EP3997164A1 - Utilisation de dérivés du sucre à substitution phénolique comme stabilisants, composition de matières plastiques, procédé de stabilisation de matières plastiques et dérivés du sucre à substitution phénolique - Google Patents

Utilisation de dérivés du sucre à substitution phénolique comme stabilisants, composition de matières plastiques, procédé de stabilisation de matières plastiques et dérivés du sucre à substitution phénolique

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Publication number
EP3997164A1
EP3997164A1 EP20737440.6A EP20737440A EP3997164A1 EP 3997164 A1 EP3997164 A1 EP 3997164A1 EP 20737440 A EP20737440 A EP 20737440A EP 3997164 A1 EP3997164 A1 EP 3997164A1
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EP
European Patent Office
Prior art keywords
acid
group
sugar
sugar derivative
agents
Prior art date
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Pending
Application number
EP20737440.6A
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German (de)
English (en)
Inventor
Rudolf Pfaendner
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Fraunhofer Gesellschaft zur Forderung der Angewandten Forschung eV
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Fraunhofer Gesellschaft zur Forderung der Angewandten Forschung eV
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Publication of EP3997164A1 publication Critical patent/EP3997164A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • C08K5/134—Phenols containing ester groups
    • C08K5/1345—Carboxylic esters of phenolcarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/005—Stabilisers against oxidation, heat, light, ozone
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • C08K5/101—Esters; Ether-esters of monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • C08K5/101—Esters; Ether-esters of monocarboxylic acids
    • C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • C08K5/134—Phenols containing ester groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/20—Carboxylic acid amides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K2201/00—Specific properties of additives
    • C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K

Definitions

  • Plastic composition Use of phenolically substituted sugar derivatives as stabilizers.
  • Plastic composition Process for stabilizing plastics such as phenolically substituted sugar derivatives
  • the present invention relates to the use of at least one phenolically substituted sugar derivative as a stabilizer of organic materials, in particular of plastics, against oxidative, thermal and / or actinic degradation.
  • the present invention relates to a corre sponding plastic composition, a method for stabilizing Plastics, a molding compound or a molded part and a phenolically substituted sugar derivative.
  • Organic materials such as plastics are subject to aging processes, which ultimately lead to a loss of the desired properties such as the mechanical parameters.
  • This process known as autoxidation, leads to changes in the polymer chain, such as the molecular weight or the formation of new chemical groups, based on radical chain scission by mechanochemical processes or by UV radiation in the presence of oxygen.
  • Stabilizers are therefore used to prevent or at least delay this aging process.
  • Important representatives of stabilizers are antioxidants that interfere with the radicals formed during autoxidation and thus interrupt the degradation process.
  • primary antioxidants which can react directly with oxygen-containing free radicals or C-radicals
  • secondary antioxidants which react with hydroperoxides formed as intermediates (see C. Kröhnke et al.
  • Antioxidants in Ullmann 's encyclopedia of industrial chemistry Wiley-VCH Verlag, Weinheim 2015.
  • Typical representatives of primary antioxidants are, for example, phenolic antioxidants, amines, but also lactones.
  • Classes of secondary antioxidants are phosphorus compounds such as phosphites and phosphonites, but also organo-sulfur compounds such as sulfides and disulfides.
  • primary and secondary antioxidants are often combined in practice, which leads to a synergistic effect.
  • Phenolic antioxidants generally consist of sterically hindered phenol groups, which are present in the form of esters to increase molecular weight, improve compatibility and reduce volatility.
  • the polyols such as pentaerythritol are used, the 4 alcohol groups of which are fully esterified dig.
  • substitution products are also one of the other They contain a higher number of phenolic antioxidants such as hexasubstituted mannitol or hexasubstituted cyclitol, all of which have in common that, for the reasons mentioned, complete esterification is achieved with the effective structures.
  • phenolic antioxidants are usually combined in a synergistic way with other stabilizers.
  • stabilizers are also known which have both primary and secondary antioxidant structures in one molecule, e.g.
  • the object of the present invention is therefore to provide stabilizers based, at least in part, on renewable raw materials which have a high stabilizing effect.
  • the task is related to a use with the features of patent claim 1, regarding a stabilized plastic composition with the features of patent claim 14, regarding a method for stabilizing plastics with the features of patent claim 17, regarding a molding compound with the features of patent claim 18 , in terms of a stabilizer composition for stabilizing plastics with the features of claim 19 and with respect to the stabilizing we kenden sugar derivatives with the features of claim 20 solved.
  • the respective dependent claims represent advantageous developments.
  • the present invention thus relates to the use of at least one phenolically substituted sugar derivative, the sugar derivative having a base structure derived from a sugar, and at least one substituent according to general formula I
  • R 1 and R 2 are identical or different on each occurrence and are selected from the group consisting of hydrogen and linear or branched alkyl radicals, with the proviso that at least one radical R 1 or R 2 is not hydrogen, an alkylene group with 1 to 18 carbon atoms or a chemical bond,
  • the group X is bound to the terminus shown on the left of the groupings Y shown above, and where the base of the phenolically substituted sugar derivative derived from a sugar has at least 3 unsubstituted hydroxyl groups and / or the base of the phenolic derived from a sugar substituted sugar derivative has at least 4 carbon atoms and at least 2, preferably at least 3 unsubstituted hydroxyl groups, as a stabilizer of organic materials, in particular plastics, against oxidative, thermal and / or actinic degradation.
  • stabilizing in the sense of the present invention is understood that the appropriately equipped organic Ma materials, for example the plastics to which a sugar derivative according to formula I are added, under oxidative, thermal and / or actinic conditions have a longer shelf life, such as retention of mechanical and / or visual properties, compared to molding compounds that are finished without the corresponding additives.
  • the stabilizing effect as defined above, can be achieved with substances which have a basic structure based on renewable raw materials.
  • the base body derived from a sugar is a monosaccharide, an oligosaccharide or a polysaccharide with at least 4 carbons.
  • the phenolic substituted sugar derivative particularly preferably comprises a maximum of 10, preferably a maximum of 5, more preferably a maximum of 3, particularly preferably 1 or 2, substituents according to formula I.
  • the base body derived from a sugar can be at least one alditol, a cyclitol, a sugar acid or an amino sugar with at least 4 carbons.
  • the alditol can have the following empirical formulas
  • the at least one alditol is particularly preferably selected from the group consisting of threitol, erythritol, galactitol, mannitol, ribitol, sorbitol, xylitol, Ara bit, isomalt, lactitol, maltitol, maltotritol and hydrogenated oligo- and polysaccharides with polyol end groups and mixtures thereof , wherein the at least one alditol is preferably selected from the group consisting of erythritol, mannitol, isomalt, maltitol and mixtures thereof.
  • the at least one cyclitol can be selected from the group consisting of inositol (myo, scyllo-, D-chiro-, L-chiro-, muco-, neo-, allo-, epi- and cis-innosite), quercitol, Viscumitol, Bornesitol, Conduritol, Ononitol, Pinitol, Pinpollitol, Ciceritol, Quebrachitol, Quinic acid, Shikimic acid and Valienol, the at least one cyclitol being preferably myo-inositol (myo-inositol).
