Resin composition, molded article, method for producing resin composition, resin additive composition, and method for thermally stabilizing synthetic resin

Abstract

Provided are: a resin composition having excellent thermal stability; a molded article; a method for producing a resin composition; a resin additive composition able to impart a synthetic resin with excellent thermal stability; and a method for thermally stabilizing a synthetic resin.　This resin composition contains a synthetic resin, a compound represented by general formula (1) and a compound represented by general formula (2). (In general formula (1), R1, R2, R3, R11, R12, R13, R4 and R5 each independently denote a hydrogen atom or the like, X denotes a single bond or the like, A denotes an alkylene group having 1-30 carbon atoms, or the like, Y and / or Z denotes a hydroxyl group, and if Y or Z is a hydroxyl group, the other is a hydrogen atom or the like.) (In general formula (2), R6 and R16 each independently denote an alkylene group having 1-30 carbon atoms, or the like.)

Description

Resin composition, molded article, method for producing resin composition, resin additive composition, and method for thermal stabilization of synthetic resin

[0001] The present invention relates to a resin composition, a molded article, a method for producing a resin composition, a resin additive composition, and a method for thermal stabilization of a synthetic resin, and more particularly to a resin composition having excellent thermal stability, a molded article, a method for producing a resin composition, a resin additive composition that can impart excellent thermal stability to a synthetic resin, and a method for thermal stabilization of a synthetic resin.

[0002] Various methods for improving the thermal stability of synthetic resins have been investigated. For example, Patent Document 1 proposes a resin composition obtained by heat-melting and mixing a specific phosphite ester with a polyolefin resin.

[0003] Japanese Patent Application Laid-Open No. 2002-212347

[0004] However, the resin composition proposed in Patent Document 1 has room for further improvement in terms of thermal stability.

[0005] Therefore, an object of the present invention is to provide a resin composition having excellent thermal stability, a molded article, a method for producing a resin composition, a resin additive composition capable of imparting excellent thermal stability to a synthetic resin, and a method for thermal stabilization of a synthetic resin.

[0006] As a result of extensive research, the present inventors have found that the above problems can be solved by a resin composition containing a synthetic resin and a specific compound, and have thus completed the present invention.

[0007] That is, the present invention is a resin composition containing a synthetic resin, a compound represented by the following general formula (1), and a compound represented by the following general formula (2). (In general formula (1), R １ , R ２ , R ３ , R １１ , R １２ , R １３ , R ４ and R ５each independently represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms which may have a substituent; X represents a single bond, a sulfur atom, or an alkanediyl group having 1 to 30 carbon atoms; A represents an alkylene group having 1 to 30 carbon atoms or a divalent group represented by *-C(=O)A'-; A' represents a single bond or an alkylene group having 1 to 30 carbon atoms; * represents a site bonding to an oxygen atom; at least one of Y and Z represents a hydroxyl group; and when only one of Y and Z is a hydroxyl group, the other represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms which may have a substituent. (In general formula (2), R ６ and R １６ each independently represents an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms which may have a substituent.

[0008] The present invention also relates to a molded article obtained by molding the above resin composition.

[0009] Furthermore, the present invention is a method for producing a resin composition, which includes a blending step of mixing a synthetic resin, a compound represented by the general formula (1) above, and a compound represented by the general formula (2) above.

[0010] Furthermore, the present invention is a resin additive composition containing a compound represented by the above general formula (1) and a compound represented by the above general formula (2).

[0011] Furthermore, the present invention is a method for thermal stabilization of a synthetic resin, comprising a blending step of mixing a synthetic resin, a compound represented by the above general formula (1), and a compound represented by the above general formula (2).

[0012] According to the present invention, it is possible to provide a resin composition having excellent thermal stability, a molded article, a method for producing a resin composition, a resin additive composition capable of imparting excellent thermal stability to a synthetic resin, and a method for thermal stabilization of a synthetic resin.

[0013] Hereinafter, an embodiment of the present invention will be described in detail. <Resin Composition> The resin composition of the present embodiment contains a synthetic resin, a compound represented by the following general formula (1), and a compound represented by the following general formula (2).

[0014]

[0015] Here, in general formula (1), R １ , R ２ , R ３ , R １１ , R １２ , R １３ , R ４ and R ５ each independently represent a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms which may have a substituent; X represents a single bond, a sulfur atom, or an alkanediyl group having 1 to 30 carbon atoms; A represents an alkylene group having 1 to 30 carbon atoms or a divalent group represented by *-C(=O)A'-; A' represents a single bond or an alkylene group having 1 to 30 carbon atoms; * represents a site bonding to an oxygen atom; at least one of Y and Z represents a hydroxyl group; and when only one of Y and Z is a hydroxyl group, the other represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms which may have a substituent.

[0016]

[0017] Here, in general formula (2), R ６ and R １６ each independently represents an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms which may have a substituent.

[0018] The resin composition of this embodiment has excellent thermal stability.

[0019] The reason why the resin composition of this embodiment has excellent thermal stability is not entirely clear, but is presumed to be as follows. That is, when the resin composition is heated and melted, the compound represented by general formula (2) quickly exerts a thermal stabilizing effect, suppressing thermal degradation of the synthetic resin in the initial state of heat and melting. On the other hand, the compound represented by general formula (1) maintains its thermal stabilizing effect for a long period of time, sufficiently suppressing thermal degradation of the synthetic resin even when the heat-molten state is maintained for a long period of time. In this way, it is presumed that the compound represented by general formula (1) and the compound represented by general formula (2) complementarily exert a thermal stabilizing effect on the synthetic resin, resulting in the resin composition of this embodiment having excellent thermal stability.

[0020] The synthetic resin may be a thermoplastic resin or a thermosetting resin. Examples of thermoplastic resins include crystalline resins such as polyolefin resins, polyamide resins, polyester resins, polyacetal resins, polylactic acid, and polyphenylene sulfide; amorphous resins such as polycarbonate resins, styrene resins, acrylic resins, urethane resins, halogen-containing resins, petroleum resins, coumarone resins, polyvinyl alcohol, polyvinyl acetate, and polyphenylene oxide; and thermoplastic elastomers. Examples of thermosetting resins include phenol resins, urea resins, melamine resins, epoxy resins, unsaturated polyester resins, alkyd resins, and synthetic rubber. One type of synthetic resin may be contained alone, or two or more types may be contained in combination. The synthetic resin may also be a copolymer or a polymer alloy.

[0021] The synthetic resin is preferably a thermoplastic resin. The thermoplastic resin preferably contains a crystalline resin, more preferably contains at least one selected from the group consisting of polyolefin resins, polyamide resins, polyester resins, polyacetal resins, polylactic acid, and polyphenylene sulfide, and even more preferably contains a polyolefin resin.

[0022] Examples of polyolefin resins include polyethylene resins such as low-density polyethylene, linear low-density polyethylene, high-density polyethylene, cross-linked polyethylene, and ultra-high molecular weight polyethylene; polypropylene resins such as homopolypropylene, random copolymer polypropylene, block copolymer polypropylene, impact copolymer polypropylene, high-impact copolymer polypropylene, and maleic anhydride-modified polypropylene; α-olefin polymers such as polybutene-1, cycloolefin polymer, poly-3-methyl-1-butene, poly-3-methyl-1-pentene, and poly-4-methyl-1-pentene; and α-olefin copolymers such as ethylene-methyl methacrylate copolymer and ethylene-vinyl acetate copolymer. Among polyolefin resins, polypropylene resins are particularly preferred from the viewpoint of improving the heat resistance of the resin composition. The molecular weight, degree of polymerization, density, softening point, proportion of solvent-insoluble matter, degree of stereoregularity, presence or absence of catalyst residue, types and blending ratios of raw material monomers, and type of catalyst used in polymerization (e.g., Ziegler catalyst, metallocene catalyst, etc.) are not particularly limited and may be selected appropriately.

[0023] In the resin composition of the present embodiment, the synthetic resin may contain a recycled resin. Conventional resin compositions containing recycled resins are prone to drawdown during molding, but in the resin composition of the present embodiment, when the synthetic resin contains a recycled resin, drawdown during molding is sufficiently suppressed.

