EP3997164A1

EP3997164A1 - Use of phenolically substituted sugar derivatives as stabilisers, plastic composition, method for stabilising plastics and phenolically substituted sugar derivatives

Info

Publication number: EP3997164A1
Application number: EP20737440.6A
Authority: EP
Inventors: Rudolf Pfaendner
Original assignee: Fraunhofer Gesellschaft zur Forderung der Angewandten Forschung eV
Current assignee: Fraunhofer Gesellschaft zur Forderung der Angewandten Forschung eV
Priority date: 2019-07-08
Filing date: 2020-07-07
Publication date: 2022-05-18
Also published as: CN114341246A; US20220267568A1; WO2021005075A1; JP2022539472A; KR20220032579A; DE102019210040A1

Abstract

The present invention relates to the use of at least one phenolically substituted sugar derivative as a stabiliser of organic materials, in particular plastics, against oxidative, thermal and/or actinic degradation. The present invention also relates to a corresponding plastic composition, to a method for stabilising plastics, to a moulding compound or a moulded part as well as a phenolically substituted sugar derivative.

Description

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. In addition, 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. A general distinction is made between primary antioxidants, which can react directly with oxygen-containing free radicals or C-radicals, and 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. Usually, primary and secondary antioxidants are often combined in practice, which leads to a synergistic effect.

Since some of the stabilizers used today can also have disadvantages (e.g. hydrolysis stability of phosphites and the release of phenol, odor of sulfur-containing stabilizers, discoloration of amines, etc.), new stabilizer solutions are still being sought.

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. To increase the effectiveness and to achieve a high concentration of phenol groups with a simultaneous low concentration of ineffective components of a molecule, the polyols such as pentaerythritol are used, the 4 alcohol groups of which are fully esterified dig. Pentaerythritol tetrakis (3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate, available for example under the trade name Irganox ™ 1010, has become one of the most important standard stabilizers. In principle, 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.

As already mentioned, phenolic antioxidants are usually combined in a synergistic way with other stabilizers. In exceptional cases, however, stabilizers are also known which have both primary and secondary antioxidant structures in one molecule, e.g.

In a separate application (WO 2019063550) it was found that combinations of alditols or cyclitols with primary or secondary antioxidants are particularly suitable for stabilizing recycled plastics. Here, too, it is advantageous according to the invention to use mixtures of different stabilizers.

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

Formula I where 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,

a grouping 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 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.

As "stabilizer" or "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. Surprisingly, it could be established according to the invention that the stabilizing effect, as defined above, can be achieved with substances which have a basic structure based on renewable raw materials.

In particular, 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.

In particular, 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.

For example, the alditol can have the following empirical formulas

HIGH [CH (OH)] _n CH OH,

Ri-OCH ₂ [CH (OH)] _n CH ₂ OH, or

HOCH ₂ [CH (OH)] _n [CH (ORi)] CH ₂ OH with n = 2-6, preferably n = 3-5, where Ri is an optionally substituted sugar residue. 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.

In the event that an amino sugar forms the basic structure of the compound according to the invention according to formula I, 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 α, -diamino-α, -dideoxyalditols such as, for example, 1,6-di-amino-1,6-dideoxy sorbitol.

The 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.

In particular, there are high stabilizing effects when 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, and 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- (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-methyl-phenol, 2,4-dimethyl-6- (l'-methylundec-l'-yl) phenol, 2,4-dimethyl-6- (l'-methylheptadec-l'-yl) phenol, 2,4-dimethyl-6- (l'-methyltridec-l'-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, 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-nonylphenol], 4,4'-methylenebis (2,6-di-tert-butylphenol, 4,4'-methylenebis (6-tert-butyl-2-methylphenol), l, l-bis (5-tert-butyl-4-hydroxy-2-methylphenyl) butane, 2,6-bis (3-tert-butyl-5-methyl- 2-hydroxybenzyl) -4-methylphenol, l, l, 3-tris (5-tert-butyl-4-hydroxy-2-methylphenyl) butane, l, l-bis (5-tert-butyl-4-hydroxy-2 -methylphenyl) -3-n-dodecylmercaptobutane, ethylene glycol bis [3,3-bis (3'-tert-butyl-4'-hydroxyphenyl) butyrate], bis (3-tert-butyl-4-hydroxy-5 -methylphenyl) dicyclopentadiene, bis [2- (3'-tert-butyl-2'-hydroxy-5'-methylbenzyl) -6-tert-butyl-4-methylphenyl] terephthalate, 1,1-bis- (3 , 5-dimethyl-2-hydroxyphenyl) butane, 2,2-bis (3,5-di-tert-butyl-4-hydroxyphenyl) propane, 2,2-bis (5-tert-butyl-4-hydroxy- 2-methyl-phenyl) -4-n-dodecylmercaptobutane, 1,1,5-tetra (5-tert-butyl-4-hydroxy-2-methylphenyl) pentane;

