JPH0717846B2 - Stabilizer for polymer materials - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a stabilizer for polymer materials, specifically 2,2,6,6-
The present invention relates to a stabilizer for polymer materials, which comprises a copolymer of a specific unsaturated carboxylic acid ester having a tetraalkylpiperidyl group.

[Prior art and its problems]

Polymers such as polyethylene, polypropylene, ABS resin, polyvinyl chloride are generally sensitive to the effects of light,
It is known that it deteriorates due to its action, causes discoloration or a decrease in mechanical strength, and cannot withstand long-term use.

Therefore, in order to prevent the deterioration of the polymer due to this light,
Conventionally, various stabilizers have been used, but the conventionally used light stabilizers have insufficient stabilizing effects, and the stabilizers themselves are unstable to heat or oxidation, or water. Since many of them are easily extracted from the polymer by a solvent such as the above, and many of them give coloring to the polymer, the polymer cannot be stabilized for a long period of time.

Among these light stabilizers which have been conventionally used, the hindered piperidine-based compounds themselves are non-coloring and have a relatively large stabilizing effect, and thus have been particularly noted in recent years.

However, the conventionally known piperidine-based compounds still have insufficient light-stabilizing ability, have a large volatility, are easily extracted from the polymer by water, or have compatibility with the polymer. Inferior to that, there were also drawbacks such as causing blooms.

In order to overcome these drawbacks, it has recently been proposed to use a high molecular weight hindered piperidine compound.

For example, JP-A-52-141883 proposes a polymer such as polyester having a hindered piperidine group,
JP-A-54-21489 and JP-A-54-71185,
A (meth) acrylate polymer having a hindered piperidine group has been proposed, and JP-A-55-157612 discloses a maleic acid ester-olefin copolymer having a hindered piperidine group. -177053 discloses an itaconic acid ester (co) polymer.

However, when using these polymers, although the volatility of the stabilizer is reduced, its stabilizing effect is not sufficient, and the compatibility with the polymer substance to be stabilized is poor,
There is a defect that causes bloom and the like, and further improvement is necessary.

[Means for solving problems]

The present inventors, in view of the present situation, as a result of repeated earnest studies, found that by using a specific unsaturated carboxylic acid ester copolymer having a polyalkylpiperidyl group, all of the above drawbacks can be solved. The present invention has been reached.

That is, the present invention has a repeating unit represented by the following formula (I) and formula (II), and may contain a comonomer having at least one double bond polymerizable therewith, and has a molecular weight of 80.
The present invention provides a stabilizer for polymer materials, which comprises a copolymer compound of 0 to 100,000.

(In the formula, R is R ₁ is a hydrogen atom, an alkyl group, oxyl (-O
.) Or an acyl group, and R ₂ represents a lower alkyl group. ) Hereinafter, the stabilizer for polymer materials of the present invention will be described in detail.

In the copolymer compound having a repeating unit represented by the above formulas (I) and (II), which is a constituent component of the stabilizer for polymer materials of the present invention, the alkyl group represented by R ₁ is, for example, Methyl, ethyl, propyl, isopropyl, butyl, amyl, hexyl, heptyl, octyl,
2-ethylhexyl, nonyl, decyl, dodecyl, octadecyl, benzyl, phenylethyl, 2-hydroxyethyl, 2-hydroxypropyl, 2-hydroxybutyl, 2,3-epoxypropyl and the like can be mentioned. Examples of the acyl group include , Acetyl, propionyl, butyroyl, acryloyl, methacryloyl, octanoyl, benzoyl and the like.

Further, the lower alkyl group represented by R ₂ is methyl,
Examples thereof include ethyl, propyl, butyl and isobutyl.

The stabilizer of the present invention includes two types of esters of 2-methylmaleic acid (mesaconic acid) and itaconic acid and a piperidyl group-containing alcohol, and, if necessary, a comonomer having at least one double bond polymerizable with the ester. The above-mentioned piperidyl group-containing alcohol is a copolymer of
For example, 2,2,6,6-tetramethyl-4-piperidinol, 1,2,2,6,6-pentamethyl-4-piperidinol,
1-benzyl-2,2,6,6-tetramethyl-4-piperidinol, 1- (2,3-epoxypropyl) -2,2,6,6-tetramethyl-4-piperidinol, 2,2,6 , 6-Tetramethyl-1-oxyl-4-piperidinol, 1-acetyl-2,2,6,6-tetramethyl-4-piperidinol, 9
-Aza-8,8,10,10-tetramethyl-3-ethyl-1,5-
Dioxaspiro [5.5] -3-undecylmethanol,
9-aza-8,8,9,10,10-pentamethyl-3-ethyl-
1,5-Dioxaspiro [5.5] -3-undecylmethanol, 9-aza-9-acetyl-8,8,10,10-tetramethyl-3-ethyl-1,5-dioxaspiro [5.5] -3-un Examples include decyl methanol.

