CH681542A5 - - Google Patents

Description

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CH 681 542 A5

description

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

It has been found that the organic phosphine and phosphonic acid compounds mentioned are very suitable for improving the dyeability and, in particular if they contain a sterically hindered amino group, the stability to light, in particular UV light, oxidation, bleaching and heat, if they are incorporated into fully or semi-synthetic, high molecular weight (especially hydrophobic) plastics and distributed homogeneously. They are thus suitable, for example, for polyolefins, in particular polyethylene and polypropylene, ethylene / propylene copolymers, polybutylene, and also polystyrene, chlorinated polyethylene and polyvinyl chloride, polyesters, polyamides, polycarbonates, polymethyl methacrylates, polyphenylene oxides, polyurethanes, polypropylene oxide, polyacetates, phenol-formaldehyde resins , Epoxy resins, polyacrylonitrile and corresponding copolymers and ABS terpolymers. The compounds according to the invention are preferably used to stabilize polypropylene, polyethylene, including high molecular weight polyethylene, ethylene / propylene copolymers, polyvinyl chloride, polyester, polyamide, polyurethanes, polyacrylonitrile, ABS tepolymers of acrylic esters, styrene and acrylonitrile, copolymers of styrene and acrylonitrile or styrene and butadiene, preferably for polypropylene, polyethylene, ethylene / propylene copolymers or ABS.

The compounds mentioned are particularly suitable for improving the properties mentioned for synthetic polyamides, the improvement in dyeability, color intensity (dye yield), fastness to bleaching, light fastness and fastness to washing of the dyeings and the noticeably increased stability of the substrate against damage to light also being particularly mentioned are.

Synthetic polyamides are understood to mean all known plastics of this type, in particular the polycondensates or polymers made from dicarboxylic acids and diamines, e.g. from adipic acid and hexamethylenediamine, from lactams, e.g. e-caprolactam, from aminocarboxylic acids, e.g. co-aminoundecanoic acid or from aromatic dicarboxylic acids (iso- or terephthalic acid) and aromatic diamines (para-phenylenediamine).

Natural substances, for example rubber, can also be stabilized. The new connections are incorporated into the materials to be protected using methods known per se. A particularly important application method is the intimate mixing of a plastic with the new compounds in the melt e.g. in a kneader or by extrusion, injection molding, blow molding, spinning to corresponding articles. Polypropylene or polyethylene in granular, semolina or powder form is preferably used. When processing e.g. extrusion, injection molding, rotary molding or blow molding gives, for example, foils, films, hoses, tubes, containers, bottles, profile parts, fibers, threads, tapes or foams.

The plastics do not necessarily have to be completely polymerized or condensed before they are mixed with the compounds according to the invention. It is also possible to mix monomers or prepolymers or precondensates with the compounds according to the invention and only afterwards to convert the plastic into the final form during or after the condensation or polymerization.

The process for stabilizing plastics against degradation by light, oxidation and heat is characterized in that the plastics to be stabilized are given one or more of the compounds mentioned in a concentration of 0.2 to 5 percent by weight, preferably 0.5 to 2, in particular by 1.0 percent by weight before, during or after polymer formation in the bulk.

As already mentioned, mono-, bi- or tri-carbocyclic phosphine and phosphonic acid compounds which contain a radical which is reactive towards hydroxyl and amino groups and at least one, preferably two, groups with sterically hindered amine are preferred, in particular for the modification of synthetic polyamides . Such connections correspond e.g. formulas I and II

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CH 681 542 A5

cv * 8 1 K «

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(I),

(II),

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45

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,

Ri represents the remainder of a compound R2 reactive towards hydroxyl and amino groups, an -NR3- or -O-bridge member,

R3 is hydrogen or Ci-4-alkyl,

R4 the atomic group necessary for completing a 5-, 6- or 7-membered ring which may optionally carry further non-water-solubilizing substituents and / or contain a further ring in a spiro bond,

R5 is hydrogen, Ci-4-alkyl or acyl,

all Rß Ci-5-alkyl, preferably methyl n zero or 1,

p represents 1, 2 or 3 and p '0, 1 or 2, the sum p + p' being 1, 2 or 3

The possibilities for the use of compounds of the formula III or are also very varied

IV

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CH 681 542 A5

C \ * 3 @ î NH®2- 0-P- (0) a-H

I.

R

(III)

(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, Ci-4-alkyl or alkoxy, preferably a phenyl radical,

Ri '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 Ci-4-alkyl,

R4 the atomic group necessary for completing a 5-, 6- or 7-membered ring which may optionally carry further non-water-solubilizing substituents and / or contain a further ring in a spiro bond,

R5 is hydrogen, Ci-4-alkyl or acyl,

all R8 Ci-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.

