BR112021016271B1 - ADDITIVE MIXTURE, COMPOSITION, METHODS FOR STABILIZING AN ORGANIC MATERIAL SUSCEPTIBLE TO OXIDATIVE, THERMAL OR LIGHT-INDUCED DEGRADATION AND FOR IMPROVING FLAME RETARDATION, AND, PROCESS - Google Patents

Abstract

ADDITIVE MIXTURE, COMPOSITION, METHODS FOR STABILIZING AN ORGANIC MATERIAL SUSCEPTIBLE TO OXIDATIVE, THERMAL OR LIGHT-INDUCED DEGRADATION AND FOR IMPROVING FLAME RETARDATION, AND, PROCESS. The present invention relates to mixtures of sterically hindered amines of formulas (1) and (2), wherein at least one of the radicals Z1, Z2, Z3, Z4, Z5 and Z6 is C1-C18 alkyloxy or C5-C7 cycloalkyloxy and the remainder of the radicals Z1, Z2, Z3, Z4, Z5 and Z6 are hydrogen, hydroxy, C1-C18 alkyloxy or C5-C7 cycloalkyloxy, and at least one of the radicals Y1, Y2, Y3, Y4, Y5 and Y6 is a group of the formula -CH2-CH=CH-R and the remainder of the radicals Y1, Y2, Y3, Y4, Y5 and Y6 are hydrogen or a group of the formula -CH2-CH=CH-R, and the other substituents are in the defined manner According to the present invention, methods for stabilizing an organic material, and a process for preparing compounds of formula (1).

Description

[001] The present invention relates to mixtures of sterically hindered amines of formulas (1) and (2), as defined herein above, methods for stabilizing an organic material, and a process for preparing specific compounds of the formula ( 1).

[002] Sterically hindered amines are known to be efficient stabilizers for organic materials against the harmful effect of light and heat - especially for synthetic polymers such as polyolefins. For example, agricultural films produced from polyolefins are stabilized by sterically hindered amine stabilizers, since light transmission has a major impact on crop growth and sustainable light transmission depends on the long-term stability of the film.

[003] There is still a need for more sterically hindered amine stabilizers, and mixtures thereof, which provide a further improvement in the long-term stabilization of organic materials.

[004] The present invention relates in particular to an additive mixture comprising a compound of formula (1) and a compound of formula (2) wherein R1, R2, R3, R4, R'1, R'2, R'3 and R'4 are independently of each other hydrogen or C1-C18 alkyl, X1 and X'1 are independently of each other C2- alkylene C12 or hydroxyl-substituted C3-C12 alkylene; at least one of the radicals Z1, Z2, Z3, Z4, Z5 and Z6 is C1-C18 alkyloxy or C5-C7 cycloalkyloxy and the remainder of the radicals Z1, Z2, Z3, Z4, Z5 and Z6 are independently of each other hydrogen, hydroxy , C1-C18 alkyloxy or C5-C7 cycloalkyloxy, at least one of the radicals Y1, Y2, Y3, Y4, Y5 and Y6 is a group of the formula -CH2-CH=CH-R and the remainder of the radicals Y1, Y2, Y3 , Y4, Y5 and Y6 are independently of each other hydrogen or a group of the formula -CH2-CH=CH-R, and R is hydrogen, C1-C18 alkyl or C5-C7 cycloalkyl.

[005] C1-C18 alkyl. and preferably C1-C15 alkyl, comprises linear and branched alkyl. Examples are methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 2-methylpropyl, 1-methylpropyl, tert-butyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1-ethylpropyl, tert-butylmethyl, hexyl, 1-methylpentyl, heptyl, isoheptyl, 2-ethylpentyl, 1-propylbutyl, octyl, isooctyl, 1-ethylhexyl, 2-ethylhexyl, 1,1,3, 3-tetramethylbutyl, 2,4,4- trimethylpentyl, nonyl, isononyl, neononyl, undecyl, lauryl, tridecyl, tetradecyl, pentadecyl.

[006] C1-C12 alkyl, especially C1-C8 alkyl, in particular C1-C4 alkyl, is more preferred. A preferred example is butyl, especially n-butyl.

[007] C1-C18 alkyloxy comprises unsubstituted and substituted alkyloxy, that is, with C1-C9 alkyl. Examples are methyloxy, ethyloxy, propyloxy (= propoxy), butyloxy, hexyloxy, octyloxy and undecyloxy.

[008] C1-C12 alkyloxy is preferred. Preferred examples are methyloxy, ethyloxy, propyloxy, octyloxy and undecyloxy. C1-C4 alkyloxy, especially propyloxy, is highly preferred.

[009] Preference is given to C1-C18 alkyloxy, in which in the case of C3-C18 alkyloxy both carbon atoms in the α and β positions close to oxygen are not branched. Examples are methyloxy, ethyloxy, n-propyloxy, n-butyloxy, n-pentyloxy, 3-methylbutyloxy, n-hexyloxy, 3-methylpentyloxy, 4-methylpentyloxy, n-heptyloxy, 3-methylhexyloxy, 4-methylhexyloxy, 5-methylhexyloxy, 3-ethylpentyloxy, 3,4-dimethylpentyloxy, n-octyloxy, 3-methylheptyloxy, 4-methylheptyloxy, 5-methylheptyloxy, 6-methylheptyloxy, 3-ethylhexyloxy, 4-ethylhexyloxy, 3,4-dimethylhexyloxy, 3,5-dimethylhexyloxy, n-nonyloxy, 3-methyloctyloxy, 4-methyloctyloxy, 5-methyloctyloxy, 6-methyloctyloxy, 7-methyloctyloxy, 3-ethyloxy heptyloxy, 4-ethylheptyloxy, 5-ethylheptyloxy, 3,4-dimethylheptyloxy, 3,5-dimethylheptyloxy, 3,6-dimethylheptyloxy, 4,5-dimethylheptyloxy, 4,6- dimethylheptyloxy, 5,6-dimethylheptyloxy, n-undecyloxy, n-lauryloxy, n-tridecyloxy, n-tetradecyloxy, n-pentadecyloxy, n-hexadecyloxy and n-octadecyloxy.

[0010] Particular preference is given to C3-C18 alkyloxy, more preferably C3-C12 alkyloxy, especially C3-C8 alkyloxy, in which both carbon atoms in the α and β positions close to the oxygen are unbranched.

[0011] Linear C1-C12 alkyloxy, especially linear C1-C4 alkyloxy, is highly preferred. Examples are methyloxy, ethyloxy, n-propyloxy, n-butyloxy, n-pentyloxy, n-hexyloxy, n-heptyloxy, n-octyloxy, n-nonyloxy, n-undecyloxy and n-lauryloxy, especially n-propyloxy.

[0012] C5-C7 cycloalkyloxy is, for example, cyclopentyloxy, cyclohexyloxy or cycloheptyloxy, preferably cyclohexyloxy.

[0013] C5-C7 cycloalkyl is, for example, cyclopentyl, cyclohexyl or cycloheptyl, preferably cyclohexyl.

[0014] C2-C12 alkylene comprises unsubstituted and substituted alkylene, that is, with one or more C1-C4 alkyl. Examples are ethylene, propylene, 1-methylethylene, butylene, pentylene, 2-methylbutylene, hexamethylene and octamethylene.

[0015] C2-C8 alkylene, in particular C2-C6 alkylene, is preferred. Preferred examples are hexamethylene, propylene and ethylene, especially hexamethylene.

[0016] Hydroxyl-substituted C3-C12 alkylene comprises additionally unsubstituted and additionally substituted hydroxyl-substituted alkylene, that is, with one or more C1-C4 alkyl. Examples are 2-hydroxypropylene, 2-hydroxy-butylene, 2,3-dihydroxybutylene, 2,5-hexamethylene and 2-hydroxy-2-methylpropylene. A preferred example is 2-hydroxypropylene.

[0017] R1, R2, R3, R4, R'1, R'2, R'3 and R'4 are preferably C1-C12 alkyl, especially C1-C8 alkyl, in particular C1-C4 alkyl. Butyl, especially n-butyl, is highly preferred.

[0018] R is preferably C1-C4 alkyl, cyclohexyl or hydrogen, preferably C1-C4 alkyl or hydrogen, especially hydrogen.

[0019] X1 and X'1 are preferably C2-C8 alkylene, more preferably C2-C6 alkylene, especially hexamethylene.

[0020] According to one embodiment, all radicals Z1, Z2, Z3, Z4, Z5 and Z6 represent C1-C18 alkyloxy or C5-C7 cycloalkyloxy, especially C1-C18 alkyloxy.

[0021] It is preferable that only one to five radicals of the radicals Z1, Z2, Z3, Z4, Z5 and Z6 are C1-C18 alkyloxy or C5-C7 cycloalkyloxy, and the remainder of the radicals Z1, Z2, Z3, Z4, Z5 and Z6 are hydrogen or hydroxy. For example, five of these radicals are C1-C18 alkyloxy or C5-C7 cycloalkyloxy and the remaining one radical is hydrogen or hydroxy.

[0022] More preferably, two to five, especially three to five, of the radicals Z1, Z2, Z3, Z4, Z5 and Z6 are C1-C18 alkyloxy or C5-C7 cycloalkyloxy and the remainder of the radicals Z1, Z2, Z3, Z4 , Z5 and Z6 is hydrogen or hydroxy.

[0023] Above all preferably four to five, especially five, of the radicals Z1, Z2, Z3, Z4, Z5 and Z6 are C1-C18 alkyloxy or C5-C7 cycloalkyloxy and the rest of the radicals Z1, Z2, Z3, Z4, Z5 and Z6 is hydrogen or hydroxy.

[0024] Alternatively, the degree of substitution by C1-C18 alkyloxy and C5-C7 cycloalkyloxy can also be expressed in percent (number of the sum of C1-C18 alkyloxy and C5-C7 cycloalkyloxy groups in relation to complete substitution by C1-C alkyloxy C18 and C5-C7 cycloalkyloxy, which are six groups). This is, for example, used to specify average values for the degree of substitution in the case of mixtures of compounds of formula (1). For such a degree of substitution by C1-C18 alkyloxy and C5-C7 cycloalkyloxy 50 to 95%, especially 50 to 90% is preferred. A degree of substitution of 50 to 85%, especially 60 to 85%, is most preferred.

[0025] Z1, Z2, Z3, Z4, Z5 and Z6 in the meaning as C1-C18 alkyloxy are preferably C1-C8 alkyloxy, more preferably C1-C4 alkyloxy and especially propyloxy, such as n-propyloxy.

[0026] Z1, Z2, Z3, Z4, Z5 and Z6 in the meaning as C1-C18 alkyloxy are more preferably a group of the formula -O-CH2-CH2-CH2-R, where R is hydrogen or C1-C15 alkyl, preferably hydrogen.

[0027] Z1, Z2, Z3, Z4, Z5 and Z6 in the meaning as C1-C18 alkyloxy or C5-C7 cycloalkyloxy are preferably C1-C18 alkyloxy.

[0028] According to an additional embodiment, all radicals Y1, Y2, Y3, Y4, Y5 and Y6 represent a group of the formula -CH2-CH=CH-R.

[0029] It is preferable that only one to five radicals of the radicals Y1, Y2, Y3, Y4, Y5 and Y6 are a group of the formula -CH2-CH=CH-R and the remainder of the radicals Y1, Y2, Y3, Y4, Y5 and Y6 are hydrogen. For example, five of these radicals are a group of the formula -CH2-CH=CH-R and the rest are hydrogen.

[0030] More preferably two to five, especially three to five, of the radicals Y1, Y2, Y3, Y4, Y5 and Y6 are a group of the formula -CH2-CH=CH- R and the remainder of the radicals Y1, Y2, Y3 , Y4, Y5 and Y6 is hydrogen.

