DE19855598A1 - Stabilization of polyamide, polyester and polyacetal - Google Patents

Description

The present invention relates to compositions containing a polyamide, polyester or polyketone, a particular phenolic anitoxidant, the use of the same for Stabilizing polyamides, polyesters or polyacetals against oxidative, thermal and / or light-induced degradation, and a method for stabilizing these plastics.

From the U.S. Patents 3,691,131 and 3,860,558 are known to be polyamides phenolic antioxidants in the presence of metal hypophosphites such as Ka lium hypophosphite or sodium hypophosphite and copper salts of organic acids sta have it bilized.

These known stabilizer mixtures can be in polyamides, polyesters or polyacetals do not meet all requirements. It is known that such a stabilizer mix the initial color as well as the color development of the polyamide during the oven reduce aging and the deterioration of the mechanical properties of the poly Reduce amids during oven aging and exposure.

It has now been found that a very specific phenolic antioxidant is selected from the U.S. Patents 3,691,131 and 3,860,558 in the absence of metal hypophos phites and copper salts of organic acids, are particularly good as stabilizers for buttocks lyamide, polyester or polyacetals. The polyamides, polyesters or Polyacetals have improved properties with regard to oxidative, thermal and / or light-induced degradation.

The present invention therefore relates to compositions containing

• a) a polyamide subjected to oxidative, thermal or light-induced degradation, Polyester or polyacetal, and
• b) the compound of formula I.
  with the condition that when component (a) is a polyamide, the composition contains no metal hypophosphite and no copper salt of an organic acid.

Component (b) of the composition according to the invention, or the connection of the Formula I is known and has the Chemical Abstracts Registry number [37042-77-6]. The Preparation of the compound of formula I is described in GB-A-1 251 840, example 1, page 5 ben.

Among polyamides are aliphatic and aromatic polyamides or copolyamides, which are diamines and dicarboxylic acids and / or aminocarboxylic acids or their corresponding derived lactams to understand. Suitable polyamides are, for example: PA 6, PA 11, PA 12, PA 46, PA 6.6, PA 4.6, PA 6.9, PA 6.10 or PA 6.12, PA 10.12, PA 12.12 as well as amorphous polyamides of the type Trogamid PA 6-3-T and Grilamid TR 55. Polyami de of the type mentioned are generally known and commercially available.

Of interest are compositions containing as component (a) polyamide 6, poly amide 6.6, polyamide 4.6, polyamide 11 or polyamide 12 or copolymers thereof, in particular other polyamide 6 or polyamide 6.6 or elastomer-modified polyamide 6 or polyamide 6.6 blinded with polypropylene.

Polyesters can be homo- or mixed polyesters, which are made from aliphatic, cycloaliphatic or aromatic dicarboxylic acids and diols or hydroxycarboxylic acid ren are built.

The aliphatic dicarboxylic acids can have 2 to 40 carbon atoms, the cycloaliphatic dicar bonic acids 6 to 10 carbon atoms, the aromatic dicarboxylic acids 8 to 14 carbon atoms, the ali phatic hydroxy carboxylic acids 2 to 12 carbon atoms and aromatic such as cycloalipha tables contain hydroxycarboxylic acids 7 to 14 carbon atoms.  

The aliphatic diols can have 2 to 12 C atoms, the cycloaliphatic diols can have 5 to 8 C atoms and the aromatic diols contain 6 to 16 carbon atoms.

Aromatic diols are those in which two hydroxyl groups are attached to one or various aromatic hydrocarbon radicals are bound.

It is also possible that the polyester with small amounts, for. B. 0.1 to 3 mol%, bezo to the existing dicarboxylic acids, more than difunctional monomers (e.g. Penta erythritol, trimellitic acid, 1,3,5-tri (hydroxyphenyl) benzene, 2,4-dihydroxybenzoic acid or 2- (4- Hydroxyphenyl) -2- (2,4-dihydroxyphenyl) propane) are branched.

In the case of polyesters composed of at least 2 monomers, these can be randomly distributed or it can be block copolymers.

Suitable dicarboxylic acids are linear and branched saturated aliphatic dicarbons acids, aromatic dicarboxylic acids and cycloaliphatic dicarboxylic acids.

As aliphatic dicarboxylic acids are those with 2 to 40 carbon atoms in question, for. B. oxalic acid right, malonic acid, dimethylmalonic acid, succinic acid, pimelic acid, adipic acid, trimethyl adipic acid, sebacic acid, azelaic acid and dimer acids (dimerization products from un saturated aliphatic carboxylic acids such as oleic acid), alkylated malonic and succinic acid ren such as octadecyl succinic acid.

Possible cycloaliphatic dicarboxylic acids are: 1,3-cyclobutanedicarboxylic acid, 1,3- Cyclopentanedicarboxylic acid, 1,3- and 1,4-cyclohexanedicarboxylic acid, 1,3- and 1,4- (dicarbo xylmethyl) cyclohexane, 4,4'-dicyclohexyldicarboxylic acid.

Suitable aromatic dicarboxylic acids are: in particular terephthalate acid, isophthalic acid, o-phthalic acid, and 1,3-, 1,4-, 2,6- or 2,7-naphthalenedicarbon acid, 4,4'-diphenyldicarboxylic acid, 4,4'-diphenylsulfone dicarboxylic acid, 4,4'-benzophenondi carboxylic acid, 1,1,3-trimethyl-5-carboxyl-3- (p-carboxylphenyl) indane, 4,4'-diphenyletherdi carboxylic acid, bis-p- (carboxylphenyl) methane or bis-p- (carboxylphenyl) -ethane.  

Aromatic dicarboxylic acids are preferred, among them especially terephthalic acid. Isophthalic acid and 2,6-naphthalenedicarboxylic acid.

Other suitable dicarboxylic acids are those containing -CO-NH groups; they are in the DE-A-24 14 349. Also dicarboxylic acids containing N-heterocyclic rings are suitable, e.g. B. those that differ from carboxylalkylated, carboxylphenylated or carboxybenzylated monoamine-s-triazinedicarboxylic acids (cf. DE-A-21 21 184 and 25 33 675), mono- or bishydantoins, optionally halogenated benzimidazoles or Derive parabanic acid. The carboxyalkyl groups can have 3 to 20 carbon atoms contain.