[0024] The recycled resin may be an in-process recycled material recovered from scraps generated when molding the resin composition of the present embodiment, or may be a material recovered from waste such as post-consumer materials or pre-consumer materials. From the viewpoint of improving the properties of the resin composition, the recycled resin is preferably an in-process recycled material.

[0025] When the synthetic resin contains a recycled resin, the content of the recycled resin can be, for example, 1 to 100% by mass of the total synthetic resin. From the viewpoint of utilizing resources as efficiently as possible and sufficiently suppressing drawdown when molding the resin composition, the recycled resin is preferably 5 to 80% by mass of the total synthetic resin, more preferably 10 to 70% by mass, even more preferably 20 to 60% by mass, and even more preferably 30 to 50% by mass.

[0026] As described above, the resin composition of the present embodiment contains the compound represented by the general formula (1).

[0027] R １ , R ２ , R ３ , R １１ , R １２ , R １３ , R ４ and R ５Examples of the alkyl group having 1 to 30 carbon atoms represented by the formula (I) include linear alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, n-eicosyl, and n-triacontyl groups; branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, tert-amyl, 2-heptyl, tert-heptyl, tert-octyl, isononyl, and isodecyl groups; and cyclic alkyl groups such as cyclopentyl, cyclohexyl, cyclooctyl, and adamantyl groups. From the viewpoint of improving the thermal stability of the resin composition, among these, a linear alkyl group and a branched alkyl group are preferred, a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an isopropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an isopentyl group, a neopentyl group, and a tert-amyl group are more preferred, a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an isopropyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group are even more preferred, and a methyl group or a tert-butyl group is even more preferred.

[0028] R １ , R ２ , R ３ , R １１ , R １２ , R １３ , R ４ and R ５ Examples of the alkoxy group having 1 to 30 carbon atoms represented by include groups having a structure in which the above alkyl group having 1 to 30 carbon atoms is bonded to an oxygen atom.

[0029] R １ , R ２ , R ３ , R １１ , R １２ , R １３ , R ４ and R ５Examples of the aryl group having 6 to 30 carbon atoms, which may have a substituent, represented by the formula (I), include a phenyl group, an o-biphenylyl group, an m-biphenylyl group, a p-biphenylyl group, an α-naphthyl group, a β-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthryl group, a 1-phenanthryl group, a 2-phenanthryl group, a 3-phenanthryl group, a 4-phenanthryl group, a 9-phenanthryl group, a phenyl group having a substituent, an o-biphenylyl group having a substituent, Examples of such aryl groups include a substituted m-biphenylyl group, a substituted p-biphenylyl group, a substituted α-naphthyl group, a substituted β-naphthyl group, a substituted 1-anthryl group, a substituted 2-anthryl group, a substituted 9-anthryl group, a substituted 1-phenanthryl group, a substituted 2-phenanthryl group, a substituted 3-phenanthryl group, a substituted 4-phenanthryl group, and a substituted 9-phenanthryl group. Among these, phenyl groups or substituted phenyl groups are preferred from the viewpoint of improving the thermal stability of the resin composition. Furthermore, the aryl group having 6 to 30 carbon atoms may be unsubstituted or substituted. Here, when the aryl group having 6 to 30 carbon atoms has a substituent, examples of the substituent include an alkyl group having 1 to 30 carbon atoms and an alkoxy group having 1 to 30 carbon atoms. Among these, an alkyl group having 1 to 30 carbon atoms is preferred from the viewpoint of improving the thermal stability of the resin composition. Here, the alkyl group having 1 to 30 carbon atoms and the alkoxy group having 1 to 30 carbon atoms include R １ , R ２ , R ３ , R １１ , R １２ , R １３ , R ４ and R ５ Examples of the alkyl group having 1 to 30 carbon atoms and the alkoxy group having 1 to 30 carbon atoms represented by the formula (I) include the same as those exemplified above.

[0030] Examples of the alkanediyl group having 1 to 30 carbon atoms represented by X include alkylene groups such as methylene, ethylene, propylene, and butylene, and alkylidene groups such as ethylidene, propan-1-ylidene, propan-2-ylidene, butan-1-ylidene, butan-2-ylidene, and cyclohexylidene. From the viewpoint of improving the thermal stability of the resin composition, among these, methylene, ethylene, ethylidene, propan-1-ylidene, and propan-2-ylidene are preferred, with methylene, ethylene, and ethylidene being more preferred, and methylene being even more preferred.

[0031] Examples of the alkylene group having 1 to 30 carbon atoms represented by A include a methylene group, an ethylene group, a propylene group, a butylene group, etc. From the viewpoint of improving the thermal stability of the resin composition, among these, a methylene group, an ethylene group, or a propylene group is preferred, and a propylene group is more preferred.

[0032] Examples of the alkylene group having 1 to 30 carbon atoms represented by A' include the same groups as those exemplified as the alkylene group having 1 to 30 carbon atoms represented by A.

[0033] As described above, at least one of Y and Z represents a hydroxyl group. Here, both Y and Z may be hydroxyl groups, or only one of Y and Z may be a hydroxyl group. Furthermore, as described above, when only one of Y and Z is a hydroxyl group, the other represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms which may have a substituent. Here, examples of the alkyl group having 1 to 30 carbon atoms, the alkoxy group having 1 to 30 carbon atoms, and the aryl group having 6 to 30 carbon atoms which may have a substituent include R １ , R ２ , R ３ , R １１ , R １２ , R １３ , R ４ and R ５Examples of the alkyl group having 1 to 30 carbon atoms, the alkoxy group having 1 to 30 carbon atoms, and the aryl group having 6 to 30 carbon atoms which may have a substituent are the same as those exemplified above.

[0034] From the viewpoint of improving the thermal stability of the resin composition, R １ and R １１ , R ２ and R １２ , and R ３ and R １３ are preferably the same group, and R １ and R １１ , R ２ and R １２ , and R ３ and R １３ are the same group and are more preferably a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an isopropyl group, an isobutyl group, a sec-butyl group, or a tert-butyl group, and R １ and R １１ , R ２ and R １２ , and R ３ and R １３ are the same group and are more preferably a hydrogen atom, a methyl group or a tert-butyl group.

[0035] Furthermore, from the viewpoint of improving the thermal stability of the resin composition, X is preferably a single bond, a methylene group, an ethylene group, or an ethylidene group, more preferably a single bond or a methylene group, and even more preferably a single bond.

[0036] Furthermore, from the viewpoint of improving the thermal stability of the resin composition, A is preferably a methylene group, an ethylene group, or a propylene group, and more preferably a propylene group.

[0037] Furthermore, from the viewpoint of improving the thermal stability of the resin composition, it is preferable that only one of Y and Z is a hydroxyl group, it is more preferable that only Y is a hydroxyl group, and it is even more preferable that Y is a hydroxyl group and Z is a hydrogen atom.

[0038] Specific examples of the compound represented by general formula (1) include 2,4,8,10-tetra-t-butyl-6-[3-(3-methyl-4-hydroxy-5-t-butylphenyl)propoxy]dibenzo[d,f][1,3,2]dioxaphosphepine, 6-[3-(3,5-di-t-butyl-4-hydroxyphenyl)propoxy]-2,4,8,10-tetra-t-butyldibenzo[d,f][1,3,2]dioxaphosphepine, Examples of suitable hydroxybenzoates include 2,4,8,10-tetra-t-butyl-6-[3-(3-methyl-4-hydroxy-5-t-butylphenyl)propoxy]dibenzo[d,f][1,3,2]dioxaphosphepine, 6-[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionyloxy]-4,8-di-t-butyl-2,10-dimethyl-12H-dibenzo[d,g][1,3,2]dioxaphosphepine, and the like. From the viewpoint of improving the thermal stability and hydrolysis resistance of the resin composition, 2,4,8,10-tetra-t-butyl-6-[3-(3-methyl-4-hydroxy-5-t-butylphenyl)propoxy]dibenzo[d,f][1,3,2]dioxaphosphepine is particularly preferred.