Examples of the comonomer usable in the present invention include ethylene, propylene, butene-1, isobutylene, hexene, octene, decene, dodecene, tetradecene, hexadecene, octadecene, eicosene, styrene, α-methyl-styrene, cyclohexene, Butadiene, vinyl chloride, acrylonitrile, methyl vinyl ketone, methyl vinyl ether, butyl vinyl ether, orthyl vinyl ether, dodecyl vinyl ether, vinyl acetate, acrylic acid, methacrylic acid, maleic anhydride, methyl acrylate, butyl acrylate, methyl methacrylate, 2 , 2,6,6-Tetramethyl-4-piperidyl-vinyl ether, 1,2,2,6,6-pentamethyl-
4-piperidyl-vinyl ether, 2,2,6,6-tetramethyl-4-piperidyl-allyl ether, 1,2,2,6,6-
Pentamethyl-4-piperidyl-allyl ether, 2,2,
6,6-tetramethyl-4-piperidyl acrylate and the like can be mentioned.

The above-mentioned copolymer compound (copolymer of unsaturated carboxylic acid ester), which is a constituent of the stabilizer of the present invention, is the above-mentioned specific unsaturated carboxylic acid ester [and, if necessary, other unsaturated monomer (the above-mentioned comonomer)]. Is polymerized using an ordinary polymerization initiator such as an organic peroxide or an azonitrile compound, or an unsaturated carboxylic acid ester having no 2,2,6,6-tetramethylalkylpiperidyl group (and, if necessary, And other unsaturated monomers) and then transesterified with a piperidine compound to facilitate production.

In the copolymer compound, the molar ratio of the 2-methyl maleic acid ester and the itaconic acid ester is preferably appropriately selected from the range of 10: 1 to 1:10, and the content ratio of the comonomer is 2 or more. It is usually 100 times mol or less, preferably 50 times mol or less, based on the total amount of the unsaturated carboxylic acid ester.

The copolymer compound has a molecular weight of 800 to 1
Those in the range of 00,000, preferably 1,000 to 50,000 can be used.

Hereinafter, the present invention will be described in more detail with reference to specific synthesis examples.

Synthesis Example 1 Bis (1,2,2,6,6-pentamethyl-4-piperidyl) itaconate / bis (1,2,2,6,6-pentamethyl-4-piperidyl) mesaconate / 2-ethylhexyl-vinyl ether copolymerization Synthesis of combined bis (1,2,2,6,6-pentamethyl-4-piperidyl) itaconate 8.7 g (0.02 mol), bis (1,2,2,6,6-pentamethyl-4-piperidyl) mesaconate 4.4 g (0.01 mol), 2-ethylhexyl-vinyl ether 12.5 g (0.0
8 mol) and 0.64 g (2.5% by weight) of azobisisobutyronitrile as a reaction initiator, and the mixture was stirred at 70 to 75 ° C. for 6 hours under a nitrogen stream. Then, unreacted 2-ethylhexyl-vinyl ether was distilled off under reduced pressure to obtain a nitrogen content (N%).
17.3 g of a pale yellow glassy solid product (stabilizer No. 1) with 4.86% and an average molecular weight of 3,000 was obtained. The itaconate / mesaconate / vinyl ether molar ratio in the product is 2/1 / 2.7
Met.