Examples of mono-, bi- or tri-carbocyclic radicals (mono-, dinuclear or trinuclear, carbocyclic radicals) are C5-7-cycloalkyl, in particular cyclohexyl, phenyl, naphthyl, tetrahydronaphthyl, acenaphthene or acenaphthylene radicals into consideration, which (in particular the mononuclear radicals) optionally unsubstituting substituents, e.g. Halogen atoms, (especially chlorine or bromine), hydroxyl, Ci-4-alkyl (eg tert. Butyl), phenyl, Ci-2-alkoxy and / or Ci-2-alkoxycarbonyl groups, but they are preferably unsubstituted.

Compounds of the formula V are also suitable as phosphinic or phosphonic acid components

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CH 681 542 A5

H— (0) -P

(V)

n

OH

P - (0) - H

. n

OH

where Rio is the direct bond, oxygen, Ci-3-alkylene or -CH = CH-.

Multinuclear carbocyclic radicals can also carry more than one phosphinic or phosphonic acid group. Preferred compounds contain at least one group with sterically hindered amine per phosphine and / or phosphonic acid group. The phenylphosphinic and phenylphosphonic acids are particularly preferred.

Residues of compounds which are reactive towards hydroxyl and amino groups are understood to mean all reactive groups known in the chemistry of reactive dyes. Cyclic groups with at least two nitrogen atoms (which are separated by one or two carbon atoms) are preferably to be understood here, e.g. Triazinyl, pyrimidyl, quinoxalyl and quinazolyl groups, but also phthalazinyl, benzoxazolyl and benzthiazolyl groups as well as groups of the formulas

-C0- (alkyl) -! T ^ j f2c-cp2

/ I

-C0-CH = CHr-CH -CH2,

-CO-CH2CH2SO2 - aryl, -C0-C = CH2,

Y

-CH2CH2-N N-C0CH = »CH2

I.

C0CH = CH "

-'CO

-N-SO2-CH = CH2 alkyl

-C0-CH = CH2,

-CO-CH-CCI2, -CO-CH2-Y,

-S02-CH2 CH2-O-SO3 Na,

-CO-CHj-NS (alkyl) 3 Ï ©,

-C0-CH-CH-C00alkyl,

Y Y

where Y is a halogen atom, preferably a chlorine atom or a radical of the formula -N © (alkyl) 3 or ■ ®o [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 Color Symposium Interlaken, p. 102 ff .; E. Siegel in "The Chemistry of Synthetic Dyes" Vol. VI, Chapter 1, edited by K.Venkataramn, Academic Press (1972)].

Preferred reactive groups are e.g. Mono- or dichlorotriazinyl, pyrimidinyl or quinoxalinyl radicals, in particular the monochlorotriazinyl radical.

Preferred acyl groups (in R5 and Re) correspond to the formula B-Yr or B'-Z-, in which B is a hydrocarbon radical which may carry substituents and / or contain heteroatoms, preferably a Ci-4-alkyl or phenyl radical,

Yi is a radical -O-CO-, -SO2- or -O-SO2-,

-SO2-NH-CHj CH2-O-SO3 Na, -C0-CH2CH2-Y and

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CH 681 542 A5

B 'is a hydrogen atom or B,

Z -CO-, -NB "-CO- or -NB" -S02- (B "only bound to the nitrogen atom) and B" hydrogen or B.

Ci-4 carboxylic acid residues are particularly preferred acyl residues.

Preferred radicals of compounds with a sterically hindered amino group, of the formula in which all R's are hydrogen, Ci-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 Ci-5-alkyl, preferably methyl,

the two Rg are independently hydrogen, Ci-2-alkyl

Rg also phenyl, or both Rg together form a group of the formula - (CH2) «- 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 bonded to the molecule in an amide or ester-like manner via an —NH or —O bridge.

Unless otherwise stated, alkyl is preferably to be understood as meaning alkyl radicals having 1 to 4 carbon atoms. The new compounds are prepared analogously to the preparation of similar, known compounds. It lies within the knowledge of a specialist. The manufacturing process is characterized in that

1 a mole of a compound with m atoms which are reactive toward hydroxyl and amino groups or atom groups with m 'mole of a monobi- or tri-carbocyclic phosphine or phosphonic acid compound containing a reactive hydroxyl or amino group, wherein m 2 or 3 and nv 1,

2 or 3, 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 tricarbocyclic phosphinic or phosphonic acid.