  • Preferred sugar acids are, for example, aldonic acids, such as in particular allonic acid, altronic acid, gluconic acid, mannonic acid, gulonic acid, idonic acid, galactonic acid, talonic acid, ribonic acid, arabonic acid, xylonic acid, lyxonic acid, erythronic acid or threonic acid or aldaric acids such as mucic acid or glucaric acid, and mixtures and combinations thereof.
  • aldonic acids such as in particular allonic acid, altronic acid, gluconic acid, mannonic acid, gulonic acid, idonic acid, galactonic acid, talonic acid, ribonic acid, arabonic acid, xylonic acid, lyxonic acid, erythronic acid or threonic acid or aldaric acids such as mucic acid or glucaric acid, and mixtures and combinations thereof.
  • the at least one amino sugar is, for example, a mono- or diamino sugar and is particularly preferably selected from the group consisting of 1-amino-l-deoxy-alditols, such as for example 1-amino-1-deoxy-galactitol, 1-amino-1-deoxy-mannitol, 1-amino-1-deoxy-sorbitol, 1-amino-1-deoxy-maltitol or ⁇ , -diamino- ⁇ , -dideoxyalditols such as, for example, 1,6-di-amino-1,6-dideoxy sorbitol.
  • 1-amino-l-deoxy-alditols such as for example 1-amino-1-deoxy-galactitol, 1-amino-1-deoxy-mannitol, 1-amino-1-deoxy-sorbitol, 1-amino-1-deoxy-maltitol or ⁇ , -diamino
  • radicals R 1 and R 2 are identical or different, particularly preferably identical.
  • the radicals R 1 and R 2 can in particular be selected from the group consisting of tert-butyl and methyl.
  • Particularly preferred phenolically substituted sugar derivatives are selected from the group consisting of the following molecules as well as mixtures and combinations thereof.
  • the at least one phenolically substituted sugar derivative can preferably be used in a total amount of 0.01 to 10% by weight, preferably 0.05 to 5% by weight, particularly preferably 0.1 to 3% by weight, based on the plastic.
  • the at least one phenolically substituted sugar derivative is used in combination with a primary and / or secondary antioxidant that differs from the at least one phenolically substituted sugar derivative
  • the at least one antioxidant preferably being selected from the group consisting of from phenolic antioxidants, amines, lactones and mixtures thereof
  • the at least one secondary antioxidant is selected from the group consisting of phosphorus compounds, in particular phosphites and phosphites, organosulfur compounds, in particular sulfides and disulfides, and mixtures thereof.
  • Suitable primary antioxidants are phenolic antioxidants, amines and
  • Lactones Suitable synthetic phenolic antioxidants are for example:
  • Alkylated monophenols such as, 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-methyl-phenol, 2- ( ⁇ -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-methyl-phenol, 2,4-dimethyl-6- (l'-methylundec-l'-yl) phenol, 2,4-
  • 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, for example, 2,6-di-tert-butyl-4-methyoxyphenol, 2,5-di-tert-butylhydroquinone, 2,5-di-tert-amylhydroquinone, 2,6-diphenyl-4 octadecyloxyphenol, 2,6-di-tert-butylhydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl -4-hydroxyphenyl stearate, bis (3,5-di-tert-butyl-4-hydroxylphenyl) adipate;
  • Hydroxylated thiodiphenyl ethers such as 2,2'-thiobis (6-tert-butyl-4-methyl-phenol), 2,2'-thiobis (4-octylphenol), 4,4'-thiobis (6-tert-butyl- 3-methyl-phenol), 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;
  • Alkylidenebisphenols such as 2,2'-methylenebis (6-tert-butyl-4-methylphenol), 2,2'-methylenebis (6-tert-butyl-4-ethylphenol), 2,2'-methylenebis [4-methyl- 6- (a-methylcyclohexyl) phenol], 2,2'-methylenebis (4-methyl-6-cyclhexylphenol), 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 ' -Methylene bis [6- (a-methylbenzyl) -4-nonyl- phenol], 2,2'-methylenebis [6- (a, a-dimethylbenzyl) -4-nonyl
  • O-, N- and S-benzyl compounds such as, for example, 3,5,3 ', 5'-tetra-tert-butyl-4,4'-dihydroxydibenzyl ether, octadecyl-4-hydroxy-3,5-dimethylbenzyl mercapto acetate , 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, didodecyl mercaptoethyl-2,2-bis (3,5-di-tert-butyl-4-hydroxy-benzyl) malonate, bis [4- (l, l, 3,3-tetramethylbutyl) phenyl] -2,2- bis (3,5-di-tert-butyl-4-hydroxybenzyl) malonate;
  • Aromatic hydroxybenzyl compounds such as, for example, 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) -2,4,6-trimethylbenzene, 1,4-bis (3,5-di-tert- butyl-4-hydroxybenzyl) -2,3,5,6-tetramethylbenzene, 2,4,6-tris (3,5-di-tert-butyl-4-hydroxybenzyl) phenol;
  • Triazine compounds such as, 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) -l, 3,5-triazine, 2-octylmercapto-4,6-bis (3,5-di-tert-butyl-4-hydroxyphenoxy) -l, 3,5-triazine, 2,4,6-tris (3,5-di-tert-butyl-4-hydroxyphenoxy) -l, 2,3-triazine, 1,3,5-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, 1,3,5-T ris (4- te / T-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyan
  • Benzyl phosphonates such as dimethyl-2,5-di-tert-butyl-4-hydroxybenzylphosphonate, diethl-3,5-di-te / T-butyl-4-hydroxybenzylphosphonate, dioctadecyl
  • Acylaminophenols such as 4-hydroxylauranilide, 4-hydroxystearanilide, octyl-N- (3,5-di-tert-butyl-4-hydroxyphenyl) carbamate;
  • Esters of ß- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid with monohydric or polyhydric alcohols e.g. methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N'-bis (hydroxyethyl) oxamide, 3-thiaund canol , 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo [2.2.2
  • Esters of ß- (5-tert-butyl-4-hydroxy-3-methylphenyl) propionic acid with mono- or polyhydric alcohols e.g. methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N'-bis (hydroxyethyl) oxamide, 3-thiaund canol , 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo [2.2.2] o
  • Esters of ß- (3,5-dicyclohexyl-4-hydroxyphenyl) propionic acid with monohydric or polyhydric alcohols e.g. 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;
  • Esters of (3,5-di-te / T-butyl-4-hydroxyphenyl) acetic acid with mono- or polyvalent alcohols for example 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 ß- (3,5-di-te / T-butyl-4-hydroxyphenyl) propionic acid such as N, N'-bis (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) hexamethylene diamide, N, N'-bis (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) hexamethylene diamide, N, N'-bis (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) hexamethylene diamide, N, N'-bis (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) hydrazide, N, N'-bis [2- (3- [3,5-di- te / T-butyl-4-hydroxyphenyl] propionyloxy) ethyl] oxamide (Naugard ® XL-l, ver driven by Sl group);
  • vitamin C Ascorbic acid (vitamin C).
