Stabiliser composition, use of the stabiliser composition, method for stabilising condensation polymers against hydrolytic degradation, and hydrolysis-stabilised composition and moulding or moulded part consisting thereof

Abstract

The present invention relates to a novel stabiliser composition based on an aziridine and at least one oxide, carbonate and / or hydroxide of calcium, magnesium, aluminium or zinc, or mixtures of a plurality of the aforementioned compounds, wherein hydrotalcites, zeolites and dawsonites are excluded. The stabiliser composition is suitable for stabilising condensation polymers, in particular aliphatic polyesters against hydrolytic degradation. The invention also relates to the use of the stabiliser composition according to the invention and to a method for stabilising condensation polymers against hydrolytic degradation. The present invention further relates to molded parts and moldings that can be produced from the composition according to the invention.

Description

[0001] Stabilizer composition, use of the stabilizer composition, process for stabilizing condensation polymers against hydrolytic degradation as well as hydrolysis-stabilized composition and shaped body or molded part made therefrom. The present invention relates to a novel stabilizer composition based on an aziridine and at least one oxide, carbonate and / or hydroxide of calcium, magnesium, aluminum or zinc or mixtures of several of the aforementioned compounds, with the exception of hydrotalcites, zeolites and dawsonites. The stabilizer composition is suitable for stabilizing condensation polymers, in particular aliphatic polyesters, against hydrolytic degradation. The invention also relates to the use of the stabilizer composition according to the invention and to a process for stabilizing condensation polymers against hydrolytic degradation.Furthermore, the present invention relates to molded parts and molded articles that can be produced from the composition according to the invention. Polycondensation polymers such as polyesters, polyamides, and polycarbonates are generally classified as hydrolysis-sensitive polymers, since the chemical bonds of these polymers can be cleaved by water. This can be advantageous for the degradation of these polymers, e.g., in the environment, but is also frequently disadvantageous, particularly for technical applications and the desired extended service life. Polymers made from fossil raw materials are increasingly being replaced by polymers made from renewable raw materials. These "bio" polymers are, for example, based on aliphatic polyesters such as polylactic acid, also known as polylactide or PLA. However, aliphatic ester groups are significantly more sensitive to hydrolysis than (partially) aromatic ester groups (see, e.g., M.Dröscher et al., Angewandte Macromolecular Chemistry 1984, 128, 203-213).

[0002] Improving the hydrolysis stability of polycondensation polymers and PLA is a well-known issue. For example, WO 2012 072 489 mentions carbodiimides, polycarbodiimides, epoxides, alkyl ketene dimers, and oxazolidinones as hydrolysis stabilizers. CN 101 759 969 describes hydrolysis-resistant PLA-based compositions containing carbodiimides, epoxy, oxoazolines, oxazines, or aziridines. Compositions are also known, for example from WO 94 / 24201, which contain further additives such as calcium oxide or calcium silicates in addition to the hydrolysis stabilizer in the form of epoxides. The use of aziridines in polyesters and PLA is also mentioned, for example, in US 3,959,228, TW 1472575, and US 2014 / 0100318. However, certain additives such as fillers can also have a negative impact on hydrolysis resistance; for example, it is known that layered silicates such as montmorillonite accelerate the hydrolysis of PLA (A.Rapacz-Kmita et al. Materials Letters 2015, 146, 73-76, Q. Zhao et al. Polymer Degradation and Stability 2008, 93, 1450-1459).

[0003] In addition, drilling fluids are known that may contain aziridines, hydrotalcites and degradable polymers (WO2015 / 065575).

[0004] Polycondensates containing aziridines are therefore considered to be the state of the art. For example, the use of aziridines in polyesters and PLA is mentioned in US 3959228, TW 1472575, US 2014 / 0100318, and US 2016 / 024297. However, there is still a need to increase the hydrolytic stability of polycondensation polymers, especially polyesters and especially aliphatic polyesters such as PLA, in order to expand the application possibilities of these polymers.

[0005] This object is achieved with respect to a stabilizer composition having the features of patent claim 1. Claim 7 specifies possible uses of the stabilizer composition, while claim 10 relates to a method for stabilizing condensation polymers against hydrolytic degradation. Claim 11 relates to a hydrolysis-stabilized composition, and claim 16 relates to a molded part or a molded body producible from the hydrolysis-stabilized composition.

[0006] The dependent patent claims each relate to advantageous further developments.

[0007] According to a first aspect, the present invention thus relates to a stabilizer composition consisting of at least one aziridine and at least one oxide, carbonate, and / or hydroxide of calcium, magnesium, aluminum, or zinc, or mixtures of several of the aforementioned compounds. However, the aforementioned oxides, carbonates, and hydroxides do not include hydrotalcites, zeolites, and dawsonites; these are thus excluded.

[0008] It is surprising that polyesters containing combinations of aziridines with at least one oxide, carbonate, and / or hydroxide of calcium, magnesium, aluminum, or zinc, or mixtures of several of the aforementioned compounds, exhibit particularly good hydrolytic stability. These combinations have not previously been described in the literature.

[0009] New hydrolysis-stabilized plastic compositions made from polycondensation polymers such as polyesters or polyamides, as well as new stabilizer compositions for improving hydrolysis stability with high effectiveness, particularly in biopolymers such as PLA, are provided. According to a preferred embodiment, the at least one aziridine is selected from the group consisting of monofunctional, difunctional, trifunctional, tetrafunctional, and / or multifunctional aziridines having, for example, the following structures:

[0010] A) Monofunctional aziridines

[0011] 1-aziridinecarboxamide, N-octadecyl-;

[0012] 1-aziridinecarboxamide, N-phenyl-;

[0013] 1-aziridinecarboxamide, N-cyclohexyl-;

[0014] 1-aziridinecarboxamide, N-1-naphthalenyl-;

[0015] 1-aziridinecarboxamide, N-decyl-;

[0016] N-benzyloxycarbonylaziridines;

[0017] (4-Methoxyphenyl)(2-methyl-1-aziridinyl)methanone;

[0018] N-(4-Cyclohexylphenyl)-1-aziridincarboxamid;

[0019] 2-[2-(1-Aziridinyl)ethoxy]-4-pyridinpyridincarbonsäure;

[0020] 6-[2-(1-Aziridinyl)ethoxy]-3-pyridinmethanamine;

[0021] 6-[2-(1-Aziridinyl)ethoxy]-2-pyridinpyridincarbonsäure;

[0022] 2-[2-(1-Aziridinyl)ethoxy]pyridin;

[0023] 2-[2-(1-Aziridinyl)ethoxy]-4-pyridinmethanamine;

[0024] 2-methyl-aziridine;

[0025] 2-[1-(1-Aziridinylmethyl)propoxy]-pyridin;

[0026] B) difunktionellen Aziridinen

[0027] N,N'-Hexamethylen-1,6-bis(1-aziridincarboxamid);

[0028] N,N'-(Methylendi-p-phenylen)bis(aziridin-1-carboxamid);

[0029] N,N'-(Methylenedi-4,1-phenylen)bis[2-methyl-1-aziridincarboxamid];

[0030] 1-Aziridinecarboxamide, N,N'-(3,3'-dimethyl[1,1'-biphenyl]-4,4'-diyl)bis-;

[0031] 1-Aziridinecarboxamide, N,N'-[1,1'-biphenyl]-4,4'-diylbis-;

[0032] 1-Aziridinecarboxamide, N,N'-(methylenedi-4,1-phenylen)bis-;

[0033] 1-Aziridinecarboxamide, N,N'-(4-methyl-1,3-phenylen)bis-;

[0034] 1-Aziridinecarboxamide, N,N'-(1,4-phenylenedi-2,1-ethanediyl)bis-;

[0035] 1-Aziridinecarboxamide, N,N'-1,4-phenylenbis-;

[0036] N,N'-(hexane-1,6-diyl)bis(2-methylaziridine-1-carboxamide);

[0037] N,N'-1,2-Ethanediylbis[1-aziridinecarboxamide]; N,N'-1,3-Propandiylbis[1-aziridinecarboxamide];

[0038] N,N'-1,4-Butanediylbis[1-aziridinecarboxamide];

[0039] N,N'-1,5-Pentandiylbis[1-aziridinecarboxamide];

[0040] N,N'-1,6-Hexanediylbis[1-aziridinecarboxamide];

[0041] N,N'-1,7-Heptanediylbis[1-aziridinecarboxamide];

[0042] N,N'-1,8-Octanediylbis[1-aziridincarboxamid];

[0043] N,N'-1,9-Nonanediylbis[1-aziridincarboxamid];

[0044] N,N'-1,10-Decanediylbis[1-aziridincarboxamid];

[0045] 1-Aziridincarboxamid, N,N'-(3-hydroxy-1,5-pentandiyl)bis-

[0046] 1-Aziridincarboxamid, N,N'-1,5-naphthalenediylbis-;

[0047] 1-Aziridincarboxamid, N,N'-(3,3'-dimethoxy[1,1'-biphenyl]-4,4'-diyl)bis- ; pentan

[0048] 1-Aziridincarboxamid, N,N'-(methyl-1,3-phenylen)bis-;

[0049] 1-Aziridincarboxamid, N,N'-[1,1'-biphenyl]-4,4'-diylbis-;

