Untitled record

<td>POLAND REPUBLIC ICE</td><td>PATENT DESCRIPTION</td><td colspan="2"> 90214</td>

<td>in</td><td>Additional Patent to patent no. -: - - Reported: November 28, 72 (P. 159154)</td><td colspan="2">MKP C08f 45/54 C08f 45/60 C08f 29/02</td>

<td rowspan="2">OFFICE PATENT PRL 4</td><td>Priority: 30.11.71 for claims 2 17.06.72 for 3 Great Britain The application was announced: 30.09.73</td><td colspan="2">Int. Cl.2 C08K 5/34 C08L 23/00</td>

<td>Patent description published: 31.12.1977</td><td></td><td>CZ and. -LNIA</td>

<td></td><td> ·</td><td></td><td>Housing Office hlski | And that: ·. L&gt; -i</td>

<td colspan="2">The inventor: -</td><td></td><td></td>

<td>• Authorized</td><td colspan="2">from patent: Ciba-Geigy AG., Basel (Switzerland)</td><td></td>

A method of stabilizing polymers, especially for photolab and thermal degradation

The subject of the invention is a method of stabilizing polymers, especially for photo- or thermodegradation, in which at least one new piperidine derivative is added as a stabilizer.

In German Patent No. 1,929,928, compounds of general formula 4 in which the R 1 and R 'sibols are described as stabilizers₂ are identical or different alkyl radicals, or together with the carbon atom to which they are attached form a saturated alicyclic radical of formula 2, and n is the integer 1, 2 or 3, and in the case where n '= 1, R's is an aliphatic acyl radical , alicyclic 'or heterocyclic monocarboxylic acid, N-substituted carbomyl radical of N-substituted carbamic acid, thiocarbamyl radical · N-substituted thiocarbamic acid, a monovalent radical obtained by disconnecting the hydroxyl group from an · ketoacid, alkyl, cycloalkyl, arylalkyl, aryl radical or a radical of formula 3 in which R 1 and R'2 are as defined above.

In the case where n '= 2, R_s is a diacyl radical of an aliphatic, alicyclic, aromatic or heterocyclic dicarboxylic acid; its dicarbamyl dicarboxylic acid radical, dithiocarbamic acid dithiocarbamyl radical, carbonyl group, divalent radical obtained by disconnection of two hydroxyl groups from ketoxy acid, alkylene radical, alkylene radical R '₈ is a triacyl radical of an aliphatic, alicyclic, aromatic or heterocyclic tri carboxylic acid, a tri-carbamyl tri-carbamic acid radical, a tri-thiocarbamyl radical of a tri-carbamylic acid, a trivalent radical obtained by disconnecting three hydroxyl groups from a ketoacid, an arylthriotinate ·

It has been found that certain piperidine derivatives substituted in positions 1 and 4 and salts of these compounds are effective polymer stabilizers especially for photo- and thermodegradation.

The subject of the invention is a method of stabilizing polymers, especially for photo- or thermodegradation by the addition of - as stabilizers at least one of the new piperidine derivatives substituted in positions 1- and 4- or their salts represented by general formula 1, in which the symbol n represents an integer 1, 2, 3 or 4, Rt is an alkyl radical with 1-20 carbon atoms, alkenyl or alkynyl radical with 3-20 carbon atoms, an aralkyl radical of 7-12, preferably 7-9 carbon atoms or a radical of formula 5 or 6, in which formulas m is the total face 1, 2 or 3, R4 is a hydrogen atom or a methyl or phenyl radical, Χ2 is an atom. halogen, cyano, -COR₅, -COOR5,

-COSR5, -CONR₅R₆ or a group of formula 7, Χχ

214

214 is a hydroxyl group, a halogen atom, a cyano group, a group -OR₅, -OCOR₅, -OCSR5, -OCONR₅R₆, -OCSNR₅R₆, -C / 0 / R5, -COOR₅, -COSR₅, -CONR₅R₆ or -CSNR₅6; R5 in X substituents_tand X2 is an alkyl radical with 1-20 carbon atoms, an alkenyl radical with 2-20 carbon atoms, an alicyclic radical with 5-12 carbon atoms, an aryl radical with 6-11 carbon atoms, an aralkyl radical with 7-14, preferably 7 - 11 carbon atoms, and in the case when R5 is connected to the nitrogen atom also a hydrogen atom, R6 in the substituents Χ4 and Χ2 is a hydrogen atom or an alkyl radical with 1-4 carbon atoms, or R6 together with the R5 radical and a nitrogen atom, in which both radicals are bound to, is a five or six membered ring further containing no heteroatoms, or containing one or more further heteroatoms, or Rj may be an acyl radical of the formula -COR₇in which R₇ means a hydrogen atom, an unsubstituted or substituted aliphatic radical of 1-20 carbon atoms, an alkenyl or alkynyl radical of 2-20 carbon atoms, a cycloalkyl radical of 5-12 carbon atoms, an aralkyl radical of 7-14 carbon atoms, an aromatic radical of 6-14 Preferably 6-12 carbon atoms, a heterocyclic radical or a carbamyl or thiocarbamyl radical of formula 8 in which Χ3 is an oxygen or sulfur atom, R₈ means a hydrogen atom or an alkyl radical with 1-4 carbon atoms, and R9 a hydrogen atom, an alkyl radical with 1-20 carbon atoms, an alkenyl radical with 3-20 carbon atoms, a cycloalkyl radical with 5-12 carbon atoms, unsubstituted or substituted aryl radical about

6-12 carbon atoms, R2 is an alkyl radical of 1-4 carbon atoms, an alkenyl or alkynyl radical of 3-20, preferably 3 or 4 carbon atoms, a cycloalkyl radical of 5-12 carbon atoms, an aryl radical of 6-11 carbon atoms or an aralkyl radical of 7-9 carbon atoms, or R2 is a hydrogen atom, and when n = 1, R8 is a monovalent radical having the meaning of Rt, or a monovalent group obtained by disconnecting the hydroxyl group from sulfonic acid, sulfonic acid, acid containing a phosphorus atom or boric acid, with an aryl, cycloalkyl radical with 5-12 carbon atoms or has the same meaning as R_b and when n = 2, R3 is a divalent alkylene radical of

1-20 carbon atoms with an alkenyl radical of

2-20, preferably 3-20 carbon atoms, an alkynylene radical of 2-20, preferably 3-20 carbon atoms, a cycloalkylidene radical of 5-12 carbon atoms, an arylene radical of 6-14 carbon atoms, an aralkylene radical of 8-14 atoms carbon, a diacyl aliphatic, aromatic or heretocyclic radical, a -CO- or -COCO- group, a dicarbamyl or dithiocarbamyl aliphatic or aromatic radical, a sulfinyl or sulfonyl group or a divalent radical obtained by the separation of two hydroxyl groups from disulfonic acid, from a phosphorus-containing acid or from boric acid, and when n = 3, R3 is a trivalent alkantriinyl, aryltriline or aryltrinetrialkylene, trialkylic or aromatic trialkyl radical o-phosphoric, o-phosphorous or o-boric acid radical, whereas when n = 4, R3 is a tetravalent radical and is an alkanotetraacyl radical or is a tetraacyl radical of an aliphatic or aromatic tetraarboxylic acid or a tetravalent o-silicic acid radical.

When n = 1, Rt and / or R3 may be alkyl radicals of 1-20, preferably 1-18 carbon atoms. Examples of such substituents are methyl, ethyl, n-propyl, n-butuline, and second radicals. butyl, ill. butyl, η-hexyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-hexadecyl, n-octadecyl and eikezyl. Due to availability and activity, compounds in which Rt is a methyl group are preferred. Due to the optimal combination with the polyolefin raw material, those compounds of formula I are preferred in which Rt and / or R3 are alkyl radicals of^;-20, preferably 5-12 carbon atoms. .

Examples of alkenyl radicals Rt and / or R3 with 3-20 carbon atoms are: allyl, 2-methylallyl, 3-hexenyl, 4-octenyl, 6-decenyl, 10-undecenyl, 8-octadecenyl, and allyl radicals are preferred and 2-methylallyl.

Examples of alkynyl radicals Rt and / or R3 are: propargyl, 1-butynyl, 2-butynyl, 1-pentynyl, 1-hexinyl, 1-octynyl, 1-decynyl, 1-dodecynyl, 1-tetradecynyl and 1-octadecynyl. 'Preferred alkynyl radicals are propargyl and methyl propargyl.

Examples of suitable Rt and / or R3 aralkyl radicals are: benzyl β-phenethyl, α-methylbenzyl, α, α-dimethylbenzyl, α-naphthylmethyl and p-methyl-α-methylbenzyl. A preferred radical from this group is the benzyl radical. t

A further subgroup of Rt and / or R3 radicals are substituted alkyl radicals of the formulas 5 and 6, in which m, R4, Χχ and Χ2 have the meanings given previously. Preferred radicals from this subgroup are those in which R4 is a hydrogen atom, m = 1.

Examples of R radicals_L and / or R3 in which Xt is a hydroxyl group are: 2-hydroxyethyl, 2- and 3-hydroxypropyl, 3- and 4-hydroxybutyl, 4-hydroxypentyl and 2-hydroxy-2-phenylethyl - and preferably 2-hydroxyethyl, 2 -hydroxypropyl and 2-hydroxy-2-phenylethyl.

Examples of R4 and / or R radicals_sin which Xx and / or Χ2 are halogen are: 2-chloro and 2-bromoethyl, 2- and 3-chloro and 2- and 3-bromopropyl, 3- and 4-chlorobutyl and 2-chloro-2-phenylethyl, and preferred 2-chloroethyl, 2-chloropropyl and 2-chloro-2-phenylethyl.

Examples of the radicals Rt and / or -R3 in which Xt and Χ2 is cyano are cyanomethyl, 1- and 2-cyanobutyl, 4-cyanopentyl, 2-cyano-2-phenylethyl, and preferably 2-cyanoethyl.

Examples of Rt and / or R3 radicals in which

214

X₂ is a group of 1,2-epoxy are radicals:

-propyl, 2,3-epoxy-methylpropyl and preferably 2,3-epoxy-n-propyl.

When Xt is a group -OR5 or a group of formula -OCOR5, -OCSRg, -OCONReR₅, -CSNR₆R₅, or when Χχ and / or X₂ is a group of the formula -COR_S, -COOR-, -COSRg, -CONR_eR5 and R5 is an alkyl radical, it is preferred if the alkyl radical contains 1-12 and preferably 1-2 carbon atoms. When R5 is an alkenyl radical, it is preferred that it contains 2-4 carbon atoms: when R5 is a cycloalkyl radical, it is preferred that it contains 6 carbon atoms; when R5 is an aryl radical, it is preferred that it contains 6 or 7 carbon atoms; when R5 is an aralkyl radical, it is preferred that it contains 7 or 8 carbon atoms.

R5 and R radicals_e they may, together with the nitrogen atom to which they are attached, be a 5 or 6 membered ring, such as pyrrolidinyl, imidazolidinyl, pyrazylidinyl, piperidinyl, piperazinyl or morpholinyl.

Examples of R substituents_x and / or R_s in this subgroup are: 2-methoxyethyl, 2-propoxyethyl, 2-ethoxyethyl, 2-butoxyethyl, 2-methoxypropyl, 2- and 3-ethoxypropyl, 2- and 3-n-butoxypropyl, 3- and 4-methoxy-butyl radicals, 3 - and

4-ethoxybutyl, 3- and 4-butoxybutyl, 4-methoxypentyl, 4-ethoxypentyl, 4-n-butoxypentyl, 2-methoxy-2-phenylethyl, 2-ethoxy-2-phenylethyl, 2-acetoxyethyl, 2-n- propionyloxyethyl, 2-benzoyloxyethyl, 2-acetoxypropyl, 2-n-propionyloxypropyl, 4-acetoxybutyl, 4-n-propionyloxybutyl, 4-acetoxypentyl, 4-n-propionyloxypentyl, 2-phenyl-2-acetoxyethyl, 2 / acetoxyethyl , 2- / ethylcarbamyloxy / ethyl, 2- / phenylcarbamyloxy / ethyl, 2- / methylcarbamyloxy / propyl, 2- / ethylcarbamyloxy / propyl, 2-phenyl-2-V-carbamyloxy / ethyl, 2- (allylthiocarbamyloxy / ethyl, 2-phenyl-2- / methyl-carbamyloxy / ethyl, 2-phenyl-2- / phenylcarbamyloxy / ethyl, methylcarbonylmethyl, 2-netylcarbonyl / ethyl, 2- (ethylcarbonyl) ethyl, 2-methylcarbonyl / propyl, and 1- (methylcarbonyl) -2-phenylethyl; methoxycarbonylmethyl, 2- / ethoxycarbonyl / ethyl, 2- / methoxycarfconyl / propyl, 2-methoxycarbonyl / -2-phenylethyl, 2- (ethylthiocarbonyl) ethyl / 2- (methylthiocarbonyl / propyl) and 2- (methylthiocarbonyl) -2 phenylethyl, carbamylmethyl, 2-carbamylethyl, 2-methylcarbamylethyl, -2-ethylcarbamylethyl, dimethylcarbamylmethyl, 2-diethylcarbamylethyl, thiocarbamylmethyl, 2-thiocarbamylmethyl, 2-thiocarbamylmethyl, 2-thiocarbamylmethyl, 2-fenylokarbamylo / ether. .

When n ^ l and Ri and / or R₃ is an acyl group

COR₇, then R7 is a hydrogen atom, an unsubstituted or substituted aliphatic radical of 1 to 20, preferably 1 'to 19 carbon atoms, such as: methyl, ethyl, propyl, butyl, n-hexyl, n-octyl, 2-ethylhexyl, n-decyl, n-undecyl, n-tridecyl, n-tetradecyl, n-hexadecyl, n-heptadecyl, eicosyl, chloroethyl, chloroethyl, chloro methylthioethyl, ethylthioethyl, ethylthioethyl, or - dodecylthioethyl, an alkenyl radical of 2 to 20, preferably 2 to 17 and most preferably 2 to '6 carbon atoms such as vinyl, allyl, 2-methylallyl, isobutenylphosphates, and hexenyl; an alkynyl radical of 2 to 20, preferably 2 to 6 carbon atoms such as propargyl, a cycloalkyl radical of 5 to 12, preferably 6 to 1Ó, and most preferably - 6 - carbon atoms such as cyclopentyl or cyclohexyl; an aralkyl radical of 7 to 14, preferably 7 to 13, and most preferably 7 to 9 carbon atoms such as henzyl, β-phenylethyl, diphenylmethyl, or styryl, unsubstituted aryl radical of 6 to 14, preferably 6 to '1' carbon atoms such as phenyl or naphthyl; an aryl radical substituted e.g. with an alkyl radical of 1 to 4 carbon atoms such as tolyl, p-tertyl-phenyl; R7 may also be a heterocyclic furan or thiophene ring radical. Compounds in which Rt and / or R3 are unsaturated acyl radicals work preferably only if only one of the radicals R_b or R₈ is an unsaturated acyl radical.

Examples of Ri and / or R acyl radicals are formyl, -acetyl, propionyl, n-butyryl, hexanoyl, heptanoyl, octanoyl, n-dodecanoyl, n-dedecanoyl, n-heptadecanoyl, n-octadecanoyl, 2-ethylhexyl 2,4 - phimethylpentanoyl, n-tetradecaroyl, n-hexadecanoyl, n-eicosyl, acryloyl. , α-methacryloyl, crotonyl, undeca-10-enoyl, octadec-9-enoyl, β-methylthiopropionyl, methylthioacetyl, β-octythiopropionyl, β-dodiylthiopropionyl, cyclopentanoyl, cyclohexylphenylacetyloylacanoyl , β-phenylpropionyl, diphenylacyl, β-phenylacryloyl, o-, m- and p-toluyl, o-, m-, p-methoxybenzoyl, o-, m-, and p-chlorobenzoyl, 2-furoyl and 2^jpikolinoilowy.

