Method for improving transparency of synthetic resin

Abstract

To provide a synthetic resin composition containing a novel nucleating agent that can impart excellent transparency to a synthetic resin, a molded article thereof, a method for producing the synthetic resin composition, and a method for improving transparency of a synthetic resin.SOLUTION: A synthetic resin composition comprises a synthetic resin and a nucleating agent, where the synthetic resin includes a polyolefin resin (excluding halogen-containing resins), the nucleating agent includes one or more triazine compounds represented by the general formula (1) in the figure, and the content of the nucleating agent is 0.001 to 10 pts.mass per 100 pts.mass of the synthetic resin.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a synthetic resin composition, a molded article thereof, a method for producing a synthetic resin composition, and a method for improving the transparency of a synthetic resin, and more particularly to a synthetic resin composition containing a novel nucleating agent that can impart excellent transparency to a synthetic resin, a molded article thereof, a method for producing a synthetic resin composition, and a method for improving the transparency of a synthetic resin. [Background technology]

[0002] Synthetic resins, particularly polyolefin resins, have advantages such as excellent moldability, heat resistance, mechanical properties, and low specific gravity, and are widely used for films, sheets, and various molded products (structural parts, etc.). However, although polyolefin resins themselves generally have excellent physical properties, their applications have been limited in some cases because the inherent excellent performance of the resins cannot be fully realized.

[0003] This drawback is due to the crystallinity of polyolefin resins. In order to improve the crystallinity of polyolefin resins and thereby enhance the transparency of the resins, various nucleating agents are widely used.

[0004] Examples of such nucleating agents include metal salts of carboxylic acids such as sodium benzoate, aluminum 4-tert-butylbenzoate, sodium adipate, and disodium bicyclo[2.2.1]heptane-2,3-dicarboxylate; metal salts of phosphates such as sodium bis(4-tert-butylphenyl)phosphate, sodium-2,2'-methylenebis(4,6-di-tert-butylphenyl)phosphate, and lithium-2,2'-methylenebis(4,6-di-tert-butylphenyl)phosphate; and polyhydric alcohol derivatives such as dibenzylidene sorbitol, bis(methylbenzylidene)sorbitol, and bis(dimethylbenzylidene)sorbitol.

[0005] Patent Document 1 proposes a trisamide compound as a nucleating agent for reducing haze in polymers. Patent Document 2 proposes a trisaryloxytriazine compound as a stabilizer for improving the thermal stability of halogen-containing resins such as vinyl chloride resins. Patent Document 3 proposes a trisaryloxytriazine compound as a flow improver for synthetic resins. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Special Publication No. 2006-518402 [Patent Document 2] Japanese Patent Application Publication No. 54-4950 [Patent Document 3] Japanese Patent Publication No. 14261 / 1983 Summary of the Invention [Problem to be solved by the invention]

[0007] However, the nucleating agent proposed in Patent Document 1 does not have sufficient performance as a nucleating agent for synthetic resins, and the improvement in optical properties such as transparency is not satisfactory. Moreover, the trisaryloxytriazine compound proposed in Patent Document 2 and the trisaryloxytriazine compound proposed in Patent Document 3 have not been investigated as nucleating agents for synthetic resins at present.

[0008] Therefore, an object of the present invention is to provide a synthetic resin composition containing a novel nucleating agent that can impart excellent transparency to a synthetic resin, a molded article thereof, a method for producing the synthetic resin composition, and a method for improving the transparency of a synthetic resin. [Means for solving the problem]

[0009] As a result of extensive research into solving the above problems, the present inventors have found that a triazine compound having a predetermined structure serves as an excellent nucleating agent for synthetic resins, and that use of this compound can solve the above problems, thereby completing the present invention.

[0010] That is, the nucleating agent of the present invention is represented by the following general formula (1): The present invention is characterized in that it contains one or more triazine compounds represented by the general formula (1), wherein Ar 1 , Ar 2 and Ar 3 each independently represents an unsubstituted phenyl group or a substituted phenyl group.

[0011] In the nucleating agent of the present invention, the number of substituents in the substituted phenyl group in the general formula (1) is preferably 1, and in this case, the position of the substituent in the substituted phenyl group in the general formula (1) is preferably the para position. 1 , Ar 2 and Ar 3 In addition, it is also preferable that all of the Ar 1 and Ar 2 are the same group, and Ar 3 Ar 1 and Ar 2 In this case, Ar in the general formula (1) may be a group different from 1 and Ar 2 is preferably an unsubstituted phenyl group. 1 , Ar 2 and Ar 3 may all be phenyl groups having a substituent, and in this case, Ar 1 and Ar 2 The substituents of Ar 3 The substituents of Ar 1 and Ar 2Furthermore, it is also preferable that at least one of the phenyl groups having a substituent in the general formula (1) has a substituent having a carbonyl group in the structure, and Ar 3 However, those having a substituent with a carbonyl group in the structure are preferred.

[0012] The synthetic resin composition of the present invention is characterized by containing a synthetic resin and one or more nucleating agents of the present invention.

[0013] In the synthetic resin composition of the present invention, the synthetic resin is preferably a polyolefin resin.

[0014] The molded article of the present invention is characterized by being obtained from the synthetic resin composition of the present invention. [Effects of the Invention]

[0015] According to the present invention, it is possible to provide a synthetic resin composition containing a novel nucleating agent that can impart excellent transparency to a synthetic resin, a molded article thereof, a method for producing a synthetic resin composition, and a method for improving the transparency of a synthetic resin. DETAILED DESCRIPTION OF THE INVENTION

[0016] Hereinafter, embodiments of the present invention will be described in detail. The nucleating agent of the present invention contains one or more triazine compounds represented by the following general formula (1).

[0017] TIFF2025169326000002.tif54164

[0018] Here, in the general formula (1), Ar 1 , Ar 2 and Ar 3 each independently represents an unsubstituted phenyl group or a substituted phenyl group.

[0019] Ar in general formula (1) 1 , Ar 2 and Ar3 Examples of the substituents on the group include a halogen atom, a hydroxy group, a carboxy group, an amino group, an aminocarbonyl group (also referred to as a carbamoyl group), a nitro group, a cyano group, a thiol group, a sulfo group, a sulfonamido group, a formyl group, an alkyl group of 1 to 20 carbon atoms which may have a substituent, an aryl group of 6 to 20 carbon atoms which may have a substituent, an arylalkyl group of 7 to 20 carbon atoms which may have a substituent, an alkoxy group of 1 to 20 carbon atoms which may have a substituent, an aryloxy group of 6 to 20 carbon atoms which may have a substituent, an alkylthio group of 1 to 20 carbon atoms which may have a substituent, an alkylamino group of 1 to 20 carbon atoms which may have a substituent, a dialkylamino group of 2 to 20 carbon atoms which may have a substituent, an arylamino group of 6 to 20 carbon atoms which may have a substituent, a diarylamino group of 12 to 20 carbon atoms which may have a substituent, an alkylarylamino group of 7 to 20 carbon atoms which may have a substituent, and an alkylcarbonyl group of 2 to 20 carbon atoms which may have a substituent. Examples of the alkylaminocarbonyl group include an arylcarbonyl group having 7 to 20 carbon atoms which may have a substituent, an arylcarbonyloxy group having 2 to 20 carbon atoms which may have a substituent, an arylcarbonyloxy group having 7 to 20 carbon atoms which may have a substituent, an alkoxycarbonyl group having 2 to 20 carbon atoms which may have a substituent, an aryloxycarbonyl group having 7 to 20 carbon atoms which may have a substituent, an alkylaminocarbonyl group having 2 to 20 carbon atoms which may have a substituent, an arylaminocarbonyl group having 7 to 20 carbon atoms which may have a substituent, a dialkylaminocarbonyl group having 3 to 20 carbon atoms which may have a substituent, a diarylaminocarbonyl group having 13 to 20 carbon atoms which may have a substituent, an alkylarylaminocarbonyl group having 8 to 20 carbon atoms which may have a substituent, an alkylcarbonylamino group having 2 to 20 carbon atoms which may have a substituent, an arylcarbonylamino group having 7 to 20 carbon atoms which may have a substituent, and a heterocyclic group having 2 to 20 carbon atoms which may have a substituent. In addition, the carboxy group and the sulfo group may form a salt. In addition, Ar 1 , Ar2 and Ar 3 In the case where the substituents of the group (I) may have a substituent, examples of the substituents include the following.

