benzyl, alpha-naphthylmethyl. Preferred is the linear or branched alkyl groups, egg 1-4 carbon atom.
Another group of compounds included in the general formula I are those in which, when kennel the symbol n is equal to 1, R j represents an alkyl group of 1. 20 carbon atoms, one group of 5-, 12-membered carbon atoms, one alkenyl group or 3-alkenyl group. 20 carbon atoms, an aralkyl group have 7 ... 12 carbon atoms or a raldylalkyl egg formula:
R-4, wherein m represents 1, 2 or 3, R 1 a hydrogen atom, a methyl or a phenyl group, X 2 a re-expressed halogen atom, a one-year group or a -CH-CH group<sub>:</sub>>, \/
OR —CORs, —CO — OR., —COCO SR<sub>5</sub> or —coNfofo, i<sub>you</sub>Symbol X1 represents a hydroxyl group, a halogen atom, a
<td>cyan group,</td><td>or 0 group</td><td>- ORs, —OCR5. II A</td>
<td>-OCR5, II</td><td>s Rs -OCN < II r<sub>6</sub></td><td>/ R5 - OCN <, It's fake</td>
<td>s</td><td> 0</td><td>S</td>
<td>, - cr<sub>5</sub></td><td>-qofo,</td><td>-CSR ;,</td>
<td>II</td><td>II</td><td>II</td>
<td> 0</td><td> 0</td><td> 0</td>
wherein Rs represents an alkyl self
1 ... 20 carbon atoms, alkenyl, with 2. 20 carbon atoms, 5 to 12 carbon atoms, 6 to 11 carbon atoms, or 7 to 14 carbon aralkyl atoms, to have one hydrogen atom, then • when d is bonded to a nitrogen atom, and Ib represents a hydrogen atom or an alkyl group of 1 ... 4 carbon atoms, sa, u Rs and -Re together with the die nitrogen atom to which they are linked form a 5- or 6-membered ring, which possibly still contains one or more many heteroatoms, the R3 symbol may represent an aryl group or a residue with the formula:
ch<sub>3</sub> cir \ z \ ____ / / \ ch<sub>3</sub> ch<sub>3</sub> in oafs R 1 represents hydrogen or has the signi fi cance of R 1; when n equals egg 2, R3 represents an alkylene group egg 1 ... 20 carbon atoms, alchemy n eu 2 ... 20 carbon atoms, 2 alkyl carbonyl ... 20 carbon atoms, oichloalkyl ketylene
3 ... 12 carbon atoms, arylene with 6,. . 14 carbon atoms or 8 acaicylenes, 14 carbon atoms, and al / one when n equals 3, R<sub>3</sub> represents an alkyl group 41, arentriyl or arylthiylalkyl group and when n is equal to 4, R3 represents a tetravalent moiety, for example an allyl group.
Another group of compounds of the general formula I are those where, when n is equal to egg 1, R 3 represents an acyl group and the formula - CO - R?, In which R? represents hydrogen, an aliphatic residue unsubstituted or substituted by 1-20 carbon atoms, an alhenhenyl or alkynyl group with
2, 20 carbon atoms, one cyclopaliphatic residue, 5 to 12 carbon atoms, one arallifaltto residue with 7-14 carbon atoms, one aromatic residue, 6. 20. Carbon atoms, a heiteirocyclic residue or a moinovalent moiety obtained by removing a hydroxyl group from a sulfinic, sulfonic acid, an allyl phosphorus or boric acid; then dud n is equal to me 2, R 1 represents a bivalent radical ur of the type of a diacyl radical union of another, aromatic or iiericocyclic; ·, o. group — CO, o <sub>:</sub> group -CO-CO-, a sulfinyl, sulfosyl group or a bivalent moiety by the removal of two hydroxyl groups from one. disulfonic acid, d.inl.v-an .adid. of phosphorus. or from boric acid; then when n is equal to egg 3, R3 does not represent a trivalent residue of the type of an aliphatic or aromatic triacyl radius or of a radiated radiate. orphanophosphoric acid, orthophosphorous or ontoborchic acid; then cinnamon n equals egg 4, R1 represents a tetravalent residue of the type of a trachea group, which comes from a teltauoanboxylylc acid or aromatic acid or aromatic silicate.
Another group of compounds of the general formula I are those in which n is equal to 1 or 2 and when n is equal to 1, R 1 represents a carbamoyl group of the formula:
Rs \) N — c—
Rto I!
one and then when there is not equal to 2, R1 represents an aliphatic dicanhaimoll group. or bivalent aromatics.
An alternate group of compounds are those in which n is equal to 1 or 2 and when n is equal to egg 1, R 1 represents a thioeairbaimioyl group with the formula:
s and when the egg is equal to 2, R 1 represents a dithiocarbyl group or aliphatic or bivalent aromatic group.
As can be seen from the examples, the process consists in the addition of a piperidimol of general formula II, with an acid halide or general formula III in the presence of an alioceptor. Organic bases, such as tretylamine, may be mentioned in accepting suitable acids, or excess amine may be used with general form II.
The reaction is carried out in the appropriate medium by heating the reagent in a solvent such as cyclohexane, benzene or tofeion, which are inert under the reaction conditions. After completion of the reaction, the desired reaction product is separated by methods. known.
Compounds of general formula I confer po<sup>;</sup>Mephita! Eloir has a very high stability against the damage normally caused by the effects of ultraviolet light or by exposure to heat, without worsening the color of the polyolefin treated. Sabilizers prepared according to the present invention provide. o .comprehensive stability towards action, light and Asa. a ·. heat ,. May. chosen for low density polyethylene, wall density * polyethylene, polypropylene and poWtiiren, praaum and..for.the basic polymers of .l-bultesna, l-pemtem, 3-methl-l-butene, 1-hexene, .. α-methyl-itopeiritene, α-methyl-1-hexene and 4.4<sup>j</sup>dilmieti4-l «penit) ence and the copolymers and polymers · ternary, based on .olefiins, millet chosen on the basis of ethylene or pnopethylene.
Other. organic products liable to be 'degraded under the action of luirmnih and thus whose properties are improved by incorporating in these products a campus with the general I onu I, natural polymers and symmetry, oum., being, for example, natural rubber and synthetic rubbers, the latter including, for example, homopolysilane, ternary oopolhners and polymers based on acrylic, butadiene and styrene. as specific synthetic poMrners. mention may be made of vinyl chloride, vininidide polyolide, vinyl chloride copolymer, vinyl polyacetate, polymers formed by condensation from ethers, from esifcers (from carboxylic, sulfonic or carbonic acids), from amide or urethane. These polymers can be oonistituted, for example the basic material for coating agents, such as paints and varnishes, they contain an oil or a resin, such as alkyd or polyamide resins.