[0039] In the resin composition of this embodiment, the content of the compound represented by general formula (1) can be, for example, 0.001 to 10 parts by mass relative to 100 parts by mass of synthetic resin. From the viewpoint of further improving the thermal stability of the resin composition, the content of the compound represented by general formula (1) is preferably 0.005 to 5 parts by mass relative to 100 parts by mass of synthetic resin, more preferably 0.01 to 3 parts by mass, even more preferably 0.03 to 1 part by mass, and even more preferably 0.05 to 0.5 parts by mass.

[0040] As described above, the resin composition of the present embodiment contains the compound represented by the general formula (2).

[0041] R ６ and R １６ The alkyl group having 1 to 30 carbon atoms and the aryl group having 6 to 30 carbon atoms which may have a substituent represented by R １ , R ２ , R ３, R １１ , R １２ , R １３ , R ４ and R ５ Examples of the alkyl group having 1 to 30 carbon atoms and the aryl group having 6 to 30 carbon atoms which may have a substituent are the same as those exemplified above.

[0042] From the viewpoint of improving the thermal stability of the resin composition, R ６ and R １６ are preferably the same group. From the viewpoint of improving the thermal stability of the resin composition and the hydrolysis resistance, R ６ and R １６ are preferably the same group and are an aryl group having 6 to 30 carbon atoms which may have a substituent, and R ６ and R １６ are the same group and are more preferably substituted aryl groups having 6 to 30 carbon atoms, and R ６ and R １６ are the same group and are more preferably phenyl groups having a substituent, and R ６ and R １６ are the same group and are even more preferably phenyl groups in which at least one hydrogen atom is substituted with an alkyl group having 1 to 30 carbon atoms; ６ and R １６ are the same group, and are particularly preferably a phenyl group in which at least one hydrogen atom has been substituted with a tert-butyl group.

[0043] Specific examples of the compound represented by general formula (2) include bis(diisodecyl)pentaerythritol diphosphite, bis(tridecyl)pentaerythritol diphosphite, bis(octadecyl)pentaerythritol diphosphite, bis(nonylphenyl)pentaerythritol diphosphite, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, bis(2,4,6-tri-tert-butylphenyl)pentaerythritol diphosphite, bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite, and bis(2,4-dicumylphenyl)pentaerythritol diphosphite. Among these, from the viewpoint of improving the hydrolysis resistance while providing excellent thermal stability to the resin composition, bis(nonylphenyl)pentaerythritol diphosphite, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, bis(2,4,6-tri-tert-butylphenyl)pentaerythritol diphosphite, bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite, and bis(2,4-dicumylphenyl)pentaerythritol diphosphite are preferred, and bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite is particularly preferred. More preferred are pentaerythritol diphosphite, bis(2,4,6-tri-tert-butylphenyl)pentaerythritol diphosphite or bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite, even more preferred are bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite or bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite, and even more preferred is bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite.

[0044] In the resin composition of this embodiment, the content of the compound represented by general formula (2) can be, for example, 0.001 to 10 parts by mass relative to 100 parts by mass of the synthetic resin. From the viewpoint of further improving the thermal stability of the resin composition, the content of the compound represented by general formula (2) is preferably 0.005 to 5 parts by mass relative to 100 parts by mass of the synthetic resin, more preferably 0.01 to 3 parts by mass, even more preferably 0.03 to 1 part by mass, and even more preferably 0.05 to 0.5 parts by mass.

[0045] Furthermore, in the resin composition of this embodiment, the content of the compound represented by general formula (2) can be, for example, 1 to 10,000 parts by mass relative to 100 parts by mass of the compound represented by general formula (1). From the viewpoint of further improving the thermal stability of the resin composition, the content of the compound represented by general formula (2) is preferably 10 to 1,000 parts by mass, more preferably 20 to 500 parts by mass, even more preferably 25 to 400 parts by mass, and even more preferably 50 to 200 parts by mass relative to 100 parts by mass of the compound represented by general formula (1).

[0046] The resin composition of the present embodiment preferably further contains a phenolic antioxidant, provided that the phenolic antioxidant in the present embodiment does not include the compound represented by the general formula (1) described above.

[0047] When the resin composition of this embodiment contains a phenolic antioxidant, the phenolic antioxidant reinforces the action of the compound represented by general formula (1) in capturing peroxy radicals generated when the resin composition is heated and melted, and as a result, when the resin composition of this embodiment contains a phenolic antioxidant, the resin composition has even better thermal stability.

[0048] Examples of phenolic antioxidants include 2,6-di-tert-butyl-4-ethylphenol, 2-tert-butyl-4,6-dimethylphenol, styrenated phenol, 2,2'-methylenebis(4-ethyl-6-tert-butylphenol), 2,2'-thiobis-(6-tert-butyl-4-methylphenol), 2,2'-thiodiethylenebis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], 2-methyl-4,6-bis(octylsulfanylmethyl)phenol, 2,2'-isobutylidenebis(4,6-dimethylphenol), isooctyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, and N,N'-hexane-1,6-diylbis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionamide], 2,2'-oxamido-bis[ethyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], 2-ethylhexyl-3-(3',5'-di-tert-butyl-4'-hydroxyphenyl)propionate, 2,2'-ethylenebis(4,6-di-tert-butylphenol), 3,5-di-tert-butyl-4-hydroxybenzenepropanoic acid and C13-15 alkyl ester, 2,5-di-tert-amylhydroquinone, hindered phenol polymer (manufactured by ADEKA POLYMER ADDITIVES EUROPE SAS), Product name "AO.OH.98"), 2,2'-methylenebis[6-(1-methylcyclohexyl)-p-cresol], 2-tert-butyl-6-(3-tert-butyl-2-hydroxy5-methylbenzyl)-4-methylphenyl acrylate, 2-[1-(2-hydroxy-3,5-di-tert-pentylphenyl)ethyl]-4,6-di-tert-pentylphenyl acrylate, 6-[3-(3-tert-butyl-4-hydroxy-5-methyl)propoxy]-2,4,8,10-tetra-tert-butylbenz[d,f][1,3,2]-dioxaphophobin, hexamethylenebis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], bis[monoethyl(3,5-di-tert-butyl-4-hydroxybenzyl)phosphonate] calcium salt, reaction products of 5,7-bis(1,1-dimethylethyl)-3-hydroxy-2(3H)-benzofuranone with o-xylene, 2,6-di-tert-butyl-4-(4,6-bis(octylthio)-1,3,5-triazin-2-ylamino)phenol, DL-α-tocopherol (vitamin E), 2,6-bis(α-methylbenzyl)-4-methylphenol, bis[3,3-bis-(4'-hydroxy-3'-tert-butyl-phenyl)butanoic acid]glycol ester, 2,6-di-tert-butyl-p-cresol, 2,6-diphenyl-4-octadecyloxyphenol, stearyl (3,5-di-tert-butyl-4-hydroxyphenyl)propionate, distearyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonate, tridecyl-3,5-tert-butyl-4-hydroxybenzylthioacetate, thiodiethylenebis[(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], 4,4'-thiobis(6-tert-butyl-m-cresol), 2,2'-methylenebis(4-methyl-6-tert-butylphenol), bis[3,3-bis(4-hydroxy-3-tert-butylphenyl)butylic acid]glycol ester, 4,4'-butylidenebis(2,6-di-tert-butylphenol), 4,4'-butylidenebis(6-tert-butyl-3-methylphenol), 2,2'-ethylidenebis(4,6-di-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-butylbenzyl)isocyanurate, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-Trimethylbenzene, 1,3,5-tris[(3,5-di-tert-butyl-4-hydroxyphenyl)propionyloxyethyl]isocyanurate, tetrakis[methylene-3-(3',5'-tert-butyl-4'-hydroxyphenyl)propionate]methane, 2-tert-butyl-4-methyl-6-(2-acryloyloxy-3-tert-butyl-5-methylbenzyl)phenol, 3,9-bis[2-(3-tert-butyl-4-hydroxy-5-methylhydrocinnamoyloxy)-1,1-dimethylethyl]-2,4,8,10-tetraoxaspiro[5.5]undecane, triethylenediamine and 3-(3,5-dialkyl-4-hydroxyphenyl)propionic acid derivatives such as ethylene glycol bis[β-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionate], stearyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid amide, palmityl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid amide, myristyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid amide, and lauryl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid amide. From the viewpoint of further improving the thermal stability of the resin composition, among these, stearyl(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate, or tetrakis[methylene-3-(3',5'-tert-butyl-4'-hydroxyphenyl)propionate]methane is preferred, and tetrakis[methylene-3-(3',5'-tert-butyl-4'-hydroxyphenyl)propionate]methane is particularly preferred.