[0020] For example, alkyl groups such as methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, isoamyl, tert-amyl, cyclopentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, bicyclohexyl, 1-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, isoheptyl, tert-heptyl, n-octyl, isooctyl, tert-octyl, 2-ethylhexyl, nonyl, isononyl, and decyl; Alkoxy groups such as methyloxy, ethyloxy, propyloxy, isopropyloxy, butyloxy, sec-butyloxy, tert-butyloxy, isobutyloxy, amyloxy, isoamyloxy, tert-amyloxy, hexyloxy, cyclohexyloxy, heptyloxy, isoheptyloxy, tert-heptyloxy, n-octyloxy, isooctyloxy, tert-octyloxy, 2-ethylhexyloxy, nonyloxy, and decyloxy; alkylthio groups such as methylthio, ethylthio, propylthio, isopropylthio, butylthio, sec-butylthio, tert-butylthio, isobutylthio, amylthio, isoamylthio, tert-amylthio, hexylthio, cyclohexylthio, heptylthio, isoheptylthio, tert-heptylthio, n-octylthio, isooctylthio, tert-octylthio, and 2-ethylhexylthio; alkenyl groups such as vinyl, 1-methylethenyl, 2-methylethenyl, 2-propenyl, 1-methyl-3-propenyl, 3-butenyl, 1-methyl-3-butenyl, isobutenyl, 3-pentenyl, 4-hexenyl, cyclohexenyl, bicyclohexenyl, heptenyl, octenyl, decenyl, pentadecenyl, eicosenyl, and tricosenyl; arylalkyl groups such as benzyl, phenethyl, diphenylmethyl, triphenylmethyl, styryl, and cinnamyl; aryl groups such as phenyl and naphthyl; aryloxy groups such as phenoxy and naphthyloxy; arylthio groups such as phenylthio and naphthylthio; heterocyclic groups such as pyridyl, pyrimidyl, pyridazyl, piperidyl, pyranyl, pyrazolyl, triazyl, pyrrolyl, quinolyl, isoquinolyl, imidazolyl, benzimidazolyl, triazolyl, furyl, furanyl, benzofuranyl, thienyl, thiophenyl, benzothiophenyl, thiadiazolyl, thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl, isothiazolyl, isoxazolyl, indolyl, 2-pyrrolidinon-1-yl, 2-piperidon-1-yl, 2,4-dioxyimidazolidin-3-yl, and 2,4-dioxyoxazolidin-3-yl; Halogen atoms such as fluorine, chlorine, bromine, and iodine; acyl groups such as acetyl, 2-chloroacetyl, propionyl, octanoyl, acryloyl, methacryloyl, phenylcarbonyl (benzoyl), phthaloyl, 4-trifluoromethylbenzoyl, pivaloyl, salicyloyl, oxaloyl, stearoyl, methoxycarbonyl, ethoxycarbonyl, t-butoxycarbonyl, n-octadecyloxycarbonyl, and carbamoyl; acyloxy groups such as acetyloxy and benzoyloxy; Substituted or unsubstituted amino groups such as amino, ethylamino, dimethylamino, diethylamino, butylamino, cyclopentylamino, 2-ethylhexylamino, dodecylamino, anilino, chlorophenylamino, toluidino, anisidino, N-methyl-anilino, diphenylamino, naphthylamino, 2-pyridylamino, methoxycarbonylamino, phenoxycarbonylamino, acetylamino, benzoylamino, formylamino, pivaloylamino, lauroylamino, carbamoylamino, N,N-dimethylaminocarbonylamino, N,N-diethylaminocarbonylamino, morpholinocarbonylamino, methoxycarbonylamino, ethoxycarbonylamino, t-butoxycarbonylamino, n-octadecyloxycarbonylamino, N-methyl-methoxycarbonylamino, phenoxycarbonylamino, sulfamoylamino, N,N-dimethylaminosulfonylamino, methylsulfonylamino, butylsulfonylamino, and phenylsulfonylamino; Examples of the sulfonamide group include sulfonyl, carboxy, cyano, sulfo, hydroxyl, nitro, mercapto, imido, carbamoyl, and sulfonamide groups, which may be further substituted. The carboxy and sulfo groups may form salts.

[0021] Ar in general formula (1) 1 , Ar 2 and Ar 3 Examples of the halogen atom in the substituent include fluorine, chlorine, bromine and iodine.

[0022] Ar in general formula (1) 1 , Ar 2 and Ar 3Examples of the alkyl group having 1 to 20 carbon atoms which may have a substituent include unsubstituted alkyl groups having 1 to 20 carbon atoms such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-amyl, 1,2-dimethylpropyl, n-hexyl, cyclohexyl, 1,3-dimethylbutyl, 1-isopropylpropyl, 1,2-dimethylbutyl, n-heptyl, 2-heptyl, 1,4-dimethylpentyl, tert-heptyl, 2-methyl-1-isopropylpropyl, and 1-ethyl-3-methyl Examples of the alkyl group include butyl, n-octyl, tert-octyl, 2-ethylhexyl, 2-methylhexyl, 2-propylhexyl, n-nonyl, isononyl, n-decyl, isodecyl, n-undecyl, isoundecyl, n-dodecyl, isododecyl, n-tridecyl, isotridecyl, n-tetradecyl, isotetradecyl, n-pentadecyl, isopentadecyl, n-hexadecyl, isohexadecyl, n-heptadecyl, isoheptadecyl, n-octadecyl, isooctadecyl, n-nonadecyl, isononadecyl, n-icosyl, isoicosyl, cyclopentyl, cyclohexyl, cyclooctyl, and cyclododecyl. The alkylene portion of the alkyl group may be interrupted 1 to 5 times by unsaturated bonds, ether bonds, thioether bonds, ester bonds, thioester bonds, amide bonds, or urethane bonds.

[0023] Ar in general formula (1) 1 , Ar 2 and Ar 3 Examples of the aryl group having 6 to 20 carbon atoms which may have a substituent include phenyl, p-methylphenyl, o-methylphenyl, p-tert-butylphenyl, p-methoxyphenyl, p-chlorophenyl, p-nitrophenyl, p-cyanophenyl, o-biphenylyl, m-biphenylyl, p-biphenylyl, α-naphthyl, β-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, and 9-phenanthryl.

[0024] Ar in general formula (1) 1 , Ar 2 and Ar 3 Examples of the arylalkyl group having 7 to 20 carbon atoms which may have a substituent include benzyl, phenethyl, 2-phenylpropan-2-yl, styryl, cinnamyl, diphenylmethyl, and triphenylmethyl.

[0025] Ar in general formula (1) 1 , Ar 2 and Ar 3 Examples of the alkoxy group having 1 to 20 carbon atoms which may have a substituent include those corresponding to the alkyl groups described above, and specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy, isopentyloxy, neopentyloxy, 1,2-dimethylpropoxy, n-hexyloxy, cyclohexyloxy, 1,3-dimethylbutoxy, and 1-isopropylpropoxy.

[0026] Ar in general formula (1) 1 , Ar 2 and Ar 3 Examples of the aryloxy group having 6 to 20 carbon atoms which may have a substituent include those corresponding to the above-mentioned aryl group, and specific examples include phenoxy, naphthyloxy, p-methylphenoxy, o-methylphenoxy, p-tert-butylphenoxy, p-methoxyphenoxy, p-chlorophenoxy, p-nitrophenoxy, p-cyanophenoxy, o-biphenylyloxy, m-biphenylyloxy, p-biphenylyloxy, α-naphthyloxy, β-naphthyloxy, 1-anthryloxy, 2-anthryloxy, 9-anthryloxy, 1-phenanthryloxy, 2-phenanthryloxy, 3-phenanthryloxy, 4-phenanthryloxy, and 9-phenanthryloxy.

[0027] Ar in general formula (1)1 , Ar 2 and Ar 3 Examples of the alkylthio group having 1 to 20 carbon atoms, which may have a substituent, include those corresponding to the alkyl groups described above, and specific examples include a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, an n-butylthio group, an isobutylthio group, a sec-butylthio group, and a tert-butylthio group.

[0028] Ar in general formula (1) 1 , Ar 2 and Ar 3 Examples of the alkylamino group having 1 to 20 carbon atoms, which may have a substituent, include those corresponding to the above alkyl groups, and specific examples include methylamino, ethylamino, n-propylamino, isopropylamino, cyclopropylamino, n-butylamino, isobutylamino, sec-butylamino, tert-butylamino, cyclobutylamino, 1-pentylamino, 2-pentylamino, 3-pentylamino, isopentylamino, neopentylamino, tert-pentylamino, cyclopentylamino, 1-hexylamino, 2-hexylamino, 3-hexylamino, cyclohexylamino, 1-methyl-n-pentylamino, 1,1,2-trimethyl-n-propylamino, 1,2,2-trimethyl-n-propylamino, 3,3-dimethyl-n-butylamino, etc.

