Use of hydroxycinnamic acid salts for stabilizing organic materials, stabilized organic materials, methods for stabilizing organic materials, specific stabilizers and stabilizer compositions

Abstract

The present invention relates to the use of specific hydroxycinnamic acid salts for stabilizing organic materials. The invention also relates to the corresponding organic materials stabilized by incorporation of specific hydroxycinnamic acid salts and to methods for stabilizing organic materials. Furthermore, aluminum salts of specific hydroxycinnamic acids are described which are suitable as organic stabilizers. The invention also relates to stabilizer compositions comprising the corresponding hydroxycinnamic acid salts.

Description

TECHNICAL FIELD

[0001] The present invention relates to the use of specific hydroxycinnamic acid salts for stabilizing organic materials. The invention also relates to the corresponding organic materials stabilized by incorporation of specific hydroxycinnamic acid salts as well as to a process for stabilizing organic materials. Furthermore, aluminum salts of specific hydroxycinnamic acids are described which are suitable as organic stabilizers. The invention also relates to stabilizer compositions comprising the corresponding hydroxycinnamic acid salts. BACKGROUND

[0002] Organic materials, such as plastics, undergo an aging process which ultimately leads to a loss of the desired properties, for example mechanical property values. This process, which is referred to as autoxidation, leads to changes in the polymer chains, for example in terms of molecular weight or the formation of new chemical groups, which are caused by free-radical chain cleavage by mechanochemical processes or by UV radiation in the presence of oxygen. Stabilizers are therefore used to prevent or at least delay the aging. An important representative of stabilizers is the antioxidant, which interferes with the free radicals formed in the autoxidation and thus interrupts the degradation process. A distinction is usually made between primary antioxidants, which are able to react directly with oxygen-containing free radicals or C-radicals, and secondary antioxidants, which react with hydroperoxides formed as intermediates (cf. C. L. Jenkins, A. J. O’Connor, in: Antioxidants in Ullmann’s encyclopedia of industrial chemistry, Wiley-VCH Verlag, Weinheim 2015). Typical representatives of primary antioxidants are, for example, phenolic antioxidants, amines and lactones. The classes of secondary antioxidants are phosphorus compounds, such as phosphites and phosphonites, and organic sulfur compounds, such as thioesters and disulfides. In practice, primary and secondary antioxidants are often used in combination, which leads to a synergistic effect.

[0003] Plastics made from fossil raw materials such as petroleum or natural gas are increasingly being supplemented or replaced by plastics based on renewable raw materials obtained by biochemical processes. The problem of durability of primary and secondary antioxidants for these (and for plastics made from fossil raw materials) also comes with it. There is therefore a need for stabilizers based on renewable and available raw materials, which have high effectiveness, low volatility and are compatible with the polymer substrate.

[0004] ​Essentially, primary antioxidants from renewable raw materials are known, which are also occasionally used in plastics. A typical example is tocopherol (vitamin E). Like conventional antioxidants, tocopherol has a sterically hindered phenolic structure and can be used alone or in combination with secondary antioxidants (e.g. S. Al-Malaika, Macromol. Symp. 2001, 176, 107-117). For example, tocopherol can be isolated from natural substances such as wheat germ oil, sunflower oil or olive oil.

[0005] Other known phenols with antioxidant effects in plastics are, for example, quercetin (B. Kirschweng et al., Eur. Pol. J. 2018, 103, 228-237), dihydromyricetin (B. Kirschweng et al., Pol. Degr. Stab. 2016, 133, 192-200), derivatives of rosmarinic acid (K. Doudin et al., Pol. Degr. Stab. 2016, 130, 126-134) or tannins (W. J. Grigsby et al., Polymers 2013, 5, 344-360).

[0006] In addition, derivatives of ferulic acid (A. F. Reano et al., ACS Sustainable Chemistry and Engineering 4 (2015), 6562-6571) and caffeic acid (V. Ambrogi et al., Biomacromolecules 15 (2014), 302-310) are also known.

[0007] However, most natural phenols require a great deal of effort in the isolation, purification or production of suitable follow-up products.

[0008] Ferulic acid and its salts are used, for example, in the cosmetics industry or as pharmaceutically active ingredients (e.g. FR 2907338, CN 101181256, DE 1957433), the production of salts is essentially known (e.g. AT 317184). In CN 107629310, a layered compound with a light stabilizer is synthesized, which can contain, for example, sodium cinnamate as a possible light stabilizer and can be used in plastics or coatings.

[0009] Furthermore, ester derivatives of ferulic acid (A. F. Reano et al., ACS Sustainable Chemistry and Engineering 4 (2015), 6562-6571, A. F. Reano et al., ACS Sustainable Chemistry and Engineering 3 (2015), 3486-3496), oligomers and polymers of ferulic acid (US2016257846) and caffeic acid (V. Ambrogi et al. Biomacromolecules 15 (2014), 302-310) are also known. However, these derivatives are produced in a relatively complex manner by enzymatic synthesis. Also known as ester compounds in the form of ferulic acid derivatives are isosorbide esters (US20070189990) and cholestanol esters (WO2018153917). SUMMARY

[0010] Starting from this, the object of the present application is to provide a persistent antioxidant for organic materials, in particular polymers based on renewable raw materials, with high effectiveness, high thermal stability and low volatility.

[0011] This object is achieved by the use of the compounds of the general formula I defined in claim 1 for stabilizing organic materials, in particular against oxidative, thermal and / or actinic degradation. Furthermore, this object is achieved by the organic materials according to claim 11. The present application also relates to a method for stabilizing organic materials as claimed in claim 14. Specific cinnamic acid salts for use as stabilizers are defined in claim 15. Furthermore, the present application relates to stabilizer compositions according to claim 16. The respective subclaims give advantageous further developments.

[0012] According to a first aspect, the present application thus relates to the use of a compound or a mixture of compounds according to the general formula I

[0013]

[0014] wherein

[0015] R 1 , R 2 and R 3 are each independently selected from the group consisting of hydroxyl, straight-chain or branched alkoxy having 1 to 6 carbon atoms and hydrogen, with the proviso that at least one of the residues R 1 , R 2 and R 3 is a hydroxyl residue, M is selected from the group consisting of metals and n is an integer from 1 to 4, for stabilizing organic materials, in particular against oxidative, thermal and / or actinic degradation.

[0016] According to the application, the cosmetic is not an organic material.

[0017] According to the application, a metal salt of a hydroxycinnamic acid, in which at least one phenolic group has steric hindrance, is used as stabilizer.

[0018] Surprisingly, it has been found that the compounds according to the application according to formula I act as stabilizers and, based on renewable raw materials, have high efficiency, environmental friendliness and a favorable cost structure.

[0019] One preferred embodiment provides that the application relates to the stabilization of plastics, coatings, lubricants, hydraulic oils, engine oils, turbine oils, transmission oils, metalworking fluids, chemicals or monomers. For example, plastics in the form of injection-molded parts, foils or films, foams, fibers, cables and pipes, profiles, hollow bodies, small strips, membranes, for example geomembranes, or adhesives, which are produced by extrusion, injection molding, blow molding, calendering, pressing processes, spinning processes, rotational molding, for example for the electrical and electronics industry, the construction industry, the transportation industry (automotive, aircraft, ships, rail), for medical applications, for household appliances and electrical appliances, automotive parts, consumer goods, packaging, furniture, textiles. Another field of application is the stabilization of varnishes, paints and coatings as well as oils and fats.

[0020] One preferred embodiment provides that the application relates to the stabilization of plastics, coatings, lubricants, hydraulic oils, engine oils, turbine oils, transmission oils, metalworking fluids, chemicals or monomers. For example, plastics in the form of injection-molded parts, foils or films, foams, fibers, cables and pipes, profiles, hollow bodies, small strips, membranes, for example geomembranes, or adhesives, which are produced by extrusion, injection molding, blow molding, calendering, pressing processes, spinning processes, rotational molding, for example for the electrical and electronics industry, the construction industry, the transportation industry (automotive, aircraft, ships, rail), for medical applications, for household appliances and electrical appliances, automotive parts, consumer goods, packaging, furniture, textiles. Another field of application is the stabilization of varnishes, paints and coatings as well as oils and fats.

[0021] the residue R 1 , R 2 and R 3 are each a hydroxyl residue,

[0022] two of the residues R 1 , R 2 and R 3 are hydroxyl residues and one of the residues R 1 , R 2 and R 3 is hydrogen or a linear or branched alkoxy group having 1 to 6 carbon atoms,

[0023] one of the residues R 1 , R 2 and R 3 is a hydroxyl residue and two of the residues R 1 , R 2 and R 3 are linear or branched alkoxy groups having 1 to 6 carbon atoms, or

[0024] each of the residues R 1 , R 2 and R 3 is a hydroxyl residue, a linear or branched alkoxy group having 1 to 6 carbon atoms and hydrogen.

[0025] According to one particularly preferred embodiment, the compound according to general formula I is selected from the group consisting of:

[0026]

[0027] wherein M and n are defined as above.