[0049] When the resin composition of this embodiment contains a phenolic antioxidant, the content of the phenolic antioxidant can be, for example, 0.001 to 10 parts by mass relative to 100 parts by mass of the synthetic resin. From the viewpoint of further improving the thermal stability of the resin composition, the content of the phenolic antioxidant is preferably 0.005 to 5 parts by mass, more preferably 0.01 to 3 parts by mass, even more preferably 0.03 to 1 part by mass, and even more preferably 0.05 to 0.5 parts by mass relative to 100 parts by mass of the synthetic resin.

[0050] When the resin composition of the present embodiment contains a phenolic antioxidant, the content of the phenolic antioxidant can be, for example, 1 to 10,000 parts by mass relative to 100 parts by mass of the compound represented by general formula (1). From the viewpoint of further improving the thermal stability of the resin composition, the content of the phenolic antioxidant is preferably 10 to 1,000 parts by mass, more preferably 20 to 500 parts by mass, even more preferably 25 to 400 parts by mass, and even more preferably 50 to 200 parts by mass relative to 100 parts by mass of the compound represented by general formula (1).

[0051] Furthermore, when the resin composition of the present embodiment contains a phenolic antioxidant, the content of the phenolic antioxidant can be, for example, 1 to 10,000 parts by mass relative to 100 parts by mass of the compound represented by general formula (2). From the viewpoint of further improving the thermal stability of the resin composition, the content of the phenolic antioxidant is preferably 10 to 1,000 parts by mass, more preferably 20 to 500 parts by mass, even more preferably 25 to 400 parts by mass, and even more preferably 50 to 200 parts by mass relative to 100 parts by mass of the compound represented by general formula (2).

[0052] The resin composition of the present embodiment preferably further contains an acid scavenger.

[0053] When the resin composition of this embodiment is heated and melted, a portion of the compound represented by general formula (2) is hydrolyzed, resulting in the generation of free phosphoric acid. This free phosphoric acid acts as a catalyst for the hydrolysis of the compound represented by general formula (2), thereby promoting the hydrolysis of the compound represented by general formula (2). Here, when the resin composition of this embodiment contains an acid scavenger, the free phosphoric acid generated when the resin composition is heated and melted is captured by the acid scavenger, thereby suppressing further hydrolysis of the compound represented by general formula (2). Due to the above-mentioned effects, when the resin composition of this embodiment contains an acid scavenger, the resin composition of this embodiment has even better thermal stability.

[0054] Examples of the acid scavenger include metal salts of organic acids such as metal salts of fatty acids and metal salts of aromatic carboxylic acids, and hydrotalcites.

[0055] Examples of fatty acid metal salts include metal salts of fatty acids having 12 to 20 carbon atoms and containing linear or branched fatty acid residues. Examples of metal ions constituting fatty acid metal salts include sodium ions, potassium ions, lithium ions, dihydroxyaluminum ions, calcium ions, zinc ions, barium ions, magnesium ions, and hydroxyaluminum ions. Of these, sodium ions, potassium ions, lithium ions, and calcium ions are more preferred, with sodium ions and calcium ions being even more preferred.Specific examples of fatty acid metal salts include sodium laurate, sodium myristate, sodium palmitate, sodium stearate, sodium oleate, sodium linoleate, sodium linolenate, sodium arachidate, sodium 12-hydroxystearate, potassium laurate, potassium myristate, potassium palmitate, potassium stearate, potassium oleate, potassium linoleate, potassium linolenate, potassium arachidate, potassium 12-hydroxystearate, lithium laurate, lithium myristate, lithium palmitate, lithium stearate, lithium oleate, lithium linoleate, lithium linolenate, lithium arachidate, lithium 12-hydroxystearate, calcium laurate, calcium myristate, calcium palmitate, calcium stearate, Examples include calcium oleate, calcium linoleate, calcium linolenate, calcium arachidate, and calcium 12-hydroxystearate. Of these, sodium myristate, sodium stearate, sodium 12-hydroxystearate, lithium myristate, lithium stearate, lithium 12-hydroxystearate, calcium myristate, calcium stearate, and calcium 12-hydroxystearate are preferred, sodium myristate, sodium stearate, sodium 12-hydroxystearate, calcium myristate, calcium stearate, and calcium 12-hydroxystearate are more preferred, calcium myristate, calcium stearate, and calcium 12-hydroxystearate are even more preferred, and calcium stearate is even more preferred.

[0056] Examples of the metal salt of an aromatic carboxylic acid include sodium salts, calcium salts, and lithium salts of aromatic carboxylic acids such as benzoic acid, phthalic acid, terephthalic acid, salicylic acid, etc. Among these, sodium benzoate, calcium benzoate, and lithium benzoate are preferred, with sodium benzoate being more preferred, from the viewpoint of further improving the thermal stability of the resin composition.

[0057] Hydrotalcites are known as natural or synthetic compounds and are complex salt compounds composed of magnesium, aluminum, hydroxyl groups, carbonate groups, and optional crystal water. Examples include compounds in which part of the magnesium or aluminum has been replaced with other metals such as alkali metals or zinc, and compounds in which the hydroxyl groups and carbonate groups have been replaced with other anionic groups. Hydrotalcites may be those in which the crystal water has been dehydrated, or may be those coated with a higher fatty acid such as stearic acid, a higher fatty acid metal salt such as an alkali metal salt of oleic acid, an organic sulfonic acid metal salt such as an alkali metal salt of dodecylbenzenesulfonic acid, a higher fatty acid amide, a higher fatty acid ester, or a wax. Hydrotalcites may be natural or synthetic. Examples of methods for synthesizing hydrotalcites include known methods described in JP-B Nos. 46-2280, 50-30039, 51-29129, JP-B No. 3-36839, JP-A Nos. 61-174270, and 5-179052. Hydrotalcites can be used without any restrictions on their crystal structure, crystal particles, etc.

[0058] When the resin composition of the present embodiment contains an acid scavenger, from the viewpoint of further improving the thermal stability of the resin composition, the acid scavenger preferably contains at least one selected from the group consisting of fatty acid metal salts and hydrotalcites, and more preferably contains hydrotalcites.

[0059] When the resin composition of this embodiment contains an acid scavenger, the content of the acid scavenger can be, for example, 0.001 to 10 parts by mass relative to 100 parts by mass of the synthetic resin. From the viewpoint of further improving the thermal stability of the resin composition, the content of the acid scavenger is preferably 0.002 to 1 part by mass, more preferably 0.003 to 0.5 parts by mass, even more preferably 0.005 to 0.1 parts by mass, and even more preferably 0.01 to 0.05 parts by mass relative to 100 parts by mass of the synthetic resin.

[0060] When the resin composition of the present embodiment contains an acid scavenger, the content of the acid scavenger can be, for example, 1 to 1,000 parts by mass relative to 100 parts by mass of the compound represented by general formula (1). From the viewpoint of further improving the thermal stability of the resin composition, the content of the acid scavenger is preferably 3 to 500 parts by mass, more preferably 5 to 200 parts by mass, even more preferably 10 to 100 parts by mass, and even more preferably 25 to 75 parts by mass relative to 100 parts by mass of the compound represented by general formula (1).

[0061] Furthermore, when the resin composition of this embodiment contains an acid scavenger, the content of the acid scavenger can be, for example, 1 to 1,000 parts by mass relative to 100 parts by mass of the compound represented by general formula (2). From the viewpoint of further improving the thermal stability of the resin composition, the content of the acid scavenger is preferably 3 to 500 parts by mass, more preferably 5 to 200 parts by mass, even more preferably 10 to 100 parts by mass, and even more preferably 25 to 75 parts by mass relative to 100 parts by mass of the compound represented by general formula (2).

