Use of substituted cinnamic acid esters as stabilizers for organic materials, stabilized organic materials, methods for stabilizing organic materials, and specific cinnamic acid esters

Abstract

The present invention relates specifically to the use of a specific cinnamic acid ester as a stabilizer for organic materials against oxidation, thermal and / or chemical radiation decomposition. The present invention also relates to an organic material stabilized in response thereto. A further aspect of the present invention relates to a method for stabilizing an organic material, wherein a specific cinnamic acid ester is incorporated into the organic material. According to the present invention, a specific novel cinnamic acid ester is also disclosed.

Description

Technology Field

[0001] The present invention relates to the use of a specific cinnamic acid ester as an organic material stabilizer, specifically to the use of a specific cinnamic acid ester as an organic material stabilizer against oxidation, heat, and / or chemical radiation decomposition. The present invention also relates to an organic material stabilized accordingly. A further aspect of the present invention relates to a method for stabilizing an organic material by incorporating a specific cinnamic acid ester into the organic material. According to the present invention, a specific novel cinnamic acid ester is also disclosed. Background Technology

[0002] Organic materials, such as plastics, undergo an aging process, which ultimately leads to a loss of value regarding desired properties, such as mechanical properties. This process, referred to as autoxidation, results in changes to polymer chains—e.g., changes in molecular weight or the creation of new chemical groups—caused by radical chain cleavage through mechanochemical processes or UV irradiation in the presence of oxygen. Therefore, stabilizers are used to prevent or at least delay this aging. Important and representative stabilizers are antioxidants, which interrupt the degradation process by interfering with free radicals generated during autoxidation. Generally, primary antioxidants, which can react directly with oxygen-containing free radicals or C-radicals, and secondary antioxidants, which react with peroxides generated in the interim [see C. Krohnke et al. Antioxidants in Ullmann's encyclopedia of industrial chemistry, Wiley-VCH Verlag, Weinheim 2015]. Representative primary antioxidants include, for example, phenolic antioxidants, amines, and lactones. The group of secondary antioxidants includes phosphorus compounds, such as phosphites and aphosphonates, as well as organic sulfur compounds, such as thioesters and disulfides. In fact, primary and secondary antioxidants often exhibit a synergistic effect when combined.

[0003] There is an increasing trend of replacing or supplementing plastics derived from fossil raw materials, such as petroleum or natural gas, with plastics based on renewable raw materials obtained through biochemical processes. Consequently, questions are also being raised regarding the sustainability of the primary and secondary antioxidants used here (and in plastics manufactured from fossil raw materials). Therefore, there is a need for stabilizers based on renewable and available raw materials that are highly effective, low volatility, and compatible with polymer substrates.

[0004] Primary antioxidants that are basically manufactured from renewable raw materials and, in some cases, can be used in plastics are known. A common 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 [see, for example, the literature (S. Al-Malaika, Macromol. Symp. 2001, 176, 107-117)]. For example, tocopherol can be isolated from natural components, such as wheat germ oil, sunflower oil, or olive oil.

[0005] Additional known phenols that exhibit antioxidant effects in plastics include, for example, quercetin (B. Kirschweng et al., Eur. Pol. J. 2018, 103, 228-237), dihydromyrecetin (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), as well as tannin (WJ Grigsby et al., Polymers 5 (2013) 344-360).

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

[0007] However, most natural phenols require significant effort to isolate, purify, or produce available secondary products. The problem to be solved

[0008] These objectives are achieved by the features of Patent Claim 1 relating to the use of any cinnamic acid ester for stabilizing organic materials. These objectives are further achieved by a method for stabilizing organic materials by the features of Patent Claim 14 and by an organic material stabilized according to Patent Claim 11 relating to a novel cinnamic acid ester that can be used as a stabilizer for the present invention by the features of Patent Claim 15. Each dependent claim represents an advantageous development.

[0009] Ferulic acid and its salts are used, for example, in the cosmetics industry or as active ingredients in pharmaceuticals (e.g., FR 2907338, CN 101181256, DE 1957433), where the formation of the salts is known in principle (e.g., AT 317184). Plastic stabilization by selected ester derivatives of ferulic acid (AF Reano et al. ACS Sustainable Chemistry and Engineering 4 (2015), 6562-6571, AF Reano et al. ACS Sustainable Chemistry and Engineering 3 (2015), 3486-3496) and plastic stabilization by selected ester derivatives of caffeic acid (V. Ambrogi et al. Biomacromolecules 15 (2014), 302-310) are also known in the prior art.

[0010] However, the above derivatives are produced in a relatively complex manner by enzymatic synthesis. In addition, known ferulic acid derivatives in the form of ester compounds include isosorbide ester (US 2007 189990), cholestanyl ester (WO 2018 / 153917), and oligomers and polymers of ferulic acid (US 2016 257846).

[0011] The objective of the present invention is to provide an antioxidant that has high efficacy and thermal stability, low volatility, is based on renewable raw materials, and is sustainable for plastics. Specific details for implementing the invention

[0012] Therefore, in a first embodiment, the present invention relates to an organic material, specifically a formula I for stabilizing the organic material against oxidation, heat and / or chemical radiation decomposition, i.e.

[0013] Chemical Formula I

[0014]

[0015] The invention relates to the use of a compound of, a mixture of multiple compounds of chemical formula I, and,

[0016] Among the above formulas,

[0017] R 1 , R 2 and R 3 Each is independently selected from the group consisting of a hydroxyl group, a linear or branched alkoxy group having 1 to 6 carbon atoms, and hydrogen, provided that R 1 , R 2 and R 3 At least one of the groups is a linear or branched alkoxy group having 1 to 6 carbon atoms and / or a hydroxyl group, and

[0018] R 4 is a linear or branched alkyl group having at least 8 carbon atoms, and groups according to the following chemical formulas IIa, IIb, and IIc, i.e.

[0019] Chemical formula IIa

[0020]

[0021] Chemical formula IIb

[0022]

[0023] Chemical formula IIc

[0024]

[0025] Selected from a group consisting of,

[0026] R 5 is the same or different in each case, and the hydroxyl group and the following chemical formula III, i.e.

[0027] Chemical Formula III

[0028]

[0029] Selected from a group consisting of the according to,

[0030] R 1 , R 2 and R 3 It is as defined above.

[0031] Surprisingly, it was discovered that the cinnamic acid derivative used according to the present invention can be used as a novel stabilizer based on renewable raw materials. It was confirmed that compared to the efficacy, environmental friendliness, and cost structure of stabilizers already known in the prior art, it has greater efficacy and environmental friendliness, and a more favorable cost structure.

[0032] Plastics, coatings, lubricants, hydraulic oils, engine oils, turbine oils, gear oils, metalworking fluids, chemicals, or monomers are particularly suitable as organic materials for the present invention.

[0033] According to the present invention, cosmetics are not considered among these organic materials.

[0034] According to a particularly preferred embodiment, the compound according to Formula I is the following compounds, namely

[0035]

[0036] Selected from a group consisting of, provided that R 4 is as defined in Claim 1.

[0037] For example, R 4 The group, i.e., a linear or branched alkyl group having at least 8 carbon atoms, may be derived from an alcohol selected from the group consisting of octan-1-ol, nonan-1-ol, decan-1-ol, undecan-1-ol, lauryl alcohol, tridecan-1-ol, myristyl alcohol, cetyl alcohol, stearyl alcohol, ceryl alcohol, myricyl alcohol, palmitoleyl alcohol, oleyl alcohol, arachidyl alcohol, behenyl alcohol, erucyl alcohol, lignoceryl alcohol, montanyl alcohol, linoleyl alcohol, isotridecyl alcohol, geraniol, rhodinool, citronellol, and cerol, and particularly preferably may be derived from an alcohol selected from the group consisting of lauryl alcohol and stearyl alcohol.

[0038] Desirable R 5 Qi refers to the following energies, that is

[0039]

[0040] It is selected from a group consisting of.

[0041] Among the compounds according to chemical formula I here Substitution patterns of the element according to and R 5 It is particularly desirable when the substitution pattern of the elements is the same.

