Granular ultraviolet absorber and resin composition

Abstract

To provide a granular ultraviolet absorber having excellent powder characteristics.SOLUTION: A granular ultraviolet absorber according to the present invention is a granular ultraviolet absorber containing a triazine-based compound, wherein, when measured by using a wet laser diffraction-type particle-size-distribution measuring method, D10 / D90 is within the range of 0.01-0.25, where D10 is the cumulative 10% particle size of the granular ultraviolet absorber in a volume-based particle size distribution, and D90 is the cumulative 90% particle size thereof.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a granular ultraviolet absorber and a resin composition. [Background technology]

[0002] Various developments have been made in the field of ultraviolet absorbers. For example, the technology described in Patent Document 1 is known as this type of technology. Patent Document 1 describes the use of a triazine-based compound obtained by crystallization as an ultraviolet absorber (paragraph 0102 of Patent Document 1, etc.). [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Laid-Open No. 2011-6517 Summary of the Invention [Problem to be solved by the invention]

[0004] However, as a result of investigations by the present inventors, it has been found that the ultraviolet absorber described in Patent Document 1 has room for improvement in terms of powder properties. [Means for solving the problem]

[0005] As a result of further investigation, the present inventors have found that the powder properties of a granular ultraviolet absorber containing a triazine compound can be appropriately controlled by using the particle size distribution determined by a wet laser diffraction particle size distribution measurement method as a guideline. Based on this finding, further intensive research has revealed that the cumulative 10% particle diameter D 10 / Cumulative 90% particle size D 90 The present inventors have found that the powder properties of the granular ultraviolet absorber can be improved by adjusting the value of the powder to fall within a predetermined range, and have completed the present invention.

[0006] According to the present invention, A granular ultraviolet absorber containing a triazine-based compound, The cumulative 10% particle size in the volume-based particle size distribution of the granular UV absorber measured by the wet laser diffraction particle size distribution measurement method is D 10 (μm), cumulative 90% particle diameter is D 90 (μm), D 10 / D 90 is in the range of 0.01 or more and 0.25 or less.

[0007] The present invention also provides a resin composition containing the above-mentioned granular ultraviolet absorber. [Effects of the Invention]

[0008] According to the present invention, there are provided a granular ultraviolet absorber having excellent powder properties and a resin composition using the same. [Brief explanation of the drawings]

[0009] The above-mentioned objects, as well as other objects, features and advantages, will become more apparent from the preferred embodiments described below and the accompanying drawings.

[0010] [Figure 1] 1 is an X-ray diffraction pattern of the granular ultraviolet absorber of Example 1. [Figure 2] 1 is an X-ray diffraction pattern of the granular ultraviolet absorber of Example 11. [Figure 3] 1 is an X-ray diffraction pattern of a granular ultraviolet absorber of Comparative Example 1. DETAILED DESCRIPTION OF THE INVENTION

[0011] The granular ultraviolet absorber of this embodiment contains a triazine-based compound. The triazine compound preferably contains a compound represented by the following general formula (I): These may be used alone or in combination of two or more. The granular ultraviolet absorber may be composed solely of the following triazine-based compound.

[0012] [ka]

[0013] In the above general formula (I), R 1 represents a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkylaryl group having 7 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or a substituent represented by the following general formula (II): R 2 and R 3 each independently represents a hydrogen atom, a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms, or -OR, in which R represents a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkylaryl group having 7 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms; R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 each independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted linear or branched alkyl group having 1 to 8 carbon atoms, or a linear or branched alkenyl group having 2 to 8 carbon atoms; R 13 and R 14 each independently represents a hydrogen atom or a hydroxy group.

[0014] However, R 1 , R 2 , R 3 and a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms represented by R, R4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 The methylene group in the substituted or unsubstituted, linear or branched alkyl group having 1 to 8 carbon atoms represented by the formula: 01 =N- and -N=CR 02 -, and in the structure R 01 and R 02 each independently represents a linear or branched alkyl group having 1 to 8 carbon atoms.

[0015] [ka]

[0016] In the above general formula (II), R 21 and R 22 each independently represents a hydrogen atom, a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms, or -OR, in which R represents a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkylaryl group having 7 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms; R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 and R 31 each independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted linear or branched alkyl group having 1 to 8 carbon atoms, or a linear or branched alkenyl group having 2 to 8 carbon atoms; R 32 and R33 each independently represents a hydrogen atom or a hydroxy group, X 1 represents a substituted or unsubstituted, linear or branched alkylene group having from 8 to 30 carbon atoms, Y 1 and Y 2 are each independently -CO-O-, -O-CO-, -L 1 -, -OL 1 O-, -OL 1 -, -L 1 -O-CO-, -L 1 -CO-O-, -CO-CH=CH-, -CH=CH-CO-, -CH=CH-CO-O-, -CH=CH-O-CO-, -CO-O-CH=CH-, L 1 is a linear or branched alkylene group having 1 to 8 carbon atoms, m and n each independently represent an integer of 0 to 8; * indicates R in formula (I). 1 represents the bond to the oxygen atom connected to the

[0017] However, R 21 , R 22 and a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms represented by R, R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 and R 31 and X is a substituted or unsubstituted, linear or branched alkyl group having 1 to 8 carbon atoms, represented by the following formula: 1 The methylene group in the linear or branched alkylene group having 8 to 30 carbon atoms represented by the formula (I) is an oxygen atom, a sulfur atom, a carbon-carbon double bond, -CO-, -CO-O-, -OC-O-, -CO-NH-, -NH-CO-, -CR 03 =N- and -N=CR 04 -, and R 03 and R 04each independently represents a linear or branched alkyl group having 1 to 8 carbon atoms.

[0018] R in the above general formula (I) 1 , R 2 , R 3 , R in the above general formula (II) 21 , R 22 Examples of the substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms represented by R include linear or branched alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, amyl, isoamyl, tert-amyl, hexyl, heptyl, n-octyl, isooctyl, tert-octyl, 2-ethylhexyl, nonyl, isononyl, decyl, undecyl, and dodecyl.

[0019] R in the above general formula (I) 1 Examples of the cycloalkyl group having 3 to 20 carbon atoms represented by R include cyclopropyl, cyclopentyl, cyclohexyl, and cycloheptyl.

[0020] R in the above general formula (I) 1 and examples of the aryl group having 6 to 20 carbon atoms represented by R include phenyl, naphthyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-vinylphenyl, 3-isopropylphenyl, 4-isopropylphenyl, 4-butylphenyl, 4-isobutylphenyl, 4-tert-butylphenyl, 4-hexylphenyl, 4-cyclohexylphenyl, 4-octylphenyl, 4-(2-ethylhexyl)phenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,4-di-tert-butylphenyl, 2,5-di-tert-butylphenyl, 2,6-di-tert-butylphenyl, 2,4-di-tert-pentylphenyl, 2,5-di-tert-amylphenyl, 2,5-di-tert-octylphenyl, biphenyl, and 2,4,5-trimethylphenyl.

[0021] R in the above general formula (I) 1 Examples of the arylalkyl group having 7 to 20 carbon atoms represented by R include benzyl, phenethyl, 2-phenylpropan-2-yl, and diphenylmethyl.

[0022] R in the above general formula (I) 1 Examples of the alkylaryl group having 7 to 20 carbon atoms represented by R include groups in which one hydrogen atom of the above alkyl groups is substituted with an aryl group, and examples of the aryl group include phenyl, cresyl, xylyl, 2,6-xylyl, 2,4,6-trimethylphenyl, butylphenyl, nonylphenyl, biphenyl, naphthyl, and anthracenyl.

[0023] R in the above general formula (I) 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 and R in the above general formula (II) 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 and R 31 Examples of the halogen atom represented by the formula (I) include fluorine, chlorine, bromine, and iodine.

[0024] R in the above general formula (I) 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 and R in the above general formula (II) 23 , R 24 , R 25 , R 26 , R27 , R 28 , R 29 , R 30 and R 31 Examples of the substituted or unsubstituted, linear or branched alkyl group having 1 to 8 carbon atoms represented by the formula (I) include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, amyl, isoamyl, tert-amyl, hexyl, heptyl, n-octyl, isooctyl, tert-octyl, 2-ethylhexyl, etc. In the granular ultraviolet absorber of the present embodiment, an alkyl group having 1 to 8 carbon atoms is preferred.

[0025] R in the above general formula (I) 1 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 and R in the above general formula (II) 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 and R 31 Examples of the linear or branched alkenyl group having 2 to 8 carbon atoms represented by the formula (I) include linear and branched propenyl, butenyl, pentenyl, hexenyl, heptenyl and octenyl, regardless of the position of the unsaturated bond.

[0026] X in the above general formula (II) 1 The substituted or unsubstituted, linear or branched alkylene group having from 8 to 30 carbon atoms, represented by the formula (I), represents an alkylene group in which from 8 to 30 methylenes are linked together, or an alkylene group in which hydrogen atoms of some methylenes are substituted with alkyl groups. In the granular ultraviolet absorber of this embodiment, an alkylene group having from 8 to 20 carbon atoms is preferred.

[0027] In the above general formula (II), L 1Examples of the linear or branched alkylene group having 1 to 8 carbon atoms represented by the formula (I) include methylene, methylmethylene, dimethylmethylene, ethylene, propylene, isopropylene, butylene, isobutylene, and pentylene.

[0028] The triazine compound is a compound represented by the general formula (I) in which R 5 , R 6 , R 8 , R 9 , R 11 and R 12 may contain a compound in which is a hydrogen atom. Moreover, examples of the triazine-based compound represented by the above general formula (I) include a compound represented by the following general formula (A) or a compound represented by the following general formula (B).

[0029] The granular ultraviolet absorber of this embodiment can use a compound represented by the following general formula (A): These can be used alone or in combination of two or more.

