JPS58108238A - Stabilized synthetic resin composition - Google Patents

Abstract

PURPOSE:To prepare a synthetic resin composition having remarkably improved light resistance, and containing a specific polymer having low volatility and high water resistance and compatibility, by compounding a polymer of an unsaturated ether compound having 2,2,6,6-tetramethylpiperidyl group to a synthetic resin. CONSTITUTION:100pts.wt. of a synthetic resin is incorporated with 0.001-5pts.wt. of a polymer or copolymer of a compound of formulaIor formula II[R1 and R2 are H or alkyl; R3 is H, oxyl (O.) or (substituted) alkyl; n is 0 or 1; A is group of formula III or formula IV; R4 is alkyl]. The molecular weight of the polymer is preferably 700-50,000, especially about 1,000-30,000. The unsaturated monomer copolymerized with the compound of formulaIor formula II is e.g. ethylene, propylene, butene-1, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention provides a stabilized synthetic resin composition, L <t
;! The present invention relates to a synthetic resin composition having improved light resistance and comprising a polymer made from an uncandyed ether compound having 2,2,6,6-titramethylpiperidyl.

Polyethylene, polypropylene, AB8 resin, polyvinyl chloride polymers are generally sensitive to the effects of light;
It is known that this effect causes deterioration, such as a decrease in color or strength, and that it cannot withstand long-term use.

In order to prevent the deterioration of polymers caused by this light, various stabilizers have been used in the past, but the stabilizing effect of the conventionally used light stabilizers is insufficient, and the stabilizers themselves are Many of these substances are unstable to heat or oxidation, are easily extracted from polymers by aqueous solvents, and also have the disadvantage that many substances color the polymers. could not be stabilized over a long period of time.

Among these conventionally used light stabilizers, hindered piperidine compounds have the characteristics of being non-coloring themselves and acting as quenchers rather than UV absorbers. It is receiving particular attention.

However, conventionally known piperidine-based compounds have insufficient photostabilizing ability, are highly volatile, and are easily extracted from polymers by water.
In addition, it also has disadvantages such as poor compatibility with polymers, which causes blue 5 and the like.

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

For example, JP-A-52-141,883 proposes a polymer such as polyester having a hindered piperidyl group, and JP-A-54721-489 and JP-A-54-
No. 71185 proposes a (meth)acrylate polymer having a hindered piperidyl group;
No. 5-157612 discloses a maleic acid ester-olefin copolymer having a hindered piperidyl group.

However, when using these polymers, although the volatility of the stabilizer is reduced, the stabilizing effect is not sufficient, and the compatibility with the polymeric substance to be photostabilized is poor.
There were some shortcomings that caused the plume, and further improvements were needed. In addition, since the above-mentioned polymer has an ester bond between the piperidine and the former, it suffers from hydrolysis and is easily extracted from the resin when used outdoors.

Further, JP-A-55-123608 discloses polymers of tetraalkylpiperidyl vinyl ether, but although these compounds improve volatility and water resistance, their stabilizing effect is still insufficient. Ashi, I needed to improve further.

The inventors of the present invention have made extensive studies regarding the current situation, and have found that:
The vinyl or allyl ether of the trihydric alcohol ketal of tetramethylpiperidone or the (co)polymer of the allyl ether of tetramethylpiperisinol has an extremely excellent stabilizing effect, has low volatility, and is easy to synthesize. It has been found that it has excellent compatibility with resins and has good water resistance.

That is, the present invention provides 0.001 to 5 parts by weight of at least one kind of polymer t or copolymer of a compound represented by the following general formula (summer) or Fi(1) to 100 parts by weight of the synthetic resin. The object of the present invention is to provide a stabilized synthetic resin composition.

L; R5 (In formulas (1) and (1), R1 and R2Fi each represent a water IJg atom, 9 represents an alkyl group, R5 represents a hydrogen atom,
Represents oxyl (O.) or an alkyl group that may have a substituent, n represents Of or 1, and among these compounds, the (co)polymer of the compound represented by general formula (1) is a compound It is particularly preferred because it has good heat resistance and its stabilizing effect does not decrease even after high-temperature processing.