[0028] According to this preferred embodiment, the hydroxycinnamic acid salt used according to the present application is thus derived from the following hydroxycinnamic acids:

[0029] a) ferulic acid

[0030]

[0031] b) isoferulic acid

[0032]

[0033] c) caffeic acid

[0034]

[0035] d) sinapic acid

[0036]

[0037] In particular, the metal M is selected from the group consisting of alkali metals, alkaline earth metals, aluminum and zinc.

[0038] The preferred alkali metals herein are lithium, sodium and potassium, with sodium being particularly preferred. The preferred alkaline earth metals are in particular magnesium and calcium.

[0039] It is a further preferred embodiment of the present application that the total amount of the compound according to general formula I, or in case of a mixture of various compounds according to general formula I, the total amount of all compounds according to general formula I, in the organic material is in the range of 0.01 to 10.00 wt.-%, preferably 0.02 to 5.00 wt.-%, particularly preferably 0.05 to 2.00 wt.-%.

[0040] In particular, the present application is suitable for the stabilization of thermoplastic, elastomeric or thermoset polymers. Examples of thermoplastic and thermoset polymers are:

[0041] a) Polymers from olefins or diolefins, for example polyethylenes (LDPE, LLDPE, VLDPE, ULDPE, MDPE, HDPE, UHMWPE), metallocene PEs (m-PE), polypropylenes, polyisobutylenes, poly-4-methyl-pent-1 -ene, polybutadienes, polyisoprenes, for example also natural rubber (NR), polyoctenamer, polyalkylene-carbon monoxide-copolymers, and copolymers in random or block form, for example polypropylene-polyethylene (EP), EPM or EPDM with, for example, 5-ethylidene-2-norbornene as comonomer, ethylene-vinyl acetate (EVA), ethylene-acrylate, such as ethylene-butyl acrylate, ethylene-acrylic acid and salts thereof (ionomers), and terpolymers, for example ethylene-acrylic acid-glycidyl (meth)acrylate, graft polymers such as polypropylene-graft-maleic anhydride, polypropylene-graft-acrylic acid, polyethylene-graft-acrylic acid, polyethylene-polybutyl acrylate-graft-maleic anhydride, and blends, for example LDPE / LLDPE or long-chain-branched polypropylene copolymers produced with alpha-olefins (such as 1 -butene, 1 -hexene, 1 -octene or 1 -octadecene) as comonomer

[0042] b) Polystyrenes, polymethylstyrenes, polyalpha-methylstyrenes, polyvinyl naphthalene, polyvinyl biphenyl, polyvinyl toluene, styrene-butadiene (SB), styrene-butadiene-styrene (SBS), styrene-ethylene-butylene-styrene (SEBS), styrene-ethylene-propylene-styrene, styrene-isoprene, styrene-isoprene-styrene (SIS), styrene-butadiene-acrylonitrile (ABS), styrene-acrylonitrile (SAN), styrene-acrylonitrile-acrylate (ASA), styrene-ethylene, styrene-maleic anhydride-polymers, including the corresponding graft copolymers such as styrene graft butadiene, maleic anhydride graft SBS or SEBS, and graft copolymers from methyl methacrylate, styrene-butadiene and ABS (MABS), and hydrogenated polystyrene derivatives, for example polyvinyl cyclohexane

[0043] c) Halogen-containing polymers, for example polyvinyl chloride (PVC), polychloroprene and polyvinylidene chloride (PVDC), copolymers of chloroethylene and vinylidene chloride or chloroethylene and vinyl acetate, chlorinated polyethylenes, polyvinylidene fluoride, epichlorohydrin homo- and copolymers (in particular with ethylene oxide (ECO))

[0044] d) Polymers of unsaturated esters, for example, polyacrylates and polymethacrylates, such as polymethyl methacrylate (PMMA), polybutyl acrylate, polylauryl acrylate, polystearyl acrylate, polyglycidyl acrylate, polyglycidyl methacrylate, polyacrylonitrile, polyacrylamide, copolymers such as polyacrylonitrile-polyacrylate,

[0045] e) Polymers of unsaturated alcohols and derivatives thereof, for example, polyvinyl alcohol, polyvinyl acetate, polyvinyl butyral, polyallyl phthalate, polyallyl melamine

[0046] f) Polyacetals, for example polyoxymethylene (POM) or copolymers with, for example, butyraldehyde,

[0047] g) Polymers of phenylene oxides and blends with polystyrene or polyamides,

[0048] h) Polymers of cyclic ethers, for example, polyethylene glycol, polypropylene glycol, polyethylene oxide, polypropylene oxide, polytetrahydrofuran,

[0049] i) Polyurethanes from hydroxyl-terminated polyethers or polyesters and aromatic or aliphatic isocyanates, for example 2,4- or 2,6-toluene diisocyanate or methylene diphenyl diisocyanate, in particular linear polyurethanes (TPU), polyureas,

[0050] j) Polyamides, for example, polyamide-6,6.6,6.10,4.6,4.10,6.12,10.10,10.12,12.12, polyamide 11, polyamide 12 and (partly) aromatic polyamides, for example polyphthalamide, which are produced, for example, from terephthalic acid and / or isophthalic acid with aliphatic diamines, such as hexamethylenediamine or m-xylylenediamine, or from aliphatic dicarboxylic acids, such as adipic acid or sebacic acid, with aromatic diamines, such as 1,4- or 1,3-diaminobenzene, blends of different polyamides, for example PA-6 and PA 6.6, or blends of polyamides and polyolefins, for example PA / PP

[0051] k) Polyimides, polyamide-imides, polyether-imides, poly- (ether) ketones, polysulfones, polyether sulfones, polyaryl sulfones, polyphenylene sulfides, polybenzimidazoles, polyhydantoins,

[0052] l) polyesters from aliphatic or aromatic dicarboxylic acids and diols or from hydroxycarboxylic acids, such as polyethylene terephthalate (PET), polybutylene terephthalate (PBT), polytrimethylene terephthalate (PTT), polyethylene naphthalate (PEN), poly-1,4-dimethylolcyclohexane terephthalate, polyhydroxybenzoate, polyhydroxynaphthoate, polylactic acid (PLA), polyhydroxybutyrate (PHB), polyhydroxyvalerate (PHV), polyethylene succinate, polytetramethylene succinate, polycaprolactone,

[0053] m) polycarbonates, polyester carbonates and blends, such as PC / ABS, PC / PBT,

[0054] PC / PET / PBT, PC / PA,

[0055] n) cellulose derivatives, such as nitrocellulose, cellulose acetate, cellulose propionate, cellulose butyrate,

[0056] o) epoxy resins consisting of di- or polyfunctional epoxide compounds in combination with curing agents, such as based on amines, anhydrides, dicyanamides, thiols, isocyanates or catalytically acting curing agents,

[0057] p) phenolic resins, such as phenol-formaldehyde resins, urea-formaldehyde resins, melamine-formaldehyde resins, q) unsaturated polyester resins made from unsaturated dicarboxylic acids and diols with vinyl compounds, such as styrene, alkyd resins, allyl resins

[0058] r) silicone resins, such as based on dimethylsiloxanes, methyl-phenyl-siloxanes or diphenylsiloxanes, such as end-capped with vinyl groups

[0059] s) and mixtures, combinations or blends of two or more of the above-mentioned polymers.

[0060] If the polymers indicated in a) to r) are copolymers, they can be present in the form of random ("statistical"), block or "tapered" structures. Furthermore, the polymers mentioned can be present in the form of linear, branched, star-shaped or hyperbranched structures.

[0061] If the polymers indicated in a) to r) are stereoregular polymers, they can be present in isotactic, syndiotactic and atactic form, or as stereoblock copolymers.

[0062] Furthermore, the polymers indicated in a) to r) can have amorphous and (partly) crystalline morphology.

[0063] Optionally, the polyolefins mentioned in a) can also be crosslinked, such as crosslinked polyethylene, which is then referred to as X-PE.

[0064] Furthermore, the compounds can be used for stabilizing rubbers and elastomers. Herein can be natural rubber (NR) or synthetic rubber materials, for example, NR (natural rubber), chloroprene (CR), polybutadiene (BR), styrene butadiene (SBR), polyisoprene (IR), butyl rubber (IIR), nitrile rubber (NBR), hydrogenated nitrile rubber (HNBR), polyester or polyether-polyurethane-rubber, silicone rubber.

[0065] In addition to new products, the plastics can also be recycled plastics, for example from industrial collections such as production waste, or from household or waste product recycling.

[0066] As plastics, thermoplastic plastics are preferred, and in particular plastics used in packaging, for example in food packaging, in particular polyolefins, polystyrene, polyesters and polyamides. Very particularly preferred are polypropylene homo- and copolymers, and polyethylene in the form of LDPE, LLDPE, HDPE, MDPE, VLDPE and polyethylene terephthalate (PET) homo- and copolymers.