Suitable aliphatic diols are the linear and branched aliphatic glycols, be especially those with 2 to 12, especially 2 to 6 carbon atoms in the molecule, e.g. E.g .: ethylene glycol, 1,2- and 1,3-propylene glycol, 1,2-, 1,3-, 2,3- or 1,4-butanediol, pentyl glycol, neo pentylglycol, 1,6-hexanediol, 1,12-dodecanediol. A suitable cycloaliphatic diol is e.g. B. 1,4-dihydroxycyclohexane. Other suitable aliphatic diols are e.g. B. 1,4-bis (hydroxymethyl) cyclohexane, aromatic aliphatic diols such as p-xylylene glycol or 2,5- Dichloro-p-xylylene glycol, 2,2- (β-hydroxyethoxyphenyl) propane and polyoxyalkylene glycols such as diethylene glycol, triethylene glycol, polyethylene glycol or polypropylene glycol. The alky Lendiols are preferably linear and contain in particular 2 to 4 carbon atoms.

Preferred diols are the alkylene diols, 1,4-dihydroxycyclohexane and 1,4-bis (hydroxy methyl) cyclohexane. Ethylene glycol, 1,4-butanediol and 1,2- and 1,3-propylene glycol.

Other suitable aliphatic diols are the β-hydroxyalkylated, especially β-hydroxy ethylated bisphenols such as 2,2-bis [4 '- (β-hydroxyethoxy) phenyl] propane. Other bisphenols are mentioned later.

Another group of suitable aliphatic diols are those in the German Offen documents 18 12 003, 23 42 432, 23 42 372 and 24 53 326 heterocyc diols. Examples are: N, N'-bis- (β-hydroxyethyl) -5,5-dimethyl-hydantoin, N, N'-bis- (β- hydroxypropyl) -5,5-dimethyl-hydantoin, methylene-bis- [N- (β-hydroxyethyl) -5-methyl-5-ethyl hydantoin], methylene-bis- [N- (β-hydroxyethyl) -5,5-dimethylhydantoin], N, N'-bis- (β-hydroxy  ethyl) benzimidazolone, N, N'-bis (β-hydroxyethyl) - (tetrachlor) benzimidazolone or N, N'-bis- (β-hydroxyethyl) - (tetrabromo) benzimidazolone.

As aromatic diols, mononuclear diphenols come into consideration and in particular bipernal ge, which carry a hydroxyl group on each aromatic nucleus. Aromatic are preferably aromatic hydrocarbon radicals such. B. phenylene or naphthylene were ver. In addition to e.g. B. hydroquinone, resorcinol or 1,5-, 2,6- and 2,7-dihydroxynaphthalene are particularly the bisphenols to be mentioned, which can be represented by the following formulas:

The hydroxyl groups can be in the m-position, but especially in the p-position, R 'and R''in these formulas can denote alkyl with 1 to 6 carbon atoms, halogen such as chlorine or bromine and in particular hydrogen atoms. A can stand for a direct bond, or can mean oxygen, sulfur, -SO-, -SO ₂ -, C = O, -P (O) (C ₁ -C ₂₀ alkyl) -, optionally substituted alkylidene, cycloalkylidene or alkylene .

Examples of optionally substituted alkylidene are: ethylidene, 1,1- or 2,2-propyli den, 2,2-butylidene, 1,1-isobutylidene, pentylidene, hexylidene, heptylidene, octylidene, dichloro ethylidene, trichloroethylidene.

Examples of optionally substituted alkylene are methylene, ethylene, phenylmethylene, Diphenylmethylene, methylphenylmethylene. Examples of cycloalkylidene are cyclopentylidene, Cyclohexylidene, cycloheptylidene and cyclooctylidene.

Examples of bisphenols are: bis (p-hydroxyphenyl) ether or thioether, bis (p-hydroxy phenyl) sulfone, bis (p-hydroxyphenyl) methane, bis (4-hydroxyphenyl) -2,2'-biphenyl, phenyl hydroquinone, 1,2-bis (p-hydroxyphenyl) ethane, 1-phenyl-bis (p-hydroxyphenyl) methane, di phenyl-bis (p-hydroxyphenyl) methane, diphenyl-bis (p-hydroxyphenyl) -ethane, bis (3,5-dimethyl- 4-hydroxyphenyl) sulfone, bis (3,5-dimethyl-4-hydroxyphenyl) -p-diisopropylbenzene, bis (3,5- dimethyl-4-hydroxyphenyl) -m-diisopropylbenzene, 2,2-bis (3 ', 5'-dimethyl-4'-hydroxyphenyl) - propane, 1,1- or 2,2-bis (p-hydroxyphenyl) butane, 2,2-bis (p-hydroxyphenyl) hexa fluoropropane, 1,1-dichloro- or 1,1,1-trichloro-2,2-bis (p-hydroxyphenyl) ethane, 1,1-bis (p- hydroxyphenyl) cyclopentane and especially 2,2-bis (p-hydroxyphenyl) propane (bisphenol-A) and 1,1-bis (p-hydroxyphenyl) cyclohexane (bisphenol-C).

Suitable polyesters of hydroxycarboxylic acids are e.g. B. polycaprolactone, polypivalolactone or the polyesters of 4-hydroxycyclohexane carboxylic acid or 4-hydroxybenzoic acid.  

Furthermore, there are also polymers which are predominantly ester bonds, but also other bonds can contain suitable, such as. B. polyester amides or polyester imides.

Polyesters with aromatic dicarboxylic acids have gained the greatest importance, especially especially the polyalkylene terephthalates. Formmas according to the invention are therefore preferred sen, in which the polyester from at least 30 mol%, preferably at least 40 mol%, aro Matic dicarboxylic acids and at least 30 mol%, preferably at least 40 mol%, is composed of alkylene diols with preferably 2 to 12 carbon atoms, based on the poly ester.

In particular, the alkylene diol is linear in this case and contains 2 to 6 carbon atoms, such as. B. Ethylene, tri, tetra or hexamethylene glycol and the aromatic dicarboxylic acid means Terephthalic and / or isophthalic acid.

Particularly suitable polyesters are PET, PETG (glycol-modified polyethylene tereph thalat) or PBT (polybutylene terephthalate) and corresponding copolymers, with PET and its copolymers are particularly preferred.

Polyacetals are, for example, homopolymers or copolymers of paraformaldehyde such as in particular polyoxymethylene (POM), and also such polyoxymethylenes, the comonomers, such as As ethylene oxide, contain and polyacetals with thermoplastic polyurethanes, Acrylates or MBS are modified.

Compositions as described above, in which the components te (b) in an amount of 0.01 to 1%, in particular 0.02 to 0.8%, for example 0.03 to 0.6%, based on the weight of component (a).

