MXPA99010921A - Block oligomers containing 1-hydrocarbyloxy-2,2,6,6-tetramethyl-4-piperidyl groups as stabilizers for organic materials - Google Patents

Abstract

A product obtainable by transferring groups of formula (G-I) being present in a block oligomer having a polydispersity Mw/Mn of 1 to 1.7 and corresponding to formula (I) to groups of formula (G-II), wherein R1 is a hydrocarbyl radical or -O-R1 is oxyl;said transfer is carried out by reaction of the block oligomer with a hydroperoxide in a hydrocarbon solvent in the presence of a peroxide decomposing catalyst;n is a number from 2 to 14;R2 is for example C2-C12alkylene;A is for example -N(R4)(R5);R4 and R5 are for example C1-C18alkyl;R is preferably a group of formula (G-I) and B and B* have one of the meanings given for A;with the proviso that in the individual recurrent units of formula (I), each of the radicals B, R and R2 has the same or a different meaning. The products are useful as light stabilizers, heat stabilizers and oxidation stabilizers for organic materials, in particular synthetic polymers.

Description

BLOCK OLIGOMERS CONTAINING 1-HIDROCARBILOX - 2,2,6,6-TETRAMETIL-4-PIPERIDIT GROUPS, 0 AS STABILIZERS FOR ORGANIC MATERIALS The present invention relates to specific block oligomers containing 1-hydrocarbyloxy-2, 2, 6, 6-tetramethyl-4-piperidyl groups, for use as light stabilizers, thermal stabilizers and oxidation stabilizers for organic materials, particularly synthetic polymers. , and with the organic materials thus stabilized. The stabilization of synthetic polymers with 2, 2, 6,6-tetramethylpiperidine derivatives has been described for example in US-A-4 086 204, US-A-4 331 586, US-A-4 335 242, US-A -4 234 707, US-A-4 459 395, US-A-4 492 791, US-A-5 204 473, EP-A-53 775, EP-A-357 223, EP-A-377 324, EP-A-462 069, EP-A-782 994 and GB-A-2 301 106. The present invention relates in particular to a product obtainable by transferring groups of the formula (GI) being presented in a block oligomer having a polydispersity Mw / Mn from 1 to 1.7 than that corresponding to formula (I) to the groups of the formula (G-II); where Ri is a hydrocarbyl radical or -O-Ri is oxyl; the transfer is carried out by reacting the block oligomer corresponding to the formula (I) with a hydroperoxide in a hydrocarbon solvent in the presence of a catalyst which decomposes the peroxide; n is a number from 2 to 14; the radicals R2 are independently of each other C2-C12 alkylene, C4-C12 alkenylene, C5-C cycloalkylene, C5-Cdi cycloalkylene (C1-C4 alkylene), C4-C4-cycloalkylene alkylene of Cs- C7), phenylendi (C? -C alkylene) or C4-C? 2 alkylene interrupted by 1,4-piperazinyl, -0- or > N-X? with Xi being acyl of C1-C12 or (C? -C? 2 alkoxy) carbonyl or having one of the definitions of R4 given below; or R2 is a group of formulas (a), (b) or (c); with m being 2 or 3, X 2 being C 1 -C 8 alkyl, C 5 -C 2 cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C 4 -C 4 alkyl; phenyl which is unsubstituted or substituted by 1, 2 or 3 C 1 -C 4 alkyl or C 1 -C 4 alkoxy; C7-C9 phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C? -C4 alkyl; and the X3 radicals independently of each other being C2-C2 alkylene; the radicals A being independently of one another -OR3, -N (R) (R5) or a group of the formula (II); R3, R and R5, which are identical or different, are Ci-Cis alkyl, C5-C2 cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C?-C4 alkyl; C3-C18 alkenyl, phenyl which is unsubstituted or substituted by 1, 2 or 3 C? -C4 alkyl or C? -C alkoxy; C7-C9 phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 Cx-C4 alkyl; tetrahydrofurfuryl or C2-C4 alkyl which is substituted in the 2, 3 or 4 position by -OH, C? -C8 alkoxy, di (C1-C4 alkyl) amino or a group of the formula (III); / \ Y N ("i) \ / with Y being -O-, -CH2-, -CH2CH2- or> N-CH3; and R3 is further hydrogen or -N (R) (R5) is additionally a group of the formula (III); X is -O- or > N-R6; R 6 is C 1 -C 18 alkyl, C 3 -C 18 alkenyl, C 5 -C 6 cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C 1 -C 4 alkyl; C7-C9 phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C1-C4 alkyl; tetrahydrofurfuryl, a group of the formula (GI), or C2-C alkyl which is substituted at the 2, 3 or 4 position by -OH, Ci-Cß alkoxy, di (C?-C4 alkyl) amino or a group of the formula (III); the radicals R independently have one of the meanings given for Re; and the radicals B and B * have independently one of the meanings given for A; with the proviso that in the individual recurring units of the formula (I), each of the radicals B, R and R2 have the same or different meaning. In the repetitive units of formula (I), the radical R and the radical can have a random distribution or a distribution of blocks The transfer of the groups of formula (GI) to the groups of the formula (G-II) can be carried out, for example, analogously to the method described in US-A-4 921 962 which is incorporated herein by reference. Polydispersity indicates the molecular weight distribution of a polymeric compound. In the present application, polydispersity is the ratio of the weights Molecular weight average (Mw) and numerical average (Mn).

A value of Mw / Mn equal to 1 means that the compound is monodisperse and has only a molecular weight and not a molecular weight distribution. A narrow molecular weight distribution is characterized by a polydispersity Mw / Mn close to 1.

When the polydispersity Mw / Mn is 1, n is preferably 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12, in particular 2, 3, 4, 5 or 6, for example 2, 4 or 6. A preferred block oligomer of the formula (I) has a polydispersity Mw / Mn of 1.1. to 1.7. Such a block oligomer is polydispersed and has a molecular weight distribution. More specifically, such a block oligomer corresponds to a mixture containing at least three different monodisperse compounds of the formula (I) which vary only in the variable n, the mixture has a polydispersity of 1.1 to 1.7.

When the polydispersity Mw / Mn is greater than 1, n is preferably a number from 2 to 12, in particular 2 to 6. The preferred block oligomers have a Polydispersity Mw / Mn from 1.1 to 1.65, 1.1 to 1.6, 1.1 to 1.55, 1.1 to 1.5, 1.1 to 1.45, 1.1 to 1.40 or 1.1 to 1.35. A Mw / Mn polydispersity of 1.1 to 1.55, eg, 1.1 to 1.5, is particularly preferred.

Additional examples of the polydispersity Mw / Mn are from 1.15 to 1.7, for example 1.15 to 1.65, 1.15 to 1.6, 1.15 to 1.55, 1.15 to 1.5, 1.15 to 1.45, 1.15 to 1.40 or 1.15 to 1.35.

A polydispersity Mw / Mn of 1.15 to 1.55, for example 1.15 to 1.5, is also particularly preferred. The meaning of Ri depends on the hydrocarbon solvent used. Ri is preferably a hydrpcarbyl radical having from 5 to 18 carbon atoms. Ri is in particular C 5 -C 8 alkyl, alkenyl C5-C18, C5-C18 alkynyl, C5-C12 cycloalkyl unsubstituted or substituted by C? -C4 alkyl; C 5 -C 2 cycloalkenyl unsubstituted or substituted by C 1 -C 4 alkyl; a bicyclic or tricyclic hydrocarbyl having from 6 to 10 carbon atoms or C7-Cg phenylalkyl unsubstituted or substituted on the phenyl by C 1 -C 4 alkyl; and the hydrocarbon solvent accordingly, depends on Rlf C5-C8 alkane, C5-C18 alkene, C5-C18 alkyne, Cs-C ?2 cycloalkane unsubstituted or substituted by C?-C4 alkyl; C5-C2-cycloalkene unsubstituted or substituted by C1-C4alkyl; a bicyclic or tricyclic hydrocarbon having 6 to 10 carbon atoms or C7-C9 phenylalanyl unsubstituted or substituted on the phenyl by C 1 -C 4 alkyl. Examples of alkyl not containing more than 18 carbon atoms are methyl, ethyl, propyl, isopropyl, butyl, 2-butyl, isobutyl, t-butyl, pentyl, 2-pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, t-octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, hexadecyl and octadecyl. Ri is preferably C 1 -C 2 alkyl, in particular heptyl or octyl. R4, R5 and R & they are preferably C?-C8 alkyl / in particular C alquilo-C- alkyl. An example of C2-C4 alkyl substituted by -OH is 2-hydroxyethyl. Examples of C 2 -C 4 alkyl substituted by C 1 -C 8 alkoxy, preferably by C 1 -C 4 alkoxy, in particular methoxy or ethoxy, are 2-methoxyethyl, 2-ethoxyethyl, 3-methoxypropyl, 3-ethoxypropyl, 3- butoxypropyl, 3-octoxypropyl and 4-methoxybutyl. Examples of C 2 -C 4 alkyl substituted by di (C 1 -C 4 alkyl) amino, preferably by dimethylamino or diethylamino, are 2-dimethylaminoethyl, 2-diethylaminoethyl, 3-dimethylaminopropyl, 3-diethylaminopropyl, 3-dibutylamino-propyl and 4-diethylaminobutyl. The group of the formula (III) is preferably / \ N O \ / Preferred examples of C2-C4 alkyl substituted by a group of formula (III) are the groups of The group The examples of C5-C2 cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C6-C4 alkyl are cyclopentyl, ethylcyclopentyl, dimethylcyclopentyl, cyclohexyl, methylcyclohexyl, dimethylcyclohexyl, trimethylcyclohexyl, t -butylcyclohexyl, cyclooctyl, cyclodecyl and cyclododecyl. Unsubstituted or substituted cyclohexyl is preferred.

A preferred example of a bicyclic or tricyclic hydrocarbyl having from 6 to 10 carbon atoms is 1,2,3,4-tetrahydronaphtenyl. A preferred example of C 5 -C 2 cycloalkenyl unsubstituted or substituted by C 1 -C 4 alkyl is cyclohexenyl. Examples of alkenyl containing not more than 18 carbon atoms are allyl, 2-methylallyl, butenyl, hexenyl, undecenyl and octadecenyl. Alkenyls in which the carbon atom in position 1 is saturated are preferred, and allyl is particularly preferred. A preferred example of C5-C18 alkynyl is octynyl. Examples of phenyl substituted by 1, 2 or 3 C 1 -C 4 alkyl or C 1 -C 4 alkoxy are methylphenyl, dimethylphenyl, trimethylphenyl, t-butylphenyl, di-t-butylphenyl, 3, 5-di-t-butyl- 4-methylphenyl, methoxyphenyl, ethoxyphenyl and butoxyphenyl. Examples of C7-C9 phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C1-C4 alkyl are benzyl, methylbenzyl, dimethylbenzyl, trimethylbenzyl, t-butylbenzyl and 2-phenylethyl. Benzyl is preferred. Examples of acyl (aliphatic, cycloaliphatic or aromatic) containing not more than 12 carbon atoms are formyl, acetyl, propionyl, butyryl, pentanoyl, hexanoyl, heptanoyl, octanoyl and benzoyl. Ci-Cß alkanoyl and benzoyl are preferred. Cetyl is especially preferred. Examples of (C 1 -C 12 alkoxy) carbonyl are methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, pentoxycarbonyl, hexoxycarbonyl, heptoxycarbonyl, octoxycarbonyl, nonyloxycarbonyl, decyloxycarbonyl, undecyloxycarbonyl and dodecyloxycarbonyl. Examples of alkylene containing not more than 12 carbon atoms are ethylene, propylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, octamethylene, decamethylene and dodecamethylene. R2 is for example C2-C8 alkylene or C4-C8 alkylene, in particular C2-Cg alkylene, preferably hexamethylene. An example of C 4 -C 2 alkenylene is 3-hexenylene. An example of C5-C7 cycloalkylene is cyclohexylene. The examples of alkylene of C-C? 2 interrupted by Examples of C4-C2 alkylene interrupted by -0-, for example 1, 2 or 3 -0-, are 3-oxapentan-l, 5-diyl, 4-oxaheptan-l, 7-diyl, 3,6-dioxaoctan-l, 8-diyl, 4,7-dioxadecan-1, 10-diyl, 4,9-dioxadodecan-l, 12-diyl, 3,6, 9-trioxaundecan-1, 11-diyl and 4, 7, 10-trioxatridecan-l, 13-diyl. Examples of C 4 -C 2 alkylene interrupted by > N-X? are -CH2CH2CH2-N (X1) -CH2CH2-N (X?) - CH2CH2CH2-, in particular -CH2CH2CH2-N (CH3) -CH2CH2-N (CH3) -CH2CH2CH2-. An example of C 5 -C 7 cycloalkylene (C 1 -C 4 alkylene) is cyclohexylenedimethylene. Examples of C? -C4alkylene (C5-C cycloalkylene) are methylenedicyclohexylene and isopropylidenedicyclohexylene. An example of phenylendi (C 1 -C 4 alkylene) is phenylenedimethylene. Ri is preferably heptyl, octyl, cyclohexyl, methylcyclohexyl, cyclooctyl, cyclohexenyl, α-methylbenzyl or 1,2,3,4-tetrahydronaphthhenyl, and the hydrocarbon solvent is accordingly, depending on Ri, heptane, octane, cyclohexane, methylcyclohexane, Cyclooctane, cyclohexene, ethylbenzene or tetralin. According to a further embodiment of this invention Ri is cyclohexyl or octyl, and the hydrocarbon solvent is, depending on Ri, cyclohexane or octane.