When n = 1, Rt and / or R3 may be a carbamyl or thiocarbamyl radical of formula 8, where X_s is an oxygen or sulfur atom, R₈ is a hydrogen atom or an alkyl radical with 1 to 4 Carbon atoms; - and R_fl is a hydrogen atom, an alkyl radical with 1 to 20 carbon atoms, or an alkenyl radical with 3 to 20 carbon atoms, or a cycloalkyl radical with 5 to 12 carbon atoms, or an unsubstituted aryl radical, or an aryl radical substituted with an alkyl radical, for example - an alkyl or chloroalkyl radical with 6 to 12, preferably 6 to 10 carbon atoms. The substituents in this group are such radicals as: carbamyl, N-methylcarbamyl, N-ethylcarbamyl, Nn-propylcarbamyl, N-isopropylcarbamyl, Nn-butylcarbamyl, Nn-pentylcarbamyl, Nn-octylcarbamyl, Nn-decylcarbamyl, Nn-decylⁿ-d ° 'decylcarbamyl, Nn-octadecylcarbamyl, Nn-eicosylcarbamyl, N-allylcarbamyl, N-methylallylcarbamyl, N-undeCenylcarbamyl, N-cyclopentylcarbamyl, N-cycloalkyl, cycloalkylcycloalkyl -perhydronaphthyl / -amyl carbam, Ń-adamantylcarbama 90 214

Iowa, N-cyclopentylmethylcarbamyl, N-benzylcarbamyl, N- (phenylethyl) -carbamyl, N- (1- and 2-naphthylmethyl) -carbamyl, N-phenylcarbamyl, Nn / Ο-, m- and p-tolyl) - carbamyl, N- / 2,4- and 2,6-xylyl / carbamyl, N-ι / α- and β-naphthyl / carbamyl, N, Nd

Ν, Ν-dimethylcarbamyl, N-methyl-N-ethylcarbamyl, N, N-diethylcarbamyl, N, N-diisopropylcarbamyl, N, N-di-n-propylcarbamyl, N, N-di-n-butylcarbamyl,

N, N-diisobutylcarbamyl, and the corresponding thiocarbamyl radicals.

Examples of suitable R radicals₂ are: alkyl radicals such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, preferably methyl; alkenyl radicals such as allyl, methylallyl, 3-hexenyl, 4-octenyl, 6-decenyl, 10-undecenyl, and 8-octadecenyl, preferably allyl and 2-methylallyl; alkynyl radicals such as propargyl, but-1- and 2-ynyl, pent-1-ynyl, hexyl, oct-1-ynyl, dec-1-ynyl, dodec-1-ynyl, tetradec-1-ynyl, octadec-1-ynyl, preferably propargyl; cycloalkyl radicals such as cyclopentyl, cyclohexyl, cyclooctyl, cyclododecyl, preferably cyclohexyl; aryl radicals such as phenyl, p-tolyl, t-butylphenyl, naphthyl, preferably phenyl and p-tolyl; aralkyl radicals such as benzyl, α-methylbenzyl, para-dimethylbenzyl, preferably benzyl.

When n = 1, the R3 radical may be the same as the Rt radical. If the R3 radical is an alkyl radical it is preferred that it has 3 to 18 carbon atoms. R_s it may also be an aryl radical with 6 to 20, preferably 6 to 12 carbon atoms, and most preferably phenyl, if R3 is a cycloalkyl radical it may be a cyclopentyl, cyclohexyl, cyclooctyl or cyclododecyl radical.

When n = 2, the R3 radical is an alkylene radical of 1-20, preferably 2-6 carbon atoms, such as methylene, ethylene, trimethylene, four-methylene, and six-methylene; an alkenylene radical with 3-20, most preferably 3 and 4 carbon atoms such as 1,3-propen-2-ene or 1,4-buten-2-ylene; an alkynyl radical of 3-20, preferably 4 carbon atoms, such as 1,4-but-2-ynylene; a cycloalkylidene radical preferably having 6-8 carbon atoms, preferably cyclohexyl dimethylene; an arylene radical preferably having from 6 to 12 carbon atoms such as 1,3-phenylene and 4,4'-diphenylene; or an ar alkyl radical such as αα, -ρ-xylene.

Examples of suitable diacyl R radicals_s are aliphatic, aromatic or heterocyclic radicals of dicarboxylic acids. Examples of aliphatic dicarboxylic acids with 2 to 20 carbon atoms are as follows: malonic, succinic, glutaric, adipic, pimelic, cork, azelaic, sebacic, decanedicarboxylic acid 1,10, hexadecanedicarboxylic acid 1,16, eicosanedicarboxylic acid -metyloiminodwuoctowy. Examples of aromatic dicarboxylic acids are: phthalic, isophthalic and terephthalic acid, each of which may be substituted on the ring with a halogen atom, an alkyl or alkoxy radical with 1-20 carbon atoms, and a hydroxyl group or a tertiary amine group. Examples of heterocyclic dicarboxylic acids are: 2,5-thiophene dicarboxylic acid, and 2,5-furanedicarboxylic acid.

Examples of suitable dicarboxyl radicals R3 are aliphatic and aromatic dicarbomyl radicals such as the alkyl divalent dicarbamyl radical, e.g. the divalent butane-1,4-dicarbamyl radical, or hexane-1,6-dicarbamyl, or the aryl divalent dicarboxyl radical, e.g. 4-dwukarbamylowy.

Examples of suitable R3 dithiocarbamyl radicals are aliphatic and aromatic dithiocarbamyl radicals such as the alkyl divalent dithiocarbamyl radical, e.g.

When n = 3, R3 can be a triacyl radical of an aliphatic tricarboxylic acid such as: triacetic acid nitrile, carboxyl allyl trinity, or aromatic tricarboxylic acid e.g. benzene tricarboxylic acid, or an inorganic acid such as * orthophosphorous, orthophosphoric, orthoboric acid, or such acid as benzene-l, 3,5-trisulfonic.

When n = 4, R3 can be a four-acyl radical of a tetra-carboxylic acid such as ethylene diamine tetra-carboxylic acid, or tetra-carboxylic acids described in British Patent No. 1080335, i.e. 1,2,4,5-benzene tetra-carboxylic acid, or orthosilicic acid.

Preferred R1 substituents are alkyl or N-substituted carbamyl radicals.

Preferred R1 substituents are alkyl, alkenyl, substituted alkyl substituted alkyl radicals such as hydroxyalkyl, or carbonyloxyalkyl.

Examples of compounds of formula I used to stabilize the polymers of the invention in which n = 1:

4-methoxy-2,2,6,6-pięciometylop.iperydyna.

4-n-butoxy-l, 2,2,6,6-pięciometylopiperydyna.

4-n-dodecyl^l-ethoxy-lL, 2,2,6,6-pięciometylopi^andperidine, 4-n-octadecyloxy-1,2,2,6,6-five-methylpiperidine, 4- / 2'-cyanoethyloxy / -1L2L2L6, ^ 6-pentomethylpiperidine,

4- / 2'-hydroxyethoxy / -1L2L2L6L6-δ-methylpiperidine, n-propyl-4-methoxy-2,2,6,6-tetramethyl-piperidine, n-propyl-4-n-deoxy-2,2,6, 6-tetramethylpiperidine, l-propyl-4-nOkt-decyloxy-2,2,6,6- &lt;isteromethylpiperidine, l-t-butyl-4-n-dodecyloxy-2,2,6,6-tetramethylpiperidine, ln -oktyiM-methoxy ^ - tetramethylpiperidine, ln-dodecyl-4-n-dodecyloxy-2,2,6,6-tetramethylpiperidine, ln-octadecyl-4-methoxy-2,2,6,6-tetramethylpiperidine, ln-octadecyl-4-n-octadecyloxy-2,2,6,6-tetramethylpiperidine, ln-eicosyl-4-methoxy-2,2,6,6-tetramethylpiperidine, 1-allyl-4-methoxy-2,2, 6,6-tetramethylpiperidine, 1-allyl-4-allyloxy-2,2,6,6-tetramethylpiperidine, 1- (1'-undecen-10'-yl) -4-n-butoxy-2,2,6 , 6-tetramethylpiperidine, 1- (1'-undecen-10'-yl) -4- / 1'-undecen-10'-yloxy / -2,2,6,6-tetramethylpiperidine, 1-oleyl-4-methoxy -2,2,6,6-tetramethylpiperidine, 1-oleyl-4-oleyloxy-2,2,6,6-tetramethylpiperidine, 1-propargyl-4-ethoxy-2,2,6,6-tetramethylpiperidine, 1-propargyl-4-propargyloxy-2,2,6,6-tetramethylpiperidine, &lt;

1-benzyl-4-n-dodecyloxy-2,2,6,6-four-methylpiperidine, 1-benzyl-4-allyl; sy-2,2,6,6-four-methylpiperidine, 1-benzyl-4-propargyloxy-2, 2,6,6-tetramethylpiperidine, 1-benzyl-4-benzyloxy-2,2,6,6-tetramethylpiperidine, 1- (2'-hydroxyethyl) -4-methoxy-2,2,6,6-tetramethylpiperidine, lV2'-hydroxy-ethyl / -4-allyloxy-2,2,6,6-four-methylpiperidine, 1- (2'-hydroxyethyl) -4-propargyloxy-2,2,6,6-tetramethylpiperidine, 1- / 2'- hydroxypropyl / -4-benzyloxy-2,2,6,6-czterometylopiperydyna. 1- / 2'-hydroxyethyl / -4-Z2'-hydroxyethoxy / -2,2,6,6-tetramethylpiperidine, 1- (2'-hydroxypropyl) -4- (2'-hydroxypropoxy)^,-2,2,6,6-tetramethylpiperidine, 1- (2'-hydroxy-2'-phenylethyl) -4-n-butoxy-2,2,6,6-tetramethylpiperidine, 1- / 2'-hydroxy-2 '-phenylethyl / -4- (2'-hydroxy-2'-phenylethoxy) -2,2,6,6-four-methylpiperidine, 1- (2'-chloroethyl) -4-n-dodecyloxy-2,2,6, 6-tetramethylpiperidine, 1- (2'-chloropropyl) -4-benzyloxy-2,2,6,6-tetramethylpiperidine, 1- (2'-bromoethyl) -4- / 2'-bromoethoxy / -2,2,6 , 6-tetramethylpiperidine, 1- (2'-chloro-2'-phenylethyl) -4-n-octyl^lxy-2,2,6,6-tetramethylpiperidine, 1- (2'-cyanoethyl) (/ - 4-phenoxy-2,2,6,6-tetramethylpiperidine)

- / 2'-cyanoethoxy / -4-benzoxy-2,2,6, '6-tetraethyl lopiperidine, 1- (2'-cyanoethyl / -4- / 2'-cyanoethoxy / -2,2, 6,6-tetramethylpiperidine, 1- (2'-cyanopropyl) -4-methoxy-2,2,6,6-tetramethylpiperidine,

1/2 ', 3'-epoxypropyl / -4-n-butoxy-2,2,6,6-czterometylopiperydyna.

1- / 2 ', 3'-epoxypropyl / -4-benzyloxy-2,2,6,6-tetramethylpiperidine, 1- (2', 3'-epoxypropyl / -4- / 2 ', 3'-epoxypropoxy) - 2,2,6,6-czterometylopiperydyna.

214 '10 1- (2'-methoxyethyl) -4-ethoxy-2,2,6,6-four-methylpiperidine, 1- (2'-methoxyethyl) / -4 - /' 2'-methoxyethoxy / -2,2,6, 6-four-methylpiperidine, 1- (2'-ethoxypropyl) -4-allyloxy-2,2,6,6-four-methylpiperidine, 1- (2'-ethoxy-2'-phenylethylZ-4-benzyloxy-2,2), 6,6-methylmeterpiperidine, 1- (2'-acetoxyethyl) -4-n-butoxy-2,2,6,6-tetra-methyl piperidine, 1- (2'-benzoyloxyethyl / -4- / 2'-benzoyloxyethoxy / -2,2,6,6-czterometylopiperydyna. l- / 2'-propionoksypropylo / 4-allyloxy-2,2,6,6-czterometylopiperydyna.

- [2 '- / finish lokarbamy loxy / ethyl] -4-benzyloxy-2,2,6,6-tetramethylpiperidine, 1- [2' - / methylcarbamyloxy] -4- [2'-methylcarbamyloxy / ethoxy] -2 , 2,6,6-tetramethylpiperidine, 1- [2 '- / phenylcarbamyloxy, / ethyl] -4- [2^,- / cyanoethoxy /] - 2,2,6,6-tetramethylpiperidine, 1- '[2' - / ethylthiocarbamyloxy / ethyl] -4- [2 '- / ethylthiocarbamyloxy / ethoxy] -2,2,6,6-tetramethylpiperidine , 1-methylcarbonylmethyl-4-methoxy-2,2,6,6-tetramethylpiperidine, 1 - [/ methylcarbonyl / ethyl] -4-n-octyloxy-2,2,6,6-tetramethylpiperidine, 1-methylcarbonylmethyl-4- methyl carbonylmethoxy-2,2,6,6-tetramethylpiperidine, 1- (2'-methoxycarbonylethyl) -4- (2'-methoxycarbonylethoxy) -2,2,6,6-tetra methylpiperidine, l- / 2'-methoxycarbonylethyl / -4-ethoxy-2,2,6,6-czterometylopiperydyna.

1- [2 '- / ethoxy barbon / ethyl] -4- / 2'-hy-oxy ethoxy Z-2,2,6,6-tetramethylpiperidine, 1- [2' - / thioethoxycarbonyl / ethyl] -4- methoxy-2,2,6,6-tetramethylpiperidine, 1-carbamylmethyl-4-benzyloxy-2,2,6,6-tetramethylpiperidine, 1- (2'-carbamylethylZ-4-dodecyloxy-2,2,6,6- tetramethylpiperidine, 1- [2 '- / methylcarbamyl / ethyl] -4- / 2'-methylcarbamylethoxyZ-2,2,6,6-tetramethylpiperidine, 1- [2' - / methylcarbamyl / ethyl] -4-methoxy-2 , 2,6,6-czterometylopiperydyna. 1-thiocarbamylmethyl-4-allyloxy-2,2,6,6-tetramethylpiperidine, 1- (dimethylthiocarbamyl) methyl-4-benzyloxy-2,2,6,6-tetramethylpiperidine, 1-acetyl-4-benzyloxy-2,2 , 6,6-tetramethylpiperidine, 1-laurolyl-4- (2'-hydroxyethoxy) -2,2,6,6-tetramethylpiperidine, 1-stearoyl-4-methoxy-2,2,6,6-tetramethylpiperidine, 1- benzoyl-4-n-butoxy-2,2,6,6-tetramethylpiperidine, 1-carbamyl-4-n-octadecyloxy-2,2,6,6-tetramethylpiperidine, 1-methylcarbamyl-4-benzyloxy-2,2, 6,6-czterometylopiperydyna. 1-phenylcarbamyl-4- (2'-hydroxyethoxyZ-2,2,6,6-tetramethylpiperidine, 1-phenylthiocarbamyl-4- (cyclohexyloxy) -2,2,0,0-tetramethylpiperidine,

214 1,1,1-dimethylcarbamyl-4-methoxy-2,2,6,6-tetramethylpiperidine, 1-methylthiocarbamyl-4-n-octyloxy-2,2,6,6-tetramethylpiperidine, 1-phenylthiocarbamyl-4-methoxy-2, 2,6,6-czterometylopiperydyna&gt;

1,2,2,6,6-pentymethyl piperate formate,

4- 1,2,2,6, -6-five-methyl piperate acetate,

1,2,2,6,6-five-methylpiper pipine isobutyrate,

1,2,2,6,6-pentathio-lopiperidine 4-n-heptane carboxylate,

1,2,2,6,6-five-methyl piperidine 4-trimethylacetate, 1,2,2,6,6-five-methyl piperidine 4-stearate, 1,2,6,6-pentylpiperidine 4-nonadecacarboxylate,

4- / 2'-ethylpentane carboxylate / 1,2,2,6,6-five-methylpiperidine,

1,2,2,6,6-five-methylpiper piperacrylate,

1,2,2,6,6-pentylpiperidyl 4-oleate, 1,2,2,6,6-pentylpiperidine 4-cyclohexane carboxylate,

1,2,2,6,6-pentymethylpiperidine 4-adamate-1-carboxylate, ».

