DE4125440A1 - MONO, BI OR TRI-CARBOCYCLIC PHOSPHINE OR PHOSPHONIC ACID COMPOUNDS - Google Patents

Description

The invention relates to mono-, bi- or tri-carbocyclic Phosphine or phosphonic acid compounds, which in the molecule (i) at least a radical reactive towards hydroxyl and amino groups and / or (ii) contain a group with sterically hindered amine, the individual Components of these compounds via nitrogen or oxygen atoms, amide, ester or salt-like bonded together.

It was found that the organic phosphine and Phosphonic acid compounds very good for improving the dyeability and, especially if they ent a sterically hindered amino group maintain stability to light, especially UV light, oxidation, Bleaching and heat are suitable when they are in fully or semi-synthetic, high molecular, (especially hydrophobic) plastics incorporated and be distributed homogeneously. For example, they are suitable for poly olefins, especially polyethylene and polypropylene, ethylene / propylene copolymers, polybutylene, as well as polystyrene, chlorinated polyethylene and Polyvinyl chloride, polyester, polyamides, polycarbonates, polymethyl meth acrylates, polyphenylene oxides, polyurethanes, polypropylene oxide, polyacetates, Phenol-formaldehyde resins, epoxy resins, polyacrylonitrile and the like Copolymers and ABS terpolymers. It is preferred to use the compounds according to the invention for stabilizing polypropylene, Polyethylene including high molecular weight polyethylene, ethylene / propylene Copolymers, polyvinyl chloride, polyester, polyamide, polyurethanes, Polyacrylonitrile, ABS polymers of acrylic ester, styrene and acrylonitrile, Copolymers of styrene and acrylonitrile or styrene and butadiene  preferably for polypropylene, polyethylene, ethylene / propylene copolymers or SECTION.

The compounds mentioned are particularly suitable for improving the mentioned properties of synthetic polyamides, here the Improvement of the dyeability, the color intensity (dye yield), the bleach fastness, the light fastness and the wash fastness of the dyeings as well as the noticeably increased stability of the substrate against light damage are also particularly noteworthy.

All known plastics are among synthetic polyamides to understand this type, in particular the polycondensates or polymers sate from dicarboxylic acids and diamines, e.g. B. from adipic acid and hexa methylenediamine, from lactams, e.g. B. ε-caprolactam, from aminocarboxylic acids, e.g. B. ω-aminoundecanoic acid or aromatic dicarboxylic acids (iso- or Terephthalic acid) and aromatic diamines (para-phenylenediamine).

Natural substances, for example rubber, can also be stabilized will. The incorporation of the new connections into those to be protected Materials are made according to known methods. A special one an important application method is the intimate mixing of a Plastic with the new compounds in the melt z. B. in one Kneaders or by extrusion, injection molding, blow molding, spinning corresponding articles. Polypropylene or poly is preferably used ethylene in granular, semolina or powder form. When processing e.g. B. by extrusion, injection molding, rotary molding or by blow molding you get for example foils, films, hoses, pipes, containers, Bottles, profile parts, fibers, threads, tapes or even foams.

The plastics do not necessarily have to be polymerized or condensed be mixed before mixing with the compounds of the invention he follows. Monomers or prepolymers or precondensates can also be used mix with the compounds of the invention and only afterwards when or after condensing or polymerizing the plastic into the  convert final form.

The process of stabilizing plastics against degradation by Light, oxidation and heat are characterized in that the stabilizing plastics one or more of the aforementioned compound dung in a concentration of 0.2 to 5 percent by weight, preferably show 0.5 to 2, in particular by 1.0 percent by weight before, during or after polymer formation in the mass.