Synthesis Example 2 of bis (1,2,2,6,6-pentamethyl-4-piperidyl) itaconate / bis (1,2,2,6,6-pentamethyl-4-piperidyl) mesaconate / isobutyl-vinyl ether copolymer Synthesis Bis (1,2,2,6,6-pentamethyl-4-piperidyl) itaconate 13.1 g (0.03 mol), bis (1,2,2,6,6-pentamethyl-4-piperidyl) mesaconate 8.7 g (0.02 mol) Mol), 10.0 g (0.1 mol) of isobutyl-vinyl ether and 0.32 g (1% by weight) of azobisisobutyronitrile were dissolved in 10 g of xylene, and the mixture was stirred at 70 to 75 ° C for 6 hours. Then, the solvent and unreacted isobutyl vinyl ether were distilled off under reduced pressure to obtain 26.2 g of a product (stabilizer No. 2) as a pale yellow glassy solid having N% = 5.34% and an average molecular weight of 2,000. The itaconate / mesaconate / vinyl ether molar ratio in the product was 3/2 / 4.4.

Synthetic Examples 3 to 10 By the same operation as in Synthetic Example 1 or Synthetic Example 2, stabilizers Nos. 3 to 10 shown in the following table were synthesized.

In the table, And the molar ratio indicates the molar ratio of itaconic acid ester: mesaconic acid ester: comonomer.

The present invention uses the above-mentioned specific unsaturated carboxylic acid ester copolymer as a stabilizer for a polymer material, and the addition amount thereof is usually 0.001 to 5 per 100 parts by weight of the polymer material.
Parts by weight, preferably 0.01 to 3 parts by weight.

Examples of the polymer material to be improved in stability in the present invention include, for example, α-olefin polymers such as polyethylene, polypropylene, polybutene, poly-3-methylbutene, ethylene-vinyl acetate copolymers, ethylene-propylene copolymers. Polyolefins such as coalesces and copolymers thereof, polyvinyl chloride, polyvinyl bromide, polyvinyl fluoride, polyvinylidene chloride, chlorinated polyethylene, chlorinated polypropylene, polyvinylidene fluoride, brominated polyethylene, chlorinated rubber, vinyl chloride- Vinyl acetate copolymer, vinyl chloride-ethylene copolymer, vinyl chloride-propylene copolymer, vinyl chloride-styrene copolymer, vinyl chloride-isobutylene copolymer, vinyl chloride-vinylidene chloride copolymer, vinyl chloride- Styrene-maleic anhydride terpolymer, salt Vinyl-styrene-acrylonitrile copolymer, vinyl chloride-butadiene copolymer, vinyl chloride-isoprene copolymer, vinyl chloride-chlorinated propylene copolymer, vinyl chloride-vinylidene chloride-vinyl acetate terpolymer, chloride Vinyl-acrylic acid ester copolymer, vinyl chloride-maleic acid ester copolymer, vinyl chloride-methacrylic acid ester copolymer, vinyl chloride-acrylonitrile copolymer, halogen-containing synthetic resin such as internally plasticized polyvinyl chloride, Petroleum resin, chroman resin,
Copolymers of polystyrene, polyvinyl acetate, acrylic resin, styrene and / or α-methylstyrene with other monomers (eg maleic anhydride, N-phenylmaleimide, butadiene, acrylonitrile, etc.), acrylonitrile-butadiene-styrene. Copolymer, acrylic acid ester-butadiene-styrene copolymer, methacrylic acid ester-butadiene-styrene copolymer, methacrylate resin such as polymethylmethacrylate, polyvinyl alcohol, polyvinyl formal, polyvinyl butyral, linear polyester, polyphenylene oxide, Polyamide, polycarbonate, polyacetal, polyurethane, fibrin resin, or phenol resin, urea resin, melamine resin, epoxy resin, unsaturated polyester resin, silicone resin It can be mentioned. Furthermore,
Isoprene rubber, butadiene rubber, acrylonitrile-
Rubbers such as butadiene copolymer rubber and styrene-butadiene copolymer rubber, and blends of these resins may be used. Further, a cross-linked polymer such as cross-linked polyethylene cross-linked by peroxide or radiation and a foamed polymer such as expanded polystyrene foamed by a foaming agent are also included.

The stabilizer of the present invention can be used alone, but can also be used in combination with other additives such as general-purpose antioxidants and stabilizers.

Particularly preferable as these other additives are:
Antioxidants such as phenol type, sulfur type, phosphite type,
Other light stabilizers such as UV absorbers may be mentioned.

