JPWO2019188953A1 - Granular ultraviolet absorber and resin composition - Google Patents

Abstract

The granular ultraviolet absorbent of the present invention is a granular ultraviolet absorbent containing a triazine-based compound, and has a sieve residue amount on a sieve having a mesh size of 4.0 mm, which is calculated based on a predetermined procedure for measuring a sieve residue amount. , 0.3 wt% or more and 1.5 wt% or less, and the sieve residue amount on the sieve with a mesh opening of 2.8 mm is 5.0 wt% or more and 25.0 wt% or less, on the sieve with a mesh opening of 2.0 mm. Satisfies the particle size distribution in which the sieve residue amount is 25.0 wt% or more and 35.0 wt% or less, and the sieve residue amount on the sieve having an opening of 1.0 mm is 35.0 wt% or more and 55.0 wt% or less. Of.

Description

  The present invention relates to a granular ultraviolet absorber and a resin composition.

  So far, various developments have been made in ultraviolet absorbers. As this type of technology, for example, the technology described in Patent Document 1 is known. Patent Document 1 describes the use of a triazine compound obtained by crystallization as an ultraviolet absorber (paragraph 0102 of Patent Document 1).

JP, 2011-6517, A

  However, as a result of the study by the present inventor, it was found that the ultraviolet absorbent described in Patent Document 1 above has room for improvement in terms of powder characteristics.

  As a result of further study, the present inventor has found that the powder characteristics of the granular ultraviolet absorbent containing the triazine compound can be appropriately controlled by using the particle size distribution based on the sieve as a guide. As a result of further studies based on such findings, the residual amount of each sieve of 4.0 mm sieve, 2.8 mm sieve, 2.0 mm sieve, and 1.0 mm sieve was determined within a predetermined numerical range. It was found that the content of the particles improves the powder characteristics of the granular ultraviolet absorbent, and thus the present invention has been completed.

According to the invention,
A granular ultraviolet absorber containing a triazine-based compound,
Calculated based on the following procedure for measuring the sieve residue,
The amount of the sieve residue on the sieve having an opening of 4.0 mm is 0.3 wt% or more and 1.5 wt% or less,
The sieve residue amount on the sieve with a mesh of 2.8 mm is 5.0 wt% or more and 25.0 wt% or less,
The amount of the screen residue on the screen having a mesh size of 2.0 mm is 25.0 wt% or more and 35.0 wt% or less,
Provided is a granular ultraviolet absorber which satisfies the particle size distribution in which the amount of the screen residue on a screen having an opening of 1.0 mm is 35.0 wt% or more and 55.0 wt% or less.
(Procedure for measuring the amount of screen residue)
A predetermined amount (g) of the granular ultraviolet absorber is sieved in this order using a mesh opening of 4.0 mm, a mesh opening of 2.8 mm, a mesh opening of 2.0 mm and a mesh opening of 1.0 mm. Then, the residual weight (g) of the granular ultraviolet absorbent remaining on each sieve is measured, and the weight ratio (wt%) of the residual weight to the predetermined amount is calculated as the residual amount of sieve.

  Moreover, according to this invention, the resin composition containing the said granular ultraviolet absorber is provided.

  According to the present invention, a granular ultraviolet absorber having excellent powder characteristics and a resin composition using the same are provided.

  The above-described object and other objects, features and advantages will be further clarified by the preferred embodiments described below and the accompanying drawings.

3 is an X-ray diffraction pattern of the granular ultraviolet absorbent of Example 1. 4 is an X-ray diffraction pattern of the granular ultraviolet absorbent of Comparative Example 1.

The granular ultraviolet absorber of the present embodiment contains a triazine compound.
The triazine-based 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 only of the following triazine compound.

In the above general formula (I),
R ¹ is 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, and 7 carbon atoms. To an alkylaryl group having 20 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 represent a hydrogen atom, a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms, or —O—R, and R is substituted or unsubstituted. A substituted, 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 represents 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 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted, straight-chain or branched carbon atom. Represents an alkyl group having 1 to 8 atoms or a linear or branched alkenyl group having 2 to 8 carbon atoms,
R ¹³ and R ¹⁴ each independently represent a hydrogen atom or a hydroxy group.

However, the substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms represented by R ¹ , R ² , R ^3, and R, R ⁴ , R ⁵ , R ⁶ , R ⁷ , and R. The methylene group in the substituted or unsubstituted linear or branched alkyl group having 1 to 8 carbon atoms represented by ⁸ , R ⁹ , R ¹⁰ , R ¹¹ and R ¹² is an oxygen atom, a sulfur atom or a carbon atom. - carbon double bond, -CO -, - CO-O -, - OC-O -, - CO-NH -, - NH-CO -, - CR 01 = N- and -N = ^{CR 02} - is selected from At least one structure may be substituted, and R ⁰¹ and R ⁰² in the above structure each independently represent 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 represent a hydrogen atom, a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms, or —O—R, wherein R is substituted or unsubstituted. A substituted, 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 represents 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 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted linear or branched carbon atom. Represents an alkyl group having 1 to 8 atoms, or a linear or branched alkenyl group having 2 to 8 carbon atoms,
R ³² and R ³³ each independently represent a hydrogen atom or a hydroxy group,
X ¹ represents a substituted or unsubstituted, linear or branched alkylene group having 8 or more and 30 or less carbon atoms,
Y ¹ and ^{Y 2} each ^{independently, -CO-O -, - O} -CO -, - L 1 -, - O-L 1 O -, - O-L 1 -, - L 1 -O-CO ^{-, - L 1 -CO-O} -, - CO-CH = CH -, - CH = CH-CO -, - CH = CH-CO-O -, - CH = CH-O-CO -, - CO- Represents 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,
* Represents a bond with an oxygen atom linked to R ¹ in formula (I).

However, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms represented by R ²¹ , R ²² and R, R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ²⁷ , R. ²⁸ , R ²⁹ , R ³⁰ and R ³¹ , a substituted or unsubstituted linear or branched alkyl group having 1 to 8 carbon atoms and a linear or branched carbon atom represented by X ¹ The methylene group in the alkylene group of 30 or more and 30 or less 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} - may be substituted with at least one or more structure selected ^{from, R 03} and ^{R 04} is independently a linear or branched carbon It represents an alkyl group having 1 to 8 atoms.

A substituted or unsubstituted, straight-chain or branched carbon atom represented by R ¹ , R ² , and R ^{3 in} the general formula (I) and R ²¹ , R ²² and R in the general formula (II). Examples of the alkyl group of the number 1 to 20, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, amyl, isoamyl, tert-amyl, hexyl, heptyl, n-octyl, isooctyl, Examples thereof include linear or branched alkyl groups such as tert-octyl, 2-ethylhexyl, nonyl, isononyl, decyl, undecyl and dodecyl.

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

Examples of the aryl group having 6 to 20 carbon atoms represented by R ¹ and R in the general 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, 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, 2,4,5-trimethylphenyl, etc. ,

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

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

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

^R 4 in the general formula ^{(I), R 5, R} 6, R 7, R 8, R 9, R 10, R 11 and ^{R 12} and ^R 23 in the general formula ^{(II), R 24, R} Examples of the substituted or unsubstituted linear or branched alkyl group having 1 to 8 carbon atoms represented by ²⁵ , R ²⁶ , R ²⁷ , R ²⁸ , R ²⁹ , R ³⁰ and R ³¹ include methyl, Examples thereof include ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, amyl, isoamyl, tert-amyl, hexyl, heptyl, n-octyl, isooctyl, tert-octyl and 2-ethylhexyl. In the granular ultraviolet absorber of this embodiment, an alkyl group having 1 to 8 carbon atoms is preferable.

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

The substituted or unsubstituted linear or branched alkylene group having 8 or more and 30 or less carbon atoms represented by X ¹ in the general formula (II) is an alkylene group in which methylene is linked with 8 or more and 30 or less. Alternatively, it represents an alkylene group in which a part of hydrogen atoms of methylene is substituted with an alkyl group. In the granular ultraviolet absorbent of this embodiment, an alkylene group having 8 or more and 20 or less carbon atoms is preferable.

In the general formula (II), the linear or branched alkylene group having 1 to 8 carbon atoms represented by L ¹ is, for example, methylene, methylmethylene, dimethylmethylene, ethylene, propylene, isopropylene or butylene. , Isobutylene, pentylene and the like.

The triazine-based compound may contain a compound in which R ⁵ , R ⁶ , R ⁸ , R ⁹ , R ¹¹ and R ^{12 in the} general formula (I) are hydrogen atoms.
Further, examples of the triazine-based compound represented by the general formula (I) include compounds represented by the following general formula (A) or compounds represented by the following general formula (B).

  In addition, as the granular ultraviolet absorber of the present embodiment, a compound represented by the following general formula (A) can be used. These may be used alone or in combination of two or more.

In the above general formula (A),
R ^A1 is 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, or 6 to 6 carbon atoms. An aryl group having 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, which} may be the same or different from each other, are 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. Represents
R ^A4 , R ^A7 and R ^{A10, which} may be the same or different, are each a hydrogen atom, a linear or branched alkyl group having 1 to 8 carbon atoms, or a linear or branched alkenyl having 3 to 8 carbon atoms. Represents a group.
R ^A13 and R ^A17 may be the same as or different from each other and represent a hydrogen atom or a hydroxy group.
However, a linear or branched alkyl group having 1 to 12 carbon atoms represented by R ^A1 , R ^A2 and R ^A3 , or a linear or branched alkyl group having 1 to 12 carbon atoms represented by R ^A2 and R ^A3 . The methylene group in the alkoxy group is an oxygen atom, a sulfur atom, a carbon-carbon double bond, -CO-, -CO-O-, -OC-O-, -CO-NH-, -NH-CO-,-. It may be substituted with at least one structure selected from CR ⁰⁵ = N- and -N = CR ^06- , and R ⁰⁵ and R ⁰⁶ in the structure are each independently a linear or branched carbon. It represents an alkyl group having 1 to 8 atoms.

Examples of the linear or branched alkyl group having 1 to 12 carbon atoms represented by R ^A1 , R ^A2 and R ^A3 in the general formula (A) include, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, a straight or branched chain such as sec-butyl, tert-butyl, amyl, isoamyl, tert-amyl, hexyl, heptyl, n-octyl, isooctyl, tert-octyl, 2-ethylhexyl, nonyl, isononyl, decyl, undecyl, dodecyl. An alkyl group is mentioned.

Examples of the linear or branched alkoxy group having 1 to 12 carbon atoms represented by R ^A2 and R ^A3 in the general formula (A) include, for example, 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, Examples include isoheptyloxy, tert-heptyloxy, 1-octyloxy, isooctyloxy, tert-octyloxy and the like.