1,2,2,6,6-pentomethylpiperidine 4-benzoate, 1,2,2,6,6-pentomethylpiperidine 4-p-toluate, 1,2,2,6-tert-butylbenzoate, 6-five you lopiperidine,

1,2,2,6-l-piperidine 4-p-methoxybenzoate,

1,2,2,6,6-pentymethylpiper piperine 4-o-chlorobenzoate,

1,2,2,6,6-pentymethylpiperidine 4-p-chlorobenzoate,

Dyne 4-α-naphthoate 1,2,2,6,6-pentymethyl pipers, 1,2,2,6,6-pentane 5-pentene dyne dyes, 4- / 1'-naphthylacetate / 1,2,2 , DJ6.6-pentyl methyl piperate, 1,2,2,6,6-pentamethyl piperidine 4-cinnamate, 1,2,2,6,6-pentamethylene diphenylacetate, 4-n-dodecylthioacetate 1,2,2 , 6.6-five thouine lopipers,

4- / furan-2'-carboxylate / 1,2,2,6,6-five-methyl piperidine, 1,2,2,6,6-pentyl methyl piperidine dimethyl mesoate, 1-n-propyl-2,2 acetate L-propyl-2,2,6,6-tetramethylpiperidine 4-n-heptane carboxylate, 6,6-tetramethylpiperidine,

1-nTpropyl-2,2,6,6-tetramethylpiperidine 4-stearate,

Ln-octyl-2,2,6,6-tetramethylpiperidine 4-benzoate,

L-dodecyl-2,2,6,6-tetramethylpiperidine 4-n-heptane carboxylate,

L-dodecyl-2,2,6,6-tetramethylpiperidine 4-p-chlorobenzoate,

Ln-octadecyl-2,2,6,6-tetramethylpiperytifin 4-benzoate,

1-allyl-2,2,6,6-tetramethylpiperidine 4-n-heptane carboxylate,

1-allyl-2,2,6,6-tetramethylpiperidine 4-cyclohexane carboxylate,

1-allyl-2,2,6,6-tetramethylpiperidine 4-benzoate, 1-methylallyl-2,2,6,6-tetramethylpiperidine 4-acetate,

1-oleyl-2, a, 6,6-tetramethylpiperidine 4-cyclohexane carboxylate,

4-p-methoxy benzoin an 1- - propar gilo / -2,2,6,6 * four ometines of dyne lopiper

1-benzyl-2,2,6,6-tetramethylpiperidine 4-n-heptane carboxylate,

4- / l-ethylhexanoate / l-benzyl-2,2 ^ 6-czterometylopiperydyny,

1-benzyl-2,2,6,6-tetramethylpiperidine 4-stearate,

1-benzyl-2,2,6,6-tetramethylpiperidine 4-benzoate,

1- (2'-hydroxyethyl) -2,2,6,6-tetramethylpiperidine 4-acetate

1- (2'-hydroxyethyl) -2,2,6,6-tetramethylpiperidine 4-laurate,

1- (2'-hydroxyethyl) -2,2,2,6-tetramethylpiperidine 4-stearate,

1- (2'-hydroxyethyl) -2,2,2,6-tetramethylpiperidine 4-benzoate,

1- (2'-hydroxypropyl) -2,2,6,6-tetramethylpiperidine 4-oleate,

1- (2'-hydroxy-2'-phenylethyl) -2,2,6,6-etertermethylpiperidine 4-phenylacetate,

1- (2'-chloroethyl) -2,2,6,6-tetramethylpiperidine 4-n-heptane carboxylate,

1- (2-bromopropyl) -2,2,6,6-tetramethylpiperidine 4-cyclohexane carboxylate 1- (2'-chloro-2'-phenylethyl) -2,2,6,6-tetramethylpiperidine, 4-p-methoxybenzoate,

1- (2'-cyanoethyl) -2,2,6,6-tetramethylpiperidine 4-benzoate,

1- (2'-cyanopropyl) -2,2,6,6-tetramethylpiperidine 4-p-chlorobenzoate,

1- / 2 - ', 3'-epoxypropyl / -2,2,6,6-tetramethyl · piperidine 4-acetate,

4- (1'-ethylpentane carboxylate) -1- (2'-ethoxypropyl) -2,2,6,6-tetramethylpiperidine, 4-diphenylacetate 1- (2'-ethoxy-2'-phenylethyl) -2,2,6 , 6 · -methylpiperidine,

1- (2'-acetoxyethyl) -2,2,6,6-tetramethylpiperidine 4-laurate,

1- [2 '- / Loxy / methyl ethyl carboxylate] -2,2,6,6-tetramethylpiperidine, 4-benzoate,

1- [2 '- / phena Loxyl Barrel Loxy / -ethyl] -2,2,6,6-tetramethylpiperidine 4-isobutyrate,

1- [2 '- / ethylthiocarbamyloxy / ethyl] -2,2,6,6-tetramethylpiperidine 4-trimethylacetate,

1-Methylcarbonylmethyl-2,2,6,6-phenylmethylpiperidine 4-phenylacetate,

1- [2'-methylcarbonyl / ethyl] -2,2,6,6-tetramethylpiperidine 4-acetate,

1-ethoxycarbonylmethyl-2,2,6,6-tetramethylpiperidine 4-p-methoxybenzoate,

1- (2 '- / methoxycarbonyl) ethyl-2,2,6,6-tetramethylpiperidine 4-p-toluate,

1-carbamylmethyl-2,2,6,6-tetramethylpiperidine 4-p-methoxybenzoate,

1- (2'-carbamylethyl) -2,2,6,6-tetramethylpiperidine 4-stearate,

1- (2 '- / methylcarbamyl / ethyl) -2,2,6,6-tetramethylpiperidine 4-heptane-carboxylate,

1- (dimethylthiocarbamyl) methyl-2,2,6,6-tetramethylpiperidine 4-isobutyrate,

1-acetyl-2,2,6,6-tetramethylpiperidine 4-acetate,

9θ · 214

4- / r-ethylpentanecarboxylate / 1-acetyl-2,2,6,6-tetramethylpiperidine,

1-acetyl-2,2,6,6-tetramethylpiperidine 4-stearate

1-isobutyryl-2,2,6,6-tetramethylpiperidine 4-n-heptane carboxylate,

1- ^^ £ ^ and ^: ^: lo5222 !,, 6,6-tetraethylpiperidine, 4-nonadecanecarboxylate,

1-stearyl 4-acetate S / G-tetramethylpiperidine, 1-phenyoyl-2,2,6,6-tetra-4-benzoate; ylpiperidine,

4- (1'-naphthylacetate) / 1 - ^^^] ^ b ^^ n ^ yl3-: 22,6,6-cz ^ eromethylpiperidine,

1-methylcarbamyl-2,2,6,6-tetramethylpiperidine 4-n-heptane carboxylate,

1-phenylcarbamyl-2,2,6,6-tetramethylpiperidine 4-phenylacetate, 1- ^ c ^ 4-laurate in ^ and ^ n ^ ^ '^ 17 &lt;^^^ r3aE ^; lo - 22i, 6, 6-cz ^ erometylopiperydyny.

4-p-H-butylbenzoate and 1-phenylthiocarboxinyl-2,2,6,6-cteromethylpiperidine,

4-carbamoyloxy-l, 2,2,6,6-pięciometylopiperydyny.

4-methylcarbamyloxy-l, 2,2,6,6-Oc € iometylopiperydyna.

4-dwumetylokarbamyloksy-l, 2,2,6,6-pięciometylopiperydyna.

4-izopropylokarbamyloksy-1,2,2,6,6-pięciometylopiperydyna.

4-nirz.butylokarbamyloksy-l, 2,2,6,6-pięeiometylopiperydyna.

4-n-heksylokarbamyloksy-l, 2,2,6,6-pięciometylopiperydyna ,.

4- / 2'-etyloheksylokarbamyloksy / l, 2,2,6,6-pięciometylopiperydyna.

4-n-dodecylokaΓramylolk »yl, 2,2,6,6-pięciometylopiperydyna.

4-n-propoxy-oktadecylokarramyl &lt;&lt; l, 2,2,6,6-pięciometylopiperydyna.

4-allylcarbamyloxy-1,2,2,6,6-five-methylpiperidine, '

4-oleilokaΓbamyloksy-l, 2,2,6,6-pięeiometylopiperydyna.

4-cycle · t] · heksylokaΓbamyl oxy-l, 2,2,6,6-pięciometylopiperydyna.

4- / 3'-methylcycloheteylcafbamyloxy / -1, 2,2,6,6-five-methylpiperidine,

4- / 4'-ΠlΓz.butyl-cyclohexylcarbamyloxy-II, 2,2,6,6-five-methylpiperidine,

4-eykloheksylometylokarbamyloksy-l, 2,2,6,6-pięeiometylopiperydyna.

4-benzylcarbamyloxy-1,2,2,6,6-five-methylpiperidine, ^v

4-phenylcarbamyloxy-1,2,2,6,6-five-methylpiperidine,.

4-fenylotiokarbamyloksy-1,2,2,6,6-pięciometylopiperydyna. _t *

4-m-tolyl-carbamyloxy-1,2,2,6,6-p-methyl-methyl piperidine, ^ p-tolyl] carbamyl-1,2,2,6,5-five] ^ thylpiperidine,

4 ~ p-ehlorofenylokaΓramyloksy-l, 2,2,6,6-pięciometylopiperydyna.

4-p-IIIrz.butylofenylokarbamyloksy ^ l ^ 2,2,6,6 pięciometylopiperydyna.

4-a-naftylokarbamyloksy-l, 2,2,6,6-pięciometylopiperydyna.

Cykloheksylokarbamyloksy-4-ethyl-2,2,6,6-czteΓometylopiperydyna. ₅ 4-metylokarramyloksy-ln-propyl-2,2,6,6-ezterome_? tylopiperydyna,

4-metylokarramyloksy-l-IIzz.buty &lt;o-2,2,6,6-czterometylopiperydyna.

4-n-oktadecylokarramyloksy-ln-butyl &lt;o-2,2,6,6-ezte₁₀ rometylopiperydyna, ^v

MetylokaΓbamyloksy-4-n-octyl ^ - 2,2,6,6-etterometylopiperydyna.

4-methylcarramyloxy-11-octaeecyl-2,2,6,6-ctteromethylpiperidine, in 4-phenylcarramyloxy-1-allyl-2,2,6,6-ezteromethyl piperidine,

4-p-tolylcarramyloxy-1-oleyl-2,2,6,6-eterteromethylpiperidine,

4-methylcarramyloxy-1-propaΓgyl-2,2,6,6-ezteΓO20 methylpiperidine,

4-fenylokarramyloksy-l-benzyl &lt;o-2,2,6,6-czteΓometylopiperydyna.

4-metylokarramyloksy-l- / 2'-hydΓl) hydroxyethyl / -2,2,6,6-czterometylopiperydyna.

4-cyclohexylcarbamyloxy-1- (2'-chloropropyl) -2,2,6,6-cteromethylpiperidine, 4-phenylcarramyloxy-1- (2'-hydroxy-2'-phenylethyl) -2,2,6,6 -ccteromethylpipeΓidine, 4-methylcarbamyloxy-1- / 2 ', 3'-epoxypropyl / 30 -2,2,2,6-ccttromethylpiperidine,

4-carbamyloxy-1 / 2'-mt &lt;oxetty &lt;o - 2,2,6,6-ctteromethylpiperidine, ·

4-dimethylcarbamyloxy-1- (2'-acetoxyethyl) -2,2,6,6 - cttomethylpipeidine, *

4-n-hexylcarbamyloxy-1- (2 '- / methylcarbamyloxy / ethyl) -2,2,6,6-tetramethylpiperidine, 4-methylcarramyloxy-1-methylcarbonylmethyl-2,2,6,6-cteromethylpiperidine,.

4-phenylcarramyloxy-1- (2'-methylcarronylethyl) 40 -2,2,6,6-cttrolmethyl piperidine,

4-renzylokarbamyloksy-l-kaΓramylometylo-2,2,6,6-czterometylopiperydyna.

4-n-dodecyloka-bamyloxy-1- (2'-carramylethyl) -2,2,6,66ccteromerylpiperidine, &lt;0 4-mrtylcarramyloxy-1- / 2 - t &lt;carbames

-2,2,6,6-ccttromethylpiperidine, 4-methylcarramyloxy-1-acetyl-2,2,6_, 6-tetra-methylpiperidine,

4-phenyloka-ramyloxy-1-stearoyl-6,2,6,6-tetra-methyl-piperidine,

4-metylotiokarbamyloksy-1-lauroyl-2,2,6,6-ęzterometylopiperydyna.

4- / 2'-etyloheksylokarbamyloksy-l-benJwilo-2,2,6,6-czterometylopiperydyna.

4-carbamoyloxy-l-carbamoyl-6,2,6,6-czterometylopiperydyna.

4-methylcarramyloxy-1-mrtylocarbamate: yl-2,2,6,6-eteromethylpiperidine, θθ 4-phenylcarbamyloxy-1-phenylcarrama 1-2,2,6,6-tetra methylpiperidine,

4-metylotiokarbamyloksy-l-metylotiokarbamylo-2,2,6,6-ccterometylopiperydyna.

4-fenylotiokarb_ANDamyoxy-1-phenylthiocarramyl '-2 -2,2,6,6-cteromerylpiperidine,'

214

16

4-dimethylcarbamyloxy-1-dimethylcarbonyl-2,2,6,6-tetramethylpiperidine, 4-stearyloxy-1,2,2,6,6-hexylpiperidine, 4-phenyl-1,2,2-heptane carboxylate, 6.6-five-methylpiperidine 5

Examples of compounds in which n = 2:

1.2- his / 1 ', 2', 2 ', 6', 6'-five-methyl-4'-piperidyloxy / ethane,

1.4- bis / 1'-n-propyl-2 ', 2', 6 ', 6'-fourmeters! O-4'-piperidine&gt; xy / butene, 1,6-bis / rn-octadecyl-2', 2 ', 6', 6'-tetra-methyl-4'-pi- and peridyloxy / hexane,

1.4- bis / l'-allyl-2^,J2 ', 6^,,6^,tetramethyl-4^AND-piperydyloksy / cyclohexane

1.4- bis / 1 '-propergyl-2', 2 ', 6', 6'-four-back-4-piperidyloxy / butene-2, 15 a, a-bis / 1-benzyl-2,2,6,6 tetramethyl-4-piperidyloxy / p-xylene,

1.3- bis / r- (2-hydroxyethyl) -; 2 ', 2',^,6^,, 6'-tetra-methyl-4'-piperidyloxy-benzene, 1, 2-bis / r- (2-cyanoethyl / -2 ', 2', 6 ', 6'-tetra methyl-4'-20-piperidyloxy) - ethane,

1.4- bis / l '-acet lo-2', 2 ', 6', 6'-tetraethyl lo-4'-piperyl dyloxy / butin-2,

4.4- bis / 1-methylcarbamyl-2,2,6,6-tetra-methyl-4-piperidyloxy / diphenylmethane, carbonate, bis / 1,2,2,6,6-five-methyl-4-piperidyl oxalate, bis / 1, 2 oxalate , 2,6,6-five-methyl-4-piperidyl), bis malonate (1,2,2,6,6-five-methyl-4-piperidyl), bis (1,2,2,6,6-pentomethyl-4 adipate) -piperidyl), bis sebacate / 1,2,2,6,6-pentomethyl-4-piperidyl- ³⁰y /, ✓ f umar an bis (1,2,2,6,6-pentomethyl-4-piperidyl), isophthalic acid bis / 1,2,2,6,6-pentomethyl-4-piperidyl /, r, 4 ' - bis / 1,2,2,6,6-pentomethyl-4-piperidyl / cyclohexyl dicarboxylate /, bis / 1,2,2,6,6-pentomethyl-4-piperidyl / thiodipropionate /, bis / 1, 2,2 , 6,6-pentomethyl-4-piperyl /, bis (1-propyl-2,2,6,6-tetra-methyl-4-pyridyl) adipate /, bis buccinate / I-t-butyl-2,2 , 6,6-tetramethyl-4-piperidyl /. bis sebacate (In-octyl-2,2,6,6-tetramethyl-4-piperidyl), bis adipate_Tdodecyl-2,2,6,6-tetra-methyl-4-piperidyl), bis sebacate (11-octadecyl-2,2,6,6-tetra-methyl-4-piperidyl), bis / 1-allyl-2,2 adipate, 6,6-tetramethyl-4-piperidyl), thiophene-2 ​​', 5'-dicarboxylate bis / 1-allyl-2,2,6,6-tetramethyl-4-piperidyl), bis thiopyropionate -2,2,6,6-tetramethyl-4-piperidyl), bis sebacate / 1-propargyl-2,2,6,6-tetra-methyl-4-piperidyl), bis sebacate / 1-benzyl-2,2, 6,6-tetramethyl-4-piperidyl /. bis (1- / 2'-hydroxyethyl) -2,2,6,6-tetraethyl-4-piperidyl) adipate, bis / 1- (2'-chloropropyl) bisuccinate / -2,2,6,6 - tetramethyl-4-piperidyl), bis sebacate (1- (2'-cyanoethyl) -2,2,6,6-tetramethyl-4-piperyl), bis azelaate (1- (2 ', 3-epoxypropyl) -2,2,6,6-tetra-methyl-4-piperidyl), bis pimelate (1- (2'-methoxy ethyl) -2,2,6,6-four ometyl-4-piperyl), bis glutarate / 1- / 2'-acetoxyethyl / -2,2,6,6-tetra-4-piperidyl), bis (1-2'-methylcarbamyloxyethyl) -2,2,6,6-tetramethyl-4-piperyl malonate, bis (1- (methylcarbonylmethyl) ethyl terephthalate) -2,2,6,6-tetramethyl-4-piperidyl. cyclohexane dicarboxylate-1,4 ', 4'-bis (1-carbamylmethyl-2,2,6,6-tetramethyl-4-piperidyl), bis / 1- (methylcarbamylethyl) thiodopropionate / -2,2,6,6-tetraethyl 4-piperidyl), bis sebacate (1-acetyl-2,2,6,6-tetra-methyl-4-piperidyl), bis biscinate (1-stearoyl-2,2,6,6-tetra-methyl-4-piperidyl), bis (1-benzoyl-2,2,6,6-tetra-methyl-4-piperidyl) decanedicarboxylate, bis (1-methylcarbamyl-2,2,6,6-tetra-adipate, tylopiperidyl) adipate, bis (1-phenylthiocarbamyl-2) phthalate , 2,6,6-tetramethylpiperidyl /, ethane-1 ', 2'-bis / 4-carbamyloxy-1,2,2,6,6-pentomethylpiperidine, he'xane-1', 6'-bis / 4- carbamoyloxy-l, 2,2,6,6-pięciometylopiperydyna /.

