DE102024207175A1 - Polymer stabilizers, stabilizer composition, stabilized polymer composition, processes for the production of polymer stabilizers, processes for stabilizing a polymer, and the use of polymer stabilizers for stabilizing polymers. - Google Patents

Abstract

Increasingly, plastics made from fossil raw materials such as petroleum or natural gas are being supplemented or replaced by plastics based on renewable raw materials obtained through biochemical processes. The question of sustainability then also arises for the plastic additives used for these plastics (and for plastics made from fossil raw materials). Therefore, there is a need for plastic additives based on renewable and readily available raw materials that are highly effective, low volatility, and compatible with polymeric substrates.

Description

Increasingly, plastics made from fossil raw materials such as petroleum or natural gas are being supplemented or replaced by plastics based on renewable raw materials obtained through biochemical processes. The question of sustainability then also arises for the plastic additives used for these plastics (and for plastics made from fossil raw materials). Therefore, there is a need for plastic additives based on renewable and readily available raw materials that are highly effective, low volatility, and compatible with polymeric substrates.

Sugar molecules such as alditols are readily available biogenic raw materials that are already used today as plastic additives in the form of stabilizers for recycled plastics ( WO2019063550 ), as costabilizers to polyphenols ( WO2020083740 ) or as metal deactivators ( WO2023198777 ) are used.

Alditols and substituted alditols are known and described in the aforementioned patent applications. Furthermore, monomeric acrylates/methacrylates have been described in JP 07316098 as dental filling materials. However, the synthesis method described there leads to a product mixture that must be separated using complex methods, e.g., chromatography. The production of the acetalized polymeric intermediate is in G. Koßmehl, J. Volkheimer, Liebigs Ann. Chem. 1991, 1079-1081 The description does not include the removal of protecting groups or use as an additive for plastics.

The next state of the art involves substituted alditols, which are used as stabilizers for recycled materials ( WO 2020/193563 ). Polymeric alditol structures in the form of polycondensation products and (meth)acrylates are also generically described there.

However, commercially available alditols such as erythritol, xylitol, or sorbitol do not meet all the aforementioned requirements regarding thermal stability, migration behavior, and/or compatibility with the respective polymers. The incorporation of alditol functionality into polymeric structures should not exhibit the aforementioned disadvantages.

The object of the present invention was therefore to develop new polymeric additives based on alditols and a corresponding manufacturing process.

This problem is solved with respect to a polymeric stabilizer having the features of claim 1, with respect to a stabilizer composition having the features of claim 11, with respect to a stabilized polymer composition having the features of claim 13, with a method for producing a polymeric stabilizer having the features of claim 16, with a method for stabilizing a polymer having the features of claim 18, and with respect to the use of a polymeric stabilizer having the features of claim 19. The respective dependent claims represent advantageous embodiments.

The present invention thus relates, according to a first aspect, to a polymeric stabilizer containing a polymer chain to which alditols and/or cyclitols are bound, wherein the polymer chain was obtained by radical polymerization.

According to the present invention, a polymer is thus provided that is produced by radical polymerization. In the radical polymerization, at least one type of monomer is used that contains the alditols and/or cyclitols, so that after completion of the radical polymerization, a polymer chain results to which the alditols and/or cyclitols are bound. Details are described explicitly below in the description of the process.

Surprisingly, it was found that the polymeric stabilizer compounds exhibit excellent stabilizing properties, particularly for other polymers. These stabilizers are partly based on renewable raw materials, such as alditols and cyclitols. Due to their polymeric structure, migration behavior can be completely avoided. The compatibility of the stabilizers according to the invention with the respective polymer systems into which they are to be incorporated can be achieved by tailoring the stabilizers to the specific polymers.

R1

ein von einem Alditol oder Cyclitol abgeleiteter Rest ist, der über ein Kohlenstoffatom gebunden ist,

R2 und R3

gleich oder verschieden sind und ausgewählt sind aus der Gruppe bestehend aus Wasserstoff sowie linearen oder verzweigten Alkylresten mit 1 bis 32 Kohlenstoffatomen, insbesondere dass R² und R³ gleich sind und je eine Methylgruppe darstellen,

A

O oder NH ist

X

eine verbrückende Gruppierung darstellt

a

1 oder 0 ist,

b

1 oder 0 ist, und

P

die Polymerkette darstellt.

A preferred embodiment provides that the polymeric stabilizer has a structure according to general formula I. where

R1

a residue derived from an alditol or cyclitol, which is bonded via a carbon atom,

R2 and R3

are the same or different and are selected from the group consisting of hydrogen and linear or branched alkyl groups with 1 to 32 carbon atoms, in particular that R ² and R ³ are the same and each represent a methyl group,

A

O or NH is

X

represents a bridging grouping

a

1 or 0,

b

1 or 0, and

P

represents the polymer chain.

c

2, 3, 4 oder 5 ist (insbesondere ist c 3 oder 5), bzw.

R4

ausgewählt ist aus der Gruppe bestehend aus Wasserstoff, -OH und -OR⁵, wobei R⁵ einen linearen oder verzweigten Alkylrest mit 1 bis 32 Kohlenstoffatomen darstellt, insbesondere Methyl ist, mit der Maßgabe, dass von allen Resten R⁴ zumindest 3 Reste R⁴ nicht Wasserstoff sind.

It is still preferred that the remainder R ¹ is selected from the group consisting of the following remainders. where

c

2, 3, 4 or 5 is (in particular, c is 3 or 5), respectively.

R4

selected is from the group consisting of hydrogen, -OH and -OR ⁵ , wherein R ⁵ represents a linear or branched alkyl group with 1 to 32 carbon atoms, in particular is methyl, with the proviso that of all R ⁴ groups at least 3 R ⁴ groups are not hydrogen.

In particular, the residues ^R1 are selected from the group consisting of the following residues.

The bridging connection X is in particular the following grouping

Preferably, the polymer chain has a repeating unit of the general formula II: wherein R ¹ , R ² , R ³ , X, a and b have the meaning specified in claim 0 and R ⁶ is the same or different in each occurrence and is selected from the group consisting of hydrogen, linear or branched alkyl group having 1 to 32 carbon atoms, in particular methyl and aromatic groups, in particular phenyl or alpha-methylphenyl.

Another preferred embodiment is characterized in that the polymeric stabilizer is a homopolymer and is formed in particular from repeating units of formula II.

It is particularly preferred that the polymeric alditol derivative is formed on the basis of arabit(ol), xylit(ol), ribit(ol) or volemitol.

Alternatively, the polymeric stabilizer is a copolymer and, in addition to the repeating unit according to general formula II, comprises at least one further repeating unit obtained by radical polymerization, wherein the at least one further repeating unit obtained by radical polymerization preferably has the following structure according to general formula III: where X, R ⁶ and b have the meanings given above.

In this case, the molar ratio of the total number of repeating units according to general formula II to the total sum of all repeating units according to general formula II and general formula III is preferably from 0.01 to 99.9, preferably 1 to 99, and particularly preferably from 5 to 95.

In particular, in formula I and formula II respectively, the residues R ² and R ³ are each methyl, A is oxygen, XC(=O)- and a and b are each 1.

Furthermore, the present invention relates to a stabilizer composition comprising or consisting of at least one polymeric stabilizer according to one of the preceding claims and at least one additive, different from the polymeric stabilizer, selected from the group consisting of primary antioxidants, secondary antioxidants, UV absorbers, light stabilizers, in particular hindered amines as light (HALS) and long-term heat stabilizers (HAS), metal deactivators, filler deactivators, antiozonants, nucleating agents, antinucleating agents, clarifiers, impact enhancers, plasticizers, lubricants, rheology or viscosity modifiers, thixotropic agents, chain extenders, processing aids, demolding aids, flame retardants, pigments, dyes, optical brighteners, antimicrobial agents, antistatic agents, slip agents, antiblocking agents, coupling agents, crosslinking agents, anticrosslinking agents, hydrophilizing agents, and hydrophobizing agents. Surface modifiers, hydrolysis stabilizers, adhesion promoters, dispersants, compatibilizers, oxygen scavengers, acid scavengers, acetaldehyde and formaldehyde scavengers, blowing agents, degradation additives (prodegradants), defoaming agents, odor traps and odor-improving substances, PVC heat stabilizers, marking agents, antifogging agents, gloss enhancers, matting agents, additives to increase electrical and/or thermal conductivity, repellents, fillers and reinforcing agents and mixtures thereof.

It is advantageous if the weight ratio of the totality of the at least one stabilizer to the total stabilizer composition is between 0.01 and 0.99, preferably between 0.2 and 0.80.

The following preferred additives are particularly suitable: Primary antioxidants act as hydrogen donors and radical scavengers, thus interrupting the radical auto-oxidation process in polymers. Suitable primary antioxidants include phenolic antioxidants, (partially) aromatic amines, hydroxylamines, and lactones.