  • Particularly preferred phenolic antioxidants are the following structures:
  • n is an integer in the aforementioned compounds and is between 2 and 10
  • phenolic antioxidants are phenolic antioxidants based on renewable raw materials such as. B. a-, ß-, g-, d-tocopherol and mixtures of these (vitamin E), tocotrienols, tocomonoenols, ubiquinol, hydroxytyrosol, flavonoids and flavonols such as chrysin, quercitin, hes peridin, neohesperidin, naringin, morin , Kaempferol, fisetin, datiscetin, lute olin, apigenin, taxifolin, isoflavones such as genistein, genistin, daidzein, daidzin, formononetin, anthocyanins such as delphinidin and malvidin, curcumin, carnosic acid, carnosol, rosmarinic acid, tannin and carotenoid resverrol with alcoholic groups, such as beta-crypto
  • Further stabilizers are copper-l-halides, for example CuJ, CuBr, optionally in mixtures with alkali halides such as KJ or KBr or Cu (l) complexes, for example with triphenylphosphine.
  • Suitable aminic antioxidants are, for example:
  • Preferred amine antioxidants are: N, N'-di-isopropyl-p-phenylenediamine, N, N'-di-sec-butyl-p-phenylenediamine, N, N'-bis (1,4-dimethylpentyl) -p -phenylenediamine, N, N'-bis (l-ethyl-3-methylpentyl) -p-phenylenediamine, N, N'-bis (l-methylheptyl) -p-phenylenediamine, N, N'-dicyclohexyl-p- phenylenediamine, N, N'-diphenyl-p-phenylenediamine, N, N'-bis (2-naphthyl) -p-phenylenediamine, N-isop- ropyl-N'-phenyl-p-phenylenediamine, N- (1,3-dimethylbutyl) -N
  • Particularly preferred aminic antioxidants are the structures:
  • n is an integer and is between 3 and 100.
  • aminic antioxidants are hydroxylamines or N-oxides (nitrones), such as, for example, N, N-dialkylhydroxylamines, N, N-dibenzylhydroxylamine, N, N-dilaurylhydroxylamine, N, N-distearylhydroxylamine, N-benzyl-a-phe - nylnitron, N-octadecyl-a-hexadecylnitron, as well as Genox TM EP (Sl Group) according to the formula:
  • R 2 C 14 -C 2 alkyl chains
  • Suitable lactones are benzofuranones and indolinones such as 3- (4- (2-ace- toxyethoxy) 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 -on), 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
  • antioxidants are isoindolo [2, l-A] quinazolines such as e.g.
  • Suitable secondary antioxidants (B) are phosphorus compounds such as phosphites and phosphonites, and organosulfur compounds such as sulphides and disulphides.
  • Suitable phosphites / phosphonites are, for example:
  • Triphenyl phosphite diphenyl alkyl phosphites, phenyl dialkyl phosphites, tri (nonyl phenyl) phosphite, trilauryl phosphites, trioctadecyl phosphite, distearyl penta- erythritol diphosphite, tris- (2,4-di-tert-butylphenyl) phosphite, bis (2,4-di-phosphite-di-phosphitol) -tertitol, diisodecylpenta-erythritol -butylphenyl) pentaerythritol diphosphite, bis (2,4-di-cumylphenyl) pentaerythritol diphosphite, bis (2,6-di-tert-butyl-4-methylphenyl) pentaery
  • Particularly preferred phosphites / phosphonites are:
  • a preferred phosphonite is:
  • Suitable sulfur compounds are, for example, distearyl thiodipropionate, dilauryl thiodipropionate; Ditridecyldithiopropionate, ditetradecylthiodipropionate, 3- (dodecylthio) -, l, l '- [2,2-bis [[3- (dodecylthio) -l-oxopropoxy] methyl] -l, 3-propanediyl] propanoic acid ester.
  • the following structures are preferred:
  • the aforementioned primary and / or secondary antioxidants can there in a total amount (ie as the sum of primary and / or secondary antioxidant), based on the total amount of the at least one phenolically substituted sugar derivative of 0.01 to 5 parts by weight , preferably from 0.02 to 3 parts by weight, particularly preferably from 0.05 to 2 parts by weight.
  • thermoplastic, thermoset or elastomeric polymers 0.04 to 6 parts by weight, preferably 0.06 to 1 part by weight, of the at least one primary antioxidant and / or of the at least one secondary antioxidant are introduced.
  • the plastics are in particular thermoplastic, thermoset or elastomeric polymers.
  • Suitable thermoplastic or thermoset polymers are in particular: a) Polymers made from olefins or diolefins such as polyethylene (LDPE,
  • polystyrene polymethylstyrene, poly-alpha-methylstyrene, polyvinylnaphtha lin, polyvinylbiphenyl, polyvinyltoluene, styrene-butadiene (SB), styrene-butadiene-styrene (SBS), styrene-ethylene-butylene-styrene (SEBS), styrene Ethylene-propylene-styrene, styrene-isoprene, styrene-isoprene-styrene (SIS), styrene-butadiene-acrylonitrile (ABS), styrene-acrylonitrile (SAN), styrene-acrylonitrile-acrylate (ASA), styrene-ethylene, Styrene-maleic anhydride polymers including appropriate graft copopoly
  • halogen-containing polymers such as polyvinyl chloride (PVC), polychloroprene and polyvinylidene chloride (PVDC), copolymers of vinyl chloride and vinylidene chloride or of vinyl chloride and vinyl acetate, chlorinated polyethylene, polyvinylidene fluoride, epichlorohydrin homo and copolymers, especially with ethylene oxide (ECO)
  • PVC polyvinyl chloride
  • PVDC polychloroprene and polyvinylidene chloride
  • PMMA polymethyl methacrylate
  • PMMA polybutyl acrylate
  • polylauryl acrylate polylauryl acrylate
  • polystearyl acrylate polyglycidyl acrylate
  • polyacetals such as polyoxymethylene (POM) or copolymers with e.g.
  • polyphenylene oxides and blends with polystyrene or polyamides h) polymers of cyclic ethers such as polyethylene glycol, polypropylene glycol, polyethylene oxide, polypropylene oxide, polytetrahydrofuran, i) polyurethanes made from hydroxy-terminated polyethers or polyesters and aromatic or aliphatic isocyanates such as 2,4- or 2,6 toluene diisocyanate or methylenediphenyl diisocyanate, especially linear polyurethanes (TPU), polyureas,
  • TPU linear polyurethanes
  • Polyamides such as 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, e.g.
  • 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 PA-6 and PA 6.6 or blends of Polyamides and polyolefins such as PA / PP
  • polyimides polyamide-imides, polyetherimides, polyesterimides, poly (ether) ketones, polysulfones, polyether sulfones, polyarylsulfones, polyphenylene sulfides, polybenzimidazoles, polyhydantoins,
  • Polyesters made from aliphatic or aromatic dicarboxylic acids and diols or from hydroxycarboxylic acids such as polyethylene terephthalate (PET), polybutylene terephthalate (PBT), polypropylene terephthalate (PTT), polyethylene naphthylate (PEN), poly-1,4-dimethylolcyclohexate, polyhydrotha-benzoate 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
  • cellulose derivatives such as cellulose nitrate, cellulose acetate, cellulose propionate, cellulose butyrate,
  • Epoxy resins consisting of di- or polyfunctional epoxy compounds in combination with e.g. hardeners based on amines, anhydrides, dicyandiamide, mercaptans, isocyanates or catalytically active hardeners,
  • Phenolic resins such as phenol-formaldehyde resins, urea-formaldehyde resins, melamine-formaldehyde resins,
  • Silicones e.g. based on dimethylsiloxanes, methyl-phenyl-siloxanes or diphenylsiloxanes, e.g. terminated with vinyl groups
  • polymers specified under a) to r) are copolymers, they can be in the form of random (“random”), block or “tape red” structures. Furthermore, the polymers mentioned can be in the form of linear, branched, star-shaped or hyperbranched structures.