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) isocyanurate, 2,4,6-tris (3,5-di-tert-butyl-4-hydroxphenylethyl) -1, 3,5-triazine, l , 3,5-Tris (3,5-di-te / T-butyl-4-hydroxyphenylpropionyl) hexahydro-1,3,5-triazine, 1,3,5-tris (3,5-dicyclohexyl-4 hydroxybenzyl isocyanurate;

Benzyl phosphonates, such as dimethyl-2,5-di-tert-butyl-4-hydroxybenzylphosphonate, diethl-3,5-di-te / T-butyl-4-hydroxybenzylphosphonate, dioctadecyl

3.5-di-te / T-butyl-4-hydroxybenzylphosphonate, dioctadecyl-5-te / T-butyl-4-hydroxy-3-methylbenzylphosphonate, the calcium salt 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 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] octane;

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] octane, 3,9-bis [2- {3- (3-tert-butyl - 4-hydroxy-5-methylphenyl) propionyloxy} -1, l-dimethylethyl] -2,4,8,10-tetraoxaspiro [5.5] undecane;

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);

Ascorbic acid (vitamin C).

Particularly preferred phenolic antioxidants are the following structures:

where n is an integer in the aforementioned compounds and is between 2 and 10

Other preferred 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-cryptoxanthin, lutein, zeaxanthin or astaxanthin

Further stabilizers, especially for polyamides, 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:

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-methyl-pentyl) -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-isopropyl-N'-phenyl-p-phenylenediamine, N- (1,3-dimethylbutyl) -N'-phenyl- p-phenylenediamine, N- (1-methylheptyl) -N'- phenyl-p-phenylenediamine, N-cyclohexyl-N'-phenyl-p-phenylenediamine, 4- (p-toluenesulfamoyl) diphenylamine, N, N'- Dimethyl-N, N'-di-sec-butyl-p-phenylenediamine, diphenylamine, N-allyldiphenylamine, 4-isopropoxydiphenylamine, N-phenyl-1-naphthylamine, N- (4-tert-octylphenyl) -l-naphthylamine , N-phenyl-2-naphthylamine, octylated diphenylamine, e.g. p, p'-di-tert-octyldiphenylamine, 4-n-butylaminophenol, 4-butyrylaminophenol, 4-nonanoylaminophenol, 4-dodecanoylaminophenol, 4-octadecanoylaminophenol, bis ( 4-methoxyphenyl) amine, 2,6-di-tert-butyl-4-dimethylaminomethyl-phen ol, 2,4'-diamino diphenyl methane, 4,4'-diaminodiphenyl methane, N, N, N ', N'-tetra-methyl-4,4'-diaminodiphenyl methane, 1,2-bis [(2-methyl- phenyl) amino] ethane, 1,2-bis (phenylamino) propane, (o-tolyl) biguanide, bis [4- (l ', 3'-dimethylbutyl) phenyl] amine, tert-octylated N-phenyl-l -naphthylamine, a mixture of mono- and dialkylated tert-butyl / tert-octyldiphenylamines, a mixture of mono- and dialkylated nonyldiphenylamines, a mixture of mono- and dialkylated dodecyldiphenylamines, a mixture of mono- and dialkylated isopropyl / isohexyl-diphenylamines a mixture of mono- and dialkylated tert-butyldiphenylamines, 2,3-dihydro-3,3-dimethyl-4H-1,4-benzothiazine, phenothiazine, a mixture of mono- and dialkylated tert-butyl / tert-octylphenothiazines , a mixture of mono- and dialkylated tert-octylphenothiazines, N-allylphenothiazine, N, N, N ', N'-tetraphenyl-1,4-diaminobut-2-ene and mixtures or combinations thereof.

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'-phenyl-p-phenylenediamine, N- (l-methylheptyl) -N'-phenyl-p-phenylenediamine , N-cyclohexyl-N'-phenyl-p-phenylenediamine

Particularly preferred aminic antioxidants are the structures:

where n is an integer and is between 3 and 100.

Further preferred 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 ™ EP (Sl Group) according to the formula:

Ri

R ₂ - N - * -0

LH3

Ri, 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) -5,7-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 also contain phosphite groups such as e.g.

Another suitable group of 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) pentaerythritol diphosphite, diisodecyloxypentaerythritol diphosphite, bis (2,4-di-tert-butyl -6-methylphenyl) pentaerythritol diphosphite, bis (2,4,6-tris (te / t-butylphenyl) pentaerythritol diphosphite, tristearylsorbitol triphosphite, tetrakis (2,4-di-tert-butylphenyl) -4,4'-biphenylenediphosphonite, 6-isooctyloxy - 2,4,8,10-tetra-tert-butyl-12H-dibenz [d, g] -l, B, 2-dioxaphosphocin, bis (2,4-di-tert-butyl-6-methylphenyl) methylphosphite, Bis (2,4-di-tert-butyl-6-methylphenyl) ethyl phosphite, 6-fluoro-2,4,8,10-tetra-tert-butyl-12-methyl-dibenz [d, g] -

1.3.2-dioxaphosphocin, 2,2'2 "-nitrilo [triethyltris (3,3", 5,5'-tetra-tert-butyl-l, l'-biphenyl-2,2'-diyl) phosphite], 2-ethylhexyl (3,3 ', 5,5'-tetra-tert-butyl-l, l'-biphenyl-2,2'-diyl)) phosphite, 5-butyl-5-ethyl-2- (2, 4,6-tri-tert-butylphenoxy) -

1.3.2-dioxaphosphirane.