• Alkylierte Monophenole, wie z.B. 2,6-Di-tert-butyl-4-methylphenol, 2-tert-Butyl-4,6-dimethylphenol, 2,6-Di-tert-butyl-4-ethylphenol, 2,6-Di-tert-butyl-4-n-butylphenol, 2,6-Di-tert-butyl-4-isobutylphenol, 2,6-Dicyclopentyl-4-methylphenol, 2-(α-Methylcyclohexyl)-4,6-dimethylphenol, 2,6-Dioctadecyl-4-methylphenol, 2,4,6-Tricyclohexylphenol, 2,6-Di-tert-butyl-4-methoxymethylphenol, lineare oder verzweigte Nonylphenole, wie z.B. 2,6-Dinonyl-4-methylphenol, 2,4-Dimethyl-6-(1'-methylundec-1'-yl)phenol, 2,4-Dimethyl-6-(1'-methylheptadec-1'-yl)phenol, 2,4-Dimethyl-6-(1'-methyltridec-1'-yl)phenol und Mischungen hiervon;
• Alkylthiomethylphenole, wie z.B. 2,4-Dioctylthiomethyl-6-tert-butylphenol, 2,4-Dioctylthiomethyl-6-methylphenol, 2,4-Dioctylthiomethyl-6-ethylphenol, 2,6-Didodecylthiomethyl-4-nonylphenol;
• Hydrochinone und alkylierte Hydrochinone, wie z.B. 2,6-Di-tert-butyl-4-methyoxyphenol, 2,5-Di-tert-butylhydrochinon, 2,5-Di-tert-amylhydrochinon, 2,6-Diphenyl-4-octadecyloxyphenol, 2,6-Di-tert-butylhydrochinon, 2,5-Di-tert-butyl-4-hydroxyanisol, 3,5-Di-tert-butyl-4-hydroxyanisol, 3,5-Di-tert-butyl-4-hydroxyphenylstearat, Bis(3,5-di-tert-butyl-4-hydroxylphenyl)adipat;
• Tocopherole, wie z.B. α-, β-, γ-, δ-Tocopherol und Mischungen aus diesen (Vitamin E);
• Hydroxylierte Thiodiphenylether, wie z.B. 2,2'-Thiobis(6-tert-butyl-4-methylphenol), 2,2'-Thiobis(4-octylphenol), 4,4'-Thiobis(6-tert-butyl-3-methylphenol), 4,4'-Thiobis(6-tert-butyl-2-methylphenol), 4,4'-Thiobis(3,6-di-secamylphenol), 4,4'-Bis(2,6-dimethyl-4-hydroxyphenyl)disulfid;
• Alkylidenbisphenole, wie z.B. 2,2'Methylenbis(6-tert-butyl-4-methylphenol), 2,2'-Methylenbis(6-tert-butyl-4-ethylphenol), 2,2'-Methylenbis[4-methyl-6-(α-methylcyclohexyl)phenol], 2,2'-Methylenbis(4-methyl-6-cyclhexylphenol), 2,2'-Methylenbis(6-nonyl-4-methylphenol), 2,2'-Methylenbis(4,6-di-tert-butylphenol), 2,2'-Ethylidenbis(4,6-di-tert-butylphenol), 2,2'-Ethylidenbis(6-tert-butyl-4-isobutylphe-nol), 2,2'-Methylenbis[6-(α-methylbenzyl)-4-nonylphenol], 2,2'-Methylenbis[6-(α,α-dimethylbenzyl)-4-nonylphenol], 4,4'-Methylenbis(2,6-di-tert-butylphenol, 4,4'-Methylenbis(6-tert-butyl-2-methyl-phenol), 1,1-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)butan, 2,6-Bis(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4-methylphenol, 1,1,3-Tris(5-tert-butyl-4-hydroxy-2-methylphenyl)butan, 1,1-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)-3-n-dodecylmercaptobutan, Ethylenglycol-bis[3,3-bis(3'-tert-butyl-4'-hydroxyphenyl)butyrat], Bis(3-tert-butyl-4-hydroxy-5-methylphenyl)dicyclopentadien, Bis[2-(3'-tert-butyl-2'-hydroxy-5'-methylbenzyl)-6-tert-butyl-4-methylphenyl]terephthalat, 1,1-Bis-(3,5-dimethyl-2-hydroxyphenyl)butan, 2,2-Bis(3,5-di-tert-butyl-4-hydroxyphenyl)propan, 2,2-Bis-(5-tert-butyl-4-hydroxy-2-methylphenyl)-4-n-dodecylmercaptobutan, 1,1,5,5-Tetra(5-tert-butyl-4-hydroxy-2-methylphenyl)pentan;
• O-, N-und S-Benzyl-Verbindungen, wie z.B. 3,5,3',5'-Tetra-tert-butyl-4,4'-dihydroxydibenzylether, Octadecyl-4-hydroxy-3,5-dimethylbenzylmercaptoacetat, Tridecyl-4-hydroxy-3,5-di-tert-butylbenzyl-mercaptoacetat, Tris(3,5-di-tert-butyl-4-hydroxybenzyl)amin, Bis(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-dithioterephthalat, Bis(3,5-di-tert-butyl-4-hydroxybenzyl)sulfid, Isooctyl-3,5-di-tert-butyl-4-hydroxybenzylmercaptoacetat;
• Hydroxybenzylierte Malonate, wie z.B. Dioctadecyl-2,2-bis(3,5-di-tert-butyl-2-hydroxybenzyl)-malonat, Dioctadecyl-2-(3-tert-butyl-4-hydroxy-5-methylbenzyl)malonat, Didodecylmercaptoethyl-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonat, Bis[4-(1,1,3,3-tetramethylbutyl)phenyl]-2,2-bis-(3,5-di-tert-butyl-4-hydroxybenzyl)malonat;
• Aromatische Hydroxybenzylverbindungen, wie z.B. 1,3,5-Tris(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzol, 1,4-Bis(3,5-di-tert-butyl-4-hydroxybenzyl)-2,3,5,6-tetramethylbenzol, 2,4,6-Tris(3,5-di-tert-butyl-4-hydroxybenzyl)phenol;
• Triazinverbindungen, wie z.B. 2,4-Bis(octylmercapto)-6-(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazin, 2-Octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazin, 2-Octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,3,5-triazin, 2,4,6-Tris(3,5-di-tert-butyl-4-hydroxyphe-noxy)-1,2,3-triazin, 1,3,5-Tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurat, 1,3,5-Tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanurat, 2,4,6-Tris(3,5-di-tert-butyl-4-hydroxphenylethyl)-1,3,5-tria-zin, 1,3,5-Tris(3,5-di-tert-butyl-4-hydroyphenylpropionyl)hexahydro-1,3,5-triazin, 1,3,5-Tris(3,5-dicyc-lohexyl-4-hydroxybenzyl)isocyanurat;
• Benzylphosphonate, wie z.B. Dimethyl-2,5-di-tert-butyl-4-hydroxybenzylphosphonat, Dietyhl-3,5-di-tert-butyl-4-hydroxybenzylphosphonat, Dioctadecyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonat, Di-octadecyl-5-tert-butyl-4-hydroxy-3-methylbenzylphosphonat, das Calciumsalz des Monoethylesters der 3,5-Di-tert-butyl-4-hydroxybenzylphosphonsäure;
• Acylaminophenole, wie z.B. 4-Hydroxylauranilid, 4-Hydroxystearanilid, Octyl-N-(3,5-di-tert-butyl-4-hydroxyphenyl)carbamat;
• Ester der β-(3,5-Di-tert-butyl-4-hydroxyphenyl)propionsäure mit ein-oder mehrwertigen Alkoholen, z.B. Methanol, Ethanol, n-Octanol, i-Octanol, Octadecanol, 1,6-Hexandiol, 1,9-Nonandiol, Ethylenglycol, 1,2-Propandiol, Neopentylglycol, Thiodiethylenglycol, Diethylenglycol, Triethylenglycol, Pentaerythritol, Tris(hydroxyethyl)isocyanurat, N,N'-Bis(hydroxyethyl)oxamid, 3-Thiaundecanol, 3-Thiapentadecanol, Trimethylhexandiol, Trimethylolpropan, 4-Hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octan;
• Ester der β-(5-tert-Butyl-4-hydroxy-3-methylphenyl)propionsäure mit ein-oder mehrwertigen Alkoholen, z.B. Methanol, Ethanol, n-Octanol, i-Octanol, Octadecanol, 1,6-Hexandiol, 1,9-Nonandiol, Ethylenglycol, 1,2-Propandiol, Neopentylglycol, Thiodiethylenglycol, Diethylenglycol, Triethylenglycol, Pentaerythritol, Tris(hydroxyethyl)isocyanurat, N,N'-bis(hydroxyethyl)oxamid, 3-Thiaundecanol, 3-Thiapentadecanol, Trimethylhexandiol, Trimethylolpropan, 4-Hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octan, 3,9-Bis[2-{3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy}-1,1-dimethylethyl]-2,4,8,10-tetraoxaspiro[5.5]undecan;
• Ester der β-(3,5-Dicyclohexyl-4-hydroxyphenyl)propionsäure mit ein-oder mehrwertigen Alkoholen, z.B. Methanol, Ethanol, Octanol, Octadecanol, 1,6-Hexandiol, 1,9-Nonandiol, Ethylenglycol, 1,2-Propandiol, Neopentylglycol, Thiodiethylenglycol, Diethylenglycol, Triethylenglycol, Pentaerythritol, Tris-(hydroxyethyl)isocyanurat, N,N'-bis(hydroxyethyl)oxamid, 3-Thiaundecanol, 3-Thiapentadecanol, Trimethylhexandiol, Trimethylolpropan, 4-Hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octan;
• Ester der (3,5-Di-tert-butyl-4-hydroxyphenyl)essigsäure mit ein-oder mehrwertigen Alkoholen, z.B. Methanol, Ethanol, Octanol, Octadecanol, 1,6-Hexandiol, 1,9-Nonandiol, Ethylenglycol, 1,2-Propandiol, Neopentylglycol, Thiodiethylenglycol, Diethylenglycol, Triethylenglycol, Pentaerythritol, Tris(hydroxyethyl)isocyanurat, N,N'-bis(hydroxyethyl)oxamid, 3-Thiaundecanol, 3-Thiapentadecanol, Trimethylhexandiol, Trimethylolpropan, 4-Hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octan;
• Amide der β-(3,5-Di-tert-butyl-4-hydroxyphenyl)propionsäure, wie z.B. N,N'-Bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylendiamid, N,N'-Bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)-hexamethylendiamid, N,N'-Bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylendiamid, N,N'-Bis-(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazid, N,N'-Bis[2-(3-[3,5-di-tert-butyl-4-hy-droxyphenyl]propionyloxy)ethyl]oxamid (Naugard^®XL-1, vertrieben durch Uniroyal);

Suitable synthetic phenolic antioxidants include, for example:

• Alkylated monophenols, such as 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-isobutylphenol, 2,6-Dicyclopentyl-4-methylphenol, 2-(α-methylcyclohexyl)-4,6-dimethylphenol, 2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, linear or branched nonylphenols, such as 2,6-dinonyl-4-methylphenol, 2,4-Dimethyl-6-(1'-methylundec-1'-yl)phenol, 2,4-Dimethyl-6-(1'-methylheptadec-1'-yl)phenol, 2,4-Dimethyl-6-(1'-methyltridec-1'-yl)phenol and mixtures thereof;
• alkylthiomethylphenols such as 2,4-dioctylthiomethyl-6-tert-butylphenol, 2,4-dioctylthiomethyl-6-methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol, 2,6-didodecylthiomethyl-4-nonylphenol;
• Hydroquinones and alkylated hydroquinones, such as 2,6-di-tert-butyl-4-methyloxyphenol, 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-hydroxyphenylstearate, bis(3,5-di-tert-butyl-4-hydroxylphenyl)adipate;
• Tocopherols, such as α-, β-, γ-, δ-tocopherol and mixtures of these (vitamin E);
• Hydroxylated thiodiphenyl ethers, such as 2,2'-thiobis(6-tert-butyl-4-methylphenol), 2,2'-thiobis(4-octylphenol), 4,4'-thiobis(6-tert-butyl-3-methylphenol), 4,4'-thiobis(6-tert-butyl-2-methylphenol), 4,4'-thiobis(3,6-di-secamylphenol), 4,4'-bis(2,6-dimethyl-4-hydroxyphenyl) disulfide;
• Alkylidene bisphenols, such as 2,2'-methylenebis(6-tert-butyl-4-methylphenol), 2,2'-methylenebis(6-tert-butyl-4-ethylphenol), 2,2'-methylenebis[4-methyl-6-(α-methylcyclohexyl)phenol], 2,2'-methylenebis(4-methyl-6-cyclohexylphenol), 2,2'-methylenebis(6-nonyl-4-methylphenol), 2,2'-methylenebis(4,6-di-tert-butylphenol), 2,2'-ethylidenebis(4,6-di-tert-butylphenol), 2,2'-ethylidenebis(6-tert-butyl-4-isobutylphenol), 2,2'-methylenebis[6-(α-methylbenzyl)-4-nonylphenol], 2,2'-methylenebis[6-(α,α-dimethylbenzyl)-4-nonylphenol], 4,4'-methylenebis(2,6-di-tert-butylphenol, 4,4'-methylenebis(6-tert-butyl-2-methyl-phenol), 1,1-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)butane, 2,6-Bis(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4-methylphenol, 1,1,3-tris(5-tert-butyl-4-hydroxy-2-methylphenyl)butane, 1,1-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)-3-n-dodecylmercaptobutane, Ethylene glycol bis[3,3-bis(3'-tert-butyl-4'-hydroxyphenyl)butyrate], Bis(3-tert-butyl-4-hydroxy-5-methylphenyl)dicyclopentadiene, bis[2-(3'-tert-butyl-2'-hydroxy-5'-methylbenzyl)-6-tert-butyl-4-methylphenyl] terephthalate, 1,1-bis-(3,5-dimethyl-2-hydroxyphenyl)butane, 2,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)propane, 2,2-bis-(5-tert-butyl-4-hydroxy-2-methylphenyl)-4-n-dodecylmercaptobutane, 1,1,5,5-tetra(5-tert-butyl-4-hydroxy-2-methylphenyl)pentane;
• O-, N- and S-benzyl compounds, such as 3,5,3',5'-tetra-tert-butyl-4,4'-dihydroxydibenzyl ether, octadecyl-4-hydroxy-3,5-dimethylbenzyl mercaptoacetate, tridecyl-4-hydroxy-3,5-di-tert-butylbenzyl mercaptoacetate, Tris(3,5-di-tert-butyl-4-hydroxybenzyl)amine, bis(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) dithioterephthalate, bis(3,5-di-tert-butyl-4-hydroxybenzyl) sulfide, isooctyl-3,5-di-tert-butyl-4-hydroxybenzyl mercaptoacetate;
• Hydroxybenzylated malonates, such as dioctadecyl 2,2-bis(3,5-di-tert-butyl-2-hydroxybenzyl) malonate, dioctadecyl 2-(3-tert-butyl-4-hydroxy-5-methylbenzyl) malonate, didodecyl mercaptoethyl 2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate, bis[4-(1,1,3,3-tetramethylbutyl)phenyl]-2,2-bis-(3,5-di-tert-butyl-4-hydroxybenzyl)malonate;
• Aromatic hydroxybenzyl compounds, such as 1,3,5-Tris(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene, 1,4-Bis(3,5-di-tert-butyl-4-hydroxybenzyl)-2,3,5,6-tetramethylbenzene, 2,4,6-Tris(3,5-di-tert-butyl-4-hydroxybenzyl)phenol;
• Triazine compounds, such as 2,4-bis(octylmercapto)-6-(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine, 2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine, 2-Octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,3,5-triazine, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,2,3-triazine, 1,3,5-Tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate, 1,3,5-Tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanurate, 2,4,6-Tris(3,5-di-tert-butyl-4-hydroxphenylethyl)-1,3,5-triazine, 1,3,5-tris(3,5-di-tert-butyl-4-hydrophenylpropionyl)hexahydro-1,3,5-triazine, 1,3,5-tris(3,5-dicyclohexyl-4-hydroxybenzyl)isocyanurate;
• Benzylphosphonates, such as dimethyl-2,5-di-tert-butyl-4-hydroxybenzylphosphonate, diethyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl-5-tert-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 β-(3,5-di-tert-butyl-4-hydroxyphenyl)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-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane;
• Esters of β-(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-thiaundecanol, 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}-1,1-dimethylethyl]-2,4,8,10-tetraoxaspiro[5.5]undecane;
• Esters of β-(3,5-Dicyclohexyl-4-hydroxyphenyl)propionic acid with mono- or polyhydric alcohols, 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-thiaondecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane;
• Esters of (3,5-di-tert-butyl-4-hydroxyphenyl)acetic acid with mono- 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;
• Amides of β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid, such as N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamide, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamide, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamide, N,N'-bis-(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazide, N,N'-bis[2-(3-[3,5-di-tert-butyl-4-hydroxydroxyphenyl]propionyloxy)ethyl]oxamide ( ^Naugard® XL-1, distributed by Uniroyal);

Vitamin C

Particularly favored phenolic antioxidants are: where in the aforementioned compounds n is an integer and lies between 2 and 10.

