GB2325239A

GB2325239A - Liquid polyfunctional additives

Info

Publication number: GB2325239A
Application number: GB9809252A
Authority: GB
Inventors: Paul Dubs; Roger Martin; Roland Boss; Samuel Evans
Original assignee: Ciba Spezialitaetenchemie Holding AG; Ciba SC Holding AG
Current assignee: BASF Schweiz AG
Priority date: 1997-05-13
Filing date: 1998-05-01
Publication date: 1998-11-18
Anticipated expiration: 2018-05-01
Also published as: FR2763340A1; CA2237279A1; GB9809252D0; FR2763340B1; CA2237279C; GB2325239B; JP4280944B2; ITMI981029A1; JPH10316986A; DE19820994A1; IT1299224B1

Abstract

Products are described which can be obtained by simultaneously reacting components a), b), c) and optionally d), where component a) is a compound of the formula I or a mixture of compounds of the formula I, component b) is a compound of the formula II or a mixture of compounds of the formula II, component c) is a compound of the formula III or a mixture of compounds of the formula III and component d) is a compound of the formula IV or a mixture of compounds of the formula IV, in which the general symbols are as defined in claim 1, the compound of the formula I being, for example, pentaerythritol, thiodiethylene glycol, 1,4-butanediol, 1,2-propanediol, diethylene glycol, triethylene glycol, diethanolamine or glycerol, the compound of the formula II being, for example, coconut fat, rapeseed oil, sunflower oil, soya oil or castor oil, the compound of the formula III being, for example, methyl 3-(3',5'-di-tert-butyl-4'-hydroxyphenyl)propionate, methyl 3-(3'-tert-butyl-4'-hydroxy-5'-methylphenyl)propionate or or an alkane having 12 to 20 carbon atoms. The abovementioned products can be used as liquid antioxidants in fuels, polymers and lubricants.

Description

2325239 Liquid polyfunctional additives The present invention relates to

novel liquid polyfunctional additives with low volatility, to compositions comprising an organic material, preferably a fuel, a polymer or lubricant, and the additives mentioned, and to their use for stabilising organic materials against oxidative, thermal or light-induced degradation.

The stabilisation, in particular of lubricants or of plastics, with antioxidants from the series of the sterically hindered phenols or reaction products thereof with other compounds is known, for example, from US-A-3 839 278, US-A-4 032 562, US-A-4 058 502, US-A-4 093 587, US-A- 4 132 702, US-A-5 478 875 and EP-A-0 644 195.

WO 91113134 describes a method for improving the solubility of antioxidants in a second medium.

The present invention relates to a product which can be obtained by reacting components a), b), c) and d), where component a) is a compound of the formula I or a mixture of compounds of the formula I, component b) is a compound of the formula II or a mixture of compounds of the formula H, component c) is a compound of the formula M or a mixture of compounds of the formula M and component d) is a compound of the formula IV or a mixture of compounds of the formula IV, CH2-OZ HO R12 0 1 11 XMa (R15) S Q-C-O-R17 A-C8-C30alkyl 1 1 'n2-u4 a (1) (11) (111) (IV) in which, in the compound of the formula I, Y independently of one another is OH, (HOCH2C112)2N- or -FINRI and CH3 CH3 L -CI2cycloalkyl, R2- N C3-C6alkenyl, R, is hydrogen, Cl-CI8alkyl, CS CH3 CH3 C7-C9plienylalkyl, phenyl, or phenyl which is substituted by 1 to 3 radicals Ap the radicals A, independently of one another being Cl-CUalkyl, halogen, hydroxyl, methoxy or etboxy, in which R2 is hydrogen, Cl-C8alkyl, 0, OH, NO, -CH2W, Cl-CI8alkoxy, CS- CI2cycloalkoxy, C3-C6alkenyl, C7-C9plienylalkyl or C7-C9phenylalkyl which is mono-, di- or trisubstituted on the phenyl ring by Cl-C4alkyl, or R2 is furthermore Cl-C8acyl or HOCH2CH2-, and a is the number 1, 2, 3, 4 or 6, where, if Y is OH and a is 1, CH3 CH3 or R2- in X is Cl-C45alkYL CYCI8alkenyl, -CH2CH2Tl(CH2CH20)bR4 CH3 H3 which R2 is as defined above, and T,, is oxygen, sulfur or N - Rs" R4 is CI-CAkyl, b is an integer ranging from 0 to 10 and R5 is hydrogen, Cl-CI8alkyl or phenyl, or, if Y is OH and a is 2, X is -CH2CH2T2(CH2CH20)bCH2CH2-, in which b is as defined above, ---CH2CH2- N / R6, -CcH2d- CH3 CH3 1 ---CH2CH2 - N CH3 H3 CH3 CH3 CH3 CH3 N - (CH2)- N -CH2-CH=CH-CH2 CH3 d CH3 CH3 CH3 0 0 1, ', C - C - NH-CH2CH2- or CH3 1 -CH2CH20 C OCH2CH2-, in which CH3 7 T2 is oxygen, sulfur, / N - RS or - S C - S - and RS is as defined above, M8 R6 is hydrogen, C,-CI8alkyl or phenyl, c is an integer ranging from 2 to 10, d is an integer ranging from 2 to 6 and R7 and R8 independently of one another are hydrogen, C, -C, 8alkyl or phenyl, or R7 and R8 together with the C atom to which they are bonded form a CS- CI2cycloalkylidene ring, or, if a is 3, X is C3-Cloalkanetriyl or N(CH2C112-)3, Or, if Y is OH and a is 4, X is C4-Cloalkanetetrayl, (-C12-lrl-kr'2)20, -CH2 0 0 CH2- -H2 CH2- -CH 0 or in which R9 is C,-C4alkyl, or, if Y is OH and a is 6, -CH2 H2- 2 0 ".o ' -' CH2 -CH2 CH2- 1 -CH2 0 0 CHp- 1 11 X is _(-;t12-U-NH -d-NH-d-CH - -C 1 H2 C 1 H2- _% 1 r'12 H2- 2 or C6-Cloalkanehexayl, or, if Y is HNR1 and a is 1, X is C,-CI8alkyl, C3-Clgalkertyl, C. 2cycloalkyl, C7-C9plienylalkyl, phenyl, CH3 CH3 Rio R2- N in which R2 is as defined above or X is furthermore C W(CH 2)e- CH3 CH3 or X together with R, is a group of the formula -CH2CH2CH2CH2CH2- or - CH2CH2OCH2CH2-, in which Rio is hydrogen or methyl and e is 2 or 3, or, if Y is -FMI and a is 2, H 1 X is -CfH2f-, -(CH2CH2N±CH2CH2- or-(CH2)6-NH-(CH2)6-,in which 9 f is an integer ranging from 2 to 10 and g is an integer ranging from 1 to 6, and, in the compound of the formula II, 0 Z is hydrogen or a group of the formula Thn2huW% 11 -R, 1 and k is an integer ranging from 0 to 6, in which h is 2 or 3, i is an integer ranging from 0 to 12 and R, j is CS-C30alkyl, CS-C30alkenyl which may be straight-chain or branched and whose chain(s) may have not more than three double bonds at any desired point on said chain(s), C8- C3Ohydroxyalkyl or C8-C3Ohydroxyalkenyl, whose alk(en)yl chain may be straight-chain or branched and whose chain(s) may have at least one hydroxyl function at any desired point on said chain(s), with the proviso that the compound of the formula II 0 11 has a group -(Chr'2h%.J)i-'.'-rll 1 in the compound of the formula III, R12 is Cl-CI8alkYl, C5-C12CYCloalkyl, phenyl or C7-C9phenylalkyl, R15 is hydrogen, Cl-C18alkyl, C5-CI2cycloalkyl, phenyl or C7-C9plienylalkyl, s is 0, 1 or 2, R15 HG- Q is _CmH2In-, -CH2-CH-. -CH2-S-(CH2)t Or H3C __ c CH3 H3C 1. CH3 R16 as defined above, m is an integer ranging from 0 to 3, R16 is Cl-C8alkY's t is 1 or 2, and n is an integer ranging from 1 to 6, where, if n is 1, in which R15 is R17 is hydrogen, Cl-C4Salkyl, CS-CI2cycloalkyl, C2-C18alkenyl, a monovalent radical of a CH20H CH3 CH3 hexose, a monovalent radical of a hexitol, -CHA-CH20H, R2 - N -, in which 1 CH20H CH3 CH3 R2 is as defined above, or furthermore R17 is -CH2CH2-T3-R19 or f(CH2)p oq CH2)pOR19, in which T3 is oxygen, sulfur or \ N-R22 R23 R24 0 R19 is 1 1 11 -CH-CH-C-O-R25 R12 - CH2-C OH RIS in which R12and R15 am as defined above, or R19 is furthermore hydrogen, Cl-C24alkyl, phenyl, CS- C12cycloalkyl or 0 -CH2-C-O-R25, in which p is an integer ranging from 2 to 4, q is an integer ranging from 2 to 20, R22 is Cl-CISalkyl, phenyl or phenyl which is substituted by 1 to 3 radicals Ap in which the radicals A, independently of one another am Cl- CI2alkyl, halogen, hydroxyl, methoxy or ethoxy, or R22 is furthermore CS-C8cycloalkyl, R23 and R24 independently of one another are hydrogen or methyl, with the proviso that R23 and R24 are not simultaneously methyl; R25 is hydrogen or Cl- C24alkyl, or, if n is 2, -CH2 1 R17 is a divalent radical of a hexose, a divalent radical of a hexitol, -CM2-k--t'2uH 1 CH20H Y R18 Cl t(CH2)p0CH2)p-, in which p and q are as Cl 1 q R20 defined above, CH3 CH3 -CH2CH2-T4-CH2CH2-9 -CH2-CH----CH-M2-, -CH2-C---C-CH2CH2CHt- N CH3 H3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 N - CHi- CH= CH- CHZ- N)9 ---QN - (CH2)Z- N CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 00 0 -CH 11 91 or in which 2-CH2-NH-C-C-NH-CH2-CH2- 0 0 1 R18 and R20 independently of one another are hydrogen or Cl-CI2alkyl or together are the radical -CH2CH2CH2CH2CH2-, r is an integer ranging from 2 to 10, 7 T4 is sulfur, N - R26 or - S - Cl - S in which R7 and R8 are as defined above, and 1 M8 R26 is hydrogen, Cl-CI8alkyl, phenyl or phenyl which is substituted by 1 to 3 radicals A,, in which the radicals A, are as defined above in formula I, or R26 is furthermore CH3 CH3 CS-CScycloalkyl or R2- N in which R2 is as defined above, or, CH3 CH3 if n is 3, CH2CH2- R17 is a trivalent radical of a hexose, a trivalent radical of a hexitol, 1 -CH2CH2-N-CH2CH2' 1 -CH, CH2-CH-CH3 1 1 or -kM2-u-R27, in which CH3-CH-CH2-N-CH2-CH-CH3 1 1 1 -CH2 R27 is hydrogen, -CH2011, Cl-C4alkyl, Cl-CI8alkylamido or 0 R12 11 1 N-C-M -C OH, in which Q, R12 and R15 are as defined above, or, RIS if n is 4, R17 is a tetravalent radical of a hexose, a tetravalent radical of a hexitol, C47C10alkanetetrayl, N-CH2CH2-N CH3-CH-CH / 2 -CH2 0 C or.

if n is 5, -CH2 '"2--ri-CH3 -CH 0 or CH2-CH-CH3 1 R17 is a pentavalent radical of a hexose or a pentavalent radical of a hexitol, or, if n is 6, -CH2 CH2- R17 is a hexavalent radical of a hexitol or -CH2-, 1 -lM2-, and -C 1 H2 C 1 H2" in the compound of the formula IV, A is hydrogen, Cl -C4alkyl or phenyl.

The liquid products of the present invention, which have low volatility, are distinguished by a very good stabilisation of organic materials, for example fuels, polymers or oils, and against oxidative, thermal and lightinduced degradation.

Alkyl having not more than 45 C atoms is a branched or unbranched radical such as, for example, methyl, ethyl, propyl, isopropyl, n-butyl, secbutyl, isobutyl, tert-butyl, 2-ethylbutyl, n-pentyl, isopentyl, Pmethylpentyl, 1,3-dimethylbutyl, n-hexyl, 1-methylhexyl, n-heptyl, isoheptyl, 1,1,3,3-tetramethylbutyl, 1-methylheptyl, 3-methylheptyl, noctyl, 2-ethylhexyl, 1,1,3-tdmethylhexyl, 1,1,3,3-tetramethylpentyl, nonyl, decyl, undecYl, Pmethylundecyl, dodecyl, 1,1,3,3,5,5hexamethylhexyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, eicosyl, docosyl or pentacosyl. One of the preferred meanings of R,, R4 and R16 is, for example, C,-C4alkyl, of R2 methyl, of R, j C,C20alkyl, of R12 and R15 C,-C4alkyl, in particular tert-butyl, and of R17 C,-C18alkyl.

Cycloalkyl having not more than 12 C atoms is, for example, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecyl or cyclododecyl. One of the preferred meanings of Rp R, I, R12 and R15 is CS-C7cycloalkyl. Cyclohexyl is particularly preferred.

CS-CUCycloalkyl which is unsubstituted or substituted by C,-C4alkyl is, for example, cyclopentyl, methylcyclopentyl, dimethylcyclopentyl, cyclohexyl, methylcyclohexyl, dimethylcyclohexyl, trimethylcyclohexyl, tert-butylcyclohexyl, cycloheptyl or cyclooctyl. CS-C8Cycloalkyl is preferred, in particular cyclohexyl and tert-butylcyclohexyl.

Alkenyl having not more than 30 C atoms is, for example, vinyl, propenyl, isopropenyl, 2-butenyl, 3-butenyl, isobutenyl, n-penta-2,4-dienyl, 3-methylbut-2-enyl, n-oct-2-enyl, n-dodec-2-enyl, iso-dodecenyl, oleyl, n-octadec-2-enyl or n- octadec-4-enyl. If R,, R2 and X are C3-C6alkenyl, then the C atom which is bonded to the nitrogen is advantageously saturated.

Hydroxyl-substituted CS-C30alkyl is a branched or unbranched radical containing preferably 1 to 3, especially 1 or 2 OH groups, for example 8hydroxyoctyl, 7-hydroxyoctyl, 6-hydroxyoctyl, 5-hydroxyoctyl, 4hydroxyoctyl, 3-hydroxyoetyl, 2-hydroxyoctyl, 9-hydroxynonyl, 1 0hydroxydecyl, 11 -hydroxyundecyl, 12-hydroxydodecyl, 13-hydroxytridecyl, 14-hydroxyten-adecyl, 15-hydroxypentadecyl, 16-hydroxyhexadecyl, 17hydroxyheptadecyl, 18-hydroxyoctadecyl, 20-hydroXyeicosyl or 22hydroxydocosyl. A preferred definition of R, 1 is hydroxyl-substituted C8C20alkyl, especially hydroxyl-substituted C8-CI2alkyl.

Hydroxyl-substituted Cg-C30alkenyl is a branched or unbranched radical containing preferably 1 to 3, especially 1 or 2 OH groups, for example 8hydroxyocten-2-yl, 7-hydroxyocten-2-yl, 6-hydroxyocten-2-yl, 5hydroxyocten-2-yl, 4-hydroxyocten-2-yl, 3-hydroxyocten-4-yl, 2hydroxyocten-4-yl, 9-hydroxynonen-2-yl, 10-hydroxydecen-2-yl, 11 hydroxyundecen-2-yl, 12-hydroxydodecen-2-yl, 13-hydroxytridecen-2-yl, 14hydroxyten-adecen-2-yl, 15-hydroxypentadecen-2-yl, 16-hydroxyhexadecen-2yl, 17-hydroxyheptadecen-2-yl, 18-hydroxyoctadecen-2-yl, 20hydroxyeicosen-2-yl or 22-hydmxydocosen-2-yl. A preferred definition of R, 1 is hydroxyl-substituted C8-C20alkenyl, especially hydroxyl-substituted C8-CI2alkenyl.

Phenylalkyl having 7 to 9 C atoms is, for example, benzyl, ccmethylbenzyl, a,ct-ffimethylbenzyl or 2-phenylethyl. Benzyl is preferred.

Examples of phenyl which is substituted by 1 to 3 radicals A, am o, m- or p-methylphenyl, 2,3-dirnethylphenyl, 2,4-dimethylphenyl, 2,5dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5dimethylphenyl, 2-methyl-6-ethylphenyl, 2-methyl-4-tert-butylphenyl, 2ethylphenyl, 2,6-diethylphenyl, 2,6-(Hethyl-4-methylphenyl, 2,6diisopropylphenyl, 4-tert-butylphenyl, p-nonylphenyl, o-, m- or pchlorophenyl, 2,3-dichlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 3,4-dichlorophenyl, 2,4,5-trichlorophenyl, 2,4,6trichlorophenyl, o-, m- or p-hydroxyphenyl, o-, m- or p-rnethoxyphenyl, oor p-ethoxyphenyl, 2,4-dimethoxyphenyl, 2,54methoxyphenyl, 2,5diethoxyphenyl, o-, m- or p-methoxycarbonyl, 2-chloro-6-methyl- phenyl, 3-chloro-2-methylphenyl, 3-chloro-4-methylphenyl, 4-chloro-2methylphenyl, 5-chloro-2-methylphenyl, 2,6-dichloro-3-methylphenyl, 2hydroxy-4-methylphenyl, 3-hydroxy-4-methylphenyl, 2-methoxy-5methylphenyl, 4-methoxy-2-methylphenyl, 3-chloro-4- methoxyphenyl, 3chloro-6-methoxyphenyl, 3-chloro-4,6-dimethoxyphenyl and 4-chloro-2,5dimethoxyphenyl. Preferred is phenyl which is substituted by 1 or 2, in particular 1, radical(s) Ap A, being, in particular, alkyl.

Phenyl which preferably has 1 to 3, in particular 1 or 2, alkyl groups and which is substituted by Cl-CIgalkyl is, for example, o-, m- or pmethylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2-methyl-6ethylphenyl, 4-tert-butylphenyl, 2-ethylphenyl, 2,6-diethylphenyl, butylphenyl, pentylphenyl, hexylphenyl, heptylphenyl, octylphenyl, nonphenyl, decylphenyl, undecylphenyl or dodecylphenyl. Phenyl which is substituted by Cl-C12alkyl is preferred, in particular phenyl which is substituted by C4-Cgalkyl.

