Stabilizers based on syringic acid, vanillic acid, isovanillic acid or 5-hydroxyveratic acid, plastic compositions, methods for stabilizing plastic compositions, and stabilizer compositions

Abstract

The present invention relates to a stabilizer based on syringeic acid, vanillic acid, isovanillic acid or 5-hydroxyveratic acid, a plastic composition, a method for stabilizing a plastic composition, and a stabilizer composition having a high stabilizing effect.

Description

[Technical field]

[0001] The present invention relates to a stabilizer based on syringic acid, vanillic acid, isovanillic acid or 5-hydroxyveratic acid, a plastic composition, a method for stabilizing a plastic composition, and a stabilizer composition having a high stabilizing effect. [Background technology]

[0002] Organic materials such as plastics are subjected to ageing processes that ultimately lead to the loss of desired properties, such as mechanical properties. This process, called autoxidation, begins with radical chain scission caused by mechanochemical processes or by UV irradiation in the presence of oxygen, resulting in changes in the polymer chain, e.g. molecular weight and / or the formation of new chemical groups. Stabilizers are therefore used to prevent or at least slow down this ageing. Important representatives of stabilizers are the antioxidants, which interfere with the radicals formed during autoxidation and thus with the decomposition process. In general, a distinction is made between primary antioxidants, which can react directly with oxygen-containing free radicals or C radicals, and secondary antioxidants, which react with the hydroperoxides formed as intermediates (see C. Kroehnke et al. Antioxidants in Ullmann's encyclopedia of industrial chemistry, Wiley-VCH Verlag, Weinheim 2015 Appendix). Typical representatives of primary antioxidants are, for example, phenolic antioxidants, amines, and lactones. Classes of secondary antioxidants include phosphorus compounds, e.g., phosphites and phosphonites, and organosulfur compounds, e.g., thioesters, thioethers and disulfides. In practice, primary and secondary antioxidants are usually combined and have a synergistic effect.

[0003] Plastics made from fossil raw materials such as oil and natural gas are increasingly being complemented or replaced by plastics based on renewable raw materials through biotechnological processes. And sustainability issues also favor the primary and secondary antioxidants used in them (and in plastics derived from fossil raw materials). There is therefore a need for stabilizers based on renewable and available raw materials with high effectiveness, low volatility and compatibility with the polymer substrate. Ideally, the antioxidants would also have a protective effect with respect to photo-oxidation to protect polymers used outside.

[0004] <Prior art> In principle, antioxidants are known to be produced from renewable raw materials and added to plastics alone as well. Tocopherol (vitamin E) is a typical example. 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). Tocopherols are isolated, for example, from natural substances such as wheat germ oil, sunflower oil, olive oil. Other known phenolic antioxidants from natural substances that have been studied in plastics are described, for example, in the following literature:

[0005] Quercetin (B. Kirschweng et al., Melt stabilisation of PE with natural antioxidants: Comparison of rutin and quercetin, Eur. Pol. J. 2018, 103, 228-237), dihydromyrecitin (B. Kirschweng et al., Melt stabilisation of polyethylene with dihydromyrecitin, a natural antioxidant, Pol. Degr. Stab. 2016, 133, 192-200), - Derivatives of rosmarinic acid (K. Doudin et al., New genre of antioxidants from renewable natural resources: Synthesis and characterisation of rosemary plant-derived antioxidants and their performance in polyolefins, Pol. Degr. Stab. 2016, 130, 126-134), ·Tannins (WJ Grigsby et al., Esterification of condensed tannins and their impact on the properties of poly (lactic acid), Polymers 5 (2013) 344-360), -Curcumin (D. Tatraaljai et al. Processing stabilisation of PE with a natural antioxidant, curcumin, European Polymer Journal 49 (2013) 1196-1203), Silymarin and silybin (B. Kirschweng et al., Melt stabilization of polyethylene with natural antioxidants: comparison of a natural extract and its main components, Journal of Thermal Analysis and Calorimetry https: / / doi.org / 10.1007 / s10973-020-09709-5), Catechins derived from tea and coffee extracts (0. Olejnik, A Masek, Bio-Based Packaging Materials Containing Substances Derived from Coffee and Tea Plants, Materials 2020, 13, 5719).

[0006] Furthermore, the authors' own applications for the stabilization of plastics with long-chain esters of ferulic acid ( WO 2021 / 191078 A1 ) and ferulate salts ( WO 2021 / 191364 A1 ) should be mentioned.

[0007] JH Swisher et al., Property impact of common linker segments in sequence-controlled polyesters, Polym. Chem., 2019, 10, 244. Here, a compound having structure (1) is used as a polyester crosslinker. [ka]

[0008] This leads to a reaction with the phenolic groups. However, free phenolic groups are essential for the stabilizing effect. Therefore, stabilization is not possible with the above compounds.

[0009] Furthermore, structures with formula (1) are used as monomers in polymerization processes, for example, N. Kasmi et al. Effective and facile solvent-free synthesis to novel biobased monomers from vanillic acid: Structure thermal-property relationships of sustainable polyesters, Pol. Degr. Stab. 2020, 181, 109315 (see Appendix for abstract), KR 2014047208 (contact lens production), or US 4362510 (additive to dental cements). Here too, no free phenol groups are present after the polymerization process.

[0010] It is known that Leonurine is used as a biocide additive in paints and varnishes (CN 104059449, CN 103881498, CN 105153852, CN 107815183, CN 107868552). The guanidine structure is crucial for its effectiveness. However, in polymers, these structures result in incompatibility or undesirable reactions.

[0011] EP 545305 and JP H01-210948 disclose phenols as phenol-alcohol coupling agents in photographic materials, where the phenol group is consumed by reaction and bond formation and is therefore no longer available as an antioxidant.

[0012] However, most of the above mentioned stabilizers from renewable raw materials have a common limitation that, although they have good effect as antioxidants, they have limited light stabilizing effect, i.e. they are not particularly effective UV stabilizers.

[0013] It is therefore an object of the present invention to make available effective antioxidants for plastics made from renewable raw materials, which at the same time provide high UV protection.

[0014] <Presentation of the present invention> This is achieved by the use of derivatives of syringic acid, vanillic acid, isovanillic acid or 5-hydroxyveratric acid as specified in claim 1, in particular for the stabilization of plastics against oxidative, thermal and / or actinic degradation. The invention further relates to plastic compositions comprising the specified derivatives of syringic acid, vanillic acid, isovanillic acid or 5-hydroxyveratric acid as stabilizers. The invention further relates to novel derivatives of syringic acid, vanillic acid, isovanillic acid or 5-hydroxyveratric acid which are particularly suitable as stabilizers for plastics, as well as to a method for the stabilization of plastic compositions using derivatives of syringic acid, vanillic acid, isovanillic acid or 5-hydroxyveratric acid. Finally, the invention relates to a stabilizer composition consisting of a derivative of syringic acid, vanillic acid, isovanillic acid or 5-hydroxyveratric acid and at least one additive.

[0015] One aspect of the invention relates to the use of a compound having general formula I or II, or a mixture of compounds having general formula I and / or II. [ka] [ka]

[0016] In the formula, R 1 , R 2 and R 3 are each independently selected from the group consisting of a hydroxyl group, a linear or branched alkoxy group having 1 to 6 carbon atoms, and hydrogen; 1 , R 2 and R 3 At least one of the R 1 , R 2 and R 3 At least one of R is a linear or branched alkoxy group having 1 to 6 carbon atoms. 1 , R 2 and R 3 The occurrences of may be the same or different, X is the same or different in each occurrence and is O, NH or NR in formula I and O or NR in formula II; n is 0 or an integer from 1 to 10, preferably 1 to 4; R is an organic group; In particular for the stabilization of plastics against oxidative, thermal and / or actinic degradation.

[0017] Thus, the above compounds having general formulas I and II are derived from naturally occurring compounds such as: a) Syringic acid [ka] b) Vanillic acid [ka] c) Isovanillic acid [ka] and d) 5-hydroxyveratric acid [ka]

[0018] The above compounds having the general formulae I and II are surprisingly distinguished by their high ability to stabilize plastics, in particular against oxidative, thermal and / or actinic degradation.

[0019] Compounds having general formula I and / or II can be prepared by methods known in the art.

[0020] The acids used as starting materials, syringic acid, vanillic acid, isovanillic acid or 5-hydroxyveratric acid, are commercially available.

[0021] Esters (formula I: X=O, n=0 or ≠0) can be prepared, for example, according to WO2010 / 043631 or analogously to WO98 / 556748. For example, aliphatic esters can be obtained by reacting aliphatic, cycloaliphatic or aromatic mono-, di- or polyalcohols with the acid groups of syringic acid, vanillic acid, isovanillic acid or 5-hydroxyveratric acid via acid catalysis (for example in the presence of sulfuric acid or p-toluenesulfonic acid in a suitable solvent or suspending agent such as toluene), removing the water formed, for example by distillation.

[0022] Another possibility is to synthesize short chain esters, such as the methyl or ethyl esters of syringic, vanillic, isovanillic or 5-hydroxyveratric acid, which in a second step are transesterified, for example, with longer chain alcohols in the presence of a suitable catalyst, such as dibutyltin butoxide, dioctyltin ketonate or tetrapropyl orthotitanate. Alternatively, the esterification and / or transesterification may be enzymatic, as described, for example, in K. Vosmann et al. Appl. Microbiol. Biotechnol. (2008) 80:29-36.

[0023] Furthermore, in the first synthetic step, the OH group can be provided with a protecting function which is removed after esterification.

[0024] The amides of the invention can be prepared according to WO 2010 / 043631 or Pearl, lrwin A.; Beyer, Donald L., Reactions of vanillin and its derived compounds. XXI. Amides of vanillic and 3-ethoxy-4-hydroxybenzoic acids, Journal of the American Chemical Society (1953), 75, 2627-30.

[0025] Anhydrides having formula II (X=O) can be synthesized as described in Z. Ahmadzadeh et al. Cu-MOF: an efficient heterogeneous catalyst for the synthesis of symmetric anhydrides via the CH bond activation of aldehydes, RSC Adv., 2018, 8, 24203-24208.

[0026] In a preferred embodiment, the group R is selected from the following group: linear or branched and saturated or unsaturated alkyl groups, preferably linear alkyl groups having 6 or more carbon atoms, particularly preferably having 6, 8, 9, 10, 11, 12, 13, 14, 16, 18, 20, 22, 24, 26, 28 or 30 carbon atoms, 11-methyldodecan-1-yl, 3,7-dimethyl-7-octen-1-yl, (R)-3,7-dimethyloct-6-en-1-yl, 2,6-dimethyl-2,6-octadien-8-yl, cis-9-hexadecen-1-yl, cis-9-octadecen-1-yl, cis-13-docosene-1-yl, cis,cis-9,12-octadecadien-1-yl, 3,7-dimethyl-trans-2,6-octadien-1-yl, aromatic groups, such as substituted or unsubstituted phenyl or benzyl; or 2,3-dihydroxypropan-1-yl, linear or branched and saturated or unsaturated alkanediyl groups, preferably 1,2-ethanediyl, 1,3-propanediyl, 1,4-butanediyl, 1,5-pentanediyl, 1,6-hexanediyl, 1,8-octanediyl; linear or branched and saturated or unsaturated oxaalkanediyl groups, in particular oxaethylenediyl or oxapropylenediyl groups, such as 3-oxapentane-1,5-diyl, 2,2′-(ethylenedioxy)diethanediyl, 2,4-dimethyl-3-oxapentane-1,5-diyl, 4-oxaheptane-2,6-diyl, 2-(2-hydroxypropyl)-1-propyl, 1,3-cyclohexanediyl, 1,4-cyclohexanediyl; aromatic groups, in particular benzene-1,4-diyl or benzene-1,3-diyl, 2-hydroxypropane-1,3-diyl, 2-aminopropane-1,3-diyl, and A divalent, trivalent or tetravalent oxaethylenediyl group derived from an alditol.