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

• N,N'-Di-isopropyl-p-phenylendiamin, N,N'-Di-sec-butyl-p-phenylendiamin, N,N'-Bis(1,4-dimethyl-pentyl)-p-phenylendiamin, N,N'-Bis(1-ethyl-3-methylpentyl)-p-phenylendiamin, N,N'-Bis(1-methyl-heptyl)-p-phenylendiamin, N,N'-Dicyclohexyl-p-phenylendiamin, N,N'-Diphenyl-p-phenylendiamin, N,N'-Bis(2-naphthyl)-p-phenylendiamin, N-Isopropyl-N'-phenyl-p-phenylendiamin, N-(1,3-Dimethyl-butyl)-N'-phenyl-p-phenylen-diamin, N-(1-Methylheptyl)-N'phenyl-p-phenylendia-min, N-Cyclohexyl-N'-phenyl-p-phenylendiamin, 4-(p-Toluolsulfamoyl)diphenylamin, N,N'-Dimethyl-N,N'-di-sec-butyl-p-phenylendiamin, Diphenylamin, N-Allyldiphenylamin, 4-Isopropoxydiphenylamin, N-Phenyl-1-naphthylamin, N-(4-tert-Octylphenyl)-1-naphthylamin, N-Phenyl-2-naphthylamin, octyliertes Diphenylamin, z.B. p,p'-Di-tert-octyldiphenylamin, 4-n-Butylaminophenol, 4-Butyrylaminophenol, 4-Nonanoylaminophenol, 4-Dodecanoylaminophenol, 4-Octadecanoylamino-phenol, Bis(4-methoxyphenyl)amin, 2,6-Di-tert-butyl-4-dimethylaminomethyl-phenol, 2,4'-Diaminodiphenylmethan, 4,4'-Diaminodiphenylmethan, N,N,N',N'-Tetra-methyl-4,4'-diaminodiphenylmethan, 1,2-Bis[(2-methyl-phenyl)amino]ethan, 1,2-Bis(phenylamino)propan, (o-Tolyl)biguanid, Bis[4-(1',3'-dimethylbutyl)phenyl]amin, tertoctyliertes N-Phenyl-1-naphthylamin, ein Gemisch aus mono-und dialkylierten tert-Butyl/tert-Octyldiphenylaminen, ein Gemisch aus mono-und dialkylierten Nonyldiphenylaminen, ein Gemisch aus mono-und dialkylierten Dodecyldiphenylaminen, ein Gemisch aus mono-und dialkylierten Isopropyl/Isohexyl-diphenylaminen, ein Gemisch aus mono-und dialkylierten tert-Butyldiphenylaminen, 2,3-Dihydro-3,3-dimethyl-4H-1,4-benzothiazin, Phenothiazin, ein Gemisch aus mono-und dialkylierten tert-Butyl/tert-Octylphenothiazinen, ein Gemisch aus mono-und dialkylierten tert-Octylphenothiazinen, N-Allylphenothiazin, N,N,N',N'-Tetraphenyl-1,4-diaminobut-2-en sowie Mischungen oder Kombinationen hiervon.
• Bevorzugte aminische Antioxidantien sind: N,N'-Di-isopropyl-p-phenylendiamin, N,N'-Di-secbutyl-p-phenylendiamin, N,N'-Bis(1,4-dimethylpentyl)-p-phenylendiamin, N,N'-Bis(1-ethyl-3-methylpentyl)-p-phenylendiamin, N, N'-Bis(1-methylheptyl)-p-phenylendiamin, N, N'-Dicyclohexyl-p-phenylendiamin, N,N'-Diphenyl-p-phenylendiamin, N,N'-Bis(2-naphthyl)-p-phenylendiamin, N-Isopropyl-N'-phenyl-p-phenylendiam in, N-(1,3-Dimethylbutyl)-N' -phenyl-p-phenylen-diamin, N-(1-Methy'lheptyl)-N'phenyl-p-phenylendiamin, N-Cyclohexyl-N'phenyl-p-phenylendiamin.
• Besonders bevorzugte aminische Antioxidantien sind die Strukturen:

Suitable amine antioxidants include, for example:

• N,N'-Di-isopropyl-p-phenylenediamine, N,N'-Di-sec-butyl-p-phenylenediamine, N,N'-Bis(1,4-dimethyl-pentyl)-p-phenylenediamine, N,N'-Bis(1-ethyl-3-methylpentyl)-p-phenylenediamine, N,N'-Bis(1-methyl-heptyl)-p-phenylenediamine, N,N'-Dicyclohexyl-p-phenylenediamine, N,N'-diphenyl-p-phenylenediamine, N,N'-bis(2-naphthyl)-p-phenylenediamine, N-isopropyl-N'-phenyl-p-phenylenediamine, N-(1,3-dimethyl-butyl)-N'-phenyl-p-phenylenediamine, N-(1-Methylheptyl)-N'phenyl-p-phenylenedi-mine, N-Cyclohexyl-N'-phenyl-p-phenylenediamine, 4-(p-toluenesulfamoyl)diphenylamine, N,N'-dimethyl-N,N'-di-sec-butyl-p-phenylenediamine, diphenylamine, N-allyldiphenylamine, 4-isopropoxydiphenylamine, N-phenyl-1-naphthylamine, N-(4-tert-octylphenyl)-1-naphthylamine, N-phenyl-2-naphthylamine, octylated diphenylamine, e.g. p,p'-di-tert-octyldiphenylamine, 4-n-butylaminophenol, 4-butyrylaminophenol, 4-nonanoylaminophenol, 4-dodecanoylaminophenol, 4-Octadecanoylamino-phenol, bis(4-methoxyphenyl)amine, 2,6-di-tert-butyl-4-dimethylaminomethyl-phenol, 2,4'-Diaminodiphenylmethane, 4,4'-Diaminodiphenylmethane, N,N,N',N'-Tetra-methyl-4,4'-diaminodiphenylmethane, 1,2-Bis[(2-methyl-phenyl)amino]ethane, 1,2-Bis(phenylamino)propane, (o-Tolyl)biguanide, Bis[4-(1',3'-dimethylbutyl)phenyl]amine, tert-octylated N-phenyl-1-naphthylamine, 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/isohexyldiphenylamines, 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-secbutyl-p-phenylenediamine, N,N'-Bis(1,4-dimethylpentyl)-p-phenylenediamine, N,N'-Bis(1-ethyl-3-methylpentyl)-p-phenylenediamine, N,N'-Bis(1-methylheptyl)-p-phenylenediamine, N,N'-Dicyclohexyl-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-methyl'lheptyl)-N'phenyl-p-phenylenediamine N-Cyclohexyl-N'phenyl-p-phenylenediamine.
• Particularly favored amine antioxidants are the following structures:

Preferred hydroxylamines or N-oxides (nitrons) are, for example, N,N-dialkylhydroxylamines, N,N-dibenzylhydroxylamine, N,N-dilaurylhydroxylamine, N,N-distearylhydroxylamine, N-benzyl-α-phenylnitrone, N-octadecyl-α-hexadecylnitrone, and Genox EP (SI Group) according to the formula:

Suitable lactones are benzofuranones and indolinones are, for example, 3-(4-(2-acetoxyethoxy)phenyl]-5,7-di-tert-butyl-benzofuran-2-one, 5,7-di-tert-butyl-3-[4-(2-stearoyloxyethoxy)phenyl]benzofuran-2-one, 3,3'-bis[5,7-di-tert-butyl-3-(4-(2-hydroxyethoxy]phenyl)benzofuran-2-one), 5,7-di-tert-butyl-3-(4-ethoxy-phenyl)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 that additionally contain phosphite groups, such as...

One particularly favored lactone has the following structure:

Another suitable group of antioxidants are isoindolo[2,1-A]quinazolines such as e.g.

Secondary antioxidants primarily act as hydroperoxide decomposers in the stabilization of plastics. Suitable secondary antioxidants are, in particular, phosphites or phosphonites such as triphenyl phosphite, diphenyl alkyl phosphites, phenyldialkyl phosphites, tri(nonylphenyl) phosphite, trilauryl phosphites, trioctadecyl phosphite, distearylpentaerythritol diphosphite, Tris-(2,4-di-tert-butylphenyl)phosphite, diisodecylpentaerythritol diphosphite, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, bis(2,4-di-cumylphenyl)pentaerythritol iphosphite, bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol di phosphite, diisodecyloxypentaerythritol diphosphite, bis(2,4-di-tert-butyl-6 methylphenyl)pentaerythritol diphosphite, bis(2,4,6-tris(tert-butylphenyl)pentaerythritol diphosphite, tristearyl sorbitol triphosphite, tetrakis(2,4-di-tert-butylphenyl)-4,4'-biphenylene diphosphonite, 6-isooctyloxy-2,4,8, 10-tetra-tert-butyl-12 H-dibenz[d,g]-1,3,2-dioxaphosphocin, bis(2,4-di-tert-butyl-6-methylphenyl)methyl phosphite, bis(2,4-di-tert-butyl-6-methylphenyl)ethyl phosphite, 6-fluoro-2,4,8, 10-tetra-tert-butyl-12-methyl-dibenz[d,g]-1,3,2-dioxaphosphocin, 2,2'2''-Nitrilo[triethyltris(3,3'',5,5'-tetra-tert-butyl-1, 1'-biphenyl-2,2'-diyl)phosphite], 2-ethyl-hexyl(3,3',5,5'-tetra-tert-butyl-1, 1'-biphenyl-2,2'-diyl))phosphite, 5-Butyl-5-ethyl-2-(2,4,6-tri-tert-butylphenoxy)-1,2-dioxaphosphiran.

Particularly favored phosphites are: with n = 1 to 100 With n = 3 to 100 with n = 3 to 100.

A preferred phosphonite is:

Suitable secondary antioxidants also include sulfur compounds such as distearylthiodipropionate, dilaurylthiodipropionate; ditridecyldithiopropionate, ditetradecylthiodipropionate, 3-(dodecylthio)-1,1'-[2,2-bis[[3-(dodecylthio)-1-oxopropoxy]methyl]-1,3-propanediyl]propanoic acid esters.

The following structures are preferred:

Suitable secondary antioxidants include sulfites. Preferably, inorganic sulfites, disulfites, or thiosulfates of a mono-, di-, tri-, or tetravalent metal are used, the metal preferably being an alkali. metal, an alkaline earth metal, aluminium and/or zinc, wherein the inorganic sulfite is used particularly in its anhydrous form.

Suitable salts include, in particular, sodium sulfite, potassium sulfite, lithium sulfite, calcium sulfite, magnesium sulfite, aluminum sulfite, and zinc sulfite. Thiosulfates, such as sodium thiosulfate, are also suitable.

Suitable fillers and reinforcing materials include synthetic or natural materials such as calcium carbonate, silicates, glass fibers, glass beads (solid or hollow), talc, mica, kaolin, barium sulfate, metal oxides and hydroxides, carbon black, graphite, carbon nanotubes, graphene, wood flour, or fibers from natural products such as cellulose or synthetic fibers. Other suitable fillers include hydrotalcites or zeolites, or layered silicates such as montmorillonite, bentonite, beidelite, mica, hectorite, saponite, vermiculite, ledikite, magadite, illite, kaolinite, wollastonite, and attapulgite.

Suitable acid scavengers (“antiacids”) are salts of monovalent, divalent, trivalent, or tetravalent metals, preferably alkali metals, alkaline earth metals, aluminum, or zinc, particularly those formed with fatty acids, such as calcium stearate, magnesium stearate, zinc stearate, aluminum stearate, calcium laurate, calcium behenate, calcium lactate, and calcium stearoyl-2-lactate. Other classes of suitable acid scavengers include hydrotalcites, especially synthetic hydrotalcites based on aluminum, magnesium, and zinc; hydrocalumites; zeolites; alkaline earth oxides, especially calcium oxide and magnesium oxide, as well as zinc oxide; alkaline earth carbonates, especially calcium carbonate, magnesium carbonate, and dolomite; and hydroxides, especially brucite (magnesium hydroxide).

Suitable costabilizers also include polyols, especially alditols or cyclitols. Examples of polyols are pentaerythritol, dipentaerythritol, tripentaerythritol, short-chain polyether polyols or polyester polyols, as well as hyperbranched polymers/oligomers or dendrimers with alcohol groups.

Preferably, the at least one alditol is selected from the group consisting of threitol, erythritol, galactitol, mannitol, ribitol, sorbitol, xylitol, arabitol, isomalt, lactitol, maltitol, altritol, iditol, maltotritol, and hydrogenated oligo- and polysaccharides with polyol end groups and mixtures thereof. Particularly preferably, the at least one preferred alditol is 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-Dgalacto-heptitol (Perseitol), D-glycero-D-gluco-heptitol, L-glycero-D-gluco heptitol, D-erythro-L-galacto-octitol, D-threo-L-galacto-octitol.

In particular, at least one cyclitol may 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, condudtol, ononitol, pinitol, pinpollitol, quebrachitol, ciceritol, quinic acid, shikimic acid and valienol, preferably myo-inositol.

Other suitable costabilizers are ester and ether derivatives of the aforementioned alditols or cyclitols, such as the following compounds:

Suitable UV absorbers include compounds based on 2-(2'-hydroxyphenyl)benzotriazoles, 2-hydroxybenzophenones, esters of benzoic acids, acrylates, oxamides and 2-(2-hydroxyphenyl)-1,3 ,5-triazines.

Suitable 2-(2'-hydroxyphenyl)benzotriazoles are, for example, 2-(2'-hydroxy-5'methylphenyl)benzotriazole, 2-(3', 5'-di-tert-butyl-2'-hydroxyphenyl)benzotriazole, 2-(5'-tert-butyl-2'-hydroxyphenyl)benzotriazole, 2-(2'-Hydroxy-5'-(1, 1,3,3-tetramethylbutyl)phenyl)benzotriazole, 2-(3',5'-di-tert-butyl-2'-hydroxyphenyl)-5-chlorobenzotriazole, 2-(3'''-tert-butyl-2'-hydroxy-5'-methylphenyl-5-chlorobenzotriazole, 2-(3'-sec-butyl-5'-tert-butyl-2'-hydroxy-phenyl)benzotriazole, 2-(2'-hydroxy-4'-octyloxyphenyl)benzotriazole, 2-(3',5'-di-tert-amyl-2'-hydroxyphenyl)benzotriazole, 2-(3',5'-bis(a,a-dimethylbenzyl)-2'-hydroxyphenyl)benzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2-octyloxycarbonylethyl)phenyl)-5-chlorobenzotriazole, 2-(3'-tert-B utyl-5'-[2-(2-ethylhexyloxy)-carbonylethyl]-2'-hydroxyphenyl)-5-chlorobenzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2-methoxycarbonylethyl)phenyl)-5-chlorobenzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2-methoxycarbonylethyl)phenyl)benzotriazole, 2-(3'-tert-Butyl-2'-hydroxy-5'-(2-octyloxycarbonylethyl)phenyl)benzotriazole, 2-(3'-tert-butyl-5'-[2-(2-ethylhexyloxy)carbonylethyl]-2'-hydroxyphenyl)benzotriazole, 2-(3'-dodecyl-2'-hydroxy-5'-methylphenyl)benzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2-isooctyloxycarbonylethyl)phenylbenzotriazole, 2,2'-methylenebis[4-(1,1,3,3-tetramethylbutyl)-6-benzotriazol-2-ylphenol]; the product of the transesterification of 2-[3'-tert-butyl-5'-(2-methoxycarbonylethyl)-2'-hydroxyphenyl]-2H-benzotriazole with polyethylene glycol 300; [R-CH ₂ CH ₂ -COO-CH ₂ CH ₂ ] ₂ , where R = 3'-tert-butyl-4'-hydroxy-5'-2H-benzotriazol-2-ylphenyl, 2-[2'-hydroxy-3'-(a,a-dimethylbenzyl)-5'-(1,1,3,3-tetramethylbutyl)phenyl]benzotriazole, 2-[2'-hydroxy-3'-(1, 1,3,3-tetramethylbutyl)-5'-(α,α-dimethylbenzyl)phenyl]benzotriazole.