[0042] This is, for example, R 5 In relation to this, it means that the substitution pattern of the groups according to the chemical formulas IIa, IIb, and IIc shown above and the cinnamic acid group according to chemical formula I is identical. These compounds are symmetric.

[0043] Preferably, the compound according to Formula I, or in the case of a mixture of multiple compounds according to Formula I, all compounds according to Formula I are present in the organic material in a weight ratio of 0.01 wt% to 10.00 wt%, preferably 0.02 wt% to 5.00 wt%, particularly preferably 0.05 wt% or 0.10 wt% to 2.00 wt%.

[0044] According to a further preferred embodiment, a compound according to Formula I or a mixture thereof is used to stabilize thermoplastic, elastomer, or duromer plastics. Specifically, the plastic

[0045] a) Olefin or diolefin-based polymers, e.g., polyethylene (LDPE, LLDPE, VLDPE, ULDPE, MDPE, HDPE, UHMWPE), metallocene PE (m-PE), polypropylene, polyisobutylene, poly-4-methyl-pentene-1, polybutadiene, polyisoprene, polycyclooctene, polyalkylene-carbon monooxide copolymer, and copolymers having a random or block structure, e.g., polypropylene-polyethylene (EP), EPM or EPDM, ethylene-vinyl acetate (EVA), ethylene-acrylate esters, e.g., butyl acrylate, ethylene-acrylic acid and salts thereof (ionomers), and trimers, e.g., ethylene-acrylic acid-(meth)acrylic acid glycidyl, graft polymers, e.g., polypropylene-graft-maleic anhydride, polypropylene-graft-acrylic acid, polyethylene-graft-acrylic acid, Polyethylene-polyacrylate butyl-graft-maleic anhydride and combinations thereof;

[0046] b) Polystyrene, polymethylstyrene, poly-alpha-methylstyrene, polyvinylnaphthalene, polyvinylbiphenyl, polyvinyltoluene, 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, e.g., corresponding graft copolymers, e.g., butadiene-phase styrene, SBS or SEBS-phase maleic anhydride, and grafts prepared from methyl methacrylate, styrene-butadiene, and ABS Copolymers (MABS), and hydrogenated polystyrene derivatives;

[0047] c) Halogen-containing polymers, e.g., polyvinyl chloride (PVC), polychloroprene and polyvinylidene chloride (PVDC), copolymers of vinyl chloride and vinylidene chloride, or copolymers of vinyl chloride and vinyl acetate, chlorinated polyethylene, polyvinylidene fluoride, epichlorohydrin homopolymers and copolymers thereof;

[0048] d) polymers of unsaturated esters, e.g., polyacrylates and polymethacrylates, e.g., polymethyl methacrylate (PMMA), polybutyl acrylate, polylauryl acrylate, polystearyl acrylate, polyglycidyl acrylate, polyglycidyl methacrylate, polyacrylonitrile, polyacrylamide, copolymers, e.g., polyacrylonitrile-alkyl polyacrylate;

[0049] e) Polymers and derivatives of unsaturated alcohols, e.g., polyvinyl alcohol, polyvinyl acetate, polyvinyl butyral, polyallyl phthalate, polyallyl melamine;

[0050] f) polyacetal, e.g., polyoxymethylene (POM), or, e.g., butanal, copolymer with polyphenylene oxide, and combination with polystyrene or polyamide;

[0051] g) Polymers of cyclic ethers, e.g., polyethylene glycol, polypropylene glycol, polyethylene oxide, polypropylene oxide, polytetrahydrofuran;

[0052] h) Polyurethanes prepared from hydroxy-terminated polyethers or polyesters and aromatic or aliphatic isocyanates, specifically linear polyurethanes (TPU) and polyureas;

[0053] i) polyamides, e.g., polyamide-6, 6.6, 6.10, 4.6, 4.10, 6.12, 10.10, 10.12, 12.12, polyamide 11, polyamide 12 and (partially) aromatic polyamides, e.g., polyphthalamides prepared with terephthalic acid and / or isophthalic acid and an aliphatic diamine or with an aliphatic dicarboxylic acid, e.g., adipic acid or sebacic acid and an aromatic diamine, e.g., 1,4- or 1,3-diaminobenzene, combinations of different polyamides, e.g., PA-6 and PA 6.6, or combinations of polyamide and polyolefin, e.g., PA / PP;

[0054] j) polyimide, polyamide-imide, polyetherimide, polyesterimide, poly(ether)ketone, polysulfone, polyethersulfone, polyarylsulfone, polyphenylene sulfide, polybenzimidazole, polyhydantoin;

[0055] k) polyesters produced from aliphatic or aromatic dicarboxylic acids and diols, or produced from hydroxycarboxylic acids, such as polyethylene terephthalate (PET), polybutylene terephthalate (PBT), polypropylene terephthalate (PTT), polyethylene naphthylate (PEN), poly-1,4-dimethylolcyclohexane terephthalate, polyhydroxybenzoate, polyhydroxynaphthalate, polylactic acid (PLA), polyhydroxybutyrate (PHB), polyhydroxyvalerate (PHV), polyethylene succinate, polytetramethylene succinate, polycaprolactone;

[0056] l) Polycarbonates, polycarbonate esters and formulations, e.g., PC / ABS, PC / PBT, PC / PET / PBT, PC / PA;

[0057] m) Cellulose derivatives, e.g., cellulose nitrate, cellulose acetate, cellulose propionic acid, cellulose butyric acid;

[0058] n) An epoxy resin formed by combining a difunctional or polyfunctional epoxy compound with, for example, an amine, anhydride, dicyandiamide, mercaptan, isocyanate-based curing agent or catalytically active curing agent;

[0059] o) Phenolic resins, e.g., phenol-formaldehyde resin, urea-formaldehyde resin, melamine-formaldehyde resin;

[0060] p) unsaturated polyester resins, alkyd resins, and allyl resins derived from unsaturated dicarboxylic acids and diols, and vinyl compounds;

[0061] q) silicones that are, for example, terminated by a vinyl group, such as silicones based on dimethylsiloxane, methylphenylsiloxane or diphenylsiloxane; and

[0062] r) A mixture, combination, or blend of two or more of the polymers described above

[0063] It is selected from a group consisting of.

[0064] If the polymer specified in a) to r) is a copolymer, it may exist in the form of a statistical (“random”), block, or “tapered” structure. Furthermore, the mentioned polymer may exist in the form of a linear, branched, stellate, or hyperbranched structure.

[0065] If the polymer specified in a) to r) is a stereoregular polymer, this polymer may exist not only in a homologous or stereoregular form, but may also exist in a hybrid form or as a stereoblock copolymer.

[0066] In addition, the polymers specified in a) to r) can have both an amorphous form and a (partially) crystalline form.

[0067] Optionally, the polyolefin mentioned in a) may also be crosslinked, for example, crosslinked polyethylene referred to as X-PE.

[0068] In addition, the present compound can be used to stabilize rubber and elastomers. This may be natural rubber (NR) or synthetic rubber materials, such as 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 urethane rubber, or silicone rubber.

[0069] Aside from new products, plastic may be recycled plastic derived from industrial collections, such as production waste, or plastic derived from household or recyclable collections.

[0070] Thermoplastic plastics, specifically plastics used in packaging, e.g., food packaging, specifically polyolefins, polystyrene, polyesters, and polyamides are preferred as plastics. Polypropylene homopolymers and copolymers, and LDPE, LLDPE, HDPE, MDPE, VLDPE, and polyethylene terephthalate (PET), as well as polyethylene in the form of homopolymers and copolymers, are particularly highly preferred.

[0071] Additionally, aliphatic polyesters derived from renewable raw materials and substantially prepared from aliphatic dicarboxylic acids and aliphatic diols, hydroxycarboxylic acids or lactones, such as polylactic acid (PLA), polyglycolic acid (PGA), polyhydroxybutyric acid (PHB), polyhydroxyvaleric acid (PHV), polyethylene succinate (PESu), polybutylene succinate (PBS), polyethylene adipate, poly(butylene succinate-co-adipate) (PBSA) or polycaprolactone (PCL) are particularly preferred.