  • polymers specified under a) to r) are stereoregular polymers, these can be in the form of isotactic, stereotactic, but also atactic forms or as stereoblock copolymers.
  • the polymers specified under a) to r) can have both amorphous and (partially) crystalline morphologies.
  • polystyrene resins mentioned under a) can also be crosslinked, e.g. crosslinked polyethylene, which is then referred to as X-PE.
  • the present compounds can be used to stabilize chewing Schuken and elastomers are used.
  • This can be natural rubber (NR) or synthetic rubber materials.
  • Polymers made from renewable raw materials such as polylactic acid (PLA), polyhydroxybutyric acid, polyhydroxyvaleric acid or polybutylene succinate are also preferred.
  • the aforementioned polymers can be in the form of fresh goods or as recycled materials.
  • the present invention also relates to a plastic composition containing or consisting of at least one plastic and at least one phenolically substituted sugar derivative, the sugar derivative having a base body derived from a sugar, and at least one substituent according to general formula I.
  • R 1 and R 2 are identical or different on each occurrence and are selected from the group consisting of hydrogen and linear or branched alkyl radicals, with the proviso that at least one radical R 1 or R 2 is not hydrogen,
  • X is an alkylene group with 1 to 18 carbon atoms or a chemical bond
  • Y is a group selected from the group consisting of the following groupings where the grouping X is attached to the terminus shown on the left of the deten groupings Y is bonded, and wherein the base of the phenolically substituted sugar derivative derived from a sugar has at least 3 unsubstituted hydroxyl groups and / or the base of the phenolic substituted sugar derivative derived from a sugar has at least 4 carbon atoms and at least 2, preferably at least 3 unsubstituted ones Has hydroxyl groups.
  • the plastic composition can preferably also contain at least one additive selected from the group consisting of UV absorbers, light stabilizers, metal deactivators, costabilizers, filler deactivators, antiozonants, nucleating agents, anti-nucleating agents, impact strength improvers, plasticizers, lubricants, rheology modifiers, chain extenders, thixotropic agents optical brightening agents, antimicrobial agents, antistatic agents, slip agents, antiblocking agents, coupling agents, crosslinking agents, anti-crosslinking agents, hydrophilizing agents, hydrophobizing agents, adhesion promoters, dispersants, compatibilizers, oxygen scavengers, acid scavengers, propellants, anti-odor agents, anti-odor agents, antifoaming agents, antioxidants Contain fillers, reinforcing agents and mixtures thereof.
  • at least one additive selected from the group consisting of UV absorbers, light stabilizers, metal deactivators, costabilizers, filler deactivators, antio
  • the plastic composition preferably also contains at least one additive selected from the group consisting of a) acid scavengers ("antiacids”) are salts of one, two, three or four-valued metals, preferably alkali, alkaline earth metals, aluminum or zinc, in particular formed with Fatty acids, such as calcium stearate, magnesium stearate, zinc stearate, aluminum stearate, calcium laurate, calcium behenate, calcium lactate, calcium stearoyl-2-lactate, Other classes of suitable acid scavengers are Hydrotalcites, in particular synthetic hydrotalcites based on aluminum, magnesium and zinc, hydrocalumites, zeolites, alkaline earth oxides, in particular calcium oxide and magnesium oxide, and zinc oxide, alkaline earth carbonates, in particular calcium carbonate, magnesium carbonate and dolomite and hydroxides, in particular brucite (magnesium hydroxide),
  • antiacids are salts of one, two, three or four-valued metals, preferably al
  • Suitable light stabilizers are, for example, compounds based on 2- (2 'hydroxyphenyl) benzotriazoles, 2-hydroxybenzophenones, esters of benzoic acids, acrylates, oxamides, and 2- (2-hydroxyphenyl) -l, 3,5-NEN Triazi-.
  • Suitable 2- (2 'hydroxyphenyl) benzotriazoles are for example 2- (2'-hy- roxy-5'-methylphenyl) benzotriazole, 2- (3', 5'-di-tert-butyl-2'-hydroxyphenyl) - benzotriazole , 2- (5'-tert-butyl-2'-hydroxyphenyl) benzotriazole, 2- (2'-hydroxy-5'- (l, l, 3,3-tetramethylbutyl) phenyl) benzotriazole, 2- (3 ', 5'-Di-tert-butyl-2'-hydroxyphenyl) -5-chlorobenzotriazole, 2- (3'-tert-butyl-2'-hydroxy-5'-methylphenyl-5-chlorobenzotriazole, 2- ( 3'-sec-butyl-5'-te / t-butyl-2'-hydroxyphenyl) benzotriazole, 2- (2'-hydroxy-4'-octy
  • Suitable 2-hydroxybenzophenones are, for example, 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-hydroxybenzophenones.
  • Suitable acrylates are, for example, ethyl a-cyano-ß, ß-diphenyl acrylate, isooctyl-a-cyano-ß, ß-diphenyl acrylate, methyl a-carbomethoxycinnamate, methyl a-cyano-ß-methyl-p-methoxycinnamate, Butyl ⁇ -cyano- ⁇ -methyl-p-methoxycinnamate, methyl- ⁇ -carbomethoxy-p-methoxycinnamate and N- ( ⁇ -carbomethoxy- ⁇ -cyanovinyl) -2-methylindoline.
  • Suitable esters of benzoic acids are, for example, 4-tert-butylphenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoyl resorcinol, bis (4-tert-butylbenzoyl) resorcinol, benzoyl resorcinol, 2,4-di-tert-butylphenyl-3,5-di-tert- butyl-4-hydroxybenzoate, hexadecyl-3,5-di-tert-butyl-4-hydroxybenzoate, octadecyl-3,5-di-tert-butyl-4-hydroxybenzoate, 2-methyl-4,6-di- tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate.
  • Suitable oxamides are, for example, 4,4'-dioctyloxyoxanilide, 2,2'-diethoxy-oxanilide, 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 its mixtures 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.