As already mentioned, particular preference is given to the modification of synthetic polyamides, mono-, bi- or tri-carbocyclic phosphine and phosphonic acid compounds which are one against hydroxyl and amino groups reactive residue and at least one, preferably two groups contain sterically hindered amine. Such connections correspond to e.g. B. formulas I and II

where in these formulas
R is a mono-, bi- or tri-carbocyclic radical which preferably carries one or two substituents from the group consisting of chlorine, bromine, C _1-4 alkyl or alkoxy, preferably a phenyl radical,
R₁ the rest of a compound reactive towards hydroxyl and amino groups
R₂ is an -NR₃- or -O bridge member,
R₃ is hydrogen or C _1-4 alkyl,
R₄ is the atomic group necessary to complete a 5-, 6- or 7-membered ring, which may carry further non-water-solubilizing substituents and / or contain another ring in a spiro bond,
R₅ is hydrogen, C _1-4 alkyl or acyl,
all R₈ C _1-5 alkyl, preferably methyl
n zero or 1,
p 1, 2 or 3 and
p ′ is 0, 1 or 2, the sum p + p ′ being 1, 2 or 3.

The options for using are also very versatile Compounds of formula III or IV

where in these formulas
R is a mono-, bi- or tri-carbocyclic radical which preferably carries one or two substituents from the group consisting of chlorine, bromine, C _1-4 alkyl or alkoxy, preferably a phenyl radical,
R₁ 'the remainder of an amide- or ester-like bonded benzene, di-, tri- or tetracarboxylic acid,
R₂ is an -NR₃- or -O bridge member,
R₃ is hydrogen or C _1-4 alkyl,
R₄ is the atomic group necessary to complete a 5-, 6- or 7-membered ring which may carry further non-water-solubilizing substituents and / or may contain another ring in a spiro bond,
R₅ is hydrogen, C _1-4 alkyl or acyl,
all R₈ C _1-5 alkyl, preferably methyl
n zero or 1,
q 1, 2, 3 or 4,
q ′ 0, 1, 2 or 3,
r and r 'each represent 1, 2 or 3
and the sum q + q ′, and r + r ′ = 2, 3 or 4.

As mono-, bi- or tri-carbocyclic radicals (mono-, dinuclear or trinuclear, carbocyclic radicals) come, for. B. C _5-7 cycloalkyl, in particular cyclohexyl, phenyl, naphthyl, tetrahydronaphthyl, acenaphthene or acenaphthylene radicals into consideration, which (in particular the mononuclear radicals) may not be water-solubilizing substituents, e.g. B. halogen atoms, (especially chlorine or bromine), hydroxyl, C _1-4 alkyl (z. B. tert. Butyl), phenyl, C _1-2 alkoxy and / or C _1-2 alkoxycarbonyl groups can wear, but they are preferably unsubstituted.

Compounds of also come as phosphinic or phosphonic acid components Formula V into consideration

wherein R₁₀ is the direct bond, oxygen, C _1-3 alkylene or -CH = CH- and n is zero or 1.

Polynuclear carbocyclic radicals can also have more than one phosphine or Wear phosphonic acid group. Preferred compounds contain per Phosphine and / or phosphonic acid group with at least one group hindered amine. The phenylphosphine are particularly preferred and phenylphosphonic acids.

Among residues of compounds that are opposite to hydroxy and amino groups are reactive, are all known in the chemistry of reactive dyes  Understand reactive groups. Cyclic groups are preferred here, with at least two nitrogen atoms (created by one or two coals atoms are separated) to understand, e.g. B. triazinyl, pyrimidyl, Quinoxalyl and quinazolyl groups, but also phthalazinyl, benzoxazolyl and benzothiazolyl groups as well as groups of the formulas

where Y is a halogen atom, preferably a chlorine atom or a radical of Formula -N⁺ (alkyl) ₃ or

is [see also the articles by K. G. Adhesive "About new reactive dyes" Angew. Chem. 76, (1964), No. 10, p. 423 ff .; E. Siegel "Chemistry of reactive dyes", Chemica, Supplement March 1968, 3rd Interlaken Color Symposium, p. 102 ff; E. Siegel in "The Chemistry of Synthetic Dyes "Vol. VI, Chapter 1, edited by K. Venkataramn, Academic Press (1972)].