Each song of compound of general formula I, is embedded in the organic product, in order to achieve maximum protection against degradation under the action of light, varies depending on the properties of the treated organic product, the intensity of the light radiation and the duration of exposure. However, for the majority of purposes, it is sufficient to use between 0.01¼ mass and 5% mass, preferably between 0.1% mass and 2% mass, given at the mass of the otiigamc product neto t.
Compounds I of the general formula I may be incorporated into the polymer by any of the cuntoiadube processes for incorporating the additives into a polymer,<sup>1</sup> Thus, - for example, the compound may be mixed with the polymer in a mixer, or the sprayed polymer may be treated with the compound prepared according to the invention, either in the form of a solution or suspension. In 64573 with a suitable solvent or a suitable dispensing agent, for example, an inert organic solvent such as meibanol, ethane was acetone, the mixture was homogenized and formed perfectly into a gasket, and the thinning solvent subsequently, or the compound prepared according to the invention may be incorporated into the polymer during the latter's production, for example, at the moment the polymer is in the latex stage, in order to obtain a pnesitalized polymer.
In the oasis where this is desired, the stalbilliea composition may contain one or more additives, especially those used in mixtures based on polymers, such as antioxidants, such as phenols or amines, radiation absorption agents · ultraviolet , opoopoifuwa lightening agents, phosphite-based stabilizers, peroxia decay agents, polyamide stabilizers, costalbilization of the base, stabilizers for vinyl polychloride, plasticizers, lubricants, emulgatonia, anitdstation agents, .ignificant agents, pigments, carbon black, asbestos, glass fibers, kaolin and talc.
As examples of suitable amyto-oxidants, mention may be made of masked phenloiltic anitioxides, such as, for example, compounds of the form:
O- (CH<sub>2</sub>) w —A, where Q 'represents a group or formula:
R
Ai represents a group -OR (COOR) j or a gnome
COOR
I - C- (CH<sub>2J</sub>)<sub>w</sub>-QI
COOR
R represents a hydrogen atom or a lower alkyl group, R<sup>!</sup> represents a lower alkyl group, R represents an alkyl group of 6 ... 24 carbon atoms, w represents an integer between 0 and 4. As examples we can mention: aha- (3,5-dii-tertiary -butyl-4-had: rioxibenizyl) di-n-ocltadcdyl halonate, di-n-ootadecll alphalonate, alpha, alpha'-bis- (3 (3-tert-ibutyl-4-hydroxy-5-methylbenzyl) - butyl material (4-hydroxy-5-methylbenzyl) - dli-n-octadecal malonate.
Other phenol compounds of formula Q — R. as examples, they can be mentioned<sup>36</sup>
2,6-dihydro-butyl-p-icrezole, 2H-methyl-4,6-diitert-butylphenol], 2,6-idl-Oidtadeoyl-jp - criezol, etc.
Also, they are compounds of the Q-C form<sub>w</sub>H<sub>2w</sub>—Q, oa, for example, 2,2'-imelthylene-biis- (d-tert -but biyl-4-imethylphen'ol 1), 2,2'-methylene-bis- (6-tert-butyl-4) (ethyl enol), 4, 4 '-bubi'liden-biis- ^, 6-ds - toro-butylphenol), 4, 4' - (2-butylidene) -bis - (2-ylter-butyl-5 -m<sup>it</sup>ethylphereol), 2,2'-methyl-bis-Jd- (2-tert-methylclohexyl) -4-methylphenol], 2,2'-smethylene-his (3-tert-butyl - S-ethylphenol), 4 , 4 '- methylenbis-tert -butyl-butyl-S -methylphenol), 2,2'-methyl-bis- (3-tert-butyl-5-methylphemoyl), etc.,
Other phenolic compounds of the formula R — O — Q, such as, for example, 2,5-d-D-tert-butylhydroxyquinone, 2,6-tert-butylhydrohequinone, and 2,5-di-tert-butyl-4-hydroxyyanisole or the like have Q —S — Q, for example, J ^ -t'io-bite-ia-.tert-ibutyl-S-mebiifenol), 4 / - 110-6118- (2-16 .: / - 13, .1111- 0-01 ^ 1,) 111-0.0.1 ul), 2,2 '-thio-bis- (6-tert -butyl- 4-methylphenol), 4,4'-thio-bis- (2- methyl-5-tert -bufilf emol).
Phenolic compounds of formula:
a
II
O- (CH<sub>2</sub>) S— (CH<sub>2</sub>) IT — C — OR.
as an example we can mention: (3,5-ιΐίΓηοΙΐ1-4-1 · ιίιάυοχ · ί, Ιθθηζί1Ιιίο) -ι, ι, οθ (η1; ι.ι1 of octadecyl and (3,5-dt-Èerț-butâ l-4-hydroxybis [nziitiio) -dopodyl propionate.
The phenolic compounds of the formula:
<sup>H</sup>\ /<sup>Q</sup>
CH- (CwHsw) —CH may be mentioned: l, l, 3Htriis- (3,5-thimethyl-4-hydroxyphenyl) -propane, 1,1,3-triis - (5-tert-butyl-4-hydroxy-2-methyl ennl) - butane, 1,1, 5,5dte'tra-oiis - (3'-tert -butyl-4'-hydroxy-6'me! typhenyl) "n.-ipen) tan.
From the phenolic compounds egg formula: CH<sub>3> x</sub> qch<sub>2</sub> - </// —ch<sub>2</sub>b<sub>2 </sub>ch / <sup>x</sup> ch<sub>2</sub>c, wherein the symbols Bi, Eh and Eh represent hydrogen atoms or methyl groups or take the same meaning egg Q, provided that when Bi and Bi have meanings identical to Q, B> - they represent a hydrogen atom or a group put it and a tuna when B<sub>2</sub> has meanings identical to Q, the symbols Bl and Bj to represent hydrogen atoms or methyl groups, the mention of: l, 4 ^ di- (3,58dÎ-: te, Îț-butyl-4-hi, dîOxibenziil) - 2, 3,5,6-tetramen tilhenzene, 1,3,5646713
3ί tri-3,3,5-idÎHterț-! ButiilM4-iliiiÎdroxdibenzii) - 2,4, 6-WmeiUdlbenzeiiUil.
Other useful compounds have the formula:
(4-hiiidlrioxy; -3,5 - jdilHterț-buHalfeiîOixâ) -6- (n · idodecffiioeitiiitiio) -1,3,54ni> a3itn | a.