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'-dimethyoxy derivatives of 2-hydroxybenzophenones.

Suitable acrylates are, for example, ethyl-a-cyano-β,β-diphenyl acrylate, isooctyl-a-cyano-β,β-diphenyl acrylate, methyl-a-carbomethoxycinnamate, methyl-a-cyano-β-methyl-p-methoxycinnamate, butyl-a-cyano-β-methyl-p-methoxycinnamate, methyl-a-carbomethoxy-p-methoxycinnamate and N-(β-carbomethoxy-β-cyanovinyl)-2-methylindoline.

Suitable esters of benzoic acids include, for example, 4-tert-butylphenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoylresorcinol, bis(4-tert-butylbenzoyl)resorcinol, benzoylresorcinol, 2,4-di-tert-butylphenyl-3,5-di-tert-butyl-4-hydroxybenzoate, hexadecyl-3,5-di-tert-butyl-4-hydroxybenzoate, octadecyl-3,5-di-tert-butyl-4-hydroxybenzoate, and 2-methyl-4,6-di-tert-butylphenyl-3,5-di-tert-butyl-4-hydroxybenzoate.

Suitable oxamides include, for example, 4,4'-dioctyloxyoxanilide, 2,2'-diethoxyoxanilide, 2,2'-dioctyloxy-5,5'-di-tert-butoxanilide, 2,2'-didodecyloxy-5,5'-di-tert-butoxanilide, 2-ethoxy-2'-ethyloxanilide, N,N'-bis(3-dimethylaminopropyl)oxamide, 2-ethoxy-5-tert-butyl-2'-ethoxanilide and 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-methylphenyl-1,3, 5-triazine, 2-(2-Hydroxy-4-dodecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3, 5-triazine, 2-(2-hydroxy-4-tridecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3, 5-triazine, 2-[2-Hydroxy-4-(2-hydroxy-3-butyloxypropoxy)phenyl]-4,6-bis(2,4-dimethyl) 1,3,5-triazine, 2-[2-Hydroxy-4-(2-hydroxy-3-octyloxypropyloxy)phenyl]-4, 6-bis(2,4-dimethyl)-1,3, 5-triazine, 2-[4-(Dodecyloxy/Tridecyloxy-2-hydroxypropoxy)-2-hydroxyphenyl]-4, 6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-[2-Hydroxy-4-(2-hydroxy-3-dodecyloxypropoxy)phenyl]-4,6-bis(2,4-dimethylphenyl-1,3,5-triazine, 2-(2-hydroxy-4-hexyloxy)phenyl-4, 6-diphenyl-1,3,5-triazine, 2-(2-Hydroxy-4-methoxyphenyl)-4,6-diphenyl-1,3,5-triazine, 2,4,6-Tris[2-hydroxy-4-(3-butoxy-2-hydroxypropoxy)phenyl]-1,3,5-triazine, 2-(2-Hydroxyphenyl)-4-(4-methoxyphenyl)-6-phenyl-1,3,5-triazine, 2-{2-Hydroxy-4-[3-(2-ethylhexyl-1-oxy)-2-hydroxypropyloxy]phenyl}-4, 6-bis(2,4-dimethylphenyl1,3, 5-triazine.

Suitable metal deactivators include, for example, N,N'-diphenyloxamide, N-salicylal-N'-salicyloylhydrazine, N,N'-bis(salicyloyl)hydrazine, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazine, 3-salicyloylamino-1,2,4-triazole, bis-(benzylidene)oxalyldihydrazide, oxanilide, isophthaloyldihydrazide, sebacoylbisphenylhydrazide, N,N'-diacetyladipoyldihydrazide, N,N'-bis(salicyloyl)oxylyldihydrazide, N,N'-bis(salicyloyl)thiopropionyldihydrazide, Tris [2-tert-butyl-4-thio (2'-methyl-4'-hydroxy-5'-tert- butyl)-phenyl-5-methyl] phenylphosphites.

Particularly suitable as metal deactivators are:

Suitable hindered amines include, for example, 1,1-bis(2,2,6,6-tetramethyl-4-piperidyl)succinate, bis(1,2,2,6,6-pentamethyl-4-piperidyl)sebazate, bis(1-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)-1,2,3,4-butanetracarboxylate, 1,1'-(1,2-Ethanediyl)-bis(3,3,5,5-tetramethyl-piper-azinone), 4-benzoyl-2,2,6,6-tetramethylpiperidine, 4-stearyloxy-2,2,6,6-tetramethylpiperidine, linear or cyclic con Densation products of N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4-morpholino-2,6-dichloro-1,3,5-triazine, the reaction product of 7,7,9,9-tetramethyl-2-cycloundecyl-1-oxa-3,8-diaza-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.

The following are particularly inhibited amines:

Preferred oligomeric and polymeric hindered amines exhibit the following structures:

With n = 2 to 100, preferably 2 to 10

With n = 3 to 200, preferably 5 to 100

With n = 1 to 100, preferably 2 to 10, or

Another suitable light stabilizer is Hostanox NOW (manufacturer: Clariant SE) with the following general structure: where R means -OC(O)-C ₁₅ H ₃₁ or -OC(O)-C ₁₇ H ₃₅ .

Compatibilizers are used, for example, in thermodynamically immiscible blends or recycled material mixtures and contain structural elements of the respective blend components being mixed. Suitable compatibilizers for polyolefin mixtures include olefin block copolymers consisting of ethylene, propylene, and alpha-olefins such as 1-octene. Other compatibilizers, especially for compatibilizing polar polymers such as PET or polyamides and nonpolar polymers such as PP or PE, often contain reactive groups derived from, for example, maleic anhydride, acrylic acid, glycidyl acrylate, or glycidyl methacrylate, and include, 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, SEBS-g-maleic anhydride, and polyethylene-polyacrylate-polyglycidyl methacrylate.

• Polyacrylate, z.B. Copolymere mit langkettigen Seitengruppen, Polyacrylat-Blockcopolymere, Alkylamide: z. B. N,N'-1,2-Ethandiylbisoctadecanamid Sor-bitanester, z.B. Monostearylsorbitanester, Titanate und Zirconate, reaktive Copolymere mit funktionellen Gruppen z. B. Polypropylen-co-Acrylsäure, Po-lypropylen-co-Maleinsäureanhydrid, Polyethylen-co-Glycidylmethacrylat, Polystyrol-alt-Maleinsäureanhydrid-Polysiloxane: z.B. Dimethylsilandiol-Ethylenoxid Copolymer, Polyphenylsiloxan Copolymer, Amphiphile Copolyme-re: z.B. Polyethylenblock-Polyethylenoxid, Dendrimere, z.B. hydroxylgrup-penhaltige Dendrimere.

Suitable dispersing agents include, for example:

• Polyacrylates, e.g., copolymers with long-chain side groups, polyacrylate block copolymers, alkylamides: e.g., N,N'-1,2-ethanediylbisoctadecanamide; sorbitan esters, e.g., monostearyl sorbitan esters; titanates and zirconates; reactive copolymers with functional groups, e.g., polypropylene-co-acrylic acid, polypropylene-co-maleic anhydride, polyethylene-co-glycidyl methacrylate; polystyrene-alt-maleic anhydride polysiloxanes: e.g., dimethylsilanediol-ethylene oxide copolymer, polyphenylsiloxane copolymer; amphiphilic copolymers: e.g., polyethylene block-polyethylene oxide; dendrimers, e.g., dendrimers containing hydroxyl groups.

1. a) Anorganische Flammschutzmittel wie z.B. Al(OH)₃, Mg(OH)₂, AlO(OH), MgCO₃ Schichtsilikate wie z. B. Montmorillonit oder Sepiolit, nicht oder organisch modifiziert, Doppelsalze, wie z.B. Mg-Al-Silikate, POSS-(Po-Iyhedral Oligomeric Silsesquioxane) Verbindungen, Huntit, Hydromagnesit oder Halloysit sowie Sb₂O₃, Sb₂O₅, MoO₃, Zinkstannat, Zinkhydroxystannat,
2. b) Stickstoffhaltige Flammschutzmittel wie z.B. Melamin, Melem, Melam, Melon, Melaminderivate, Melaminkondensationsprodukte oder Melaminsalze, Benzoguanamin, Polyisocyanurate, Allantoin, Phosphacene, insbesondere Melamincyanurat, Melaminphosphat, Dimelaminphosphat, Melaminpyrophosphat, Melaminpolyphosphat, Melamin-Metall-Phosphate wie z.B. Melaminaluminiumphosphat, Melaminzinkphosphat, Melaminmagnesiumphosphat, sowie die entsprechenden Pyrophosphate und Polyphosphate, Poly-[2,4-(piperazin-1,4-yl)-6-(morpholin-4-yl)-1,3,5-triazin], Ammoniumpolyphosphat, Melaminborat, Melaminhydrobromid,
3. c) Radikalbildner, wie z.B. Alkoxyamine, Hydroxylaminester, Azoverbindungen, Sulfenamide, Sulfenimide, Dicumyl oder Polycumyl, Hydroxyimide und deren Derivate wie z. B. Hydroxyimidester oder Hydroxyimidether
4. d) Phosphorhaltige Flammschutzmitteln wie z.B. roter Phosphor, Phosphate wie z.B. Resorcindiphosphat, Bisphenol-A-diphosphat und ihre Oligomere, Triphenylphosphat, Ethylendiamindiphosphat, Phosphinate wie z.B. Salze der hypophosphorigen Säure und Ihrer Derivate wie Alkylphosphinatsalzen z.B. Diethylphosphinataluminium oder Diethylphosphinat-Zink oder Aluminiumphosphinat, Aluminiumphosphit, Aluminiumphosphonat, Phosphonatester, oligomere und polymere Derivate der Methanphosphonsäure, 9,10-Dihydro-9-oxa-10-phosphoryl-phenanthren-10-oxid (DOPO) und deren substituierte Verbindungen,
5. e) Halogenhaltige Flammschutzmittel auf Chlor- und Brombasis wie z. B. polybrominierte Diphenyloxide, wie z.B. Decabromdiphenyloxid, Tris(3-brom-2,2-bis(brommethyl)propyl-phosphat, Tris(tribromneopentyl)-phosphat, Tetrabromphthalsäure, 1,2-Bis(tribromphenoxy)ethan, Hexabromcyclododecan, bromiertes Diphenylethan, Tris-(2,3-dibrompropyl)isocyanurat, Ethylen-bis-(tetrabromphthalimid), Tetrabrom-bisphenol A, bromiertes Polystyrol, bromiertes Polybutadien bzw, Polystyrol-bromiertes Polybutadien-Copolymere, bromierter Polyphenylenether, bromiertes Epoxidharz, Polypentabrombenzylacrylat, ggf. in Kombination mit Sb₂O₃ und/oder Sb₂O₅,
6. f) Borate wie z. B. Zinkborat oder Calciumborat, ggf. auf Trägermaterial wie z.B. Silica
7. g) Schwefelhaltige Verbindungen wie z.B. elementarer Schwefel, Disulfide und Polysulfide, Thiuramsulfid, Dithiocarbamate, Mercaptobenzthiazol und Sulfenamide,
8. h) Antidrip-Mitteln wie z.B. Polytetrafluorethylen,
9. i) Siliciumhaltige Verbindungen wie z. B. Polyphenylsiloxane,
10. j) Kohlenstoffmodifikationen wie z.B. Carbon-Nanoröhren (CNT), Blähgraphit oder Graphen
11. k) sowie Kombinationen oder Mischungen hieraus.