For example, the compounds of the formula I are prepared by reacting 1 mol of a compound of the formula I '

are e.g. those of the formulas a to e

A ô

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CH 681 542 A5

(I ')

with p moles of a phosphine or phosphonic acid of the formula

0

II

HO-P-R <0) "- H

(I ")

implemented (neutralized).

The compounds of the formula II are obtained by condensing a mole of a p + p '+ optionally 1 (if p + p' = 1 or 2 and if a reactive radical is to be left behind) a compound containing reactive atoms or atomic groups with p mole of a compound of the formula II '

f / (ov

\

OH

(II ')

and p 'mole of a compound of formula (II ")

/ 8 C \ R8

HR -R, / N-R, -C-Rr

\

8th

8th

(II ").

The compounds of formula III are e.g. by salt formation of one mole of a compound of the formula III '

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CH 681 542 A5

(HI'),

obtained with q mol of a mono-, di- or tri-carbocyclic phosphinic or phosphonic acid.

The compounds of the formula IV are obtained by reacting (esterification or amide formation) 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 the formula II "(above) and q 'mole of a compound of formula II'.

j / CoVH \

xOH

(II »)

The compounds of the formula I 'are obtained by condensation of a mole of p + p' + if appropriate 1 (if p + p '= 1 or 2 and if a reactive radical is to be left behind) containing atoms or atom groups which are reactive toward hydroxyl and amino groups Compound with p mole of a compound of formula I '"

H ~ R2-R <

and p 'mole of a compound lîv

(I "')

s-R2-R4

(Iiv).

The condensation of the compounds II ', II ", I'" and liv with the reactive compounds takes place in a generally known manner, e.g. in an aqueous, if appropriate (soda) alkaline medium, at temperatures up to about 100 ° C., with stirring, if appropriate with an increase in the pH by addition of alkali.

The compounds of the formula III 'are obtained by condensing a mole of a benzene-di, tri- or tetra-carboxylic acid, or a functional derivative of such an acid, preferably the acid chloride, with q mole of a compound of the formula III "

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CH 681 542 A5

/ 8th

S * ~ C \ r8

i NH

■ R,

h-R2-R4

(III ")

and q 'mole of a compound of the formula (III' ")

'5

(III "')

produced. These condensations (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 parts by weight and percentages are percentages by weight. The temperatures are given in degrees Celsius.

423.5 parts of 2-chloro-4,6-bis (2 /, 2 ', 6', 6'-tetramethylpiperidyl-4'-amino) triazine (known from DE-PS 2 319 816) are in 1500 parts Suspended water and mixed with 142.0 parts of phenylphosphinic acid, heated to 50 ° and stirred at this temperature for 2 hours. The insoluble salt is filtered off, washed with water and dried in vacuo. 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)%, 0 6.9 (5.7)%

Example 2

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

example 1

Cl

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CH 681 542 A5

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

Examples 5 to 9

If the procedure is as described in Example 1, but instead of the stated 142.0 parts of phenylphosphinic acid, 284.0 parts of phenylphosphinic acid (Ex. 5) or 316.0 parts of phenylphosphonic acid (Ex. 6) are used, compounds are obtained which are hydrophobic Make plastics noticeably easier to color and protect these plastics, colored or uncolored, excellently against the damaging effects of light and heat.

The procedure of Example 1 is followed, but 544.0 parts of 2,4,5-tris (2 ', 2', 6 ', 6'-tetramethylpiperidyl-4'-amino) -triazine (prepared according to DE- PS 2 319 816) and 284.0 parts of phenylphosphinic acid (Ex. 7) or 316.0 parts of phenylphosphonic acid (Ex. 8), similarly effective compounds are obtained.

With 556.0 parts 2- (1 ', 2', 6 ', 6-pentamethylpiperidyl-4'-amino) -4,6-bis- (2 ", 2", 6 ", 6" -tetramethylpiperidyl) -4-amino) -triazine (obtainable analogously to the procedure described in DE-PS 2 319 816) and 284.0 parts of phenylphosphinic acid (Example 9) or 316.0 parts of phenylphosphonic acid, reacted analogously to Example 1, are likewise effective Links.

Example 10

2- (phenylphosphinic acid-4'-amino) -4,6-bis- (2 ", 2", 6 ", 6" -tetramethylpiperidyl-4 "-amino) -triazine is prepared by condensation of 423.5 parts of 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

Stirring at 80 ° for 5-8 hours, acidifying the reaction mixture with dilute HCl to a pH of about 2, filtering, washing with water and drying the insoluble product.