A CS-CI2cycloalkylidene ring is, for example, cyclopentylidene, cyclohexylidene, cycloheptylidene, cyclooctylidene or cyclononylidene. Cyclohexylidene is preferred.

Alkoxy having 1 to 18 C atoms is, for example, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, pentoxy, isopentoxy, hexoxy, heptoxy, octoxy, decyloxy, tetradecyloxy, hexadecyloxy or octadecyloxy. One of the preferred meanings of R2 is C6-CUalkoxy. Heptoxy and octoxy are particularly preferre& Cycloalkoxy having 5 to 12 C atoms is, for example, cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy, cyclodecyloxy or cyclododecyloxy. One of the preferred meanings of R2 is CS-C8cycloalkoxy. Cyclopentoxy and cyclohexoxy are particularly preferred.

Examples of GrC9phenylalkyl which is mono-, di- or trisubstituted on the phenyl ring by Cl-C4alkyl are methylbenzyI, dimethylbenzyI, trimethylbenzyl or tert-butylbenzyI.

Acyl having 1 to 8 C atoms is, for example, formyl, acetyl, propionyl, butyryl, pentanoyl, hexanoyl, heptanoyl, octanoyl, benzoyl, acryloyl or crotonyl.

Cl-C8Alkanoyl, C3-Cgalkenoyl or benzoyl, in particular acetyl, are preferred.

- 11 Alkanetdyl having 3 to 10 C atoms is, for example, 1 -CH -;M2-Uti-uH2- 1 2-CH2'H-CH2-, -CH 1 -CH2 2H-CH2-CH2-, -CH2-CH2"CH-CH2-CH2-CH2- or --CH2-CH2-CH2-H-CH2-CH2-CH2-. Glyceryl is preferred.

CH2- 1 Alkanetetrayl having 4 to 10 C atoms is, for example, -CM2-k 1;-;M2- CH2- 9 -CH2-CH2-dH-CH-CH2- 1 1 11 1 1 1 1 1 -CH2-CH2-CH-CH2-CH-CH2-CH2- or --CH2-CH2-CH-CH2--1r'2-tn-,H2-CHZ-Pentaertyl is preferred.

1 1 1 Alkanehexayl having 6 to 10 C atoms is, for example, -CH2-CH-CH-CHH-CH2 1 1 1 1 1 1 1 -CH2- H-CH-CH2-CH-CH-CH2- or -,CH2-CH-H-CH2-CH2-CH-CH-CH2- If R17 with n = 1 to 6 is an n-valent radical of a hexose, then this radical is derived, for example, from allose, altrose, glucose, mannose, gulose, idose, galactose or talose, i.e. to obtain the corresponding compounds of the formula III, one, two, three, four, five or six -OH groups must be replaced by the ester group E-1, R12 HO 0 11 (R15) 76- a-C-0- S in which R12, RIS, s and Q are as defined above. For example, R17 with n = 5 can be a group CH20- H 0 H _0 eH( 0_ f 0- H c 0- H 0- If R17 is the n-valent radical of a hexitol, then the corresponding compounds of the formula HI are obtained by replacing n -OH groups by the abovementioned ester group E-1. R17 as a hexavalent radical of a hexitol can be, for example, 1 U 1 -0-CH H-CH-CH-CH-CH2-0-. This group is derived from D-sorbitol.

2-Cl 1 1 0 0 0 1 1 1 Alkylamido having 1 to 18 C atoms is, for example, CH3-CO-NH-, CH3CH2-M- NH-, C6RO-CO-NH- or C181137-M-NH-.

Nk means that the phenyl ring can be ortho-, meta- or para-substituted.

The four components a), b), c) and d) can be reacted with each other to give the products of the present invention in any desired sequence.

Preferably, the four components a), b), c) and d) are initially introduced and reacted simultaneously.

Component d) can, however, also be added to reaction mixtures a) and b), b) and c) or a) and c) and the missing fourth component can then be reacted.

A particularly preferred embodiment is the addition of component d) after the reaction of the three components a), b) and c).

The reaction is advantageously carried out in the presence of a catalyst. Suitable catalysts are Uwis acids or bases.

Examples of suitable basic catalysts are metal hydrides, metal alkylides, metal arylides, metal hydroxides, metal alcoholates, metal phenolates, metal amides or metal carboxylates.

Examples of preferred metal hydrides are lithium hydride, sodium hydride or potassium hydride.

Examples of preferred metal alkylides are butyllithium or methyllithium.

An example of a preferred metal arylide is phenyllithium.

Examples of preferred metal hydroxides are lithium hydroxide, sodium hydroxide, potassium hydroxide, caesium hydroxide, rubidium hydroxide, magnesium hydroxide, calcium hydroxide, barium hydroxide or aluminium hydroxide.

An example of a particularly preferred metal hydroxide is potassium hydroxide.

Examples of preferred metal alcoholates are lithium methanolate, sodium methanolate, sodium ethanolate, potassium methanolate, potassium ethanolate, sodium isopropylate or potassium tert-butylate. Iliese can be employed in the pure state or as a solution.

An example of a particularly preferred metal alcoholate is lithium methanolate.

Examples of preferred metal phenolates are sodium phenolate or potassium phenolate.

Examples of preferred metal amides are sodium amide or lithium amide.

Examples of preferred metal carboxylates are calcium acetate and calcium salicylate.

An example of a particularly preferred metal carboxylate is superbasic calcium salicylate.

0 R32 0--R34 or R33 O-C-R35 11 R30 Examples of suitable Lewis acid catalysts are "'Sn-0 R31 11 0 OR37 1 R360-TI -OR38, the radicals R30, R31, R32, R33, R34 R35, R36, R37, R38 and R39 being, 1 OR39 independently of one another, for example Cl-Clgalkyl or phenyl. Cl- C8Alkyl is preferred. A particularly preferred Lewis acid catalyst is dibutyltin oxide.

In a two-stage - -Son regime it is also possible to employ different catalysts.

The catalyst is Jed to components a), b), c) and, if used, d) in an amount, for example, of from 0.03 to -0 parts per thousand by weight, preferably in an amount of from 0. 1 to 10 parts per thousand by weight, based on the sum of the weight of components a), b) and c). Particular preference is given to the addition of from 1 to 10 parts per thousand by weight of SAPO-001.

The reaction can also be performed in the presence of a catalyst which is adsorbed on a carrier and which comprises as the active material an alkali metal compound of the formula VII M.An (VII) where m is Li, Na, K, Rb or Cs, v is the valency of An, and An is a fluoride, hydroxide, phosphate, formate, acetate (generally, carboxylate) or -OR40 radical, and R40 is alkyl having 1 to 4 C atoms or a phenolate radical, and comprising as carrier an alkaline material which measured in 10% by weight aqueous suspension has a pH of greater than 10 and is selected from one or more substances from the series of the alkaline earth metal oxides, hydroxides, aluminates or silicates.

The carder substances from the series of the alkaline earth metal compounds mentioned can be present in hydrated or anhydrous form; the hydrated forms are preferred.

JL.ficious suppor,--d Catalysts are those comprising the oxides, hydroxides, aluminates or silicates of the alkaline earth metals Mg, Ca, Sr and Ba or mixtures thereof as carriers.

Particularly judicious carriers are the compounds MgO, Mg(OH)2, CaO, CafflH)2, BaO, BafflH)2, Ba(OH).2.8H0, calcined dolomite MgO.CaO, calcined and hydrated dolomite MgCafflH)4, calcined barytocalcite BaO-CaO, calcined and hydrated barytocalcite BaCafflH)4, spinel MgAI204, MgAI204- nH20, CaA1204, W1204.nH20, hydrocalumite 2Ca(OH)2-AI(OH)3-nH20, Ca2SiO4, hillebrandite Ca2SiO4.H20, foskagite and mixtures thereof.

Preference is given to CaO, MgO or a mixture of these, produced for example by burning dolomite CaCO3-MgCO3, as carrier.

Preferably, the carrier substances are essentially free from iron; in other words, the content of iron, including iron in the form of its compounds, should judiciously not exceed 10 ppin. Overall, the carrier materials should be of high purity,.also with respect to further metals, such as copper, lead and other heavy metals, for example. The copper content should judiciously be below 10 ppm, as should the content of heavy metals; for example, the lead content should be below 10 ppin, and overall (all heavy metals) the content should be, for example, below 40 ppin.

Likewise preferably, the carriers are substantially free from carbonate groups. A carbonate content of less than 0. 1 % by weight should judiciously be observed. Oxygen-transferring anions, such as MnO,-, CrO4-, AsQ43-, N03-, for example, should judiciously be present at not more than 100 ppm, judiciously overall at not more than 200 ppm. Active oxygen should judiciously not exceed 100 ppm. Strongly acidic anions, examples being S04- or C17, should judiciously be present at not more than 500 ppm each and judiciously overall at not more than 1000 ppm.

Judicious supported catalysts are those comprising as the active material the hydroxides or fluorides of the alkali metals Na, K, Rb or Cs.

Preferred active material is KOH, KF, NaOH, NaF or CsF; KOH or KF is particularly preferred.

The proportion of the active material is, for example, from 0. 15 to 30% by weight mathematically based on the anhydrous carrier. Ilie percentage relates mathematically to the corresponding alkali metal ion alone, i.e. without taking into account the respective anion, whereas the figure for the carrier relates to the carrier as a whole.

Judiciously, ftorn 0. 15 to 10% by weight of active material is provided, and, in a preferred embodiment, there is from 1 to 10% by weight of active material, based in each case on the alkali metal ion and on the anhydrous carrier.

The reaction of components a), b) and c) can be carried out in component d) as solven examples being NorparO Ex 15 or ExxsolO D- 110 (from EXXON) or MarlicanO (linear alkylbenzene from HOLS AG). The reaction of components a) and b) and c) is preferably carried out without solvent. Ilie solvent and component d), for example NorparO Ex 15 or ExxsolO D110, is added subsequently.

The reaction temperature lies, for example, between 120 and 250T. Ilie reaction is preferably carried out in a temperature range from 150 to 2000C, particular preference being given to the range from 1600C to 1900C.

If components a), b) and c) are not commercially available, they can be prepared by known processes or analogously. Possible preparation processes for the compounds of the formula M can be found, for example, in the following publications: GB-A-0 996 502, US-A-3 330 859, US-A-3 944 594, US-A-4 593 057, EP-A-0 154 518 or US-A-3 960 928.

In formula III, s is preferably the number 1 or 2.

The invention also preferably relates to products in which, in the compound of the formula I, Y independently of one another is OH, (HOCH2C142)2N- or -HNRI and CH3 C H, 9 R, is hydrogen, C,-Cloalkyl, C5-C7cycloalkyl, R2- N -, C3-C6alkenyl, benzyl CH3 CH3 or phenyl, in which R2 is hydrogen, C,-C4alkyl, OH, -CH2CN, C6-CUalkoxy, C_5-CScycloalkoxy, allyl, benzyl, acetyl or HOCH2CH2- and a is the number 1, 2, 3, 4 or 6, where, 1 if Y is OH and a is 1, CH3 CH3 X is Cl-C30alkyl, C3-C18alkenyl, -CH2CH2TI(CH2CH20)bR4 or R27 L CH3 H3 which R2 is as defined above, and TI is oxygen, sulfur or N - Rs, R4 is Cl-Cloalkyl, b is an integer ranging from 0 to 10 and RS is hydrogen, Cl-Cloalkyl or phenyl, or, if Y is OH and a is 2, X is -CH2CH2T2(CH2CH20)bCH2CH2-1, in which b is as defined above, / R6 CH3 CH3 -CH2CH2- N \, -CcH2d- CH2CH2 - N CH3 H3 CH3 CH3 CH3 CH3 N (CH2)- N -CH2-CH=CH-CH2 -'C:CH3 d CH3 CH3 CH3 0 0 ---CH2CH2-NH - C - C NH-CH2CH2- or 9 CH3 1 CH2CH20---1 C OCH2CH2-, in which 1 Cr13 T2 is oxygen, sulfur, N - R's or - S - Cl - S - and RS is as defined above, H8 R6 is hydrogen, Cl-Cloalkyl or phenyl, c is an integer ranging from 2 to 10, 1 d is an integer ranging from 2 to 6 and R7 and R8 independently of one another are hydrogen, Cl-Cloalkyl or phenyl, or R7 and RS together with the C atom to which they are bonded form a CS-C7cycloalkyl ring, or, if Y is -HNRI and a is 1, CH3 CH3 Xis Cl-Cloalkyl, C3-CI8alkenyl, CS-C7eycloalkyl, benzyl, phenyl, R2-N in CH3 H3 R10 which R2 is as defined above, or X is furthermore ( W(CH2)e - or X together with R, is a group of the formula -CH2CH2CH2CH2CE12- or -CH2CH2OCH2CE12-, in which R10 is hydrogen or methyl and e is 2 or 3, and, in the compound of the formula H, 0 11 Z is hydrogen or a group of the formula -(ChH2ho)i-C-Rl 1 and k is an integer ranging from 0 to 4, in which h is 2 or 3, i is an integer ranging from 0 to 6 and R, j is C8-C20alkyl, C8-C20alkenyl which may be straight-chain or branched and whose chain(s) may have not more than three double bonds at any desired point on said chain(s), C8- C2Ohydroxyalkyl or CS-C2Ohydroxyalkenyl, whose alk(en)yl chain may be straight-chain or branched and whose chain(s) may have at least one hydroxyl function at any desired point on said chain(s), with the proviso that the compound of the formula 11 0 11 comprises a group -k"lhn2h'jji-k. ,-Rl 1 in the compound of the formula III, R12 is Cl-C6alkyl, C5-C7cycloalkyl, phenyl or benzyl RIS is hydrogen, Cl- C6alkyl, CS-C7cycloalkyl, phenyl or benzyl, s is 1 or 2, 1 R15 1 HO- Q is -C.H2._, -CH2-CH-, -CH2-S-(CH2)t- or H3C - C CH3 H3C 1 '-, CH3 is as defined above, R16 m is an integer ranging from 0 to 3, R16 is Cl-COlkYL t is 1 or 2, and n is an integer ranging from 1 to 6, where, if n is 1, in which Rj_5 R17 is hydrogen, Cl-C30alkyl, CS-C7cycloalkyl, C2-CI8alkenyl, a monovalent radical of a hexose, a monovalent radical of a hexitol, -CH2--CH20H, 1 CH20H CH20H CH3 CH3 R27 N in which CH3 CH3 R2 is as defined above, or furthermore R17 is -CH2CH2-TyRI9 or f (CH2)p oq CH2)pOR19, in which T3 is oxygen, sulfur or N-R22 F 12 R23R240 CH OH Rig is 1 1 11 or 2 in which R12 and RIS are as defined _CH-CH-C-O-R25 R15 above or Rig is furthermore hydrogen, Cl-Clgalkyl, phenyl, C5C7cycloalkyl or 0 -CH2-C-O-R2., in which p is an integer ranging from 2 to 4, q is an integer ranging from 2 to 20, R22 is Cl-Cloalkyl, phenyl or CS-Cgcycloalkyl, R23 and R24 independently of one another are hydrogen or methyl with the proviso that R23 and R24 are not simultaneously methyl; R25 is hydrogen or Cl-CI8alkyl, or, if n is 2, -CH2 1 R17 is a divalent radical of a hexose, a divalent radical of a hexitol, - CH2-;-;"2U", 1 't'2U" R118 1 '20 f poq defined above, -CH2CH2-T4-CH2CH2-, -CH2-CH--CH-CH2-, CH3 CH3 -CH2-C-C-CH2- -CH2CH2-N CH3 CH3 9 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 - -< N Hr- CH= CH- CH2- N N- (CH 11:- N CH 3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 00 0 1111, in which -CH2-C.H2-NH-C-C-NH-CH2-CH2- or 01 R18 and R20 independently of one another are hydrogen or Cl-C6alkyl or together are the radical -CH2CH2CH2CH2CH2-, r is an integer ranging from 2 to 10, 7 T4 is sulfur, N - R26 or - S - C, - S in which R7 and R8 are as defined above and HS CH3 CH3 R26 is hydrogen, Cl-Cloalkyl, phenyl, CS-C8cycloalkyl or R2-N in which R2 CH3 H3 is as defined above.

The invention particularly preferably relates to products 1 in which, in the compound of the formula I, Y independently of one another is OH, (HOCH2CH2)2W or -HNRI and CH3 CH3 R, is hydrogen, Cl-C4alkyl or R2 - N -, in which CH3 H3 R2 is hydrogen, Cl-C4alkyl, OH, allyl, benzyl, acetyl or HOCH2CH2- and a is the number 1, 2, 3, 4 or 6, where, if Y is OH and a is 1, CH3 CH3 Xis Ci-Ci8alkYl, C3-C18alkenyl, -CH2CH2TI(CH2CH20)bR4 or R2- N in CH3 CH3 which R2 is as defined above, and T1 is oxygen, R4 is C, -C4aIkyl and b is an integer ranging from 0 to 10, or, if Y is OH and a is 2, X is -CH2CH2T2(CH2CH20)bCH2CH2-, in which b is as defined above, or furthermore X CH3 CH3 is -CcH2d-, ---CH2CH2 -N _ or -CH2-CH=CH-CH2 - in which CH3 CH3 T2 is oxygen, sulfur or \ N - R5, R5 is hydrogen, b is the number 0 or 1 and c is an integer ranging from 2 to 8, or, if a is 3, 1 X 'S or N(CH2CH2-)3. Or, if Y is OH and a is 4, CH21 1 1 Cl H2 X is -CM2-k 1 "k-;M2-, k-%''12-'rl-,H2)20 or ---CH2-CH-CH2-0-CH-CH2-, Or.