[0027] More preferably, always independently of one another: R 1 is a linear or branched alkoxy group having 1 to 6 carbon atoms, in particular a methoxy group; R 2 is a hydroxy group, R 3 is a straight-chain or branched alkoxy group having 1 to 6 carbon atoms, particularly a methoxy group, or hydrogen.

[0028] For example, the esters (X=O, formula I: n=0) can be derived from linear or branched aliphatic alcohols, preferably having at least 6 carbon atoms, such as hexan-1-ol, octan-1-ol, nonan-1-ol, decan-1-ol, undecan-1-ol, lauryl alcohol, tridec.n-1-ol, myristyl alcohol, cetyl alcohol, stearyl alcohol, ceryl alcohol or myricyl alcohol, palmitoleyl alcohol, oleyl alcohol, arachidyl alcohol, behenyl alcohol, erucyl alcohol, lignoceryl alcohol, montanyl alcohol, linoleyl alcohol, isotridecyl alcohol, geraniol, rhodinol, citronellol or nerol, particularly preferably from lauryl esters and stearyl esters.

[0029] When the compound of general formula I is an amide (X=NH, formula I:n=0), its structure can be derived from a linear or branched amine, preferably having at least 6 carbon atoms, such as hexan-1-amine, laurylamine or stearylamine.

[0030] Also suitable are esters of di- or polyols (Formula I: X=O, n 0 or ≠0) or amides of polyamines (Formula I: X=NH, n≠0).

[0031] Examples of diols are alkanediols such as 1,2-ethanediol, 1,3-propanediol, 1,4-butanediol, 1-6-hexanediol, diethylene glycol, triethylene glycol, dipropylene glycol, tripropylene glycol, or higher glycol homologues. Examples of cycloaliphatic diols are 1,4-cyclohexanediol or 1,3-cyclohexanediol.

[0032] Examples of phenols are hydroquinone or resorcinol.

[0033] Also suitable are polyols, such as, for example, glycerol and alditols, and also the following polyalcohols: [ka]

[0034] Examples of diamines are 1,4-butanediamine, 1,5-pentanediamine, 1,6-hexamethylenediamine, 1,10-decanediamine or 1,12-dodecanediamine. In the di- or polyfunctional alcohols or amines mentioned, OH- or NH 2 One, more, or all of the functionalities are capable of forming esterification or amide bonds with the acid groups of the acids presented above.

[0035] Particularly preferred are tetrasubstituted esters of pentaerythritol.

[0036] Preferred representatives of compounds having general formula I are selected from the group consisting of the following compounds: [ka] [ka] [ka] [ka] [ka] [ka] and a compound having the general formula II: [ka] Most preferred are the following compounds: [ka] [ka] [ka]

[0037] Further preferred compounds having aromatic esters or amides are, for example: [ka] [ka] [ka]

[0038] Another preferred embodiment provides that the compound having the general formula I or II or, in the case of a mixture of several compounds having the general formula I and / or II, the sum of all compounds having the general formula I and / or II, is contained in the plastic in a weight percentage of 0.01 to 10.00% by weight, preferably 0.02 to 5.00% by weight, particularly preferably 0.05 to 3.00% by weight.

[0039] The plastic to be stabilized is, for example, a thermoplastic, thermosetting or elastomeric polymer.

[0040] The compounds having the general formula I and / or II are particularly suitable for the stabilization of plastics, said plastics being selected from the group consisting of: a) polymers of olefins or diolefins, such as polyethylene (LDPE, LLDPE, VLDPE, ULDPE, MDPE, HDPE, UHMWPE), metallocene-PE (m-PE), polypropylene, polyisobutylene, poly-4-methylpentene-1, polybutadiene, polyisoprene, such as, in addition to natural rubber (NR), poly(cyclooctene), polyalkylene-carbon monoxide copolymers, as well as statistical or block copolymers, such as polypropylene-polyethylene (EP), EPM or EPDM (e.g. 5-ethylidene-2-norbornane). polypropylene grafted maleic anhydride, as well as blends such as LDPE / LLDPE or long chain polypropylene copolymers prepared with alpha-olefins as comonomers, such as 1-butene, 1-hexene, 1-octene or 1-octadecene, b) polystyrene, polymethylstyrene, poly-α-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), acrylonitrile-butadiene-styrene (ABS), styrene-acrylonitrile (SAN), styrene-acrylonitrile acrylate (ASA), styrene-ethylene, styrene-maleic anhydride polymers including the corresponding graft polymers, e.g. styrene to butadiene, maleic anhydride to SBS or SEBS, and methyl methacrylate, graft polymers from styrene butadiene and ABS (MABS), and hydrogenated polystyrene derivatives, e.g. polyvinylcyclohexane, c) halogen-containing polymers, such as polyvinyl chloride (PVC), polychloroprene and polyvinyl dichloride (PVDC), copolymers of vinyl chloride and vinylidene chloride or vinyl acetate, chlorinated polyethylene, polyvinylidene fluoride, epichlorohydrin homopolymers and copolymers, especially with ethylene oxide (ECO); d) polymers of unsaturated esters, such as polyacrylates and polymethacrylates, for example polymethyl methacrylate (PMMA), polybutyl acrylate, polylauryl acrylate, polystearyl acrylate, polyglycidyl acrylate, polyglycidyl methacrylate, polyacrylonitrile, polyacrylamide, copolymers such as polyacrylonitrile-polyalkyl acrylates, etc. e) polymers of unsaturated alcohols and derivatives, such as polyvinyl alcohol, polyvinyl acetate, polyvinyl butyral, polyallyl phthalate, polyallyl melamine, f) polyacetalenes, such as polyoxymethylene (POM) or copolymers from butanal, etc. g) Polyphenylene oxide and its blends with polystyrene or polyamide h) polymers of cyclic ethers, such as polyethylene glycol, polypropylene glycol, polyethylene oxide, polypropylene oxide, polytetrahydrofuran; i) polyurethanes, in particular linear polyurethanes (TPUs), polycarbamides, based on hydroxy-terminated polyethers or polyesters and aromatic or aliphatic isocyanates, such as 2,4- or 2,6-toluylene diisocyanate or methylene diphenyl diisocyanate; 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 (partially) aromatic polyamides, such as, for example, polyphthalamides, prepared for example from terephthalic acid and / or isophthalic acid and aliphatic diamines, such as hexamethylenediamine or m-xylylenediamine, or from aliphatic dicarboxylic acids, such as adipic acid or sebacic acid, and aromatic diamines, such as 1,4- or 1,3-diaminobenzene, blends of different polyamides, such as PA6 and PA6.6, or blends of polyamides with polyolefins, such as PA / PP; k) polyimides, polyamideimides, polyetherimides, polyesterimides, poly(ether)ketones, polysulfones, polyethersulfones, polyarylsulfones, polyphenylene sulfides, polybenzimidazoles, polyhydantoins, l) polyesters of aliphatic or aromatic dicarboxylic acids and diols, or polyesters of hydroxycarboxylic acids, such as polyethylene terephthalate (PET), polybutylene terephthalate (PBT), polypropylene terephthalate (PTI), polyethylene naphthalate (PEN), poly-1,4-dimethylolcyclohexane terephthalate, poly(hydroxybenzoate), polyhydroxynaphthalate, polylactic acid (PLA), polyhydroxybutyrate (PHB), polyhydroxyvalerate (PHV), polyethylene succinate, polytetramethylene succinate, polycaprolactone, m) Polycarbonates, polyester carbonates and blends such as PC / ABS, PC / PBT, PC / PET / PBT, PC / PA, n) cellulose derivatives, such as cellulose nitrate, cellulose acetate, cellulose propionate, cellulose butyrate o) epoxy resins consisting of a combination of di- or polyfunctional epoxides with hardeners based, for example, on amines, anhydrides, dicyandiamides, mercaptans, isocyanates or catalytically active hardeners; p) phenolic resins, such as phenol formaldehyde resins, urea formaldehyde resins, melamine formaldehyde resins, q) unsaturated polyester resins prepared from unsaturated dicarboxylic acids and diols with vinyl compounds, e.g. styrene, alkyd resins, r) silicones, such as those based on dimethylsiloxane, methylphenylsiloxane or diphenylsiloxane, for example those terminated with vinyl groups; s) and mixtures, combinations or blends of two or more of the foregoing polymers.

[0041] When the polymers shown in a) through r) are copolymers, they may be in the form of statistical ("random"), block or "tapered" structures. Furthermore, the polymers may be linear, branched, star or hyperbranched in structure.

[0042] When the polymers represented by a) through r) are stereoregular polymers, they can be isotactic, stereotactic, in atactic form, or in the form of stereoblock copolymers.

[0043] The polyolefins designated a) may be crosslinked, for example crosslinked polyethylene, in which case they are called X-PE.

[0044] Additionally, these compounds can be used to stabilize rubbers and elastomers, which may be natural rubber (NR) or synthetic rubber materials.

[0045] Suitable synthetic rubber materials are in particular butadiene (BR), styrene-butadiene (SBR), chloroprene (CR), isoprene (IR), isobutylene-isoprene, acrylonitrile-butadiene (NBR or hydrogenated HNBR). Other suitable rubbers and elastomers are ethylene propylene diene terpolymers (EPDM) and ethylene propylene copolymers (EPM), polyester urethanes (AU), polyether urethanes (EU) and silicones (MQ).

[0046] The plastics may be recycled plastics from industrial collections, such as manufacturing waste, or plastics from household or recycling collections, in addition to virgin materials.

[0047] Additionally, particularly preferred polymers are those from renewable sources, such as, for example, polylactic acid (PLA), polyhydroxybutanoic acid (PHB), polyhydroxyvaleric acid (PHV), polybutylene succinate (PBS), polybutylene succinate-co-adipate (PBSA), polyethylene succinate, polytetramethylene succinate, etc.

[0048] Furthermore, the polymers depicted in a) through r) can have both amorphous and (partially) crystalline morphologies.

[0049] Preferred plastics are thermoplastics, particularly preferred polymers are those from the olefin or diolefin and polystyrene polymers.

[0050] Another preferred group of polymers are polyamides and polyesters.

[0051] Another preferred embodiment is characterized in that at least one other additive selected from the group consisting of primary and / or secondary antioxidants, in particular 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, UV absorbers, light stabilizers, hydroxylamine stabilizers, benzofuranone stabilizers, nucleating agents, toughening agents, plasticizers, lubricants, rheology modifiers, chain extenders, processing aids, pigments, dyes, gloss agents, antimicrobial agents, antistatic agents, slip agents, antiblocking agents, coupling agents, dispersants, compatibilizers, oxygen scavengers, acid scavengers, co-stabilizers, marking agents and antifogging agents, is contained and / or added to the plastic during use.

[0052] The at least one additive is preferably selected from the group consisting of phosphites, phosphonites, sulfites, polyols, acid scavengers, hindered amines, and mixtures and combinations thereof.

[0053] Primary antioxidants act as hydrogen donors and free radical scavengers, thus hindering the radical autoxidation process within the polymer. Suitable primary antioxidants are phenolic antioxidants, (partially) aromatic amines, hydroxylamines and lactones.