[0072] For example, the plastic may include and / or be added to the plastic during use at least one additional additive selected from the group consisting of primary and / or secondary antioxidants, specifically phosphites, aphosphonates, thiols, phenolic antioxidants, sterically hindered amines, hydroxylamines, and mixtures or combinations thereof, UV absorbers, light stabilizers, hydroxylamine-based stabilizers, benzofuranone-based stabilizers, nucleating agents, impact modifiers, plasticizers, lubricants, rheology modifiers, chain extenders, processing aids, pigments, dyes, fluorescent whitening agents, antimicrobial agents, antistatic agents, antislip agents, anti-stick agents, coupling agents, dispersants, compatibilizers, oxygen scavengers, acid scavengers, co-stabilizers, marking agents, and anti-fogging agents.

[0073] When additional additives or multiple additives are contained in the plastic, the additives are contained in a total amount of 0.01 wt% to 9.99 wt%, preferably 0.01 wt% to 4.98 wt%, and particularly preferably 0.02 wt% to 2.00 wt%, based on the sum of at least one compound according to Formula I, an organic material, and at least one additive, or are added during use.

[0074] The present invention also relates to organic materials, specifically compounds of formula I, i.e.

[0075] Chemical Formula I

[0076] [In the middle of the meal, R 1 , R 2 , R 3 and R 4 [is as defined in either claim 1 and claim 5]

[0077] It also relates to a plastic composition comprising at least one or a mixture of multiple compounds according to Formula I as a stabilizer.

[0078] With respect to the compound according to Formula I, all of the preferred formulations expressed as formulas as above are also applied without limitation to the organic material according to the present invention.

[0079] The organic material preferably has the following composition, and these components together make up 100 weight percent:

[0080] In the case of a compound according to Formula I, or a mixture of multiple compounds according to Formula I, 0.01 wt% to 10.00 wt% of the total of all compounds according to Formula I, preferably 0.02 wt% to 5.00 wt%, particularly preferably 0.10 wt% to 2.00 wt%;

[0081] At least one organic material selected from the group consisting of organic materials, preferably plastics, coatings, lubricants, hydraulic oils, engine oils, turbine oils, gear oils, metalworking fluids, chemicals, or monomers, in an amount of 99.99 wt% to 90.00 wt%, preferably 99.89 wt% to 95.00 wt%, particularly preferably 99.90 wt% to 98.00 wt%; and

[0082] At least one additive in an amount of 0% to 9.99% by weight, preferably 0% to 4.98% by weight, particularly preferably 0.02% to 2.00% by weight.

[0083] According to a further preferred embodiment, at least one additive is selected from the group consisting of primary and / or secondary antioxidants, specifically primary and / or secondary antioxidants selected from the group consisting of phosphites, aphosphonates, thiols, phenolic antioxidants, sterically hindered amines, hydroxylamines, and mixtures or combinations thereof, UV absorbers, light stabilizers, hydroxylamine-based stabilizers, benzofuranone-based stabilizers, nucleating agents, impact modifiers, plasticizers, lubricants, rheology modifiers, chain extenders, processing aids, pigments, dyes, fluorescent whitening agents, antimicrobial agents, antistatic agents, antislip agents, anti-stick agents, coupling agents, dispersants, compatibilizers, oxygen scavengers, acid scavengers, co-stabilizers, marking agents, and anti-fogging agents;

[0084] Specifically, a secondary antioxidant selected from the group consisting of phosphites, aphosphonates, and thiols, at least one co-stabilizing agent selected from the group consisting of polyols, an acid scavenger, and a sterically hindered amine.

[0085] Suitable primary antioxidant (A) Examples include phenolic antioxidants, amines, and lactones.

[0086] Suitable synthetic phenolic antioxidants As, for example

[0087] 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, linear or branched nonylphenol, e.g., 2,6-dinonyl-4-methylphenol, 2,4-dimethyl-6-(1'-methylundek-1'-yl)phenol, 2,4-dimethyl-6-(1'-methylheptadek-1'-yl)phenol, 2,4-dimethyl-6-(1'-methyltridek-1'-yl)phenol and mixtures thereof;

[0088] Alkylthiomethyl phenol, e.g., 2,4-dioctylthiomethyl-6- tert -butylphenol, 2,4-dioctylthiomethyl-6-methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol, 2,6-didodecylthiomethyl-4-nonylphenol;

[0089] Hydroquinone and alkylated hydroquinone, e.g., 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 -Butylhydroquinone, 2,5-di- tert -butyl-4-hydroxyanisole, 3,5-di- tert -butyl-4-hydroxyanisole, 3,5-di-stearic acid tert -butyl-4-hydroxyphenyl, adipic acid bis(3,5-di- tert -butyl-4-hydroxyphenyl);

[0090] Tocopherols, e.g., α-, β-, γ-, δ-tocopherols and mixtures thereof (vitamin E);

[0091] 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);

[0092] Alkylidene bisphenol, 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-methylphenyl)-3-n-dodecylmercaptobutane, ethylene glycol butyrate-bis[3,3-bis(3'- tert -butyl-4'-hydroxyphenyl)], bis(3- tert -butyl-4-hydroxy-5-methylphenyl)dicyclopentadiene, bis[2-(3'- terephthalate tert -butyl-2'-hydroxy-5'-methylbenzyl)-6- tert -butyl-4-methylphenyl], 1,1-bis-(3,5-dimethyl-2-hydroxyphenyl)butane, 2,2-bis(3,5-di- tert -butyl-4-hydroxyphenyl)propane, 2,2-bis-(5- tert -butyl-4-hydroxy-2-methylphenyl)-4-n-dodecylmercaptobutane, 1,1,5,5-tetra(5- tert -butyl-4-hydroxy-2-methylphenyl)pentane;

[0093] O-, N- and S-benzyl compounds, e.g., 3,5,3',5'-tetra- tert -butyl-4,4'-dihydroxydibenzyl ether, octadecyl acetate-4-hydroxy-3,5-dimethylbenzyl mercapto, tridecyl acetate-4-hydroxy-3,5-di- tert -butylbenzylmercapto, tris(3,5-di- tert -butyl-4-hydroxybenzyl)amine, bis(4- dithioterephthalate) tert -butyl-3-hydroxy-2,6-dimethylbenzyl), bis(3,5-di- sulfide tert -butyl-4-hydroxybenzyl), isooctyl-3,5-di- tert -butyl-4-hydroxybenzylmercaptoacetate;

[0094] Hydroxybenzyl malonate, e.g., dioctadecyl malonicate-2,2-bis(3,5-di- tert -butyl-2-hydroxybenzyl), dioctadecyl-2-(3- malonicate tert -butyl-4-hydroxy-5-methylbenzyl), didodecil mercaptoethyl malonate-2,2-bis(3,5-di- tert -butyl-4-hydroxybenzyl), bis-malonicate[4-(1,1,3,3-tetramethylbutyl)phenyl]-2,2-bis(3,5-di- tert -butyl-4-hydroxybenzyl);

[0095] Aromatic hydroxybenzyl compounds, such as 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;

[0096] Triazine compounds, for example, 2,4-bis(octylmercapto)-6-(3,5-di- tert -butyl-4-hydroxyanilino)-1,3,5-triazine, 2-octylmercapto-4,6-bis(3,5-di- tert -butyl-4-hydroxyanilino)-1,3,5-triazine, 2-octylmercapto-4,6-bis(3,5-di- tert -butyl-4-hydroxyphenoxy)-1,3,5-triazine, 2,4,6-tris(3,5-di- tert -butyl-4-hydroxyphenoxy)-1,2,3-triazine, isocyanuric acid 1,3,5-tris(3,5-di- tert -butyl-4-hydroxybenzyl), isocyanuric acid 1,3,5-tris(4- tert -butyl-3-hydroxy-2,6-dimethylbenzyl), 2,4,6-tris(3,5-di- tert -butyl-4-hydroxyphenylethyl)-1,3,5-triazine, 1,3,5-tris(3,5-di- tert -butyl-4-hydroxyphenylpropionyl)hexahydro-1,3,5-triazine, isocyanuric acid 1,3,5-tris(3,5-dicyclohexyl-4-hydroxybenzyl);