Examples of the phenolic antioxidant include 2,6-di-tert-butyl-p-cresol and 2,6-diphenyl-4.
-Octoxyphenol, stearyl- (3,5-di-methyl-4-hydroxybenzyl) thioglycolate, stearyl-β- (4-hydroxy-3,5-di-tert-butylphenyl) propionate, distearyl- 3,5-di-tert-butyl-4-hydroxybenzylphosphonate,
2,4,6-Tris (3 ', 5'-di-tert-butyl-4-hydroxybenzylthio) 1,3,5, -triazine, distearyl (4-hydroxy-3-methyl-5-third Butyl) benzyl malonate, 2,2'-methylenebis (4-methyl-6-tert-butylphenol), 4,4'-methylenebis (2,6-di-tert-butylphenol), 2,2'-methylenebis [6 -(1-methylcyclohexyl) p-cresol], bis [3,5-bis (4-hydroxy-3-tert-butylphenyl) butyric acid] glycol ester, 4,4'-butylidene bis (6-tert-butyl) -M-cresol), 2,2'-ethylidene bis (4,6-di-tert-butylphenol), 2,2'-ethylidene bis (4-second)
Butyl-6-tert-butylphenol), 1,1,3-tris (2-methyl-4-hydroxy-5-tert-butylphenyl) butane, bis [2-tert-butyl-4-methyl-6-]
(2-Hydroxy-3-tert-butyl-5-methylbenzyl) phenyl] terephthalate, 1,3,5-tris (2,6-
Dimethyl-3-hydroxy-4-tert-butyl) benzyl isocyanurate, 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) -2,4,6-trimethylbenzene, tetrakis [Methylene-3- (3,5-di-third
Butyl-4-hydroxyphenyl) propionate] methane, 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, 1,3,5-tris [(3,5- Di-tert-butyl-4-hydroxyphenyl)
Propionyloxyethyl] isocyanurate, 2-octylthio-4,6-di (4-hydroxy-3,5-di-tertiary
Butyl) phenoxy-1,3,5-triazine, 4,4'-thiobis (6-tert-butyl-m-cresol), 2,2'-methylenebis (6-tert-butyl-4-methylphenol)
Monoacrylate, triethylene glycol bis [3-
(3-tert-butyl-4-hydroxy-5-methylphenyl) propionate], 3,9-bis (1,1-dimethyl-2)
-Hydroxyethyl) 2,4,8,10-tetraoxaspiro [5.5] undecane bis [3- (3-tert-butyl-4-
Hydroxy-5-methylphenyl) propionate] and the like.

Examples of the sulfur-based antioxidant include dialkylthiodipropionates such as dilauryl-, dimyristyl-, and distearyl- and polyhydric alcohols of alkylthiopropionic acids such as butyl-, octyl-, lauryl-, stearyl-. (For example, glycerin, trimethylolethane, trimethylolpropane, pentaerythritol, trishydroxyethyl isocyanurate) esters (for example, pentaerythritol tetralauryl thiopropionate) can be mentioned.

Further, as the phosphite-based antioxidant, for example,
Trioctyl phosphite, trilauryl phosphite, tridecyl phosphite, octyl-diphenyl phosphite, tris (2,4-di-tert-butylphenyl)
Phosphite, triphenyl phosphite, tris (butoxyethyl) phosphite, tris (nonylphenyl) phosphite, distearyl pentacerithritol diphosphite, tetra (tridecyl) 1,1,3-tris (2-methyl- 5-tert-butyl-4-hydroxyphenyl) butane diphosphite, tetra (C ₁₂ ~ ₁₅ mixed alkyl) -4,4'-isopropylidene diphenyl diphosphite, tetra (tridecyl) -4,4'-Buchirudenbisu ( 3-methyl-6-tert-butylphenol) diphosphite, tris (3,5-di-tert-butyl-4-hydroxyphenyl) phosphite, tris (mono / di mixed nonylphenyl) phosphite, hydrogenated-4,4 ′ -Isopropylidene diphenol polyphosphite, bis (octylphenyl) · bis [4,4′-butyl Ridene bis (3-methyl-6-tert-butylphenol)]-1,6-hexanediol diphosphite, phenyl 4,4'-isopropylidene diphenol pentaerythritol diphosphite, bis (2,4-di- Tert-Butylphenyl) pentaerythritol diphosphite, bis (2,6-tert-butyl-4-methylphenyl) pentaerythritol diphosphite, tris [4,4'-isopropylidenebis (2
-Tert-butylphenol)] phosphite, phenyl
Diisodecyl phosphite, di (nonylphenyl) pentaerythritol diphosphite, tris (1,3-di-
Stearolyloxyisopropyl) phosphite, 4,
4'-isopropylidene bis (2-tert-butylphenol) -di (nonylphenyl) phosphite, 9,10-di-
Hydro-9-oxa-10-phosphaphenanthrene-10-oxide, tetrakis (2,4-di-tert-butylphenyl) -4,4'-biphenylene diphosphonite and the like can be mentioned.