[0054] Suitable synthetic phenolic antioxidants include, for example: Alkylated monophenols, for example, 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 nonylphenols, such as 2,6-dinonyl-4-methylphenol, 2,4-dimethyl-6-(1'-methylundec-1'-yl)phenol, 2,4-dimethyl-6-(1'-methylheptadec-1'-yl)-phenol, 2,4-dimethyl-6-(1'-methyltridec-1'-yl)phenol and mixtures thereof; Alkylthiomethylphenols, such as 2,4-dioctylthiomethyl-6-tert-butylphenol, 2,4-dioctylthiomethyl-6-methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol, 2,6-didodecylthiomethyl-4-nonylphenol; Hydroquinones and alkylated hydroquinones, such as 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-hydroquinone, 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-tert-butyl-4-hydroxyphenyl stearate, bis(3,5-di-tert-butyl-4-hydroxyphenyl)adipate; Tocopherols, such as α-, β-, γ-, δ-tocopherol and mixtures thereof (vitamin E); Hydroxylated thiodiphenyl ethers, such as 2,2'-thiobis(6-tert-butyl-4-methylphenol), 2,2'-thiobis(4-octylphenol), 4,4'-thiobis(6-tert-butyl-3-methylphenol), 4,4'-thiobis(6-tert-butyl-2-methylphenol), 4,4'-thiobis(3,6-di-sec-amylphenol), 4,4'-bis(2,6-dimethyl-4-hydroxyphenyl) disulfide; Alkylidene bisphenols, 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-n-dodecylmercaptobutane, ethylene glycol-bis[3,3-bis(3'-tert-butyl-4'-hydroxyphenyl)butyric acid], 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-hydroxyphenylbutane, 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; O-, N-, and S-benzyl compounds, such as 3,5,3',5'-tetra-tert-butyl-4,4'-dihydroxydibenzyl ether, octadecyl-4-hydroxy-3,5-dimethylbenzyl mercaptoacetate, tridecyl-4-hydroxy-3,5-di-tert-butylbenzyl mercaptoacetate, tris(3,5-di-tert-butyl-4-hydroxybenzyl)amine, bis(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)dithioterephthalate, bis(3,5-di-tert-butyl-4-hydroxybenzyl)sulfide, isooctyl-3,5-di-tert-butyl-4-hydroxybenzyl mercaptoacetate; Hydroxybenzylated malonates, such as dioctadecyl-2,2-bis(3,5-di-tert-butyl-2-hydroxybenzyl)-malonate, dioctadecyl-2-(3-tert-butyl-4-hydroxy-5-methylbenzyl)malonate, didodecylmercaptoethyl-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate, bis[4-(1,1,3,3-tetramethylbutyl)phenyl]-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate; 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; 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, 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-hydrophenylpropionyl)hexahydro-1,3,5triazine, 1,3,5-tris(3,5-dicyclohexyl-4-hydroxybenzyl)isocyanurate; Benzylphosphonates, such as dimethyl-2,5-di-tert-butyl-4-hydroxybenzylphosphonate, diethyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate, di-octadecyl-5-tert-butyl-4-hydroxy-3-methylbenzylphosphonate, calcium salts of the monoethyl ester of 3,5-di-tert-butyl-4-hydroxybenzylphosphonic acid; Acylaminophenols, such as 4-hydroxylauranilide, 4-hydroxystearanilide, octyl-N-(3,5-di-tert-butyl-4-hydroxyphenyl)carbamate; Esters of β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid with mono- or polyhydric alcohols, such as methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane; β-(5-tert-butyl-4-hydroxy-3-methylphenyl)propionic acid and monohydric or polyhydric alcohols, such as 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 esters of 3,9-bis[2-{3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy}-1,1-dimethylethyl]-2,4,8,10-tetraoxaspiro[5.5]undecane; Esters of β-(3,5-dicyclohexyl-4-hydroxyphenyl)propionic acid with mono- or polyhydric alcohols, such as methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane; Esters of β-(3,5-di-tert-butyl-4-hydroxyphenyl)acetic acid with mono- 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, 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; Amides of β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid, such as N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamide, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamide, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamide, 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 sold by Uniroyal); It is vitamin C.

[0055] Particularly preferred phenolic antioxidants are as follows: [ka] [ka]

[0056] Other particularly preferred phenolic antioxidants are based on renewable sources, such as tocopherols (vitamin E), tocotrienols, tocomonoenols, carotenoids, hydroxytyrosol, flavonols such as chrysin, quercitin, hesperidin, neohesperidin, naringin, morin, kaempferol, fisetin, anthocyanins such as delphinidin and malvidin, curcumin, carnosic acid, carnosol, rosmarinic acid, resveratrol, and tannins.

[0057] Examples of suitable antioxidants are N,N'-di-isopropyl-phenylenediamine, N,N'-di-sec-butyl-p-phenylenediamine, N,N'-bis(1,4-dimethylpentyl)-p-phenylenediamine, N,N'-bis(1-methyl-heptyl)-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 Phenylenediamine, diphenylamine, N-allyldiphenylamine, 4-isopropoxydiphenylamine, N-phenyl-1-naphthylamine, N-(4-tert-octylphenyl)-1-naphthylamine, N-phenyl-2-naphthylamine, octylated diphenylamines such as p,p'-di-tert-octyldiphenylamine, 4-n-butylaminophenol, 4-butyrylaminophenol, 4-nonanoylaminophenol, 4-dodecanoylaminophenol, 4-octadecanoylaminophenol, bis(4-methoxyphenyl)amine, 2,6-di-tert-butyl-4-dimethylaminomethylphenol, 2,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, N,N,N',N'-tetramethyl-4,4'-diaminodiphenylmethane, 1,2-bis[(2-methylphenyl)amino]ethane, 1,2-Bis(phenylamino)propane, (o-tolyl)biguanide, bis[4-(1',3'-dimethylbutyl)phenyl]amine, tert-octylated N-phenyl-1-naphthylamine, mixtures of mono- and dialkylated tert-butyl / tert-octyldiphenylamines, mixtures of mono- and dialkylated nonyldiphenylamines, mixtures of mono- and dialkylated dodecyldiphenylamines, and mono- and dialkylated isopropyl / isohexyldiphenylamines. mixtures of mono- and dialkylated tert-butyldiphenylamines, 2,3-dihydro-3,3-dimethyl-4H-1,4-benzothiazine, phenothiazine, mixtures of mono- and dialkylated tert-butyl / tert-octylphenothiazines, mixtures of mono- and dialkylated tert-octylphenothiazines, N-allylphenothiazine, N,N,N',N'-tetraphenyl-1,4-diaminobut-2-ene, and mixtures or combinations thereof.

[0058] Preferred amine antioxidants are N,N'-di-isopropyl-p-phenylenediamine, N,N'-di-secbutyl-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 ... N-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.

[0059] Particularly preferred amine antioxidants are those having the following structure: [ka]

[0060] Examples of preferred hydroxylamines or N-oxides (nitrones) are N,N-dialkylhydroxylamines, N,N-dibenzylhydroxylamine, N,N-dilaurylhydroxylamine, N,N-distearylhydroxylamine, N-benzyl-α-phenylnitrone, N-octadecyl-α-hexadecylnitrone, as well as Genox® EP (SI Group) having the formula: [ka]

[0061] Examples of suitable lactones are benzofuranones and indolinones are 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-pivaloyloxyphenyl)-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 which further have a phosphorous group, such as [ka]

[0062] Particularly preferred lactones have the following structure: [ka]

[0063] Another suitable group of antioxidants are the isoindolo[2,1-A]quinazolines, for example: [ka]

[0064] Secondary antioxidants stabilize plastics primarily by decomposing hydroperoxides.

[0065] Suitable secondary antioxidants are in particular phosphites or phosphonites, such as triphenyl phosphite, diphenyl alkyl phosphites, phenyl dialkyl phosphites, tri(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) phosphite, 1,2,4-tris(tert-butylphenyl)pentaerythritol diphosphite, bis(2,4-dicumylphenyl)pentaerythritol diphosphite, bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite, diisodecyloxypentaerythritol diphosphite, bis(2,4-di-tert-butyl-6-methylphenyl)pentaerythritol diphosphite, bis(2,4,6-tris(tert-butylphenyl)pentaerythritol diphosphite, tristearyl sorbitol Toltriphosphite, tetrakis(2,4-di-tert-butylphenyl)-4,4'-biphenylene-diphosphonite, 6-isooctyloxy-2,4,8,10-tetra-tert-butyl-12H-dibenzo[d,g]-1,3,2dioxaphosphocin, bis(2,4-di-tert-butyl-6-methylphenyl)methyl phosphite, bis(2,4-di-tert-butyl-6-methylphenyl)ethyl phosphite, 6-fluoro-2,4,8,10-tetra-tert-butyl- 12-methyl-dibenzo[d,g]-1,3,2 dioxaphosphocin, 2,2'2''-nitrilo[triethyl-tris(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)-1,2-dioxaphosphirane, etc.

[0066] Particularly preferred phosphites are as follows: [ka] [ka]

[0067] Preferred phosphonites are as follows: [ka]

[0068] Still other suitable secondary antioxidants are sulfur compounds such as distearylthiodipropionate, dilaurylthiodipropionate, ditridecyldithiopropionate, ditetradecylthiodipropionate, 3-(dodecylthio)-1,1'-[2,2-bis[[3-(dodecylthio)-1-oxopropoxy]methyl]-1,3-propanediyl]propanoic acid ester. The following structures are preferred: [ka]

[0069] Other suitable secondary antioxidants are sulfites.

[0070] Preferred sulfite antioxidants are inorganic sulfites, disulfites, or thiosulfates of mono-, di-, tri-, or tetravalent metals, preferably of alkali metals, alkaline earth metals, aluminum and / or zinc, the inorganic sulfites being used in particular in anhydrous form.

[0071] Suitable salts are in particular sodium sulfite, potassium sulfite, lithium sulfite, calcium sulfite, magnesium sulfite, aluminum sulfite or zinc sulfite. Other suitable salts are thiosulfates, such as, for example, sodium thiosulfate.

[0072] Suitable fillers and reinforcing substances are, for example, synthetic or natural substances, examples of which are calcium carbonate, silicates, glass fibres, glass beads (solid or hollow), talc, mica, kaolin, barium sulphate, metal oxides and hydroxides, soot, graphite, carbon nanotubes, graphene, wood flour or fibres of natural products such as cellulose, or synthetic fibres. Other suitable fillers are hydrotalcites, or zeolites, or layered silicates, for example montmorillonite, bentonite, beidellite, mica, hectorite, saponite, vermiculite, hydrobiotite, magadiite, illite, kaolinite, wollastonite, attapulgite.

[0073] Suitable acid scavengers ("antacids") are salts of mono-, di-, tri- or tetravalent metals, preferably alkali metals, alkaline earth metals, aluminum or zinc, especially those formed with fatty acids, such as calcium stearate, magnesium stearate; zinc stearate, aluminum stearate, calcium laurate, calcium behenate, calcium lactate, calcium stearoyl-2-lactylate, etc. Another class of suitable acid scavengers is hydrotalcite, especially synthetic hydrotalcites based on aluminum, magnesium and zinc, hydrocalumites, zeolites, alkaline earth oxides, especially calcium oxide and magnesium oxide and zinc oxide, alkaline earth carbonates, especially calcium carbonate, magnesium carbonate and dolomite, and hydroxides, especially brucite (magnesium hydroxide).

[0074] Other suitable costabilizers are polyols, in particular alditols or cyclitols, such as pentaerythritol, dipentaerythritol, tripentaerythritol, short-chain polyether polyols or polyester polyols, as well as hyperbranched polymers / oligomers or dendrimers carrying alcohol groups. [ka]

[0075] Preferably, the at least one alditol is selected from the group consisting of threitol, erythritol, galactitol, mannitol, ribitol, sorbitol, xylitol, arabitol, isomalt, lactitol, maltitol, altritol, iditol, maltotritol, and hydrogenated oligosaccharides and polysaccharides having polyol end groups, and mixtures thereof. It is particularly preferred that the at least one preferred alditol is selected from the group consisting of erythritol, mannitol, isomalt, maltitol, and mixtures thereof.

[0076] Other examples of suitable sugar alcohols are heptitols and octitols: meso-glycero-alloheptitol, D-glycero-D-altro-heptitol, D-glycero-D-mannoheptitol, meso-glycero-glucoheptitol, D-glycero-D-galactoheptitol (perseitol), D-glycero-D-glucoheptitol, L-glycero-D-glucoheptitol, D-erythro-L-galactooctitol, D-threo-L-galactooctitol.