[0030] [ka]

[0031] In the above general formula (A), R A1 represents a linear or branched alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a linear or branched alkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 18 carbon atoms, an alkylaryl group having 7 to 18 carbon atoms, or an arylalkyl group having 7 to 18 carbon atoms, R A2 and R A3 may be the same or different and represent a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, or a linear or branched alkoxy group having 1 to 12 carbon atoms; R A4 , R A7 , R A10may be the same or different and represent a hydrogen atom, a linear or branched alkyl group having 1 to 8 carbon atoms, or a linear or branched alkenyl group having 3 to 8 carbon atoms, R A13 and R A17 may be the same or different and represent a hydrogen atom or a hydroxy group. However, R A1 , R A2 and R A3 a linear or branched alkyl group having 1 to 12 carbon atoms represented by the formula: A2 and R A3 The methylene group in the linear or branched alkoxy group having 1 to 12 carbon atoms represented by the formula (I) is not limited to an oxygen atom, a sulfur atom, a carbon-carbon double bond, -CO-, -CO-O-, -OC-O-, -CO-NH-, -NH-CO-, -CR 05 =N- and -N=CR 06 -, and in the structure R 05 and R 06 each independently represents a linear or branched alkyl group having 1 to 8 carbon atoms.

[0032] R in the above general formula (A) A1 , R A2 and R A3 Examples of the linear or branched alkyl group having 1 to 12 carbon atoms represented by the formula (I) include linear or branched alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, amyl, isoamyl, tert-amyl, hexyl, heptyl, n-octyl, isooctyl, tert-octyl, 2-ethylhexyl, nonyl, isononyl, decyl, undecyl, and dodecyl.

[0033] R in the above general formula (A) A2 and R A3Examples of the linear or branched alkoxy group having 1 to 12 carbon atoms represented by the formula (I) include methyloxy, ethyloxy, isopropyloxy, butyloxy, sec-butyloxy, tert-butyloxy, isobutyloxy, amyloxy, isoamyloxy, tert-amyloxy, hexyloxy, 2-hexyloxy, 3-hexyloxy, cyclohexyloxy, 4-methylcyclohexyloxy, heptyloxy, 2-heptyloxy, 3-heptyloxy, isoheptyloxy, tert-heptyloxy, 1-octyloxy, isooctyloxy, and tert-octyloxy.

[0034] R in the above general formula (A) A1 Examples of the cycloalkyl group having 3 to 8 carbon atoms represented by the formula include cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, and the like.

[0035] R in the above general formula (A) A1 Examples of the aryl group having 6 to 18 carbon atoms or the alkylaryl group having 7 to 18 carbon atoms represented by the formula (I) include phenyl, naphthyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-vinylphenyl, 3-isopropylphenyl, 4-isopropylphenyl, 4-butylphenyl, 4-isobutylphenyl, 4-tert-butylphenyl, 4-hexylphenyl, 4-cyclohexylphenyl, 4-octylphenyl, 4-(2-ethylhexyl)phenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, Examples of the arylalkyl group having 7 to 18 carbon atoms include benzyl, phenethyl, 2-phenylpropan-2-yl, and diphenylmethyl.

[0036] In the above general formula (A), R A1 , R A4 , R A7 , and R A10 Examples of the linear or branched alkenyl group having 3 to 8 carbon atoms represented by the formula (I) include linear and branched propenyl, butenyl, pentenyl, hexenyl, heptenyl and octenyl, regardless of the position of the unsaturated bond.

[0037] In the above general formula (A), R A4 , R A7 , R A10 Examples of the linear or branched alkyl group having 1 to 8 carbon atoms represented by the formula (I) include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, tert-amyl, octyl, tert-octyl, etc. Among these, the methyl group is preferred because of its excellent ultraviolet absorbing ability.

[0038] The triazine compound represented by the general formula (A) preferably includes one or more triazine compounds represented by any one of Compound No. 1A to Compound No. 5A below.

[0039] [ka]

[0040] The triazine compound represented by the general formula (A) preferably includes one or more triazine compounds represented by any one of Compound No. 6A to Compound No. 8A below. [ka]

[0041] The granular ultraviolet absorber of the present embodiment can use a compound represented by the following general formula (B): These can be used alone or in combination of two or more.

[0042] [ka]

[0043] In the above general formula (B), R B4 , R B5 , R B7 ~R B9 , R B10 ~R B12 , R B23 , R B24 , R B26 ~R B28 , R B29 ~R B31 each independently represents a hydrogen atom, a hydroxy group, a halogen atom, a linear or branched alkyl group having 1 to 8 carbon atoms, a linear or branched alkenyl group having 2 to 8 carbon atoms, a linear or branched alkoxy group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms, and n represents an integer of 8 to 14. However, of the three benzene rings linked to the triazine ring, the para-positions of two benzene rings represent a hydrogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms, or a linear or branched alkoxy group having 1 to 20 carbon atoms, and one of the ortho-positions represents a hydrogen atom or a hydroxy group.

[0044] In the above general formula (B), R B4 , R B5 , R B7 ~R B9 , R B10 ~R B12 , R B23 , R B24 , R B26 ~R B28 , R B29 ~R B31 Examples of the halogen atom represented by the formula (I) include a fluorine atom, a chlorine atom, and a bromine atom.

[0045] In the above general formula (B), R B4 , R B5 , R B7 ~R B9 , R B10 ~R B12 , R B23 , R B24 , R B26 ~RB28 , R B29 ~R B31 Examples of the linear or branched alkyl group having 1 to 20 carbon atoms represented by the formula include methyl, ethyl, propyl, 2-propynyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, decyl, dodecyl, and octadecyl.

[0046] In the above general formula (B), R B4 , R B5 , R B7 ~R B9 , R B10 ~R B12 , R B23 , R B24 , R B26 ~R B28 , R B29 ~R B31 Examples of the linear or branched alkenyl group having 2 to 8 carbon atoms represented by the formula (I) include vinyl, 1-propenyl, isopropenyl, 2-methyl-1-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-ethyl-1-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 4-methyl-3-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, and 5-hexenyl.

[0047] In the above general formula (B), R B4 , R B5 , R B7 ~R B9 , R B10 ~R B12 , R B23 , R B24 , R B26 ~R B28 , R B29 ~R B31Examples of the linear or branched alkoxy group having 1 to 20 carbon atoms represented by the formula (I) include methyloxy, ethyloxy, isopropyloxy, butyloxy, sec-butyloxy, tert-butyloxy, isobutyloxy, amyloxy, isoamyloxy, tert-amyloxy, hexyloxy, 2-hexyloxy, 3-hexyloxy, cyclohexyloxy, 4-methylcyclohexyloxy, heptyloxy, 2-heptyloxy, 3-heptyloxy, isoheptyloxy, tert-heptyloxy, 1-octyloxy, isooctyloxy, and tert-octyloxy.

[0048] In the above general formula (B), R B4 , R B5 , R B7 ~R B9 , R B10 ~R B12 , R B23 , R B24 , R B26 ~R B28 , R B29 ~R B31Examples of the aryl group having 6 to 20 carbon atoms represented by the formula (I) include phenyl, naphthyl, anthracenyl, phenanthryl, fluorenyl, indenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-vinylphenyl, 3-isopropylphenyl, 4-isopropylphenyl, 4-butylphenyl, 4-isobutylphenyl, 4-tert-butylphenyl, 4-hexylphenyl, 4-cyclohexylphenyl, 4-octylphenyl, 4-(2-ethylhexyl)phenyl, 4-stearylphenyl, 2,3-dimethylphenyl, 2,4-diphenyl ... Examples thereof include methylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,4-di-tert-butylphenyl, 2,5-di-tert-butylphenyl, 2,6-di-tert-butylphenyl, 2,4-di-tert-pentylphenyl, 2,5-di-tert-amylphenyl, 2,5-di-tert-octylphenyl, 2,4-dicumylphenyl, 4-cyclohexylphenyl, (1,1'-biphenyl)-4-yl, 2,4,5-trimethylphenyl, and ferrocenyl.

[0049] The triazine compound represented by the general formula (B) preferably includes one or more triazine compounds represented by any one of Compound No. 1B to Compound No. 4B below. [ka]

[0050] Among the above compounds No.1B to Compound No.4B, R A1 , R A2 , R B1 , R B2 , R C1 , R C2 , R D1 and R D2 may be the same or different and represent a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched alkoxy group having 1 to 4 carbon atoms.

[0051] The synthesis method of the triazine compound is not particularly limited and may be any synthesis method commonly used for synthesizing compounds having a triazine structure. For example, a method of adding a phenol derivative or a resorcinol derivative to cyanuric chloride using aluminum trichloride may be mentioned. The substituent on the benzene ring connected to the triazine ring by a single bond may be introduced after the triazine structure is formed, or may be introduced into the phenol compound or the resorcinol derivative before the triazine structure is formed.

[0052] An example of a method for synthesizing the triazine-based compound is, for example, an esterification reaction or transesterification reaction of 2-[2-hydroxy-4-(2-hydroxyethyloxy)phenyl]-4,6-diphenyl-1,3,5-triazine as an alcohol component with a corresponding ester-derived compound (carboxylic acid, carboxylic acid halide, carboxylic acid ester), and these reactions may be sequential reactions or batch reactions. Examples of the alcohol component include ester-derived compounds of monocarboxylic acids (monocarboxylic acids, monocarboxylic acid halides, and monocarboxylic acid esters), ester-derived compounds of dicarboxylic acids (dicarboxylic acids, dicarboxylic acid halides, and dicarboxylic acid esters), etc.

[0053] The triazine compounds can be purified after synthesis. Purification methods that can be used include distillation, recrystallization, reprecipitation, and methods using a filtering agent or adsorbent. These methods can be used alone or in combination of two or more.

[0054] The triazine-based compound may be subjected to processing such as pulverization, granulation, classification, melting, and solidification after purification, as needed. These may be used alone or in combination of two or more. This allows the desired powder properties of the granular triazine-based compound to be obtained.