In addition to components (a) and (b), the compositions according to the invention can contain additional additives or costabilizers, for example the following:

• 1. Antioxidants
  • 1.1. Alkylated monophenols, e.g. B. 2,6-di-tert-butyl-4-methylphenol, 2-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-di-cyclopentyl-4-methylphenol, 2- (α-methylcyclohexyl) -4,6-dimethylphenol, 2, 6-di-octadecyl-4-methylphenol-2,4,6-tri-cyclohexylphenol, 2,6-di-tert-butyl-4-methoxy methylphenol, linear or branched nonylphenols such as e.g. B. 2,6-di-nonyl-4-methylphenol, 2,4-dimethyl-6- (1'-methyl-undec-1'-yl) phenol, 2,4-dimethyl-6- (1'- methyl-heptadec-1'-yl) phenol, 2,4-dimethyl-6- (1'-methyl-tridec-1'-yl) phenol and mixtures thereof.
  • 1.2. Alkylthiomethylohenols, e.g. B. 2,4-Di-octylthiomethyl-6-tert-butylphenol, 2,4-di-octylthio methyl-6-methylphenol, 2,4-di-octylthiomethyl-6-ethylphenol, 2,6-di-dodecylthiomethyl-4 -no nylphenol.
  • 1.3. Hydroquinones and alkylated hydroquinones, e.g. B. 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butyl-hydroquinone, 2,5-di-tert-amyl-hydroquinone, 2,6-diphenyl-4-octadecyloxyphenol, 2,6-di-tert-butyl hydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxy anisole, 3,5-di-tert-butyl -4-hydroxyphenyl stearate, bis (3,5-di-tert-butyl-4-hydroxyphenyl) adipate.
  • 1.4. Tocopherols, e.g. B. α-tocopherol, β-tocopherol, γ-tocopherol, δ-tocopherol and Mi mixtures thereof (vitamin E).
  • 1.5. Hydroxylated thiodiphenyl ethers, e.g. B. 2,2'-thio-bis (6-tert-butyl-4-methylphenol), 2,2'-thio-bis (4-octylphenol), 4,4'-thio-bis (6-tert-butyl -3-methylphenol), 4,4'-thio-bis- (6-tert-butyl-2-methylphenol), 4,4'-thio-bis (3,6-di-sec.-amylphenol), 4, 4'-bis (2,6-dimethyl-4-hydroxyphenyl) disulfide.
  • 1.6. Alkylidene bisphenols, e.g. B. 2,2'-methylene-bis (6-tert-butyl-4-methylphenol), 2,2'-methylene-bis (6-tert-butyl-4-ethylphenol), 2,2'-methylene-bis [4-methyl-6- (α-methylcyclohexyl) phenol], 2,2'-methylene-bis (4-methyl-6-cyclohexylphenol), 2,2'-methylene-bis (6-nonyl-4-methylphenol ), 2,2'-methylene-bis (4,6-di-tert-butylphenol), 2,2'-ethylidene-bis (4,6-di-tert-butylphenol), 2,2'-ethylidene-bis (6-tert-butyl-4-isobutylphenol), 2,2'-methylene-bis [6- (α-methylbenzyl) 4-nonyl phenol], 2,2'-methylene-bis [6- (α, α- dimethylbenzyl) -4-nonylphenol], 4,4'-methylene-bis (2,6-di-tert-butylphenol), 4,4'-methylene-bis (6-tert-butyl-2-methylphenol), 1, 1-bis (5-tert-butyl-4-hydroxy-2-methylphenyl) butane, 2,6-bis (3-tert-butyl-5-methyl-2-hydroxybenzyl) -4-methylphenol, 1.1 , 3-tris (5-tert-butyl-4-hydroxy-2-methylphenyl) butane, 1,1-bis (5-tert-butyl-4-hydroxy-2-methylphenyl) -3-n-dodecyl mercaptobutane , 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-dodecylmercapto-butane, 1,1,5,5-tetra (5-tert-butyl-4-hydroxy-2-methylphenyl) pentane.
  • 1.7. O-, N- and S-benzyl compounds, e.g. B. 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.
  • 1.8. Hydroxybenzylated malonates, e.g. B. Dioctadecyl-2,2-bis (3,5-di-tert-butyl-2-hydroxybenzyl) malonate, di-octadecyl-2- (3-tert-butyl-4-hydroxy-5-methylbenzyl) - malonate, di-dodecyl mercaptoethyl-2,2-bis (3,5-di-tert-butyl-4-hydroxybenzyl) malonate, di- [4- (1,1,3,3-tetramethyl butyl) phenyl] -2,2-bis (3,5-di-tert-butyl-4-hydroxybenzyl) malonate.
  • 1.9. Hydroxybenzyl aromatics, e.g. B. 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.
  • 1.10. Triazine compounds, e.g. B. 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) isocyanate, 1,3,5-tris (4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate, 2,4,6 tris (3,5-di- tert-butyl-4-hydroxyphenylethyl) -1,3,5-triazine, 1,3,5-tris (3,5-di-tert-butyl-4-hydroxyphenyl propionyl) hexahydro-1,3,5-triazine , 1,3,5-tris (3,5-dicyclohexyl) -4-hydroxybenzyl) isocyanurate.
  • 1.11. Benzylphosphonates, e.g. B. Dimethyl-2,5-di-tert-butyl-4-hydroxybenzylphosphonate, diethyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl-3,5-di-tert-butyl-4-hydroxy benzylphosphonate, dioctadecyl-5-tert-butyl-4-hydroxy-3-methylbenzylphosphonate, Ca salt of 3,5-di-tert-butyl-4-hydroxybenzylphosphonic acid monoethyl ester.
  • 1.12. Acylaminophenols, e.g. B. 4-Hydroxy-lauric anilide, 4-hydroxystearic anilide, N- (3,5-di-tert-butyl-4-hydroxyphenyl) carbamic acid octyl ester.
  • 1.13. Esters of β- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid with mono- or polyhydric alcohols, such as. B. with methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6-He xandiol, 1,9-nonandiol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, Tris ( hydroxyethyl) isocyanurate, N, N'-bis (hydroxyethyl) oxalic acid diamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo- [2.2.2 ] octane.
  • 1.14. Esters of β- (5-tert-butyl-4-hydroxy-3-methylphenyl) propionic acid with mono- or more polyhydric alcohols, such as. B. with 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) oxalic acid diamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo- [2.2.2] octane.
  • 1.15. Esters of β- (3,5-dicyclohexyl-4-hydroxyphenyl) propionic acid with mono- or polyhydric alcohols, such as. B. with 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) oxalic acid diamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethyl propane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo [2.2.2] octane.
  • 1.16. Esters of 3,5-di-tert-butyl-4-hydroxyphenylacetic acid with mono- or polyhydric alcohols, such as. B. with 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) oxalic acid diamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylol propane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo [2.2.2] octane.