[0077] In particular, the at least one cyclitol may be selected from the group consisting of inositol (myo-, scyllo-, D-chiro-, L-chiro-, muco-, neo-, allo-, epi-, cis-inositol), 1,2,3,4-tetrahydroxycyclohexane, 1,2,3,4,5-pentahydroxycyclohexane, quercitol, biscumitol, bornesitol, conduritol, ononitol, pinitol, pinpollitol, quebrachitol, cisceritol, quinic acid, shikimic acid and valienol, with myoinositol being preferred.

[0078] Other suitable co-stabilisers are the ester and ether derivatives of the abovementioned alditols or cyclitols, such as the following compounds: [ka]

[0079] Examples of suitable UV absorbers are compounds based on 2-(2'-hydroxyphenyl)benzotriazolene, 2-hydroxybenzophenone, benzoate esters, acrylates, oxamides, and 2-(2-hydroxyphenyl)-1,3,5 triazinene.

[0080] 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-(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'-hydroxyphenyl)benzotriazole, 2-(2'-hydroxy-4'-octyloctyphenyl)benzotriazole, 2-(2'-hydroxy-5'-(1,1,3,3-tetramethylbutyl)phenyl)benzotriazole, 2-(3',5'-di-tert-amyl-2'-hydroxyphenyl)benzotriazole, 2-(3',5'-bis(a,a-dimethylbenzyl)-2'-hydroxyphenyl)benzotriazole, 2-(3'-tert-butyl-2'-hydroxphenyl)benzotriazole 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-benzotriazol-2-ylphenol];Transesterification product of 2-[3'-tert-butyl-5'-(2-methoxycarbonylethyl)-2'-hydroxyphenyl]-2H-benzotriazole with polyethylene glycol 300;[R-CH, 2 CH 2 -COO-CH 2 CH 2 ] 2 , where R=3'-tert-butyl-4'-hydroxy-5'-2H-benzotriazol-2-ylphenyl, [2'-hydroxy-3'-(a,a-dimethylbenzyl)-5'-(1,1,3,3-tetramethylbutyl)phenyl]benzotriazole, 2-[2'-hydroxy-3'-(1,1,3,3-tetramethylbutyl)-5'-(α,α-dimethylbenzyl)phenyl]benzotriazole.

[0081] Examples of suitable 2-hydroxybenzophenones are the 4-hydroxy-, 4-methoxy-, 4-octyloxy-, 4-decyloxy-4-dodecyloxy, 4-benzyloxy, 4,2',4'-trihydroxy- and 2'-hydroxy-4,4'-dimethoxy-derivatives of 2-hydroxybenzophenone.

[0082] Examples of suitable acrylates are ethyl-a-cyano-β,β-diphenylacrylate, isooctyl-a-cyano-β,β-diphenylacrylate, methyl-a-carbomethoxycinnamic acid, methyl-a-cyano-β-methyl-p-methoxycinnamic acid, butyl-a-cyano-β-methyl-p-methoxycinnamic acid, methyl-a-carbomethoxy-p-methoxycinnamic acid and N-(β-carbomethoxy-β-cyanovinyl)-2-methylindoline.

[0083] Examples of suitable esters of benzoic acid are 4-tert-butylphenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoylresorcinol, bis(4-tert-butylbenzoyl)resorcinol, benzoylresorcinol, 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.

[0084] Examples of suitable oxanilides are 4,4'-dioctyloxyoxanilide, 2,2'-diethoxyoxanilide, 2,2'-dioctyloxy-5,5'-di-tert-butoxanilide, 2,2'-didodecyloxy-5,5'-di-tert-butoxanilide, 2-ethoxy-2'-ethyloxanilide, N,N'-bis(3-dimethylaminopropyl)oxamide, 2-ethoxy-5-tert-butyl-2'-ethoxanilide and mixtures thereof with 2-ethoxy-2'-ethyl-5,4'-di-tert-butoxanilide, mixtures of o- and p-methoxy-disubstituted oxanilides, and mixtures of o- and p-ethoxy-disubstituted oxanilides.

[0085] 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-hydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5 triazine, 2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(4-methylphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-dodecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-tridecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-[2-hydroxy-4-(2-hydroxy-3-butyloxypropoxy)phenyl]-4,6-bis(2,4-dimethyl)1,3,5-triazine, 2-[2-hydroxy-4-( 2-Hydroxy-3-octyloxypropyloxy)phenyl]-4,6-bis(2,4-dimethyl)-1,3,5-triazine, 2-[4-dodecyloxy / tridecyloxy-2-hydroxypropoxy)-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-[2-hydroxy-4-2-hydroxy-3-dodecyloxypropoxy)phenyl]-4,6-bis(2,4-dimethylphenyl-1,3,5-triazine, 2-2-hydroxy-4-hexyloxy)phenyl-4,6-diphenyl- 1,3,5-triazine, 2-(2-hydroxy-4-methoxyphenyl)-4,6-diphenyl-1,3,5-triazine, 2,4,6-tris[2-hydroxy-4-(3-butoxy-2-hydroxypropoxy)phenyl]-1,3,5-triazine, 2-(2-hydroxyphenyl)-4-(4-methoxyphenyl)-6-phenyl-1,3,5-triazine, 2-{2-hydroxy-4-[3-(2-ethylhexyl-1-oxy)-2-hydroxypropyloxy]phenyl}-4,6-bis(2,4-dimethylphenyl-1,3,5-triazine).

[0086] Examples of suitable metal deactivators are N,N'-diphenyloxamide, N-salicylal-N'-salicyloylhydrazine, N,N'-bis(salicyloyl)hydrazine, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazine, 3-salicyloylamino-1,2,4-triazole, bis(benzylidene)oxalyl dihydrazide, oxanilide, isophthalamide, N,N'-bis(salicyloyl)oxylyl dihydrazide, N,N'-bis(salicyloyl)thiopropionyl dihydrazide, and tris[2-tert-butyl-4-thio(2'-methyl-4'-hydroxy-5'-tert-butyl)-phenyl-5-methyl]phenyl phosphite.

[0087] Particularly preferred metal deactivators are as follows: [ka]

[0088] Examples of sterically hindered amines 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-hiperidinyl. hydroxybenzyl malonate, condensation products of 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxy-piperidine 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-butanetetracarboxylate, 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 tetramethylpiperidine, linear or cyclic condensation product of N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine with 4-morpholino-2,6-dichloro-1,3,5-triazine, reaction product of 7,7,9,9-tetramethyl-2-cycloundecyl-1-oxa-3,8-diaza-4-oxospiro-[4,5]decane and epichlorohydrin.

[0089] Particularly preferred hindered amines are as follows: [ka] [ka] [ka]

[0090] Preferred oligomers and polymers of hindered amines have the following structures: [ka] In the above formula, each n is 2-100, preferably 2-10. [ka] In the above formula, each n is 2-100, preferably 3-20. [ka] In the above formula, each n is 3-200, preferably 5-100. [ka] [ka] In the above formula, each n is 1 to 100, preferably 2 to 10. Alternatively, it is the following formula: [ka]

[0091] Another suitable light stabilizer is Hostanox NOW (manufacturer: Clariant SE), which has the following general structure: [ka] In the formula, R is -OC(O)-C 15 H 31 or -OC(O)-C 17 H 35 means...

[0092] Compatibilizers are used, for example, in thermodynamically immiscible blends or recycle mixtures, and contain structural elements of the respective blend components to be mixed. An example of a compatibilizer suitable for polyolefin blends is an olefin block copolymer consisting of ethylene, propylene, and an α-olefin such as 1-octene. Other compatibilizers, especially for compatibilizing polar polymers such as PET or polyamides with non-polar polymers such as PP or PE, often contain reactive groups derived, for example, from maleic anhydride, acrylic acid, glycidyl acrylate or glycidyl methacrylate, for example polypropylene-g-maleic anhydride, polyethylene-g-maleic anhydride, polypropylene-g-acrylic acid, polyethylene-g-acrylic acid, polyethylene-co-maleic anhydride), SBS-g-maleic anhydride, SEBS-g-maleic anhydride, polyethylene-polyacrylate-polyglycidyl methacrylate.

[0093] Examples of suitable dispersants are as follows: Polyacrylates, e.g. copolymers with long chain side groups, polyacrylate block copolymers, alkylamides, e.g. N,N'-1,2-ethanediylbisoctadecaneamide sorbitan esters, e.g. monostearyl sorbitan esters, titanates and zirconates, reactive copolymers with functional groups, e.g. polypropylene-co-acrylic acid, polypropylene-co-maleic anhydride, polyethylene-co-glycidyl methacrylate, polystyrene-alt-maleic anhydride-polysiloxanes, e.g. dimethylsilanediol-ethylene oxide copolymers, polyphenylsiloxane copolymers, amphiphilic copolymers, e.g. polyethylene block polyethylene oxide, dendrimers, e.g. dendrimers with hydroxyl groups.

[0094] Particularly suitable flame retardants are: a) Inorganic flame retardants, e.g. Al(OH) 3、 Mg(OH) 2、 AlO(OH), MgCO 3Layered silicates, such as montmorillonite or sepiolite, unmodified or organically modified, double salts, such as Mg-Al silicates, POSS (polyhedral oligomeric silsesquioxane) compounds, huntite, hydromagnesite or halloysite, as well as Sb 2 O 3 , Sb 2 O 5 , MoO 3 , zinc stannate, zinc hydroxystannate, b) nitrogen-containing flame retardants, such as zB melamine, melem, melam, melon, melamine derivatives, melamine condensation products or melamine salts, benzoguanamine, polyisocyanurates, allantoin, phosphacenes, in particular melamine cyanurate, melamine phosphates, dimelamine phosphates, melamine pyrophosphates, melamine polyphosphates, 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, c) radical formers, such as alkoxyamines, hydroxylamine esters, azo compounds, sulfenamides, sulfenimides, dicumyl or polycumyl, hydroxyimides and their derivatives, such as hydroxyimide esters or hydroxyimide ethers; d) phosphorus-containing flame retardants, for example red phosphorus, for example resorcinol diphosphate, bisphenol-A-diphosphate and their oligomers, triphenyl phosphate, ethylenediamine diphosphate, phosphinates, for example hypophosphites and their derivatives, for example alkylphosphinate salts, for example aluminium diethylphosphinate or zinc diethylphosphinate or aluminium phosphinate, aluminium phosphites, aluminium phosphonates, phosphonic acid esters, oligomeric and polymeric derivatives of methanephosphonic acid, 9,10-dihydro-9-oxa-10-phosphophenanthrene-10-oxide (DOPO) and substituted compounds thereof, e) halogen-containing flame retardants based on chlorine and bromine, such as decabromodiphenyl oxide, tris(3-bromo-2,2-bis(bromomethyl)propyl phosphate, tris(tribromoneopentyl)phosphate, tetrabromophthalic acid, 1,2-bis(tribromophenoxy)ethane, hexabromocyclododecane, brominated diphenylethane, tris-(2,3-dibromopropyl)isocyanurate, ethylene-bis-(tetrabromophthalimide), tetrabromo-bisphenol A, brominated polystyrene, brominated polybutadiene or polystyrene-brominated polybutadiene copolymers, brominated polyphenylene ethers, brominated epoxy resins, polypentabromobenzyl acrylate, optionally Sb 2 O 3 and / or Sb 2 O 5 Combined with f) Borates, for example zinc or calcium borates, optionally on a substrate such as silica; g) sulfur-containing compounds, such as elemental sulfur, disulfides and polysulfides, thiuram sulfides, dithiocarbamates, mercaptobenzothiazoles and sulfenamides; h) drip-proofing agents, such as polytetrafluoroethylene; i) Silicon-containing compounds, such as polyphenylsiloxanes j) carbon modifications, such as carbon nanotubes (CNTs), expandable graphite or graphene; k) as well as combinations or mixtures thereof.