[0067] Furthermore, aliphatic polyesters from renewable raw materials are particularly preferred, which are produced mainly from aliphatic dicarboxylic acids and aliphatic diols, from hydroxycarboxylic acids or lactones, for example polylactic acid (PLA), polyglycolic acid (PGA), polyhydroxybutyric acid (PHB), polyhydroxyvaleric acid (PHV), polyethylene succinate (PESu), polybutylene succinate (PBS), polyethylene adipate, poly(butylene succinate copolymer) (PBSA) or polycaprolactone (PCL).

[0068] According to the application, the plastics can be in particular in the form of injection-molded parts, foils or films, foams, fibers, cables and pipes, profiles, hollow bodies, small strips, membranes, for example geomembranes, or adhesives, which are produced by extrusion, injection molding, blow molding, calendering, pressing processes, spinning processes, rotational molding, for example for the electrical and electronics industry, the construction industry, the transport industry (automotive, aircraft, ships, rail), for medical applications, for household appliances and electrical appliances, automotive parts, consumer goods, packaging, furniture, textiles. Another field of application is the stabilization of varnishes, paints and coatings, and oils and fats.

[0069] Another advantageous embodiment of the invention is characterized in that the plastic is added to and / or contains at least one additional additive during use, said additive being selected from the group consisting of: primary and / or secondary antioxidants, especially primary and / or secondary antioxidants selected from the group consisting of: phosphites, phosphonites, thiols, phenolic antioxidants, sterically hindered amines, hydroxylamines, and mixtures or combinations thereof; ultraviolet absorbers, light stabilizers, hydroxylamine-based stabilizers, benzofuranone-based stabilizers, nucleating agents, impact toughness modifiers, plasticizers, lubricants, rheology modifiers, chain extenders, processing aids, pigments, dyes, fluorescent whitening agents, antibacterial agents, antistatic agents, lubricants, antiblocking agents, coupling agents, dispersants, compatibilizers, oxygen scavengers, acid scavengers, co-stabilizers, marking agents, and antifogging agents.

[0070] Suitable primary antioxidants (A) It contains phenolic antioxidants, amines, and lactones.

[0071] Suitable synthetic phenolic antioxidants The example is:

[0072] Alkylated monophenols, such as 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-bis(octadecyl)-4-methylphenol, 2 4,6-Tricyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, linear or branched nonylphenol, such as 2,6-dinonyl-4-methylphenol, 2,4-dimethyl-6-(1'-methylundecane-1'-yl)phenol, 2,4-dimethyl-6-(1'-methylheptadecane-1'-yl)phenol, 2,4-dimethyl-6-(1'-methyltetrazane-1'-yl)phenol and mixtures thereof;

[0073] Alkylthiomethylphenols, such as 2,4-dioctylthiomethyl-6-tert-butylphenol, 2,4-dioctylthiomethyl-6-methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol, and 2,6-bis(dodecylthiomethyl-4-nonylphenol;

[0074] Hydroquinone and alkylated hydroquinone, for example, 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butylhydroquinone, 2,5-di-tert-pentylhydroquinone, 2,6-diphenyl-4-octadecyloxyphenol, 2,6-di-tert-butylhydroquinone, 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;

[0075] Tocopherols, for example α-, β-, γ-, δ-tocopherol, and mixtures of these (vitamin E);

[0076] Hydroxylated thiodiphenyl ethers, for example 2,2'-thiobis(6-tert-butyl-4-methylphenol), 2,2'-thiobis(4-octylphenol), 4,4'-thiobis(6-tert-butyl-3-methylphenol), 4,4'-thiobis(6-tert-butyl-2-methylphenol), 4,4'-thiobis(3,6-di-sec-amylphenol), 4,4'-bis(2,6-di-tert-butyl-4-hydroxyphenyl) disulfide;

[0077] Alkylidenebisphenols, for example 2,2'-methylenebis(6-tert-butyl-4-methylphenol), 2,2'-methylenebis(6-tert-butyl-4-ethylphenol), 2,2'-methylenebis[4-methyl-6-(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-methylphenyl)-3-ndodecylmercapto butane, ethylene glycol bis[3,3-bis(3'-tert-butyl-4'-hydroxyphenyl)butyrate], bis(3-tert-butyl-4-hydroxy-5-methylphenyl)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-hydroxy-2-methylphenyl)-4-ndodecylmercapto butane, 1,1,5,5-tetra(5-tert-butyl-4-hydroxy-2-methylphenyl)pentane;

[0078] O-, N- and S-benzyl compounds, for example 3,5,3',5'-tetra-tert-butyl-4,4'-dihydroxydibenzyl ether, 4-hydroxy-3,5-di-tert-butylbenzyl mercaptan octadecyl ester, 4-hydroxy-3,5-di-tert-butylbenzyl mercaptan tridecyl ester, 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, 3,5-di-tert-butyl-4-hydroxybenzyl mercaptan isooctyl ester;

[0079] Hydroxybenzyl propionates, for example 2,2-bis(3,5-di-tert-butyl-2-hydroxybenzyl)propionates, 2-(3-tert-butyl-4-hydroxy-5-methylbenzyl)propionic acid bisoctadecyl ester, didodecylmercaptoethyl 2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)propionate, bis[4-(1,1,3,3-tetramethylbutyl)phenyl]-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)propionate;

[0080] 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;

[0081] Triazine compounds, for example 2,4-bis(octylmercapto)-6-(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine, 2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine, 2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,3,5-triazine, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,3,5-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;

[0082] Benzyl phosphonates, for example, dimethyl 2,5-di-tert-butyl-4-hydroxybenzylphospho- nate, diethyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl 3,5-di-tert-butyl- 4-hydroxybenzylphosphonate, dioctadecyl 5-tert-butyl-4-hydroxy-3-methylbenzylphos- phonate, calcium salt of the monoethyl ester of 3,5-di-tert-butyl-4-hydroxybenzylphos- phonate;

[0083] Acylaminophenols, for example, 4-hydroxylauranilide, 4-hydroxystearanilide, octyl N-(3,5-di-tert-butyl-4-hydroxyphenyl)carbamate;

[0084] Esters of β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid with mono- or polyhydric alcohols, for example, with methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethyl hexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane;

[0085] Esters of β-(5-tert-butyl-4-hydroxy-3-methylphenyl)propionic acid with mono- or polyhydric alcohols, for example, with methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethyl hexanediol, 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;

[0086] Esters of β-(3,5-di-cyclohexyl-4-hydroxyphenyl)propionic acid with mono- or polyhydric alcohols, for example, 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;

[0087] esters of beta-(3,5-di-tert-butyl-4-hydroxyphenyl)acetic acid with mono- or polyhydric alcohols, for example, with methanol, ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-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;

[0088] amides of beta-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid, for example, 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 XL-1, sold by Uniroyal);

[0089] ascorbic acid (vitamin C).

[0090] Particularly preferred phenolic antioxidants having the structure:

[0091]

[0092] wherein n = 2... to 10...

[0093]

[0094]

[0095]

[0096] Very particularly preferred phenolic antioxidants is 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid octadecyl ester and pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate).

[0097] Other particularly preferred phenolic antioxidants based on renewable raw materials, for example, tocopherols (vitamin E), tocotrienols, tocopherols, carotenoids, hydroxytyrosol, flavonols, for example, chrysin, quercetin, hesperidin, neohesperidin, naringin, morin, kaempferol, fisetin, anthocyanidins, for example, cyanidin and malvidin, curcumin, carnosic acid, carnosol, rosmarinic acid, and resveratrol.

[0098] Examples of suitable aminic antioxidants are:

[0099] 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-toluenesulfonyl)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, octyl- diphenylamine, for example p,p'-di-tert-octyl-diphenylamine, 4-n- butylaminophenol, 4-butyrylaminophenol, 4-nonylaminophenol, 4- dodecylaminophenol, 4-octadecanoylaminophenol, bis(4- methoxyphenyl)amine, 2,6-di-tert-butyl-4-dimethylamino-methylphenol, 2,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, N,N,N',N'-tetramethyl-4,4'-diaminodiphenylmethane, 1,2-bis[(2- methyl-phenyl)amino]ethane, 1,2-bis(phenylamino)propane, (o- tolyl)biguanide, bis[4-(1 ',3'-dimethylbutyl)phenyl]amine, tert-octylated N- phenyl-1 -naphthylamine, mixtures of mono- and dialkylated tert- butyl / tert-octyl diphenylamines, mixtures of mono- and dialkylated nonyl diphenylamines, mixtures of mono- and dialkylated dodecyl diphenylamines, mixtures of mono- and dialkylated isopropyl / isohexyl diphenylamines, mono- and dialkylated tert-butyl diphenylamines, mixtures of 2,3-dihydro-3,3-dimethyl-4H-1,4- benzothiazine, phenothiazine, mixtures of mono- and dialkylated tert- butyl / tert-octyl phenothiazines, mono- and dialkylated tert-octyl phenothiazines, N-allylphenothiazine, mixtures of N,N,N',N'-tetraphenyl-1,4- diamino but-2-ene, and mixtures or combinations thereof.

[0100] Preferred aminic antioxidantsIt is: N,N'-diisopropyl-p-phenylenediamine, N,N'-disec-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.