CH2- if Y is OH and a is 6, -CH2 CH2 1 1 - X is -C'12-k-.12-u-CH2-C-CH2or -CH2-CIH-CIH-CIH-H-CH2 - Or. 1 1 -CH2 CH2 if Y is -HNR, and a is 1, CH3 CH3 X is Cl-Cloalkyl,

CYCI8alkenyl, CS-C7cycloalkyl or R2- N where R2 is as CH3 H3 defined above, or, if Y is -HNR, and a is 2, X is -Cffi2r- in which f is an integer ranging from 2 to 10 and, in the compound of the formula II, 0 11 Z is hydrogen or a group of the formula -k'hn2h%JPi-i,-Rl 1 and k is 1, 2 or 3, h is 2 or 3, i is an integer ranging from 0 to 4 and R,, is C8-C20alkyl, C8-C20alkenyl which may be straight-chain or branched and whose chain(s) may have not more than three double bonds at any desired point on said chain(s), Cg- C2Ohydroxyalkyl or Cg-C2Ohydroxyalkenyl, whose alk(en) chain may be straight-chain or branched and whose chain(s) may have at least one hydroxyl function at any desired point on said chain(s), with the proviso that the compound of the formula II 0 comprisesagroup in the compound of the formula M, R12 is Cl-C6alkYl Or CS-C7CYCI0alkYL RIS is hydrogen, Cl-C6alkyl or C5- C7CYCloalkyl, s is 1 or 2, Q is -C.H2.- or -CH2-CH- 1 9 R16 m is an integer ranging from 0 to 3, R16 is Cl-C4alkyl and n is an integer ranging from 1 to 6, where, if n is 1, R17 is hydrogen, Cl-CI8alkyl, C5-C7CYCloalkyl, C2-CI8alkenyl, a monovalent radical of a CH20H CH3 "' CH3 hexose, a monovalent radical of a hexitol, -CH2-A-CH20H or R2- N - in which 1 CH20H R2 is as defined above, or furthermore R17 is f (CH2)p oq CH2)pOR19 in which R19 is hydrogen, Cl-CI8alkyl or CS-C7cycloalkyl, in which p is an integer ranging from 2 to 4, q is an integer ranging from 2 to 10, or, CH3 CH3 if n is 2, -CH2 1 R17.is a divalent radical of a hexose, a divalent radical of a hexitol, -Ct'2-t-M2uH, 1 "'2Ul 1 -C,Hw, f (CH2)p oq CH2)p-, in which P and q are as defined above, CH3 CH3 -(M2CH2-T4-CH2(H2-,, Or - CH2CH2- N in which CH3 CH3 r is an integer ranging from 2 to 10, T4 is sulfur or N - R26 and R26 is hydrogen, Cl-Cloalkyl or C5- Cscycloalkyl, or, if n is 3, R17 is a trivalent radical of a hexose, a trivalent radical of a hexitol, 1 CH2-CH-CH3 or 1 CH3-CH-CH2-N-CH2-CH-CH3 1 1 if n is 4, or, CH2CH21 -CH2CH2-N-CH2CH2- -CH 1 4:

R17 is a tetravalent radical of a hexose, a tetravalent radical of a hexitol, -CH2-C-CH2- or 1 M3-CH-CH2 N-CH2CH2-N CH -CH 1 \ CH -CH-CH 3 1 2 2 1 3 The invention furthermore preferably relates to products in which, in the compound of the formula I, Y independently of one another is hydroxyl or -NH2 and a is an integer ranging fTom 1 to 4, where, if a is 1, CH3 CH3 X is R2- N - and CH3 H3 R2 is hydrogen, methyl or HOCH2CH2-, or, if Y is OH and a is 2, CH3 CH3 X is -CH2CH2T2(CH2CH20)bCH2CH2-, -CcH2d- Or N CH3 H3 in which T2 is oxygen, sulfur or N - R5, R5 is hydrogen, b is the number 0 or I and c is the number 2, 3 or 4, or, if Y is OH and a is 3, 1 X 'S 'or, if Y is OH and a is 4, CH2- X is and, in the compound of the formula II, 0 11 Z is hydrogen or a group of the formula -C-R, 1, k is the number 1 and R, j is CK20alkYL C8-C20alkenyl which may be straight-chain or branched and whose chain(s) may have not more than three double bonds at any desired point on said chain(s), C8-C2Ohydroxyalkyl or C8-C2Ohydroxyalkenyl, whose alk(en)yl chain may be straight-chain or branched and whose chain(s) may have at least one hydroxyl function at any desired point on said chain(s), with the proviso that the compound of the formula H 0 11 comprises a group -C-R,,and, in the compound of the formula HI, R12 is tert-butyl, R15 is C,-C4alkyl and is bonded in the ortho-position relative to the OH group, s is the number 1, Q is -C.H2.- and is bonded in the para-position relative to the OH group, where m is the number 2, n is 1 and R17 is Cl-COlkYl.

The invention furthermore preferably relates to products in which, in the compound of the formula IH, R12 is Cl-C4alkyl or cyclohexyl, R15 is Cl-C4alkyl or cyclohexyl and is bonded in the ortho-position relative to the OH group, s is the number 1, Q is -C,H2,n- and is bonded in the para-position relative to the OH group, where m is an integer ranging from 0 to 3 and n is an integer ranging from 1 to 4, where, if n is 1, CH20H R17 is hydrogen, Cl-Cloalkyl, cyclohexyl, C2-CI8alkenyl or -CHA, -CH20H, or, CH20H if n is 2, -CH2 R17 is -M2-U-Um20H, -CHW, (CH2)p CH2)p_ Or -CH2CH2-T4-CH2CH2- in 1 oq CH20H which p is an integer,ranging from 2 to 4, q is an integer ranging from 2 to 10, r is an integer ranging from 2 to 6, T4 is sulfur or / N - R26 and R26 is hydrogen or Cl-C4alkyl, or, if n is 3, CH2CH2- R17 1S - 1 or CH2CH2-N-CH2CH2- if n is 4, R17iS or -CH2 CH3-CH-CH2-N-CH2-CH-CH3 1 1 -CH2 CH3-1- 1 or, N-CH2CH2-N CH3-CH-CH " \ CH2-CH-CH3 1 2 1 lle invention furthermore particularly preferably relates to products in which, in the compound of the formula III, R12 'S tert-butyl, R15 is Cl-C4alkyl and is bonded in the ortho-position relative to the OH group, s is the number 1, Q is -C.H2,,j- and is bonded in the para-position relative to the OH group, where n is the number 2 and n is an integer 1, 2 or 4, where, if n is 1, R17 is Cl-C4alkyl, or, if n is 2, R17 is f (CH2)p oq CH2)p- or -CH2CH2-T4-CH2CH2-, in which p is the number 2, q is the number 2 and T4 is sulfur, or, if n is 4, -CH2 R17 is -CH2 Examples of preferred compounds of the formula I are pentaerythritol, thiodiethylene glycol, 1,4-butanediol, 1,2-propanediol, diethylene glycol, triethylene glycol, CH3 CH3 CH3 CH3 diethanolamine, glycerol, HOCH2CH2 - N - OH HN: OH or CH3 CH3 CH3 H3 CH3 CH3 HN CH3 CH3 Glycerol is particularly preferred.

Preferred compounds of the formula II are naturally occurring vegetable oils, fats and waxes, animal oils and fats as well as artificial polyol derivatives.

Preferred vegetable oils, fats and waxes are, for example, coconut fat, rapeseed oil, sunflower oil, soya oil, castor oil, maize germ oil, safflower oil, olive oil, groundmit oil, cottonseed oil, sesame seed oil, tallow oil, pumpkin seed oil or linseed oil.

Preferred animal oils and fats are, for example, butter fat, lard, fish oil, sperm oil, neat's foot oil or train oils.

Examples of preferred artificial polyol derivatives are Radiamuls (glycerol td C&IC10) or sorbitan derivatives. The sorbitan derivatives are commercially available, for example, under the names Span1020, SpanO4O, SpanO6O, Span065, Span080, Span085, Tween02O, TweenO4O, TweenO6O, Tween065, Tween08O or Tween085.

Coconut fat, rapeseed oil, sunflower oil or castor oil are particularly preferred, coconut fat is very particularly preferred.

Preferred compounds of the formula Ill are (CH3)39 0 W, UH2ALA12- C - 0 CH3 (CH3)3C (CH3)3C _ (CH3)3C - 0 11 - H Y_ CH2CH2-C-O-CH2 ----C, (CH3)3C -14 0 11 H CH2-CH2-C-O-CH2-CH2-0-CH2- - o- ? (CH3)3C -12 (CH3) 0 11 3C HO YCH2-CHZ-(;-u-%,.o,8n37, (CH3)3C (CH3)3C 0 19 HO- CH __S 2-CH2-C-O-CH2-CH2 (CH3)3C (CH3W 0 H10 11 CH2-CH2- C - 0 - iSOC18H37, (CH3)3C (CH3)3-C 0 11 HO CH2-S-CH2- C - 0 - CH3, (CH3)3C -2 (CH3)3C 0 11 HO-H2-CH2-C-O-CH:f L (CH3)3 CH2 or J 2 OH C(CH3)3 0 H3C C(CH3)3 H -2 Particularly preferred compounds of the formula Ill are methyl 3-(3',5'di-tert-butyl-4'hydroxyphenyl)propionate and methyl 3-(3'-tert-butyl-4'hydroxy-5'-methylphenyl)propionate.

Particularly preferred compounds of the formula IV are alkanes having 12 to 18 carbon atoms and/or C9-Cl3alkylbenzene.

In a specifically preferred manner, the invention relates to products which can be obtained by reacting components a), b), c) and d), the component a) being a compound of the formula 1, in particular pentaerythritol, thiodiethylene glycol, 1,4-butanediol, 1,2-propanediol, diethylene glycol, triethylene glycol, diethanolamine or glycerol, or a mixture of these, component b) is a compound of the formula II, in particular coconut fat, rapeseed oil, sunflower oil,.a oil or castor oil or a mixture of these, component c) is a compound of the formula IL. -.n particular methyl 3-(3',5'-di-tert-butyl-4'-hydroxyphenyl)propionate, methyl 3-(3'-tert-butyl-4'-hydroxy-S'-methylphenyl)propionate or (CH3)3C 0 11 HO CH2-S-CH2- C - 0 - CH3 or a mixture of these, and component d) is a (CH3)3C compound of the formula IV, in particular C9-Cl3alkylbenzene or an alkane having 12 to 20 carbon atoms or a mixture of these.

Components a), b), c) and d) are expediently present in a molar quantitative ratio of 0. 1: LO. L0.1 to 15: 1:30:10. A molar quantitative ratio of 1: LL0.5 to 10: 1:20:10 is preferred. A molar quantitative ratio of 1: L2:2 to 10: 1: 10: 10 is particularly preferred.

The products according to the invention can comprise, for example, 5 to 95 % by weight, preferably 30 to 80 % by weight, in particular 50 to 80 % by weight, of the active group E-2 R12 HO 0 AI (R15) S Q - C - (E-2).

Particularly judicious products are those obtainable by reacting components a) and b) with methyl 3-(3',5"-di-tert-butyl-4'-hydroxyphenyl)propionate and with a C12-CI8alkane.

This invention additionally relates to a product obtainable by reacting components a), b), e) and f), where components a) and b) are defined as described above and e) corresponds to one or more compounds of the formula V R12 HO N (V) (Rj_5.1 It% and f) corresponds to one or more compounds of the formula VI 0 11 H2C C - C - 0 - R28 (VI) 1 K X in which R28 is hydrogen or C,-CI8alkyl and R. is hydrogen or methyl and R12, RIS and s are defined as described above.

Particular preference is given to products in which R28 is C,-C4alkyl, especially methyl.

Preference is also given to products where in addition the abovedescribed component d) of the formula IV is added.

Very particular. preference is given to products where component e) of the formula V is 2,6-di-tert-butylphenol and component f) of the formula VI is methyl acrylate.

This reaction takes place with particular advantage with the aid of potassium hydroxide (30% strength solution) at from 80 to 15TC, in particular from 100 to UTC. Within this temperature range the sterically hindered phenol is reacted with a small molar excess of unsaturated alkyl ester in, for example, a one-hour reaction and, following the removal of the excess ester by distillation the product is reacted with, for example, coconut fat and glycerol in the course, for example, of five hours at, for example, 190T. If desired, the reaction is performed under vacuum or under an inert gas atmosphere. Lithium methanolate, for example, is preferably employed as catalyst. However, it is also possible for the originally employed potassiL. iydroxide solution to catalyse the reaction.

Preferably, components e) and f) are first of all reacted with one another and then with components a) and b) and, if used, d) are reacted in any desired sequence, the process conditions corresponding accordingly to those mentioned above.

The present invention also relates to products obtainable by reacting components a), b) and c), all three components being initially introduced and reacted simultaneously. Catalysts, proportions and reaction conditions correspond, accordingly, to those indicated above for the first subject of the invention.

As already mentioned, the products according to the invention are suitable above all for stabilising organic materials against oxidative, thermal or light-induced degradation. Particular mention is made of their outstanding action as antioxidants in the stabilisation of organic materials.

Examples of such materials are:

1. Polymers of monoolefins and diolefins, for example polypropylene, polyisobutylene, polybut- 1 -ene, poly-4-methylpent- I -ene, polyisoprene or polybutadiene, and polymers of cycloolefins, for example of cyclopentene or norbomene; furthermore polyethylene (which optionally can be crosslinked), for example high density polyethylene (HDPE), high density polyethylene of high molecular weight (HDPE-HMW), high density polyethylene of ultrahigh molecular weight (HDPE-UHMW), medium density polyethylene (NOPE), low density polyethylene (LDPE), linear low density polyethylene (LI,DPE), (BLDPE) and (ULDPE).

Polyolefins, i.e. polymers of monoolefins exemplified in the preceding paragraph, in particular polyethylene and polypropylene, can be prepared by different, and especially by the following, methods:

a) by means of free radicals (normally under high pressure and at elevated temperature).

b) by means of a catalyst, the catalyst normally containing one or more metals of group 1Vb, Vb, VIb or VIII of the Periodic Table. These metals usually have one or more ligands, such as oxides, halides, alcoholates, esters, ethers, amines, alkyls, alkenyls and/or aryls that may be either 7c- or cF-Coordinated. These metal complexes may be in the free form or fixed on substrates, for example on activated magnesium chloride, titanium(III) chloride, alumina or silicon oxide. These catalysts may be soluble or insoluble in the polymerisation medium. The catalysts can be active as such in the polymerisation or further activators may.be used, for example metal alkyls, metal hydrides, metal alkyl halides, metal alkyl oxides or metal alkyloxanes, the metals being elements of groups Ia, Ha and/or IlIa of the Periodic Table. The activators may be modified, for example, with further ester, ether, arnine or silyl ether groups. These catalyst systems are usually termed Phillips, Standard Oil Indiana, Ziegler (-Natta), TNZ (DuPont), metallocene or single site catalysts (SSQ.

2. Mixtures of the polymers mentioned under 1), for example mixtures of polypropylene with polyisobutylene, polypropylene with polyethylene (for example PP/HDPE, PP/LDPE) and mixtures of different types of polyethylene (for example LDPE/HDPE).

3. Copolymers of monoolefins and diolefins with each other or with other vinyl monomers, for example ethylene/propylene copolymers, linear low density polyethylene (LLDPE) and mixtures thereof with low density polyethylene (LDPE), propyIene-butI-ene copolymers, propylene-isobutylene copolymers, ethylene-but-l-ene copolymers, ethylene-hexene copolymers, ethylene-methylpentene copolymers, ethylene-heptene copolymers, ethyleneoctene copolymers, propylene-butadiene copolymers, isobutyleneisoprene copolymers, ethylene-alkyl acrylate copolymers, ethylene-alkyl methacrylate copolymers, ethylene-vinyl acetate copolymers and their copolymers with carbon- mon- oxide, or ethylene-acrylic acid copolymers and their salts (ionomers), and terpolymers of ethylene with propylene and a diene, such as hexadiene, dicyclopentadiene or ethylidenenorbomene; furthermore mixtures of such copolymers with one another and with polymers mentioned under 1), for example polypropylenelethylene-propylene copolymers, WPEjethylene-vinyl acetate copolymers, LDPE/ethylene-acrylic acid copolymers, LIDPEjethylene- vinyl acetate copolymers, LLDPEJethylene-acrylic acid copolymers and alternating or random polyalkylene-carbon monoxide copolymers and mixtures thereof with other polymers, for example polyarnides.

4. Hydrocarbon resins (for example CS-C9) including hydrogenated modifications thereof (e.g. tackifiers) and mixtures of polyalkylenes and starch.

5. Polystyrene, poly(p-methylstyrene), poly((x-methylstyrene).

6. Copolymers of styrene or a-methylstyrene with dienes or acrylic derivatives, for example styrene-butadiene, styrene-acrylonitrile, styrene-alkyl methacrylate, styrene-butadiene-alkyl acrylate, styrenebutadiene-alkyl methacrylate, styrene-maleic anhydride, styreneacrylonitiile-methyl acrylate; mixtures of high impact strength of styrene copolymers and another polymer, for example a polyacrylate, a diene polymer or an ethylenepropylene-diene terpolymer, and block copolymers of styrene, such as styrene-butadienestyrene, styrene-isoprene- styrene, styrene-ethylene-butylene-styrene or stymne-ethylene-propylene- styrene.

7. Graft copolymers of styrene or a-methylstyrene, for example styrene on polybutadiene, styrene on polybutadiene-styrene or polybutadieneacrylonitrile copolymers, styrene and acrylonitrile (or methacrylonitrile) on polybutadiene; styrene, acrylonitrile and methyl methacrylate on polybutadiene; styrene and maleic anhydride on polybutadiene; styrene, ar -lonitrile and maleic anhydride or maleimide on polybutadiene; styrene and maleimide o" polybutadiene, styrene and alkyl acrylates or alkyl 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, and mixtures thereof with the copolymers mentioned under 6), for example the copolymer mixtures known as ABS, MBS, ASA or AES polymers.

8. Halogen-containing polymers, such as polychloroprene, chlorinated rubber, chlorinated and brominated copolymer of isobutylene/isoprene (halobutyl rubber), chlorinated or sulfochlorinated polyethylene, copolymers of ethylene and chlorinated ethylene, epichlorohydrin homo- and copolymers, especially polymers of halogen-containing vinyl compounds, for example polyvinyl chloride, polyvinylidene chloride, polyvinyl fluoride, polyvinylidene fluoride; as well as copolymers thereof, such as vinyl chlorideMnylidene chloride, vinyl chloride/vinyl acetate or vinylidene chloride/vinyl acetate.