[0050] Poly(oxy-1,4-butanediyl),a-[[[3-[(1-aziridinylcarbonyl)amino]-4-methyl- phenyl]amino]carbonyl]-ω -[[[[3-[(1-aziridinylcarbonyl)amino]-4- methylphenyl]amino]carbonyl]oxy]-;

[0051] N,N"-(methylenedi-4,1-phenylen)bis[N'-1-aziridinyl-harnstoff;

[0052] C) Trifunktionellen Aziridinen

[0053] Pentaerythritol tris[3-(1-aziridinyl)propionat];

[0054] Trimethylolpropan tris[3-(2-methylaziridin-1-yl)propionat];

[0055] Trimethylolpropan Tris[3-(aziridin-1-yl)propionat];

[0056] 1-Aziridinpropionsäure, 2-[[3-(1-aziridinyl)-1-oxopropoxy]methyl]-1,3- propandiylester;

[0057] 1-Aziridinpropionsäure, α- methyl -, 1, 1'-[2-[[3-(1-aziridinyl)-2-methyl-1- oxopropoxy]methyl]-2-ethyl-1,3-propandiyl]ester;

[0058] 1-Aziridinpropionsäure, 2-[[(1-aziridinylacetyl)oxy]methyl]-2-ethyl-1,3- propandiylester;

[0059] 1-Aziridinpropionsäure, 2-methyl-, 1,1',1"-(2-ethyl-1,2,3-pro- pantriyl)ester;

[0060] 1-Aziridincarboxamid, N,N',N"-(methylidynetri-4,1-phenylen)tris; 1-Aziridincarboxamid, N,N'-[[[6-[(1-aziridinylcarbonyl)amino]hexyl]- imino]bis(carbonylimino-6,1-hexanediyl)]bis-;

[0061] 1-Aziridinpropionsäure, 2-methyl-, 1, 1'-[2-ethyl-2-[[3-(2-methyl-1- aziridinyl)-1-oxopropoxy]methyl]-1,3-propandiyl]ester;

[0062] 1-Aziridinpropionsäure, 1,1'-[2-[[3-(1-aziridinyl)-1-oxopropoxy]methyl]-

[0063] 2-ethyl-1,3-propandiyl]ester;

[0064] 1-Aziridinpropionsäure, 1,1’-[2-[[3-(1-aziridinyl)-1-oxopropoxy]methyl]-

[0065] 2-(hydroxymethyl)-1,3-propandiyl]ester;

[0066] Poly(oxy-1,2-ethanediyl),α,α, α"-1,2,3-propantriyltris[ ω -[[[[3-[(1- aziridinylcarbonyl)amino]-4-methylphenyl]amino]carbonyl]oxy]-; Aziri- dine, 1,1',1"-(s-phenenyltricarbonyl)tris[2-methyl-;

[0067] D) Tetrafunktionellen Aziridinen

[0068] Pentaerythritol tetrakis(ß-aziridino)propionat;

[0069] 1-Aziridinpropionsäure, 1,1'-[2,2-bis[[3-(1-aziridinyl)-1-oxopropoxy]- methyl]-1,3-propandiyl]ester;

[0070] 1-Aziridinpropionsäure, 2-methyl-, 1, 1'-[2,2-bis[[3-(2-methyl-1-aziridi- nyl)-1-oxopropoxy]methyl]-1,3-propandiyl]ester;

[0071] 1 -Aziridinethanol, a,a'-[[2,2-bis[2-hydroxy-3-(2-methyl-1-aziridinyl)- propoxy]methyl]-1,3-propandiyl]bis(oxymethylene)]bis[2-methyl-;

[0072] Ethanon, 2,2',2",2'"-[[2,2'-bipyridin]-6,6'-diylbis(methylenenitrilo)]- tetrakis[1-(2-methyl-1-aziridinyl)-;

[0073] 1,5-Pentandion, 2-[bis[2-(2-methyl-1-aziridinyl)-2-oxoethyl]amino]-1,5- bis(2-methyl-1-aziridinyl)-;

[0074] Ethanon, 2,2',2",2"'-(1,2-ethanediyldinitrilo)tetrakis[1-(2-methyl-1- aziridinyl)-;

[0075] Methanon, 1,1',1",1'"-(1,4,5,8-naphthalenetetrayl)tetrakis[1-(2-me- thyl-1-aziridinyl)-;

[0076] 1 -Aziridinethanol, α,α'-[[2,2-bis[2-hydroxy-3-(2-methyl-1-aziridi- nyl)propoxy]methyl]-1,3-propandiyl]bis(oxymethylen)]bis[2-methyl-;

[0077] E) Multifunktionellen Aziridinen

[0078] 1-aziridinepropionic acid, 1,1'-[2-[[3-[3-(1-aziridinyl)-1-oxopropoxy]-2,2-bis[[3-(1-aziridinyl)-1-oxopropoxy]methyl]propoxy]methyl]-2-[[3-(1-aziridinyl)-1-oxopropoxy]methyl]-1,3-propanediyl]ester; 1-aziridinepropionic acid, 2-methyl-, 1, 1'-[2-[[3-[3-(1-aziridinyl)-1-ox-opropoxy]-2-(hydroxymethyl)-2-[[3-(2-methyl-1-aziridinyl)-1-ox-opropoxy]methyl]propoxy]methyl]-2-[[3-(2-methyl-1-aziridinyl)-1-ox- opropoxy]methyl]-1,3-propanediyl]ester;

[0079] 1-Aziridinepropionic acid, ß,2-dimethyl-, benzylhexaylhexamethylene ester;

[0080] 1-Aziridinepropionic acid, 2-ethyl-ß-methyl-, benzylhexaylhexakis(methylene) ester; as well as mixtures and combinations of the aforementioned aziridines.

[0081] Particularly suitable aziridines are:

[0082] N,N'-(methylenedi-p-phenylene)bis(aziridine-1-carboxamide),

[0083] Pentaerythritol tris[3-(1-aziridinyl)propionate]

[0084] N,N'-(hexane-1,6-diyl)bis(2-methylaziridine-1-carboxamide)

[0085]

[0086] Trimethylolpropane tris[3-(2-methylaziridin-1-yl)propionate]

[0087] Trimethylolpropane tris[3-(aziridin-1-yl)propionate]

[0088] Further preferred aziridines are described in WO 2020 / 020714 and WO 2021 / 148570. The disclosure content of these patent applications regarding the mentioned aziridines is incorporated into the disclosure content of the present invention.

[0089] Particularly preferred aziridines are the following compounds:

[0090]

[0091] Some of the aziridines mentioned are commercially available, e.g. from Menadiona (Barcelona, ​​Spain), Polyaziridine LLC (Palm Beach, USA) or Covestro (Leverkusen, Germany)

[0092] According to an advantageous embodiment, the oxide, carbonate and / or hydroxide of calcium, magnesium, aluminum or zinc has a pK s -value of at least 10.

[0093] For example, and particularly preferably, the oxide, carbonate and / or hydroxide of calcium, magnesium, aluminum or zinc is selected from the group consisting of CaO, CaCO3, Ca(OH)2, MgO, MgCO3, Mg(OH)2, CaMg(CO3)2(dolomite), Al2O3, Al2(CO3)3, Al(OH)3, ZnO, ZnCO3, and Zn(OH)2, as well as mixtures and combinations thereof.

[0094] In the stabilizer composition according to the present invention, it is further advantageous if the weight ratio of the total of the aziridines to the total of the at least one oxide, carbonate or hydroxide of calcium, magnesium, aluminum or zinc is 20:1 to 1:20, preferably from 10:1 to 1:10, particularly preferably from 5:1 to 1:5, in particular 1:1 to 1:4.

[0095] In addition, the present invention relates to the use of a previously described stabilizer composition according to the invention for stabilizing condensation polymers against hydrolytic degradation.

[0096] In a further aspect, the present invention relates to a process for stabilizing condensation polymers against hydrolytic degradation, in which a stabilizer composition according to the invention as described above is admixed or blended with the condensation polymer.

[0097] Both the use according to the invention and the process according to the invention are advantageously characterized in that the stabilizer composition is used or admixed in a weight ratio of 0.01 to 10% by weight, preferably 0.05 to 5% by weight, particularly preferably 0.1 to 3% by weight, based on the polycondensation polymer.

[0098] In a preferred embodiment of the use, method or composition, it is provided that the condensation polymer is selected from the group consisting of a) polyamides, such as polyamide 6, 6.6, 6.9, 6.10, 4.6, 4.10, 6.12, 10.10, 10.12, 12.12, polyamide 4, polyamide 7, polyamide 8, polyamide 9, polyamide 11, polyamide 12 and (partially) aromatic polyamides such as polyphthalamides, e.g. prepared 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, referred to e.g. as polyamide 6T, polyamide 9T, polyamide 61, polyamide 6-3-T, blends of different polyamides such as PA-6 and PA 6.6, PA6T and PA6I, PA-6.6 and PA6T or blends of polyamides and polyolefins such as PA / PP or PA / PE.b) Polyesters made from aliphatic or aromatic dicarboxylic acids and diols or from hydroxycarboxylic acids, in particular aliphatic polyesters, such as polyethylene terephthalate (PET), polybutylene terephthalate (PBT), polytrimethylene terephthalate (PTT), polyethylene naphthylate (PEN), poly-1,4-dimethylhydroxycyclohexane terephthalate, polyhydroxybenzoate, polyhydroxynaphthalate, polylactic acid (PLA), polyhydroxybutyrate (PHB), polyhydroxyvalerate (PHV), polybutylene succinate (PBS), polybutylene succinate adipate (PBSA), polyethylene succinate, polycaprolactone, c) Polycarbonates, polyester carbonates, and blends such as PC / ABS, PC / PBT, PC / PET / PBT, PC / PA, d) and mixtures, combinations or blends of two or more of the aforementioned polymers.