  • Suitable 2- (2-hydroxyphenyl) -1, 3,5-triazines are, for example, 2,4,6-tris (2-hydroxy-4-octyloxyphenyl) -1, 3,5-triazine, 2- (2-hydroxy -4-octyloxyphenyl) -4,6- bis (2,4-dimethylphenyl) -1, 3,5-triazine, 2- (2,4-dihydroxyphenyl) -4,6-bis (2,4-dimethylphenyl ) -1, 3,5-triazine, 2,4-bis (2-hydroxy-4-propyloxyphenyl) -6- (2,4-dimethylphenyl) -1, 3,5-triazine, 2- (2- Hydroxy-4-octyloxyphenyl) -4,6-bis (4-methyl-phenyl-1,3,5-triazine, 2- (2-hydroxy-4-dodecyloxyphenyl) -4,6-bis (2,4-dimethyl - phen
  • Suitable metal deactivators are, for example, N, N'-diphenyloxamide, N-
  • metal activators are:
  • Suitable hindered amines are, for example, l, l-bis (2,2,6,6-tetramethyl-
  • 4-piperidyl) succinate bis (1,2,2,6,6-pentamethyl-4-piperidyl) sebacate, bis (l- octyloxy-2,2,6,6-tetramethyl-4-piperidyl) sebazate, bis (1,2,2,6,6-pentamethyl-4-piperidyl) -n-butyl-3,5-di-tert-butyl -4-hydroxybenzylmalonate, the condensation product of 1- (2-hydroxyethyl) -2,2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid, linear or cyclic condensation products of N, N'-bis (2.2 , 6,6-tetramethyl-4-piperidyl) hexamethylenediamine and 4-tert-octylamino-2,6-di-chloro-1,3,5-triazine, tris (2,2,6,6-tetramethyl-4 -piperidyl) nitrilotriacetate,
  • the structures given above also include the sterically hindered NH, N-alkyl such as N-methyl or N-octyl, the N-alkoxy derivatives such as N-methoxy or N-octyloxy, the cycloalkyl derivatives such as N- cyclohexyloxy and the N- (2-hydroxy-2-methylpropoxy) analogs.
  • Preferred hindered amines also have the following structures:
  • Preferred oligomeric and polymeric hindered amines have the following structures:
  • n 3 to 100 in each case.
  • Suitable dispensing agents are, for example:
  • Polyacrylates for example copolymers with long-chain side groups, polyacrylate block copolymers, alkylamides: for example N, N'-1,2-ethanediylbisoctadecanamide, sorbitan esters, for example monostearyl sorbitan esters, titanates and zirconates, reactive copolymers with functional groups, for example polypropylene-co-acrylic acid, polypro - pylene-co-maleic anhydride, polyethylene-co-glycidyl methacrylate, polystyrene-alt-maleic anhydride-polysiloxanes: e.g.
  • Suitable costabilizers are also polyols, in particular alditols or cyclitols.
  • Polyols are, for example, pentaerythritol, dipentaerythritol, tripentaerythritol, short-chain polyether polyols or short-chain polyester polyols, and hyper-branched polymers / oligomers or dendrimers with alcohol groups, for example
  • the at least one alditol is preferably selected from the group consisting of threitol, erythritol, galactitol, mannitol, ribitol, sorbitol, xylitol, arabitol, isomalt, lactitol, maltitol, altritol, iditol, maltotritol and hydrogenated oligo- and polysaccharides with polyol End groups and mixtures thereof.
  • the at least one preferred alditol is particularly preferably selected from the group consisting of erythritol, mannitol, isomalt, maltitol and mixtures thereof.
  • heptitols and octitols meso-glycero-allo-heptitol, D-glycero-D-altro-heptitol, D-glycero-D-manno-heptitol, meso-glycero-gulo-heptitol, D-glycero D-galacto-heptitol (Perseitol), D-glycero-D-gluco-heptitol, L-glycero-D-gluco heptitol, D-erythro-L-galacto-octitol, D-threo-L-galacto-octitol.
  • the at least one cyclitol can be selected from the group consisting of inositol (myo, scyllo-, D-chiro-, L-chiro-, muco-, neo-, allo-, epi- and cis-inositol), 1,2 , 3,4-tetrahydroxycyclohexane, 1, 2,3,4, 5-pentahydroxycyclohexane, quercitol, viscumitol, bornesitol, conduritol, ononitol, pinitol, pinpollitol, quebrachitol, ciceritol, quinic acid, shikimic acid and valienol, myo being preferred -inositol (myo-inositol).
  • inositol myo, scyllo-, D-chiro-, L-chiro-, muco-, neo-, allo-, epi- and cis-inos
  • Suitable nucleating agents are, for example, talc, alkali or alkaline earth salts of monofunctional and polyfunctional carboxylic acids such as benzoic acid, succinic acid, adipic acid, e.g. sodium benzoate, zinc glycerolate, aluminum hydroxy bis (4-tert-butyl) benzoate, benzylidene sorbitols such as 1, 3: 2,4-bis (benzylidene) sorbitol or l, 3: 2,4-bis (4-methylbenzylidene) sorbitol, 2,2 '-me- Thylen-bis- (4,6-di-tert-butylphenyl) phosphate, as well as trisamides and diamides such as trimesic acid tri-cyclohexylamides, trimesic acid tri (4-methylcyclohexyl amide), trimesic acid tri (tert-butyl amide), N, N ' , N "
  • Suitable anti-nucleation agents are azine dyes such as nigrosine.
  • Suitable flame retardants are, for example: a) Inorganic flame retardants such as Al (OH) 3, Mg (OH) 2, AIO (OH), MgCC> 3, sheet silicates such as montmorillonite or sepiolite, unmodified or organically modified, double salts such as Mg- Al silicates, POSS (Polyhedral Oligomeric Silsesquioxane) compounds, huntite, hydromagnite or halloysite as well as Sb2Ü3, Sb 2 0s, M0O3, zinc stannate, zinc hydroxystannate,
  • Inorganic flame retardants such as Al (OH) 3, Mg (OH) 2, AIO (OH), MgCC> 3, sheet silicates such as montmorillonite or sepiolite, unmodified or organically modified, double salts such as Mg- Al silicates, POSS (Polyhedral Oligomeric Silsesquioxane) compounds, huntite, hydromagnite or halloysite as well as Sb
  • Nitrogen-containing flame retardants such as melamine, melamine, melam, melon, melamine derivatives, melamine condensation products or melamine salts, benzoguanamine, polyisocyanurates, allantoin, phosphacenes, in particular melamine cyanurate, melamine phosphate, dimelamine phosphate, melamine pyrophosphate, such as melamine phosphate phosphate, melamine polyphosphate, melamine polyphosphate, melamine polyphosphate, melamine polyphosphate, melamine polyphosphate, melamine polyphosphate, melamine polyphosphate, melamine polyphosphate, melamine polyphosphate, melamine polyphosphate, melamine polyphosphate, melamine polyphosphate, for example, melamine polyphosphate, for example melamine condensation products or melamine condensation products , Melamine zinc phosphate, melamine magnesium phosphate and the corresponding pyrophosphates and polyphosphates, poly-
  • Radical formers such as alkoxyamines, hydroxylamine esters, azo compounds, dicumyl or polycumyl, hydroxyimides and their derivatives such as hydroxyimide esters or hydroxyimide ethers
  • Phosphorus-containing flame retardants such as red phosphorus, phosphates such as resorcinol diphosphate, bisphenol A diphosphate and their oligomers, triphenyl phosphate, ethylenediamine diphosphate, phosphinates such as salts of hypophosphorous acid and its derivatives such as alkyl phosphine phosphine or aluminum phosphine phosphine salts such as zinc phosphine or diethyl phosphine salts , Aluminum phosphite, aluminum phosphonate, phosphonate esters, oligomeric and polymeric derivatives of methane phosphonic acid, 9,10-dihydro-9-oxa-10-phosphorylphenanthrene-10-oxide (DOPO) and their substituted compounds,
  • DOPO 9,10-dihydro-9-oxa-10-phosphorylphenanthrene-10-oxide
  • Halogen-containing flame retardants based on chlorine and bromine such as polybrominated diphenyloxides, such as decabromodiphenyloxide, tris (3-bromo-2,2-bis (bromomethyl) propyl phosphate, tris (tribromoneopentyl) phosphate, tetrabromophthalic acid, l, 2-bis (tribromophenoxy) ethane, hexabromocyclododecane, brominated diphenylethane, tris (2,3-dibromopropyl) isocyanurate, ethylene bis (tetrabromophthalimide), tetrabromobisphenol A, brominated polystyrene, brominated polybutadiene - Rol-brominated polybutadiene copolymers, brominated polyphenylene ether, brominated epoxy resin, polypentabromobenzyl acrylate, possibly in combination with Sb2Ü3
  • Sulfur-containing compounds such as elemental sulfur, disulfides and polysulfides, thiuram sulfide, dithiocarbamates, mercaptobenzothiazole and sulfenamides,
  • antidrip agents such as polytetrafluoroethylene
  • Silicon-containing compounds such as polyphenylsiloxanes
  • Carbon modifications such as carbon nanotubes (CNT) or graphs, as well as combinations or mixtures thereof.