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

Examples of the aryl group having 6 to 18 carbon atoms or the alkylaryl group having 7 to 18 carbon atoms represented by R ^A1 of the above general formula (A) include, for example, phenyl, naphthyl, 2-methylphenyl and 3-methyl. Phenyl, 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-t ert-butylphenyl, 2,6-di-tert-butylphenyl, 2,4-di-tert-pentylphenyl, 2,5-di-tert-amylphenyl, 2,5-di-tert-octylphenyl, biphenyl , 2,4,5-trimethylphenyl and the like, and examples of the arylalkyl group having 7 to 18 carbon atoms include benzyl, phenethyl, 2-phenylpropan-2-yl, diphenylmethyl and the like.

In the general formula (A), examples of the linear or branched alkenyl group having 3 to 8 carbon atoms represented by R ^A1 , R ^A4 , R ^A7 , and R ^A10 include linear and branched propenyl, Butenyl, pentenyl, hexenyl, heptenyl, octenyl are mentioned regardless of the position of the unsaturated bond.

In the general formula (A), examples of the linear or branched alkyl group having 1 to 8 carbon atoms represented by R ^A4 , R ^A7 , and R ^A10 include, for example, methyl, ethyl, propyl, isopropyl, butyl, sec. -Butyl, tert-butyl, isobutyl, amyl, tert-amyl, octyl, tert-octyl and the like. Of these, a methyl group is preferable because it has excellent ultraviolet absorbing ability.

  The triazine-based compound represented by the general formula (A) is the following compound No. 1A to compound No. It is preferable to include one or more triazine compounds represented by any of 5A.

Further, the triazine-based compound represented by the general formula (A) is the following compound No. 6A-Compound No. It is preferable to include one or more triazine compounds represented by any of 8A.

  In addition, as the granular ultraviolet absorber of the present embodiment, a compound represented by the following general formula (B) can be used. These may be used alone or in combination of two or more.

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

In the above general formula (B), as a halogen atom represented by R ^B4 , R ^B5 , R ^{B7 to} R ^B9 , R ^{B10 to} R ^B12 , R ^B23 , R ^B24 , R ^{B26 to} R ^B28 , and R ^{B29 to} R ^B31. Examples of the fluorine atom include a fluorine atom, a chlorine atom and a bromine atom.

In the general formula (B), a straight chain represented by R ^B4 , R ^B5 , R ^{B7 to} R ^B9 , R ^{B10 to} R ^B12 , R ^B23 , R ^B24 , R ^{B26 to} R ^B28 , and R ^{B29 to} R ^B31. Examples of the branched alkyl group having 1 to 20 carbon atoms include methyl, ethyl, propyl, 2-propynyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, decyl, dodecyl and octadecyl. To be

In the general formula (B), a straight chain represented by R ^B4 , R ^B5 , R ^{B7 to} R ^B9 , R ^{B10 to} R ^B12 , R ^B23 , R ^B24 , R ^{B26 to} R ^B28 , and R ^{B29 to} R ^B31. Examples of the branched alkenyl group having 2 to 8 carbon atoms 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, 5-hexenyl and the like.

In the general formula (B), a straight chain represented by R ^B4 , R ^B5 , R ^{B7 to} R ^B9 , R ^{B10 to} R ^B12 , R ^B23 , R ^B24 , R ^{B26 to} R ^B28 , and R ^{B29 to} R ^B31. Examples of the branched alkoxy group having 1 to 20 carbon atoms 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, tert. -O Yloxy, and the like.

In the general formula (B), the number of carbon atoms represented by R ^B4 , R ^B5 , R ^{B7 to} R ^B9 , R ^{B10 to} R ^B12 , R ^B23 , R ^B24 , R ^{B26 to} R ^B28 , and R ^{B29 to} R ^B31. 6-20 aryl groups 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-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, 2,4-dicumylphenyl, 4-cyclohexylphenyl, (1,1′-biphenyl) -4-yl, 2,4,5-trimethylphenyl, ferrocenyl and the like can be mentioned.

In addition, the triazine-based compound represented by the general formula (B) is the following compound No. 1B to compound No. It is preferable that one or more triazine-based compounds represented by any of 4B are included.

The above compound No. 1B to compound No. In 4B, R ^A1 , R ^A2 , R ^B1 , R ^B2 , R ^C1 , R ^C2 , R ^D1 and R ^{D2, which} may be the same or different, are each a hydrogen atom, a linear or branched carbon atom number of 1 to 4 Represents an alkyl group or a linear or branched alkoxy group having 1 to 4 carbon atoms.

  The method for synthesizing the above triazine-based compound is not particularly limited and may be any of the synthesizing methods usually used for synthesizing a compound having a triazine structure. For example, there may be mentioned a method of adding a phenol derivative or a resorcinol derivative to cyanuric chloride using aluminum trichloride. The substituent provided on the benzene ring linked to the triazine ring by a single bond may be introduced after forming the triazine structure, or may be introduced into the phenol compound or the resorcinol derivative before forming the triazine structure.

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

  The triazine-based compound may be purified after synthesis. As the purification method, distillation, recrystallization, reprecipitation, a method using a filtering agent / adsorbent, or the like can be appropriately used. These may be used alone or in combination of two or more.

  If necessary, the triazine-based compound may be subjected to processing such as pulverization, granulation, classification, and melt solidification after purification. These may be used alone or in combination of two or more. This makes it possible to obtain desired powder characteristics of the granular triazine-based compound.

  The granular shape of the granular ultraviolet absorber of the present embodiment means a granular shape. This granular ultraviolet absorber may be used as it is in the form of granules, but may be used after being processed into a fixed shape such as pellets, briquettes, tablets and the like.

  The granular ultraviolet absorbent of this embodiment has the characteristics defined by the following particle size distribution.

With respect to the granular ultraviolet absorbent of the present embodiment, the screen residual amount on each screen can be calculated based on the following measurement procedure.
A predetermined amount (g) of the granular ultraviolet absorber is sieved in this order using a mesh opening of 4.0 mm, a mesh opening of 2.8 mm, a mesh opening of 2.0 mm and a mesh opening of 1.0 mm. Then, the residual weight (g) of the granular ultraviolet absorbent remaining on each sieve is measured, and the weight ratio (wt%) of the residual weight to a predetermined amount is calculated as the residual amount of sieve.

  According to the knowledge of the present inventor, by adopting a sieving condition in which a plurality of sieves having appropriate openings are used, the particle size distribution is broad to some extent and stable even for powders containing relatively large particles. It turned out that it is possible to measure the particle size distribution.

In the present embodiment, the sieve residue amount of the mesh opening of 4.0 mm is, for example, 0.3 wt% or more and 1.5 wt% or less, preferably 0.4 wt% or more and 1.4 wt% or less, and more preferably 0.4 wt%. It is above 1.3 wt%.
Further, the amount of the screen residue on the screen having a mesh of 2.8 mm is, for example, 5.0 wt% or more and 25.0 wt% or less, preferably 5.5 wt% or more and 24.5 wt% or less, and more preferably 6.0 wt% or more. It is 24.0 wt% or less.
In addition, the amount of the screen residue on the screen having an opening of 2.0 mm is, for example, 25.0 wt% or more and 35.0 wt% or less, preferably 25.5 wt% or more and 34.0 wt% or less, and more preferably 26.0 wt% or more. It is 33.0 wt% or less.
Further, the sieve residue amount on the sieve having a mesh size of 1.0 mm is, for example, 35.0 wt% or more and 55.0 wt% or less, preferably 36.0 wt% or more and 54.0 wt% or less, and more preferably 37.0 wt% or more. It is 53.0 wt% or less.
By setting the sieve residue amount of each of the sieves within the above numerical range, it has an appropriate particle size distribution in the range of 1 mm or more, so that dustiness, fluidity and melt-kneading property can be enhanced. Therefore, a granular ultraviolet absorber having excellent powder characteristics can be realized.

  Further, the granular ultraviolet absorbent according to the present embodiment can be configured such that the amount of non-passage when passing through a sieve with an opening of 5.0 mm is 0 wt%. By cutting the coarse particles in this manner, it is possible to realize a granular ultraviolet absorbent having excellent powder characteristics and ultraviolet absorption characteristics. Further, the melt-kneading property can be improved.

  Further, in the granular ultraviolet absorbent of the present embodiment, the amount of passage through the 1.0 mm aperture mesh is, for example, 1.0 wt% or more and 15.0 wt% or less, preferably 2.0 wt% or more and 14.5 wt% or less, It is preferably 3.0 wt% or more and 14.0 wt% or less. When the content is not more than the above upper limit, dustiness and fluidity can be enhanced.

  In the granular ultraviolet absorbent of the present embodiment, the total value of the sieve residue amounts of the above-mentioned mesh opening of 4.0 mm, mesh of 2.8 mm, mesh of 2.0 mm and mesh of 1.0 mm is 100 wt. % Or less. In addition, the total value of the residual amounts of the above-mentioned 4.0 mm sieve, the 2.8 mm aperture, the 2.0 mm aperture, and the 1.0 mm aperture of the sieve and the total amount of the passing amount of the 1 mm aperture of the sieve. Can be configured to be 100 wt%.

  In the present embodiment, it is possible to control the sieve residue amount of each of the above sieves by appropriately selecting the type and shape of the triazine compound, the method for preparing the triazine compound, and the like. Among these, for example, appropriately adopting the processing conditions of the triazine-based compound such as melting and solidifying, pulverizing and classifying are mentioned as factors for setting the sieve residual amount of each of the above sieves to a desired numerical range. To be

  Further, as a result of further study, the present inventor has found that the powder characteristics of the triazine-based compound and the granular ultraviolet absorber using the same can be appropriately controlled by using the X-ray diffraction analysis pattern as a guide. As a result of further studies based on these findings, by setting the diffraction angle 2θ at which the maximum peak in the powder X-ray diffraction analysis pattern is present within a predetermined numerical range, the above-mentioned triazine-based compound and granular ultraviolet rays using the same can be obtained. It has been found that the powder properties in the absorbent are improved.

  The triazine-based compound (granular ultraviolet absorber) of the present embodiment may have the characteristics defined by the following powder X-ray diffraction analysis pattern.

The triazine-based compound of the present embodiment has a maximum peak in a powder X-ray diffraction analysis pattern within a diffraction angle 2θ range of 5.00 ° to 6.50 °, preferably 5.20 ° to 6.00 °. , And more preferably 5.40 ° or more and 5.80 ° or less. As a result, the feed property and the compression granulation property can be enhanced, so that a triazine-based compound and a granular ultraviolet absorber having excellent powder properties can be realized.
Here, the maximum peak is the maximum peak intensity in the X-ray diffraction pattern obtained within the scanning range in the powder X-ray diffraction measurement (for example, diffraction angle 2θ = 3 ° to 60 ° or 3 ° to 90 °). I have.