[0099] Furthermore, the polymers listed under a) to c) can have both amorphous and (partially) crystalline morphologies.

[0100] Particularly preferred polyesters are aliphatic polyesters, ie polyesters that can be produced from aliphatic dicarboxylic acids and aliphatic diols or from aliphatic lactones.

[0101] Suitable diols for aliphatic polyesters are, for example, ethylene glycol, 1,3-propanediol, 1,2-propanediol, 1,4-butanediol, neopentyl glycol, 1,5-pentanediol, 1,6-hexanediol, 2,5-hexanediol, 3-methyl-2,4-pentanediol, 2-methyl-2,4-pentanediol, 2,2,4-trimethyl-1,3-pentanediol, 1,8-octanediol, 1,10-decanediol, 1,12-dodecanediol, 1,6,2-ethylhexanediol-1,3, 2,2-diethylpropanediol-1,3, 2,2-bis-(4-hydroxycyclohexyl)-propane, 2,2-bis-(4-hydroxypropoxyphenyl)-propane, 1,4-cyclohexanediol, 1,3-Cyclohexanediol, 1,4-Cyclohexanedimethanol, 1,3-Cyclohexanedimethanol.

[0102] Suitable dicarboxylic acids for aliphatic polyesters are, for example, malonic acid, dimethylmalonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, dodecanedioic acid, brassylic acid, tetradecanedioic acid, hexadecanedioic acid, cyclohexane-1,3-dicarboxylic acid or cyclohexane-1,4-dicarboxylic acid.

[0103] In addition to aliphatic structures, aromatic structures may also be present in minor amounts up to 20 mol%, preferably less than 10 mol%, most preferably less than 1 mol%. Suitable aromatic structures for diols are hydroquinone, resorcinol, 2,6-naphthalenediol, 1,8-naphthalenediol, and bisphenol A; for dicarboxylic acids, suitable aromatic structures are terephthalic acid, isophthalic acid, and naphthalene-2,6-dicarboxylic acid. An example of a heterocyclic aromatic dicarboxylic acid is 2,5-furandicarboxylic acid.

[0104] Suitable hydroxycarboxylic acids include lactic acid, glycolic acid, 4-hydroxybutyric acid, 3-hydroxybutyric acid or 3-hydroxyvaleric acid; a hydroxycarboxylic acid with aromatic moieties is mandelic acid.

[0105] Further preferred polyesters are in particular polybutylene terephthalate (PBT) and copolymers of 1,4-butanediol with terephthalic acid, adipic acid or sebacic acid, as well as polyethylene furanoate (PEF), obtainable from ethylene glycol and 1,4-furandicarboxylic acid.

[0106] Preferred polyamides are in particular polyamide 6, polyamide 6.6, blends of polyamide 6 with polyamide 6.6, polyamide 10.10, polyamide 10.12, polyamide 12.12, polyamide 11 and polyamide 12.

[0107] Particularly preferably, the at least one condensation polymer is selected from the group consisting of aliphatic polyesters, in particular polylactic acid (PLA), polybutylene succinate (PBS), polyethylene terephthalate (PET), polybutylene terephthalate (PBT), polyethylene furanoate (PEF), polyamide-6 or polyamide-6.6.

[0108] The present invention also relates to a hydrolysis-stabilized composition containing or consisting of at least one condensation polymer and a stabilizer composition according to the invention as described above. The preferred embodiments for the stabilizer composition and its use described above also apply without restriction to the hydrolysis-stabilized composition.

[0109] The hydrolytic stability is particularly evident in the slight increase in the melt volume flow rate (MVR) of the hydrolysis-stabilized composition when exposed to hydrolyzing conditions, which indicates a reduction in the molecular weight of the polymers used and thus a degradation caused by hydrolysis. For example, the hydrolysis-stabilized composition is characterized by a melt volume flow rate (MVR), determined according to DIN EN ISO 1133-1:2012 after storage of an extruded polymer granulate with a granule diameter between 1 and 3 mm (for example 2 mm) in deionized water for a period of 336 hours at a temperature of 60 °C (aliphatic polyesters) or 936 hours at a temperature of 85 °C ((partially) aromatic polyesters), which is increased by a maximum of 100%, preferably a maximum of 90%, compared to the melt volume flow rate (MVR) of the same sample before storage.Or over a period of 1344 hours at a temperature of 85 °C ((partially) aromatic polyesters), this is increased by a maximum of 250%, preferably a maximum of 200%, compared to the melt volume flow rate (MVR) of the same sample before storage.

[0110] Furthermore, high hydrolysis stability is demonstrated by a slight reduction in mechanical properties such as tensile and flexural strength when the hydrolysis-stabilized composition is exposed to hydrolyzing conditions, which indicate a reduction in the molecular weight of the polymers used and thus degradation caused by hydrolysis. For example, the hydrolysis-stabilized composition is characterized by a tensile strength, determined according to DIN EN ISO 527-1:2012, and a flexural strength, determined according to DIN EN ISO 178:2013, after storage of an injection-molded test specimen according to DIN EN ISO 527-2:2012 in deionized water for a period of 1334 hours at a temperature of 85 °C ((semi-)aromatic polyesters), which is reduced by a maximum of 40%, preferably a maximum of 10%, compared to the tensile or flexural strength of the same test specimen before storage.

[0111] In addition, the compositions may contain further additives selected from the group consisting of primary antioxidants, secondary antioxidants, UV absorbers, light stabilizers, metal deactivators, filler deactivators, antiozonants, nucleating agents, antinucleating agents, impact modifiers, plasticizers, lubricants, rheology modifiers, thixotropic agents, chain extenders, processing aids, mold release agents, flame retardants, pigments, dyes, optical brighteners, antimicrobial agents, antistatic agents, slip agents, antiblocking agents, coupling agents, crosslinking agents, anticrosslinking agents, hydrophilizing agents, hydrophobizing agents, hydrolysis stabilizers, adhesion promoters, dispersants, compatibilizers, oxygen scavengers, acid scavengers, blowing agents, degradation additives, Defoaming agents, odor absorbers, marking agents, antifogging agents, fillers and reinforcing agents.In a preferred embodiment, the compositions contain in particular phenolic antioxidants, phosphites or phosphonites, fillers or reinforcing fibers such as glass fibers.

[0112] Suitable phenolic antioxidants include:

[0113] 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-(a-methylcyclohexyl)-4,6-dimethylphenol, 2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, linear or branched nonylphenols, such as 2,6-dinonyl-4-methyl-phenol, 2,4-Dimethyl-6-(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;

[0114] alkylthiomethylphenols such as 2,4-dioctylthiomethyl-6-tert-butylphenol, 2,4-dioctylthiomethyl-6-methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol, 2,6-didodecylthiomethyl-4-nonylphenol;

[0115] 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-hydroxyphenyl stearate, bis(3,5-di-tert-butyl-4-hydroxylphenyl)adipate;

[0116] Tocopherols, such as α-, β-, γ-, 5-tocopherol and mixtures of these (vitamin E);

[0117] Hydroxylierte Thiodiphenylether, wie z.B. 2,2'-Thiobis(6-tert-butyl-4-methyl- phenol), 2,2'-Thiobis(4-octylphenol), 4,4'-Thiobis(6-tert-butyl-3-methyl- phenol), 4,4'-Thiobis(6-tert-butyl-2-methylphenol), 4,4'-Thiobis(3,6-di-sec- amylphenol), 4,4'-Bis(2,6-dimethyl-4-hydroxyphenyl)disulfid;

[0118] 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-butylphe- nol), 2,2'-Ethylidenbis(4,6-di-tert-butylphenol), 2,2'-Ethylidenbis(6-tert-butyl- 4-isobutylphenol), 2,2'-Methylenbis[6-(α-methylbenzyl)-4-nonylphenol], 2,2' - Methylenbis[6-(a,a-dimethylbenzyl)-4-nonylphenol], 4,4'-Methylenbis(2,6-di- tert-butylphenol, 4,4'-Methylenbis(6-tert-butyl-2-methylphenol), 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-methyl- phenyl)butan, 1,1-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)-3-n-dodecyl- mercaptobutan, Ethylenglycol-bis[3,3-bis(3'-tert-butyl-4'-hydroxyphenyl)buty- rat], Bis(3-tert-butyl-4-hydroxy-5-methylphenyl)dicyclo-pentadien,Bis[2-(3'- tert-butyl-2'-hydroxy-5'-methylbenzyl)-6-tert-butyl-4-methylphenyl]tereph- thalat, 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;,

[0119] O-, N- und S-Benzyl-Verbindungen, wie z.B. 3,5,3',5'-Tetra-tert-butyl-4,4'- dihydroxydibenzylether, Octadecyl-4-hydroxy-3,5-dimethylbenzylmercapto- acetat, Tridecyl-4-hydroxy-3,5-di-tert-butyl-benzyl-mercaptoacetat, Tris(3,5-di- tert-butyl-4-hydroxybenzyl)amin, Bis(4-tert-butyl-3-hydroxy-2,6-dimethyl- benzyl)dithioterephthalat, Bis(3,5-di-tert-butyl-4-hydroxybenzyl)sulfid, Iso- octyl-3,5-di-tert-butyl-4-hydroxybenzylmercaptoacetat;