[0029] Ar in general formula (1) 1 , Ar 2 and Ar 3Examples of the dialkylamino group having 2 to 20 carbon atoms, which may have a substituent, include those corresponding to the above alkyl groups, such as dimethylamino, diethylamino, di-n-propylamino, diisopropylamino, dicyclopropylamino, di-n-butylamino, diisobutylamino, di-sec-butylamino, di-tert-butylamino, dicyclobutylamino, di-1-pentylamino, di-2-pentylamino, di-3-pentylamino, diisopentylamino, di-neopentylamino, di-tert-pentylamino, dicyclopentylamino, di-1-hexylamino, di-2-hexylamino, di-3-hexylamino, dicyclohexylamino, di-(1-methyl-n-pentyl)amino, di-(1,1,2-trimethyl-n-propyl)amino, di-(1,2,2-trimethyl-n-propyl)amino, di-(3,3-dimethyl-n-butyl)amino, methyl(ethyl)amino, methyl(n-propyl)amino, methyl(isopropyl)amino, methyl(cyclopropyl)amino, methyl(n-butyl)amino, methyl(isobutyl)amino, methyl(sec-butyl)amino, methyl(tert-butyl)amino, methyl(cyclobutyl)amino, ethyl(n-propyl)amino, ethyl(isopropyl)amino, ethyl(cyclopropyl)amino, ethyl(n-butyl)amino, ethyl(isobutyl)amino, ethyl(sec-butyl)amino, ethyl(tert-butyl)amino, ethyl(cyclobutyl)amino, n-propyl(isopropyl)amino, n-propyl(cyclopropyl)amino, n-propyl(n-butyl)amino, n-propyl(isobutyl)amino, n-propyl(sec-butyl)amino, n-propyl(tert-butyl)amino, n-propyl(cyclobutyl)amino Examples of the amino groups include isopropyl(cyclopropyl)amino, isopropyl(n-butyl)amino, isopropyl(isobutyl)amino, isopropyl(sec-butyl)amino, isopropyl(tert-butyl)amino, isopropyl(cyclobutyl)amino, cyclopropyl(n-butyl)amino, cyclopropyl(isobutyl)amino, cyclopropyl(sec-butyl)amino, cyclopropyl(tert-butyl)amino, cyclopropyl(cyclobutyl)amino, n-butyl(isobutyl)amino, n-butyl(sec-butyl)amino, n-butyl(tert-butyl)amino, n-butyl(cyclobutyl)amino, isobutyl(sec-butyl)amino, isobutyl(tert-butyl)amino, isobutyl(cyclobutyl)amino, sec-butyl(tert-butyl)amino, sec-butyl(cyclobutyl)amino, and tert-butyl(cyclobutyl)amino.

[0030] Ar in general formula (1) 1 , Ar 2 and Ar 3Examples of the arylamino group having 6 to 20 carbon atoms, which may have a substituent, include those corresponding to the above-mentioned aryl groups, and specific examples include phenylamino, naphthylamino, p-methylphenylamino, o-methylphenylamino, p-tert-butylphenylamino, p-methoxyphenylamino, p-chlorophenylamino, p-nitrophenylamino, p-cyanophenylamino, o-biphenylylamino, m-biphenylylamino, p-biphenylylamino, α-naphthylamino, β-naphthylamino, 1-anthrylamino, 2-anthrylamino, 9-anthrylamino, 1-phenanthrylamino, 2-phenanthrylamino, 3-phenanthrylamino, 4-phenanthrylamino, and 9-phenanthrylamino.

[0031] Ar in general formula (1) 1 , Ar 2 and Ar 3 Examples of the diarylamino group having 12 to 20 carbon atoms which may have a substituent include those corresponding to the above aryl groups, and specific examples include diphenylamino, dinaphthylamino, phenylnaphthylamino, etc.

[0032] Ar in general formula (1) 1 , Ar 2 and Ar 3 Examples of the alkylarylamino group having 7 to 20 carbon atoms, which may have a substituent, include those corresponding to the alkyl and aryl groups described above, and specific examples include methylphenylamino, ethylphenylamino, isopropylphenylamino, sec-butylphenylamino, tert-butylphenylamino, n-hexylphenylamino, cyclohexylphenylamino, methylnaphthylamino, and ethylnaphthylamino.

[0033] Ar in general formula (1) 1 , Ar 2 and Ar 3Examples of the alkylcarbonyl group having 2 to 20 carbon atoms, which may have a substituent, include those corresponding to the above alkyl groups, and specific examples include methylcarbonyl (also called acetyl), ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, isobutylcarbonyl, sec-butylcarbonyl, tert-butylcarbonyl, 1-pentylcarbonyl, 2-pentylcarbonyl, 3-pentylcarbonyl, isopentylcarbonyl, neopentylcarbonyl, tert-pentylcarbonyl, 1-hexylcarbonyl, 2-hexylcarbonyl, 3-hexylcarbonyl, cyclohexylcarbonyl, etc.

[0034] Ar in general formula (1) 1 , Ar 2 and Ar 3 Examples of the arylcarbonyl group having 7 to 20 carbon atoms, which may have a substituent, include those corresponding to the above-mentioned aryl groups, and specific examples include benzoyl, p-methylbenzoyl, p-tert-butylbenzoyl, p-methoxybenzoyl, p-chlorobenzoyl, p-nitrobenzoyl, p-cyanobenzoyl, o-biphenylylcarbonyl, m-biphenylylcarbonyl, p-biphenylylcarbonyl, α-naphthylcarbonyl, β-naphthylcarbonyl, 1-anthrylcarbonyl, 2-anthrylcarbonyl, 9-anthrylcarbonyl, 1-phenanthrylcarbonyl, 2-phenanthrylcarbonyl, 3-phenanthrylcarbonyl, 4-phenanthrylcarbonyl, and 9-phenanthrylcarbonyl.

[0035] Ar in general formula (1) 1 , Ar 2 and Ar 3Examples of the alkylcarbonyloxy group having 2 to 20 carbon atoms, which may have a substituent, include those corresponding to the above alkyl groups, and specific examples include methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, isopropylcarbonyloxy, n-butylcarbonyloxy, isobutylcarbonyloxy, sec-butylcarbonyloxy, tert-butylcarbonyloxy, pentylcarbonyloxy, hexylcarbonyloxy, cyclohexylcarbonyloxy, heptylcarbonyloxy, and heptan-3-ylcarbonyloxy.

[0036] Ar in general formula (1) 1 , Ar 2 and Ar 3 Examples of the arylcarbonyloxy group having 7 to 20 carbon atoms, which may have a substituent, include those corresponding to the above-mentioned aryl group, and specific examples include benzoyloxy, p-methylbenzoyloxy, p-tert-butylbenzoyloxy, p-methoxybenzoyloxy, p-chlorobenzoyloxy, p-nitrobenzoyloxy, p-cyanobenzoyloxy, o-biphenylylcarbonyloxy, m-biphenylylcarbonyloxy, p-biphenylylcarbonyloxy, α-naphthylcarbonyloxy, β-naphthylcarbonyloxy, 1-anthrylcarbonyloxy, 2-anthrylcarbonyloxy, 9-anthrylcarbonyloxy, 1-phenanthrylcarbonyloxy, 2-phenanthrylcarbonyloxy, 3-phenanthrylcarbonyloxy, 4-phenanthrylcarbonyloxy, and 9-phenanthrylcarbonyloxy.

[0037] Ar in general formula (1) 1 , Ar 2 and Ar 3Examples of the alkoxycarbonyl group having 2 to 20 carbon atoms, which may have a substituent, include those corresponding to the above alkyl groups, and specific examples include methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, 1-pentyloxycarbonyl, 2-pentyloxycarbonyl, 3-pentyloxycarbonyl, isopentyloxycarbonyl, neopentyloxycarbonyl, tert-pentyloxycarbonyl, 1-hexyloxycarbonyl, 2-hexyloxycarbonyl, 3-hexyloxycarbonyl, cyclohexyloxycarbonyl, etc.

[0038] Ar in general formula (1) 1 , Ar 2 and Ar 3 Examples of the aryloxycarbonyl group having 7 to 20 carbon atoms, which may have a substituent, include those corresponding to the above-mentioned aryl groups, and specific examples include phenoxycarbonyl, p-methylphenoxycarbonyl, naphthyloxycarbonyl, biphenylyloxycarbonyl, anthryloxycarbonyl, and phenanthryloxycarbonyl.

[0039] Ar in general formula (1) 1 , Ar 2 and Ar 3Examples of the alkylaminocarbonyl group having 2 to 20 carbon atoms, which may have a substituent, include those corresponding to the above alkyl groups, and specific examples include methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, isopropylaminocarbonyl, n-butylaminocarbonyl, isobutylaminocarbonyl, sec-butylaminocarbonyl, tert-butylaminocarbonyl, 1-pentylaminocarbonyl, 2-pentylaminocarbonyl, 3-pentylaminocarbonyl, i-pentylaminocarbonyl, neopentylaminocarbonyl, tert-pentylaminocarbonyl, 1-hexylaminocarbonyl, 2-hexylaminocarbonyl, 3-hexylaminocarbonyl, cyclohexylaminocarbonyl, etc.