  • 1.17. Amides of β- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid, such as e.g. B. N, N'-bis (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) hexamethylenediamide, N, N'-bis (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) trimethylendiamide , 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 (Nau gard®-XL-1 from Uniroyal).
  • 1.18. Ascorbic acid (vitamin C).
  • 1.19. Amine antioxidants, such as. B. N, N'-di-isopropyl-p-phenylene diamine, N, N'-di-sec-butyl-p-phenylene diamine, N, N'-bis (1,4-dimethyl-pentyl) -p-phenylene diamine, N, N'-bis (1-ethyl-3-methyl-pentyl) -p-phenylenediamine, N, N'-bis (1-methyl-heptyl) -p-phenylenediamine, N, N'-dicyclohexyl-p- phenylenediamine, N, N'-diphenyl-p-phenylenediamine, N, N'-di- (2-naphthyl) -p-phenylenediamine, N-isopropyl-N'-phenyl-p-phenylenediamine, N- (1.3 -Dimethyl-butyl) -N'-phenyl-p-phenylenediamine, N- (1-methyl-heptyl) -N'-phenyl-p-phenylenediamine, N-cyclohexyl-N'-phenyl-p-phenylenediamine, 4- (p-toluenesulfonamido) diphenylamine, N, N'-dimethyl-N, N'-di-sec-butyl-p-phenylenediamine, diphenylamine, N-allyldiphenylamine, 4-isopropoxy-diphenylamine, N-phenyl- 1- naphthylamine, N- (4-tert-octylphenyl) -1-naphthylamine, N-phenyl-2-naphthylamine, octylated diphenylamine, e.g. B. p, p'-di-tert-octyldiphenylamine, 4-n-butylaminophenol, 4-butyrylamino-phenol, 4-nonanoylamino-phenol, 4-dodecanoylamino-phenol, 4-octadecanoylamino-phenol, di- (4-methoxyphenyl) amine, 2,6-di-tert-butyl-4-dimethylamino-methyl-phenol, 2,4'-diamino-diphenylmethane, 4,4'-diamino-diphenylmethane, N, N, N ', N'-tetramethyl -4,4'-diamino-diphenylmethane, 1,2-di - [(2-methylphenyl) amino] ethane, 1,2-di- (phenylamino) propane, (o-tolyl) biguanide, Di- [4- (1 ', 3'-dimethylbutyl) phenyl] amine, tert-octylated N-phenyl-1-naphthylamine, mixture of mono- and dialkylated tert-butyl / tert-octyldiphenylamines, mixture of mono and dialkylated nonyldiphenylamines, mixture of mono- and dialkylated dodecyldiphenylamines, mixture of mono- and dialkylated isopropyl / isohexyldiphenylamines, mixtures of mono- and dialkylated tert-butyldiphenylamines, 2,3-dihydro-3,3-dimethyl-4H- 1,4-benzothiazine, phenothiazine, mixture of mono- and dialkylated tert-butyl / tert-octyl-phenothiazines, mixture of mono- and dialkylated tert-octyl-phenothiazines, N-allylphenothiazine, N, N, N ', N'-tetraphenyl-1,4-diaminobut-2-ene, N, N-bis- (2,2,6,6- tetramethyl-piperidin-4-yl-hexamethylenediamine, bis (2,2,6,6-tetramethylpiperidin-4-yl) sebacat, 2,2,6,6-tetramethypiperidin-4-one, 2,2,6 , 6-tetramethylpiperidin-4-ol.
• 2. UV absorber and light stabilizer
  • 2.1. 2- (2'-hydroxyphenyl) benzotriazoles, such as. B. 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-chloro-benzotriazole, 2- (3'-tert-butyl-2'-hydroxy-5'-methylphenyl) -5-chloro-benzotriazole, 2- (3'-sec-butyl -5'-tert-butyl-2'-hydroxyphenyl) benzotriazole, 2- (2'-hydroxy- 4'-octoxyphenyl) benzotriazole, 2- (3 ', 5'-di-tert-amyl-2'- hydroxyphenyl) benzotriazole, 2- (3 ', 5'- bis (α, αdimethylbenzyl) -2'-hydroxyphenyl) benzotriazole, 2- (3'-tert-butyl-2'-hydroxy-5' - (2- octyloxycarbonylethyl) phenyl) -5-chloro-benzotriazole, 2- (3'-tert-butyl-5 '- [2- (2-ethylhexyloxy) - carbonylethyl] -2'-hydroxyphenyl) -5-chloro-benzotriazole, 2- (3'-tert-Butyl-2'-hydroxy-5 '- (2-methoxycarbonylethyl) phenyl) -5-chloro-benzotriazole, 2- (3'-tert-butyl-2'-hydroxy-5' - ( 2-methoxy carbonylethyl) phenyl) benzotriazole, 2- (3'-tert-butyl-2'-hydroxy-5 '- (2-octyloxycarbonylethyl) phenyl) benzot riazole, 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) phenyl-benzotriazole, 2,2'-methylene-bis [4- (1,1,3 , 3-tetra methylbutyl) -6-benzotriazol-2-yl-phenol], transesterification product of 2- [3'-tert-butyl-5 '- (2-methoxycarbonylethyl) -2'-hydroxy-phenyl] -benzotriazole with Polyethylene glycol 300;
    with R = 3'-tert-butyl-4'-hydroxy-5'-2H-benzotriazol-2-ylphenyl; 2- [2'-Hydroxy-3 '- (α, α-dimethylbenzyl) -5' - (1,1,3,3-tetramethylbutyl) phenyl] benzotri azole; 2- [2'-Hydroxy-3 '- (1,1,3,3-tetramethylbutyl) -5' - (α, α-dimethylbenzyl) phenyl] benzotriazole.
  • 2.2. 2-hydroxybenzophenones such as e.g. B. 4-hydroxy, 4-methoxy, 4-octoxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy, 4,2 ', 4'-trihydroxy, 2'-hydroxy-4 , 4'-dimethoxy derivative.
  • 2.3. Esters of optionally substituted benzoic acids, such as. B. 4-tert-butyl-phenylsalicylic acid, phenyl salicylate, octylphenyl salicylate, dibenzoylresorcinol, bis (4-tert-butylbenzoyl) -re sorcinol, benzoylresorcinol, 3,5-di-tert-butyl-4-hydroxybenzoic acid 2,4 -di-tert-butylphenyl ester, 3,5-di-tert-butyl-4-hydroxybenzoic acid, hexadecyl ester, 3,5-di-tert-butyl-4-hydroxybenzoic acid, octadecyl ester, 3,5-di-tert-butyl-4- 2-methyl-4,6-di-tert-butylphenyl hydroxybenzoate.
  • 2.4. Acrylates such as B. α-cyan-β, β-diphenylacrylic acid ethyl or isooctyl ester, α-car bomethoxy-cinnamic acid methyl ester, α-cyano-β-methyl-p-methoxy-cinnamic acid methyl ester or butyl ester, α-carbomethoxy-p-methoxy -cinnamic acid methyl ester, N- (β-carbomethoxy-β-cya novinyl) -2-methyl-indoline.
  • 2.5. Nickel compounds such as B. nickel complexes of 2,2'-thio-bis [4- (1,1,3,3-tetramethyl butyl) phenol], such as the 1: 1 or the 1: 2 complex, optionally with additional ligands , such as n-butylamine, triethanolamine or N-cyclohexyl-diethanolamine, nickel dibutyldithio carbamate, nickel salts of 4-hydroxy-3,5-di-tert-butylbenzylphosphonic acid monoalkyl esters, such as of the methyl or ethyl ester, nickel complexes of ketoximes, such as of 2 -Hydroxy- 4-methyl-phenyl-undecylketoxim, nickel complexes of 1-phenyl-4-lauroyl-5-hydroxy-pyrazole, optionally with additional ligands.