[0095] Particularly suitable flame retardants are: It is a radical product, preferably selected from the group consisting of N-alkoxyamines, -CC- radical products, radical products having an azo group (-N=N-), radical products having a hydrazine group (-NH-HN-), radical products having a hydrazone group (>C=N-NH-), radical products having an azine group (>C=NN=C<), radical products having a triazene group (-N=NN<), or from the group of iminoxytriazines.

[0096] Suitable preparations of azo compounds are described, for example, in M. Aubert et al. Macromol. Sci. Eng. 2007, 292, 707-714. or WO 2008101845; the preparation of hydrazones and azines in M. Aubert et al., Pol. Adv. Technol. 2011, 22, 1529-1538.; the preparation of triazenes in W. Pawelec et al., Pol. Degr. Stab. 2012, 97, 948-954. The synthesis of iminoxytriazines is described in WO 2014 / 064064.

[0097] Particularly useful radical generators are selected from the following group: a) N-alkoxyamines having the following structural formula: [ka] In the above formula, R 3 represents hydrogen or an optionally substituted alkyl-, cycloalkyl-, arylheteroaryl- or acyl-group, in particular a C1-C4-alkyl group, R 4 represents an alkoxy-, aryloxy-, cycloalkoxy-, aralkoxy- or acyloxy- group, Z represents hydrogen or an optionally substituted alkyl-, cycloalkyl-, arylheteroaryl- or acyl-group, where two Z groups may form a closed ring or may be substituted by an ester-, ether-, amine, amide, carboxy- or urethane group; E represents an alkoxy group, an aryloxy group, a cycloalkoxy group, an aralkoxy group, or an acyloxy group. b) An azo compound having the following structural formula: [ka] In the above formula, R 5means an alkyl group, a cycloalkyl group, or an aryl group, R 6 are the same or different and represent a linear or branched alkyl group, R 7 are the same or different and each represents a hydrogen atom or a linear or branched alkyl group, R 8 are the same or different and represent an alkyl, alkoxy, aryloxy-cycloalkyloxy, aralkoxy or acyloxy group. c) Dicumyl, having the following structural formula: [ka] In the formula, R 7 has the meaning given above and is preferably methyl. d) and / or polycumyl having the following structural formula: [ka] In the formula, R 7 has the above meaning, preferably is methyl, 2 <n<100である。

[0098] Typical examples of N-alkoxyamines having the above structure are: 1-Cyclohexyloxy-2,2,6,6-tetramethyl-4-octadecylaminopiperidine: Bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacate; 2,4-Bis[(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-6-(2-hydroxyethylamino-S-triazine; Bis(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)adipate; 2,4-Bis[(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-6-chloro-S-triazine;1-(2-hydroxy-2-methylpropoxy)-4-hydroxy-2,2,6,6-tetramethylpiperidine;1-(2-hydroxy-2-methylpropoxy)-4-oxo-2,2,6,6-tetramethylpiperidine;1-(2-hydroxy-2-methylpropoxy)-4-octadecanoic acid 2,4-Bis{N-[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]-2,2,6,6-tetramethylpiperidine;Bis(1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl)-sebacic acid salt;Bis(1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl)-adipate salt;2,4-Bis{N-[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]-2,2,6,6-tetramethylpiperidine-4-yl ]-N-butylamino}-6-(2-hydroxyethylamino)-S-triazine;4-Piperidinol, 2,2,6,6-tetramethyl-1-(undecyloxy)-4,4'-carbonate;2,4-Bis[(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-6-chloro-S-triazine with N,N'-bis(3-aminopropylethylenediamine);4,4'-Hexa Oligomeric compounds which are condensation products of methylene-bis(amino-2,2,6,6-tetramethylpiperidine) with 2,4-dichloro-6-[(1-cyclohexyloxy-2,2,6,6-tetramethyl-4-yl)butylamino]-S-triazine and are terminated with 2-chloro-4,6-bis(dibutylamino)-S-triazine; aliphatic hydroxylamines such as disterarylhydroxylamine; and compounds having the formula: [ka] Or the following compound: [ka] In the above formula, each n is 1 to 15.

[0099] Some of the above compounds are commercially available and sold under the following trade names: FLAMESTAB NOR 116®, TINUVIN NOR 371®, IRGATEC CR 76® from BASF SE, Hostavin NOW® from Clariant, or ADK Stab LA 81® from Adeka. Dicumyl and polycumyl are commercially available products available, for example, from United Initiators.

[0100] b) Phosphorus-containing flame retardants, such as phosphinates having the following structure: [ka] In the formula, R 1 and R 2 are preferably the same or different and are selected from linear or branched C1-C6 alkyl and / or aryl; M is selected from Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Ce, Bi, Sr, Mn, Li, Na, K, Zn and / or protonated nitrogen bases, preferably from the group consisting of calcium ions, magnesium ions, aluminum ions and / or zinc ions; and m=1-4, preferably 2 or 3; n=1-4, preferably 1 or 3; and x=1-4, preferably 1 or 2. In a particularly preferred embodiment, R 1 is alkyl, R 2 is alkyl, and M is Al or Zn.

[0101] A particularly preferred example of a phosphinate is the commercial product Exolit OP® from Clariant SE.

[0102] Other preferred phosphorus-containing flame retardants are metal salts of hypophosphorous acid having the following structure: [ka] In the formula, Met is a metal selected from Groups I, II, III and IV of the Periodic Table of Elements, and n is a number from 1 to 4 corresponding to the charge of the corresponding metal ion. n+ For example, Na+, Ca 2+ , Mg 2+ , Zn 2+ , Ti 4+ , or Al 3+ and Ca 2+ , Zn 2+ and Al 3+ is particularly preferred.

[0103] Some of the above hypophosphites are commercially available, for example, from Italmatch Chemicals under the name Phoslite®.

[0104] Another preferred group of phosphorus-containing flame retardants are the phosphonates or phosphonic acid diaryl esters having the structure: [ka] In the formula, R 8 and R 10 is H, alkyl, preferably C1-C4, R 9 is C1-C4 alkyl, u=1-5, and v=1-5.

[0105] The corresponding structure can be in the form of phosphonate oligomers, polymers and copolymers.Linear or branched phosphonate oligomers and polymers are known from the prior art.For branched phosphonate oligomers and polymers, refer to US patents US 2716101, US 3326852, US 4328174, US 4331614, US 4374971, US 4415719, US 5216113, US 5334692, US 3442854, US 6291630B1, US 6861499B2 and US 7816486B2. For phosphonate oligomers, see US Patent Applications US 2005 / 0020800A1, US 2007 / 0219295A1, and US 2008 / 0045673A1. For linear phosphonate oligomers and polymers, see US Patent Applications US 3946093, US 3919363, US 6288210B1, US 2682522, and US 2891915.

[0106] Phosphonates are available, for example, from FRX Polymers under the trade name Nofia®.

[0107] Another preferred group of phosphorus-containing flame retardants are compounds based on oxaphosphorine oxides and their derivatives, for example having the following structure: [ka] [ka] [ka] [ka] In the formula, M is a metal selected from Group 2, 3, 12, or 13 of the Periodic Table of the Elements; x=2 or 3; n≧10; m=0 to 25; R=H, a halogen, or an aliphatic or aromatic group having 1 to 32 carbon atoms; and R 1 is H, C1-C6 alkyl or phenyl.

[0108] Products based on oxophosphorin oxide are commercially available, for example, under the trade name Ukanol® from Schill and Seilacher GmbH. Other compounds can be prepared, for example, according to patent specifications WO 2013020696, WO 2010135398, WO 03070736, WO 2006084488, WO 2006084489, WO 2011000019, WO 2013068437, WO 2013072295.

[0109] Other suitable phosphorus-containing flame retardants are cyclic phosphonates having a structure according to one of the following formulas: [ka] In the formula, A 1 and A 2 each independently represents a substituted or unsubstituted linear or branched alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted benzyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group; A 3 and A 4 are each independently a methyl or ethyl group; A 5 represents a straight-chain or branched alkyl group having 1 to 4 carbon atoms, or a phenyl group or a benzyl group, each of which may have up to three methyl groups.

[0110] Cyclic phosphonates are commercially available, for example, from Thor GmbH under the trade name Aflammit® or can be prepared according to EP 2450401.

[0111] Other synergistic phosphorus-containing flame retardants are phosphacenes, in particular polymeric phosphacenes, corresponding products being commercially available, for example, from Otsuka Chemical under the name SPB-100.

[0112] a) Nitrogen-containing flame retardants Preferred nitrogen-containing flame retardants are melamine polyphosphate, melamine cyanurate, melamine metal phosphate, poly-[2,4-(piperazin-1,4-yl)-6-morpholin-4-yl)-1,3,5 triazine] and ammonium polyphosphate, which are commercially available under the trade names Melapur® from BASF SE, Budit® from Chemische Fabrik Budenheim, Exolit® from Clariant, Safire® from Huber Chemicals or MCA PPM Triazine from MCA Technologies GmbH.

[0113] c) Preferred sulfur-containing flame retardants are, for example, the following compounds: [ka] Particularly preferred flame retardants are halogen-free and are the following compounds: Al(OH) 3 , Mg(OH) 2 [ka] [ka]

[0114] Suitable lubricants and processing aids are, for example, polyethylene waxes, polypropylene waxes, fatty acid salts such as calcium stearate, zinc stearate, or amide waxes such as montan wax, erucamide or oleamide, fluoropolymers, silicones or salts of neoalkoxy titanates and zirconates.

[0115] Examples of heat stabilizers that are particularly suitable for PVC recycling are metal soaps of divalent metals such as Ba, Zn, Ca, e.g. zinc stearate, calcium stearate, organotin compounds, e.g. methyl and octyltin compounds such as dioctyltin bisisooctylthioglycolate or dioctyltin maleate, aminouracils, aminocrotonates, perchlorates, as well as phosphites, epoxides, polyols, diketones, dihydropyridines, hydrotalcites, zeolites.

[0116] Suitable pigments can be inorganic or organic in nature.Examples of inorganic pigments are titanium dioxide, zinc oxide, zinc sulfide, iron oxide, ultramarine, soot.Examples of organic pigments are anthraquinone, anthanthrone, benzimidazolone, quinacridone, diketopyrrolopyrrole, dioxazine, indanthrone, isoindolinone, azo compound, perylene, phthalocyanine or pyranthrone.Other suitable pigments are effect pigments based on metal or pearlescent pigments based on metal oxide.

[0117] Examples of suitable brighteners are bisbenzoxazoles, phenylcoumarins or bis(styryl)biphenyls, and in particular brighteners having the formula: [ka]

[0118] Examples of suitable filler deactivators are polysiloxanes, polyacrylates, especially block copolymers such as polymethacrylic acid-polyalkylene glycols or polyglycidyl (meth)acrylates, and copolymers thereof, such as copolymers with styrene and epoxides, for example having the following structure: [ka]

[0119] Examples of suitable antistatic agents are ethoxylated alkylamines, fatty acid esters, alkylsulfonates, and polymers that form co-continuous networks with the polymer matrix, such as polyetheramides, polyesteramides, polyetheresteramides or polyether block copolymers, to which ionically conductive metal salts can be added.

[0120] Suitable antiozonants are the amines mentioned above, such as N,N'-di-isopropyl-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.

[0121] For example, examples of suitable rheology modifiers for the preparation of controlled rheology polypropylene (CR-PP) are peroxides, alkoxyamine esters, oxyimide sulfonate esters, and especially the following structures: [ka]

[0122] Suitable additives for increasing the molecular weight of polycondensation polymers (chain extenders) are diepoxides, bis-oxazolines, bis-oxazolones, bis-oxazines, diisocyanates, dianhydrides, bis-acyllactams, bis-maleimides, dicyanates, carbodiimides, and polycarbodiimides. Other suitable chain extenders are polymeric compounds such as, for example, polystyrene-polyacrylate-polyglycidyl (meth)acrylate copolymers, polystyrene-maleic anhydride copolymers, and polyethylene-maleic anhydride copolymers.