[0040] Ar in general formula (1) 1 , Ar 2 and Ar 3 Examples of the arylaminocarbonyl group having 7 to 20 carbon atoms, which may have a substituent, include those corresponding to the above aryl group, and specific examples include phenylaminocarbonyl, naphthylaminocarbonyl, p-methylphenylaminocarbonyl, o-methylphenylaminocarbonyl, p-tert-butylphenylaminocarbonyl, p-methoxyphenylaminocarbonyl, p-chlorophenylaminocarbonyl, p-nitrophenylaminocarbonyl, p-cyanophenylaminocarbonyl, carboxyl, o-biphenylylaminocarbonyl, m-biphenylylaminocarbonyl, p-biphenylylaminocarbonyl, α-naphthylaminocarbonyl, β-naphthylaminocarbonyl, 1-anthrylaminocarbonyl, 2-anthrylaminocarbonyl, 9-anthrylaminocarbonyl, 1-phenanthrylaminocarbonyl, 2-phenanthrylaminocarbonyl, 3-phenanthrylaminocarbonyl, 4-phenanthrylaminocarbonyl, 9-phenanthrylaminocarbonyl, and the like.

[0041] Ar in general formula (1) 1 , Ar 2 and Ar3Examples of the optionally substituted dialkylaminocarbonyl group having 3 to 20 carbon atoms include those corresponding to the above alkyl groups, and specific examples include dimethylaminocarbonyl, diethylaminocarbonyl, di-n-propylaminocarbonyl, diisopropylaminocarbonyl, dicyclopropylaminocarbonyl, di-n-butylaminocarbonyl, diisobutylaminocarbonyl, di-sec-butylaminocarbonyl, di-tert-butylaminocarbonyl, dicyclobutylaminocarbonyl, di-1-pentylaminocarbonyl, di-2-pentylaminocarbonyl, di-3-pentylaminocarbonyl, diisopentylaminocarbonyl, di-neopentylaminocarbonyl, di-tert-pentylaminocarbonyl, dicyclopentylaminocarbonyl, di-1-hexylaminocarbonyl, di-2-hexylaminocarbonyl, di-3-hexylaminocarbonyl, dicyclohexylaminocarbonyl, di-(1-methyl-n-pentyl)aminocarbonyl, di-(1,1,2-trimethyl-n-propyl)aminocarbonyl, di-(1,2,2-trimethyl- (n-propyl)aminocarbonyl, di-(3,3-dimethyl-n-butyl)aminocarbonyl, methyl(ethyl)aminocarbonyl, methyl(n-propyl)aminocarbonyl, methyl(isopropyl)aminocarbonyl, methyl(cyclopropyl)aminocarbonyl, methyl(n-butyl)aminocarbonyl, methyl(isobutyl)aminocarbonyl, methyl(sec-butyl)aminocarbonyl, methyl(tert-butyl)aminocarbonyl, methyl(cyclobutyl)aminocarbonyl, ethyl(n-propyl)aminocarbonyl, ethyl(isopropyl)aminocarbonyl n-propyl)aminocarbonyl, ethyl(cyclopropyl)aminocarbonyl, ethyl(n-butyl)aminocarbonyl, ethyl(isobutyl)aminocarbonyl, ethyl(sec-butyl)aminocarbonyl, ethyl(tert-butyl)aminocarbonyl, ethyl(cyclobutyl)aminocarbonyl, n-propyl(isopropyl)aminocarbonyl, n-propyl(cyclopropyl)aminocarbonyl, n-propyl(n-butyl)aminocarbonyl, n-propyl(isobutyl)aminocarbonyl, n-propyl(sec-butyl)aminocarbonyl,n-Propyl(tert-butyl)aminocarbonyl, n-Propyl(cyclobutyl)aminocarbonyl, isopropyl(cyclopropyl)aminocarbonyl, isopropyl(n-butyl)aminocarbonyl, isopropyl(isobutyl)aminocarbonyl, isopropyl(sec-butyl)aminocarbonyl, isopropyl(tert-butyl)carbonylamino, isopropyl(cyclobutyl)aminocarbonyl, cyclopropyl(n-butyl)aminocarbonyl, cyclopropyl(isobutyl)aminocarbonyl, cyclopropyl(sec-butyl)aminocarbonyl, cyclopropyl(tert-butyl)aminocarbonyl )aminocarbonyl, cyclopropyl(cyclobutyl)aminocarbonyl, n-butyl(isobutyl)aminocarbonyl, n-butyl(sec-butyl)aminocarbonyl, n-butyl(tert-butyl)aminocarbonyl, n-butyl(cyclobutyl)aminocarbonyl, isobutyl(sec-butyl)aminocarbonyl, isobutyl(tert-butyl)aminocarbonyl, isobutyl(cyclobutyl)aminocarbonyl, sec-butyl(tert-butyl)aminocarbonyl, sec-butyl(cyclobutyl)aminocarbonyl, tert-butyl(cyclobutyl)aminocarbonyl, and the like.

[0042] Ar in general formula (1) 1 , Ar 2 and Ar 3 Examples of the diarylaminocarbonyl group having 13 to 20 carbon atoms, which may have a substituent, include those corresponding to the above-mentioned aryl group, and specific examples include diphenylaminocarbonyl, dinaphthylaminocarbonyl, di(p-methylphenyl)aminocarbonyl, phenylnaphthylaminocarbonyl, etc.

[0043] Ar in general formula (1) 1 , Ar 2 and Ar 3Examples of the alkylarylaminocarbonyl group having 8 to 20 carbon atoms, which may have a substituent, include those corresponding to the above alkyl and aryl groups, and specific examples include methylphenylamino, ethylphenylamino, isopropylphenylamino, sec-butylphenylamino, tert-butylphenylamino, n-hexylphenylamino, cyclohexylphenylamino, methylnaphthylamino, ethylnaphthylamino, etc.

[0044] Ar in general formula (1) 1 , Ar 2 and Ar 3 Examples of the alkylcarbonylamino group having 2 to 20 carbon atoms, which may have a substituent, include those corresponding to the above alkyl groups, and specific examples include methylcarbonylamino, ethylcarbonylamino, n-propylcarbonylamino, isopropylcarbonylamino, n-butylcarbonylamino, isobutylcarbonylamino, sec-butylcarbonylamino, tert-butylcarbonylamino, 1-pentylcarbonylamino, 2-pentylcarbonylamino, 3-pentylcarbonylamino, isopentylcarbonylamino, neopentylcarbonylamino, tert-pentylcarbonylamino, 1-hexylcarbonylamino, 2-hexylcarbonylamino, 3-hexylcarbonylamino, cyclohexylcarbonylamino, etc.

[0045] Ar in general formula (1) 1 , Ar 2 and Ar 3Examples of the arylcarbonylamino group having 7 to 20 carbon atoms, which may have a substituent, include those corresponding to the above aryl group, and specific examples include phenylcarbonylamino, naphthylcarbonylamino, p-methylphenylcarbonylamino, o-methylphenylcarbonylamino, p-tert-butylphenylcarbonylamino, p-methoxyphenylcarbonylamino, p-chlorophenylcarbonylamino, p-nitrophenylcarbonylamino, p-cyanophenylcarbonylamino, arylamino, o-biphenylylcarbonylamino, m-biphenylylcarbonylamino, p-biphenylylcarbonylamino, α-naphthylcarbonylamino, β-naphthylcarbonylamino, 1-anthrylcarbonylamino, 2-anthrylcarbonylamino, 9-anthrylcarbonylamino, 1-phenanthrylcarbonylamino, 2-phenanthrylcarbonylamino, 3-phenanthrylcarbonylamino, 4-phenanthrylcarbonylamino, and 9-phenanthrylcarbonylamino.

[0046] Ar in general formula (1) 1 , Ar 2 and Ar 3 Examples of the heterocyclic group having 2 to 20 carbon atoms which may have a substituent include 5- to 7-membered heterocyclic rings such as pyridyl, pyrimidyl, furyl, thienyl, tetrahydrofuryl, dioxolanyl, benzoxazol-2-yl, tetrahydropyranyl, pyrrolidyl, imidazolidyl, pyrazolidyl, thiazolidyl, isothiazolidyl, oxazolidyl, isoxazolidyl, piperidyl, piperazyl, and morpholinyl.

[0047] In the triazine compound represented by general formula (1), the number of substituents on the substituted phenyl group is preferably 1, from the viewpoint of transparency of the synthetic resin.

[0048] In this case, it is particularly preferable that the triazine compound represented by the general formula (1) has the substituent on the phenyl group at the para position.

[0049] Furthermore, the triazine compound represented by the general formula (1) is preferably Ar 1 , Ar 2 and Ar 3 are preferably all different groups.

[0050] Furthermore, the triazine compound represented by the general formula (1) is preferably Ar 1 and Ar 2 are the same group, and Ar 3 Ar 1 and Ar 2 It is preferable that the group is different from the group.

[0051] In this case, the triazine compound represented by the general formula (1) is selected from the group consisting of Ar 1 and Ar 2 is preferably an unsubstituted phenyl group.