  • 2.6. Sterically hindered amines, e.g. B. bis (2,2,6,6-tetramethyl-piperidin-4-yl) sebacate, bis (2,2,6,6-tetramethyl-piperidin-4-yl) succinate, bis (1,2, 2,6,6-pentamethylpiperidin-4-yl) sebacat, bis (1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, n-butyl-3,5-di-tert -butyl-4-hy droxybenzyl-malonic acid bis (1,2,2,6,6-pentamethylpiperidyl) ester, condensation product of 1-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-dichloro-1,3,5-s-triazine , Tris (2,2,6,6-tetramethyl-4-piperidyl) nitrilotriacetate, tetrakis (2,2,6,6-tetramethyl-4-piperidyl) -1,2,3,4-butanetetraoate, 1, 1 '- (1,2-ethanediyl) bis (3,3,5,5-tetramethyl-piperazinone), 4-benzoyl-2,2,6,6-tetramethyl-piperidine, 4-stearyloxy-2,2,6, 6-tetramethylpiperidine, bis (1,2,2,6,6-pentamethylpiperidyl) -2-n-butyl-2- (2-hydroxy-3,5-di-tert-butylbenzyl) malonate, 3-n-octyl -7,7,9,9-tetramethyl-1,3,8-triazaspiro [4.5] decane-2,4-dione, Bis (1-octyloxy-2,2,6,6-tetramethylpiperidyl) sebacate, bis (1-octyloxy-2,2,6,6-tetramethylpiperidyl) succinate, linear or cyclic condensation products of N, N'-bis- (2,2,6,6-tetramethyl-4-piperidyl) hexamethylene diamine and 4-morpholino-2,6-dichloro-1,3,5-triazine, condensation product from 2-chloro-4,6-di- ( 4-n-butylamino-2,2,6,6 tetramethylpiperidyl) - 1,3,5-triazine and 1,2-bis (3-aminopropylamino) ethane, condensation product from 2-chloro-4,6-di- (4th -n-butylamino-1,2,2,6,6-pentamethylpiperidyl) -1,3,5-triazine and 1,2-bis (3-aminopropylamino) ethane, 8-acetyl-3-dodecyl-7, 7,9,9-tetramethyl-1,3,8 triazaspiro [4.5] decan-2,4-dione, 3-dodecyl-1- (2,2,6,6-tetramethyl-4-piperidyl) pyrrolidin-2, 5-dione, 3-dodecyl-1- (1,2,2,6,6-pentamethyl-4-piperidyl) pyrrolidine-2,5-dione, mixture of 4-hexadecyloxy and 4-stearyloxy-2,2 , 6,6-tetramethylpiperidine, condensation product of N, N'-bis (2,2,6,6-tetra methyl-4-piperidyl) hexamethylene diamine and 4-cyclohexylamino-2,6-dichloro-1,3,5- triazine, condensation product 1,2-bis (3-aminopropylamino) ethane and 2,4,6-trichloro-1,3,5-triazine as well as 4-butylamino-2,2,6,6-tetramethyl-piperidine (CAS Reg. No . [136504-96-6]); N- (2,2,6,6-tetramethyl-4-piperidyl) -n-dodecylsuccinimide, N- (1,2,2,6,6-pentamethyl-4-piperidyl) - n-dodecylsuccinimide, 2-undecyl- 7,7,9,9-tetramethyl-1-oxa-3,8-diaza-4-oxo-spiro [4,5] decane, reaction product of 7,7,9,9-tetramethyl-2-cycloundecyl-1- oxa-3,8-diaza-4-oxospiro [4,5] decane and epichlorohydrin, 1,1-bis (1,2,2,6,6-pentamethyl-4-piperidyloxycarbonyl) -2- (4-methoxyphenyl ) -ethene, N, N'-bis-formyl-N, N'-bis (2,2,6,6-tetramethyl-4-piperidyl) -hexamethylene diamine, diester of 4-methoxy-methylene-malonic acid with 1, 2,2,6,6-Pentamethyl-4-hy droxy-piperidine, poly [methylpropyl-3-oxy-4- (2,2,6,6-tetramethyl-4-piperidyl)] siloxane, reaction product of maleic anhydride -α-olefin copolymer and 2,2,6,6-tetramethyl-4-amino piperidine or 1,2,2,6,6-pentamethyl-4-aminopiperidine.
  • 2.7. Oxalic acid diamides, such as. B. 4,4'-di-octyloxy-oxanilide, 2,2'-diethoxy-oxanilide, 2,2'-di-octyloxy-5,5'-di-tert-butyl-oxanilide, 2,2'- Di-dodecyloxy-5,5'-di-tert-butyl-oxanilide, 2-ethoxy-2'-ethyl-oxanilide, N, N'-bis (3-dimethylaminopropyl) oxalamide, 2-ethoxy-5-tert- butyl-2'-ethylox anilide and its mixture with 2-ethoxy-2'-ethyl-5,4'-di-tert-butyl-oxanilide, mixtures of o- and p-methoxy and of o- and p-ethoxy- di-substituted oxanilides.
  • 2.8. 2- (2-hydroxyphenyl) -1,3,5-triazines such as e.g. B. 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-propyl oxyphenyl) 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-butyloxypropyloxy) phenyl] -4,6-bis ( 2,4-dimethylphenyl) -1,3,5-triazine, 2- [2-hydroxy-4- (2-hydroxy-3-octyloxypropyloxy) phenyl] -4,6-bis (2,4-dimethylphenyl ) - 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-tri azine, 2- (2-hydroxy-4-methoxyphenyl) -4,6- diphenyl-1,3,5-triazine, 2,4,6-tris [2-hydroxy-4- (3-butoxy-2-hydroxy-propoxy) phenyl] -1,3,5-triazine, 2- (2nd -Hydroxyphenyl) -4- (4-methoxyphenyl) -6-phenyl-1,3,5-triazine, 2- (2-hydroxy-4- [3- (2-ethylhexyl-1-oxy) -2-hydroxypropyloxy] phenyl) -4,6- bis (2,4-dimethylphenyl) -1,3,5-triazine.
• 3. Metal deactivators, such as. B. N, N'-diphenyloxalic acid diamide, N-salicylal-N'-salicyloyl hydrazine, N, N'-bis (salicyloyl) hydrazine, N, N'-bis (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) - hydrazine, 3-salicyloylamino-1,2,4-triazole, bis (benzylidene) oxalic acid dihydrazide, oxanilide, iso phthalic acid dihydrazide, sebacic acid bis-phenylhydrazide, N, N'-diacetyl-adipic acid dihy drazid, N, N'-bis-salicyloyl-oxalic acid dihydrazide, N, N'-bis-salicyloyl-thiopropionic acid dihy drazid.
• 4. Phosphites and phosphonites, such as. B. triphenyl phosphite, diphenylalkyl phosphites, phenyl dialkyl phosphite, tris (nonylphenyl) phosphite, trilauryl phosphite, trioctadecyl phosphite, diste aryl-pentaerythritol diphosphite, tris (2,4-di-tert-butylphenyl) phosphite, diisodecylpentaerythritol-di phosphite, bis (2,4-di-tert-butylphenyl) pentaerythritol diphosphite, bis- (2,6-di-tert-butyl-4-methyl) phenyl) pentaerythritol diphosphite, bis-isodecyloxy-pentaerythritol diphosphite, bis (2,4-di-tert-butyl- 6-methylphenyl) pentaerythritol diphosphite, bis (2,4,6-tri-tert-butylphenyl) pentaerythritol di phosphite, tristearyl sorbitol triphosphite, tetrakis (2,4-di-tert-butylphenyl) -4,4'-biphenylene-di phosphonite, 6-isooctyloxy-2,4,8,10-tetra-tert-butyl-12H-dibenz [d, g] -1,3,2-dioxaphosphocin, 6-fluoro-2,4,8,10-tetra-tert-butyl-12-methyl-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, 2,2 ', 2' 'nitrilo [triethyl-tris (3,3', 5,5'-tetra-tert-butyl-1,1'-biphenyl-2,2'-diyl) phosphite], 2 -Ethylhe xyl- (3,3 ', 5,5'-tetra-tert-butyl-1,1'-biphenyl-2,2'-diyl) phosphite.