[0123] Examples of suitable additives for increasing electrical conductivity are the above-mentioned antistatic agents, soot, carbon compounds such as carbon nanotubes and graphene, metal powders such as copper powder, and conductive polymers such as polypyrrole, polyaniline, and polythiophene.

[0124] Examples of suitable infrared-active additives are aluminum silicates, hydrotalcites, or dyes such as phthalocyanines or anthraquinones.

[0125] Examples of suitable crosslinking agents are peroxides such as dialkyl peroxides, alkylaryl peroxides, peroxyesters, peroxycarbonates, diacyl peroxides, peroxyketals, silanes such as vinyltrimethoxysilane, vinyltriethoxysilane, vinyltriacetoxysilane, vinyltris(2-methoxyethoxy)silane, 3-methacryloyloxypropyltrimethoxysilane, vinyldimethoxymethylsilane, or ethylene-vinylsilane copolymers.

[0126] Suitable prodegradants are additives that intentionally promote or control the degradation of polymers in the environment, for example, transition metal fatty acid esters such as manganese or iron promote oxidative and / or photooxidative degradation, such as enzymes that induce hydrolysis of polyolefins or aliphatic polyesters.

[0127] Examples of suitable chemical propellants are azo compounds such as azodicarboxylic acid amides, sulfonyl semicarbazides such as p-toluenesulfonyl semicarbazide, tetrazoles such as 5-phenyltetrazole, hydrazides such as p-toluenesulfonyl hydrazide, 4,4'-oxybis(benzolsulfonyl)hydrazide, N-nitroso compounds such as N,N'-dinitrosopentamethylenetetramine, or carbonates such as sodium bicarbonate or zinc carbonate.

[0128] Examples of suitable slip agents are amide waxes such as erucamide or oleamide.

[0129] Examples of suitable antiblocking agents are silica, talc, or zeolites.

[0130] Examples of suitable anti-fog additives are ethoxylated sorbitan esters, ethoxylated fatty acid alcohols, or ethoxylated alkylamine esters.

[0131] Examples of suitable biocides are quaternary ammonium or silver salts, colloidal silver or silver complexes, or derivatives of natural substances such as chitosan.

[0132] Suitable aldehyde scavengers are amines, hydroxylamines, poly(vinyl alcohol), zeolites or cyclodextrins, and suitable formaldehyde scavengers are melamine derivatives such as benzoguanamine, or urea derivatives such as allantoin.

[0133] Suitable odor binding or odor preventing materials are silicates such as calcium silicate, zeolites, or salts of hydroxy fatty acids, for example zinc ricenolate.

[0134] Examples of suitable marking agents are fluorescent dyes or rare earth metals.

[0135] Suitable nucleating agents are, for example, talc, alkali or alkaline earth salts of mono- and polyfunctional carboxylic acids, such as, for example, benzoic acid, succinic acid, adipic acid, for example, sodium benzoate, zinc glycerate, aluminum hydroxybis(4-tert-butyl)benzoate, 2,2'-methylene-bis-(4,6-di-tert-butylphenyl)phosphoric acid, as well as triamides and diamides, such as, for example, trimesic acid tricyclohexylamide, trimesic acid (4-methylcyclohexylamide), trimesic acid tris(tert-butylamide), N,N',N''-1,3,5-benzoltriyltris(2,2-dimethylpropanamide), or 2,6-naphthalenedicarboxylic acid dicyclohexylamide.

[0136] Suitable clarifiers (clarifiers) are, in particular, for example, sorbitol derivatives. [ka]

[0137] Suitable antinucleating agents are, for example, azine dyes such as nigrosine or ionic liquids.

[0138] Examples of suitable additives for increasing the thermal conductivity of plastic recycles are inorganic fillers such as boron nitride, aluminum nitride, aluminum oxide, aluminum silicate, silicon carbide, and carbon nanotubes (CNTs).

[0139] Suitable toughening agents are usually selected for each recyclate and are, for example, from the group of functionalized or non-functionalized polyolefins, for example ethylene copolymers such as EPDM or maleic anhydride or styrene-acrylonitrile modified EPDM, glycidyl methacrylate modified ethylene-acrylic acid copolymers or ionomers, core-shell polymers based on MBS (methacrylic acid-butadiene-styrene copolymers) or acrylate-poly(methyl methacrylate) thermoplastic elastomers (TPEs), for example the base of which is a styrene-block copolymer (styrene-butadiene (SB), styrene-butadiene-styrene (SBS), optionally hydrogenated (SEBS) or modified with maleic anhydride (SEBS-g-MAH), thermoplastic polyurethanes, copolyesters or copolyamides.

[0140] Examples of suitable plasticizers are esters of phthalic acid, terephthalic acid, adipic acid, 1,2-cyclohexanedicarboxylic acid, trimellitic acid, citric acid or phosphoric acid, such as benzyl butyl phthalate (BBP), butyl nonyl phthalate (BNP), didecyl phthalate (DDP), diisobutyl adipate (DIBA), diisodecyl adipate (DIDA), dioctyl terephthalate (DOTP), diisotridecyl phthalate (DTDP), tributyl O-acetylcitrate (TBAC), triethyl O-acetylcitrate (TOAC), tetrahydrofurfuryl oleate (THFO), triisooctyl trimellitate (TIOTM), tributyl phosphate (TBP), as well as epoxidized soybean oil (ESO) or epoxidized linseed oil (ELO).

[0141] Examples of suitable release agents are silicones, soaps, and waxes such as montan wax.

[0142] Preferably, the additive of the present invention, which may be in the form of a powder, liquid, fluid, oil, compressed onto a substrate, or in the form of granules, solutions or flakes, is mixed with the polymer to be stabilized, the polymer matrix is ​​converted into a melt and then cooled. Alternatively, it is also possible to introduce the additive into the polymer melt in the molten state.

[0143] Furthermore, the additive composition of the present invention can be prepared and introduced in the form of a so-called masterbatch or concentrate, for example, 10 to 90% of the composition of the present invention is contained in a polymer or polymer recyclate.

[0144] In another preferred embodiment, the composition comprises a secondary antioxidant, in particular a light stabilizer from the group of the phosphites / phosphonites, sulfites, polyols, acid scavengers, hindered amines, polyol-based co-stabilizers, and / or hindered amines (HALS).

[0145] In the aforementioned embodiments, it is advantageous if the at least one additive is contained and / or added in an amount of 0.01 to 80% by weight, preferably 0.01 to 9.99% by weight, more preferably 0.01 to 4.98% by weight, particularly preferably 0.02 to 2.00% by weight, based on the total of the at least one compound having the general formula I or II or, in the case of a mixture of several compounds having the general formula I and / or II, based on the total of all compounds having the general formula I and / or II of the plastic and the at least one additive.

[0146] Another aspect of the invention relates to a plastic composition comprising at least one plastic and at least one compound having general formula I and / or II as defined above or a mixture of several compounds having general formula I and / or II.

[0147] A preferred embodiment provides that the plastic composition has the following composition:

[0148] 0.01 to 10.00% by weight, preferably 0.01 to 7.50% by weight, more preferably 0.02 to 5.00% by weight, particularly preferably 0.05 to 3.00% by weight, of the compound having the general formula I or II or, in the case of a mixture of several compounds having the general formula I and / or II, of the sum of all the compounds having the general formula I and / or II, 99.99 to 10.00% by weight, preferably 99.99 to 90.00% by weight, more preferably 99.89 to 95.00% by weight, particularly preferably 99.90 to 98.00% by weight of at least one plastic, % by weight, preferably 0 to 9.99% by weight, more preferably 0.01 to 4.98% by weight, particularly preferably 0.02 to 2.00% by weight of at least one additive, The total of the above components is 100% by weight.

[0149] Preferably, the at least one additive is selected from the group consisting of primary and / or secondary antioxidants, in particular selected from the group consisting of phosphites, phosphonites, thiols, phenolic antioxidants, sterically hindered amines, hydroxylamines and mixtures or combinations thereof, UV absorbers, light stabilizers, hydroxylamine stabilizers, benzofuranone stabilizers, nucleating agents, toughening agents, plasticizers, lubricants, rheology modifiers, chain extenders, processing aids, pigments, dyes, gloss agents, antimicrobial agents, antistatic agents, slip agents, antiblocking agents, coupling agents, dispersants, compatibilizers, oxygen scavengers, acid scavengers, co-stabilizers, marking agents and antifogging agents, The at least one additive is preferably selected from the group consisting of phosphites, phosphonites, sulfites, polyols, acid scavengers, hindered amines, and mixtures and combinations thereof.

[0150] Particularly preferred plastic compositions are (A) 0.02 to 2 parts, particularly preferably 0.05 to 1 part, of at least one compound having the above general formula I or II, or a mixture of several compounds having the general formula I and / or II. (B) 43 to 99.96 parts plastic. (C) 0.02 to 4 parts, particularly preferably 0.05 to 2 parts (a) a phosphite or phosphonite and / or (b) sulfites and / or (c) polyol and / or (d) acid scavengers and / or (e) hindered amines, (D) 0 to 50 parts, particularly preferably 0 to 2 parts, of another additive The total number of copies is 100.

[0151] If the plastic composition (or equivalently the polymer composition) has other added components, they can be added to the polymer in the form of a liquid, powder, granules or compressed product, or separately from the additive composition of the invention described above (i.e. at least one compound having general formula I or II, or a mixture of several compounds having general formula I and / or II, in some cases additive).

[0152] The additive composition and optionally further additives are incorporated into the plastic by conventional processing methods, preferably in a mixer, kneader or extruder. Preferred processing machines are extruders, such as single-screw extruders, twin-screw extruders, planetary gear extruders, ring extruders, co-kneaders, etc., which are preferably equipped with a vacuum degassing device. Processing can be carried out in air or under inert gas conditions.

[0153] The processing of the plastic compositions comprising the described additive compositions can be carried out by conventional plastic processing methods in continuous and discontinuous processes, such as, for example, extrusion, calendaring, blow molding, pultrusion, injection molding, press molding, transfer molding, molding, blow molding, rotational molding, deep drawing, sintering, foaming, or by additive manufacturing processes to prepare granules, molded parts, semi-finished products, fibers and films.

[0154] Suitable extruders are piston extruders, screw-type extruders, single-screw extruders, twin-screw extruders, multi-screw extruders, planetary gear extruders, in particular for preparing plastic granules, tubes, rods, hoses, profiles, jackets, plates, films, V-belts, toothed belts, gaskets, foam sheets (XPS), fibers, and filaments for additive manufacturing processes.

[0155] Suitable injection molding machines can have hydraulic or electromechanical design and can include multi-component injection molding and in-mold processes. Examples of molded parts manufactured by injection molding are bottles, containers, screw plug boxes, housings, barrels, buckets, pallets, technical parts for automobiles and transportation, such as bumpers, cladding parts, handles, headlight covers, fittings and functional parts, electrical and electronic applications, such as housing parts and accessories for television sets, computers, mobile phones, washing machines, dishwashers, coffee machines, drills, plug and socket connectors, storage media, household, leisure and sports equipment, such as flower vases, coat hangers, game pieces, model making, furniture parts such as brackets and clips.

[0156] Examples of parts produced by blow molding are hollow bodies such as bottles, fuel tanks, canisters, windshield washer fluid reservoirs, and equalizing tanks, among others.

[0157] Parts produced by rotational molding are especially tanks, such as heating oil tanks and rainwater tanks, housings for machines, transport containers, leisure and water sports equipment, such as kayaks.

[0158] Calendering is used in particular to produce films such as decorative films, wallpapers and floor coverings.