[0055] The term "granular" in the granular ultraviolet absorber of the present embodiment means a powder or granule form. This granular ultraviolet absorber may be used in the form of powder or granules as it is, or may be processed into a specific shape such as pellets, briquettes, or tablets before use.

[0056] The granular ultraviolet absorber of this embodiment has properties defined by the following particle size distribution.

[0057] When the particle size distribution of the granular ultraviolet absorber of this embodiment is measured by a wet laser diffraction particle size distribution measurement method, the cumulative 10% particle size in the volume-based particle size distribution is D 10 (μm), cumulative 90% particle diameter is D 90 (μm), the cumulative 98% particle size in the volume-based particle size distribution is D 98 (μm), the volume average particle size in the particle size distribution based on volume is MV (μm), and the number average particle size is MN (μm).

[0058] According to the findings of the present inventors, it has been found that by adopting wet conditions, it is possible to measure the particle size distribution of powders having a relatively wide particle size distribution and containing fine particles more stably than under dry conditions.

[0059] In this embodiment, D 10 / D 90 is, for example, in the range of 0.01 or more and 0.25 or less, preferably 0.02 or more and 0.20 or less, and more preferably 0.03 or more and 0.15 or less. 10 / D 90 By setting D to the above upper limit or less, the particle size distribution can be broadened over a relatively wide range, which improves the compressive granulation properties and melt-kneading properties. As a result, a granular ultraviolet absorber with excellent powder properties can be realized. 10 / D 90 By making the above lower limit or more, it is possible to realize a granular ultraviolet absorber that is excellent in melt-kneadability and production stability.

[0060] Although the detailed mechanism is unclear, it is thought that by broadening the particle size distribution appropriately, fine particles can enter the gaps between particles, reducing the void ratio, thereby suppressing lamination and increasing thermal conductivity and compatibility with resins.

[0061] In this embodiment, D 98 / D 90 is, for example, in the range of 1.70 or more and 5.00 or less, preferably 1.80 or more and 4.50 or less, and more preferably 1.90 or more and 4.00 or less. By setting it within such a numerical range, a granular ultraviolet absorber excellent in powder properties and ultraviolet absorbing properties can be realized.

[0062] In this embodiment, D 10 is, for example, in the range of 8.0 μm or more and 22.0 μm or less, preferably 9.0 μm or more and 20.0 μm or less, and more preferably 10.0 μm or more and 18.0 μm or less. By keeping it within such a numerical range, the powder properties can be improved.

[0063] In this embodiment, D 90 is, for example, in the range of 120.0 μm or more and 500.0 μm or less, preferably 125.0 μm or more and 450.0 μm or less, and more preferably 130.0 μm or more and 400.0 μm or less. By keeping it within such a numerical range, the powder properties can be improved.

[0064] In this embodiment, MV / MN is, for example, in the range of 5.0 or more and 30.0 or less, preferably 8.0 or more and 28.0 or less, and more preferably 10.0 or more and 25.0 or less. By setting it within such a numerical range, a granular ultraviolet absorber having excellent powder properties and ultraviolet absorption properties can be realized.

[0065] In this embodiment, for example, by appropriately selecting the type and shape of the triazine-based compound, the preparation method of the triazine-based compound, etc., the above D 10 / D 90 , D 98 / D 90Among these, it is possible to control the MV / MN ratio. Among these, for example, the above D can be achieved by appropriately adopting the processing conditions of triazine compounds, such as melt solidification, pulverization, and classification. 10 / D 90 , D 98 / D 90 , are factors for setting MV / MN in a desired numerical range.

[0066] Furthermore, the present inventors have further studied and found that the powder properties of triazine compounds and granular UV absorbers using the same can be appropriately controlled by using X-ray diffraction analysis patterns as a guideline. Based on this finding, the present inventors have conducted further intensive research and found that the powder properties of the above-mentioned triazine compounds and granular UV absorbers using the same can be improved by setting the diffraction angle 2θ at which a maximum peak exists in a powder X-ray diffraction analysis pattern within a predetermined numerical range.

[0067] The triazine compound (particulate ultraviolet absorber) of this embodiment may have properties defined by the following powder X-ray diffraction analysis pattern.

[0068] The triazine compound of this embodiment may have a maximum peak in a powder X-ray diffraction analysis pattern with a diffraction angle 2θ of 5.00° or more and 6.50° or less, preferably 5.20° or more and 6.00° or less, and more preferably 5.40° or more and 5.80° or less. This can improve feedability and compression granulation properties, thereby realizing a triazine compound or a granular UV absorber with excellent powder properties. Here, the maximum peak is one having the maximum peak intensity in an X-ray diffraction pattern obtained within the scanning range (for example, diffraction angle 2θ=3° to 60° or 3° to 90°) in powder X-ray diffraction measurement.

[0069] In addition, in the powder X-ray diffraction analysis pattern of the triazine compound, the half-value width of the maximum peak is, for example, 0.05° to 0.20°, preferably 0.10° to 0.19°, and more preferably 0.15° to 0.18°. By appropriately setting the peak width of the maximum peak (largest peak) so that it falls within this numerical range, a granular ultraviolet absorber with excellent powder properties and ultraviolet absorption properties can be realized.

[0070] In addition, in the powder X-ray diffraction analysis pattern of the triazine compound, when the relative intensity of the maximum peak is taken as 100, the triazine compound is configured so that, for example, no diffraction peak has a relative intensity of 30 or more and 60 or less, preferably a relative intensity of 25 or more and 60 or less, more preferably a relative intensity of 22 or more and 60 or less, within a diffraction angle 2θ range of 3.0° or more and 45.0° or less. In other words, by relatively increasing the peak intensity of the maximum peak value, a granular ultraviolet absorber with excellent powder properties and ultraviolet absorption properties can be realized.

[0071] Furthermore, in the powder X-ray diffraction analysis pattern of the triazine compound, when the relative intensity of the maximum peak is taken as 100, the diffraction peak having a relative intensity of 1 or more and 5 or less is configured not to exist, for example, in a range of diffraction angle 2θ greater than 45.0° and less than 60.0°, preferably greater than 45.0° and less than 90.0°. In other words, by setting the region where no weak intensity peak exists within an appropriate numerical range, a granular ultraviolet absorber having excellent powder properties and ultraviolet absorption properties can be realized.

[0072] In this embodiment, it is possible to control the powder X-ray diffraction analysis pattern, such as the diffraction angle 2θ of the maximum peak and the half-width of the maximum peak, by appropriately selecting, for example, the type and shape of the triazine-based compound, the preparation method of the triazine-based compound, etc. Among these, for example, appropriately adopting processing conditions for the triazine-based compound, such as melt-solidification, pulverization, and classification, is an element for setting the powder X-ray diffraction analysis pattern, such as the diffraction angle 2θ of the maximum peak and the half-width of the maximum peak, within a desired numerical range.

[0073] The resin composition of this embodiment will be described.

[0074] The resin composition contains the granular ultraviolet absorber. This resin composition may contain a synthetic resin. This allows desired resin properties to be obtained according to various applications.

[0075] Examples of the synthetic resin include thermoplastic resins, thermosetting resins, elastomers, etc. These may be used alone or in combination of two or more.

[0076] Specific examples of the synthetic resin include the following. Examples of the thermoplastic resin 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; polyolefins such as ethylene-vinyl acetate copolymer, ethylene-ethyl acrylate copolymer, and ethylene-propylene copolymer, and 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 acid ester copolymer, vinyl chloride-cyclohexylmaleimide copolymer; Examples of the polyester include: aromatic polyesters such as polyalkylene terephthalates (e.g., polyethylene terephthalate, polybutylene terephthalate, polycyclohexanedimethylene terephthalate), polyalkylene naphthalates (e.g., polyethylene naphthalate, 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); polyamides (e.g., polyphenylene oxide, polycaprolactam, and polyhexamethylene adipamide), polycarbonate, branched polycarbonate, polyacetal, polyphenylene sulfide, polyurethane, and cellulose-based resins.

[0077] Examples of the thermosetting resin include phenol resin, urea resin, melamine resin, epoxy resin, and unsaturated polyester resin.

[0078] Examples of the elastomer include fluorine-based resins, silicone resins, silicone rubber, polyethersulfone, polysulfone, polyphenylene ether, polyetherketone, polyetheretherketone, liquid crystal polymers, etc. Further examples include isoprene rubber, butadiene rubber, acrylonitrile-butadiene copolymer rubber, styrene-butadiene copolymer rubber, fluorine rubber, silicone rubber, etc. More specific examples of the elastomer 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.

[0079] Examples of synthetic resins with excellent transparency include polyethylene, polypropylene, polystyrene, copolymers of polyethylene and cycloolefins such as norbornene, vinyl compounds and addition polymers of vinyl compounds such as polyacrylic acid, polyacrylic acid esters, polyvinyl acetate, polyacrylonitrile, polyvinyl chloride, and polyvinyl fluoride, copolymers of vinyl compounds or fluorine-based compounds such as polymethacrylic acid, polymethacrylic acid esters, polyvinylidene chloride, polyvinylidene fluoride, polyvinylidene cyanide, vinylidene fluoride / trifluoroethylene copolymer, vinylidene fluoride / tetrafluoroethylene copolymer, and vinylidene cyanide / vinyl acetate copolymer, fluorine-containing compounds such as polytrifluoroethylene, polytetrafluoroethylene, and polyhexafluoropropylene, polyamides such as nylon 6 and nylon 66, polyimides, polyurethanes, polypeptides, polyesters such as polybutylene terephthalate and polyethylene terephthalate, polyethers such as polycarbonate, polyoxymethylene, polyethylene oxide, and polypropylene oxide, epoxy resins, polyvinyl alcohol, and polyvinyl butyral.

[0080] From the viewpoint of compatibility and transparency, examples of synthetic resins include polycarbonate resin, polyester resin, acrylic resin, and ABS resin.

[0081] The above synthetic resins may be used alone or in combination of two or more kinds, or may be alloyed.