When -O-Ri is oxyl, the hydrocarbon solvent is conveniently an inert organic solvent, preferably toluene or, 2-dichloroethane. The catalyst that decomposes the peroxide is, for example, a metal carbonyl, metal oxide, metal acetylacetonate or a metal alkoxide where the metal is selected from groups IVb, Vb, VIb, Vllb and VIII of the periodic table, preferably vanadium (III) acetylacetonate, cobalt carbonyl, chromium (VI) oxide, titanium (IV) isopropoxide, titanium tetrabutoxide, • n-hexacarbonyl of molybdenum, molybdenum trioxide and the like. The most preferred catalyst is Mo03. Suitable hydroperoxides are t-butyl hydroperoxide, t-amyl hydroperoxide, t-hexyl hydroperoxide, t-octyl hydroperoxide, ethylbenzene hydroperoxide, tetralin hydroperoxide or eumeno hydroperoxide (= isopropylbenzene). The most preferred hydroperoxide is t-butyl hydroperoxide. 2 to 8 moles, preferably 3 to 6 moles, of the hydroperoxide, 0.001 to 0.1 moles, preferably 0.005 to 0.05 moles, of the peroxide decomposing catalyst and 5 to 30 moles, are applied preferably from 10 to 20 moles, of the hydrocarbon solvent, for example, per mole of the hindered amine portion of the formula (GI) which is present in the block oligomer. The transfer of the hindered amine portions of the formula (G-I) to the groups of the formula is, for example, from 75 to 160 ° C, preferably from 100 to 150 ° C. When the hindered amine portions of the formula (GI) are first treated with aqueous hydroperoxide in the presence of the catalyst that decomposes the peroxide in an inert organic solvent (for example analogously to the method described in US-A-4 691 015) , the initial reaction product obtained in a relatively short time is the corresponding N-oxyl intermediate (-OR? = oxyl) which is highly colored and can be isolated per se. When the organic solvent is a hydrocarbon having a labile hydrogen atom, when there is still a sufficient molar excess of hydroperoxide beyond what is necessary to convert the amine to the corresponding N-oxyl derivative, and when the reaction mixture is heated to moderate temperatures (preferably 100 to 150 ° C) and for a further period, an additional reaction takes place between the N-oxyl compound (either prepared in situ from the original amine or used as a starting intermediate initial in the process), and the hydrocarbon solvent to give the corresponding N-hydrocarbyloxy derivative. The original reaction mixture is colorless, but becomes highly colored as the N-oxyl intermediate is formed.This color disappears when the N-oxyl compound is converted to the colorless N-hydrocarbyloxy product. In essence, it has a color indicator that shows the degree of the reaction.When the reaction mixture becomes colorless, it shows that the colored N-oxyl intermediate has been completely converted to the N-hydroxycarbyloxy product. The product according to this invention can be purified by one of the following methods: a) The residual peroxide is decomposed and the solvent is evaporated to obtain a crude solid product The solid is stirred with an inert solvent such as cyclohexane, octane, hexane, petroleum ether, xylene, toluene, acetone, methyl ethyl ketone, ethyl acetate, butyl acetate, t-butyl alcohol, t-amyl alcohol, isopropyl alcohol, ethanol, methanol, chlorine formed, dichloromethane, acetonitrile, diethyl ether, dibutyl ether and / or water. The mixture can be heated while stirring. After stirring, the mixture is cooled and the solid product is collected by filtration and dried. b) The residual peroxide decomposes and the solvent evaporates partially. The residue is filtered to obtain a solid which is washed with an inert solvent such as one of the above, which can be cooled and then dried. c) The residual peroxide decomposes and the solvent evaporates at elevated temperature to obtain a molten mass. The hot melt is mixed with an inert solvent, such as one of the above, which can be cooled, and the resulting precipitate is collected by filtration and dried. Variations of this process include mixing the hot melt with solvent and then cooling the mixture to obtain a precipitate, or mixing the hot melt with solvent, heating to bring any solids to a solution, and then cooling to obtain a precipitate. d) The residual peroxide is decomposed and the solvent is removed at elevated temperature to obtain a melt. The melt is dissolved in an inert solvent, such as one of the above, with or without heating, and the resulting solution can be concentrated by distilling some of the excess solvent. The solution is then mixed with a second solvent, such as one of the above, at a temperature such that the product precipitates. The solid is collected by filtration and dried. More specifically, the product according to this invention is preferably purified as follows: After completion of the reaction, the crude reaction mixture is cooled to 50 ° C and treated with 20% aqueous sodium sulfite until the concentration of the residual peroxide falls below 0.5% The aqueous layer is divided, and the organic layer is concentrated heating the product solution under reduced pressure The crude product is dissolved in an excess of t-butyl alcohol, and the solvent is removed by heating the solution under reduced pressure until the concentration of the solids is 50%. slowly to cold methanol The resulting precipitate is filtered, washed with methanol, and dried under vacuum.The starting material of the block oligomer of the formula (I) having a polydispersity of 1 to 1.7 is described in the US Patent Serial No. 08 / 756,225 and EP-A-782, 994. The starting material of the block oligomer has a polydispersity Mw / Mn of a value greater than 1 at a value of 1.7 can be prepared, for example, as follows: 1) by reacting a compound of the formula (A) with a compound of the formula (B) in a stoichiometric ratio to obtain a compound of the formula (C); 2) by reacting a compound of formula (C) with a compound of formula (B) in a molar ratio of 1: 2 to 1: 3, preferably 1: 2, to obtain a mixture of at least three compounds different monodisperses of the formula (D) with n being 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14, in particular 2, 4, and 6; 3) by reacting the mixture obtained in 2) with a compound of the formula (E) in a stoichiometric ratio to obtain the desired product with the indicated polydispersity; reactions 1) to 3) are carried out in an organic solvent in the presence of an inorganic base. Examples for suitable organic solvents are toluene, xylene, trimethylbenzene, isopropylbenzene, diisopropylbenzene, and essentially water-insoluble organic ketones such as for example methyl ethyl ketone and methyl isobutyl ketone. Xylene is preferred. Examples for an inorganic base are sodium hydroxide, potassium hydroxide, sodium carbonate and potassium carbonate. Sodium hydroxide is preferred. Reaction 1) is carried out, for example, at a temperature of 40 ° C to 70 ° C, preferably 50 ° C to 60 ° C. Reaction 2) is carried out, for example, at a temperature of 110 ° C to 180 ° C, preferably 140 ° C to 160 ° C. Reaction 3) is carried out, for example, at a temperature of 110 ° C to "180 ° C, preferably 140 ° C to 160 ° C. Possible by-products are the compounds of the formulas (BI) and (B-II).

Each of these compounds, which are known from US-A-4 108 829 and US-A-4 442 250 can be present in the mixtures in an amount of, for example, up to 30 mol%, so preferably up to 20 mol% or up to 10 mol%, in particular up to 8 mol%, relative to the total mixture. The compound of the formula (A) can be prepared, for example, by reacting cyanuric chloride with a compound B-H in a stoichiometric ratio in the presence of an organic solvent and an inorganic base.

In addition, the compound of the formula (E) can be prepared, for example, by reacting cyanuric chloride with the compounds of the formulas A-H and B * -H in a stoichiometric ratio in the presence of an organic solvent and an inorganic base. It is appropriate to use the preparation of the compounds of formulas (A) and (E) the same solvent and the same inorganic base as in the reactions indicated above 1) to 3). The initial materials used in the above process are known. In case they are not commercially available, they can be prepared analogously to known methods. For example, some starting materials of the formula (B) are described in WO-A_95 / 21157, US-A-4, 316, 837 and US-A-4,743, 688. A particularly preferred starting material is a product having a polydispersity Mw / Mn of 1.1 to 1.7 or more specifically a mixture with the indicated polydispersity, the mixture contains at least three monodisperse compounds which differ only in the number of repetitive units and which are a) a compound of the formula (S-Ia) b) a compound of the formula (S-Ib) and c) a compound of the formula (S-Ic), the radicals A, B, B *, R and R2 are as defined above and the ratio of the compounds of the formulas (S-Ia) to ^ (S-Ib) to (S-Ic) in mol% is 2: 1.6: 1 to 2: 0.4: 0.04, preferably 2: 1.2: 0.5 to 2: 0.4: 0.04, in particular 2: 1: 0.4 to 2: 0.45: 0.04. The initial materials of the formula (I) that have a polydispersity Mw / Mn of 1 can be prepared by building the compound step by step. Some representative examples of such a procedure are shown below.

I) A compound of the formula (I) wherein R is a group of the formula (GI) and n is 2 can be conveniently prepared by reacting a compound of the formula (E) with a large excess of a compound of the formula (I) B) to obtain a compound of the formula (F) according to Scheme 1-1. The molar ratio of the compound of the formula (E) to the compound of the formula (B) can be for example 1: 4.

Scheme 1-1: (E) (B) (F) Subsequently, the compound of the formula (F) can be reacted with the compound of the formula (C) in a stoichiometric ratio to obtain the desired compound as shown in Scheme 1-2.

Scheme 1-2: (F) (C) II) A compound of the formula (I) wherein R is a group of the formula (GI) and n is 3 can be prepared conveniently by reacting a compound of the formula (F) with a compound of the formula (A) in a stoichiometric ratio to obtain a compound of the formula (G) according to Scheme II-1.

Scheme I -l: (F) (A) (G) Next, the compound of the formula (G) can be reacted with a large excess of a compound of the formula (B) to obtain a compound of the formula (H) as shown in ei- Esquela II-2 . The molar ratio of the compound of the formula (G) to the compound of the formula (B) can be for example 1: 4.

Scheme II-2: (G) (B) (H) Subsequently, the compound of the formula (H) can be reacted with a compound of the formula (A) in a stoichiometric ratio to obtain a compound of the formula (K), following Scheme II-3.

Scheme II-3: (HE HAS) (K) III) A compound of the formula (I) wherein R is a group of the formula (GI) and n is 4 can be conveniently prepared by reacting a compound of the formula (H) with a compound of the formula ( C) in a stoichiometric ratio to obtain a compound of the formula (L).

(H) (C) (D Reactions I) to III) are carried out, for example, in an organic solvent such as toluene, xylene, trimethylbenzene, in the presence of an inorganic base such as sodium hydroxide at a temperature of 110 ° C. 180 ° C, preferably from 140 ° C to 160 ° C. The preferred products of this invention are those, where R is a group of the formula (G-I). Preferred products of this invention are also those, where R 2 is C 2 -C 2 alkylene, C 5 -C 7 cycloalkylene, C 5 -C 7 cycloalkylene di (C 1 -C 4 alkylene), C 1 -C 4 alkylene cycloalkylene di (cycloalkylene) of C5-C7), phenylendi (C1-C4 alkylene) or C4-C2 alkylene interrupted by -O- or > N-X? with Xi being acyl of C? ~ C? 2 or (C? -C? 2 alkoxy) carbonyl or having one of the definitions of R4; or R2 is a group of the formula (b); R3, R4 and R5, which are identical or different, are C? -Ci8 alkyl, Cs-C? 2 cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C? -C4 alkyl; phenyl, which is unsubstituted or substituted by 1, 2 or 3 C 1 -C 4 alkyl or C 1 -C 4 alkoxy; C7-Cg phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C 1 -C 4 alkyl; and R3 is further hydrogen or -N (R4) (R5) is further a group of the formula (III); R6 is Ci-Cis alkyl, C5-C2 cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 alkyl. C1-C4; C7-Cg phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C 1 -C 4 alkyl; or a group of the formula (G-I). A further preferred embodiment of this invention relates to those products, where n is a number from 2 to 12; R 2 is C 2 -C 12 alkylene, C 5 -C 7 cycloalkylene, C 5 -C 7 cycloalkylene di (C 1 -C 4 alkylene), C 1 -C 4 alkylene (C 5 -C 7 cycloalkylene) or phenylene (C 1 -C alkylene) C4); R6 is C? -C? 8 alkyl, Cs-C? 2 cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 alkyl C? ~ C4; phenylalkyl of C-Cg, which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C1-C4 alkyl; or a group of the formula (G-I); and R is a group of the formula (G-I). Those products are of interest, where R2 is C2-C6 alkylene, cyclohexylene, cyclohexylendi (C? -C4 alkylene), C? -C4 alkylene dicyclohexylene, or phenylendi (C1-C4 alkylene); R3, R4 and R5, which are identical or different, are C1-C12 alkyl, C5-C7 cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4 alkyl, phenyl which is unsubstituted or substituted by 1, 2 or 3 C 1 -C 4 alkyl; or benzyl which is unsubstituted or substituted on the phenyl by C? -C4 alkyl; or -N (R4) (R5) is additionally a group of the formula (neither); and R6 is C1-C12 alkyl, C5-C7 cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 alkyl C1-C4; benzyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C 1 -C 4 alkyl; or a group of the formula (G-I). Also of interest are those products, where R2 is alkylene of C2-Cs; R3, R4 and R5, which are identical or different, are Ci-Cß alkyl, cyclohexyl which is unsubstituted or substituted by methyl; phenyl which is not substituted or substituted by methyl; or benzyl; or -N (R4) (R5) is further 4-morpholinyl; and Rd is C? -C8 alkyl / cyclohexyl which is unsubstituted or substituted by methyl; benzyl or a group of the formula (G-I). Of additional interest is a product, where n is a number from 2 to 6; R2 is C2-C6 alkylene; A is -N (R4) (R5) or a group of the formula (II); R 4 and R 5, which are identical or different, are C 1 -C 8 alkyl; or -N (R4) (R5) is further 4-morpholinyl; X is > NR6; Re is C? -C4 alkyl; and the radicals B and B * independently of one another have one of the definitions given for A. A further preferred product is that, where B * is different from B and each of the radicals B, R and R2 have the same meaning in the individual recurring units of the formula (I). An embodiment of this invention is also a product obtainable by the hydrogenation of a product wherein -ORi in the formula (G-II) is oxyl to obtain a block oligomer with groups of the formula (G-III).