Preferred reactive radicals are e.g. B. mono- or dichlorotriazinyl, pyrimidinyl or quinoxalinyl residues, especially the monochlor triazinyl residue.

Preferred acyl groups (in R₅ and R₆) correspond to the formula B-Y₁- or B'-Z-, therein
B is a hydrocarbon radical which can carry substituents and / or contain heteroatoms, preferably a C _1-4 alkyl or phenyl radical,
Y₁ is a radical -O-CO-, -SO₂- or -O-SO₂-,
B ′ is a hydrogen atom or B,
Z -CO-, -NB '' - CO- or -NB '' - SO₂- (B '' only bound to the nitrogen atom) and
B ′ ′ hydrogen or B.

Particularly preferred acyl residues are the C _1-4 carboxylic acid residues.

Preferred residues of compounds with a sterically hindered amino group, of the formula

are z. B. those of the formulas a to e

wherein all R'₅ hydrogen, C _1-4 alkyl, acyl or in the form of the phosphinic or phosphonic acid salt, together with the sterically hindered nitrogen atom, a group of the formula

all R₈ C _1-5 alkyl, preferably methyl,
the two R₉ are independently hydrogen, C _1-2 alkyl
R₉ also phenyl, or both R₉ together form a group of the formula - (CH₂) ₁₁- and
Y is a group of the formula -N-CO- or -CO-N-.

The radicals of the formulas a, c, d and e are preferably via an -NH- or -O bridge bound to the molecule in the manner of an amide or ester.

Unless otherwise stated, alkyl is preferably alkyl radicals to understand with 1 to 4 carbon atoms. The production of the new Connections take place in analogy to the production of similar, known Links. It lies within the knowledge of a specialist. The Manufacturing process is characterized in that

• i) one mole of a compound with m versus hydroxyl and Amino groups reactive atoms or atom groups with m ′ mol one a reactive hydroxyl or amino group containing mono bi- or tri-carbocyclic phosphine or phosphonic acid compound dung condenses, where m is 2 or 3 and m ′ is 1, 2 or 3, or  
• ii) optionally one against hydroxyl and amino groups reactive radical containing compound with at least one sterically hindered amine, with a mono-, bi- or tri- converts carbocyclic phosphine or phosphonic acid.

So z. B. the compounds of formula I prepared in that 1 mol of a compound of the formula I ′

with p mol of a phosphinic or phosphonic acid of the formula I ′ ′

implemented (neutralized).

The compounds of formula II are obtained by condensing one mole a p + p ′ + possibly 1 (if p + p ′ = 1 or 2 and if a reactive residue should remain) reactive atoms or groups of atoms containing compound with p mol of a compound of formula II '

and p ′ mol of a compound of the formula (II ′ ′)

The compounds of formula III z. B. by salt formation from one Mole of a compound of formula III ′

with q mol of a mono-, di- or tri-carbocyclic phosphine or Get phosphonic acid.

The compounds of formula IV are obtained by reaction (esterification or amide formation) of a mole of a di-, tri- or tetracarboxylic acid (or a functional derivative of such an acid, preferably the acid chloride) with r mole of a compound of formula II '' (above) and q 'mole a compound of formula II '.

The compounds of formula I 'are obtained by condensing one mole a p + p ′ + possibly 1 (if p + p ′ = 1 or 2 and if a reactive residue should remain) towards hydroxyl and amino groups reactive atom or atom-containing compound with p mol of a  Compound of the formula I ′ ′ ′

and p ′ mol of a compound I ^iv

The condensation of the compounds II ', II'',I''' and I ^iv with the reactive compounds takes place in a generally known manner, for. B. in an aqueous, optionally (soda) alkaline medium, at temperatures up to about 100 ° C, with stirring, optionally with increasing the pH by adding alkali.