  In the powder X-ray diffraction analysis pattern of the triazine-based compound, the full width at half maximum at the maximum peak is, for example, 0.05 ° or more and 0.20 ° or less, preferably 0.10 ° or more and 0.19 ° or less. It is preferably 0.15 ° or more and 0.18 ° or less. By appropriately setting the peak width of the maximum peak (maximum peak) within such a numerical range, it is possible to realize a granular ultraviolet absorber having excellent powder characteristics and ultraviolet absorption characteristics.

  In the powder X-ray diffraction analysis pattern of the triazine-based compound, when the relative intensity of the maximum peak is 100, the diffraction angle 2θ falls within a range of 3.0 ° or more and 45.0 ° or less, for example, the relative intensity. It is configured such that there are no diffraction peaks having a relative intensity of 30 or more and 60 or less, preferably a relative intensity of 25 or more and 60 or less, and more preferably a relative intensity of 22 or more and 60 or less. That is, by making the peak intensity of the maximum peak value relatively high, it is possible to realize a granular ultraviolet absorbent having excellent powder characteristics and ultraviolet absorbing characteristics.

  Further, in the powder X-ray diffraction analysis pattern of the above-mentioned triazine-based compound, when the relative intensity of the maximum peak is set to 100, a diffraction peak having a relative intensity of 1 or more and 5 or less, for example, a diffraction angle 2θ of more than 45.0 ° 60. It is configured not to exist within the range of 0.0 ° or less, preferably more than 45.0 ° and 90.0 ° or less. That is, by setting the region where the peak of slight intensity does not exist within an appropriate numerical range, it is possible to realize a granular ultraviolet absorber having excellent powder properties and ultraviolet absorption properties.

  In the present embodiment, for example, the powder X-ray diffraction analysis pattern of the maximum peak diffraction angle 2θ, the maximum peak half-width, etc. can be obtained by appropriately selecting the type and shape of the triazine compound, the method for preparing the triazine compound, and the like. It is possible to control Among these, for example, by appropriately adopting the processing conditions of the triazine-based compound such as melting and solidifying, pulverizing and classifying, powder X-ray diffraction analysis such as the diffraction angle 2θ of the maximum peak and the full width at half maximum of the maximum peak is performed. It is mentioned as an element for setting the pattern within a desired numerical range.

  The resin composition of this embodiment will be described.

  The resin composition contains the granular ultraviolet absorber. This resin composition may contain a synthetic resin. As a result, desired resin properties can be obtained according to various uses.

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

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, ultrahigh-molecular-weight polyethylene, polybutene-1, and poly-3-methylpentene, or Polyolefins such as ethylene-vinyl acetate copolymer, ethylene-ethyl acrylate copolymer, ethylene-propylene copolymer, and their copolymers, polyvinyl chloride, polyvinylidene chloride, chlorinated polyethylene, chlorinated polypropylene, polyfluorinated Vinylidene, rubber chloride, 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 -Halogen-containing resins such as maleic acid ester copolymers and vinyl chloride-cyclohexylmaleimide copolymers; petroleum resins, coumarone resins, polystyrene, polyvinyl acetate, acrylic resins, polymethyl methacrylate, polyvinyl alcohol, polyvinyl formal, polyvinyl butyral; Polyalkylene terephthalates such as polyethylene terephthalate, polybutylene terephthalate and polycyclohexane dimethylene terephthalate, aromatic polyesters such as polyalkylene naphthalate such as polyethylene naphthalate and polybutylene naphthalate, and linear polyesters such as polytetramethylene terephthalate; polyhydroxy Butyrate, polycaprolactone, polybutylene succinate, polyethylene succinate, polylactic acid resin, polyphosphorus Degradable aliphatic polyesters such as goric acid, polyglycolic acid, polydioxane and poly (2-oxetanone); polyamides such as polyphenylene oxide, polycaprolactam and polyhexamethylene adipamide, polycarbonates, branched polycarbonates, polyacetals, polyphenylene sulfides, Examples include polyurethane and fibrin-based resins.

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

In addition, examples of the elastomer include fluororesins, silicone resins, silicone rubber polyethersulfones, polysulfones, polyphenylene ethers, polyetherketones, polyetheretherketones, and liquid crystal polymers. Further, isoprene rubber, butadiene rubber, acrylonitrile-butadiene copolymer rubber, styrene-butadiene copolymer rubber, fluororubber, silicone rubber and the like can be mentioned.
More specific elastomers include, for example, olefin-based thermoplastic elastomer, styrene-based thermoplastic elastomer, polyester-based thermoplastic elastomer, nitrile-based thermoplastic elastomer, nylon-based thermoplastic elastomer, vinyl chloride-based thermoplastic elastomer, and polyamide-based thermoplastic elastomer. Examples include plastic elastomers and thermoplastic polyurethane elastomers.

  Further, as the synthetic resin excellent in transparency, for example, polyethylene, polypropylene, polystyrene, a copolymer of polyethylene and cycloolefin such as norbornene, polyacrylic acid, polyacrylic acid ester, polyvinyl acetate, polyacrylonitrile, poly Vinyl compounds such as vinyl chloride and polyvinyl fluoride, addition polymers of vinyl compounds, polymethacrylic acid, polymethacrylic acid esters, polyvinylidene chloride, polyvinylidene fluoride, polyvinylidene cyanide, vinylidene fluoride / trifluoroethylene copolymer, fluorine Vinyl compound / fluorine compound copolymer such as vinylidene fluoride / tetrafluoroethylene copolymer, vinylidene cyanide / vinyl acetate copolymer, polytrifluoroethylene, polytetrafluoroethylene, polyhexaph Fluorine-containing compounds such as propylene, polyamides such as nylon 6 and nylon 66, polyimides, polyurethanes, polypeptides, polyesters such as polybutylene terephthalate and polyethylene terephthalate, polycarbonates, polyethers such as polyoxymethylene, polyethylene oxide and polypropylene oxide. , Epoxy resin, polyvinyl alcohol, polyvinyl butyral and the like.

  From the viewpoint of compatibility and transparency, examples of the synthetic resin include polycarbonate resin, polyester resin, acrylic resin, ABS resin and the like.

  The above synthetic resins may be used alone or in combination of two or more, and may be alloyed.

The blending amount of the particulate ultraviolet 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 0.1. Even more preferably 1 to 5 parts by weight. When it is at least the above lower limit, a sufficient effect of the granular ultraviolet absorber can be obtained. Further, when the content is not more than the above upper limit, desired resin properties can be realized while improving the effect of adding the particulate ultraviolet absorber.
In the present specification, “to” indicates that the upper limit and the lower limit are included unless otherwise specified.

  The resin composition of the present embodiment may include other additive components than the above-mentioned components, if necessary. Examples of other additive components include an antioxidant, an ultraviolet absorber other than the triazine-based compound according to the present embodiment, a hindered amine-based light stabilizer, a near-infrared absorber, a nucleating agent (clearing agent), and an antistatic agent. , Lubricant, plasticizer, light absorbing pigment, filler (filler), pigment, dye, metal soap, processing aid, flame retardant, flame retardant aid, zeolite compound, foaming agent, (heavy) metal deactivator , A cross-linking agent, an epoxy stabilizer, a matting agent, an antifogging agent, a plate-out preventing agent, a surface treatment agent, a fluorescent brightening agent, a mildew proofing agent, an antibacterial agent, and a release agent.

  Examples of the antioxidant include phenol-based antioxidants, phosphorus-based antioxidants, sulfur-based antioxidants and the like.

  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-hexamethylene bis [(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′-ethylidene bis (4,6-di-tert-butylphenol), 2 2'-ethylidene bis (4-sec-butyl-6-tert-butylphenol), 1,1,3-tris (2-methyl-4-hydroxy-5-tert-butylphenyl) butane, 1,3,5- Tris (2,6-dimethyl-3-hydroxy-4-tert-butylbenzyl) isocyanurate, 1,3,5-Tris (3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, 1, 3,5-Tris (3,5-di-tert-butyl-4-hydroxybenzyl) -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, Trakis [methyl 3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate] methane, thiodiethylene glycol bis [(3,5-di-tert-butyl-4-hydroxyphenyl) propionate], 1 , 6-hexamethylene bis [(3,5-di-tert-butyl-4-hydroxyphenyl) propionate], bis [3,3-bis (4-hydroxy-3-tert-butylphenyl) butyric acid] glycol Ester, bis [2-tert-butyl-4-methyl-6- (2-hydroxy-3-tert-butyl-5-methylbenzyl) phenyl] terephthalate, 1,3,5-tris [(3,5-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] and the like can be mentioned.

  Examples of the phosphorus-based antioxidant include trisnonylphenylphosphite, tris [2-tert-butyl-4- (3-tert-butyl-4-hydroxy-5-methylphenylthio) -5-methylphenyl]. Phosphite, tridecyl phosphite, triisodecyl phosphite, trilauryl phosphite, octyl diphenyl phosphite, di (decyl) monophenyl phosphite, di (tridecyl) pentaerythritol diphosphite, di (nonylphenyl) pentaerythritol Diphosphite, bis (2,4-di-tert-butylphenyl) pentaerythritol diphosphite, bis (2,6-di-tert-butyl-4-methylphenyl) pentaerythritol diphosphite, bis (2,2 4,6-tri-tert Butylphenyl) pentaerythritol diphosphite, bis (2,4-dicumylphenyl) pentaerythritol diphosphite, tetra (tridecyl) isopropylidene diphenol diphosphite, tetra (tridecyl) -4,4'-n-butylidene bis (2-tert-butyl-5-methylphenol) diphosphite, hexa (tridecyl) -1,1,3-tris (2-methyl-4-hydroxy-5-tert-butylphenyl) butane triphosphite, tetrakis (2,2. 4-di-tert-butylphenyl) biphenylenediphosphonite, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 2,2'-methylenebis (4,6-tert-butyl) Phenyl) -2-ethylhexylphosph , 2,2'-methylenebis (4,6-tert-butylphenyl) -octadecylphosphite, 2,2'-ethylidenebis (4,6-di-tert-butylphenyl) fluorophosphite, tris (2- [(2,4,8,10-Tetrakis-tert-butyldibenzo [d, f] [1,3,2] dioxaphosphapin-6-yl) oxy] ethyl) amine, 2-ethyl-2- Examples include phosphite of butyl propylene glycol and 2,4,6-tri-tert-butylphenol.

