JPH04253988A - One, two or three carbocyclic phosphinic acid or phosphonic acid compound - Google Patents

Abstract

PURPOSE: To provide a compd. which is useful for improving the dyeability of a plastic material and has a group having reactivity with hydroxy, amino and a group contg. stereoscopically hindered amine.

CONSTITUTION: The compds. of, for example, formula I, formula II [R is (halogen, ≥1 pieces of 1 to 4C alkyl, etc., and substd.) mono, bi or tri-carbocyclic groups; R₁ is group reactive with hydroxy and/or amine; R₂ is NR₃ (R₃ is H, etc.), O; R₄ forms a 5-, 6- or 7-membered cyclic group together with two pieces of C coupled with R₈; etc.; R₅ is H, etc.; R₈ is 1 to 6C alkyl; (n) is 0, 1; (p) is 1 to 3; pa is 0 to 2 and p+pa is 1 to 3]. The compds. of the formula I, the formula II are obtd. by condensing the compds. contg. one or plural groups reactable with the hydroxy and/or amino and the mono, bi or tri-carbocyclic amino or hydroxy-contg. phosphine or phosphinic acid. For example, the compd. of formula III.

COPYRIGHT: (C)1992,JPO

Description

[Detailed description of the invention]

[0001] According to the invention, a mono-, di-containing compound comprising i) at least one group reactive with hydroxy and/or amino and/or ii) at least one group comprising a sterically hindered amine is provided. Or a tricarbon cyclic phosphinic acid or phosphonic acid compound is provided.

Preferably, hydroxy- and amino-reactive groups and sterically hindered amines are bonded to each other through nitrogen or oxygen atoms or by esters, amides or bases.

Preferably, the mono-, di- or tricarbocyclic phosphine and phosphonic acid compounds of the invention contain i) one group reactive with hydroxy and/or amino and ii) at least one, preferably two It contains a sterically hindered amine group.

Preferred mono-, di- or tricarbocyclic groups are C
5-7 cycloalkyl (preferably cyclohexyl)
, phenyl, naphthyl, tetrahydronaphthyl,
It is an acenaphthene or acenaphthylene group. More preferably, the cyclic group is unsubstituted or contains halogen (especially chloro or bromo), hydroxyl, C1-4 alkyl (e.g. tert-butyl), phenyl, C1-4 alkoxy and/or C1-4 alkoxy It is a -cyclic group mono- or di-substituted with a water-insoluble substituent selected from carbonyl groups. Preferably the mono-, di- or tricarbocyclic groups are unsubstituted.

Polycyclic carbocyclic groups can contain one or more phosphinic acid or phosphonic acid groups. However, preferred compounds contain at least one sterically hindered group per phosphinic acid or phosphonic acid group. Groups reactive with hydroxy and/or amino groups are well known in reactive dyeing chemistry. Preferably they carry at least one reactive group,
and cyclic groups having at least two nitrogen atoms (which may be separated by 1 or 2 carbon atoms), such as triazinyl, pyrimidinyl, quinoxalinyl, quinazocnyl, phthalazinyl, benzoxazolyl, benzithiazolyl groups and the following general formulas: :

[In the formula, R30 is a halogen atom (preferably chlorine) or a group -N+(C1-4 alkyl)3 or the following general formula:

[Image Omitted] and A- is an anion, such as halide.

Such groups are known from K. G. Kleb,”
Ueber neueReaktivfarbstof
fe”, Angew, Chem. 76 (1964)
No. 10, P. 423+ff; E. Sie
gel, ”Chemie clarer Reaktiv
farbstoffe”, Chemica, Supp
element March 1968, 3. Farb
ensymposium Interlaken, P
．． 102+ff; E. Siegel in “T”
he Chemistry of Synthetic
Dyes”, Volume VI, Chapter 1, K.Ven
Katarama Publishing, Academic Press
(1972). The contents of these documents are incorporated herein by reference.

More preferred groups reactive with hydroxy and amino are mono- and dichlorotriazinyl, mono- and dichloro-pyrimidinyl or mono- or dichloro-quinoxalinyl, most preferably -chlorotriazinyl. .