The compounds of formula III 'are by condensation of a mole a benzene di, tri- or tetracarboxylic acid, or a functional Derivative of such an acid, preferably the acid chloride, with q mol a compound of the formula III ′ ′

and q ′ mol of a compound of the formula (III ′ ′ ′)

produced. This condensation (amide or ester formation) of the acid derivatives with the compounds of the formulas III ′ ′, III ′ ′ ′, IV ′ and IV ′ ′  take place in a generally known manner.

In the following examples, parts are by weight and Percentages by weight. The temperatures are in degrees Celsius specified.

Example 1

423.5 parts of 2-chloro-4,6-bis- (2 ′, 2 ′, 6 ′, 6′-tetramethylpiperidyl-4′-amino) - triazine (known from DE-PS 23 19 816) are sus in 1500 parts of water oscillates and the mixture is mixed with 142.0 parts of phenylphosphinic acid, warmed to 50 ° and stirred at this temperature for 2 hours. You fil removes the insoluble salt, washes it with water and dries it in Vacuum. The hygroscopic product melts at 218-220 °.

The product corresponds to the formula

Elemental analysis:
C 56.6 (57.2)%, H 8.3 (8.0)%, Cl 6.3 (6.3)%
N 17.1 (17.3)%, P 5.3 (5.5)%, O 6.9 (5.7)%

Example 2

184.5 parts of 2,4,6-trichlorotriazine and 314 parts of 4-aminophenylphosphine acid are stirred into 1300 parts of water and ge at 50 ° for 2 hours stirs. The undissolved reaction product is filtered off, with water acid washed free and dried in vacuo. This gives 2-chloro-4,6-bis- (4'-phosphinic acid-phenylamino) triazine with a melting point of <300 °.

Instead of the phosphinic acid used in Example 1, 158 Parts of phenylphosphonic acid (Ex. 3), and instead of that in Example 2 put phosphinic acid can 346.0 parts of 4-aminophenylphosphonic acid (Ex. 4) can be used.

Examples 5 to 9

The procedure is as given in Example 1, but instead of indicated 142.0 parts phenylphosphinic acid 284.0 parts phenylphosphine acid (Ex. 5) or 316.0 parts of phenylphosphonic acid (Ex. 6) compounds that make hydrophobic plastics noticeably easier to dye make and these plastics, colored or uncolored, excellent against protect the harmful effects of light and heat.

The procedure described in Example 1 is followed, but 544.0 is used Parts of 2,4,5-tris- (2 ', 2', 6 ', 6'-tetramethylpiperidyl-4'-amino) -triazine (prepared according to DE-PS 23 19 816) and 284.0 parts of phenylphosphinic acid (Ex. 7) or 316.0 parts of phenylphosphonic acid (Ex. 8) are obtained similarly effective connections.

With 556.0 parts of 2- (1 ′, 2 ′, 6 ′, 6′-pentamethylpiperidyl-4′-amino) -4,6- bis - () 2 ′ ′, 2 ′ ′, 6 ′ ′, 6 ′ ′ - tetramethylpiperidyl-4-amino) -triazine (analogous to that in the method described in DE-PS 23 19 816 available) and 284.0 Parts of phenylphosphinic acid (Ex. 9) or 316.0 parts of phenylphosphone Acid, implemented analogously to Example 1, also gives an effective compound fertilize.  

Example 10

2- (phenylphosphinic acid-4'-amino) -4,6-bis- (2 '', 2 '', 6 '', 6 '' - tetramethy-l piperidyl-4 ′ ′ - amino) -triazine is produced by condensation of 423.5 Share 2-chloro-4,6-bis- (2 ', 2', 6 ', 6'-tetramethylpiperidyl-4-amino) triazine with 157 parts of 4-aminophosphinic acid, in 25 percent aqueous soda solution by stirring for 5-8 hours at 80 °, acidifying the reaction mixture mix with dilute HCl to a pH of about 2, filter off, Wash out with water and dry the insoluble product.