Particularly preferred phosphites / phosphonites are:

where n = 3-100.

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.

In particular, it has proven to be advantageous if, based on 91 to 99.94 parts by weight, preferably 98.5 to 99.91 parts by weight, of the plastic

(A) 0.02 to 3 parts by weight, preferably 0.03 to 0.5 parts by weight, of the at least one phenolic substituted sugar derivative, and

(B) 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,

LLDPE, VLDPE, ULDPE, MDPE, HDPE, UHMWPE), metallocene-PE (m-PE), polypropylene, polyisobutylene, poly-4-methyl-pentene-1, polybutadiene, polyisoprene, such as natural rubber (NR), polycyclooctene , Polyalkylene-carbon monoxide copolymers, and copolymers in the form of statistical or block structures such as polypropylene-polyethylene (EP), EPM or EPDM with, for example, 5-ethylidene-2-norbornene as comonomer, ethylene-vinyl acetate (EVA), ethylene Acrylic esters, such as ethylene-butyl acrylate, ethylene-acrylic acid and their salts (ionomers), and terpolymers such as ethylene-acrylic acid-glycidyl (meth) acrylate, graft polymers such as polypropylene-graft-maleic anhydride, polypropylene-graft Acrylic acid, polyethylene-graft-acrylic acid, polyethylene-polybutyl acrylate-graft-maleic anhydride and blends such as LDPE / LLDPE or long-chain branched polypropylene copolymers which are produced with alpha-olefins as comonomers such as, for example, 1-butene , 1-hexene, 1-octene or 1-octadecene

b) 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 copolymers such as styrene on butadiene, maleic anhydride on SBS or SEBS, and graft copolymers made 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 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) d) Polymers of unsaturated esters such as polyacrylates and polymethacrylates such as polymethyl methacrylate (PMMA), polybutyl acrylate, polylauryl acrylate, polystearyl acrylate, polyglycidyl acrylate, polyglycidyl methacrylate, polyacrylonitrile, polyacrylamides, copolymers such as polyacrylonitrile

e) Polymers of unsaturated alcohols and derivatives, such as polyvinyl alcohol, polyvinyl acetate, polyvinyl butyral, polyallyl phthalate, polyalyl melamine

f) polyacetals such as polyoxymethylene (POM) or copolymers with e.g.

Butanal,

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,

j) 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. made 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 PA-6 and PA 6.6 or blends of Polyamides and polyolefins such as PA / PP

k) polyimides, polyamide-imides, polyetherimides, polyesterimides, poly (ether) ketones, polysulfones, polyether sulfones, polyarylsulfones, polyphenylene sulfides, polybenzimidazoles, polyhydantoins,

L) 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

n) cellulose derivatives such as cellulose nitrate, cellulose acetate, cellulose propionate, cellulose butyrate,

o) 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,

p) Phenolic resins such as phenol-formaldehyde resins, urea-formaldehyde resins, melamine-formaldehyde resins,

q) unsaturated polyester resins made from unsaturated dicarboxylic acids and diols with vinyl compounds e.g. styrene, alkyd resins,

r) Silicones, e.g. based on dimethylsiloxanes, methyl-phenyl-siloxanes or diphenylsiloxanes, e.g. terminated with vinyl groups

s) and also mixtures, combinations or blends of two or more of the aforementioned polymers.

If the 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.

If the 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.

Furthermore, the polymers specified under a) to r) can have both amorphous and (partially) crystalline morphologies.

If necessary, the polyolefins mentioned under a) can also be crosslinked, e.g. crosslinked polyethylene, which is then referred to as X-PE.

Furthermore, 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.

Formula I where 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.

With regard to the phenolic substituted sugar derivatives according to formula I, reference is made to the above embodiments, which also apply without restriction to the plastic composition according to the invention.

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.

Possible additives are listed below, but they are not to be understood as exhaustive.

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),

b) light stabilizers, preferably light stabilizers from the group of hindered amines,

c) dispersants, as well as

d) mixtures thereof.

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'-octyloxyphenyl) 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'-hydroxy-5 '- (2-octyloxycarbonylethyl) phenyl) -5-chlorobenzotriazole, 2- (3'-te / t-butyl-5' - [2- (2-ethylhexyloxy) carbonyl- ethyl] -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'-th rt-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- (l, l, 3,3-tetramethylbutyl) -6-benzotriazol-2-ylphenol]; the product of the transesterification of 2- [3'-tert-butyl-5 '- (2-methoxycarbonylethyl) -2'-hydroxyphenyl] -2H-benzotriazole with polyethylene glycol 300; [R— CH2CH2— COO— CH2CH2 + 2 where R = 3 '-tert- Butyl-4'-hydroxy-5'-2H-benzotriazol-2-ylphenyl, 2- [2'-hydroxy-3 '- (a, a-dimethylbenzyl) -5' - (l, l, 3.3 -tetramethylbutyl) phenyl] benzotriazole, 2- [2'-hydroxy-3'- (1,1,3,3-tetramethylbutyl) -5 '- (a, a-dimethylbenzyl) phenyl] benzotriazole.

