DD262439B5 - METHOD FOR STABILIZING POLYMERS - Google Patents

Description

Field of application of the invention

The invention relates to a process for stabilizing higher molecular weight organic compounds and synthetic polymers by means of polymeric polyalkylpiperidine compounds.

Characteristic of the known technical solutions

The stabilization of high molecular weight organic compounds by polyalkyipiperidine derivatives substituted at the 4-position or at the 1- and 4-positions against the damaging influence of light is known. The use of such piperidine derivatives as effective light stabilizers is limited to a few high molecular weight compounds, such as polypropylene, since high volatility and incompatibility of the well-known light protection effect preclude. According to DE-OS 2920918 above disadvantages are eliminated when copolymers prepared from a polyalkylpiperidine of the general formula

O O

and one or more comonomers of the formula

the polymers to be stabilized are added, the radicals of the general formulas preferably having the following meaning:

R '= hydrogen or a C _r to C ₄ alkyl group

R ² = R ³ = hydrogen

R ⁴ = methyl

with R ¹ to R ⁴ in the meaning indicated above

X = oxygen or -NR ^e with R ⁶ = hydrogen or C _r to C ₁₈ -alkyl R ⁷ = hydrogen or a COOR ¹⁰ group with R ¹⁰ = hydrogen R ⁸ = hydrogen

R ⁹ = hydrogen or C 1 - to C ₁₈ -alkyl or phenyl, or chlorine, or acetyl or also OR ¹¹ with R ¹¹ = alkyl or hydroxyalkyl having 1 to 6 carbon atoms.

According to OE-OS 2,920,918, the stated polymeric light stabilizers are obtained by copolymerization of, for example, bis (2,2,6,6-tetramethyl-4-piperidyl) fumarate or fumaric acid 1 '- (2,2,6,6- tetramethylpiperidyl) -4-ethyl ester or of analogous maleic acid derivatives with ethylene, styrene, vinyl acetate or acrylates and methacrylates. On the other hand, it is also assumed that copolymers of maleic anhydride with α-olefins or styrene, with compounds of the general formula

wherein X is oxygen or an NR ⁶ structure and R ¹ to R ^{6 have} the abovementioned meaning preferably.

Disadvantage of the known solution is the microheterogeneity after incorporation of the polymeric light stabilizers in the polymers to be stabilized, which occurs in the stabilizers obtained by chemical modification of α-olefin or styrene-maleic anhydride. It is known that a permanent homogeneous distribution of a stabilizer is given only if it is sufficiently compatible. Another condition for a statistical distribution of a stabilizer to achieve good efficacy with good compatibility is a melting range that substantially coincides with the softening or melting range of the polymer in question.

Object of the invention

The object of the invention is a process for stabilizing organic compounds and synthetic polymers by means of stabilizers which have improved compatibility and cause co-microcurity.

Explanation of the essence of the invention

The invention has for its object to use polymeric stabilizers with high efficiency and improved compatibility with organic compounds to be stabilized and synthetic polymers. Dieso object is achieved by a method for stabilizing polymers against light and oxidation with stabilizers based on polymeric piperidines, according to the invention ter, multi or graft polymers consisting of one or more polyalkylpiperidines of the general formula

0 «c c * ο

\ X

and / or the general formula

-CH -

! i

O = C C = O

^ H ₃

(2)

and / or the general formulas

-CH-

C-O

OH

0 - C I

OH

C I

CH - CH 1 I

0 0

O O

H ₂ C

H ₃ C

CH

and one or more structural elements of the general formula

-CH-C

and one or more Strukturolementon de ^r general formula

- CH - CH -

O = C C = O

(6)

OH X

and / or the general formula -CH-CH-

O = C C = O

(7)

and / or a structural element of the formula

-CH-CH-

I i

O = C C = O

in which

However, to C ₂ 4 * alky I, preferably is hydrogen, acetyl and C ₁ - - C ₄ alkyl, X is oxygen or-NR ³ -GruppemitR ³ - R ¹ is hydrogen, oxyl, formyl, acetyl or C ₁ -alkyl ^ WasserstoffoderCrbisC , C ₁ - to C ₄ -alkyl, preferably ethyl,

Is hydrogen or a group of formula-COOR ⁸ wherein R ⁸ = hydrogen or Cr to C ₈ alkyl, hydrogen, phenyl, chloro, acetyl or C _t - C ₁₈ alkyl,

Is hydrogen, methyl or -OR ⁹ radical with R ⁹ = C ₁ - to C ₁₈ -alkyl, preferably C ₁ - to C ₈ -alkyl, or-CN or-CONH ₂

Hydrogen, C ₁ - to C ₁₈ -alkyl, C, - to Cs-aralkyl or phenyl, exist, be used alone or in combination with known additives for stabilizing high and low molecular weight organic compounds.