Hereinafter, the compounds used in the present invention will be explained in detail.

Examples of the alkyl group represented by R1wR2 in the general formulas (1) and (II) include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and sec-butyl.

Examples of the alkyl group that may have a substituent represented by R5 include methyl, ethyl, propyl, butyl, hexyl, octyl, 2-ethylhexyl, tecyl, dodecyl,
Benzyl, 2-hydroxyethyl, 2-hydroxypropyl, 2-hydroxybutyl, 2-hydroxyoctyl, 2-hydroxy-2-phenylethyl, 2,3-dihydroxypropyl, 2-hydroxy-3-phenoxypropyl, 2. ! ! -Epoxyprobyl, 2-acetoxyethyl, 2-benzoyloxyethyl and the like.

The alkyl groups represented by 8 units include methyl, ethyl,
Examples include propyl and butyl.

In addition, the monomer represented by the general formula (1) t &#1 (1) can be obtained, for example, by the reaction of acetone with a ketal compound of nato-2-methylpiperidone and a trihydric alcohol, or by the reaction of halogenated propenes such as allyl chloride. The compound can be easily produced by reaction with the above-mentioned ketal compound, tetramethylpiperisinol, vinyl alkyl ether, or allyl alkyl ether.

of the compound represented by the general formula (1) or (厘)
Co)polymers can be produced by known methods such as free radical polymerization and cationic polymerization.

Free radical polymerization is carried out by ultraviolet irradiation or by using an organic peroxide or an organic azonitrile compound as an initiator. Further, cationic polymerization is carried out using a catalyst such as boron trifluoride, boron trifluoride etherate, phosphorous pentafluoride, aluminum chloride, tin tetrachloride, or the like.

In the present invention, other unsaturated monomers that can be copolymerized with the monomer represented by the general formula (1) include ethylene, propylene, butene-1, imbutylene,
Hexene, octene, decene, dodecene, tetradecene, hexadecene, oftatecene, eicosene, styrene, α-methyl-styrene, cyclohexene, butadiene, vinyl chloride, acrylonitrile, methyl vinyl ketone, methyl vinyl ether, vinyl acetate, acrylic acid, methacrylic acid, anhydride Maleic acid, methyl acrylate, butyl acrylate, methyl methacrylate, dimethyl maleate, diethyl maleate, dibutyl maleate, 1,2,2,4,6-pentamethylpiperidyl acrylate,
Fumar Il-1,2,2,6,6-pentamethylpiperidyl, bis(9-aza-5-ethyl-8,8゜9.10
．． 10-pentamethyl-1,5-dioxaspiro(5,
5)-! l-undecylmethyl) fumarate and the like.

Further, the molecular weight of the polymer used as a stabilizer in the present invention is preferably about 700 to 50.000, more preferably about 1. OOO~50. It's OOO.

Specific synthesis examples of the compounds represented by the general formula (1) or (1) and their (co)polymers are shown below,
The present invention will be further explained.

Synthesis example 1゜ Vinyl-9-aza-5-ethyl-8,8,? .

10.10-Pentamethyl-1,5-dioxaspiro (
5,5) Synthesis of -5-undecyl methyl ether 9-aza-3-ethyl-3-hydroxymethyl-8,8
,9,10,10-pentamethyl-1,5-dioxaspiro[5,5]undecane 15.1F.

59.4 f of vinyl-butyl ether and 0.72 f of mercury acetate were taken and heated and stirred under reflux for 50 hours. After removing unreacted vinyl-n-butyl ether and by-product butanol under reduced pressure, the mixture was treated with silica gel to obtain 114f colorless oil (monomer 1).

As a result of gas chromatography analysis, there was one peak, and as a result of infrared spectroscopy, the absorption based on the ether bond was at 1100cy+-1, the absorption based on the c=c double bond was at 1620cWI-', and N- There was an absorption based on CH3 at 2840 m-', indicating that it was the target product.