The following phosphites are particularly preferably used:
Tris (2,4-di-tert-butylphenyl) phosphite (Irgafos®168, Ciba-Geigy), tris (nonylphenyl) phosphite,

• 5. Hydroxylamines such as B. N, N-dibenzylhydroxylamine, N, N-diethylhydroxylamine, N, N-dioctyl hydroxylamine, N, N-dilaurylhydroxylamine, N, N-ditetradecylhydroxylamine, N, N-dihexadecylhy hydroxylamine, N, N-dioctadecylhydroxylamine, N-hexadecyl-N-octadecylhydroxylamine, N-Hep tadecyl-N-octadecylhydroxylamine, N, N-dialkylhydroxylamine from hydrogenated tallow fatty amines.
• 6. Nitrons such as B. N-benzyl-alpha-phenyl-nitrone, N-ethyl-alpha-methyl-nitrone, N-octyl-alpha heptyl-nitrone, N-lauryl-alpha-undecyl-nitrone, N-tetradecyl-alpha-tridecyl-nitrone, N-He xadecyl-alpha-pentadecyl-nitron, N-octadecyl-alpha-heptadecyl-nitron, N-hexadecyl-alpha heptadecyl-nitrone, N-octadecyl-alpha-pentadecyl-nitrone, N-heptadecyl-alpha-heptadecyl-ni tron, N-octadecyl-alpha-hexadecyl-nitrone, nitrones derived from N, N-dialkylhydroxylamines made from hydrogenated tallow fatty amines.
• 7. Thiosynergists such as B. thiodipropionic acid-di-lauryl ester or thiodipropionic acid-di- stearyl ester.
• 8. Peroxide-destroying compounds, such as. B. esters of β-thio-dipropionic acid, for example se the lauryl, stearyl, myristyl or tridecyl ester, mercaptobenzimidazole, the zinc salt of 2-mercaptobenzimidazole, zinc dibutyl dithiocarbamate, dioctadecyl disulfide, pentaery thrit-tetrakis (β-dodecylmercapto) propionate.
• 9. Basic co-stabilizers, such as. B. melamine, polyvinylpyrrolidone, dicyandiamide, tri allyl cyanurate, urea derivatives, hydrazine derivatives, amines, polyamides, polyurethanes, alkali and Alkaline earth metal salts of higher fatty acids, for example Ca stearate, Zn stearate, Mg behenate, Mg stearate, Na ricinoleate, K palmitate, antimony pyrocatecholate or zinc pyrocatecholate.
• 10. Nucleating agents, such as. B. inorganic substances such. B. talc, metal oxides such as titanium dioxide or magnesium oxide, phosphates, carbonates or sulfates of preferably earth alkali metals, organic compounds such as mono- or polycarboxylic acids and their salts such as B. 4-tert-butylbenzoic acid, adipic acid, diphenylacetic acid, sodium succinate or Sodium benzoate, polymeric compounds such as. B. ionic copolymers ("ionomers").  
• 11. Fillers and reinforcing agents, such as. As calcium carbonate, silicates, glass fibers, glass balls, talc, kaolin, mica, barium sulfate, metal oxides and hydroxides, carbon black, graphite, Wood flour and flours or fibers of other natural products, synthetic fibers.
• 12. Other additives, such as. B. plasticizers, lubricants, emulsifiers, pigments, rheolo giadditives, catalysts, flow control agents, optical brighteners, flame retardants, anti static, propellant.
• 13. Benzofuranones or indolinones, such as. B. in U.S. 4,325,863; U.S. 4,338,244; U.S. 5,175,312, U.S. 5,216,052; U.S. 5,252,643; DE-A-43 16 611; DE-A-43 16 622; DE-A-43 16 876; EP-A-0589839 or EP-A-0591102, or 3- [4- (2-acetoxyethoxy) phenyl] -5,7-di- tert-butyl-benzofuran-2-one, 5,7-di-tert-butyl-3- [4- (2-stearnyloxyethoxy) phenyl] benzofuran-2- on, 3,3'-bis [5,7-di-tert-butyl-3- (4- [2-hydroxyethoxy] phenyl) benzofuran-2-one], 5,7-di-tert-bu tyl-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-pivaloyloxy-phenyl) -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.

The costabilizers, with the exception of the benzofuranones listed under point 13, who for example in concentrations of 0.01 to 10%, based on the total weight of the stabilizing polyamide, polyester or polyacetal added.