The hydrogenation is carried out according to known methods, for example in an organic solvent, for example methanol or ethanol, in the presence of a hydrogenation catalyst, preferably palladium or carbon or Pt02, as described for example in US-A-4 691 015. Another embodiment of this invention is a mixture containing a) a monodisperse compound of the formula (la), b) a monodisperse compound of the formula (Ib) and c) a monodisperse compound of the formula (le) the compounds of the formulas (la), (Ib) and (le) differ only in the number of repetitive units, the ratio of the compounds of the formulas (la) to (Ib) ) a (le) in mol% is 2: 1.6: 1 to 2: 0.4: 0.04, preferably 2: 1.2: 0.5 to 2: 0.4: 0.04, in particular 2: 1: 0.4 to 2: 0.45: 0.04; and Ri is hydrogen, a hydrocarbyl radical or "-0-R" is oxyl, R2 is C2-C2 alkylene, C4-C2 alkenylene, C5-C7 cycloalkylene, C5-C7 cycloalkylene (alkylene) of C? -C4), alkylene of C? -C4 di- (C5-C7 cycloalkylene), phenylendi (C? -C4 alkylene) or C4-C? 2 alkylene interrupted by 1,4-piperazinyl, -O - or> NX? with X being C1-C12 acyl or (C1-C12 alkoxy) carbonyl or having one of the definitions of R4 given below, or R2 is a group of the formula (a), (b) or (c); with m being 2 or 3, X2 being Ci-Ciß alkyl, C5-C12 cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C? -C alkyl; phenyl which is unsubstituted or substituted by 1, 2 or 3 C 1 -C 4 alkyl or C 1 -C 4 alkoxy; phenylalkyl of C-Cg which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C 1 -C 4 alkyl; and the X3 radicals independently of each other being C2-C2 alkylene; A * is -OR3, -N (R4) (R5) or a group of the formula (G-IV); R 3, R 4 and R 5, which are identical or different, are C 1 -C 8 alkyl, C 5 -C 7 cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C 1 -C 4 alkyl; C 3 -C 8 alkenyl, phenyl which is unsubstituted or substituted by 1, 2 or 3 C 1 -C 4 alkyl or C 1 -C 4 alkoxy; phenylalkyl of C-Cg which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C 1 -C 4 alkyl; tetrahydrofurfuryl or C2-C4 alkyl which is substituted in the 2, 3 or 4 position by -OH, Ci-Cs alkoxy, di (C? -C4 alkyl) amine or a group of the formula (III); AND N- (III) with Y being -O-, -CH2-, -CH2CH2- or > N-CH3; and R3 is further hydrogen or -N (R4) (R5) is further a group of the formula (III); X * is -O- or > N-R6 *; Re * is C 1 -C 8 alkyl, C 3 -C 8 alkenyl, C 5 -C 12 cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C 1 -C 4 alkyl; C7-C8 phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C1-C4 alkyl; tetrahydrofurfuryl, a group of the formula (G-II), or C-C4 alkyl which is substituted in the 2, 3 or 4 position by -OH, C? -C8 alkoxy, di (C? -C4 alkyl) amino or a group of the formula (III); R * has one of the meanings given for Re *; and the radicals B * and B ** have independently one of the meanings given for A *. After the transfer of the groups of the formula (G-l) being present in the initial material of the block oligomer with a polydispersity of, for example, 1.1 to 1.7 (mixture containing the compounds of the formulas (S-Ia), (S-Ib) and (S-Ic)) at the groups of the formula (G-II), the ratio of the compounds of the formula (a) to (Ib) a (le) corresponds to the ratio of the initial compounds shown above of the formula (S-Ia) to (S-Ib) to (S-Ic), since the skeleton of these compounds is not affected during the reaction. The preferred is a mixture, wherein Ri is cyclohexyl or octyl; R2 is C2-C6 alkylene; A * and B ** which are identical or different are -N (C? -Cs alkyl) 2 or a group of the formula (G-IV-I) B * is a group of the formula (G-IV-1); and R * is a group of the formula (G-II). In the mixtures according to this invention, the radical Ri can act as a linking group between two or more block oligomers of the formula (la), (Ib) and / or (le). In this case, the bridges of the formula (L-1) are formed between the indicated oligomers of blocks.

The meaning of Ri * can be deduced from the meaning of Rx. The only difference between these two radicals is that Ri * has one or two additional valences. Thus, Rx as cyclohexyl corresponds to Ri * as cyclohexanediyl or cyclohexantriyl and Ri as octyl corresponds to Ri * as octandiyl or octantriil. The products of this invention as well as the mixtures described are very effective in improving the resistance to light, heat and oxidation of organic materials, especially synthetic polymers and copolymers. In particular, a low pigment interaction as well as a very good color are observed in polypropylene, especially polypropylene fibers, in particular in the presence of flame retardants as well as in low density polyethylene (LDPE) films for agricultural uses. It is further notable that the product of this invention and the mixtures described are flame retardant in themselves. Examples of organic materials that can be stabilized are: 1. Polymers of monoolefins and diolefins, for example polypropylene, polyisobutylene, polybut-1-ene, poly-4-methylpent-l-ene, polyisoprene or polybutadiene, as well as cycloolefin polymers , for example of cyclopentene or norbornene, polyethylene (which may be optionally crosslinked), for example high density polyethylene (HDPE), high molecular weight high density polyethylene (HDPE-HM), high density polyethylene and ultra high molecular weight (HDPE-UHMW), medium density polyethylene (MDPE), low density polyethylene (LDPE), linear low density polyethylene (LLDPE), (VLDPE) and (ULDPE). The polyolefins, ie the polymers of the monoolefins exemplified in the preceding paragraph, preferably polyethylene and polypropylene, can be prepared by different methods, and especially by the following: a) radical polymerization (usually under high pressure and at elevated temperature). b) catalytic polymerization using a catalyst that normally contains one or more than one of the metals of groups IVb, Vb, VIb or VIII of the Periodic Table. These metals usually have one or more than one ligand, typically oxides, halides, alcoholates, esters, ethers, amines, alkyls, alkenyls and / or aryls which may be either coordinated or coordinated. These metal complexes may be in free form or fixed on substrates, typically on activated magnesium chloride, titanium (III) chloride, alumina or silicon oxide. These catalysts can be soluble or insoluble in the polymerization medium. The catalysts can be used by themselves in the polymerization or additional activators can be used, typically metal alkyls, metal hydrides, metal alkyl halides, metal alkyl oxides or metal alkyloxanes, the metals being the elements of the groups la, lía and / or Illa of the Periodic Table. These activators can be conveniently modified with additional ester, ether, amine or silyl ether groups. These catalyst systems are usually called Phillips catalysts, from Oil Indiana Standard, from Ziegler (-Natta), TNZ (DuPont), metallocene or single-site catalysts (SSC). 2. The polymer mixtures mentioned under 1), for example mixtures of polypropylene with polyisobutylene, polypropylene with polyethylene (for example PP / HDPE, PP / LDPE) and mixtures of the different types of polyethylene (for example LDPE / HDPE). 3. Copolymers of monoolefins and diolefins with one another or with other vinyl monomers, for example ethylene / propylene copolymers, linear low density polyethylene (LLDPE) and mixtures thereof with low density polyethylene (LDPE), propylene copolymers / but-1-ene, propylene / isobutylene copolymers, ethylene / but-1-ene copolymers, ethylene / hexene copolymers, ethylene / methylpentene copolymers, ethylene / heptene copolymers, ethylene / octene copolymers, propylene copolymers / butadiene, isobutylene / isoprene copolymers, ethylene / alkyl acrylate copolymers, ethylene / alkyl methacrylate copolymers, ethylene / vinyl acetate copolymers and their copolymers with carbon monoxide or copol mers of ethylene / acrylic acid and their salts (ionomers) and terpolymers of ethylene with propylene and a diene such as hexadiene, dicyclopentadiene or ethylidenenorbornene; and blends of such copolymers with others and with the polymers mentioned in 1) above, for example polypropylene / ethylene-propylene copolymers, LDPE / ethylene vinyl acetate (EVA) copolymers, LDPE / ethylene acrylic acid (EAA) copolymers , LLDPE / EVA, LLDPE / EAA and alternating or random polyalkylene / carbon monoxide copolymers and mixtures thereof with other polymers, for example polyamides. 4. Hydrocarbon resins (eg C5-C9) including hydrogenated modifications thereof (eg adhesives) and mixtures of polyalkylenes and starch. 5. Polystyrene, poly (p-methylstyrene), poly (α-methylstyrene). 6. Copolymers of styrene or α-methylstyrene with dienes or acrylic derivatives, for example styrene / butadiene, styrene / acrylonitrile, styrene / alkyl methacrylate, styrene / butadiene / alkyl acrylate, styrene / butadiene / alkyl methacrylate, styrene / maleic anhydride, styrene / acrylonitrile / methyl acrylate; mixtures of high impact strength or copolymers of styrene and another polymer, for example a polyacrylate, a diene polymer or an ethylene / propylene / diene terpolymer; and styrene block copolymers such as styrene / butadiene / styrene, styrene / iso-prene / styrene, styrene / ethylene / butylene / styrene or styrene / ethylene / propylene / styrene. 7. The grafted copolymers of styrene or α-methylstyrene, for example copolymers of styrene on polybutadiene, styrene on polybutadiene-styrene or polybutadiene-acrylonitrile; styrene and acrylonitrile (or methacrylonitrile) on polybutadiene; styrene, acrylonitrile and methyl methacrylate on polybutadiene; styrene and maleic anhydride on polybutadiene; styrene, acrylonitrile and maleic anhydride or maleimide on polybutadiene; styrene and maleimide on polybutadiene; styrene and alkyl acrylates or methacrylates on polybutadiene; styrene and acrylonitrile on ethylene / propylene / diene terpolymers; styrene and acrylonitrile on polyalkyl acrylates or polyalkyl methacrylates, styrene and acrylonitrile on acrylate / butadiene copolymers, as well as mixtures thereof with the copolymers listed under 6), for example the copolymer mixtures known as ABS, MBS, ASA or AES 8. Halogen-containing polymers such as polychloroprene, chlorinated rubbers, chlorinated and brominated copolymer of isobutylene-isoprene (halobutyl rubber), chlorinated or sulfochlorinated polyethylene, copolymers of ethylene and chlorinated ethylene, homo and epichlorohydrin copolymers, especially polymers of vinyl compounds containing halogen, for example polyvinyl chloride, polyvinylidene chloride, polyvinyl fluoride, polyvinylidene fluoride, as well as copolymers thereof such as vinyl chloride / vinylidene chloride, vinyl chloride / vinyl acetate or sodium chloride copolymers vinylidene / vinyl acetate. 9. Polymers derived from acids, β-unsaturates and derivatives thereof, such as polyacrylates and polymethacrylates; polymethyl methacrylates, polyacrylamides and polyacrylonitriles, modified by impact with butyl acrylate. 10. Copolymers of the monomers mentioned under 9) with each other or with other unsaturated monomers, for example acrylonitrile / butadiene copolymers, acrylonitrile / alkyl acrylate copolymers, acrylonitrile / alkoxyalkyl acrylate or acrylonitrile / vinyl halide copolymers or terpolymers of acrylonitrile / alkyl methacrylate / butadiene. 11. Polymers derived from unsaturated alcohols and amines or the acyl derivatives or acetals thereof, for example, polyvinyl alcohol, polyvinyl acetate, polyvinyl stearate, polyvinyl benzoate, polyvinyl maleate, polyvinyl butyral, polyallyl phthalate or polyallyl melamine; as well as their copolymers with the olefins mentioned in 1) above. 12. Homopolymers and copolymers of cyclic ethers such as polyalkylene glycols, polyethylene oxide, polypropylene oxide or copolymers thereof with bisglycidyl ethers. 13. Polyacetals such as polyoxymethylene and those polyoxy ethylenes containing ethylene oxide such as a comonomer; polyacetals modified with thermoplastic polyurethanes, acrylates or MBS. 14. Polyphenylene oxides and sulphides, and mixtures of polyphenylene oxides with styrene polymers or polyamides. 15. Polyurethanes derived from polyethers terminated in hydroxyl, polyesters or polybutadienes on the one hand and aliphatic or aromatic polyisocyanates on the other, as well as precursors thereof. 16. Polyamides and copolyamides derived from diamines and dicarboxylic acids and / or aminocarboxylic acids or the corresponding lactams, for example polyamide 4, polyamide 6, polyamide 6/6, 6/10, 6/9, 6/12, 4/6 , 12/12, polyamide 11, polyamide 12, aromatic polyamides starting from m-xylene diamine and adipic acid; polyamides prepared from hexamethylenediamine and isophthalic acid and / or terephthalic acids and with or without an elastomer as a modifier, for example poly-2,4,4-trimethylhexamethylene terephthalamide or poly-m-phenylene isophthalamide; and also block copolymers of the polyamides mentioned above with polyolefins, olefin copolymers, ionomers or chemically bonded or grafted elastomers; or with polyethers, for example with polyethylene glycol, polypropylene glycol or polytetramethylene glycol; as well as polyamides or copolyamides modified with EPDM or ABS; and polyamides condensed during processing (RIM polyamide systems). 17. Polyureas, polyimides, polyamide-iides, polyetherimides, polyesterimides, polyhydantoins and polybenzimidazoles. 18. Polyesters derived from dicarboxylic acids and / or from hydroxycarboxylic acids or the corresponding lactones, for example polyethylene terephthalate, polybutylene terephthalate, poly-1,4-dimethylolcyclohexane terephthalate and polyhydroxybenzoates, as well as block copolyether esters derived from polyethers finished in hydroxyl; and also polyesters modified with polycarbonates or MBS. 19. Polycarbonates and polyester carbonates. 20. Polysulfones, polyether sulfones and polyether ketones. 21. Cross-linked polymers derived from aldehydes on the one hand and phenols, ureas and melamines on the other hand, such as phenol / formaldehyde resins, urea / formaldehyde resins and melamine / formaldehyde resins. 22. Alkyd resins with staining and without staining. 23. Unsaturated polyester resins derived from copolyesters of saturated and unsaturated dicarboxylic acids with polyhydric alcohols and vinyl compounds as crosslin agents, and also halogen-containing modifications of low flammability. 24. Crosslinkable acrylic resins derived from substituted acrylates, for example epoxy acrylates, urethane acrylates or polyester acrylates 25. Alkyd resins, polyester resins and acrylate resins crosslinked with melamine resins, urea resins, isocyanates , isocyanurates, polyisocyanates or epoxy resins 26. Crosslinked epoxy resins derived from aliphatic, cycloaliphatic, heterocyclic or aromatic glycidyl compounds, for example the products of the diglycidyl ethers of bisphenol A and bisphenol F, which are crosslinked with customary hardeners such as anhydrides or amines, with or without accelerators 27. Natural polymers such as cellulose, rubber, gelatin and chemically modified homologous derivatives thereof, for example cellulose acetate, cellulose propionates and cellulose butyrates, or cellulose ethers such like methyl cellulose; as well as resins and their derivatives. 28. Mixtures of the polymers mentioned above (polyblends), for example PP / EPDM, Polyamide / EPDM or ABS, PVC / EVA, PVC / ABS, PVC / MBS, PC / ABS, PBTP / ABS, PC / ASA, PC / PBT, PVC / CPE, PVC / acrylates, POM / PUR thermoplastic, PC / PUR thermoplastic, POM / acrylic, POM / MBS, PPO / HIPS, PPO / PA 6.6 and copolymers, PA / HDPE, PA / PP, PA / PPO, PBT / PC / ABS or PBT / PET / PC. 29. Natural and synthetic organic materials which are pure monomeric compounds or mixtures of such compounds, for example mineral oils, animal and vegetable fats, oils and waxes, or oils, fats and waxes based on synthetic esters (for example phthalates, adipates, phosphates or trimellitrates and also mixtures of synthetic esters with mineral oils in any weight ratios, typically those used as spinning compositions, as well as aqueous emulsions of such materials.