Other phenolic compounds have the formula:
z \
I NI II
Q — HN '<sup>Z</sup>'^ N'<sup>/</sup>'<sup>X</sup> wherein Z represents a group -NHQ, a group -S-D or a group -O-Q, D represents an alkyl ignipous with 6 ... 12 ion atoms or a group - (C,<sub>v</sub> H<sub>aw</sub>) —S — R, In the examples given, the following may be mentioned: 2,4-b ^ (n-Odtttfbo) - 6 -> (3,5-, di-tert-butyl-4-hydroxydioxyl)> -; l, 3, 5-toiazrina, 6 ~ (4- hildroxy3-im (etijl-5-iterțr-, buitiÎan) lli'nio) -3,4-biis - (n-octdiltli | o) -fl, 3, '5- rMaiZÎInia, 6<sup>j</sup>(4-hddroxy-3,5-ddme tilanilino) -2,4-bis - (n.-OQtylthio) -l, 3,5-itriazma, 6- (4-hydroxy-3,5-di-tert-) butylunilino) - 2,4hiis-tn-otetiiiLliiioJ-ibB ^ -itiriiazi.na, 6- (4-hii | droxi3,5Hdâ! -. tjeirț-hu! tiillainiSlitniD) -4-i (4 - hi | droxi-3, 5di-iterert-buitillphenioxy) - 2 - • (n-oictiylthio) -1,3,5-thiazilnia and 2,44biis- (4-hlIdroÎxi-3<sub>)</sub>5-idii-t0rţ-! BUrtilanbliMo) -6- (n-iaatilrtto) 4,3,5-fbraizina.
Also, phenloyl compounds of formula:
Z '
I z \, NN
Q — O / 9<sub>N</sub>Z \ in the cane Z 'represents a group -O-Q, a group -S-D or a group -S- (C<sub>w</sub>H<sub>2w</sub>) -SD. 40
Examples include: 2,3-bis- (3,5-di-tert-butyl-4-hydroxyphen! Oxy) -6- (n-octylthio) -1,3,5-fcriazine, 2,4,6-tri- (4-hydroxy) -3,5-diifcețrț-buÎiifenoxy) -1,3,5-thiazdna ·, 6- (4-hii | dno xi-3,5-di-tert ^ butfflphenioxy) -2,4-his - :( n- oidti, l-45 tioetiimo) -l, SS-fcriatzinla, 6- (4-hydroxy-3-onetLlfcnoxi) - 2,44Μ3- (η-οο1ΐ11ΐο) -4, · 3,5-ιΐϊ · Ϊ9 · ,na, 6 - (4-4u | diroxy-3-tert - bultylphenioxy) -2,4 bjfe -. (N-ocOlto0tilltoo) -l, 3 ^ -4oaEina, 6- (4-hydroxy-S-tethyl-S-'tetabiiIthiylphenoxy) - 2,4-taiis- 50 (no: etdiMo) -4,3,5-frişriaia, 2,4-ibis- (4-hi (droxy ^ S-methyl-S-beirtt-bultylphenoxy-6- (01-oicylthio'o) -1,3,5-ibriilazinia, 2,4-to- (4-<sup>,</sup>hydroxy-3-m ethyl-5 <sup>J</sup>tert -bultiylphenoxy) -l, 3,5-triazine,, 6- (4-hydroxy-3,5-Jdl-iterythi-beithiylphenoxy) - 2,4-bis- 55 (n-ootyltopropyl) lt4o) -yl, 3, i5 -trdiazinla, 6- (4-hi- -droxide-S-di-tert-butylphenX'i) - 2,4-bis- (ndoide'cÎ3Jt! ioetiilfcio) -l, 3,5-thyriazinine, 2,4- bils- (4-hydroxy-3, S-dd-tert -bultftiifenioxy-e-'b'utiilltito1,3,5-toizine, 2,4-ibtis- (4-hydroxide-roxb3,5-di-t'e (rt - <sub>M </sub>bultiiJÎenjoxiQ-e-fnHpcitladlefcdiltio) - 1,3,5-triiazirna, '2,4-biB- (4-h (idmoxN3, S-idi-'beirț-Mbutilfe'noxil) -6- (n-idddeciltdo ·) - l, 3,5-trâa0in.a ·, 2,4bi, s- (4-ihlihydroxy-3,5-oxy-torch - buitdlfenox'i) -6 (n-iodt'iiltioptio | p! iÎ] Itiio) - il, 3,5-itiriia0In, 2,4-bis- 65 (Q-Cz Haz —COO — Qz H 2z) p - R "(R) op in layers p is between 2 and 4, iiatr R<sup>r</sup>"Is a tetravulxmt natdieal of choice, dinitre hi'dnocarburiite alylfartfiicte with 1 ... 30 carbon atoms, the other worlds of aliifaitdioi and idittoetheri alitoltilci with 1 ... 30 atoms of carbon, monomer and dietsul alifiatilcl · ou 1 ... 30 atam! L of earibon, and Z represents a whole number between 0 and 6. As examples, I can mention:
ia) 3- (3,5-ddi-> tert - butyl-4-hihdnoxyphenyl) propylomaltjull of m-octodecal, 2- (3,5-yl-tert-butyl-4-hydroxy-phenyl) -acceptable n-ootadiene ' 1,4-di-tert-1,4-hydroxybenzoate die n-octadee, 3,5-idi-tert-butyl-4-hydroxyphenylbenzoate of n-hexyl, 3,5-di-tert -butyl-4-hydroxylphenitoenithioid ide n-; dddecii; l, 3- (3,5-dithiothyrite-ibiu'tâiM-hildnoixiÎfenil) - prppdloinaib of neoidoideicdl, ibeitoH (3,5MdMerț-ibultdl-4-h.idroX'il pi'ppiomait of dodecyl, alpha- (4-hl, droxy-3,5-iterate-buiteenlil) -isobultylate ide, ethyl, alpha- (4-hildlroxy-3,5Hdi-tert-Mbutylphenyl) -isdbutdnatuil of loctadecyl, θ1ΐη- (4-Μάίηοχΐ3. 5- di-tert-biultilfeniii) -proipi [oniatuÎ de ont'a'decâil;
ib) 3,5-idyl-butyryl-4-hydroxybenziohydate ide 2- (n-oxycylthiyl) -ethyl, 3-d-yl-oxybutyl-4-hihydroxyphenylacetate ide 2- (n.-ocylthio) -ethyl , 3.5<sub>!</sub>cl<sub>it</sub>i-] tei'ț-bu! til-4-hiÎdr <). xiflenilace't'a | ti of 2 (n-potade.ciiltâio) Methyl<sub>I</sub> B ^ -datterț-'buifciW-hiiidroxalbenzloialui of 2- (no-'crt; aid.eciiltio) -eitiiâ,
3,5- di-tert9> ufâl-4-hÎldhoxiben0oaW dfe 2 (2-hiildroxyÎetiltiO) -ieltil, bte- (3,5-di.Aeirț-buti, l4-hidrexdlfeml) -ia | ceit0rt | ul of 2, i2'- tithioidiethainOl, bis - [(3,5-! di-tert-butyl-4-hydroxyphenyl) - propionophenyl] diethylthiol, 3- (3,5-idyl-to'rt- <bu.Ιί<sup>ι</sup>Ι-4-1ιί<sup>,</sup>ί1ΐ '; θχϋ © ηίι1) & -ρ.ιΡρίοη<sup>!,</sup>(; υ · 1 of 2- (ui »: tiadeoiiltjio) -ethyl, biis-iS-ÎB ^ -ldi-tert-ibulbiMhidroxifenill) -pnopioniatio 2,2'-tio! dfetano.1, slteair £ wnliidio4N, N- 't0s- [© tdien-3-Î3,54ir teirț-ibuitil-d-hdnoxiÎenilJ-propionialbul], n'butyliminio ^ NjiN-lbils - [' etHlein-3- (3,5-icli-tertbutyl-4-hdidroxy®) endl) -pnopioinaitul], 3,5-fditerț-: bu: ti<sup>r</sup>l-4-liihydroxib.eni20, the idea of 2- (2-stelaroiilioxi & tiit! iio) -ethyl, 7- (3-me! tiil-5-tert-ibuItdil ~ 4-hidmxifeindij-heptanoa'tiuil of 2- (2-) hi <diroxyethylthio) -ethyl, 7 - (3HmPfIl-5-teTt-bu! t-4-hydroxyl-xylfendlj-heptaniolaib of .2 - (, 2-Sfbearoitoxyethyl), c) bis- [3- (3,5-idi tert -butyl-4-hydroxytryxy (eml) -propyloin] die 1,2-propylene glycol, biis [3- (3,5-'-di-tert-butyl-4-hydroxyphenyl) - pnopionate] from letbi'lenlglifcal, bi | s - [! 3 -. (3,5-di-Jteirțbutyl-4-hydroxyphenyl) - propionate] of neOnp'entiig.lâdol, bis- (3,5-di-'tert Jbutyl-4-hihydroxitonylalceibatatl) ide teitiileniglitool , mixed glycerin ester with 1-n-oiohaidecanoic acid and with 2,3-bis- (3,5- (di-tert-butyld-hildroxyphonyl) J-aioeite, teitrariciis- [3- (3,5 ^ di64573 t. 'eryth-butyl-hydroxyphenylj-'PTOpionate] of penitaerylritis etc.