[0062] Furthermore, when the resin composition of this embodiment contains a phenolic antioxidant and an acid scavenger, the content of the acid scavenger can be, for example, 1 to 1,000 parts by mass per 100 parts by mass of the phenolic antioxidant. From the viewpoint of further improving the thermal stability of the resin composition, the content of the acid scavenger is preferably 3 to 500 parts by mass, more preferably 5 to 200 parts by mass, even more preferably 10 to 100 parts by mass, and even more preferably 25 to 75 parts by mass per 100 parts by mass of the phenolic antioxidant.

[0063] The resin composition of this embodiment may further contain additives such as a nucleating agent, a phosphorus-based antioxidant (excluding the compounds represented by general formula (1) and the compounds represented by general formula (2)), a sulfur-based antioxidant, other antioxidants, a hindered amine compound, an ultraviolet absorber, a flame retardant, a flame retardant aid, a lubricant, a filler antistatic agent, a fluorescent brightener, a pigment, and a dye (hereinafter referred to as "other additives"). The content of the other additives relative to the synthetic resin can be appropriately set within a range that does not impair the effects of this embodiment.

[0064] From the viewpoint of improving the color tone of the resin composition of the present embodiment, it is preferable that the resin composition does not contain bis(3,4-dimethylbenzylidene)sorbitol, and it is preferable that the resin composition does not contain a nucleating agent made of a polyol derivative such as dibenzylidene sorbitol, bis(methylbenzylidene)sorbitol, bis(3,4-dimethylbenzylidene)sorbitol, bis(p-ethylbenzylidene)sorbitol, bis(dimethylbenzylidene)sorbitol, or 1,2,3-trideoxy-4,6:5,7-o-bis(4-propylbenzylidene)nonitol.

[0065] <Method for producing resin composition> The method for producing a resin composition of the present embodiment includes a blending step of mixing a synthetic resin, a compound represented by the general formula (1) above, and a compound represented by the general formula (2) above.

[0066] According to the method for producing a resin composition of this embodiment, a resin composition having excellent thermal stability can be produced.

[0067] The method for mixing the synthetic resin, the compound represented by general formula (1), the compound represented by general formula (2), and, if necessary, the phenolic antioxidant, the acid scavenger, and the other additives is not particularly limited, and examples thereof include a method in which the synthetic resin, the compound represented by general formula (1), the compound represented by general formula (2), and, if necessary, the phenolic antioxidant, the acid scavenger, and the other additives are added, and then mixed using a mixing device such as an FM mixer, a mill roll, a Banbury mixer, or a super mixer. Here, at least one of the components to be mixed with the synthetic resin may be added before or during polymerization of the synthetic resin monomer or oligomer, and the remaining components may be added to the resulting polymer.

[0068] In the blending step, recycled resin may be further mixed in addition to the above components.

[0069] Furthermore, in the blending step, after mixing the synthetic resin and each component, the resulting blend may be melt-kneaded using a melt-kneading device such as a single-screw extruder or a twin-screw extruder. Here, the melt-kneading temperature may be, for example, 160 to 260°C. In addition, in the blending step, the synthetic resin and each component may be mixed, the resulting blend may be melt-kneaded, and the melt-kneaded product obtained by melt-kneading may be granulated into a shape such as pellets using a granulating device such as a pelletizer.

[0070] <Molded Article> The molded article of this embodiment is obtained by molding the resin composition described above.

[0071] The molded article of this embodiment is produced from a resin composition having excellent thermal stability, and therefore has excellent properties such as color tone.

[0072] Examples of molded articles of this embodiment include injection molded articles, fibers, flat yarns, biaxially stretched films, uniaxially stretched films, unstretched films, sheets, thermoforming molded articles, extrusion blow molded articles, injection blow molded articles, injection stretch blow molded articles, profile extrusion molded articles, rotational molded articles, etc. More specific examples of molded articles of this embodiment include automobile exterior parts, automobile interior parts, housings, containers, piping, etc.

[0073] The method for molding the molded article of this embodiment is not particularly limited, and examples thereof include injection molding, extrusion molding, blow molding, rotational molding, vacuum molding, inflation molding, calendar molding, slush molding, dip molding, and thermoforming.

[0074] <Resin Additive Composition> The resin additive composition of the present embodiment contains a compound represented by the above general formula (1) and a compound represented by the above general formula (2).

[0075] The resin additive composition of this embodiment can impart excellent thermal stability to synthetic resins.

[0076] Examples of the compound represented by general formula (1) and the compound represented by general formula (2) contained in the resin additive composition of this embodiment include the same compounds as those contained in the resin composition of this embodiment described above.

[0077] The content of the compound represented by general formula (1) in the resin additive composition of this embodiment can be, for example, 1 to 99% by mass of the entire resin additive composition. From the viewpoint of imparting even better thermal stability to the synthetic resin, the content of the compound represented by general formula (1) is preferably 5 to 90% by mass, more preferably 15 to 75% by mass, and even more preferably 20 to 50% by mass of the entire resin additive composition.

[0078] The content of the compound represented by general formula (2) in the resin additive composition of this embodiment can be, for example, 1 to 99% by mass of the entire resin additive composition. From the viewpoint of imparting even better thermal stability to the synthetic resin, the content of the compound represented by general formula (2) is preferably 5 to 90% by mass, more preferably 15 to 75% by mass, and even more preferably 20 to 50% by mass of the entire resin additive composition.

[0079] Furthermore, the content of the compound represented by general formula (2) in the resin additive composition of this embodiment can be, for example, 1 to 10,000 parts by mass per 100 parts by mass of the compound represented by general formula (1). From the viewpoint of imparting even better thermal stability to the synthetic resin, the content of the compound represented by general formula (2) is preferably 10 to 1,000 parts by mass, more preferably 20 to 500 parts by mass, even more preferably 25 to 400 parts by mass, and even more preferably 50 to 200 parts by mass per 100 parts by mass of the compound represented by general formula (1).

[0080] The resin additive composition of the present embodiment preferably further contains a phenolic antioxidant. Here, examples of the phenolic antioxidant include the same as those exemplified as the phenolic antioxidant that may be contained in the resin composition of the present embodiment described above.

[0081] When the resin additive composition of this embodiment contains a phenolic antioxidant, when the resin additive composition of this embodiment is added to a synthetic resin, the phenolic antioxidant reinforces the action of the compound represented by general formula (1) in capturing peroxy radicals generated when the synthetic resin is heated and melted. As a result, when the resin additive composition of this embodiment contains a phenolic antioxidant, the resin additive composition can impart even better thermal stability to the synthetic resin.

[0082] When the resin additive composition of this embodiment contains a phenolic antioxidant, the content of the phenolic antioxidant in the resin additive composition can be, for example, 1 to 99 mass% of the entire resin additive composition. From the viewpoint of imparting even better thermal stability to the synthetic resin, the content of the phenolic antioxidant is preferably 5 to 90 mass%, more preferably 15 to 75 mass%, and even more preferably 20 to 50 mass% of the entire resin additive composition.

[0083] When the resin additive composition of the present embodiment contains a phenolic antioxidant, the content of the phenolic antioxidant can be, for example, 1 to 10,000 parts by mass relative to 100 parts by mass of the compound represented by general formula (1). From the viewpoint of imparting even better thermal stability to the synthetic resin, the content of the phenolic antioxidant is preferably 10 to 1,000 parts by mass, more preferably 20 to 500 parts by mass, even more preferably 25 to 400 parts by mass, and even more preferably 50 to 200 parts by mass relative to 100 parts by mass of the compound represented by general formula (1).

[0084] Furthermore, when the resin additive composition of the present embodiment contains a phenolic antioxidant, the content of the phenolic antioxidant can be, for example, 1 to 10,000 parts by mass relative to 100 parts by mass of the compound represented by general formula (2). From the viewpoint of imparting even better thermal stability to the synthetic resin, the content of the phenolic antioxidant is preferably 10 to 1,000 parts by mass, more preferably 20 to 500 parts by mass, even more preferably 25 to 400 parts by mass, and even more preferably 50 to 200 parts by mass relative to 100 parts by mass of the compound represented by general formula (2).

[0085] The resin additive composition of the present embodiment preferably further contains an acid scavenger. Examples of the acid scavenger include the same acid scavengers as those exemplified above as acid scavengers that may be contained in the resin composition of the present embodiment.