Synthesis example 2゜vinyl-9-aza-5-ethyl-8,8,10゜10-
Tetramethyl-1,5-dioxaspiro[5゜5]-5
-Synthesis of undecyl methyl ether 9-aza-3-ethyl-3-hydroxymethyl-8,8,10,10-tetramethyl-1,5-dioxaspiro[5,5]undecane5. Of, vinyl-n-butyl ether25. O
f and 0.6 t of aqueous acetic acid were taken and heated and stirred under reflux for 20 hours.

After removing unreacted vinyl-n-butyl ether and by-product butanol under reduced pressure, the product was treated with silica gel to form a colorless clear product (
Monomers 1)s and 1t were obtained.

1 Result of analysis by gas chromatography 1□ Peak is strong, and infrared spectroscopic analysis shows absorption based on ether bond is 110! In Sew-1, there is an absorption based on the C-C double bond at 1620" and an absorption based on NH at !1575 cm-", which is the desired product. Synthesis Example 3 Allyl-9-aza-3-ethyl- 8,8,9゜10.1
0-Pentamethyl-1,5-dioxaspiro(5,5)
-Synthesis of 3-undecyl methyl ether 9-aza-3-ethyl-3-hydroxymethyl-8,8
,9,10,10-pentamethyl-1,5-dioxaspiro I''s,s) undecane 5.2 F, xylene 5
- and 2.21 kg of sodium hydroxide were heated and dissolved.

Allyl chloride 7, Of was added to this, and the mixture was heated and stirred for 15 hours at reflux and filtration under a nitrogen atmosphere.

Cooled drained water was added, and the mixture was extracted with benzene. After drying the benzene solution, remove the solvent under reduced pressure, 6. A pale yellow oily product (monomer carbonate) of Of was obtained.

As a result of gas chromatography analysis, there is one peak, and as a result of infrared spectroscopy, the absorption based on the ether bond is 110051-', the absorption based on the c=c double bond is 1650ffi-', and the absorption based on N-CH3 is 110051-'. absorption is 28
20efR-' and confirm that it is the target object.9.

Synthesis Example Table Synthesis of allyl-1,2,2,4,6-bentamethyl-4-piperidyl ether 1.2,2,16.6-bentamethyl-4-piperidyl ether 4.9f, sodium hydroxide 3.32 and xylene 10- After heating and dissolving, add 9°Of allyl chloride,
The mixture was heated and stirred at reflux temperature for 15 hours under a nitrogen stream. After cooling, the mixture was extracted with benzene, and the benzene solution was dried and the solvent was removed under reduced pressure to obtain a yellow liquid. This yellow liquid is distilled and has a boiling point of 10
0-108'C/9 haze HH colorless liquid (monomer IV) 4
．． Obtained 5F.

Analysis by gas chromatography shows 1 peak, and infrared spectroscopy shows absorption based on ether bond at 10B5m-', absorption based on c=c double bond at 1645cm-', and N-CH5fC. based absorption is 2
It was located at 820m-1 and was confirmed to be the target object.

Synthesis Example 5゜Poly(vinyl-9-aza-3-ethyl-8,8゜?, 1
0.10-pentamethyl-1,5-dioxaspiro(5
, 53-3-undecyl methyl ether)'' synthesis
(Monomer I5.r3t obtained in Synthesis Example 1, benzene 4-
and tertiary butyl peroxide 180 capes were taken and heated and stirred at 160° C. for 7 hours under a nitrogen atmosphere. After removing benzene, it was treated with a methanol/water mixed solvent to reduce the molecular weight to 2.0.
00-2.500, melting point 65-75°C, nitrogen content 4.
47'l of light brown powder (stabilizer N11) was obtained.

The following polymer was synthesized in the same manner as in Synthesis Example 5.