Suitable flame retardants are in particular

1. a) Inorganic flame retardants such as Al(OH) ₃ , Mg(OH) ₂ , AlO(OH), _MgCO3; layered silicates such as montmorillonite or sepiolite, unmodified or organically modified; double salts such as Mg-Al silicates, POSS (Po-Iyhedral Oligomeric Silsesquioxane) compounds, huntite, hydromagnesite or halloysite _, as well as _Sb₂O₃ , _Sb₂O₅ , _MoO₃ , zinc _stannate , zinc hydroxystannate,
2. b) Nitrogen-containing flame retardants such as melamine, melem, melam, melon, melamine derivatives, melamine condensation products or melamine salts, benzoguanamine, polyisocyanurates, allantoin, phosphacenes, in particular melamine cyanurate, melamine phosphate, dimelamine phosphate, melamine pyrophosphate, melamine polyphosphate, melamine metal phosphates such as melamine aluminum phosphate, melamine zinc phosphate, melamine magnesium phosphate, as well as the corresponding pyrophosphates and polyphosphates, poly-[2,4-(piperazine-1,4-yl)-6-(morpholin-4-yl)-1,3,5-triazine], ammonium polyphosphate, melamine borate, melamine hydrobromide,
3. c) Radical initiators, such as alkoxyamines, hydroxylamine esters, azo compounds, sulfenamides, sulfenimides, dicumyl or polycumyl, hydroxyimides and their derivatives such as hydroxyimide esters or hydroxyimide ethers
4. 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 phosphinate salts e.g. diethylphosphinate aluminum or diethylphosphinate zinc or aluminum phosphinate, aluminum phosphite, aluminum phosphonate, phosphonate esters, oligomeric and polymeric derivatives of methanephosphonic acid, 9,10-dihydro-9-oxa-10-phosphorylphenanthrene-10-oxide (DOPO) and their substituted compounds,
5. e) Halogen-containing flame retardants based on chlorine and bromine, such as polybrominated diphenyl oxides, e.g., decabromodiphenyl oxide, tris(3-bromo-2,2-bis(bromomethyl)propyl phosphate, tris(tribromoneopentyl) phosphate, tetrabromophthalic acid, 1,2-bis(tribromphenoxy)ethane, hexabromocyclododecane, brominated diphenylethane, tris-(2,3-dibromopropyl)isocyanurate, ethylene bis-(tetrabromophthalimide), tetrabromobisphenol A, brominated polystyrene, brominated polybutadiene or polystyrene-brominated polybutadiene copolymers, brominated polyphenylene ether, brominated epoxy resin, polypentabromenzyl acrylate, _possibly in combination with _Sb₂O₃ and/or _{Sb₂O₅ .}
6. f) Borates such as zinc borate or calcium borate, possibly on a carrier material such as silica
7. g) Sulfur-containing compounds such as elemental sulfur, disulfides and polysulfides, thiuram sulfide, dithiocarbamates, mercaptobenzthiazole and sulfenamides,
8. h) Anti-drip agents such as polytetrafluoroethylene,
9. i) Silicon-containing compounds such as polyphenylsiloxanes,
10. j) Carbon modifications such as carbon nanotubes (CNTs), expandable graphite or graphene
11. k) as well as combinations or mixtures thereof.

• Radikalbildner bevorzugt ausgewählt aus der Gruppe bestehend aus N-Alkoxyaminen, -C-C- Radikalbildnern, Radikalbildnern mit Azogruppen (-N=N-), Radikalbildnern mit Hydrazingruppen (-NH-HN-), Radikalbildnern mit Hydrazongruppen (>C=N-NH-), Radikalbildnern mit Azingruppen (>C=N-N=C<), Radikalbildnern mit Triazengruppen (-N=N-N<) oder aus Iminoxytriazinen.

Particularly suitable flame retardants are:

• Radical initiators preferably selected from the group consisting of N-alkoxyamines, -CC- radical initiators, radical initiators with azo groups (-N=N-), radical initiators with hydrazine groups (-NH-HN-), radical initiators with hydrazone groups (>C=N-NH-), radical initiators with azine groups (>C=NN=C<), radical initiators with triazine groups (-N=NN<) or from iminoxytriazines.

The production of suitable azo compounds is possible, for example, in M. Aubert et. al. Macromol. Sci. 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 production of triazenes in W. Pawelec et al., Pol. Degr. Rod. 2012, 97, 948-954 The synthesis of iminoxytriazines is described in WO 2014/064064 described.

• a) N-Alkoxyaminen gemäß der nachfolgend abgebildeten Strukturformel wobei

  R3

  für Wasserstoff oder einen gegebenenfalls substituierter Alkyl-, Cycloalkyl-, Aryl-Heteroaryl- oder Acyl-Rest steht, insbesondere ein Cl, bis C4- Alkylrest ist,

  R4

  für einen Alkoxy-, Aryloxy-, Cycloalkoxy-, Aralkoxy- oder Acyloxy-Rest steht,

  Z

  für Wasserstoff oder einen gegebenenfalls substituierter Alkyl-, Cycloalkyl-, Aryl-Heteroaryl- oder Acyl-Rest steht, wobei die beiden Reste Z auch einen geschlossenen Ring bilden können, der ggf. durch Ester-, Ether-, Amin, Amid, Carboxy- oder Urethangruppen substituiert sein kann,

  E

  für einen Alkoxy-, Aryloxy- Cycloalkyloxy-, Aralkoxy oder Acyloxyrest steht,

• b) Azo-Verbindungen gemäß der nachfolgend abgebildeten Strukturformeln wobei

  R5

  einen Alkly-, Cycloalkyl- oder Arylrest bedeutet,

  R6

  bei jedem Auftreten gleich oder verschieden ist und einen linearen oder verzweigten Alkylrest bedeutet,

  R7

  bei jedem Auftreten gleich oder verschieden ist und Wasserstoff oder einen linearen oder verzweigten Alkylrest bedeutet, und

  R8

  bei jedem Auftreten gleich oder verschieden ist und einen Alkyl, Alkoxy-, Aryloxy-Cycloalkyloxy-, Aralkoxy oder Acyloxyrest bedeutet,

  c)

  Dicumyl gemäß der nachfolgend abgebildeten Strukturformel

  wobei R⁷ die zuvor angegebene Bedeutung aufweist, bevorzugt Methyl ist,
• d) und/oder Polycumyl gemäß der nachfolgend abgebildeten Strukturformel wobei R⁷ die zuvor angegebene Bedeutung aufweist, bevorzugt Methyl ist, und 2 <n < 100.

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

• a) N-Alkoxyamines according to the structural formula shown below where

  R3

  for hydrogen or an optionally substituted alkyl, cycloalkyl, aryl heteroaryl or acyl group, in particular a Cl, up to C4 alkyl group,

  R4

  stands for an alkoxy, aryloxy, cycloalkoxy, aralkoxy or acyloxy residue,

  Z

  for hydrogen or an optionally substituted alkyl, cycloalkyl, aryl-heteroaryl or acyl residue, wherein the two residues Z can also form a closed ring which may optionally be substituted by ester, ether, amine, amide, carboxy or urethane groups,

  E

  stands for an alkoxy, aryloxy, cycloalkyloxy, alkoxy or acyloxy residue,

• b) Azo compounds according to the structural formulas shown below where

  R5

  means an alkyl, cycloalkyl or aryl residue,

  R6

  is the same or different in each occurrence and signifies a linear or branched alkyl group,

  R7

  is the same or different in each occurrence and signifies hydrogen or a linear or branched alkyl group, and

  R8

  is the same or different in each occurrence and represents an alkyl, alkoxy, aryloxy-cycloalkyloxy, aralkoxy or acyloxy residue,

  c)

  Dicumyl according to the structural formula shown below

  where R ⁷ has the meaning given above, preferably is methyl,
• d) and/or polycumyl according to the structural formula shown below where R ⁷ has the meaning given above, preferably is methyl, and 2 <n < 100.

• 1-Cyclohexyloxy-2,2,6,6-Tetramethyl-4-Octadecylaminopiperidin: Bis(1-Octyloxy-2,2,6,6-Tetramethylpiperidin-4-yl) Sebacat; 2,4-Bis[(1-Cyclohexyloxy-2,2,6,6-Tetramethylpiperidin-4-yl)Butylamino]-6-(2-Hydroxyethylamino-S-Triazin; Bis(1-Cyclohexyloxy-2,2,6,6-Tetramethylpiperidin-4-yl) Adipat;
• 2,4-Bis[(1-Cyclohexyloxy-2,2,6,6-Tetramethylpiperidin-4-yl)Butylamino]-6-chlor-S-Triazin; 1-(2-Hydroxy-2-Methylpropoxy)-4-Hydroxy-2,2,6,6-Tetramethylpiperidin; 1-(2-Hydroxy-2-Methylpropoxy)-4-Oxo-2,2,6,6-Tetramethylpiperidin; 1-(2-Hydroxy-2-Methylpropoxy)-4-Octadecanoyloxy-2,2,6,6-tetramethylpiperidin; Bis(1-(2-Hydroxy-2-Methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl)sebacat; Bis(1 -(2-Hydroxy-2-Methylpropoxy)-2,2,6,6-Tetramethylpiperidin-4-yl)adipat; 2,4-Bis{N-[1-(2-Hydroxy-2-Methylpropoxy)-2,2,6,6-Tetramethylpiperidin-4-yl]-N-Butylamino}-6-(2-Hydroxyethylamino)-S-Triazin); 4-Piperidinol, 2,2,6,6-Tetramethyl-1-(undecyloxy)-4,4'-carbonat; das Reaktionsprodukt von 2,4-Bis[(1-Cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-6-chlor-S-triazin mit N,N'-Bis(3-Aminopropylethylendiamin); die Oligomer-Verbindung, welche das Kondensationsprodukt ist von 4,4'-Hexamethylen-Bis(Amino-2,2,6,6-Tetramethylpiperidin) und 2,4-Dichlor-6-[(1-cyclohexyloxy-2,2,6,6-tetramethyl-4-yl)butylamino]-S-triazin, an den Enden verschlossen mit 2-Chlor-4,6-bis(dibutylamino)-S-Triazin; aliphatische Hydroxylamin wie z.B. Disterarylhydroxylamin; sowie Verbindungen der nachfolgenden Formeln. oder wobei n = 1-15 ist

Typical examples of the aforementioned N-alkoxyamines of the given structure are:

• 1-Cyclohexyloxy-2,2,6,6-tetramethyl-4-octadecylaminopiperidine: bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate; 2,4-Bis[(1-Cyclohexyloxy-2,2,6,6-Tetramethylpiperidin-4-yl)butylamino]-6-(2-Hydroxyethylamino-S-triazine; Bis(1-Cyclohexyloxy-2,2,6,6-Tetramethylpiperidin-4-yl) adipate;
• 2,4-Bis[(1-Cyclohexyloxy-2,2,6,6-Tetramethylpiperidin-4-yl)butylamino]-6-chloro-S-triazine; 1-(2-Hydroxy-2-Methylpropoxy)-4-Hydroxy-2,2,6,6-Tetramethylpiperidine; 1-(2-Hydroxy-2-Methylpropoxy)-4-Oxo-2,2,6,6-Tetramethylpiperidine; 1-(2-Hydroxy-2-Methylpropoxy)-4-Octadecanoyloxy-2,2,6,6-tetramethylpiperidine; bis(1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl) sebacate; bis(1-(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[(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-6-chloro-S-triazine with N,N'-bis(3-aminopropylethylenediamine); the oligomeric compound which is the condensation product of 4,4'-hexamethylene-bis(amino-2,2,6,6-tetramethylpiperidine) and 2,4-dichloro-6-[(1-cyclohexyloxy-2,2,6,6-tetramethyl-4-yl)butylamino]-S-triazine, sealed at the ends with 2-chloro-4,6-bis(dibutylamino)-S-triazine; aliphatic hydroxylamines such as disterarylhydroxylamine; and compounds of the following formulas. or where n = 1-15

• b) Phosphorhaltige Flammschutzmittel z.B. Phosphinate der folgenden Strukturen: wobei bevorzugt R1 und R2 identisch oder verschieden sind und ausgewählt sind aus linearem oder verzweigtem C1-C6-Alkyl und/oder Aryl; M ausgewählt ist aus der Gruppe bestehend aus Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Ce, Bi, Sr, Mn, Li, Na, K, Zn und/oder einem protonierten Stickstoff-Base, vorzugsweise Calcium-Ionen, Magnesium-Ionen, Aluminium-Ionen, und/oder Zink-Ionen; und m = 1-4, bevorzugt 2 oder 3, ist; n = 1-4, bevorzugt 1 oder 3, ist; x = 1-4, bevorzugt 1 oder 2, ist. In einer besonders bevorzugten Ausführungsform ist R¹ = Alkyl, R₂ = Alkyl und M = Al oder Zn.

The compounds mentioned above are partly 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.

• b) Phosphorus-containing flame retardants, e.g. phosphinates of the following structures: wherein preferably R1 and R2 are 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, ^R1 = alkyl, _R2 = alkyl, and M = Al or Zn.

A particularly favored example of a phosphinate is the commercially available product Exolit OP (RTM) from Clariant SE.

Other 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 elements, and n is a number from 1 to 4 corresponding to the charge of the corresponding metal ion Met. Met ⁿ⁺ is, for example, Na ⁺ , Ca2 ⁺ , Mg2 ⁺ , Zn2 ⁺ , Ti4 ⁺ , or Al3 ⁺ , with Ca2 ⁺ , Zn2 ⁺ , and Al3 ⁺ being particularly preferred.

The above-mentioned salts of hypophosphorous acid are partly 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 diaryls of a structure according to the following formula: where R ₈ , and R ₁₀ = H, alkyl, preferably C1-C4, R ₉ = C1-C4 alkyl u = 1-5st and v = 1-5ist.

Corresponding structures can also exist 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 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 Reference is made to the US patent applications for phosphonate oligomers. US 2005/0020800 A1 , US 2007/0219295 A1 and US 2008/0045673 A1 Reference is made to the US patent documents concerning linear phosphonate oligomers and polymers. US 3,946,093 , US 3,919,363 , US 6 288 210 B1 , US 2,682,522 and US 2,891,915 referred.

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

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 elements, x=2 or 3, n ≥ 10, m=0-25, R=H, halogen or an aliphatic or aromatic residue with 1-32 C atoms and R ₁ = H, C1 -C6 alkyl or phenyl.

Products based on oxophosphorine oxide are available, for example, under the trade name Ukanol (RTM) from Schill und Seilacher GmbH. Further compounds can be found, for example, according to the patent specifications. WO 2013020696 , WO 2010135398 , W003070736, WO2006084488 , WO 2006084489 , WO 2011000019 , WO 2013068437 , WO 2013072295 be manufactured.

Other suitable phosphorus-containing flame retardants are cyclic phosphonates of a structure according to one of the following formulas: wherein 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 wherein A ³ and A ⁴ independently represent methyl or ethyl, and A ⁵ represents a straight-chain or branched alkyl group with 1 to 4 carbon atoms, or a phenyl or benzyl group, each of which may have up to 3 methyl groups.

Cyclic phosphonates are, for example, commercially available from Thor GmbH under the trade name Aflammit (RTM) or can be produced according to EP 2450401 be manufactured.