9. Polymers derived from a,p-unsaturated acids and derivatives thereof, such as polyacrylates and polymethacrylates; polymethyl methacrylates, polyacrylamides and polyacrylonitriles, impact-modified with butyl acrylate.

10. Copolymers of the monomers mentioned under 9) with each other or with other unsaturated monomers, for example acTylonitrile-butadiene copolymers, acrylonitrile-alkyl acrylate copolymers, acrylonitrilealkoxyalkyl acrylate copolymers, acrylonitrile-vinyl halide copolymers or acrylonitrile-alkyl methacrylate-butadiene terpolymers.

11. Polymers derived from unsaturated alcohols and amines or the acyl derivatives or acetals thereof, such as polyvinyl alcohol, polyvinyl acetate, polyvinyl stearate, polyvinyl benzoate, polyvinyl maleate, polyvinylbutyral, polyallyl phthalate or polyallyl melamine; and their copolymers with olefins mentioned in item 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 polyoxymethylenes which contain ethylene oxide as a comonomer, polyacetals modified with thermoplastic polyurethanes, acrylates or MBS.

14. Polyphenylene oxides and sulfides, and mixtures thereof with stymne polymers or polyamides.

15. Polyurethanes derived from hydroxyl-terminated polyethers, polyesters and polybutadienes on the one hand and aliphatic or aromatic polyisocyanates on the other, and precursors thereof.

1 16. Polyamides and copolyamides derived from diamines and dicarboxylic acids and/or from aminocarboxylic acids or the corresponding lactams, such as polyamide 4, polyamide 6, polyamide 6/6, 6/10, 6/9, 6/12, 4/6, 12/12, polyamide 11, polyamide 12, aromatic polyamides made from m-xylene, diamine and adipic acid, polyamides prepared from hexamethylenediamine and isophthalic and/or terephthalic acid with or without an elastomer as modifier, for example poly-2,4,4-trimethylhexamethyleneterephthalamide or poly-m-phenyleneisophthalamide. Block copolymers of the aforementioned polyamides with polyolefins, olefin copolymers, ionomers or chemically bonded or grafted elastomers; or with polyethers, e.g. with polyethylene glycol, polypropylene glycol or polytetramethylene glycol. Furthermore polyamides or copolyamides modified with EPDM or ABS; and polyamides condensed during processing (RIM polyamide systems).

17. Polyureas, polyimides, polyamide-imides, polyether-imides, polyesterimides, polyhydantoins and polybenzimidazoles.

18. Polyesters derived from dicarboxylic acids and diols and/or from hydroxycarboxylic acids or the corresponding lactones, such as polyethylene terephthalate, polybutylene terephthalate, poly- 1,4dimethylolcyclohexane tereplithalate and polyhydroxybenzoates, and block polyether esters derived from hydroxyl-terTninated polyethers; furthermore polyesters modified with polycarbonates or MBS.

19. Polycarbonates and polyester carbonates.

20. Polysulfones, polyether sulfones and polyether ketones.

21. Crosslinked polymers derived from aldehydes on the one hand and phenols, urea or melamine on the other hand, such as phenollfonnaldehyde resins, urealforinaldehyde resins and melamine/formaldehyde resins.

22. Drying and non-drying alkyd resins.

23. Unsaturated polyester resins derived from copolyesters of saturated and unsaturated dicarboxylic acids with polyhydric alcohols, vinyl compounds as crosslinking agents, and also halogen-containing modifications thereof of low flammability.

24. Crosslinkable acrylic resins derived from substituted acrylates, for example from 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 products of bisphenol A diglycidyl ethers, bisphenol F diglycidyl ethers, which have been crosslinked by means of conventional curing agents, such as anhydrides or amines, with or without accelerators.

27. Natural polymers such as cellulose, natural rubber, gelatin and chemically modified polymer-homologous derivatives thereof, such as cellulose acetates, cellulose propionates and cellulose butyrates, or the cellulose ethers such as methylcellulose; and rosins and derivatives.

28. Blends (polyblends) of the aforementioned polymers, for example PP/EPDM, polyamide/EPDM or ABS, PVC/EVA, PVC/ABS, PVC/MBS, PCtABS, PBTPIABS, PC/ASA, PC/PBT, PVC/CPE, PVC/acrylates, POWthermoplastic PUR, PC/thermoplastic PUR, POWacrylate, POM/MBS, PPO/HIPS, PPO/PA 6.6 and copolymers, PA/HDPE, PA/PP, PA/PPO, PBTIPC/ABS or PBTIPETIPC.

29. Naturally occurring and synthetic organic materials which are pure monomeric compounds or mixtures of such compounds, for example mineral oils, animal or vegetable fats, oil and waxes, or oils, waxes and fats based on synthetic esters (e.g. phthalates, adipates, phosphates or trimellitates), as well as mixtures of synthetic esters with mineral oils in any weight ratios, typically those used as spinning compositions, and aqueous emulsions of such materials.

30. Aqueous emulsions of natural or synthetic rubbers, e.g. natural rubber latex or latices of carboxylated styrene-butadiene copolymers.

The invention therefore furthermore relates to compositions comprising an organic material which is sensitive to oxidative, thermal or lightinduced degradation and at least one product obtainable by reacting components a), b), c) and optionally d), and to the use of these products for stabilising organic material against oxidative, thermal or lightinduced degradation.

The invention therefore also relates to a process for stabilising organic material against thermal, oxidative or light-induced degradation, which comprises adding, to this material, at least one product obtainable by reacting components a), b), c) and optionally d).

The use of these products as antioxidants in organic materials is of particular interest.

Preferred organic materials are polymers, for example synthetic polymers, in particular thermoplastic polymers. Particularly preferred organic materials are polyolefins and styrene copolymers, for example those mentioned above under items 1 to 3 and items 6 and 7, in particular polyethylene and polypropylene as well as ABS and styrene/butadiene copolymers. The invention therefore preferably relates to compositions in which the organic material is a synthetic organic polymer or a mixture of such polymers, in particular a polyolefin or a styrene copolymer.

As a rule, the products are added to the material to be stabilised in amounts from 0.01 to 10 %, preferably 0.01 to 5 %, in particular 0.0 ' 1 to 2 %, relative to the total weight of the material to be stabilised. It is particularly preferred to employ the products according to the invention in amounts of 0.01 to 0.5 %, in particular 0.05 to 0.3 %.

The invention additionally relates to compositions comprising cc) an organic material which is subjected to oxidative, thermal or lightinduced degradation, and P) at least one product according to the invention.

Component cc) can be an optionally oxygen-containing hydrocarbon fuel, a lubricant a hydraulic fluid, a metalworking fluid or a synthetic polymer. Mixtures of the respective components (x) are also possible.

As already mentioned, the products according to the invention [component (0)] also possess wear- and corrosion-inhibiting properties in fuels. Particularly noteworthy is their outstanding increase of the lubricity (antiwear properties) in fuels having a low sulfur content and/or aromatics content.

The present invention therefore also relates to the use of the products of component (0) as antiwear additives in an engine fuel system.

In general, the products of component (0) are added to the fuel in an amount of fTom 0.0001 to 10%, preferably from 0.001 to 5% and, in particular, from 0.005 to 1%, based on the weight of component (cc).

The products of component (0) can also be mixed with liquid carriers compatible with the end-product fuels in order to produce concentrates which are added subsequently to base fuels or formulated fuels. Such concentrates may facilitate the mixing, intermixing, pouring or transfer (on mass or in units/portions) of the products of component (p).

The carriers are customarily organic solvents for the products of component (0), examples being hydrocarbons such as xylol or toluene, ethers, alcohols or mixtures thereof, or they may be constituents of the base fuels or of the formulated fuels which are desired as end products. The addition of the concentrates to the base materials. of formulated fuels in order to obtain end-product fuels can be carried out discontinuously, for example from unit containers with concentrates which are obtainable in retail or at other points of sale, or by means of additions within refineries or fuel distribution sites. Further methods of addition are likewise possible.

The products of component (0) may be present in different amounts in the concentrate, depending on the desired properties of the concentrate, such as its viscosity. A suitable amount in the carrier medium, in general, is from approximately 10 to 90% by weight more usually from approximately 20 to 50% by weight,'of the products of component (p).

The end-product fuels can be hydrocarbons, oxygen-containing compounds or mixtures thereof. The hydrocarbon fractions which can be used for the fuel compositions include distillate fuels whose boiling points are in the kerosene and gas-oil range (165 to 565"C). Customary middle- distillate fuels of this kind include road diesel and other diesel oils having boiling points in the range from 200 to 370"C, and also jet fuels, kerosenes, gas-oil and cycle oils. Middle-distillate fuels of this kind can be straight-run distillate oils, catalytically or thermally cracked distillate fuel oils or mixtures of straight-run combustion oils/heavy oils/heating oils/oils, naphthas and similar materials with cracked distillate materials. These fuels are normally derived from petroleum, but may also derive at least partly from other sources, for example slate, tar sands, coal, lignite, biomass and the like. The fuels may include a proportion of oxygen-containing co-components, for example alcohols or ethers, including methyl tert-butyl ether (MTBE). The fuels may also comprise in their entirety oxygen-containing compounds such as methanol and/or ethanol.

Also suitable are those fuels which have been subjected to conventional treatment processes, for example a treatment with an acid or base, hydrogenation, solvent refining or an earthing treating.

Of particular interest are compositions in which component (cc) is a diesel fuel.

The fuels can be employed, for example, in the operation of jet, motorvehicle, gas turbine or diesel engines. In a preferred embodiment of thisinvention a fuel is used which is suitable for use in a diesel engine.

The composition of these diesel fuels is highly variable, in accordance with the nature of the crude oil, the refining process, the components with which the crude oil is mixed and the climate in which the fuel is to be sold. As noted earlier above, this invention is employed primarily in the diesel fuels with a reduced sulfur content and/or aromatics content, which are produced nowadays to comply with local statutory requirements/regulations. These fuels normally have a sulfur content of less than 500 pprn (0.05%) and/or an aromatics content of less than 35% by weight.

Consequently, compositions of particular interest include those in which component ((x) is a fuel which contains less than 0. 10% by weight, preferably less than 0.05% by weight and, in particular, less than 0.0 1% by weight of sulfur.

The composition of the fuel, and hence also its inherent lubricity, can vary in accordance with the level of the requirements of the local statutory regulations.

The invention is also employed in aviation fuels, for r - - mple in those which generally are used in jet turbine engines. Fuels of this kind have a composition close to that of the diesel oils with a low content of aromatics and of sulfur. The addition of the products of component (P) according to the invention to these fuels may reduce wear in the engine.

The invention could also be employed in lead-free oT formed automotive fuels which are now generally used in aircraft piston engines and in motor vehicles. The addition of the products of component (0) to these fuels may improve engine performance and makes it possible to employ the fuel in place of leaded fuels, in use for example in aircraft piston engines where leaded fuel is currently used.

Therefore, the present invention alsorelates to a method of reducing wear in an engine fuel system, which comprises adding a product of component (0) to the fuel.

In addition to the products of component (0) the compositions according to the invention may also include conventional additives which are added in order to improve still further the basic properties of the fuel, as is described in the handbook "Lubricant and Fuel Additives", Kline & Company Inc., International Business Consultants, Fairfield, NJ, USA, pages 309320 (1990). These additives include: antioxidants, metal passivators, rust protection agents, viscosity improvers, pour-point depressants, dispersants, detergents, high-pressure additives, friction-reducing additives, antiwear additives, demulsifiers, cloud-point depressants, waxlike antisettling additives, antistatic additives, defoamers, evaporation additives, biocides, odour masks, colorants, ignition accelerators, antifreezes, antiknock additives, conductivity improvers, PM4VI) purity additives and other lubricity additives.

In addition to the product, the compositions according to the invention can also contain conventional additives, for example those mentioned below.

1. Antioxidants 1. 1. Alkylated monophenols, for example 2,6-di-tert-butyl-4-methylphenol, 2-butyl-4,6dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert- butyl-4-n-butylphenol, 2,6-ditert-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-ditert-butyl- 4-methoxymethylphenol, nonylphenols which are linear or branched in the side chain, such as 2,6-di-nonyl-4-methylphenol, 2,4-dimethyl-6-(1'- methylundec-l'-yl)phenol, 2,4-dimethyl-6-(1'-methylheptadec- V-y1)phenol, 2,4-dimethyl6-(1'-methyltridec-1'-yl)phenol and mixtures thereof.

1.2. Alkyldiiomethylphenols, for example'2,4-dioctylthiomethyl-6-tertbutylphenol, 2,4-dioctylthiornethyl-6-methylphenol, 2,4-dioctylthiomethyl6-ethylphenol, 2,6-di-dodecylthiomethyl-4-nonylphenol.

1.3. Hydroquinones and alkylated hydroquinones. for example 2,6-di-tertbutyl-4methoxyphenol, 2,5-di-tert-butylhydroquinone, 2,5-di-tenamylhydroquinone, 2,6-diphenyl-4-octadecyloxyphenol, 2,6-di-tertbutylhydroqui none, 2,5-di-tert-butyl-4-hydroxy- 1 anisole, 3,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4- hydroxyphenyl stearate, bis(3,5-di-tert-butyl-4-hydroxyphenyl) adipate.

1.4. Tocopherols for example cc-tocopherol, P-tocopherol, y-tocopherol, 8tocopherol and mixtures thereof (vitamin E).

1.5. Hydroxylated. thiodiphenyl ethers, for example 2,2'-thiobis(6-tenbutyl-4-methylphenol), 2,2'-thiobis(4-octylphenol),4,4'-thiobis(6-tertbutyl-3-methylphenol), 4,4'-thiobis(6-tert-butyl-2-methylphenol), 4,4'thiobis(3,6-di-sec-amylphenol), 4,4-bis(2,6-dimethyl-4-hydroxyphenyl) disulfide.

1.6. AlkylidenebiEhenols. for example 2,2"-methylenebis(6-tert-butyl-4methylphenol),. 2,2'-methylenehis(6-tert-butyl-4-ethylphenol), 2,2'methylenebis[4-methyl-6-(ct-methylcyclohexyl)phenol], 2,2'-methylenebis(4methyl-6-cyclohexylphenol), 2,2'-methylenebis(6-nonyl-4-methylphenol), 2, 2'-methylenebis(4,6-di-tert-butylphenol), 2,2'-ethylidenebis(4,6-di-tertbutylphenol), 2,2'-ethylidenebis(6-tert-butyl-4-isobutylphenol), 2,2methylenebis[6-((x-methylbenzyl)-4-nonylphenoll, 2,2'-methylenebis[6-(aadimethylbenzyl)4-nonylphenoll, 4,4'-methylenebis(2,6-di-tert-butylphenol), 4,4'-methylenebis(6-tertbutyl-2-methylphenol), 1,1-bis(5-tert-butyl-4hydroxy-2-methylphenyl)butane, 2,6-bis(3tert-butyl-5-methyl-2hydroxybenzyl)-4-methylphenol, 1,1,3-tds(5-tert-butyl-4-hydroxy2-methylphenyl)butane, 1,1-bis(S-tert-butyl-4-hydroxy-2-methylphenyl)-3-ndodecylmer- captobutane, ethylene glycol bis[3,3-bis(3'-tert-butyl-4'hydroxyphenyl)butyrate], bis(3tert-butyl-4-hydroxy-5methylphenyl)dicyclopentadiene. bis[2-(3'-tert-liutyl-2'-hydroxy5'methylbenzyl)6-tert-butyl-4-methylphenyllterephthalate, 1,1-bis(3,.' iimethyl-2hydroxyphenyl)butane, 2,2-bis(3,5-di-tert-butyl-4hydroxyphenyl)propane, 2,2-bis(5-tertbutyl-4-hydroxy-2-methylphenyl)-4-ndodecylmercaptobutane, 1,1,5,5-tetra-(5-tert-butyl4-hydroxy-2methylphenyl)pentane.

1.7. 0-, N- and S-benzyl compounds for example 3,5,3',5'-tetra-tert-butyl4,4'-dihydroxydibenzyl ether, ocmdecyl-4-hydroxy-3,5dimethylbenzylmercaptoacemte, tridecyl 4-hydroxy-3,5-di-tertbutylbenzylmercaptoacetate, tris(3,5-di-tert-butyl4-hydr,oxybenzyl)amine, bis(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) dithioterephthalate, bis(3, 5-di-tert-butyl-4-hydroxybenzyl) sulfide, isooctyl 3,5-di-tert-butyl4hydroxybenzylmercaptoacetate.

1.8. Hydroxybenzylated majonates, for example dioctadecyl 2,2-bis(3,5-ditert-butyl-2- 1 hydroxybenzy1)malonate, dioctadecyl 2-(3-tert-butyl-4-hydroxy-5- methylbenzyl)malonate, didodecyImercaptoethyl 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)malonate.

1.9. Aromatic hydroxvbenzyl communds for example 1,3,5-tris(3,5-di-tertbutyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene, 1,4-bis(3,5-di-tert-butyl4-hydroxybenzyl)-2,3,5,6tetramethylbenzene, 2,4,6-tris(3,5-di-tert-butyl4-hydroxybenzyl)phenol.

1. 10. Triazine compounds for example 2,4-bis(octylmercapto)-6-(3,5-ditert-butyl-4hydroxyanilino)-1,3,5-triazine, 2-octyimercapto-4,6-bis(3,5di-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-tertbutyl-4-hydroxyphenoxy)-1,2,3-triazine, 1,3,5-tris(3,5-di-tert-butyl-4hydroxybenzyl)isocyanurate, 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6dimethylbenzyl)isocyanurate, 2,4,6-tris(3,5-di-tert-butyl-4hydroxyphenylethyl)-1,3,5-triazine, 1,3,5-tris(3,5-di-tert-butyl-4hydroxyphenylpropionyl)-hexahydro-1,3,5-tda zine, 1,3,5-tds(3,5dicyclohexyl-4-hydroxybenzyl)isocyanurate. 1 1. 11. Benzvlvhosiphonates, for example dimethyl 2,5-di-tert-butyl-4- hydroxybenzylphosphonate, diethyl 3,5-di-tert-butyl-4- hydroxybenzylphosphonate, dioctadecyl 3,5-di-tertbutyl-4- hydroxybenzylphosphonate, dioctadecyl 5-tert-butyl-4-hydroxy-3- methylbenzylphosphonate, the calcium salt of the monoethyl ester of 3,5- di-tert-butyl-4-hydroxybenzylphosph6 hic acid.