[0120] 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-methyl- benzyl)malonat, Didodecylmercaptoethyl-2,2-bis(3,5-di-tert-butyl-4-hydroxy- benzyl)malonat, Bis[4-(1,1,3,3-tetramethylbutyl)phenyl]-2,2-bis(3,5-di-tert- butyl-4-hydroxybenzyl)malonat;

[0121] 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-hydroxy- benzyl)-2,3,5,6-tetramethylbenzol, 2,4,6-Tris(3,5-di-tert-butyl-4-hydroxy- benzyl)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-hyd- roxyanilino)-1,3,5-triazin, 2-Octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxy- phenoxy)-1,3,5-triazin, 2,4,6-Tris(3,5-di-tert-butyl-4-hydroxyphenoxy)-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-triazin, 1,3,5-Tris(3,5-di-tert-butyl-4-hydroy- phenylpropionyl)hexahydro-1,3,5-triazin, 1,3,5-Tris(3,5-dicyclohexyl-4-hydro- xybenzyl)isocyanurat;

[0122] Benzylphosphonate, wie z.B. Dimethyl-2,5-di-tert-butyl-4-hydroxybenzylphos- phonat, Dietyhl-3,5-di-tert-butyl-4-hydroxybenzylphosphonat, Dioctadecyl-

[0123] 3.5-di-tert-butyl-4-hydroxybenzylphosphonat, Dioctadecyl-5-tert-butyl-4-hyd- roxy-3-methylbenzylphosphonat, das Calciumsalz des Monoethylesters der

[0124] 3.5-Di-tert-butyl-4-hydroxybenzylphosphonsäure;

[0125] Acylaminophenole, wie z.B. 4-Hydroxylauranilid, 4-Hydroxystearanilid, Octyl-N- (3,5-di-tert-butyl-4-hydroxyphenyl)carbamat;

[0126] Ester der ß-(3,5-Di-tert-butyl-4-hydroxyphenyl)propionsäure mit ein- oder mehrwertigen Alkoholen, z.B. Methanol, Ethanol, n-Octanol, i-Octanol, Octade- canol, 1,6-Hexandiol, 1,9-Nonandiol, Ethylenglycol, 1,2-Propandiol, Neopen- tylglycol, Thiodiethylenglycol, Diethylenglycol, Triethylenglycol, Pentaerythri- tol, Tris(hydroxyethyl)isocyanurat, N,N'-Bis(hydroxyethyl)oxamid, 3-Thiaunde- canol, 3-Thiapentadecanol, Trimethylhexandiol, Trimethylolpropan, 4-Hydro- xymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octan;

[0127] Esters of ß-(5-tert-butyl-4-hydroxy-3-methylphenyl)propionic acid with mono- or polyhydric alcohols, e.g. methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, Diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxamide, 3-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 ß-(3,5-dicyclohexyl-4-hydroxyphenyl)propionic acid with mono- or polyhydric alcohols, e.g.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;.

[0128] Ester der (3,5-Di-tert-butyl-4-hydroxyphenyl)essigsäure mit ein- oder mehrwer- tigen Alkoholen, z.B. Methanol, Ethanol, Octanol, Octadecanol, 1,6-Hexandiol, 1,9-Nonandiol, Ethylenglycol, 1,2-Propandiol, Neopentylglycol, Thiodiethylen- glycol, Diethylenglycol, Triethylenglycol, Pentaerythritol, Tris(hydroxyethyl)iso- cyanurat, N,N'-bis(hydroxyethyl)oxamid, 3-Thiaundecanol, 3-Thiapentadeca- nol, Trimethylhexandiol, Trimethylolpropan, 4-Hydroxymethyl-1-phospha- 2,6,7-trioxabicyclo[2.2.2]octan;

[0129] Amides of ß-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid, such as N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamide, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamide, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamide, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazide, N,N'-bis[2-(3-[3,5-di-tert-butyl-4-hydroxyphenyl]propionyloxy)ethyl]oxamide (Naugard®XL-1, distributed by Uniroyal);

[0130] Ascorbic acid (vitamin C).

[0131] Particularly preferred phenolic antioxidants are the following structures:

[0132] where in the above-mentioned compounds n is an integer and lies between 2 and 10.

[0133] Other preferred phenolic antioxidants are phenolic antioxidants based on renewable raw materials such as: B. α-, ß-, γ-, δ-tocopherol and mixtures of these (vitamin E), tocotrienols, tocomonoenols, ubiquinol, hydroxytyrosol, flavonoids and flavonols such as chrysin, quercetin, hesperidin, neohesperidin, naringin, morin, kaempferol, fisetin, datiscetin, luteolin, apigenin, taxifolin, isoflavones such as genistein, genistin, daidzein, daidzin, formononetin, anthocyanins such as delphinidin and malvidin, curcumin, carnosic acid, carnosol, rosmarinic acid, tannin and resveratrol as well as carotenoids with alcoholic groups such as beta-cryptoxanthin, lutein, zeaxanthin or astaxanthin.

[0134] Suitable aminic antioxidants include:

[0135] N,N'-Di-isopropyl-p-phenylendiamin, N,N'-Di-sec-butyl-p-phenylendiamin, N,N'-Bis(1,4-dimethylpentyl)-p-phenylendiamin, N,N'-Bis(1-ethyl-3-methyl- pentyl)-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-lsopropyl-N'-phenyl-p-phenylendiamin, N-(1,3-Dimethylbutyl)-N'-phenyl-p-phenylen-diamin, N-(1-Methylheptyl)-N'- phenyl-p-phenylendiamin, N-Cyclohexyl-N'-phenyl-p-phenylendiamin, 4-(p- Toluolsulfamoyl)diphenylamin, N,N'-Dimethyl-N,N'-di-sec-butyl-p-phenylen- diamin, Diphenylamin, N-Allyldiphenylamin, 4-lsopropoxydiphenylamin, 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-methoxyphe- nyl)amin, 2,6-Di-tert-butyl-4-dimethylaminomethylphenol, 2,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, N,N,N',N'-tetra-methyl-4,4'-diaminodiphenylmethane, 1,2-bis[(2-methylphenyl)amino]ethane, 1,2-bis(phenylamino)propane, (o-tolyl)biguanide, bis[4-(1',3'-dimethylbutyl)phenyl]amine, tert-octylated N-phenyl-1-naphthylamine, 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.

[0136] Preferred aminic antioxidants are: N,N'-diisopropyl-p-phenylenediamine, N,N'-di-sec-butyl-p-phenylenediamine, N,N'-bis(1,4-dimethylpentyl)-p-phenylenediamine, N,N'-bis(1-ethyl-3-methylpentyl)-p-phenylenediamine, N,N'-bis(1-methylheptyl)-p-phenylenediamine, N,N'-dicyclohexyl-p-phenylenediamine, N,N'-diphenyl-p-phenylenediamine, N,N'-bis(2-naphthyl)-p-phenylenediamine, N-isopropyl-N'-phenyl-p-phenylenediamine, N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine, N-(1-Methylheptyl)-N'-phenyl-p-phenylenediamine, N-cyclohexyl-N'-phenyl-p-phenylenediamine

[0137] Particularly preferred amine antioxidants are the structures:

[0138]

[0139] Preferred hydroxylamines or N-oxides (nitrones) 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:

[0140] Suitable lactones are benzofuranones and indolinones such as 3-(4-(2-acetoxyethoxy)phenyl]-5,7-di-tert-butyl-benzofuran-2-one, 5,7-di-tert-butyl-3-[4-(2-stearoyloxyethoxy)phenyl]benzofuran-2-one, 3,3'-bis[5,7-di-tert-butyl-3-(4-(2-hydroxyethoxy]phenyl)benzofuran-2-one), 5,7-di-tert-butyl-3-(4-ethoxyphenyl)benzofuran-2-one, 3-(4-acetoxy-3,5-dimethylphenyl)-5,7-di- tert-butyl-benzofuran-2-one, 3-(3,5-dimethyl-4-pivaloyloxyphenyl)-5,7-di- tert-butyl-benzofuran-2-one, 3-(3,4-dimethylphenyl)-5,7-di-tert-butyl-benzofuran-2-one, 3-(2,3-di-methylphenyl)-5,7-di-tert-butyl-benzofuran-2-one, as well as lactones that additionally contain phosphite groups such as

[0141]

[0142] Preferred fillers are calcium carbonate, silicates, talc, mica, kaolin, metal oxides and metal hydroxides, carbon black, graphite, wood flour, or fibers from natural products such as cellulose. Other suitable fillers are hydrotalcites or zeolites or phyllosilicates such as montmorillonite, bentonite, beidelite, mica, hectorite, saponite, vermiculite, ledikite, magadite, illite, kaolinite, wollastonite, and attapulgite. Other suitable organic fillers include rosin, starch, chitin, and chitosan.