[0031] Above all preferably four to five, especially five, of the radicals Y1, Y2, Y3, Y4, Y5 and Y6 are a group of the formula -CH2- CH=CH-R and the remainder of the radicals Y1, Y2, Y3 , Y4, Y5 and Y6 is hydrogen.

[0032] Alternatively, the degree of substitution by a group of the formula -CH2-CH=CH-R can also be expressed in percent (number of group -CH2-CH=CH-R in relation to complete substitution by six groups - CH2-CH=CH-R). This is, for example, used to specify average values for the degree of substitution in the case of mixtures of compounds of formula (2). For such a degree of substitution by a group of the formula -CH2-CH=CH-R 40 to 95%, especially 40 to 90% is preferred. A degree of substitution of 50 to 90%, especially 60 to 90%, is most preferred.

[0033] More preferably, one to five radicals of radicals Z1, Z2, Z3, Z4, Z5 and Z6 are C1-C18 alkyloxy or C5-C7 cycloalkyloxy and the remainder of radicals Z1, Z2, Z3, Z4, Z5 and Z6 are hydrogen or hydroxy, and one to five radicals of the radicals Y1, Y2, Y3, Y4, Y5 and Y6 are a group of the formula -CH2-CH=CH- R, and the remainder of the radicals Y1, Y2, Y3, Y4, Y5 and Y6 is hydrogen.

[0034] In the formula -CH2-CH=CH-R, the radical R is preferably hydrogen, C1-C15 alkyl or cyclohexyl, more preferably hydrogen or C1-C15 alkyl, especially hydrogen.

[0035] Of special interest are additive mixtures, in which R1, R2, R3, R4, R'1, R'2, R'3 and R'4 are C1-C12 alkyl, X1 and X'1 are C2 alkylene -C8, one to five radicals of radicals Z1, Z2, Z3, Z4, Z5 and Z6 are C1-C18 alkyloxy or C5-C7 cycloalkyloxy and the remainder of radicals Z1, Z2, Z3, Z4, Z5 and Z6 are hydrogen or hydroxy , especially hydrogen, one to five radicals of the radicals Y1, Y2, Y3, Y4, Y5 and Y6 are a group of the formula -CH2-CH=CH-R and the remainder of the radicals Y1, Y2, Y3, Y4, Y5 and Y6 is hydrogen, and R is hydrogen or cyclohexyl. Z1, Z2, Z3, Z4, Z5 and Z6 as C1-C18 alkyloxy are preferably n-propyloxy.

[0036] Additive mixtures are of great importance, in which R1, R2, R3, R4, R'1, R'2, R'3 and R'4 are C1-C12 alkyl, X1 and X'1 are alkylene C2-C8, one to five radicals of radicals Z1, Z2, Z3, Z4, Z5 and Z6 are C1-C18 alkyloxy and the remainder of radicals Z1, Z2, Z3, Z4, Z5 and Z6 are hydrogen or hydroxy, especially hydrogen, one to five radicals of the radicals Y1, Y2, Y3, Y4, Y5 and Y6 are a group of the formula -CH2-CH=CH-R and the remainder of the radicals Y1, Y2, Y3, Y4, Y5 and Y6 is hydrogen, and R is hydrogen. Z1, Z2, Z3, Z4, Z5 and Z6 and C1-C18 alkyloxy are preferably n-propyloxy.

[0037] More preferred compounds of formula (1) are compounds of the following formula (1-A) where for Z1, Z2, Z3, Z4, Z5 and Z6 the settings and preferences provided here previously apply.

[0038] More preferred compounds of formula (2) are compounds of the following formula (2-A) where for Y1, Y2, Y3, Y4, Y5 and Y6 the settings and preferences provided here previously apply.

[0039] A mixture of compounds of formulas (1-A) and (2-A) is highly preferred.

[0040] The weight ratio of compound of formula (1) to compound of formula (2) is preferably 1:99 to 99:1, especially 5:95 to 95:5. A weight ratio of 10:90 to 90:10, especially 20:80 to 80:20, is highly preferred. Of special interest is a weight ratio of 30:70 to 70:30, especially 40:60 to 60:40.

[0041] Compounds of formula (1) or formula (2) can be prepared according to known methods, for example, in the manner provided in WO 2011/029744.

[0042] A further embodiment of this invention is a composition comprising a) an organic material that is susceptible to oxidative, thermal or light-induced degradation; and b) a mixture of compounds of formulas (1) and (2).

[0043] For example, an organic material comprises natural, semi-natural and synthetic polymers, especially synthetic polymers.

[0044] Examples for polymers are:

[0045] 1. Polymers of mono-olefins and diolefins, for example, polypropylene, polyisobutylene, polybut-1-ene, poly-4-methylpent-1-ene, polyvinylcyclohexane, polyisoprene or polybutadiene, as well as polymers of cycloolefins, e.g. of cyclopentene or norbornene, polyethylene (which may optionally be cross-linked), e.g. high density polyethylene (HDPE), high molecular weight high density polyethylene (HDPE-HMW), high density and ultra high molecular weight (HDPE-UHMW), medium density polyethylene (MDPE), low density polyethylene (LDPE), linear low density polyethylene (LLDPE), (VLDPE) and (ULDPE).

[0046] Polyolefins, that is, the mono-olefin polymers exemplified in the preceding paragraph, preferably polyethylene and polypropylene, can be prepared by different methods, and especially by the following: a) radical polymerization (normally at high pressure and at elevated temperature) . b) catalytic polymerization using a catalyst that normally contains one or more metals from groups IVb, Vb, VIb or VIII of the periodic table. These metals generally have one or more than one ligand, typically oxides, halides, alcoholates, esters, ethers, amines, alkyls, alkenyls and/or aryls that can be either π- or o-coordinated. These metal complexes can be in free form or fixed on substrates, typically activated magnesium chloride, titanium(III) chloride, aluminum oxide or silicon. These catalysts can be soluble or insoluble in the polymerization medium. The catalysts may themselves be used in the polymerization or additional activators may be used, typically metal alkyls, metal hydrides, metal alkyl halides, metal alkyl oxides or metal alkyloxanes, said metals being elements of groups Ia, IIa and/or IIIa of the periodic table. Activators can be conveniently modified with further ester, ether, amine or silyl ether groups. These catalyst systems are generally called Phillips, Standard Oil Indiana, Ziegler (-Natta), TNZ (DuPont), metallocene or single site catalysts (SSC).

[0047] 2. Mixtures of the polymers mentioned in 1., for example, mixtures of polypropylene with polyisobutylene, polypropylene with polyethylene (e.g. PP/HDPE, PP/LDPE) and mixtures of different types of polyethylene (e.g. LDPE /HDPE).

[0048] 3. Copolymers of mono-olefins 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 ), propylene/but-1-ene copolymers, propylene/isobutylene copolymers, ethylene/but-1-ene copolymers, ethylene/hexene copolymers, ethylene/methylpentene copolymers, ethylene/heptene copolymers, ethylene/ octene, ethylene/vinylcyclohexane copolymers, ethylene/cyclolefin copolymers (e.g., ethylene/norbornene as COC), ethylene/1-olefin copolymers, where the 1-olefin is generated in situ; propylene/butadiene copolymers, isobutylene/isoprene copolymers, ethylene/vinylcyclohexene copolymers, ethylene/alkyl acrylate copolymers, ethylene/alkyl methacrylate copolymers, ethylene/vinyl acetate copolymers or ethylene/acrylic acid copolymers and their salts (ionomers), as well as terpolymers of ethylene with propylene, and a diene such as hexadiene, dicyclopentadiene or ethylidene norbornene; and mixtures of such copolymers with each other, and with polymers mentioned in 1. above, for example, polypropylene/ethylene-propylene copolymers, LDPE/ethylene-vinyl acetate (EVA) copolymers, LDPE/ethylene-acrylic acid copolymers (EAA), LLDPE/EVA, LLDPE/EAA and alternative or random polyalkylene/carbon monoxide copolymers and mixtures thereof with other polymers, for example polyamides.

[0049] 4. Hydrocarbon resins (e.g., C5-C9) including hydrogenated modifications thereof (e.g., tackifiers) and mixtures of polyalkylenes and starch.

[0050] Homopolymers and copolymers of 1.-4. they can present any stereostructure, including syndiotactic, isotactic, hemi-isotactic or atactic; where atactic polymers are preferred. Stereoblock polymers are also included.

[0051] 5. Polystyrene, poly(p-methylstyrene), poly(α-methylstyrene).

[0052] 6. Aromatic homopolymers and copolymers derived from aromatic vinyl monomers including styrene, α-methylstyrene, all isomers of vinyl toluene, especially p-vinyltoluene, all isomers of ethyl styrene, propyl styrene, vinyl biphenyl, vinyl naphthalene, and vinyl anthracene and mixtures thereof. Homopolymers and copolymers can have any stereostructure, including syndiotactic, isotactic, hemi-isotactic or atactic; where atactic polymers are preferred. Stereoblock polymers are also included.

[0053] 6a. Copolymers including the aforementioned aromatic vinyl monomers and comonomers selected from ethylene, propylene, dienes, nitriles, acids, maleic anhydrides, maleimides, vinyl acetate and vinyl chloride, or acrylic derivatives and mixtures thereof, for example, styrene/butadiene, styrene/ acrylonitrile, styrene/ethylene (interpolymers), styrene/alkyl methacrylate, styrene/butadiene/alkyl acrylate, styrene/butadiene/alkyl methacrylate, styrene/maleic anhydride, styrene/acrylonitrile/methyl acrylate; high impact resistance mixtures of copolymers of styrene and another polymer, for example, a polyacrylate, a diene polymer or an ethylene/propylene/diene terpolymer; and styrene block copolymers such as styrene/butadiene/styrene, styrene/isoprene/styrene, styrene/ethylene/butylene/styrene or styrene/ethylene/propylene/styrene.

[0054] 6b. Hydrogenated aromatic polymers Hydrogenated aromatic polymers derived from the hydrogenation of polymers mentioned in 6.), including especially polycyclohexylethylene (PCHE) prepared by hydrogenating atactic polystyrene, often referred to as polyvinylcyclohexane (PVCH).

[0055] 6c. Hydrogenated aromatic polymers derived from the hydrogenation of polymers mentioned in 6a.

[0056] Homopolymers and copolymers can have any stereostructure, including syndiotactic, isotactic, hemi-isotactic or atactic; where atactic polymers are preferred. Stereoblock polymers are also included.

[0057] 7. Graft copolymers of aromatic vinyl monomers such as styrene or α-methylstyrene, for example, styrene in polybutadiene, styrene in polybutadiene-styrene or polybutadiene-acrylonitrile copolymers; styrene and acrylonitrile (or methacrylonitrile) in polybutadiene; styrene, acrylonitrile and methyl methacrylate in polybutadiene; styrene and maleic anhydride in polybutadiene; styrene, acrylonitrile and maleic anhydride or maleimide in polybutadiene; styrene and maleimide in polybutadiene; styrene and alkyl acrylates or methacrylates in polybutadiene; styrene and acrylonitrile in ethylene/propylene/diene terpolymers; styrene and acrylonitrile in polyalkyl acrylates or polyalkyl methacrylates, styrene and acrylonitrile in acrylate/butadiene copolymers, as well as mixtures thereof with the copolymers listed in 6), for example, the copolymer mixtures known as ABS, MBS, ASA or AES polymers.

[0058] 8. Halogen-containing polymers such as polychloroprene, chlorinated rubbers, chlorinated and brominated isobutylene-isoprene copolymer (halobutyl rubber), chlorinated or sulfochlorinated polyethylene, chlorinated ethylene and ethylene copolymers, homo- and epichlorohydrin copolymers, especially chlorinated ethylene polymers halogen-containing vinyl compounds, for example, polyvinyl chloride, polyvinylidene chloride, polyvinyl fluoride, polyvinylidene fluoride, as well as copolymers thereof such as vinyl chloride/vinylidene chloride copolymers, vinyl chloride/vinyl acetate or vinyl chloride vinylidene/vinyl acetate.