Phenolic compounds of the formula may also be used:
ot
O- (CH<sub>2</sub>) Î — P — OR ί
OR in cane x is equal to 1 or 2, for example: di-n-octaideoyl 3,5-di-iterert-butyl-4-hydroxybenzylphosphonate, 3-'-tert-butyl'-4-hidiOXI-5-methylbenzylphosphonate di-n-octadecyl, 1- (3,5-di-tert-butyl - 4-hydroxyphenyl enyl) di-n-actadecyl ethanophosphonate, 3,5-dihydroxybenzyl-4-hydroxybenzylphosphonate and din-tetwaid 'ecH, di-n-hexadecyl, di-nd'ocoBiil.or di-n-odtadeoil.
Other phenolic compounds have the formula:
(CH<sub>2</sub>) WQ!
QW H<sub>2</sub>Ct-N N— (CH<sub>2</sub>) WQ \ z
II o
in which W and Q have the above meanings, for example: tri / SS-di-'terț-buti.Mhidroxiben'ziljriaociainurate.l and tri- (3-'terțbu<sup>and</sup>til-4-hiihydroxy-5-methylbenzyl - isocyanurate
White examples of antioxidants are nminoaryl-derivative-asyloir compounds, such as -aniline and n-affifyamine derivatives, as well as their respective heteroidal derivatives such as: phenyl-1-naphthylamine, phenyl-S-raaftdlamine, N, N ' -difenyl-p-phenylenediamine, Ν, Ν'-di-sec-butylp-ifenylidenylamine, 6-ethoxy-2,2,4-trdmethyl-1,2-d<sup>it</sup>ibidioch<sup>and</sup>inoline, 6-d od-eryl-2,2,4-trimethyl-1,2-dihydrachiinolinyl, moniooylctilimino d-ibenzdluyl, idio-ethylthio-methyl-benzyl and 2,2,4-trimethyl-1-dihydroquinoline.
Ultraviolet radiation absorbers and light protection agents include the following substances:
ia) 2- (2'-Bildyroxyphenyl) -benzotriazophenes, such as, for example, 5'-methyl, 3 ', 5'-tert-butyl, 5'-tert-butyl, 5-dor-3', 5 '-detert-butyl, 5-chloro-3<sup>r</sup>- tert-butyl-5 '- methyl, 3'sec-Imtil-5'-tert-butyl, 3' - [alpha-methylbenzyl] S'-mertyl, 3 '- [[α-methylbenzene] -5' -methyl, 5elor, 4'-aotoxy<sub>(</sub> 3 ', 5'-give-tert-am.il, 3'-me'tilS'-catrbom & toxiietiil and 5-chloro-3', 5'-di-iterț ~ amil;
b) 2,4-bils- (2'-bildroxy'phenyl) -6-alkyl'-t-niazymes such as, for example, 6-effects-derivative or 6-unidec-derivative;
e) 2-hydroxybenzoic enenzymes, such as, for example, the 4-hydroxy derivative, 4-mefoxy,
4-ootoxy, 4-dehyloxy, 4-doderoyloxy, 4.2<sup>r</sup>, 4-trihydroxy or 2'-hiid.roxy-4,4<sup>,</sup>-dim<sup>and</sup>e<sup>,</sup>fox'i;
d) 1,3-biB- (2'-hi) droxdibenzooyl) - benzenes such as, for example, 1,3-bis "(2'-hydroxide'-hexyloxybenzoyl) - benzene, 1,3-bis- (2 '-hydro-oxy-4' -oct.loxyibenzoyl) -benzene, 1,3bis- (2'-hildyroxy-4'-dodeic: oxybenzyl (l) -benzene;
e) substituted aryl-benzyl benzoyl esters, such as, for example, phenyl salidlate, octaylphenyl sialide, diibenzoylrezoinrime, bis- (4-tert -butylbenzylOdjl) -rozoriciraa, benaoilnezoncinia 2,4-di-tert-butylfemyl, 3,5-di-tert-butyl-4-hiidiro'Xi 2,3-tert-butyl-4-bidiroxybenzoate; ocfaide-oil and 3,5-di-tertiary benzoyl bu'ti! l ~ 4-h'idrox.ibenzoiatu.1 -die 2-motii-4,6-dd-tert-hurt) iilfen) il;
f) -aimylations of oum would be, for example, ialfaciian-beat, betita-diphenylacrylate, alpha-cyan-beta ·, iso-octyl beta-diphenylphenylacrylate, methyl alpha-camboimphytoxidiniamatuil-methyl, alpha-o-'-bomethoxyamine. 'of butyls and N (bsta-oarbcmetoxivmll) -2-meitiildradoliinn;
g) nickel-based compounds such as nickel -composed ones with 2 ', 2'-thio-biis (4-tert-oatylphenol), such as, for example, 1: 1, and 1: 2 complexes, which possibly possess other oum binders - such as n-buitilaramu, trieitamo-lamina or N-etalohexyldietanolaminia, nickel or bis ((4-tert-octylphenyl)) complexes - or oum would be the 2: 1 complex, - possibly possessing - others binders such as 2-ethitaapmiic acid, diib-utiyldi-tiiocairbamates of niich-el, the nickel salts of 4-hildrioxy-3,5-tert -butylbenzylphosphonationyl monoalkyl ide, oum ar fî, de. for example, half-1-ionic, ethyl or butyl estons; the egg-nickel complex 2-hydroxy-4-methylphenylunide! kiloeitonoxiime and 3,5-di-teirt-butyl-4-hid |
h) diarnine / oxaflic acid, such as, for example, d ^ '- aniontiloxiox-amlide, 2,2'-άίίοοΐ3ΐΌΧΪS ^' - ditoterţ-buitliiloxianlillildia, 2,2'-di- <doderi, loxi-5,5 ' -di-tert-bubylX'anyl! dia, 2-efoxl-5toirt-'b'U'fcil-S '-eibiloxyanilide, 2-eitoxy-2' - ethyloxanesIliid'a, -mixtures oonlstiituilte d-in ox-aniIl- the di-subsliylid iides in ortho positions and bet with methoxy and efoxy groups, precium and -compound of formula:
CH<sub>3</sub>,, CH,) n— (CH<sub>2</sub>)<sub>3</sub>-nhcoconh (CH<sub>2</sub>), n ς CH / <sup>X</sup>CII
Phosphate-based stabilizers include trif-eimill phosphite phosphite, difenifefchyl f-osphyl, phenildiiaihch.il, Îosîiitufl. of itrimoniylphen.il, die toilauril, triiodtaldehyde, 3,9-dS-foiodecyloxy-2,4,8,10-tetraoxa - 3,9-diphosphorus! spiro (3,5) -undee-angi and triphosphite - (4-h.idroxi) -3,5-di-iterţ-bubilfeniil).