[0082] The amount of the granular UV absorber in the resin composition is, for example, preferably 0.001 to 20 parts by mass, more preferably 0.01 to 10 parts by mass, and even more preferably 0.1 to 5 parts by mass, relative to 100 parts by mass of the synthetic resin. By adjusting the amount to be equal to or greater than the lower limit, the sufficient effect of the granular UV absorber can be obtained. On the other hand, by adjusting the amount to be equal to or less than the upper limit, the desired resin properties can be achieved while improving the effect of adding the granular UV absorber. In this specification, unless otherwise specified, the symbol "to" indicates that the upper and lower limits are included.

[0083] The resin composition of this embodiment may contain additives other than the above-described components as needed. Examples of such additives include antioxidants, ultraviolet absorbers other than the triazine-based compound of this embodiment, hindered amine-based light stabilizers, near-infrared absorbers, nucleating agents (clarifying agents), antistatic agents, lubricants, plasticizers, light-absorbing dyes, fillers, pigments, dyes, metal soaps, processing aids, flame retardants, flame retardant assistants, zeolite compounds, foaming agents, (heavy) metal deactivators, crosslinking agents, epoxy-based stabilizers, matting agents, antifogging agents, anti-plateout agents, surface treatment agents, fluorescent brighteners, antifungal agents, antibacterial agents, and mold release agents.

[0084] Examples of the antioxidant include phenol-based antioxidants, phosphorus-based antioxidants, and sulfur-based antioxidants.

[0085] Examples of the phenolic antioxidant 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'-butylidenebis(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-ditert-butyl-4-hydroxybenzyl) benzyl) isocyanurate, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-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-hexamethylenebis[(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], bis[3,3-bis(4-hydroxy-3-tert-butylphenyl)butylic 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-di-tert-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.

[0086] Examples of the phosphorus-based antioxidant include trisnonylphenyl phosphite, tris[2-tert-butyl-4-(3-tert-butyl-4-hydroxy-5-methylphenylthio)-5-methylphenyl]phosphite, tridecyl phosphite, triisodecyl phosphite, trilauryl phosphite, octyldiphenyl phosphite, di(decyl)monophenyl phosphite, di(tridecyl)pentaerythritol diphosphite, and di(nonylphenyl)pentaerythritol diphosphite. diphosphite, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite, bis(2,4,6-tri-tert-butylphenyl)pentaerythritol diphosphite, bis(2,4-dicumylphenyl)pentaerythritol diphosphite, tetra(tridecyl)isopropylidenediphenol diphosphite, tetra(tridecyl)-4,4'-n-butylphenyl Hexylidenebis(2-tert-butyl-5-methylphenol)diphosphite, hexa(tridecyl)-1,1,3-tris(2-methyl-4-hydroxy-5-tert-butylphenyl)butanetriphosphite, tetrakis(2,4-di-tert-butylphenyl)biphenylene diphosphonite, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 2,2'-methylenebis(4,6-tert-butylphenyl)-2-ethylhexylphospha phosphite, 2,2'-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, phosphite of 2-ethyl-2-butylpropylene glycol and 2,4,6-tri-tert-butylphenol, and the like.

[0087] Examples of the sulfur-based antioxidant include dialkylthiodipropionates such as dilauryl thiodipropionate, dimyristyl thiodipropionate, and distearyl thiodipropionate, and pentaerythritol tetra(β-alkylthiopropionic acid) esters.

[0088] Examples of ultraviolet absorbers other than the triazine-based compound according to the present embodiment 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, 2-(2'-hydroxy-3'-tert-butyl-5'-methylphenyl)-5-chlorobenzotriazole, 2-(2'-hydroxy-5'-tert-octylphenyl)benzotriazole, 2-(2'-hydroxy-3',5'-dicumylphenyl)benzotriazole, and 2,2'-methylenebis(4-tert-octyl-6-(benzylphenyl)benzotriazole). 2-(2'-hydroxyphenyl)benzotriazoles such as 2-(2'-hydroxy-3'-tert-butyl-5'-carboxyphenyl)benzotriazole; phenyl salicylate, resorcinol monobenzoate, 2,4-di-tert-butylphenyl-3,5-di-tert-butyl-4-hydroxybenzoate, 2,4-di-tert-amylphenyl-3,5-di-tert- Benzoates such as butyl-4-hydroxybenzoate and hexadecyl-3,5-di-tert-butyl-4-hydroxybenzoate; substituted oxanilides such as 2-ethyl-2'-ethoxyoxanilide and 2-ethoxy-4'-dodecyloxanilide; and cyanoacrylates such as ethyl-α-cyano-β,β-diphenylacrylate and methyl-2-cyano-3-methyl-3-(p-methoxyphenyl)acrylate.

[0089] 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-tetramethyl-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)·di(tridecyl)-1,2,3,4-butanetetracarboxylate, bis(1,2,2,6,6-pentamethyl-4-piperidyl)·di(tridecyl)-1,2,3,4-butanetetracarboxylate, bis(1,2,2,4,4-pentamethyl-4-piperidyl)-2-butyl-2-(3,5-di-tert-butyl- 4-Hydroxybenzyl)malonate, 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-piperidinol / diethyl succinate 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-piperidylamino)hexane] 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-yl]aminoundecane, 1,6,11-tris[2,4-bis(N-butyl-N-(1,Examples of hindered amine compounds include 2,2,6,6-pentamethyl-4-piperidyl)amino)-s-triazin-6-yl)aminoundecane.

[0090] Examples of the near-infrared absorber include polymethine dyes (cyanine dyes), indolinocyanine dyes, phthalocyanine dyes, naphthalocyanine dyes, naphthol metal complex dyes, squarylium dyes, triazo dyes, dithiol metal complex dyes, pyrylium dyes, thiapyrylium dyes, indoaniline dyes, azoanthraquinone dyes, naphthoquinone dyes, anthroquinone dyes, bis(dithiolene) dyes, triphenylmethane dyes, aminium (aluminum) dyes, and diimonium dyes. Furthermore, inorganic near-infrared absorbers may also be used, such as carbon black, tin oxide doped with antimony oxide or indium oxide, and oxides, carbides, or borides of metals belonging to Group 4A, 5A, or 6A of the periodic table.

[0091] Examples of the nucleating agent include metal salts of benzoic acids such as aluminum p-tert-butylbenzoate and sodium benzoate, metal salts of aromatic phosphates such as sodium bis(2,4-di-tert-butylphenyl)phosphate, sodium methylenebis(2,4-di-tert-butylphenyl)phosphate, and bis[methylenebis(2,4-di-tert-butylphenyl)phosphate]hydroxyaluminum, and mixtures of metal salts of aromatic phosphates with alkali metal compounds, dibenzylidene sorbitol, bis(methyl dibenzylidene sorbitols such as bis(p-ethylbenzylidene)sorbitol, bis(dimethylbenzylidene sorbitol), amino acid metal salts, rosin acid metal salts, amide compounds such as N,N',N"-tris[2-methylcyclohexyl]-1,2,3-propanetricarboxamide, N,N',N"-tricyclohexyl-1,3,5-benzenetricarboxamide, N,N'-dicyclohexylnaphthalenedicarboxamide, and 1,3,5-tri(dimethylisopropoylamino)benzene, and the like.

[0092] Examples of the antistatic agent include cationic antistatic agents such as fatty acid quaternary ammonium ion salts and polyamine quaternary salts; anionic antistatic agents such as higher alcohol phosphate ester salts, higher alcohol EO adducts, polyethylene glycol fatty acid esters, anionic alkyl sulfonates, higher alcohol sulfate ester salts, higher alcohol ethylene oxide adduct sulfate ester salts, and higher alcohol ethylene oxide adduct phosphate ester salts; nonionic antistatic agents such as polyhydric alcohol fatty acid esters, polyglycol phosphate esters, and polyoxyethylene alkyl allyl ethers; amphoteric alkyl betaines such as alkyl dimethyl amino acetic acid betaine, and amphoteric antistatic agents such as imidazoline-type amphoteric surfactants; and polymeric antistatic agents containing ionomers or block polymers having polyethylene glycol as the hydrophilic moiety.

[0093] Examples of the lubricant include hydrocarbon-based lubricants such as liquid paraffin, paraffin wax, and polyethylene wax; aliphatic-based lubricants such as stearyl alcohol, stearic acid, and 12-hydroxystearic acid; amide-based lubricants such as stearic acid amide, oleic acid amide, erucic acid amide, methylene bisstearic acid amide, and ethylene stearic acid amide; metal soap-based lubricants such as calcium stearate, zinc stearate, magnesium stearate, lead stearate, aluminum stearate, barium stearate, a barium stearate / zinc stearate complex, and a zinc stearate / calcium stearate complex; and ester-based lubricants such as hydrogenated fats and oils, glycerin monostearate, butyl stearate, pentaerythritol stearate, and stearyl stearate.

[0094] Examples of the plasticizer include phthalates, dibasic acid esters, chlorinated paraffins, polyesters, epoxidized esters, phosphate esters, and trimellitates.

[0095] Examples of the light-absorbing dye include cyanine-based, quinoline-based, coumarin-based, thiazole-based, oxonol-based, azulene-based, squarylium-based, azomethine-based, azo-based, benzylidene-based, xanthene-based, phthalocyanine-based, and dithiol metal complex-based compounds.

[0096] Examples of the filler include metal silicates such as calcium carbonate, calcium oxide, calcium hydroxide, zinc hydroxide, zinc carbonate, zinc sulfide, magnesium oxide, magnesium hydroxide, magnesium carbonate, aluminum oxide, aluminum hydroxide, alumina sodium silicate, hydrocalumite, aluminum silicate, magnesium silicate, calcium silicate, and zeolite; activated clay, talc, clay, red iron oxide, asbestos, antimony trioxide, silica, glass beads, mica, sericite, glass flakes, asbestos, wollastonite, potassium titanate, PMF (mineral fiber), gypsum fiber, zonolite, MOS (magnesium hydroxide sulfate hydrate, a fibrous magnesium compound), phosphate fiber, glass fiber, carbon fiber, aramid fiber, and cellulose nanofiber.