  Examples of the sulfur-based antioxidants include dilauryl thiodipropionate, dimyristyl thiodipropionate, dialkylthiodipropionates such as distearyl thiodipropionate, and pentaerythritol tetra (β-alkylthiopropionate). Esters may be mentioned.

  Examples of the ultraviolet absorber other than the triazine-based compound according to the present embodiment include 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-octoxybenzophenone, 5,5. 2-hydroxybenzophenones such as'-methylenebis (2-hydroxy-4-methoxybenzophenone); 2- (2'-hydroxy-5'-methylphenyl) benzotriazole, 2- (2'-hydroxy-3 ', 5 '-Di-tert-butylphenyl) -5-chlorobenzotriazol, 2- (2'-hydroxy-3'-tert-butyl-5'-methylphenyl) -5-chlorobenzotriazole, 2- (2'-hydroxy-5'-tert-octylphenyl) benzotriazole, 2- (2'-hi) Roxy-3 ′, 5′-dicumylphenyl) benzotriazole, 2,2′-methylenebis (4-tert-octyl-6- (benzotriazolyl) phenol), 2- (2′-hydroxy-3 ′) 2- (2′-hydroxyphenyl) benzotriazoles such as -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-butyl-4-hydroxybenzoate, hexadecyl-3,5-di-tert-butyl-4 -Benzoates such as hydroxybenzoate; 2-ethyl-2'-ethoxyoxa Substituted oxanilides such as lido and 2-ethoxy-4′-dodecyloxanilide; ethyl-α-cyano-β, β-diphenyl acrylate, methyl-2-cyano-3-methyl-3- (p-methoxyphenyl) Examples include cyanoacrylates such as acrylate.

  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, 2,2,2. 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-butane tetracarboxylate, 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-piperidinole / 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-piperidi Amino) hexane / 2,4-dichloro-6-tert-octylamino-s-triazine polycondensate, 1,5,8,12-tetrakis [2,4-bis (N-butyl-N- (2,2 , 6,6-Tetramethyl-4-piperidyl) amino) -s-triazin-6-yl] -1,5,8,12-tetraazadodecane, 1,5,8,12-tetrakis [2,4- Bis (N-butyl-N- (1,2,2,6,6-pentamethyl-4-piperidyl) amino) -s-triazin-6-yl] -1,5,8-12-tetraazadodecane, 1 , 6,11-Tris [2,4-bis (N-butyl-N- (2,2,6,6-tetramethyl-4-piperidyl) amino) -s-triazin-6-yl] aminoundecane, 1 , 6,11-Tris [2,4-bis (N-butyl-N) Examples thereof include hindered amine compounds such as-(1,2,2,6,6-pentamethyl-4-piperidyl) amino) -s-triazin-6-yl] aminoundecane.

  Examples of the near infrared absorbing agent include polymethine dyes (cyanine dyes), indolinocyanine dyes, phthalocyanine dyes, naphthalocyanine dyes, naphthol metal complex dyes, squarylium dyes, triazo dyes, dithiol metal complex salt dyes. , Pyrylium dyes, thiapyrylium dyes, indoaniline dyes, azoanthraquinone dyes, naphthoquinone dyes, anthroquinone dyes, bis (dithiolene) dyes, triphenylmethane dyes, aminium (aluminum) dyes, diimonium dyes, and the like. Further, an inorganic near-infrared absorber may be used, for example, tin oxide doped with carbon black, antimony oxide or indium oxide, oxides, carbides or borides of metals belonging to Group 4A, 5A or 6A of the periodic table. Compound It is below.

  Examples of the nucleating agent include metal salts of benzoic acids such as aluminum p-tert-butylbenzoate and sodium benzoate, sodium bis (2,4-di-tert-butylphenyl) phosphate, methylenebis (2,2). 4-di-tert-butylphenyl) phosphoric acid ester sodium, bis [methylenebis (2,4-di-tert-butylphenyl) phosphoric acid ester] hydroxyaluminum, etc. aromatic phosphoric acid ester metal salt and aromatic phosphoric acid ester Mixtures of metal salts and alkali metal compounds, dibenzylidene sorbitol, bis (methylbenzylidene) sorbitol, bis (p-ethylbenzylidene) sorbitol, bis (dimethylbenzylidene sorbitol) and other dibenzylidene sorbitols, amino acid metal salts, metal rosinates , N N ', N "-tris [2-methylcyclohexyl] -1,2,3-propanetricarboxamide, N, N', N" -tricyclohexyl-1,3,5-benzenetricarboxamide, N, N'- Examples thereof include amide compounds such as dicyclohexylnaphthalene dicarboxamide and 1,3,5-tri (dimethylisopropoylamino) benzene.

  Examples of the antistatic agent include cationic antistatic agents such as fatty acid quaternary ammonium ion salt and polyamine quaternary salt; higher alcohol phosphate ester salt, higher alcohol EO adduct, polyethylene glycol fatty acid ester, and anionic type Anionic antistatic agents such as alkyl sulfonate, higher alcohol sulfate ester salt, higher alcohol ethylene oxide adduct sulfate ester salt, higher alcohol ethylene oxide adduct phosphate ester salt; polyhydric alcohol fatty acid ester, polyglycol phosphate ester, poly Nonionic antistatic agents such as oxyethylene alkyl allyl ethers; amphoteric alkyl betaines such as alkyldimethylaminoacetic acid betaines; amphoteric antistatic agents such as imidazoline type amphoteric activators; ionomers and polyethylene glycols. Polymeric antistatic agent containing a block polymer and a hydrophilic portion and the like.

  Examples of the lubricant include hydrocarbon lubricants such as liquid paraffin, paraffin wax, and polyethylene wax; aliphatic lubricants such as stearyl alcohol, stearic acid, and 12-hydroxystearic acid; stearic acid amide, oleic acid amide, and erucic acid. Amides, amide lubricants such as methylenebisstearic acid amide and ethylene stearic acid amide; calcium stearate, zinc stearate, magnesium stearate, lead stearate, aluminum stearate, barium stearate, barium stearate / zinc stearate complex , Metal soap lubricants such as zinc stearate / calcium stearate complex; hardened oil and fat, glycerin monostearate, butyl stearate, pentaerythritol stearate, stearate stearate Include ester lubricant Lil and the like.

  Examples of the plasticizer include phthalic acid ester, dibasic acid ester, chlorinated paraffin, polyester, epoxidized ester, phosphoric acid ester, trimellitic acid ester, and the like.

  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, dithiol metal complex-based A compound etc. are mentioned.

  Examples of the filler include calcium carbonate, calcium oxide, calcium hydroxide, zinc hydroxide, zinc carbonate, zinc sulfide, magnesium oxide, magnesium hydroxide, magnesium carbonate, aluminum oxide, aluminum hydroxide, sodium alumina silicate, Hydrocalumite, aluminum silicate, magnesium silicate, calcium silicate, metal silicates such as 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, fibrous magnesium compound), phosphate Fibers, glass fibers, carbon fibers, aramid fibers, cellulose nanofibers, and the like.

  As the pigment, for example, a commercially available pigment may be used, and for example, 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, 184, 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, 9 , 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 and the like.

  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. , Dyes such as phthalocyanine dyes and cyanine dyes.

  Examples of the metal soap include metals such as lithium, sodium, potassium, magnesium, calcium, aluminum, hydroxyaluminum, barium and zinc, and lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid and oleic acid. Saturated or unsaturated fatty acid salts are used.

  The processing aid may be appropriately selected from known processing aids, but acrylic acid-based processing aids are preferred. Examples of processing aids include homopolymers or copolymers of alkylmethacrylates such as methylmethacrylate, ethylmethacrylate, butylmethacrylate; and the above-mentioned alkylmethacrylates and alkylacrylates such as methylacrylate, ethylacrylate, butylacrylate. Copolymer; Copolymer of the alkyl methacrylate with an aromatic vinyl compound such as styrene, α-methylstyrene, vinyltoluene; Copolymerization of the alkyl methacrylate with a vinyl cyan compound such as acrylonitrile and methacrylonitrile Examples include coalescing.

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

  Examples of the triazine ring-containing compound include melamine, ammeline, benzguanamine, acetoguanamine, phthalodiguanamine, melamine cyanurate, melamine pyrophosphate, butylene diguanamine, norbornene diguanamine, methylene diguanamine, ethylene dimelamine, trimethylene. Examples thereof include dimelamine, tetramethylene dimelamine, hexamethylene dimelamine, and 1,3-hexylene dimelamine.

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

  Examples of the above-mentioned phosphate ester flame retardant include, for example, 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, isopropylphenyldiphenylpho Feto, bis - (isopropylphenyl) diphenyl phosphate, tris - (isopropylphenyl) phosphate, and the like.

  Examples of the condensed phosphate ester flame retardant include 1,3-phenylene bis (diphenyl phosphate), 1,3-phenylene bis (dixylenyl phosphate), bisphenol A bis (diphenyl phosphate), and the like. Examples of the mescent flame retardant include ammonium salts and amine salts of (poly) phosphoric acid such as ammonium polyphosphate, melamine polyphosphate, piperazine polyphosphate, ammonium pyrophosphate, melamine pyrophosphate and piperazine pyrophosphate.

  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, TIPAQUE R-680 (titanium oxide: Ishihara Sangyo Various commercial products such as Kyowamag 150 (magnesium oxide: manufactured by Kyowa Chemical Industry Co., Ltd.) and the like can be used.

  Examples of other organic flame retardant aids include pentaerythritol and dipentaerythritol.

  The above-mentioned zeolite compound is an aluminosilicate of an alkali or alkaline earth metal having a unique three-dimensional zeolite crystal structure, and typical examples thereof include A-type, X-type, Y-type and P-type zeolite, monodenite, and anal. Examples thereof include cite, sodalite aluminosilicate, clinobuchilorite, erionite, chabazite, etc., and a water-containing substance having crystal water of these zeolite compounds (so-called zeolite water) or an anhydride obtained by removing crystal water. Any of these may be used, and those having a particle size of 0.1 to 50 μm can be used, and those having a particle size of 0.5 to 10 μm are particularly preferable.

  Examples of the foaming agent include azodicarbonamide, azobisisobutyronitrile, p, p′-oxybisbenzenesulfonyl hydrazide, n, n′-dinitrosopentamethylenetetramine, p-toluenesulfonyl semicarbazide, trihydrazo. Examples thereof include decomposition-type organic foaming agents such as triazine and decomposition-type inorganic foaming agents such as sodium bicarbonate, ammonium carbonate, ammonium bicarbonate, ammonium nitrite, azide compounds, and sodium borohydride.

  Examples of the (heavy) metal deactivator include salicylamide-1,2,4-triazol-3-yl, bissalicylic acid hydrazide, dodecanedioyl bis (2- (2-hydroxybenzoyl) hydrazide), and bis (3 -(3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid) hydrazide and the like.