2 ', 4', 4'-trimethylhexan-1 ', 6'-bis / 4-carbamyloxy-1,2,2,6,6-five-methylpiperidine /, cyclohexan-1', 3'-bis / 4-carbamy curls -1,2,2,6,6-five-methylpiperidine /, benzene-1 ', 4'-bis / 4-carbamyloxy ^ 1,2,2,6,6-five-methylpiperidine /, toluene-2', 4'-bis / 4-carbamyloxy-1,2,2,6,6-five-methylpiperidine /, toluene-2^,, 4'-bis / 4-thiocarbamyloxy-1,2,2,6,6-five-, methylpiperidine /, naphthalene-1 ', 5'-bis / 4-carbamyloxy-1,2,2,6,6- pentomethylpiperidine /, diphenylmethane-4 ', 4-bis / 4-carbamyloxy-2,2,6,6-pentomethylpiperidine /, toluene-2', 4'-bis / 4-carbamyloxy-ln-propyl-2,2 , 6,6-tetramethylpiperidine /, hexane-1 ', 6'-bis / 4-carbamyloxy-1n-butyl-2,2,6,6-four ometopes of lopiperidine /, hexane-1', 6'-bis / 4-carbamoyloxy-ln-octyl-2,2,6,6-czterometylopiperydyna /.

2 ', 4', 4'-trimethylhexane-1 ', 6'-bis (4-carbamyloxy-1-octadecyl-2,2,6,6-four-methylpiperidine), cyclohexane-1', 4'-bis / 4- carbamoyloxy-allyl-2,2,6,6-czterometylopiperydyna /.

2',4^,, 4'-trimethylhexane-1 ', p'-bis (4-carbamyloxy-1-allyl-2,2,6,6-tetra-methylpiperidine), benzene-1', 4'-bis / 4-carbanyloxy-1-propargyl - -2,2,6,6-tetramethylpiperidine /, toluene-2 ​​', 4'-bis / 4-carbamyloxy-1-benzyl-2,2,6,6-tetramethylpiperidine /, toluene-2,4'-bis / 4-carbamoyloxy-l- / 2'-hadroksyetylo / 2,2,6,6-czterometylopiperydyna /._v diphenylmethane-4 ', 4-bis (4-carbamyloxy-1- (2'-cyanoethyl) -2,2,6,6-tetramethylpiperidine), i.e., fluene-2,4-bis (4-carbamyloxy-1-) 2-acetoxyethyl / 2,2,6,6-czterometylopiperydyna /.

214 ethane-1 ', 2'-bis (4-cariamamyloxy-1-methylcarbonyl-methyl-2,2,6,6-four-methylpiperidine), hexane-1,6-bis (4-carbamyloxy-1- (2'-methylcarbamylethyl) (-2,2,6,6-tetramethylpiperidine), naphthalene-1 ', 5'-bis / 4-carbamyloxy-acetyl-2,2,6,6-tetramethylpiperidine /, 2', 4 ', 4' - Ri-methylhexane-1,6 '- (4-carbamyloxy-1-stearoyl-2,2,6,6-tetramethyl-piperidine), hexane-1^,, 6'-bis (4-carbamyloxy-methyl-carbamyl-2,2,6,6-tetra-methyl piperidine), bis (1,2,2,6, e-pentomethyl-piperidinyl) ether.

Examples of Compounds in which n = 3: nitrilotriacetate trisZl, 2,2, ^, ^ - ^ and &lt;^ &lt;zi ^ &lt;^ and ^ et ^^; L &lt;^^^^^; pipe: ridinyl, tris / 1-tricarbylate, 2,2,6,6 p-dimethyl-4-piperidinyl /, tris trimethylate (1,2,2,6,6-five-methyl-4-piptryridinyl), Sris trimellitate / 1,2,2,6,6-five-five-Silyl-4- piperidinyl), tris phosphite (1,2,2,6-five-methyl-4-piperidinyl), Sris phosphate (1,2,2,6-five-methylmethyl-4-piperidinyl), »tris borate / 1 2,2,6,6-pięciometylΌ-4-piperydynylrwy /. tris / mesyl-2,2,6,6-tetra-tris-4-piperidine] mesylate, tris phosphite (1, allyl-2,2,6,6-czStromethyl-4-piperidinyl), tris borate (1-proppropyl-2,2,6,6-tetra-methyl-4.-piptridinyl), t-mal-α-tris / 1-benzyl-2,2,6,6-tetra-methyl-4-piperidinyl), tris tris mesylate / 1- / 2'-hydroxytty] o / p2,2,6,6-tetra-methyl-4-piperidinyl), tris phosphite / 1- / 2'-cyanoethyl 1 / -22,2,6,6-tetra methyl] -4-piperidinyl), Sris borate (1-acetyl-2,2,6,6-tetramethyl &lt;1- 4-piperidinyl),

tris tris mesanate (1-mtSyk&gt; carbamyl-2,2,6,6pCzStrpp methyl-piperidinyl).

Examples of compounds in which n = 4: tetrakis (1,2,2,6,6-pentomethyl-4-piperidinyl) eSylene, diamine di-tetra-carboxylate, pyrakym tetrakis (1,2,2,6,6-pentomethyl-4-pipepidinyl) /, silicosilicate Setrakis / 1,2,2, 6,6-pentetyl-4-piptp-ridinyl), Setrakis pyrimethylitanate (1-rycl-2,2,6,6-phenyl-4-piperidinyl) /, teSrakis pyromethylitanoate / 1-α-alkyl-2,2,6,6p C-tetra-rt-pyridinyl] /, tetrakis orthosilicate / 1 -propargilr-2,2,6,6-tetra-octylr-4-piptryridinyl) /, Tetylene (1-benzyl-2,2,6,6-red-methyl-4-piperidinyl) tetrahydro-carbamic acid, tetrakis / 1- (2'-hydroxypropy] r / -2, 2, 6, 6 -SeromeSyl-4- piperidinyl ·, tetrakii pyruvate (1-stearril-2,2,6,6-tetra-methyl-4-piperidinyl), tetra-silicanate, phenylcarbamyl-2,2,6,6-czSeromethyl-4- piperidinyl /.

The invention also includes adding as a stabilizer the salts of the compounds of general formula 1, e.g. salts of inorganic acids such as phosphates, carbonates, sulfates and chlorides, and salts of organic acids such as acetates, stearates, malonates, citrates, tartrates, oxalates, benzoates, and salts of substituted carbamyl acids.

Examples of salt are:

4-n-butoxyyl dihydrogen phosphate, 2,2,6,6-pentameters] rpiperidine, 4-n-dodecyloxy hydrochloride 1,2,2,6,6-pentameters Sy10 lopiperidine, bis / 1,2,2,6 , 6-five-methyl-4-piperidinyl), 1,2,2,6-propionate bicarbonate 1,2,2,6, methyl piperidine] rwy-4-β- / 3 ', 5'-bis - t-butyl-4'-hydroxyfe15 nyl /, 4-methylcarbamyloxy-1, 2,2,6,6-pyrimethyl piperidine acetate, 1, 6-bis / 4'-carbamyloxy-1 ', 2', 2 ', 6', 5'-five-tertyl] opiptridine-hexane /,.

4-phenylcarbamic benzoate] okiy-1,2,2,6,6-pentameters] rpiperidine,

3 ', 5'-di-tert-butyl-4'-hydroxybenzenotsanr-4-n-heptane'α-carboxylate 1,2,2,6,6-methylene piperidylphenyl,.

monoxal oxalate / 1,4-bis / r, 2 ', 2', 6 ', 6'-pentomethyl-4'-piptrydy ^ oxy / butanoic, mono-meleate (4 "/ 2'-pylanoethoxy / -1, 2) , 2,6,6-pentomethylpiperidine /, 4-strearylcarbamate citrate] 1,2,2,6,6-pentylmethylpiperidine, 1-4-n-heptane-carboxylate tartrate 1- (2'-hydroxyethy lr / -2), 2,6,2-csp-methylpiperidinyl, 4-benzoate-dibutylcarbamate 1,2,2,6,6-pentyl] piperidinyl,

Rj or R3 can be a mono-, di-, or trivalent radical obtained by disconnecting 1, 2, or 3 hydroxyl groups from the following acids: sulfonic, sulfinic, disulfonic, phosphorus-containing acids such as orthophosphoric, rrtof · rsfrraw, and from acid boric.

Examples of compounds in which Rt and / or R5 are acid radicals:

a / when n = 1.

1,2,2,6,6 ^ 0 ^ methylpiperidinyl 4-benzenesulfinate,

1,2,2,6,6-parethyl sulfonyl 4-benzenesulfonate,

1,2,2,6,6-pentiomethylpiperidinyl 50-mutyrate],

4-dimethylbrran 1,2,2,6,6-five-methylethylpiperidinyl,

1,2,2,6,6-pentylmethyl pipinyl piperiphenyl 4-phenyls,.

1,2,2,2,6-five-methyl-piperidinyl 4-dimethylphosphran,

4-diphenylrfrsfrranene 1,2,2,6,6-pietermethylpiperidinyl, θθ b / when n = 2 bis / 1,2,2,6,6-piekyrmethyl-4-piperidinyl sulphate /, bis phosphonate, 2,2 , 6,6-five) methylpiperidinyl), monophenyl bis phosphate (1,2,2,6,6-pentomethyl piperidinyl),

SO 214 benzene-1,3-d bis / 1,2,2,6,6-five methylpiperidinyl sulfate, c / when n-3

b.enzene-1,3,5-tris / 1,2,2-trisulfonate, -, - pentomethyl-4-piperidinyl), benzene-1,3,5-tris / 1,2,2-trisulfinate - pięciometylo-4-piperidinyl /.

A subgroup of compounds of general formula 1 having advantageous properties are compounds of general formula 10 and their salts. In the formula and general formula 10, Y is an alkyl radical with 1 to 20 carbon atoms, an alkenyl radical with 3 to 20 carbon atoms, or an aralkyl radical having

7-9 carbon atoms, while, n is 1, 'or 2, and when n_t = 1, R is a hydrogen atom, or a monovalent aliphatic radical with 1-20 carbon atoms, or a monovalent alicyclic radical with 5-12 carbon atoms, or a monovalent aromatic radical with up to 20 carbon atoms and when ^ = 2,

R is a divalent aliphatic radical with 20 to 20 carbon atoms, a divalent alicyclic radical with 5 to 12 carbon atoms, a divalent aromatic radical with -14 carbon atoms. *

Another subgroup 'of compounds of general formula 1 are the compounds of general formula 11 or their. salts. 25

In compounds of the general formula 11, Ya is an alkyl radical of 1-12 carbon atoms, an alkenyl radical of 3-12 carbon atoms, or an aralkyl radical of 7-9 carbon atoms. R ^ is a hydrogen atom,. an alkyl or alkylene radical containing up to 20 carbon atoms, a substituted alkyl radical of the formulas 5 or - in which m is 1, 2 or 3, R4 is a hydrogen atom, or a methyl radical, X_tis a halogen atom or a methoxy radical, and Χ2 is a halogen atom, or R1 is an alkenyl or alkenylene radical having up to 20 carbon atoms, a cycloalkyl or cycloalkylidene group with 5-12 carbon atoms, or an aryl radical, or arylene with -12 carbon atoms. In these compounds q = 1 or 2.

Compounds of formulas 1, 10 and 11 can be prepared by methods known in the art which are outside the scope of the invention, and are described in the following preparation examples. 45

It has been found that by the method of the invention polyolefins can be stabilized by the addition of compounds of general formulas 1, 10 and 11 on the effect of ultraviolet radiation. and heat, while maintaining the color of the stabilized material. These compounds used as stabilizers according to the invention effectively increase the luminous and / or thermal stability of polymers, especially such as: polyethylene, polypropylene and polystyrene 'with varying degrees of polymerization, as well as polymers obtained_;of such compounds as: butene-1, pentene-1,3-methylbuten-1, hexene-1,4-methylpentene-1,4-methylhexene-1, · 4,4-dimethylpenton-1, and copolymers and terpolymers oleifins, especially ethylene and propylene. 60

Other light-sensitive polymers whose properties are improved by the method according to. of the invention by introducing into them the compounds of general formulas 1, 10 and. 11 are those that contain natural and synthetic -5, polymers e.g. natural and synthetic rubbers, 0raz. homo-, co- and terpolymers of acrylonitrile, butadiene and styrene, as well as synthetic polymers containing polyvinyl chloride, polyvinylidene chloride, copolymers with vinyl chloride, polyvinyl acetate, and polymers obtained as a result of polycondensation with ethers, esters / obtained from carboxylic acids, sulfonic acids carbon /, and with amides or urethanes. Polymers can, for example, constitute an essential component of paints or varnishes, which also contain oil or resin, e.g. alkyd or polyamide resin.

Compounds of general formula 1, 10 or 11 are added to the organic raw material in order to minimize the destructive impact in various amounts depending on the properties of the organic raw material, the sharpness of the light radiation and the exposure time. The most suitable amount of compounds of formulas 1, 10 and 11 is 0.01-5%, preferably 0.1-2% by weight based on the weight of the organic raw material. The compounds can be introduced into polymers by known methods. Eg. the compound of formula 1, 10 or 11 and the polymer may be combined in a mixer, or these compounds may be added in the form of a solution or a thick suspension in a suitable solvent or diluent, e.g. in an inert organic solvent such as methanol, ethanol , or acetone to a powdered polymer and mixed in a mixer. Then the solvent is removed. Another method of stabilizing additive according to the invention may be added to the polymer at a later stage of production e.g.^from at the latex stage to obtain a pre-stabilized crude polymer.

The stabilization of polymers by the method of the invention may be accompanied by the addition of one or more admixtures used in the formation of polymers such as: phenol or amine type antioxidants, ultraviolet absorbers, light stabilizers, phosphite stabilizers, peroxide decomposing compounds, polyamide stabilizers, basic co-stabilizers, polyvinyl chloride stabilizers, spore formation agents, cataract polymers, plasticizers, lubricants, emulsifiers, anti-static agents, impregnants flame retardants, pigments, soot, asbestos, glass fibers, kaolin and talc. Together with compounds of formula 1, 10 or 11 added in. in order to stabilize the polymers according to the invention, the addition of the other mentioned substances may range from 0.01 to 5% by weight based on the unstabilized polymeric material.

In a two-component mixture with one or more of the antioxidants mentioned above, or in a three-component mixture with the antioxidant and UV absorber mentioned above, compounds of formulas 1, 10 and 11 are very effective packaging stabilizers made of polyolefin type polymers.

The examples below give methods / preparation of compounds used for. stabilizing polymers by the method of the invention.

Unless otherwise specified, parts and percentages mean parts and percentages by weight.