[0097] As the pigment, for example, commercially available pigments can be used, such as Pigment Red 1, 2, 3, 9, 10, 17, 22, 23, 31, 38, 41, 48, 49, 88, 90, 97, 112, 119, 122, 123, 144, 149, 166, 168, 169, 170, 171, 177, 179, 180, 181, 182, 183, 184, 185, 186, 187, 188, 189, 190, 191, 192, 193, 194, 195, 196, 197, 198, 199, 200, 201, 202, 203, 204, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 216, 217, 218, 219, 220, 221, 222, 223, 224, 225, 226, 227, 228, 229, 230, 231, 232, 233, 234, 235, 236, 237, 238, 239, 240, 241, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 4, 185, 192, 200, 202, 209, 215, 216, 217, 220, 223, 224, 226, 227, 228, 240, 254; Pigment Orange 13, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64, 65, 71; Pigment Yellow 1 , 3, 12, 13, 14, 16, 17, 20, 24, 55, 60, 73, 81, 83, 86, 93, 95, 97, 98, 100, 109, 110, 113, 114, 117, 120, 125, 126, 127, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 166, 168, 175, 180, 185; Pigment Green 7, 10, 36; Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:5, 15:6, 22, 24, 56, 60, 61, 62, 64; Pigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 50, etc.

[0098] Examples of the dyes include azo dyes, anthraquinone dyes, indigoid dyes, triarylmethane dyes, xanthene dyes, alizarin dyes, acridine dyes, stilbene dyes, thiazole dyes, naphthol dyes, quinoline dyes, nitro dyes, indamine dyes, oxazine dyes, phthalocyanine dyes, and cyanine dyes.

[0099] Examples of the metal soap include salts of metals such as lithium, sodium, potassium, magnesium, calcium, aluminum, hydroxyaluminum, barium, and zinc with saturated or unsaturated fatty acids such as lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, and oleic acid.

[0100] The processing aid can be appropriately selected from known processing aids, but acrylic acid-based processing aids are preferred. Examples of processing aids include homopolymers or copolymers of alkyl methacrylates such as methyl methacrylate, ethyl methacrylate, and butyl methacrylate; copolymers of the alkyl methacrylates with alkyl acrylates such as methyl acrylate, ethyl acrylate, and butyl acrylate; copolymers of the alkyl methacrylates with aromatic vinyl compounds such as styrene, α-methylstyrene, and vinyltoluene; and copolymers of the alkyl methacrylates with vinyl cyan compounds such as acrylonitrile and methacrylonitrile.

[0101] Examples of the flame retardant and the flame retardant aid include the following triazine ring-containing compounds, metal hydroxides, other inorganic phosphorus, halogen-based flame retardants, silicone-based flame retardants, phosphate ester-based flame retardants, condensed phosphate ester-based flame retardants, intumescent-based flame retardants, antimony oxides such as antimony trioxide, other inorganic flame retardant aids, and organic flame retardant aids.

[0102] Examples of the triazine ring-containing compound include melamine, ammeline, benzguanamine, acetoguanamine, phthalodiguanamine, melamine cyanurate, melamine pyrophosphate, butylenediguanamine, norbornenediguanamine, methylenediguanamine, ethylenedimelamine, trimethylenedimelamine, tetramethylenedimelamine, hexamethylenedimelamine, and 1,3-hexylenedimelamine.

[0103] Examples of the metal hydroxide include magnesium hydroxide, aluminum hydroxide, calcium hydroxide, barium hydroxide, zinc hydroxide, and Kismer 5A (magnesium hydroxide: manufactured by Kyowa Chemical Industry Co., Ltd.).

[0104] Examples of the 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, tert-butylphenyl diphenyl phosphate, bis-(tert-butylphenyl)phenyl phosphate, tris-(tert-butylphenyl)phosphate, isopropylphenyl diphenyl phosphate, bis-(isopropylphenyl)diphenyl phosphate, and tris-(isopropylphenyl)phosphate.

[0105] Examples of the condensed phosphate ester flame retardants include 1,3-phenylene bis(diphenyl phosphate), 1,3-phenylene bis(dixylenyl phosphate), bisphenol A bis(diphenyl phosphate), and the like. Examples of the intumescent flame retardants include ammonium salts and amine salts of (poly)phosphoric acids, such as ammonium polyphosphate, melamine polyphosphate, piperazine polyphosphate, ammonium pyrophosphate, melamine pyrophosphate, and piperazine pyrophosphate.

[0106] Examples of the other inorganic flame retardant aids include inorganic compounds such as titanium oxide, aluminum oxide, magnesium oxide, and talc, and surface-treated products thereof. For example, various commercially available products such as TIPAQUE R-680 (titanium oxide: manufactured by Ishihara Sangyo Kaisha Ltd.) and Kyowamag 150 (magnesium oxide: manufactured by Kyowa Chemical Industry Co., Ltd.) can be used.

[0107] Other organic flame retardant aids include, for example, pentaerythritol and dipentaerythritol.

[0108] The zeolite compound is an aluminosilicate of an alkali or alkaline earth metal having a unique three-dimensional zeolite crystal structure. Representative examples include A-type, X-type, Y-type, and P-type zeolite, monodenite, analcite, sodalite-group aluminosilicates, clinobutyrolite, erionite, and chabazite. These zeolite compounds may be either hydrous compounds containing water of crystallization (so-called zeolite water) or anhydrous compounds from which the water of crystallization has been removed. Zeolite compounds having a particle size of 0.1 to 50 μm can be used, with 0.5 to 10 μm being particularly preferred.

[0109] Examples of the foaming agent include decomposition-type organic foaming agents such as azodicarbonamide, azobisisobutyronitrile, p,p'-oxybisbenzenesulfonylhydrazide, n,n'-dinitrosopentamethylenetetramine, p-toluenesulfonylsemicarbazide, and trihydrazotriazine; and decomposition-type inorganic foaming agents such as sodium bicarbonate, ammonium carbonate, ammonium bicarbonate, ammonium nitrite, azide compounds, and sodium borohydride.

[0110] Examples of the (heavy) metal deactivators include salicylamide-1,2,4-triazol-3-yl, bis-salicylic acid hydrazide, dodecandioyl bis(2-(2-hydroxybenzoyl)hydrazide), bis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid)hydrazide, and the like.

[0111] Examples of the crosslinking agent include benzoyl peroxide, di-tert-butyl peroxide, dicumyl peroxide, 2,5-dimethyl-2,5-di(tert-butylperoxy)hexane, 2,5-dimethyl-2,5-di(tert-butylperoxy)hexyne, 1,3-bis(tert-butylperoxyisopropyl)benzene-tert-butyl-hydroperoxide, cumene hydroperoxide, polysulfone azide, azidoformate, tetramethylisophthalyl di-tert-butylbisperoxide, tetramethylisophthalyl dicumylbisperoxide, alkanolamines such as diethanolamine and triethanolamine, hexamethylenediamine, and 4,4'-diaminodiphenylmethane.

[0112] Examples of the epoxy stabilizer include compounds having an aliphatic, aromatic, alicyclic, aromatic aliphatic, or heterocyclic structure and an epoxy group as a side chain. The epoxy group is preferably a glycidyl group bonded to the residue of the molecule via an ether or ester bond, or may be an N-glycidyl derivative of a heterocyclic amine, amide, or imide. Specific examples include epoxidized soybean oil, epoxidized linseed oil, and epoxidized monoester. Commercially available epoxy stabilizers include those manufactured by ADEKA Corporation under the product names "ADEKA CIZER O-130P," "ADEKA CIZER O-180A," "ADEKA CIZER D-32," "ADEKA CIZER EP-13," and "ADEKA CIZER FEP-13."

[0113] As the matting agent, silicon dioxide fine particles are preferred. Examples of silicon dioxide fine particles include Aerosil R972, R972V, R974, R812, 200, 200V, 300, R202, OX50, and TT600 (all manufactured by Nippon Aerosil Co., Ltd.), and Aerosil 200V, Aerosil R972V, and Aerosil R812 are preferred because they have a significant effect of reducing the coefficient of friction while maintaining low film haze.

[0114] Examples of the anti-fogging agent include glycerin fatty acid esters, alkyldiethanolamines, and alkyldiethanolamine fatty acid esters. Examples of the above-mentioned plate-out inhibitor include silicon dioxide and those containing an alkylene oxide adduct of a saponified ethylene-saturated carboxylic acid vinyl ester copolymer as an active ingredient.

[0115] As the surface treatment agent, for example, a surface treatment agent containing one or more of an aminosilane compound and an epoxy resin is preferably used.

[0116] Examples of the aminosilane compound include γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, and γ-(2-aminoethyl)aminopropyltrimethoxysilane.

[0117] Examples of the epoxy resin contained in the surface treatment agent include novolac epoxy resins and bisphenol epoxy resins, and novolac epoxy resins are preferably used. Examples of novolac epoxy resins include polyfunctional epoxy resins such as phenol novolac epoxy resins and cresol novolac epoxy resins.

[0118] In addition to the aminosilane compound and epoxy resin, the surface treatment agent may contain other components such as a urethane resin, an acrylic resin, an antistatic agent, a lubricant, and a water repellent agent, provided that the properties are not impaired. Further examples of other surface treatment agents include epoxy resins other than novolac-type and bisphenol-type, and coupling agents.

[0119] The fluorescent brightener is a compound that absorbs ultraviolet light from sunlight or artificial light, converts it into violet to blue visible light, and radiates it as a fluorescent light, thereby enhancing the whiteness and blueness of molded articles. Examples of the fluorescent brightener include the benzoxazole-based compound CI Fluorescent Brightner 184, the coumarin-based compound CI Fluorescent Brightner 52, and the diaminostilbene disulfonic acid-based compounds CI Fluorescent Brightner 24, 85, and 71.