More preferably, according to the invention, the following general formula I or II:

[In the formula, R is unsubstituted or halogen, C1-4
is a mono-, di- or tri-carbon cyclic group (preferably a phenyl group) substituted with one or more substituents selected from alkyl or C1-4 alkoxy groups; R1 is a group reactive with hydroxy and amide; and R2 is a group -N
R3 - or -O- (where R3 is hydrogen or C
1-4 alkyl); R4 together with the two carbon atoms to which the group R8 is attached and the nitrogen atom to which R5 is attached forms a 5-, 6- or 7-membered cyclic group, and optionally further substituted with a water-insoluble substituent and/or to which an additional cyclic group is attached to form a spiro group; R5 is a hydrogen atom, C1-4 alkyl or acyl; each R8 is independently C1
-6 alkyl group, preferably methyl or ethyl, more preferably methyl; n is 0 or 1; P is 1
, 2 or 3; and Pa is 0, 1 or 2;
where the sum of P+Pa is 1, 2 or 3] is supplied.

Preferred sterically hindered amine-containing groups have the following general formula:

embedded image In the formula, the symbols are as described above.

More preferred sterically hindered amine groups have the following general formulas a) to e):

embedded image [wherein R5' is hydrogen, C1-4 alkyl (preferably methyl) or acyl, each R9 is independently hydrogen, C1-4 alkyl or one R9 is phenyl, and the other R9 is hydrogen or C1-4 alkyl, or both R9 groups together are the group -(CH2
) 11-, and Y is -N-CO- or -C
O-N-].

Preferably, groups a) to e) are -NH-
or attached to the rest of the molecule by an -O- bridging group. Preferred acyl groups have the formula R20-A1- or A21-
A2-, where R20 is an unsubstituted or substituted hydrocarbon group and also includes a heteroatom; however, preferably such a group is a phenyl group or a C1-4 alkyl group. is a group; A1
is a bridging group -O-CO-, -SO2 - or O-SO2
-; R21 is hydrogen or a group R2 unrelated to R20
0; A2 is a group -CO-NR22-CO- or -
NR22-SO2-, where R22 may simply be bonded to the nitrogen atom, and R22 is hydrogen or a group R20 unrelated to R20. More preferably, the acyl group is
-CO-C1-4 is an alkyl group.

On the other hand, preferred compounds of the present invention have the following general formula III or IV:

[Formula 12] [wherein n is 0 or 1; r and r' are each independently 1, 2 or 3; P' is 1, 2, 3 or 4
and Pa' is 0, 1, 2 or 3, provided that the sum of P' and Pa' and the sum of r and r' is 2, 3 or 4; R10 is an amide or ester-bonded phenyl group; , and other symbols are as defined above.

Preferred phosphine and phosphonic acid groups also have the following general formula V:

It is derived from a compound represented by [wherein R10a is a direct bond, oxygen, C1-4 alkylene or -CH=CH-].

The compounds of the invention can be prepared by known methods; for example, a) a suitable amount of a compound containing one or more groups capable of reacting with hydroxy and/or amino; or b) an appropriate amount of a mono-, di- or tri-carbocyclic phosphine or phosphonic acid and an appropriate amount of a sterically hindered amine. The latter compound can be prepared from known compounds by reacting the latter with a compound containing one or more groups capable of reacting with hydroxy and/or amino groups. Such appropriate amounts will be apparent to those skilled in the art.

Preferably, the method for preparing compounds of formula I comprises the following general formula I':

[Chemical formula 14] 1 mol of the compound represented by the following general formula I'':

[Chemical 1
5] is reacted with P mole of phosphine or phosphonic acid.

Preferably, the compound of formula II comprises 1 mole of a compound containing a reactive group (where P+Pa is optionally 1, the final compound should contain groups reactive with hydroxy and amino) and the general formula II':

[Chemical formula 16] Compound P mol represented by and the following general formula II'':

It is prepared by condensing a compound represented by the following formula with Pamol.

The condensation is carried out under known conditions, for example 20 to 10
It is carried out in an aqueous medium at a temperature of 0° C. with stirring, the pH optionally being increased by the addition of alkali. The compound of the general formula III is the compound of the general formula III
′:

embedded image It can be prepared by forming a salt of 1 mole of the compound represented by the formula (in which the symbols are as above) with 1 mole of mono-, di- or tricarbocyclic phosphine or phosphonic acid P'.