Example I. A mixture of 10.2 parts, 1,2,2, -, - 90,214

- five-methylpleridinol-4, 6.06 parts of sebacic acid, and 1.0 parts of tetra-n-butyl titanate in 100 · parts of xylene are heated to reflux for 60 hours. Then, xylene is distilled off under reduced pressure to obtain a thick oil, to which 0.5 parts of sodium carbonate, 0.5 parts of carbon and 25 parts of water are added. All v

Refluxed and heated to reflux for 1 hour. Water is distilled off under reduced pressure, and the black residue obtained is repeatedly extracted with ether. The combined ether extracts are dried, and then the ether is distilled off under reduced pressure to obtain 5.0 parts of bis-4,4'-sebacate. (1,2,2,6,6-pentylpiperidine)

Table I

<td rowspan="2">Example No.</td><td rowspan="2">ri</td><td rowspan="2">R2</td><td rowspan="2">^R3</td><td rowspan="2">Melting point or boiling point</td><td rowspan="2">Summary formula</td><td colspan="3">Values ​​calculated in%</td><td colspan="3">Elemental analysis. Values ​​found in%</td>

<td>C</td><td>h</td><td>N</td><td>C</td><td>h</td><td>N</td>

<td> 1</td><td> 2</td><td> 3</td><td> 4</td><td> 5</td><td> 6</td><td> 7</td><td> 8</td><td> 9</td><td> 10</td><td> 11</td><td> 12</td>

<td>II</td><td>ch₃</td><td>h</td><td>formula 12</td><td>88 ° C</td><td>C₂H₃₈WELL₂</td><td> 76,09</td><td> 10,03</td><td> 4,23</td><td> 76,36</td><td> 9,90</td><td> 3,99</td>

<td>III</td><td>ch₂= ch.ch₂-</td><td>h</td><td>formula 13</td><td>130 ° C under pressure 0.05 mmHg</td><td>c₁₉h₃₃Well₂</td><td> 74,22</td><td> 10,82</td><td> 4,56</td><td> 74,96</td><td> 10,65</td><td> 4,26</td>

<td>IV</td><td>ch₃</td><td>h</td><td>formula 14</td><td>200 ° C after 4 pressures 0.1 mmHg</td><td>C₂2H₅₃NO2</td><td> 77,18</td><td> 12,26</td><td> 3,21</td><td> 78,10</td><td> 12,30</td><td> 3,06</td>

<td>V</td><td>ch₃</td><td>h</td><td>formula 15</td><td>81-3 ° under pressure 0.05 mmHg</td><td>C₁₄H2₇NO2</td><td> 69,67</td><td> 11,27</td><td> 5,80</td><td> 70,16</td><td> 11,37</td><td> 5,90</td>

<td>VI</td><td>ch_s</td><td>h</td><td>formula 16</td><td>228-30 ° C under pressure 0.1 mmHg</td><td>C28H50N2O4</td><td> 70,25</td><td> 10,53</td><td> 5,85</td><td> 70,26</td><td> 10,44</td><td> 5,38</td>

<td>V1T</td><td>ch₃</td><td>h</td><td>model 17</td><td>91-2 ° C</td><td>^C24^H42^N2^ABOUT4</td><td> 68,21</td><td> 10,02</td><td> 6,63</td><td> 68,05</td><td> 9,97</td><td> 6,47</td>

<td>VIII</td><td>ch_s</td><td>h</td><td>model 18</td><td>210-20 ° C under pressure 0.4 mmHg</td><td> ^26^48^048</td><td> 64,40</td><td>9.98 S =</td><td> 5,78 6,60</td><td> 64,26</td><td>9.89 S =</td><td> 5,51 6,59</td>

<td>IX</td><td>ch_s</td><td>h</td><td>model 19</td><td> 64—5^aboutC</td><td>c₂.₆h₄4N₂about₄s</td><td> 68,99</td><td> 10,69</td><td> 6,19</td><td> 69,53</td><td> 10,62</td><td> 6,02</td>

<td>X</td><td>CHs</td><td>h</td><td>formula 20</td><td> 57^ABOUTC</td><td>C19H27NO2</td><td> 75,71</td><td> 9,03</td><td> 4,65</td><td> 75,50</td><td> 8,97</td><td> 4,71</td>

<td>XI</td><td>ch₃</td><td>h</td><td>formula 21</td><td>120 ° C under pressure 0.2 mmHg</td><td>C1H27NO2</td><td> 74,70</td><td> 9,40</td><td> 4,84</td><td> 74,99</td><td> 9,70</td><td> 4,85</td>

<td>XII</td><td>CH</td><td>h</td><td>formula 22</td><td>148 ° C under pressure 0.4 mmHg</td><td>CiqH2₇NO2</td><td> 74,70</td><td> 9,40</td><td> 4,84</td><td> 74,98</td><td> 9,42</td><td> 4,70</td>

<td>XIII</td><td>ch₈</td><td>h</td><td>formula 23</td><td> 51^ABOUTC</td><td>^C18^27^WELL3</td><td> 70,79</td><td> 8,91</td><td> 4,59</td><td> 70,49</td><td> 8,71</td><td> 4,50</td>

<td>XIV</td><td>ch₃</td><td>h</td><td>formula 24</td><td>147 ° C under pressure 0.1 mmHg</td><td>c₁₇h₂₄Well₂these</td><td> 66,00</td><td> 7,81</td><td>4.52 cl =</td><td> 65,98 11,44</td><td>7.65 cl =</td><td> 4,53 11,56</td>

<td>XV</td><td>ch,</td><td>h</td><td>formula 25</td><td>152-4 ° C under pressure 0.2 mmHg</td><td>these₇H₂₄NO "£ L</td><td> 66,00</td><td> 7,81</td><td>4.52 cl =</td><td> 65,89 11,44</td><td>7.65 cl =</td><td> 4,53 11,56</td>

<td>XVI</td><td>ch,</td><td>h</td><td>formula 26</td><td>100 ° C under pressure 0.2 mmHg</td><td>CisH3₅WELL₂</td><td> 72,68</td><td> 11,68</td><td> 4,71</td><td> 72,53</td><td> ,11,96</td><td> 4,50</td>

<td>XVII</td><td>ch,</td><td>h</td><td>Formula 27</td><td> 65^ABOUTC under pressure 0.4 mmHg</td><td>^C13^H22^WELL2</td><td> 69,29</td><td> 10,29</td><td> 6,22</td><td> 69,64</td><td> 10,30</td><td> 6,15</td>

<td>XVIII</td><td>ch,</td><td>h</td><td>formula 28</td><td>196 ° C under pressure 12 mmHg</td><td>C NO</td><td> 74,14</td><td> 9,15</td><td> 5,09</td><td> 74,35</td><td> 9,23</td><td> 5,13</td>

<td>nineteenth</td><td>ch,</td><td>h</td><td>formula 13</td><td>180 ° C under pressure 0.5 mmHg</td><td>C17H31NO2</td><td> 72,55</td><td> 11,10</td><td> 4,98</td><td> 72,84</td><td> 11,04</td><td> 4,77</td>

<td>XX</td><td>ch,</td><td>h</td><td>model 29</td><td>44 ° C</td><td>C28'H5sNO₂</td><td> 76,83</td><td> 12,66</td><td> 3,20</td><td> 76,71</td><td> 12,35</td><td> 3,22</td>

<td>XXI</td><td>ch, ·</td><td>h</td><td>formula 30</td><td>116-17 ° C under pressure 0.2 mmHg</td><td>⁸*8⁸^33^5X'°2</td><td> 72,68</td><td> 11,86</td><td> 4,71</td><td> 72,56</td><td> 11,50</td><td> 4,99</td>

214

table 1 cd

<td> 1</td><td> 2</td><td> 3</td><td colspan="2"> 4</td><td> 5</td><td> 6</td><td> 7</td><td> 8</td><td> 9</td><td> 10</td><td> 11</td><td> 12</td>

<td>XXII</td><td>ch₂= ch.ch₂-</td><td>H</td><td>pattern</td><td> 31</td><td>129-30 ° C under pressure 0.05 mmHg</td><td>CjL7^hr25^WELL3</td><td> 70,07</td><td> 8,65</td><td> 4,81</td><td> 70,70</td><td> 8,86</td><td> 4,42</td>

<td>XXIII</td><td>CH,</td><td>H</td><td>pattern</td><td> 32</td><td>41-2 ° C</td><td> ^,30^59^02</td><td> 77,36</td><td> 12,77</td><td></td><td> 75,84</td><td> 12,25</td><td></td>

<td>XXIV</td><td>formula 33</td><td>H</td><td>pattern</td><td> 34</td><td>183-5 ° C under pressure 0.1 mmHg</td><td>c₂₄h₃₉Well₂</td><td> 77,16</td><td> 10,52</td><td> 3,75</td><td> 77,43</td><td> 10,39</td><td> 3,54</td>

<td>XXV</td><td>formula 33</td><td>H</td><td>ά / ór</td><td> 35</td><td>55-6 ° C</td><td>^C34^H59^WELL2</td><td> 79,47</td><td> 11,57</td><td> 2,73</td><td> 79,32</td><td> 11,59</td><td> 2,45</td>

<td>XXVI</td><td>ch₃</td><td>H</td><td>pattern</td><td> 36</td><td> 174—8^aboutC under pressure 0.1 mmHg</td><td>^C22^H29^WELL2</td><td> 77,84</td><td> 8,61</td><td> 4,13</td><td> 78,35</td><td> 8,63</td><td> 4,12</td>

<td>XXVII</td><td>CH / CHG / n</td><td>H</td><td>pattern</td><td> 30</td><td>190 ° C under pressure 0.05 mmHg</td><td>C₂2H₅₇NO2</td><td> 77,10</td><td> 12,72</td><td> 3*10</td><td> 7.7,20</td><td> 13,02</td><td> 3,08</td>

<td>XXVIII</td><td>CH_S</td><td>H</td><td>pattern</td><td> 37</td><td> 90^about,C under pressure 0.1 mmHg</td><td>C1H2NO2</td><td> 70,54</td><td> 11,45</td><td> 5,48</td><td> 69,99</td><td> 11,24</td><td> 5,25</td>

<td>XXIX</td><td>ch₃</td><td>H</td><td>pattern</td><td> 38</td><td> 69—70^aboutC</td><td>C H_S1WELL₂</td><td> 78,87</td><td> 8,55</td><td> 3,83</td><td> 79,38</td><td> 8,80</td><td> 3,69</td>

<td>XXX</td><td>CHG / CH / n</td><td>H</td><td>pattern</td><td> 24</td><td>56 ° C</td><td>C2₈h₄₆Well₂C1</td><td> 72,60</td><td> 9,90</td><td> 3,02</td><td> 71,98</td><td> 10,19</td><td> 3,01</td>

<td></td><td></td><td></td><td></td><td></td><td></td><td></td><td></td><td></td><td>CI = 7,6B</td><td></td><td>cl =</td><td> -7,35</td>

<td>XXXI</td><td>ch₃</td><td>H</td><td> Zor</td><td> 39</td><td>200 ° C under pressure 0.2 mmHg</td><td>C2₄H₄₇WELL₂S</td><td> 60,70</td><td> 11,45</td><td> 3,39</td><td> 69,69</td><td> 11,48</td><td> 3,31</td>

<td>XXXII</td><td>ch₃</td><td>H</td><td>pattern</td><td> 40</td><td> 119^ABOUTC</td><td>C21H35NO2</td><td> 75,63</td><td> 10,58</td><td> 4,20</td><td> 75,94</td><td> 10,30</td><td> 3,93</td>

<td>XXXIII</td><td>CHgdHr</td><td>H</td><td>pattern</td><td> 28</td><td>Purification</td><td>^C34^H59^WELL2</td><td></td><td>mass</td><td colspan="4">molecular calculated</td>

<td></td><td></td><td></td><td></td><td></td><td>through</td><td></td><td></td><td colspan="5">na = 513 Molecular weight</td>

<td></td><td></td><td></td><td></td><td></td><td>matografię</td><td></td><td></td><td colspan="5">measured with the help of</td>

<td></td><td></td><td></td><td></td><td></td><td></td><td></td><td></td><td colspan="4">mass trometry.</td><td></td>

in the form of a colorless oil with a boiling point of 220-222 ° C at 0.2 mm / Hg. Elemental analysis: values ​​calculated for the sum formula C₃₀H₅₆N₂O4 C = 70.82%, H = 11.10%, N = 5.51%, found values ​​C = 0.0.60%, H = 11.00%, N = 44.81%. The properties of esters obtained by the method described in Example 1 are shown in Table I.

Example XXXIV. To a solution of 17.17 parts, 2,2,6,6-five-methylpiperidin-4 in 50 parts are distilled under reduced pressure, and the remaining yellow oil is distilled under reduced pressure, collecting the boiling fraction at 218-20 ° C under pressure. 0.4 mmHg. Bis (1,2,2,6,6-five-methylpiperidine) 4-sebacate is obtained in the form of a colorless oil. Elemental analysis: calculated values ​​for formula C₃₀H₅₆N2O4 C = 70.82%, H = 11.10%, N = 5.51%; found values ​​C = 70.99%, H = 10.97%, N = 5.26%.

Properties of esters obtained by the opiTable II method

<td rowspan="3">Example</td><td rowspan="3">ri</td><td rowspan="3">R₂</td><td rowspan="3">rg</td><td rowspan="3">Boiling point or melting point</td><td rowspan="3">Summary formula</td><td colspan="6">Elemental analysis</td>

<td colspan="3">calculated</td><td colspan="3">found</td>

<td>C</td><td>H</td><td>N</td><td>C</td><td>H</td><td>N</td>

<td>XXXV</td><td>ch₃</td><td>H</td><td>formula 41</td><td>Purified By</td><td>C₂₆H₄₂N₂G₄S</td><td></td><td></td><td> 5,86</td><td></td><td></td><td> 5,64</td>

<td></td><td></td><td></td><td></td><td>chromatography</td><td></td><td></td><td></td><td></td><td></td><td></td><td></td>

<td>XXXVI</td><td>ch₃</td><td>H</td><td>formula 42</td><td>118 ° C</td><td>C ^^ o ^ N 2^ABOUT4</td><td> 66,63</td><td> 10,17</td><td> 7,06</td><td> 66,94</td><td> 10,22</td><td> 6,95</td>

<td>XXXVII</td><td>CH3</td><td>H</td><td>formula 43</td><td>123 ° C</td><td>C₂8^H44^N2'^ABOUT4</td><td> 70,15</td><td> 9,38</td><td> 5,93</td><td> 70,75</td><td> 9,68</td><td> 5,69</td>

<td>XXXVIII</td><td>CHG</td><td>H</td><td>formula 44</td><td>75-6 ° C</td><td>C^{2 and H}27^WELL2</td><td> 77,50</td><td> 8,36</td><td> 4,30</td><td> 77,78</td><td> 8,45</td><td> 4,06</td>

<td>XXXIX</td><td>CHG</td><td>H</td><td>CHgCO-</td><td>138 ° C under pressure</td><td>^Ci2^H22!^WELL2</td><td> 67,57</td><td> 10,87</td><td> 6,57</td><td> 67,90</td><td> 10,72</td><td> 6,53</td>

<td></td><td></td><td></td><td></td><td>German 12. mmHg</td><td></td><td></td><td></td><td></td><td></td><td></td><td></td>

<td>XL</td><td>CHG</td><td>H</td><td>formula 45</td><td>142 ° C</td><td>C H₄₁nog</td><td> 74,40</td><td> 10,24</td><td> 3,47</td><td> 74,80</td><td> 9,99</td><td> 3,43</td>

anhydrous benzene mixed at 15-20 ° C, 6.0 parts of sebacyloyl chloride are added dropwise within 15 minutes. The mixture is then stirred for 12 hours at room temperature, then the precipitated 1,2,2,6,6-pentymethylpiperidinol-4 hydrochloride is filtered off. The benzene used in Example XXXIV is shown in Table II.

Example XLI. A mixture of 17.17 parts, 2,2,6,6-pentylpiperidinol-4,3, 13.60 parts methyl benzoate, and 2.0 parts lithium amide are heated at a temperature of

214

160 ° C, within 6 hours. The methyl alcohol formed in the reaction is distilled off_v Heating continues over. a further 2 hours, simultaneously connecting the reaction vessel with water by a vacuum pump. The reaction mixture is cooled, the residue obtained is dissolved in chloroform and the lithium amide is filtered off. Chloroform is distilled off under reduced pressure to give a yellow oil which is subjected to fractionated distillation under reduced pressure. 6.40 parts of 1,2,2,6,6-pentymethylpiperidine 4-benzoate are obtained with a boiling point of 126 ° C under a pressure of 0.1 mmHg. Elemental analysis: calculated values ​​for the formula CnHtfNO, C = 74.14%, H = 9.15%, N = 5.09%; found values ​​C = · 74.35%, H = 9.23%, N = 5.13%. .