. Aqueous emulsions of natural or synthetic rubber, for example latex or natural latexes of carboxylated styrene / butadiene copolymers. The invention thus also relates to a composition comprising an organic material susceptible to degradation induced by light, heat or oxidation and a product or mixture according to this invention. The organic material is preferably a synthetic polymer, more particularly one selected from the groups mentioned above. Polyolefins are preferred and polyethylene and polypropylene are particularly preferred. A further embodiment of this invention is a method for stabilizing an organic material against degradation induced by light, heat or oxidation, which comprises incorporating a product or a mixture according to this invention into the organic material. The product or mixture according to this invention can be used in various proportions depending on the nature of the material to be stabilized, the end use and the presence of other additives. In general, it is appropriate to use, for example, the 0. 01 to 5% by weight of the product or the mixture "according to this invention, in relation to the weight of the material to be stabilized, preferably from 0.05 to 2%, in particular 0.05 to 1% .The product or the mixture of According to this invention it can be added, for example, to the polymeric materials before, during or after the polymerization or crosslinking of the materials In addition, they can also be incorporated into the polymeric materials in pure form or encapsulated in waxes, oils or polymers. In general, the product or mixture according to this invention can be incorporated into the polymeric materials by various processes, such as dry mixing in the form of powder, or wet mixing in the form of solutions or suspensions or else in the form of a masterbatch which contains the product or mixture according to this invention in a concentration of 2.5 to 25% by weight, in such operations, the polymer can be used in the form of powder, granules, solutions, suspensions, or in the form of latices. The materials stabilized with the product or mixture according to this invention can be used for the production of moldings, films, tapes, monofilaments, fibers, surface coatings and the like. If desired, other conventional additives can be added for synthetic polymers, such as antioxidants, UV absorbers, nickel stabilizers, pigments, fillers, plasticizers, corrosion inhibitors and metal deactivators, to the organic materials containing the product or mixture according to this invention. The "particular examples of such conventional additives are: 1. Antioxidants 1.1. Alkylated monophenols, for example 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4,6-di-methylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6 -di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-isobutylphenol, 2,6-dicyclopentyl-4-methylphenol, 2- (a-methylcyclohexyl) -4,6-dimethylphenol , 2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, nonylphenols which are linear or branched in the side chains, for example 2, 6-di-nonyl-4-methylphenol, 2,4-dimethyl-6- (1'-methylundec-1'-yl) phenol, 2,4-di-methyl-6- (1-methylheptadec-1- il) phenol, 2,4-dimethyl-6- (! '-methyltridec-l' -yl) phenol and mixtures thereof. 1. 2. Alkyltiomethylphenols, for example 2,4-dioctylthiomethyl-6-tert-butylphenol, 2,4-dioctylthiomethyl-6-methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol, 2,6-di-dodecylthiomethyl-4-nonylphenol. 1. 3. Hydroquinones and alkylated hydroquinones, for example 2, 6-di-tert-butyl-4-methoxy-phenol, 2,5-di-tert-butylhydroquinone, 2,5-di-tert-amylhydroquinone, 2,6-diphenyl -4-octadicyloxyphenol, 2,6-di-tert-butylhydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyanisole, 3,5-di stearate -tert-butyl-4-hydroxyphenyl, bis (3, 5-di-tert-butyl-4-hydroxyphenyl) adipate. 1. 4. Tocopherols, for example α-tocopherol, β-tocopherol, β-tocopherol, d-tocopherol and mixtures thereof (Vitamin E) . 1. 5. Hydroxylated thiodiphenyl ethers, for example 2,2'-thiobis (6-tert-butyl-4-methylphenol), 2,2'-thiobis (4-octylphenol), 4,4'-thiobis (6-tert-butyl) 3-methylphenol), 4,4'-thiobis (6-tert-butyl-2-methylphenol), 4,4'-thiobis- (3,6-di-sec-amylphenol), 4,4'-disulfide bis (2,6-dimethyl-4-hydroxyphenyl). 1. 6. Alkylidenebisphenols, for example 2,2'-methylenebis (6-tert-butyl-4-methylphenol), 2,2'-methylenebis (6-tert-butyl-4-ethylphenol), 2,2'-methylenebis [4] -methyl-6- (a-methylcyclohexyl) -phenol], 2,2'-methylenebis (4-methyl-6-cyclohexylphenol), 2,2'-methylenebis (6-nonyl-methylphenol), 2,2 '-methylenebis (4,6-di-tert-butylphenol), 2,2'-ethylidebis (4,6-di-tert-butyl-phenol), 2,2'-ethylidebis (6-tert-butyl-4-) isobutylphenol), 2,2'-methylenebis [6- (a-methylbenzyl) -4-nonylphenol], 2,2'-methylenebis [6- (a, a-dimethylbenzyl) -4-nonylphenol], 4,4'- methylenebis (2,6-di-tert-butylphenol), 4,4'-methylenebis (6-tert-butyl-2-methylphenol), 1,1-bis (5-tert-butyl-4-hydroxy-2-methylphenyl) ) butane, 2,6-bis (3-tert-butyl-5-methyl-2-hydroxybenzyl) -4-methylphenol, 1, 1,3-tris (5-tert-butyl-4-hydroxy-2-methylphenyl) butane, 1, 1-bis (5-tert-butyl-4-hydroxy-2-methyl-phenyl) -3-n-dodecyl mercaptobutane, ethylene glycol bis [3, 3-bis (3'-tert-butyl) butyrate 4 '-hydroxyphenyl)], bis (3-tert-butyl-4-hydroxy-5-methyl-phenyl) di-cyclopen tadiene, bis [2- (3'-tert-butyl-2'-hydroxy-5'-methylbenzyl) -6-tert-butyl-4-methyl "phenyl] terephthalate, 1,1-bis- (3, 5) -dimethyl-2-hydroxyphenyl) butane, 2, 2-bis- (3, 5-di-tert-butyl-4-hydroxyphenyl) propane, 2, 2-bis- (5-tert-butyl-4-hydroxy-2) -methylphenyl) -4-n-dodecyl mercaptobutane, 1,1,5,5-tetra- (5-tert-butyl-4-hydroxy-2-methylphenyl) pentane. 1. 7. Compounds of O-, N- and S-benzyl, for example 3, 5, 3 ', 5' -tetra-tert-butyl-4,4'-dihydroxydi-benzyl ether, octadecyl-4-hydroxy-mercaptoacetate 3, 5-dimethylbenzyl, tridecyl-4-hydroxy-3,5-di-tert-butyl-benzyl mercaptoacetate, tris (3,5-di-tert-butyl-4-hydroxybenzyl) amine, dithio-terephthalate from "bis (4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl), bis (3,5-di-tert-butyl-4-hydroxy-benzyl) sulfide, isooctyl-3, 5-diol-mercaptoacetate tert-butyl-4-hydroxybenzyl. 1. 8. Hydroxybenzylated malonates, for example dioctadecyl-2, 2-bis- (3, 5-di-tert-butyl-2-hydroxybenzyl) malonate, di-octadecyl-2- (3-tert-butyl-4-malonate) hydroxy-5-methylbenzyl), di-dodecylmercaptoethyl-2,2-bis- (3, 5-di-tert-butyl-4-hydroxybenzyl) malonate, bis [4- (1, 1, 3, 3- tetramethylbutyl) phenyl] -2, 2-bis (3,5-di-tert-butyl-4-hydroxybenzyl). 1. 9. Aromatic hydroxybenzyl compounds, for example l, 3,5-tris- (3,5-di-tert-butyl-4-hydroxy-benzyl) -2,4,6-trimethylbenzene, 1,4-bis (3 , 5-di-tert-butyl-4-hydroxybenzyl) -2,3,5,6-tetramethylbenzene, 2,4,6,6-tris (3,5-di-tert-butyl-4-hydroxybenzyl) phenol. 1. 10. Triazine compounds, for example 2,4-bis (octylmercapto) -6- (3,5-di-tert-butyl-4-hydroxyanilino) -1,3,5-triazine, 2-octylmercapto-4,6 -bis (3, 5-di-tert-butyl-4-hydroxyanilino) -1,3,5-triazine, 2-octylmercapto-4,6-bis (3,5-di-tert-butyl-4-hydroxyphenoxy) -1,3,5-triazine, 2,4,6-tris (3,5-di-tert-butyl-4-hydroxyphenoxy) -1,2,3-triazine, isocyanurate of 1, 3, 5-tris- (3, 5-di-tert-butyl-4-hydroxy-benzyl), isocyanurate 1, 3, 5-tris (4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl), 2,4,6- tris (3, 5-di-tert-butyl-4-hydroxyphenylethyl) -1,3,5-triazine, 1,3,5-tris (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) -hexahydro- 1, 3, 5-triazine, isocyanurate of 1, 3, 5-tris (3,5-dicyclohexyl-4-hydroxybenzyl). 1. 11. Benzylphosphonates, for example dimethyl-2,5-di-tert-butyl-4-hydroxybenzyl phosphonate, diethyl-3,5-di-tert-butyl-4-hydroxybenzyl phosphonate, dioctadecyl-3, 5- phosphonate. di-tert-butyl-4-hydroxybenzyl, dioctadecyl-5-tert-butyl-4-hydroxy-3-methylbenzyl phosphonate, - the calcium salt of the 3,5-di-tert-butyl-4- monoethyl ester hydroxybenzylphosphonic 1. 12. Acylaminophenols, for example 4-hydroxylauranylide, 4-hydroxysteatenylidene, N- (3,5-di-tert-butyl-4-hydroxyphenyl) octyl carbamate.1. 13. Esters of ß- (3- (3,5-di-tert-butyl-4-hydroxy enyl) propionic acid with mono- or polyhydric alcohols, for example with methanol, ethanol, n-octanol, i-octanol, octadecanol , 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N'-bis ( hydroxyethyl) oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexandiol, trimethylolpropane, 4-hydroxymethyl-l-phospha-2,6,7-trioxabicyclo [2.2.2] octane. 1. 14. Esters of β- (5-tert-butyl-4-hydroxy-3-methyl enyl) propionic acid with mono- or polyhydric alcohols, for example with methanol, ethanol, n-octanol, i-octanol, octadecanol, , 6-hexan-diol, 1, 9-nonandiol, ethylene glycol, 1,2-propanediol, neopentyl glycol, tiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N'bis (hydroxyethyl) ) oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexandiol, trimethylolpropane, 4-hydroxymethyl-l-phospha-2, 6,7-trioxabicyclo [2.2.2] octane. 1. 15. Esters of ß- (3,5-dicyclohexyl-4-hydroxyphenyl) propionic acid with mono- or polyhydric alcohols, for example with methanol, ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-nonandiol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N'-bis (hydroxyethyl) oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexandiol, trimethylolpropane, 4-hydroxymethyl-l-phospha-2, 6, 7-trioxabicyclo [2.2.2] octane. 1. 16. Esters of 3,5-di-tert-butyl-4-hydroxyphenyl acetic acid with mono- or polyhydric alcohols, for example with methanol, ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-nonandiol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N'-bis (hydroxyethyl) oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexandiol, trimethylolpropane, 4-hydroxymethyl-l-phospha-2, 6, 7-trioxabicyclo [2.2.2] octane. 1. 17. Amides of ß- (3,5-di-tert-butyl-4-hydroxy enyl) propionic acid for example N, N'-bis (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) examethylenediamide, N , N'-bis (3,5-di-tert-butyl-4-hydroxy-phenylpropionyl) trimethylene-diamide, N, N'-bis (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) -hydrazide, N, N '-bis [2- (3, 5-di-tert-butyl-4-hydroxyphenyl] pro-phenyloxy) ethyl] oxamide (Naugard®XL-1 distributed by Uniroyal). 1. 18. Ascorbic acid (vitamin C) 1. 19. Aminic antioxidants, for example N, N'-di-isopropyl-p-phenylenediamine, N, N'-di-sec-butyl-p-phenylene-diamine, N, N'-bis (1,4-dimethylpentyl) -p-phenylenediamine, N, N'-bis (l-ethyl-3-methylpentyl) -p-phenylenediamine, N, N'-bis (1-methyl-heptyl) -p-phenylenediamine, N, N'-dicyclohexyl- p-phenylenediamine, N, '-diphenyl-p-phenylenediamine, N, N' -bis (2-naphthyl) -p-phenylene-diamine, N-isopropyl-N '-phenyl-p-phenylenediamine, N- (l, 3-dimethylbutyl) -N'-phenyl-p-phenylenediamine, N- (1-methylheptyl) -N'-phenyl-p-phenylenediamine, N-cyclohexyl-N '-phenyl-p-phenylene-diamine, 4- (p. -toluensulfamoyl) diphenylamine, N, '-dimethyl-N, N' -di-sec-butyl-p-phenylene-diamine, diphenylamine, N-allyldiphenylamine, 4-isopropoxy-diphenylamine, N-phenyl-1-naphthylamine, N- (4-tert-octylphenyl) -1-naphthylamine, N-phenyl-2-naphthylamine, octylated diphenylamine, for example p, p'-di-tert-octyldiphenylamine, 4-n-butylaminophenol, 4-butyrylaminophenol, 4-nonanoylaminophenol, 4-dodecanoylamino-phenol, 4-octadecane-ylaminophenol, bis (4-methoxyphenyl) amine, 2, 6-di-tert-butyl-4-dimethylaminomethylphenol, 2,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, N, N, ', N' -tetramethyl-4,4'-diaminodiphenylmethane, 1, 2- bis [(2-methylphenyl) amino] ethane, 1,2-bis (phenylamino) propane, (o-tolyl) biguanide, bis [4- (1 ', 3'-dimethylbutyl) phenyl] amine, N-phenyl-1 -Ter-octylated naphthylamine, a mixture of mono- and dialkylated tert-butyl / tert-octyldiphenylamines, a mixture of mono- and dialkylated nonildyphenylamines, a mixture of mono- and dialkylated dodecyldiphenylamines, a mixture of mono- and dialkylated isopropyl / isohexyldiphenylamines, a mixture of mono- and dialkylated tert-butyldiphenylamines, 2,3-dihydro-3, 3-dimethyl-4H-1, 4- benzothiazine, phenothiazine, a mixture of mono- and dialkylated ter-butyl / tert-octylphenothiazines, a mixture of mono- and dialkylated ter-octylphenotiazines, N-allylphenothiazine, N, N, N ', N' -tetraphenyl-1, 4- diaminobut-2-ene, N, N-bis (2,2,6,6-tetramethyl-piperid-4-yl-hexamethylenediamine, bis (2,2,6,6-tetramethylpiperid-4-yl) -sebacate, 2 , 2,6,6-tetramethylpiperidin-4-one, 2,2,6,6-tetramethylpiperidin-4-ol. 2. UV absorbers and photostabilizers 2.1. 2- (2'-Hydroxyphenyl) benzotriazoles, for example 2- (2'-hydroxy-5'-methylphenyl) -benzotriazole, 2- (3 ', 5'-di-tert-butyl-2'-hydroxyphenyl) benzotriazole, 2- (5'-tert-butyl-2'-hydroxyphenyl) benzotriazole, 2- (2'-hydroxy-5 '- (1,1,3,3-tetra-methylbutyl) phenyl) benzotriazole, 2- (3') , 5'-di-tert-butyl-2'-hydroxyphenyl) -5-chloro-benzotriazole, 2- (3'-tert-butyl-2'-hydroxy-5'-methylphenyl) -5-chloro-benzotriazole, - (3 '-sec-butyl-5'-tert-butyl-2'-hydroxyphenyl) benzotriazole, 2- (2'-hydroxy-4'-octylOxyphenyl) benzotriazole, 2- (3', 5'-di-ter) -amil-2'-hydroxy-phenyl) benzotriazole, 2- (3 ', 5'-bis- (a, a-dimethylbenzyl) -2' -hydroxyphene) benzotriazole, 2- (3'-tert-butyl-2 ' -hydroxy-5 '- (2-octyloxycarbonylethyl) phenyl) -5-chloro-benzotriazole, 2- (3'-tert-butyl-5' - [2- (2-ethylhexyloxy) -carbonylethyl] -2'-hydroxy- phenyl) -5'-chloro-benzotriazole, 2- (3'-tert-butyl-2'-hydroxy-5 '- (2-methoxycarbonylethyl) phenyl) -5-chloro-benzotriazole, 2- (3'-ter- Butyl-2 '-hydroxy-5' - (2-methoxycarbonylethyl) phenyl) benz otriazole, 2- (3'-tert-butyl-2'-hydroxy-5 '- (2-octyloxy-carbonylethyl) phenyl) benzotriazole, 2- (3'-tert-butyl-5' - [2- (2- ethylhexyloxy) carbonylethyl] -2 '-hydroxyphenyl) benzotriazole, 2- (3'-dodecyl-2'-hydroxy-5' -methylphenyl) benzotriazole, 2- (3'-tert-butyl-2'-hydroxy-5 '- (2-isooctyloxycarbonylethyl) phenylbenzotriazole, 2,2'-methylene-bis- [4- (1,1,3,3-tetramethylbutyl) -6-benzotriazol-2-ylphenol]; the product of the transesterification of 2- [3'-tert-butyl-5 '- (2-methoxycarbonylethyl) -2'-hydroxyphenyl] 2H-benzotriazole with polyethylene glycol 300; [R-CH2CH-COO-CH2CH2-] - where R = 3'-tert-butyl-4'-hydroxy-5'r-2H-benzotriazol-2-ylphenyl, 2- [2'-hydroxy-3 '- ( a, a-dimethylbenzyl) -5 '- (1,1,3,3-tetramethylbutyl) -phenyl] enzotriazole; 2- [2'-hydroxy-3 '(1,1,3,3-tetramethylbutyl) -5' - (a, -dimethylbenzyl) -phenyl] benzotriazole. 2. 2-Hydroxybenzophenones, for example the 4-hydroxy, 4-methoxy, 4-octyloxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy, 4, 2 ',' -trihydroxy and 2'-hydroxy-4, 4 derivatives '-dimetoxi. ,? 2. 3. Esters of substituted and unsubstituted benzoic acids, such as for example 4-tert-butyl phenyl salicylate, phenyl salicylate, octyl phenyl salicylate, dibenzoyl resorcinol, bis (4-tert-butylbenzoyl) resorcinol, benzoyl resorcinol, 3, 5 2,4-di-tert-butylphenyl di-tert-butyl-4-hydroxybenzoate, hexadecyl 3, 5-di-tert-butyl-4-hydroxybenzoate, 3,5-di-tert-butyl-4-benzoate hydroxy-octadecyl, 3, 5-di-tert-butyl-4-hydroxybenzoate of 2-methyl-1,4-, 6-di-tert-butylphenyl. 2. 4. Acrylates, for example a-cyano-β, ethyl β-diphenylacrylate, α-cyano-β, isooctyl β-diphenylacrylate, methyl a-carbomethoxycinnamate, α-cyano-β-methyl-p-methoxy-cinnamate methyl, butyl a-cyano-β-methyl-p-methoxy-cinnamate, methyl α-carbomethoxy-p-methoxycinnamate and N- (β-carbomethoxy-β-cyanovinyl) -2-methylindoline. 2. 5. Nickel compounds, for example 2, 2'-thio-bis- [4- (1, 1, 3, 3-tetramethylbutyl) phenol] nickel complexes, such as the 1: 1 or 1: 2 complex, with or without additional ligands such as n-butylamine, triethanolamine or N-cyclohexyldiethanolamine, nickel dibutyldithiocarbamate, nickel salts of monoalkylated esters, for example the methyl or ethyl ester of 4-hydroxy-3,5-di-ter- butylbenzylphosphonic, ketoximes nickel complexes, for example 2-hydroxy-4-methylphenyl undecylketoxime, nickel complexes of 1-phenyl-4-lauroyl-5-hydroxypyrazole, with or without additional ligands. 2. 6. Sterically hindered amines, for example bis (2, 2, 6,6-tetramethyl-4-piperidyl) sebacate, bis (2, 2, 6,6-tetramethyl-4-piperidyl) succinate, bis ( 1, 2, 2, 6, 6-pentamethyl-4-piperidyl), bis (l-octyloxy-2, 2,6,6,6-tetramethyl-4-piperidyl) sebacate, bis (1,2,2, 6,6-pentamethyl-4-piperidyl) n-butyl-3,5-di-tert-butyl-4-hydroxybenzyl, the condensate of 1- (2-hydroxy-ethyl) -2,6,6-tetramethyl -4-hydroxypiperidine and succinic acid, linear or cyclic condensates of N, '-bis (2, 2, 6, 6-tetramethyl-4-piperidyl) hexamethylenediamine and 4-tert-octylamino-2,6-dichloro-l, 3, 5-triazine, tris-triacetate (2, 2, 6 , 6-tetramethyl-4-piperidyl) nitrile, tetracis (2,2,6,6-tetramethyl-4-piperidyl) -1,2,3,4-butane-tetracarboxylate, 1,1 '- (1, 2- ethanediyl) -bis (3, 3, 5, 5-tetramethylpiperazinone), 4-benzoyl-2,2,6,6-tetramethylpiperidine, 4-stearyloxy-2,6,6,6-tetramethylpiperidine, bis (1 2, 2, 6, 6-pentamethylpiperidyl) -2-n-butyl-2- (2-hydroxy-3,5-di-tert-butyl-benzyl), 3-n-octyl-7, 7, 9 , 9-tetramethyl-l, 3, 8-triazaspiro [4.5] decan-2,4-dione, bis (l-octyloxy-2, 2,6,6,6-tetramethylpiperidyl) sebacate, bis (l-) succinate octyloxy-2, 2,6,6,6-tetramethylpiperidyl), linear or cyclic condensates of N, N '-bis- (2,2,6,6-tetramethyl-4-piperidyl) hexa-methylenediamine and 4-morpholino-2, 6-dichloro-l 3,5-triazine, the condensate of 2-chloro-4,6-bis (4-n-butylamino-2, 2,6,6,6-tetramethylpiperidyl) -1, 3, 5-triazine and 1 2-bis (3-aminopropylamino) ethane, the condensate of 2-chloro-4,6-di- (4-n-butylamino-1,2,6,6-pentamethylpiperidyl) -1,3,5-triazine and 1,2-bis- ( 3-aminopropylamino) ethane, 8-acetyl-3-dodecyl-7, 7,9, 9-tetra-methyl-1,3,8-triazaspiro [4.5] decan-2,4-dione, 3-dodecyl-1- (2,2,6,6-tetramethyl-4-piperidyl) pyrrolidin-2, 5-dione, 3-dodecyl-1- (1,2,2,6,6-pentamethyl-4-piperidyl) pyrrolidin-2, 5-dione, a mixture of 4-hexadecyloxy- and 4-stearyloxy-2,2,6,6-tetramethylpiperidine, a condensation product of N, N'-bis (2, 2, 6, 6-tetramethyl-4-) piperidyl) hexamethylenediamine and 4-cyclohexylamino-2,6-dichloro-1,3,5-triazine, a product of the condensation of 1,2-bis (3-aminopropylamino) ethane and 2,4,6-trichloro-1, 3, 5-triazine as well as 4-butylamino-2, 2,6,6,6-tetramethylpiperidine (CAS Reg. No. [136504-96-6]); N- (2, 2, 6, 6-tetramethyl-4-piperidyl) -n-dodecyl succinimide, N- (1,2,2,6,6-pentamethyl-4-piperidyl) -n-dodecyl succinimide, 2-undecyl- 7, 7,9, 9-tetramethyl-l-oxa-3,8-diaza-4-oxo-spiro [4,5] -decano, a reaction product of 7, 7, 9, 9-tetramethyl-2- cycloundecyl-l-oxa-3,8-diaza-4-oxospiro [4,5] decane and epichlorohydrin, 1,1-bis (1,2,1,6,6-pentamethyl-4-piperidyloxy-carbonyl) -2 - (4-methoxyphenyl) ethene, N, N'-bis-formyl-N, N'-bis (2,2,6,6-tetramethyl-4-piperidyl) hexamethylenediamine, 4-methoxy-methylene-malonic acid diester with 1, 2, 2, 6, 6-pentamethyl-4-hydroxypiperidine, poly [methylpropyl-3-oxy-4- (2,2,6,6-tetramethyl-4-piperidyl)] siloxane, the reaction product of the of the anhydride-to-olefinic acid copolymer of maleic acid with 2, 2, 6, 6-tetramethyl-4-aminopiperidine or 1, 2, 2, 6, 6-pentamethyl-4-aminopiperidine. 2. 7. Oxamides, for example 4,4'-dioctyloxyoxanilide, 2,2 '-dietoxyoxanilide, 2,2' -dioctyloxy-5,5'-di-tert-butoxyanilide, 2,2'-didodecyloxy-5, 5 '- di-tert-butoxyanilide, 2-ethoxy-2'-ethyloxanilide, N, N'-bis (3-dimethyl-aminopropyl) oxamide, 2-ethoxy-5-tert-butyl-2'-ethoxyanilide and their mixtures with 2- ethoxy-2'-ethyl-5,4'-di-tert-butoxanilide, mixtures of oxanilides substituted with methoxy in the ortho and para positions and mixtures of oxanilides substituted with ethoxy in the ortho and para positions. 2. 8. 2- (2-Hydroxyphenyl) -1,3,5-triazines, for example 2,4,6-tris (2-hydroxy-4-octyloxyphenyl) -1,3,5-triazine, 2- (2- hydroxy-4-octyloxyphenyl) -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2- (2,4-dihydroxyphenyl) -4,6-bis (2,4-dimethylphenyl) -1, 3, 5-triazine, 2,4-bis (2-hydroxy-4-pro-piloxyphenyl) -6- (2,4-dimethylphenyl) - 1, 3, 5-triazine, 2- (2- hydroxy-4-octyloxyphenyl) -4,6-bis- (-methylphenyl) -1,3,5-triazine, 2- (2-hydroxy-4-dodecyloxyphenyl) -4,6-bis (2,4-dimethylphenyl) -1,3, 5-triazine, 2- (2-hydroxy-4-tridecyloxyphenyl) -4,6-bis (2, -dimethylphenyl) -1,3,5-triazine, 2- [2-hydroxy-4- (2-hydroxy-3-butyloxy-propoxy) phenyl] -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2- [2-hydroxy-4- (2-hydroxy-3 -octyloxy-propyloxy) phenyl] -4,6-bis- (2,4-dimethyl) -1,3,5-triazine, 2- [4- (dodecyloxy / tridecyloxy-2-hydroxypropoxy) -2-hydroxy-phenyl ] -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2- [2-hydroxy-4- (2-hydroxy-3-dodecyloxy-propoxy) phenyl] -4,6- bis (2,4-dimethyl-phenyl) -1, 3, 5-triazine, 2- (2-hydroxy-4-hexyloxy) phenyl-4,6-diphenyl-1,3,5-triazine, 2- (2-hydroxy-4-methoxyphenyl) -4,6-diphenyl -l, 3, 5-triazine, 2,4,6-tris [2-hydroxy-4- (3-butoxy-2-hydroxy-propoxy) phenyl] -1,3,5-triazine, 2- (2- hydroxyphenyl) -4- (4-methoxyphenyl) -6-phenyl-1,3,5-triazine, 2-. { 2-hydroxy-4- [3- (2-ethylhexyl-1-oxy) -2-hydroxy-propyloxy] phenyl} -4,6-bis (2,4-di-methylphenyl) -1,3,5-triazine. 3. Metal deactivators, for example N, N'-diphenyloxamide, N-salicylal-N '-salicyloyl hydrazine, N, N'-bis (salicyloyl) hydrazine, N, N'-bis (3,5-di-tert-butyl) 4-hydroxyphenylpropionyl) hydrazine, 3-salicyloylamino-1,2,4-triazole, bis (benzylidene) oxalyl dihydrazide, oxanilide, isophthaloyl dihydrazide, sebacoyl bisphenylhydrazide, N, N'-diacetyladipyl dihydrazide, N, N'-bis (salicyloyl) ) oxalyl dihydrazide, N, N'-bis (salicyloyl) thiopropionyl dihydrazide. 4. Phosphites and phosphonites, for example triphenyl phosphite, diphenyl alkyl phosphites, phenyl dialkyl phosphites, tris (nonylphenyl) phosphite, trilauryl phosphite, trioctadecyl phosphite, distearyl pentaerythritol diphosphite, tris (2, 4-dihydrogenphosphite) tert-butylphenyl), diisodecyl pentaerythritol diphosphite, bis (2,4-di-tert-butylphenyl) pentaerythritol diphosphite, bis (2,6-di-tert-butyl-4-methylphenyl) -pentaerythritol diphosphite, diisodecyldoxypentaerythritol diphosphite diphosphite of bis (2,4-di-tert-butyl-6-methylphenyl) pentaerythritol, diphosphite of bis (2,4,6-tris (tert-butylphenyl) pentaerythritol, tristearyl sorbitol triphosphite, tetracis diphosphonite (2, 4-di-tert-butylphenyl) 4,4 '-biphenylene, 6-isooctyloxy-2,4,8,10-tetra-tert-butyl-12H-di-benz [d, g] -1, 3, 2- dioxaphosphocin, 6-fluoro-2, 4,8, 10-tetra-tert-butyl-12-methyl-dibenz [d, g] -1, 3, 2-dioxaphosphocin, bis (2,4-di-ter) phosphite -butyl-6-methylphenyl) methyl, bis (2,4-di-tert-butyl-6-methylphenyl) ethyl phosphite, 2, 2 ' , 2"-nitrile [triethyltris (3, 3 ', 5, 5' -tetra-tert-butyl-1,1 '-biphenyl-2,2'-diyl) phosphite], 2-ethylhexyl (3,3', 5, 5'-tetra-tert-butyl-1, 1-biphenyl-2,2'-diyl) phosphite.