Examples of the other light stabilizers described above include 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-n-octoxybenzophenone, 2,2'-di-hydroxy-4-methoxybenzophenone, 2 Hydroxybenzophenones such as 4,4-dihydroxybenzophenone, 2- (2'-hydroxy-3'-t-butyl-5 '
-Methylphenyl) -5-chlorobenzotriazole,
2- (2'-hydroxy-3 ', 5'-di-t-butylphenyl) -5-chlorobenzotriazole, 2- (2'
-Hydroxy-5'-methylphenyl) benzotriazole, 2- (2'-hydroxy-3'5'-di-t-amylphenyl) benzotriazole and other benzotriazoles, phenyl salicylate, pt-butylphenyl salicylate , 2,4-di-t-butylphenyl-3,5-
Benzoates such as di-t-butyl-4-hydroxybenzoate and hexadecyl-3,5-di-t-butyl-4-hydroxybenzoate, 2,2'-thiobis (4-t
-Octylphenol) Ni salt, [2,2'-thiobis (4
-T-octylphenolate)]-n-butylamine N
i, (3,5-di-t-butyl-4-hydroxybenzyl)
Nickel compounds such as phosphonic acid monoethyl ester Ni salt, substituted acrylonitriles such as α-cyano-β-methyl-β- (p-methoxyphenyl) acrylmethyl and N-2-ethylphenyl-N′-2- Ethoxy-5
Examples thereof include oxalic acid dianilides such as tert-butylphenyl oxalic acid diamide and N-2-ethylphenyl-N'-2-ethoxyphenyl oxalic acid diamide.

Other heavy metal deactivators, nucleating agents, metallic soaps, organotin compounds, plasticizers, epoxy compounds, pigments, fillers, foaming agents, antistatic agents, flame retardants, lubricants, processing aids, etc., as required. Can be used together.

The polymeric material stabilized by the stabilizer of the present invention can be used in a wide variety of forms, for example, as films, fibers, tapes, sheets, various molded articles, and also as paints, binders for lacquers, adhesives, putties. It can also be used as a base material in photographic materials.

Next, the present invention will be specifically described with reference to examples. However, the invention is not limited to these examples.

Example 1 <Compounding> 100 parts by weight of polypropylene Tetrakis [methylene-3- (3,5-ditertiary butyl-4]
-Hydroxyphenyl) propionate] methane 0.1
Calcium stearate 0.05 Stabilizer (see Table-1) 0.2 A press sheet having a thickness of 0.3 mm was prepared with the above composition, and a light resistance test was performed on this sheet using a high pressure mercury lamp. A light resistance test was also conducted on the sheet after being immersed in hot water at 80 ° C for 24 hours. The results are shown in Table 1 below.

Example 2 It is known that ordinary stabilizers lose their effects remarkably due to volatilization, decomposition and the like during high temperature processing of resins.

In this example, the effect of high temperature processing was confirmed by repeating extrusion processing.

Resin and additives were mixed with a mixer for 5 minutes according to the following formulation, and then compound was prepared with an extruder (cylinder temperature 230 ° C, 240 ° C, head die temperature 250 ° C, rotation speed 20r
pm). After repeating the extrusion 10 times, a test piece was prepared using this compound with an injection molding machine (cylinder temperature 240 ° C., nozzle temperature 250 ° C., injection pressure 475 kg / cm ² ).

A light resistance test was conducted using a high pressure mercury lamp using the obtained test piece. Further, the same tests were carried out for one and five extrusions. The results are shown in Table 2 below.