-Poly(vinyl-9-aza-3-ethyl-8,8°10
．． 10-tetramethyl-1,5-dioxaspiro[s,
5]-g-undecyl methyl ether) (stabilizer N12
) Molecular weight 2,200-2.300: Nitrogen content 466f4
・Poly(allyl-9-aza-3-ethyl-8,8゜9.
01,10-pentamethyl-1,5-dioxaspiro[
5,5)-3-undecyl methyl ether) (stability factor 3) Molecular weight 1,500-1.700: Nitrogen content 4.25% poly(allyl-1,2,2,4,6-bentamethyl-4) -piperidyl ether) (stable side 4) molecular weight 1.0
00-1.100; Nitrogen content 6.56% Synthesis example 6゜vinyl-9-aza-5-ethyl-8,8,9゜10.1
0-Pentamethyl-1,5-dioxaspiro(5,5)
Synthesis of i-undecyl methyl ether/vinyl-n-butyl ether copolymer Monomer 1 obtained in Synthesis Example 1!
1. ．． ．． 1 F (0.01 mol), vinyl-n-butyl ether 2.0f (0.02 mol) in Heyasan 10-
0.1% of boron trifluoride
Dissolved in dt ether 5- and slowly added the solution,
It was held at -20°C for 10 hours. Then, methylene chloride was added, washed with water, dried, desolvated, and treated with a methanol/water mixed solvent to obtain a pale brown powder (stabilizer Na5) with a molecular weight of 15,800, a melting point of 68 to 77°C, and a nitrogen content of 2.79. Obtained.

Synthesis Example 7゜Allyl-? -Other 3-Ethyl 8.8,9゜10.1
0-Pentamethyl-1,5-dioxaspiro(5,5)
-5-undecyl methyl ether/bis(9-aza-5
-Ethyl-8,8,? , 10.10-pentamethyl-1
．． Synthesis of 5-dioxaspiro[5°5)-3-undecylmethyl) fumarate copolymer Monomer obtained in Synthesis Example 5 11. Of (0,003 mol), bis(9-aza-3-ethyl-8,8°9.01
,1G-pentamethyl-1,5-dioxaspiro[5,
5:1-3-undecylmethyl) fumarate) 4. Of
(0,006 mol) and dicumyl peroxide 0.
Dissolve 5F in benzene 4-7.7 at 160-170℃
The mixture was heated and stirred for hours. After removing the solvent under reduced pressure, the resulting brown solid was treated with methanol/water solvent and reduced to a molecular weight of 1.
700, a melting point of 68 DEG -74 DEG C., and a nitrogen content of 4.30 DEG C., a light brown powder product (stabilizer 6) was obtained.

In the same manner as in Synthesis Example 7, the stabilizers shown in the table below were synthesized by varying the monomers and copolymerization components.

In the present invention, the specific unsaturated ether (co)polymer is added to a synthetic resin to improve its light resistance, and the amount added is usually 0.000 parts by weight per 100 parts by weight of synthetic #Jfh.
001-5 parts by weight, preferably Fio, 01-S parts by weight.

Examples of synthetic resins to be improved in light resistance in the present invention include α-olefin polymers such as polyethylene, polypropylene, polybutene, and poly-5-methylbutene, ethylene-vinyl acetate copolymers, and ethylene-vinyl acetate copolymers.
Polyolefins such as propylene copolymers and their copolymers, 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, vinyl chloride-styrene-acrylonitrile copolymer, vinyl chloride-butadiene copolymer, vinyl chloride-isopsine copolymer, vinyl chloride-chlorinated propylene copolymer, Vinyl chloride - vinylidene chloride -
Vinyl acetate terpolymer, vinyl chloride-acrylic acid ester copolymer, vinyl chloride-maleic acid ester copolymer, vinyl chloride-methacrylic acid ester copolymer, vinyl chloride-acrylonitrile copolymer, internally plasticized polyester Halogen-containing synthetic resins such as vinyl chloride, petroleum resins, coumaron resins, polystyrene, polyvinyl acetate, acrylic resins, copolymers of styrene and other monomers (e.g. maleic anhydride, butadiene, acrylonitrile, etc.), acrylonitrile- Butadiene-styrene copolymer, acrylic ester-butadiene-styrene copolymer, methacrylic ester-butadiene-styrene copolymer, methacrylate resin such as polymethyl methacrylate, polyvinyl alcohol, polyvinyl formal, polyvinyl butyral, linear polyester, Examples include polyphenylene oxide, boria zeta, polycarbonate, polyacetal, polyurethane, rutted cellulose resin, #-j phenol resin, area resin, melamine resin, epoxy resin, unsaturated polyester resin, silicone resin, etc. . Furthermore, rubbers such as isoprene rubber, butadiene rubber, acrylonitrile-butadiene copolymer rubber, styrene-butadiene copolymer rubber, and blends of these resins may also be used.