1. 12. Acylaminophenols for example 4-hydroxylauranilide, 4hydroxystearanilide, octyl N-(3,5-di-tert-butyl-4-hydroxyphenyl)carbamate.

1. 13. Esters of D-(3,5-di-tert-butyl-4-hydroxyphenyl)l)ropionic acid with mono- or polyhydric alcohols, e.g. 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, 3thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4hydroxymethyl- 1 -phospha-2,6,7-trioxabicyclo[2.2.21 octane.

1. 14. Esters of 0-(5-tert-butyl-4-hydroxy-3-methylphen-Yl)propionic acid with mono- or polyhydric alcohols, e.g. 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)oxwnide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropahe, 4-hydroxymethyl- 1 -phospha-2,6, 7-trioxabicyclo[2.2.2]octane.

1. 15. Esters of B-(3,5-dicyclohexyl-4-hydroxyRhenyl)RmRionic acid with mono- or poly- hydric alcohols, e.g. with methanol, ethanol, octanol, octadecanol, 1,6- hexanediol, 1,9nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl) isocyanurate, NN'bis(hydroxyethyl)oxalamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-l-phospha-2,6,7- trioxabicyclo[2.2.2]octane.

1. 16. Esters of 3,5-di-tert-butyl-4-hydroxyphenyI acetic acid with monoor polyhydric alcohols, e.g. with methanol, ethanol, 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)oxalamide, 3-thiaundecanol, 3-thiapentadecanol, tdrnethylhexanediol, trimethylolpropane, 4-hydroxymethyl- I -phospha-2,6, 7-trioxabicyclo[2.2.2] octane.

1.17. Amides of D-(3,5-di-tert-butyl-4-hydroxyphenyl)proRionic aci e.g. NN'-bis(3,5di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamide, N, N'-bis(3,5-di-tertbutyl-4-hydroxyphenylpropionyl)trimethylenediamide, N, N'-bis(3,5-di-tertbutyl-4-hydroxyphenylpropionyl)hydrazide, N,N'-bis[2-(3[3,5-di-tert-butyl-4-hydroxyphenyl]propionyloxy)ediylloxalamid e (NaugardOXL-1 from Uniroyal).

1.18. Ascorbic acid (vitamin C).

1. 19. Amine antioxidants for example N,N'--(iiisopropyl-pphenylenediamine, N,N'-di-sec-butyl-p-phenylenediamine, N,N'-bis(1,4dimethylpentyl)-p-phenylenediamine, N,N'-bis(l-ethyl-3-methylpentyl)-pphenylenediamine, N,N'-bis(l-methylheptyl)-p-phenylenediamine, N,N'dicyclohexyl-p-phenylenediamine, N,N'-ffiphenyl-p-phenylenediamine, N,N'di-(naphthyl-2-)-p-phenylenediamine, N-isopropyl-N'-phenyl-pphenylenediamine, 1 N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine, N-(I-methylheptyl)-N'- phenyl-p-phenylenediamine, N-cyclohexyl-N'-phenyl-p-phenylenediamine, 4(P-toluenesulfonamido)diphenylamine, N,N'-dimethyl-N,N'-di-sec-butyl-pphenylenediamine, diphenylamine, N-allyldiphenylamine, 4isopropoxydiphenylamine, N-phenyl-l-naphthylamine, N-(4-tert-octylphenyl)l-naphthylamine, N-phenyl-2-naphthylamine, octylated diphenylamine, e.g. p,p'-di-tert-octyldiphenylamine, 4-n-butylaminophenol, 4butyrylaminophenol, 4-nonanoylaminophenol, 4-dodecanoylaminophenol, 4octadecanoylwninophenol, di-(4-methoxyphenyl)amine, 2,6-di-tert-butyl-4dimethylaminomethylphenol, 2,4'-di-aminodiphenyhnethane, 4,4'diaminodiphenylmethane, N,N,N',N'-tetramethyl-4,4'-diaminodiphenylmethane, 1,2-di[(2-methylphenyl)amino]ethane, 1,2-di(phenylamino)propane, (otolyl)biguanide, di-[4-(l',3'-dimethylbutyl)phenyllamine, tert-octylated N-phenyl-l-naphthylamine, a mixture of mono- and dialkylated tertbutyl/tert-octyldiphenylamines, a mixture of monoand dialkylated nonyldiphenylamines, a mixture of mono- and dialkylated dodecy1diphenylamines, a mixture of mono- and dialkylated isopropyLrisohexyl-diphenylamines, mixtures of mono- and dialkylated, tert-butyldiphenylamines, 2,3-dihydro-3,3-dimethyl-4H-1,4-benzothiazine, phenothiazine, a mixture of mono- and dialkylated tert-butyl/tertoctylphenothiazines, a mixture of monoand dialkylated tertoctylphenothiazines, N-allylphenothiazine, N,N,N',N'-tetraphenyl-1,4diaminobut-2-ene, N,N-bis(2,2,6,6-tetmmethylpiperidin-4yl)hexamethylenediamine, bis(2,2,6,6-tetramethylpiperidin-4-yl) sebacate, 2,2,6,6-tetramethylpiperidin-4-one, 2,2,6,6-temmethylpiperidin-4-ol.

2. UV absorbers and light stabilisers 2.1. 2-(2'-HydroxvPhenyl)benzotriazoles, for example 2-(2'-hydroxy-S'methylphenyl)benzotriazole, 2-(3',5'-di-tert-butyl-2'hydroxyphenyl)benzotriazole, 2-(5'-tert-butyl2hydroxyphenyl)benzotriazole, 2-(2'-hydroxy-S'-(1,1,3,3tetramethylbutyl)phenyl)benzotriazole, 2-(3',5'-di-tert-butyl-2'hydroxyphenyl)-5-chloro-benzotriazole, 2-(Y-tert-butyl2'-hydroxy-S'methylphenyl)-5-chloro-benzotriazole, 2-(3'-sec-butyl-S'-tert-butyl-2'hyd. roxyphenyl)benzotriazole, 2-(2'-hydroxy-4'-octoxyphenyl)benzotriazole, 2(Y,Y-ditert-amyl-2'-hydroxyphenyl)benzotdazole, 2-(3',5'-bis(ct,ctdirnethylbenzyl)-2'-hydroxyphenyl)benzotriazole, 2-(3'-tert-butyl-2'hydroxy-5'-(2-octyloxycarbonylethyl)phenyl)-5chloro-benzotriazole, 2-(3'tert-butyl-S'-[2-(2-ethylhexyloxy)-carbonylethyll-2-hydroxyphenyl)-5-chloro-benzotriazole, 2-(3'-tert-butyl-2-hydroxy-5'-(2methoxycarbonylethyl)phenyl)-5-chloro-benzotriazole, 2-(3'-tert-butyl-2'hydroxy-5'-(2-methoxycarbonylethyl)phenyl)benzotriazole, 2-(3'-tert-butyl2'-hydroxy-5'-(2-octyloxycarbonylethyl)phenyl)- benzotriazole, 2-(3'-tert-butyl-5'-[2-(2-ethylhexyloxy)carbonylethyll-2'hydroxyphenyl)benzotriazole, 2-(3'-dodecyl-2-hydroxy-5methylphenyl)benzotriazole, 2-(T-tert-butyl2'-hydroxy-5'-(2isooctyloxycarbonylethyl)phenylbenzotriazo le, 2,2'-methylenebis[4(1,1,3,3-tetramethylbutyl)-6-benzotriazol-2-ylphenoll; the transesterification product of 2-[3'-tert-butyl-5'-(2methoxycarbonylethyl)-2'-hydroxyphenyl]-benzotriazo le with polyethylene glycol 300; [R-CH2CH2-COO-CH2CH&, where R = T-tert-butyl4'hydroxy-5'-2H-benzotriazol-2-ylphenyl; 2-[2'-hydroxy-3'-(cc,a-dimethylbenzyl)-5'-(1,1,3,3-tetmmethyI butyl)phenyl]benzotriazole; 2-[2'-hydroxy-3'-(I, 1,3,3-tetramethylbutyl)-5'-(ct,a- dimethylbenzyl)phenyl]benzotriazole.

2.2. 2-Hvdroxybenzolphenones for example the 4-hydroxy, 4-methoxy, 4octoxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy, 4,2',4-trihydroxy and Thydroxy-4,4'-ditnethoxy deri- vatives.

2.3. Esters of substituted and unsubstituted benzoic acids. for example 4tert-butyl-phenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoyl resorcinol, bis(4-tert-butylbenzoyl) resorcinol, benzoyl resorcinol, 2,4-di-tertbutylphenyl 3,5-di-tert-butyl-4- hydroxybenzoate, hexadecyl 3,5-di-tert-butyl-4-hydroxybenzoate, octadecyl 3,5-di-tertbutyl-4-hydroxybenzoate, 2-methyl-4,6-di-tert-butylphenyI 3,5di-tert-butyl-4-hydroxybenzoate.

2.4. Acrylates. for example ethyl a-cyano-p,p-diphenylacrylate, isooctyl a-cyano-p,p-diphenylacrylate, methyl (x-carbomethoxycinnamate, methyl (xcyano-o-methyl-p-methoxycinnamate, butyl ct-cyano-o-methyl-pmethoxycinnamate, methyl wcarbomethoxy-p- methoxycinnamate and N-(0-carbomethoxy-o-cyanovinyl)-2-methylindoline.

2.5. Nickel compounds for example nickel complexes of 2,2'-thiobis[4-(1,1, 3,3-tetramethylbutyl)phenol], such as the 1: 1 or 1:2 complex, with or without additional ligands such as n-butylamine, triethanolamine or NcyclohexyIdiethanolamine, nickel dibutyIdithiocarbamate, nickel salts of the monoalkyl esters, e.g. the methyl or ethyl ester, of 4hydroxy-3,5-ditert-butylbenzylphosphonic acid, nickel complexes of ketoximes, e.g. of 2-hydroxy-4-methylphenyl undecyl ketoxime, nickel complexes of 1-phenyl-41auroyl-5hydroxypyrazole, with or without additional ligands.

2.6. Sterically hindered amines, for example bis(2,2,6,6-tetramethylpiperidin4-yl) sebacate, bis(2,2,6,6-tetramethyl-piperidin4-yl) succinate, bis(1,2,2,6,6-pentamethylpiperidin4-yl) sebacate, bis(l-octyloxy-2,2,6,6tetmmethylpiperidin-4-yl) sebacate, bis(1,2,2,6,6-pentamethylpiperidyl) nbutyl 3,5-di-tert-butyl4-hydroxybenzylmalonate, the condensate of 1hydroxyethyl-2,2,6,6-tetramethyl4-hydroxypiperidine and succinic acid, linear or cyclic condensates of N,N-bis(2,2,6,6-tetramethyl-4piperidyl)hexamethylenediamine and 4-tert-,OCtylamino-2,6-dichloro-1,3,5s-triazine, tris(2,2,6,6-tetramethyl4-piperidyl) nitrilotriacetate, teadlds(2,2,6,6-tetramethyl-4-piperidyl)-1,2,3,4butanetetraoate, 1,1'-(1,2ethanediyl)bis(3,3,5,5-tetramethylpiperazinone), 4-benzoyl-2,2,6,6tetramethylpipexidine, 4-stearyloxy-2,2,6,6-tetramethylpiperidine, bis(1, 2,2,6,6-pentamethylpiperidyl) 2-n-butyl-2-(2-hydroxy-3,5-di-tertbutylbenzyl)malonate, 3-n-octyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4. 5]decane-2,4-dione, bis(I-octyloxy-2,2,6,6-tetramethylpiperidyl) sebacate, bis(I-octyloxy-2,2,6,6-tetramethylpiperidyl) succinate, linear or cyclic condensates of NN'-bis-(2,2,6,6-tetramethyl4piperidyl)h"amethylenediamine and 4-morpholino-2,6-dichlom-1,3,5-triazine, the condensate of 2-chloro-4,6-bis(4-n-butylamino-2,2,6,6-tetiamethylpiperidyI)-1,3,5triazine and 1,2-bis(3-aminopropylamino)ethane, the condensate of 2-chlorb4,6-<H(4-n-butylamino-1,2,2,6,6pentamethylpiperidyl)-1,3,5-triazi ne and 1,2-bis(3aminopropylamino)ethane, 8-acetyl-3-dodecyl-7,7,9,9-tea-amethyl-1,3,8triaza piro[4.5]decane-2,4-dione, 3-dodecyl-l-(2,2,6,6-tetramethyl-4piperidyl)pyn-olidine-2,5-dione, 3-dodecyl-l-(1,2,2,6,6-pentamethyl-4piperidyl)pyrrolidine-2,5-dione, a mixture of 4-hexadecyloxy- and 4stearyloxy-2,2,6,6-tetramethylpiperidine, the condensate of N,N'-bis(2,2, 6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4-cyclohexylamino-2, 6-dichloro-1,3,5-triazine, the condensate of 1,2-bis(3aminopropylamino)ethane and 2,4,6-trichloro-1,3,5-triazine and also 4butylamino-2,2,6,6-tetramethylpiperidine (CAS Reg. No. [136504-96-6]); N(2,2,6,6-tetramethyl-4-piperidyl)-n-docdcylsuccinimide, N-(1,2,2,6,6pentamethyl-4-piperidyl)-n-dodecylsuccinimide, 2-undecyl-7,7,9,9tetramethyl-l-oxa-3,8-diaza-4-oxospiro[4.5]decane, the reaction product of 7,7,9,9-tetramethyl-2-cycloundecyl- I -oxa-3,8-diaza-4-oxospiro (4. 5]decane and epichlorohydrin, 1,1-bis(1,2,2,6,6-pentamethyl-4piperidyloxycarbonyl)-2(4-methoxyphenyl)ethene, N,N'-bisfonnyl-N,N'-bis(2, 2,6,6-tetramethyl-4piperidyl)hexam ethylenediamine, the diester of 4methoxymethylenemalonic: acid with 1,2,2,6,6-pentamethyl-4-hydroxypiperidine, poly[methylpropyl-3-oxy-4-(2,2, 6,6-tetramethyl-4-piperidyl)lsiloxane, the reaction product of maleic anhydride-(x-olefin copolymer and 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-diethoxyoxanilide, 2,T-dioctyloxy-5,5'-di-tert-butoxanilide, 2,2'-didodecyloxy-5,5'-di-tertbutoxanilide, 2-ethoxy-2'ethoxanilide, N,N-bis(3dimethylaminopropyl)oxalamide, 2-ethoxy-5-tert-butyl-2'-ethoxanilide and its mixture with 2-ethoxy-2'-ethyl-5,4'-di-tert-butoxanilide and mixtures of oand p-methoxy-disubstituted oxanilides and mixtures of o- and pethoxy-disubstituted oxanilides.

2.8. 2-(2-Hydroxyphenyl)-1,3,5-triazines, for example 2,4,6-tris(2hydroxy-4-octyloxyphenyl)-1,3,5-tdazine, 2-(2-hydroxy-4-octyloxyphenyl)-4, 6-bis(2,4-dimethylphenyl)1,3,5-triazine, 2-(2,4-dihydroxyphenyl)-4,6bis(2,4-dimethylphenyl)-1,3,5-tdazine, 2,4-bis(2-hydroxy-4propyloxyphenyl)-6-(2,4-dimethylphenyl)-1,3,5-triazine, 2-Q-hydroxy-4octyloxyphenyl)-4,6-bis(4-methylphenyl)-1,3,5-triazine, 2-(2-hydroxy-4dodecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin e, 2-(2hydroxy-4-tridecyloxylphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triaz ine, 2-[2-hydroxy-4-(2-hydroxy-3-butyloxypropyloxy)phenyl]-4,6-bis(2,4dimethyl phenyl)1,3,5-triazine, 2-[2-hydroxy-4-(2-hydroxy-3octyloxypropyloxy)phenyl]-4,6-bis(2,4dimethylphenyl)-1,3,5-triazine, 2-[4dodecyloxy/tridecyloxy-2-hydroxypropoxy)-2hydroxyphenyll-4,6-bis(2,4dimethylp henyl)-1,3,5-triazine, 2-[2-hydroxy-4-(2-hydroxy3dodecyloxypropoxy)phenyll-4,6-bis(2,4-dimethylp henyl)-1,3,5-triazine, 2(2-hydroxy-4-hexyloxy)phenyl-4,6-diphenyl-1,3,5-tdazine, 2-(2-hydroxy-4methoxyphenyl)-4,6-diphenyl-1,3,5-triazine, 2,4,6-tris[2-hydroxy-4-(3butoxy-2-hydroxypropoxy)phenyll-1,3,5-tdazine, 2-(2-hydroxyphenyl)-4-(4methoxyphenyl)-6-phenyl- 1,3,5-tdazine, 2- (2-hydroxy-4-[3-(2-ethylhexyl1 -oxy)-2-hydroxypropyloxylphenyl) -4,6-bis(2,4-dimethylphenyl)-1,3,5tdazine.

3. Metal deactivators, for example N,W-diphenyloxamide, N-salicylal-Wsalicyloyl hydrazine, N,W-bis(salicyloyl) hydrazine, N,N-bis(3,5-di-tertbutyl-4-hydroxyphenylpropionyl) hydrazine, 3-salicyloylamino-1,2,4triazole, bis(benzylidene)oxalyl dihydrazide, oxanilide, isophthaloyl dihydrazide, sebacoyl bisphenylhydrazide, N,M-diacetyladipoyl dihydrazide, N,M-bis(salicyloyl)oxalyl dihydrazide, N,NAis(salicyloyl)- /.,.. w 1 thiopropionyl dihydrazide.