[0143] Suitable secondary antioxidants are in particular phosphites or phosphonites such as

[0144] Triphenylphosphit, Diphenylalkylphosphite, Phenyldialkylphosphite, Tri(nonyl- phenyl)phosphit, Trilaurylphosphite, Trioctadecylphosphit, Distearylpenta- erythritoldiphosphit, Tris-(2,4-di-tert-butylphenyl)phosphit, Diisodecylpenta- erythritoldiphosphit, Bis(2,4-di-tert-butylphenyl)pentaerythritoldiphosphit, Bis(2,4-di-cumylphenyl)pentaerythritoldiphosphit, Bis(2,6-di-tert-butyl-4-me- thylphenyl)pentaerythritoldiphosphit, Diisodecyloxypentaerythritoldiphosphit, Bis(2,4-di-tert-butyl-6-methylphenyl)pentaerythritoldiphosphit, Bis(2,4,6- tris(tert-butylphenyl)pentaerythritoldiphosphit, Tristearylsorbitoltriphosphit, Tetrakis(2,4-di-tert-butylphenyl)-4,4'-biphenylendiphosphonit, 6-lsooctyloxy- 2,4,8,10-tetra-tert-butyl-12H-dibenz[d,g]-1,3,2-dioxaphosphocin, Bis(2,4-di- tert-butyl-6-methylphenyl)methylphosphit, Bis(2,4-di-tert-butyl-6-methylphe- nyl)ethylphosphit, 6-Fluoro-2,4,8,10-tetra-tert-butyl-12-methyl-dibenz[d,g]-

[0145] 1.3.2-dioxaphosphocin, 2,2'2"-nitrilo[triethyltris(3,3",5,5'-tetra-tert-butyl-1,1'-biphenyl-2,2'-diyl)phosphite], 2-ethylhexyl(3,3',5,5'-tetra-tert-butyl-1,1'- biphenyl-2,2'-diyl))phosphite, 5-butyl-5-ethyl-2-(2,4,6-tri-tert-butylphenoxy)-

[0146] 1.3.2-dioxaphosphirane.

[0147] Particularly preferred phosphites are:

[0148] with n= 3-100

[0149] A preferred phosphonite is: Suitable secondary antioxidants also include organosulfur compounds such as sulfides and disulfides, e.g., distearyl thiodipropionate, dilauryl thiodipropionate, ditridecyl dithiopropionate, ditetradecyl thiodipropionate, 3-(dodecylthio)-, 1,1'-[2,2-bis[[3-(dodecylthio)-1-oxopropoxy]methyl]-1,3-propanediyl]propanoic acid esters. The following structures are preferred:

[0150] Suitable acid scavengers ("antacids") are salts of monovalent, divalent, trivalent, or tetravalent metals, preferably alkali metals, alkaline earth metals, aluminum, or zinc, especially formed with fatty acids, such as calcium stearate, magnesium stearate, zinc stearate, aluminum stearate, calcium laurate, calcium behenate, calcium lactate, calcium stearoyl-2-lactate. Other classes of suitable acid scavengers are hydrotalcites, especially synthetic hydrotalcites based on aluminum, magnesium, and zinc, hydrocalumites, zeolites, alkaline earth oxides, especially calcium oxide and magnesium oxide, and zinc oxide, alkaline earth carbonates, especially calcium carbonate, magnesium carbonate, and dolomite, and hydroxides, especially brucite (magnesium hydroxide).

[0151] Suitable costabilizers are also polyols, especially alditols or cyclitols. Polyols include pentaerythritol, dipentaerythritol, tripentaerythritol, short-chain polyether polyols or polyester polyols, as well as hyperbranched polymers / oligomers or dendrimers with alcohol groups, e.g.

[0152] Preferably, the at least one alditol is selected from the group consisting of threitol, erythritol, galactitol, mannitol, ribitol, sorbitol, xylitol, arabitol, isomalt, lactitol, maltitol, altritol, iditol, maltotritol, and hydrogenated oligosaccharides and polysaccharides 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-D-galacto-heptitol (Perseitol), D-glycero-D-gluco-heptitol, L-glycero-D-gluco heptitol, D-erythro-L-galacto-octitol, D-threo-L-galacto-octitol.

[0153] In particular, the at least one cyclitol can be selected from the group consisting of inositol (myo, scyllo-, D-chiro-, L-chiro-, muco-, neo-, allo-, epi- and cis-inositol), 1,2,3,4-tetrahydroxycyclohexane, 1, 2,3,4, 5-pentahydroxycyclohexane, quercitol, viscumitol, bornesitol, conduritol, ononitol, pinitol, pinpollitol, quebrachitol, ciceritol, quinic acid, shikimic acid and valienol, preference being given to myo-inositol (myo-inositol).

[0154] Light stabilizers are, for example, compounds based on 2-(2'-hydroxyphenyl)benzotriazoles, 2-hydroxybenzophenones, esters of benzoic acids, acrylates, oxamides and 2-(2-hydroxyphenyl)-1,3,5-triazines.

[0155] Geeignete 2-(2'-Hydroxyphenyl)benzotriazole sind beispielsweise 2-(2'-Hyd- roxy-5'methylphenyl)benzotriazol, 2-(3',5'-Di-tert-butyl-2'-hydroxyphenyl)- benzotriazol, 2-(5'-tert-Butyl-2'-hydroxy-phenyl)benzotriazol, 2-(2'-Hydroxy-5'- (1,1,3,3-tetramethylbutyl)phenyl)benzotriazol, 2-(3',5'-Di-tert-butyl-2'-hydro- xyphenyl)-5-chlorobenzotriazol, 2-(3'-tert-Butyl-2'-hydroxy-5'-methylphenyl-5- chlorobenzotriazol, 2-(3'-sec-Butyl-5'-tert-butyl-2'-hydroxy-phenyl)benzotria- zol, 2-(2'-Hydroxy-4'-octyloxyphenyl)benzotriazol, 2-(3',5'-Di-tert-amyl-2'-hyd- roxyphenyl)benzotriazol, 2-(3',5'-Bis(a,a-dimethylbenzyl)-2'-hydroxyphe- nyl)benzotriazol, 2-(3'-tert-Butyl-2'-hydroxy-5'-(2-octyloxycarbonylethyl)phe- nyl)-5-chlorobenzotriazol, 2-(3'-tert-Butyl-5'-[2-(2-ethylhexyloxy)carbonyl- ethyl]-2'-hydroxyphenyl)-5-chlorobenzotriazol, 2-(3'-tert-Butyl-2'-hydroxy-5'- (2-methoxycarbonyl-ethyl)phenyl)-5-chlorobenzotriazol, 2-(3'-tert-Butyl-2'- hydroxy-5'-(2-methoxycarbony-lethyl)phenyl)-benzotriazol,2-(3'-tert-Butyl-2'- hydroxy-5'-(2-octyloxycarbonylethyl)-phenyl)-benzotriazol, 2-(3'-tert-Butyl-5'- [2-(2-ethylhexyloxy)carbonylethyl]-2'-hydroxyphenyl)benzotriazol, 2-(3'-Dode- cyl-2'-hydroxy-5'-methylphenyl)benzotriazol, 2-(3'-tert-Butyl-2'-hydroxy-5'-(2- isooctyloxycarbonylethyl)-phenyl-benzotriazol, 2,2'-Methylenbis[4-(1,1,3,3- tetramethylbutyl)-6-benzotriazol-2-ylphenol]; das Produkt der Umesterung von 2-[3'-tert-Butyl-5'-(2-methoxycarbonylethyl)-2'-hydroxyphenyl]-2H-ben- zotriazol mit Polyethylenglycol 300; [R— CH2CH2— COO— CH2CH2+2, wobei 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]-benzotriazol, 2-[2'- hydroxy-3'-(1,1,3,3-tetramethylbutyl)-5'-(a,a-dimethylbenzyl)phenyl]benzotri- azol.,

[0156] Suitable 2-hydroxybenzophenones are, for example, 4-hydroxy, 4-methoxy, 4-octyloxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy, 4,2',4'-trihydroxy and 2'-hydroxy-4,4'-dimethoxy derivatives of 2-hydroxybenzophenones. Suitable acrylates are, for example, ethyl-a-cyano-ß,ß-diphenyl acrylate, isooctyl-a-cyano-ß,ß-diphenyl acrylate, methyl-a-carbomethoxycinnamate, methyl-a-cyano-ß-methyl-p-methoxycinnamate, butyl-a-cyano-ß-methyl-p-methoxycinnamate, Methyl-a-carbomethoxy-p-methoxycinnamate and N-(ß-carbo-methoxy-ß-cyanovinyl)-2-methylindoline.

[0157] Suitable esters of benzoic acids are, 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, 2-methyl-4,6-di-tert-butylphenyl-

[0158] 3.5-di-tert-butyl-4-hydroxybenzoate.

[0159] Suitable oxamides are, 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.