Example XLII. A mixture of 17.17 parts, 2,2,6,6-pentylpiperidinol-4, 14.60 parts methyl-0- (3,5-di-tert-butyl-4-hydroxyphenyl) propiomate, and 1.0 parts lithium amide, heated at 130 ° C. Then a water vacuum pump is connected to the reaction vessel and heated at 125-135 ° C for 3 hours. The reaction mixture, in turn, is maintained. at 160 ° C and 0.5-1 mmHg pressure for 1 hour. It is then cooled, dissolved in chloroform and filtered. Chloroform is distilled off under reduced pressure to obtain a brown oil. The oil is triturated in ether to give a white solid which is filtered, thoroughly washed with ether and dried. Thus, 16.0 parts of bicarbonate propionate, lopiperidinol-4-3 - (), and ^^^ d \ ^ and ^ -] ^^^ are obtained from butyl-4'-hydroxyphenyl. melting 210-11⁰C. Elemental analysis: calculated values ​​for · formula C₂₈H₄₇WELL₆ C = 68.10%, H = 9.60%, N = 2.84%; found values ​​C = 68.90%, H = 9.56%, N = 2.91%.

Example XLIII. 15.0 parts of the compound obtained in Example XLII are dissolved in water and neutralized with aqueous sodium hydroxide solution. The resulting aqueous solution is extracted with ether, the ether extracts are combined and dried over anhydrous MgSO4. The ether is distilled off under reduced pressure to obtain a white solid, which is recrystallized from alcohol to give 9.30 parts of 1,2,2,6,6-pentylpiperidinol-4-β-335'5-tb-butyl-4 '' propionate. -hydroxyphenyl / melting point 124-5 ° C. Elemental analysis: calculated values ​​for formula C₂₇H ^ NO₈ C = 55.30%, H = 10.20%, N = 3.30%; values ​​found C = 55.00%, N = 3.50%.

Example XLIV. A mixture of 10.26 parts 1,2,2,

6.6- pentomethylpiperidinol-4, 5.04 parts of trimethyl tri-mesoate and 0.20 parts of lithium amide, heated in 100 parts of xylene at 137 ° C for 7 hours. The methanol formed in the reaction is distilled off. Then the reaction mixture is cooled, the amide is filtered off. lithium and distilled from the filtrate xylene. Reaction products of trimethylandvumethyl- (1,2,2,6,6-five-methylpiperidinyl-4), and methyl-bi s- (1,2,2,6,6-pi and γ-methyl dynyl-piperidine-4 / tetrasinate) are separated and purified by technique thin layer chromatography. Determination of molecular weight by mass spectrometer: for dimethyl- / 1,2,2,6,6-pentomethyl-piperidine-4-trimethanoate was calculated for formula C₂1H₂₉NO6 - 391, found 391; for 4,4'-methyl bis- / 1, 2,2-tris mesanoate,

6.6- five-methylpiperidine was calculated for the formula

C₃₀H44N₂ABOUT_e - 530, found 530.

XLV example. A mixture of 16.4 parts of 1,2,2,6,6-pentylpiperidinol-4, 6.27 parts of methyl isocyanate and 0.5 parts of 1,4-diazabicyclo / 2.2.2 / octane is heated to reflux. under reflux in 150 parts of dry benzene for 24 hours. Benzene is distilled off under reduced pressure to obtain a thick oil, which is purified by leaving it for 24 hours with 200 parts of water. The resulting solid is filtered off, dried and crystallized from n-hexane. 14.2 parts of 4-methylcarbamyloxy are obtained Table III

<td rowspan="3">At- Quad</td><td rowspan="3"></td><td rowspan="3">R-2</td><td rowspan="3"></td><td rowspan="3">Boiling point or melting point ..</td><td rowspan="3">Summary formula</td><td colspan="6">Elemental analysis</td>

<td colspan="3">calculated</td><td colspan="3">found</td>

<td>C</td><td>H</td><td>Ν.</td><td>C</td><td>H</td><td>N</td>

<td> 1</td><td> 2</td><td> 3</td><td> 4</td><td> 5</td><td> 6</td><td> 7</td><td> 6</td><td> 9</td><td> 10</td><td> 11</td><td> 12</td>

<td></td><td></td><td></td><td>ABOUT II</td><td></td><td></td><td></td><td></td><td></td><td></td><td></td><td></td>

<td>XLVI</td><td>ch₃</td><td>H</td><td>II CH, / CHG / NBC-</td><td>63 ° C</td><td>^C17^H84^N2^ABOUT2</td><td> 66,41</td><td> 11,46</td><td> 9,39</td><td> 66,17</td><td> 11,32</td><td> 9,16</td>

<td></td><td></td><td></td><td>* ABOUT</td><td></td><td></td><td></td><td></td><td></td><td></td><td></td><td></td>

<td>XLVII</td><td>ch,</td><td>H</td><td>|| ch₃/ ch₂/₇nhc-</td><td>56u-7 ° C</td><td>· ^ 29 ^ 55 ^ 2θ2</td><td> 74,62</td><td> 12,52</td><td> 6,00</td><td> 74,56</td><td> 12,34</td><td> 5,96</td>

<td></td><td></td><td></td><td>about</td><td></td><td></td><td></td><td></td><td></td><td></td><td rowspan="2"> 10,27</td><td></td>

<td>XLVIII</td><td>CH_S</td><td rowspan="2">H</td><td>ch₂CH. II</td><td>62 ° C</td><td>C14H26N2O2</td><td> 66,11</td><td> 10,30</td><td> 11,01</td><td> 66,40</td><td> 10,92</td>

<td></td><td></td><td>.CHjNHC-</td><td></td><td></td><td></td><td></td><td></td><td></td><td rowspan="2"> 10,64</td><td></td>

<td rowspan="2">XLLX</td><td rowspan="2">OH</td><td rowspan="2">H</td><td rowspan="2">model 46</td><td rowspan="2">186 ^ 6 ° C at 2 mm pressure</td><td rowspan="2">C ^ H ^ gO.</td><td rowspan="2"> 66,66</td><td rowspan="2"> 10,66</td><td rowspan="2"> 9,45</td><td rowspan="2"> 66,96</td><td rowspan="2"> 9,43</td>

<td></td>

<td></td><td></td><td></td><td></td><td>mg</td><td></td><td></td><td></td><td></td><td></td><td></td><td></td>

214

cd tahl. III

<td> 1</td><td> 2</td><td> 3</td><td> 4</td><td> 5</td><td> -</td><td> 7</td><td> 8</td><td> 9</td><td> 10</td><td> 11</td><td> 12</td>

<td>L</td><td>ch₃</td><td>H</td><td>formula 47</td><td>109-10 ° C</td><td>^C17^H26^N2^ABOUT2</td><td> 70,31</td><td> 9,02</td><td> 9,-5</td><td> 70,-1</td><td> 8,80</td><td> 9,53</td>

<td>LI</td><td>ch₃</td><td>H</td><td>formula 48</td><td>10--7 ° C</td><td>C18H28N2O2</td><td> 71,02</td><td> 9,27</td><td> 9,20</td><td> 71,42</td><td> 9,41</td><td> 9,02</td>

<td>LII</td><td>ch₃</td><td>H</td><td>model 49</td><td>121 ° C</td><td>C₁₇H2₅N2O₂C1</td><td> -2,8-</td><td> 7,70</td><td> 8,-8</td><td> -2,92</td><td> 7,75</td><td> 8,87</td>

<td>LIII</td><td>ch₃</td><td>H</td><td>formula 50 ABOUT</td><td>129 ° C</td><td></td><td> 74,08</td><td> 8,29</td><td> 8,23</td><td> 74,37</td><td> 8,07</td><td> 8,41</td>

<td>LIV</td><td>ch₃</td><td>H</td><td>II -CNH / CH 2 /</td><td>101-4 ° C</td><td>^C28^H54^4N4^ABOUT4</td><td> -5,84</td><td> 10,—</td><td> 10,97</td><td> -5,8-</td><td> 10,40</td><td> 10,-4</td>

<td></td><td></td><td></td><td> /₆NHCO-</td><td></td><td></td><td></td><td></td><td></td><td></td><td></td><td></td>

<td>LV</td><td>CH3</td><td>H</td><td>model 51</td><td>1-3-5 ° C</td><td>^C29^H48^N4^ABOUT4</td><td> -7,41</td><td> 9,3-</td><td> 10,84</td><td> -7,21</td><td> 9,52</td><td> 10,83</td>

<td>LVI</td><td>CH3</td><td>H</td><td>model 52</td><td>183 ° C</td><td>^C3^5H52^4^ABOUT4</td><td> 70,91</td><td> 8,84</td><td> 9,45</td><td> 70,-4</td><td> 8,79</td><td> 9,24</td>

<td>LVII</td><td>CH3</td><td>H</td><td>formula 53</td><td>178 ° C</td><td>C₃₂H₄₃N4O4</td><td> -9,53</td><td> 8,75</td><td> 10,14</td><td> 70,39</td><td> 8,71</td><td> 9,8-</td>

<td>LVIII</td><td>ch₂= ch.ch₂-</td><td>H</td><td>model 46</td><td>165 ° C under pressure</td><td>^C^9^H34^4N4^ABOUT4</td><td> 70,7-</td><td> 10,-3</td><td> 8,-9</td><td> 70,-4</td><td> 10,80</td><td> 9,04</td>

<td></td><td></td><td></td><td></td><td>0.05 mm</td><td></td><td></td><td></td><td></td><td></td><td></td><td></td>

<td></td><td></td><td></td><td></td><td>hg</td><td></td><td></td><td></td><td></td><td></td><td></td><td></td>

<td>LIX</td><td>ch₂= ch.ch₂-</td><td>H</td><td>/CH2/6./NHCO-/2</td><td></td><td></td><td></td><td></td><td></td><td></td><td></td><td></td>

<td>LX</td><td>CH 3 CH₂CH₂-</td><td>H</td><td>formula 48</td><td></td><td></td><td></td><td></td><td></td><td></td><td></td><td></td>

<td>LXI</td><td>formula 33</td><td></td><td>model 49</td><td></td><td></td><td></td><td></td><td></td><td></td><td></td><td></td>

-1,2,2,6,6-five-methylpiperidine with a melting point of 96-7^ABOUTC. Elemental analysis: calculated values ​​for formula C₁₂H₂₄N₂ABOUT₂ C = 63.12%, H = 25 = 10.59%, N = 12.27%; found values ​​C = = -3.28%, H = 10.70%, N = 12.09%. The properties of carbamyloxy esters obtained by the method described in Example XLV are presented in Table III. thirty

Example LXII. A mixture of 28.3 parts of 2,2,6,6-tetramethylpiperidine n-heptane carboxylate and 8.55 parts of benzyl bromide are stirred at 105 ° C for 72 hours. It is then cooled, ether added and the 4-n-heptanecarboxylate 2,4-, - tetra-methylpiperidine hydrobromide produced by reaction is filtered off. The ether is distilled off under reduced pressure, and the obtained residue is distilled under reduced pressure. 1-, 40 parts of 4-n-heptane carboxylate 1T abl and a IV are obtained

<td rowspan="2">At- Quad</td><td rowspan="2">ri</td><td rowspan="2">R2</td><td rowspan="2">rj</td><td rowspan="2">Boiling point or melting point</td><td rowspan="2">Summary formula</td><td colspan="3">calculated</td><td colspan="3">found</td>

<td>C</td><td>Η</td><td>N</td><td>C</td><td>H</td><td>N</td>

<td>LXIII</td><td>formula 33 ABOUT II</td><td>H</td><td>formula 54</td><td>98-9 ° 'C</td><td>^C42H-4^N2^ABOUT4</td><td> 7-,32</td><td> 9,7-</td><td> 4,24</td><td> 7-,04</td><td> 9,49</td><td> 4,04</td>

<td>LXIV</td><td>CH₃CH₂CO-CH2-</td><td>H</td><td>formula 23</td><td>191-2 ° C under pressure 0.1 mm hg</td><td>c₂₁H3₁Well₅</td><td> --,82</td><td> 8,28</td><td> 3,71</td><td> --,81</td><td> 9,52</td><td> 3,84</td>

<td>LXV</td><td>CH2^{and =}CH-CH 2</td><td>H</td><td>formula 30</td><td>142-4 ° C under pressure 0.2 mm Hg</td><td>C20H37NO,</td><td> 74,25</td><td> 11,53</td><td> 4,33</td><td> 74,0-</td><td> 11,3-</td><td> 4,32</td>

<td>LXVI</td><td>CH = C: CH₂-</td><td>H</td><td>formula 23</td><td> -8—9⁰'C</td><td>C20H27NO3</td><td> 72,92</td><td> 8,2-</td><td> 4,25</td><td> 72,82</td><td> 8,28</td><td> 4,55</td>

<td>LXVII</td><td>CH 2 = CHCH 2</td><td>H</td><td>formula 28</td><td>150 ° C under pressure 0.05 mm hg</td><td>Ci9H²7^NABOUT₂</td><td> 75,71</td><td> 9,03</td><td> 4,-5</td><td> 75,58</td><td> 9,25</td><td> 4,45</td>

<td>LXVIII</td><td>CH 2 = CHCH 2</td><td>H</td><td>formula 54</td><td>250 ° C under pressure 0.5 mm Hg</td><td>⁰34ΗθθΝ2 °₄</td><td> 72,81</td><td> 10,78</td><td> 4,99</td><td> 73,07</td><td> 10,-0</td><td> 4,77</td>

<td>LXIX</td><td>formula 55</td><td>H</td><td>formula 13</td><td>139-42 ° C under pressure 0.2 mm Hg</td><td>^C11^H;!5^WELL3</td><td> 70,55</td><td> 10,28</td><td> 4,33</td><td> 70,37</td><td> 10,38</td><td> 4,39</td>

-benzyl-2,2,6,6-tetramethyl-opiperidine with a boiling point of 180 ° C under a pressure of 0.1 mmHg. Elemental analysis: calculated value 'for formula C₂₄H₃₉WELL₂ C = 777.16%, H-10.52%, N = 3.75%; · found values ​​C = 77.46%, H = 10.50%, N = 3.86%. Properties of esters obtained by the method described in Example LXII are presented in Table IV.

Example LXX. A mixture of 17.17 parts of 1,2,2, 6,6-pentylpiperidinol-4 and 3.50 parts of sodium metal in 125 parts of toluene is heated under reflux for 24 hours. The toluene solution is decanted from excess sodium and heated with 38.60 parts of n-octadecyl bromide at reflux for a further 24 hours. The solution is then cooled, the NaBr formed in the reaction is filtered off and the toluene is distilled off under reduced pressure. The residue is subjected to fractionated distillation under reduced pressure to obtain 4-octadecyloxy-1,2,2,6,6-five-methylpiperidine with a boiling point of 184 ° C

214 distilled under reduced pressure to obtain 2.90 parts of 1-n-propyl-2,2,6,6-tetramethylpiperidine 4-n-heptane carboxylate with a boiling point of 128 ° C under a pressure of 0.05 mmHg. Elemental analysis: calculated values ​​for the formula C20H39NO2 C — 73.79%, Hn / M, N = 4.30%; found values ​​C = 733.50%, H = 12.26%, N = 4.31%.

The properties of the compounds obtained as described in Example LXXVII are shown in and in Table VI. .