  Examples of the cross-linking 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, tetramethylisophthalyldi-tert-butylbisperoxide, Examples thereof include tetramethylisophthalyldicumylbisperoxide, alkanolamines such as diethanolamine and triethanolamine, hexamethylenediamine, and 4,4′-diaminodiphenylmethane.

  Examples of the epoxy-based stabilizer include compounds having an aliphatic, aromatic, alicyclic, aromatic-aliphatic or heterocyclic structure and having an epoxy group as a side chain. The epoxy group is preferably attached to the residue of the molecule by an ether or ester bond as a glycidyl group or may be an N-glycidyl derivative of a heterocyclic amine, amide or imide. Specific examples thereof include epoxidized soybean oil, epoxidized linseed oil, and epoxidized monoester. Examples of commercially available epoxy stabilizers include ADEKA product names "ADEKA CIZER O-130P", "ADEKA CIZER O-180A", "ADEKA CIZER D-32", "ADEKA CIZER EP-13", and "ADEKA CIZER EP-13". Adeka Sizer FEP-13 "and the like.

  As the matting agent, fine particles of silicon dioxide are preferable. Examples of the fine particles of silicon dioxide include Aerosil R972, R972V, R974, R812, 200, 200V, 300, R202, OX50, TT600 (manufactured by Nippon Aerosil Co., Ltd.). Aerosil 200V, Aerosil R972V, and Aerosil R812 are preferable because they have a large effect of lowering the coefficient.

Examples of the antifogging agent include glycerin fatty acid ester, alkyldiethanolamine, alkyldiethanolamine fatty acid ester and the like.
Examples of the plate-out preventing agent include those containing silicon dioxide, an alkylene oxide adduct of an ethylene-saturated carboxylic acid vinyl ester copolymer saponification product as an active ingredient.

  As the surface treatment agent, for example, a surface treatment agent containing at least one of an aminosilane compound and an epoxy resin is preferably used.

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

  Examples of the epoxy resin contained in the surface treatment agent include novolac type epoxy resin and bisphenol type epoxy resin, and the novolac type epoxy resin is preferably used. Examples of novolac type epoxy resins include multifunctional epoxy resins such as phenol novolac type epoxy resins and cresol novolac type epoxy resins.

  In addition to the above aminosilane compound and epoxy resin, the surface treatment agent may be blended with components such as urethane resin, acrylic resin, antistatic agent, lubricant, water repellent, etc. within a range that does not impair the properties. . Further, other surface treatment agents include epoxy resins other than novolac type and bisphenol type, coupling agents and the like.

  The fluorescent whitening agent is a compound that absorbs ultraviolet rays of sunlight or artificial light and converts them into visible rays of purple to blue to radiate them, thereby promoting whiteness and bluishness of the molded body. . Examples of the fluorescent whitening agent include benzoxazole-based compounds C.I. I. Fluorescent Brightner 184; coumarin-based compound C.I. I. Fluorescent Brightner 52; diaminostilbene disulphonic acid compound C.I. I. Fluorescent Brightner 24, 85, 71 and the like.

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

  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, silver-based zeolites containing zinc and apatite, and apatite. Inorganic antibacterial agents such as a system, a silica-alumina system, a ceramic system, a zirconium phosphate system, a silica gel system, a hydroxyapatite system or a calcium silicate system can be mentioned.

  Examples of the release agent include sodium montanate, potassium montanate, calcium montanate, magnesium montanate and the like.

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

As an example of the method for producing the resin composition, the granular ultraviolet absorber of the present embodiment, the above-mentioned synthetic resin, each component such as other additive components as necessary, various mixers such as a tumbler and a Henschel mixer. And a melt mixing method using a Banbury mixer, a roll, a Brabender, a single-screw kneading extruder, a twin-screw kneading extruder, a kneader and the like.
Alternatively, the resin composition may be produced by premixing each of the components or premixing only some of the components and supplying the mixture to an extruder using a feeder and melt-kneading. Further, a resin composition obtained by mixing some of the components in advance and supplying them to an extruder and melt-kneading them into a masterbatch, and again mixing with other components and melt-kneading to produce a resin composition. You can also do it.
Further, the synthetic resin used in the above mixing / kneading step may have a predetermined shape such as powder, pellets or the like, or a fibrous shape.

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

A molded product can be obtained by molding the resin composition of the present embodiment.
The molding method is not particularly limited, and injection molding method, extrusion molding method, blow molding method, rotational molding, vacuum molding method, inflation molding method, calender molding method, slush molding method, dip molding method, foam molding method. Law etc. are mentioned.

  The above-mentioned molded article can have various forms depending on the application, but has various shapes such as a resin plate, a sheet, a film, a container (bottle, tray, bag), a fiber and various molded articles. obtain.

  Further, the resin composition of the present embodiment, the granular ultraviolet absorber of the present embodiment, the above-mentioned synthetic resin used as a binder resin, each component such as other additive components as necessary, dissolved in a solvent varnish resin (Varnish resin composition that is liquid at room temperature) may be used. As the solvent, an organic solvent or an aqueous solvent can be used. The resin varnish may be used as an emulsion in which a powdery ultraviolet absorber is dispersed by using an emulsifier if necessary.

As a method for preparing the resin varnish, the order of mixing the respective components is not particularly limited, all the components may be mixed at the same time, or the particulate ultraviolet absorber of the present embodiment and other additive components are mixed in advance. The resulting mixture may be mixed with a synthetic resin, a plurality of components prepared in advance may be mixed with other components, or a plurality of components prepared in advance. You may further mix each other.
The resin varnish can be processed into a film or sheet by using, for example, a cast film method. The resin varnish can also be used as a paint material for coating on a predetermined substrate.

  The resin composition of the present embodiment is electric / electronic / communications, agriculture, forestry and fisheries, mining, construction, food, textiles, clothing, medical care, coal, oil, rubber, leather, automobiles, precision equipment, wood, building materials, civil engineering, furniture. Can be used in a wide range of industrial fields such as printing, musical instruments, etc.

  More specific applications include, for example, printers, personal computers, word processors, keyboards, PDAs (small information terminals), telephones, copiers, facsimiles, ECRs (electronic cash registers), calculators, electronic organizers, cards, holders, Office work such as stationery, office automation equipment, washing machines, refrigerators, vacuum cleaners, microwave ovens, lighting equipment, game machines, home appliances such as irons and kotatsu, TVs, VTRs, video cameras, radio cassette recorders, tape recorders, mini disks, CD players. , AV equipment such as speakers, liquid crystal displays, connectors, relays, capacitors, switches, printed circuit boards, coil bobbins, semiconductor encapsulation materials, LED encapsulation materials, electric wires, cables, transformers, deflection yokes, distribution boards, clocks, etc.・ Electronic parts and communication equipment, interior and exterior materials for automobiles, film for plate making, adhesive film, Torr, food containers, food packaging films, pharmaceutical and pharmaceutical wrap film, product packaging film, agricultural film, agricultural sheeting, greenhouse film, and the like.

Also, as specific applications, seats (filling, outer material, etc.), belts, ceiling coverings, compatible tops, armrests, door trims, rear package trays, carpets, mats, sun visors, wheel covers, mattress covers, airbags, insulation. Materials, hangers, straps, electric wire coating materials, electrical insulation materials, paints, coating materials, upholstery materials, floor materials, corner walls, carpets, wallpapers, wall covering materials, exterior materials, interior materials, roof materials, decks Materials such as wood, wall materials, pillar materials, floor boards, fence materials, skeletons and moldings, window and door profiles, shingles, siding, terraces, balconies, soundproof boards, heat insulation boards, window materials, etc. , Aircraft, buildings, housing and construction materials and civil engineering materials, clothing, curtains, sheets, non-woven fabrics, plywood, synthetic fiber boards, carpets, entrance mats, sheets, buckets, hoses, containers, glasses, bags, cases, goggles , Skis, rackets, tents, household goods of the musical instrument or the like, and include various applications, such as sporting goods. In addition to these, paints, cosmetics and the like can be mentioned.
Also, pharmaceutical containers for medicines, vitamins, drinks, eye drops, etc .; cosmetic containers for lotions, emulsions, sunscreens, etc .; food containers, liquor, wine, beer, fruit juice, soft drinks, tea, tea, coffee, etc. Beverage containers; applications such as shampoos, rinses, mouthwashes, toothpastes, disinfectants, and other daily necessities containers are also included.

  Further, the resin composition of the present embodiment is not particularly limited, but can be suitably used as an optical material such as an optical film or an optical sheet by molding it into a sheet or a film. As the optical material, for example, an image display device such as a liquid crystal display device (LCD), a plasma display panel (PDP), an electroluminescence display (ELD), a cathode ray tube display device (CRT), a fluorescent display tube, a field emission display is used. It is useful as an optical film or an optical sheet, and is particularly useful as an optical film such as an optical correction film for a liquid crystal display device or an organic EL display that uses an organic material having poor ultraviolet resistance for a display element, or a light emitter protection film. As liquid crystal display device applications, polarizing plate protective film or protective sheet, retardation film, viewing angle widening film, antiglare film, brightness enhancement film, light diffusion film and light diffusion sheet, lens film and lens sheet, anti-fog film, An antistatic film, an optical correction film, an antireflection film, a color adjustment film, a light guide plate, and the like are included, and in particular, an optical film or an optical sheet installed on the outer surface side of a polarizing plate that is in contact with a liquid crystal display element, or polarized light. It can be suitably used for a plate protective film or an optical sheet.

  Although the embodiments of the present invention have been described above, these are examples of the present invention, and various configurations other than the above can be adopted.

  Hereinafter, the present invention will be described in detail with reference to examples, but the present invention is not limited to the description of these examples.

[Preparation of granular UV absorber]
(Example 1)
2,4,6-Tris [2-hydroxy-3-methyl-4-hexyloxyphenyl] triazine was synthesized by the following procedure.
In a 300 ml four-necked flask, 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 1-bromo. 11.07 g of hexane was added, the temperature was raised to 80 ° C., and the reaction was performed for 9 hours. After performing neutralization treatment with hydrochloric acid, washing with water, desolvation under reduced pressure, and recrystallization of the residue from toluene: isopropyl alcohol = 1: 1, crystals were obtained. Thereafter, the melted target substance (crystal) was dropped onto a metal plate and cooled to obtain flakes (melt solidification treatment). The obtained flakes were coarsely pulverized and classified to obtain 11.89 g (yield: 76%) of pale yellow granules having a melting point of 145 ° C.
¹ H-NMR measurement was performed on the obtained compound (pale yellow granule). The pale yellow granules obtained from the following analysis results are represented by the following formula No. It was identified as a granular compound represented by 1 (granular ultraviolet absorber).