. Hydroxylamines, for example, N, N-dibenzylhydroxylamine, N, N-diethylhydroxylamine, N, N-dioctylhydroxylamine, N, N-dilaurylhydroxylamine, N, N-ditetradecylhydroxylamine, N, N-dihexadecylhydroxylamine, N, N-dioctadecylhydroxylamine, N-hexadecyl N-octadecylhydroxylamine, N-heptadecyl-N-octadecylhydroxylamine, N, N-dialkylhydroxylamine derived from hydrogenated tallow amine. 6. Neither ronas, for example, N-benzyl-alpha-phenylnitrona, N-ethyl-alpha-methyl-nitrona, N-octyl-alpha-heptyl-nitrona, N-lauryl-alpha-undecyl-nitrone, N-tetradecyl-alpha- tridicil-nitrona, N-hexadecyl-alpha-pentadecyl-nitrone, N-octadecyl-alpha-heptadecyl-nitrone, N-hexadecyl-alpha-hepta-decyl-nitrone, N-ochatadecyl-alpha-pentadecyl-nitrone, N-heptadecyl- alpha-heptadecyl-nitrone, N-octadecyl-alpha-hexa-decyl-nitrone, nitrone derived from N, N-dialkylohydroxyl-a-ina derived from hydrogenated tallow amine. 7. Tiosynergists, for example, dilauryl thiodipropionate or distearyl thiodipropionate. 8. Peroxide scavengers, for example esters of β-thiodipropionic acid, for example lauryl, stearyl, myristyl or tridecyl esters, mercaptobenzimidazole or the zinc salt of 2-mercapto-benzimidazole, zinc dibutyldithiocarbamate, dioctadecyl disulfide, tetracis (β -dodecylmercapto) pentaerythritol propionate. r • 9. Polyamide stabilizers, for example, copper salts in combination with iodides and / or phosphorus compounds and divalent manganese salts.