[0160] Geeignete 2-(2-Hydroxyphenyl)-1,3,5-Triazine sind beispielsweise 2,4,6-Tris(2- hydroxy-4-octyloxyphenyl)-1,3,5-triazin, 2-(2-Hydroxy-4-octyloxyphenyl)-4,6- bis(2,4-dimethylphenyl)-1,3,5-triazin, 2-(2,4-Dihydroxyphenyl)-4,6-bis(2,4-di- methylphenyl)-1,3,5-triazin, 2,4-Bis(2-hydroxy-4-propyloxyphenyl)-6-(2,4-di- methylphenyl)-1,3,5-triazin, 2-(2-Hydroxy-4-octyloxyphenyl)-4,6-bis(4-methyl- phenyl-1,3,5-triazin, 2-(2-Hydroxy-4-dodecyloxyphenyl)-4,6-bis(2,4-dimethyl- phenyl)-1,3,5-triazin, 2-(2-Hydroxy-4-tridecyloxyphenyl)-4,6-bis(2,4-dimethyl- phenyl)-1,3,5-triazin, 2-[2-Hydroxy-4-(2-hydroxy-3-butyloxypropoxy)-phenyl]-

[0161] 4.6-bis(2,4-dimethyl)-1,3,5-triazin, 2-[2-Hydroxy-4-(2-hydroxy-3-octyloxypro- pyloxy)phenyl]-4,6-bis(2,4-dimethyl)-1,3,5-triazin, 2-[4-(Dodecyloxy / Tridecy- loxy-2-hydroxypropoxy)-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5- triazin, 2-[2-Hydroxy-4-(2-hydroxy-3-dodecyloxypropoxy)phenyl]-4,6-bis(2,4- dimethylphenyl-1,3,5-triazin, 2-(2-Hydroxy-4-hexyloxy)phenyl-4,6-diphenyl- 1,3,5-triazin, 2-(2-Hydroxy-4-methoxyphenyl)-4,6-diphenyl-1,3,5-triazin, 2,4,6- Tris[2-hydroxy-4-(3-butoxy-2-hydroxypropoxy)phenyl]-1,3,5-triazin, 2-(2-Hyd- roxyphenyl)-4-(4-methoxyphenyl)-6-phenyl-1,3,5-triazin, 2-{2-Hydroxy-4-[3-(2- ethylhexyl-1-oxy)-2-hydroxypropyloxy]phenyl}-4,6-bis(2,4-dimethylphenyl- 1,3,5-triazin.

[0162] Suitable metal deactivators are, 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.

[0163] Particularly preferred as metal deactivators are:

[0164] Suitable low molecular weight hindered amines are for example

[0165] 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-tetramethylpiperazinone), 4-benzoyl-2,2,6,6-tetramethylpiperidine or 4-stearyloxy-2,2,6,6-tetramethylpiperidine.

[0166] 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) analogues.

[0167] Preferred low molecular weight hindered amines also have the following structures:

[0168]

[0169] Preferred oligomeric or polymeric hindered amines are:

[0170] For the compounds mentioned above, n is 3 to 100. Another suitable light stabilizer is Hostanox NOW (manufacturer: Clariant SE) with the following general structure: where R -OC(O)-C 15 H 31 or -OC(O)-C 17 H 35 means.

[0171] 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) analogues.

[0172] Suitable dispersants are, 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.

[0173] Suitable antinucleating agents are azine dyes such as nigrosine.

[0174] Suitable flame retardants are in particular 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 (Polyhedral Oligomeric Silsesquioxane) compounds, huntite, hydromagnesite or halloysite as well as Sb2O3, Sb2O5, MoO3, zinc stannate, zinc hydroxystannate, 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 asMelamine aluminum phosphate, melamine zinc phosphate, melamine magnesium phosphate, as well as the corresponding pyrophosphates and polyphosphates, poly-[2,4-(piperazin-1,4-yl)-6-(morpholin-4-yl)-1,3,5-triazine], ammonium polyphosphate, melamine borate, melamine hydrobromide, c) radical formers, such as alkoxyamines, hydroxylamine esters, azo compounds, sulfenamides, sulfenimides, dicumyl or polycumyl, hydroxyimides and their derivatives such as hydroxyimide esters or hydroxyimide ethers d) phosphorus-containing flame retardants 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 their 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, e) Halogen-containing flame retardants based on chlorine and bromine, such as polybrominated diphenyl oxides, such as decabromodiphenyl oxide, tris(3-bromo-2,2-bis(bromomethyl)propyl phosphate, tris(tribromoneopentyl)phosphate, tetrabromophthalic acid, 1,2-bis(tribromophenoxy)ethane, hexabromocyclododecane, brominated diphenylethane, tris(2,3-dibromopropyl)isocyanurate, Ethylene bis(tetrabromophthalimide), tetrabromobisphenol A, brominated polystyrene, brominated polybutadiene or polystyrene-brominated polybutadiene copolymers, brominated polyphenylene ether, brominated epoxy resin, polypentabromobenzyl acrylate, optionally in combination with Sb2O3 and / or Sb2O5, f) borates such as zinc borate or calcium borate, optionally.on a carrier material such as silica g) sulfur-containing compounds such as elemental sulfur, disulfides and polysulfides, thiuram sulfide, dithiocarbamates, mercaptobenzothiazole and sulfenamides, h) anti-drip agents such as polytetrafluoroethylene, i) silicon-containing compounds such as polyphenylsiloxanes, j) carbon modifications such as carbon nanotubes (CNT), expanded graphite or graphene k) and combinations or mixtures thereof. Suitable plasticizers are, for example, phthalic acid esters, adipic acid esters, esters of citric acid, esters of 1,2-cyclohexanedicarboxylic acid, trimellitic acid esters, isosorbide esters, phosphate esters, epoxides such as epoxidized soybean oil or aliphatic polyesters.

[0175] Suitable lubricants and processing aids are, for example, polyethylene waxes, polypropylene waxes, salts of fatty acids such as calcium stearate, zinc stearate or salts of montan waxes, amide waxes such as erucic acid amide or oleic acid amides, fluoropolymers, silicones or neoalkoxy titanates and zirconates.

[0176] Suitable pigments can be inorganic or organic. Inorganic pigments include, for example, titanium dioxide, zinc oxide, zinc sulfide, iron oxide, ultramarine, and carbon black. Organic pigments include, for example, anthraquinones, anthanthrones, benzimidazolones, quinacridones, diketopyrrolopyrroles, dioxazines, indanthrones, isoindolinones, azo compounds, perylenes, phthalocyanines, or pyranthrones. Other suitable pigments include metal-based effect pigments or metal oxide-based pearlescent pigments.

[0177] Suitable optical brighteners are, for example, bisbenzoxazoles, phenylcoumarins or bis(styryl)biphenyls and in particular optical brighteners of the formulas:

[0178]

[0179] Suitable filler deactivators are, for example, polysiloxanes, polyacrylates, especially block copolymers such as polymethacrylic acid polyalkylene oxide or

[0180] Polyglycidyl(meth)acrylates and their copolymers e.g. with styrene as well as epoxides e.g. of the following structures:

[0181]

[0182] Suitable antistatic agents include ethoxylated alkylamines, fatty acid esters, alkylsulfonates and polymers such as polyetheramides.

[0183] Suitable antiozonants are the above-mentioned amines such as N,N'-di-isopropyl-p-phenylenediamine, N,N'-di-sec-butyl-p-phenylenediamine, N,N'-bis-(1,4-dimethylpentyl)-p-phenylenediamine, N,N'-dicyclohexyl-p-phenylenediamine, N-isopropyl-N'-phenyl-p-phenylenediamine, N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine, N-(1-methylheptyl)-N'-phenyl-p-phenylenediamine, N-cyclohexyl-N'-phenyl-p-phenylenediamine.

[0184] Suitable nucleating agents are talc, alkali or alkaline earth metal salts of mono- and polyfunctional carboxylic acids such as benzoic acid, succinic acid, adipic acid, e.g. sodium benzoate, zinc glycerolate, aluminum hydroxy-bis(4-tert-butyl)benzoate, 2,2'-methylene-bis-(4,6-di-tert-butylphenyl)phosphate, as well as trisamides 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-dimethylpropanamide) or 2,6-naphthalenedicarboxylic acid dicyclohexylamide.

[0185] Suitable additives for increasing the molecular weight of polycondensation polymers (chain extenders) are diepoxides, bis-oxazolines, bis-oxazolones, bis-oxazines, diisocyanates, dianhydrides, bis-acyl lactams, bis-maleimides, dicyanates, and carbodiimides. Other suitable chain extenders are polymeric compounds such as polystyrene-polyacrylate-polyglycidyl (meth)acrylate copolymers, polystyrene-maleic anhydride copolymers, and polyethylene-maleic anhydride copolymers.

[0186] 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 additives for increasing thermal conductivity include, for example, aluminum nitrides and boron nitrides.

[0187] Suitable infrared-active additives include aluminum silicates, hydroalcites or dyes such as phthalocyanines or anthraquinones.

[0188] Suitable demoulding aids include silicones, soaps and waxes such as montan waxes.

[0189] The above-described additive composition and any additional additives are incorporated into the plastic using conventional processing methods, whereby the polymer is melted and mixed with the additive composition according to the invention and any other additives, preferably using a mixer, kneader, or extruder. Preferred processing machines are extruders such as single-screw extruders, twin-screw extruders, planetary roller extruders, ring extruders, and co-kneaders, which are preferably equipped with vacuum degassing. Processing can take place under air or, if appropriate, under inert gas conditions.

[0190] Furthermore, the additive compositions according to the invention can be prepared 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.

[0191] Furthermore, the present invention relates to a molded part or a molded body that can be produced from a hydrolysis-stabilized composition according to the present invention. In particular, the molded part or the molded body is selected from the group consisting of foils, films, foams, fibers, cables and pipes, profiles, hollow bodies, tapes, membranes, such as geomembranes, or adhesives that are produced via extrusion, injection molding, blow molding, calendering, pressing processes, spinning processes, or rotomolding, e.g. for the electrical and electronics industry, the construction industry, the transport industry (cars, aircraft, ships, trains), for medical applications, for household and electrical appliances, vehicle parts, consumer goods, packaging, furniture, and textiles.