Compounds of formula IV are di-, tri- or tetracarboxylic acids (or functional derivatives thereof, such as acid halides).
1 mol and the following general formula II':

The organic phosphine and phosphonic acid compounds described above may be prepared by reacting r' moles of a compound of formula II'' with r moles of a compound of formula II''. When applied to (especially hydrophobic) plastics and homogeneously mixed, dyeing ability and, especially when sterically hindered amine groups are present, stability against light, especially UV light, oxidation, bleaching and heat. It has been found to be very useful for improving the

Preferred plastic materials are, for example, polyolefins (especially polyethylene and polypropylene).
, ethylene/propylene copolymer, polybutylene, polystyrene, chlorinated polyethylene, polyvinyl chloride, polyester, polyamide, polycarbonate, polymethyl methacrylate, polyphenylene oxide, polyurethane, polypropylene oxide, polyacetate, phenyl-formaldehyde resin, epoxide resin, poly acrylonitriles and their copolymers,
For example, ABS-terpolymer. Preferably, the compounds of the invention are polypropylene, polyethylene (e.g. high molecular weight polyethylene), ethylene/propylene copolymers, polyvinyl chloride, polyesters, polyamides, polyurethanes, polyacrylonitrile, ABS-terpolymers of acrylic acid, styrene and acrylonitrile, It is used to stabilize copolymers of styrene and acrylonitrile or styrene and butadiene, most preferably polypropylene, polyethylene, ethylene/propylene copolymers or ABS.

The compounds of the invention are used to improve the above-mentioned properties of synthetic polyamides, in particular to improve dyeability and dye tonicity (dye yield), and to provide good light fastness and washing fastness properties. It is particularly useful for dyeing with chromatography as well as for imparting improved stability of the support against damage by light.

Synthetic polyamides include various plastic materials, in particular polycondensates or polymers of dicarboxylic acids and diamines, such as adipic acid and hexamethylene diamine, lactams, such as ε-caprolactam, aminocarboxylic acids, such as ω-amino undecane or a polycondensate or polymer of a dicarboxylic acid (isophthalic acid or terephthalic acid) and an aromatic diamine, such as para-phenylenediamine.

Natural materials, such as rubber, can also be treated with the compounds of the invention. The compounds of the invention can be processed into the material to be protected by known methods. A particularly useful application method is intimate mixing of the plastic material and the novel compound in the melt. Examples are kneader or through extrusion, spray casting, blow molding or spinning. Preferably, polypropylene or polyethylene is used in granular, granular or powdered form. Methods for processing compounds into polymers include extrusion, spray casting,
By rotary casting or through blow molding, films, sheets, hoses, pipes, containers, flasks, profile parts, threads, fibers, bands or foams are formed. The plastics should not be completely polymerized or condensed before the mixtures thereof with the compounds of the invention are formed. So-called monomers or prepolymers or precondensates can be added to the compounds of the invention and then produced into the final form simultaneously with or after the condensation or polymerization of the plastic. In the following examples, all parts and percentages are by weight. All temperatures exist in °C.

[0023]

[Example] Example 1 2-chloro-4,6-bis-(2',2',6',6'
423.5 parts of -tetramethylpiperidyl-4'-amino)-triazine (known from DE-PS 2319816) (compound 1b) are suspended in 1500 parts of water and the mixture is reacted with 142 parts of phenylphosphinic acid. Cool and stir at this temperature for 2 hours. The resulting insoluble salt is filtered, washed with water and dried under vacuum. The hygroscopic product melts at 218-220°.

This product has the following general formula 1a:

It is represented by: Elemental analysis is as follows:
C56.6 (57.2)%, H8.3 (8.0)%, C
l6.3(6.3)%N17.1(17.3)%, P5
．． 3 (5.5)%, O6.9 (5.7)%

[0025]
Example 2 184.5 parts of 2,4,6-trichlorotriazine and 4
-314 parts of amino-phenylphosphinic acid to 1300 parts of water
and the mixture is stirred at 50° C. for 2 hours. The reaction product, which is insoluble, is filtered, washed with water, acid-free and dried in vacuo. The product obtained is 2-chloro-4,6-bis-(4'-phosphinic acid phenylamino)-triazine with a melting point above 300°C.

Example 3 Example 1 is repeated using 158 parts of phenylphosphonic acid instead of phosphinic acid.

Example 4 Example 2 is repeated using 346.0 parts of 4-amino-phenyl-phosphonic acid instead of phosphinic acid.

Examples 5-6 Phenylphosphinic acid [instead of 142.0 parts] (Example 5) 284.0 parts or phenylphosphonic acid (Example 6) 31
Repeat Example 1 using 6.0 parts. The products of Examples 1 to 6 enable hydrophobic plastic materials to have significantly improved dyeability, and these plastics (
Dyed or non-dyed) exhibit excellent fastness to light and heat.