[0120] Examples of the antifungal agent include organic antifungal agents such as nitrogen-containing, sulfur-containing, organic bromine-containing, nitrogen-containing and arsenic-containing agents, and inorganic antifungal agents such as silver compounds.

[0121] Examples of the antibacterial agent include organic antibacterial agents such as chlorine-based, phenol-based, imidazole-based or thiazole-based compounds, and quaternary ammonium compounds, and inorganic antibacterial agents such as zeolite-based, apatite-based, silica alumina-based, ceramic-based, zirconium phosphate-based, silica gel-based, hydroxyapatite-based or calcium silicate-based agents containing metals such as silver or zinc.

[0122] Examples of the release agent include sodium montanate, potassium montanate, calcium montanate, and magnesium montanate.

[0123] The method for producing the resin composition of the present embodiment is not particularly limited, and any conventionally known method can be employed.

[0124] An example of a method for producing the resin composition includes a method in which the components, such as the granular ultraviolet absorber of the present embodiment, the synthetic resin described above, and other additive components as necessary, are pre-mixed using various mixers such as a tumbler or a Henschel mixer, and then melt-kneaded using a Banbury mixer, a roll, a Brabender mixer, a single-screw kneading extruder, a twin-screw kneading extruder, a kneader, or the like. Alternatively, the resin composition may be produced by premixing only some of the components, feeding the premixed components into an extruder using a feeder, and melt-kneading the components.Furthermore, a resin composition obtained by premixing some of the components, feeding the premixed components into an extruder, and melt-kneading the resulting masterbatch may be mixed with other components and melt-kneaded again to produce a resin composition. The synthetic resin used in the above mixing and kneading step may be in a predetermined shape such as powder or pellets, or may be in a fibrous shape.

[0125] The resin composition of the present embodiment may be solid at room temperature, and may have a fixed shape such as powder, granules, pellets, briquettes, or tablets, or may be in the form of a sheet.

[0126] A molded article can be obtained by molding the resin composition of this embodiment. The molding method 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 foam molding.

[0127] The molded article can have various forms depending on the application, and can have various shapes such as a resin plate, sheet, film, container (bottle, tray, bag), fiber, various molded products, and the like.

[0128] The resin composition of this embodiment may also be prepared as a varnish resin (a varnish-like resin composition that is liquid at room temperature) by dissolving the granular UV absorber of this embodiment, the synthetic resin used as the binder resin, and other additive components as needed in a solvent. An organic solvent or an aqueous solvent can be used as the solvent. The resin varnish may also be used as an emulsion in which a powdered UV absorber is dispersed using an emulsifier as needed.

[0129] As a method for preparing the above-mentioned resin varnish, the order in which the components are mixed is not particularly limited, and all components may be mixed simultaneously, or a synthetic resin may be mixed with a mixture obtained by previously mixing the granular ultraviolet absorber of this embodiment and other additive components, or multiple components that have been prepared in advance may be mixed with other components, or multiple components that have been prepared in advance may be further mixed together. The resin varnish can be processed into a film or sheet by, for example, a cast film method, and can also be used as a paint material for coating a predetermined substrate.

[0130] The resin composition of the present embodiment can be used in a wide range of industrial fields, such as electricity, electronics, and communications, agriculture, forestry, and fisheries, mining, construction, food, textiles, clothing, medicine, coal, petroleum, rubber, leather, automobiles, precision instruments, wood, building materials, civil engineering, furniture, printing, and musical instruments.

[0131] More specific applications include, for example, office and office equipment such as printers, personal computers, word processors, keyboards, PDAs (personal digital assistants), telephones, copiers, facsimiles, ECRs (electronic cash registers), calculators, electronic organizers, cards, holders, and stationery; home appliances such as washing machines, refrigerators, vacuum cleaners, microwave ovens, lighting fixtures, game consoles, irons, and kotatsu tables; audio-visual equipment such as TVs, VTRs, video cameras, radio-cassette players, tape recorders, minidiscs, CD players, speakers, and liquid crystal displays; electrical and electronic components and communication equipment such as connectors, relays, capacitors, switches, printed circuit boards, coil bobbins, semiconductor encapsulation materials, LED encapsulation materials, electric wires, cables, transformers, deflection yokes, distribution boards, and clocks; automotive interior and exterior materials; plate-making films, adhesive films, bottles, food containers, food packaging films, pharmaceutical and medical wrap films, product packaging films, agricultural films, agricultural sheets, and greenhouse films.

[0132] Specific uses include various applications such as seats (padding, outer material, etc.), belts, ceiling coverings, convertible tops, armrests, door trims, rear package trays, carpets, mats, sun visors, wheel covers, mattress covers, airbags, insulation materials, hand straps, hand straps, wire covering materials, electrical insulation materials, paints, coating materials, covering materials, flooring materials, corner walls, carpets, wallpaper, wall coverings, exterior materials, interior materials, roofing materials, deck materials, wall materials, pillar materials, flooring boards, fence materials, frames and moldings, window and door profiles, shingles, paneling, terraces, balconies, soundproofing boards, heat insulating boards, window materials, and other construction materials and civil engineering materials for automobiles, vehicles, ships, aircraft, buildings, houses, and civil engineering materials; clothing; curtains, sheets, nonwoven fabrics, plywood, synthetic fiber boards, rugs, entrance mats, sheets, buckets, hoses, containers, eyeglasses, bags, cases, goggles, skis, rackets, tents, musical instruments, and other daily necessities; and sporting goods. Other examples include paints and cosmetics. Other uses include containers for medicines, vitamins, energy drinks, eye drops, etc.; containers for cosmetics such as lotions, emulsions, and sunscreens; containers for food, and containers for beverages such as alcohol, wine, beer, fruit juice, soft drinks, tea, black tea, and coffee; and containers for daily necessities such as shampoo, conditioner, mouthwash, toothpaste, and disinfectant.

[0133] Furthermore, the resin composition of this embodiment can be molded into a sheet or film and suitably used as an optical material such as an optical film or optical sheet, although there are no particular limitations on the optical material. Examples of optical materials include optical films or optical sheets used in image display devices such as liquid crystal displays (LCDs), plasma display panels (PDPs), electroluminescent displays (ELDs), cathode ray tube displays (CRTs), fluorescent display tubes, and field emission displays. These optical materials are particularly useful as optical compensation films and light emitter protection films for liquid crystal displays and organic EL displays that use organic materials with poor UV resistance in their display elements. Applications for liquid crystal displays include polarizing plate protective films or sheets, retardation films, viewing angle widening films, antiglare films, brightness enhancement films, light diffusion films and sheets, lens films and sheets, antifog films, antistatic films, optical compensation films, antireflection films, color tone adjustment films, and light guide plates. These optical materials are particularly suitable for optical films or optical sheets installed on the outer surface of a polarizing plate in contact with a liquid crystal display element, or polarizing plate protective films or optical sheets.