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

a) Nitrogen-containing flame retardants

Preferred nitrogen-containing flame retardants are melamine polyphosphate, melamine cyanurate, melamine metal phosphates, poly-[2,4-(piperazine-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 include, for example, the following compounds

Particularly preferred flame retardants are halogen-free and include the following compounds: Al(OH) ₃ , Mg(OH) ₂ n=1-100 with n= 2-20 n=2-20 with n=3-100 n=1-3 n= 3-100 with R = alkyl, phenyl and n = 3-20

Suitable lubricants and processing aids include, 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 erucamide or oleamide, fluoropolymers, silicones or neoalkoxy titanates and zirconates.

Suitable heat stabilizers, especially for PVC recyclates, include, for example, metal soaps of divalent metals such as Ba, Zn, Ca (e.g., zinc stearate, calcium stearate), organotin compounds (e.g., methyl and octyl tin compounds such as dioctyltin bisisooctylthioglycolate or dioctyltin maleate), aminouracils, aminocrotonic acid esters, perchlorate salts, and, as costabilizers, phosphites, epoxides, polyols, diketones, dihydropyridines, hydrotalcites, and zeolites.

Suitable pigments can be inorganic or organic. Examples of inorganic pigments include titanium dioxide, zinc oxide, zinc sulfide, iron oxide, ultramarine, and carbon black. Examples of organic pigments include anthraquinones, anthanthrones, benzimidazolones, quinacridones, diketopyrrolopyrroles, dioxazines, indanthrones, isoindolinones, azo compounds, perylenes, phthalocyanines, and pyranthrones. Other suitable pigments include metal-based effect pigments and metal oxide-based pearlescent pigments.

Suitable optical brighteners include, for example, bisbenzoxazoles, phenylcoumarins or bis(styryl)biphenyls, and in particular optical brighteners of the following formulas:

Suitable filler deactivators include, for example, polysiloxanes, polyacrylates, especially block copolymers such as polymethacrylic acid-polyalkylene oxide or polyglycidyl(meth)acrylates and their copolymers, e.g. with styrene, as well as epoxides, e.g. of the following structures:

Suitable antistatic agents include, for example, ethoxylated alkylamines, fatty acid esters, alkyl sulfonates and polymers that form a co-continuous network with the polymer matrix, such as polyetheramides, polyesteramides, polyetheresteramides or polyether block copolymers, possibly with the addition of ionically conductive metal salts.

Suitable antiozonants are the amines mentioned above, 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), include peroxides, alkoxyamine esters, oxyimide sulfonic acid esters, and in particular the following structures:

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

Suitable additives for increasing electrical conductivity include, for example, the aforementioned antistatic agents, carbon black and carbon compounds such as carbon nanotubes and graphene, metal powders such as copper powder and conductive polymers such as polypyrroles, polyanilines and polythiophenes.

Suitable infrared-active additives include, for example, aluminum silicates, hydrotalcites, or dyes such as phthalocyanines or anthraquinones.

Suitable crosslinking agents include, for example, peroxides such as dialkyl peroxides, alkyl aryl peroxides, peroxy esters, peroxy carbonates, diacyl peroxides, peroxy ketals, silanes such as vinyltrimethoxysilane, vinyltriethoxysilane, vinyltriacetoxysilane, vinyltris(2-methoxyethoxy)silane, 3-methacryloyloxypropyltrimethoxysilane, vinyldimethoxymethylsilane or ethylene-vinylsilane copolymers.

Suitable prodegradants are additives that selectively accelerate or control the degradation of a polymer in the environment. Examples include transition metal fatty acid esters, e.g., of manganese or iron, which accelerate oxidative and/or photooxidative degradation of, for example, polyolefins, or enzymes that induce hydrolytic degradation of, for example, aliphatic polyesters.

Suitable chemical blowing agents include, for example, azo compounds such as azodicarboxylic acid diamide, sulfonyl semicarbazides such as p-toluenesulfonyl semicarbazide, tetrazoles such as 5-phenyltetrazol, hydrazides such as p-toluenesulfonyl hydrazide, 4,4'-oxibis(benzenesulfonyl)hydrazide, N-nitroso compounds such as N,N'-dinitrosopentamethylenetetramine or carbonates such as sodium hydrogen carbonate or zinc carbonate.

Suitable slip agents include, for example, amide waxes such as erucamide or oleamide.

Suitable antiblocking agents include silica, talc, or zeolites.

Suitable antifogging additives include, for example, ethoxylated sorbitan esters, ethoxylated fatty acid alcohols, or ethoxylated alkylamine esters.

Suitable biocides include, 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 riceneolate.

Suitable marking agents include, for example, fluorescent dyes or rare earth elements.

Suitable nucleating agents are talc, alkali or alkaline earth salts of mono- and polyfunctional carboxylic acids such as benzoic acid, succinic acid, adipic acid, e.g. sodium benzoate, zinc glycerolate, aluminum hydroxybis(4-tert-butyl)benzoate, 2,2'-methylene-bis-(4,6-di-tert-butylphenyl)phosphate, as well as triamides and diamides such as trimesic acid tricyclohexylamide, trimesic acid tri(4-methylcyclohexylamide), trimesic acid tri(tert-butylamide), N,N',N''-1,3,5-benzenetriyltris(2,2-dimethyl-propanamide) or 2,6-naphthalenedicarboic acid dicyclohexylamide.

Suitable transparency improvers (clarifiers) include, in particular, sorbitol derivatives such as, for example,

Suitable antinuclear agents are azine dyes such as nigrosine or ionic liquids,

Suitable additives for increasing thermal conductivity include, for example, inorganic fillers such as boron nitride, aluminum nitride, aluminum oxide, aluminum silicate, silicon carbide, but also carbon nanotubes (CNTs).

Suitable impact strength enhancers include, for example, functionalized or non-functionalized polyolefins, such as ethylene copolymers like EPDM or maleic anhydride or styrene-acrylonitrile-modified EPDM, glycidyl methacrylate-modified ethylene-acrylate copolymers or ionomers, core-shell polymers e.g. based on MBS (methacrylate-butadiene-styrene copolymer) or acrylic ester polymethyl methacrylate, thermoplastic elastomers (TPE) e.g. based on styrene block copolymers (styrene-butadiene (SB), styrene-butadiene-styrene (SBS) possibly hydrogenated (SEBS) or modified by maleic anhydride (SEBS-g-MAH), thermoplastic polyurethanes, copolyesters or copolyamides.

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

Suitable demolding aids include silicones, soaps and waxes such as montan waxes.

Preferably, the additive according to the invention, which can be in the form of a powder, liquid, oil, compacted on a carrier material, as granules, solution, or flakes, is mixed with the polymer to be stabilized, the polymer matrix is transferred into the melt, and then cooled. Alternatively, it is also possible to introduce the additive into a polymer melt in a molten state.

Furthermore, the additive compositions according to the invention can be produced and introduced in the form of so-called masterbatches or concentrates, which contain, for example, 10-90% of the compositions according to the invention in a polymer or a polymer recyclate.

In a further preferred embodiment, the compositions contain secondary antioxidants, in particular phosphites/phosphonites, sulfites, acid scavengers, costabilizers based on polyols and/or light stabilizers from the group of hindered amines (HALS).

Furthermore, the present invention relates to a stabilized polymer composition comprising or consisting of a polymer stabilizer contained in the foregoing or a stabilizer composition described in the foregoing and at least one polymer.

1. a) Polymeren aus Olefinen oder Diolefinen wie z.B. Polyethylen (LDPE, LLDPE, VLDPE, ULDPE, MDPE, HDPE, UHMWPE), Metallocen-PE (m-PE), Polypropylen, Polyisobutylen, Poly-4-methyl- penten-1, Polybutadien, Polyisopren, wie z.B. auch Naturkautschuk (NR), Polycycloocten, Polyalkylen-Kohlenmonoxid-Copolymere, sowie Copolymere in Form von statistischen oder Blockstrukturen wie z.B. Polypropylen-Polyethylen (EP), EPM oder EPDM mit z.B. 5-Ethyliden-2-Norbornen als Comonomer, Ethylen-Vinylacetat (EVA), Ethylen-Acrylester, wie z.B. Ethylen- Butylacrylat, Ethylen-Acrylsäure und deren Salze (lonomere), sowie Terpolymere wie z.B. Ethylen-Acrylsäure-Glycidyl(meth)acrylat, Pfropfpolymere wie z.B. Polypropylen-graft-Maleinsäureanhydrid, Polypropylen-graft-Acrylsäure, Polyethylen-graft-Acrylsäure, Polyethylen-Polybutylacrylat-graft-Maleinsäureanhydrid sowie Blends wie z.B. LDPE/LLDPE oder auch langkettenverzweigte Polypropylen-Copolymere die mit alpha-Olefinen als Comonomere hergesellt werden wie z.B. mit 1-Buten, 1-Hexen, 1-Octen oder 1-Octadecen,
2. b) Polystyrol, Polymethylstyrol, Poly-alpha-methylstyrol, Polyvinylnaphthalin, Polyvinylbiphenyl, Polyvinyltoluol, Styrol-Butadien (SB), Styrol-Butadien-Styrol (SBS), Styrol-Ethylen-Butylen- Styrol (SEBS), Styrol-Ethylen-Propylen-Styrol, Styrol-Isopren, Styrol-Isopren-Styrol (SIS), Styrolutadienacrylnitril (ABS), Styrol-acrylnitril (SAN), Styrol-acrylnitrilacrylat (ASA), Styrol- Ethylen, Styrol-Maleinsäureanhydrid-Polymere einschl. entsprechender Pfropfcopolymere wie z.B. Styrol auf Butadien, Maleinsäureanhydrid auf SBS oder SEBS, sowie Pfropfcopolymere aus Methylmethacrylat, Styrol-Butadien und ABS (MABS), sowie hydrierte Polystyrol-Derivate wie z.B. Polyvinylcyclohexan,
3. c) halogenenthaltenden Polymeren wie z.B. Polyvinylchlorid (PVC), Polychloropren und Polyvinylidenchlorid (PVDC), Copolymere aus Vinylchlorid und Vinylidenchlorid oder aus Vinylchlorid und Vinylacetat, chloriertes Polyethylen, Polyvinylidenfluorid, Epichlorhydrin- Homo und Copolymere insbes. mit Ethylenoxid (ECO),
4. d) Polymeren von ungesättigten Estern wie z.B. Polyacrylate und Polymethacrylate wie Polymethylmethacrylat (PMMA), Polybutylacrylat, Polylaurylacrylat, Polystearylacrylat, Polyglycidylacrylat, Polyglycidylmethacrylat, Polyacrylnitril, Polyacrylamide, Copolymere wie z.B. Polyacrylnitril-Polyalkylacrylat,
5. e) Polymeren aus ungesättigten Alkoholen und Derivaten, wie z.B. Polyvinylalkohol, Polyvinylacetat, Polyvinylbutyral, Polyallylphthalat, Polyallylmelamin,
6. f) Polyacetalen, wie z.B. Polyoxymethylen (POM) oder Copolymere mit z.B. Butanal,
7. g) Polyphenylenoxiden und Blends mit Polystyrol oder Polyamiden,
8. h) Polymeren von cyclischen Ethern wie z.B. Polyethylenglycol, Polypropylenglycol, Polyethylenoxid, Polypropylenoxid, Polytetrahydrofuran,
9. i) Polyurethanen, aus hydroxyterminierten Polyethern oder Polyestern und aromatischen oder aliphatischen Isocyanaten wie z.B. 2,4-oder 2,6 Toluylendiisocyanat oder Methylendiphenyldiisocyanat insbesondere auch lineare Polyurethane (TPU), Polyharnstoffen,
10. j) Polyamiden wie z.B. Polyamid-6, 6.6, 6.10, 4.6, 4.10, 6.12, 10.10, 10.12, 12.12, Polyamid 11, Polyamid 12 sowie (teil-)aromatische Polyamide wie z.B. Polyphthalamide, z.B. hergestellt aus Terephthalsäure und/oder Isophthalsäure und aliphatischen Diaminen wie z.B. Hexamethylendiamin oder m-Xylylendiamin oder aus aliphatischen Dicarbonsäuren wie z.B. Adipinsäure oder Sebazinsäure und aromatischen Diaminen wie z.B. 1,4- oder 1,3-Diaminobenzol, Blends von unterschiedlichen Polyamiden wie z.B. PA-6 und PA 6.6 bzw. Blends von Polyamiden und Polyolefinen wie z.B. PA/PP,
11. k) Polyimiden, Polyamidimiden, Polyetherimiden, Polyesterimiden, Poly(ether)ketonen, Polysulfonen, Polyethersulfonen, Polyarylsulfonen, Polyphenylensulfiden, Polybenzimidazolen, Polyhydantoinen,
12. l) Polyestern aus aliphatischen oder aromatischen Dicarbonsäuren und Diolen oder aus Hydroxy-Carbonsäuren wie z.B. Polyethylenterephthalat (PET), Polybutylenterephthalat (PBT), Polypropylenterephthalat (PTI), Polyethylennaphthylat (PEN), Poly-1,4-dimethylolcyclohexanterephthalat, Polyhydroxybenzoat, Polyhydroxynaphthalat, Polymilchsäure (PLA), Polyhydroxybutyrat (PHB), Polyhydroxyvalerat (PHV), Polyethylensuccinat,Polytetramethylensuccinat, Polycaprolacton,
13. m) Polycarbonaten, Polyestercarbonaten, sowie Blends wie z.B. PC/ABS, PC/PBT, PC/PET/PBT, PC/PA,
14. n) Cellulosederivaten wie z.B. Cellulosenitrat, Celluloseacetat, Cellulosepropionat, Cellulosebutyrat,
15. o) Epoxidharzen, bestehend aus di-oder polyfunktionellen Epoxidverbindungen in Kombination mit z.B. Härtern auf der Basis von Aminen, Anhydriden, Dicyandiamid, Mercaptanen, Isocyanaten oder katalytisch wirkenden Härtern,
16. p) Phenolharzen wie z.B. Phenol-Formaldehyd-Harze, Harnstoff-Formaldehyd-Harze, Melamin- Formaldehydharze,
17. q) ungesättigten Polyesterharzen aus ungesättigten Dicarbonsäuren und Diolen mit Vinylverbindungen z.B. Styrol, Alkydharze,
18. r) Silikonen, z.B. auf der Basis von Dimethylsiloxanen, Methyl-Phenyl-siloxanen oder Diphenylsiloxanen z.B. Vinylgruppen terminiert,
19. s) sowie Mischungen, Kombinationen oder Blends aus zwei oder mehr der zuvor genannten Polymere.