It is advantageous to mix mixtures of terpolymers, multi- and / or graft polymers for stabilization. Advantageously, the compounds used for stabilizing structural elements of the general formulas (6 / and (7) with a ratio of

Σ structural elements of the formulas (1) to (4)

Σ structural elements of the formulas (6) to (7)

equal to 9: 1 to 1: 1.

As polymers are advantageously stabilized homo- and copolymers of olefins and dienes, copolymers of ethylene and vinyl acetate, homo-, co- and graft polymers of styrene, polyacrylates, polymethacrylates, polyesters, polyamides, polyurethanes, polycarbonates. The polymeric stabilizers have relative molecular weights between 800 and 150,000, preferably 800 to 12,000.

It was surprising that the polymers provided with these stabilizers have good light and oxidation stability and, compared to copolymers and terpolymers which contain no structural units of the general formulas (6) to (8), a significantly improved compatibility between structurally different synthetic Polymers and the stabilizers occurs. This is partly achieved in addition by the favorable softening ranges of the stabilizers. Furthermore, the stabilizers are characterized by a low volatility and excellent migration resistance. The stabilizers used according to the invention are preferably obtained by partial and / or mixed modification of co-, ter- and graft polymers of maleic anhydride. Corresponding chemical processes for the modification of polymers

maleic anhydride are feasible based on known reactions. The preparation of the stabilizers by co-

u. Terpolymerization is also possible. The stabilizers thus represent polymeric compounds having in the side chain sterically hindered 2,2,6,6-tetraalkylpiperidine-type amines in random distribution, which are connected via ester and / or amide and / or imide bonds with the backbone chain , In addition, however, the side chains formed by modification contain structural elements of the formulas (6) and (7) which bring about the favorable melting behavior of the stabilizers and the excellent compatibility with the higher molecular weight organic compounds and synthetic polymers to be stabilized.

Of the large number of polymers of maleic anhydride which are fundamentally suitable for the preparation of the stabilizers, non-limiting examples are to be mentioned below:

Copolymers of maleic anhydride with α-olefins having 2 to 24 carbon atoms, such as ethylene, propylene, isobutylene, 4-methylpentone, hexene, diisobutylene, 2-ethylhexene, octene, decene, dodecene, tetradecene, octadecene.

Copolymers of maleic anhydride with acrylates containing 4 to 11 carbon atoms, such as methyl, ethyl, propyl, isopropyl, isobutyl, hexyl, octyl and 2-ethylhexyl esters of acrylic acid.

Copolymer of maleic anhydride with methacrylic acid esters containing from 5 to 12 carbon atoms, such as methyl, ethyl, propyl, butyl, hexyl, octyl and 2-ethylhexyl esters of methacrylic acid.

Copolymers of maleic anhydride with vinyl ethers containing 3 to 24 carbon atoms, such as methyl, ethyl, propyl, butyl, isobutyl-2-ethylhexyl, octyl, dedecyl, hexadecyl and octadecyl vinyl ether.

Copolymers of maleic anhydride with vinyl esters such as vinyl acetate and vinyl propionate, copolymers of maleic anhydride with acrylamide and methylacrylamide.

The copolymers of maleic anhydride listed in many cases have an alternating structure. However, copolymers which contain up to 66 mol% of maleic anhydride or which contain less than 50 mol% of maleic anhydride are also advantageously suitable as the base body.

Tor and multipolymers of maleic anhydride furthermore represent suitable basic bodies of the stabilizers. Particularly advantageous are terpolymers of ethylene, vinyl acetate and maleic anhydride. While the content of ethylene and vinyl acetate is variable within larger limits, the content of maleic anhydride groups in polymers should be between 10% by weight and 30% by weight. Further examples are terpolymers of maleic anhydride α-olefins having 2 to 24 carbon atoms and acrylic esters having 4 to 11 carbon atoms.

Examples of multipolymers are: polymers of maleic anhydride, styrene, Acrylestsestem having 4 to 11 carbon atoms and acrylonitrile, polymers of maleic anhydride, acrylic esters having 4 to 11 carbon atoms, acrylamide and styrene.