[0059] 9. Polymers derived from α, β-unsaturated acids and derivatives thereof, such as polyacrylates and polymethacrylates; polymethyl methacrylates, polyacrylamides and polyacrylonitriles, modified by impact with butyl acrylate.

[0060] 10. Copolymers of the monomers mentioned in 9. with each other or with other unsaturated monomers, for example, acrylonitrile/butadiene copolymers, acrylonitrile/alkyl acrylate copolymers, acrylonitrile/alkoxyalkyl acrylate or acrylonitrile/vinyl halide copolymers or acrylonitrile/alkyl methacrylate/butadiene terpolymers.

[0061] 11. Polymers derived from unsaturated alcohols and amines, or their acyl derivatives or acetals, for example, polyvinyl alcohol, polyvinyl acetate, polyvinyl stearate, polyvinyl benzoate, polyvinyl maleate, polyvinyl butyral, polyallyl phthalate or polyallyl melamine; as well as its copolymers with olefins mentioned in 1. previously.

[0062] 12. Homopolymers and copolymers of cyclic ethers such as polyalkylene glycols, polyethylene oxide, polypropylene oxide or copolymers thereof with bisglycidyl ethers.

[0063] 13. Polyacetals such as polyoxymethylene and those polyoxymethylenes that contain ethylene oxide as a comonomer; polyacetals modified with thermoplastic polyurethanes, acrylates or MBS.

[0064] 14. Polyphenylene oxides and sulfides, and mixtures of polyphenylene oxides with styrene polymers or polyamides.

[0065] 15. Polyurethanes derived from polyethers, polyesters or polybutadienes terminated with hydroxyl on the one hand and aliphatic or aromatic polyisocyanates on the other, as well as precursors thereof.

[0066] 16. Polyamides and copolyamides derived from diamines and dicarboxylic acids and/or aminocarboxylic acids, or the corresponding lactams, for example, polyamide 4, polyamide 6, polyamide 6/6, 6/10, 6/9, 6/ 12, 4/6, 12/12, polyamide 11, polyamide 12, aromatic polyamides from m-xylene diamine and adipic acid; polyamides prepared from hexamethylenediamine and isophthalic or/and terephthalic acid, and with or without an elastomer as modifier, for example, poly-2,4,4,-trimethylhexamethylene terephthalamide or poly-m-phenylene isophthalamide; and also block copolymers of the aforementioned polyamides with polyolefins, olefin copolymers, ionomers or chemically bonded or grafted elastomers; or with polyethers, for example with polyethylene glycol, polypropylene glycol or polytetramethylene glycol; as well as polyamides or copolyamides modified with EPDM or ABS; and polyamides condensed during processing (RIM polyamide systems).

[0067] 17. Polyureas, polyimides, polyamide-imides, polyetherimides, polyesterimides, polyhydantoins and polybenzimidazoles.

[0068] 18. Polyesters derived from dicarboxylic acids and diols, and/or carboxylic acids or the corresponding lactones or lactides, for example, polyethylene terephthalate, polybutylene terephthalate, poly-1,4-dimethylolcyclohexane terephthalate, polyalkylene naphthalate and poly - hydroxybenzoates, as well as copolyether esters derived from hydroxyl-terminated polyethers, and also polyesters modified with polycarbonates or MBS. Copolyesters may comprise, for example, - but without limitation - polybutylenesuccinate/terephthalate, polybutyleneadipate/terephthalate, polytramethyleneadipate/terephthalate, polybutylenesuccinate/adipate, polybutylenesuccinate/carbonate, poly-3-hydroxybutyrate/octanoate copolymer, poly-3-hydroxybutyrate terpolymer/ hexanoate/decanoate. Furthermore, aliphatic polyesters may comprise, for example, - but without limitation - the class of poly(hydroxyalkanoates), in particular, poly(propiolactone), poly(butyrolactone), poly(pivalolactone), poly(valerolactone) and poly(caprolactone). ), polyethylenesuccinate, polypropylenesuccinate, polybutylenesuccinate, polyhexamethylenesuccinate, polyethyleneadipate, polypropyleneadipate, polybutyleneadipate, polyhexamethyleneadipate, polyethylene oxalate, polypropylene oxalate, polybutylene oxalate, polyhexamethylene oxalate, polyethylenesebacate, polypropylenesebacate, polybutylenesebacate bacate and polylactic acid (PLA ), as well as corresponding polyesters modified with polycarbonates or MBS. The term “polylactic acid (PLA)” indicates a homopolymer of preferably poly-L-lactide and any of its unions or alloys with other polymers; a copolymer of lactic acid or lactide with other monomers such as hydroxycarboxylic acids, for example as glycolic acid, 3-hydroxybutyric acid, 4-hydroxybutyric acid, 4-hydroxyvaleric acid, 5-hydroxyacid -valeric, 6-hydroxycaproic acid and cyclic forms thereof; The terms "lactic acid" or "lactide" include L-lactic acid, D-lactic acid, mixtures and dimers thereof, that is, L-lactide, D-lactide, mesolactide and any mixtures thereof.

[0069] 19. Polycarbonates and polyester carbonates.

[0070] 20. Polytones.

[0071] 21. Polysulfones, polyether sulfones and polyether ketones.

[0072] 22. Cross-linked polymers derived from aldehydes on the one hand, and phenols, ureas and melamines on the other hand, such as phenol/formaldehyde resins, urea/formaldehyde resins and melamine/formaldehyde resins.

[0073] 23. Drying and non-drying alkyd resins.

[0074] 24. Unsaturated polyester resins derived from copolyesters of saturated and unsaturated dicarboxylic acids, with polyhydric alcohol and vinyl compounds as crosslinking agents, and also halogen-containing modifications of these with low flammability.

[0075] 25. Crosslinkable acrylic resins derived from substituted acrylates, for example, epoxy acrylates, urethane acrylates or polyester acrylates.

[0076] 26. Alkyd resins, polyester resins and acrylate resins crosslinked with melamine resins, urea resins, isocyanate resins, isocyanurates, polyisocyanates or epoxy.

[0077] 27. Cross-linked epoxy resins derived from aliphatic, cyclo-aliphatic, heterocyclic or aromatic glycidyl compounds, for example, diglycidyl ether products of bisphenol A and bisphenol F, which are cross-linked with common hardeners such as anhydrides or amines, with or without accelerators.

[0078] 28. Natural polymers such as cellulose, rubber, gelatin and chemically modified homologous derivatives thereof, for example, cellulose acetates, cellulose propionates and cellulose butyrates, or cellulose ethers such as methyl cellulose; as well as rosin rosins and their derivatives.

[0079] 29. Unions of the aforementioned polymers (poly-unions), for example, PP/EPDM, Polyamide/EPDM or ABS, PVC/EVA, PVC/ABS, PVC/MBS, PC/ABS, PBTP/ABS, PC /ASA, PC/PBT, PVC/CPE, PVC/acrylates, thermoplastic POM/PUR, thermoplastic PC/PUR, POM/acrylate, POM/MBS, PPO/HIPS, PPO/PA 6.6 and copolymers, PA/HDPE, PA/ PP, PA/PPO, PBT/PC/ABS or PBT/PET/PC.

[0080] A coating binder is, for example, an acid-catalyzed two-component system or an air-drying system.

[0081] A preferred polymer for component a) is a thermoplastic polymer or a coating binder.

[0082] In particular, component a) is a thermoplastic polymer polymer. The group of thermoplastic polyolefins is of great relevance, especially homo- or copolymers containing polymerized propylene or ethylene. Especially preferred is polypropylene or polyethylene, in particular polyethylene.

[0083] Preferred as component a) are also biodegradable polymers of both natural and synthetic origin.

[0084] Examples are polyethylene succinate (Lunare SE (RTM, Nihon Shokubai)), polybutylenesuccinate (Bionolle 1000 (RTM, Showa Highpolymer)), polybutylenesuccinate/adipate (Bionolle 3000 (RTM, Showa Highpolymer)), polybutylenesuccinate/carbonate (Iupec (RTM , Mitsubishi Gas Chemicals)), polybutylenesuccinate/terephthalate (Biomax (RTM, Dupont), Ecoflex (RTM, BASF), EasterBio (RTM, Eastman Chemicals)), polycaprolactone (CelGreen PH (RTM, Daicel Kagaku), Tone (RTM, UCC )), poly(hydroxyalkanoates) (Nodax (RTM, Procter and Gamble), from Metabolix), poly-3-hydroxybutyrate (Biogreen (RTM, Mitsubishi Gas Chemicals)), polylactic acid (NatureWorks (RTM, Cargill), LACEA (RTM , Mitsui Chemicals), Lacty (RTM, Shimadzu Seisakusho)), polyester amides or unions of these materials with natural or modified starch, polysaccharides, lignin, wood flour, cellulose and chitin.

[0085] The amount used of component b) in relation to component a) varies with the particular organic material and the selected application.

[0086] In general, component b) of the present invention is used from about 0.01 to about 10% by weight of component a). An advantageous range is 0.05% to 5%, in particular 0.05% to 3%. Especially preferred is 0.1% to 1.5%.

[0087] Another advantageous range is, in particular for improving flame retardancy, from 0.6% to 3%, especially from 0.7% to 1.5%.

[0088] The composition as described above, comprising component a) and component b), may contain additional additives.

[0089] Examples of additional additives are provided below:

1. Antioxidants

[0090] 1.1. Alkylated monophenols, e.g. 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6- di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-isobutylphenol, 2,6-dicyclopentyl-4-methylphenol, 2-(α-methylcyclohexyl)-4,6- dimethylphenol, 2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, nonylphenols that are linear or branched in the side chains, e.g. ,6-di-nonyl-4-methylphenol, 2,4-dimethyl-6-(1'-methylundec-1'-yl)phenol, 2,4-dimethyl-6-(1'-methylheptadec-1' -yl)phenol, 2,4-dimethyl-6-(1'-methyltridec-1'-yl)phenol and mixtures thereof.

[0091] 1.2. Alkylthiomethylphenols, for example, 2,4-dioctylthiomethyl-6-tert-butylphenol, 2,4-dioctylthiomethyl-6-methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol, 2,6-didodecylthiomethyl-4-nonylphenol.

[0092] 1.3. Alkylated hydroquinones and hydroquinones, for example, 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butylhydroquinone, 2,5-di-tert-amylhydroquinone, 2,6- diphenyl-4-octadecyloxyphenol, 2,6-di-tert-butyl-hydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyanisole, 3,5- di-tert-butyl-4-hydroxyphenyl stearate, bis(3,5-di-tert-butyl-4-hydroxyphenyl) adipate.

[0093] 1.4. Tocopherols, for example, α-tocopherol, β-tocopherol, δ-tocopherol, δ-tocopherol and mixtures thereof (vitamin E).

[0094] 1.5. Hydroxylated thiodiphenyl ethers, e.g. 2,2'-thiobis(6-tert-butyl-4-methylphenol), 2,2'-thiobis(4-octylphenol), 4,4'-thiobis(6-tert-butyl- 3-methylphenol), 4,4'-thiobis(6-tert-butyl-2-methylphenol), 4,4'-thiobis(3,6-di-sec-amylphenol), 4,4'-bis(2, 6-dimethyl-4-hydroxyphenyl)disulfide.