. Basic co-stabilizers, for example, melamine, polyvinylpyrrolidone, dicyandiamide, triallyl cyanurate, urea derivatives, hydrazine derivatives, amines, polyamides, polyurethanes, alkali metal salts and alkaline earth metal salts of higher fatty acids, for example calcium stearate, zinc stearate, magnesium behenate, sodium ricinoleate and potassium palmitate, antimony pyrocatechol or zinc pyrocatechol. 11. Nucleating agents, for example, inorganic substances such as talcum, metal oxides such as titanium dioxide or magnesium oxide, phosphates, tr-carbonates or sulfates of, preferably, alkaline earth metals; organic compounds such as mono- or polycarboxylic acids and salts thereof, for example 4-tert-butylbenzoic acid, adipic acid, diphenylacetic acid, sodium succinate or sodium benzoate; polymeric compounds such as ionic copolymers (ionomers) 12. Fillers and fillers, for example, calcium carbonate, silicates, glass fibers, glass bulbs, asbestos, talc, kaolin, mica, barium sulfate, metal oxides and hydroxides, carbon black, graphite, sawdust and flours or fibers of other natural products, synthetic fibers. 13. Other additives, for example, plasticizers, lubricants, emulsifiers, pigments, rheology additives, catalysts, flow control agents, optical brighteners, flameproofing agents, antistatic agents, and blowing agents. 14. Benzofuranones and indolinones, for example those described in the U.S. 4,325,863; U.S. 4,338,244; U.S. 5,175,312; U.S. 5,216,052; U.S. 5,252,643; DE-A-4316611; DE-A-4316622; DE-A-4316876; EP-A-0589839 or EP-A-0591102 or 3- [4- (2-acetoxyethoxy) -phenyl] -5,7-di-tert-butyl-benzofuran-2-one, 5,7-di-ter- butyl-3- [4- (2-stearoyloxyethoxy) phenyl] benzofuran-2-one, 3,3 '-bis [5,7-di-tert-butyl-3- (4- [2-hydroxyethoxy] phenyl) benzofuran -2-one], 5, 7-di-tert-butyl-3- (4-ethoxyphenyl) benzo-furan-2-one, 3- (4-acetoxy-3,5-dimethylphenyl) -5,7-di -te-butyl-benzofuran-2-one, 3- (3,5-dimethyl-4-pivaloyloxyphenyl) -5,7-di-tert-butyl-benzofuran-2-one, 3- (3,4-dimethylphenyl) -5,7-di-tert-butyl-benzofuran-2-one, 3- (2,3-di-methylphenyl) -5,7-di-tert-butyl-benzofuran-2-one. The weight ratio of the product or the mixture according to this invention with the conventional additives can be, for example, from 1: 0.5 to 1: 5. The products or mixtures of this invention can also be used as stabilizers, especially as photostabilizer, for almost all materials known in the photographic reproduction art and other such reproduction techniques, as for example, as described in Research Disclosure 1990, 31429 (pages 474 to 480). The invention is illustrated in more detail by the following Examples. All percentages and parts are by weight, unless otherwise indicated. The following Examples S-1 and S-2 are representative of the preparation of the starting materials. Examples 1 to 4 are representative of the preparation of the products according to this invention. GPC (Gel Permeation Chromatography) was used as an analytical procedure to separate from molecules by their difference in size and to obtain the averages of molecular weights (Mw, Mn) or information on the molecular weight distribution of the polymers. The technique is well known and is described, for example, in "Modern Size - Exclusion Liquid Chromatography" by .W.Yan et al., Edited by J. iley & Sons, N.Y., USA, 1979, pages 4-8, 249-283 and 315-340. A random molecular weight distribution is characterized by a polydispersity (Mw / Mn) close to 1.

The GPC analyzes shown in the following Examples S-1 and S-2 were carried out with a GPC®Perkin-Elmer LC 250 chromatograph equipped with an Rl ®Perkin-Elmer LC 30 detector and with the Furkin-Elmer LC oven. 101. All analyzes were carried out at 45 ° C using 3 μm E PLGEL mixture of three columns of 300 mm length x 7.5 mm internal diameter (from Polymers Laboratories Ltd. Shropshire, UK). Tetrahydrofuran was used as eluent (flow rate of 0.40 ml / min) and the samples were dissolved in tetrahydrofuran (2%) (% w / v). In the structural formulas of the following examples, n 'indicates that there are repetitive units in the molecules and that the products obtained are not uniform.

Example S-1: Preparation of the product of the formula A solution of 74.3 g (0.35 mol) of N- (2, 2,6,6-tetramethyl-4-piperidinyl) -n-butylamine in 50 ml of water was added slowly, at 0 ° C to a solution of 64.5 g (0.35 moles) of cyanuric chloride in 500 ml of xylene, maintaining the temperature during the addition and for an additional 1 hour. The mixture was cooled for 2 hours at room temperature then at 0 ° C and an aqueous solution of 14.7 g (0.368 mol) of sodium hydroxide in 50 ml of water was added. After 1/2 hour at 0 ° C and an additional 2 hours at room temperature, the aqueous solution was separated and 69.2 g- (0.175 moles) of N, N'-bis (2, 2, 6, 6 tetramethyl-4-piperidinyl) -1,6-hexandiamine. The mixture was heated at 50 ° C for 1 hour and 48.4 g (0.35 moles) of crushed potassium carbonate was added and heated at 60 ° C for 4 hours. After washing with water, the organic phase was concentrated under vacuum to 60-70 ° C / 10 mbar, 250 ml of xylene being recovered, and 138.1 g (0.35 mole) of N, N'-bis (2) were added. , 2, 6, 6-tetramethyl-4-piperidinyl) -1,6-hexandiamine and the mixture was heated at 150 ° C for 2 hours, cooled again and added with 14 g (0.35 mole) of crushed sodium hydroxide. .

The mixture was heated at 140 ° C for an additional 4 hours, removing the residual water from the reaction azeotropically and for an additional 4 hours at 160 ° C. After cooling to 60 ° C, the mixture was diluted with 300 ml of xylene, filtered and washed three times with 100 ml of ethylene glycol. After concentrating under vacuum at 60 ° C / 10 mbar, 78.7 g (0.147 mol) of 2-chloro-4,6-bis [N-2, 2,6,6-tetramethyl-4-piperidinyl] -n- were added. butylamino-1,3,5-triazine. The mixture was heated at 140 ° C for 3 hours and 5.9 g (0.147 moles) of crushed sodium hydroxide was added, heating the mixture to reflux and removing the water from the reaction azeotropically. The mixture was heated at 160 ° C for 4 hours, added with an additional 5.9 g (0.147 moles) of crushed sodium hydroxide and heated again at 160 ° C for 2 hours. After cooling to 60 ° C, the mixture was diluted with 300 ml of xylene, filtered and concentrated under vacuum at 140 ° C / 1 mbar-: A solid with a melting range of 166-170 ° C was obtained after to dry.

Mn (per GPC): 3360 g / mol Polydispersity Mw / Mn: 1.18 Analysis by GPC shows a chromatogram as in Figure 1.

The ratio of the three main components ((n '= 2): (n' = 4): (n '= 6)) of the polydispersed product obtained in a molar% of 2: 0.53: 0.05.

Example S-2: Preparation of the product of the formula A solution of 74.3 g (0.35 mol) of N- (2,2,6,6-tetramethyl-4-piperidinyl) -n-butylamine in 50 ml of water was slowly added at 0 ° C to a solution of 64.5 g ( 0.35 moles) of cyanuric chloride in 500 ml of xylene, maintaining the temperature during the addition and for an additional hour. After 2 hours at room temperature, the mixture was cooled to 0 ° C and an aqueous solution of 14.7 g (0.368 mole) of sodium hydroxide in 50 ml of water was added. 1/2 hours later at 0 ° C and for an additional 2 hours at room temperature, the aqueous solution was separated and 69.2 g (0.175 moles) of N, N'-bis (2, 2, 6, 6-tetramethyl) were added. -4-piperidinyl) -1, ß-hexanediamine.

The mixture was heated at 50 ° C for 1 hour and 48.4 g (0.35 mol) of crushed potassium carbonate was added and heated at 60 ° C for 4 hours. After washing with water, the organic phase was concentrated under vacuum at 60-70 ° C / 10 mbar, with 250 ml of xylene being recovered. 138.1 g (0.35 mole) of N, N'-bis (2, 2, 6,6-tetramethyl-4-piperidinyl) -1,6-hexandiamine were added and the mixture was heated at 150 ° C for 2 hours. cooled again and 14 g (0.35 moles) of crushed sodium hydroxide were added. The mixture was heated at 140 ° C for an additional 4 hours, azeotropically removing the residual water from the reaction and for an additional 4 hours at 160 ° C. After cooling to 60 ° C, the mixture was diluted with 300 ml of xylene was filtered and washed three times with 100 ml of ethylene glycol. After concentrating under vacuum at 60 ° C / 10 mbar, 54.4 g (0.147 mol) of 2-chloro-4,6-bis- (dibutylamino) -1,3,5-triazine was added. The mixture was heated at 140 ° C for 3 hours and 20.3 g (0.147 mol) of crushed potassium carbonate was added, heating the mixture to reflux and azeotropically removing the water of reaction.

The mixture was heated at 160 ° C for 4 hours, 20.3 g (0.147 moles) of crushed potassium carbonate was added and it was heated again at 160 ° C for 2 hours. After cooling to 160 ° C, the mixture was diluted with 300 ml of xylene, filtered and concentrated under vacuum at 140 ° C / 1 mbar. A solid with a melting range of 130-136 ° C was obtained after drying.

Mn (per GPC): 2830 g / mol Polydispersity Mw / Mn: 1.22 The GPC analysis shows a chromatogram as in Figure 2. The ratio of the three main simple components- ((n '= 2):' (n '= 4): (n' = 6) ) of the polydispersed products obtained in a molar% of 2: 0.96: 0.33.

Example 1: Preparing the product of the formula A 500 ml, 4-neck, spherical bottom flask, with magnetic stirring, was charged with 25.0 g (0.115 mole) of the product of Example S-1 and 200 ml of cyclohexane. The mixture was heated to reflux and 0.10 g of M0O3 was added thereto. 51.9 g (0.403 mole) of 70% t-butyl hydroperoxide were added over 3 hours and the water was removed by azeotropic distillation. Three additional portions of 0.10 g of M0O3 were added during the course of this addition. The contents were transferred to a magnetically agitated ®Fisher-Porter pressurized bottle and heated to 125 ° C for four hours, then cooled to below 60 ° C and the M0O3 filtered. The filtrate was stirred in the presence of 200 ml of 5% Na 2 SO 3 for 90 minutes. The phases were separated and the organic phase was washed with water and saturated aqueous NaCl. The organic phase was dried over MgSO4 and evaporated to a pale yellow solid. Yield: 35.7 g (99% of theory). Melting range: 130-170 ° C. 1H RM: 0.85-2.40 ppm (complex mixture); 3.20-3.45 ppm (s, broad, NCH2); 3.54-3.70 ppm (s, broad, NOCH); 4.90-5.50 ppm (s, broad, NCH). The ratio of protons to 3.20, 3.54 and 4.90 ppm is 2: 1: 1. 13 NMR: 82 ppm (NOC) 165 ppm (triazine C).

Example 2: Preparation of the product of the formula A 500 ml, 4-neck, spherical bottom flask, with magnetic stirring, was charged with 25.0 g (0.0962 moles) of the product of Example S-2 and 200 ml of cyclohexane. The mixture was heated to reflux and 0.10 g of Mo03 was added. 43.3 g (0.337 moles) of 70% t-butyl hydroperoxide were added over 2 hours and the water was removed by azeotropic distillation. Two additional portions of 0.10 g of Mo03 were added during the course of this addition. The contents together with 0.3 g of Mo03 were transferred to a pressurized ®Fisher-Porter bottle with magnetic stirring and heated at 125 ° C for eleven hours, then cooled below 60 ° C and the Mo03 filtered. The filtrate was stirred in the presence of 200 ml of 5% Na 2 SO 3 for 90 minutes. The phases were separated and the organic phase was washed with water and saturated aqueous NaCl. The organic phase was dried over MgSO4 and evaporated to a pale yellow solid. Yield: 34.4 g (99% of theory). Melting range: 128-169 ° C. XH NMR: 0.80-2.50 ppm (complex mixture); 3.20-3.40 ppm (s, broad, NCH2); 3.40-3.50 ppm (s, broad, NCH2 of NCH9); 3.54-3.70 (s, broad, NOCH); 4.90-5.40 ppm (s, broad, NCH). The ratio of protons to 3.20, 3.54 and 4.90 ppm is 2: 1: 1. 13 C NMR: 82 ppm (NOC); 165 ppm (triacin C).