This Multipolymerisato have a statistical distribution of the individual components. The content of maleic anhydride groups should not fall below 10 mol% and is preferably from 30 to 50 mol%. Other examples of multipolymers are polymers of industrial olefin mixtures having 10 to 14 carbon atoms or 14 to 18 carbon atoms, and maleic anhydride.

Suitable bases of the stabilizers are also graft polymers of maleic anhydride obtainable by grafting maleic anhydride onto, for example, polyolefins, polystyrenes, styrene-acrylic esters, copolymers, polybutadienes or polyacrylates. The graft polymers should have a content of at least 5 mol% dicarboxylic anhydride units.

The effectiveness of the stabilizers depends essentially on the ratio of the proportions of the structural elements of the general formulas (1) to (4) to those of the structural elements of the general formulas (6) and (7). Based on 100 structural elements of the formulas (1) to (4) and (6) to (7) of any polymer chain, the proportion of the structural elements of formulas (6) and (7) not having a stabilizer function should not be less than 5, preferably However, between 10 and 50 are.

Larger proportions of the structural element of the formula (8) reduce the compatibility behavior. According to the invention, however, stabilizers with 5 to 10 mol% of the Strukturelemer.tes of formula (8) are used to stabilize reactive polymers. Examples of these are: polyamides, polyesters, partially and completely hydrolyzed ethylene-vinyl acetate copolymers, polyethylen lenimin, Polyacrylsäurehydroxyalkylester. According to the opinion that the stabilizers are multipolymers which are derived by partial and / or mixed modification of dicarboxylic anhydride groups of co-, ter- and grafting of maleic anhydride, the structures of the formulas (1) to (4) as half-esters, half-amides and View Imide, which arise by chemical reaction of polyalkylpiperidines having a reactive functional group in the 4-position, with the above-explained base polymers.

As such polyalkylpiperidines having a reactive functional group, for example, tetramethylpiperidines of the general formulas,

XH

H.:.J

H ₃ C

Leu,

- Ov-CH ₁ OH I

0 0

in which

R ^{1 is} hydrogen, oxyl, formyl, acetyl or a C ¹ to C ₂₄ alkyl, preferably hydrogen, acetyl or a C 1 to C ₄ alkyl and X is oxygen or an NR ³ group with R ^{3 is} hydrogen or C 1 to C ₄ alkyl , used for partial and / or mixed modification of polymers of maleic anhydride. The syntheses of the above compounds are known. They are based for example on the 2,2,6,6-tetramethylpiperidin-4-one, which is hydrogenated by conventional methods, reductively animated or reacted with trivalent alcohols under diketal formation. The stabilizers contain structural elements of the general formulas (6) and (7) with a ratio of

£ structural elements of the formulas (1) to (4) Σ structural elements of the formulas (6) to (7)

equal to 9: 1 to 1: 1.

A reduction of this ratio from 1: 1 to 1: 2 is possible in principle. In this case, larger amounts of stabilizers than is common practice to apply to ensure adequate efficacy.

The structural elements of the general formula (6) represent half-ester or half-amide side chains of maleic acid polymers.

As is known, these polymers are obtained by reacting polymers of maleic anhydride with alcohols and amines, often using basic or acidic catalysts.

Of the multitude of possible alcohols and amines, particularly primary aliphatic or aromatic-aliphatic alcohols and amines having 1 to 24 carbon atoms are suitable for the preparation of the stabilizers, with less branched alkyl radicals being more favorable than strongly branched. For this purpose, the following alcohols and amines should be mentioned:

Butanol, hexanol, octanol, 2-ethylhexanol, dodecanol, hexadecanol, octadecanol, benzyl alcohol, butylamine, hexylamine, octylamine, 2-ethylhexylamine, decylamine, dodecylamine, hexadecylamine, heptadecylamine, octadecylamine, benzylamine. The use of technical alcohol and amine mixtures having 16 to 18 carbon atoms is also possible. The use of secondary alcohols and amines, preferably containing from 4 to 24 carbon atoms, to form structural elements of formula (6) is also possible. The structural elements of the general formula (7) represent substituted maleimides which are formed by reaction of the polymers of maleic anhydride with primary amines under conditions which, after hemamide formation, permit elimination of water with cyclization. These imide formation reactions are well known; they require reaction temperatures greater than 370K or the addition of dehydrating agents such as acetic anhydride.