[0052] In addition, the triazine compound represented by the general formula (1) is preferably Ar 1 , Ar 2 and Ar 3 are preferably all phenyl groups having a substituent.

[0053] In this case, Ar 1 and Ar 2 The substituents of Ar 3 The substituents of Ar 1 and Ar 2 It is preferable that the substituents are different from those of the groups.

[0054] In addition, in the triazine compound represented by general formula (1), from the viewpoint of transparency of the synthetic resin, it is preferable that at least one of the substituted phenyl groups has a substituent having a carbonyl group in the structure. 3 However, it is preferable that the structure of the compound has a substituent having a carbonyl group.

[0055] Examples of substituents having a carbonyl group in their structure include a carboxy group, an aminocarbonyl group, an alkylcarbonyl group having 2 to 20 carbon atoms, an arylcarbonyl group having 7 to 20 carbon atoms, an alkylcarbonyloxy group having 2 to 20 carbon atoms, an arylcarbonyloxy group having 7 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, an alkylaminocarbonyl group having 2 to 20 carbon atoms, an arylaminocarbonyl group having 7 to 20 carbon atoms, a dialkylaminocarbonyl group having 3 to 20 carbon atoms, a diarylaminocarbonyl group having 13 to 20 carbon atoms, an alkylarylaminocarbonyl group having 8 to 20 carbon atoms, an alkylcarbonylamino group having 2 to 20 carbon atoms, and an arylcarbonylamino group having 7 to 20 carbon atoms, which may be substituted with the aforementioned substituents. The carboxy group may also form a salt.

[0056] Among the substituents having a carbonyl group in these structures, from the viewpoint of transparency of the synthetic resin, a carboxy group, an aminocarbonyl group, an alkylaminocarbonyl group having 2 to 20 carbon atoms, an arylaminocarbonyl group having 7 to 20 carbon atoms, a dialkylaminocarbonyl group having 3 to 20 carbon atoms, a diarylaminocarbonyl group having 13 to 20 carbon atoms, or an alkylarylaminocarbonyl group having 8 to 20 carbon atoms is preferred, a carboxy group or an aminocarbonyl group is more preferred, and an aminocarbonyl group is even more preferred.

[0057] The triazine compound represented by the general formula (1) may also be Ar 1 , Ar 2 and Ar 3Among these, it is preferable from the viewpoint of transparency of the synthetic resin that one of them is a phenyl group having a substituent with a carbonyl group in its structure; it is more preferable that one of them is a phenyl group having a substituent with a carbonyl group in its structure and the remaining two are phenyl groups having a substituent without a carbonyl group in its structure; or it is more preferable that one of them is a phenyl group having a substituent with a carbonyl group in its structure and the remaining two are phenyl groups having no substituent; and it is even more preferable that one of them is a phenyl group having a substituent with a carbonyl group in its structure and the remaining two are phenyl groups having substituents without a carbonyl group in its structure.

[0058] In these structures, the substituent having a carbonyl group is preferably a carboxy group, an aminocarbonyl group, an alkylaminocarbonyl group having 2 to 20 carbon atoms, an arylaminocarbonyl group having 7 to 20 carbon atoms, a dialkylaminocarbonyl group having 3 to 20 carbon atoms, a diarylaminocarbonyl group having 13 to 20 carbon atoms, or an alkylarylaminocarbonyl group having 8 to 20 carbon atoms, from the viewpoint of transparency of the synthetic resin, more preferably a carboxy group or an aminocarbonyl group, and even more preferably an aminocarbonyl group. Furthermore, in terms of transparency of the synthetic resin, the substituent not having a carbonyl group in the structure is preferably an alkyl group having 1 to 20 carbon atoms which may have a substituent or an aryl group having 6 to 20 carbon atoms which may have a substituent, more preferably an alkyl group having 1 to 8 carbon atoms or an aryl group having 6 to 12 carbon atoms, more preferably a methyl group, a cyclohexyl group, or a phenyl group which may have a substituent, and even more preferably a phenyl group or a cyclohexyl group.

[0059] Specific examples of the triazine compound represented by general formula (1) include the following compounds No. 1 to No. 59. Among these, the triazine compounds No. 49, No. 50, No. 58, and No. 59 are particularly preferred from the viewpoint of imparting particularly excellent transparency to synthetic resins.

[0060] TIFF2025169326000003.tif165164TIFF2025169326000004.tif247164TIFF2025169326000005.t if240170TIFF2025169326000006.tif250170TIFF2025169326000007.tif250165TIFF20251693260 00008.tif238170TIFF2025169326000009.tif248170TIFF2025169326000010.tif238166TIFF202 5169326000011.tif248170TIFF2025169326000012.tif238170TIFF2025169326000013.tif157170

[0061] The compound represented by the general formula (1) can be produced, for example, by using cyanuric acid chloride as a raw material in an organic solvent, and adding 1 equivalent of Ar 1 , Ar 2 , Ar 3 can be obtained by sequentially reacting the corresponding phenol compounds in the presence of one equivalent of a base (triatylamine, sodium hydroxide, etc.).

[0062] The nucleating agent of the present invention contains one or more triazine compounds represented by general formula (1). The nucleating agent of the present invention is used by blending it with a synthetic resin. The nucleating agent of the present invention can improve the transparency of the synthetic resin. Therefore, the nucleating agent of the present invention exhibits excellent effects as a clarifying agent that improves the transparency of the synthetic resin, and is therefore also preferably used as a clarifying agent.

[0063] The blending amount of the nucleating agent of the present invention to the synthetic resin is preferably 0.001 to 10 parts by mass, more preferably 0.01 to 2.0 parts by mass, even more preferably 0.02 to 1.0 parts by mass, still more preferably 0.02 to 0.5 parts by mass, and particularly preferably 0.02 to 0.3 parts by mass, per 100 parts by mass of the synthetic resin, from the viewpoint of the transparency of the synthetic resin.

[0064] Next, the synthetic resin composition containing the nucleating agent of the present invention will be described in more detail. Specific examples of synthetic resins that can be used with the nucleating agent of the present invention include α-olefin polymers such as polypropylene, high-density polyethylene, low-density polyethylene, linear low-density polyethylene, cross-linked polyethylene, ultra-high molecular weight polyethylene, polybutene-1, and poly-3-methylpentene, and polyolefin resins such as ethylene-vinyl acetate copolymer, ethylene-ethyl acrylate copolymer, and ethylene-propylene copolymer, as well as copolymers thereof; halogen-containing resins such as polyvinyl chloride, polyvinylidene chloride, chlorinated polyethylene, chlorinated polypropylene, polyvinylidene fluoride, chlorinated rubber, vinyl chloride-vinyl acetate copolymer, vinyl chloride-ethylene copolymer, vinyl chloride-vinylidene chloride copolymer, vinyl chloride-vinylidene chloride-vinyl acetate terpolymer, vinyl chloride-acrylic acid ester copolymer, vinyl chloride-maleic acid ester copolymer, and vinyl chloride-cyclohexylmaleimide copolymer; petroleum resin, coumarone resin, polystyrene, polyvinyl acetate, acrylic resin, polymethyl methacrylate, polyvinyl alcohol, polyvinyl formal, polyvinyl butyral; polyethylene terephthalate, polybutylene terephthalate, and the like. aromatic polyesters such as polyalkylene terephthalates such as polycyclohexanedimethylene terephthalate, polyalkylene naphthalates such as polyethylene naphthalate and polybutylene naphthalate, and linear polyesters such as polytetramethylene terephthalate; degradable aliphatic polyesters such as polyhydroxybutyrate, polycaprolactone, polybutylene succinate, polyethylene succinate, polylactic acid resin, polymalic acid, polyglycolic acid, polydioxane, and poly(2-oxetanone); polyphenylene oxide, polycaprolactone Examples of the resin include polyamides such as acetal and polyhexamethylene adipamide, thermoplastic resins such as polycarbonate, branched polycarbonate, polyacetal, polyphenylene sulfide, polyurethane, and cellulose-based resins, and blends thereof; thermosetting resins such as phenolic resin, urea resin, melamine resin, epoxy resin, and unsaturated polyester resin; fluorine-based resin, silicone resin, silicone rubber, polyethersulfone, polysulfone, polyphenylene ether, polyether ketone, polyether ether ketone, and liquid crystal polymers.Other examples include isoprene rubber, butadiene rubber, acrylonitrile-butadiene copolymer rubber, styrene-butadiene copolymer rubber, fluororubber, and silicone rubber. Specific examples of synthetic resins include olefin-based thermoplastic elastomers, styrene-based thermoplastic elastomers, polyester-based thermoplastic elastomers, nitrile-based thermoplastic elastomers, nylon-based thermoplastic elastomers, vinyl chloride-based thermoplastic elastomers, polyamide-based thermoplastic elastomers, and polyurethane-based thermoplastic elastomers. These synthetic resins may be used alone or in combination. Furthermore, the synthetic resins may be alloyed.