[0134] Although the embodiments of the present invention have been described above, these are merely examples of the present invention, and various other configurations can also be adopted. Below, examples of reference forms are added. 1. A granular ultraviolet absorber containing a triazine-based compound, The cumulative 10% particle size in the volume-based particle size distribution of the granular UV absorber measured by the wet laser diffraction particle size distribution measurement method is D 10 (μm), and the cumulative 90% particle diameter is D 90 (μm), D 10 / D 90 A granular ultraviolet absorber having a value in the range of 0.01 or more and 0.25 or less. 2. The granular ultraviolet absorber according to 1., The granular ultraviolet absorber, wherein the triazine compound comprises a compound represented by the general formula (I) above. [In the above general formula (I), R 1 represents a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkylaryl group having 7 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or a substituent represented by the above general formula (II), R 2 and R 3 each independently represents a hydrogen atom, a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms, or -OR, in which R represents a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkylaryl group having 7 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms; R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 and R 12 each independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted linear or branched alkyl group having 1 to 8 carbon atoms, or a linear or branched alkenyl group having 2 to 8 carbon atoms; R 13 and R 14 each independently represents a hydrogen atom or a hydroxy group. However, R 1 、R 2 、R 3 and a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms represented by R, R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 and R 12 The methylene group in the substituted or unsubstituted, linear or branched alkyl group having 1 to 8 carbon atoms represented by the formula: 01 =N- and -N=CR 02 -, and in the structure R 01 and R 02 each independently represents a linear or branched alkyl group having 1 to 8 carbon atoms. [In the above general formula (II), R 21 and R 22 each independently represents a hydrogen atom, a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms, or -OR, where R represents a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkylaryl group having 7 to 20 carbon atoms, or an arylalkyl group having 7 to 20 carbon atoms; R 23 、R 24 、R 25 、R26 、R 27 、R 28 、R 29 、R 30 and R 31 each independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted linear or branched alkyl group having 1 to 8 carbon atoms, or a linear or branched alkenyl group having 2 to 8 carbon atoms; R 32 and R 33 each independently represents a hydrogen atom or a hydroxy group, X 1 represents a substituted or unsubstituted, linear or branched alkylene group having from 8 to 30 carbon atoms, Y 1 and Y 2 are each independently -CO-O-, -O-CO-, -L 1 -, -OL 1 O-, -OL 1 -、-L 1 -O-CO-, -L 1 -CO-O-, -CO-CH=CH-, -CH=CH-CO-, -CH=CH-CO-O-, -CH=CH-O-CO-, -CO-O-CH=CH-, L 1 is a linear or branched alkylene group having 1 to 8 carbon atoms, m and n each independently represent an integer of 0 to 8; * indicates R in formula (I). 1 represents the bond to the oxygen atom connected to the However, R 21 、R 22 and a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms represented by R, R 23 、R 24 、R 25 、R 26 、R 27 、R 28 、R 29 、R 30 and R 31 and X 1 The methylene group in the linear or branched alkylene group having 8 to 30 carbon atoms represented by the formula (I) is an oxygen atom, a sulfur atom, a carbon-carbon double bond, -CO-, -CO-O-, -OC-O-, -CO-NH-, -NH-CO-, -CR 03 =N- and -N=CR 04 -, and R 03 and R 04 each independently represents a linear or branched alkyl group having 1 to 8 carbon atoms. 3. A granular ultraviolet absorber according to 1. or 2., The granular ultraviolet absorber, wherein the triazine compound comprises a compound represented by the general formula (A). (In the above general formula (A), R A1 represents a linear or branched alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a linear or branched alkenyl group having 3 to 8 carbon atoms, an aryl group having 6 to 18 carbon atoms, an alkylaryl group having 7 to 18 carbon atoms, or an arylalkyl group having 7 to 18 carbon atoms, R A2 and R A3 may be the same or different and represent a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, or a linear or branched alkoxy group having 1 to 12 carbon atoms; R A4 、R A7 、R A10 may be the same or different and represent a hydrogen atom, a linear or branched alkyl group having 1 to 8 carbon atoms, or a linear or branched alkenyl group having 3 to 8 carbon atoms, R A13 and R A17 may be the same or different and represent a hydrogen atom or a hydroxy group. However, R A1 、R A2 and R A3 a linear or branched alkyl group having 1 to 12 carbon atoms represented by the formula: A2 and R A3 The methylene group in the linear or branched alkoxy group having 1 to 12 carbon atoms represented by the formula (I) is not limited to an oxygen atom, a sulfur atom, a carbon-carbon double bond, -CO-, -CO-O-, -OC-O-, -CO-NH-, -NH-CO-, -CR 05 =N- and -N=CR 06 -, and in the structure R 05 and R 06 each independently represents a linear or branched alkyl group having 1 to 8 carbon atoms. 4. A granular ultraviolet absorber according to 1. or 2., The granular ultraviolet absorber comprises one or more triazine compounds represented by any one of Compound No. 1A to Compound No. 8A. 5. A granular ultraviolet absorber according to 1. or 2., The granular ultraviolet absorber, wherein the triazine compound comprises a compound represented by the general formula (B) above. (In the above general formula (B), R B4 、R B5 、R B7 ~R B9 、R B10 ~R B12 、RB23 、R B24 、R B26 ~R B28 、R B29 ~R B31 each independently represents a hydrogen atom, a hydroxy group, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms, and n represents an integer of 8 to 14. However, the para positions of two of the three benzene rings linked to the triazine ring represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 20 carbon atoms, and one of the ortho positions represents a hydrogen atom or a hydroxy group. 6. The granular ultraviolet absorber according to 5., The granular ultraviolet absorber comprises one or more triazine compounds represented by any one of Compound No. 1B to Compound No. 4B. (In the above compounds No. 1B to Compound No. 4B, R A1 、R A2 、R B1 、R B2 、R C1 、R C2 、R D1 and R D2 may be the same or different and represent a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched alkoxy group having 1 to 4 carbon atoms. 7. A granular ultraviolet absorber according to any one of 1. to 6., When the volume average particle diameter in the volume-based particle diameter distribution of the granular ultraviolet absorber measured by a wet laser diffraction particle size distribution measurement method is MV (μm) and the number average particle diameter is MN (μm), A granular ultraviolet absorber having an MV / MN in the range of 5.0 or more and 30.0 or less. 8. A granular ultraviolet absorber according to any one of 1. to 7., The cumulative 98% particle size in the volume-based particle size distribution of the granular UV absorber measured by the wet laser diffraction particle size distribution measurement method is D 98 (μm), D 98 / D 90 A granular ultraviolet absorber having a refractive index in the range of 1.70 or more and 5.00 or less. 9. A granular ultraviolet absorber according to any one of 2. to 4., The granular ultraviolet absorber is characterized in that the triazine compound has a maximum peak in a powder X-ray diffraction analysis pattern at a diffraction angle 2θ in the range of 5.00° to 6.50°. 10. The granular ultraviolet absorber according to 9., The granular ultraviolet absorber, wherein the half width of the maximum peak of the triazine compound is 0.05° or more and 0.20° or less. 11. A granular ultraviolet absorber according to 9. or 10., A granular ultraviolet absorber characterized in that, when the relative intensity of the maximum peak of the triazine-based compound is taken as 100, no diffraction peak having a relative intensity of 30 or more and 60 or less exists within a range of a diffraction angle 2θ of 3.0° or more and 45.0° or less. 12. A granular ultraviolet absorber according to any one of 9. to 11., A granular ultraviolet absorber characterized in that, when the relative intensity of the maximum peak of a triazine-based compound is taken as 100, no diffraction peak having a relative intensity of 1 or more and 5 or less exists within a diffraction angle 2θ range of more than 45.0° and not more than 60.0°. 13. A resin composition containing the granular ultraviolet absorber described in any one of 1. to 12. 14. A resin composition according to 13., which contains a synthetic resin. [Example]

[0135] The present invention will be described in detail below with reference to examples, but the present invention is not limited to the descriptions of these examples.

[0136] [Preparation of Granular UV Absorber] Example 1 2,4,6-Tris[2-hydroxy-3-methyl-4-hexyloxyphenyl]triazine was synthesized by the following procedure. A 300 ml four-neck flask was charged with 10.00 g of 2,4,6-tris(2,4-dihydroxy-3-methylphenyl)triazine, 22.68 g of sodium hydroxide, 80.00 g of dimethylformamide, and 11.07 g of 1-bromohexane. The mixture was heated to 80 °C and reacted for 9 hours. After neutralization with hydrochloric acid, the mixture was washed with water and desolvated under reduced pressure. The residue was recrystallized from a 1:1 mixture of toluene and isopropyl alcohol to obtain crystals. The molten target product (crystals) was then dripped onto a metal plate and cooled to obtain flakes (melting and solidification process). The resulting flakes were crushed in a mortar to obtain 11.89 g of a pale yellow powder with a melting point of 145 °C (76% yield). The obtained compound (pale yellow powder) was 1 H-NMR measurement was carried out. Based on the following analytical results, the obtained pale yellow powder was identified as a powdery compound (granular ultraviolet absorber) represented by the following formula No. 1.

[0137] [ka]

[0138] Examples 2 to 10 In the same manner as in Example 1, a powdery compound No. 1 (granular ultraviolet absorber) represented by the above formula No. 1, which was a different lot, was obtained.

[0139] Example 11 2-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)-3-hydroxyphenoxy)ethyl 2-ethylhexanoate was synthesized by the following procedure. 10.00 g of 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-(2-hydroxyethoxy)phenol, 0.25 g of paratoluenesulfonic acid monohydrate, 70.00 g of toluene, and 4.12 g of 2-ethylhexanoic acid were added to a 300 mL four-neck flask and allowed to react under reflux for 10 hours. The mixture was washed with water and recrystallized from a 1:2 toluene:isopropyl alcohol mixture to obtain crystals. The molten target product (crystals) was then dripped onto a metal plate and cooled to obtain flakes (melting and solidification process). The resulting flakes were crushed in a mortar to obtain 9.56 g of a pale yellow powder with a melting point of 108 °C (72% yield). The obtained compound (pale yellow powder) was 1 H-NMR measurement was carried out. Based on the following analytical results, the obtained pale yellow powder was identified as a powdery compound (granular ultraviolet absorber) represented by the following formula No. 2.

[0140] [ka]

[0141] (Comparative Example 1) The crystals obtained in Example 1 were crushed in a mortar without being subjected to melt-solidification treatment, to obtain a powdery compound (granular ultraviolet absorber) represented by the above formula No. 1.

[0142] (Comparative Examples 2 to 5) In the same manner as in Comparative Example 1, a powdery compound (granular ultraviolet absorber) represented by the above formula No. 1 was obtained, which was a different lot.

[0143] (Comparative Example 6) The flakes obtained in Example 11 were coarsely pulverized to obtain a granular compound (granular ultraviolet absorber) represented by the above formula No. 2.

[0144] The granular ultraviolet absorbers obtained as described above were evaluated based on the following evaluation items. The evaluation results are shown in Table 1.

[0145] [Table 1]

[0146] (particle size distribution) Cumulative 10% particle size D 10 , Cumulative 90% particle size D 90 , Cumulative 98% particle size D 98 The volume average particle diameter MV and number average particle diameter MN were measured using a laser diffraction particle size distribution analyzer (Microtrac MT3000II) under wet conditions while dispersing a solution prepared by adding the obtained granular UV absorber to methanol and mixing it with ultrasonic waves.

[0147] (Compression granulation) The obtained granular ultraviolet absorber was compressed and granulated using a briquetting machine to form almond-shaped briquettes. The appearance of the obtained briquettes was observed, and the compression granulation properties were evaluated based on the following evaluation criteria. ◯: Laminating (the phenomenon in which the briquette breaks into layers) did not occur. ×: Lamination occurred in part or on the whole.

[0148] (melt-mixing ability) The resulting granular UV absorber was blended in an amount of 1 part by mass per 100 parts by mass of acrylic resin, and the mixture was melt-kneaded and granulated at 250°C using a twin-screw extruder (L / D = 30) to obtain pellets. The pellets were observed when the discharge rate was set to 0.3 kg / h, and the melt-kneadability was evaluated based on the following evaluation criteria. ◯: The resin and the granular ultraviolet absorber were uniformly dispersed, and melt-kneading was possible. Δ: The resin and the granular ultraviolet absorber were slightly separated, but could be melt-kneaded. ×: The resin and the granular ultraviolet absorber separated, and melt-kneading was not possible.

[0149] Furthermore, X-ray diffraction analysis was carried out on the obtained granular ultraviolet absorbents of Examples 1 and 11 and Comparative Example 1. The evaluation results are shown in Tables 2 to 5.