According to the present invention stabilizers are used for the stabilization of higher molecular weight organic compounds and synthetic polymers, preferably by partial and / or mixed modification of co-, ter-, multi-, and graft polymers of maleic anhydride with polyalkylpiperidines listed above and primary or secondary alcohols and / or amines, preferably containing from 4 to 24 carbon atoms. These reactions can be carried out either in the polymer melt or in organic solutions.

A preferred embodiment of the partial and / or mixed modification consists of initially reacting the polymers of maleic anhydride with above-characterized polyalkylpiperidine compounds to provide the statistical distribution of the structural elements of the general formulas (1) to (4) necessary for the stabilizer function.

Subsequently, the further reaction with the above-described alcohols and amino compounds.

The terpolymers or multipolymers are outstandingly suitable as stabilizers against light and oxidation for relatively high molecular weight organic compounds, preferably synthetic polymers.

Examples of such synthetic polymers are:

Polymers of monoolefins and diolefins and copolymers thereof, such as high and low density polyethylene, polypropylene, polybutadiene, polyisoprene, polyisobutylene, ethylene-propylene copolymers, ethylene-butene copolymers; Polystyrene and copolymers of styrene or α-methylstyrene, such as styrene-butadiene, styrene-acrylonitrile, styrene-acrylonitrile-methacrylate, or block polymers of styrene, such as styrene-butadiene-styrene; halogen-containing polymers such as polyvinyl chloride and copolymers such as vinylchloride-vinylidene chloride, vinyl chloride-vinyl acetate; Polymers derived from α, β-unsaturated acids and their derivatives, such as polyacrylates, polymethacrylates and polyacrylonitrile;

Polymers derived from vinyl acetate, such as polyvinyl acetate, polyvinyl alcohol, ethylene-vinylarate acetate copolymers or ethylene-vinyl alcohol copolymers; Polyurethanes and polyureas; Polyamides and copolyamides; polycarbonates;

polysulfones; polyacetals; Polymers of epoxies, such as polypropylene oxide; Polyesters, unsaturated polyester resins; epoxy resins; alkyd resins; crosslinked homopolymers and copolymers, such as crosslinked polyethylene or crosslinked ethylene-vinyl acetate copolymers; Graft polymers, such as styrene on polybutadiene, styrene and acrylonitrile on polybutadiene or vinyl chloride on ethylene-vinyl acetate copolymers.

In the stabilization of polymers containing hydroxyl or primary or secondary amino groups, such as polyesters, ethylene-vinyl alcohol copolymers and polyamides, the use of terpolymers and multipolymers containing parts of structure (8) is advantageous. These stabilizers can be connected in the process of incorporation with the polymer to be stabilized via ester or amide groups. Depending on the proportion of the structure (8), this can have an advantageous effect on the mechanical properties of the overall polymer.

The stabilizers are added in amounts of 0.05 to 5.0 wt .-%, preferably from 0.1 to 1.0%, based on the total mass to be stabilized higher molecular weight organic compounds and synthetic polymers. The incorporation can be carried out by mixing at least one of these compounds and optionally further Zucätze by the usual methods before or during the shaping. The application of the stabilizers to the material to be stabilized in dissolved or dispersed form is also possible.

The stabilizers may also be added to the plastics to be stabilized in the form of a masterbatch containing at least one of the compounds in a concentration of 2.0 to 25.0% by weight.

Of course, the polymers stabilized in this way may also contain other stabilizers or other additives, as are customary in plastics technology. Examples include:

phenolic or aminic antioxidants, such as β- (3,5-di-tert-butyl-4-hydroxyphenyl) -propionic acid ester; 4,4'-thiobis (3-methyl-6-tert-butyl-phenol);

Phenyl-2-naphthylamine; N, N'-diphenyl-p-phenylenediamine; Metal deactivators, such as the hydrazide of 3,5-dialkyl-4-hydroxyphenyl-propionic acid; Thio or phosphorus compounds such as didodecyl dithiopropionate, organic disulfides, dialkyldithiocarbamates, trisnonylphenyl phosphite and esters of pentaerythritol phosphite; Sunscreens such as 2-hydroxybenzophenones; Salicylates, 2- {2'-hydroxyphonyl) -benzotriazoles, nickel chelates, polyalkylpiperidine compounds, oxalic acid disilicides, optionally dyes, antistatics, flame retardants, pigments, PVC stabilizers, epoxy stabilizers. In the additional use of known stabilizers, especially in sunscreens or organic ι phosphites often occur synergistic effects.

embodiments

The following stabilizers are used in the examples.