[0095] 1.6. Alkylidenebisphenols, e.g. 2,2'-methylenebis(6-tert-butyl-4-methylphenol), 2,2'-methylenebis(6-tert-butyl-4-ethylphenol), 2,2'-methylenebis[4- methyl-6-(α-methylcyclohexyl)phenol], 2,2'-methylenebis(4-methyl-6-cyclohexylphenol), 2,2'-methylenebis(6-nonyl-4-methylphenol), 2, 2'-methylenebis(4,6-di-tert-butylphenol), 2,2'-ethylidenebis(4,6-di-tert-butylphenol), 2,2'-ethylidenebis(6-tert-butyl-4-isobutylphenol ), 2,2'-methylenebis[6-(α-methylbenzyl)-4-nonylphenol], 2,2'-methylenebis[6-(α,α-dimethylbenzyl)-4-nonylphenol], 4,4'-methylenebis (2,6-di-tert-butylphenol), 4,4'-methylenebis(6-tert-butyl-2-methylphenol), 1,1-bis(5-tert-butyl-4-hydroxy-2-methylphenyl) butane, 2,6-bis(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4-methylphenol, 1,1,3-tris(5-tert-butyl-4-hydroxy-2-methylphenyl)butane , 1,1-bis(5-tert-butyl-4-hydroxy-2-methyl-phenyl)-3-n-dodecylmercaptobutane, ethylene glycol bis[3,3-bis(3'-tert-butyl-4'- hydroxyphenyl)butyrate], bis(3-tert-butyl-4-hydroxy-5-methyl-phenyl)dicyclopentadiene, bis[2-(3'-tert-butyl-2'-hydroxy-5'-methylbenzyl)- 6-tert-butyl-4-methylphenyl]terephthalate, 1,1-bis-(3,5-dimethyl-2-hydroxyphenyl)butane, 2,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl )propane, 2,2-bis(5-tert-butyl-4-hydroxy2-methylphenyl)-4-n-dodecylmercaptobutane, 1,1,5,5-tetra-(5-tert-butyl-4-hydroxy-2 - methylphenyl)pentane.

[0096] 1.7. O, N and S-benzyl compounds, e.g. 3,5,3',5'-tetra-tert-butyl-4,4'-dihydroxydibenzyl ether, octadecyl-4-hydroxy-3,5-dimethylbenzylmercaptoacetate , tridecyl-4-hydroxy-3,5-di-tert-butylbenzylmercaptoacetate, tris(3,5-di-tert-butyl-4-hydroxybenzyl)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-butyl-4-hydroxybenzylmercaptoacetate.

[0097] 1.8. Hydroxybenzylated malonates, e.g. dioctadecyl-2,2-bis(3,5-di-tert-butyl-2-hydroxybenzyl)malonate, di-octadecyl-2-(3-tert-butyl-4-hydroxy-5-methylbenzyl )malonate, di-dodecylmercaptoethyl-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate, bis[4-(1,1,3,3-tetramethylbutyl)phenyl]- 2,2 -bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate.

[0098] 1.9. Aromatic hydroxybenzyl compounds, for example, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene, 1,4-bis(3,5-di -tert-butyl-4-hydroxybenzyl)-2,3,5,6-tetramethylbenzene, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)phenol.

[0099] 1.10. Triazine compounds, e.g. 2,4-bis(octylmercapto)-6-(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine, 2-octylmercapto-4,6- bis(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine, 2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyphenoxy)- 1,3,5-triazine, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,2,3-triazine, 1,3,5-tris(3,5 -di-tert-butyl-4-hydroxybenzyl)isocyanurate, 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanurate, 2,4,6-tris(3,5 -di-tert-butyl-4-hydroxyphenylethyl)- 1,3,5-triazine, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)-hexahydro- 1,3 ,5-triazine, 1,3,5-tris(3,5-dicyclohexyl-4-hydroxybenzyl)isocyanurate.

[00100] 1.11. Benzylphosphonates, e.g. dimethyl-2,5-di-tert-butyl-4-hydroxybenzylphosphonate, diethyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl3,5-di-tert-butyl-4-hydroxybenzylphosphonate , dioctadecyl-5-tert-butyl-4-hydroxy-3-methylbenzylphosphonate, the calcium salt of 3,5-di-tert-butyl-4-hydroxybenzylphosphonic acid monoethyl ester.

[00101] 1.12. Acylaminophenols, e.g. 4-hydroxylauranilide, 4-hydroxystearanilide, octyl N-(3,5-di-tert-butyl-4-hydroxyphenyl)carbamate.

[00102] 1.13. β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid ester 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, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane.

[00103] 1.14. e-(5-tert-butyl-4-hydroxy-3-methylphenyl)propionic acid ester with mono- or polyhydric alcohols, for example with methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6 -hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxamide, 3 -thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane; 3,9-bis[2-{3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy}-1,1-dimethylethyl]-2,4,8,10-tetraoxaspiro[5.5]undecane.

[00104] 1.15. β-(3,5-dicyclohexyl-4-hydroxyphenyl)propionic acid ester with mono- or 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)oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethyl - hexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane.

[00105] 1.16. 3,5-Di-tert-butyl-4-hydroxyphenyl acetic acid ester with mono- or 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)oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol , trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane.

[00106] 1.17. β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid amides, e.g., N,N-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamide, N,N '-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)trimethylenediamide, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazide, N,N'-bis[ 2-(3-[3,5-di-tert-butyl-4-hydroxyphenyl]propionyloxy)ethyl]oxamide (Naugard XL-1, (RTM, supplied by Uniroyal).

[00107] 1.18. Ascorbic acid (vitamin C)

[00108] 1.19. Amine antioxidants, e.g. N,N-diisopropyl-p-phenylenediamine, N,N'-di-sec-butyl-p-phenylenediamine, N,N'-bis(1,4-dimethylpentyl)-p-phenylenediamine , N,N'-bis(1-ethyl-3-methylpentyl)-p-phenylenediamine, N,N'-bis(1-methylheptyl)-p-phenylenediamine, N,N'-dicyclohexyl-p- phenylenediamine, N,N'-diphenyl-p-phenylenediamine, N,N'-bis(2-naphthyl)-p-phenylenediamine, N-isopropyl-N'-phenyl-p-phenylenediamine, N-(1,3-dimethylbutyl )- N'-phenyl-p-phenylenediamine, N-(1-methylheptyl)-N'-phenyl-p-phenylenediamine, N-cyclohexyl-N'-phenyl-p-phenylenediamine, 4-(p- toluenesulfamoyl)diphenylamine, N,N'-dimethyl-N,N'-di-sec-butyl-p-phenylenediamine, diphenylamine, N-allyldiphenylamine, 4-isopropoxydiphenylamine, N-phenyl-1-naphthylamine, N-(4-tert - octylphenyl)-1-naphthylamine, N-phenyl-2-naphthylamine, octylated diphenylamine, e.g. p,p'-di-tert-octyldiphenylamine, 4-n-butylaminophenol, 4-butyrylaminophenol, 4-nonanoylaminophenol, 4-dodecanoylaminophenol , 4-octadecanoylaminophenol, bis(4-methoxyphenyl)amine, 2,6-di-tert-butyl-4-dimethylaminomethylphenol, 2,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, N,N,N',N' -tetramethyl-4,4'-diaminodiphenylmethane, 1,2-bis[(2-methylphenyl)amino]ethane, 1,2-bis(phenylamino)propane, (o-tolyl)biguanide, bis[4-(1', 3'-dimethylbutyl)phenyl]amine, tert-octylated N-phenyl-1-naphthylamine, a mixture of mono- and dialkyllated tert-butyl/tert-octyldiphenylamines, a mixture of mono- and dialkyllated nonyldiphenylamines, a mixture of mono- and dialkylated dodecyldiphenylamines, a mixture of mono- and dialkyllated isopropyl/isohexyl-diphenylamines, a mixture of mono- and dialkyllated tert-butyldiphenylamines, 2,3-dihydro-3,3-dimethyl-4H-1,4-benzothiazine, phenothiazine, a mixture of mono and dialkyl tert-butyl/tert-octylphenothiazines, a mixture of mono and dialkyl tert-octylphenothiazines, N-allylphenothiazine, N,N,N',N'-tetraphenyl-1,4-diaminobut-2-ene. 2. UV absorbers and light stabilizers

[00109] 2.1. 2-(2'-Hydroxyphenyl)benzotriazoles, e.g. 2-(2'-hydroxy-5'-methylphenyl)-benzotriazole, 2-(3',5'-di-tert-butyl-2'-hydroxyphenyl)benzotriazole , 2-(5'-tert-butyl-2'-hydroxyphenyl)benzotriazole, 2-(2'-hydroxy-5'-(1,1,3,3-tetramethylbutyl)phenyl)benzotriazole, 2-(3', 5'-di-tert-butyl-2'-hydroxyphenyl)-5-chloro-benzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-methylphenyl)-5-chloro-benzotriazole, 2- (3'-sec-butyl-5'-tert-butyl-2'-hydroxyphenyl)benzotriazole, 2-(2'-hydroxy-4'-octyloxyphenyl)benzotriazole, 2-(3',5'-di-tert- amyl-2'-hydroxyphenyl)benzotriazole, 2-(3',5'-bis-(α,α-dimethylbenzyl)-2'-hydroxyphenyl)benzotriazole, 2-(3'-tert-butyl-2'-hydroxy- 5'-(2-octyloxycarbonylethyl)phenyl)-5-chloro-benzotriazole, 2-(3'-tert-butyl-5'-[2-(2-ethylhexyloxy)-carbonylethyl]-2'-hydroxyphenyl)- 5-chloro-benzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2-methoxycarbonylethyl)phenyl)-5-chloro-benzotriazole, 2-(3'-tert-butyl-2' -hydroxy-5'-(2-methoxycarbonylethyl)phenyl)benzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2-octyloxycarbonylethyl)phenyl)benzotriazole, 2-(3'-tert- butyl-5'-[2-(2-ethylhexyloxy)carbonylethyl]-2'-hydroxyphenyl)benzotriazole, 2-(3'-dodecyl-2'-hydroxy-5'-methylphenyl)benzotriazole, 2-(3' -tert-butyl-2'-hydroxy-5'-(2-iso-octyloxycarbonylethyl)phenylbenzotriazole, 2,2'-methylene-bis[4-(1,1,3,3-tetramethylbutyl)-6-benzotriazol-2 -ylphenol]; the transesterification product of 2- [3'-tert-butyl-5'-(2-methoxycarbonylethyl)-2'-hydroxyphenyl]-2H-benzotriazole with [R— CH2CH2-COO-CH2CH,-)- 2 polyethylene glycol 300 ; , where R' = 3'-tert-butyl-4'-hydroxy-5'-2H-benzotriazol-2-ylphenyl, 2-[2-hydroxy-3-(a,a-dimethylbenzyl)-5'-(1 ,1,3,3-tetramethylbutyl)-feml]-benzotriazole; 2-[2'-hydroxy-3'-(1,1,3,3-tetramethylbutyl)-5-(α,α-dimethylbenzyl)-phenyl]benzotriazole.

[00110] 2.2. 2-Hydroxybenzophenones, e.g. the derivatives of 4-hydroxy, 4-methoxy, 4-octyloxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy, 4,2',4'-trihydroxy and 2'-hydroxy -4,4'-dimethoxy.

[00111] 2.3. Ester of substituted and unsubstituted benzoic acids, for example, 4-tert-butyl-phenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoyl resorcinol, bis(4-tert-butylbenzoyl)resorcinol, benzoyl resorcinol, 2,4-di-tert -butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate, hexadecyl 3,5-di-tert-butyl-4-hydroxybenzoate, octadecyl 3,5-di-tert-butyl-4-hydroxybenzoate, 2-methyl- 4,6-di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate.