Also included are crosslinked polymers such as crosslinked polyethylene crosslinked with peroxide or radiation, and foamed polymers such as expanded polystyrene foamed with a foaming agent.

Oxidative stability can be improved by further adding a phenolic antioxidant to the composition of the invention.

These phenolic antioxidants include 9, 2,
6-di-tert-butyl-p-cresol, stearyl-(
3,5-di-methyl-4-hydroxybenzyl)thioglycolate, stearyl-β-(4-hydroxy-3,
5-di-5-butyl phenyl) glopionate, distearyl-3,5-di-5-butyl-4-hydroxybenzylphosphonate, 2.4.6-) lis(3', 5'
-di-5-butyl-4'-hydroxybenzylthio)
-1,is,5-) riazine, distearyl(4-hydroxy-3-meth-5-tert-butyl)benzylmalonate, 2,2'-methylenebis(4-methyl-6-tert-butylphenol) , 414'-methylenebis(2,
6-di-tert-butylphenol), 2゜2'-meth/bis[6-(1-methylcyclohexyl)p-cresol], bis[3,5-bis(4-human,
5th Butylphenyl＼) Butyric acid coglycol ester, 4゜4'-
butylidene bis(6-tert-butyl-m-cresol),
1,1,3-tris(2-methyl-4-human tetraxy-5
4g5butylphenyl)butane, bis[2-Igsbutyl-4-methyl-6-(2-hydroxy-3-tert-butyl-5-monotylphenyl)phenyl]terephthalate,
1°3.5-)lis(2,6-dimethyl-3-hydroxy-4-M3butyl)penzyl isocyanurate, 1.
! S, 5-) lis(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene,
Tetrakis[methylene-S-(S,S-di-5-butyl-4-hydroxyphenyl)propio*-))methane,
1゜3.5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanuride), 1゜3.5-)
Lis((5,5-di-tert-butyl-4-hydroxyphenyl)propionyloxyethyl)isocyanurate,
2-octylthio-4,6-di(4-hydroxy-3,
5-G? I! 5-butyl) phenoxy-1,! 5.5-
) riazine, 4,4'-thiobis(6-5-butyl-
7 enols such as
, 6, 7, 8, 9, 10, etc.).

It is also possible to further add a sulfur-based antioxidant to the composition of the present invention to improve its oxidative stability. Examples of these sulfur-based antioxidants include dialkylthiodigropionates such as dilauryl, similystyl, and distearyl, and alcohols of alkylthiopropionic acids such as butyl, octyl, lauryl, and stearyl (e.g., glycerol). , trimethylolethane, trimethylolpropane, pentaerythritol, trishydroxyethyl isocyanurate) (eg, pentaerythritol tetralauryl thioprobionate).