[0065] The synthetic resin used in the present invention can be used regardless of 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, type of polymerization catalyst (e.g., Ziegler catalyst, metallocene catalyst, etc.), etc. Among these synthetic resins, polyolefin resins are preferred from the viewpoint of improving transparency.

[0066] Examples of these polyolefin resins include polyethylene, low-density polyethylene, linear low-density polyethylene, high-density polyethylene, polypropylene, homopolypropylene, random copolymer polypropylene, block copolymer polypropylene, impact copolymer polypropylene, high-impact copolymer polypropylene, isotactic polypropylene, syndiotactic polypropylene, hemiisotactic polypropylene, maleic anhydride-modified polypropylene, polybutene, cycloolefin polymer, stereoblock polypropylene, α-olefin polymers such as poly-3-methyl-1-butene, poly-3-methyl-1-pentene, and poly-4-methyl-1-pentene, ethylene / propylene block or random copolymers, and α-olefin copolymers such as ethylene-methyl methacrylate copolymer and ethylene-vinyl acetate copolymer.

[0067] Furthermore, the synthetic resin composition of the present invention may contain various additives, such as conventionally known plasticizers, antioxidants, heat stabilizers, light stabilizers, ultraviolet absorbers, pigments, colorants, various fillers, antistatic agents, mold release agents, fragrances, lubricants, flame retardants, foaming agents, bulking agents, antibacterial agents, antifungal agents, and crystal nucleating agents other than the crystal nucleating agent of the present invention, as needed.

[0068] In the synthetic resin composition of the present invention, the method for blending the nucleating agent of the present invention with the synthetic resin is not particularly limited and can be carried out by any conventionally known method. For example, the synthetic resin powder or pellets may be dry-blended with the nucleating agent (and other additives, if necessary), or a portion of the nucleating agent (and other additives, if necessary) may be pre-blended and then dry-blended with the remaining components. After dry-blending, the components may be mixed using, for example, a mill roll, a Banbury mixer, or a super mixer, and then kneaded using a single-screw or twin-screw extruder. In the case of polyolefin-based resins, this mixing and kneading is typically carried out at a temperature of about 120 to 220°C. Other methods that can be used include adding the additive during the polymerization stage of the synthetic resin (e.g., polyolefin-based resin); pre-mixing with binders, waxes, solvents, granulation aids such as silica, etc. in the desired ratio, followed by granulation to form a one-pack composite additive, which is then added to the synthetic resin; or preparing a masterbatch containing a high concentration of the nucleating agent (and other additives, if necessary) and adding this masterbatch to the synthetic resin.

[0069] If necessary, various additives such as phenolic antioxidants, phosphorus-based antioxidants, thioether-based antioxidants, ultraviolet absorbers, and hindered amine-based light stabilizers can be added to the synthetic resin composition of the present invention, thereby stabilizing the resin composition of the present invention. These various additives such as antioxidants may be blended into the nucleating agent of the present invention before being blended with the synthetic resin.

[0070] Examples of phenolic antioxidants include 2,6-di-tert-butyl-p-cresol, 2,6-diphenyl-4-octadecyloxyphenol, distearyl (3,5-di-tert-butyl-4-hydroxybenzyl)phosphonate, 1,6-hexamethylenebis[(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid amide], 4,4'-thiobis(6-tert-butyl-m-cresol), 2,2'-methylenebis(4-methyl-6-tert-butylphenol), 2,2'-methylenebis(4-ethyl-6-tert-butylphenol), 4,4'-butyl- Ethylidenebis(6-tert-butyl-m-cresol), 2,2'-ethylidenebis(4,6-di-tert-butylphenol), 2,2'-ethylidenebis(4-sec-butyl-6-tert-butylphenol), 1,1,3-tris(2-methyl-4-hydroxy-5-tert-butylphenyl)butane, 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)isocyanurate, diethyl)-2,4,6-trimethylbenzene, 2-tert-butyl-4-methyl-6-(2-acryloyloxy-3-tert-butyl-5-methylbenzyl)phenol, stearyl (3,5-di-tert-butyl-4-hydroxyphenyl)propionate, tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)methylpropionate]methane, thiodiethylene glycol bis[(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], 1,6-hexamethylene bis[(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] ], bis[3,3-bis(4-hydroxy-3-tert-butylphenyl)butyric acid] glycol ester, bis[2-tert-butyl-4-methyl-6-(2-hydroxy-3-tert-butyl-5-methylbenzyl)phenyl] terephthalate, 1,3,5-tris[(3,5-ditert-butyl-4-hydroxyphenyl)propionyloxyethyl] isocyanurate, 3,9-bis[1,1-dimethyl-2-{(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy}ethyl]-2,4,8,10-tetraoxaspiro[5,5]undecane, triethylene glycol bis[(3-tert-butyl-4-hydroxy-5-methylphenyl)propionate], etc. The amount of these phenolic antioxidants added is preferably 0.001 to 10 parts by mass, more preferably 0.05 to 5 parts by mass, per 100 parts by mass of the synthetic resin.

[0071] Examples of phosphorus-based antioxidants include trisnonylphenyl phosphite, tris[2-tert-butyl-4-(3-tert-butyl-4-hydroxy-5-methylphenylthio)-5-methylphenyl]phosphite, tridecyl phosphite, octyldiphenyl phosphite, di(decyl)monophenyl phosphite, di(tridecyl)pentaerythritol diphosphite, di(nonylphenyl)pentaerythritol diphosphite, bis(2,4-ditert-butylphenyl)pentaerythritol diphosphite, bis(2,6-ditert-butyl-4-methylphenyl)pentaerythritol diphosphite, bis(2,4,6-tritert-butylphenyl)pentaerythritol diphosphite, bis(2,4-dicumylphenyl)pentaerythritol diphosphite, tetra(tridecyl)isopropylidenediphenol diphosphite, tetra(tridecyl)-4,4'-n-butylidenebis(2- tert-butyl-5-methylphenol) diphosphite, hexa(tridecyl)-1,1,3-tris(2-methyl-4-hydroxy-5-tert-butylphenyl)butane triphosphite, tetrakis(2,4-ditert-butylphenyl) biphenylene diphosphonite, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 2,2'-methylenebis(4,6-tert-butylphenyl)-2-ethylhexyl phosphite, 2 Examples of suitable phosphorus-based antioxidants include 2'-methylenebis(4,6-tert-butylphenyl)octadecyl phosphite, 2,2'-ethylidenebis(4,6-di-tert-butylphenyl)fluorophosphite, tris(2-[(2,4,8,10-tetrakis-tert-butyldibenzo[d,f][1,3,2]dioxaphosphepin-6-yl)oxy]ethyl)amine, and phosphite of 2-ethyl-2-butylpropylene glycol and 2,4,6-tri-tert-butylphenol. The amount of these phosphorus-based antioxidants added is preferably 0.001 to 10 parts by mass, and more preferably 0.05 to 5 parts by mass, per 100 parts by mass of the synthetic resin.

[0072] Examples of thioether-based antioxidants include dialkylthiodipropionates such as dilauryl thiodipropionate, dimyristyl thiodipropionate, and distearyl thiodipropionate, and pentaerythritol tetra(β-alkylthiopropionic acid) esters. The amount of these thioether-based antioxidants added is preferably 0.001 to 10 parts by mass, and more preferably 0.05 to 5 parts by mass, per 100 parts by mass of the synthetic resin.

[0073] Examples of the ultraviolet absorber include 2-hydroxybenzophenones such as 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-octoxybenzophenone, and 5,5'-methylenebis(2-hydroxy-4-methoxybenzophenone); 2-(2'-hydroxy-5'-methylphenyl)benzotriazole, 2-(2'-hydroxy-3',5'-di-tert-butylphenyl)-5-chlorobenzotriazole, and 2-(2'-hydroxy-3',5'- 2-(2'-hydroxyphenyl)benzotriazoles such as 2-(tert-butyl-5'-methylphenyl)-5-chlorobenzotriazole, 2-(2'-hydroxy-5'-tert-octylphenyl)benzotriazole, 2-(2'-hydroxy-3',5'-dicumylphenyl)benzotriazole, 2,2'-methylenebis(4-tert-octyl-6-(benzotriazolyl)phenol), and 2-(2'-hydroxy-3'-tert-butyl-5'-carboxyphenyl)benzotriazole; phenyl Benzoates such as ricinate, resorcinol monobenzoate, 2,4-ditert-butylphenyl-3,5-ditert-butyl-4-hydroxybenzoate, 2,4-ditert-amylphenyl-3,5-ditert-butyl-4-hydroxybenzoate, hexadecyl-3,5-ditert-butyl-4-hydroxybenzoate; substituted oxanilides such as 2-ethyl-2'-ethoxyoxanilide, 2-ethoxy-4'-dodecyloxanilide; ethyl-α-cyano-β,β-diphenylacrylate, methyl and triaryltriazines such as 2-(2-hydroxy-4-octoxyphenyl)-4,6-bis(2,4-di-tert-butylphenyl)-s-triazine, 2-(2-hydroxy-4-methoxyphenyl)-4,6-diphenyl-s-triazine, and 2-(2-hydroxy-4-propoxy-5-methylphenyl)-4,6-bis(2,4-di-tert-butylphenyl)-s-triazine. The amount of these ultraviolet absorbers added is preferably 0.001 to 30 parts by mass, and more preferably 0.05 to 10 parts by mass, per 100 parts by mass of the synthetic resin.