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 α-cyano-β-methyl-p-methoxycinnamate, methyl-α-carbomethoxy-p-methoxycinnamate and N- (β-carbomethoxy-β-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 - phenyl) -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- (2nd -hydroxy-3-octyloxypropyloxy) phenyl] -4,6-bis (2,4-dimethyl) -1, 3,5-triazine, 2- [4- (dodecyloxy / tridecy-

5 loxy-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] -l, 3,5-triazine, 2- (2-hyd-

10 roxyphenyl) -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.

Suitable metal deactivators are, for example, N, N'-diphenyloxamide, N-

15 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, isophthaloyl dihydrazide, sebacoyl bisphenyl hydrazide, N, N'-diacetyladipoyl dihydrazide, N, N'-bis (salicyloyl) oxylyldihydrazide, N, N'-bis (salicyloyl) dihydrazide-picyloyl

20th

Particularly preferred as metal activators are:

25th

BO

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, tetrakis (2, 2,6,6-tetra-methyl-4-piperidyl) -l, 2,3,4-butanetetracarboxylate, l, l '- (l, 2-ethanediyl) bis (3,3,5,5-tetramethylpiperazinon), 4-benzoyl-2,2,6,6-tetramethylpiperidine, 4-stearyloxy-2,2,6,6-tetramethylpiperidine, linear or cyclic condensation products from N, N'-bis (2,2,6,6-tetramethyl-4-piperidyl) hexamethylenediamine and 4-morpholino-2,6-dichloro-1,3,5-triazine the reaction product of 7,7,9,9-tetramethyl -2-cycloundecyl-1-oxa-3,8-di-aza-4-oxospiro- [4,5] decane and epichlorohydrin.

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:

In the compounds mentioned above, n is 3 to 100 in each case.

Another suitable light stabilizer is Hostanox NOW (manufacturer: Clariant SE) with the following general structure:

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. dimethylsilanediol-ethylene oxide copolymer, polyphenylsiloxane copolymer, amphiphilic copolymers: e.g. polyethylene-block-group-polyethylene denoxide, dendrimers, e.g. drimere of the following structures: 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.

Examples of other suitable sugar alcohols are 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. In particular, 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).

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 ^" -l, 3,5-benzene triyl tris (2,2-dimethyl propanamide) or 2, 6-naphthalenedicarboxylic acid dicyclohexylamide.

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,

b) 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, 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- [2,4- (piperazin-1,4-yl) -6- (morpholin-4- yl) -l, 3,5-triazine], ammonium polyphosphate, melamine borate, melamine hydrobromide,

c) Radical formers, such as alkoxyamines, hydroxylamine esters, azo compounds, dicumyl or polycumyl, hydroxyimides and their derivatives such as hydroxyimide esters or hydroxyimide ethers

d) 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,

e) 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 and / or Sb ₂ 0s,

f) Borates such as zinc borate or calcium borate, possibly on a carrier material such as silica

g) Sulfur-containing compounds such as elemental sulfur, disulfides and polysulfides, thiuram sulfide, dithiocarbamates, mercaptobenzothiazole and sulfenamides,

h) antidrip agents such as polytetrafluoroethylene,

i) Silicon-containing compounds such as polyphenylsiloxanes,

j) Carbon modifications such as carbon nanotubes (CNT) or graphs, as well as combinations or mixtures thereof. Particularly suitable flame retardants are radical formers preferably selected from the group consisting of N-alkoxyamines, -CC- radical formers, radical formers with azo groups (-N = N-), radical formers with hydrazine groups (-NH-HN-), radical formers with hydrazone groups (> C = N-NH-), radical formers with azine groups (> C = NN = C <), radical formers with triazene groups (-N = NN <) or from iminoxytriazines.

The preparation of 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.

In particular, radical formers to be used are selected from the group consisting of

a) N-alkoxyamines according to the structural formula shown below

in which

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,

E stands for an alkoxy, aryloxy, cycloalkyloxy, aralkoxy or acyloxy radical, b) Azo compounds according to the structural formulas shown below

in which

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, and

R ^{8 is} identical or different on each occurrence and denotes an alkyl, alkoxy, aryloxy, cycloalkyloxy, aralkoxy or acyloxy radical,

c) Dicumyl according to the structural formula shown below

where R ^{7 has} the meaning given above, is preferably methyl, d) and / or polycumyl according to the structural formula shown below

where R ^{7 has} the meaning given above, is preferably methyl, and 2 <n <100.