Example LXXX. a. A mixture of 2.83 parts of 2,2,6,6-tetramethylpiperidine n-heptane carboxylate and 1.50 parts by volume of liquid ethylene oxide are placed in an autoclave with a capacity of 50 ml pre-cooled to -50 ° C. The autoclave is filled with nitrogen to a pressure of 100 atmospheres, raised the temperature to 200 ° C and stirred for 3 hours at this temperature. The reaction mixture is then cooled and fractionated. 2.30 · parts of 4-n-heptane carboxylate 1- (2'-hydroxyethoxy) -2,2,6,6-cttero are obtained Table V

<td rowspan="2">Example</td><td rowspan="2">ri</td><td rowspan="2">R2</td><td rowspan="2">^R3</td><td rowspan="2">Boiling point or melting point</td><td rowspan="2">Summary formula</td><td colspan="3">calculated</td><td colspan="3">found</td>

<td>C</td><td>H</td><td>N</td><td>C</td><td>H</td><td>N</td>

<td>LXXI LXXII LXXIII</td><td>CH3 CH3 ch₃</td><td>Η H H</td><td>CH2 = C ^ H. CH2 formula 33 CH₈/ CH₂/ N /</td><td> - </td><td></td><td></td><td></td><td></td><td></td><td></td><td></td>

<td>LXXIV</td><td>CH3</td><td>H</td><td>- / ch₂/₄-</td><td> 62-63^</td><td>C₂₁H4₈N₂AT₂</td><td> 72,74</td><td> 12,09</td><td> 7,07</td><td> 73,00</td><td> 11,99</td><td> 6,85</td>

<td>LXXV</td><td>ch₃</td><td>H</td><td>CH = CCH₂-</td><td>73-74 ° C at 0.3 mm Hg</td><td>^ ΗμΝΟ</td><td> 74,59</td><td> 11,07</td><td> 6,69</td><td> 74,48</td><td> 10,95</td><td> 6,41</td>

<td>• LXXVI</td><td>CH3</td><td>H</td><td>^CH3^/CH2^/3-</td><td>• 103-124 ^ at 19 mm Hg pressure</td><td>c₁₄h₂₉Well</td><td> 73,95</td><td> 12,85</td><td> 6,16</td><td> 74,05</td><td> 12,93</td><td> 6,10</td>

Board . VI

<td rowspan="2">Example</td><td rowspan="2">R |</td><td rowspan="2">R2</td><td rowspan="2">rg</td><td rowspan="2">Boiling point or melting point</td><td rowspan="2">Summary formula</td><td colspan="2">Elemental analysis</td>

<td>calculated</td><td>| found</td>

<td>LXXVIII</td><td>CH / CH2CH2-</td><td>H</td><td>CH3CH2CH2-</td><td></td><td></td><td></td><td></td>

<td>LXXIX</td><td>CH₃</td><td>H</td><td>CH3CH2CH2-</td><td></td><td></td><td></td><td></td>

at 0.25 mmHg. Elemental analysis: calculated values ​​for 'formula C2₈H₅₇NO C = 79.36%, H = 13.58%, N = 33.31%; found values ​​C = 78.66%, H = 13.77%, N = 2.99%. .

Properties of ethers obtained by the method described in Example LXX are presented in Table V.

Example LXXVII. 3.23 parts of 1-aliao-2,2,6,6-tetramethylpiperidine 4-n-hepta-carboxylate in 50 parts of ethanol are exposed to hydrogen at 1 atmosphere pressure at room temperature in the presence of 0.1 part 5% Pd / C as a catalyst. The catalyst is removed by filtration, ethylene piperidine ethanol, boiling point 186-7^ABOUTC at 0.25 mmHg. Elemental analysis: calculated values ​​for formula C₁₉hl₇NÓl C = 69.68%, H = H, 99%, N = 4.28%; found values ​​C = 99.93%, H = H, 99%, N = 4.37%.

b. 11.32 parts of 2,2'-phif-tetramethylpiperidine 4-n-heptane carboxylate and 2.50 'parts of 2-bromoethanol are stirred at 100 ° C for 65 hours. The reaction mixture is cooled, petroleum ether / boiling point 40-60 is added^QC / and the 2,2,6,6-tetra-methyl-4-piperidinyl 4-n-heptanecarboxylate hydrobromide formed by filtration is filtered off. The petroleum ether distils off

214 under reduced pressure. Distillation of the residue gives 1- (2'-hydroxyethyl) 2,2,6,6-tetramethylpiperidine 4-heptane carboxylate with a boiling point of 176 ° C at 0.2 mm / Hg. The obtained compound is identical to that obtained in Example LXXX a.

Example LXXXI. A mixture of · 11.45 parts of 4-phenylcarbamyloxy-2,2-, - tetramethylpiperidine and -0 parts of styrene oxide in -0 parts of n-hexanol is heated to reflux for 18 hours. n-Hexanol and unreacted styrene oxide are distilled off under reduced pressure to obtain a light yellow crystalline solid. The product is purified by trituration · in hot petroleum ether (boiling point -0-80 ° C) to give 4-phenylcarbomyloxy-1- (2'-hydroxy-2'-phenylethyl) / -2.2, -, - tetramethylpiperidine with a melting point of 18-7^ABOUTC. Elemental analysis: calculated values ​​for the formula C24H3₂N₂ABOUT₈ C— = 72.70%, H = 8.13%, N = 7.0-%; found values ​​C = 22.51%, H = 7.92%, N = 6.91%.

Example LXXXII. A mixture of 5, -1 part of 4-n-heptane carboxylate 2, ^, ^, ^ ^ 1: ^ and α ^ and ^ ^ 1 ^ t ^; ipyeridine and 5.0 parts of propylene oxide are placed in autoclave, into which nitrogen is introduced to a pressure of 100 atmospheres and heated at 200 ° C for 3 hours. The product is purified by successively fractionated distillation under reduced pressure, collecting a fraction with a boiling point of 1-0-183 ° C under a pressure of 0.1 mmHg, chromatography on a column filled with aluminum oxide type H, eluting with chloroform. The semi-solid 4-n- heptane carboxylate 1 - (2'-hydroxypropyl) -2,2,6,6-tetra-methylpiperidine is obtained. Elemental analysis: · calculated values ​​for formula C2₀H₃₉NO3 C = 00.34%, H = 11.51%, N = 4.10%; found values ​​C = 70.20%, H = II, 55%, N = 3.89%.

Example LXXXIII. A mixture of 3.27 parts of the product obtained in Example LXXXa. 0.10 acetic acid and 0.1 part tetra-n-butyl titanate in 40 parts xylene, heated at reflux for 24 hours. Xylene is distilled off under reduced pressure, the residue is subjected to fractionated distillation to obtain 1- 22'-aceto'-xyethyl-2 -2,2-4-n-heptanecarboxylate, -, - tetramethylpiperidine with a boiling point of 190-2^ABOUTC at 1 mmHg. Elemental analysis: calculated values ​​for formula C2iH3₉NO4 C = 88.25%, H = 00.64%, N = 3.79%; found values ​​C = 68.17%, H = 00.65%, N-3.36%.

Example LXXXIV. A mixture of 3.27 parts of the product obtained in Example L} CXXa, 0.3 parts of methyl isocyanate and 0.1 part of 1,4cdazabicyclo2 / 2.2.2_/octane in 30 parts of anhydrous benzene, refluxed for 24 hours. Benzene is distilled off under reduced pressure. The residue is crystallized from anhydrous ethanol to give 1- (2'-methylcarbamyloxyethyl) -2-n-heptanecarboxylate / -2.2, -, - tetramethylpiperidine with a melting point of -1-3^ABOUTC. Elemental analysis: calculated values ​​for the formula

C! ^. C = 55.59%, H = 10.48%, N = 7.28%; found values ​​C = 55.72%, H = 0O, ​​37%, N = 7, 11%.

Example LXXXV. A mixture of 3.0 parts of the product obtained in Example LXXXI, 0.90 parts of phenyl isocyanate and 0.1 part of 1,4-diazabicyclic // 2.2.2 / octane in 25 parts of anhydrous benzene is heated to reflux under reflux condenser within 24 hours. The benzene solvent is distilled off under reduced pressure, and the residue is recrystallized from petroleum ether / boiling point -0-80^aboutC to give 4-phenylcarbamyloxy-1-2 / 2'-2-phenylcarbamyloxy / -2^,-phenyl-yyl / -2.2, -, - -methylpiperidine, m.p. 173 ° C. Elemental analysis: calculated values ​​for formula C3₁H₃₇N_sOl C = 72.21%, H ^, 2 ^^%, N = 8.15%; found values ​​C = 72, -5%, H = 7.22%, N = 7.97%.

Example LXXXVI. A mixture of 3.14 parts,

2.2, -.- tetramethylpiperidinol-4 and 3.50 parts of acetic anhydride are heated on a water bath for 1 hour. 20 parts of water are then added and heating continues under previous conditions for the next hour. ' The solution is carefully neutralized with saturated sodium bicarbonate solution and extracted with ether. The ether extract is washed twice with 5% sodium bicarbonate solution, then twice with hydrochloric acid solution dried over anhydrous MgSO4 and the ether is distilled off under reduced pressure. 1-Acetyl-2,2, -, 6-tetraethylpiperidine 4-acetate is obtained, mp 33-4⁰C. Elemental analysis: for formula C₁₃H2₃WELL₃ calculated values ​​C = -4.73%, N = 5.81%; found values ​​C = -4.51%, H = 9.69%, N = · 5, -7%.

Example LXXXVII. A mixture of 15.70 parts

2.2. -.-- z-tettermethylpiperidinol-4,22.80 parts methyl isocyanate and 0.5 parts 1,4-diabicyclo / 2.2.2 / -Octane in 100 parts anhydrous benzene is heated under reflux for 24 hours. Benzene is distilled off under reduced pressure, 150 parts of water are added to the residue and left at room temperature overnight. The crystalline solid is filtered off and dried, yielding 19.0% of a colorless substance, m.p. 1-7-8 ° C. As shown by microanalysis and nuclear magnetic resonance spectrum, this substance contains 80% 4-methylcarbamyloxy-1-methylcarbamyl-2,2, -, - tetramethylpiperidine.

Example LXXXVIII. a. 2.5-5 parts of acrylonitrile are added dropwise while stirring to a solution of 8.55 parts 1,2,2,6,6-pentomethyl · opiperidinol-4 and 0.30 parts 40% potassium hydroxide solution in 80 parts benzene. It is stirred for a further 1 hour at room temperature, washed with water and dried. Benzene is distilled off under reduced pressure, the residue is subjected to fractionated distillation under reduced pressure to obtain 1.70 parts of 4- / 2'-cyanoethoxy / -1, 2.2, -, 6-pentomethylpiperidine with a boiling point of 105 ° -C under pressure 0.1 mmHg. Elemental analysis: values ​​calculated for the formula

214

CIEH_f4N₂OC = 69.60%, 'H = 10.78%', N = 12.49%; found values ​​C = 69.27%, H = 10.66%, N = 12.40%. b. To 51 parts of 1,2,2,6,6-five-methylpiperidinol-4 is added a solution of sodium metal in 1 part of T-butanol and 51.5 parts of acrylonitrile are added dropwise with vigorous stirring. The reaction mixture is allowed to stand at room temperature for 1 day and then heated at 80 ° C for 1 hour. The resulting 4- / 1'-cyanoethoxy / -1, 1,2,6,6-five-methylpipine dyne is distilled by collecting the boiling fraction at 171-4 ° C under a pressure of 17 mmHg. The obtained compound was identical to the obtained compound - in Example LXXXVIIIa. .

Example LXXXIX. A mixture of 13.1 parts

4-dodecyloxy-1,1-, 6-tetramethylpiperidine and 3.41 parts of benzyl bromide are heated at 100 ° C for 48 hours. It is then cooled, petroleum ether / boiling 40-1-1^ABOUTC / i filter 4-dodecyloxy-1,1, -, - tetramethylpiperidine hydrobromide. The petroleum ether is distilled off under reduced pressure, the residue is subjected to fractionated distillation to give 4-d-decyloxy-1-b-benzyl-1,2, -, - isomerylpylpridridinium at a boiling point of 100 ° C under a pressure of 0.5 mmHg. Elemental analysis: calculated values ​​for formula C₂$ H₄₉NO C = = 80.60%, H = 11, 88%, N = 3.37% ;, values ​​found C = 00.67%, H = H, 12%, N = 3.34%.

Example XC. A mixture of 4-benzyloxy-1,1, -, - tetramethylpropylidine and 1.7 parts of α-bromoacetate in 30 parts of ethyl alcohol is heated to reflux for 115 hours. The ethyl alcohol is then distilled off under reduced pressure, and the residue is fractionated to obtain. 4-benzyl-loxy-1-ethoxycarbanylmethyl-2,1, -, - tetramethylpiperidinide at a temperature of 145—-^ABOUTC at a pressure of 0.1 mmHg. Elemental analysis: calculated values ​​for the formula C ^ HuNOg C = 12.04%, H = 9.37%, N = 4.20%; found values ​​C = 71, -1%, H = 8.90%, N = 3.64%.

Example XCI. A mixture of 15.7 parts, 1,1,1, -, pentomethylpiperidinol and 3.06 parts of boric acid in 100 parts of toluene is heated to reflux with an azeotropic cap for 14 hours. Toluene is distilled off under reduced pressure, and the residue is tris (1,1,6,6-pentomethyl-4-piperidyl) 4-borate, mp 83 ° -6 ° C. Elemental analysis: values ​​calculated for the formula Cu ^ NgO ^ C = -6.05%, H = 11.56%, N = 8.0-%; found values ​​C = 88.85%, H = 11-8%, N = 7.7-%.

Example XCII. 4 parts of sodium metal are added to 30 parts of 1,2,2,6,6-pentylpiperidinol-4 in 150 parts of benzene. The solution is heated at reflux overnight, cooled, 38 parts of tosylate are added dropwise.

Of the 2-phenoxyethanol solution and the resulting solution is heated under reflux for 5 hours. The mixture is cooled, filtered and the filtrate is concentrated under reduced pressure. The residue is treated with dilute hydrochloric acid and then basified with dilute sodium hydroxide solution to pH = 10 and extracted with ether. After distilling off the ether, a light yellow oil is obtained, which is purified by an alumina column chromatography. 4- / 2'-phenoxyethoxyV-1,1,2,6,6-pentylpiperidine is thus obtained in the form of a colorless oil. Elemental analysis: calculated values ​​for the formula C1H29NO1 C = f7 ^ 18%, H = 10.03%, N = 4.81%; values ​​found C = 2ί6 / ^ ί)%, H = 9.86%, N = 4.91%.

Example XCilI. A mixture of 6.87 parts of 4-allyloxy-2,1-, - tetramethylpiperidine and 3.03 parts of allyl bromide is heated at 60 ° Ο for 6 hours, then cooled, added ether and filtration of the resulting hydrobromide 4 Allyloxy-1,1, -, 6-czterometylopiperydyny. Dter is distilled off under reduced pressure, and the residue is purified by chromatography to give 4-allyloxy-1-allyl-2,2,2,6-tetramethylpiperidine.

Examples XCIV — CXVI. Testing in polypropylene film 38 parts of polypropylene are homogenised with 0.07 parts of n-octadecyl-P- / 4'-hydroxy-3 ', 5'-t-butylphenyl propionate / in a kneader for 3 minutes at 100 ° C. which 0.16 parts of the product obtained in Example 13 is added and homogenization continued for a further 7 minutes. The mixture is formed into a film of 0.1 mm thickness at a temperature of 1-0 ° C in minutes - and then cooled quickly in cold water. A 44X100 mm sample cut from 0.1 mm annealed polypropylene film is exposed to light radiation in a fademotraction device consisting of a circular base on which 10 watt fluorescent lamps are alternately placed, and maximum! emissions at 3100 A and fluorescent radiation emitters with a power of 10 watts and a maximum emission of 3500 A. The length of both types of radiators is 0, -1 m. The specimen rotates over the radiators in such a way that their radiation is evenly distributed over its entire surface. The exposed sample is periodically subjected to a tensile strength test, determining the exposure time after which the sample breaks at 50% elongation. Similar tests are carried out with polypropylene samples containing no stabilizer or containing known stabilizers, among others those listed in German Patent No. 1616 618. The results obtained are given in Table VII.