(Examples 2 to 5)
In the same manner as in Example 1, different lots of granular compound No. 1 (granular ultraviolet absorber) was obtained.

(Comparative Example 1)
The crystal obtained in Example 1 was crushed in a mortar without carrying out the melt solidification treatment to obtain the above formula No. A powdery compound represented by 1 (granular ultraviolet absorber) was obtained.

(Comparative example 2)
The granular compound having a large particle size obtained in the classification in Example 1 was collected to obtain a granular ultraviolet absorber.

  The granular ultraviolet absorbent obtained as described above was evaluated based on the following evaluation items. The evaluation results are shown in Table 1.

(Particle size distribution)
The particle size distribution of the obtained granular ultraviolet absorber was sieved using a plurality of sieves, and the residual ratio was calculated from the weight of the residue on each sieve. Specifically:
First, about 200 g (total amount) of the obtained granular ultraviolet absorber was put in the uppermost sieve, and a vibrating and sieving device (Lecce's AS300) equipped with a sieve was used under the conditions of the following sieve and amplitude. And shaken for 3 minutes (sieving operation). The weight (g) of the granular ultraviolet absorber remaining on each sieve was measured, and the weight ratio (wt%) to the total amount introduced was calculated as the sieve residue amount with respect to the weight.
・ Opening: 4.0 mm, 2.8 mm, 2.0 mm, 1.0 mm (set from the top in this order)
・ Amplitude: 1.00 mm, 3 min

In Table 1, the residual amount of the sieve indicates the weight ratio of the particulate ultraviolet absorber remaining on the sieve by the sieving operation. The passing amount indicates the weight ratio of the particulate ultraviolet absorber that has passed through a sieve having an opening of 1.0 mm.
In addition, Table 1 shows the results of the residual amount (wt%) of the sieve on the 5.0 mm sieve when the obtained granular ultraviolet absorber was sieved using a 5.0 mm sieve.

(Dustiness)
Handling property A mixture of 0.2 parts by mass of the obtained granular ultraviolet absorber with 100 parts by mass of the polycarbonate resin was mixed for 10 minutes by a Henschel mixer to obtain a mixture. The handling property was evaluated based on the following evaluation criteria.
A: Almost no dusting was observed.
X: A large amount of dusting was observed.
-Work environment property The obtained granular ultraviolet absorber was dropped from the upper portion of 30 cm onto a saucer, and the amount put on the saucer was measured. The work environment was evaluated based on the following evaluation criteria.
○: The amount remaining in the saucer is relatively large.
X: Remaining amount in the saucer was relatively small, and most of it protruded from the saucer.

(Liquidity)
What mixed 0.2 mass part of obtained granular ultraviolet absorbers with respect to 100 mass parts of polycarbonate resin was mixed for 10 minutes with a Henschel mixer, and the obtained mixture was supplied to the extruder from the hopper of an extruder. did. The fluidity in the hopper was evaluated based on the following evaluation criteria.
⊚: The fluidity of the mixture was good, and no poor charging occurred. ◯: The mixture was relatively fluid, and no defective charging occurred within a practically acceptable range.
X: The fluidity of the mixture was lowered, and defective charging occurred.

(Melting and kneading properties)
The obtained particulate ultraviolet absorber was mixed in an amount of 1 part by mass with 100 parts by mass of an acrylic resin, and melt-kneaded at 250 ° C. using a twin-screw extruder (L / D = 30). Granulation was performed to obtain pellets. The pellets were observed when the discharge rate was set to 0.3 kg / h, and the melt-kneading property 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 separated slightly, but melt kneading was possible.
X: The resin and the granular ultraviolet absorber were separated and could not be melt-kneaded.

  Further, X-ray diffraction analysis was performed on the obtained granular ultraviolet absorbents of Example 1 and Comparative Example 1. The evaluation results are shown in Tables 2-4.

(X-ray diffraction)
Powder X-ray diffraction measurement was performed on the obtained particulate ultraviolet absorber using Ultima IV (Rigaku Corporation) under the following measurement conditions.
(Measurement condition)
X-ray tube: CuKα ray (CuKα1 = 1.540562Å, CuKα2 = 1.544398Å, CuKα2 not removed)
Tube voltage / tube current: 40kV / 40mA
Attachment: Multipurpose thin film sample stage Monochromator: Fixed filter: None Divergence slit: 2/3 °
Divergence vertical restriction slit: 10 mm
Scattering slit: 1.17mm
Light receiving slit: 0.3mm
Scan type: Continuous scan Scan speed: 4 ° / min
Sampling width: 0.02 °
Scanning axis: 2θ / ω
Scanning range: = 3 ° to 90 °

  The result of the powder X-ray diffraction analysis for the granular ultraviolet absorbent of Example 1 is shown in FIG. Table 3 shows the diffraction angle 2θ, the d value, and the relative intensity corresponding to each peak in FIG. In Table 3, deg represents °, and the threshold of peak intensity was set to 1/100 of the maximum peak.

  The result of the powder X-ray diffraction analysis for the granular ultraviolet absorbent of Comparative Example 1 is shown in FIG. Table 4 shows the diffraction angles 2θ, d values, and relative intensities corresponding to the respective peaks in FIG. In Table 4, the threshold of peak intensity was set to 1/100.

(Feedability)
1 kg of the obtained granular ultraviolet absorber was put into a hopper, and a weight type feeder (manufactured by K-Tron, length: 25 cm x outer diameter: 1.4 cm, groove width: 2.0 cm, groove depth: 0. Using a 3 cm Twin spiral type twin screw), the material was discharged for 30 minutes under the condition of the feeder discharge rate: 0.3 kg / h (feed property test).
-Quantitativeness The amount discharged from the gravimetric feeder (feeder amount) was measured at time intervals of 10 minutes. The case where the variation in the feed amount was small was marked with ◯, and the case where the variation in the feed amount was large was marked with x.
-Long run property The above feed test was carried out in the same manner except that the discharge time condition was changed from 30 minutes to 3 hours. The case where the discharge was continued for 3 hours was marked with ◯, and the case where the operation was stopped before the lapse of 3 hours was marked with x.

(Compression granulation)
Using a roller compactor (manufactured by Hosokawa Micron Co., Ltd., granulator M-25 type), the obtained granular ultraviolet absorber was compression-granulated under the conditions of roll gap: 3.2 mm and roll rotation speed: 14 rpm to obtain a plate. A plate-like granule having a thickness of 4 mm was obtained. The obtained plate-like granules were crushed, coarse powder was removed with a 5-mesh vibrating screen, and then fine powder was removed with a 24-mesh vibrating screen (size control), and then remained on a 24-mesh vibrating comb. A plate-shaped granulated product was obtained.
The appearance of the obtained granulated product was observed, and the disintegration degree of the granulated product was evaluated based on the following criteria.
Out of 10 granules, disintegration could not be observed in 10 granules, and in 1 granules from 1 to 4 granules, some disintegration was dissipated, and in 10 granules. The one in which 5 or more granules were observed to be partially or wholly disintegrated was defined as x.

[Preparation of resin composition]
(Production of film)
A mixture of 100 parts by mass of a synthetic resin (polycarbonate resin: product name E-2000 manufactured by Mitsubishi Engineering Plastics Co., Ltd.) with 0.2 parts by mass of the granular ultraviolet absorber of each of the obtained Examples, A resin composition was prepared by dissolving it in 230 parts by mass of a solvent (toluene / cyclohexane = 9/1). A film having a thickness of 40 μm was produced from the obtained resin composition by a casting method to obtain a square film test piece having a side of 2 cm.
The retention rate (%) of the total light transmittance (%) after 240, 360, and 480 hours of the obtained film test piece was measured with a sunshine weatherometer (83 ° C., no rain, light source carbon arc). The light resistance was evaluated.
From the result that the retention rate (%) after 240, 360 and 480 hours was high, it was found that excellent light resistance can be realized by using the granular ultraviolet absorbent of each Example.
It was also found that even when a methacrylic resin, a norbornene resin, a polyethylene terephthalate resin, or a polystyrene resin was used as the synthetic resin instead of the polycarbonate resin, similarly excellent light resistance could be realized.

(Production of container)
To 100 parts by mass of polyethylene terephthalate (intrinsic viscosity: 0.8 dL / g), 0.3 parts by mass of the obtained particulate ultraviolet absorber of each example was added and mixed to obtain a resin composition. The obtained resin composition was dried in a gear oven at 160 ° C. for 4 hours, and then, a preform (outer diameter 25 mm, weight 23 g) was molded by an injection molding machine at a molding temperature of 280 ° C. Next, the obtained preform was biaxially stretch blow-molded at a mold temperature of 130 ° C. to produce a plastic bottle having a capacity of 500 mL and a thickness of 0.7 mm. The transmittance of visible light having a wavelength of 500 nm and the transmittance of ultraviolet light having a wavelength of 400 nm were measured for the obtained plastic bottle. From the results of high transmittance at wavelength of 500 nm and low transmittance at wavelength of 400 nm, the obtained plastic bottle (container) efficiently absorbs ultraviolet rays and sufficiently secures visible light transmittance. I understood.

(Preparation of coating material)
-Ultraviolet absorbing layer 0.5 parts by mass of the obtained granular ultraviolet absorbent of each example and 2000 parts by mass of dichloromethane as a solvent, relative to 100 parts by mass of norbornene resin (JSR Corporation, product name: ARTON F5023). The parts were mixed to obtain a resin solution (resin composition). The obtained resin solution was cast on a surface-polished glass plate using a bar coater, preliminarily dried at 50 ° C. for 20 minutes and dried at 90 ° C. for 30 minutes to give a film having a thickness of 80 to 90 μm. After the production, a square film test piece (ultraviolet absorbing layer) having a side of 2 cm was obtained.
-Preparation of NIR absorption layer For 100 parts by mass of norbornene resin (manufactured by JSR Corporation, product name: ARTON F5023), a diimmonium compound (manufactured by Nippon Kayaku Co., Ltd., product name: IRG-) as a near-infrared absorber. 068) A resin solution consisting of 0.3 parts by mass and 2000 parts by mass of dichloromethane as a solvent was cast on a surface-polished glass plate using a bar coater, pre-dried at 50 ° C. for 20 minutes, and 90 ° C. for 30 minutes. After producing a film having a film thickness of 50 to 60 μm, a square film test piece having a side of 2 cm was obtained.
The test piece obtained by superimposing the NIR absorption layer and the ultraviolet absorption layer on top of each other was measured with a sunshine weather meter (Suga Test Instruments Co., Ltd .; 83 ° C., no rain, light source carbon arc), and the test light was emitted from the ultraviolet absorption layer side. Exposure was for 360 (or 540) hours. The transmittance at the maximum wavelength (NIR absorption layer: 1100 nm) in the NIR region before and after the light resistance test was measured, and the light resistance was evaluated by the attenuation factor (Δ transmittance) of the transmittance.
From the results that the Δ transmittance could be reduced in each of the examples, it was confirmed that the effect on the photodegradation of the near-infrared absorber was exhibited. This proves that the near-infrared absorbing layer in the near-infrared absorbing layer is excellent in preventing photo-deterioration.