The compound thus obtained also promotes the ability to be dyed synthetically Polymers, especially synthetic polyamides, and increases the stocks resistance of plastics to light and heat.

Examples 11 to 14

Analogous to the procedure of the first example, 442.0 parts of tere are used phthalic acid bis- (2,2,6,6-tetramethylpiperidyl-4 -) - diamide with 142.0 Parts (Ex. 11) or 284.0 parts (Ex. 12) phenylphosphinic acid, or with 158.0 parts (Ex. 13) or 316.0 parts (Ex. 14) phenylphosphone acid around.

Examples 15 to 18

Analogously to the procedure of Example 1, 442.0 parts of Iso are used phthalic acid bis (2,2,6,6-tetramethylpiperidyl-4) diamide with 142.0 parts (Ex. 15) or 284.0 parts (Ex. 16) phenylphosphinic acid, or with 158.0 Divide (Ex. 17) or 316 parts (Ex. 18) phenylphosphonic acid by and each receives a product with very good light and heat stability sieren, as well as the dyeability properties.

Examples 19 to 30

Analogous to the procedure of the first example, 576.0 parts of trimesine acid tris (2,2,6,6-tetramethylpiperidyl-4) triamide (DE-PS 20 40 975) with 142.0 parts (Ex. 19), 284.0 parts (Ex. 20) and 426.0 parts (Ex. 21) phenylphosphinic acid, and with 158.0 parts (Ex. 22), 316.0 parts (Ex. 23) or 474.0 parts (Ex. 24) phenylphosphonic acid under salt education implemented. This way you get products with a very good effect.  Other products with practically the same effect can be obtained when on Place the same amount of trimellitic acid tris (2,2,4,4- tetramethylpiperidyl-4) triamide is used (Examples 25 to 30).

Examples 31 to 38

Analogously to the procedure of Example 1, 710.0 parts of pyromellite Acid tetrakis (2,2,6,6-tetramethylpiperidyl-4) tetramide with 142.0 parts (Ex. 31), 284.0 parts (Ex. 32), 426.0 parts (Ex. 33) and 568.0, respectively Parts (Ex. 34) phenylphosphinic acid, as well as 158.0 parts (Ex. 35), 316.0 parts (Ex. 36), 474.0 parts (Ex. 37), or 632.0 parts (Ex. 38) phenylphosphonic acid reacted with salt formation, again Products with very good effects as dyeability improvers and as Stabilizers received.

Examples 39 and 40

Analogous to the procedure of Example 1, 423.5 parts of 2-chloro-4,6- bis- (2 ', 2', 6 ', 6'-tetramethylpiperidyl-4'-amino) triazine as in Example 1 indicated, with 282.0 parts of a diphenyl-diphosphinic acid mixture (Ex. 39), or 314.0 parts of a diphenylphosphonic acid mixture (Ex. 40) a salt, which is also very good as a stabilizer and suitable as a dyeability improver.

Examples 41 to 46

442.0 parts of terephthalic acid bis (2,2,6,6-tetramethylpiperidyl-4) diamide are, analogous to the procedure of Example 1 with 282.0 parts of one Diphenyl-diphosphinic acid mixture (Ex. 41), or 314.0 parts of one Diphenyl-diphosphonic acid mixture (Ex. 42) converted to a salt. Instead of the 442.0 parts of terephthalic acid diamide, each can also 442.0 parts of isophthalic acid bis (2,2,6,6-tetramethylpiperidyl-4) diamide (Examples 43 and 44), or 576.0 parts of trimesic acid tris (2,2,6,6- tetramethylpiperidyl-4 -) - triamide (Examples 45 and 46), or 576.0 parts Trimellitic acid tris (2,2,6,6-tetramethylpiperidyl-4) triamide used will.  