[00112] 2.4. Acrylates, e.g. ethyl α-cyano-β,β-diphenylacrylate, iso-octyl α-cyano-β,β-diphenylacrylate, methyl α-carbomethoxycininmate, methyl α-cyano-β-methyl-p-methoxycininmate, butyl α- cyano-β-methyl-p-methoxy-cinimate, methyl α-carbomethoxy-p-methoxycinimate, N-(β-carbomethoxy-β-cyanovinyl)-2-methylindoline, neopentyl tetra(α-cyano-β,β-diphenylacrylate.

[00113] 2.5. Nickel compounds, for example, nickel complexes of 2,2'-thio-bis[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 N-cyclohexyldiethanolamine, nickel dibutyldithiocarbamate, nickel salts of the monoalkyl ester, for example, the methyl or ethyl ester, of 4-hydroxy-3,5-di-tert acid -butylbenzylphosphonic acid, nickel complexes of ketoximes, for example, of 2-hydroxy-4-methylphenylundecylketoxime, nickel complexes of 1-phenyl-4-lauroyl-5-hydroxypyrazole, with or without additional ligands.

[00114] 2.6. Sterically hindered amines, for example, bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate, bis(2,2,6,6-tetramethyl-4-piperidyl)succinate, bis(1,2,2 ,6,6-pentamethyl-4-piperidyl)sebacate, bis(1-octyloxy-2,2,6,6-tetramethyl-4-piperidyl)sebacate, bis(1,2,2,6,6-pentamethyl-4 - piperidyl) n-butyl-3,5-di-tert-butyl-4-hydroxybenzylmalonate, the condensate of 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid, condensates linear or cyclic forms of N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4-tert-octylamino-2,6-dichloro-1,3,5-triazine, tris(2 ,2,6,6-tetramethyl-4-piperidyl)nitrilotriacetate, tetrakis(2,2,6,6-tetramethyl-4-piperidyl)-1,2,3,4-butanetetracarboxylate, 1,1'-(1, 2-ethanedyl)-bis(3,3,5,5-tetramethylpiperazinone), 4-benzoyl-2,2,6,6-tetramethylpiperidine, 4-stearyloxy-2,2,6,6-tetramethylpiperidine, bis(1, 2,2,6,6-pentamethylpiperidyl)-2-n-butyl-2-(2-hydroxy-3,5-di-tert-butylbenzyl)malonate, 3-n-octyl-7,7,9,9- tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione, bis(1-octyloxy-2,2,6,6-tetramethylpiperidyl)sebacate, bis(1-octyloxy-2,2,6, 6-tetramethylpiperidyl)succinate, linear or cyclic condensates of N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4-morpholino-2,6-dichloro-1,3,5- triazine, the condensate of 2-chloro-4,6-bis(4-n-butylamino-2,2,6,6-tetramethylpiperidyl)-1,3,5-triazine and 1,2-bis(3-aminopropylamino) ethane, the condensate of 2-chloro-4,6-di-(4-n-butylamino-1,2,2,6,6-pentamethylpiperidyl)-1,3,5-triazine and 1,2-bis(3 -aminopropylamino)ethane, 8-acetyl-3-dodecyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione, 3-dodecyl-1-(2, 2,6,6-tetramethyl-4-piperidyl)pyrrolidine-2,5-dione, 3-dodecyl-1-(1,2,2,6,6-pentamethyl-4-piperidyl)pyrrolidine-2,5-dione , a mixture of 4-hexadecyloxy and 4-stearyloxy-2,2,6,6-tetramethylpiperidine, a condensate of N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4- cyclohexylamino-2,6-dichloro-1,3,5-triazine, a condensate of 1,2-bis(3-aminopropylamino)ethane and 2,4,6-trichloro-1,3,5-triazine, as well as 4-butylamino-2,2,6,6-tetramethylpiperidine (CAS Reg. No. [136504-96-6]); a condensate of 1,6-hexanediamine and 2,4,6-trichloro-1,3,5-triazine, as well as N,N-dibutylamine and 4-butylamino-2,2,6,6-tetramethylpiperidine (CAS Reg. No. [192268-64-7]); N-(2,2,6,6-tetramethyl-4-piperidyl)-n-dodecylsuccinimide, N-(1,2,2,6,6-pentamethyl-4-piperidyl)-n-dodecylsuccinimide, 2-undecyl- 7,7,9,9-tetramethyl-1-oxa-3,8-diaza-4-oxo-spiro[4,5]decane, a reaction product of 7,7,9,9-tetramethyl-2-cycloundecyl -1-oxa-3,8-diaza-4-oxospiro-[4,5]decane and epichlorohydrin, 1,1-bis(1,2,2,6,6-pentamethyl-4-piperidyloxycarbonyl)-2-( 4-methoxyphenyl)ethene, N,N'-bis-formyl-N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine, a diester of 4-methoxymethylenemalonic acid with 1,2, 2,6,6-pentamethyl-4-hydroxypiperidine, poly[methylpropyl-3-oxy-4-(2,2,6,6-tetramethyl-4-piperidyl)]siloxane, an acid anhydride copolymer reaction product maleic-α-olefin with 2,2,6,6-tetramethyl-4-aminopiperidine or 1,2,2,6,6-pentamethyl-4-aminopiperidine, 2,4-bis[N-(1-cyclohexyloxy -2,2,6,6-tetramethylpiperidin-4-yl)-N-butylamino]-6-(2-hydroxyethyl)amino-1,3,5-triazine, 1-(2-hydroxy-2-methylpropoxy)- 4-octadecanoyloxy-2,2,6,6-tetramethylpiperidine, 5-(2-ethylhexanoyl)oxymethyl-3,3,5-trimethyl-2-morpholinone, Sanduvor (RTM, Clariant; CAS Reg. No. 106917-31-1], Adk Stab La-81 (CAS Reg. No. 705257-84-7), Hostavin® NOW (available from Clariant AG), Flamestab® NOR 116 (CAS Reg. No. 191680-81-6), Tinuvin® NOR 371 (mixture of oligomeric compounds that are the formal condensation products of N,N'-bis-(2,2,6,6-tetramethyl-1-propoxy-piperidin-4- yl)-hexane1,6-diamine and 2,4-dichloro-6-{n-butyl-(2,2,6,6-tetramethyl-1-propoxy-piperidin-4-yl)-amino}-[1, 3,5]triazine, terminated with 2-chloro-4,6-bis-(di-n-butylamino)-[1,3,5]triazine), 5-(2-ethylhexanoyl)oxymethyl-3,3 ,5-trimethyl-2-morpholinone, the reaction product of 2,4-bis[(1-cyclohexyloxy-2,2,6,6-piperidin-4-yl)butylamino]-6-chloro-s- triazine with N,N'-bis(3-aminopropyl)ethylenediamine), 1,3,5-tris(N-cyclohexyl-N-(2,2,6,6-tetramethylpiperazine-3-one-4 -yl)amino)-s-triazine, 1,3,5-tris(N-cyclohexyl-N-(1,2,2,6,6-pentamethylpiperazine-3-one-4-yl)amino)- s-triazine.

[00115] 2.7. Oxamides, e.g. 4,4'-dioctyloxyoxanilide, 2,2'-diethoxyoxanilide, 2,2'-dioctyloxy-5,5'-di-tert-butoxanilide, 2,2'-didodecyloxy-5,5'-di -tert-butoxanilide, 2-ethoxy-2'-ethyloxanilide, N,N'-bis(3-dimethylaminopropyl)oxamide, 2-ethoxy-5-tert-butyl-2'-ethoxanilide and their mixture with 2-ethoxy-2 '-ethyl-5,4'-di-tert-butoxanilide, mixtures of o- and p-methoxy-disubstituted oxanilides and mixtures of o- and p-ethoxy-disubstituted oxanilides.

[00116] 2.8. 2-(2-Hydroxyphenyl)-1,3,5-triazines, e.g. 2,4,6-tris(2-hydroxy-4-octyloxyphenyl)-1,3,5-triazine, 2-(2-hydroxy -4-octyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl )-1,3,5-triazine, 2,4-bis(2-hydroxy-4-propyloxyphenyl)-6-(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2-hydroxy- 4-octyloxyphenyl)-4,6-bis(4-methylphenyl)- 1,3,5-triazine, 2-(2-hydroxy-4-dodecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1 ,3,5- triazine, 2-(2-hydroxy-4-tridecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5- triazine, 2-[2-hydroxy-4-( 2-hydroxy-3-butyloxypropoxy)phenyl]-4,6-bis(2,4-dimethyl)-1,3,5-triazine, 2-[2-hydroxy-4-(2-hydroxy-3-octyloxypropyloxy) phenyl]-4,6-bis(2,4-dimethyl)-1,3,5-triazine, 2-[4-(dodecyloxy/tridecyloxy-2-hydroxypropoxy)-2-hydroxyphenyl]-4,6-bis( 2,4-dimethylphenyl)-1,3,5-triazine, 2-[2-hydroxy-4-(2-hydroxy-3-dodecyloxypropoxy)phenyl]-4,6-bis(2,4-dimethylphenyl)- 1 ,3,5-triazine, 2-(2-hydroxy-4-hexyloxy)phenyl-4,6-diphenyl-1,3,5-triazine, 2-(2-hydroxy-4-methoxyphenyl)-4,6- diphenyl-1,3,5-triazine, 2,4,6-tris[2-hydroxy-4-(3-butoxy-2-hydroxypropoxy)phenyl]-1,3,5-triazine, 2-(2-hydroxyphenyl )-4-(4-methoxyphenyl)-6-phenyl-1,3,5-triazine, 2-{2-hydroxy-4-[3-(2-ethylhexyl-1-oxy)-2-hydroxypropyloxy] phenyl}-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2,4-bis(4-[2-ethylhexyloxy]-2-hydroxyphenyl)-6-(4- methoxyphenyl)-1,3,5-triazine.

[00117] 3. Metal deactivators, for example, N,N-diphenyloxamide, N-salicylal-N'-salicyloyl hydrazine, N,N'-bis(salicyloyl)hydrazine, N,N'-bis(3,5- di-tert-butyl-4-hydroxyphenylpropionyl)hydrazine, 3-salicyloylamino-1,2,4-triazole, bis(benzylidene)oxalyl dihydrazide, oxanilide, isophthaloyl dihydrazide, sebacoyl bisphenylhydrazide, N,N'- diacetyladipoyl dihydrazide, N,N'-bis(salicyloyl)oxalyl dihydrazide, N,N'-bis(salicyloyl)thiopropionyl dihydrazide.

[00118] 4. Phosphites and phosphonites, for example, triphenyl phosphite, diphenylalkyl phosphites, phenyldialkyl phosphites, tris(nonylphenyl) phosphite, trilauryl phosphite, trioctadecyl phosphite, distearylpentaerythritol diphosphite, tris(2,4-di-tert-butylphenyl) phosphite, di-isodecyl pentaerythritol diphosphite, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, bis(2,4-dicumylphenyl)pentaerythritol diphosphite, bis(2,6-di-tert-butyl-4-methylphenyl) pentaerythritol diphosphite, diisodecyloxypentaerythritol pentaerythritol diphosphite, bis(2,4,6-tris(tert-butylphenyl)pentaerythritol diphosphite, triestearyl sorbitol triphosphite, tetrakis(2,4-di-tert-butylphenyl) 4,4'-biphenylene diphosphonite, 6-iso-octyloxy-2,4,8,10-tetra-tert-butyl-12H-dibenz[d,g]-1,3,2- dioxaphosphocin, bis(2,4-di-tert-butyl-6 -methylphenyl)methyl phosphite, bis(2,4-di-tert-butyl-6-methylphenyl)ethyl phosphite, dibenz[d,g]-1,3,2-dioxaphosphocine, butyl-1,1'-biphenyl-2 ,2'-diyl)phosphite], biphenyl-2,2'-diyl)phosphite, dioxaphosphiran.