[0192] The present invention is explained in more detail with reference to the following examples, without the examples being understood as limiting the subject matter of the present invention.

[0193] Examples of implementation:

[0194] To test the effectiveness of the stabilizer composition according to the invention, a polylactide (PLA) (Luminy L130, supplier: Total Corbion) was compounded together with the additives listed in Table 1 at a maximum temperature of 200 °C in a twin-screw extruder (Process 11, manufacturer: ThermoScientific) at a throughput of 800 g / h. The polymer and additives were dried overnight in a vacuum dryer prior to processing. After compounding, the compounds were aged in deionized water at 60 °C in an oven for 14 days (336 hours). After aging, the samples were dried overnight, and the MVR was determined (190 °C / 2.16 kg).

[0195] Table 1 : Hydrolysis stability of PLA

[0196]

[0197] To test the effectiveness of the stabilizer composition according to the invention, a polybutylene terephthalate (PBT) (Pocan B1204, supplier: Lanxess AG) was compounded together with the additives listed in Table 1 at a maximum temperature of 250 °C in a twin-screw extruder (Process 11, manufacturer: ThermoScientific) at a throughput of 800 g / h. The polymer and additives were dried overnight in a vacuum dryer prior to processing. After compounding, the compounds were aged in deionized water at 85 °C in an oven for 39 days (936 hours). After aging, the samples were dried overnight, and the MVR was determined (250 °C / 2.16 kg).

[0198] Table 2 : Hydrolytic stability of PBT

[0199] The stabilizing effect was further tested with another polybutylene terephthalate grade (PBT) (Arnite T06 200 / D, supplier: DSM) together with the additives listed in Table 1 at a maximum of 250 °C in a twin-screw extruder (Leistritz MIC 27, manufacturer: Leistritz) at a throughput of 6 kg / h. Tensile test specimens (according to DIN EN 527-2 Type 1A) were then injection molded on an injection molding machine (Arburg Allrounder 320 C, manufacturer: Arburg) at a maximum of 250 °C. The polymer, additives, and compounds were dried in a dry air dryer for at least 6 hours before processing. After compounding, the compounds and test specimens were aged in deionized water at 85 °C in an oven for 56 days (1344 hours). After aging, the samples were dried overnight and the MVR (250 °C / 2.16 kg) as well as tensile and flexural strength were determined.

[0200] Table 3: Hydrolytic stability of PBT (MVR) Table 4: Hydrolytic stability of PBT (mechanics)

[0201] The examples according to the invention show a much higher hydrolysis stability than the comparative examples, which is reflected in a smaller increase in the MVR value and a smaller reduction in the tensile and flexural strength after

[0202] Water storage is demonstrated. The MVR is a measure of the flowability of the melt and thus also of the molecular weight of the polymer. The lower the molecular weight, the higher the MVR and thus also the degradation of the polymer through hydrolysis. The smaller the increase in MVR, the higher the hydrolytic stability. Tensile and flexural strengths are a measure of the mechanical properties of the compounds and indirectly also of the molecular weight of the polymer. The lower the molecular weight, the lower the tensile and flexural strength and the greater the degradation of the polymer through hydrolysis. The smaller the reduction in tensile and flexural strength, the higher the hydrolytic stability. The combinations according to the invention therefore demonstrate excellent hydrolytic stability.

Claims

Patent claims 1. Stabilizer composition consisting of at least one aziridine and at least one oxide, carbonate and / or hydroxide of calcium, magnesium, aluminum or zinc or mixtures of several of the aforementioned compounds, wherein hydrotalcites, zeolites and dawsonites are excluded from the aforementioned oxides, carbonates and hydroxides.

2. Stabilizer composition according to claim 1, characterized in that the at least one aziridine is selected from the group consisting of monofunctional, difunctional, trifunctional, tetrafunctional and / or multifunctional aziridines having, for example, the following structures: A) monofunctional aziridines 1-aziridinecarboxamide, N-octadecyl-; 1-aziridinecarboxamide, N-phenyl-; l-aziridinecarboxamide, N-cyclohexyl; l-aziridinecarboxamide, Nl-naphthalenyl-; 1-aziridinecarboxamide, N-decyl-; N-Benzyloxycarbonylaziridine; (4-Methoxyphenyl)(2-methyl-l-aziridinyl)methanon N-(4-Cyclohexylphenyl)-l-aziridincarboxamid; 2-[2-(l-Aziridinyl)ethoxy]-4-pyridincarboxylsäure; 6-[2-(l-Aziridinyl)ethoxy]-3-pyridinmethanamin; 6-[2-(l-Aziridinyl)ethoxy]-2-pyridincarboxylsäure; 2-[2-(l-Aziridinyl)ethoxy]pyridin; 2-Methyl-aziridin; 2-[l-(l-Aziridinylmethyl)propoxy]-pyridin; 2-[2-(l-Aziridinyl)ethoxy]-4-Pyridinemethanamine; B) difunktionellen Aziridinen N,N'-Hexamethylen-1,6-bis(1-aziridincarboxamid); N,N'-(Methylendi-p-phenylen)bis(aziridin-1-carboxamid); N,N'-(Methylenedi-4,1-phenylene)bis[2-methyl-1-aziridincarboxamid]; 1-Aziridincarboxamid, N,N'-(3,3'-dimethyl[1,1'-biphenyl]-4,4'-diyl)bis-; 1-Aziridincarboxamid, N,N'-[1,1'-biphenyl]-4,4'-diylbis-; 1-Aziridinecarboxamide, N,N'-(methylenedi-4,1-phenylene)bis-; 1-Aziridinecarboxamide, N,N'-(4-methyl-1,3-phenylene)bis-; 1-Aziridinecarboxamide, N,N'-(1,4-phenylenedi-2,1-ethanediyl)bis-; 1-Aziridinecarboxamide, N,N'-1,4-phenylenebis-; N,N'-(Hexan-1,6-diyl)bis(2-methylaziridin-1-carboxamide); N,N'-1,2-Ethandiylbis[1-aziridinecarboxamide]; N,N'-1,3-Propandiylbis[1-aziridinecarboxamide]; N,N'-1,4-Butanediylbis[1-aziridinecarboxamide]; N,N'-1,5-Pentandiylbis[1-aziridinecarboxamide]; N,N'-1,6-Hexandiylbis[1-aziridinecarboxamide]; N,N'-1,7-Heptandiylbis[1-aziridinecarboxamide]; N,N'-1,8-Octanediylbis[1-ziridinecarboxamide]; N,N'-1,9-Nonandiylbis[1-aziridinecarboxamide]; N,N'-1,10-Decandiylbis[1-aziridinecarboxamide]; 1-Aziridinecarboxamide, N,N'-(3-hydroxy-1,5-pentanediyl)bis- 1-Aziridinecarboxamide, N,N'-1,5-naphthalenediylbis-; 1-Aziridincarboxamid, N,N'-(3,3'-dimethoxy[1,1'-biphenyl]-4,4'-diyl)bis- ; 1-Aziridincarboxamid, N,N'-(methyl-1,3-phenylen)bis-; 1-Aziridincarboxamid, N,N'-[1,1'-biphenyl]-4,4'-diylbis-; Poly(oxy-1,4-butanediyl), α-[[[3-[(1-aziridinylcarbonyl)amino]-4- methylphenyl]amino]carbonyl]-(ω -[[[[3-[(1-aziridinylcarbonyl)amino]-4- methylphenyl]amino]carbonyl]oxy]-; N,N"-(Methylendi-4,1-phenylen)bis[N'-1-aziridinyl-harnstoff; C) Trifunktionellen Aziridinen Pentaerythritol-tris[3-(1-aziridinyl)propionat]; Trimethylolpropan-tris[3-(2-methylaziridin-1-yl)propionat]; Trimethylolpropan-tris[3-(aziridin-1-yl)propionat]; 1-Aziridinproprionsäure-2-[[3-(1-aziridinyl)-1-oxopropoxy]methyl]-1,3- propandiylester; 1-Aziridinproprionsäure-a-methyl-, 1, 1'-[2-[[3-(1-aziridinyl)-2-methyl- 1-oxopropoxy]methyl]-2-ethyl-1,3-propandiyl]ester; 1-Aziridinproprionsäure-2-[[(1-aziridinylacetyl)oxy]methyl]-2-ethyl-1,3- propandiylester; 1-Aziridinproprionsäure-2-methyl-1,1',1"-(2-ethyl-1,2,3-propantriyl)es- ter; 1-Aziridincarboxamid-N,N',N"-(methylidyntri-4,1-phenylen)tris; 1-Aziridincarboxamid,N,N'-[[[6-[(1-aziridinylcarbonyl)amino]hexyl]- imino]bis(carbonylimino-6,1-hexanediyl)]bis-; 1-Aziridinproprionsäure-2-methyl-, 1,1'-[2-ethyl-2-[[3-(2-methyl-1- aziridinyl)-1-oxopropoxy]methyl]-1,3-propandiyl]ester; 1-Aziridinproprionsäure-1,1'-[2-[[3-(1-aziridinyl)-1-oxopropoxy]me- thyl]-2-ethyl-1,3-propandiyl]ester; 1-Aziridinproprionsäure-1,1'-[2-[[3-(1-aziridinyl)-1-oxopropoxy]me- thyl]-2-(hydroxymethyl)-1,3-propandiyl]ester; Poly(oxy-1,2-ethanediyl)-a,a',a"-1,2,3-propantriyltris[(jj-[[[[3-[(1- aziridinylcarbonyl)amino]-4-methylphenyl]amino]carbonyl]oxy]-; Aziri-din-1,1',1"-(S-phenenyltricarbonyl)tris[2-methyl-]; D) Tetrafunktionellen Aziridinen Pentaerythritoltetrakis(ß-aziridino)propionat; 1-Aziridinproprionsäure-1,1'-[2,2-bis[[3-(1-aziridinyl)-1-oxopropoxy]- methyl]-1,3-propandiyl]ester; 1-Aziridinproprionsäure-2-methyl-, 1, 1'-[2,2-bis[[3-(2-methyl-1-aziridi- nyl)-1-oxopropoxy]methyl]-1,3-propandiyl]ester; 1-Aziridinethanol-a,a'-[[2,2-bis[2-hydroxy-3-(2-methyl-1-aziridinyl)- propoxy]methyl]-1,3-propandiyl]bis(oxymethylene)]bis[2-methyl-; Ethanon-2,2',2",2"'-[[2,2'-bipyridine]-6,6'-diylbis(methyleneni- trilo)]tetrakis[1-(2-methyl-1-aziridinyl)-; 1,5-Pentandion-2-[bis[2-(2-methyl-1-aziridinyl)-2-oxoethyl]amino]-1,5- bis(2-methyl-1-aziridinyl)-; Ethanon-2,2',2",2"'-(1,2-ethanediyldinitrilo)tetrakis[1-(2-methyl-1- aziridinyl)-; Methanon-1,1',1",1"'-(1,4,5,8-naphthalintetrayl)tetrakis[1-(2-methyl- 1-aziridinyl)-; 1-Aziridineethanol-α,α'-[[2,2-bis[2-hydroxy-3-(2-methyl-1-aziridinyl)propoxy]methyl]-1,3-propanediyl]bis(oxymethylene)]bis[2-methyl-; E) Multifunctional aziridines 1-aziridinepropionic acid 1,1'-[2-[[3-[3-(1-aziridinyl)-1-oxopropoxy]-2,2-bis[[3-(1-aziridinyl)-1-oxopropoxy]methyl]propoxy]methyl]-2-[[3-(1-aziridinyl)-1-oxopropoxy]methyl]-1,3-propanediyl] ester; 1-aziridineproprioic acid-2-methyl-, 1,1'-[2-[[3-[3-(1-aziridinyl)-1-ox-opropoxy]-2-(hydroxymethyl)-2-[[3-(2-methyl-1-aziridinyl)-1-ox-opropoxy]methyl]propoxy]methyl]-2-[[3-(2-methyl-1-aziridinyl)-1-ox- opropoxy]methyl]-1,3-propanediyl]ester; 1-Aziridinepropionic acid-ß,2-dimethyl-, benzylhexaylhexamethylene ester; 1-Aziridinepropionic acid 2-ethyl-ß-methyl-, benzylhexaylhexakis(methylene) ester; as well as mixtures and combinations of the aforementioned aziridines.