Typical examples of the aforementioned 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-tetramethylpiperidine; 1- (2-hydroxy-2-methylpropoxy) -4-oxo-2,2,6,6-tetramethylpiperidine; 1- (2-hydroxy-2-methylpropoxy) - 4-octadecanoyloxy-2,2,6,6-tetramethylpiperidine; bis (l- (2-hydroxy-2-methylpropoxy) -2,2,6,6-tetramethylpiperidin-4-yl) sebacate; bis (l- (2-Hydroxy-2-methylpropoxy) -2,2,6,6-tetramethylpiperidin-4-yl) adipate; 2,4-bis {N- [1- (2-hydroxy-2-methylpropoxy) -2.2 , 6,6-tetramethylpiperidin-4-yl] -N-butylamino} -6- (2-hydroxyethylamino) -S-triazine); 4-piperidinol,

2.2.6.6-tetramethyl-1- (undecyloxy) -4,4'-carbonate; the reaction product of 2,4-bis [(l-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) butylamino] -6-chloro-S-triazine with N, N'-bis (3-aminopropylethylenediamine) ; the oligomer compound, which is the condensation product of 4,4'-hexamethylene bis (amino-2,2,6,6-tetramethylpiperidine) and 2,4-dichloro-6 - [(l-cyclohexyloxy-

2.2.6.6-Tetramethyl-4-yl) butylamino] -S-triazine, closed at the ends with 2-chloro-4,6-bis (dibutylamino) -S-triazine; aliphatic hydroxylamine such as e.g.

in which n = 1-15, such as, for example, disterarylhydroxylamine.

Some of the above-mentioned compounds are commercial products and are traded under the following trade names: FLAMESTAB NOR 116 (RTM), TINUVIN NOR 371 (RTM), IRGATEC CR 76 (RTM) from BASF SE, Hostavin NOW (RTM) from Clariant or ADK Stab LA 81 (RTM) from Adeka. Dicumyl and Polycumyl are commercial products available, for example, from United Initiators. a) Phosphorus-containing flame retardants, e.g. phosphinates of the following structures:

where RI and R2 are preferably identical or different and are selected from linear or branched C1-C6-alkyl and / or aryl; M is selected from the group consisting of Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Ce, Bi, Sr, Mn, Li, Na, K, Zn and / or a protonated nitrogen base, preferably 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; x = 1-4, preferably 1 or 2. In a particularly preferred embodiment, Ri = alkyl, R2 = alkyl and M = Al or Zn.

A particularly preferred example of a phosphinate are the commercially available Exolit OP (RTM) products from Clariant SE.

Further preferred phosphorus-containing flame retardants are metal salts of hypophosphorous acid with a structure according to the formula

where 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. For example, Met ^{n +} is Na ⁺ ,

Ca ²⁺ , Mg ²⁺ , Zn ²⁺ , Ti ⁴⁺ or Al ³⁺ , with Ca ²⁺ , Zn ²⁺ and Al ^{3+ being} particularly preferred.

Some of the above-mentioned salts of hypophosphorous acid are commercially available, e.g. under the name Phoslite (RTM) from Italmatch Chemicals.

Another preferred group of phosphorus-containing flame retardants are phosphonates or phosphonic acid diaryl esters with a structure according to the following formula:

where Rs, and Rio = H, alkyl, preferably C1-C4, Rg = C1-C4 alkyl, u = 1-5st and v = 1-5.

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. For branched phosphonate oligomers and polymers, reference is made to US patents US

US 2,716,101, US 3,326,852, US 4,328,174, US 4,331,614, US 4,374,971, US

4 415 719, US 5 216 113, US 5 334 692, US 3 442 854, US 6 291 630 B1, US 6 861 499 B2 and US 7816486 B2 are referred to. For phosphonate oligomers, reference is made to US patent applications US 2005/0020800 A1, US 2007/0219295 A1 and US 2008/0045673 A1. With respect to linear phosphonate oligomers and polymers, see US Patent Documents, US 3,946,093, US

3,919,363, US 6,288,210 B1, US 2,682,522 and US 2,891,915 are referred to.

Phophonate are for example under the trade name Nofia (RTM) from FRX Polymers available.

Another preferred group of phosphorus-containing flame retardants are compounds based on oxaphosphorine oxide and their derivatives with, for example, the following structures:

where M is a metal selected from the second, third, twelfth or thirteenth group of the Periodic Table of the Elements, x = 2 or 3, n> 10, m = 0-25, R = H, halogen or an aliphatic or an aromatic radical with 1-32 carbon atoms and Ri = H, C1-C6 alkyl or phenyl.

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

2006084489, W02011000019, WO2013068437, WO2013072295.

Further suitable phosphorus-containing flame retardants are cyclic phosphonates with a structure according to one of the following formulas:

where 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

Trade names Aflammit (RTM) are commercially available or can be produced in accordance with EP 2450401.