[0101] The particularly preferred amine antioxidants have the following structures:

[0102]

[0103] Where n = 3 to 100.

[0104] Other preferred aminic antioxidants Yes: hydroxylamine or N-oxide (nitrone), for example, N,N-dialkylhydroxylamine, N,N-dibenzylhydroxylamine, N,N-dilaurylhydroxylamine, N,N-distearylhydroxylamine, N-benzyl-α-phenyl nitrone, N-octadecyl-α-hexadecyl nitrone, and Genox EP (Group SI) according to the following formula:

[0105]

[0106] Suitable lactones are benzofuranones and indolinones For example, 3-(4-(2-acetoxyethoxy)phenyl]-5,7-di-tert-butyl-benzofuran-2-one, 5,7-di-tert-butyl-3-[4-(2-stearoyloxyethoxy)phenyl]benzofuran-2-one, 3,3'-bis[5,7-di-tert-butyl-3-(4-(2-hydroxyethoxy)phenyl)benzofuran-2-one), 5,7-di-tert-butyl-3-(4-ethoxyphenyl)benzofuran-2-one, 3-(4 [-acetoxy-3,5-dimethylphenyl]-5,7-di-tert-butyl-benzofuran-2-one, 3-(3,5-dimethyl-4-neopentyloxyphenyl)-5,7-di-tert-butyl-benzofuran-2-one, 3-(3,4-dimethylphenyl)-5,7-di-tert-butyl-benzofuran-2-one, 3-(2,3-dimethylphenyl)-5,7-di-tert-butyl-benzofuran-2-one, and lactones additionally containing a phosphite group, such as

[0107]

[0108] Another suitable group of antioxidants is isoindolo[2,1-A]quinazoline, for example

[0109]

[0110] Suitable secondary antioxidants phosphites or phosphonites, such as triphenyl phosphite, diphenyl alkyl phosphite, dialkyl phenyl phosphite, 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(2,4-dicumylphenyl) pentaerythritol diphosphite, bis(2,6-di-tert-butyl-4-methylphenyl) pentaerythritol diphosphite, diisodecyloxy pentaerythritol diphosphite, bis(2,4-di-tert-butyl-6-methylphenyl)) pentaerythritol diphosphite, bis(2,4,6-tri-tert-butylphenyl) pentaerythritol diphosphite, tristearyl sorbitol triphosphite, tetrakis(2,4-di-tert-butylphenyl)-4,4'-biphenylene diphosphonite, 6-isooctyloxy-2,4,8,10-tetra-tert-butyl-12H-dibenzo[d,g]-1,3,2-dioxaphosphocin, bis(2,4-di-tert-butyl-6-methylphenyl) methylphosphite, bis(2,4-di-tert-butyl-6-methylphenyl) ethylphosphite, 6-fluoro-2,4,8,10-tetra-tert-butyl-12-methyl-dibenzo[d,g]-1,3,2-dioxaphosphon, 2,2'2"-nitrilo[triethyltris(3,3",5,5'-tetra-tert-butyl-1,1 '-biphenyl-2,2'-diyl)phosphite], 2-ethylhexyl(3,3',5,5'-tetra-tert-butyl-1,1 '-biphenyl-2,2'-diyl)phosphite, 5-butyl-5-ethyl-2-(2,4,6-tri-tert-butylphenoxy)-1,3,2-dioxaphosphiran.

[0111] Particularly preferred phosphites / phosphonites is:

[0112]

[0113]

[0114] wherein n = 3-100.

[0115] One preferred phosphonite is:

[0116]

[0117] Very particularly preferred phosphites for use as secondary antioxidants is tris-(2,4-di-tert-butylphenyl) phosphite.

[0118] Suitable secondary antioxidants There are also organic sulfur compounds, for example sulfides and disulfides, such as distearyl thiodipropionate, dilauryl thiodipropionate; ditridecyl dithiopropionate, ditetradecyl thiodipropionate, 3-(dodecylthio)-1,1 '-[2,2-bis[[3-(dodecylthio)-1 -oxopropoxy]methyl]-1,3- propanediyl]propanoate. The following structures are preferred:

[0119]

[0120] Other suitable organic sulfur compounds are sulfur-containing amino acids, in particular cysteine, cystine or methionine .

[0121] Suitable acid scavengers ("antacids") are salts of monovalent, divalent, trivalent or tetravalent metals, preferably alkali metals, alkaline earth metals, aluminum or zinc, in particular with fatty acids, such as calcium stearate, magnesium stearate, zinc stearate, aluminum stearate, calcium laurate, calcium behenate, calcium lactate, calcium stearoyl-2-lactate. Other classes of suitable acid scavengers are hydrotalcites, in particular synthetic hydrotalcites based on aluminum, magnesium and zinc, hydrocalumite, zeolites, alkaline earth metal oxides, in particular calcium oxide and magnesium oxide as well as zinc oxide, alkaline earth metal carbonates, in particular calcium carbonate, magnesium carbonate and dolomite, and hydroxides, in particular brucite (magnesium hydroxide),

[0122] Suitable co-stabilizers are also polyols, in particular sugar alcohols or cyclic alcohols. Polyols such as pentaerythritol, dipentaerythritol, tripentaerythritol, short-chain polyether polyols or short-chain polyester polyols, and hyperbranched polymers / oligomers or dendrimers having alcohol groups, for example

[0123]

[0124] Preferably, the at least one sugar alcohol is selected from the group consisting of threitol, erythritol, galactitol, mannitol, ribitol, sorbitol, xylitol, arabitol, isomalt, lactitol, maltitol, dulcitol, iditol, maltotriitol and hydrogenated oligo- and polysaccharides having polyol end groups and mixtures thereof. Particularly preferably, the at least one preferred sugar alcohol is selected from the group consisting of erythritol, mannitol, isomalt, maltitol and mixtures thereof.

[0125] Examples of other suitable sugar alcohols are heptitol and octitol: meso-glycero-allo- heptitol, D-glycero-D-altro-heptitol, D-glycero-D-manno-heptitol, meso-glycero-gulo- heptitol, D-glycero-D-galacto-heptitol (mannoheptitol), D-glycero-D-glucose- heptitol, L-glycero-D-glucose-heptitol, D-erythro-L-galacto-octitol, D-threo-L- galacto-octitol

[0126] In particular, the at least one cyclic sugar alcohol can be selected from the group consisting of inositol (myo-Inositol, scyllitol, D-chiro-inositol, L-chiro-inositol, myo-inosose, neoinositol, allo-inositol, exo-inositol and cis-inositol), 1,2,3,4-tetrahydroxycyclohexane, 1,2,3,4,5-pentahydroxycyclohexane, quercitol, myriocin, borneol, conduritol, ononitol, pinakonitol, pinpollitol, populitol, cicuronul, quercetin, quinic acid and valiol.

[0127] Suitable light stabilizers Examples are compounds based on 2-(2'-hydroxyphenyl)benzotriazoles, 2-hydroxybenzophenones, esters of benzoic acid, acrylates, oxamides and 2-(2-hydroxyphenyl)-1,3,5-triazines.

[0128] Examples of suitable 2-(2'-hydroxyphenyl)benzotriazoles are 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-chlorobenzotriazole, 2-(3'-tert-butyl-2'- hydroxy-5'-methylphenyl-5-chlorobenzotriazole, 2-(3'-sec-butyl-5'-tert-butyl-2'- hydroxy-phenyl)benzotriazole, 2-(2'-hydroxy-4'-octyloxyphenyl)benzotriazole, 2-(3',5'-di- tert-amyl-2'-hydroxyphenyl)benzotriazole, 2-(3',5'-bis(alpha,alpha-dimethylbenzyl)-2'- hydroxyphenyl)benzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2-octyloxycarbonylethyl)phenyl)- 5-chlorobenzotriazole, 2-(3'-tert-butyl-5'-[2-(2-ethylhexyloxy)carbonylethyl]-2'- hydroxyphenyl)-5-chlorobenzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2- methoxy-carbonylethyl)phenyl)-5-chlorobenzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2- methoxy-carbonylethyl)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- isooctyloxycarbonylethyl)phenyl)benzotriazole, 2,2'-methylenebis[4-(1,1,3,3-tetramethylbutyl)- 6-benzotriazol-2-ylphenol]; the ester exchange product of 2-[3'-tert-butyl-5'-(2- methoxy-carbonylethyl)-2'-hydroxyphenyl]-2H-benzotriazole and polyethylene glycol 300; [R— CH2CH2— COO— CH2CH2-]-2, wherein R = 3'-tert-butyl-4'-hydroxy-5'-2H- benzotriazol-2-ylphenyl, 2-[2'-hydroxy-3'-(alpha,alpha-dimethylbenzyl)-5'-(1,1,3,3- tetramethylbutyl)phenyl]benzotriazole, 2-[2'-hydroxy-3'-(1,1,3,3-tetramethylbutyl)-5'- (alpha,alpha-dimethylbenzyl)phenyl]benzotriazole.