[0159] Additive manufacturing processes include, for example, binder jetting (BJ), laser sintering (LS), selective laser melting (SLM), electron beam melting (EBM), fused deposition modeling (FDM), filament fusion fabrication (FFF), multi-jet modeling (MJM), polyjet modeling (PJM), layered laminate manufacturing (LLM), thermal transfer sintering (TIS), digital light processing (DLP), photopolymer jetting (PJ), and stereolithography (SL).

[0160] Examples of molded parts which can be produced from the compositions of the invention are foils or films, foams, fibres, cables and pipes, profiles, hollow bodies, tapes, membranes such as geomembranes, e.g. geomembranes or adhesives produced by extrusion, injection moulding, blow moulding, calendar moulding, pressing, spinning, rotational moulding etc., e.g. adhesives in the form of films, bottles, bags, screw plug boxes for packaging of food, detergents, cosmetics, storage and transport containers, e.g. boxes, crates, barrels, buckets, pallets, automobiles, railways, aircraft, ships and equipment, e.g. bumpers, exterior parts, fittings and functional parts, pads and architectural applications, e.g. profiles, construction films, cable ducts, housing cladding, soundproof walls, drains, profile boards, flooring, roads and constructions. applications such as movable bollards and signs, stakes, barriers, bases for geotextiles, electrical and electronic applications such as housing parts and accessories for television sets, computers, mobile phones, washing machines, dishwashers, coffee makers, drills, plug-socket connectors, storage media, cable insulation and pipes for water, gas, wastewater, irrigation etc., drainage pipes, hygiene products such as diapers etc., furniture, textiles such as curtains and cushions, work surfaces, household items, leisure items, sports equipment such as balls, tennis rackets, skis etc., flower vase, rainwater tanks, coat hangers, landscaping applications such as pharmaceuticals, plant protection applications for encapsulation of active ingredients and bioactive substances, suture materials, bandage materials, orthotics and prosthetics in medical engineering.

[0161] The present invention further relates to a method for stabilizing a plastic composition, in particular against oxidative, thermal and / or actinic degradation, by incorporating at least one compound having general formula I or II, or a mixture of several compounds having general formula I and / or II, into at least one plastic or into a blend of at least two plastics.

[0162] Furthermore, the present invention relates to novel compounds according to the above general formula I or II.

[0163] Another aspect of the present invention relates to a stabilizer composition comprising the following compound: a) at least one compound having the general formula I or II or a mixture of several compounds having the general formula I and / or II (component A) according to any one of claims 1 to 4, and b) at least one additive (component B) selected from the group consisting of primary and / or secondary antioxidants, in particular selected from the group consisting of phosphites, phosphonites, thiols, phenolic antioxidants, sterically hindered amines, hydroxylamines and mixtures or combinations thereof, UV absorbers, light stabilizers, hydroxylamine stabilizers, benzofuranone stabilizers, nucleating agents, toughening agents, plasticizers, lubricants, rheology modifiers, chain extenders, processing aids, pigments, dyes, gloss agents, antimicrobial agents, antistatic agents, slip agents, antiblocking agents, coupling agents, dispersants, compatibilizers, oxygen scavengers, acid scavengers, co-stabilizers, marking agents and antifogging agents, The at least one additive is preferably selected from the group consisting of phosphites, phosphorous salts, sulfites, polyols, acid scavengers, hindered amines, and mixtures and combinations thereof.

[0164] In the stabilizer composition, the weight ratio of component A to component B is preferably 100:1 to 1:100, more preferably 10:1 to 1:10, and particularly preferably 5:1 to 1:5.

[0165] The present invention will be described in detail by the following embodiments, but the present invention is not limited to the specific embodiments presented.

[0166] Exemplary embodiments To test the effectiveness of the stabilizers of the present invention, commercial polypropylene (Moplen HP 500N, Lyondell Basell Industries) was homogenized with the stabilizers of the present invention in a powder mixture and cycled in a twin screw microcompounder (DSM MC 5) at 200°C and 90 rpm for 30 minutes and the loss in strength was recorded. The strength is a direct measure of the molecular weight of the polypropylene; the smaller the loss, the better the stabilization effect.

[0167] The addition of 0.1-0.3% vanillic acid hexyl ester prepared according to WO 98 / 56748 improves the processing stability, i.e., residual strength, of polypropylene compared to the absence of vanillic acid hexyl ester. Furthermore, the addition of 0.2% mannitol or 0.2% tris-(2,4-di-tert-butylphenyl) phosphorous acid in addition to 0.2% vanillic acid hexyl ester improves processing stability.

[0168] Furthermore, the powder-powder mixture was mixed and granulated at 210°C with 0.5% vanillic acid hexyl ester using a twin-screw extruder (11 mm). The granules were injection molded to prepare test specimens, which were then irradiated with light in a weathering tester (bundle wheel). The test specimens without additives showed chalk formation on the surface, i.e., polymer damage, already after 100 hours, while the compositions containing the stabilizer of the present invention remained unchanged even after 300 hours.

[0169] The present invention will be described in detail below based on the embodiments, but the present invention is not limited to these.

[0170] 1. General synthetic methods for the preparation of the phenolic antioxidants and light stabilizers of the present invention The phenol ester (1 equivalent, 20 mmol) and the alcohol (0.3-1.5 equivalents, or 7-30 mmol) are placed in a dry Schlenk flask equipped with a condensation bridge and a cold trap. The reaction is stirred under an inert atmosphere and then briefly degassed. The tin catalyst (0.04 equivalents, 0.8 mmol) is added to the melt under a nitrogen counterflow. The temperature is increased to 130 ° C-140 ° C and the flask is slightly evacuated. The course of the reaction is 1 Check with H-NMR spectrum. After the reaction is complete, increase the temperature to 150°C-160°C and reduce the pressure to 1 mbar to separate the unreacted reactants from the product. Again 1 The progress is monitored by H-NMR spectroscopy. The vacuum is then broken and the product is cooled to room temperature. The solid is taken up in dichloromethane and 2.8 g of bleaching clay are added. After heating at reflux for 30 minutes, the mixture is filtered through a short pad of silica and the dichloromethane is evaporated off.

[0171] [2. Detailed synthesis method: Preparation of lauryl vanillate] [ka] 3.64 g vanillic acid methyl ester (methyl vanillate, 1 eq., 20 mmol) and 5.58 g lauryl alcohol (1.5 eq., 30 mmol) are placed in a dry 200 mL Schlenk flask equipped with a condensation bridge and a cold trap. The reactants are melted at a temperature of 90 °C under an inert nitrogen atmosphere with stirring (250 rpm) and then briefly degassed. 199.15 mg (0.04 eq., 0.8 mmol) of dibutyltin oxide are added under a nitrogen counterflow. The temperature is increased to 130 °C and the flask is slightly evacuated (≈800 mbar). Furthermore, the cold trap of the second flask is filled with liquid nitrogen, creating a slight negative pressure in the closed apparatus. The course of the reaction is monitored. 1 The reaction is confirmed by H-NMR spectroscopy (formation of a triplet at δ≈4.3 ppm). After the reaction is complete, the temperature is increased to 150° C., the pressure is reduced to 1 mbar and the excess vanillic acid methyl ester is separated from the product. Again 1The progress is monitored by H-NMR spectrum (disappearance of the double peak at δ≈3.8 ppm). Afterwards, nitrogen is introduced to break the vacuum and the product is cooled to room temperature. The solid is taken up in dichloromethane and 2.8 g of bleaching clay (Optimum 210FF) is added. After 30 min of heating at reflux (oil bath, temperature 60 °C), the mixture is filtered through a short silica pad and the dichloromethane is removed under reduced pressure. The remaining solid is crushed in a mortar and transferred to a snap-on cap bottle.

[0172] [3. Product] The following products were synthesized according to the general specifications: Vanillate Structure: Lauryl vanillate (LauVan), dodecyl 4-hydroxy-3-methoxybenzoate [ka] Stearyl vanillate (SteaVan), octadecyl 4-hydroxy-3-methoxybenzoate [ka] Hexane divanillate (HexDiVan), Hexane-1,6-diylbis(4-hydroxy-3-methoxybenzoate) [ka] Hexane trivanillate (HexTriVan), Hexane-1,2,6-triyltris(4-hydroxy-3-methoxybenzoate) [ka] Tetraethyleneglycylvanillic acid (TEGVan), ((oxybis(ethane-2,1-diyl))bis(oxy)bis(ethane-2,1-diyl)bis(4-hydroxy-3-methoxybenzoic acid) [ka] Octane divanillate (OctDiVan), Octane-1,8-diylbis(4-hydroxy-3-methoxybenzoate) [ka] Syringe gate structure: Lauryl syringate (LauSyr), dodecyl 4-hydroxy-3,5-dimethoxybenzoate [ka] Stearyl syringate (SteaSyr), octadecyl 4-hydroxy-3,5-dimethoxybenzoate [ka] Hexanedisilyngate (HexDiSyr), Hexane-1,6-diylbis(4-hydroxy-3,5-dimethoxybenzoic acid) [ka] Hexanetrisyringate (HexTriSyr), Hexane-1,2,6-triyltris(4-hydroxy-3,5-dimethoxybenzoic acid) [ka] N-SteaSyr (4-hydroxy-3,5-dimethoxyphenyl)(octadecyl-2-azaneyl)methanone [ka]

[0173] [4. Features] The properties measured for the synthesized compounds are shown in the table below.

[0174] [Table 1]

[0175] [Application example] In another series to test the effectiveness of the stabilizers of the present invention in commercial polypropylene (Moplen HF 501N, Lyondell Basell Industries), selected synthetic compounds were homogenized in a powder-powder mixture at a concentration of 0.035 mmol and cycled at 200° and 200 rpm for 30 minutes in a twin-screw microcompounder (MC 5, DSM) and the loss in strength was recorded. The strength is a direct measure of the molecular weight of the polypropylene; the smaller the loss, the better the stabilization effect.

[0176] The data were evaluated as follows: the measured intensity was measured every 5 min. To equalize the fluctuations occurring during the measurements, the average of the measurements was calculated every 30 s before the point of interest. For comparison between individual compounds, each measurement was normalized to the starting value. The percentage of residual intensity in each case is shown.

[0177] [Table 2]

[0178] In all cases, the additives of the present invention provide improved stability over the comparative examples.

Claims

1. Use of a compound having the general formula I or II, or a mixture of compounds having the general formula I and / or II: 【Chemistry 1】 【Chemistry 2】 In the formula, R １ , R ２ and R ３ are each independently selected from the group consisting of a hydroxy group, a linear or branched alkoxy group having 1 to 6 carbon atoms, and hydrogen; １ , R ２ and R ３ At least one of the R １ , R ２ and R ３ At least one of R is a linear or branched alkoxy group having 1 to 6 carbon atoms; １ , R ２ and R ３ The occurrences of may be identical or different, R is an organic group; X is the same or different in each occurrence and is O, NH, or NR in formula I, and O or NR in formula II; n is 0 or an integer from 1 to 10, preferably 1 to 4; Use for the stabilization of plastics, especially against oxidative, thermal and / or actinic degradation.