Examples 47 to 50

710.0 parts of pyromellitic acid tetrakis (2,2,6,6-tetramethylpiperidyl-4) - Tetramid are analogous to the information in the first example, with 282.0 parts (Ex. 47), or 564.0 parts (Ex. 48) of a diphenyldiphosphinic acid mixture, as well as 314.0 parts (Example 49) or 628.0 parts (Example 50) implemented and isolated a diphenyldiphosphonic acid mixture.

Examples 51 and 52

Analogous to the information in Example 1, 423.5 parts of 2-chloro-4,6- bis- (2 ', 2', 6 ', 6'-tetramethylpiperidyl-4'-amino / triazine with 132.0 parts a naphthalenephosphinic acid mixture (Ex. 51), or 148.0 parts of one Naphthalinphosphonsäurememisch (Ex. 52) implemented, where after Pure representation of a product with very good, the dyeability and the Light and heat stability of plastics improving properties receives.

Examples 53 and 54

Analogous to the procedure of the second example, 184.5 parts of 2,4,6-tri chlorotriazine first with 108 parts of 2,2,6,6-tetramethyl-4-aminopiperidine and then with 157.0 parts of 4-aminophenylphosphinic acid (Ex. 53), or 173.0 parts of 4-aminophenylphosphonic acid (Ex. 54).

Examples 55 and 56

Analogous to the information in the second example, 218.0 parts of tetrachlor pyrimidine with 314 parts of 4-aminophenylphosphinic acid (Ex. 55), or 346 Share 4-aminophenylphosphonic acid (Ex. 56) implemented. The received Product shows practically the same effect as that according to Example 2 he held.

Examples 57 to 60

Analogous to the information in Examples 11 to 14, 444.0 parts of the Terephthalic acid bis (2,2,6,6-tetramethylpiperidyl-4) diester (herge represents from terephthalic acid dichloride and 2,2,6,6-tetramethyl-4-hydroxy piperidine) with 142.0 parts (Ex. 57) or 284.0 parts (Ex. 58) Phenylphosphinic acid, as well as with 158.0 parts (Ex. 59) or 316.0 parts  (Ex. 60) implemented phenylphosphonic acid. These products also show one excellent effect as a dye enhancer, light and heat stabilizers.

Examples 61 and 62

The procedure is as given in Example 1, but instead of Phenylphosphinic or phenylphosphonic acid 200 parts acenaphthenyl-phos phinic acid (Example 61) or 216 parts of acenaphthenylphosphonic acid (Example 62) and thus also receives very valuable stabilizers.

Application example

99 parts of poly-ε-caprolactam in the form of a powder are mixed with 1 part of the Phosphinic acid compound prepared according to Example 1 in a drum mixer mixed. The powder distributes itself very evenly after a short time moderate. After about 10 minutes, the mixture is dried at 220 ° for 16 hours net, placed in a melt spinning machine and after 8 minutes Ver spun into fibers at 275-280 ° C under a nitrogen atmosphere.

The fiber material thus obtained can be made with the usual acidic color dye fabrics lightly in deep tones, the dyeings obtained are very good brilliant and excellent light, wash, oxidation and rub fast.

Claims (9)