[0129] Examples of suitable 2-hydroxybenzophenones are the 4-hydroxy, 4-methoxy, 4-octyloxy, 4-decyl- oxy, 4-dodecyloxy, 4-benzyloxy, 4,2',4'-trihydroxy and 2'-hydroxy-4,4'-dimethoxy derivatives of 2-hydroxybenzophenone.

[0130] Examples of suitable acrylates are α-cyano-β,β-diphenylacrylate, α-cyano-β,β-diethoxyacrylate, methyl α-methylcinnamoate, methyl α-cyano-β-methyl-p-methoxycinnamate, butyl α-cyano-β-methyl-p- methoxycinnamate, methyl α-methyI-p-methoxycinnamate and N-(β-methyI-β-cyano-vinyl)-2- methyldihydroindole.

[0131] Examples of suitable benzoic acid esters are 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.

[0132] Examples of suitable oxamides are 4,4'-di-octyloxyoxanilide, 2,2'-di-ethyloxyoxanilide, 2,2'-di-octyloxy-5,5'-di-tert-octyl-oxanilide, 2,2'-didodecyloxy-5,5'-di-tert-octyl-oxanilide, 2- ethyloxy-5-tert-octyl-2'-acetyl-oxanilide and mixtures thereof with 2-ethyloxy-2'-ethyl-5,4'-di-tert- octyl-oxanilide, mixtures of o-methoxy and p-methoxy disubstituted oxanilides and mixtures of o-ethoxy and p-ethoxy disubstituted oxanilides.

[0133] Examples of suitable 2-(2-hydroxyphenyl)-1,3,5-triazines are 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-octyloxypropoxy)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-butyloxy-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-hydroxypropoxy]phenyl}-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine.

[0134] Suitable metal deactivators Examples are N,N'-diphenyl oxamide, N-salicylidene-N'-salicyl hydrazide, N,N'-bis(salicyl) hydrazide, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl) hydrazide, 3-salicylidenamino- 1,2,4-triazole, bis(benzylidene) oxalyldihydrazide, oxanilide, isophthalic acid dihydrazide, sebacic acid bisphenylhydrazide, N,N'-diacetyladipic acid dihydrazide, N,N'-bis(salicyl) oxyacetic dihydrazide, N,N'-bis(salicyl) thiopropionic dihydrazide.

[0135] Particularly preferred metal deactivators is:

[0136]

[0137] Suitable sterically hindered amines Examples are 1,1-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 condensation product of 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid, linear or cyclic condensation products 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-butanetracarboxylic acid, 1,1 '-(1,2-ethanediyl)-bis(3,3,5,5-tetramethylpiperazinone), 4-benzoyl-2,2,6,6-tetramethylpiperidine, 4-stearyloxy-2,2,6,6-tetramethylpiperidine, linear or cyclic condensation products of N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4-morpholino-2,6-dichloro-1,3,5-triazine, the reaction product of 7,7,9,9-tetramethyl-2-cycloundecyl-1-oxo-3,8-diaza-4-oxaspiro[4,5]decane and epichlorohydrin.

[0138] Also included in the above structures herein are: sterically hindered N-H, N-alkyl such as N-methyl or N-octyl, N-alkoxy derivatives such as N-methoxy or N-octyloxy, cycloalkyl derivatives such as N-cyclohexyloxy and N-(2-hydroxy-2-methylpropyloxy) analogs.

[0139] Preferred sterically hindered amines Also having the following structure:

[0140]

[0141]

[0142]

[0143] Preferred oligomeric and polymeric sterically hindered amines Having the following structure:

[0144]

[0145]

[0146]

[0147] In the above compounds, n is 3 to 100, respectively.

[0148] Another suitable light stabilizer is Hostanox NOW (manufacturer: Clariant SE) having the following general structure:

[0149]

[0150] wherein R is -O-C(O)-C 15 H 31 or -O-C(O)-C 17 H 35 .

[0151] Suitable dispersants Examples are:

[0152] polyacrylates, for example copolymers with long-chain side groups, polyacrylate block copolymers, alkyl amides: for example N,N'-1,2-ethanediyl bistea- radoylamide, sorbitan esters, for example sorbitan monostearate, titanates and zirconates, reactive copolymers with functional groups, for example polypropylene- acrylic acid copolymers, polypropylene-maleic anhydride copolymers, polyethylene-glycidyl methacrylate copolymers, polystyrene-alternating-maleic anhydride- polysiloxanes: for example dimethylsilanediol-ethylene oxide copolymers, polyphenylsiloxane copolymers, amphoteric copolymers: for example polyethylene-block-poly- oxyethylene, dendrimers, for example hydroxyl-containing dendrimers.

[0153] Suitable antinucleating agents are azine dyes, for example aniline black.

[0154] Suitable flame retardants In particular

[0155] a) inorganic flame retardants, such as AI(OH)3, Mg(OH)2, AIO(OH), MgCO3, layered silicates, such as montmorillonite or sepiolite, unmodified or organically modified, double salts, such as Mg-Al silicates, POSS (polyhedral oligomeric silsesquioxane) compounds, humboldtine, hydromagnesite or halloysite and Sb203, Sb205, M0O3, zinc stannate, zinc hydroxystannate, b) nitrogen-containing flame retardants, such as melamine, melem, melam, melon, melamine derivatives, melamine condensation products or melamine salts, benzoguanamine, polyisocyanurate, allantoin, phosphazenes, in particular melamine cyanurate, melamine phosphate, ditrimelamine phosphate, melamine pyrophosphate, melamine polyphosphate, melamine metal phosphates such as melamine aluminum phosphate, melamine zinc phosphate, melamine magnesium phosphate, and the corresponding pyrophosphates and polyphosphates, poly-[2,4-(piperazin-1,4-yl)-6-(morpholin-4-yl)-1,3,5-triazine], ammonium polyphosphate, melamine borate, melamine hydrobromide,

[0156] c) radical-forming agents, such as alkoxyl amines, hydroxyl amine esters, azo compounds, triazine compounds, disulfides, polysulfides, thiols, thiuram sulfides, dithiocarbamates, mercaptobenzothiazoles, sulfenamides, sulfenimides

[0157] d) di- or polyisopropylphenyl, hydroxyimides and derivatives thereof, such as hydroxyimide esters or hydroxyimide ethers

[0158] e) phosphorus-containing flame retardants, such as red phosphorus, phosphoric acid esters, such as resorcinol diphosphate, bisphenol-A-diphosphate and oligomers thereof, triphenyl phosphate, ethylenediamine diphosphate, phosphinates, such as salts of hypophosphorous acid and derivatives thereof, such as alkylphosphinates, such as aluminum diethylphosphinate or zinc diethylphosphinate or aluminum phosphinate, aluminum phosphite, aluminum phosphonate, phosphoric acid esters, oligomeric and polymeric derivatives of methane phosphonate, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) and substituted compounds thereof.

[0159] f) halogen-containing flame retardants based on chlorine and bromine, such as polybrominated diphenyl ethers, such as decabromodiphenyl ether, tris(3-bromo-2,2-bis(bromomethyl)propyl phosphate, tris(trisbromoneopentyl)phosphate, tetrabromophthalic acid, 1,2-bis(trisbromophenoxy)ethane, hexabromocyclododecane, brominated diphenylethane, tris(2,3-dibromopropyl)isocyanurate, ethylenebis(tetrabromophthalimide), tetrabromobisphenol A, brominated polystyrene, brominated polybutadiene or, polystyrene-brominated polybutadiene copolymer, brominated polyphenylene ether, brominated epoxy resin, poly(penta-bromobenzyl acrylate), optionally in combination with Sb203and / or Sb205.

[0160] g) borates such as zinc borate or calcium borate, optionally on a carrier material such as silicon dioxide

[0161] h) sulfur-containing compounds, such as elemental sulfur, disulfides and polysulfides, thiurams, dithiocarbamates, mercaptobenzothiazoles and sulfenamides,

[0162] i) anti-dripping agents, such as polytetrafluoroethylene,

[0163] j) silicon-containing compounds, such as polyvinylsiloxanes,

[0164] k) carbon modifications, such as carbon nanotubes (CNT), expandable graphite or graphene

[0165] l) and combinations or mixtures thereof.

[0166] Very particularly preferred flame retardants are halogen-free and are the following compounds:

[0167] Al(OH)3, Mg(OH)2,

[0168]

[0169]

[0170] wherein each R = alkyl, phenyl and wherein n = 3 to 20

[0171]

[0172] Suitable plasticizers Examples are phthalates, adipates, citrates, 1,2-cyclohexane dicarboxylates, trimellitates, isosorbide esters, phosphates, epoxides such as epoxidized soybean oil, or aliphatic polyesters.

[0173] Suitable lubricants and processing aids Examples are polyethylene waxes, polypropylene waxes and salts of fatty acids, such as calcium stearate, zinc stearate, or salts of montan wax, amide waxes, such as erucamide or oleamide, fluoropolymers, silicones or neoalkoxy titanates and zirconates.