<Blend> Ethylene-propylene copolymer resin 100 parts by weight Calcium stearate 0.2 Stearyl-β-3,5-di-tert-butyl-4-hydroxyphenylpropionate 0.1 Dilaurylthiodipropionate 0.3 Stabilizer (see Table-2) ) 0.2 Example 3 <Formulation> Polyethylene 100 parts by weight Ca-stearate 1.0 Tetrakis [methylene-3- (3,5-di-tertiary butyl-]
4-hydroxyphenyl) propionate] methane 0.1
Distearyl thiodipropionate 0.3 Stabilizer (see Table 3) 0.2 The above composition was kneaded and then pressed to form a sheet having a thickness of 0.5 mm. Using this sheet, the light resistance was measured in an Ubezometer and the time until embrittlement was measured. The results are shown in Table 3 below.

Example 4 <Formulation> Polyvinyl chloride 100 parts by weight Dioctyl phthalate 48 Epoxidized soybean oil 2 Trisnonylphenyl phosphite 0.2 Ca-stearate 1.0 Zn-stearate 0.1 Stabilizer (see Table 4) 0.2 Roll the above composition The above was kneaded to form a sheet having a thickness of 1 mm. Using this sheet, a light resistance test in a weatherometer was conducted. The results are shown in Table 4 below.

Example 5 <Compounding> Polyurethane resin (U-100 manufactured by Asahi Denka Co., Ltd.) 100 parts by weight Ba-stearate 0.7 Zn-stearate 0.3 2,6-di-tert-butyl-p-cresol 0.1 Stabilizer (see Table-5) 0.3) The above composition was kneaded on a roll at 70 ° C. for 5 minutes and pressed at 120 ° C. for 5 minutes to prepare a sheet having a thickness of 0.5 mm. Using this sheet, the elongation residual ratio after irradiation for 50 hours and 100 hours was measured with a fade meter. The results are shown in Table-5 below.
Shown in.

Example 6 The compounds of the present invention are also useful as light stabilizers for coatings. In this example, the effect was observed with a double metallic luster paint comprising a base coat containing a metallic pigment and a transparent top coat.

a) Base coat paint 100 g of methyl methacrylate, 66 g of n-butyl acrylate,
Take 30 g of 2-hydroxyethyl methacrylate, 4 g of methacrylic acid, 80 g of xylene and 20 g of n-butanol, and add 110
2 g of asobisisobutyronitrile while heating and stirring at ℃
A solution consisting of 0.5 g of dodecyl mercaptan, 80 g of xylene and 20 g of n-butanol was added dropwise over 3 hours. Then, the mixture was stirred at the same temperature for 2 hours to prepare an acrylic resin solution having a resin solid content of 50%.

12 parts by weight of the acrylic resin solution, butoxylated methylol melamine (manufactured by Mitsui Toatsu Co., Ltd .; Uban 20SE60; resin solid content 6)
0%) 2.5 parts by weight, cellulose acetate butyrate resin (20% butyl acetate solution) 50 parts by weight, aluminum pigment (Toyo Aluminum Co., Ltd .; Alpac 1123N) 5.5 parts by weight, xylene 10 parts by weight, butyl acetate 20 parts by weight and copper. 0.2 parts by weight of phthalocyanine blue was taken as a base coat paint.

b) Top coat paint 48 parts by weight of the acrylic resin solution, 10 parts by weight of butoxylated methylol melamine, 10 parts by weight of xylene, 4 parts by weight of butyl glycol acetate and 0.12 parts by weight of a stabilizer (see Table 6) (0.4 based on solid content). %) To obtain a top coat paint.

The base coat paint was sprayed on the primer-treated steel sheet to a dry film thickness of 20 μ, and after standing for 10 minutes, the top coat paint was sprayed to a dry film thickness of 30 μ.
After leaving it for 15 minutes, it was baked at 140 ° C for 30 minutes to obtain a test piece.

The test piece was put in a weatherometer and the time until the crack of the coating film was generated was measured. The results are shown in Table 6 below.

[Effects of the Invention] The stabilizer for polymer materials of the present invention has excellent stabilizing ability and also has effects such as excellent compatibility with the polymer material to be stabilized.

Claims (1)

[Claims] 1. A molecular weight of 800 to 1, which has a repeating unit represented by the following formulas (I) and (II) and which can contain a comonomer having at least one double bond polymerizable with them.
Stabilizer for polymeric materials consisting of 00,000 copolymer compounds. (In the formula, R is R ₁ is a hydrogen atom, an alkyl group, oxyl (-O
.) Or an acyl group, and R ₂ represents a lower alkyl group. )