[00119] The following phosphites are especially preferred:

[00120] Tris(2,4-di-tert-butylphenyl) phosphite (Irgafos 168 (RTM, Ciba Inc.), tris(nonylphenyl) phosphite,

[00121] 5. Hydroxylamines, for example, N,N-dibenzylhydroxylamine, N,N-dioctylhydroxylamine, N,N-dilaurylhydroxylamine, N,N-dioctadecylhydroxylamine, N-hexadecyl-N-octadecyl- hydroxylamine, N-heptadecyl-N-octadecylhydroxylamine, N,N-dialkylhydroxylamine derived from hydrogenated tallow amine.

[00122] 6. Nitrones, for example, N-benzyl-a-phenylnitrone, N-ethyl-a-methylnitrone, N-octyl-α-heptylnitrone, N-lauryl-α-undecylnitrone, N-tetradecyl- N-hexadecyl- a-pentadecylnitrone, N-octadecyl-a- N-hexadecyl-a-heptadecylnitrone, N-octadecyl-a- N-heptadecyl-a-heptadecylnitrone, N-octadecyl-a-hexa-decylnitrone, nitrone derived from N,N-dialkyl -hydroxylamine, derived from hydrogenated tallow amine.

[00123] 7. Thiosynergists, for example, dilauryl thiodipropionate, dimistryl thiodipropionate, distearyl thiodipropionate or distearyl disulfide.

[00124] 8. Peroxide removers, for example, β-thiodipropionic acid ester, for example, lauryl, stearyl, myristyl or tridecyl ester, mercaptobenzimidazole or the zinc salt of 2-mercaptobenzimidazole, zinc dibutyldithiocarbamate, dioctadecyl disulfide, pentaerythritol tetrakis-(β-dodecylmercapto)propionate.

[00125] 9. Polyamide stabilizers, for example, copper salts in combination with iodides and/or phosphorous compounds and divalent manganese salts.

[00126] 10. Basic co-stabilizers, for example, melamine, polyvinylpyrrolidone, dicyandiamide, triallyl cyanurate, urea derivatives, hydrazine derivatives, amines, polyamides, polyurethanes, alkali metal salts and alkaline earth metal salts of higher fatty acids , for example, calcium stearate, zinc stearate, magnesium behenate, magnesium stearate, sodium ricinoleate and potassium palmitate, antimony pyrocatecholate or zinc pyrocatecholate.

[00127] 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 the salts thereof, for example, 4-tert-butylbenzoic acid, adipic acid, diphenylacetic acid, sodium succinate or sodium benzoate; polymeric compounds, such as ionic copolymers (ionomers), or Irgaclear XT 386 (RTM, Ciba). Especially preferred are 1,3:2,4-bis(3',4'-dimethylbenzylidene)sorbitol, 1,3:2,4-di(paramethyl-dibenzylidene)sorbitol, and 1,3:2,4-di( benzylidene)sorbitol.

[00128] 12. Fillers and reinforcing agents, for example, calcium carbonate, silicates, glass fibers, glass spheres, asbestos, talc, kaolin, mica, barium sulfate, metal oxides and hydroxides, carbon black, graphite, wood flour and flours or fibers from other natural products, synthetic fibers.

[00129] 13. Other additives, for example, pigments, such as carbon black, titanium dioxide in its rutile or anatase forms, color pigments; plasticizers; lubricants; emulsifiers; rheology additives; anti-slip/anti-block additives; catalysts; flow control agents; optical brighteners; antistatic agents and blowing agents.

[00130] 14. Benzofuranones and indolinones, for example, those described in U.S. 4,325,863; U.S. 4,338,244; U.S. 5,175,312; U.S. 5,216,052; U.S. 5,252,643; DE-A-4316611; DE-A-4316622; DE-A-4316876; EP-A-0589839, EP-A-0591102; EP-A-1291384 or 3-[4-(2-acetoxyethoxy)phenyl]-5,7-di-tert-butylbenzofuran-2-one, 5,7-di-tert-butyl-3-[4-(2 -stearoyloxy-ethoxy)phenyl]benzofuran-2-one, 3,3'-bis[5,7-di-tert-butyl-3-(4-[2-hydroxyethoxy]phenyl)benzofuran-2-one], 5 ,7-di-tert-butyl-3-(4-ethoxyphenyl)benzofuran-2-one, 3-(4-acetoxy-3,5-dimethylphenyl)-5,7-di-tert-butylbenzofuran-2-one, 3-(3,5-dimethyl-4-pivaloyloxyphenyl)-5,7-di-tert-butylbenzofuran-2-one, 3-(3,4-dimethylphenyl)-5,7-di-tert-butylbenzofuran-2- one, 3-(2,3-dimethylphenyl)-5,7-di-tert-butylbenzofuran-2-one, 3-(2-acetyl-5-iso-octylphenyl)-5-iso-octylbenzofuran-2-one.

[00131] 15. Terpene derivatives, for example, those described in WO 2003/080011, those mentioned in the complete list of Kirk-Othmer, Encyclopedia of Chemical Technology, John Wiley & Sons, 4th edition (1994), Vol. 23, P. 833-882. 16. Flame retardants

[00132] 16.1 phosphorus-containing flame retardants, for example, tetraphenyl resorcinol diphosphite (Fyrolflex RDP, RTM, Akzo Nobel), tetrakis(hydroxymethyl)phosphonium sulfide, triphenyl phosphate, diethyl-N,N-bis(2-hydroxyethyl) -aminomethyl phosphonate, hydroxyalkyl ester of phosphoric acids, ammonium polyphosphate (APP), resorcinol diphosphate oligomer (RDP), phosphazene or ethylenediamine diphosphate (EDAP) flame retardants.

[00133] 16.2 nitrogen-containing flame retardants, for example, melamine-based flame retardants, isocyanurates, polyisocyanurate, isocyanuric acid ester, such as tris-(2-hydroxyethyl)isocyanurate, tris(hydroxymethyl)isocyanurate, tris( 3-hydroxy-n-propyl)isocyanurate, triglycidyl isocyanurate, melamine cyanurate, melamine borate, melamine phosphate, melamine pyrophosphate, melamine polyphosphate, melamine ammonium polyphosphate, melamine ammonium pyrophosphate, dimelamine phosphate, melamine pyrophosphate dimelamine, benzoguanamine, allantoin, glycoluril, urea cyanurate, a melamine condensation product of the melem series, melam, melon, and/or a higher condensed compound or a melamine reaction product with phosphoric acid or a mixture thereof.

[00134] 16.3 organohalogen flame retardants, e.g., polybrominated diphenyl oxide (DE-60F, Great Lakes), decabromodiphenyl oxide (DBDPO; Saytex 102E (RTM, Albemarle)), tris[3-bromo-2 ,2-bis(bromomethyl)propyl] phosphate (PB 370, (RTM, FMC Corp.)), tris(2,3-dibromopropyl)phosphate, tris(2,3-dichloropropyl)phosphate, chlorendic acid, tetrachlorophthalic acid, tetrabromophthalic, mixture of poly-β-chloroethyl triphosphonate, tetrabromobisphenol A-bis(2,3-dibromopropyl ether) (PE68), brominated epoxy resin, ethylene-bis(tetrabromophthalimide) (Saytex BT-93 (RTM, Albemarle)), bis(hexachlorocyclopentadiene) cyclooctane (Declorane Plus (RTM, Oxichem)), chlorinated paraffins, octabromodiphenyl ether, hexachlorocyclopentadiene derivatives, 1,2-bis(tribromophenoxy)ethane (FF680), tetrabromobisphenol A (Saytex RB100 (RTM, Albemarle) ), ethylene bis-(dibromonorbornanedicarboximide) (Saytex BN-451 (RTM, Albemarle)), bis-(hexachlorocycloentadene)cyclooctane, PTFE, tris(2,3-dibromopropyl) isocyanurate, or ethylene-bis-tetrabromophthalimide.

[00135] The previously mentioned halogenated flame retardants are routinely combined with an inorganic oxide synergist.

[00136] 16.4 inorganic flame retardants, for example, aluminum trihydroxide (ATH), boehmite (AlOOH), magnesium dihydroxide (MDH), zinc borates, CaCO3, organically modified layered silicates, double hydroxides organically modified layer and mixtures thereof. Regarding synergistic combination with halogenated flame retardants, the most common inorganic oxide synergists are zinc oxides, antimony oxides such as Sb2O3 or Sb2O5, or boron compounds.

[00137] An additional additive selected from the group of antioxidants, UV absorbers, hindered amine light stabilizers, nickel compounds, metal deactivators, phosphites and phosphonites, hydroxylamines, thiosynergists, nucleating agents, peroxide scavengers, fillers is preferred. or reinforcing agents and terpene derivatives.

[00138] A composition comprising components a), b), a metal oxide and a phenolic antioxidant selected from lists 1.1-1.18, in the manner provided above, is especially preferred. An especially preferred metal oxide in such a combination is zinc oxide.

[00139] Particularly, a composition comprising components a), b) and a phenolic antioxidant selected from lists 1.1-1.18, in the manner provided above, is preferred.

[00140] Most preferred phenolic antioxidants in these compositions are β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid ester with mono- or polyhydric alcohols (i.e. list 1.13.). Especially preferred are tetrakis-[3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-propionyloxymethyl]-methane and octadecyl ester of acid 3-(3,5-di-tert-butyl-4- hydroxy-phenyl)-propionic.

[00141] Preferred is a composition comprising components a), b), a phenolic antioxidant selected from lists 1.1-1.18 in the manner provided above, a phosphite stabilizer selected from list 4, in the manner provided above, and a basic co-stabilizer selected from list 10, as provided above. Especially preferred is the composition in which said basic co-stabilizer is calcium stearate.

[00142] Further preferred is a composition comprising a flame retardant selected from the group consisting of phosphorus-containing flame retardants, nitrogen-containing flame retardants, organohalogen flame retardants and inorganic flame retardants, for example, those provided in previous lists 16.1 to 16.4.

[00143] The following flame retardants are most preferred: tris(tribromoneopentyl)phosphate, resorcinol-bis-diphenylphosphate, pentaerythritol-dimethyl phosphonate, guanidine phenylphosphonate, melamine phenylphosphonate, dimethylaluminum phosphinate, methylethylaluminum phosphinate, diethylaluminum phosphinate, poly -[2,4-(piperazine-1,4-yl)-6-morpholine-4-yl)-1,3,5-triazine] and ammonium polyphosphate.

[00144] The optional additional additive in the stabilized compositions of the invention can be contained from 0.01% to 5%, preferably from 0.025% to 2%, and especially from 0.1% to 1% by weight of the stabilized composition.

[00145] In the case of a flame retardant as an optional additional additive, the flame retardant is advantageously contained in the composition of the invention in an amount of 0.5% to 60.0% by weight of the organic material; for example, from 1.0% to 40.0%; for example, from 5.0% to 35.0% by weight of organic material.

[00146] Component b), as well as an optional additional additive of the invention, can be easily incorporated into the organic material as component a) by conventional techniques, at any convenient stage before manufacturing articles molded from it.

[00147] Component b) as well as an optional additional additive can be incorporated judiciously by one of the following methods: - as an emulsion or dispersion (for example, to latex or emulsion polymers) - as a dry mix during joining - by introduction directly into the processing apparatus (e.g. extruders, internal mixers) - as a solution in an organic solvent - as a melt.

[00148] The organic material as component a) can be in the form of a solid, solution, suspension or emulsion.

[00149] The incorporation of component b), as well as an optional additional additive, is carried out, in the case of thermoplastic polymers as component a), best in a thermal compounding step. The complete joining of component a), component b), as well as an optional additional additive is followed by an extrusion of the physical joint at elevated temperature. Typically, an extruder with suitable screw configuration is used for this step.