1. Mono-, bi- or tri-carbocyclic phosphinic or phosphonic acid compounds which have at least one hydroxyl- and amino groups reactive radical and / or (ii) a group with contain sterically hindered amine, the individual components of these compounds via nitrogen or oxygen atoms, amide, are bound together like an ester or salt. 2. Mono-, bi- or tri-carbocyclic phosphinic or phosphonic acid Compounds according to claim 1, which one against hydroxyl and Amino group reactive radical and at least one, preferably two Contain groups with sterically hindered amine. 3. phosphine or phosphonic acid compounds according to claim 1, the formula I and II where in these formulas
R is a mono-, bi- or tri-carbocyclic radical which preferably carries one or two substituents from the group consisting of chlorine, bromine, C _1-4 alkyl or alkoxy, preferably a phenyl radical,
R₁ the rest of a compound reactive towards hydroxyl and amino groups
R₂ is an -NR₃- or -O bridge member,
R₃ is hydrogen or C _1-4 alkyl,
R₄ is the atomic group necessary to complete a 5-, 6- or 7-membered ring, which may carry further non-water-solubilizing substituents and / or contain another ring in a spiro bond,
R₅ is hydrogen, C _1-4 alkyl or acyl,
all R₈ C _1-5 alkyl, preferably methyl
n zero or 1,
p 1, 2 or 3 and
p ′ is 0, 1 or 2, the sum p + p ′ being 1, 2 or 3. 4. phosphine or phosphonic acid compounds according to claim 1, of formula III or IV where in these formulas
R is a mono-, bi- or tri-carbocyclic radical which preferably carries one or two substituents from the group consisting of chlorine, bromine, C _1-4 alkyl or alkoxy, preferably a phenyl radical,
R₁ 'the remainder of an amide- or ester-like bonded benzene, di-, tri- or tetracarboxylic acid,
R₂ is an -NR₃- or -O bridge member,
R₃ is hydrogen or C _1-4 alkyl,
R₄ is the atomic group necessary to complete a 5-, 6- or 7-membered ring, which may optionally carry further non-water-solubilizing substituents and / or contain another ring in a spiro bond,
R₅ is hydrogen, C _1-4 alkyl or acyl,
all R₈ C _1-5 alkyl, preferably methyl
n zero or 1,
q 1, 2, 3 or 4,
q ′ 0, 1, 2 or 3,
r and r 'each represent 1, 2 or 3
and the sum q + q ′, and r + r ′ = 2, 3 or 4. 5. Organic phosphine and phosphonic acid compounds according to one of the preceding claims, wherein the groups with sterically hindered amine correspond to the formulas a to e: wherein all R₅ 'is hydrogen, C _1-4 alkyl, acyl or in the form of the phosphinic or phosphonic acid salt, together with the sterically hindered nitrogen atom, a group of the formula R is a mono-, bi- or tri-carbocyclic radical which preferably carries one or two substituents from the group consisting of chlorine, bromine, C _1-4 alkyl or alkoxy, preferably a phenyl radical,
all R₈ C _1-5 alkyl, preferably methyl, the two R₉ independently of one another hydrogen, C _1-2 alkyl, one R₉ also phenyl, or both R₉ together form a group of the formula - (CH₂) ₁₁- and
Y is a group of the formula -N-CO- or -CO-N- and n is 0 or 1. 6. Phosphine or phosphonic acid compounds according to one of the previously outgoing claims, wherein the against hydroxyl and amino groups reactive radical is a mono- or dichlorotriazinyl radical, a mono- or Dichloropyrimidinyl residue or a mono- or dichloroquinoxalinyl residue, is preferably a mono- or dichlorotriazinyl radical.   7. A process for the preparation of the phosphine and phosphonic acid compounds according to claim 1, characterized in that

• i) one mole of a compound with m atoms which are reactive toward hydroxyl and amino groups or atom groups with m ′ mole of a mono- or tri-carbocyclic phosphine or phosphonic acid compound containing a reactive hydroxyl or amino group, wherein m 2 or 3 and m '1, 2 or 3 means, or
• ii) a compound which optionally contains a radical which is reactive toward hydroxyl and amino groups and with at least one sterically hindered amine is reacted with a mono-, bi- or tri-carbocyclic phosphinic or phosphonic acid.

8. Use of the mono-, di- or tri-carbocyclic phosphine and Phosphonic acid compounds according to claim 1, for improving the Dyeability of plastics and especially one steric hindered amino group-containing compounds also for ver improvement of the light stability of the colored and unstained Plastic. 9. Process for stabilizing plastics against degradation Light, oxidation and heat, characterized in that the stabilizing plastics 0.2 to 5, preferably 0.5 to 2, ins especially by 1.0 percent by weight of one or more compounds according to claim 1, before, during or after polymer formation in which Mass adds.