Agents for the decomposition of peroxides intended to be embedded in the poly-iolefin-include beta-thiodipropionic arid esters, such as, for example, lauryl esters, stearlJlc, myrrh, lic or threecylyl, to G457Î3 myriaaptobenzylorphidylamine, e.g. of <tinnitus, as well. and difeniliâoiuteea.
SțaMliEatarîll · Suitable for polylamides imctad s'alriufriilie d'e oupi and pomblination with the urns of ipdi and / lsalu or other compounds of phosphorus and with the salts of carnivorous bivialeut. in oaditpafte die eosfebifcalicKii basic ae poit mcfnți'oma, de. for example, then, the lifelike lithium, the myfliamine, the benzine, Maanina, the dianiusrat idle triallll, the diidiinidiamma, the urea derivatives, the derivatives of Mdiriarine, the amines, the p.i. calcium ideation. Stabilizers for polychloride ide Vinii include their compoundsglanlo ^ eibalicl per. .stanliu base, of lead and eurynuria of ivary and oaldmium of fatty bleaches.
In the cailljtate idea the agents of mUdieiieiue may be mentioned the arid 4-4emț-bultSlbeiiizophiic, the arid auxypic and the laidium diiienilacietic.
The same way .da and in the case of those with the foramen, general lamb I, mriide at illt ladliltlv · are used in moid avamitajtots in a ratio of 0.01, .. 5 ° /<sub>0</sub> mass in ratio egg mass paliMeruM. oetrateit. in the. binary combinations see one or thousands of antioxlidants eniumerated upstream or in tenuous comhilnaatiiil. with these tarititoxSSdianants and with agents for absorption of raidiation <ultrasraViolets enumerated to myriad ones, the compounds I have the most effective formula for the basic properties. of compounds of general formula I in a film d<sup>!</sup>is polypropylene: an attnejsitec consisting of 38 parts polypropylene and 0.076 parts beta (ă'-hydroxy-S'.S'-tert - butylphenyl) -propionate by nMotcfacteaiO. homogenise in a mixer at 200 ° C at a temperature of 3 minutes. The mixture is treated with 0.19 parts of the capillary Rî is me'tiil, Rs is hydrogen, iair -R3 is p-miPtoxlbenzoitt<sup>1</sup> .and then homogenize in oonilân'u'are for another 7 mi5 mites. The resulting composition is formed by idomprim) it is possible to produce the leaf by taking the thickness of 0.1 mm, the operation, of formation carried out inside. - At a temperature of 260 ° C for a period of time of 6 months. The relliculeflle lastfiel obtained cool the citrus in the race mare.
- From the film · of polypropylene with thickness d, e, 0.1 mm so · cut out a portion with ddimienisiunSle of 44 mm X
100 mim, .which is exposed to the whole luminous Irradiation of a feidieoimeitru. arranged from a bench hereiraufllar egg · 28 lamps icu sunlight and egg black light, arranged alternately. The lamps produce light soB0 box sffin / t represented by fluorescent lamps die; 20 W icu ide length 60 cm, grounded by a maximum emission of 3100 Â; The lamps for the black Illumina are represented as egg lamps, ultraviolet radiations of 20 W egg, the length of 60 icm egg, an emission of 3500 Â. The specimen rotates concentric in the groove of the lampshade, so that the radiation emitted by the garment will be diisitribuiife uinltfionm throughout the entire test subject to the experience. The evidence thus laid out is examined and the period examined; from the left of the probationary society, the little euphysius vase is subjected to the test of medainnjceț for the purpose of deitenmilnia uiiungiinea the total pronoun at break and the interval of time after cape the test reaches 50% of the initial elongation<sup>1</sup> the break.
A series of sdlmlllaire disputes are carried out on some polypinopainic flour / bile / bileziatot, rejspe'atifv trials, which we name known to the known users. The results obtained in these experiences are presented in (Table 2.