[00150] Additives can also be added to the polymer as component a) in the form of a master mix (“concentrate”), which contains component b), as well as an optional additional additive incorporated into an additional polymer of the master mix. The concentration for the additives is, for example, 1% to 50%, in particular 2.5% to 30% by weight of the standard mixture. Said additional masterbatch polymer need not necessarily be of identical structure to that of the polymer as component a). The polymer of the master mix may be produced in a different way than the polymer as component a). The standard mixture may be in the form of a powder, granules, solutions, suspensions or in the form of latex.

[00151] In the case of a polymer as component a), the polymer compositions of this invention can be employed in various forms and/or processed to provide various final products, for example, as to obtain films, fibers, tapes, molding compositions , profiles or as binders for coating materials, adhesives or putties

[00152] In more detail, the final product, respectively, article, can be any type of polymeric article, which needs stabilization in natural sunlight and/or humidity at low, ambient or elevated temperatures. For example, the polymer component can be used to manufacture polymeric films, sheets, bags, bottles, tubes, cables, Styrofoam cups, plates, utensils, blister packaging, boxes, packaging packages, plastic fibers, tapes, articles agricultural, such as twine, liner films, straw protective layer films, small tunnel films, silage films, silage bags, stretched bale wraps, banana bags, direct covers, non-wovens, pots for agricultural use, geotextiles, landfill covers, industrial covers, waste covers, temporary scaffolding sheets, construction films, silt fences, bird curtains, films for the development of temporary shelter constructions, disposable diapers, disposable garments or the like.

[00153] Polymeric articles may be manufactured by any process available to those skilled in the art including, but not limited to, extrusion, blow extrusion, film casting, film blowing, calendering, injection molding, blow molding, molding. compression, thermoforming, spinning, blow extrusion or rotational casting.

[00154] For the production of the desired polymeric article from the polymeric compositions of this invention, any appropriate equipment may be used, depending on the final form of the article, for example, a blow extruder in the case of films, an extrusion machine in the case of sheets or an injection molding machine.

[00155] Mixtures of the compounds of formulas (1) and (2), as well as the compounds of formula (2), are excellent stabilizers against the harmful effect of oxidation by light and heat in different applications such as, but not limited to, for agriculture, with or without the use of pesticides. The mixtures are also excellent flame retardants.

[00156] An additional embodiment of this invention is a method for stabilizing an organic material susceptible to oxidative, thermal or light-induced degradation, which comprises incorporating into it or applying to it the additive mixture of formulas (1) and ( two).

[00157] It is also preferred to use the additive mixture of formulas (1) and (2) for stabilizing an organic material susceptible to oxidative, thermal or light-induced degradation.

[00158] As for the compounds of formulas (1) and (2), the definitions and preferences provided here previously apply.

[00159] An additional embodiment of this invention is a method for improving the flame retardancy of an organic material, which comprises incorporating into it or applying to it the additive mixture of formulas (1) and (2). It is also preferred to use the additive mixture of formulas (1) and (2) to improve the flame retardancy of an organic material.

[00160] As for compounds of formulas (1) and (2), the definitions and preferences provided here previously apply.

[00161] An additional embodiment of this invention is a method for stabilizing an organic material susceptible to oxidative, thermal or light-induced degradation, which comprises incorporating into it or applying to it a compound of formula (2).

[00162] It is also preferred to use the compound of formula (2) for stabilizing an organic material susceptible to oxidative, thermal or light-induced degradation.

[00163] As for the compound of formula (2), the definitions and preferences provided here previously apply.

[00164] Another aspect of this invention is a process for preparing a compound of formula (1') comprising subjecting a compound of formula (2) to an oxidation reaction, followed by a hydrogenation reaction, in which R1, R2, R3, R4, R'1, R'2, R'3 and R'4 are independently of each other hydrogen or C1-C18 alkyl, X1 and X'1 are independently of each other C2-C12 alkylene or hydroxyl-substituted C3-C12 alkylene; one to five radicals of the radicals Z1, Z2, Z3, Z4, Z5 and Z6 are a group of the formula -O-CH2-CH2-CH2-R and the remainder of the radicals Z1, Z2, Z3, Z4, Z5 and Z6 is hydrogen or hydroxy, especially hydrogen, one to five radicals of the radicals Y1, Y2, Y3, Y4, Y5 and Y6 are a group of the formula -CH2-CH=CH-R and the remainder of the radicals Y1, Y2, Y3, Y4, Y5 and Y6 is hydrogen, and R is hydrogen or C1-C15 alkyl. R is preferably hydrogen.

[00165] The preferences given here above may apply to the compounds of formulas (1') and (2) of the previous preparation process, as applicable. Highly preferred for these compounds are those of formulas (1-A) and (2-A), in which the substituents are defined in the manner provided for the previous preparation process, and for which the substituents in addition to the applicable preferences provided apply. here previously

[00166] Compounds of formula (2), which are used for the preparation of compounds of formula (1'), for example, can be prepared by reacting a corresponding compound of formula (3) wherein R'1, R'2, R'3, R'4 and X'1 are defined in the manner given previously for formula (2), with an allyl halide of the formula Hal-CH2-CH=CH-R (4), wherein Hal is halogen, preferably chlorine or especially bromine, and R is as defined above.

[00167] The reaction, for example, can be carried out in the presence of an organic solvent, such as xylene, toluene, mesitylene or ethylbenzene, especially xylene or toluene. A base is generally added, such as sodium carbonate, potassium carbonate, sodium hydroxide or sodium phosphate, preferably sodium carbonate or potassium carbonate. It is preferable to carry out the reaction at a temperature of 130°C to 180°C, especially 130°C to 160°C. Instead of an allyl halide of formula (4), corresponding allyl alcohols or corresponding allyl carbonates can also be used.

[00168] Allyl halide is, as a rule, used in sub-stoichiometric quantities, since for the preparation of compounds of formula (1') compounds of formula (2) are used, in which only one to five of the radicals Y1, Y2, Y3, Y4, Y5 and Y6 are a group of the formula -CH2-CH=CH-R. For example, for the preparation of compounds of formula (2), wherein five of the radicals Y1, Y2, Y3, Y4, Y5 and Y6 are a group of the formula -CH2-CH=CH- R, an amount of about 5 /6 of the stoichiometric amount of allyl halide can be used.

[00169] Allyl halide can preferably be used in amounts that are 40 to 95%, especially 40 to 90% of the stoichiometric amount. An amount of 50 to 90%, especially 60 to 90% of the stoichiometric amount, is more preferred.

[00170] The compound of formula (3) can be prepared according to known methods, or in analogy to known methods, for example, in the manner described in WO 2011/029744, Example 1.

[00171] If desired, the compounds of formula (2) can be isolated, for example, by removing the organic solvent under reduced pressure.

[00172] For a further reaction, it is preferable to use the reaction mixture without isolation, in the manner obtained after the previous reaction of the compound of formula (3) with the allyl halide of formula (4).

[00173] To prepare the compound of formula (1'), the compound of formula (2) is subjected to an oxidation reaction, followed by a hydrogenation reaction.

[00174] Oxidation is generally carried out with peracetic acid. Alternatively, hydrogen peroxide, meta-chloroperoxybenzoic acid or tert-butyl hydroperoxide can also be used. The reaction can be carried out, for example, in the presence of an organic solvent such as xylene, toluene, mesitylene or ethylbenzene, especially xylene or toluene. Likewise, dichloromethane can be used. A base such as sodium carbonate, sodium hydrogen carbonate, potassium carbonate, sodium hydroxide, or sodium phosphate, especially sodium carbonate or potassium carbonate, is generally used. It is preferable to carry out the reaction at a temperature of 0°C to 40°C, especially 0°C to 30°C. According to the oxidation step, the groups of the formula -CH2-CH=CH-R can be converted into the groups of the formula -O-CH2-CH=CH-R.

[00175] If desired, the resulting intermediates can be isolated, for example, by removing the organic solvent under reduced pressure. For a further reaction, it is preferable to use the reaction mixture without isolation, in the manner obtained after the previous oxidation step.

[00176] Hydrogenation is generally carried out with hydrogen. As a catalyst, it is preferable to use palladium. Alternative catalysts can be Pt, Rh, Ru or Ni. The catalyst loading can be 0.05 to 2% by weight. The reaction can be carried out, for example, in the presence of an organic solvent, such as xylene, toluene, mesitylene, ethylbenzene, methanol, especially toluene or xylene. It is also possible to use water. It is preferable to carry out the reaction at a temperature of 50°C to 90°C, especially 60°C to 80°C. Hydrogen pressure can be 10 to 50 bar.

[00177] The compounds resulting from formula (1') can be isolated, for example, by removing the organic solvent under reduced pressure.

Examples Examples of synthesis and preparation

[00178] Example 1: Synthesis of a compound of formula (1-A), in which 70 mol% of Z1, Z2, Z3, Z4, Z5 and Z6 are n-propyloxy and the remainder of these radicals is hydrogen or hydroxy. In the following, this compound is referred to as compound (101).

[00179] a) Synthesis of a compound of formula (2-A), in which 80 mol% of Y1, Y2, Y3, Y4, Y5 and Y6 are an allyl group and the remainder of these radicals is hydrogen. Hereinafter, this compound is referred to as compound (201).

[00180] In a one-liter autoclave equipped with a mechanical stirrer, 0.94 mol of Na2CO3 and 0.14 mol of the compound of formula (301) dissolved in xylene to reach a concentration of 45% by weight are added, then 0.79 mol of allyl bromide is added. The mixture is heated to 145°C for 7 hours, cooled to 60°C and washed with 26.7 mol of water at 85°C. A second wash is performed with 0.05 mol of Na2CO3 dissolved in 11.1 mol of water. The organic phase is used directly in the following step without any further purification. Conversion: 80%. b) Oxidation of compound of formula (201)

[00181] The reaction mixture obtained according to previous step a) is diluted to a concentration of 32% by weight with xylene, and is placed in a glass reactor equipped with a mechanical stirrer, thermocouple and a funnel with tap. 1.13 mol of Na2CO3 is added. The suspension is cooled to 0°C and 0.86 mol of peracetic acid solution (35% by weight in water) is added slowly over 3 hours. Subsequently, 16.7 mol of water is added and the mixture is heated and stirred at 75°C for 1 hour. The organic phase is separated, washed with 0.07 mol of Na2CO3 and 5.56 mol of water. The organic phase is used directly in the following steps without any further purification. Conversion: 93% c) Final synthesis of compound (101)

[00182] From the reaction mixture, as obtained according to previous step b), the solvent is removed to obtain a final concentration between 45 and 60% by weight. The solution is filled into a one liter autoclave along with 0.14 mmol Pd/C (5% by weight). The total mixture is heated to 70°C in hydrogen 3,000,000 Pascals (30 bar) for 4 hours.

[00183] The solution is cooled to room temperature, filtered to remove the catalyst and dried under reduced pressure. A slightly pinkish solid is obtained. Conversion: 98%. Softening range: 110-150°C.

[00184] Example 2: Synthesis of compound of formula (2-A), in which all of Y1, Y2, Y3, Y4, Y5 and Y6 are an allyl group. Hereinafter, this compound is referred to as compound (202).

[00185] The synthesis is carried out according to Example 1 a), but using 1.29 mol of allyl bromide (instead of 0.79 mol of allyl bromide).

[00186] The compound (202) is isolated by removing the solvent under reduced pressure to obtain a solid.

[00187] Example 3: Synthesis of a compound of formula (2-A), in which 50 mol% of Y1, Y2, Y3, Y4, Y5 and Y6 are an allyl group and the remainder of these radicals is hydrogen. Hereinafter, this compound is referred to as compound (203).