[0174] Suitable pigments They can be inorganic or organic in nature. Examples of inorganic pigments are titanium dioxide, zinc oxide, zinc sulfide, iron oxide, ultramarine, carbon black, examples of organic pigments are anthraquinone, anthrone, benzimidazolone, chinacridone, diketopyrrolopyrrole, dioxazine, indanthrone, isoindolinone, azo compound, perylene, phthalocyanine or pyranine. Other suitable pigments are metal-based effect pigments or metal oxide-based pearlescent pigments.

[0175] Suitable optical brightenersExamples are bisbenzoxazoles, phenylcoumarins or bis(styryl)biphenyls, in particular the following fluorescent whitening agents of the formulae:

[0176]

[0177] Suitable filler deactivators Examples are polysiloxanes, polyacrylates, in particular block copolymers such as polymethacrylic acid-polyalkylenoxid or poly(glycidyl) (meth)acrylate and copolymers thereof, for example with styrene, and also, for example, epoxides having the following structure:

[0178]

[0179]

[0180] Suitable antistatic agents Examples are ethoxylated alkylamines, fatty acid esters, alkylsulfonates and polymers such as polyetheramides.

[0181] Suitable antiozonants are the above-mentioned amines, for example N,N'-diisopropyl-p-phenylenediamine, N,N'-di-sec-butyl-p-phenylenediamine, N,N'-bis(1,4-dimethylpentyl)-p- phenylenediamine, N,N'-dicyclohexyl-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.

[0182] Suitable rheology modifiers Examples are peroxides, alkoxylamine esters, imide sulfonates and, in particular, the following structures for the production of controlled rheology polypropylene (CR-PP):

[0183]

[0184] Suitable nucleating agents are talc, alkali metal or alkaline earth metal salts of monofunctional and polyfunctional carboxylic acids, such as benzoic acid, succinic acid, adipic acid, for example sodium benzoate, zinc glycerolate, aluminium hydroxybis(4-tert-butyl)benzoate, 2,2'-methylenebis(4,6-di-tert-butylphenyl)phosphate, and tri- and diamides, for example tris(4-methylcyclohexyl)amidotribenzene, tris(4-methylcyclohexyl)amidotribenzene, tris(tert-butylamido)trimesate, N,N',N"-1,3,5-benzenetriyltris(2,2-dimethylpropionamide) or dicyclohexylamido-2,6-naphthalene dicarboxylate.

[0185] Suitable additives for molecular weight building of polycondensation polymersExamples of chain extenders are diepoxides, bisoxazolines, bisoxazolones, bisoxazines, diisocyanates, diacid anhydrides, bisacyl lactams, bismaleimides, dicyanates, carbodiimides. Other suitable chain extenders are polymeric compounds such as polystyrene-polyacrylate-poly(glycidyl (meth)acrylate) copolymers, polystyrene-maleic anhydride copolymers and polyethylene-maleic anhydride copolymers.

[0186] Suitable additives for increasing the electrical conductivity Examples are the mentioned antistatic agents, carbon black and carbon compounds such as carbon nanotubes and graphene, metal powders such as copper powder and conductive polymers such as polypyrrole, polyaniline and polythiophene. Examples of suitable additives for increasing the thermal conductivity are aluminum nitride and boron nitride.

[0187] Suitable infrared active additives Examples are aluminum silicates, hydrotalcites or dyes such as phthalocyanines or anthraquinones.

[0188] Suitable release agents Examples are silicone resins, soaps and waxes such as montan wax.

[0189] Furthermore, the additives according to the application can be used for stabilizing oils, fats and chemical products. If the organic material is an oil and a fat, they can be based on, for example, mineral oil, vegetable fat or animal fat or on synthetic ester-based oils, fats or waxes. Vegetable oils are, for example, palm oil, olive oil, rapeseed oil, linseed oil, soybean oil, sunflower oil, castor oil; animal fats are, for example, fish oil or beef tallow. The compounds according to the application can also be used as stabilizers for lubricants, hydraulic oils, engine oils, turbine oils, transmission oils, metalworking fluids or as greases. These mineral or synthetic lubricants are mainly based on hydrocarbons. Chemical products are used, for example, for stabilizing polyols in the production of polyurethanes or for stabilizing monomers for transport and storage, such as styrene, acrylates or methacrylates.

[0190] The above-mentioned additives and optional additional additives can be incorporated into the plastics using conventional processing methods, in which the polymer is melted and mixed with the additive composition according to the application and optionally other additives, preferably using a mixer, kneader or extruder. As processing machine, an extruder is preferred, for example a single-screw extruder, a twin-screw extruder, a planetary roller extruder, a ring extruder, a co-kneader, which preferably has a vacuum degassing device. The processing can be carried out under air or optionally under inert gas.

[0191] Furthermore, the additive composition according to the application can be produced and introduced in the form of a so-called masterbatch or concentrate, which comprises, for example, 10-90% of the stabilizer or composition according to the application in the polymer.

[0192] The above additives are particularly suitable as possible additives. Here, particular preference is given, for example, to secondary antioxidants selected from the group consisting of phosphites, phosphonites and mercaptans, to stabilizer assistants selected from the group consisting of polyols, acid scavengers, and sterically hindered amines, or mixtures and combinations thereof.

[0193] It is particularly preferred that the content or addition amount of the at least one additive is from 0.01 to 80% by weight, preferably from 0.01 to 9.99% by weight, more preferably from 0.01 to 4.98% by weight, particularly preferably from 0.02 to 2.00% by weight, based on the total amount of the at least one compound according to formula I, the organic material and the at least one additive.

[0194] The present application also relates to an organic material, in particular a plastics composition, which comprises at least one compound according to the general formula I or a mixture of a plurality of compounds according to the general formula I as stabilizer

[0195]

[0196] wherein R 1 , R 2 , R 3 , M and n are as defined above.

[0197] All advantageous embodiments described in connection with the use according to the present application also apply to the organic material without restriction.

[0198] In a preferred embodiment, the organic material has the following composition:

[0199] from 0.01 to 10.00% by weight, preferably from 0.01 to 7.50% by weight, more preferably from 0.02 to 5.00% by weight, particularly preferably from 0.050 to 2.00% by weight of a compound according to the general formula I, or in the case of a mixture of a plurality of compounds according to the general formula I, the above-mentioned content is the total amount of all compounds according to the general formula I.

[0200] from 99.99 to 10.00% by weight, preferably from 99.99 to 90.00% by weight, preferably from 99.89 to 95.00% by weight, particularly preferably from 99.90 to 98.00% by weight of at least one organic material, which is preferably selected from the group consisting of plastics, paints, lubricating oils, hydraulic oils, engine oils, turbine oils, transmission oils, metalworking fluids, chemicals or monomers, and

[0201]

[0202] from 0 to 80.00% by weight, preferably from 0 to 9.99% by weight, more preferably from 0.01 to 4.98% by weight, particularly preferably from 0.02 to 2.00% by weight of at least one additive,

[0203] wherein the components add up to 100 % by weight.

[0204] The present application also relates to a method for stabilizing organic materials, in particular against oxidative, thermal and / or actinic degradation, wherein one or more compounds according to the general formula I are incorporated into the organic material.

[0205]

[0206] wherein R 1 , R 2 , R 3 and M and n are defined as above.

[0207] Furthermore, the present application relates to a compound of the general formula I

[0208]

[0209] wherein

[0210] R 1 , R 2 and R 3 are each independently selected from the group consisting of hydroxyl, straight-chain or branched alkoxy having 1 to 6 carbon atoms and hydrogen, with the proviso that at least one of the residues R 1 , R 2 and R 3 is a hydroxyl residue, and

[0211] M is aluminum, and

[0212] n is 3.

[0213] Another aspect of the present application relates to a stabilizer composition, comprising or consisting of

[0214] a) a compound according to the general formula I or a mixture of a plurality of compounds according to the general formula I

[0215]

[0216] wherein R 1 , R 2 , R 3 , M and n are defined as above (component A), and

[0217] b) at least one secondary antioxidant selected from the group consisting of phosphites, phosphonites or mercaptans, at least one co-stabilizer selected from the group consisting of polyols, acid scavengers, or sterically hindered amines, and

[0218] mixtures and combinations consisting of the group of phosphites, phosphonites or mercaptans, at least one co-stabilizer selected from the group consisting of polyols, acid scavengers, or sterically hindered amines (component B).

[0219] It is particularly advantageous if the weight ratio of component A to component B in the stabilizer composition is from 100:1 to 1 :100, preferably from 10:1 to 1 :10, particularly preferably from 4:1 to 1 :4.

[0220] The application will be elucidated in more detail with reference to the following embodiments, without the application being limited to the specific examples. DETAILED DESCRIPTION

[0221] Examples

[0222] A) Preparation of the hydroxycinnamic acid salt according to the application

[0223] A1 ) Synthesis of sodium ferulate (NaFa)

[0224]

[0225] First, 12.00 g (1.00 eq, 61.80 mmol) of ferulic acid (1 ) were dissolved in 620 mL of methanol in a beaker. Then 2.47 g (1.00 eq, 61.80 mmol) of sodium hydroxide were dissolved in 60 mL of distilled water and the resulting NaOH solution was added dropwise to the ferulic acid solution via a dropping funnel. After the addition was complete, the yellowish solution was poured into 1.5 1 of acetone. The yellow precipitate that separated was filtered off and washed 3 times with 200 mL of acetone each time and finally dried in a vacuum drying cabinet at 80°C for 2 days. 10.51 g of a yellow, fine-powdered precipitate were obtained. The yield was 78.66%.