Further synergistic phosphorus-containing flame retardants are phosphacenes, especially polymeric phosphacenes. A corresponding product is commercially available from Otsuka Chemicals under the name SPB-100, for example. b) Nitrogen-containing flame retardants

Preferred nitrogen-containing flame retardants are melamine polyphosphate, melamine cyanurate, melamine metal phosphates, poly- [2,4- (piperazin-1,4-yl) -6-

(morpholin-4-yl) -1, 3,5-triazine] and ammonium polyphosphate. These compounds are commercial products and are available under the trade names Melapur (RTM) from BASF SE, Budit (RTM) from Budenheim Chemische Fabrik, Exolit (RTM) from Clariant, Safire (RTM) from Huber Chemicals or MCA PPM Triazine from MCA Technologies GmbH . c) Preferred sulfur-containing flame retardants are, for example, the following compounds

Particularly preferred flame retardants are halogen-free and are the following compounds:

Al (OH) ₃ , Mg (OH) _2,

n = 2-20 with n = 3 to 100 ⁿ with each R = alkyl, phenyl and n = 3 to 20

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 (chain extenders) are diepoxides, bis-oxazolines, bis-oxazolones, bis-oxazines, diisocyanates, dianhydrides, bis-acyllactams, bis-maleimides, dicyanates, carbodiimides. Other suitable chain extenders are polymeric compounds such. B. polystyrene-polyacrylate-polyglycidyl (meth) acrylate copolymers, polystyrene-maleic anhydride copolymers and polyethylene-maleic anhydride copolymers.

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. Other 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.

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.

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.

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. With regard to 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. As an alternative to this, it is also possible to introduce the additive in a molten state into a polymer melt.

In the event that further constituents are added to the polymer composition, 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.

The above-described 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.

Furthermore, the 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.

If the organic materials are 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.

Furthermore, the 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. Formula I where 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.

Finally, 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

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.

With regard to the special and preferred embodiment of the phenolically substituted sugar derivative according to the invention, reference is made to the statements made above.

The present invention is described in more detail with reference to the following Ausführungsbei, game without restricting the invention thereto. Embodiment

To test the effect of the stabilizers according to the invention, 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.

The addition of 0.1 to 0.3% of a 3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid ester of mannitol (> 90% monosubstituted), produced by transesterification of the 3- (3,5-di -te / t-butyl-4-hydroxyphenyl) propionic acid methyl ester with mannitol, leads to increased processing stabilization, ie to a higher residual force, compared to a polypropylene without addition or to a polypropylene that contains only mannitol. 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.

In an analogous manner, 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.

The 3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid ester of mannitol (> 90% monosubstituted) was also added to the following polymers at the specified processing temperatures in a concentration of 0.2%, 30 minutes processed and the force curve determined:

HDPE, 230 ° C

LLDPE, 200 ° C

Polystyrene, 230 ° C

ABS, 230 ° C

PC / ABS, 250 ° C PET, 260 ° C (myo-inositol derivative)

PA-6.6, 260 ° C (myo-inositol derivative)

Recycled polyolefin, consisting of a PE / PP mixture, 210 ° C

In all cases, a stabilizing effect with the additives according to the invention in contrast to the starting polymers without additives can be demonstrated by a constant force profile over the test time.

Claims

1. Use of at least one phenolically substituted sugar derivative, the sugar derivative having a basic structure derived from a sugar, and at least one substituent according to general formula I.

Formula I.

in which

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

H H

where the group X is bound to the terminus shown on the left of the groupings Y shown above, and where the sugar-derived base of the phenolic substituted sugar derivative has at least 3 unsubstituted hydroxyl groups and / or the base of the sugar-derived phenolic substituted sugar derivative at least - has at least 4 carbon atoms and at least 2, preferably at least 3 unsubstituted hydroxyl groups,

as a stabilizer of organic materials, especially plastics, against oxidative, thermal and / or actinic degradation.

2. Use according to claim 1, characterized in that the base body derived from a sugar is a monosaccharide, an oligosaccharide or a polysaccharide with at least 4 carbon atoms.

3. Use according to one of the preceding claims, characterized in that the phenolically substituted sugar derivative 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.

4. Use according to one of the preceding claims, characterized in that the basic body derived from a sugar is at least one alditol, a cyclitol, a sugar acid or an amino sugar with at least 4 carbon atoms.

5. Use according to the preceding claim, characterized in that the at least one alditol has the empirical formula

HIGH [CH (OH)] n CH OH,

Ri-OCH ₂ [CH (OH)] _n CH ₂ OH, or

HIGH ₂ [CH (OH)] n [CH (ORi)] CH ₂ OH

with n = 2-6, preferably n = 3-5, where Ri is an optionally substituted sugar residue.