Examples 7-9 Repeat Example 1. However, instead of compound 1b, 2,4
,5-tris-(2',2',6',6'-tetramethylpiperidyl-4'-amino)-triazine 544.0
284.0 parts (1 part) of phenylphosphinic acid (Example 7)
42.0 parts) or phenylphosphonic acid (Example 8)
) 316.0 parts.

Repeat Example 1. However, 2-(1', 2'
,6',6'-pentamethylpiperidyl-4'-amino)-4,6-bis-(2'',2'',6'',6''-tetramethylpiperidyl-4-amino)-triazine556.
0 parts are reacted with either 284.0 parts of phenylphosphinic acid (Example 9) or 316 parts of phenylphosphonic acid (Example 9a). The product has good fastness properties to light and heat and gives rise to improved dyeability properties.

Example 10 2-(phenylphosphinic acid-4'-amino)-4,6
-bis-(2″,2″,6″,6″-tetramethylpiperidyl-4″-amino)-triazine, 2-chloro-
423.5 parts of 4,6-bis-(2',2',6',6'-tetramethylpiperidyl-4-amino)-triazine and 157 parts of 4-aminophosphinic acid were dissolved in a 25% aqueous sodium hydroxide solution. by condensation by stirring at 80° C. for 5 to 8 hours. The reaction mixture is then acidified with dilute hydrochloric acid, where the pH is approximately 2. The insoluble reaction product is filtered, washed with water and dried. The compounds obtained improve the dyeability of synthetic polymers, especially in synthetic polyamides, and improve the fastness of plastics to the effects of light.

Examples 11-14 Repeat Example 1. However, terephthalic acid-bis-(2,2
,6,6,-tetramethylpiperidyl-4)-diamide and 142 parts of phenylphosphinic acid (Example 11) or 284 parts of phenylphosphinic acid (Example 12) or 158 parts of phenylphosphonic acid (Example 13) or phenylphosphonic acid. (Example 14) 316 parts.

Examples 15-18 Repeat Example 1. However, isophthalic acid-bis-(2,2
,6,6-tetramethylpiperidyl-4)-diamide 1
, 442 parts and phenylphosphinic acid (Example 15) 142 parts
or 284 parts of phenylphosphinic acid (Example 16) or 158 parts of phenylphosphonic acid (Example 17) or 316 parts of phenylphosphonic acid (Example 18). The resulting product has good light and thermal stability and improved fastness properties.

Examples 19-30 Repeat Example 1. However, trimesic acid-tris-(2,
576 parts of 2,6,6-tetramethylpiperidyl-4)-triamide (DE-PS2040975) and 142 parts of phenylsulfonic acid (Example 19) or 284 parts of phenylphosphinic acid (Example 20) or phenylsulfinic acid (Example 2)
1) 426 parts or phenylsulfonic acid (Example 22) 158 parts
or 316 parts of phenylphosphonic acid (Example 23) or 474 parts of phenylphosphonic acid (Example 24) to form a salt. The resulting product has good stability to light and heat and has improved dyeability. Replacing trimesic acid with the same amount of trimellitic acid-tris-(2,2,6,6-tetramethylpiperidyl-4)-triamide (Examples 25-30) for an additional product with the same effect. can be generated by

Examples 31-38 Repeat Example 1. However, tetrakis pyromellitate (
710 parts of 2,2,6,6-tetramethylpiperidyl-4)-tetramid were added to 1 part of phenylsulfinic acid (Example 31).
42 parts of phenylphosphinic acid (Example 32) or 426 parts of phenylphosphinic acid (Example 33) or 568 parts of phenylphosphinic acid (Example 34). Repeat example 1. However, tetrakis pyromellitate (
710 parts of 2,2,6,6-tetramethylpiperidyl-4)-tetramid were added to 15 parts of phenylphosphonic acid (Example 35).
8 parts or 316 parts of phenylphosphonic acid (Example 36) and 474 parts of phenylphosphonic acid (Example 37) or 632 parts of phenylphosphonic acid (Example 38).

Examples 39 and 40 Repeat Example 1. However, 2-chloro-4,6-bis-(
2',2',6',6'-tetramethylpiperidyl-4
423.5 parts of '-amino)-triazine are reacted with 282 parts of a diphenyl-diphosphinic acid mixture (Example 39) or 314 parts of a diphenyl-diphosphonic acid mixture (Example 40) to give the salt. The product obtained has good fastness to light and heat.