[0074] Examples of the hindered amine light stabilizer include 2,2,6,6-tetramethyl-4-piperidyl stearate, 1,2,2,6,6-pentamethyl-4-piperidyl stearate, 2,2,6,6-tetramethyl-4-piperidyl benzoate, bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate, bis(1,2,2,6,6-pentamethyl-4-piperidyl)sebacate, bis(1-octoxy-2,2,6,6-tetramethyl-4-piperidyl)sebacate, tetrakis(2,2,6,6-tetramethyl-4-piperidyl)- 1,2,3,4-Butanetetracarboxylate, Tetrakis(1,2,2,6,6-pentamethyl-4-piperidyl)-1,2,3,4-butanetetracarboxylate, Bis(2,2,6,6-tetramethyl-4-piperidyl)·bis(tridecyl)-1,2,3,4-butanetetracarboxylate, Bis(1,2,2,6,6-pentamethyl-4-piperidyl)·bis(tridecyl)-1,2,3,4-butanetetracarboxylate, Bis(1,2,2,6,6-pentamethyl-4-piperidyl)·bis(tridecyl)-1,2,3,4-butanetetracarboxylate, Bis(1,2,2,6,6-pentamethyl-4-piperidyl)-2-butyl-2-(3,5-di-tert-butyl) (4-hydroxybenzyl)malonate, 1,2,2,6,6-pentamethyl-4-piperidyl methacrylate, poly[{6-(1,1,3,3-tetramethylbutyl)amino-1,3,5-triazine-2,4-diyl}{(2,2,6,6-tetramethyl-4-piperidyl)imino}hexamethylene{(2,2,6,6-tetramethyl-4-piperidyl)imino}], 1,2,3,4-butanecarboxylic acid / 2,2-bis(hydroxymethyl)-1,3-propanediol / 3-hydroxy-2,2-dimethylpropanal / 1,2,2,6,6 -Pentamethyl-4-piperidinyl ester polycondensate, bis(1,2,2,6,6-pentamethyl-4-piperidyl) decanedioate / methyl 1,2,2,6,6-pentamethyl-4-piperidyl sebacate mixture, 2,2,6,6-tetramethyl-4-piperidyl methacrylate, 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-piperidinol / diethyl succinate polycondensate, 1,6-bis(2,2,6,6-tetramethyl-4-piperidylamino)hexane / dibromoethane polycondensate, 1,6-bis(2,2,6,6-tetramethyl-4-piperidylamino)hexane / 2,4-dichloro-6-morpholino-s-triazine polycondensate, 1,6-bis(2,2,6,6-tetramethyl-4-piperidylamino)hexane / 2,4-dichloro-6-tert-octylamino-s-triazine polycondensate, 1,5,8,12-tetrakis[2,4-bis(N-butyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino)-s-triazin-6-yl]-1,5,8,12-tetraazadodecane, 1, 5,8,12-Tetrakis[2,4-bis(N-butyl-N-(1,2,2,6,6-pentamethyl-4-piperidyl)amino)-s-triazin-6-yl]-1,5,8,12-tetraazadodecane, 1,6,11-tris[2,4-bis(N-butyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino-s-triazin-6-ylamino]undecane, 1,6,11-tris[2,4-bis(N-butyl-N-(1,2,2,6,6-pentamethyl-4-piperidyl)amino] Amino-s-triazin-6-ylamino]undecane, 3,9-bis[1,1-dimethyl-2-{tris(2,2,6,6-tetramethyl-4-piperidyloxycarbonyl)butylcarbonyloxy}ethyl]-2,4,8,10-tetraoxaspiro[5.5]undecane, 3,9-bis[1,1-dimethyl-2-{tris(1,2,2,6,6-pentamethyl-4-piperidyloxycarbonyl)butylcarbonyloxy}ethyl]-2,4,8,10-tetraoxaspiro[5. 5) Examples of hindered amine compounds include undecane, bis(1-undecyloxy-2,2,6,6-tetramethylpiperidin-4-yl) carbonate, 2,2,6,6-tetramethyl-4-piperidyl hexadecanoate, and 2,2,6,6-tetramethyl-4-piperidyl octadecanoate. The amount of these hindered amine light stabilizers added is preferably 0.001 to 30 parts by mass, and more preferably 0.05 to 10 parts by mass, per 100 parts by mass of the synthetic resin.

[0075] Furthermore, when a polyolefin resin is used as the synthetic resin, it is preferable to further add a known neutralizing agent, if necessary, to neutralize residual catalyst in the polyolefin resin, within a range that does not impair the effects of the present invention. Examples of the neutralizing agent include fatty acid metal salts such as calcium stearate, lithium stearate, and sodium stearate, and fatty acid amide compounds such as ethylene bis(stearamide), ethylene bis(12-hydroxystearamide), and stearic acid amide. These neutralizing agents may be used in combination.

[0076] Other additives that may be added to the synthetic resin composition of the present invention, if necessary, include nucleating agents such as metal salts of aromatic carboxylic acids, metal salts of alicyclic alkylcarboxylic acids, aluminum p-tert-butylbenzoate, metal salts of aromatic phosphates, and dibenzylidene sorbitols, metal soaps, hydrotalcites, triazine ring-containing compounds, metal hydroxides, phosphate ester-based flame retardants, condensed phosphate ester-based flame retardants, phosphate-based flame retardants, inorganic phosphorus-based flame retardants, (poly)phosphate-based flame retardants, halogen-based flame retardants, silicon-based flame retardants, antimony oxides such as antimony trioxide, other inorganic flame retardant aids, other organic flame retardant aids, fillers, pigments, lubricants, foaming agents, antistatic agents, and the like, within limits that do not impair the effects of the present invention.

[0077] Examples of triazine ring-containing compounds include melamine, ammeline, benzguanamine, acetoguanamine, phthalodiguanamine, melamine cyanurate, melamine pyrophosphate, butylenediguanamine, norbornenediguanamine, methylenediguanamine, ethylenedimelamine, trimethylenedimelamine, tetramethylenedimelamine, hexamethylenedimelamine, and 1,3-hexylenedimelamine.

[0078] Examples of metal hydroxides include magnesium hydroxide, aluminum hydroxide, calcium hydroxide, barium hydroxide, zinc hydroxide, and Kismer 5A (magnesium hydroxide: manufactured by Kyowa Chemical Industry Co., Ltd.).

[0079] Examples of phosphate ester-based flame retardants include trimethyl phosphate, triethyl phosphate, tributyl phosphate, tributoxyethyl phosphate, trischloroethyl phosphate, trisdichloropropyl phosphate, triphenyl phosphate, tricresyl phosphate, cresyl diphenyl phosphate, trixylenyl phosphate, octyl diphenyl phosphate, xylenyl diphenyl phosphate, trisisopropylphenyl phosphate, 2-ethylhexyl diphenyl phosphate, t-butylphenyl diphenyl phosphate, bis-(t-butylphenyl)phenyl phosphate, tris-(t-butylphenyl)phosphate, isopropylphenyl diphenyl phosphate, bis-(isopropylphenyl)diphenyl phosphate, and tris-(isopropylphenyl)phosphate.

[0080] Examples of condensed phosphate ester flame retardants include 1,3-phenylenebis(diphenyl phosphate), 1,3-phenylenebis(dixylenyl phosphate), and bisphenol A bis(diphenyl phosphate).

[0081] Examples of the (poly)phosphate flame retardant include ammonium salts and amine salts of (poly)phosphoric acid, such as ammonium polyphosphate, melamine polyphosphate, piperazine polyphosphate, melamine pyrophosphate, and piperazine pyrophosphate.

[0082] Examples of other inorganic flame retardant aids include inorganic compounds such as titanium oxide, aluminum oxide, magnesium oxide, hydrotalcite, talc, and montmorillonite, and surface-treated products thereof, and various commercially available products can be used, such as TIPAQUE R-680 (titanium oxide: manufactured by Ishihara Sangyo Kaisha), Kyowamag 150 (magnesium oxide: manufactured by Kyowa Chemical Industry Co., Ltd.), DHT-4A (hydrotalcite: manufactured by Kyowa Chemical Industry Co., Ltd.), and Alkamiser 4 (zinc-modified hydrotalcite: manufactured by Kyowa Chemical Industry Co., Ltd.). Examples of other organic flame retardant aids include pentaerythritol.