Light resistance and heat resistance can be improved by further adding a phosphorus-containing compound such as phosphite to the composition of the present invention. Examples of the phosphorus-containing compound include trioctyl phosphite, trilauryl phosphite,
Tridecyl phosphite, octyl diphenyl phosphite, tris(2,4-di-tert-butylphenyl) phosphite, triphenyl phosphite, tris(butoxyethyl) phosphite, tris(nonylphenyl)
Phosphite, distearylpentaerythritol diphosphite, tetra(tridecyl)-'*L! I-) Lis(2-methyl-5-tert-butyl-4-hydroxyphenyl)butane diphosphite, tetra(c12-15 mixed alkyl)-4,4'-isopropylidene diphenyl diphosphite, tetra(tridecyl) -4, 4'
-butylidene bis(3-methyl-6-tert-butylphenol) diphosphite, tris(5,5-di-tert-butyl-4-hydroxyphenyl) phosphite, tris(
Mono/dimixed nonylphenyl) phosphite, hydrogenated-
4,4'-isopropylidene diphenol polyphosphite, bis(octylphenyl) bis[4,4'-butylidene bis(5-methyl-6-tert-butylphenol)]·1, . 6-hedFf diol diphosphite, phenyl-4,4'-isopropylidene diphenol pentaerythritol diphosphite, bis(2,4
-di-tert-butyl phenyl) pentaerythritol diphosphite, bis(2,6-di-tert-butyl-4-methylphenyl) pentaerythritol diphosphite, tris[4,4'-isopropylidene bis(2-tert-butyl-4-methylphenyl) butylphenol)] phosphite, phenyl diisodecyl phosphite, di(nonylphenyl) pentaerythritol diphosphite, tris(1,S-di-stearoyloxyisopropyl) phosphite, 4,4'-
Isopropylidene bis(2-tert-butylphenol)・
cy(nonylphenyl-)phosphite, 9.10-di-
Hydro-9-oxa-10-7 osphafluorene-10-oxide, tetrakis (2,4-di-3
butylphenyl) -4,4'-biphenylene diphosphonite, etc.

By adding other light stabilizers to the compositions of the invention, their lightfastness can be further improved. Examples of these light stabilizers include 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-11-octoxybenzophenone, 2,2'-di-hydroxy-4-
Hydroxybenzophenones such as methoxybenzophenone and 2,4-dihydroxybenzophenone, 2-(2
'-Hydroxy-5'-1-butyluda-methylphenyl)-5-chloropenttriazole, 2- (2'-
Hydroxy-sl, sl-di-t-butylphenyl)-5-chlorobenzotriazole, 2-(2'-hydroxy-51-methylphenyl)benzotriazole,
Benzotriazoles such as 2-(2'-hydroxy-3', s'-t-amylphenyl)benzotriazole, phenyl salicylate, p-1-butylphenyl salicylate, 2,4-di-t-butylphenyl- 3,5
-di-t-butyl-4-hydroxybenzoate, benzoates such as subcyl-5,5-di-t-butyl-4-human-xybenzoate, 2,2'-thiobis(
4-t-octylphenol) Nl salt, (2,2'-thiobis(4-t-octylphenolate))-n-butylamine N1, (3,5-di-t-butyl-4-hydroxybenzyl)phosphonic acid Monoethyl ester Ni salt Misaki menickel compounds, α-cyano-β-methyl-β-(
(p-methoxyphenyl) acrylics Substituted acrylonitriles such as methyl and HN-2-ethylphenyl-N'
-2-Ethoxy-5-tert-butylphenyl oxalic acid diamide, N-2-ethylphenyl-N'-2-ethoxyphenyl oxalic acid diamide and oxalic acid dianilides.

If necessary, the composition of the present invention may also contain heavy metal deactivators, nucleating agents, metal soaps, organic tin compounds, plasticizers, epoxy compounds, pigments, fillers, blowing agents, antistatic agents, flame retardants, and lubricants. 1. Processing aids and the like can be included.

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

Example 1 Polyvinyl chloride 100 parts by weight Dioctyl phthalate 48 parts by weight Epoxidized soybean oil 2 Trisnonylphenyl phosphite 0.2 Ca-stearate 1. .

Zn-stearate 0.1 Stabilizer (Table 1) o, s The above formulation was kneaded on a roll to form a sheet with a thickness of 1 inch. A light resistance test in a weather offter was conducted using this sheet. The results are shown in Table-1.