[0097] Benzyl phosphonate, e.g., dimethyl-2,5-di- tert -butyl-4-hydroxybenzylphosphonate, diethyl-3,5-di- tert -Butyl-4-hydroxybenzylphosphonate, dioctadecyl-3,5-di- tert -Butyl-4-hydroxybenzylphosphonate, dioctadecyl-5- tert -butyl-4-hydroxy-3-methylbenzylphosphonate, 3,5-di- tert -Calcium salt of butyl-4-hydroxybenzylphosphonic acid monoethyl ester;

[0098] Acylaminophenols, e.g., 4-hydroxylauranilide, 4-hydroxystearanilide, octyl-N-(3,5-di-carbamate tert -butyl-4-hydroxyphenyl);

[0099] β-(3,5-d- tert-butyl-4-hydroxyphenyl)propionic acid and a monohydric alcohol or polyhydric alcohol, e.g., 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, isocyanuric acid tris(hydroxyethyl), N,N'-bis(hydroxyethyl)oxamide, 3-thioundecanol, 3-thipentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane ester;

[0100] β-(5- tert -butyl-4-hydroxy-3-methylphenyl)propionic acid and monohydric or polyhydric alcohols, e.g., 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, isocyanuric acid tris(hydroxyethyl), N,N'-bis(hydroxyethyl)oxamide, 3-thioundecanol, 3-thipentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane, 3,9-bis[2-{3-(3- tert ester of -butyl-4-hydroxy-5-methylphenyl)propionyloxy}-1,1-dimethylethyl]-2,4,8,10-tetraoxaspiro[5.5]undecane;

[0101] β-(3,5-dicyclohexyl-4-hydroxyphenyl)propionic acid and esters of monohydric or polyhydric alcohols, such as methanol, ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, isocyanuric acid tris(hydroxyethyl), N,N'-bis(hydroxyethyl)oxamide, 3-thioundecanol, 3-thipentadecanol, trimethylhexanediol, trimethylolpropane, and 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane;

[0102] (3,5-d- tert -butyl-4-hydroxyphenyl)acetic acid and esters of monohydric or polyhydric alcohols, such as methanol, ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, isocyanuric acid tris(hydroxyethyl), N,N'-bis(hydroxyethyl)oxamide, 3-thioundecanol, 3-thipentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane;

[0103] β-(3,5-d- tert Amides of -butyl-4-hydroxyphenyl)propionic acid, e.g., N,N'-bis(3,5-di- tert -butyl-4-hydroxyphenylpropionyl)hexamethylene diamide, N,N'-bis(3,5-di- tert -butyl-4-hydroxyphenylpropionyl)hexamethylene diamide, N,N'-bis(3,5-di- tert -butyl-4-hydroxyphenylpropionyl)hexamethylene diamide, 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, marketed by Uniroyal);

[0104] Ascorbic acid (Vitamin C)

[0105] There is.

[0106] Particularly desirable phenolic antioxidants include those having the following structures. :

[0107]

[0108]

[0109]

[0110] [In the formula, n is 2 to 10]

[0111] Particularly highly desirable phenolic antioxidants Examples include octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid and pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)) propionic acid.

[0112] Additionally, particularly desirable phenolic antioxidants It is based on renewable raw materials such as, for example, tocopherol (vitamin E), tocotrienol, tocomomomonoenol, carotenoids, hydroxytyrosol, flavonoids such as chrysine, quercetin, hesperidin, neohesperidin, naringin, morin, kaempferol, fisetin, anthocyanins such as delphinidin and malvidin, curcumin, carnosolic acid, carnosol, rosmarinic acid and resperatrol.

[0113] Suitable amine-based antioxidants As, for example

[0114] N,N'-di-isopropyl-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-octadecanoylamino-phenol, bis(4-methoxyphenyl)amine, 2,6-di-tert-butyl-4-dimethylaminomethyl-phenol, 2,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, N,N,N',N'-tetra-methyl-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, monoalkylation and dialkylation tert -Butyl / tert - Mixture of octyldiphenylamine, mixture of monoalkylated and dialkylated nonyldiphenylamine, mixture of monoalkylated and dialkylated dodecyldiphenylamine, mixture of monoalkylated and dialkylated isopropyl / isohexyl-diphenylamine, monoalkylated and dialkylated tert - Butyldiphenylamine, 2,3-dihydro-3,3-dimethyl-4H-1,4-benzothiazine, mixture of phenothiazines, monoalkylation and dialkylation tert -Butyl / tert - Mixture of octylphenothiazines, monoalkylation and dialkylation tert There are mixtures of octylphenothiazine, N-allylphenothiazine, N,N,N',N'-tetraphenyl-1,4-diaminobut-2-ene, and mixtures and combinations of these.

[0115] Desirable amine-based antioxidants As N,N'-di-isopropyl-p-phenylenediamine, N,N'-di- sec There are 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, and N-cyclohexyl-N'-phenyl-p-phenylenediamine.

[0116] Particularly desirable amine-based antioxidants As for, there are things that have the following structures:

[0117]

[0118] [In the formula, n is 3 to 100]

[0119] Additional desirable amine-based antioxidants As hydroxylamine or N-oxide (nitron), such as N,N-dialkylhydroxylamine, N,N-dibenzylhydroxylamine, N,N-dilaurylhydroxylamine, N,N-distearylhydroxylamine, N-benzyl-α-phenylnitron, N-octadecyl-α-hexadecylnitron, and the following chemical formula, i.e.

[0120]

[0121] There is Genox EP (SI group) according to.

[0122] Suitable lactoneBenzofuranone and indolinone, e.g., 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, There are 3-(3,5-dimethyl-4-pivaloyloxyphenyl)-5,7-di-tert-butyl-benzofuran-2-one, 3-(3,4-dimethylphenyl)-5,7-di-tert-butyl-benzofuran-2-one, and 3-(2,3-dimethylphenyl)-5,7-di-tert-butyl-benzofuran-2-one, and

[0123]

[0124] There are also lactones that contain phosphites, such as the one mentioned above.

[0125] Suitable for the addition of antioxidants As isoindoleol[2,1-A]quinazoline, for example

[0126]

[0127] There is.

[0128] Suitable secondary antioxidants As, specifically, phosphites or aphosphonates, such as triphenyl phosphite, diphenylalkyl phosphite, phenyldialkyl phosphite, tri(nonylphenyl) phosphite, trilauryl phosphite, trioctadecyl phosphite, distearylpentaerythritol phosphite, tris-(2,4-di-phosphite tert -butylphenyl), diisodecylpentaerythritol phosphite, bis(2,4-di-phosphite tert -butylphenyl)pentaerythritol, bis(2,4-di-cumylphenyl)pentaerythritol phosphite, bis(2,6-di-phosphite tert -butyl-4-methylphenyl)pentaerythritol, diisodecyloxypentaerythritol phosphite, bis(2,4-di-phosphite tert -butyl-6-methylphenyl)pentaerythritol, dibis(2,4,6-tris( tert -butylphenyl)pentaerythritol, tristearylsorbitol phosphate, 2-tetrakis(2,4-di-aphosphonicate) tert -butylphenyl)-4,4'-biphenylene, 6-isooctyloxy-2,4,8,10-tetra- tert -butyl-12H-dibenz[d,g]-1,3,2-dioxaphosphosine, bis(2,4-di-methylphosphorate tert -butyl-6-methylphenyl), bis(2,4-di-ethylphosphorate tert -butyl-6-methylphenyl), 6-fluoro-2,4,8,10-tetra- tert -butyl-12-methyldibenz[d,g]-1,3,2-dioxaphosphosine, 2,2'2''-nitrilo[triethyltris(3,3'',5,5'-tetra- tert -butyl-1,1'-biphenyl-2,2'-diyl)], 2-ethylhexyl phosphite(3,3',5,5'-tetra- tert -butyl-1,1'-biphenyl-2,2'-diyl)), 5-butyl-5-ethyl-2-(2,4,6-tri- tert -Butylphenoxy-1,3,2-dioxaphosphiran is present.

[0129] Particularly desirable phosphite / aphosphonate As

[0130]

[0131]

[0132]

[0133] [In the formula, n is 3 to 100]

[0134] There is.