Examples 41-46 Repeat Example 1. However, terephthalic acid-bis-(2,2,
6,6-tetramethylpiperidyl-4)-diamide 44
2 parts of the diphenyl-diphosphinic acid mixture (Example 41)
282 parts or diphenyl-diphosphonic acid mixture (Example 42)
) react with any of the 314 parts. Examples 41 and 42
isophthalic acid-bis-(2,2,6,6-tetramethylpiperidyl-4) instead of terephthalic diamide
-diamide (Examples 43 and 44) 442 parts or trimesic acid-tris-(2,2,6,6-tetramethylpiperidyl-4)-triamide (Examples 45 and 46) 576 parts or trimellitic acid-tris-(2 ,2,6,6-tetra-
Methylpiperidyl-4)-triamide (Example 46a) 57
6 parts can be used.

Examples 47 to 50 710 parts of pyromellitic acid-tetrakis-(2,2,6,6-tetramethylpiperidyl-4)-tetramid were prepared in a manner similar to Example 1 to form a diphenyl-diphosphinic acid mixture (Example 47). ) or 564 parts of a diphenyl-diphosphinic acid mixture (Example 48) or 314 parts of a diphenyl-diphosphonic acid mixture (Example 49) or 628 parts of a diphenyl-diphosphonic acid mixture (Example 50).

Examples 51 and 52 Repeat Example 1. However, 2-chloro-4,6-bis-(2
',2',6',6'-tetramethylpiperidyl-4'
-amino)-triazine, 423.5 parts of naphthalene-
React with either 132 parts of a phosphinic acid mixture (Example 51) or 148 parts of a naphthalene-phosphonic acid mixture (Example 52). After purification of the product, a product is produced which has very good dyeability and good fastness to light and heat on plastic materials.

Examples 53 and 54 Repeat Example 2. However, 184.5 parts of 2,4,6-trichlorotriazine is first reacted with 108 parts of 2,2,6,6-tetramethyl-4-aminopiperidine, and then 4-amino-phenyl-phosphonic acid (e.g. 53) 157 parts or 4-amino-phenyl-phosphonic acid (Example 54) 17
Make it react with any of the three parts.

Examples 55 and 56 Repeat Example 2. However, tetrachloro-pyrimidine 21
8 parts of 4-amino-phenyl-phosphinic acid (Example 55)
) or 346 parts of 4-amino-phenyl-phosphonic acid (Example 56). The product obtained is as effective as the product of Example 2.

Examples 57-60 Repeat Examples 11-14. However, terephthalic acid bis-
(2,2,6,6-tetramethylpiperidyl-4)-diester (terephthalic acid di-chloride and 2,2,6,6
444 parts of phenylphosphinic acid (Example 57)
142 parts of phenylphosphinic acid (Example 58) or 158 parts of phenylphosphonic acid (Example 59) or 316 parts of phenylphosphonic acid (Example 60). These products also exhibit excellent fastness to light and heat and improve the dyeability of plastic materials.

Examples 61 and 62 Repeat Example 1. However, instead of phenylphosphinic acid, 200 parts of acenaphthenylphosphinic acid (Example 61) or 216 parts of acenaphthenylphosphonic acid (Example 62) is used.

APPLICATION EXAMPLE 99 parts of polyε-caprolactam in powder form were added to Example 1.
1 part of the product in a mixer. The powder is
Mix very quickly and homogeneously. After about 10 minutes, the mixture is dried for 16 hours at 220°C, transferred to a melt rotary machine, and after an 8 minute hold at 275-280°C, spun into fibers under a nitrogen atmosphere. The resulting fiber material can be dyed with acid dyes in light to deep shades and exhibits excellent light, wash, oxidation and rubfastness. The application example is that instead of 1 part of the product of Example 1, Examples 2 to 6
0 can be repeated using 1 part of the product of any one example.