6. Use according to one of the two preceding claims, characterized in that

the at least one alditol is selected from the group consisting of threitol, erythritol, galactitol, mannitol, ribitol, sorbitol, xylitol, arabitol, isomalt, lactitol, maltitol, maltotritol and hydrogenated oligo- and polysaccharides with polyol end groups and mixtures thereof, the at least an alditol is preferably selected from the group consisting of erythritol, mannitol, isomalt, maltitol and mixtures thereof, the at least one cyclitol is selected from the group consisting of inositol, quercitol, viscumitol, bornesitol, conduritol, ononitol, pinitol, pinpollitol, ciceritol, Quebrachitol, quinic acid, shikimic acid and valienol, the at least one cyclitol preferably being myo-inositol,

the at least one sugar acid is an aldonic acid such as 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 and mixtures or glucaric acid and combinations thereof, and / or

the at least one amino sugar is a mono- or diamino sugar and is in particular selected from the group consisting of 1-amino-1-deoxy-alditols, such as, for example, 1-amino-1-deoxy-galactitol, 1-amino-1-deoxy-mannitol , 1-amino-l-deoxy-sorbitol, 1-amino-l-deoxy-maltitol or a, (j-diamino-a, (j-dideoxyalditols, such as l, 6-diamino-1,6-dideoxysorbitol .

7. Use according to any one of the preceding claims, characterized in that R ¹ and R ^{2 are} identical or different and are selected from the group consisting of tert-butyl and methyl.

8. Use according to one of the preceding claims, characterized in that the phenolically substituted sugar derivative is selected from the group consisting of the following molecules

as well as mixtures and combinations thereof.

9. Use according to one of the preceding claims, characterized in that the at least one phenolically substituted sugar derivative in a total amount of 0.01 to 10 wt .-%, preferably 0.05 to 5 wt .-%, particularly preferably 0, 1 to 3% by weight, based on the plastic, is used.

10. Use according to one of the preceding claims, characterized in that the at least one phenolically substituted sugar derivative is used in combination with a primary and / or secondary antioxidant which differs from the at least one phenolically substituted sugar derivative, the at least one preferably being selected from the group consisting of phenolic antioxidants, amines, lactones and mixtures here of, and

the at least one secondary antioxidant is selected from the group consisting of phosphorus compounds, in particular phosphites and phosphonites, organosulfur compounds, in particular sulfides and disulfides, and mixtures thereof.

11. Use according to the preceding claim, characterized in that the at least one primary and / or secondary antioxidant in a total amount, based on the total amount of the min least one phenolic substituted sugar derivative of 0.01 to 5 parts by weight, preferably of 0.02 to 3 parts by weight, particularly before given from 0.05 to 2 parts by weight. Is used.

12. Use according to one of the preceding claims, characterized in that based on 91 to 99.94 parts by weight, preferably 98.5 to 99.91 parts by weight of the plastic

(A) 0.02 to 3 parts by weight, preferably 0.03 to 0.5 parts by weight of the min least one phenolically substituted sugar derivative, and

(B) 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

be introduced.

13. Use according to one of the preceding claims, characterized in that the plastic is a thermoplastic and is in particular selected from the group consisting of

a) Polymers made from olefins or diolefins, such as polyethylene, in particular LDPE, LLDPE, VLDPE, ULDPE, MDPE, HDPE and UHMWPE, metallocene PE (m-PE), polypropylene, polyisobutylene, poly-4-methyl-pentene-1 , Polybutadiene, polyisoprene, polycyclooc- ten, polyalkylene-carbon monoxide copolymers, as well as corresponding copolymers in the form of random or block structures such as polypropylene-polyethylene (EP), EPM or EPDM, ethylene-vinyl acetate (EVA), ethylene Acrylic esters, such as ethylene-butyl acrylate, ethylene-acrylic acid-glycidyl acrylate, and correspond to graft polymers such as polypropylene-g-maleic anhydride, polypropylene-g-acrylic acid and polyethylene-g-acrylic acid, b) polystyrene, polymethylstyrene, polyvinylnaphthalene, 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-acrylate (ASA), styrene-ethylene, styrene-maleic acid an ydride polymers including corresponding graft copolymers such as styrene on butadiene, maleic anhydride on SBS or SEBS, as well as graft copolymers made of methyl methacrylate, styrene butadiene and ABS (MABS),

c) Polymers of unsaturated esters such as polyacrylates and polymethacrylates such as polymethyl methacrylate (PMMA), polybutyl acrylate, polylauryl acrylate, polystearyl acrylate, polyacrylonitrile, polyacrylamides, and corresponding copolymers such as polyacrylonitrile-polyalkyl acrylate,

d) Polymers made from unsaturated alcohols and derivatives, such as polyvinyl alcohol, polyvinyl acetate, polyvinyl butyral,

e) Polyacetals, such as polyoxymethylene (POM), and correspond to copolymers, such as copolymers with butanal,

f) Polyphenylene oxides and blends of these with polystyrene or polyamides,

g) Polymers of cyclic ethers such as polyethylene glycol, polypropylene glycol, polyethylene oxide, polypropylene oxide,

h) Polyurethanes made from hydroxy-terminated polyethers or polyesters and aromatic or aliphatic isocyanates, in particular linear polyurethanes, polyureas,

i) Polyamides such as polyamide-6, 6.6, 6.10, 4.6, 4.10, 6.12, 12.12, polyamide 11, polyamide 12 and (partially) aromatic polyamides such as polyphthalamides, e.g. made from terephthalic acid and / or isophthalic acid and aliphatic diamines or from aliphatic dicarboxylic acids such as adipic acid or sebacic acid and aromatic diamines such as 1,4- or 1,3-diaminobenzene,