Preferably, at least one polymer is selected from the group consisting of:

1. 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-methylpentene-1, polybutadiene, polyisoprene, such as natural rubber (NR), polycyclooctene, polyalkylene-carbon monoxide copolymers, as well as 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 a comonomer, ethylene-vinyl acetate (EVA), ethylene acrylates such as ethylene-butyl acrylate, ethylene-acrylic acid and their salts (ionomers), as well as 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 produced with alpha olefins as comonomers, such as 1-butene, 1-hexene, 1-octene, or 1-octadecene.
2. b) Polystyrene, polymethylstyrene, poly-alpha-methylstyrene, polyvinylnaphthalene, polyvinylbiphenyl, polyvinyltoluene, styrene-butadiene (SB), styrene-butadiene-styrene (SBS), styrene-ethylene-butylene-styrene (SEBS), styrene-ethylene-propylene-styrene, styrene-isoprene, styrene-isoprene-styrene (SIS), styrolutadiene acrylonitrile (ABS), styrene-acrylonitrile (SAN), styrene-acrylonitrile acrylate (ASA), styrene-ethylene, styrene-maleic anhydride polymers including corresponding graft copolymers such as styrene on butadiene, maleic anhydride on SBS or SEBS, as well as graft copolymers of methyl methacrylate, styrene-butadiene and ABS (MABS), and hydrogenated Polystyrene derivatives such as polyvinylcyclohexane,
3. 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),
4. 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-polyalkyl acrylate,
5. e) Polymers made from unsaturated alcohols and derivatives, such as polyvinyl alcohol, polyvinyl acetate, polyvinyl butyral, polyallyl phthalate, polyallyl melamine,
6. f) Polyacetals, such as polyoxymethylene (POM) or copolymers with, for example, butanal,
7. g) Polyphenylene oxides and blends with polystyrene or polyamides,
8. h) Polymers of cyclic ethers such as polyethylene glycol, polypropylene glycol, polyethylene oxide, polypropylene oxide, polytetrahydrofuran,
9. i) Polyurethanes, made from hydroxy-terminated polyethers or polyesters and aromatic or aliphatic isocyanates such as 2,4- or 2,6-toluene diisocyanate or methylene diphenyl diisocyanate, in particular also linear polyurethanes (TPU), polyureas,
10. 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., produced 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.
11. k) polyimides, polyamidimides, polyetherimides, polyesterimides, poly(ether) ketones, polysulfones, polyethersulfones, polyarylsulfones, polyphenylene sulfides, polybenzimidazoles, polyhydantoins,
12. 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 (PTI), polyethylene naphthylate (PEN), poly-1,4-dimethylolcyclohexane terephthalate, polyhydroxybenzoate, polyhydroxynaphthalate, polylactic acid (PLA), polyhydroxybutyrate (PHB), polyhydroxyvalerate (PHV), polyethylene succinate, polytetramethylene succinate, polycaprolactone,
13. m) Polycarbonates, polyester carbonates, and blends such as PC/ABS, PC/PBT, PC/PET/PBT, PC/PA,
14. n) Cellulose derivatives such as cellulose nitrate, cellulose acetate, cellulose propionate, cellulose butyrate,
15. o) Epoxy resins consisting of di- or polyfunctional epoxy compounds in combination with, for example, hardeners based on amines, anhydrides, dicyandiamide, mercaptans, isocyanates or catalytically acting hardeners,
16. p) Phenolic resins such as phenol-formaldehyde resins, urea-formaldehyde resins, melamine-formaldehyde resins,
17. q) unsaturated polyester resins made from unsaturated dicarboxylic acids and diols with vinyl compounds, e.g., styrene, alkyd resins,
18. r) Silicones, e.g. based on dimethylsiloxanes, methylphenylsiloxanes or diphenylsiloxanes, e.g. vinyl groups terminated,
19. s) as well as mixtures, combinations or blends of two or more of the aforementioned polymers.

If the polymers listed under a) to r) are copolymers, they can exist in the form of random, block, or tapered structures. Furthermore, the polymers mentioned can exist in the form of linear, branched, star-shaped, or hyperbranched structures.

If the polymers listed under a) to r) are stereoregular polymers, they can be in the form of isotactic, stereotactic, but also atactic forms or as stereoblock copolymers.

The polyolefins mentioned under a) may also be cross-linked, e.g. cross-linked polyethylene, which is then referred to as X-PE.

Furthermore, the compounds described above can be used to stabilize rubbers and elastomers. These can be natural rubber (NR) or synthetic rubber materials.

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

Besides new products, the plastics can be recycled plastics, e.g. from industrial collections such as production waste, or plastics from household or recycling collections.

Polymers made from renewable raw materials such as polylactic acid (PLA), polyhydroxybutyric acid (PHB), polyhydroxyvaleric acid (PHV), polybutylene succinate (PBS), polybutylene succinate coadipate (PBSA), polyethylene succinate, and polytetramethylene succinate are particularly preferred.

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

Preferred polymers are thermoplastic polymers, particularly polymers made of olefins or diolefins and polystyrene polymers. Another preferred group of polymers are polyamides and polyesters.

In the event that further additives are added to the polymer composition, these can be added separately, in the form of liquids, powders, granules or compacted products, or together with the polymeric stabilizer or stabilizer composition according to the invention as described above.

The incorporation of the polymeric stabilizer or stabilizer composition described above, and any additional additives, into the polymer is carried out using conventional processing methods, preferably by mixers, kneaders, or extruders. Preferred processing machines include extruders such as single-screw extruders, twin-screw extruders, planetary roller extruders, ring extruders, and co-kneaders, which are pre- Some units are equipped with vacuum degassing. Processing can take place under air or, if necessary, under inert gas conditions.

The processing of plastic compositions containing polymeric stabilizers or stabilizer compositions can be carried out using conventional plastic processing methods in continuous and discontinuous processes, such as extrusion, calendering, blow molding, pultrusion, injection molding, pressing, injection molding, casting, blow molding, rotational molding, deep drawing, sintering, foaming or also by additive manufacturing processes for the production of granules, molded parts, semi-finished products, fibers and films.

Suitable extruders include piston extruders and screw extruders, single-screw extruders, twin-screw extruders, multi-screw extruders, and planetary roller extruders, especially for the production of plastic granules, pipes, rods, hoses, profiles, coatings, sheets, films, V-belts, timing belts, seals, foam boards (XPS), fibers, and filaments for additive manufacturing processes.

Suitable injection molding machines can be hydraulic or electromechanical and include multi-component injection molding and in-mold processes. Examples of parts produced by injection molding include bottles, containers, screw-top jars, boxes, barrels, buckets, pallets, technical parts for the automotive and transport sectors such as bumpers, trim panels, handles, headlight covers, fittings and functional parts, electrical and electronic applications such as housing parts and accessories for televisions, computers, mobile phones, washing machines, dishwashers, coffee machines, drills, connectors, storage media, household, leisure and sporting goods such as flower pots, clothes hangers, toy figures, model kits, and furniture components such as clamps and clips.

Parts produced by blow molding are especially hollow bodies such as bottles, fuel tanks, canisters, wash water tanks and expansion tanks.

Parts manufactured by rotational molding include, in particular, tanks such as heating oil and rainwater tanks, housings for machines, transport containers, leisure and water sports equipment such as kayaks.

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

Additive manufacturing processes include, for example, Binder jetting (BJ), Laser Sintering (LS), Selective Laser Melting (SLM), Electron Beam Melting (EBM), Fused Deposition Modeling (FDM), Fused Filament Fabrication (FFF), Multi-Jet Modeling (MJM), Poly-Jet Modeling (PJM), LayerLaminated Manufacturing (LLM), Thermal Transfer Sintering (TIS), Digital Light Processing (DLP), Photopolymer Jetting (PJ) and Stereolithography (SL).

Exemplary molded parts that can be produced from the polymer composition according to the invention are films or foils, foams, fibers, cables and tubes, profiles, hollow bodies, tapes, membranes, such as geomembranes, or adhesives, which are produced by extrusion, injection molding, blow molding, calendering, pressing processes, spinning processes, rotomoulding, e.g. for packaging, e.g. for food, detergents, cosmetics, adhesives in the form of films, bottles, bags, screw-top containers, storage and transport containers such as... B. Boxes, crates, barrels, buckets, pallets; automotive, railway, aircraft, ship and machine parts such as bumpers, trim parts, fittings and functional parts, upholstery; construction applications such as profiles, construction films, cable ducts, house cladding, noise barriers, drainage channels, profile boards, floor coverings; road and landscaping applications such as beacon bases, posts, barriers, geotextiles; electrical and electronic applications such as housing parts and accessories for televisions, computers, mobile phones, washing machines, dishwashers, coffee machines, drills, connectors, storage media, cable insulation, pipes for e.g. water, gas, wastewater, irrigation; Drainage pipes, hygiene products such as diapers, furniture and textile applications such as curtains and upholstery, worktops, household, leisure and sports products such as balls, tennis rackets, skis, flower pots, rain barrels, clothes hangers, agricultural applications such as mulch, tunnel or perforated films, plant pots, pharmaceutical and plant protection applications such as for the encapsulation of active ingredients and biologically active substances, in medical technology for the production of suture material, dressing material, orthoses and prostheses.

The at least one stabilizer or stabilizer composition is preferably contained in the stabilized polymer composition in a quantity of 0.01 to 10 wt.%, preferably 0.05 to 5.0 wt.%, particularly preferably 0.1 to 2.0 wt.%.

Furthermore, the present invention relates to the production of a stabilizer according to the invention as described above, in which at least one monomer of general formula IV is used. where R ¹ , R ² , R ³ , A, X and R ⁶ are defined as above and one of the residues R ⁷ is a residue R ⁶ and the other residue R ⁷ is hydrogen, is polymerized by radicals.

If only monomers of formula IV are used, in particular only one type of monomer according to IV, a homopolymer is formed. Copolymers are also possible; in this case, the radical polymerization is carried out in the presence of at least one other radically polymerizable monomer, which preferably has a structure according to general formula V: where X, R ⁶ , R ⁷ and b have the preceding meaning.

Furthermore, the present invention relates to a method for stabilizing a polymer, in particular against thermal, actinic or oxidative degradation, by incorporating at least one polymeric stabilizer according to the invention according to a polymeric stabilizer composition according to the invention.

Furthermore, the present invention relates to the use of a polymeric stabilizer according to a stabilizer composition according to the invention for stabilizing polymers, in particular against thermal, actinic or oxidative degradation.

The present invention is described in more detail below, without limiting the present invention to the specific embodiments shown.

Stabilizers for thermoplastic halogen-free plastic recyclates, especially polyolefin recyclates in the form of injection-molded parts, foils or films, foams, fibers, cables and pipes, profiles, hollow bodies, tapes, membranes such as geomembranes, or adhesives, which are produced by extrusion, injection molding, blow molding, calendering, pressing processes, spinning processes, rotomoulding, e.g., for the electrical and electronics industry, construction industry, transport industry (car, aircraft, ship, rail), for medical applications, for household and electrical appliances, vehicle parts, consumer goods, packaging, furniture, textiles.

Preferred are the acrylates, methacrylates and styrene derivatives of the C5-alditols arabite, xylitol or ribitol or of the C7-alditol volemitol, in particular the following structure:

The depicted monomer units are arranged statistically in the polymer chain.

Copolymers of structure (A) are also preferred. These are prepared by co-polymerization of the protected acetalized monomers with polymerizable monomers containing at least one polymerizable group. Suitable co-monomers are, in particular, based on acrylates, methacrylates, or styrene derivatives such as methyl acrylates, ethyl acrylates, propyl acrylates, butyl acrylates, hexyl acrylates, lauryl acrylates, stearyl acrylates, benzyl acrylates, phenyl acrylates, or the corresponding methacrylates, acrylamide, methacrylamide, styrene, and alpha-methylstyrene.

In the production of the polymeric stabilizers according to the invention, protecting groups can also be used to block free OH groups of the alditols or cyclitols. Preferred protecting groups are acetals, in particular isopropylidenes obtainable by acetalization with acetone. Other suitable protecting groups are, for example, isobutylidenes, 2-methyl-4-pentylidenes, or cyclohexylidenes. The removal of the protecting groups is carried out, for example, under acidic conditions, e.g., in the presence of HCl.

The preferred radical polymerization method is free radical polymerization. Controlled radical polymerization is also possible.

Examples of implementation:

a) Syntheses

Diacetone xylitol

A mixture of 10.0 g crystalline xylitol (65.7 mmol, 1.00 eq), 200 mL acetone (2.70 mol, 4.11 eq), 20.0 g anhydrous copper sulfate, and 0.2 mL concentrated sulfuric acid was stirred at room temperature for 48 hours. The copper sulfate was removed by filtration, and the filtrate was stirred with 10.0 g powdered calcium hydroxide for one hour to neutralize the acid. The solid was filtered using ^Celite® Hyflo Super Cel, and the solvent was removed under reduced pressure. The oily crude product was purified by vacuum distillation (oil bath temperature: 210 °C, head temperature: 150–160 °C) to obtain 10.8 g racemic diacetonexylitol (46.2 mmol, 70%) as a colorless oil.