4. PhosOites 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-di-tert-butylphenyl) phosphite, diisodecyl pentaerythritol diphosphite, bis(2,4-di-tert-butylphenyl) pentaerythritol diphosphite, bis(2,6-di-tert-butyl-4-methylphenyl)-pentaerythritol diphosphite, diisodecyIoxypentaerythritol diphosphite, bis(2,4-di-tertbutyl-6-methylphenyl)pcntaerythritol diphosphite, bis(2,4,6-tri-tertbutylphenyl)pentaerythritol diphosphite, tristearyl sorbitol triphosphite, tes(2,4-di-tert-butylphenyl) 4,4'-biphenylene: diphosphonite, 6isooctyloxy-2,4,8,10-tetra-tert-butyl-12H-dibenz[d,g]-1,3,2-dioxaphospho cin, 6-fluoro-2,4,8,10tetra-tert-butyl-12-methyl-dibenz[d,g]-1,3,2dioxaphospho cin, bis(2,4-di-tert-butyl-6methylphenyl) methyl phosphite, bis(2,4-di-tert-butyl-6-methylphenyl) ethyl phosphite, 2,2',2"nitrilo[triethyl tris(3,3'5,5'-tetra-tert-butyl-1,1'-biphenyl-2,2'diy1) phosphite], 2-ethylhexyl 3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl-2,2'diyl) phosphite.

Particular preference is given to using the following phosphites:

Tris(2,4-di-tert-butylphenyl) phosphite (Irgafosl 168, Ciba-Geigy), tris(nonylphenyl) phosphite, (CH3)3C C(CH3)3 Z, 1 0 (A) H3c- P - F 1 0 (CH3)3C C(CH3)3 (CH3)3C C(CH3)3 0 p - 0 CH2CH2 0 C (CH3)3C C(CH3)3 (CH3)3C ' 1 C(CH3)3 0 - N (B) -j 3 p - 0 - CH2CH(C4HOCH2CH3 0 -& c (CH3)3C C(CH3)3 (C) 01-W 0 1 - (CH3)3C 0-pOxj-0 -0-- C(CH3)3 C(CH3)3 C(CH3)3 (CH3)3C (CH3)3C H3C-( do C 0-P oxd P-O-: CH3 C(CH3h (CH3)3C P -;,- q (F) H37C18- 0 - p -OX6 p - 0 - C18H37 1 (D) (E) CH3 1 "3.;- C - CH3 0- H3C H3C '0' C, CH3 CH3 - P - OCH2CH3 (G) 2 5. Hydroxylamines for example N,N-dibenzylhydroxylamine, N,N- diethylhydroxylarnine, N,N-dioctylhydroxylarnine, N,N- dilaurylhydroxylarnine, N,N-ditetradecylhydroxylarnine, N,N- dihexadecylhydroxylarnine, N,N-dioctadecylhydroxylarnine, N-hexadecyPN- octadecylhydroxylamine, N-heptadecyl-N-octadecylhydroxylamine, N,N- dialkylhydroxylarnine from hydrogenated tallow fatty amines.

6. Nitrones. for example N-benzyl alpha-phenyl nitrone, N-ethyl alphamethyl nitrone, N-octyl alpha-heptyl nitrone, N-lauryl alpha-undecyl nitrone, N-tetradecyl alpha-tridecyl nitrone, N-hexadecyl alphapentadecyl nitrone, N-octadecyl alpha-heptadecyl nitrone, N-hexadecyl alpha heptadecyl nitrone, N-octadecyl alpha-pentadecyl nitrone, Nheptadecyl alpha-heptadecyl nitrone, N-octadecyl alpha-hexadecyl nitrone, nitrones derived from N,N-dialkylhydroxylarnines prepared from hydrogenated tallow fatty arnines.

7. Thiosynergists, for example dilauryl thiodipropionate or distearyl thiodipropionate.

8. Peroxide scavengers, for example esters of 0-thiodipropionic acid, for example the lauryl, stearyl, myristyl or tridecyl ester, mercaptobenzimidazole, the zinc salt of 2-mercaptobenzimidazole, zinc dibutyldithiocarbamate, dioctadecyl disulfide, pentaerythritol ten-aids(pdodecylmercapto)propionate.

9. Polyamide stabilisers, for example copper salts in combination with iodides andlor phosphorus compounds and salts of divalent manganese.

10. Basic co-stabilisers, for example melamine, polyvinylpyrrolidone, dicyandiamide, triallyl cyanurate, urea derivatives, hydrazine derivatives, amines, polyarnides, polyurethanes, alkali metal salts and alkaline earth metal salts of higher fatty acids, for example 1 calcium stearate, zinc stearate, magnesium behenate, magnesium stearate, sodium ricinoleate and potassium palmitate, antimony pyrocatecholate or tin pyrocatecholate.

11. Nucleating agents, for example inorganic substances, such as talc, metal oxides, such as titanium dioxide or magnesium oxide, phosphates, carbonates or sulfates of preferably alkaline earth metals; organic compounds, such as mono- or polycarboxylic acids, and their salts, such as 4-tert-butylbenzoic acid, adipic acid, diphenylacetic: acid, sodium succinate or sodium benzoate; polymeric compounds, such as ionic copolymers (ionomers).

12. Fillers and reinforcing agents, for example calcium carbonate, silicates, glass fibres, glass beads, talc, kaolin, mica, barium sulfate, metal oxides and hydroxides, carbon black, graphite, wood meal and meals or fibres of other natural products, synthetic fibres.

13. Other additives for example plasticisers, lubricants, emulsifiers, pigments, rheological additives, catalysts, flow-control auxiliaries, optical brighteners, flameproofing agents, antistatic agents and blowing agents.

14, Benzofuranones and indolinones for example those described in US 4 325 863; US 4 338 244; US 5 175 312; US 5 216 052; US 5 252 DE-A-4 316 611, DE-A-4 316 622; DE-A-4 316 876; EP-A-0 589 839 or EP-A-0 591 102, or 3-[4(2-acet oxyethoxy)phenyl]-5,7-ffi-tert-butyl-benzofuran-2-one, 5,7-di-tert-butyl- 3-[4-(2-stearoyl- oxyethoxy)phenyllbenzofuran-2-one, 3,3'-bis[5,7-di-tert-butyl-3-(4-[2- hydroxyethoxy]phenyl)benzofuran-2-onel, 5,7-di-tert-butyl-3-(4-ethoxyphenyl)benzofuran2-one, 3-(4 acetoxy-3,5-dimethylphenyl)-5,7-di-tert-butyl-benzofuran-2-one, 3-(3,5dimethy1-4-piva loyloxyphenyl)-5,7-di-tert-butyl-benzofuran-2-one, 3-(3,4-dimethylphenyl) 5,7-di-tert-butyl-benzofuran-2-one, 3-(2,3-ffimethylphenyl)-5,7-di-tert- butyl-benzofuran- 2-one.

The conventional additives are added for example at concentrations of 0. 01 to 10 % based on the total weight of the material to be stabilised.

The products and, if desired, other additives, can be incorporated into the organic material by known methods. They can be incorporated in the materials for example by admixing or applying the products and, if desired, other additives by the methods conventionally used in the art. If the materials are polymers, in particular synthetic polymers, the products can be incorporated before or during shaping or by applying the dissolved or dispersed products to the polymer, with or without subsequent evaporation of the solvent. In the case of elastomers, the latter can also be stabilised in the form of the latices. A further possibility of incorporating the products according to the invention into polymers is the addition of the former before, during or immediately after polymerization of the monomers in question, or before crosslinking. The products according to the invention can be added as they are, but also in encapsulated form (for example in waxes, oils or polymers). If they are added before or during polymerization, the products according to the invention can also act as chain length regulators for the polymers (chain terminators). The products according to the invention can also be added to the materials to be stabilised in the form of a masterbatch comprising, for example, a concentration of 2.5 to 25 % by weight of the product according to the invention.

The materials which have been stabilised in this manner can be used in a multitude of ways, for example in the form of films, fibres, tapes, moulding materials, sections or as binders for varnishes, adhesives or cements.

Preference, is given to compositions according to the invention comprising a) a lubricant, a hydraulic fluid, a metal-working fluid or a fuel, forexample for driving engines of the 4-stroke Otto, 2-stroke, diesel, Wankel and also the orbital type, and) at least one product according to the invention.

Particularly preferred as lubricants are the mineral oils, the synthetic oils or mixtures of these.

The products known per se are used from the series of the lubricants, the hydraulic fluids and the metal-working fluids.

The lubricants and hydraulic fluids which are suitable are known to those skilled in the art and described, for example, in Dieter Klamann "Schmierstoffe und verwandte Produkte" [Lubricants and Related Products], Verlag Chemie, Weinheim, 1982, in Schewe-Kobek, "Das SchmierinittelTaschenbuch" [Lubricants Guide], Dr. Alfred Hiithig-Verlag, Heidelberg, 1974, or in "Ullmanns Encyklopddie der technischen Chemie" (Ullmann's Encyclopedia of Industrial Chemistry], Volume 13, pages 85-94 (Verlag Chemie, Weinheim, 1977).

Exprnples are lubricants and hydraulic fluids based on mineral oil or synthetic lubricants or hydraulic fluids, in particular those which are derivatives of carboxylic esters and which are used at temperatures of 200T and above.

Examples of synthetic lubricants embrace lubricants based on a diester of a dibasic acid with a monovalent alcohol, for example dioctyl sebacate or dinonyl adipate, a triester of trimethylolpropane with a monobasic acid or a mixture of such acids, for example trirnethylolpropane tripelargonate, trimethylolpropane tricaprylate or mixtures of these, a tetraester of pentaerythritol with a monobasic acid or with a mixture of such acids, for example pentaerythritol tetracaprylate, or a complex ester of monobasic and dibasic acids with polyhydric alcohols, for example a complex ester of trimethylolpropane with caprylic and sebacic acid or a mixture of these.

Particularly suitable are, besides mineral oils, for example poly-(xolefins, lubricants based on esters, or phosphates, glycols, polyglycols and polyalkylene glycols, and mixtures of these with water.

The products according to the invention are oils and readily soluble lubricants and therefore particularly suitable as additives to lubricants, and mention must be made of their surprisingly good antioxidative and anticorrosive action.

The products according to the invention can display their surprising properties for example in lubricants for combustion engines, for example in combustion engines operating by the Otto principle. The products according to the invention prevent the formation of deposits (sludge), or reduce these deposits to a surprising extent.

So-called masterbatches can also be- prepared.

The products according to the invention are active as additives in lubricants even when used in very small amounts. They are admixed to the lubricants advantageously in an amount of 0.01 to 5 % by weight, preferably in an amount of 0.05 to 3 % by weight and particularly preferably in an amount of 0.1 to 2 % by weight, in each case based on the lubricant.

The lubricants can additionally comprise other additives which are added to improve the basic properties of lubricants even further, these include: antioxidants, metal passivators, 1 rust inhibitors, viscosity index improvers, pour-point depressers, dispersants, detergents, high-pressure additives, antifriction additives and antiwear additives.

A series of such compounds can be found, for example, in the above list " 1. Antioxidants", in particular items 1. 1 to 1. 16. The following additives must be mentioned additionally by way of example:

Examples of further antioxidants: Aliphatic or aromatic phosphites, esters of thiodipropionic acid or of thiodiacetic acid, or salts of dithiocarbamic or dithiophosphoric acid, 2,2,12,12-tetramethyl-5,9dihydroxy-3,7,1 1-trithiatridecane and 2,2,15,15-tetramethyl-S, 12dihydroxy-3,7,10,14-tetrathiahexadecane.

Examples of metal passivators, e.g. for copper, are: a) Benzotriazoles and their derivatives, e.g. 4- or 5-alkylbenzotriazoles (e.g. tolutdazole) and derivatives thereof, 4,5,6,7-tetrahydrobenzotriazole, 5, 5'-methylenebisbenzotriazole; Mannich bases of benzotriazole or tolutriazole, such as 1-[di(2-ethylhexyl)aminomethyl)tolutriazole and 1[di(2-ethylhexyl)aniinomethyl)benzotriazole; alkoxyalkylbenzotriazoles, such as 1-(nonyloxymethyl)benzotdazole, 1-(1-butoxyethyl)benzotriazole and 1-(1-cyclohexyloxybutyl)tolutriazole.

b) 1,2,4-Triazoles and their derivatives, e.g. 3-alkyl (or aryl)-1,2,4triazoles, Mannich bases of 1,2,4-triazoles, such as 1-[di(2-ethylhexyl)aminomethyl-12,4- triazole; alkoxyalkyl-1,2,4-triazoles, such as 1-(1-butoxyethyl)-1,2,4- triazole; acylated 3-amino-1,2,4-triazoles.

c) Imidazole derivatives, e.g. 4,4'-methylenebis(2-undecyl-5methylimidazole), bis[(N-methyl)imidazol-2-yllcarbinoI octyl ether.

d) Sulfur-containing heterocyclic compounds, e.g. 2-mercaptobenzothiazole, 2,5-dimercapto- 1,3,4-thiadiazole and derivatives thereof-, 3,5-bis[di(2ethylhexyl)aminomethyl]-1,3,4-thiadiazolin-2-one.

e) Amino compounds, e.g. salicylidenespropylenediamine, salicylarninoguanidine and salts thereof.

Examples of rust inhibitors are: a) Organic acids, their esters, metal salts, amine salts and ahydrides, e.g. alkyl- and alkenylsuccinic acids and partial esters thereof with alcohols, diols or hydroxycarboxylic acids, partial amides of alkyl- and alkenylsuccinic acids, 4nonylphenoxyacetic acid, alkoxy- and alkoxyethoxycarboxylic acids, such as dodecyloxyacetic acid, dodecyloxy(ethoxy)acetic acid and amine salts thereof, and also N-oleoylsarcosine, sorbitan monooleate, lead naphthenate, alkenylsuccinic anhydrides, e.g. dodecenylsuccinic anhydride, 2-carboxymethyl- I -dodecyl-3-methylglycerol and its amine salts.

b) Nitrogen-containing compounds, e.g.: 1. Primary, secondary or tertiary aliphatic or cycloaliphatic amines and amine salts of organic and inorganic acids, e.g. oil-soluble alkylammoniurn carboxylates, and also 1[N,N-bis(2-hydroxyethyl)amino]-3-(4-nonylphenoxy)propan-2-ol.

* U. Heterocyclic compounds, e.g.: Substituted imidazolines and oxazolines, 2-heptadecenyl-l-(2-hydroxyethyl)imidazoline.

c) Phosphorus-containing compounds, e.g.: Amine salts of phosphoric acid partial esters or phosphonic acid partial esters, zinc dialkyldithiophosphates.

d) Sulfur-containing compounds, e.g.: Barium dinonylnaphthalenesulfonates, calcium petroleurnsulfonates, alkylthio-substituted aliphatic carboxylic acids, esters of aliphatic 2-sulfocarboxylic acids and salts thereof.

e) Gycerol derivatives, e.g.:

Glyceryl monooleate, 1-(alkylphenoxy)-3(2-hydroxyethyl)glycerols, 1(alkylphenoxy)-3-(2,3-dihydroxypropyl)glycerols, 2-carboxyalkyl- 1,3dialkylglycerols.

Examples of viscosity index improvers are: Polyacrylates, polymethacrylates, vinylpyrrolidone-methacrylate copolymers, polyvinylpyrrolidones, polybutenes, olefin copolymers, styrenelacrylate copolymers, polyethers.

Examples of pour-point depressants are: Polymethacrylate, alkylated naphthalene derivatives.

Examples of dispersants/surfactants are: Polybutenylsuccinamides or imides, polybutenylphosphonic acid derivatives, basic magnesium, calcium and barium sulfonates and phenolates.

Examples of antiwear additives are: Sulfur- and/or phosphorus- and/or halogen-containing compounds, such as sulfurized olefins and vegetable oils, zinc dialkyldithiophosphates, alkylated triphenyl phosphates, tritolyl phosphate, tricresyl phosphate, chlorinated paraffins, alkyl and aryl di- and trisulfides, amine salts of mono- and dialkyl phosphates, amine salts of methylphosphonic acid, diethanolaminomethyltolyltriazole, di(2-ethylhexyl)aminomethyltolyltriazole, derivatives of 2,5-dimercapto-1, 3,4-thiadiazole, ethyl 3-[(bisisopropyloxyphosphinothioyl)thio]propionate, triphenyl thiophosphate (triphenyl phosphorothioate), tris(alkylphenyl)phosphorothioates and mixtures thereof, (e.g. tris(isononylphenyl)phosphorothioate), diphenyl monononylphenyl phosphorothioate, isobutylphenyl diphenyl phosphorothioate, dodecylamine salt of 3-hydroxy-1,3-thiaphosphetan 3-oxide, trithiophosphoric acid 5,5, 5-tris[isooctyl 2-acetate], derivatives of 2-mercaptobenzothiazole, such as 1-[N,N-bis(2-ethylhexyl)aminomethyl-2-mercapto-IH-1,3-benzothiazole, ethoxycarbonyl-5-octyldithiocarbamate.

Specifically preferred additional additives in lubricants are amine antioxidants, in particular mixtures of mono- and dialkylated tertbutylltert-octyl diphenylamines.

The examples which follow illustrate the invention in greater detail. Parts and percentages are by weight therein and in the rest of the description, unless otherwise indicated.

NorparO Ex 15 n-paraffinic hydrocarbon mixture from EXXON [boiling range: 245-285'C] ExxsolOO D- I 10 dearomaticized aliphatic hydrocarbon mixture, SAPO -001 partially hydrogenated, from EYMN [boiling range: 240-275'C; Mn = 206 g mol- 11 superbasic calcium salicylate from Shell Preparation Examples Example 1:

A mixture of 500 g (=- 0.737 mol) of coconut fat (MW E 678 g/mol), 403 g (4.376 mol) of glycerol, 1875 g (6.412 mol) of methyl 3-(3',5'-di-tertbutyl-4'-hydroxyphenyl)propionate and 8.7 g (0.3% by weight) of SAP&Offl is heated at 220C for 2 hours under nitrogen in a sulfonation flask provided with reflux condenser and mechanical stirrer. The reaction mixture is stirred at a temperature of 220-230'C for a further 6 hours, in the course of which methanol (and any water) is distilled off. After the mixture has cooled, 613 g of NorparO Ex 15 are added. Filtration gives 3 100 g (98 % of theory) of the product as a yellow oil with a refractive index nD 20 of 1.49 10.