In addition to components (a) and (b), further preferred compositions contain still further additives, in particular phenolic antioxidants, light stabilizers or / and Processing stabilizers.

Particularly preferred additives are phenolic antioxidants (item 1 of the list), steric hindered amines (item 2.6 of the list), phosphites and phosphonites (item 4 of the list) and peroxide destroying compounds (item 8 of the list).

Compositions containing the components are of particular interest (a) and (b) as a further additive at least one compound of the organic phos type phite or phosphonite (item 4 of the list).  

Also particularly preferred additional additives (stabilizers) are benzofuran-2-ones, as they e.g. B. in U.S. 4,325,863; U.S. 4,338,244; U.S. 5,175,312; U.S. 5,216,052; U.S. 5,252,643; DE-A-43 16 611, DE-A-43 16 622, DE-A-43 16 876, EP-A-0 589 839 or EP-A-0 591102.

Examples of such benzofuran-2-ones are compounds of the formula

wherein
R _{'11 represents} an unsubstituted or substituted carbocyclic or heterocyclic aromatic ring system;
R _{'12 is} hydrogen;
R _{'14 is} hydrogen, alkyl of 1 to 12 carbon atoms, cyclopentyl, cyclohexyl or chlorine;
R _{'13 has} the meaning of R' ₁₂ or R _'14 or a radical of the formula

is what
R _{'16 is} hydrogen, alkyl having 1 to 18 carbon atoms, alkyl interrupted by oxygen or sulfur having 2 to 18 carbon atoms, dialkylaminoalkyl having a total of 3 to 16 carbon atoms, cyclopentyl, cyclohexyl, phenyl or substituted by 1 to 3 alkyl radicals with a total of at most 18 carbon atoms Is phenyl;
s is 0.1 or 2;
the substituents R _'17 independently of one another hydrogen, alkyl having 1 to 18 carbon atoms, cyclopentyl, cyclohexyl, phenyl, phenyl substituted by 1 or 2 alkyl radicals having a maximum of 16 carbon atoms, a radical of the formula —C ₂ H ₄ OH, —C ₂ H ₄ -OC _t H _{2t + 1} or

are or together with the nitrogen atom to which they are attached form a piperidine or morpholine residue;
t 1 to 18;
R _{'20 is} hydrogen, alkyl of 1 to 22 carbon atoms or cycloalkyl of 5 to 12 carbon atoms;
A is an alkylene with 2 to 22 carbon atoms which may be interrupted by nitrogen, oxygen or sulfur;
R _{'18 is} hydrogen, alkyl having 1 to 18 carbon atoms, cyclopentyl, cyclohexyl, phenyl, phenyl or benzyl substituted by 1 or 2 alkyl radicals having a total of at most 16 carbon atoms;
R _{'19 represents} alkyl of 1 to 18 carbon atoms;
D is -O-, -S-, -SO-, -SO ₂ - or -C (R _'21 ) ₂ -;
the substituents R _{'21 are} independently hydrogen or C ₁ -C ₁₆ alkyl, the two R' ₂₁ together containing 1 to 16 carbon atoms, or R _'21 phenyl or a radical of the formula

is where s, R _'16 and R' _{17 have} the meanings given above;
E is a remainder of the formula

wherein R _'11 , R' ₁₂ and R _{'14 have} the meanings given above; and
R _{'15 is} hydrogen, alkyl having 1 to 20 carbon atoms, cyclopentyl, cyclohexyl, chlorine or a radical of the formula

is in which R _'16 and R' _{17 have} the meanings given above, or R _'15 together with R' ₁₄ forms a tetra methylene radical.

Preferred benzofuran-2-ones are those in which R _{'13 is} hydrogen, alkyl having 1 to 12 carbon atoms, cyclopentyl, cyclohexyl, chlorine or a radical of the formula

or -DE is where s, R _'16 , R' ₁₇ , D and E have the meanings given above, R _'16 in particular has the meaning of hydrogen, alkyl having 1 to 18 carbon atoms, cyclopentyl or cyclohexyl.

Preference is furthermore given to those benzofuran-2-ones in which R _{'11 is} phenyl or phenyl substituted by 1 or 2 alkyl radicals with a total of at most 12 carbon atoms; R _{'12 is} hydrogen; R _{'14 is} hydrogen or alkyl of 1 to 12 carbon atoms;
R _{'13 is} hydrogen, alkyl having 1 to 12 carbon atoms,

or -DE; R _{'15 is} hydrogen, alkyl having 1 to 20 carbon atoms,

or R _'15 together with R' ₁₄ forms a tetramethylene radical, where s, R _'16 , R' ₁₇ , D and E have the meanings given at the beginning.

Also of particular interest are those benzofuran-2-ones in which R _'13 is hydrogen, alkyl having 1 to 12 carbon atoms or -DE; R _'12 and R' _{14 are} independently hydrogen or alkyl of 1 to 4 carbon atoms; and R _{'15 is} alkyl of 1 to 20 carbon atoms, where D and E have the meanings given above.

Finally, of particular interest are also those benzofuran-2-ones in which R _{'13 is} alkyl having 1 to 4 carbon atoms or -DE; R _'12 and R' _{14 are} hydrogen; and R _{'15 is} alkyl of 1 to 4 carbon atoms, cyclopentyl or cyclohexyl, where D is a group -C (R' ₂₁ ) ₂ - and E is a radical of the formula

, where the substituents R _{'21 are} identical or different from one another and are each alkyl having 1 to 4 carbon atoms, and R' ₁₁ , R _'12 , R' ₁₄ and R _{'15 have} the meaning given.

The amount of additional benzofuran-2-ones used can vary within wide limits ken. For example, they can be 0.0001 to 5, preferably 0.001 to 2, in particular 0.01 to 2% by weight can be contained in the compositions according to the invention.

Incorporation of component (b) and any other additives into the compo nente (a) [polyamide, polyester or polyacetal] is carried out according to known methods, for example as before or during shaping or by applying the dissolved or dis Pearled component (b) on component (a), optionally with subsequent Evaporation of the solvent. Component (b) can also be in the form of a masterbat ches, which contains these for example in a concentration of 2.5 to 25 wt .-%, to stabilizing materials [component (a)] are added.

Component (b) can also be used before or during the polymerization or before the crosslinking be added.

Component (b) can cap in pure form or in waxes, oils or polymers rarely be incorporated into component (a) to be stabilized.

Component (b) can also be sprayed onto component (a) to be stabilized the. It is able to add other additives (e.g. the conventional Additi  ve) or their melts to be diluted, so that they also together with these additives can be sprayed onto component (a) to be stabilized. Particularly advantageous is the addition by spraying during the deactivation of the polymerization catalyst goals, z. B. the steam used for deactivation is used for spraying that can.