[0135] Desirable aphosphonates are

[0136]

[0137] am.

[0138] tris-(2,4-di-) phosphate tert -butylphenyl)phosphite is It is used very particularly favorably as a secondary antioxidant. .

[0139] Furthermore, suitable secondary antioxidants include organic sulfur compounds, such as sulfides and disulfides, such as distearylthio2propionate, dilaurylthio2propionate; ditridecyldithio2propionate, ditetradecylthio2propionate, and 3-(dodecylthio)-,1,1'-[2,2-bis[[3-(dodecylthio)-1-oxopropoxy]methyl]-1,3-propanediyl]propanoic acid esters. Those having the following structures are preferred:

[0140]

[0141] Suitable acid scavenger (“Antacids”) are specifically monovalent, divalent, trivalent, or tetravalent metals produced from fatty acids, preferably salts of alkali metals, alkaline earth metals, aluminum, or zinc, such as calcium stearate, magnesium stearate, zinc stearate, aluminum stearate, calcium laurate, calcium behenate, calcium lactate, and calcium stearoyl-2-lactic acid. An additional group of suitable acid scavengers includes hydrolactites, specifically synthetic hydrolactites based on aluminum, magnesium, and zinc, hydrocalumite, zeolites, alkaline earth oxides, specifically calcium oxide, magnesium oxide, and zinc oxide, alkaline earth carbonates, specifically calcium carbonate, magnesium carbonate, dolomite, and hydroxides, specifically brucite (magnesium hydroxide).

[0142] also Suitable public security purification agent Examples include polyols, specifically alditols or cyclitols. Examples of polyols include, for instance, pentaerythritol, dipentaerythritol, tripentaerythritol, short-chain polyether polyols or polyester polyols, and superbranched polymers / oligomers or dendrimers having alcohol groups, such as

[0143]

[0144] There is.

[0145] At least one alditol is preferably selected from the group consisting of threitol, erythritol, galactitol, mannitol, ribitol, sorbitol, xylitol, arabitol, isomalt, lactitol, maltitol, altritol, iditol, maltotritol, hydrogenated oligosaccharides and polysaccharides having polyol terminal groups, and mixtures thereof. At least one preferred alditol is particularly preferably selected from the group consisting of erythritol, mannitol, isomaltol, maltitol, and mixtures thereof.

[0146] Examples of additional suitable sugar alcohols include heptitol and octitol: mesoglycero-allo-heptitol, D-glycero-D-altro-heptitol, D-glycero-D-mannno-heptitol, mesoglycero-gullo-heptitol, D-glycero-D-galacto-heptitol (perceitol), D-glycero-D-gluco-heptitol, L-glycero-D-gluco-heptitol, D-erythro-L-galacto-octitol, and D-threo-L-galacto-octitol.

[0147] In particular, at least one cyclitol may be selected from the group consisting of inositol (mio-, silo-, D-chiro-, L-chiro-, muco-, neo-, allo-, epi-, and cis-inositol), 1,2,3,4-tetrahydroxycyclohexane, 1,2,3,4,5-pentahydroxycyclohexane, quercetol, biscumitol, borneositol, conduritol, ononitol, pinitol, pinpolitol, quebrachitol, cyceritol, quinic acid, shikimic acid, and valienol; in this case, myo-inositol is preferred.

[0148] Suitable light stabilizer Examples include compounds based on 2-(2'-hydroxyphenyl)benzotriazole, 2-hydroxybenzophenone, esters of benzoic acid, acrylates, oxamides, and 2-(2-hydroxyphenyl)-1,3,5-triazine.

[0149] Suitable 2-(2'-hydroxyphenyl)benzotriazoles include, for example, 2-(2'-hydroxy-5'methylphenyl)benzotriazole, 2-(3',5'-di- tert-butyl-2'-hydroxyphenyl)benzotriazole, 2-(5'- tert -butyl-2'-hydroxy-phenyl)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(α,α-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-methoxycarbonylethyl)phenyl)-5-chlorobenzotriazole, 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-isooctyloxycarbonylethyl)phenylbenzotriazole, 2,2'-methylenebis[4-(1,1,3,3-tetramethylbutyl)-6-benzotriazole-2-ylphenol]; 2-[3'- tertEster exchange product of -butyl-5'-(2-methoxycarbonylethyl)-2'-hydroxyphenyl]-2H-benzotriazole and polyethylene glycol 300; [R―CH2CH2―COO―CH2CH2-]-2, (wherein R is 3'- tert -butyl-4'-hydroxy-5'-2H-benzotriazole-2-ylphenyl, 2-[2'-hydroxy-3'-(α,α-dimethylbenzyl)-5'-(1,1,3,3-tetramethylbutyl)phenyl]benzotriazole, 2-[2'-hydroxy-3'-(1,1,3,3-tetramethylbutyl)-5'-(α,α-dimethylbenzyl)phenyl]benzotriazole)

[0150] Suitable 2-hydroxybenzophenones include, for example, 4-hydroxy-, 4-methoxy-, 4-octyloxy-, 4-decyloxy-, 4-dodecyloxy, 4-benzyloxy, 4,2',4'-trihydroxy-, and 2'-hydroxy-4,4'-dimethyloxy derivatives of 2-hydroxybenzophenone.

[0151] Suitable acrylates include, for example, ethyl-α-cyano-β-β-diphenyl acrylate, isooctyl-α-cyano-β,β-diphenyl acrylate, methyl-α-carbomethoxycinnamate, methyl-α-cyano-β-methyl-p-methoxycinnamate, butyl-α-cyano-β-methyl-p-methoxycinnamate, methyl-α-carbomethoxy-p-methoxycinnamate, and N-(β-carbomethoxy-β-cyanovinyl)-2-methylindoline.

[0152] Suitable esters of benzoic acid include, for example, salicylic acid 4- tert -butylphenyl, phenyl salicylate, octylphenyl salicylate, dibenzoylesorcinol, bis(4- tert -Butylbenzoyl)resorcinol, benzoylesorcinol, 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 is present.

[0153] Suitable oxamides include, for example, 4,4'-dioctyloxyoxanilide, 2,2'-diethoxyoxanilide, 2,2'-dioctyloxy-5,5'-di- tert -Butoxanilide, 2,2'-Didodecyloxy-5,5'-D- tert -Butoxanilide, 2-ethoxy-2'-ethyloxanilide, N,N'-bis(3-dimethylaminopropyl)oxamide, 2-ethoxy-5- tert -Butyl-2'-ethoxanilide, this and 2-ethoxy-2'-ethyl-5,4'-di- tert There are mixtures of butoxanilide, mixtures of o- and p-methoxy-disubstituted oxanilides, and mixtures of o- and p-ethoxy-disubstituted oxanilides.

[0154] Suitable 2-(2-hydroxyphenyl)-1,3,5-triazines include, for example, 2,4,6-tris(2-hydroxy-4-octyloxyphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2,4-bis(2-hydroxy-4-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, There are 2-(2-hydroxyphenyl)-4-(4-methoxyphenyl)-6-phenyl-1,3,5-triazine and 2-{2-hydroxy-4-[3-(2-ethylhexyl-1-oxy)-2-hydroxypropyloxy]phenyl}-4,6-bis(2,4-dimethylphenyl-1,3,5-triazine.

[0155] Suitable metal inertExamples include N,N'-diphenyloxamide, N-salicilal-N'-salisilylhydrazine, N,N'-bis(salisilyl)hydrazine, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazine, 3-salisilylamino-1,2,4-triazole, bis(benzylidene)oxalyldihydrazide, oxanilide, isophthaloyldihydrazide, sebacoyl-bis-phenylhydrazide, N,N'-diacetyladipoyldihydrazide, N,N'-bis(salisilyl)oxyldihydrazide, and N,N'-bis(salisilyl)thiopropionyldihydrazide.

[0156] As a particularly desirable metal inert,

[0157]

[0158] There is.