Example 2:

A mixture of 109.53 g (=- 0. 162 mol) of coconut fat (MW =- 678 g/mol) and 109.53 g (=- 0. 119 mol) of castor oil (MW a 922 g/mol) in a sulfonation flask provided with reflux condenser and mechanical stirrer is admixed with 53.32 g (0.579 mol) of glycerol, 247.40 g (0.846 mol) of methyl 3-(3',5'-di-tert-butyl-4'-hydroxyphenyl)propionate and 3.96 g (0. 8% by weight) of SAPO-001, and the mixture is held under nitrogen at 180- 190C for 18 to 19 hours. Cooling and filtration. give 469 g (96% of theory) of the product as a yellow oil with a refractive index nD 20 of 1. 4999.

Example 3:

A mixture of 80.0 g ( 0. 118 mol) of coconut fat (MW -= 678 g/mol) and 20. 0 g (-= 0.022 mol) of castor oil (MW -= 922 g/mol) in a sulfonation flask provided with reflux condenser and mechanical stirrer is admixed with 75. 77 g (0.823 mol) of glycerol, 355.21 g (1.215 mol) of methyl 3-(3',5'-ditert-butyl-4'-hydroxyphenyl)propionate and 3.71 g (0.76% by weight) of SAPO-001, and the mixture is held under nitrogen at 180-190'C for 18 to 19 hours. Cooling and filtration give 478 g (98% of theory) of the product as a yellow syrup with a refractive index nD 20 of 1.5114.

Example 4:

A mixture of 80.0 g (=- 0. 118 mol) of coconut fat (MW a 678 g/mol) and 20.0 g (E 0.022 mol) of castor oil (MW =- 922 g/mol) in a sulfonation flask provided with reflux condenser and mechanical stirrer is admixed with 75. 77 g (0.823 mol) of glycerol, 355.21 g (1.215 mol) of methyl 3-(3,5'-di- tert-butyl-4'-hydroxyphenyl)propionate and 3.71 g (0.76% by weight) of SAPO-00 1, and the mixture is held under nitrogen at 180-190C for 18 to 19 hours. After the mixture is cooled, 121.4 g of NorparO Ex 15 are added. Filtration gives 594.9 g (98% of theory) of the product as a yellow oil with a refractive index nD 20 of 1.4913.

Example 5:

A mixture of 100 g ( 0. 147 mol) of coconut fat (MW =- 678 g/mol), 80.6 g (0,875 mol) of glycerol, 324 g (1.294 mol) of methyl 3-(3'-tert-butyl-S'methyl-4'-hydroxyphenyl)propionate and 7.62 g (0. 16% by weight) of lithium methanolate (10% strength solution in methanol) is heated at 1. 80C for 1 hour under nitrogen in a sulfonation flask provided with reflux condenser and mechanical stirrer. The reaction mixture is stirred at this temperature for a further 12 hours, in the course of which water and methanol are distilled off. Extractic with citric acid and subsequent washing with warm water give 448 g (99% of theory) of the product as a yellow syrup with a refractive index nD 20 of 1.5147.

Example 6:

g (=- 0. 147 mol) of coconut fat (MW =- 678, g/mol), 80 g (0.869 mol) of glycerol and 347.5 g (1.281 mol) of methyl 3-(3',5-di-tert-butyl-4'hydroxyphenyl)propionate are melted at 1OWC under a nitrogen atmosphere in a sulfonation flask provided with reflux condenser and mechanical stirrer. 122.5 g of NorparIO Ex 15 and 1.74 g (0.3% by weight) of SAPO - 001 are added to the reaction mixture, which is stirred at a temperature of 180-190'C for a further 15 hours, in the course of which water and methanol are distilled off. Cooling and filtration give 614.5 g (98% of theory) of the product as a yellow oil with a refractive index nD 20 of 1. 4913.

Example 7:

456.78 g (5.306 mol) of methyl acrylate are added over 1 hour to a mixture of 1001.3 g (4.835 mol) of 2,6-di-tert-butylphenol and 27.31 g (0. 146 mol) of 30% strength potassium hydroxide solution, this addition taking place in a sulfonation flask provided with reflux condenser and mechanical stirrer, under vacuum and at 1 ITC. After a reaction time of one hour and following the removal of excess methyl acrylate by distillation, 372.5 g (=- 0.549 mol) of coconut fat (MW =- 678 g/mol) and 302.3 g (3.282 mol) of glycerol are added. Over the course of 2 hours under vacuum the mixture is heated to a temperature of 19TC. The reaction mixture is stirred at this temperature for 3 hours more, in the course of which water and methanol are distilled off. After the mixture has been cooled to room temperature, 456 g of NorparO Ex 15 are added. Extraction with citric acid and subsequent washing with warm water give 2263 g (97% of theory) of the product as a reddish oil with a refractive index nD20 of 1.4905.

Example 8:

79.36 g (0.922 mol) of methyl acrylate are added over 1 hour to a mixture of 173.9 g (0.843 mol) of 2,6-di-tert-butylphenol and 4.75 g (0.025 mol) of 30% strength potassium hydroxide solution, this addition taking place in a sulfonating flask provided with reflux condenser and mechanical stirrer, under vacuum and at 1 WC. After a reaction time of one hour and following the removal of excess methyl acrylate by distillation, 109.53 g (=- 0. 162 mol) of coconut fat (MW =- 678 g/mol), 109.53 g ( 0. 119 mol) of castor oil (MW -= 922 g/mol) and 53.32 g (0.579 mol) of glycerol are added. Over the course of 18 to 19 hours, the reaction mixture is held at a temperature of 180 to 190C under a nitrogen atmosphere. Cooling and filtration give 469 g (97% of theory) of the product as a orange-coloured oil with a refractive index nD 20 of 1.4999.

Example 9:

116.25 g (1.350 mol) of methyl acrylate are added over 1 hour to a mixture of 254.83 g (1.235 mol) of 2,6-di-tert-butylphenol and 6.95 g (0. 037 mol) of 30% strength potassium hydroxide solution, this addition taking place in a sulfonating flask provided with reflux condenser and mechanical stirrer, under vacuum and at 1 ITC. After a reaction time of one hour and following the removal of excess methyl acrylate by distillation, 80.0 g (=- 0. 118 mol) of coconut fat (?YW =- 678 g/mol), 20.0 g (a 0.022 mol) of castor oil (MW =- 922 g/mol) and 75.77 g (0.823 mol) of glycerol are added. Over the course of 18 to 19 hours, the reaction mixture is held at a temperature of 180 to 190C under a nitrogen atmosphere. After the mixture has been cooled to room temperature, 121.4 g of Norpar@ Ex 15 are added. Filtration gives 594.9 g (98% of theory) of the product as a reddish oil with a refractive index nD 20 of 1.4913.

Example 10:

106.05 g (1.232 mol) of methyl acrylate are added over 1 hour to a ndxture of 185.06 g (1. 127 mol) of 2-tert-butyl-6-methylphenol and 6.34 g (0.034 mol) of 30% strength potassium hydroxide solution, this addition taking place in a sulfonating flask provided with reflux condenser and mechanical stirrer, under vacuum and at 1 WC. After a reaction time of one hour and following the removal of excess methyl acrylate by distillation, 100.0 g (-= 0. 147 mol) of coconut fat (MW -= 678 g/mol) and 8 1.0 g (0.880 mol) of glycerol are added. Over the course of 1 hour under a nitrogen atmosphere the mixture is heated to a temperature of 18WC. The reaction mixture is stirred at this temperature for 9 hours more, in the course of which water and methanol are distilled off. The cooled, crude product is taken up in toluene and water and the phases are neutralized with citric acid. After multiple washing with water the organic phase is dried and is subsequently concentrated by evaporation, giving 387.5 g (96% of theory) of the product as a orange-coloured syrup with a refractive index nD 20 of 1.5148.

Example_ A: "Deposit and Oxidation Panel TesC (DOPT) The deposit and oxidation panel test (DOPT) is a variant of a test method for engine oils, in particular for diesel engine oils, which has been described by G. Abellaneda et al., HIrd Symposium CEC, 1989, 6 1, New Cavendish Street, London 8AR, England. The suitability of the oils with stabiliser for preventing deposits on the pistons is tested.

The test time is 20 hours, the panel temperature 260C and the oil flex 1 mIlminutes. The humid atmospheric environment is enriched with 260 ppm of N02 and 26 PPM Of S02. After the test, the metal panel onto which the oil drops is weighed and assessed visually. The lower the weight, the better. The lubricating oil used is a commercial CD oil which is diluted with the basic oil STANCO 150. The stabilisers according to the invention are admixed to this prepared oil in amounts of 0.6 % by weight based on the oil, and this is subjected to a DOPT test.

The products according to the invention exhibit a good stabilising effect.

Example B: Test for antiwear protection.

To test the stabilisers according to the invention for their suitability as antiwear protection agents, the ASTM standard method D 2783-81 using the Shell four ball apparatus is used. The basic oil used is BB oil [Mobil Stock, carbon (aromatic) 6.5 %; carbon (aliphatic) 72 %; carbon (naphthylic) 21.5 %]. The parameter measured during one hour is the mean wear scar diameter in mm. at a load of 40 kg. The stabilisers according to the invention are added to this oil in an amount of 1.0 % by weight. The lower the values, the better the stabilising effect.

The products according to the invention exhibit a good stabilising effect.

Claims

WHAT IS CLAINffiD IS:

1. A product obtainable by reacting components a), b), c) and d), where component a) is a compound of the formula I or a n-dxture of compounds of the formula I, component b) is a compound of the formula H or a mixture of compounds of the formula II, component c) is a compound of the formula HI or a mixture of compounds of the formula HI and component d) is a compound of the formula IV or a mixture of compounds of the formula iv, CH2-OZ HO R12 0 XMa kCH-u4)k (R15)S Q-C-O-R17 A-C8-C30alkyl 1, n -1r'2-u4 M (111) UID (rv) in which, in the compound of the formula I, Y independently of one another is OH, (HOCH2CH2)2N- or -HNR1 and CH3 CH3 R, is hydrogen, Cl-CIgalkyl, CS-CI2cycloalkyl, R27 N -, C3-C6alkertyl, CH3 H3 C7-C9phertylalkyl, phenyl, or phenyl which is substituted by 1 to 3 radicals A,, the radicals A, independently of one another being ClC12alkyl, halogen, hydroxyl, methoxy or ethoxy, in which R2 is hydrogen, Cl-C8alkyl, 0, OH, NO, -CH2W, Cl-CI8alkoxy, CS- CUCYCloalkoxy, C3-C6alkenyl, C7-C9phenylalkyl or C7-C9phenylalkyl which is mono-, di- or trisubstituted on the phenyl ring by Cl-C4alkyl, or R2 is furthermore Cl-C8acyl or HOCH2CH2-, and a is the number 1, 2, 3, 4 or 6, where, if Y is OH and a is 1, CH3 CH3 X is Cl-c45alkyl, C3-CI8alkenyl, -CH2CH2TI(CH2CH20)bR4 or R27 N in CH3 CH3 which R2 is as defined above, and T, is oxygen, sulfur or / N - R5, R4 is Cl-C20alkyl, b is an integer ranging from 0 to 10 and RS is hydrogen, C 1 -C 1 8alkyl or phenyl, or, if Y is OH and a is 2, X is -CH2CH2T2(CH2CH20)bCH2CH2-, in which b is as defined above, -CH2CH2- N / R6, -CcH2d- CH3 CH3 9 ---CH2CH2 - N ? CH 3 CH3 CH3 CH3 CH3 CH3 N - (cH2)- N -CH2-CH=CH-CH2- --C CH3 d CH3 CH3 CH3 0 0 C - C - NH-CH2CH2- or 1 CH3 1 ' -CH2CH20 -0- C OCH2CH2-, in which CH3 7 T2 is oxygen, sulfur, / N - R5 or - S - Cl - S - and R5 is as defined above, M8 R6 is hydrogen, C 1 -C 1 8alkyl or phenyl, c is an integer ranging from 2 to 10, d is an integer ranging from 2 to 6 and R7 and R8 independently of one another are hydrogen, C 1 -C 1 8alkyl or phenyl, or R7 and R8 together with the C atom to which they are bonded form a C5CI2cycloalkylidene ring, or, if a is 3, X 'S C3-C 1 Oalkanetriyl or N(CH2CH2-)3, or, if Y is OH and a is 4, 1 X is C4-Cloalkanetetrayl, (-CH2-M-2)2U' -CH2 0 0 CH2- -H2 CH2- -CH 0 -CH -CH-CH -CH CH R9--NH-9--NH--Rg 2 2-0 2- or in which R9 is Cl-COlkyl, or, if Y is OH and a is 6, -CH2 CH2- -CH2 CH2- -CH2 0 0 CH2- -CH2 0 111 CH2 1 1 1 Xis -CH2-C-NH-C-C-NH-C-CH2-or C6-Cloalkanehexayl, or, -CH2 CH2- -CH2 CH2- if Y is HNRI and a is 1, X is Cl-CI8alkyl, C3-CI8alkenyl, CS-CI2cycloalkyl, C7-C9phenylalkyl, phenyl, CH3 CH3 Rr N in which R2 is as defined above or X is furthermore W(CH2)e_ CH3 CH3 or X together with R, is a group of the formula -CH2CH2CH2CH2CH2- or - CH2CH2OCH2CH2-, in which RIO is hydrogen or methyl and e is 2 or 3, or, if Y is -HNR1 and a is 2, RjO X is -CfH2f-, 1 1-1 t5 /0"" H 1 -(CH2CH2N ± CH2CH2- or -(CH2)6-NW(CH2)6-, in which 9 f is an integer ranging from 2 to 10 and g is an integer ranging from 1 to 6, and, in the compound of the formula H, 0 Z is hydrogen or a group of the formula 11 -(ChH2h0)i-C-n11 and k is an integer ranging from 0 to 6, in which h is 2 or 3, i is an integer ranging from 0 to 12 and R, j is C8-C30alkyl, CS- C30alkenyl which may be straight-chain or branched and whose chain(s) may have not more than three double bonds at any desired point on said chain(s), C8-C30hydroxyalkyl or C8-C30hydroxyalkenyl, whose alk(en)yl chain may be straight-chain or branched and whose chain(s) may have at least one hydroxyl function at any desired point on said chain(s), with the proviso that the compound of the formula H 0 11 has a group (Chn2hu)i-.,-nll; in the compound of the formula M, R12 is Cl-CI8alkyl, Cs-CI2cycloalkyl, phenyl or C7-C9plienylalkyl, R15 is hydrogen, Cl-CI8alkyl, CS-C12CYcloalkyl, phenyl or C7-C9phenylalkyl, s is 0, 1 or 2, Q is -CmH2m-, -CH2-CH-, -CH2-S-(CH2)t- or 1 R16 is as defined above, m is an integer ranging from 0 to 3, R16'S Cl-C8alkyl, R15 HO- H3C - C CH3 H3C 1 '-. CH3 k; - UM2' in which RIS t is 1 or 2, and n is an integer ranging from 1 to 6, where, if n is 1, R17 is hydrogen, Cl-C45alkyl, CS-C12CYCloalkyl, C2-CI8alkenyl, a monovalent radical of a CH20H CH3 CH3 1 hexose, a monovalent radical of a hexitol, -CH2-;-;M2UM Y R2 - N -, in which 1 CH20H CH3 H3 R2 is as defined above, or furthermore R17 is -CH2CH2-T3-RI9 or f (CH2)p oq CH2)pOR19, in which T3 is oxygen, sulfur or N - R22 R23 R240 R19 is 1 1 11 or CH-CH-C-O-R25 R12 CH2 -C- OH, in which R12 and R15 are as defined R15 above, or R19 is furthermore hydrogen, Cl-CMalkyl, phenyl, CS- CI2cycloalkyl or 0 11 in which -CH2-C-O-R251 p is an integer ranging from 2 to 4, q is an integer ranging from 2 to 20, R22 is Cl-CISalkyl, phenyl or phenyl which is substituted by 1 to 3 radicals A,, in which the radicals A, independently of one another are Cl-C12alkyl, halogen, hydroxyl, methoxy or ethoxy, or R22 is furthermore CS-C8cycloalkyl, R23 and R24 independently of one another are hydrogen or methyl, with the proviso that R23 and R24 are not simultaneously methyl; R25 is hydrogen or Cl-C24alkyl, or, if n is 2, -CH2 1 R17 is a divalent radical of a hexose, a divalent radical of a hexitol, - C"2-;-;M2UM, 1 "2UM R18 1 R20 defined above, CH3 C H.3 2CH2-T CH CH2- N -CH 4-M2CH2-, -CH2-CH=CH-CH2-, -CH2-C=C-CH2- 2 CH3. CH3 CH3 CH3 N - CHr CH= CH- CH2- N CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH,1 CH3 CH3 3 CH3 N - (CH2) 4 N \ 00 0 11 or in which -CH2-CH2-NH-C-C-NH-CH2-CH2- 01 1 R18 and R20 independently of one another are hydrogen or Cl-C12alkyl or together are the radical -CH2CH2CH2CH2CH2-, r is an integer ranging from 2 to 10, 7 T4 is sulfur, / N - R26 or - S - Cl - S in which R7 and R8 are as defined above, and R8 R26 is hydrogen, Cl-CI8alkyl, phenyl or phenyl which is substituted by 1 to 3 radicals A,, in which the radicals A, are as defined above in formula I, or R26 is furthermore CH3 CH3 CS-C8CYCloalkyl or R2- N ined above, or, in which R2 is as def CH3 CH3 if n is 3, R17 is a trivalent radical of a hexose, a trivalent radical of a hexitol, 1 -CH2 CH2CH2- 1 1 or -';"2-t;-R27, in which -CH2CH2-N-CH2CH2- ' CH3-CH-CH2-N-CH2-CH-CH3 1 1 1 -CH2 R27 is hydrogen, -CH20H, Cl-C4alkyl, Cl-CI8alkylamido or 0 R12 j 11 -HN-C-0 -o OH, in which Q, R12 and RIS are as defined above, or, R15 if n is 4, R17 is a tetravalent radical of a hexose, a tetravalent radical of a hexitol, 1 - H2 - 1 C4-Cloalkanetetrayl, CH3-CH-CH / 1 2 -CH2 0 ,,,. or, CH2 if n is 5, \ N-CH2CH2-N 'r'2-.,rl-k.,H3 CH 0 CH2-CH-CH3 or 1 R17 is a pentavalent radical of a hexose or a pentavalent radical of a hexitol, or, if n is 6, -CH2 CH2- 1 1 R17 is a hexavalent radical of a hexitol or and, -C 1 H2 C 1 H2- in the compound of the formula IV, A is hydrogen, C I -C4alkyl or phenyl.