Table 2
<td rowspan="2">(additive</td><td>Time factor up to a proportion of 50% of the • initial elongation at break (egg samples • additive)</td>
<td>time up to a proportion of 50% of the initial elongation at break (blank test)</td>
<td>them</td><td> 2</td>
<td>Absent</td><td> 1,0</td>
<td>2 ^ (2'-hiidroxi-3<sup>,</sup>, 5'-di-tert-butiilfeinÎl) -5-clorbenzo.tri'azolul</td><td> 3,2</td>
<td>4-Ieml<sup>it</sup>carbamoyloxy-2<sub>)</sub>"2,6,6-tetramethyl} ipcii<sup>,</sup>dina</td><td> 1|8</td>
<td>l, 6-bib [(4<sup>,</sup>-oarbamoîloxi) -2<sup>,</sup>, 2i<sup>,</sup>,6<sup>,</sup>,&<sup>,</sup>-tetranieibi'lpiiperidin] hexane</td><td> 2·,4</td>
<td>Benzoate of 2,2; 6,6-teitiramettlpineri <bml- (4)</td><td> 2,6</td>
<td>Sebacate idea with 2,2,6,6-tetramethyl-4-piperidinyl)</td><td> 4,7</td>
<td>Phenylacetate of 1,2, .2, G, 6-pentaethyldipylidinyl- (4)</td><td> 5;2,</td>
<td>Bis- (1,2v,6,6,6 ^ pentamethyl-4-piparidine terephthalate)</td><td> .5,3·</td>
<td>p-matoxibenzoate of, 2v2,6,6 ^ pen, tametilpip © rid3n, the (4)</td><td> 5,3</td>
<td>l'-naphthoate of 1,2,6,6,6-penjtameepitieiădi'ml- (4)</td><td> 5,4</td>
44 (continue table 2)
<td> 1</td><td> 2</td>
<td>1,2,2,6,6-pen.thamethylpiperidinyl- (4) octanoate (4)</td><td> 6,2</td>
<td>Isobutlate of l, 3<sub>r</sub>2,6,6-pentametilpiperidinill- (4)</td><td> 6,2</td>
<td>Bis- (1,2,2,6,6-pentamethyl-4-piperidinyl) Sebacate</td><td> 8,0</td>
<td>3,4-ble- (4'-oarbamoHoxi it<sup>it</sup>,2',2<sup>r</sup>,6<sup>,</sup>, 6'-pentameti3pipeiridin) toluene</td><td> 5,2</td>
<td>4-ρ-Ιο]! 'Ο & ΓΒ &-1,2,2 ™ οί1οχί, ϋ, 6-ροηί & ΐΐκίί1ρΐρθΐ'ίάίΐϊ7ΐ</td><td> 5,2</td>
<td>4-alilcarbamoi1 () xi-l<sub>r</sub>-2,2,6,6-pentametiipiperidină</td><td> 5,5</td>
<td>4-fenilcarbamoiloxi-l, 2, <2,6,6-pentametilpiperi of pyridine</td><td> 5,6</td>
<td>4-meftilcarbamoiloxi-l, 2, 2.6<sub>></sub>6-pentamethylpiperidine</td><td> 5,8</td>
<td>l, 6-bis (4'-oarbamoiloxi it<sup>,</sup>,2',2<sup>,</sup>, 6 ', 6'-pentametilpiparidin) hexane</td><td> 9,2</td>
<td>Bis- (1-benzyl) -2,2,6,6-tetramethyl-4-pi <peridinyl) Sebacate</td><td> 5,0</td>
<td>1-ethoxycarbonylmethyl p-methoxybenzoate; GS-tetramethylpiperidinyl- (4)</td><td> 5,1</td>
<td>2'-ethyl] 1-benzyl-2 hexanoate<sub>)</sub>2,6,6-tetramethylpiperidine, yl- (4)</td><td> 5,2</td>
<td>(N-dodecyl) octanoate -2<sub>1</sub>-2,6<sub>1</sub>6-tert-dizzy-lpiper'idinil- (4)</td><td> 5,2</td>
<td>Octanoate (2)<sup>,</sup>hydroxyethyl<sup>and</sup>l) -2,2,6,6-tetrametilpiperidinil- (4)</td><td> 5,8</td>
<td>, (N-propyl) -2,2,6,6-tetramethylpiperidine- (4) octanoate (4)</td><td> 6,0</td>
<td>4- (n-dodeciIoxi) -l, 2,2,6,6-pen.tametiipilperidină</td><td> 5,5</td>
<td> 4-(2<sup>r</sup>-<sub>a</sub>ii<sub>us</sub>ţoxl) -l, 2,2 ', 6,6-pentametilpăiperidină</td><td> > 6,0</td>
<td>l, 4-bis (l ', 2', 2 '<sub>r</sub>6',6<sup>it</sup>-p<sub>en</sub>tametil-4'-piperidinyloxy) -butan</td><td> >6,0</td>
<td>TrI- (i, 2,2,6,6-pentamethyl-4-piperidyl-nyl) borate</td><td> 5,0</td>
Repeat the Otter mode described above, except that it is used a proportion of 0.25% mial of the stabilized hippocampus protection against the action of light subjected to exasperation, instead of propitone using a polyethylene of low density. The pressing is effected at a temperature of 180 ° C, and the pressed articles are formed by compression spne and plates with a thickness of 11 mm are obtained, this formation process is effected at a temperature of 150 ° C. The plates are stored at a temperature of 20 ° C and - visually hypeadodilc is examined, to detect - the exudation signs. The results obtained are presented in Table 3, - they also contain, - also, a series of data referring to some comparative tests performed with the help of - some photositailization of ounosautuses.
Table 3
<td>Photoshop used</td><td>Time elapsed until exudation (days)</td>
<td>2,2,6,6-tefcramethylpiperidinyl- (4) stearate</td><td> 1-5</td>
<td>Sebacate bis- (2,2,6,6-tetramethyl-4-piperidyl)</td><td> 20</td>
<td>4-steariloaî-2,2,6,6-tetramethylpiperidine-bamoiloxi</td><td> 13</td>
<td>1,2,2,6,6-pentamethylpiperidinyl- (4) stearate</td><td> > 50</td>
<td>Bis- (1,2,2,6,6-pentamethyl-4-piperidinyl) Sebacate</td><td> > 50</td>
<td>4-stearilcarbarnoilox! -L, 3,2,6,6-pentainetilpÎ, peri-Dina</td><td> >60</td>
The working mode described in the second series of samples is repeated, except that the compression formation is carried out at a temperature of -200 ° C, and the substrate used is a high density polytothionite. The obtained results are presented in tables 4, which also contains a series of dahlias made in comparative tests, based on the use of a known photosensitizer.
<td colspan="2">Table 4</td>
<td>Photostabilizer used</td><td>Time elapsed until exudation (days)</td>
<td>2,2,6,6-tetramethylpiperidiml stearate (4)</td><td> 40</td>
<td>1,2 'stearate | 2,6,6-pentamethylpiperidines -] - (4)</td><td> >75</td>
<td>4-starzrilcaj'bamoi] oxy-1, 2,2,6,6- tetramethyl Upiperidine.</td><td> >75</td>
<td>1- (n-dodecyl) -2,2 <, 6,6-tetramethylpiperidinyl- (4) octanoate</td><td> > 75</td>
An equivalent amount of egg 100 parts of crystalline granules in powder form is mixed with 0.25 parts of stearate-l, 2,2,6,6-penitialin) & tillipdperiidinium (4), and the dry mixture is homogenized <sup>20</sup> by pressing. The stabilized granules, thus obtained, are subjected to an injection molding operation towards α, plates with a thickness of 2 mm are produced. These plates are exposed for a period of 3000 hours to initiate an apparatus for exposure, subsequently measured even. / buaia ingaăLbenine of their plates by determining the nourishment of the yellowing faction with the help of the equation below:<sup>A</sup>> d <sub>x</sub> ioo T (560) in the Δ T tubing the degree of .reduction, .a tnainism of the eipiruveta sieve Ja iltuingimea de
4 waves of 420 nun and respectively takes the wavelength of 680 mm after exposure in the apparatus, T (5 (, o) represents the frianismisita corresponding to an unexposed proof, at an idea wavelength of 560 mimes.