j) polyimides, polyamide-imides, polyetherimides, polyesterimides, poly (ether) ketones, polysulfones, polyether sulfones, polyarylsulfones, polyphenylene sulfide, polybenzimidazoles, polyhydantoins, k) Polyesters from aliphatic or aromatic dicarboxylic acids and diols or from hydroxycarboxylic acids such as, for example, polyethylene terephthalate (PET), polybutylene terephthalate (PBT), polypropylene terephthalate, polyethylene naphthylate, poly-1,4-dimethylocyclohexane phthalate, polyhydroxybenzoilchthalate, polyhydroxy phthalic acid ,

L) Polycarbonates, polyester carbonates and blends of these such as PC / ABS, PC / PBT, PC / P ET / P BT,

m) cellulose derivatives, such as cellulose nitrate, cellulose acetate, cellulose propionate, cellulose butyrate,

n) and mixtures, combinations or blends of two or more of the aforementioned polymers,

wherein the polymers mentioned can be available as fresh goods or as recycled materials.

14. Plastic composition containing or consisting of

at least one plastic, as well

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

Formula I.

in which

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

H H

where the group X is bound to the terminus shown on the left of the groupings Y shown above, and where the sugar-derived base of the phenolically substituted sugar derivative has at least 3 unsubstituted hydroxyl groups and / or the base of the phenolically substituted sugar derivative derived from a sugar has at least 4 carbon atoms and at least 2, preferably at least 3, unsubstituted hydroxyl groups.

15. Plastic composition according to the preceding claim,

characterized in that the plastic composition additionally contains at least one additive selected from the group consisting of UV absorbers, light stabilizers, metal deactivators, costabilizers, filler deactivators, antiozonants, nucleating agents, antinucleating agents, impact strength improvers, plasticizers, lubricants, rheology modifiers , Thixotropic agents, chain extenders, optical brighteners, antimicrobial agents, antistatic agents, slip agents, antiblocking agents, coupling agents, crosslinking agents, anti-crosslinking agents, hydrophilicizing agents, hydrophobizing agents, adhesion promoters, dispersing agents, compatibilizers, defoaming agents, defoaming agents, propellants, acid scavengers , Marking agents, anti-fogging agents, fillers, reinforcing agents and mixtures thereof.

16. Plastic composition according to one of the two preceding claims, characterized in that the plastic together Settlement additionally contains at least one additive which is selected from the group consisting of

a) Acid scavengers, preferably salts of one, two, three or four-valent 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 stearate, calcium lactate, Calcium stearoyl-2-lactate, hydrotalcites, especially synthetic hydrotalcites based on aluminum, magnesium and zinc, hydrocalumites, zeolites, alkaline earth oxides, in particular special calcium oxide and magnesium oxide, alkaline earth metal carbonates, in particular calcium carbonate, magnesium carbonate and dolomite, and hydroxides, in particular brucite,

c) dispersants, as well as

d) mixtures thereof.

17. 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 body derived from a sugar, and at least one substituent according to general formula I

Formula I.

in which

Y is a group selected from the group consisting of the following groupings

H H

where the group X is bound to the terminus shown on the left of the groupings Y shown above, and where the sugar-derived base of the phenolically substituted sugar derivative has at least 3 unsubstituted hydroxyl groups and / or the base of the phenolically substituted sugar derivative derived from a sugar has at least 4 carbon atoms and at least 2, preferably at least 3 unsubstituted hydroxyl groups,

is incorporated into a plastic.

18. Molding compound or molded part can be produced from a plastic composition according to one of claims 14 to 16, in particular in the form of injection molded parts, foils, films, paints, coatings, foams, fibers, cables, pipes, profiles, hollow bodies, tapes, membranes, for example Geomembranes, lubricants, colorants and / or adhesives that are manufactured via extrusion, injection molding, blow molding, Ka landrieren, pressing processes, spinning processes and / or rotomoulding, e.g. for the electrical industry, for the construction industry, for the transport industry, for medical applications, for households - and electrical devices, for vehicle parts, for consumer articles, for packaging, for furniture and / or for textiles.

19. Stabilizer composition for stabilizing plastics against oxidative, thermal and / or actinic degradation, consisting of

at least one phenolically substituted sugar derivative, the sugar derivative having a base body derived from a sugar has, and at least one substituent according to general formula I

Formula I.

in which

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

H H

and

at least one primary antioxidant and / or at least one secondary antioxidant.

20. 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

Formula I.

in which

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

H H

where the group X is bound to the terminus shown on the left of the groupings Y shown above, and where the sugar-derived base of the phenolically substituted sugar derivative has at least 3 unsubstituted hydroxy groups and / or the base of the phenolically substituted sugar derivative derived from a sugar at least has at least 4 carbon atoms and at least 2, preferably at least 3, unsubstituted hydroxyl groups.