  The granular ultraviolet absorbers of Examples 1 to 5 are superior in dusting property and fluidity as compared with Comparative Example 1 and are superior in melt-kneading property as compared with Comparative Example 2 and therefore exhibit good powder characteristics. I understood. Further, it was found that the compounds of Examples 1 to 5 were excellent in ultraviolet absorbing properties and could be suitably used as ultraviolet absorbers.

  This application claims priority based on Japanese Patent Application No. 2018-067812 filed on Mar. 30, 2018 and Japanese Patent Application No. 2018-067830 filed on Mar. 30, 2018. , The entire disclosure of which is incorporated herein.

（上記一般式（Ｉ）中、
Ｒ ^１ は、置換又は無置換の、直鎖又は分岐の炭素原子数１〜２０のアルキル基、炭素原子数３〜２０のシクロアルキル基、炭素原子数６〜２０のアリール基、炭素原子数７〜２０のアルキルアリール基、炭素原子数７〜２０のアリールアルキル基、炭素原子数２〜８のアルケニル基、又は下記一般式（ＩＩ）で表される置換基を表し、
Ｒ ^２ 及びＲ ^３ は、それぞれ独立に、水素原子、置換又は無置換の、直鎖又は分岐の炭素原子数１〜２０のアルキル基、または−Ｏ−Ｒを表し、このＲは、置換又は無置換の、直鎖又は分岐の炭素原子数１〜２０のアルキル基、炭素原子数３〜２０のシクロアルキル基、炭素原子数６〜２０のアリール基、炭素原子数７〜２０のアルキルアリール基、又は炭素原子数７〜２０のアリールアルキル基を表し、
Ｒ ^４ 、Ｒ ^５ 、Ｒ ^６ 、Ｒ ^７ 、Ｒ ^８ 、Ｒ ^９ 、Ｒ ^１０ 、Ｒ ^１１ 及びＲ ^１２ は、それぞれ独立に、水素原子、ハロゲン原子、置換又は無置換の、直鎖又は分岐の炭素原子数１〜８のアルキル基又は直鎖又は分岐の炭素原子数２〜８のアルケニル基を表し、
Ｒ ^１３ 及びＲ ^１４ は、それぞれ独立に、水素原子またはヒドロキシ基を表す。
ただし、Ｒ ^１ 、Ｒ ^２ 、Ｒ ^３ 及びＲで表される置換又は無置換の、直鎖又は分岐の炭素原子数１〜２０のアルキル基、Ｒ ^４ 、Ｒ ^５ 、Ｒ ^６ 、Ｒ ^７ 、Ｒ ^８ 、Ｒ ^９ 、Ｒ ^１０ 、Ｒ ^１１ 及びＲ ^１２ で表される置換又は無置換の、直鎖又は分岐の炭素原子数１〜８のアルキル基中のメチレン基は、酸素原子、硫黄原子、炭素−炭素二重結合、−ＣＯ−、−ＣＯ−Ｏ−、−ＯＣ−Ｏ−、−ＣＯ−ＮＨ−、−ＮＨ−ＣＯ−、−ＣＲ ^０１ ＝Ｎ−および−Ｎ＝ＣＲ ^０２ −から選択される少なくとも一以上の構造で置換されていてもよく、前記構造中のＲ ^０１ 及びＲ ^０２ は、それぞれ独立に、直鎖又は分岐の炭素原子数１〜８のアルキル基を表す。）

（上記一般式（ＩＩ）中、
Ｒ ^２１ 及びＲ ^２２ は、それぞれ独立に、水素原子、置換又は無置換の、直鎖又は分岐の炭素原子数１〜２０のアルキル基、または、−Ｏ−Ｒを表し、このＲは、置換又は無置換の、直鎖又は分岐の炭素原子数１〜２０のアルキル基、炭素原子数３〜２０のシクロアルキル基、炭素原子数６〜２０のアリール基、炭素原子数７〜２０のアルキルアリール基、又は炭素原子数７〜２０のアリールアルキル基を表し、
Ｒ ^２３ 、Ｒ ^２４ 、Ｒ ^２５ 、Ｒ ^２６ 、Ｒ ^２７ 、Ｒ ^２８ 、Ｒ ^２９ 、Ｒ ^３０ 及びＲ ^３１ は、それぞれ独立に、水素原子、ハロゲン原子、置換又は無置換の、直鎖又は分岐の炭素原子数１〜８のアルキル基、又は直鎖又は分岐の炭素原子数２〜８のアルケニル基を表し、
Ｒ ^３２ 及びＲ ^３３ は、それぞれ独立に、水素原子またはヒドロキシ基を表し、
Ｘ ^１ は、置換又は無置換の、直鎖又は分岐の炭素原子数８以上３０以下のアルキレン基を表し、
Ｙ ^１ 及びＹ ^２ は、それぞれ独立に、−ＣＯ−Ｏ−、−Ｏ−ＣＯ−、−Ｌ ^１ −、−Ｏ−Ｌ ^１ Ｏ−、−Ｏ−Ｌ ^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−を表し、
Ｌ ^１ は、直鎖又は分岐の炭素原子数１〜８のアルキレン基であり、
ｍ及びｎは、それぞれ独立に、０〜８の整数を表し、
＊は、式（Ｉ）中のＲ ^１ と連結する酸素原子との結合手を表す。
ただし、Ｒ ^２１ 、Ｒ ^２２ 及びＲで表される置換又は無置換の、直鎖又は分岐の炭素原子数１〜２０のアルキル基、Ｒ ^２３ 、Ｒ ^２４ 、Ｒ ^２５ 、Ｒ ^２６ 、Ｒ ^２７ 、Ｒ ^２８ 、Ｒ ^２９ 、Ｒ ^３０ 及びＲ ^３１ で表される前記置換又は無置換の、直鎖又は分岐の炭素原子数１〜８のアルキル基およびＸ ^１ で表される直鎖又は分岐の炭素原子数８以上３０以下のアルキレン基中のメチレン基は、酸素原子、硫黄原子、炭素−炭素二重結合、−ＣＯ−、−ＣＯ−Ｏ−、−ＯＣ−Ｏ−、−ＣＯ−ＮＨ−、−ＮＨ−ＣＯ−、−ＣＲ ^０３ ＝Ｎ−および−Ｎ＝ＣＲ ^０４ −から選択される少なくとも一以上の構造で置換されていてもよく、Ｒ ^０３ 及びＲ ^０４ は、それぞれ独立に、直鎖又は分岐の炭素原子数１〜８のアルキル基を表す。）
According to the invention,
A granular ultraviolet absorber containing a triazine-based compound,
The triazine-based compound includes a compound represented by the following general formula (I),
Calculated based on the following procedure for measuring the sieve residue,
The amount of the sieve residue on the sieve having an opening of 4.0 mm is 0.3 wt% or more and 1.5 wt% or less,
The sieve residue amount on the sieve with a mesh of 2.8 mm is 5.0 wt% or more and 25.0 wt% or less,
The amount of the screen residue on the screen having a mesh size of 2.0 mm is 25.0 wt% or more and 35.0 wt% or less,
Provided is a granular ultraviolet absorber which satisfies the particle size distribution in which the amount of the screen residue on a screen having an opening of 1.0 mm is 35.0 wt% or more and 55.0 wt% or less.
(Procedure for measuring the amount of screen residue)
A predetermined amount (g) of the granular ultraviolet absorber is sieved in this order using a mesh opening of 4.0 mm, a mesh opening of 2.8 mm, a mesh opening of 2.0 mm and a mesh opening of 1.0 mm. Then, the residual weight (g) of the granular ultraviolet absorbent remaining on each sieve is measured, and the weight ratio (wt%) of the residual weight to the predetermined amount is calculated as the residual amount of sieve.

(In the above general formula (I),
R ¹ is 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, or 7 carbon atoms. To an alkylaryl group having 20 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 represent a hydrogen atom, a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms, or —O—R, and R is substituted or unsubstituted. A substituted, 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 represents 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 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted, straight-chain or branched carbon atom. Represents an alkyl group having 1 to 8 atoms or a linear or branched alkenyl group having 2 to 8 carbon atoms,
R ¹³ and R ¹⁴ each independently represent a hydrogen atom or a hydroxy group.
However, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms represented by R ¹ , R ² , R ^3, and R, R ⁴ , R ⁵ , R ⁶ , R ⁷ , and R. The methylene group in the substituted or unsubstituted linear or branched alkyl group having 1 to 8 carbon atoms represented by ⁸ , R ⁹ , R ¹⁰ , R ¹¹ and R ¹² is an oxygen atom, a sulfur atom or a carbon atom. - carbon double bond, -CO -, - CO-O -, - OC-O -, - CO-NH -, - NH-CO -, - CR 01 = N- and -N = ^{CR 02} - is selected from At least one structure may be substituted, and R ⁰¹ and R ⁰² in the above structure each independently represent 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 represent a hydrogen atom, a substituted or unsubstituted, straight-chain or branched alkyl group having 1 to 20 carbon atoms, or —O—R; Unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, cycloalkyl group having 3 to 20 carbon atoms, aryl group having 6 to 20 carbon atoms, alkylaryl group having 7 to 20 carbon atoms Or represents 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 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted linear or branched carbon atom. Represents an alkyl group having 1 to 8 atoms, or a linear or branched alkenyl group having 2 to 8 carbon atoms,
R ³² and R ³³ each independently represent a hydrogen atom or a hydroxy group,
X ¹ represents a substituted or unsubstituted, linear or branched alkylene group having 8 or more and 30 or less carbon atoms,
Y ¹ and ^{Y 2} each ^{independently, -CO-O -, - O} -CO -, - L 1 -, - O-L 1 O -, - O-L 1 -, - L 1 -O-CO ^{-, - L 1 -CO-O} -, - CO-CH = CH -, - CH = CH-CO -, - CH = CH-CO-O -, - CH = CH-O-CO -, - CO- Represents 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,
* Represents a bond with an oxygen atom linked to R ¹ in formula (I) .
However, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms represented by R ²¹ , R ²² and R, R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ²⁷ , R. ²⁸ , R ²⁹ , R ³⁰ and R ³¹ , the substituted or unsubstituted linear or branched alkyl group having 1 to 8 carbon atoms and the linear or branched carbon atom represented by X ^1. The methylene group in the alkylene group of 8 or more and 30 or less 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} - may be substituted with at least one or more structure selected ^{from, R 03} and ^{R 04} is independently a linear or branched It represents an alkyl group having 1 to 8 carbon atoms. )