[0159] Suitable hindering amines As such, for example, 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)-n-butyl-3,5-di-tert-butyl-4-hydroxybenzylmalonicate, condensation product of 1-(2-hydroxyethyl)--2,2,6,6-tetramethyl-4-hydroxypiperidine and succinate, N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4- tert- Octylamino-2,6-Dichloro-1,3,5-Triazine, triacetic acid tris(2,2,6,6-tetramethyl-4-piperidyl)nitrilo, tetrakis(2,2,6,6-tetramethyl-4-piperidyl)-1,2,3,4-butanetetracarboxylate, 1,1'-(1,2-ethandiyl)-bis(3,3,5,5-tetramethylpiperazinone), linear or cyclic condensation product of 4-benzoyl-2,2,6,6-tetramethylpiperidine and 4-stearyloxy-2,2,6,6-tetramethylpiperidine, linear or cyclic condensation of N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4-morpholino-2,6-dichloro-1,3,5-triazine There are reaction products, 7,7,9,9-tetramethyl-2-cyclodecyl-1-oxa-3,8-diaza-4-oxosspiro-[4,5]decane and epichlorohydrin.

[0160] Sterile hindered NH, N-alkyl, e.g. N-methyl or N-octyl, N-alkoxy derivatives, e.g. N-methoxy or N-octyloxy, cycloalkyl derivatives, e.g. N-cyclohexyloxy and N-(2-hydroxy-2-methylpropoxy) analogs are also each included in the structures presented above.

[0161] The desirable hindering amine also has the following structure:

[0162]

[0163]

[0164] Desirable oligomers and polymer-disrupted amines It has the following structure:

[0165]

[0166]

[0167]

[0168] In the compounds named above, n means 3 to 100, respectively.

[0169] An additional suitable light stabilizer is Hostanox NOW (Manufacturer: Clariant SE) having the following chemical formula:

[0170]

[0171] [In the formula, R is -OC(O)-C 15 H 31 or -OC(O)-C 17 H 35 [means]

[0172] Suitable dispersant Examples include polyacrylates, such as copolymers having long-chain side groups, polyacrylate block copolymers, alkylamides, such as N,N'-1,2-ethanediylbis-octadecaneamide, sorbitan esters, such as monostearyl sorbitan esters, titanates and zirconates, reactive copolymers having functional groups, such as polypropylene-co-acrylic acid, polypropylene-co-maleic anhydride, polyethylene-co-glycidyl methacrylate, polystyrene-alt-maleic anhydride-polysiloxane: such as dimethylsilanediol-ethylene oxide copolymer, polyphenylsiloxane copolymer, amphiphilic copolymers: such as polyethylene block-polyethylene oxide, dendrimers, such as dendrimers containing hydroxyl groups.

[0173] Suitable antinucleating agent Examples include azine dyes, such as nigrosine.

[0174] Suitable flame retardant As, specifically

[0175] a) Inorganic flame retardants, e.g., AI(OH)3, Mg(OH)2, AIO(OH), MgCO3, sheet silicates, e.g., montmorillonite or sepiolite, unmodified or organically modified double salts, e.g., Mg-Al silicate, POSS (polyhedral oligomeric silsesquioxane) compounds, huntite hydromagnesite or halloysite and Sb2O3, Sb2O5, MoO3, zinc tartrate, zinc hydroxytartarrate;

[0176] b) nitrogen-containing flame retardants, e.g., melamine, melem, melam, melon, melamine derivatives, melamine condensation products or melamine salts, benzoguanamine, polyisocyanurates, allantoin, phosphacene, specifically melamine cyanurate, melamine phosphate, dimelamine phosphate, melamine pyrophosphate, melamine polyphosphate, melamine metal phosphates, e.g., melamine aluminum phosphate, melamine zinc phosphate, melamine magnesium phosphate, and corresponding pyrophosphates and polyphosphates, poly-[2,4-(piperazine-1,4-yl)-6-(morpholin-4-yl)-1,3,5-triazine], ammonium polyphosphate, melamine borate, melamine hydrobromide;

[0177] c) radical generating agents, e.g., alkoxyamines, hydroxylamine esters, azo compounds, sulfenamides, sulfenimide, dicumyl or polycumyl, hydroxyimide and derivatives thereof, e.g., hydroxyimide esters or hydroxyimide ethers;

[0178] d) phosphorus-containing flame retardants, e.g., red phosphorus; phosphates, e.g., resorcinol diphosphate, bisphenol A diphosphate and oligomers thereof; triphenyl phosphate, ethylenediamine diphosphate; phosphinates, e.g., salts of hypophosphoric acid and its derivatives, e.g., alkyl phosphinate salts, e.g., aluminum diethyl phosphinate or zinc diethyl phosphinate or aluminum phosphinate; aluminum phosphite; aluminum phosphonicate; phosphonate esters; oligomers and polymer derivatives of methanephosphonic acid; 9,10-dihydro-9-oxa-10-phosphorylphenanthrene-10-oxide (DOPO) and substituted compounds thereof;

[0179] e) Optionally combined with Sb2O3 and / or Sb2O5, chlorine and bromine-based halogenated flame retardants, e.g., polybrominated diphenyl oxide, e.g., decabromodiphenyl oxide, tris(3-bromo-2,2-bis(bromomethyl)propyl-phosphate, tris(tribromoneopentyl)phosphate, tetrabromophthalic acid, 1,2-bis(tribromophenoxy)ethane, hexabromocyclododecane, brominated diphenylethane, isocyanuric acid tris-(2,3-dibrompropyl), ethylene-bis-(tetrabromophthalimide), tetrabromo-bisphenol A, brominated polystyrene, brominated polybutadiene or polystyrene brominated polybutadiene copolymer, brominated polyphenylene ether, brominated epoxy resin, Pentabromobenzyl polyacrylate;

[0180] f) Optionally a carrier material, e.g., silicate borates, e.g., zinc borate or calcium borate;

[0181] g) Sulfur-containing compounds, e.g., elemental sulfur, disulfides and polysulfides, thiuram sulfide, dithiocarbamate, mercaptobenzothiazole and sulfenamide;

[0182] h) anti-drip agent, e.g., polytetrafluoroethylene;

[0183] i) silicon-containing compounds, e.g., polyphenylsiloxanes;

[0184] j) carbon variants, e.g., carbon nanotubes (CNT), expanded graphite, or graphene; and

[0185] k) A combination or mixture of these

[0186] There is.

[0187] Suitable plasticizer Examples include phthalic acid esters, adipic acid esters, citric acid esters, 1,2-cyclohexanedicarboxylic acid esters, trimellitic acid esters, isolovid esters, phosphate esters, epoxides, such as epoxidized soybean oil or aliphatic polyesters.

[0188] Suitable release lubricants and processing aids Examples include polyethylene wax, polypropylene wax, salts of fatty acids, such as calcium stearate, zinc stearate, or salts of montan wax, amide waxes, such as erucic acid amide or oleic acid amide, fluoropolymers, silicones, or neoalkoxycarbonates and zirconates.

[0189] Suitable pigment The pigments may have inorganic or organic properties. Examples of inorganic pigments include titanium dioxide, zinc oxide, zinc sulfide, iron oxide, ultramarine, and black carbon; examples of organic pigments include anthraquinone, antantron, benzimidazolone, quinacridone, diketoptyrolopyrrole, dioxazine, inanthrone, isoindoline, azo compounds, perylene, phthalocyanine, or pyranthrone. Additional suitable pigments include pigments exhibiting a metallic effect or metal oxide-based pearlescent pigments.

[0190] Suitable fluorescent whitening agent Examples include bis-benzozoxazole, phenylcoumarin, or bis(styryl)biphenyl, and specifically, there are fluorescent whitening agents having the following chemical formula:

[0191]

[0192]

[0193] Suitable inert filling agent Examples include polysiloxanes, polyacrylates, specifically block copolymers, such as polymethacrylic acid-polyalkylene oxide or poly(meth)acrylic acid glycidyl, and, for example, styrene and copolymers thereof, and epoxides having the following structure:

[0194]

[0195] Suitable antistatic agent Examples include polymers such as ethoxylated alkylamines, fatty acid esters, alkylsulfonates, and polyetheramides.

[0196] Suitable ozone decomposition inhibitoris the aforementioned amine, e.g., N,N'-di-isopropyl-p-phenylenediamine, N,N'-di- sec There are 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, and N-cyclohexyl-N'-phenyl-p-phenylenediamine.