Example 2-A: Preparation of the product of the formula A mixture of 885 g (3.39 moles) of the product of Example S-2, 6000 g (71.4 moles) of cyclohexane and 2.2 g of molybdenum trioxide was heated to reflux. A solution of 3360 g of 70% aqueous t-butyl hydroperoxide (26.1 moles) was added to the reflux mixture for 1-2 hours and the water was removed by azeotropic distillation. The reaction mass was transferred to a pressure reactor and heated to 125 ° C at 30-50 psig (2.1-3.5 bar) until the red color disappeared. The crude reaction mass was cooled and treated with aqueous sodium sulfite to destroy the residual peroxide. The aqueous layer was separated and the organic phase was concentrated under reduced pressure to a molten mass, which was slowly fed to cold methanol to obtain, after filtration, a matt white solid product. Average transmission values (10% toluene): 425 nm 44.2%; 450 nm = 56.0%; 475 nm = 67.5% Example 2-B: Preparation of the product of the formula The procedure of Example 2-A was repeated, except that during the work, the melt obtained after the removal of the cyclohexane was diluted with t-butyl alcohol and concentrated to 50% solids. The solution was cooled and cold methanol was quickly added to give, after filtration, a matt white solid product. Average transmission values (10% toluene): 425 nm 46.5%; 450 nm = 63.3 0%; 475 nm = 74.0% Example 3-A: Preparation of the product of the formula (Method 1) A 500 ml 4-neck, bottom-bottom flask was charged with 30.0 g (0.138 mole) of the product of Example S-1, 240 ml of n-octane, 36 g (0.27 mole) of t-butyl hydroperoxide at 70 % and 0.2 g of Mo03. The reaction mixture was heated to reflux and the water was removed by azeotropic distillation. 15 minutes later an additional amount of 35.1 (0.27 moles) of t-butyl hydroperoxide and 0.1 g of Mo03 was added and the reflux was continued until the reaction temperature was brought to 110 ° C. At this point the reaction mixture was transferred to a pressure bottle ®Fisher-Porter with magnetic stirring and heated at 150 ° C for 3.5 hours. The catalyst was filtered and the filtrate was suspended with 200 ml of 5% Na 2 SO for two hours. The organic phase was washed with water and saturated aqueous NaCl, dried over MgSO4 and evaporated to a pale yellow solid. Yield: 43.3 g (91% of theory). Melting range: 93-117 ° C. H NMR: 0.70-2.50 ppm (complex mixture); 3.20-3.45 ppm (s, broad, NCH2); 3.55-3.95 ppm (broad, NOCH, mixture of isomers in C8H?); 4.90-5.50 ppm (s, broad, NCH). The ratio of protons to 3.20, 3.55 and 4.90 ppm is 2: 1: 1. 13C RM: 78, 84 ppm (NOC, mixture of isomers in CsH? 7); 165 ppm (triazine C) Example 3-B: Preparation of the product of the formula (Method 2) A 500 ml 4-neck round bottom flask was charged with 25.0 g (0.115 mole) of the product of Example S-1, 200 ml of n-octane and 0.3 g of Mo03. The mixture was heated to reflux and 59.2 g (0.46 moles) of 70% t-butyl hydroperoxide were added over a period of 45 minutes with the continuous separation of the water by azeotropic distillation. 5 hours later 22.2 g (0.17 'moles) of additional t-butyl hydroperoxide and 0.2 g of M0O3. After a total reaction time of 9 hours, the catalyst was filtered and the filtrate was suspended with 200 ml of 5% Na 2 SO 3 for two hours. The organic phase was washed with water and saturated aqueous NaCl, dried over MgSO4 and evaporated to a pale yellow solid. Yield: 37.3 g (99% of theory).

Melting range: 108-124 ° C. XH- and 13C NMR: The NMR is identical to that of the product prepared according to Method 1 as described in Example 3-A.

Example 4: Preparation of the product of the formula A 500-ml, 4-neck, bottom-bottomed flask was charged with 30.0 g (0.115 moles) of the product of Example S-2, 240 ml of n-octane, 30 g (0.23 moles) of t-butyl hydroperoxide at 70 % and 0.2 g of M0O3. The reaction mixture was heated to reflux and the water was removed by azeotropic distillation. 30 minutes later an additional amount of -29.4 (0.23 mole) of t-butyl hydroperoxide and 0.2 g of M0O3 was added and the reflux was continued until the reaction temperature was raised to 110 ° C. In this point, the reaction mixture was transferred to a ®Fisher-Porter pressure bottle _ with magnetic stirring and heated at 150 ° C for 3.5 hours. The catalyst was filtered and the filtrate was suspended with 200 ml of 5% Na 2 SO 3 for two hours. The organic phase was washed with water and saturated aqueous NaCl, dried over MgSO 4 and evaporated to a pale yellow solid. Yield: 41.0 g (92% of theory). Melting range: 95-125 ° C. 1H RM: 0.80-2.50 ppm (complex mixture); 3.20-3.41 ppm (s, broad, NCH2); 3.41-3.55 (s, broad, NCH2 of NC4Hg); 3.55-3.95 ppm (broad, NOCH, isomer mixture in CaHi7); 4.90-5.50 ppm (s, broad, NCH). The ratio of protons to 3.20, 3.55 and 4.90 ppm is 2: 1: 1. 13 C NMR: 76-84 ppm (NOC, isomer mixture in C8H17); 165 ppm (triacin C).

Example 4-A: Preparation of the product of the formula A mixture of 1304 g (5.0 moles) of the product of Example S-2, 10.3 kg (90.2 moles) of octane and 8.95 g of molybdenum trioxide was heated to reflux. A solution of 3873 g of 70% aqueous t-butyl hydroperoxide (30.1 moles) was added to the reflux mixture for 1-2 hours and the water was removed by azeotropic distillation. The reaction mass was heated to reflux at spheric pressure until the red color disappeared. The crude reaction mass was cooled and treated with aqueous sodium sulfite to destroy the residual peroxide. The aqueous layer was divided and the organic layer was concentrated under reduced pressure to a molten mass, which was slowly fed to the cold methanol to obtain, after filtration, a matt white solid product. Average transmission values (10% toluene): 425 nm 47.7%; 450 nm = 76.0%; 475 nm = 84.6% Example 4-B: Preparation of the product of the formula The procedure of Example 4-A was repeated, except that during work, the melt obtained after the octane was removed and diluted with t-butyl alcohol and concentrated to 50% solids. The solution was cooled and cold methanol was added quickly to give, after filtration, a matt white solid product. Average transmission values (10% toluene): 425 nm 47.6%; 450 nm = 80.0%; 475 nm = 91.4% Example A: Pigmented thermoplastic olefin (TPO) granules were prepared by mixing a polyolefin blend (polypropylene containing an ethylene-propylene copolymer; ® Polytrope TTP 518-01 from A. A. Schulman, Inc.; Akron, Ohio, USA) with the additives listed below in a single screw extruder ®Superior / WMP 1"(2.54 cm) with a screw for all general purpose (L / D of 24: 1) at 200 ° C, cooling in a water bath water and granulating Before the extrusion and molding, the additives were mixed dry in a drum dryer.

Additives: 0.25% * of ® Red 3B (Pigment Red 177, Color Index 65300), 0.2% * > 2- (2'-Hydroxy-3,5'-di-tert-amylphenyl) -benzotriazole), 0.2% * 'of bis (l-octyloxy-2, 2,6,6-tetramethyl-4-piperidyl sebacate ), 0.1% * 'of calcium stearate, approximately 10% *' of talc and the stabilizers listed in Table 1 * 'percent by weight based on the polyolefin mixture The resulting granules were molded into 2"x2" (5.08 cm x 5.08 cm) plates of 1524 mm thickness at approximately 190 ° C in an Injection Molding Machine ®B0Y 30M. The test plates were mounted in metal frames and exposed in an "Atlas Ci65 Xenon Are eather-O-Meter, at a black panel temperature of 70 ° C, 0.55 W / m2 at 340 nanometers and a relative humidity of 50 ° C. % with intermittent light / dark and water spray cycles (SAE J 1960 Test Procedure of the Society of Automotive Engineers - Exterior Automotive Conditions) Brightness measurements of the test specimens were conducted on an Opacity / Brightness Meter ® BYK-GARDENER at 60 ° C according to ASTM D 523.

The results are shown in Table 1. Table 1 Retention of gloss after Stabilizers of hours in the eather-O-Meter 0 hours 1890 hours (= 0 J / m2 ** 1) (= 2500 kJ / m2 ** 1) 0. 05% *) of pentaerythritol tetracis- [3- (3,5-di-tert-butyl-4-hydroxyphenyl)] propionate, 0.05% *) of tris [2,4-di-tert-butylphenyl] phosphite, 100.0 ^ 57. 0.20% * 'of the compound of Example 2 0.05% *) of pentaerythritol tetracis- [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate, 0.05% *) of phosphite of tris [2,4-di-tert-butylphenyl], 100.0% 89.3% 0.20% * 'of the compound of Example 4 0.05%' *) of di (hydrogenated tallow) hydroxylamine 0.20% * 'of the compound of Example 2 100.0% 88.3% 0.05% *) of di (hydrogenated tallow) hydroxylamine 0.20% * 'of the compound of Example 4 100. 0% 83. 4% weight percent based on the polyolefin mixture ** 'refers to the incident energy expressed as kJ / m measured at 340nm. The formulations containing the stabilizers listed in Table 1 show a much greater resistance to photodegradation than those without such stabilizers. The unstabilized test specimens fail rapidly under the UV exposure discussed above.

Example B: Stabilization of polypropylene tapes 1.0 g of the compound of Example 2 6 4 were mixed, 0. 5 g of pentaerythritol tetracis- [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], and 1 g of calcium stearate in a mixing tube with 1000 g of polypropylene powder (PP ®) MOPLEN S 30 S) that had a melt index of 2.1 (measured at 230 ° C and 2.16 kg). The mixtures are extruded at 200-230 ° C to granules; these granules are subsequently converted to stretched tapes 50 μm thick and 2.5 mm wide using a pilot plant (®Leoñard, Sumirago / VA, Italy) under the following conditions: Extruder temperature 210-230 ° C Head temperature: 240 -260 ° C Stretch ratio 1: 6 The tapes thus pretreated are mounted on a white board and exposed on a Weather-O-Meter 65 WR (ASTM D 2565-85) with a black panel temperature of 63 ° C. The residual tenacity was measured, by means of a constant speed tensometer, on a sample taken after several times of exposure to light; from this, the exposure time (in hours) required for half the initial tenacity (T50) was measured. The results reveal that the compound of Example 2 6 4 stabilizes polypropylene tapes excellently.

Example C: Stabilization of polyethylene films - treated and not treated with pesticides The compound of Example 2 or 4 was mixed via a master batch with low density polyethylene granules (LDPE) (Riblene® FF 29 distributed by ®ENICHEM, Milan, Italy, density: 0.921g / cm3, melt flow index at 190 ° C and 2.16 kg: 0.60 g / 10 min) in a slow mixer. The masterbatch was pre-prepared by extruding the powder LDPE and 5% by weight of the compound of Example 2 or 4 with a twin-screw extruder at 200 ° C.

The mixture was blown at 200 ° C. Films 150 μm thick, with a content of 0.2% of the compound of Example 2 or 4 were obtained. Some of the films were treated with pesticides as follows: The films were stored before exposure to the Weather-O-Meter for 20 minutes. days on a concentrated solution of VAPAM® in water (ratio of 1: 1 in parts per volume) without direct contact with the solution. (VAPA "(®BASLINI SpA, Treviglio / BG, Italy) is an aqueous solution of 382 g per liter of metam-sodium which has the formula CH3-NH-CS-SNa.) After the previous treatment, the samples were exposed from film to a white cardboard in a Weather-O-Meter Type 65WR with a black panel temperature of 63 ° C. The untreated films were also exposed under the same conditions.The degradation process was verified by measuring the carbonyl increase In the sample with an Infrared Spectrophotometer with Fourier Transformation, a high increase in carbonyl indicates a high degradation.The degradation was also verified by measuring the residual elongation, by means of a constant speed tensiometer, on a sample taken after several times of The exposure time, in hours, required for half the initial elongation (T50) was calculated.The results reveal that the compound of Example 2 or 4 stabilizes the s polyethylene films in excellent way. ~ '' Example D: Greenhouse Application The compound of Example 2 or 4 was mixed via the masterbatch with low density polyethylene granules (LDPE) (Riblene® EF 2100 V distributed by ®ENICHEM, Milan, Italy, density: 0.921g / cm3, melt flow index at 190 ° C and 2.16 kg: 0.25) in a slow mixer. The masterbatch was pre-prepared by extruding LDPE powder and 10% by weight of the compound of Example 2 or 4. The mixture was "blown extruded at 200 ° C, and films of 150 microns thickness were obtained, with a content of 0.3. % or 0.4% of the compound of Example 2 or 4. The films were exposed on the greenhouse south roof at Pontecchio Marconi (Bologna, Italy) without support, or galvanized iron support on a pine wood support. applied the following pesticides in the greenhouse: (VAPAM® (®BASLINI SpA, Treviglio / BG, Italy) which is an aqueous solution of 382 g per liter of metam-sodium which has the formula CH3-NH-CS-SNa). SESMETRIN® (®BIMEX SpA, Isola / VI, Italy) which is an aqueous solution at 23.75% (% by weight / weight) of permethrin which has the formula The greenhouse was treated with a solution of 4 liters of ®VAPAM in 10 liters of water every 6 months, and with ®SESMETRIN (5 g in 5 liters of water) every month. During the exposition, performance was periodically evaluated by measuring the residual elongation (in% of initial elongation of the polyethylene film) by means of a dynamometer at constant speed. - The results reveal that the compound of Example 2 or 4 stabilizes the LDPE film in excellent manner.

Example E: Stabilization of low density films - outdoor exposure. The compound of Example 2 or 4 was mixed via a masterbatch with low density polyethylene (LDPE) granules (Riblene® EF 2100 V distributed by ®ENICHEM, Milan, Italy, density: 0.921g / cm3; cast melt at 190 ° C and 2.16 kg: 0.25) in a slow mixer. The master batch was previously prepared by extruding Powdered LDPE and 10% by weight of the compound of Example 2 or 4. The mixture was extruded by blowing at 200 ° C, and films of 150 microns thickness were obtained, with a content of 0.3% or 0.4% of the compound of Example 2 or 4. The films were exposed in Pontecchio Marconi (approximately 110 kLys / annual radiation) without support, on galvanized iron and on the support of pine wood, without the application of pesticides. The surfaces of the films were fixed at an inclination of 45 ° to the south. During the exposition, the operation was evaluated periodically by measuring the residual elongation (in% of initial elongation of the polyethylene film) by means of a dynamometer at constant speed. The results reveal that the compound of Example 2 or 4 stabilizes the LDPE films in an excellent way.