The polyamides, polyesters or polyacetals stabilized in this way can be in a wide variety of forms be applied, e.g. B. as films, fibers, tapes, molding compounds, profiles or as a bin detergent for paints, adhesives or putties.

Component (b) is particularly suitable as a processing stabilizer (heat stabilizer). For this purpose, it is advantageous before or during the processing of component (a) added.

A preferred embodiment of the present invention is therefore the use of the Component (b) as a stabilizer, in particular processing stabilizer (thermostabilisa tor), for polyamides, polyesters or polyacetals against oxidative, thermal and / or light-induced degradation.

Component (b) is characterized by an advantageous color behavior, i. H. slight discoloration Exercise of polyamides, polyesters and polyacetals during processing.

The present invention also relates to a method for stabilizing a polyamide, Polyesters or polyacetals against oxidative, thermal and / or light-induced degradation, characterized in that at least one component (b) is incorporated therein or applies to them.

The following examples further illustrate the invention. Parts or percentages relate to weight.

example 1 Stabilization of polyamide 12

100 parts of unstabilized polyamide 12 granules (Grilamid®L 20 G, company EMS, Switzerland) who pulverized by cryogenic grinding and with the stabilizers shown in Table 1  ren moved. The mixture is mixed with a Henschel mixer at 70 ° C for 2 minutes mixed. The powder thus obtained is then dried at 80 ° C. for 6 hours net and then extru in a twin-screw extruder (type Berstorff) at a maximum of 210 ° C diert and then granulated. The granules obtained are on an injection molding machine (Engel type) sprayed at a maximum of 220 ° C to 1.0 mm thick and 67 mm long dumbbells. From The yellowness index (YI) of these dumbbells is determined in accordance with ASTM D 1925-70. Low YI values mean little discoloration, high YI values strong discoloration of the pattern. Ever ger the discoloration, the more effective the stabilizer or the stabilizer mixture. The Results are summarized in Table 1.  

Table 1

• a) Comparative example.
• b) Example according to the invention.
• c) Irganox®245 (Ciba Specialty Chemicals Ltd) means a compound of formula AO-1
  
• d) Irganox®1098 (Ciba Specialty Chemicals AG) means a compound of formula AO2
  
• e) Component (b) means the compound of the formula I.
  
• f) Irgafos®168 (Ciba Specialty Chemicals AG) means tris (2,4-di-tert-butylphenyl) phos phit.
• g) Irgafos®12 (Ciba Specialty Chemicals AG) means 2,2 ', 2' '- Nitrilo [triethyl-tris (3,3'5,5'- tetra-tert-butyl-1,1'-biphenyl-2,2'-diyl) phosphite]; Chemical Abstract "Registry" number: 80410-33-9 and represents the compound of formula B.

Example 2 Stabilization of polyamide 6

100 parts of unstabilized polyamide 6 granules (Ultramid®B3S, from BASF) are pulverized by cryogenic grinding and the stabilizers specified in Table 2 are added. The mixture is mixed with a Henschel mixer at 70 ° C for 2 minutes. The powder thus obtained is then dried at 80 ° C. for 6 hours and then extruded in a twin-screw extruder (Berstorff type) at a maximum of 240 ° C. and then granulated. The granules obtained are sprayed on an injection molding machine at a maximum of 240 ° C. to 4 x 6 mm thick and 50 mm long rods. These sticks are aged in a forced air oven at 150 ° C. The time is measured in hours until the impact strength of the rods has dropped to 80 KJ / m ² . The longer the time, the better the stabilization. The results are summarized in Table 2.

Table 2

Impact resistance in an oven aging test at 150 ° C

Example 3 Stabilization of polyoxymethylene copolymer (POM)

100 parts of unstabilized POM copolymer (Hostaform®C, Hoechst) is made with 0.3% calcium stearate and mixed with the stabilizers given in Tables 3, 4 and 5. On the powder is then extruded at a maximum of 190 ° C. A part of this granulate is on an injection molding machine at a maximum of 200 ° C to 2 mm thick, 40 mm wide and 60 mm long splashed against platelets. The other part of the granulate is on an injection molding machine sprayed at a maximum of 200 ° C into 4 x 6 mm thick and 50 mm long sticks.

A part of these platelets is thermothermally under an air stream at 220 ° C gravimetric measurement carried out. The time is measured in minutes until the Lose 3%, 6% and 10% of their weight. The longer the time, the better the stabilization. The results are summarized in Table 3.

Table 3

Thermogravimetric measurement at 220 ° C

Another part of the platelets is subjected to an oven aging test at 140 ° C. There at the plates are aged in a forced air oven at 140 ° C and the time in hours measure until the plates lose 2% of their weight. The longer the time, the better the stabilization. The results are summarized in Table 4.  

Table 4

Weight loss in oven aging test at 140 ° C

An oven aging test is also carried out in a convection oven at 140 ° C of the 4 x 6 mm thick and 50 mm long sticks. The time is measured in hours until the impact strength of the rods has dropped from originally 110 KJ / m ² to 90 KJ / m ² . The longer the time, the better the stabilization. The results are summarized in Table 5.

Table 5

Impact resistance in an oven aging test at 140 ° C

Claims (11)

1. Composition containing

• a) an oxidative, thermal or light-induced degradation subject to polyamide, polyester or polyacetal, and
• b) the compound of formula I.
  with the condition that when component (a) is a polyamide, the composition contains no metal hypophosphite and no copper salt of an organic acid.

2. Composition according to claim 1, wherein the polyamide is a polyamide 6, polyamide 6.6, polyamide 4.6, polyamide 11 or polyamide 12 or a copolymer thereof. 3. A composition according to claim 1, wherein the polyester is a PET, PETG or PBT or a copolymer thereof. 4. The composition according to claim 1, wherein the polyacetal is a homopolymer or Is copolymer. 5. The composition according to claim 1, wherein component (b) in an amount of 0.01 to 1% based on the weight of component (a) is present. 6. Composition according to claim 1, comprising in addition to components (a) and (b) additional additives. 7. Composition according to claim 6, containing as further additives phenolic anti oxidants, light stabilizers and / or processing stabilizers.   8. The composition according to claim 6, comprising at least one as a further additive Organic phosphite or phosphonite type compound. 9. The composition according to claim 6, comprising at least one as a further additive Benzofuran-2-one type compound. 10. A method for stabilizing a polyamide, polyester or polyacetal against oxide tive, thermal and / or light-induced degradation, characterized in that one this incorporates or onto at least one component (b) according to claim 1 applies. 11. Use of component (b) according to claim 1 as a stabilizer for polyamides, Polyester or polyacetals against oxidative, thermal and / or light-induced degradation.