[00188] The synthesis is carried out according to Example 1 a), but adjusting the amount of allyl bromide used accordingly. Example 4: Preparation of mixtures

[00189] Compounds (101), (201), (202) and (203) are isolated in the manner provided in example 2 above. The mixtures given in application example 1 below, table 1, are prepared by homogeneously mixing the solids of the corresponding compounds in the indicated weight ratio.

[00190] Alternatively, it is also possible to directly mix the reaction mixtures of the compounds to be mixed, and then remove the solvent under reduced pressure to obtain solid mixtures.

Application Examples

[00191] Application example 1: Stabilization of LDPE (low density polyethylene) multilayer films.

[00192] Standard mix formulations are prepared containing 10% by weight in total of the light stabilizer(s) indicated in table 1 below, 0.4% by weight of tris{2,4- di-tert-butylphenyl} phosphite and 0.1% by weight of octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate as process stabilizers, and the remainder of polyethylene powder(Polimeri Europa Riblene ® FC 30, distinguished by a density of 0.922 g/cm3 and a melt flow index (190°C/2.16Kg) of 0.27 g/10min). Standard blend formulations are mixed in a turbo-mixer. Each standard blend formulation is extruded at a maximum temperature of 200°C on a laboratory scale OMC twin screw extruder (0 19mm, L/D=25). 360 g of the granules thus obtained for each masterbatch formulation are mixed with 30 g of a polyethylene masterbatch containing 0.4% by weight of tris{2,4-di-tert-butylphenyl} phosphite and 0.1% in weight of octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate as process stabilizers, and with 5610 g of the previously indicated virgin polyethylene in granules, in a Rhonarad® slow mixer for 10 minutes, resulting in the final formulation that contains 0.6% in total of the light stabilizer(s) indicated in table 1 below. Subsequently, each final formulation is blown into a Collin® laboratory scale 5-layer blow extruder (0 20-25-30mm, L/D 25), at a maximum temperature of 210°C, to provide a 5 layers of total thickness of 150 μm (45-5-50-5-45 μm), with the same formulation in all layers. The following formulations are prepared: Table 1: Application example 2

[00193] Film specimens for each formulation are exposed on a piece of Q-Panel QUV/se equipment (QUV, per ASTM G154, 1.55 W/m2 at 340 nm, cycle 6) for light accelerated weathering. Such specimens are obtained at defined intervals and evaluated for embrittlement. The longer the embrittlement time, the better the stabilization effect of sterically hindered stabilizers in different formulations. The results are reported in table 2 below. It can be observed that formulation 2, based on the compound (201) object of the present invention, is better than formulation 1C and that formulations 4, 5 and 6, based on mixtures with compound (201) or its homologues, are better than the 3C formulation.

[00194] Longer times for embrittlement are desired. Application example 3

[00195] This test aims to combine light irradiation and the use of agrochemicals, known to have a detrimental effect on the light stability performance of the light stabilizers contained therein. To achieve a purpose like this, an agrochemical treatment is carried out on the films prepared before artificial weathering. Film specimens for each formulation are mounted in a small experimental greenhouse (geographical coordinates: Lat. 44°25'40”N Long.11°16'39”E), within which a treatment with metam sodium, a fumigant to sulfur base used in agricultural practice, is carried out. After treatment, the small greenhouse is covered with a single piece of opaque film to block direct exposure of the sample to sunlight, in order to minimize in turn the effects of solar irradiation, and consequently possible differences in samples exposed in the series. subsequent testing. The experimental conditions are carefully monitored in order to obtain the desired level of sulfur contamination in the film samples, measured by inductively coupled plasma.

[00196] After agrochemical treatment, film specimens for each formulation are exposed on a Weather-O-Meter Atlas (WOM, according to ASTM G155, 0.35 W/m2 at 340 nm, dry cycle), for weathering light accelerated. Specimens of the required formulations are obtained at defined time intervals after exposure and subjected to evaluation of carbonyl increase. Carbonyl increase is measured using a Perkin-Elmer® Spectrum 100 FT-IR spectrophotometer as a measure of the degree of oxidation of the polymer, so low levels of carbonyl are desired. The results are reported in table 3. It can be seen that formulation 2, based on compound (201), object of the present invention, is better than formulation 1C, and that formulations 4, 5 and 6, based on mixtures with compound (201) or its homologues, are better than formulation 3C.

[00197] Little carbonyl increase is desired. Application example 4

[00198] An agrochemical treatment is carried out in the manner described in application example 3. After the agrochemical treatment, film specimens for each formulation are exposed on a Weather-O-Meter Atlas (WOM, according to ASTM G155, 0. 35 W/m2 at 340 nm, dry cycle), for light accelerated weathering. Specimens of the required formulations are obtained at defined time intervals after exposure, and subjected to evaluation of mechanical properties. The residual elongation at break is measured, using a Zwick® Z1.0 constant speed tensiometer (according to modified ISO 527), in order to evaluate the degradation of the mechanical properties of the plastic film, as a consequence of polymer degradation after its oxidation.

[00199] The results are reported in table 4.

[00200] High values are desired. Application example 5

[00201] As in application example 3, this test aims to combine light irradiation and the use of agrochemicals. Also in this test, an agrochemical treatment is carried out on the films prepared before artificial weathering. Film specimens for each formulation are assembled outdoors, in an experimental cabinet (geographical coordinates: Lat. 44°25'40”N Long.11°16'39”E), inside which some burners of the type used in practice Common agricultural compounds are added to allow sublimation of elemental sulfur, a widely used fungicide. The so-called “sulfur burning” is carried out in such a way as to burn a specific weighted quantity of sulfur. The amount of sulfur burned is regulated and the weathering conditions are carefully monitored in order to obtain the desired level of sulfur contamination in the film samples, measured by inductively coupled plasma.

[00202] After agrochemical treatment, film specimens for each formulation are exposed on a Weather-O-Meter Atlas (WOM, according to ASTM G155, 0.35 W/m2 at 340 nm, dry cycle), for weathering light accelerated. Specimens of the required formulations are obtained at defined time intervals after exposure, and subjected to evaluation of carbonyl increase. Carbonyl increase is measured using a Perkin-Elmer® Spectrum 100 FT-IR spectrometer as a measure of the polymer's degree of oxidation. The results are reported in table 4 below. It can be observed that formulation 5, based on the mixture between compound (201) and compound (101), object of the present invention, is better than formulation 3C, showing better stabilization in light, when in the presence of agrochemical treatment. .

[00203] Little carbonyl increase is desired. Application example 6

[00204] An agrochemical treatment is carried out in the manner described in application example 5. After the agrochemical treatment, film specimens for each formulation are exposed on a Weather-O-Meter Atlas (WOM, in accordance with ASTM G155, 0 .35 W/m2 at 340 nm, dry cycle), for light accelerated weathering. Specimens of the desired formulations are obtained at defined time intervals after exposure, and subjected to evaluation of mechanical properties, in the manner described in application example 4. The results are reported in table 6 below.

[00205] High values are desired.

Claims (14)

1. Additive mixture, characterized by the fact that it comprises a compound of formula (1) and a compound of formula (2) wherein R1, R2, R3, R4, R'1, R'2, R'3 and R'4 are independently of each other hydrogen or C1-C18 alkyl, X1 and X'1 are independently of each other C2-alkylene C12 or hydroxyl-substituted C3-C12 alkylene; at least one of the radicals Z1, Z2, Z3, Z4, Z5 and Z6 is C1-C18 alkyloxy or C5-C7 cycloalkyloxy and the remainder of the radicals Z1, Z2, Z3, Z4, Z5 and Z6 are independently of each other hydrogen, hydroxy , C1-C18 alkyloxy or C5-C7 cycloalkyloxy, and at least one of the radicals Y1, Y2, Y3, Y4, Y5 and Y6 is a group of the formula -CH2-CH=CH-R and the remainder of the radicals Y1, Y2, Y3, Y4, Y5 and Y6 are independently of each other hydrogen or a group of the formula -CH2-CH=CH-R, where R is hydrogen, C1-C18 alkyl or C5C7 cycloalkyl. 2. Additive mixture according to claim 1, characterized by the fact that R1, R2, R3, R4, R'1, R'2, R'3 and R'4 are C1-C12 alkyl. 3. Additive mixture according to claim 1 or 2, characterized by the fact that X1 and X'1 are C2-C8 alkylene. 4. Additive mixture according to any one of claims 1 to 3, characterized in that one to five radicals of radicals Z1, Z2, Z3, Z4, Z5 and Z6 are C1-C18 alkyloxy or C5-C7 cycloalkyloxy and the The remainder of the radicals Z1, Z2, Z3, Z4, Z5 and Z6 is hydrogen or hydroxy. 5. Additive mixture according to any one of claims 1 to 4, characterized in that Z1, Z2, Z3, Z4, Z5 and Z6 in the meaning as C1-C18 alkyloxy are a group of the formula -O-CH2-CH2 - CH2-R, where R is hydrogen or C1-C15 alkyl. 6. Additive mixture according to any one of claims 1 to 5, characterized in that one to five radicals of the radicals Y1, Y2, Y3, Y4, Y5 and Y6 are a group of the formula -CH2-CH=CH- R and the rest of the radicals Y1, Y2, Y3, Y4, Y5 and Y6 are hydrogen. 7. Additive mixture according to any one of claims 1 to 6, characterized by the fact that R is hydrogen. 8. Additive mixture according to claim 1, characterized by the fact that R1, R2, R3, R4, R'1, R'2, R'3 and R'4 are C1-C12 alkyl, X1 and X' 1 are C2-C8 alkylene, one to five radicals of radicals Z1, Z2, Z3, Z4, Z5 and Z6 are C1-C18 alkyloxy or C5-C7 cycloalkyloxy and the remainder of radicals Z1, Z2, Z3, Z4, Z5 and Z6 is hydrogen or hydroxy, one to five radicals of the radicals Y1, Y2, Y3, Y4, Y5 and Y6 are a group of the formula -CH2-CH=CH-R and the remainder of the radicals Y1, Y2, Y3, Y4, Y5 and Y6 is hydrogen, and R is hydrogen. 9. Additive mixture according to any one of claims 1 to 8, characterized in that the weight ratio of compound of formula (1) to compound of formula (2) is 5:95 to 95:5. 10. Composition, characterized by the fact that it comprises a) an organic material that is susceptible to oxidative, thermal or light-induced degradation; and b) an additive mixture as defined in claim 1. 11. Method for stabilizing an organic material susceptible to oxidative, thermal or light-induced degradation, characterized by the fact that it comprises incorporating into it or applying to it an additive mixture as defined in claim 1. 12. Method for improving flame retardancy of an organic material, characterized by the fact that it comprises incorporating into it or applying to it an additive mixture as defined in claim 1. 13. Method for stabilizing an organic material susceptible to oxidative, thermal or light-induced degradation, characterized by the fact that it comprises incorporating into it or applying to it a compound of formula (2) as defined in claim 1. 14. Process, characterized by the fact that it is for the preparation of a compound of formula (1') comprising subjecting a compound of formula (2) to an oxidation reaction, followed by a hydrogenation reaction, in which R1, R2, R3, R4, R'1, R'2, R'3 and R'4 are independently of each other hydrogen or C1-C18 alkyl, X1 and X'1 are independently of each other C2-C12 alkylene or hydroxyl-substituted C3-C12 alkylene; one to five radicals of the radicals Z1, Z2, Z3, Z4, Z5 and Z6 are a group of the formula -O-CH2-CH2-CH2-R and the remainder of the radicals Z1, Z2, Z3, Z4, Z5 and Z6 is hydrogen or hydroxy, one to five radicals of the radicals Y1, Y2, Y3, Y4, Y5 and Y6 are a group of the formula -CH2-CH=CH-R and the remainder of the radicals Y1, Y2, Y3, Y4, Y5 and Y6 are hydrogen, and R is hydrogen or C1-C15 alkyl, preferably hydrogen.