Table-1 Example 2 Polypropylene 100 parts by weight Stearyl-β-3,5-di-5-butyl-0,24-
Hydroxyphenylpropionate stabilizer (Table-2)
0. ! S Thickness 0.3- with the above formulation
A press sheet was prepared and a light resistance test was conducted using a high-pressure mercury lamp. A light resistance test was also conducted on the sheet after being irradiated with light for 100 hours and immersed in hot water at 80° C. for 15 hours. The results are shown in Table-2.

Table 2 Example 3 Ethylene-vinyl acetate copolymer 100 parts by weight 2.6-di-5-butyl-p-cresol 0.1
0a-stearate 0.1Z
n stearate 0.1
Diisodecyl phenyl phosphite 0.2 Stabilizer (Table s) 0.2 The above blend was mixed on a roll at 130°C, and then pressed at 140°C to form a press sheet (thickness: 0.4 cm). The residual tensile strength of this sheet was measured after 500 hours of irradiation in a weather heater.

The results are shown in Table-3.

! I-s Practical meeting.

Polyethylene 100 parts by weight Cm-stearate 1.0 Tetrakis [methylene-5-(S,S-di-tert-butyl-
4-Hydroxyphenyl 0.1) propionate comethanedistearylthiodipropionate 0.3
Stabilizer (Table 4) 0.2 The above blend was mixed and pressed to make a sheet with a thickness of 0.5.

Using this sheet, the light resistance was measured in a weather oven, and the time until it became brittle was measured. Table 4 shows the results.
Shown below.

Table-4 Example 5゜ABS resin 10 parts by weight 4.4'
-Butylidene bis(2-30.1-butyl-m-cresol) Stabilizer (Table 5) o, s The above formulation was kneaded with rolls and then pressed to make a 3-thick sheet. Using this sheet, the residual tensile strength after 800 hours of irradiation was measured using a weatherometer. The results are shown in Table-5.

Table 5 Example 6 It is known that ordinary stabilizers evaporate during high-temperature processing of resins and lose their effectiveness due to pollution, etc.

In this example, the effect of high-temperature processing was confirmed by repeatedly performing extrusion processing.

After mixing the resin and additives at 5 mixers for 5 minutes according to the following formulation, a compound was prepared using an extruder. (Cylinder salt [2SO℃, 240℃, head die temperature 250℃
After extrusion was repeated five times (at a rotation speed of 20° C. and a rotational speed of 2 rpm), a test piece was prepared using an injection molding machine using this compound.

(Cylinder temperature 240°C, nozzle temperature 250°C, injection pressure 4751'l/cd) Using the obtained test piece, a light resistance test was conducted using a high pressure mercury lamp. In addition, the same test was performed on the extruded product once, and the results are shown in Table 6.

<Blend> Ethylene-propylene copolymer resin 100 parts by weight Stearyl-β-5,5-di-tert-butyl 0.1-
4-Hydroxyphenylpropionate dilaurylthiodipropionate 0.2 Stabilizer (Table 61
0,2 1! -6 Example 7 Polyurethane resin (U-1on manufactured by Asahi Denka) 1o
o Part by weight Ba-stearate
0.7 Zn-stearate 0.
32.6-di-tert-butyl-p-cresol 0.
1 Stabilizer (Table-7) 0. ! 1 The above mixture was kneaded on a roll at 70°C for 5 minutes and pressed at 120°C for 5 minutes to prepare seeds with a thickness of 0.5 m+. The residual elongation of this sheet after 50 hours of irradiation was measured using a fade meter.

The results are shown in Table-7.

Claims (1)

[Claims] For 100 parts by weight of synthetic resin, the following general formula (1) or H
At least one type of polymer or copolymer of the compound represented by (1) is 0. A stabilized synthetic resin composition containing 1 to 5 parts by weight of OO. CH5 (In the formulas (+) and (v, R1 and R2 each represent a hydrogen atom or an alkyl group, R5 represents a hydrogen atom, oxyl (0.) or an alkyl group that may have a substituent, and n#io or 1, ACH2-Rq\yC
R2- tj -CH2-CH-t ft:,, u -CH2
/C\CH2fr L, RII represents an alkyl group,
,)