[0086] When a resin composition containing the resin additive composition of this embodiment is heated and melted, a portion of the compound represented by general formula (2) is hydrolyzed, resulting in the generation of free phosphoric acid. This free phosphoric acid acts as a catalyst for the hydrolysis of the compound represented by general formula (2), thereby promoting the hydrolysis of the compound represented by general formula (2). When the resin additive composition of this embodiment contains an acid scavenger, the free phosphoric acid generated when the resin composition containing the resin additive composition of this embodiment is heated and melted is captured by the acid scavenger, thereby suppressing further hydrolysis of the compound represented by general formula (2). Due to the above-mentioned effects, when the resin additive composition of this embodiment contains an acid scavenger, the resin additive composition can impart even better thermal stability to synthetic resins.

[0087] Furthermore, when the resin additive composition of this embodiment is heated, a portion of the compound represented by general formula (2) is hydrolyzed, resulting in the generation of free phosphoric acid. This free phosphoric acid acts as a catalyst for the hydrolysis of the compound represented by general formula (2), thereby promoting the hydrolysis of the compound represented by general formula (2). Here, when the resin additive composition of this embodiment contains an acid scavenger, the free phosphoric acid generated when the resin additive composition of this embodiment is heated is captured by the acid scavenger, resulting in the suppression of further hydrolysis of the compound represented by general formula (2). Due to the above-mentioned effects, when the resin additive composition of this embodiment contains an acid scavenger, the resin additive composition itself has excellent thermal stability.

[0088] When the resin additive composition of the present embodiment contains an acid scavenger, the content of the acid scavenger in the resin additive composition can be, for example, 1 to 99 mass% of the entire resin additive composition. From the viewpoint of imparting even better thermal stability to the synthetic resin, the content of the acid scavenger is preferably 3 to 50 mass%, more preferably 5 to 30 mass%, and even more preferably 10 to 25 mass% of the entire resin additive composition.

[0089] When the resin additive composition of the present embodiment contains an acid scavenger, the content of the acid scavenger can be, for example, 0.1 to 100 parts by mass relative to 100 parts by mass of the compound represented by general formula (1). From the viewpoint of imparting even better thermal stability to the synthetic resin, the content of the acid scavenger is preferably 0.5 to 50 parts by mass, more preferably 1 to 30 parts by mass, even more preferably 3 to 25 parts by mass, and even more preferably 5 to 15 parts by mass relative to 100 parts by mass of the compound represented by general formula (1).

[0090] Furthermore, when the resin additive composition of the present embodiment contains an acid scavenger, the content of the acid scavenger can be, for example, 0.1 to 100 parts by mass relative to 100 parts by mass of the compound represented by general formula (2). From the viewpoint of imparting even better thermal stability to the synthetic resin, the content of the acid scavenger is preferably 0.5 to 50 parts by mass, more preferably 1 to 30 parts by mass, even more preferably 3 to 25 parts by mass, and even more preferably 5 to 15 parts by mass relative to 100 parts by mass of the compound represented by general formula (2).

[0091] Furthermore, when the resin additive composition of the present embodiment contains a phenolic antioxidant and an acid scavenger, the content of the acid scavenger can be, for example, 0.1 to 100 parts by mass relative to 100 parts by mass of the phenolic antioxidant. From the viewpoint of imparting even better thermal stability to the synthetic resin, the content of the acid scavenger is preferably 0.5 to 50 parts by mass, more preferably 1 to 30 parts by mass, even more preferably 3 to 25 parts by mass, and even more preferably 5 to 15 parts by mass relative to 100 parts by mass of the phenolic antioxidant.

[0092] The resin additive composition of this embodiment may further contain other additives exemplified as those that may be contained in the resin composition described above. The content of the other additives in the resin additive composition can be appropriately set within a range that does not impair the effects of this embodiment.

[0093] <Method for Thermal Stabilization of Synthetic Resin> The method for thermal stabilization of a synthetic resin according to the present embodiment includes a blending step of mixing a synthetic resin, a compound represented by the general formula (1) above, and a compound represented by the general formula (2) above.

[0094] According to the method for thermal stabilization of a synthetic resin of this embodiment, excellent thermal stability can be imparted to the synthetic resin.

[0095] Further embodiments of the present invention include, for example, the following: [1] A resin composition comprising a synthetic resin, a compound represented by the following general formula (1), and a compound represented by the following general formula (2). (In general formula (1), R １ , R ２ , R ３ , R １１ , R １２ , R １３ , R ４ and R ５ each independently represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms which may have a substituent; X represents a single bond, a sulfur atom, or an alkanediyl group having 1 to 30 carbon atoms; A represents an alkylene group having 1 to 30 carbon atoms or a divalent group represented by *-C(=O)A'-; A' represents a single bond or an alkylene group having 1 to 30 carbon atoms; * represents a site bonding to an oxygen atom; at least one of Y and Z represents a hydroxyl group; and when only one of Y and Z is a hydroxyl group, the other represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms which may have a substituent. (In general formula (2), R ６ and R １６each independently represents an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms which may have a substituent.) [2] The resin composition according to [1], wherein the synthetic resin comprises a polyolefin-based resin, preferably a polypropylene-based resin. [3] The compound represented by general formula (2) is selected from the group consisting of bis(diisodecyl)pentaerythritol diphosphite, bis(tridecyl)pentaerythritol diphosphite, bis(octadecyl)pentaerythritol diphosphite, bis(nonylphenyl)pentaerythritol diphosphite, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, bis(2,4,6-tri-tert-butylphenyl)pentaerythritol diphosphite, bis(2,6-di at least one selected from the group consisting of bis(nonylphenyl)pentaerythritol diphosphite, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, bis(2,4,6-tri-tert-butylphenyl)pentaerythritol diphosphite, bis(2,6-di-t At least one selected from the group consisting of bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite and bis(2,4-dicumylphenyl)pentaerythritol diphosphite, more preferably bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, bis(2,4,6-tri-tert-butylphenyl)pentaerythritol diphosphite and bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol The resin composition according to [1] or [2], which contains at least one selected from the group consisting of bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite and bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite, more preferably at least one selected from the group consisting of bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite and bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite, and even more preferably bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite.[4] The resin composition according to any one of [1] to [3], further comprising a phenolic antioxidant. [5] The resin composition according to any one of [1] to [4], further comprising an acid scavenger. [6] The resin composition according to any one of [1] to [5], wherein the synthetic resin comprises a recycled resin. [7] The resin composition according to [6], wherein the recycled resin is an in-process recycled material, a post-consumer material, or a pre-consumer material, more preferably an in-process recycled material. [8] The resin composition according to [6] or [7], wherein the recycled resin content is 1 to 100% by mass, preferably 5 to 80% by mass, more preferably 10 to 70% by mass, even more preferably 20 to 60% by mass, and even more preferably 30 to 50% by mass, of the total synthetic resin. [9] A molded product obtained by molding the resin composition according to any one of [1] to [8].

[10] A method for producing a resin composition, comprising a blending step of mixing a synthetic resin, a compound represented by the following general formula (1), and a compound represented by the following general formula (2): (In general formula (1), R １ , R ２ , R ３ , R １１ , R １２ , R １３ , R ４ and R ５ each independently represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms which may have a substituent; X represents a single bond, a sulfur atom, or an alkanediyl group having 1 to 30 carbon atoms; A represents an alkylene group having 1 to 30 carbon atoms or a divalent group represented by *-C(=O)A'-; A' represents a single bond or an alkylene group having 1 to 30 carbon atoms; * represents a site bonding to an oxygen atom; at least one of Y and Z represents a hydroxyl group; and when only one of Y and Z is a hydroxyl group, the other represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms which may have a substituent. (In general formula (2), R ６ and R １６each independently represents an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms which may have a substituent.)

[11] The method for producing a resin composition according to

[10] , wherein the synthetic resin comprises a polyolefin-based resin, preferably a polypropylene-based resin.