[0197] Suitable nucleating agent As such, talc, alkali or alkaline earth salts of monofunctional and polyfunctional carboxylic acids, e.g., benzoic acid, succinic acid, adipic acid, e.g., sodium benzoate, zinc glycerolate, aluminum hydroxy-bis(4 -tert- Butyl benzoate, 2,2 ' There are methylene-bis-(4,6-di-tert-butylphenyl)phosphate, and trisamides and diamides, such as trimethic acid tricyclohexylamide, trimethic acid tri(4-methylcyclohexylamide), trimethic acid tri(tert-butylamide), N,N',N"- 1,3,5-benzoltriyltris(2,2-dimethyl-propanamide) or 2,6-naphthalene dicarboxylic acid cyclohexylamide.

[0198] Additives suitable for increasing the molecular weight of polycondensation polymers Examples of (chain extenders) include diepoxys bis-oxazoline, bis-oxazolone, bis-oxazine, diisocyanates, dianhydrides, bis-acyllactams, bis-maleimide, dicyanates, and carbodiimide. Additional suitable chain extenders include polymer compounds, such as polystyrene-polyacrylate-poly(meth)acrylate glycidyl copolymer, polystyrene-maleic anhydride copolymer, and polyethylene-maleic anhydride copolymer.

[0199] Additives suitable for increasing electrical conductivityExamples include the aforementioned 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 additives suitable for increasing thermal conductivity include aluminum nitride and boron nitride.

[0200] Suitable infrared active additive Examples include aluminum silicate or dye components, such as phthalocyanine or anthraquinone.

[0201] Suitable release agent Examples include silicone, soap, and wax, such as montan wax.

[0202] In addition, the additive according to the present invention can be used to stabilize oils, fats, and chemical products. If the organic material is an oil or fat, the additive may be based on mineral oil, vegetable fat, or animal fat or oil, or may be based on fat or wax, for example, based on synthetic esters. Examples of vegetable oils and fats include palm oil, olive oil, rapeseed oil, linseed oil, soybean oil, sunflower oil, and castor oil; examples of animal fats include fish oil or beef tallow. The compound according to the present invention may also be used as a stabilizer for lubricants, hydraulic oils, motor oils, turbine oils, gear oils, and metalworking fluids, or as a lubricating grease. Such mineral or synthetic lubricants are mainly based on hydrocarbons. Examples of chemical products include those used to stabilize polyols used in the manufacture of polyurethanes or to stabilize monomers during transport and storage, such as styrene, acrylic resin, and methacrylate ester.

[0203] The present invention also provides, specifically, a method for stabilizing an organic material against oxidation, heat and / or chemical radiation decomposition, wherein the material is of formula I, i.e.

[0204] Chemical Formula I

[0205] [In the middle of the meal, R 1 , R 2 , R 3 and R 4 [is as defined in any one of claims 1 and 5]

[0206] The invention relates to a method of incorporating a compound or a plurality of such compounds into an organic material.

[0207] All preferred statements relating to the compound of Formula I represented by the above formula also apply without limitation to the method according to the present invention.

[0208] The present invention also uses the formula I, i.e.

[0209] Chemical Formula I

[0210]

[0211] It relates to a compound according to, provided that, among the above formula,

[0212] R 1 , R 2 and R 3 Each is independently selected from the group consisting of a hydroxyl group and a linear or branched alkoxy group having 1 to 6 carbon atoms and hydrogen, provided that R 1 , R 2 and R 3 At least one of the groups is a hydroxyl group and / or a linear or branched alkoxy group having 1 to 6 carbon atoms, and the following chemical formulas IIa, IIb, and IIc, i.e.

[0213] Chemical formula IIa

[0214]

[0215] Chemical formula IIb

[0216]

[0217] Chemical formula IIc

[0218] However,

[0219] Single R 5 is the same or different in each case, and the hydroxyl group and the following chemical formula III, i.e.

[0220] Chemical Formula III

[0221]

[0222] Selected from a group consisting of the corresponding ,

[0223] R 1 , R 2 and R 3 It is as defined above.

[0224] As stated above, the R 1 ~ R 5 All desirable statements related thereto also apply without limitation to the compounds according to the present invention.

[0225] The aforementioned additives, optionally additional additives, are applied to plastic through conventional processing methods. incorporation In this case, after the polymer is melted, a mixer, dough mixer, or extruder is preferably used to mix the additive composition according to the present invention and optionally additional additives. Preferably, an extruder equipped with a vacuum degassing device, such as a single-screw extruder, a twin-screw extruder, a planetary roller extruder, a ring extruder, or a cci-dough mixer, is preferred as the processing machine. Here, processing can be carried out in air, or optionally under inert gas conditions, such as nitrogen.

[0226] In addition, the additive composition according to the present invention can be prepared and introduced in the form of a so-called masterbatch or concentrate, for example, a masterbatch or concentrate containing 10% to 90% of the additive according to the present invention in a polymer.

[0227] The applications of the present invention for stabilizing organic materials according to the present invention are, specifically, those manufactured through extrusion, injection molding, blow molding, calendering, pressing process, spinning process, and rotomolding, such as the electrical and electronic industry, construction industry, transportation industry (automobiles, airplanes, ships, trains), medical field, household and electrical appliances, automotive parts, consumer goods, packaging, furniture, injection molded parts for textiles, foils or films, foams, fibers, cables and pipes, profiles, hollow bodies, ribbons, membranes, such as geomembranes or plastics in the form of adhesives. Additional applications include paints, colorants and coatings, and oils and fats.

[0228] The present invention will be described in more detail below with reference to exemplary environments, without being limited to the specific embodiments presented.

[0229] Implementation example

[0230] A) Preparation of hydroxycinnamate salt according to the present invention

[0231] A1) Synthesis of methyl ferulate

[0232]

[0233] 15 g (1.00 eq., 77.24 mmol) of ferulic acid was dissolved in 300 mL (95.77 eq., 237.00 g, 7397.00 mmol) of methanol in a 500 mL round-bottom flask while slowly heating. Then, 3.1 mL (0.75 eq., 57.99 mmol) of 95% sulfuric acid was added to the solution, and the solution turned yellow. The solution was heated at 70°C for 3 hours, then cooled and added to 375 mL of chloroform. The solution was then washed twice with 300 mL of distilled water, with one wash with a saturated sodium bicarbonate solution during each wash. The organic phase was dried on 100 g of sodium sulfate, and then the chloroform was distilled. As a result of drying under high vacuum, 14.03 g (67.39 mmol) of white solid was obtained. The yield was 87.25%.

[0234] A2) Synthesis of Octadecyl Ferulate

[0235]

[0236] First, 3.00 g (1.00 eq., 14.41 mmol) of methyl ferulate and 4.68 g (1.20 eq., 17.30 mmol) of stearyl alcohol were placed in a heated 100 mL round-bottom flask equipped with a condensation bridge and a cooling trap, under a counterflow of nitrogen. The reaction mixture was melted under an inert nitrogen atmosphere at 95°C while being gently stirred. 0.15 g (0.04 eq., 0.60 mmol) of dibutyltin oxide (DBTO) was added to this clear melt under a counterflow of nitrogen. The reaction temperature was raised to 140°C, and the pressure was set to 200 mbar to 800 mbar. After the reaction time (24 hours) had elapsed, the temperature was raised to 155°C, and the pressure was set to 1 x 10⁻⁶ -3Excess stearyl alcohol was removed by condensation under reduced pressure of bar. The vacuum was released by supplying nitrogen, and the pale yellow reaction melt was cooled to room temperature. Next, it was taken in dichloromethane, treated with 2.80 g of Fullertot (OPTIMUM 21OFF), and refluxed for 30 minutes. After filtration through a short silica pad, the solvent was removed by distillation under vacuum. 4.11 g (9.20 mmol, 64.84%) of white solid remained.