2. A product according to claim 1, in which, in the compound of the formula III, s is the number 1 or 2.

3. A product according to claim 1, in which, in the compound of the formula 1, Y independently of one another is OH, (HOCH2CH2)2N- or -HNRI and CH3 CH3 R, is hydrogen, Cl-Cloalkyl, CS-C7CYCloalkyl, R27 -C6alkenyl, benzyl C3 CH3 H3 or phenyl, in which R2 is hydrogen, Cl-C4alkyl, OH, -CH2CN, C6-CI2alkoxy, C5-C8CYCloalkoxy, allyl, benzyl, acetyl or HOCH2CH2and a is the number 1, 2, 3, 4 or 6, where, if Y is OH and a is 1, CH3, CH3 X'S Cl-C30alkyl, C3-CI8alkenyl, -CH2CH2TI(CH2CH20)bR4 or R27 Nr in t^w 3 H3 which R2 is as defined above, and TI is oxygen, sulfur or / N - R5, R4 is Cl-Cloalkyl, b is an integer ranging from 0 to 10 and RS is hydrogen, Cl-CI()alkyl or phenyl, or, if Y is OH and a is 2, X is -CH2CH2T2(CH2CH20)bCH2CH2-, in which b is as defined above, -CH2CH2-N / R6 -CcH2d-- CH, CH3 CH3 --- CH2CH2 - N:Y- CH3 CH3 CH 9 J CH3 CH3 NC (CH2)- N -CH H3 d CH3 1 Y_ 2-CH=CH-CH2- CH3 CH3 0 0 or CH3 1 -CH2CH20 c, OCH2CH2-, in which CH3 7 T2 is oxygen, sulfur, / N - R5 or - S - C, - S - and R5 is as defined above, H8 R6 is hydrogen, Cl-Cloalkyl or phenyl, c is an integer ranging from 2 to 10, d is an integer ranging from 2 to 6 and R7 and R8 independently of one another are hydrogen, Cl-Cloalkyl or phenyl, or R7 and R8 together with the C atom to which they are bonded form a CS-C7CYCloalkyl ring, or, if Y is -HNRI and a is 1, CH3 CH3 Xis Cl-Cloalkyl, C3-C18alkertyl, CS-C7eycloalkyl, benzyl, phenyl, R2-N in CH3 H3 R10 which R2 is as defined above, or X is furthermore ( W(CH2)e-, or X together with R, is a group of the formula -CH2CH2CH2CH2CH2- or -CH2CH2OCH2CH2-, in which RIO is hydrogen or methyl and e is 2 or 3, and, in the compound of the formula H, 0 11 H,, and Z is hydrogen or a group of the formula -(%..hn2hJ)1-l k is an integer ranging from 0 to 4, in which h is 2 or 3, i is an integer ranging from 0 to 6 and R, 1 is C8-C20alkyl, C8-C20alkertyl which may be straight-chain or branched and whose chain(s) may have not more than three double bonds at any desired point on said chain(s), C8-C2Ohydroxyalkyl or C8-C2Ohydroxyalkenyl, whose alk(en)yl chain may be, straight-chain or branched and whose chain(s) may have at least one hydroxyl function at any desired point on said chain(s), with the proviso that the compound of the formula 11 0 comprises a group H 11 (Ch 2hO)i-C-Rl in the compound of the formula III, 1; R12'S Cl-C6alkyl, C5-C7cycloalkyl, phenyl or benzyl RIS is hydrogen, Cl- C6alkyl, C5-C7cycloalkyl, phenyl or benzyl, s is 1 or2, R15 HO Q is -CInH2.,-, -CH2,CH-, -CH2-S-(CH2)t- or 1 H3C-C CH3 R16 H3C/ " CH3 is as defined above, m is an integer ranging from 0 to 3, R16 is Cl- C4alkyl, t is 1 or 2, and n is an integer ranging from 1 to 6, where, if n is 1, in which R15 R17 is hydrogen, Cl-C30alkyl, CS-C7cycloalkyl, C2-CI8alkertyl, a monovalent radical of a - 74 CH20H CH3 CH3 hexose, a monovalent radical of a hexitol, -CH2--CH20H, R2- N - in which 1 CH20H CH3 CH.3 R2 is as defined above, or furthermore R17 is -CH2CH2-T3-RI9 or f (CH2)p oq (CH2)pOR19, in which T3 is oxygen, sulfur or / N-R22 R23 F124 0 R19 is 1 1 11 CH-CH-C-O-R25 R12 or - CH2 -C OH in which R12 and R15 are as defined R15 above, or R19 is furthermore hydrogen, Cl-C18alkyl, phenyl, CSC7cycloalkyl or 0 11 in which -CH2-C-O-R25' p is an integer ranging from 2 to 4, q is an integer ranging from 2 to 20, R22 is Cl-Cloalkyl, phenyl or CS- C8cycloalkyl, R23 and R24 independently of one another are hydrogen or methyl with the proviso that R23 and R24 are not simultaneously methyl; R25 is hydrogen or Cl-C18alkyl, or, if n is 2, -CH2 1 R17 is a divalent radical of a hexose, a divalent radical of a hexitol, - CH2-;-';M2UM, 1 ;"2Ul R 118 C -CrH2r-, f (CH2)p oq CH2)p-, in which p and q are as R20 defined above, -CH2CH2-T4-CH2CH2-, -CH2-CH=CH-CH2-, CH3 CH3 -CH2-C=-C-CH2CH2CH2- N)_ CH3 CH3 -75 CH3 CH3 CH., CH3 CH3 CH3 CH3 CH3 - CH- CH= CHCH2- N -'C N CH3 hN CH (CH2)-- N CH CH3: 3 CH3 3 H3 CH3 CH3 00 0 -CH2-CH2-M-C-C-NH-CH2-CH2- or 0 in which R18 and R20 independently of one another are hydrogen or Cl-C6alkyl or together are the radical -CH2CH2CH2CH2CH2-, r is an integer ranging from 2 to 10, 7 T4 is sulfur, / N - R26 or - S - C, - S in which R7 and R8 are as defined above and N CH3 CH3 R26 is hydrogen, Cl-Cloalkyl, phenyl, CS-C8cycloalkyl or R2 - N -, in which R2 CH3 H3 is as defined above.

4. A product according to claim 1, in which, in the compound of the formula I, Y independently of one another is OH, (HOCH2CH2)2N- or -HNRI and CH3 CH3 R, is hydrogen, Cl-C4alkyl or R2 - N -, in which CH3 H3 R2 is hydrogen, Cl -C4alkyl, OH, allyl, benzyl, acetyl or HOCH2CH2- and a is the number 1, 2, 3, 4 or 6, where, if Y is OH and a is 1, CH3 CH3 X is Cl-C18alkyl, CYCI8alkertyl, -CH2CH2TI(CH2CH20)bR4 or R2- N in CH3 CH3 which R2 is as defined above, and TI is oxygen, R4 is Cl-C4alkyl and b is an integer ranging from 0 to 10, or, if Y is OH and a is 2, X 'S -CH2CH2T2(CH2CH20)bCH2CH2-, in which b is as defined above, or furthermore X CH3 CH3 is -CcH2d-, T2 is oxygen, sulfur or / N - R5, R5 is hydrogen, b is the number 0 or 1 and ---CH2CH2 - N or -CH2-CH=CH-CH2-, in which CH3 CH3 c is an integer ranging from 2 to 8, or, if a is 3, 1 X iS -CH2-CH-CH2- or N(CH2CH2)3, or, if Y is OH and a is 4, CH2- 1 1 1 C, H2 X is -CH2- 1;-M2-, (-CM2-M-;M2)20 or --CH 2-;"-;12-u-CH-CH2-, or, CH2- if Y is OH and a is 6, -CH2 CH2 1 1 1 1 1 1 X is or -CH2-CH-CH-CH-CH-CH2 - or, 1 1 -CH2 CH2- if Y is -HNRI and a is 1, CH3 CH3 XisC,-Cloalkyl,C3-CI8alkenyl,CS-C7cycloalkylor R27N where R2 is as CH3 H3 defined above, or, if Y is -HNRI and a is 2, X is -CfH2f- in which f is an integer ranging from 2 to 10 and, in the compound of the formula H, 0 11 Z is hydrogen or a group of the formula -(ChH2hO)i-C-Rl 1 and k is 1, 2 or 3, h is 2 or 3, i is an integer ranging from 0 to 4 and R, 1 is C8-C20alkyl, C8-C20alkenyl which may be straight-chain or branched and whose chain(s) may have not more than three double bonds at any desired point on said chain(s), C8-C2Ohydroxyalkyl or C8-C2Ohydroxyalkenyl, whose alk(en)yl chain may be straight-chain or branched and whose chain(s) may have at least one hydroxyl function at any desired point on said chain(s), with the proviso that the compound of the formula II 0 comprises a group 11 -(ChH2hO)i-C-Rl in the compound of the formula M, 1; R12'S Cl-C6alkyl or CS-C7cycloalkyl, RIS is hydrogen, Cl-C6alkyl or CS- C7cycloalkyl, s is 1 or 2, Q is -CmH2m- or -CH2-CH1 R16 m is an integer ranging from 0 to 3, R16 is Cl-C4alkyl and n is an integer ranging from 1 to 6, where, 9 if n is 1, R17 is hydrogen, Cl-CI8alkyl, C5-C7cycloalkyl, C2-CI8alkenyl, a monovalent radical of a CH20H 1 hexose, a monovalent radical of a hexitol, -CH2-C-CH20H or 1 CH20H R2 is as defined above, or furthermore R17 'S i (CH2)p oq CH2)pOR, gin which R19 is hydrogen, Cl-CI8alkyl or C5-C7CYCloalkyl, in which p is an integer ranging from 2 to 4, q is an integer ranging from 2 to 10, or, if n is 2, CH3 CH3 R27- in which CH3 H3 -CH e 1 R17 is a divalent radical of a hexose, a divalent radical of a hexitol, - CH2-';-k;M2U" 1 2UM -CrEI2C, i (CH2)p oq CH2)p-, in which p and q are as defined above, CH3 CH3 -CH2CH2-T4-CH2CH2-, or - CH2CH2- N in which CH3 CH3 r is an integer ranging from 2 to 10, T4 is sulfur or / N R26 and R26 is hydrogen, CI-Cloalkyl or C5- C8Cycloalkyl, or, if n is 3, CH2CH2- R17 is a trivalent radical of a hexose, a trivalent radical of a hexitol, 1 -CH2CH2-N-CH2CH2- or CH3-CH-CH2-N-CH2-CH-CH3 1 1 if n is 4, or, -CH2 1 R17 is a tetravalent radical of a hexose, a tetravalent radical of a hexitol, or 1 UM2 1 U"3-CH-CH2 1 CH2-C"-;"3 CH3-CH-CH2 CH2-CH-CH3 1 1

5. A product according to claim 1, in which, in the compound of the formula I, Y independently of one another is hydroxyl or -NH2 and a is an integer ranging from 1 to 4, where, if a is 1, CH3 CH3 X is R- N and CH3 H3 R2 is hydrogen, methyl or HOCH2CH2-, or, if Y is OH and a is 2, CH3 CH3 X is -CH2CH2T2(CH2CH20)bCH2CH2-, -CcH2d- or ---CH2CH2 - N CH3 H3 in which T2 is oxygen, sulfur or \ N - R5 R5 is hydrogen, b is the number 0 or I and c is the number 2, 3 or 4, or, if Y is OH and a is 3, X is or, if Y is OH and a is 4, CH2- 1 X is -CH2- 1;--;M2- and, CH2- in the compound of the formula H, 0 11 Z is hydrogen or a group of the formula -C-R 11, k is the number 1 and R, 1 is C8-C20alkyl, C8-C20alkenyl which may be straight-chain or branched and whose chain(s) may have not more than three double bonds at any desired point on said chain(s), C8-C2Ohydroxyalkyl or C8C2Ohydroxyalkenyl, whose alk(en)yl chain may be straight-chain or branched and whose chain(s) may have at least one hydroxyl function at any desired point on said chain(s), with the proviso that the compound of the formula H 0 11 comprises a group -C-R,,and, in the compound of the formula IH, R12 'S tert-butyl, RIS is Cl-C4alkyl and is bonded in the ortho-position relative to the OH group, s is the number 1, Q is -C.,,H2,,,- and is bonded in the para-position relative to the OH group, where, m is the number 2, n is 1 and R17 is Cl-C4alkyl.

6. A product according to claim 1, in which, in the compound of the formula M, R12 is Cl-C4alkyl or cyclohexyl, RIS 'S Cl-COlkyl or cyclohexyl and is bonded in the ortho-position relative to the OH group, s is the number 1, Q is -C.H2.- and is bonded in the para-position relative to the OH group, where m is an integer ranging from 0 to 3 and n is an integer ranging from 1 to 4, where, if n is 1, CH20H 1 R17 is hydrogen, Cl-Cloalkyl, cyclohexyl, C2-CI8alkenyl or -CH2-- M2UM, or, 1 CH20H if n is 2, -CH2 I R17 is --;"2-;--;M20H, -CAC (CH2)p CH2)p-or -CH2CH2-T4-CH2CH2in Oq which p is an integer ranging from 2 to 4, q is an integer ranging from 2 to 10, r is an integer ranging from 2 to 6, T4 is sulfur or / N R26 and R26 is hydrogen or Cl -C4alkyl, or, if n is 3, CH2CH2- R17'S or CH2CH2-N-CH2CH2- CH3-CH-CH2-N-CH2-CH-CH3 1 1 or, if n is 4, 1 C12-A-1-;M3 -CH2 CH R17'S -CH2-;-12- or N-CH2CH2-N CH -CH-CH / \ CH2-CH-CH3 3 1 2 1

7. A product according to claim 1, in which, in the compound of the formula lH, R12 '

S tert-butyl, RIS 'S Cl-C4alkyl and is bonded in the ortho-position relative to the OH group, s is the number Q is -CmH2m- and is bonded in the para-position relative to the OH group, in which is the number 2 and is an integer 1, 2 or 4, where, if n is 1, R17 is Cl-COlkyl, or, if n is 2, R17 is f (CH2) poq CH2)p- or -CH2CH2-T4-CH2CH2-, in which p is the number 2, q is the number 2 and T4 is sulfur, or, if n is 4, -CH2 1 R17 is -CH2--;-;"21 -;M2 8. A product according to claim 1, in which the compound of the formula 1 is pentaerythritol, thiodiethylene glycol, 1,4-butanediol, 1,2- propanediol, diethylene glycol, triethylene glycol, diethanolamine or glycerol, the compound of the formula H is coconut fat, rapeseed oil, sunflower oil, soya oil or castor oil, the compound of the formula M is methyl 3-(3',5'-di-tert-butyl-4- hydroxyphenyl)propionate, methyl 3-(3'-tert-butyl-4'- (CH3) hydroxy-5'-methylphenyl)propionate or 3 0 11 HC CH2-S-CH2- C - 0 - CH3 and the (CH3)3C compound of the formula IV is C9-Cl3alkylbenzene or an alkane having 12 to 20 carbon atoms.

9. A product according to claim 1, in which the molar quantitative ratio of components a), b), c) and d) is 0. 1: LO. 1:0. 1 to 15:1:30: 10.

10. A product according to claim 1, in which the amount by weight of active group E-2 R12 HO 0

11 (R15) 0 C - (E-2) is 5 to 95 % by weight.

S 11. A product according to claim 1, where the compound of the formula I is glycerol.

12. A product according to claim 1, where the compound of the formula H is coconut fat, rapeseed oil, sunflower oil or castor oil.

13. A product according to claim 1, where the compound of the formula H is coconut fat.

14. A product according to claim 1, where component d) is an alkane having 12 to 18 carbon atoms.

15. A product according to claim 1, where component d) is a C9CI3alkylbertzene.

16. A product according to claim 1, where components a) and b) are reacted with methyl 3-(3',5'-di-tert-butyl-4'-hydroxyphenyl)propionate in a C12-CI8alkane.

17. A product obtainable by reacting the components a), b) and c) defined in claim 1, where all three components are initially introduced and are reacted simultaneously.

18. A product according to claim 17, where additionally the component d) defined in claim 1 is added.

19. A product according to claim 18, where component d) is added after the reaction of components a), b) and c).

20. A product obtainable by reacting components a), b), e) and f), components a) and b) being as defined in claim 1 and e) corresponding to one or more compounds of the formula V R12 HO 11 (V) (R15 S and f) corresponding to one or more compounds of the formula VI 0 11 HIC= C - C 0 - R28 (V,) 1 K X in which R28 is hydrogen or C,-CI8alkyl and R,, is hydrogen or methyl, and R12, RIS and s are as defined in claim 1.

21. A product according to claim 20, in which R28 is C,-C4alkyl.

22. A product according to claim 20, where additionally the component d) defined in claim 1 is added.

23. A product according to claim 20, where component e) is 2,6-di-tertbutylphenol and component f) is methyl acrylate.

24. A composition comprising cc) an organic material subjected to oxidative, thermal o- light-induced degradation and 0) at least one product as claimed in claim 1, 17 or 20.

25. A composition according to claim 24, in which component cc) is a fuel, a lubricant, a hydraulic fluid, a metal-working fluid or a synthetic polymer.

26. A composition according to claim 24, in which component a) is a hydrocarbon fuel, an oxygen-containing fuel or a mixture of these.

27. A composition according to claim 24, in which component cc) is a lubricant from the series of the mineral oils, the synthetic oils or a mixture of these.

28. A composition according to claim 24, in which component cc) is a synthetic polymer.

29. A composition according to claim 24, in which component a) is a polyolefin or a styrene copolymer.

30. A composition according to claim 24 which contains, in addition to components cc) and 0), additional further additives.

31. A composition according to claim 30 which contains amine antioxidants as further additives.

32. The use of a product according to claim 1, 17 or 20 for stabilising fuels, polymers and oils against oxidative, thermal or light-induced degradation..

33. A process for stabilising fuels, polymers or oils against oxidative, thermal or light-induced degradation, which comprises incorporating a product according to claim 1, 17 or 20 into these polymers or oils.