2. 2. The use according to claim 1, characterized in that R is selected from the following group: linear or branched and saturated or unsaturated alkyl groups, preferably linear alkyl groups having 6 or more carbon atoms, particularly preferably having 6, 8, 9, 10, 11, 12, 13, 14, 16, 18, 20, 22, 24, 26, 28 or 30 carbon atoms, 11-methyldodecan-1-yl, 3,7-dimethyl-7-octen-1-yl, (R)-3,7-dimethyloct-6-en-1-yl, 2,6-dimethyl-2,6-octadien-8-yl, cis-9-hexadecen-1-yl, cis-9-octadecen-1-yl, cis-13-docosene-1-yl, cis,cis-9,12-octadecadien-1-yl, 3,7-dimethyl-trans-2,6-octadien-1-yl, aromatic groups, such as substituted or unsubstituted phenyl or benzyl; or 2,3-dihydroxypropan-1-yl, linear or branched and saturated or unsaturated alkanediyl groups, preferably 1,2-ethanediyl, 1,3-propanediyl, 1,4-butanediyl, 1,5-pentanediyl, 1,6-hexanediyl, 1,8-octanediyl; linear or branched and saturated or unsaturated oxaalkanediyl groups, in particular oxaethylenediyl or oxapropylenediyl groups, such as 3-oxapentane-1,5-diyl, 2,2′-(ethylenedioxy)diethanediyl, 2,4-dimethyl-3-oxapentane-1,5-diyl, 4-oxaheptane-2,6-diyl, 2-(2-hydroxypropyl)-1-propyl, 1,3-cyclohexanediyl, 1,4-cyclohexanediyl; aromatic groups, in particular benzene-1,4-diyl or benzene-1,3-diyl, 2-hydroxypropane-1,3-diyl, 2-aminopropane-1,3-diyl, and A divalent, trivalent or tetravalent oxaethylenediyl group derived from an alditol.

3. R １ is a linear or branched alkoxy group having 1 to 6 carbon atoms, in particular a methoxy group, R ２ is a hydroxy group, R ３ is a linear or branched alkoxy group having 1 to 6 carbon atoms, in particular a methoxy group, or hydrogen; 2. The use according to claim 1.

4. The compound having general formula I is selected from the group consisting of the following compounds: 【Transformation 3】 【Chemistry 4】 【Transformation 5】 【Transformation 6】 【Transformation 7】 【Transformation 8】 【Chemistry 9】 and a compound having the general formula II 【Chemistry 10】 2. The use according to claim 1, characterized in that:

5. 2. The use according to claim 1, characterized in that the compound having the general formula I or II, or in the case of a mixture of several compounds having the general formula I and / or II, the sum of all compounds having the general formula I and / or II, is contained in the plastic in a weight percentage of 0.01 to 10.00% by weight, preferably 0.02 to 5.00% by weight, particularly preferably 0.05 to 3.00% by weight.

6. 2. The use according to claim 1 for the stabilization of plastics, wherein the plastics are selected from the following group: a) polymers of olefins or diolefins, such as polyethylene (LDPE, LLDPE, VLDPE, ULDPE, MDPE, HDPE, UHMWPE), metallocene-PE (m-PE), polypropylene, polyisobutylene, poly-4-methylpentene-1, polybutadiene, polyisoprene, for example, but also natural rubber (NR), poly(cyclooctene), polyalkylene-carbon monoxide copolymers, and also copolymers with statistical or block structure, such as polypropylene-polyethylene (EP), EPM or EPDM (for example 5-ethylidene-2-norbornane). polypropylene copolymers such as ethylene glycol as a comonomer), ethylene vinyl acetate (EVA), ethylene acrylates, e.g., ethylene butyl acrylate, ethylene acrylic acid and their salts (ionomers), and terpolymers, e.g., ethylene acrylic acid (meth)acrylate, graft polymers, e.g., polypropylene graft maleic anhydride, and blends, e.g., LDPE / LLDPE or long chain polypropylene copolymers made with alpha olefins as comonomers, e.g., 1-butene, 1-hexene, 1-octene or 1-octadecene, b) polystyrene, polymethylstyrene, poly-α-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), acrylonitrile-butadiene-styrene (ABS), styrene-acrylonitrile (SAN), styrene-acrylonitrile acrylate (ASA), styrene-ethylene, styrene-maleic anhydride polymers including the corresponding graft polymers, for example styrene to butadiene, maleic anhydride to SBS or SEBS, and graft polymers from methyl methacrylate, styrene butadiene and ABS (MABS), and hydrogenated polystyrene derivatives, such as polyvinylcyclohexane, c) halogen-containing polymers, such as polyvinyl chloride (PVC), polychloroprene and polyvinyl dichloride (PVDC), copolymers of vinyl chloride and vinylidene chloride or vinyl chloride and vinyl acetate, chlorinated polyethylene, polyvinylidene fluoride, epichlorohydrin homopolymers and copolymers, especially with ethylene oxide (ECO); d) polymers of unsaturated esters, such as polyacrylates and polymethacrylates, for example polymethyl methacrylate (PMMA), polybutyl acrylate, polylauryl acrylate, polystearyl acrylate, polyglycidyl acrylate, polyglycidyl methacrylate, polyacrylonitrile, polyacrylamide, copolymers such as polyacrylonitrile-polyalkyl acrylate, etc. e) polymers of unsaturated alcohols and derivatives, such as polyvinyl alcohol, polyvinyl acetate, polyvinyl butyral, polyallyl phthalate, polyallyl melamine, f) polyacetalenes, such as copolymers of polyoxymethylene (POM) or butanal, g) Polyphenylene oxide and blends with polystyrene or polyamide h) polymers of cyclic ethers, such as polyethylene glycol, polypropylene glycol, polyethylene oxide, polypropylene oxide, polytetrahydrofuran; i) polyurethanes, in particular linear polyurethanes (TPU), polycarbamides, based on hydroxy-terminated polyethers or polyesters and aromatic or aliphatic isocyanates, such as 2,4- or 2,6-toluylene diisocyanate or methylene diphenyl diisocyanate, 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 (partially) aromatic polyamides, such as polyphthalamides, prepared, for example, from terephthalic acid and / or isophthalic acid and aliphatic diamines, such as hexamethylenediamine or m-xylylenediamine, or from aliphatic dicarboxylic acids, such as adipic acid or sebacic acid, and aromatic diamines, such as 1,4- or 1,3-diaminobenzene, blends of different polyamides, such as PA6 and PA6.6, or blends of polyamides with polyolefins, such as PA / PP; k) polyimides, polyamideimides, polyetherimides, polyesterimides, poly(ether)ketones, polysulfones, polyethersulfones, polyarylsulfones, polyphenylene sulfides, polybenzimidazoles, polyhydantoins, l) polyesters of aliphatic or aromatic dicarboxylic acids and diols or polyesters of hydroxycarboxylic acids, such as polyethylene terephthalate (PET), polybutylene terephthalate (PBT), polypropylene terephthalate (PTI), polyethylene naphthalate (PEN), poly-1,4-dimethylolcyclohexane terephthalate, poly(hydroxybenzoate), polyhydroxynaphthalate, polylactic acid (PLA), polyhydroxybutyrate (PHB), polyhydroxyvalerate (PHV), polyethylene succinate, polytetramethylene succinate, polycaprolactone, m) polycarbonates, polyester carbonates and blends such as PC / ABS, PC / PBT, PC / PET / PBT, PC / PA, n) cellulose derivatives, such as cellulose nitrate, cellulose acetate, cellulose propionate, cellulose butyrate o) epoxy resins consisting of a combination of di- or polyfunctional epoxides with curing agents based, for example, on amines, anhydrides, dicyandiamide, mercaptans, isocyanates or catalytically active curing agents; p) phenolic resins, such as phenol formaldehyde resins, urea formaldehyde resins, melamine formaldehyde resins, q) unsaturated polyester resins prepared from unsaturated dicarboxylic acids and diols with vinyl compounds, such as styrene, alkyd resins; r) silicones, such as those based on dimethylsiloxane, methylphenylsiloxane, or diphenylsiloxane, for example vinyl-terminated; s) and mixtures, combinations or blends of two or more of the foregoing polymers.

7. 2. The use according to claim 1, characterized in that at least one other additive selected from the group consisting of primary and / or secondary antioxidants, in particular 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, UV absorbers, light stabilizers, hydroxylamine stabilizers, benzofuranone stabilizers, nucleating agents, toughening agents, plasticizers, lubricants, rheology modifiers, chain extenders, processing aids, pigments, dyes, brighteners, antibacterial agents, antistatic agents, slip agents, antiblocking agents, coupling agents, dispersants, compatibilizers, oxygen scavengers, acid scavengers, co-stabilizers, marking agents, and antifogging agents, is contained in and / or added to the plastic during use.

8. 8. The use according to claim 7, characterized in that the at least one additive is selected from the group consisting of phosphites, phosphonites, sulfites, polyols, acid scavengers, hindered amines, and mixtures and combinations thereof.

9. 9. Use according to claim 7 or 8, characterized in that the at least one additive is contained and / or added in an amount of 0.01 to 80% by weight, preferably 0.01 to 9.99% by weight, more preferably 0.01 to 4.98% by weight, particularly preferably 0.02 to 2.00% by weight, based on the total of the at least one compound having the general formula I or II or, in the case of a mixture of several compounds having the general formula I and / or II, based on the total of all compounds having the general formula I and / or II of the plastic and the at least one additive.

10. A plastic composition comprising at least one plastic and at least one compound having the general formula I and / or II according to any one of claims 1 to 4 or a mixture of several compounds having the general formula I and / or II.

11. 0.01 to 10.00% by weight, preferably 0.01 to 7.50% by weight, more preferably 0.02 to 5.00% by weight, particularly preferably 0.05 to 3.00% by weight, of the compound having the general formula I or II, or, in the case of a mixture of several compounds having the general formula I and / or II, of the sum of all compounds having the general formula I and / or II, 99.99 to 10.00% by weight, preferably 99.99 to 90.00% by weight, more preferably 99.89 to 95.00% by weight, particularly preferably 99.90 to 98.00% by weight of at least one plastic, 0 to 80.00 wt. %, preferably 0 to 9.99 wt. %, more preferably 0.01 to 4.98 wt. %, and particularly preferably 0.02 to 2.00 wt. % of at least one additive; The plastic composition according to claim 10, wherein the total of the components is 100% by weight.

12. at least one additive is selected from the group consisting of primary and / or secondary antioxidants, in particular 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, UV absorbers, light stabilizers, hydroxylamine stabilizers, benzofuranone stabilizers, nucleating agents, toughening agents, plasticizers, lubricants, rheology modifiers, chain extenders, processing aids, pigments, dyes, brighteners, antimicrobial agents, antistatic agents, slip agents, antiblocking agents, coupling agents, dispersants, compatibilizers, oxygen scavengers, acid scavengers, co-stabilizers, marking agents, and antifogging agents; 12. The plastic composition of claim 11, wherein the at least one additive is preferably selected from the group consisting of phosphites, phosphonites, sulfites, polyols, acid scavengers, hindered amines, and mixtures and combinations thereof.

13. 10. A method for stabilizing a plastic composition, in particular against oxidative, thermal and / or actinic degradation, comprising incorporating at least one compound having the general formula I or II, or a mixture of compounds having the general formula I and / or II, according to any one of claims 1 to 4, into at least one plastic or into a blend of at least two plastics.

14. A compound having the formula: 【Chemistry 11】 【Chemistry 12】

15. A stabilizer composition comprising the following compounds: a) at least one compound of general formula I or II or a mixture of several compounds of general formula I and / or II (component A) according to any one of claims 1 to 4, and b) at least one additive (component B) selected from the group consisting of primary and / or secondary antioxidants, in particular 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, UV absorbers, light stabilizers, hydroxylamine stabilizers, benzofuranone stabilizers, nucleating agents, toughening agents, plasticizers, lubricants, rheology modifiers, chain extenders, processing aids, pigments, dyes, brighteners, antimicrobial agents, antistatic agents, slip agents, antiblocking agents, coupling agents, dispersants, compatibilizers, oxygen scavengers, acid scavengers, co-stabilizers, marking agents, and antifogging agents, The at least one additive is preferably selected from the group consisting of phosphites, sulfites, polyols, acid scavengers, hindered amines, and mixtures and combinations thereof.

16. 16. The stabilizer composition according to claim 15, characterized in that the weight ratio of component A to component B is from 100:1 to 1:100, preferably from 10:1 to 1:10, particularly preferably from 5:1 to 1:5.

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