3. Stabilizer composition according to one of the preceding claims, characterized in that at least one aziridine is selected from the group consisting of the following compounds 4. Stabilizer composition according to one of the preceding claims, characterized in that the oxide, carbonate and / or hydroxide of calcium, magnesium, aluminum or zinc has a pK s - value of at least 10.

5. Stabilizer composition according to one of the preceding claims, characterized in that the oxide, carbonate and / or hydroxide of calcium, magnesium, aluminum or zinc is selected from the group consisting of CaO, CaCO3, Ca(OH)2, MgO, MgCO3, Mg(OH)2, CaMg(CO3)2, Al2O3, Al2(CO3)3, Al(OH)3, ZnO, ZnCO3, and Zn(OH)2, as well as mixtures and combinations thereof.

6. Stabilizer composition according to one of the preceding claims, characterized in that the weight ratio of the total of the aziridines to the total of the at least one oxide, carbonate or hydroxide of calcium, magnesium, aluminum or zinc is 20:1 to 1:20, preferably from 10:1 to 1:10, particularly preferably from 5:1 to 1:5, in particular 1:1 to 1:

4.

7. Use of a stabilizer composition according to one of claims 1 to 6 for stabilizing condensation polymers against hydrolytic degradation.

8. A process for stabilizing condensation polymers against hydrolytic degradation, in which a stabilizer composition according to any one of claims 1 to 6 is admixed with or blended with the condensation polymer.

9. Use or method according to one of claims 7 or 8, characterized in that the stabilizer composition is used or admixed in a weight ratio of 0.01 to 10% by weight, preferably of 0.05 to 5% by weight, particularly preferably of 0.1 to 3% by weight, based on the polycondensation polymer.

10. Use or method according to one of claims 7 to 9, characterized in that the polycondensation polymer is selected from the group consisting of a) polyamides, such as polyamide-6, 6.6, 6.9, 6.10, 4.6, 4.10, 6.12, 10.10, 10.12, 12.12, Polyamide 4, Polyamide 7, Polyamide 8, Polyamide 9, Polyamide 11, Polyamide 12 and (partially) aromatic poly- amides such as polyphthalamides, e.g. made from terephthalic acid and / or isophthalic acid and aliphatic diamines such as hexamethylenediamine or m-xylylenediamine or from aliphatic dicarboxylic acids such as adipic acid or sebacic acid and aromatic diamines such as 1,4- or 1,3-diaminobenzene, referred to e.g. as polyamide 6T, polyamide 9T, polyamide 61, polyamide-6-3-T, blends of different polyamides such as PA-6 and PA 6.6, PA6T and PA6I, PA-6.6 and PA6T or blends of polyamides and polyolefins such as PA / PP or PA / PE, b) polyesters made from aliphatic or aromatic dicarboxylic acids and diols or from hydroxycarboxylic acids, in particular aliphatic polyesters, such asPolyethylene terephthalate (PET), polybutylene terephthalate (PBT), polytrimethylene terephthalate (PTT), polyethylene naphthalate (PEN), poly-l,4-dimethylhydroxycyclohexane terephthalate, polyhydroxybenzoate, polyhydroxynaphthalate, polylactic acid (PLA), polyhydroxybutyrate (PHB), polyhydroxyvalerate (PHV), polybutylene succinate (PBS), polybutylene succinate adipate (PBSA), polyethylene succinate, polycaprolactone, polyethylene furanoate (PEF), c) polycarbonates, polyester carbonates, and blends such as PC / ABS, PC / PBT, PC / PET / PBT, PC / PA, d) as well as mixtures, combinations or blends of two or more of the aforementioned polymers.

11. Hydrolysis-stabilized composition containing or consisting of at least one condensation polymer and a stabilizer composition according to one of claims 1 to 8.

12. Hydrolysis-stabilized composition according to the preceding claim, characterized in that the stabilizer composition is present in a weight ratio of 0.01 to 10% by weight, preferably from 0.05 to 5% by weight, particularly preferably from 0.1 to 3% by weight, based on the polycondensation polymer.

13. Hydrolysis-stabilized composition according to one of the two preceding claims, characterized in that at least one additive selected from the group consisting of primary or secondary antioxidants, UV absorbers, light stabilizers, metal deactivators, filler deactivators, antiozonants, nucleating agents, antinucleating agents, impact strength improvers, plasticizers, lubricants, rheology modifiers, thixotropic agents, chain extenders, processing aids, mold release agents, flame retardants, pigments, dyes, optical brighteners, antimicrobial agents, antistatic agents, slip agents, antiblocking agents, coupling agents, crosslinking agents, anticrosslinking agents, hydrophilizing agents, hydrophobizing agents, hydrolysis stabilizers, adhesion promoters, dispersants, compatibilizers, oxygen scavengers, acid scavengers, blowing agents, degradation additives, defoaming aids, odor scavengers, marking agents,Antifogging agents, fillers and reinforcing agents are included.

14. Hydrolysis-stabilized composition according to one of claims 11 to 13, characterized in that the at least one condensation polymer is selected from the group consisting of aliphatic polyesters, in particular polylactic acid (PLA), polybutylene succinate (PBS), polyethylene terephthalate (PET), polybutylene terephthalate (PBT), polyethylene furanoate (PEF), polyamide-6 or polyamide-6.

6.

15. Hydrolysis-stabilized composition according to one of claims 11 to 14, characterized by a melt volume flow rate (MVR), determined according to DIN EN ISO 1133-1:2012 after storage of an extruded polymer granulate with a granule diameter between 1 and 3 mm in deionized water for a period of 336 hours at a temperature of 60 °C (aliphatic polyesters) or 936 hours at a temperature of 85 °C ((partially) aromatic polyesters), which is increased by a maximum of 100%, preferably a maximum of 90%, compared to the melt volume flow rate (MVR) of the same sample before storage.

16. A molded part or molded body, producible from a hydrolysis-stabilized composition according to any one of claims 11 to 15, in particular foils or films, foams, fibers, cables and pipes, profiles, hollow bodies, tapes, membranes, such as geomembranes, or adhesives, which are produced via extrusion, injection molding, blow molding, calendering, pressing processes, spinning processes, rotomoulding, for example 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.

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