  • Suitable azo compounds is for example in M. Aubert et. al. Macromol. Be. Closely. 2007, 292, 707-714 or in WO 2008101845, the production 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. Rod. 2012, 97, 948-954.
  • the synthesis of iminoxytriazines is described in WO 2014/064064.
  • radical formers to be used are selected from the group consisting of
  • R 3 represents hydrogen or an optionally substituted alkyl, cycloalkyl, aryl, heteroaryl or acyl radical, in particular a C1 to C4 alkyl radical,
  • R 4 represents an alkoxy, aryloxy, cycloalkoxy, aralkoxy or acyloxy radical
  • Z represents hydrogen or an optionally substituted alkyl, cycloalkyl, aryl, heteroaryl or acyl radical, where the two radicals Z can also form a closed ring, which is optionally replaced by ester, ether, amine, Amide, carboxy or urethane groups can be substituted,
  • R 5 denotes an alkyl, cycloalkyl or aryl radical
  • R 6 is identical or different on each occurrence and denotes a linear or branched alkyl radical
  • R 7 is identical or different on each occurrence and denotes hydrogen or a linear or branched alkyl radical
  • R 8 is identical or different on each occurrence and denotes an alkyl, alkoxy, aryloxy, cycloalkyloxy, aralkoxy or acyloxy radical,
  • R 7 has the meaning given above, is preferably methyl, d) and / or polycumyl according to the structural formula shown below
  • R 7 has the meaning given above, is preferably methyl, and 2 ⁇ n ⁇ 100.
  • N-alkoxyamines of the structure indicated are: 1-cyclohexyloxy-2,2,6,6-tetramethyl-4-octadecylaminopiperidine; Bis (1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate; 2,4-bis [(l-cyclohexyloxy- 2.2.6.6-Tetramethylpiperidin-4-yl) butylamino] -6- (2-hydroxyethylamino-S-triazine; bis (l-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) adipate; 2, 4-bis [(l-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) butylamino] -6-chloro-S-triazine; l- (2-hydroxy-2-methylpropoxy) -4- Hydroxy-2,2,6,6-te
  • n 1-15, such as, for example, disterarylhydroxylamine.
  • RI and R2 are preferably identical or different and are selected from linear or branched C1-C6-alkyl and / or aryl;
  • Ri alkyl
  • R2 alkyl
  • M Al or Zn.
  • a particularly preferred example of a phosphinate are the commercially available Exolit OP (RTM) products from Clariant SE.
  • phosphorus-containing flame retardants are metal salts of hypophosphorous acid with a structure according to the formula
  • Met is a metal selected from groups I, II, III and IV of the Periodic Table of the Elements, and n is a number from 1 to 4 which corresponds to the charge of the corresponding metal ion Met.
  • Met n + is Na + ,
  • phosphorus-containing flame retardants are phosphonates or phosphonic acid diaryl esters with a structure according to the following formula:
  • Corresponding structures can also be in the form of phosphonate oligomers, polymers and copolymers.
  • Linear or branched phosphonate oligomers and polymers are known from the prior art.
  • branched phosphonate oligomers and polymers reference is made to US patents US
  • Phophonate are for example under the trade name Nofia (RTM) from FRX Polymers available.
  • phosphorus-containing flame retardants are compounds based on oxaphosphorine oxide and their derivatives with, for example, the following structures:
  • Products based on oxophosphorine oxide are, for example, on the market under the trade name Ukanol (RTM) from Schill und Seilacher GmbH. Further compounds can for example according to the patent specifications WO 2013020696, WO 2010135398, W003070736, W02006084488, WO
  • phosphorus-containing flame retardants are cyclic phosphonates with a structure according to one of the following formulas:
  • a 1 and A 2 independently represent a substituted or unsubstituted, straight-chain or branched alkyl group with 1 to 4 carbon atoms, substituted or unsubstituted benzyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl and where A 3 and A 4 are independently methyl or ethyl and A 5 is a straight-chain or branched alkyl group having 1 to 4 carbon atoms or a phenyl or benzyl group, each of which can have up to 3 methyl groups.
  • Cyclic phosphonates are, for example, from Thor GmbH under the
  • phosphacenes especially polymeric phosphacenes.
  • SPB-100 commercially available from Otsuka Chemicals under the name SPB-100, for example.
  • Nitrogen-containing flame retardants are phosphacenes, especially polymeric phosphacenes.
  • SPB-100 commercially available from Otsuka Chemicals under the name SPB-100, for example.
  • Preferred nitrogen-containing flame retardants are melamine polyphosphate, melamine cyanurate, melamine metal phosphates, poly- [2,4- (piperazin-1,4-yl) -6-
  • Particularly preferred flame retardants are halogen-free and are the following compounds:
  • Suitable fillers and reinforcing materials are, for example, synthetic or natural materials such as calcium carbonate, silicates, glass fibers, glass spheres (solid or hollow), talc, mica, kaolin, barium sulfate, metal oxides and metal hydroxides, carbon black, graphite, carbon nanotubes, graphene, wood flour or fibers from natural products such as cellulose or synthetic fibers.
  • Further suitable fillers are hydrotalcites or zeolites or sheet silicates such as montmorillonite, bentonite, beidelite, mica, hectorite, saponite, ver miculite, ledikite, magadite, lllite, kaolinite, wollastonite, attapulgite.
  • Suitable pigments can be of an inorganic or organic nature.
  • Inorganic pigments are, for example, titanium dioxide, zinc oxide, zinc sulfide, iron oxide, ultramarine, carbon black, organic pigments are, for example, anthraquinones, anthanthrones, benzimidazolones, quinacridones, diketopyrrolopyrroles, dioxazines, indanthrones, isoindolinones, azo compounds, perylenes, phthalocyanines or azo compounds Pyranthrones.
  • Further suitable pigments are effect pigments based on metal or pearlescent pigments based on metal oxide.