[0237] A3) Synthesis of Pentaerythritol Ester of Ferulic Acid

[0238]

[0239] Initially, 2.00 g (1.00 eq., 14.69 mmol) of pentaerythritol and 12.85 g (4.20 eq., 61.76 mmol) of methyl ferulate were introduced into a heated 100 mL round-bottom flask equipped with a condensation bridge and a cooling trap, under a counterflow of nitrogen. The reaction mixture was melted under an inert nitrogen atmosphere at 100°C while being gently stirred. 0.18 g (0.05 eq., 0.72 mmol) of dibutyltin oxide (DBTO) was added to the clear melt under the counterflow of nitrogen. The reaction temperature was raised to 170°C, and the pressure was set to 600 mbar–800 mbar. After the reaction time (27 hours) had elapsed, the temperature was set to 155°C, and the pressure was 1 x 10⁻⁶ -3 Excess methyl ferulate was removed by condensation under reduced pressure of bar. The vacuum was released by supplying nitrogen, and the yellow reaction melt was cooled to room temperature. Next, it was taken in dichloromethane, treated with 2.80 g of Fullertoir (OPTIMUM 21OFF), and refluxed for 30 minutes. After filtration through a short silica pad, the solvent was removed by distillation under vacuum. 10.02 g (11.92 mmol, 81.12%) of a fine powder yellow solid remained.

[0240] B) Review of Application Examples

[0241] To examine the effect of the stabilizer according to the present invention, commercially available polypropylene (Moplen HP 501N, Lyondell Basell Industries) was homogenized in a powder-powder mixture with the stabilizer stated in the table, circulated at 200 rpm at 200°C for 30 minutes in a twin-screw microextruder (MC 5, manufacturer DSM), and the reduction in force was recorded. Force is a direct measure of the molecular weight of polypropylene: the smaller the reduction, the greater the stabilization effect.

[0242]

[0243] As the degradation of the polymer was reduced throughout the testing process, the additive according to the present invention showed a clear stabilizing effect.

Claims

Claim 1 A method for stabilizing an organic material using a compound according to Chemical Formula I or a mixture of multiple compounds of Chemical Formula I, wherein Chemical Formula I Among the above formula, the above R 1 , R 2 and R 3 Each is independently selected from the group consisting of a hydroxyl group, a linear or branched alkoxy group having 1 to 6 carbon atoms, and hydrogen, provided that R 1 and R 2 At least one of the groups is a hydroxyl group, and the R 4 is a linear or branched alkyl group having at least 8 carbon atoms, and groups according to the following chemical formulas IIa, IIb, and IIc, i.e., chemical formula IIa Chemical formula IIb Chemical formula IIc The alkyl group is selected from the group consisting of octan-1-ol, nonan-1-ol, decan-1-ol, undecan-1-ol, lauryl alcohol, tridecan-1-ol, myristyl alcohol, cetyl alcohol, stearyl alcohol, ceryl alcohol, myricyl alcohol, palmitoleyl alcohol, oleyl alcohol, arachidyl alcohol, behenyl alcohol, erucyl alcohol, lignoceryl alcohol, montanyl alcohol, linoleyl alcohol, isotridecyl alcohol, geraniol, rhodinol, citronellol, and cerol, and the R 5 are the same or different in each case, and the hydroxyl group and the following chemical formula III, i.e., chemical formula III Selected from a group consisting of a channel according to, wherein the above R 1 , R 2 and R 3 An organic material stabilization method characterized by being as defined above, and wherein the organic material does not contain cosmetics. Claim 2 A method for stabilizing plastics, coatings, lubricants, hydraulic oils, engine oils, turbine oils, gear oils, metalworking fluids, chemicals, or monomers according to claim 1. Claim 3 In claim 1 or 2, the compound according to the above formula I is the following compounds, i.e. Selected from a group consisting of, provided that the above R 4 A method characterized by the same as defined in paragraph 1. Claim 4 In paragraph 1 or 2, the above R 4 A method characterized in that the group, i.e., a linear or branched alkyl group having at least 8 carbon atoms, is derived from an alcohol selected from the group consisting of lauryl alcohol and stearyl alcohol. Claim 5 In paragraph 1 or 2, the above R 5 Gi refers to the following gis, that is A method characterized by being selected from a group consisting of Claim 6 In paragraph 1 or 2, the above R 4 is selected from the group consisting of groups according to the following chemical formulas IIa, IIb, and IIc, and chemical formula IIa Chemical formula IIb Chemical formula IIc Among the compounds according to chemical formula I Substitution patterns of the element according to and R 5 A method characterized by having the same substitution pattern of the elements. Claim 7 A method according to claim 1 or 2, characterized in that, in the case of a compound according to the formula I or a mixture of multiple compounds according to the formula I, all compounds according to the formula I are contained in an organic material in a weight ratio of 0.01 wt% to 10.00 wt%. Claim 8 A method for stabilizing a thermoplastic, elastomer, or duromerplastic according to claim 1 or 2, wherein the plastic comprises: a) an olefin or diolefin-based polymer; b) polystyrene, polymethylstyrene, poly-alpha-methylstyrene, polyvinylnaphthalene, polyvinylbiphenyl, polyvinyltoluene, 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 polymer, e.g., a corresponding graft copolymer. and hydrogenated polystyrene derivatives; c) halogen-containing polymers; d) polymers of unsaturated esters; e) polymers and derivatives of unsaturated alcohols; f) polyacetals; g) polymers of cyclic ethers; h) hydroxy-terminated polyethers or polyesters and aromatic or aliphatic isocyanates; i) polyamides; j) polyimides; k) polyesters produced from aliphatic or aromatic dicarboxylic acids and diols, or from hydroxycarboxylic acids; l) polycarbonates, polycarbonate esters, and combinations; m) cellulose derivatives; n) epoxy resins formed by combining difunctional or polyfunctional epoxy compounds with amines, anhydrides, dicyandiamides, mercaptans, isocyanate-based curing agents, or catalytically active curing agents; o) phenolic resins; p) unsaturated dicarboxylic acids and diols, and vinyl compounds; q) silicones; And a method selected from the group consisting of two or more mixtures, combinations, or blends of the polymers described above. Claim 9 A method according to claim 1 or 2, characterized in that the plastic comprises at least one additional additive selected from the group consisting of primary and / or secondary antioxidants. Claim 10 A method according to claim 9, characterized in that the at least one additive is contained or added in an amount of 0.01% to 9.99% by weight based on the total amount of at least one compound according to formula I, the organic material, and the at least one additive. Claim 11 Chemical formula I, that is, chemical formula I [In the middle of the meal, R 1 , R 2 , R 3 and R 4 An organic material comprising at least one compound according to [as defined in Claim 1] or a mixture of multiple compounds according to the above formula I as a stabilizer, wherein cosmetics are not included in the organic material. Claim 12 An organic material having the following composition in claim 11: a compound according to Chemical Formula I, or in the case of a mixture of multiple compounds according to Chemical Formula I, 0.01% to 10.00% by weight of all compounds according to Chemical Formula I; at least one organic material 99.99% to 90.00% by weight; and at least one additive 0% to 9.99% by weight, provided that the sum of all said components is 100% by weight. Claim 13 An organic material according to claim 12, characterized in that at least one additive is selected from the group comprising primary and / or secondary antioxidants. Claim 14 As a method for stabilizing organic materials, the following chemical formula I, i.e., chemical formula I [In the middle of the meal, R 1 , R 2 , R 3 and R 4 A method characterized by including a compound according to [as defined in claim 1] or a plurality of such compounds being introduced into an organic material, wherein the cosmetic is not included in the organic material. Claim 15 Chemical formula I, that is, chemical formula I As a compound according to, wherein R in the above formula 1 , R 2 and R 3 Each is independently selected from the group consisting of a hydroxyl group, a linear or branched alkoxy group having 1 to 6 carbon atoms, and hydrogen, provided that R 1 , R 2 and R 3 At least one of the groups is a hydroxyl group, and the R 4 are groups according to the following chemical formulas IIa, IIb, and IIc, i.e., chemical formula IIa Chemical formula IIb Chemical formula IIc Selected from a group consisting of, wherein R 5 are the same or different in each case, and the hydroxyl group and the following chemical formula III, i.e., chemical formula III Selected from a group consisting of a channel according to, wherein the above R 1 , R 2 and R 3 is a compound as defined above.

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