Stabilizer I

Stabilizer I is obtained by reacting an ethylene-maleic anhydride copolymer having a maleic anhydride content of 78% by weight and a molecular weight of 1500, with 4-amino-2,2,6,6-tetramethylpiperidine and octyl alcohol in the Way that half of the starting anhydride groups are converted to the 2,2,6,6-Tetramethylpiperidinylhalbamid and the rest of the dicarboxylic anhydride groups in the Octylhalbester. The product is obtained as a white powder having a softening range of 435 to 450K.

Stabilizer Il

Stabilizer II is obtained from a dodecane-maleic anhydride copolymer having a maleic anhydride content of 36.8% by weight and a molecular weight of 25,000, by adding the dicarboxylic anhydride groups in each case in the 2,2,6,6-tetramethyl-4 piperidinyl half ester and converted into the Dodecylhalbamid. The product is available as a slightly yellow colored powder with a softening range of 408 to 420 K.

Stabilizer III

Stabilizer III is obtained from a polymer obtained by copolymerization of maleic anhydride with a technical mixture of C ₁₀ - to C was recovered _t4 -a-olefins, and a maleic anhydride content of 33,6Gew .-% and a molecular weight of 1700 has, by the Half of the dicarboxylic anhydride groups with the cyclic ketal, which was prepared from 2,2,6,6-tetramethyl-4-piperidino and trimethylolpropane, esterified and the remainder of the dicarboxylic anhydride groups was amidated with butylamine. The product is a slightly yellow colored powder with a softening range of 421 to 435K.

Stabilizer IV

Stabilizer IV is obtained from a maleic anhydride-acrylic acid (2-ethyllexyl) ester copolymer having a maleic anhydride content of 22.3% by weight and a molecular weight of 4000 by amidation with 2,2,6,6-tetramethyl-4-aminopiperidine and octadecylamine wherein 80 mol% of the starting anhydride groups were converted to the 2,2,6,6-tetramethyl-4-piperidinyl-haloamide. The product is obtained as a white powder with a softening range of 395 to 401K.

Stabilizer V

Stabilizer V is from a terpolymer consisting of 45.3Gew .-% maleic anhydride, 14.5Gew .-% of propylene and 40.2Gew .-% butyl acrylate, which has a molecular weight of 3600, after amidation of 90Mol-% of dicarboxylic anhydride with 2,2,6,6-Tetramethyl-4-aminopiperidine and 10 mol% of the dicarboxylic anhydride groups with octadecylamine as a white powder having a softening range of 416 to 421K.

example 1

100 parts of a low-density polyethylene and an amount of the stabilizers I, II, III added according to Table 1 were kneaded in a plastograph at 453 K10 minutes for homogenization. The solid which had not yet solidified was taken from the plaque graph and pressed with a laboratory press at 413K into plates about 1.0 mm thick. Parts of the plates thus produced were processed between two high-gloss films using the laboratory press at 413 K to 423 K and a pressure of 30 MPa to test films of a thickness of 0.1 mm. From these test films were test specimen of the dimension 10mm χ 20mm

manufactured. The production of a control sample which does not reveal a stabilizer was carried out under the same conditions. The test specimens thus prepared were exposed to UV irradiation in Xenotester 450. In Zoitabständen vorv.250 hours, the test films were examined in an IR spectrometer for their carbonyl content. As a measure of the degree of degradation, the time taken to reach a difference in carbonyl absorbance at 1720 cm -1 to the starting sample of 0.1 was used

 The effect of the stabilizers against the action of light can be seen from Table 1.

Table 1

stabilizer Weight part / exposure time 100 parts by weight polymer bisAE-.o = O, 1 without stabilizer 0 300 h Stabilisatori 0.4 1820 h Stabilizer Il 0.6 2570 h Stabilizer III 0.6 2350 h

Example 2

As in Example 1, an ethylene-vinyl acetate copolymer having a vinyl acetate content of about 21% by weight was homogenized with the stabilizer IV or stabilizer V at 393 K in a plastograph and pressed at 345 K into films of thickness> 0.05 mm , A corresponding comparative sample without stabilizer was prepared under the same conditions. From these films, samples of 50 mg each in an apparatus for determining oxygen uptake at 443 K were investigated. The induction period of the oxygen uptake, which is clearly observable in the case of the phenolic antioxidants, was not detectable to that extent in the stabilizers used according to the invention, but a significantly lower absorption rate of the oxygen was noted. As a measure of the stabilizing effect against thermo-oxidative degradation, the oxygen uptake achieved after different storage times was used. The results shown in Table 2 show the effect of the stabilizers against thermo-oxidative degradation.