The compound thus obtained also promotes the dyeability of synthetic polymers, in particular synthetic polyamides, and increases the resistance of the plastics to light and heat.

Examples 11 to 14

Analogously to the procedure of Example 1, 442.0 parts of terephthalic acid bis- (2,2,6,6-tetra-methyipiperidyl-4 -) - diamide with 142.0 parts (Example 11) or 284.0 parts are used (Ex. 12) phenylphosphinic acid, or with 158.0 parts (Ex. 13) or 316.0 parts (Ex. 14) phenylphosphonic acid.

Examples 15 to 18

Analogously to the procedure of Example 1, 442.0 parts of isophthalic acid bis- (2,2,6,6-tetramethylpiperidyl-4) -diamide are used with 142.0 parts (Example 15) or 284.0 parts ( Ex. 16) phenylphosphinic acid, or with 158.0 parts (Ex. 17) or 316 parts (Ex. 18) phenylphosphonic acid and thus each obtains a product with very good light and heat stabilizing properties and improving the dyeability.

Example 19-30

Analogous to the procedure of Example 1, 576.0 parts of trimesic acid tris (2,2,6,6-tetramethyl-piperidyl-4) triamide (DE-PS 2 040 975) with 142.0 parts (Example 19 ), 284.0 parts (Ex. 20) or 426.0 parts (Ex. 21) phenylphosphinic acid, and with 158.0 parts (Ex. 22), 316.0 parts (Ex. 23) or 474.0 Share (Ex. 24) phenylphosphonic acid reacted with salt formation. This way you get products with a very good effect.

Further products with practically the same effect are obtained if the same amount of trimellitic acid tris (2,2,4,4tetramethylpiperidyl-4) triamide is used instead of trimesic acid (Examples 25 to 30).

Examples 31 to 38

Analogously to the procedure of Example 1, 710.0 parts of pyromellitic 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) or 568.0 parts (Ex. 34) phenylphosphinic acid, as well as with 158.0 parts (Ex. 35), 316.0 parts (Ex. 36), 474.0 parts ( Ex. 37) or 632.0 parts (Ex. 38) of phenylphosphonic acid reacted with salt formation, again giving products with very good activity as colorability improvers and as stabilizers.

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CH 681 542 A5

Examples 39 and 40

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

Examples 41 to 46

442.0 parts of terephthalic acid bis (2,2,6,6-tetramethylpiperidyl-4) diamide, analogous to the procedure of Example 1, with 282.0 parts of a diphenyldiphosphinic acid mixture (Ex. 41), or 314, 0 parts of a diphenyl-diphosphonic acid mixture (Ex. 42) converted to a salt. Instead of the 442.0 parts of terephthalic acid diamide, 442.0 parts of isophthalic acid bis- (2,2,6,6-t-tramethylpiperidyl-4) diamide (Examples 43 and 44) or 576.0 parts can also be used Trimesic acid tris (2,2,6,6-tetramethylpiperidyl-4 -) triamide (Examples 45 and 46), or 576.0 parts of trimellitic acid tris (2,2,6,6-tetramethylpiperidyl-4) triamide be used.

Examples 47 to 50

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

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 of a naphthalenephosphinic acid mixture (Ex. 51) or 148.0 parts of a naphthalenephosphonic acid mixture (Ex. 52) are reacted, a product having very good properties which improve the dyeability and the light and heat stability of plastics being obtained after preparation.

Examples 53 and 54

Analogous to the procedure of Example 2, 184.5 parts of 2,4,6-trichlorotriazine are first mixed 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

Analogously to the information in the second example, 218.0 parts of tetrachloropyrimidine are reacted with 314 parts of 4-aminophenylphosphinic acid (Ex. 55) or 346 parts of 4-aminophenylphosphonic acid (Ex. 56). The product obtained shows practically the same effect as that obtained in Example 2.

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 (prepared from terephthalic acid dichloride and 2,2,6,6-tetra- methyl-4-hydroxypiperidine) with 142.0 parts (Ex. 57) or 284.0 parts (Ex. 58) phenylphosphinic acid, and with 158.0 parts (Ex. 59) or 316.0 parts (Ex 60) implemented phenylphosphonic acid. These products also have an excellent effect as dyeability improvers, light and heat stabilizers.

Examples 61 and 62

The procedure described in Example 1 is followed, but 200 parts of acenaphthenylphosphinic acid (Example 61) or 216 parts of Acenaphthenylphosphonic acid (Example 62) are used in place of the phenylphosphinic or phenylphosphonic acid, respectively, and thus also very much are obtained valuable stabilizers.