The results obtained from these experiments, as well as the data relating to any blank test and other compositions are presented in Table 5.
Table 5
<td>Photostabilizer used</td><td>The yellowing factor after 3000 hours</td>
<td>Absent,</td><td> 35,0</td>
<td>Stearate of 1,2,6,6-B-pentaminesLlypiperyclinyl- (4)</td><td> 10,0</td>
<td>2'-ethylhexane. 1-benzyl-2,2,6,6-tctramethylpi.pi'idinyl- (4)</td><td> 9,8</td>
<td>1,2,2,6-m-oetanoate G-pentaraethylpiperidinyl- (4)</td><td> 9,5</td>
<td>4- (2 .'- cianetoxl) -l, 2,2,6,6-pentamethylpiperidine</td><td> 8,0</td>
<td>4-steairilearbamoiloxi "l, 2,2,6<sub>1</sub>G-pentatnctiipiperidi! Na</td><td> 7,5</td>
<td>Bis- (1,2,2,6, G-pentamethyl-4-piperidinyl) Sebacate</td><td> 6,6</td>
In 75 parts of the dinihr mass - a mixture of dimeiWoirmiamide and .acetone (the egg of the mixing voters die 1: 1), dissolve 25 parts of the mass of di- ntin- um ipoliuneltan-peliciliiliogen on the basis of the .polyester and then add it /<sub>B</sub> mass 4- (2'-aian © toxi) -l, 2,2,6,6penitpimettaiipiipei-itdina. The clear and homogeneous us-tfel solution obtained is flattened. By an attic plate to produce a -peiiiiou with a thickness of 400. .. 500 mitenones, which is dried. Then for 4 minutes Ja [50 ° C temperature and 6 minutes at 140 ° C. The final thickness of the breast is 80. .. 100 microns. The upright patiaulos are detached from the glass plate, mounted on a .alb carbon and exposed in a .dapatary die (exposure, a proportion of 50¼ of the surface of the exposed specimen being covered in order to facilitate the subsequent visual estimation of gra15 dudi dte galgeine caused by the exposure Try to examine the visuals at the interlvie idea for a period of 100 hours, your opportunity is evaluated the results obtained. The results obtained are presented in the table
6, which alludes, from lăsemleniaa, the iretecitoaire residues to an inicercaine witness (egg epnuveba devoid of fatostehilizador) and to other experiences in which the stahiilizaltioirlI were prepared, according to the present invention.
Table 6
<td>Photostabilizer used</td><td>The time elapsed until the yellowing starts (hours)</td>
<td>Absent</td><td> > 100</td>
<td> 4-(2<sup>/</sup>-oianetoxi) -l, 2,2,6, G-penfometÎ.lpiperidina</td><td> 200</td>
<td>1,2,2 ', 6,6-pentamethylpiperidinyl- (4) octanoate (4)</td><td> 300.</td>
<td>Bis- (1,2 -, - 2,6, e-pentatnetyl-4-piperidinyl) sebacate</td><td> 300</td>
<td>4-phenylcarbamoyloxy-1-n-propyl-2,2-yl 6-tetramethylpyridine</td><td> 400,</td>
It mixes well 1000 parts non-unstabilized polypropylene mass powder with one part befa- (4'-hiidatox.i-3 mass)<sup>r</sup>, 5 '-! Fendtl) toothpick -ptroiptantalt of n-oefcadacitl and 2 parts table 3<sup>r</sup>, 5 '-. Di-iterț «bult: il-4'-hydroxy- 30 benzoalt of l ^^. Ee-.penibalmcrtâl-i-ipâperildirail, the operation of mixing ex ecu ecuate with the products in utsaafa state. The dry mixture thus obtained is quenched at tem-<sub>35 </sub>petuaihuri laie cillinidirullui .included in 180 ... 220 ° C, and the extruded material is granulated. The stabilized preparation, thus obtained, is subjected to a spinning operation from topitfure and to an ephemeral idea operation in<sup>40 </sup>the conditions below: the temperatures of the extruder 230 ° CJ.265<sup>c,</sup>C / 275<sup>a</sup>C; melting temperature at the die 270 ° C; spinning speed 400 m / min; stretch ratio 1: 5; titruil mUWitamenifaikii 130/137 deniteir; resistance to fraction 6 g / dieier.
The multifilmite thus obtained is applied on a sample holder, as a support on white cardboard. In the course, the oil is exposed to exposure, at intervals of as much as 200 hours, 5 fiber samples are taken, to which the resistance to the iramanenib all is measured. The obtained results are a graph according to the duration of the exposure; from the diagram, the period is calculated, the exposure (T) needed to reduce the resistance to the initial fnaicțiusnle, 50%. The same value is considered as the necessary amount until the deterioration.
Table 7
<td>F & tostabilizatorul</td><td>Time (T) up to 50% reduction in resistance to traction</td><td>Faotorul stabilizer T witness</td>
<td>Absent</td><td> 430</td><td> 1,0</td>
<td>to ta'-hfdi-oxy-S '^' - ^ di-tert-butyl-S-clorbenzotriazol lfeniP</td><td> 530</td><td> 1,2</td>
<td> 3’,5-<sup>,</sup>1,2,2,6,6-pentamethyl-4-piperidinyl-di-tert-butyl-4'-hydroxybenzoate</td><td> 1400</td><td> 3,3</td>
<td>Beta - (. 3<sup>,</sup>15'-di-tei-t-butyl-4'-hydroxylenyl) -piOpononate 1,2,2,6,6-penta-nethyl-4-piperidinyl</td><td> 1600</td><td> 3,7</td>
<td>Bis (1, 2,2, e, 6-pentamethyl-4-pyridinyl) Sebacate</td><td> 2600</td><td> 6,0</td>
The way of working described in the first series of tests is repeated, except for the fact that epmuveibes die paldipropillena treated iter- 5 miles are exposed to the action of the luminous nadilaițiitoir luminous in an exhibition apparatus and not in the latteamcta. The achievable outcomes are presented in Table 8, including the data relating to a blank sample (egg without foieostabilizaftoir) and a comparative experience in which the sample contains a known phofostebiilizialist.