[0226] A2) Synthesis of aluminum ferulate (AlFa)

[0227]

[0228] First, 11.18 g (3.07 eq, 57.57 mmol) of ferulic acid (1 ) were dissolved in 50 mL of methanol. To the yellow solution, 57 mL of a 1 M NaOH solution were added. After the solution had been stirred for half an hour, a solution consisting of 2.5 g (1.00 eq, 18.75 mmol) of aluminum trichloride and 2.8 mL of distilled water was added dropwise via a dropping funnel. At this point, a white precipitate immediately separated out, which was stirred for a further hour and then filtered off. After washing 3 times with 200 mL of distilled water and 200 mL of acetone each time, 5.32 g of a white, coarse-grained solid were obtained, which were dried in a vacuum drying cabinet at 80°C overnight.

[0229] A3) Synthesis of magnesium ferulate (MgFa)

[0230]

[0231] First, 2.5 g (1.00 eq, 42.86 mmol) of magnesium hydroxide was suspended in 600 mL of distilled water in a beaker. Then 16.91 g (2.03 eq, 87.08 mmol) of ferulic acid was heated to dissolve in 250 mL of methanol and the resulting light yellow solution was added to the magnesium hydroxide suspension. The suspension was stirred overnight at room temperature during which the magnesium hydroxide went into solution. The resulting light yellow solution was poured into 1.5 l of acetone. The precipitated yellow powder was filtered off and washed 3 times with 200 mL of acetone each and finally dried in a vacuum oven at 80 °C for 2 days. 2.80 g of yellow fine powder precipitate was obtained. The yield was 15.90%.

[0232] A4) Synthesis of calcium ferulate (CaFa)

[0233]

[0234] First, 2.00 g (1.00 eq, 26.99 mmol) of calcium hydroxide was suspended in 100 mL of distilled water in a beaker. Then 10.48 g (2.00 eq, 53.97 mmol) of ferulic acid was heated to dissolve in 100 mL of methanol and the resulting light yellow solution was added to the calcium hydroxide suspension. The suspension was stirred overnight at room temperature during which the calcium hydroxide went into solution. In the meantime the remaining silver-colored residue was filtered off. The filtrate was poured into 1.5 l of acetone. The precipitated yellow powder was filtered off and washed 3 times with 200 mL of acetone each and finally dried in a vacuum oven at 80 °C for 2 days. 7.42 g of yellow fine powder precipitate was obtained. The yield was 64.47%.

[0235] B) Application test

[0236] To test the effect of the stabilizers according to the application, commercially available polypropylene (Moplen HP 501 N, LyondellBasell Industries) was homogenized with the stabilizers or combinations of stabilizers specified in the table in a powder-powder mixture and circulated in a twin-screw mini-extruder (MC5, manufacturer DSM) at 200 °C and 200 revolutions per minute for 30 minutes and the drop in force was recorded. This force is a direct measure of the molecular weight of the polypropylene, the smaller the drop, the higher the stabilizing effect.

[0237] Table 1: Stabilization of polypropylene

[0238]

[0239] Table 2: Stabilization of polypropylene

[0240]

[0241] Table 3: Stabilization of polypropylene

[0242]

[0243] Table 3: Stabilization of polypropylene

[0244]

[0245]

[0246] DSDTP = distearyl thiodipropionate

[0247] Phosphite = tris-(2,4-di-tert-butylphenyl) phosphite

[0248] The additives according to the present application show a clear stabilizing effect, since the degradation of the polymer is less during the test.

[0249] C) Oxidation Induction Time (OIT)

[0250] The oxidation induction time is a standardized test performed in a differential scanning calorimeter. This method allows determining the thermal stability of the material under test. Here the time between melting and the onset of decomposition under isothermal conditions (here 220 °C) is determined. Until the material under test melts, a nitrogen atmosphere is present, then synthetic air is passed through. In Table 4 the additive combinations that were incorporated and investigated in a commercially available polypropylene (Moplen HP 500N, Lyondell Basell Industries) at an extrusion temperature of 200 °C by means of a co-rotating twin-screw laboratory extruder (Process 11, Thermo Fisher Scientific) are summarized.

[0251] Table 4: Oxidation induction time of compounds incorporated in polypropylene.

[0252]

[0253] It has been shown that the addition of 0.5% sodium ferulate can significantly improve the oxidative stability of polypropylene.

Claims

1. The use of compounds or mixtures of compounds according to general formula I. in R 1 R 2 and R 3 Each is independently selected from the group consisting of a hydroxyl group, a straight-chain or branched alkoxy group having 1 to 6 carbon atoms, and hydrogen, provided that the residue R 1 R 2 and R 3 At least one of them is a hydroxyl residue, M is selected from the group consisting of alkali metals, alkaline earth metals, aluminum and zinc, and n is an integer from 1 to 4. For stabilizing plastics, wherein the plastics are selected from the group consisting of: a) Polymers of olefins or dienes b) Polystyrene, polymethylstyrene, polyα-methylstyrene, polyvinylnaphthalene, polyvinylbiphenyl, polyvinyltoluene, styrene-butadiene polymer (SB), styrene-butadiene-styrene polymer (SBS), styrene-ethylene-butene-styrene polymer (SEBS), styrene-ethylene-propylene-styrene polymer, styrene-isoprene polymer, styrene-isoprene-styrene polymer (SIS), styrene-butadiene-acrylonitrile polymer (ABS), styrene-acrylonitrile polymer (SAN), styrene-acrylonitrile-acrylate polymer (ASA), styrene-ethylene polymer, styrene-maleic anhydride polymer, including the corresponding graft copolymers. c) Polymers of unsaturated esters d) Polymers of unsaturated alcohols and their derivatives e) Polyacetal f) Polyphenylene ether and blends with polystyrene or polyamide, g) Polymers of cyclic ethers, h) Polyurethane, derived from hydroxyl-terminated polyethers or polyesters and aromatic or aliphatic isocyanates, i) Polyamide, j) Polyimide, polyamide-imide, polyether-imide, polyester-imide, poly(ether)ketone, polysulfone, polyethersulfone, polyarylsulfone, polyphenylene sulfide, polybenzimidazole, polyhydantoin. k) Polyesters derived from aliphatic or aromatic dicarboxylic acids and diols or from hydroxycarboxylic acids. l) Polycarbonate, polyester carbonate, and blends m) Cellulose derivatives, n) Epoxy resin, which is composed of the following substances: Difunctional or polyfunctional epoxy compounds are combined with curing agents based on amines, acid anhydrides, dicyandiamides, thiols, isocyanates, or catalytic curing agents. o) Phenolic resin, p) Unsaturated polyester resins made from unsaturated dicarboxylic acids and diols with vinyl compounds. q) Silicone resin, r) and mixtures, combinations or blends of two or more of the above polymers.

2. The use according to claim 1, characterized in that, Residue R 1 R 2 and R 3 They represent hydroxyl residues, Residue R 1 R 2 and R 3 The two in the text represent hydroxyl residues, and residue R 1 R 2 and R 3 One of them represents hydrogen or a straight-chain or branched alkoxy group having 1 to 6 carbon atoms. Residue R 1 R 2 and R 3 One of them represents a hydroxyl residue, and residue R 1 R 2 and R 3 The two in the text represent straight-chain or branched alkoxy groups having 1 to 6 carbon atoms, or Residue R 1 R 2 and R 3 Each of the following represents a hydroxyl residue, a straight-chain or branched alkoxy group having 1 to 6 carbon atoms, and hydrogen.

3. The use according to claim 1 or 2, characterized in that, Compounds based on general formula I are selected from the group consisting of the following compounds: Where M and n are as defined in claim 1.

4. The use according to claim 1 or 2, characterized in that, According to the compounds of general formula I, or in the case of a mixture of multiple compounds of general formula I, the total amount of all compounds of general formula I in the plastic is in the weight proportion of 0.01 to 10.00% by weight.