Table 2

stabilizer

without stabilizer stabilizer IV stabilizer V

Weight / amount of oxygen absorbed

100 parts by weight of time

Polymer 50ml 100ml 150ml

0.0 0.4 0.4

25 min 35 min 43 min

95 min 135 min 165 min

110min 185min 245min

Example 3

As in Example 1, 100 parts of a high-density polyethylene and an amount of stabilizers I and III listed in Table 3 were homogenized at 463 K and at 423 K to 433 K to give plates and then to films of thickness

0.1 mm processed.

To test the stabilizing effect, the films are exposed in a Xenotestgerät 450 of UV radiation.

The effect of the compounds is shown in Table 3.

Table 3

stabilizer Parts by weight / Belicht 100 parts by weight polymer without stabilizer 0.0 500 h Stabilisatori 0.4 2130 h Stabilizer III 0.6 2870 h

Exposure time to AEc-o = 0.1

Example 4

100 parts of a polypropylene were homogenized with a table 4 removable amount of stabilizers I, II, IV in a Plastograph at 483 K and then extruded at the same temperature to a film of 0.15 mm thickness.

Test specimens of 65 mm × 22 mm (in the extrusion direction) were cut out of this film.

The specimens thus prepared were exposed in a Xenotestgerät 450 of UV irradiation and then the

Elongation at break determined.

As a measure of the degradation behavior, the negative change in the elongation at break = 100 (1 - = - -!

Stretching at the time to

The results obtained are shown in Table 4.

Table 4 Stabilizer

Weight part /

100 parts by weight

polymer

exposure time

Negative change in elongation at break

without stabilizer stabilizer I stabilizer II StabiiicatorlV

0.0 0.4 0.6 0.4

h h

H

80% 60% 55% 50%

Claims (3)

1. A process for stabilizing polymers against light and oxidation with stabilizers based on polymeric piperidines, characterized in that ter, multi or graft polymers consisting of one or more polyalkylpiperidines of the general formula and / or the general formula
-CH - CH- I \ O = C CO HaC J JLCH ₃ and / or the general formulas
-CH-C H - o- = c C = O ¹ 'o \ - \ o OW .0 s l CH ⁽³⁾ Λ i i oo (1) in which R ^{1 is} hydrogen, oxyl, formyl, acetyl or C ₁ to C ₂ alkyl, R ² is C ₁ to C r alkyl, X is oxygen or NR ³ , with R ³ = hydrogen or C _{1 to} C ₁₈ alkyl , and one or more structural elements of the general formula - C H - C - II and one or more structural elements of the general formula - CH - CH - I i O = C C = , "OH X R ⁷ and / or the general formula - CH - CH - I i O = CC = O (7) R ⁷ and / or structural units of the formula - CH - CH - ¹ I (8 ,, O = C C = in which R ^{4 is} hydrogen or a group of the formula COOR ⁸ , where R ⁸ = hydrogen or C ₁ - to C ₈ -alkyl, R ^{5 is} hydrogen, phenyl, chlorine, acetyl or C ₁ - to C ₁₈ -alkyl, R ⁶ Is hydrogen, methyl or an OR ⁹ radical with R ⁹ = C ₁ - to C ₁₈ -alkyl, or a-CN or a -CONH ₂ -ReSt and R ^{7 is} hydrogen, C ₁ - to C ₁₈ -alkyl, C ₇ - to C ₉ -aralkyl or phenyl, exist, alone or in combination with known additives for stabilizing high and low molecular weight organic compounds are used, wherein the stabilizing compounds used structural elements of the general formulas (6) and (7) with a ratio of Structural elements of the formulas (1) to (4) Σ structural elements of the formulas (6) to (7) equal to 9: 1 to 1: 1 and the structural element of the formula (8) is used in the compounds in proportions of from 5 to 10 mol% to stabilize reactive polymers. 2. The method according to item 1, characterized in that mixtures of ter, multi- and / or graft polymers are used for stabilizing. 3. The method according to item 1, characterized in that homo- and copolymers of olefins and dienes, copolymers of ethylene and vinyl acetate, homo-, co- and graft polymers of styrene, polyacrylates, polymethacrylates, polyesters, polyamides, polyurethanes and polycarbonates are stabilized.