Application example

99 parts of poly-e-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. The powder distributes itself very evenly after a short time. After about 10 minutes, the mixture is dried at 220 ° for 16 hours, introduced into a melt spinning machine and, after an 8-minute residence time at 275-280 °, spun into fibers under a nitrogen atmosphere.

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CH 681 542 A5

The fiber material obtained in this way can easily be dyed in deep tones with the customary acid dyes; the dyeings obtained are very brilliant and have excellent fastness to light, washing, oxidation and rubbing.

Claims (1)

Claims 1. mono-, bi- or tri-carbocyclic phosphine or phosphonic acid compounds which contain in molecule (i) at least one radical which is reactive towards hydroxyl and amino groups and / or (ii) a group with sterically hindered amine, the individual components of these Connections via nitrogen or oxygen atoms, amide, ester or salt-like are bonded together. 2. mono-, bi- or tri-carbocyclic phosphine or phosphonic acid compounds according to claim 1, which contain a reactive towards hydroxyl and amino groups and at least one, preferably two groups with sterically hindered amine. 3. phosphine or phosphonic acid compounds according to claim 1, of formula I or II NK © 2 '© 0-P- (0) a-H I. (I), (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, Ci-4-alkyl or alkoxy, preferably a phenyl radical, Ri represents the remainder of a compound R2 reactive towards hydroxyl and amino groups, an -NR3- or -O-bridge member, R3 is hydrogen or Ci-4-alkyl, R4 is the atomic group necessary to complete a 5-, 6- or 7-membered ring which optionally carries further non-water-solubilizing substituents and / or contains a further ring in a spiro bond, R5 is hydrogen, Ci-4-alkyl or acyl, all R8 Ci-5-alkyl, preferably methyl n zero or 1, p represents 1, 2 or 3 and p '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 12th CH 681 542 A5 10th 15 / ° 0 C \ R8 a Ì ^ NHî ^ O-P-CO ^ -H -R, ' (III), 20th 25th 30th 35 40 45 50 55 (IV), where in these formulas R is a mono-, bi- or tri-carbocyclic radical which preferably carries one or two substituents from the group chlorine, bromine, Gi-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 Ci-4-alkyl, FU is the atomic group necessary to complete a 5-, 6- or 7-membered ring which optionally carries further non-water-solubilizing substituents and / or contains a further ring in a spiro bond, R5 is hydrogen, Ci-4-alkyl or acyl, all Rs Ci-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: 60 65 13 5 10th 15 20th 25th 30th 35 40 45 50 55 60 CH 681 542 A5 (b), R8 R8 I 9 9 (c), R, "8th * 8 (d) or R R8 Ii R8 R5 'R8 (e), wherein R5 'is hydrogen, Ci-4-alkyl or acyi or in the form of the phosphinic or phosphonic acid salt, together with the sterically hindered nitrogen atom, a group of the formula R optionally one or two substituents from the group chlorine, bromine, Ci_4-alkyl or Al- koxy-bearing mono-, bi- or tri-carbocyclic radical, preferably a phenyl radical, all R8 Ci-5-alkyl, preferably methyl, the two Rg independently of one another hydrogen, C1-2-AI- kyl, an Rg also phenyl, or both Rg together form a group of the formula - (CH2) n-, 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 any one of the preceding claims, wherein the radical reactive towards hydroxyl and amino groups is a mono- or dichlorotriazinyl radical, a mono- or dichloropirimidinyl radical or a mono- or dichloroquinoxalinyl radical, 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 one mole of a compound having m atoms which are reactive toward hydroxyl and amino groups or atom groups having m 'mole of a mono- containing a reactive hydroxyl or amino group. or tri-carbocyclic phosphine or phosphonic acid compound, where m is 2 or 3 and m 'is 1, 2 or 3 8. A process for the preparation of the phosphine and phosphonic acid compounds according to claim 1, characterized in that a compound which optionally contains a radical which is reactive toward hydroxyl and amino groups and has at least one sterically hindered amine, with a mono-, bi- or tri-carbocyclic compound Converts phosphine or phosphonic acid. 9. Use of the mono-, di- or tri-carbocyclic phosphine and phosphonic acid compounds according to claim 1, to improve the dyeability of non-textiles plastics and the compounds containing a sterically hindered amino group also to improve the light stability of the colored and undyed non-textiles plastics. 10. A method for stabilizing plastics against degradation by light, oxidation and heat, characterized in that the non-textile plastics to be stabilized are 0.2 to 5 percent by weight of one or more compounds according to claim 1, before, during or after the polymer formation , clumps in bulk. ^ H2-09-P - (0) n-H, * \ 14