5. The use according to claim 1 or 2, for stabilizing plastics, wherein: a) The polymer of the olefin or diene is selected from the group consisting of: polyethylene, polypropylene, polyisobutylene, poly-4-methyl-pent-1-ene, polybutadiene, polyisoprene, polycyclooctene, polyalkylene-carbon monoxide copolymer, random or block copolymers, terpolymers, graft polymers, and blends thereof. b) The polymer of the unsaturated ester is selected from the group consisting of: polyacrylates and polymethacrylates, and copolymers thereof. c) The polymers of the unsaturated alcohols and their derivatives are selected from the group consisting of: polyvinyl alcohol, polyvinyl acetate, polyvinyl butyral, allyl phthalate, and polyallyl melamine. d) The polyacetal is selected from the group consisting of polyoxymethylene (POM) or copolymers with butyraldehyde. e) The polymer of the cyclic ether is selected from the group consisting of polyethylene oxide, polypropylene oxide, and polytetrahydrofuran. f) The polyamide is selected from the group consisting of: polyamide-6, 6.6, 6.10, 4.6, 4.10, 6.12, 10.10, 10.12, 12.12, polyamide 11, polyamide 12, and aromatic polyamides, blends of different polyamides, or blends of polyamides and polyolefins; g) The polyester derived from aliphatic or aromatic dicarboxylic acids and diols or from hydroxycarboxylic acids is selected from the group consisting of: polyethylene terephthalate (PET), polybutylene terephthalate (PET) (PBT), polypropylene terephthalate (PTT), polyethylene naphthalate (PEN), poly(1,4-dimethylolcyclohexane terephthalate), polyhydroxybenzoate, polyhydroxynaphthalate, polylactic acid (PLA), polyhydroxybutyrate (PHB), polyhydroxyvalerate (PHV), polyvinyl succinate, polytetramethylene succinate, polycaprolactone, h) The cellulose derivative is selected from the group consisting of nitrocellulose, cellulose acetate, cellulose propionate, and cellulose butyrate. i) The phenolic resin is selected from phenol-formaldehyde resin, urea-formaldehyde resin, and melamine-formaldehyde resin. A group that is formed.

6. The use according to claim 5, wherein the polyethylene is selected from the group consisting of: LDPE, LLDPE, VLDPE, ULDPE, MDPE, HDPE, UHMWPE and metallocene PE.

7. The use according to claim 1 or 2, characterized in that, The plastic contains at least one additional additive and / or at least one additional additive is added to the plastic during use, the additive being selected from the group consisting of: primary and / or secondary antioxidants, ultraviolet absorbers, light stabilizers, hydroxylamine-based stabilizers, benzofuranone-based stabilizers, nucleating agents, impact toughness modifiers, plasticizers, lubricants, rheology modifiers, chain extenders, processing aids, pigments, dyes, fluorescent whitening agents, antibacterial agents, antistatic agents, lubricants, antiblocking agents, coupling agents, dispersants, compatibilizers, oxygen scavengers, acid scavengers, auxiliary stabilizers, marking agents, and antifogging agents.

8. The use according to claim 7, wherein the primary and / or secondary antioxidant is selected from the group consisting of: phosphites, phosphonites, thiols, phenolic antioxidants, sterically hindered amines, hydroxylamines, and mixtures or combinations thereof.

9. The use according to claim 7, characterized in that, Based on the total amount of the at least one compound according to Formula I, the plastic, and the at least one additive, the content or amount of the at least one additive is from 0.01 to 80% by weight.

10. The use according to claim 1 or 2, characterized in that, Compounds of general formula I or mixtures thereof are used in combination with a stabilizer, wherein the stabilizer is selected from polyols.

11. The use according to claim 10, wherein the polyol is selected from the group consisting of: sugar alcohols and / or cyclic alcohols, short-chain polyether polyols or short-chain polyester polyols, hyperbranched polymers / oligomers or dendritic polymers having alcohol groups, hydrogenated oligosaccharides and polysaccharides with polyol ends, and mixtures thereof.

12. A plastic composition comprising at least one compound according to general formula I or a mixture of multiple compounds according to general formula I as a stabilizer. Where R 1 R 2 R 3 M and n are as defined in any one of claims 1 and 2, wherein the plastic is selected from the group consisting of: a) Polymers of olefins or dienes b) Polystyrene, polymethylstyrene, polyα-methylstyrene, polyvinylnaphthalene, polyvinylbiphenyl, polyvinyltoluene, styrene-butadiene polymer (SB), styrene-butadiene-styrene polymer (SBS), styrene-ethylene-butene-styrene polymer (SEBS), styrene-ethylene-propylene-styrene polymer, styrene-isoprene polymer, styrene-isoprene-styrene polymer (SIS), styrene-butadiene-acrylonitrile polymer (ABS), styrene-acrylonitrile polymer (SAN), styrene-acrylonitrile-acrylate polymer (ASA), styrene-ethylene polymer, styrene-maleic anhydride polymer, including the corresponding graft copolymers. c) Polymers of unsaturated esters d) Polymers of unsaturated alcohols and their derivatives e) Polyacetal f) Polyphenylene ether and blends with polystyrene or polyamide, g) Polymers of cyclic ethers, h) Polyurethane, derived from hydroxyl-terminated polyethers or polyesters and aromatic or aliphatic isocyanates; i) Polyamides; j) Polyimide, polyamide-imide, polyether-imide, polyester-imide, poly(ether)ketone, polysulfone, polyethersulfone, polyarylsulfone, polyphenylene sulfide, polybenzimidazole, polyhydantoin. k) Polyesters derived from aliphatic or aromatic dicarboxylic acids and diols or from hydroxycarboxylic acids. l) Polycarbonate, polyester carbonate, and blends m) Cellulose derivatives, n) Epoxy resin, which is composed of the following substances: Difunctional or polyfunctional epoxy compounds are combined with curing agents based on amines, acid anhydrides, dicyandiamides, thiols, isocyanates, or catalytic curing agents. o) Phenolic resin, p) Unsaturated polyester resins made from unsaturated dicarboxylic acids and diols with vinyl compounds. q) Silicone resin, r) and mixtures, combinations or blends of two or more of the above polymers.

13. The plastic composition according to claim 12, comprising the following components: 0.01 to 10.00% by weight of a compound according to general formula I, or in the case of a mixture of multiple compounds according to general formula I, where the above content refers to the total amount of all compounds according to general formula I. At least one type of plastic, comprising 99.99 to 10.00% by weight, and At least one additive, ranging from 0 to 80.00% by weight. The total weight of all components is 100%.

14. The plastic composition according to claim 12, characterized in that, The at least one additive is selected from the group consisting of: primary and / or secondary antioxidants, ultraviolet absorbers, light stabilizers, hydroxylamine-based stabilizers, benzofuranone-based stabilizers, nucleating agents, impact toughness modifiers, plasticizers, lubricants, rheology modifiers, chain extenders, processing aids, pigments, dyes, fluorescent whitening agents, antibacterial agents, antistatic agents, lubricants, antiblocking agents, coupling agents, dispersants, compatibilizers, oxygen scavengers, acid scavengers, co-stabilizers, markers, and antifogging agents.

15. The plastic composition of claim 14, wherein the at least one additive is selected from the group consisting of: a minor antioxidant selected from the group consisting of phosphites, phosphonites and thiols; at least one co-stabilizer selected from the group consisting of polyols and acid scavengers; and a sterically hindered amine.

16. The plastic composition of claim 14, wherein the primary and / or secondary antioxidant is selected from the group consisting of phosphites, phosphonites, thiols, phenolic antioxidants, sterically hindered amines, hydroxylamines, and mixtures or combinations thereof.

17. A method for stabilizing a plastic, wherein one or more compounds according to general formula I are incorporated into the plastic. Where R 1 R 2 R 3 M and n are as defined in any one of claims 1 and 2, wherein the plastic is selected from the group consisting of: a) Polymers of olefins or dienes b) Polystyrene, polymethylstyrene, polyα-methylstyrene, polyvinylnaphthalene, polyvinylbiphenyl, polyvinyltoluene, styrene-butadiene polymer (SB), styrene-butadiene-styrene polymer (SBS), styrene-ethylene-butene-styrene polymer (SEBS), styrene-ethylene-propylene-styrene polymer, styrene-isoprene polymer, styrene-isoprene-styrene polymer (SIS), styrene-butadiene-acrylonitrile polymer (ABS), styrene-acrylonitrile polymer (SAN), styrene-acrylonitrile-acrylate polymer (ASA), styrene-ethylene polymer, styrene-maleic anhydride polymer, including the corresponding graft copolymers. c) Polymers of unsaturated esters d) Polymers of unsaturated alcohols and their derivatives e) Polyacetal f) Polyphenylene ether and blends with polystyrene or polyamide, g) Polymers of cyclic ethers, h) Polyurethane, derived from hydroxyl-terminated polyethers or polyesters and aromatic or aliphatic isocyanates, i) Polyamide, j) Polyimide, polyamide-imide, polyether-imide, polyester-imide, poly(ether)ketone, polysulfone, polyethersulfone, polyarylsulfone, polyphenylene sulfide, polybenzimidazole, polyhydantoin. k) Polyesters derived from aliphatic or aromatic dicarboxylic acids and diols or from hydroxycarboxylic acids. l) Polycarbonate, polyester carbonate, and blends m) Cellulose derivatives, n) Epoxy resin, which is composed of the following substances: Difunctional or polyfunctional epoxy compounds are combined with curing agents based on amines, acid anhydrides, dicyandiamides, thiols, isocyanates, or catalytic curing agents. o) Phenolic resin, p) Unsaturated polyester resins made from unsaturated dicarboxylic acids and diols with vinyl compounds. q) Silicone resin, r) and mixtures, combinations or blends of two or more of the above polymers.

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