Diacetone xylitol methacrylate

A mixture of 3.76 g rac-diacetonexylitol (16.2 mmol, 1.0 eq), 1.37 mL methacrylic acid (16.2 mmol, 1.0 eq), 0.40 g 4-(dimethylamino)pyridine (3.20 mmol, 0.20 eq), 5.16 g dicyclohexylcarbodiimide (25.0 mmol, 1.5 eq), and a spatula tip of hydroquinone (stabilizer) were stirred in 40 mL of chloroform overnight. The crude product is a yellowish oil. The approximate composition of the crude product was determined by 1H-NMR spectroscopy (70 wt% rac-diacetonexylitol methacrylate, 5 wt% dicyclohexyl urea, 25 wt% dicyclohexylcarbodiimide). With 4.43g of crude product, the yield is 3.11g of product (10.4 mmol) and a yield of 64%.

Poly(xylitol-1-monomethacrylate)

4.13 g of rac-diacetonexylitol methacrylate crude (rac-diacetonexylitol methacrylate 2.89 g, 9.63 mmol, 1.00 eq; purified via a basic aluminum oxide column prior to use), 40.0 mg AIBN (0.24 mmol, 2.6 mol%), and 30 mL of toluene were placed in a 100 mL Schlenk flask. The solution was degassed by three consecutive freeze-pump-thaw cycles and stirred overnight at 70 °C under a nitrogen atmosphere. The solution was then cooled to room temperature. The settling reaction mixture was concentrated, and the polymer was precipitated in cold MeOH. 1.36 g of poly(rac-diacetonexylitol methacrylate) was obtained as a colorless solid. The protected polymer was added to 5 mL of methanol acidified with HCl (pH = 1) and stirred at 70 °C for 3 h. The solution was then cooled. The polar polymer was precipitated in tetrahydrofuran, washed several times with tetrahydrofuran, and dried in a vacuum oven at 80 °C, yielding 1.00 g of poly(rac-xylitol-1-monomethacrylate) as a colorless solid.

a) Application testing

To test the effectiveness of the stabilizer composition according to the invention, a polypropylene (Moplen HF 501N, manufacturer: LyondellBasell) was fed in a continuous cycle at 90 revolutions per minute for 30 minutes in a twin-screw microextruder (MC 15 HT, manufacturer: Xplore) at 200 °C, together with the additives listed in the table. The force applied was measured as torque after 10, 20, and 30 minutes. The force is a measure of the viscosity of the melt and thus of the molecular weight. The higher the remaining force or torque, the lower the polymer degradation. Additional information Torque retention [%] after 10/20/30 minutes Comparative example 1 0.13 w% FeCl2 4H2O (≙ 350 ppm Fe) 50/22/10 Example according to the invention 1 0.13 w% FeCl2 4H2O0.50 w% PXMMA 61/36/21 Example 2 according to the invention 0.13 w% FeCl2 4H2O0.25 w% PXMMA0.25 w% Irganox 1076 89/84/84 PXMMA= Poly(xylitol-1-monomethacrylate)

QUOTES INCLUDED IN THE DESCRIPTION

This list of documents cited by the applicant was automatically generated and is included solely for the reader's convenience. The list is not part of the German patent or utility model application. The DPMA accepts no liability for any errors or omissions.

Cited patent literature

• WO 2019063550 [0002]
• WO 2020083740 [0002]
• WO 2023198777 [0002]
• JP 07316098 [0003]
• WO 2020/193563 [0004]
• WO 2008101845 [0066]
• WO 2014/064064 [0066]
• US 2 716 101 [0074]
• US 3 326 852 [0074]
• US 4 328 174 [0074]
• US 4 331 614 [0074]
• US 4 374 971 [0074]
• US 4 415 719 [0074]
• US 5 216 113 [0074]
• US 5 334 692 [0074]
• US 6 291 630 B1 [0074]
• US 6 861 499 B2 [0074]
• US 7816486 B2 [0074]
• US 2005/0020800 A1 [0074]
• US 2007/0219295 A1 [0074]
• US 2008/0045673 A1 [0074]
• US 3 946 093 [0074]
• US 3 919 363 [0074]
• US 6 288 210 B1 [0074]
• US 2 682 522 [0074]
• US 2 891 915 [0074]
• WO 2013020696 [0077]
• WO 2010135398 [0077]
• WO 2006084488 [0077]
• WO 2006084489 [0077]
• WO 2011000019 [0077]
• WO 2013068437 [0077]
• WO 2013072295 [0077]
• EP 2450401 [0079]

Cited non-patent literature

• G. Koßmehl, J. Volkheimer, Liebigs Ann. Chem. 1991, 1079-1081 [0003]
• M. Aubert et. al. Macromol. Sci. Closely. 2007, 292, 707-714 [0066]
• M. Aubert et al., Pol. Adv. Technol. 2011, 22, 1529-1538 [0066]
• W. Pawelec et al., Pol. Degr. Rod. 2012, 97, 948-954 [0066]

Claims (19)

Polymer stabilizer containing a polymer chain to which alditols and/or cyclitols are bound, wherein the polymer chain was obtained by radical polymerization. Polymer stabilizer after Claim 1 , with a structure according to general formula I wherein R ¹ is a residue derived from an alditol or cyclitol, which is bonded via a carbon atom, wherein the alditol has at least 4 carbon atoms, R ² and R ³ are the same or different and are selected from the group consisting of hydrogen and linear or branched alkyl residues having 1 to 32 carbon atoms, in particular that R ² and R ³ are the same and each represent a methyl group, AO or NH is X is a bridging group, a is 1 or 0, b is 1 or 0, and P is the polymer chain. Polymer stabilizer according to the preceding claim, characterized in that R ¹ is selected from the group consisting of the following residues wherein c is 2, 3, 4 or 5, or R ⁴ is selected from the group consisting of hydrogen, -OH and -OR ⁵ , wherein R ⁵ represents a linear or branched alkyl group with 1 to 32 carbon atoms, in particular is methyl, with the proviso that of all R ⁴ groups at least ³ groups are not hydrogen. Polymer stabilizer according to one of the two preceding claims, characterized in that R ¹ is selected from the group consisting of the following residues: Polymer stabilizer according to one of the Claims 2 until 4 , characterized in that b equals 1 and X is the subsequent grouping: Polymer stabilizer according to one of the preceding claims, characterized in that the polymer chain has a repeating unit according to general formula II. where R ¹ , R ² , R ³ , X, a and b are the in Claim 2 specified meaning and R ⁶ is the same or different in each occurrence and is selected from the group consisting of hydrogen, linear or branched alkyl group with 1 to 32 carbon atoms, in particular methyl and aromatic groups, in particular phenyl or alpha-methylphenyl. Polymer stabilizer according to one of the preceding claims, characterized in that the polymer stabilizer is a homopolymer and is in particular formed from repeating units of formula II. Polymer stabilizer according to one of the Claims 1 until 6 , characterized in that the polymeric stabilizer is a copolymer and, in addition to the repeating unit according to general formula II, comprises at least one further repeating unit obtained by radical polymerization, wherein the at least one further repeating unit obtained by radical polymerization preferably has the following structure according to general formula III: where X, R ⁶ and b have the meanings given above. Polymer stabilizer according to the preceding claim, characterized in that the molar ratio of the totality of repeating units according to general formula II to the totality of the sum of all repeating units according to general formula II and general formula III is from 0.01 to 99.9, preferably from 0.05 to 0.95. Polymer stabilizer according to one of the preceding claims, characterized in that in formula I or II R ² and R ³ are each methyl, A is oxygen, X is -C(=O)- and a and b are each 1. Stabilizer composition comprising or consisting of at least one polymeric stabilizer according to any of the preceding claims and at least one additive, distinct from the polymeric stabilizer, selected from the group consisting of primary antioxidants, secondary antioxidants, UV absorbers, light stabilizers, in particular hindered amines as light (HALS) and long-term heat stabilizers (HAS), metal deactivators, filler deactivators, antiozonants, nucleating agents, antinucleating agents, clarifiers, impact enhancers, plasticizers, lubricants, rheology or viscosity modifiers, thixotropic agents, chain extenders, processing aids, demolding aids, flame retardants, pigments, dyes, optical brighteners, antimicrobial agents, antistatic agents, slip agents, antiblocking agents, coupling agents, crosslinking agents, anticrosslinking agents, hydrophilizing agents, hydrophobizing agents, and surface modifiers. Hydrolysis stabilizers, adhesion promoters, dispersants, compatibilizers, oxygen scavengers, acid scavengers, acetaldehyde and formaldehyde scavengers, blowing agents, degradation additives (prodegradants), defoaming agents, odor traps and odor-improving substances, PVC heat stabilizers, marking agents, antifogging agents, gloss enhancers, matting agents, additives to increase electrical and/or thermal conductivity, repellents, fillers and reinforcing agents and mixtures thereof. Stabilizer composition according to the preceding claim, characterized in that the weight ratio of the totality of the at least one stabilizer to the total stabilizer composition is from 0.01 to 0.99, preferably from 0.2 to 0.80. Stabilized polymer composition containing at least one polymeric stabilizer according to one of the Claims 1 until 9 or a stabilizer composition according to one of the two preceding claims, and at least one polymer. Stabilized polymer composition according to the preceding claim, characterized in that the at least one polymer is selected from the group consisting of a) polymers of olefins or diolefins such as polyethylene (LDPE, LLDPE, VLDPE, ULDPE, MDPE, HDPE, UHMWPE), metallocene-PE (m-PE), polypropylene, polyisobutylene, poly-4-methylpentene-1, polybutadiene, polyisoprene, such as natural rubber (NR), polycyclooctene, polyalkylene-carbon monoxide copolymers, as well as 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 a comonomer, ethylene-vinyl acetate (EVA), ethylene acrylates, such as ethylene-butyl acrylate, ethylene-acrylic acid and their salts (ionomers), as well as terpolymers such as, for example, Ethylene-acrylic acid-glycidyl(meth)acrylate, graft polymers such as polypropylene-graft-maleic anhydride, polypropylene-graft-acrylic acid, polyethylene-graft-acrylic acid, polyethylene-polybutylacrylate-graft-maleic anhydride, and blends such as LDPE/LLDPE or long-chain branched polypropylene copolymers produced with alpha-olefins as comonomers such as 1-butene, 1-hexene, 1-octene, or 1-octadecene; b) polystyrene, polymethylstyrene, polyalphamethylstyrene, polyvinylnaphthalene, polyvinylbiphenyl, polyvinyltoluene, styrene-butadiene (SB), styrene-butadiene-styrene (SBS), styrene-ethylene-butylene-styrene (SEBS), styrene-ethylene-propylene-styrene, styrene-isoprene. Styrene-isoprene-styrene (SIS), styrolutadiene acrylonitrile (ABS), styrene-acrylonitrile (SAN), styrene-acrylonitrile acrylate (ASA), styrene-ethylene, styrene-maleic anhydride polymers including corresponding graft copolymers such as styrene on butadiene, maleic anhydride on SBS or SEBS, as well as graft copolymers of 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 like polymethyl methacrylate (PMMA), polybutyl acrylate, polylauryl acrylate, polystearyl acrylate, polyglycidyl acrylate, polyglycidyl methacrylate rylate, polyacrylonitrile, polyacrylamides, copolymers such as polyacrylonitrile-polyalkyl acrylate, e) polymers of unsaturated alcohols and derivatives, such as polyvinyl alcohol, polyvinyl acetate, polyvinyl butyral, polyallyl phthalate, polyallyl melamine, f) polyacetals, such as polyoxymethylene (POM) or copolymers with, for example, 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, of hydroxy-terminated polyethers or polyesters and aromatic or aliphatic isocyanates such as 2,4- or 2,6-toluene diisocyanate or methylene diphenyl diisocyanate, in particular also 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., produced 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, polyethersulfones, polyarylsulfones, polyphenylene sulfides, polybenzimidazoles, Polyhydantoins, I) Polyesters made from aliphatic or aromatic dicarboxylic acids and diols or from hydroxycarboxylic acids such as polyethylene terephthalate (PET), polybutylene terephthalate (PBT), polypropylene terephthalate (PTI), polyethylene naphthylate (PEN), poly-1,4-dimethylolcyclohexane terephthalate, polyhydroxybenzoate, 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, for example, Hardeners based on amines, anhydrides, dicyandiamide, mercaptans, isocyanates or catalytically acting 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, methylphenylsiloxanes or diphenylsiloxanes, e.g. vinyl group terminated, s) as well as mixtures, combinations or blends of two or more of the aforementioned polymers. Stabilised polymer composition according to one of the two preceding claims, characterized in that the at least one polymeric stabilizer or the stabilizer composition is contained in the stabilized polymer composition in an amount of 0.01 to 10 wt.%, preferably 0.1 to 5.0 wt.%, particularly preferably 0.2 to 1.0 wt.%. Method for producing a polymeric stabilizer according to one of the Claims 1 until 9 , in which at least one monomer of the general formula IV where R ¹ , R ² , R ³ , A, X and R ⁶ are defined as above and one of the residues R ⁷ is a residue R ⁶ and the other residue R ⁷ is hydrogen, is polymerized by radical means. Method according to the preceding claim, characterized in that the radical polymerization is carried out in the presence of at least one further radically polymerizable monomer, which preferably has a structure according to general formula V: where X, R ⁶ , R ⁷ and b have the preceding meaning. Method for stabilizing a polymer, in particular against thermal, actinic or oxidative degradation, by incorporating at least one polymeric stabilizer according to one of the Claims 1 until 10 or a stabilizer composition according to one of the Claims 11 and 12 into the polymer. Use of a polymeric stabilizer according to one of the Claims 1 until 10 or a stabilizer composition according to one of the Claims 11 and 12 for stabilizing polymers, especially against thermal, actinic or oxidative degradation.