[0150] [Table 2]

[0151] (X-ray diffraction) The obtained granular ultraviolet absorber was subjected to powder X-ray diffraction measurement using Ultima IV (Rigaku Corporation) under the following measurement conditions. (Measurement conditions) X-ray tube: CuKα radiation (CuKα1=1.540562Å, CuKα2=1.544398Å, no CuKα2 removal) Tube voltage / current: 40kV / 40mA Attachment: Multipurpose thin film sample holder Monochromator: Fixed Filter: None Divergence slit: 2 / 3° Divergence vertical limit slit: 10 mm Scattering slit: 1.17 mm Receiving slit: 0.3 mm Scan Type: Continuous Scan Scan speed: 4° / min Sampling width: 0.02° Scan axis: 2θ / ω Scanning range: 3°~90°

[0152] The results of powder X-ray diffraction analysis of the granular ultraviolet absorber of Example 1 are shown in Figure 1. The diffraction angle 2θ, d value, and relative intensity corresponding to each peak in Figure 1 are shown in Table 3. In Table 3, deg represents degrees, and the threshold value of the peak intensity was set to 1 / 100 of the maximum peak.

[0153] [Table 3]

[0154] The results of powder X-ray diffraction analysis of the granular ultraviolet absorber of Example 11 are shown in Figure 2. The diffraction angle 2θ, d value, and relative intensity corresponding to each peak in Figure 2 are shown in Table 4. In Table 4, the threshold value of the peak intensity was set to 1 / 100 of the maximum peak. However, the measurement conditions for the powder X-ray diffraction measurement in Example 11 were the same as those in Example 1, except that the following conditions were used. Divergence slit: 1 / 2° Divergence vertical limit slit: 10 mm Scattering slit: 0.93 mm Scanning range: 2°~60°

[0155] [Table 4]

[0156] The results of powder X-ray diffraction analysis of the granular ultraviolet absorber of Comparative Example 1 are shown in Figure 3. The diffraction angle 2θ, d value, and relative intensity corresponding to each peak in Figure 3 are shown in Table 5. In Table 5, the threshold value of the peak intensity was set to 1 / 100.

[0157] [Table 5]

[0158] (Feedability) 1 kg of the obtained granular ultraviolet absorber was placed in a hopper, and discharged for 30 minutes using a gravimetric feeder (manufactured by K-Tron Co., Ltd., twin spiral type biaxial screw with length: 25 cm × outer diameter: 1.4 cm, groove width: 2.0 cm, groove depth: 0.3 cm) at a feeder discharge rate of 0.3 kg / h (feedability test). ·Quantitativeness The amount discharged from the gravimetric feeder (feeder amount) was measured over time at 10-minute intervals. A small variation in the feed amount was marked with a circle, and a large variation in the feed amount was marked with an ×. Long-lasting The above-mentioned feed test was carried out in the same manner except that the discharge time condition was changed from 30 minutes to 3 hours. When discharge continued for 3 hours, it was marked with an O, and when operation was stopped before 3 hours had elapsed, it was marked with an X.

[0159] [Preparation of Resin Composition] (Film Preparation) A resin composition was prepared by blending 0.2 parts by mass of the granular UV absorber of each example obtained with 100 parts by mass of synthetic resin (polycarbonate resin: Mitsubishi Engineering-Plastics Corporation, product name E-2000) and dissolving the blend in 230 parts by mass of a solvent (toluene / cyclohexane = 9 / 1). A film with a thickness of 40 μm was produced from the obtained resin composition by a casting method, and a square film test piece with a side length of 2 cm was obtained. The obtained film test pieces were measured for the retention (%) of total light transmittance (%) after 240, 360 and 480 hours using a sunshine weatherometer (83°C, no rain, carbon arc light source) to evaluate light resistance. The results showed that the retention rates (%) after 240, 360 and 480 hours were high, indicating that excellent light resistance could be achieved by using the granular ultraviolet absorbers of each Example. It was also found that similarly excellent light resistance could be achieved when methacrylic resin, norbornene resin, polyethylene terephthalate resin, or polystyrene resin was used as the synthetic resin instead of polycarbonate resin.

[0160] (Container manufacturing) A resin composition was obtained by adding 0.3 parts by mass of the granular UV absorber of each Example to 100 parts by mass of polyethylene terephthalate (intrinsic viscosity: 0.8 dL / g) and mixing. The resulting resin composition was dried for 4 hours in a gear oven at 160°C and then molded into a preform (mouth outer diameter 25 mm, weight 23 g) using an injection molding machine at an injection temperature of 280°C. The resulting preform was then biaxially stretched and blow-molded at a mold temperature of 130°C to produce a plastic bottle with a capacity of 500 mL and a thickness of 0.7 mm. The transmittance of the resulting plastic bottle to visible light with a wavelength of 500 nm and ultraviolet light with a wavelength of 400 nm was measured. The results, which showed high transmittance at 500 nm and low transmittance at 400 nm, indicated that the resulting plastic bottle (container) efficiently absorbed ultraviolet light and also ensured sufficient transmittance to visible light.

[0161] (Preparation of coating material) UV absorbing layer A resin solution (resin composition) was obtained by mixing 0.5 parts by mass of the granular UV absorber of each Example obtained with 100 parts by mass of norbornene resin (product name: ARTON F5023, manufactured by JSR Corporation) and 2,000 parts by mass of dichloromethane as a solvent. The obtained resin solution was cast onto a surface-polished glass plate using a bar coater, pre-dried at 50°C for 20 minutes, and dried at 90°C for 30 minutes to produce a film with a thickness of 80 to 90 μm, and then a square film test piece (UV absorbing layer) with a side length of 2 cm was obtained. Fabrication of NIR absorption layer A resin solution consisting of 100 parts by mass of norbornene resin (manufactured by JSR Corporation, product name: ARTON F5023), 0.3 parts by mass of a diimonium compound (manufactured by Nippon Kayaku Co., Ltd., product name: IRG-068) as a near-infrared absorber, and 2,000 parts by mass of dichloromethane as a solvent was cast onto a surface-polished glass plate using a bar coater, pre-dried at 50°C for 20 minutes and dried at 90°C for 30 minutes to produce a film with a thickness of 50 to 60 μm, and then a square film test piece with a side length of 2 cm was obtained. The resulting test piece with the NIR absorbing layer and the UV absorbing layer superposed on top of each other was exposed to test light from the UV absorbing layer side using a Sunshine Weather Meter (manufactured by Suga Test Instruments Co., Ltd.; 83°C, no rain, carbon arc light source) for 360 (or 540) hours. The transmittance at the maximum wavelength in the NIR region (NIR absorbing layer: 1100 nm) was measured before and after the light resistance test, and the light resistance was evaluated based on the attenuation rate of transmittance (Δtransmittance). In each example, the results of the reduction in Δtransmittance confirmed that the film was effective in preventing photodegradation of the near-infrared absorbent, demonstrating that the film was excellent in preventing photodegradation of the near-infrared absorbent in the near-infrared absorbing layer.

[0162] It was found that the granular ultraviolet absorbers of Examples 1 to 11 exhibited excellent powder properties, as they were superior in melt-kneading properties and compression granulation properties compared to Comparative Examples 1 to 5, and superior in melt-kneading properties compared to Comparative Example 6. It was also found that the compounds of Examples 1 to 11 were excellent in ultraviolet absorption properties, and therefore could be suitably used as ultraviolet absorbers.

[0163] This application claims priority based on Japanese Patent Application No. 2018-067822, filed March 30, 2018, and Japanese Patent Application No. 2018-067830, filed March 30, 2018, the disclosures of which are incorporated herein in their entireties.

Claims

1. A granular ultraviolet absorber containing a triazine-based compound, The triazine compound includes one or more compounds represented by any one of Compound No. 1A to Compound No. 8A below, The cumulative 10% particle size in the volume-based particle size distribution of the granular ultraviolet absorber measured by a wet laser diffraction particle size distribution measurement method is D １０ (μm), and the cumulative 90% particle diameter is D ９０ (μm), D １０ / D ９０ is in the range of 0.01 or more and 0.25 or less, Granular ultraviolet absorber. 【Chemical 1】 【change】

2. The granular ultraviolet absorber according to claim 1, When the volume average particle diameter of the granular ultraviolet absorber in the volume-based particle diameter distribution measured by a wet laser diffraction particle size distribution measurement method is defined as MV (μm) and the number average particle diameter is defined as MN (μm), A granular ultraviolet absorber having an MV / MN ratio in the range of 5.0 or more and 30.0 or less.

3. The granular ultraviolet absorber according to claim 1 or 2, The cumulative 98% particle size in the volume-based particle size distribution of the granular ultraviolet absorber measured by a wet laser diffraction particle size distribution measurement method is D ９８ (μm), D ９８ / D ９０ A granular ultraviolet absorber having a molecular weight of 1.70 or more and 5.00 or less.

4. The granular ultraviolet absorber according to any one of claims 1 to 3, The granular ultraviolet absorber is characterized in that the triazine compound has a maximum peak in a powder X-ray diffraction analysis pattern at a diffraction angle 2θ in the range of 5.00° to 6.50°.

5. The granular ultraviolet absorber according to claim 4, The granular ultraviolet absorber, wherein the half width of the maximum peak of the triazine compound is 0.05° or more and 0.20° or less.

6. The granular ultraviolet absorber according to claim 4 or 5, A granular ultraviolet absorber characterized in that, when the relative intensity of the maximum peak of the triazine-based compound is taken as 100, no diffraction peak having a relative intensity of 30 or more and 60 or less exists within a range of a diffraction angle 2θ of 3.0° or more and 45.0° or less.

7. The granular ultraviolet absorber according to any one of claims 4 to 6, A granular ultraviolet absorber characterized in that, when the relative intensity of the maximum peak of the triazine-based compound is taken as 100, no diffraction peak having a relative intensity of 1 or more and 5 or less exists within a range where the diffraction angle 2θ is more than 45.0° and 60.0° or less.

8. A resin composition comprising the granular ultraviolet absorber according to any one of claims 1 to 7.

9. The resin composition according to claim 8, comprising a synthetic resin.

Images