  • Suitable lubricants and processing aids are, for example, polyethylene waxes, polypropylene waxes, salts of fatty acids such as calcium stearate, zinc stearate or salts of montan waxes, amide waxes such as erucic acid amide or oleic acid amides, fluoropolymers, silicones or neoalkoxy titanates and zirconates.
  • Suitable optical brighteners are, for example, bisbenzoxazoles, phenylcuma rine or bis (styryl) biphenyls and especially optical brighteners of the formulas:
  • Suitable filler deactivators are, for example, polysiloxanes, polyacrylates, in particular block copolymers such as polymethacrylic acid-polyalkylene oxide or polyglycidyl (meth) acrylates and their copolymers, e.g. with styrene, and epoxides e.g. of the following structures:
  • Suitable antistatic agents are, for example, ethoxylated alkylamines, fatty acid esters, alkyl sulfonates and polymers such as polyether amides.
  • Suitable antiozonants are the above-mentioned amines such as N, N'-diisopropyl-p-phenylenediamine, N, N'-di-sec-butyl-p-phenylenediamine, N, N'-bis (1,4-dimethylpentyl) -p-phenylenediamine, N, N'-dicyclohexyl-p-phenylenediamine, N-isopropyl-N'-phenyl-p-phenylenediamine, N- (1,3-dimethylbutyl) -N'-phenyl-p- phenylenediamine, N- (1-methylheptyl) -N'-phenyl-p-phenylenediamine, N-cyclohexyl-N'-phenyl-p-phenylenediamine
  • Suitable rheology modifiers e.g. for the production of controlled rheology polypropylene (CR-PP) are, for example, peroxides, alkoxyamine esters, oxyimidesulfonic acid esters and in particular the following structures:
  • Suitable additives for increasing the molecular weight of polycondensation polymers are diepoxides, bis-oxazolines, bis-oxazolones, bis-oxazines, diisocyanates, dianhydrides, bis-acyllactams, bis-maleimides, dicyanates, carbodiimides.
  • Other suitable chain extenders are polymeric compounds such.
  • Suitable additives for increasing the electrical conductivity are, for example, the aforementioned antistatic agents, soot and carbon compounds such as carbon nanotubes and graphene, metal powder such as copper powder and conductive polymers such as Polypyrroles, polyanilines and polythiophenes.
  • Suitable additives for increasing the thermal conductivity are, for example, aluminum nitrides and boron nitrides.
  • Suitable infrared-active additives are, for example, aluminum silicates, hydrotalcites or dyes such as phthalocyanines or anthraquinones.
  • Suitable mold release agents are, for example, silicones, soaps and waxes such as montan waxes.
  • Suitable impact modifiers are, for example, ethylene copolymers with acrylates, methacrylates and / or ethylenically unsaturated carboxylic acids, which can be completely or partially neutralized, for example with zinc, or copolymers of ethylene, propylene and dienes, and core-shell particles, for example of polybutyl acrylate and polymethyl methacrylate.
  • Compatibilizers or compatibilizers are used, for example, in thermodynamically immiscible blends or also in recycled mixtures and contain structural elements of the respective blend components that are mixed.
  • Suitable compatibilizers for polyolefin mixtures are, for example, olefin block copolymers consisting of ethylene, propylene and alpha-olefins such as, for example. 1-octene.
  • compatibilizers especially for compatibilizing polar, such as PET or polyamides, and non-polar, such as PP or PE polymers are, for example, polypropylene-g-maleic anhydride, polyethylene-g-maleic anhydride, polypropylene-g-acrylic acid, polyethylene-g-acrylic acid, poly (ethylene-co-maleic anhydride), SBS-g-maleic anhydride or SEBS-g-maleic anhydride.
  • Suitable crosslinking agents are, for example, peroxides such as dialkyl peroxides, alkylaryl peroxides, peroxyesters, peroxycarbonates, diacylproxides, peroxyketals, silanes such as, for example, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltriacetoxysilane, vinyltris (2-methoxyethimoxy) silane, 3-methoxyethylethyltrisylane, vinyldoxymethyltris (2-methoxyethimoxy) silane, 3-methoxyethyl-tri-methoxy-tri-methoxy-methyl propane or ethylene-vinylsilane copolymers.
  • peroxides such as dialkyl peroxides, alkylaryl peroxides, peroxyesters, peroxycarbonates, diacylproxides, peroxyketals
  • silanes such as, for example, vinyltrimethoxysilane, vinyltriethoxysilane,
  • Suitable prodegradants are additives that break down a polymer in Accelerate or control the environment in a targeted manner.
  • Examples are transition metal fatty acid esters, for example of manganese or iron, which accelerate oxidative and / or photooxidative degradation, for example of polyolefins, or enzymes which induce hydrolytic degradation, for example of aliphatic polyesters.
  • Suitable chemical blowing agents include azo compounds such as azodicarbonamide, sulfonyl semicarbazides such as p-Toluolsulfonylsemi- carbazide, tetrazoles such as 5-phenyltetrazole, hydrazides such as p-Toluolsulfonylhydra- zid, 4,4 '-Oxibis (benzenesulfonyl) hydrazide, N-nitroso compounds such as N, N' -Di- nitrosopentamethylenetetramine or carbonates such as sodium hydrogen carbonate or zinc carbonate.
  • azo compounds such as azodicarbonamide
  • sulfonyl semicarbazides such as p-Toluolsulfonylsemi- carbazide
  • tetrazoles such as 5-phenyltetrazole
  • hydrazides such as p
  • Suitable slip agents are, for example, amide waxes such as erucic acid amide or oleic acid amide.
  • Suitable antiblocking agents are, for example, silica, talc or zeolites.
  • Suitable anti-fogging additives are, for example, ethoxylated sorbitan esters, ethoxylated fatty acid alcohols or ethoxylated alkylamine esters.
  • Suitable biocides are, for example, quaternary ammonium salts or silver salts, colloidal silver or silver complexes or natural product derivatives such as Chitosan
  • Suitable aldehyde scavengers are amines, hydroxylamines, polyvinyl alcohol, zeolites or cyclodextrins
  • suitable formaldehyde scavengers are melamine derivatives such as benzoguanamine or urea derivatives such as allantoin.
  • Suitable odor-binding or odor-preventing substances are silicates such as calcium silicate, zeolites or salts of hydroxy fatty acids such as zinc cricene enolate.
  • Suitable marking agents are, for example, fluorescent dyes or rare earths.
  • the present invention further relates to a method for stabilizing plastics against oxidative, thermal and / or actinic degradation, in which at least one phenolically substituted sugar derivative, the sugar derivative having a base substance derived from a sugar, and at least one substituent according to general formula I.
  • R 1 and R 2 are identical or different on each occurrence and are selected from the group consisting of hydrogen and linear or branched alkyl radicals, with the proviso that at least one radical R 1 or R 2 is not hydrogen,
  • X is an alkylene group with 1 to 18 carbon atoms or a chemical bond
  • Y is a group selected from the group consisting of the following groupings where the group X is bound to the terminus shown on the left of the groupings Y shown above, and where the base of the phenolically substituted sugar derivative derived from a sugar has at least 3 unsubstituted hydroxyl groups and / or the base of the phenolically substituted one derived from a sugar Sugar derivative has at least 4 carbon atoms and at least 2, preferably at least 3 unsubstituted hydroxyl groups, is incorporated into a plastic.