Claims (15)

[Claims] 1. A mono-, di- or tricarbocyclic phosphinic acid or phosphonic acid compound containing i) at least one group reactive with hydroxy and/or amino and/or ii) sterically hindered. A compound comprising at least one group containing an amine. 2. The mono-, di- or tricarbocyclic group is unsubstituted or halogen, hydroxyl, C1-4 alkyl, phenyl, C1-4 alkoxy and/or C
1-4 C5-7 cycloalkyl, phenyl, naphthyl, tetrahydronaphthyl, mono- or di-substituted with a water-insoluble substituent selected from alkoxycarbonyl groups,
2. The compound according to claim 1, which is an acenaphthene or acenaphthylene group. 3. A cyclic group in which the group reactive with hydroxy and amino groups carries at least one reactive group and has at least two nitrogen atoms (which may be separated by 1 or 2 carbon atoms). Claim 1 selected from the group
or the compound described in 2. 4. The group reactive with hydroxy and amino groups is a triazinyl, pyrimidinyl, quinoxalinyl, quinazocnyl, phthalazinyl, benzoxazolyl, benzithiazolyl group and the following general formula: [Formula 1] , R30 is a halogen atom or a group -N+ (C1-
4 alkyl)3 or -N+ A- (pyridinium) and A- is an anion. 5. A compound according to claim 1, wherein the groups reactive with hydroxy and amino groups are selected from mono- and dichlorotriazinyl, mono- and dichloropyrimidinyl and mono- or dichloroquinoxalinyl. [Claim 6] The following general formula I or II: [In the formula, R is unsubstituted or halogen, C1-4
is a mono-, bi- or tricarbocyclic group substituted with one or more substituents selected from alkyl or C1-4 alkoxy groups; R1 is a group reactive with hydroxy and amine; R2 is a group -NR3- or -O- (where R3 is hydrogen or C1-4 alkyl)
R4, together with the two carbon atoms to which the group R8 is attached and the nitrogen atom to which R5 is attached, forms a 5-, 6- or 7-membered cyclic group, and optionally further contains a water-insoluble and/or to which an additional cyclic group is attached to form a spiro group;
is a hydrogen atom, C1-4 alkyl or acyl; each R8 is independently a C1-6 alkyl group, preferably methyl or ethyl, more preferably methyl; n
is 0 or 1; P is 1, 2 or 3; and P
a is 0, 1 or 2, where the sum of P+Pa is 1,
2 or 3]. [Claim 7] The following general formula III or IV:
] [wherein n is 0 or 1; r and r' are, independently of each other, 1, 2 or 3; P' is 1, 2, 3 or 4
and Pa' is 0, 1, 2 or 3, provided that the sum of P' and Pa' and the sum of r and r' is 2, 3 or 4; R10 is an amide or ester-bonded phenyl group; , and the other symbols are as defined in claim 1. 8. The phosphine and phosphonic acid groups are
The compound according to claim 1, which is derived from a compound represented by the following general formula V: embedded image wherein R10a is a direct bond, oxygen, C1-4 alkylene or -CH=CH-. 9. The amine-containing group according to claim 1, wherein the sterically hindered amine-containing group is represented by the following general formula: [Image Omitted] [wherein the symbols are as described in claim 6] Compound. 10. The sterically hindered amine-containing group has the following general formulas a) to e): [Image Omitted] wherein R5' is hydrogen, C1-4 alkyl or acyl, and each R9 are independently hydrogen, C1-4
alkyl or one R9 is phenyl and the other R9 is hydrogen or C1-4 alkyl, or both R9 groups together form the group -(CH2)11-,
and -Y- is -N-CO- or -CO-N-]
The compound according to claim 1, which is represented by: 11. A method for preparing a compound according to claim 1, comprising: a) a suitable amount of a compound containing one or more groups capable of reacting with hydroxy and/or amino; b) an appropriate amount of mono-, di- or tri-carbocyclic phosphine or phosphonic acid and an appropriate amount of steric phosphine or phosphonic acid; a amine-containing compound, which latter compound may contain one or more groups capable of reacting with hydroxy and/or amino groups. 12. A method for improving the dyeability of plastic materials, comprising applying a compound according to claim 1 to the plastic materials. 13. A plastic material to which the compound according to claim 1 is applied. 14. The material is polyolefin, ethylene/propylene copolymer, polybutylene, polystyrene, chlorinated polyethylene, polyvinyl chloride, polyester, polyamide, polycarbonate, polymethyl methacrylate, polyphenylene oxide, polyurethane, polypropylene oxide, polyacetate. , phenyl-formaldehyde resin, epoxide resin,
14. Plastic material according to claim 13, selected from polyacrylonitrile and copolymers thereof, such as ABS-terpolymers. 15. The material is an ABS-terpolymer of polypropylene, polyethylene (eg, high molecular weight polyethylene), ethylene/propylene copolymer, polyvinyl chloride, polyester, polyamide, polyurethane, polyacrylonitrile, acrylic acid, styrene and acrylonitrile, Plastic material according to claim 13, selected from copolymers of styrene and acrylonitrile or styrene and butadiene.