Table 8
<td>Photostabilizer used</td><td>Time to deterioration (hours)</td>
<td>Absent (witness test)</td><td> 800</td>
<td>2- (2'-hîd i'Oxi-3<sup>1</sup> ^ '- di-tert-butylphenyl) -5- corbenzotriazole</td><td> 1630</td>
<td>Bis Sebate (lp ^ GS-pent-amethyl-piperidinyl)</td><td> > 9000</td>
<td>1,2,2,6,6p bet-a-tert-butyl-tert-butyyl-tet-hi-droxiphenip-propionate (4)</td><td> 10000</td>
<td> 3-<sup>,</sup>1,2,3,6,6-pentamcrylpi.peridinyl-1, 5'-di-tert-butyl-4'-hydroxybenzoate (4)</td><td> >8600</td>
<td>1,2,2,6,6-pentamethyl octanoate<sub>!</sub>piperidiinil- (4)</td><td> 6500</td>
<td>4-feni'lcarbanîoiloxi it, 2,2i, 6.6 - pentamethylpiperidine</td><td> > 7000</td>
<td>4-metiilcarbamoiloxî-l ', 2,2,6<sup>and</sup>16-pentamethylpiperidine</td><td> 6000</td>
<td>1,2-, 2 ', 6,6-pentamethylpiperidinyl- (4) cyclohex-ancar-boxylate (4)</td><td> > 6000</td>
<td>1,2,2,6,6-penta-methylp.-hyperidi-niyl- (4) stearate</td><td> > 60-00</td>
<td>1-, 2-, 2,6,6-pentamethylpiperidinyl- (4) benzoate</td><td> > 5000</td>
An amount ledhdjvialeaite with 100 parts milled polyamide-6 (in grain form), <sup>I0 </sup>caries contains 1.8 parts millet titanium bibx & d, it is mixed in dry stroke 0.5 parts 4-benzyloxy, -1,2,2,6,6-penitaimietiilpiiiper-id'ina. The resulting amiedtecuil is directly subjected to a spinning idea operation from the melt<sub>15 </sub>to produce 20 dental moniophysiologists. The monioifiilllattîentefle is applied to a cantilever aflib without phenytenesisate and then exposed to the action-brightness of the luminous initr-u-η-apparatus of exposure. After 20 days of exposure of 500 hours, 1000 hours, 1500 sheep and 2000 hours, respectively, take 5 fibers from each preparation and take each interval of time, the tests will be answered and tested, for the purpose of the idea of determining their re-efficiency, they gain traction. The arylthymietic average of the percentage ratios of your traction resistance (in relation to the total value and the resistance and traction) is plotted, in fungi of the duration of exposure. From the obtained diagrams, the points corresponding to the deibenioirareii are determined, that is to say, the time pediment elapsed until the moment when the value of the tensile strength represents 50% of the tensile strength initiated.
Table 9
<td>Photostables-used drone</td><td>Time up to 50% reduction of initial resistance to traction (hours)</td>
<td>Absent (witness testimony</td><td> 475</td>
<td>L ,, 4-benzyloxy-2,2,6,6-pentamethylpiperidine</td><td> 1412-0'</td>
<td>Bis- (1,2,2, S, 6-pentamethyl-4-piperidiinyl) sebacate</td><td> 1600</td>
<td>Octanate of 1,2,2,6,6: -pentamethylpiperidinyl - (4)</td><td> 14-50</td>
<td>1-phenylarbamoyloxy-1,2,3,6,6-pentamethylpiperidine</td><td> 1450</td>
<td>1,6-bis (4'-carb of nooxyl-1 ', 2', 2 ', 6', 6 '-pentamethylpiperidine) - hexane</td><td> -1500</td>
<td>4,4-bis (l ',' 2 ', 2<sup>it</sup>,6<sup>it</sup>> 6'-pentamethyl-4<sup>it</sup>-piperidiiiiiiloxi) -butan</td><td> 1600</td>
Pwaceide, according to the invention, (reported by AvianlBojiul that extends the range of hereditary to the pharyngitis of new compounds whose caries are suitable for a foitos.tabili'ZaîtoinÎ and lamtiioxiidants with long secondary action in polymyal myelateria.
Contents19
3 sheets
Sheet 1 Sheet 2 Sheet 3
46 members in 25 offices
Priority claims3
| Document | Office | Kind | Date |
|---|---|---|---|
| 5548771 | United Kingdom | A | |
| 2845872 | United Kingdom | A | |
| 3547372 | United Kingdom | A |
Members46
| Document | Office | Kind | |
|---|---|---|---|
| IL40888A0 | Israel | A0 | |
| BE792043A | Belgium | A | |
| NL7216278A | Netherlands (Kingdom of the) | A | |
| DE2258752A1 | Germany | A1 | |
| ZA728468B | South Africa | B | |
| JPS4865180A | Japan | A | |
| BR7208426D0 | Brazil | D0 | |
| FR2182789A1 | France | A1 | |
| FR2183293A1 | France | A1 | |
| FR2183294A1 | France | A1 | |
| IT971346B | Italy | B | |
| AU4940972A | Australia | A | |
| DD106190A5 | German Democratic Republic (until 1990) | A5 | |
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| PL90214B1 | Poland | B1 | |
| CH585714A5 | Switzerland | A5 | |
| CH585715A5 | Switzerland | A5 | |
| CH586252A5 | Switzerland | A5 | |
| US4021432A | United States of America | A | |
| FR2183293B1 | France | B1 | |
| HU170685B | Hungary | B | |
| US4046737A | United States of America | A | |
| US4049647A | United States of America | A | |
| HK47877A | Hong Kong, China | A | |
| RO62513A | Romania | A | |
| SU584795A3 | Soviet Union (until 1991) | A3 | |
| FR2183294B1 | France | B1 | |
| MY7800025A | Malaysia | A | |
| CS190377B2 | Czechoslovakia (until 1993) | B2 | |
| RO64573AThis record | Romania | A | |
| SU721008A3 | Soviet Union (until 1991) | A3 | |
| RO71050A | Romania | A | |
| USRE31342E | United States of America | E | |
| USRE31343E | United States of America | E | |
| NL174942B | Netherlands (Kingdom of the) | B | |
| JPS5920709B2 | Japan | B2 | |
| NL174942C | Netherlands (Kingdom of the) | C | |
| SE454277B | Sweden | B | |
| DE2258752C2 | Germany | C2 |
Numbers
- Application
- 7283993
Titles2
- French
- PROCEDE POUR LA PREPARATION DES DERIVES DU PIPERYDINE
- English
- PROCESS FOR THE PREPARATION OF PIPERYDIN DERIVATIVES
Classification
- CPC, 4
- C08K5/3435
- C07D211/46
- C07F5/04
- C09K15/30
- IPC, 30
- C07D211 44
- C08K5 00
- C07D211 46
- C07D405 12
- C07D409 12
- C07F5 04
- C08K5 34
- C08K5 3412
- C08K5 3435
- C08L1 00
- C08L7 00
- C08L21 00
- C08L23 00
- C08L23 02
- C08L27 00
- C08L33 00
- C08L33 02
- C08L51 00
- C08L51 02
- C08L67 00
- C08L77 00
- C08L101 00
- C09K15 30
- C09K15 32
- D06M13 02
- D06M13 322
- D06M13 35
- D06M13 355
- D06M101 00
- D06M101 16