  • the phenolic substituted sugar derivative according to the general formula I reference is made to the statements made above.
  • the additive according to the invention which can be present as a powder, liquid, oil, compacted, on a carrier material, as granules, solution or flakes, is preferably mixed with the polymer to be stabilized, the polymer matrix is transferred into the melt and then cooled.
  • a carrier material as granules, solution or flakes
  • these can be added to the polymers separately, in the form of liquids, powders, granules or compacted products or together with the additive composition according to the invention as described above.
  • additive composition and any additional additives are incorporated into the plastic by customary processing methods, the polymer being melted and mixed with the additive composition according to the invention and any further additives, preferably by mixers, kneaders and extruders.
  • Preferred processing machines are extruders such as single-screw extruders, twin-screw extruders, planetary roller extruders, ring extruders, co-kneaders, which are preferably equipped with vacuum degassing. Processing can take place under air or, if necessary, under inert gas conditions.
  • additive compositions according to the invention can be produced and introduced in the form of so-called masterbatches or concentrates which, for example, contain 10-90% of the compositions according to the invention in a polymer.
  • the invention further relates to a molding compound or a molded part, producible from a plastic composition according to the invention as described above, in particular in the form of injection molded parts, foils, films, lacquers, coatings, foams, fibers, cables, pipes, profiles, hollow bodies pern, ribbons, membranes, e.g. geomembranes, lubricants, colorants and / or adhesives that are manufactured via extrusion, injection molding, blow molding, calendering, pressing processes, spinning processes and / or rotomoulding, e.g. for the electrical industry, for the construction industry, for Transport industry, for medical applications, for household and electrical appliances, for vehicle parts, for consumer goods, for packaging, for furniture and / or for textiles.
  • Another area of application are paints, paints and coatings, as well as fats and oils.
  • oils and fats they can be based on mineral oils, vegetable fats or animal fats or oils, fats or waxes based on e.g. synthetic esters.
  • Vegetable oils and fats are, for example, palm oil, olive oil, rapeseed oil, linseed oil, soybean oil, sunflower oil, castor oil, animal fats are, for example, fish oils or beef tallow.
  • the compounds according to the invention can also be used as stabilizers for lubricants, hydraulic oils, motor oils, turbine oils, gear oils, metal processing fluids or as lubricating greases.
  • These mineral or synthetic lubricants are primarily based on hydrocarbons.
  • antioxidants according to the invention can be used to stabilize monomers in order to prevent premature polymerization or oxidation if necessary, e.g. for styrene or acrylates or for the stabilization of polyols in polyurethane synthesis.
  • the present invention also relates to a stabilizer composition for stabilizing plastics against oxidative, thermal and / or actinic degradation, consisting of at least one phenolic substituted sugar derivative, the sugar derivative having a base derived from a sugar, and at least one substituent according to the general formula I.
  • a stabilizer composition for stabilizing plastics against oxidative, thermal and / or actinic degradation consisting of at least one phenolic substituted sugar derivative, the sugar derivative having a base derived from a sugar, and at least one substituent according to the general formula I.
  • R 1 and R 2 are identical or different on each occurrence and are selected from the group consisting of hydrogen and linear or branched alkyl radicals, with the proviso that at least one radical R 1 or R 2 is not hydrogen,
  • X is an alkylene group with 1 to 18 carbon atoms or a chemical bond
  • Y is a group selected from the group consisting of the following groupings where the group X is bound to the terminus shown on the left of the groupings Y shown above, and where the base of the phenolically substituted sugar derivative derived from a sugar has at least 3 unsubstituted hydroxyl groups and / or the base of the phenol derived from a sugar Lisch substituted sugar derivative has at least 4 carbon atoms and at least 2, preferably at least 3 unsubstituted hydroxyl groups, and at least one primary antioxidant and / or at least one secondary antioxidant.
  • the present invention relates to a phenolically substituted sugar derivative, the sugar derivative having a base structure derived from a sugar, as well as at least one substituent according to formula I in general
  • R 1 and R 2 are identical or different on each occurrence and are selected from the group consisting of hydrogen and linear or branched alkyl radicals, with the proviso that at least one radical R 1 or R 2 is not hydrogen,
  • X is an alkylene group with 1 to 18 carbon atoms or a chemical bond
  • Y is a group selected from the group consisting of the following groupings
  • the group X is bound to the terminus shown on the left of the groupings Y shown above, and where the base of the phenolically substituted sugar derivative derived from a sugar has at least 3 unsubstituted hydroxyl groups and / or the base of the phenol derived from a sugar Lisch substituted sugar derivative has at least 4 carbon atoms and at least 2, preferably at least 3 unsubstituted hydroxyl groups.
  • a commercially available polypropylene (Moplen HP 500N, Lyondell Basell Industries) was homogenized in a powder-powder mixture with the specified stabilizers and in a twin-screw microextruder (MC 5, manufacturer DSM) for 30 minutes at 200 ° C and 90 revolutions per minute and recorded the decrease in force.
  • the force is a direct measure of the molecular weight of polypropylene; the lower the decrease, the higher the stabilization effect.
  • a further improvement in the processing stability is achieved by adding 0.1% primary antioxidant (pentaerythritol tetrakis [3- (3rd)) to 0.2% of the 3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid ester of mannitol , 5-di-tert-butyl-4-hydroxyphenyl) propionate) or 0.1% secondary antioxidant (tris- (2,4-di-tert-butylphenyl) phosphite) can be added.
  • primary antioxidant penentaerythritol tetrakis [3- (3rd)
  • secondary antioxidant tris- (2,4-di-tert-butylphenyl) phosphite
  • the monofunctional derivatives with more than 80% monosubstitution are obtained by transesterifying 3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid methyl ester with erythritol, myo-inositol and sorbitol.
  • Recycled polyolefin consisting of a PE / PP mixture, 210 ° C

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)

Abstract

La présente invention concerne l'utilisation d'au moins un dérivé du sucre à substitution phénolique comme stabilisant de matières organiques, en particulier de matières plastiques, contre la dégradation oxydative, thermique et/ou actinique. La présente invention concerne en outre une composition de matières plastiques correspondante, un procédé de stabilisation de matières plastiques, une matière à mouler ou une pièce moulée, ainsi qu'un dérivé du sucre à substitution phénolique.
EP20737440.6A 2019-07-08 2020-07-07 Utilisation de dérivés du sucre à substitution phénolique comme stabilisants, composition de matières plastiques, procédé de stabilisation de matières plastiques et dérivés du sucre à substitution phénolique Pending EP3997164A1 (fr)

Applications Claiming Priority (2)

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DE102019210040.6A DE102019210040A1 (de) 2019-07-08 2019-07-08 Verwendung von phenolisch substituierten Zuckerderivaten als Stabilisatoren, Kunststoffzusammensetzung, Verfahren zur Stabilisierung von Kunststoffen sowie phenolisch substituierte Zuckerderivate
PCT/EP2020/069153 WO2021005075A1 (fr) 2019-07-08 2020-07-07 Utilisation de dérivés du sucre à substitution phénolique comme stabilisants, composition de matières plastiques, procédé de stabilisation de matières plastiques et dérivés du sucre à substitution phénolique

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