214

Table VII

<td rowspan="2">Example No.</td><td></td><td>Co-ordinate, n = Time of exposure, after which breaks at 50% elongation (from</td>

<td>Addition and</td><td>addition) Exposure time followed by a break at 5 ° / 0 ° (with no addition)</td>

<td> 1</td><td> 2</td><td> 3</td>

<td></td><td>No additions</td><td> 1,0</td>

<td></td><td>2 -. / 2'-hydroxy-3 ', 5'-di-III riz.buty^llof € nylo / - 5-chloroben zo ztria sol</td><td> 3,2</td>

<td></td><td>4-fenylokarbamyloksy- -2,2,6,6-czterometylopi- piperidine</td><td> 1,8</td>

<td></td><td>1,6-bis / 4&gt; karbamyLLoksy-2 ', 2', 6 ', 6'-czterometylopiperydyno / hexane</td><td> 2,4</td>

<td></td><td>2,2,6,6-4-benzoate -czterometylopipery- dynes</td><td> 2,6</td>

<td></td><td>. bissebate / 2.2; 6.6- tetramethyl-4-piperidone pyridine with /</td><td> 4,7</td>

<td>χσν</td><td>4H-Phenylacetate 1,2,2,6,6- -pięcioimetylopipery- dynes</td><td> 5,2</td>

<td>xcv</td><td>ibis- / 1,2,2,-pentomethyl-4-piperidine terephthalate /</td><td> 5,3</td>

<td>xcviii</td><td>1,2,2,6,6-pentoxyl 4-p-methoxybenzoate back piperidine</td><td> 5,3</td>

<td>XCVII</td><td>4- / l'-naftoesain / 1,2,2,6, E-pięciometylopipery- dynes</td><td> .5,4</td>

<td>XCVIII</td><td>4-hepfanokarboksylani 1,2,2,6,6-pięciometylo- piperidine</td><td> 6,2</td>

<td>XCIX</td><td>1,2,6,6-butyrate 4-isobutyric acid</td><td> 6,2</td>

<td>c</td><td>bis- / 1,2,2,6, 6-pentomethyl-4-piperidine isbacate</td><td> 8,0</td>

table VII

<td> 1</td><td> 2</td><td> 3</td>

<td>CI</td><td>2,4-.bis- / 4'-caribamyl-xy-r, 2 ', 2', 6 ', 6'-pentameters lopip eridino / to luen</td><td> 5,2</td>

<td>CII</td><td>4 -p-yloyl carbamyloxy - -ljŹ them ^ ^ -pięciometylo- piperidine</td><td> 5,2</td>

<td>CIII</td><td>4- allylcarbonamyloxes -1 2,6,6-pentameters lo- pip era dyna</td><td> 5,5</td>

<td>CIV</td><td>4-fenylokarbamyloksy- -1,2,2,6,6-pięciometylo- piperidine</td><td> 5,6</td>

<td>CV</td><td>4-.metylokaćbamyloksy- -1,2,2,6,6-piięcioimetylo- piipe.ry-dy.na</td><td> 6,8</td>

<td>CVI</td><td>1,6-bis- / 4'-carbamyloxy-1 ', 2', 2 ', 6', 6'-five-methylpipine dyno / hexane</td><td> 9,2</td>

<td>CVII</td><td>bis- / l-ben- sebacate benzyl-2,2,6,6-czterome- methyl-4-piperidine /</td><td> 5,0</td>

<td>CVIII</td><td>1-ethoxycarbonylmethyl-2,2,6,6-tetraethyl lopiperidine 4-p-imethoxybenzoate</td><td> ' 5,1</td>

<td>CIX</td><td>4- / 1'-ethylpentane carboxylate / 1-benzyl -2,2,6,6-tetramethylpiperidine</td><td> 5,2</td>

<td>cx</td><td>4-h eptainoka carboxy la nn-dodecyl-2 ^ 2,6,6-tetramethylpiperidine: ny</td><td> 5,2</td>

<td>CXI</td><td>4-heptanokarboklsylain 1- / 2'-hydroxy-ethyl - / - 2,2,6,6-tetramethylpiperidyme.</td><td> 5,8</td>

<td>CXII</td><td>4-hep tanocarboxylate 1-nHpropyl-2,2,6; 6-tetrahydrate lopiperidine</td><td> 6,0</td>

<td>cxv</td><td>4-n-dodecyloxy-l, 2,2,6, E-pięciometylopipery- dyne</td><td> 5,5</td>

<td>CXIV</td><td>4- / 2'-cyano toxins / -1,2, 2,6,6-tetramethylpiperidine</td><td> &gt;6,0</td>

<td>CXV</td><td>l, 4-bis ^ l ', 2', 2 ', 6', 6'-pięciometylo-4'-piperidinyloxy / butane</td><td> &gt;6,0</td>

<td>CXVI</td><td>tris- / l borane, 2,2,6,6- -pięciometylo-4-piperidone pyridine with /</td><td> 5,0</td>

Examples CXVII-CXIX. The method described in Examples XCIV-CXVI is repeated with the use of 0.25% light stabilizer and low pressure polyethylene instead of polypropylene. Kneading is carried out at 180 ° C, and film forming at 150 ° C. A 1 mm thick pellet is formed. This lozenge is stored at 20 ° C and periodically checked visually for the first sign of sweating. The obtained results are presented in Table VIII, which also contains data on comparative experiments / additions of known light stabilizers /.

Table VIII

<td>Example</td><td>Light stabilizer added</td><td>Exposure time in days until sweating</td>

<td> —</td><td>2,2,6,6- 4-stearate -czterometylopipery- dynes</td><td> 15</td>

<td></td><td>bis- / 2,2,6,6-four methylpyrosinate sebacate /</td><td> 20</td>

<td></td><td>4-stearylcarbamyl x2, 2,6, 6-thylpiperidine</td><td> 13</td>

<td>0X711</td><td>1,2,2,6,6-five-methylpiperidine 4-stearate</td><td> &gt;50</td>

<td>οχνιιι</td><td>bis sebacate - / 1,2,2,6, 6-pięciometylopipery- dynes /</td><td> &gt;50</td>

<td>CXIX</td><td>4-s tearylcarfoamyl xy-1,2,2,6,6-five-methylpiperidine</td><td> &gt;50 • 1</td>

Examples CXX — CXXII. The method described in examples CXVII-ΌΧΙΧ is repeated with the fact that the molding is carried out at 200 ° C and high pressure polyethylene is used. The results obtained are presented in Table IX, which also contains data on comparative experiments (using known light stabilizers). \

Table IX

<td>Example</td><td>Light stabilizer</td><td>Exposure time in bagpipes until sweating</td>

<td> —</td><td>2,2,6,6-tetra-4-stearate and ethyl dipol</td><td> 40</td>

<td>ΟΧΧ</td><td>1,2,2,6,6-pentymethylpiperidine 4-stearate</td><td> &gt;75</td>

<td>CXXI</td><td>4-s teary loka rbamyl ksy-1,2,2,2,6-five-methylpiperidine</td><td> &gt;75</td>

<td>0ΧΧΙΙ</td><td>1-in-dodecyl-2,2,6,6-carboxylic acid carboxylate 4-heptane carboxylate</td><td> &gt;75</td>

Examples ΟΧΧΙΙΙ — CXXVIII. 10 parts of crystalline polystyrene pellets are mixed with 0.25 parts of 1,2,2,6,6-pentylpiperidine 4-stearate, and then homogenized. Injection-stabilized pellets are held for 3000 hours in the illuminating part of the "Xenotest 150" apparatus. The color change is determined by calculating the yellowing index according to the equation:

ΔΤ / 420 / Δ-T_/680, yellowness factor = ~ X 100 in

T /₅₆₀/ which ΔΤ is the value of the decrease in permeability of the non-exposed sample for a 560 mm light wavelength. The results obtained, the results of the control experiments, and the results for the compositions obtained according to the invention are presented in Table X.

Table X

<td>Example¹</td><td>Light stabilizer</td><td>Yellowness factor after 3000 hours</td>

<td></td><td>Without stabilizer</td><td> 35,0</td>

<td>ΟΧΧΙΙΙ</td><td>1,2,2,6,6-five dye piperipearate</td><td> 10,0</td>

<td>CXXIV</td><td>1-benzyl-2,2,6,6-tetramethylpiperidine 4- / 1'-ethylpentanecarboxylate</td><td> 9,8</td>

<td>CXXV</td><td>4-n-Heptanocar Xylan 1,2,2,6,6 D Five Lopiperidine Finish</td><td> 9,5</td>

<td>CXXVI</td><td>4- / 2'-cyanoethoxy / -. -1,2,2,6,6-pięciometylopiperydyna</td><td> 8,0</td>

<td>οχχνιι</td><td>4-teary lolkarbamyl xy-1,2,2,6,6-five-methylpiperidine</td><td> 7,5</td>

<td>CXXVIII</td><td>bis- / l succinate, 2,2,6, 6-pięciometylopipery- dynes /</td><td> 6,6</td>

Examples CXXIX-0ΧΧΧΙΙ. 25 parts of a film-forming polyurethane based on polyester are dissolved in 75 parts of a mixture of dimethylformamide and acetone in a 1: 1 volume ratio, and 1% 4- / 2'-cyanoethoxy / -1, 2,2,6,6, -pentomethylpiperidine is added. A clear, homogeneous solution is drawn between the glass plates to obtain a 400-500 micron film that is dried for 4 minutes at 50 ° C and 6 minutes at 140 ° C. The final film thickness is 80-100 microns. The dried film is removed from between the glass plates, placed on a white cardboard and illuminated in the "Xenotest 450". Half of the sample is covered to facilitate visual assessment of yellowing caused by exposure. The sample is inspected and visually evaluated within 100 hours. The results obtained are given in Table XI, which also contains the results of the respective control experiments (without the addition of light stabilizers) and other experiments using the stabilizers obtained by the methods of the invention.

Table XI

<td>Example</td><td>Light stabilizer</td><td>Yellowing time in hours</td>

<td> —</td><td>Without stabilizer</td><td> &lt;100</td>

<td>ΟΧΧΙΧ</td><td>4- / 2'-cyanoethoxy / l, 2, 2,6,6-pentyl, methyl piperidine</td><td> 200</td>

<td>Cxxx</td><td>1,2,2,6,6-pentomethyl piperidine 4-heptanecarboxylate</td><td> 300</td>

<td>CXXXI</td><td>bis- (1,2,6, 6-pentomethyl-4-piperidine) sebacate /</td><td>3Ό0</td>

<td>ΟΧΧΧΙΙ</td><td>4-phenylcarbamyloxy-ln-propyl-2,2,6,6-pentone ethyl ethyl piperidine</td><td> 400</td>

Examples CXXXIII — CXXXV. 1000 parts of unstabilized polypropylene powder are mixed with 1 part of n-octadecyl-β- / hydroxy-3 ', 5'-di-tert-butylphenyl propionate and 2 parts of / 3',5'-tert-butyl-4'- 1,2,2,6,6-pentomethylpiperidine hydroxy / benzoate, then pressed at a cylinder temperature of 180-220 ° C and granulated. The molten raw material is spun under the following conditions: extrusion temperature - 230/265 / / 275 ° C, dyeing temperature - 270 ° C, drawing speed - 400 m / minute, stretching ratio 1: 5, titer of multifilament yarn -

cd of table XII

<td> 1</td><td> 2</td><td> 3</td><td> 4</td>

<td>cxxxvi</td><td>4-P / 3 ', 5'-two-III rows -butyl-4'-hydroxyphenyl / propionate 1,2, 2,6,6-pentimethylpiperidine</td><td> 1600</td><td> 3,7</td>

<td>CXXXV</td><td>bis- / 1,2,2,6,6-pentachylate-4-.piperidine /</td><td> 2600</td><td> 6,0</td>

130/137 denier, tensile strength 6 g / denier.

Samples of the obtained multifilament yarn are placed in an apparatus "Xenotest 150" (with quartz lamp GmbH) and, using white cardboard as background, irradiated for 200 hours. During this time, 5 fiber samples are taken and their tensile strength is measured. The obtained results are presented on the graph as a function of exposure time / TA. Based on this graph, the exposure time after which the tensile strength drops to 50% of the initial value was calculated.

Examples CXXXVI — CXLIV. The procedure described in Examples XCIV-CXVI is followed, except that analogous substances are exposed to polypropylene in the radiation part of the "Xenotest 450" apparatus and not in the fadeometric device. The obtained results are presented in Table XIII, which also includes the results of control experiments (without the use of light stabilizers), as well as the results of comparative experiments (using a known light stabilizer).

Table XII

<td rowspan="2">Example</td><td rowspan="2">Stabilizer light</td><td rowspan="2">Exposure time T after which the sample breaks at a $ 50 elongation</td><td>Co- factor Stabilized T</td>

<td>T comparison</td>

<td> 1</td><td> 2</td><td> 3</td><td> 4</td>

<td></td><td>Without stabilizer</td><td> 430</td><td> 1,0</td>

<td></td><td>2- / 2'-hydroxy- -3 ', 5'-di-IIIrz.- butylphenyl / -5- -chlorobenzo- triazole</td><td> 530</td><td> 1,2</td>

<td>CXXXIII</td><td>4- / 3 ', 5'-di-tert-butyl-4'-hydroxyybenzoate 1,2,2,6,6-pentylpiperidine</td><td> 1400</td><td> 3,3</td>

Table XIII

<td>Example</td><td>Light stabilizer</td><td>Time of destruction In hours</td>

<td> 1</td><td> 2</td><td> 3</td>

<td> —</td><td>Without stabilizer</td><td> 800</td>

<td></td><td>2- / 2'-hydroxy-3 ', 5'-di-tert-butylphenyl / -5-chlorobenzo triazole</td><td> 1630</td>

<td>CXXXVI</td><td>bis- / l, 2,2,6, 6-pięciometylopipery- dynes /</td><td> &gt;9000</td>

<td>CXXXVII</td><td>4-p / 3^,,5^,-dw^andt-butyl-4'-hydroxyphenyl 1,2,2,6,6-pentylpiperidyl propionate</td><td></td>

<td></td><td>ny</td><td> 19000</td>

<td>CXXXVIII</td><td>4- / 3 ', 5'-two-III-T-shoes lo - 4'- hy d.roxy'be n z esan 1,2,2,6,6-pentylpiperidine</td><td> &gt;8600</td>

<td>CXXXIX</td><td>4-heptanokafboksylan 1,2,2,6,6-five-methyl pip of the dyna era</td><td> 6500</td>

214

<td></td><td>, cont</td><td>table XIII</td>

<td> 1</td><td> 2</td><td> 3</td>

<td></td><td>4-fenylokarbamyloksy-</td><td></td>

<td>CXL ·</td><td>-1,2,2,6,6-piięiometylo- piperidine 4-th locarlbamyloxy-</td><td> &gt; 7000</td>

<td>CXLI</td><td>-1,2,2,6,6 6p-methylcyciperidine 4-cyclohexylcarbo -</td><td> 6000</td>

<td>CXLII</td><td>1,2,2,6,6-pyrimethylpiperidine xylan 4-siteerate 1,2,2,6,6-</td><td> &gt;6000</td>

<td>CXLIH</td><td>-pięoiometylopiperydy- ny 1,2,2,6,6-4-benzoate</td><td> 6000</td>

<td>CXLIV</td><td>-pięciometylopipery- dynes</td><td> 5000</td>

Examples CXLV — CL ·. 100 parts of polyamide-6 pellets containing 1.8 parts of TiO₂ dry mixed with 0.5 parts of 4-benzyloxy-1, 2.2,

6,6-pięciometylopiperydyny. The molten mixture is spun into 20 denier fibers. The unstressed fiber is placed on a white cardboard and exposed to light radiation in the "Xenotest 450".

After 500, 1000, 1500 and 2000 hours of exposure, it tests the breaking strength of 5 fibers from each sample. Arithmetic mean percentages of initial tensile strength were presented as functions of exposure time. Destruction point - exposure time, after which a 50% decrease in the beginning of the year occurs. XIV

<td>Example</td><td>Stabilizer, light</td><td>Time: 50% decrease in initial tensile strength in him d 'Zanach</td>

<td></td><td>Without stabilizers</td><td> 4175</td>

<td>CXLV</td><td>4-benzyloxy-1,2,2,6,6-five-methyl pipers -</td><td></td>

<td></td><td>on</td><td> 1420</td>

<td>cxlviii</td><td>bis sebacate - / ^ 20, · 0.6, 6-pentomethyl-piperidine /</td><td> 1600</td>

<td>cxlix</td><td>4-heptane carboxylate 1,2,2,6,6-pfca: iomethyl-</td><td> *</td>

<td></td><td>piperidine</td><td> 1450</td>

<td>CXLVIII</td><td>1-phenylcarbamyloxy -1,2,2,6,6-p ^ ^: LiDi ^ eylpiperidine</td><td> 1450</td>

<td>CXLIX</td><td>1,6-bis- / 4'-carbaimyl xyrimir, 2 '; 2', 6 ', 6'-pentimethylpiperidine / hex</td><td></td>

<td></td><td>san</td><td> 1500</td>

<td>CL</td><td>l 44&gt; IS- / l ',, 2', 2 ', 6', 6'-five. methyl-4&gt; diphenyloxy / butane piper</td><td> 1600</td>

initial tensile strength - calculated from this graph.