[12] The compound represented by the general formula (2) is bis(diisodecyl)pentaerythritol diphosphite, bis(tridecyl)pentaerythritol diphosphite, bis(octadecyl)pentaerythritol diphosphite, bis(nonylphenyl)pentaerythritol diphosphite, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, bis(2,4,6-tri-tert-butylphenyl)pentaerythritol diphosphite, bis(2,6-di-t At least one selected from the group consisting of bis(nonylphenyl)pentaerythritol diphosphite, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, bis(2,4,6-tri-tert-butylphenyl)pentaerythritol diphosphite, bis(2,6-di-tert at least one selected from the group consisting of bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, bis(2,4,6-tri-tert-butylphenyl)pentaerythritol diphosphite, and bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite, more preferably bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, bis(2,4,6-tri-tert-butylphenyl)pentaerythritol diphosphite, and bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite;

[10] A method for producing a resin composition according to

[10] or

[11] , further comprising at least one selected from the group consisting of bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite and bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite, more preferably at least one selected from the group consisting of bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite and bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite, even more preferably bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite.

[13] A method for producing a resin composition according to any one of

[10] to

[12] , further comprising a phenolic antioxidant.

[14] A method for producing a resin composition according to any one of

[10] to

[13] , further comprising an acid scavenger.

[15] A method for producing a resin composition according to any one of

[10] to

[14] , wherein the synthetic resin comprises a recycled resin.

[16] A method for producing a resin composition according to

[15] , wherein the recycled resin is an in-process recycled material, a post-consumer material, or a pre-consumer material, more preferably an in-process recycled material.

[17] A method for producing a resin composition according to

[15] or

[16] , wherein the content of the recycled resin is 1 to 100% by mass, preferably 5 to 80% by mass, more preferably 10 to 70% by mass, even more preferably 20 to 60% by mass, and still more preferably 30 to 50% by mass, of the total synthetic resin.

[18] A resin additive composition comprising a compound represented by the following general formula (1), and a compound represented by the following general formula (2): (In general formula (1), R １ , R ２ , R ３ , R １１ , R １２ , R １３ , R ４ and R ５ each independently represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms which may have a substituent; X represents a single bond, a sulfur atom, or an alkanediyl group having 1 to 30 carbon atoms; A represents an alkylene group having 1 to 30 carbon atoms or a divalent group represented by *-C(=O)A'-; A' represents a single bond or an alkylene group having 1 to 30 carbon atoms; * represents a site bonding to an oxygen atom; at least one of Y and Z represents a hydroxyl group; and when only one of Y and Z is a hydroxyl group, the other represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms which may have a substituent. (In general formula (2), R ６ and R １６each independently represents an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms which may have a substituent.)

[19] The resin additive composition according to

[18] , which is used for a synthetic resin, preferably a synthetic resin containing a polyolefin-based resin, more preferably a synthetic resin containing a polypropylene-based resin.

[20] The resin additive composition according to

[19] , wherein the synthetic resin contains a recycled resin.

[21] The resin additive composition according to

[20] , wherein the recycled resin is an in-process recycled material, a post-consumer material, or a pre-consumer material, more preferably an in-process recycled material.

[22] The resin additive composition according to

[20] or

[21] , wherein the content of the recycled resin is 1 to 100% by mass, preferably 5 to 80% by mass, more preferably 10 to 70% by mass, even more preferably 20 to 60% by mass, and even more preferably 30 to 50% by mass of the total synthetic resin.

[23] The compound represented by the general formula (2) is bis(diisodecyl)pentaerythritol diphosphite, bis(tridecyl)pentaerythritol diphosphite, bis(octadecyl)pentaerythritol diphosphite, bis(nonylphenyl)pentaerythritol diphosphite, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, bis(2,4,6-tri-tert-butylphenyl)pentaerythritol diphosphite, bis(2,6-di-t at least one selected from the group consisting of bis(nonylphenyl)pentaerythritol diphosphite, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, bis(2,4,6-tri-tert-butylphenyl)pentaerythritol diphosphite, bis(2,6-di-tert-butylphenyl)pentaerythritol diphosphite, at least one selected from the group consisting of bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite and bis(2,4-dicumylphenyl)pentaerythritol diphosphite, more preferably bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, bis(2,4,6-tri-tert-butylphenyl)pentaerythritol diphosphite and bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite; The resin additive composition according to any one of

[18] to

[22] , further comprising at least one selected from the group consisting of bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite and bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite, more preferably at least one selected from the group consisting of bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite and bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite, even more preferably bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite.

[24] The resin additive composition according to any one of

[18] to

[23] , further comprising a phenolic antioxidant.

[25] The resin additive composition according to any one of

[18] to

[24] , further comprising an acid scavenger.

[26] A method for thermal stabilization of a synthetic resin, comprising a blending step of mixing a synthetic resin with a compound represented by the following general formula (1), and a compound represented by the following general formula (2): (In general formula (1), R １ , R ２ , R ３ , R １１ , R １２ , R １３ , R ４ and R ５ each independently represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms which may have a substituent; X represents a single bond, a sulfur atom, or an alkanediyl group having 1 to 30 carbon atoms; A represents an alkylene group having 1 to 30 carbon atoms or a divalent group represented by *-C(=O)A'-; A' represents a single bond or an alkylene group having 1 to 30 carbon atoms; * represents a site bonding to an oxygen atom; at least one of Y and Z represents a hydroxyl group; and when only one of Y and Z is a hydroxyl group, the other represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms which may have a substituent. (In general formula (2), R ６ and R １６ each independently represents an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms which may have a substituent.)

[27] A heat stabilizer for use in the resin additive composition according to any one of items

[18] to

[25] , the heat stabilizer comprising a compound represented by the following general formula (1): (In general formula (1), R １ , R ２ , R ３ , R １１ , R １２ , R １３ , R ４ and R ５each independently represent a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms which may have a substituent; X represents a single bond, a sulfur atom, or an alkanediyl group having 1 to 30 carbon atoms; A represents an alkylene group having 1 to 30 carbon atoms or a divalent group represented by *-C(=O)A'-; A' represents a single bond or an alkylene group having 1 to 30 carbon atoms; * represents a site bonding to an oxygen atom; at least one of Y and Z represents a hydroxyl group; and when only one of Y and Z is a hydroxyl group, the other represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms which may have a substituent.)

[28] A heat stabilizer for use in the resin additive composition according to any one of items

[18] to

[25] , comprising a compound represented by the following general formula (2): (In general formula (2), R ６ and R １６ each independently represents an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms which may have a substituent.

[0096] The present invention will be explained in more detail below by way of examples, but the present invention is not limited to the following examples in any way.

[0097] The synthetic resins, compounds represented by general formula (1), compounds represented by general formula (2), phenolic antioxidants and acid scavengers used in the present examples are as follows: [Synthetic Resins] Synthetic Resin-1: Homopolypropylene (MFR 3.0 g / 10 min measured in accordance with ISO 1133 at a resin temperature of 230°C) [Compounds Represented by General Formula (1)] Compound 1-1: 2,4,8,10-tetra-t-butyl-6-[3-(3-methyl-4-hydroxy-5-t-butylphenyl)propoxy]dibenzo[d,f][1,3,2]dioxaphosphepine (Sumitomo Chemical Co., Ltd., Sumilizer GP) [Compounds Represented by General Formula (2)] Compound 2-1: bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite (ADEKA Corporation, Adeka STAB PEP-36) [Comparative Compounds] Comparative Compound-1: Tris(2,4-di-tert-butylphenyl)phosphite (ADEKA Corporation, Adeka STAB 2112) [Phenol-based antioxidants] Antioxidant-1: tetrakis[methylene-3-(3',5'-tert-butyl-4'-hydroxyphenyl)propionate]methane (ADEKA CORPORATION, Adekastab AO-60) [Acid scavenger] Acid scavenger-1: hydrotalcite (Kyowa Chemical Industry Co., Ltd., DHT-4V)

[0098] (Examples 1 and 2 and Comparative Example 1) <Preparation of Resin Additive Compositions> The compound represented by general formula (1), the compound represented by general formula (2), the comparative compound, the phenolic antioxidant, and the acid scavenger were blended in the amounts shown in Table 1 below, and mixed for 30 minutes using a rocking mixer (RM-150, manufactured by Aichi Electric Co., Ltd.) to prepare resin additive composition-1, resin additive composition-2, and resin additive composition-3. In Table 1, the blending amount of each component is expressed in parts by mass.