[0083] In addition, additives that are usually used in synthetic resins, such as crosslinking agents, antifogging agents, anti-plate-out agents, surface treatment agents, plasticizers, lubricants, flame retardants, fluorescent agents, antifungal agents, bactericides, foaming agents, metal deactivators, release agents, pigments, processing aids, antioxidants, and light stabilizers, may be blended into the synthetic resin composition of the present invention, as needed, within the range that does not impair the effects of the present invention.

[0084] The additives to be blended in the resin composition of the present invention may be added directly to the synthetic resin, or may be blended in the nucleating agent of the present invention and then added to the synthetic resin.

[0085] The molded article of the present invention is obtained from the synthetic resin composition of the present invention. By molding the synthetic resin composition of the present invention, a molded article having excellent transparency can be efficiently obtained. The molding method is not particularly limited, and examples thereof include extrusion processing, extrusion molding, calendaring, injection molding, vacuum molding, rolling, compression molding, blow molding, and rotational molding, and molded articles of various shapes such as resin plates, sheets, films, bottles, rods, containers, fibers, and irregularly shaped articles can be obtained. [Example]

[0086] The present invention will be described in more detail below using examples, but the present invention is not limited to these examples.

[0087] [Synthesis of Compound Represented by General Formula (1)] Synthesis of nucleating agent (compound No. 5) A solution was prepared by dissolving 4.8 g of sodium hydroxide and 11.29 g of phenol in 300 mL of water. In a separate flask, 11.1 g of cyanuric chloride was dissolved in 300 mL of acetone and cooled to 5°C in an ice bath. The prepared phenol solution was slowly added dropwise over 30 minutes so that the temperature in the system remained below 10°C, and after addition, the mixture was stirred at room temperature for 1 hour. 300 mL of water was then added to the reaction solution, and the precipitate was filtered, washed with distilled water, and dried under reduced pressure to obtain a white solid.

[0088] Next, 2.06 g of 4-hydroxybenzamide and 1.59 g of sodium carbonate were dissolved in a 60 mL distilled water / 90 mL acetone mixed solvent in another flask, 4.49 g of the white solid was added, and the mixture was stirred at room temperature for 3 hours. 120 mL of water was then added, and the resulting precipitate was filtered, washed with distilled water, and dried to obtain approximately 5 g of compound No. 5 as a white solid.

[0089] Compounds No. 1 to No. 4, No. 6 to No. 11, No. 30 to No. 35, and No. 49 to No. 59 shown in Tables 1 to 8 were synthesized using the same procedure.

[0090] [Examples 1 to 46, Reference Examples 1 to 5] 100 parts by mass of polypropylene (melt flow rate = 12 g / 10 min) was mixed with 0.05 parts by mass of tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyloxymethyl]methane (phenolic antioxidant, Adeka STAB AO-60, manufactured by ADEKA CORPORATION), 0.1 part by mass of tris(2,4-di-tert-butylphenyl)phosphite (phosphorus-based antioxidant, Adeka STAB 2112, manufactured by ADEKA CORPORATION), 0.05 part by mass of calcium stearate (lubricant), and a nucleating agent shown in Tables 1 to 8 below in the amounts (parts by mass) shown in Tables 1 to 8 using a Henschel mixer (FM200, manufactured by Mitsui Mining Co., Ltd.) at 1,000 rpm for 1 minute, and extruded using a twin-screw extruder (TEX-28V, manufactured by The Japan Steel Works, Ltd.) at 220 °C and a screw speed of 150 rpm to produce pellets. The obtained pellets were dried at 80° C. for 4 hours and then evaluated as follows: Before mixing, the nucleating agent was crushed in a mortar and passed through a 300 μm mesh.

[0091] However, for Example 3, pellets were produced and evaluated in the same manner as in Example 1, except that 0.05 parts by mass of calcium stearate (lubricant) was not added, and for Example 4, pellets were produced and evaluated in the same manner as in Example 2, except that 0.05 parts by mass of calcium stearate (lubricant) was not added.

[0092] Comparative Example 1 Comparative Example 1 was evaluated in the same manner as Example 1, except that no nucleating agent was added.

[0093] Comparative Example 2 Evaluation was carried out in the same manner as in Comparative Example 1, except that 0.05 parts by mass of calcium stearate (lubricant) was not blended.

[0094] [Comparative Examples 3 and 4] Comparative Examples 3 and 4 were evaluated in the same manner as in Example 1, except that the following comparative compounds-1 and -2 were used as nucleating agents.

[0095] TIFF2025169326000014.tif74166

[0096] [Crystallization temperature measurement method] Each pellet was heated to 230°C at a rate of 50°C / min using a differential scanning calorimeter (Diamond, manufactured by PerkinElmer), held for 10 minutes, and then cooled to 50°C at a rate of -10°C / min. The crystallization temperature was determined by the peak top of the exothermic peak that appeared during the cooling process. The results are shown in Tables 1 to 8 below.

[0097] [Transparency evaluation (Haze value)] Each pellet was injected into a mold using an injection molding machine (EC100-2A; manufactured by Toshiba Machine Co., Ltd.) at an injection temperature of 200°C and an injection pressure of 40–60 MPa for 40 seconds. The mold was then cooled for 20 seconds at 40°C before being removed from the mold. This injection molding process yielded a 60 mm square sheet with a thickness of 1 mm. The resulting sheet was then placed in a constant temperature bath at 23°C for one week. The haze value of the test specimens was then measured using a Haze Guard 2 (manufactured by Toyo Seiki Seisakusho Co., Ltd.). The lower the value, the better the transparency of the test specimen. These results are summarized in Tables 1–8 below.

[0098] [Bending modulus evaluation] Each pellet was injected into a mold using an injection molding machine (EC100-2A; manufactured by Toshiba Machine Co., Ltd.) at an injection temperature of 200°C and an injection pressure of 40 to 60 MPa for 40 seconds. The pellets were then cooled in the mold at 40°C for 20 seconds and removed from the mold. Bending test specimens measuring 80 mm in length, 10 mm in width, and 4 mm in thickness were then produced. The resulting bending test specimens were then placed in a thermostatic chamber at 23°C for one week immediately after injection molding, and their flexural modulus (MPa) was measured using a bending tester (manufactured by Shimadzu Corporation; AG-IS). The results are shown in Tables 1 to 8 below.

[0099] [Head deflection temperature (HDT)] Each pellet was injected into a mold using an injection molding machine (EC100-2A; manufactured by Toshiba Machine Co., Ltd.) at an injection temperature of 200°C and an injection pressure of 40–60 MPa for 40 seconds. The pellets were then cooled in the mold at 40°C for 20 seconds before being removed from the mold. HDT test specimens measuring 80 mm in length, 10 mm in width, and 4 mm in thickness were prepared by injection molding. The obtained HDT test specimens were immediately placed in a thermostatic chamber at 23°C for one week after injection molding and then measured using an automatic HDT tester (manufactured by Toyo Seiki Co., Ltd.) using the flatwise method. Testing was performed at a heating rate of 120°C / h and a bending stress of 1.8 MPa. The temperature at which the specimen reached a load-induced deflection of 0.34 mm was recorded as the deflection temperature under load (HDT). These results are summarized in Tables 1–8 below.

[0100] [Table 1]

[0101] [Table 2]

[0102] [Table 3]

[0103] [Table 4]

[0104] [Table 5]

[0105] [Table 6]

[0106] [Table 7]

[0107] [Table 8]

[0108] The results shown in Tables 1 to 8 show that the transparency of synthetic resins can be improved by the nucleating agent of the present invention.

Claims

1. The method includes a step of blending a nucleating agent into a synthetic resin, the synthetic resin includes a polyolefin resin (excluding halogen-containing resins), A method for improving transparency of a synthetic resin, wherein the nucleating agent contains one or more triazine compounds represented by the following general formula (1): (In general formula (1), Ar １ , Ar ２ and Ar ３ each independently represents an unsubstituted phenyl group or a substituted phenyl group, Ar １ and Ar ２ are the same group, and Ar ３ Ar １ and Ar ２ is a different group from

2. The method includes a step of blending a nucleating agent into a synthetic resin, the synthetic resin includes a polyolefin resin (excluding halogen-containing resins), A method for improving transparency of a synthetic resin, wherein the nucleating agent contains one or more triazine compounds represented by the following general formula (1): (In general formula (1), Ar １ , Ar ２ and Ar ３ each independently represents an unsubstituted phenyl group or a substituted phenyl group, Ar １ , Ar ２ and Ar ３ are all different groups.)

3. 3. The method for improving transparency of a synthetic resin according to claim 1, wherein the blending amount of the nucleating agent is 0.001 to 10 parts by mass per 100 parts by mass of the synthetic resin.

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