Example F: Polypropylene grade fibers containing 0.05% by weight of calcium stearate and 0.05% by weight of di (hydrogenated tallow) hydroxylamine as base stabilization, mixed dry with the stabilizer indicated in Table 2 and then melted in a manner composed at 234 ° C in granules. The fully granulated formulated resin was then isolated at 246 ° C or 274 ° C to fiber using a laboratory model "Hills" fiber extruder The 41 filament spun tow was stretched at a ratio of 1: 3: 2 to give a final denier 615/41"Socks" were woven from stabilized propylene in an ®Lawson-Hemphill analysis weaver and exposed in an "Atlas Xenon-Arc-Weather-O-Meter using the SAE J1885 Automotive Interior Conditions at 89 ° C bpt, 0.55 kW / cm2 at 340 nm with a no spray cycle.The failure in this test was determined by observing the physical failure of the sock when it was "scratched" with a blunt glass rod. time passes before this catastrophic failure occurs, the stabilizer is more effective.The results are shown in Table 2.

Table 2: Table 2: (Continued)

Claims (3)

1. A product obtainable by transfer of groups of the formula (G-I) to be presented in a block oligomer that has a polydispersity Mw / Mn from 1 to 1.7 and that corresponding to formula (I) to the groups of the formula (G-II); characterized in that Ri is a hydrocarbyl radical or -O-Ri is oxyl; the transfer is carried out by a reaction of the corresponding block oligomers of the formula (I) with a hydroperoxide in a hydrocarbon solvent in the presence of a catalyst which decomposes the peroxide; n is a number from 2 to 14; the radicals R 2 are independently of each other C 2 -C 2 alkylene, C 4 -C 2 alkenylene, C 5 -C 7 cycloalkylene, C 5 -C 7 cycloalkylene (C 1 -C 4 alkylene), C 1 -C 4 alkylene-alkylene. (Cs-C7 cycloalkylene), phenylendi (C? -C alkylene) or C4-C? 2 alkylene interrupted by 1,4-piperazinyl, -O- or > N-X? with Xi being acyl of C1-C12 or (C? -C? 2 alkoxy) carbonyl or having one of the definitions of R4 given above; or R2 is a group of formulas (a), (b) or (c); with m being 2 or 3, X 2 being C 1 -C 8 alkyl, C 5 -C 6 cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C 1 -C 4 alkyl; phenyl which is unsubstituted or substituted by 1, 2 or 3 C 1 -C 4 alkyl or C 4 C 4 alkoxy; C7-C9 phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C? -C4 alkyl; and the X3 radicals independently of each other being C2-C2 alkylene; the radicals A being independently of one another -OR3, -N (R4) (R5) or a group of the formula (II); 3, 4 and s, which are identical or different, are Ci-Ciß alkyl, Cs-C 2 cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C 1 -C 4 alkyl; C3-C18 alkenyl, phenyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4 alkyl or C1-C4 alkoxy; C7-Cg phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C1-C4 alkyl; tetrahydrofurfuryl or C2-C4 alkyl which is substituted at the 2, 3 or 4 position by -OH, C? -C8 alkoxy, di (C? -C4 alkyl) amino or a group of the formula (III); with Y being -O-, -CH2-, -CH2CH2- or > N-CH3; and R3 is further hydrogen or -N (R4) (R5) is further a group of the formula (III); X is -O- or > N-R6; RQ is Ci-Ciß alkyl, C3-C18 alkenyl, C5-C12 cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4 alkyl; C7-Cg phenylalkyl which is not "substituted or substituted on the phenyl by 1, 2 or 3 C 1 -C 4 alkyl, tetrahydrofurfuryl, a group of the formula (GI), or C 2 -C 4 alkyl which is substituted on the position 2, 3 or 4 by -OH, Ci-Cs alkoxy, di (C 1 -C 4 alkyl) amino or a group of the formula (III); the radicals R have independently one of the meanings given for Re; and the radicals B and B * have independently one of the meanings given for A; with the proviso that in the individual recurring units of the formula (I), each of the radicals B, R and R2 have the same or different meaning.

2. The product according to claim 1, characterized in that Ri is C5-C18 alkyl, C5-C18 alkenyl, C5-C8 alkynyl, C5-C2 cycloalkyl unsubstituted or substituted by C1 alkyl. -C4; C5-C12 cycloalkenyl unsubstituted or substituted by C1-C4 alkyl; a bicyclic or tricyclic hydrocarbyl having 6 to 10 carbon atoms or C7-Cg phenylalkyl unsubstituted or substituted on the phenyl by C 1 -C 4 alkyl; and the hydrocarbon solvent is, depending on Ri, C 5 -C 8 alkane, C 5 -C 18 alkene, C 5 -C 8 alkyne, C 5 -C 12 cycloalkane unsubstituted or substituted by C 1 -C 4 alkyl; C5-C12 cycloalkene unsubstituted or substituted by C? -C4 alkyl; a bicyclic or tricyclic hydrocarbon having from 6 to 10 carbon atoms or C7-Cg phenylalancan unsubstituted or substituted on the phenyl by C 1 -C 4 alkyl.

3. The product according to claim 1, characterized in that the hydroperoxide is t-butyl hydroperoxide and the catalyst of the decomposition of the peroxide is M0O3. 8. The product according to claim 1, characterized in that per mole of the group of the formula (G-I) are present in the block oligomer corresponding to the formula (I), 2 to 8 moles of the hydroperoxide, 0.001 to 0.1 moles of the peroxide decomposition catalyst and 5 to 30 moles of the hydrocarbon solvent are applied. 9. The product according to claim 1, characterized in that the polydispersity Mw / Mn of the block oligomer corresponding to formula (I) is 1.1 to 1.7. 10. The product according to claim 1, characterized in that R is a group of the formula (G-I).

11. The product according to claim 1, characterized in that R2 is C2-C2 alkylene, C5-C7 cycloalkylene, Cs-Cdi cycloalkylene (C?-C4 alkylene), C?-C4 alkylene (cycloalkylene) of C5-C7), phenylendi (C? -C4 alkylene) or C4-C? alkylene interrupted by -0- or > N-X? with Xi being acyl of C-C? 2 or (C? -C? 2 alkoxy) carbonyl or having one of the definitions of R; or R2 is a group of the formula (b); R 3, R 4 and R 5, which are identical or different, are C 1 -C 8 alkyl, C 5 -C 6 cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C 1 -C 4 alkyl; phenyl, which is unsubstituted or substituted by 1, 2 or 3 C 1 -C 4 alkyl or C 1 -C alkoxy; C7-C9 phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C? -C4 alkyl; and R3 is further hydrogen or -N (R) (R5) is additionally a group of the formula (III); R 6 is Ci-Cis alkyl, Cs-C 2 cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C 1 -C 4 alkyl; C7-Cg phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C? -C4 alkyl; or a group of the formula (G-I). 12. The product according to claim, characterized in that n is a number from 2 to 12; R 2 is C 2 -C 2 alkylene, C 5 -C 7 cycloalkylene, C 5 -C 7 cycloalkylene (C 1 -C 4 alkylene), C 4 -C 4 alkylene (Cs-C 7 cycloalkylene) or phenylene (C 1 alkylene) alkylene; C4); Re is C? -C? 8 alkyl, C5-C? 2 cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 alkyl C? ~ C4; phenylalkyl of C-Cg which is unsubstituted or substituted on the phenyl by 1, 2 or 3 of C? -C4 alkyl; or a group of the formula (G-I); and R is a group of the formula (G-I). 13. The product according to claim 1, characterized in that R2 is alkylene of CC? 0, cyclohexylene, cyclohexylendi (alkylene of C? ~ C4), alkylene of C? -C4 dicyclohexylene, or phenylene (alkylene of C? ~ C4) ); R 3, R 4 and R 5, which are identical or different, are C 1 -C 2 alkyl, C 5 -C 7 cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C 1 -C 4 alkyl, phenyl which it is not substituted or substituted by 1, 2 or 3 C? _-C4 alkyl; or benzyl which is unsubstituted or substituted on the phenyl by C? -C4 alkyl; or -N (R4) (R5) is additionally a group of the formula (III); and Re is C 1 -C 2 alkyl, C 5 -C 7 cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C 1 -C 4 alkyl; benzyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C 1 -C 4 alkyl; or a group of the formula (G-I). 14. The product according to claim 1, characterized in that R2 is C2-Ca alkylene; R3, R and R5, which are identical or different, are C?-C8 alkyl, cyclohexyl which is unsubstituted or substituted by methyl; phenyl which is not substituted or substituted by methyl; or benzyl; or -N (R4) (R5) is further 4-morpholinyl; and Re is C? -C8 alkyl, cyclohexyl which is unsubstituted or substituted by methyl; benzyl or a group of the formula (G-I). 15. The product according to claim 1, characterized in that n is a number from 2 to 6; R2 is C2-Ce alkylene; A is -N (R4) (R5) or a group of the formula (II); R and R5, which are identical or different, are C? -C8 alkyl; or -N (R) (R5) is further 4-morpholinyl; X is > NR5; Re is C? -C4 alkyl; and the radicals B and B * have independently the definitions given for A.

16. The product according to claim 1, characterized in that B * is different from B and each of the radicals B, R and R2 have the same meaning in the individual recurring units of the formula (I). 17. The product obtainable by the hydrogenation of a product according to claim 1, characterized in that -ORi in the formula (G-II) is oxyl to obtain a block oligomer with groups of the formula (G-III).

18. A mixture characterized in that it contains a) a monodisperse compound of the formula (la), b) a monodisperse compound of the formula (Ib) and c) a monodisperse compound of the formula (le] the compounds of the formulas (la), (Ib) and (le) differ only in the number of repetitive units, the ratio of the compounds of the formula (la) to (Ib) to (le) in mol% is 2: 1.6: 1 to 2: 0.4: 0.04: and Ri is hydrogen, a hydrocarbyl radical or -O-Ri is oxyl; R2 is C2-C2 alkylene, C4-C2 alkenylene, Cs-C7 cycloalkylene, C-C7 cycloalkylene (C1-C4 alkylene), C4-C4-cycloalkylene (C5-cycloalkylene) alkylene. C7), phenylendi (C 1 -C 4 alkylene) or C 4 -C 2 alkylene interrupted by 1,4-piperazinyl, -O- or > N-X? with X being C1-C12 acyl or (C1-C12 alkoxy) carbonyl or having one of the definitions of R4 given above; or R2 is a group of the formula (a), (b) or (c); c) a monodisperse compound of the formula (le) the compounds of the formulas (la), (Ib) and (le) differ only in the number of repetitive units, the ratio of the compounds of the formula (la) to (Ib) to (le) in mol% is 2: 1.6: 1 to 2: 0.4: 0.04: and Ri is hydrogen, a hydrocarbyl radical or -0-R? it is oxyl; R2 is C2-C12 alkylene, C4-C12 alkenylene, Cs-C7 cycloalkylene, C5-Cdi cycloalkylene (-C1-C4 alkylene), C4-C4-cycloalkylene (C5-C7 cycloalkylene), phenylenyl (C 1 -C 4 alkylene) or C 4 -C 2 alkylene interrupted by 1,4-piperazinyl, -O- or > N-X? with X being C1-C12 acyl or (C1-C12 alkoxy) carbonyl or having one of the definitions of R4 given above; or R2 is a group of the formula (a), (b) or (c); with m being 2 or 3, X 2 being C 1 -C 8 alkyl, C 5 -C 12 cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C 1 -C 4 alkyl; phenyl which is unsubstituted or substituted by 1, 2 or 3 C 1 -C alkyl or C 1 -C 4 alkoxy; C7-C9 phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C1-C alkyl; and the X3 radicals independently of each other being C2-C2 alkylene; A * is -OR3, -N (R) (R5) or a group of the formula (G-IV); R 3, R 4 and R 5, which are identical or different, are C 1 -C 8 alkyl, C 1 -C 4 cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C 1 -C 4 alkyl; C3-C18 alkenyl, phenyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4 alkyl or C1-C4 alkoxy; C7-Cg phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C1-C4 alkyl; tetrahydrofurfuryl or C2-C4 alkyl which is substituted in the 2, 3 or 4 position by -OH, C? ~ C8 alkoxy, di (C1-C4 alkyl) amine or a group of the formula (III); / \ Y N (III) \ / with Y being -O-, -CH2-, -CH2CH2- or > N-CH3; and R3 is additionally hydrogen or -N (R4) (R5) is adjointly a group of the formula (III); X * is -O- or > N-R6 *; Re * is C 1 -C 8 alkyl, C 3 -C 18 alkenyl, C 5 -C 12 cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C 1 -C 4 alkyl; C7-C9 phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C 1 -C 4 alkyl; tetrahydrofurfuryl, a group of the formula (G-II), or C2-C4 alkyl which is substituted in the 2, 3 or 4 position by -OH, C? -C8 alkoxy, di (C1-C4 alkyl) amino or a group of the formula (III); R * has one of the meanings given for Re *; and the radicals B * and B ** have independently one of the meanings given for A *. 19. The mixture according to claim 18, characterized in that the ratio of the compounds of the formula (la) to (Ib) to (le) in mol% is 2: 1. : 0.5 to 2: 0.4: 0.04. • The mixture according to claim 18, characterized in that the ratio of the compounds of the formula (la) to (Ib) to (le) in mole% is 2: 1: 0.4 to 2: 0.45: 0.04. 21. The mixture according to claim 18, characterized in that Ri is cyclohexyl or octyl; R2 is C2-C6 alkylene; A * and B ** which are identical or different are -N (C? -C8 alkyl) 2 or a group of the formula (G-IV-1) B * is a group of the formula (G-IV-1); and R * is a group of the formula (G-II) -. 22. A composition characterized in that it contains an organic material susceptible to degradation induced by light, heat or oxidation and a product according to claim 1. 23. The composition according to claim 22, characterized in that the organic material is a synthetic polymer. 24. The composition according to claim 22, characterized in that the organic material is polyethylene or polypropylene. 25. A composition characterized in that it contains an organic material susceptible to degradation induced by light, heat or oxidation and a mixture according to claim 18.

26. A method for stabilizing an organic material against degradation induced by light, heat or oxidation, characterized in that it comprises incorporating into the organic material a product according to claim 1. SUMMARY OF THE INVENTION The present invention relates to a product obtainable by transferring groups of the formula (G-I) to be presented in a block oligomer that has a polydispersity M w / M n from 1 to 1. 7 and that corresponding to formula (I) to the groups of the formula (G-II); where Ri is a hydrocarbyl radical or -O-Ri is oxyl; the transfer is carried out by the reaction of the block oligomer with a hydroperoxide in a hydrocarbon solvent in the presence of a catalyst that decomposes the peroxide; n is a number from 2 to 14; R2 is, for example, C2-C12 alkylene; A is for example -N (R4) (R5); R 4 and R 5 are, for example, C 1 -C 8 alkyl; R is preferably a group of the formula (G-I) and B and B * have one of the meanings given for A; with the proviso that the individual recurring units of the formula (I), each of the radicals B, R and R2 have the same or different meaning. The products are useful as light stabilizers, thermal stabilizers and oxidation stabilizers for organic materials, in particular synthetic polymers.