[0099]

[0100] <Preparation of Resin Composition> The synthetic resin, resin additive composition, and acid scavenger were blended in the amounts shown in Table 2 below and mixed for 30 minutes using a rocking mixer (RM-150, manufactured by Aichi Electric Co., Ltd.). In Table 2, the blending amount of each component is expressed in parts by mass. The mixture thus obtained was charged into a twin-screw extruder (TEX28V, manufactured by The Japan Steel Works, Ltd.), melt-kneaded at a melt temperature of 200°C and a screw speed of 150 rpm, and then granulated to obtain resin pellets. The resin pellets thus obtained were dried at 60°C for 8 hours to obtain the resin compositions of Examples 1 and 2 and Comparative Example 1. In Table 2, the blending amount of each component is expressed in parts by mass.

[0101]

[0102] The amounts of the synthetic resin, compound represented by general formula (1), compound represented by general formula (2), phenolic antioxidant, and acid scavenger contained in the resin compositions of Examples 1 and 2 and Comparative Example 1 are as shown in Table 3. In Table 3, the blending amount of each component is expressed in parts by mass.

[0103]

[0104] <Evaluation of Properties> The resin compositions of Examples 1 and 2 and Comparative Example 1 obtained as described above were subjected to the following operations (A) to (E).

[0105] Procedure (A): The resin compositions of Examples 1 and 2 and Comparative Example 1 (hereinafter referred to as "PASS0") were charged into a twin-screw extruder (TEX28V manufactured by The Japan Steel Works, Ltd.), melt-kneaded at a melt temperature of 230°C and a screw speed of 150 rpm, and granulated to obtain resin pellets, which were then dried at 60°C for 8 hours. Hereinafter, the resin composition thus obtained will be referred to as "PASS1".

[0106] Procedure (B): PASS0 and PASS1 were blended in a mass ratio of 1:1 and mixed for 30 minutes using a rocking mixer (RM-150 manufactured by Aichi Electric Co., Ltd.), and the resulting mixture was fed into a twin-screw extruder (TEX28V manufactured by The Japan Steel Works, Ltd.), melt-kneaded at a melt temperature of 230°C and a screw speed of 150 rpm, and granulated to obtain resin pellets, which were then dried at 60°C for 8 hours. Hereinafter, the resin composition thus obtained will be referred to as "PASS2".

[0107] Procedure (C): PASS0 and PASS2 were blended in a mass ratio of 1:1 and mixed for 30 minutes using a rocking mixer (RM-150 manufactured by Aichi Electric Co., Ltd.), and the resulting mixture was fed into a twin-screw extruder (TEX28V manufactured by The Japan Steel Works, Ltd.), melt-kneaded at a melt temperature of 230°C and a screw speed of 150 rpm, and granulated to obtain resin pellets, which were then dried at 60°C for 8 hours. Hereinafter, the resin composition thus obtained will be referred to as "PASS3".

[0108] Procedure (D): PASS0 and PASS3 were blended in a mass ratio of 1:1 and mixed for 30 minutes using a rocking mixer (RM-150 manufactured by Aichi Electric Co., Ltd.), and the resulting mixture was fed into a twin-screw extruder (TEX28V manufactured by The Japan Steel Works, Ltd.), melt-kneaded at a melt temperature of 230°C and a screw speed of 150 rpm, and granulated to obtain resin pellets, which were then dried at 60°C for 8 hours. Hereinafter, the resin composition thus obtained will be referred to as "PASS4".

[0109] Procedure (E): PASS0 and PASS4 were blended in a mass ratio of 1:1 and mixed for 30 minutes using a rocking mixer (RM-150 manufactured by Aichi Electric Co., Ltd.), and the resulting mixture was fed into a twin-screw extruder (TEX28V manufactured by The Japan Steel Works, Ltd.), melt-kneaded at a melt temperature of 230°C and a screw speed of 150 rpm, and granulated to obtain resin pellets, which were then dried at 60°C for 8 hours. Hereinafter, the resin composition thus obtained will be referred to as "PASS5".

[0110] The MFR of PASS5 was measured at a resin temperature of 230°C in accordance with ISO 1133 and used as an index of molecular weight reduction due to heat. The YI of PASS5 was measured in accordance with JIS K 7373 and used as an index of coloration due to heat. The MFR and YI values ​​thus measured are shown in Table 2.

[0111] The results shown in Table 2 indicate that the resin compositions of Examples 1 and 2 are more inhibited from decreasing in molecular weight and from discoloring due to heat than the resin composition of Comparative Example 1.

[0112] From the above, it was confirmed that the resin composition of the present invention has excellent thermal stability.

Claims

1. A resin composition comprising a synthetic resin, a compound represented by the following general formula (1), and a compound represented by the following general formula (2): (In general formula (1), R １ , R ２ , R ３ , R １１ , R １２ , R １３ , R ４ and R ５ each independently represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms which may have a substituent; X represents a single bond, a sulfur atom, or an alkanediyl group having 1 to 30 carbon atoms; A represents an alkylene group having 1 to 30 carbon atoms or a divalent group represented by *-C(=O)A'-; A' represents a single bond or an alkylene group having 1 to 30 carbon atoms; * represents a site bonding to an oxygen atom; at least one of Y and Z represents a hydroxyl group; and when only one of Y and Z is a hydroxyl group, the other represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms which may have a substituent. (In general formula (2), R ６ and R １６ each independently represents an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms which may have a substituent.

2. The resin composition according to claim 1, further comprising a phenolic antioxidant (excluding the compound represented by the general formula (1)).

3. The resin composition according to claim 1, further comprising an acid scavenger.

4. The resin composition according to claim 1, wherein the synthetic resin comprises a recycled resin.

5. A molded article obtained by molding the resin composition according to any one of claims 1 to 4.

6. A method for producing a resin composition, comprising a compounding step of mixing a synthetic resin, a compound represented by the following general formula (1), and a compound represented by the following general formula (2): (In general formula (1), R １ , R ２ , R ３ , R １１ , R １２ , R １３ , R ４ and R ５ each independently represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms which may have a substituent; X represents a single bond, a sulfur atom, or an alkanediyl group having 1 to 30 carbon atoms; A represents an alkylene group having 1 to 30 carbon atoms or a divalent group represented by *-C(=O)A'-; A' represents a single bond or an alkylene group having 1 to 30 carbon atoms; * represents a site bonding to an oxygen atom; at least one of Y and Z represents a hydroxyl group; and when only one of Y and Z is a hydroxyl group, the other represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms which may have a substituent. (In general formula (2), R ６ and R １６ each independently represents an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms which may have a substituent.

7. A resin additive composition comprising: a compound represented by the following general formula (1); and a compound represented by the following general formula (2): (In general formula (1), R １ , R ２ , R ３ , R １１ , R １２ , R １３ , R ４ and R ５ each independently represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms which may have a substituent; X represents a single bond, a sulfur atom, or an alkanediyl group having 1 to 30 carbon atoms; A represents an alkylene group having 1 to 30 carbon atoms or a divalent group represented by *-C(=O)A'-; A' represents a single bond or an alkylene group having 1 to 30 carbon atoms; * represents a site bonding to an oxygen atom; at least one of Y and Z represents a hydroxyl group; and when only one of Y and Z is a hydroxyl group, the other represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms which may have a substituent. (In general formula (2), R ６ and R １６ each independently represents an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms which may have a substituent.

8. A method for thermal stabilization of a synthetic resin, comprising a blending step of mixing a synthetic resin with a compound represented by the following general formula (1), and a compound represented by the following general formula (2): (In general formula (1), R １ , R ２ , R ３ , R １１ , R １２ , R １３ , R ４ and R ５ each independently represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms which may have a substituent; X represents a single bond, a sulfur atom, or an alkanediyl group having 1 to 30 carbon atoms; A represents an alkylene group having 1 to 30 carbon atoms or a divalent group represented by *-C(=O)A'-; A' represents a single bond or an alkylene group having 1 to 30 carbon atoms; * represents a site bonding to an oxygen atom; at least one of Y and Z represents a hydroxyl group; and when only one of Y and Z is a hydroxyl group, the other represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms which may have a substituent. (In general formula (2), R ６ and R １６ each independently represents an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms which may have a substituent.

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