［上記一般式（Ｉ）中、
Ｒ^１は、置換又は無置換の、直鎖又は分岐の炭素原子数１〜２０のアルキル基、炭素原子数３〜２０のシクロアルキル基、炭素原子数６〜２０のアリール基、炭素原子数７〜２０のアルキルアリール基、炭素原子数７〜２０のアリールアルキル基、炭素原子数２〜８のアルケニル基、又は下記一般式（ＩＩ）で表される置換基を表し、
Ｒ^２及びＲ^３は、それぞれ独立に、水素原子、置換又は無置換の、直鎖又は分岐の炭素原子数１〜２０のアルキル基、または−Ｏ−Ｒを表し、このＲは、置換又は無置換の、直鎖又は分岐の炭素原子数１〜２０のアルキル基、炭素原子数３〜２０のシクロアルキル基、炭素原子数６〜２０のアリール基、炭素原子数７〜２０のアルキルアリール基、又は炭素原子数７〜２０のアリールアルキル基を表し、
Ｒ^４、Ｒ^５、Ｒ^６、Ｒ^７、Ｒ^８、Ｒ^９、Ｒ^１０、Ｒ^１１及びＲ^１２は、それぞれ独立に、水素原子、ハロゲン原子、置換又は無置換の、直鎖又は分岐の炭素原子数１〜８のアルキル基又は直鎖又は分岐の炭素原子数２〜８のアルケニル基を表し、
Ｒ^１３及びＲ^１４は、それぞれ独立に、水素原子またはヒドロキシ基を表す。
ただし、Ｒ^１、Ｒ^２、Ｒ^３及びＲで表される置換又は無置換の、直鎖又は分岐の炭素原子数１〜２０のアルキル基、Ｒ^４、Ｒ^５、Ｒ^６、Ｒ^７、Ｒ^８、Ｒ^９、Ｒ^１０、Ｒ^１１及びＲ^１２で表される置換又は無置換の、直鎖又は分岐の炭素原子数１〜８のアルキル基中のメチレン基は、酸素原子、硫黄原子、炭素−炭素二重結合、−ＣＯ−、−ＣＯ−Ｏ−、−ＯＣ−Ｏ−、−ＣＯ−ＮＨ−、−ＮＨ−ＣＯ−、−ＣＲ^０１＝Ｎ−および−Ｎ＝ＣＲ^０２−から選択される少なくとも一以上の構造で置換されていてもよく、前記構造中のＲ^０１及びＲ^０２は、それぞれ独立に、直鎖又は分岐の炭素原子数１〜８のアルキル基を表す。］

［上記一般式（ＩＩ）中、
Ｒ^２１及びＲ^２２は、それぞれ独立に、水素原子、置換又は無置換の、直鎖又は分岐の炭素原子数１〜２０のアルキル基、または、−Ｏ−Ｒを表し、このＲは、置換又は無置換の、直鎖又は分岐の炭素原子数１〜２０のアルキル基、炭素原子数３〜２０のシクロアルキル基、炭素原子数６〜２０のアリール基、炭素原子数７〜２０のアルキルアリール基、又は炭素原子数７〜２０のアリールアルキル基を表し、
Ｒ^２３、Ｒ^２４、Ｒ^２５、Ｒ^２６、Ｒ^２７、Ｒ^２８、Ｒ^２９、Ｒ^３０及びＲ^３１は、それぞれ独立に、水素原子、ハロゲン原子、置換又は無置換の、直鎖又は分岐の炭素原子数１〜８のアルキル基、又は直鎖又は分岐の炭素原子数２〜８のアルケニル基を表し、
Ｒ^３２及びＲ^３３は、それぞれ独立に、水素原子またはヒドロキシ基を表し、
Ｘ^１は、置換又は無置換の、直鎖又は分岐の炭素原子数８以上３０以下のアルキレン基を表し、
Ｙ^１及びＹ^２は、それぞれ独立に、−ＣＯ−Ｏ−、−Ｏ−ＣＯ−、−Ｌ^１−、−Ｏ−Ｌ^１Ｏ−、−Ｏ−Ｌ^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−を表し、
Ｌ^１は、直鎖又は分岐の炭素原子数１〜８のアルキレン基であり、
ｍ及びｎは、それぞれ独立に、０〜８の整数を表し、
＊は、式（Ｉ）中のＲ^１と連結する酸素原子との結合手を表す。
ただし、Ｒ^２１、Ｒ^２２及びＲで表される置換又は無置換の、直鎖又は分岐の炭素原子数１〜２０のアルキル基、Ｒ^２３、Ｒ^２４、Ｒ^２５、Ｒ^２６、Ｒ^２７、Ｒ^２８、Ｒ^２９、Ｒ^３０及びＲ^３１で表される前記置換又は無置換の、直鎖又は分岐の炭素原子数１〜８のアルキル基およびＸ^１で表される直鎖又は分岐の炭素原子数８以上３０以下のアルキレン基中のメチレン基は、酸素原子、硫黄原子、炭素−炭素二重結合、−ＣＯ−、−ＣＯ−Ｏ−、−ＯＣ−Ｏ−、−ＣＯ−ＮＨ−、−ＮＨ−ＣＯ−、−ＣＲ^０３＝Ｎ−および−Ｎ＝ＣＲ^０４−から選択される少なくとも一以上の構造で置換されていてもよく、Ｒ^０３及びＲ^０４は、それぞれ独立に、直鎖又は分岐の炭素原子数１〜８のアルキル基を表す。］ According to the invention,
A granular ultraviolet absorber containing a triazine-based compound,
The triazine-based compound includes a compound represented by the following general formula (I),
When the following procedure for measuring the residual amount of sieve was carried out, the amount of non-passage when the granular ultraviolet absorbent was passed through a 5.0 mm sieve with an opening of 0 wt%,
When the following procedure for measuring the residual amount of sieve is carried out, the amount of the granular ultraviolet absorbent passing through the 1.0 mm sieve is 1.0 wt% or more and 15.0 wt% or less,
Calculated based on the following procedure for measuring the sieve residue,
The amount of the sieve residue on the sieve having an opening of 4.0 mm is 0.3 wt% or more and 1.5 wt% or less,
The sieve residue amount on the sieve with a mesh of 2.8 mm is 5.0 wt% or more and 25.0 wt% or less,
The amount of the screen residue on the screen having a mesh size of 2.0 mm is 25.0 wt% or more and 35.0 wt% or less,
Provided is a granular ultraviolet absorber which satisfies the particle size distribution in which the amount of the screen residue on a screen having an opening of 1.0 mm is 35.0 wt% or more and 55.0 wt% or less.
(Procedure for measuring the amount of screen residue)
A predetermined amount (g) of the granular ultraviolet absorber is sieved in this order using a mesh opening of 4.0 mm, a mesh opening of 2.8 mm, a mesh opening of 2.0 mm and a mesh opening of 1.0 mm. Then, the residual weight (g) of the granular ultraviolet absorbent remaining on each sieve is measured, and the weight ratio (wt%) of the residual weight to the predetermined amount is calculated as the residual amount of sieve.

[In the above general formula (I),
R ¹ is 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, and 7 carbon atoms. To an alkylaryl group having 20 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 represent a hydrogen atom, a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms, or —O—R, and R is substituted or unsubstituted. A substituted, 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 represents 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 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted, straight-chain or branched carbon atom. Represents an alkyl group having 1 to 8 atoms or a linear or branched alkenyl group having 2 to 8 carbon atoms,
R ¹³ and R ¹⁴ each independently represent a hydrogen atom or a hydroxy group.
However, the substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms represented by R ¹ , R ² , R ^3, and R, R ⁴ , R ⁵ , R ⁶ , R ⁷ , and R. The methylene group in the substituted or unsubstituted linear or branched alkyl group having 1 to 8 carbon atoms represented by ⁸ , R ⁹ , R ¹⁰ , R ¹¹ and R ¹² is an oxygen atom, a sulfur atom or a carbon atom. - carbon double bond, -CO -, - CO-O -, - OC-O -, - CO-NH -, - NH-CO -, - CR 01 = N- and -N = ^{CR 02} - is selected from At least one structure may be substituted, and R ⁰¹ and R ⁰² in the above structure each independently represent 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 represent a hydrogen atom, a substituted or unsubstituted, straight-chain or branched alkyl group having 1 to 20 carbon atoms, or —O—R; Unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, cycloalkyl group having 3 to 20 carbon atoms, aryl group having 6 to 20 carbon atoms, alkylaryl group having 7 to 20 carbon atoms Or represents 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 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted linear or branched carbon atom. Represents an alkyl group having 1 to 8 atoms, or a linear or branched alkenyl group having 2 to 8 carbon atoms,
R ³² and R ³³ each independently represent a hydrogen atom or a hydroxy group,
X ¹ represents a substituted or unsubstituted, linear or branched alkylene group having 8 or more and 30 or less carbon atoms,
Y ¹ and ^{Y 2} each ^{independently, -CO-O -, - O} -CO -, - L 1 -, - O-L 1 O -, - O-L 1 -, - L 1 -O-CO ^{-, - L 1 -CO-O} -, - CO-CH = CH -, - CH = CH-CO -, - CH = CH-CO-O -, - CH = CH-O-CO -, - CO- Represents 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,
* Represents a bond with an oxygen atom linked to R ¹ in formula (I).
However, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms represented by R ²¹ , R ²² and R, R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ²⁷ , R. ²⁸ , R ²⁹ , R ³⁰ and R ³¹ , the substituted or unsubstituted linear or branched alkyl group having 1 to 8 carbon atoms and the linear or branched carbon atom represented by X ^1. The methylene group in the alkylene group of 8 or more and 30 or less 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} - may be substituted with at least one or more structure selected ^{from, R 03} and ^{R 04} is independently a linear or branched It represents an alkyl group having 1 to 8 carbon atoms. ]

Although the embodiments of the present invention have been described above, these are examples of the present invention, and various configurations other than the above can be adopted.
Hereinafter, an example of the reference mode will be additionally described.
1. A granular ultraviolet absorber containing a triazine-based compound,
Calculated based on the following procedure for measuring the sieve residue,
The amount of the sieve residue on the sieve having an opening of 4.0 mm is 0.3 wt% or more and 1.5 wt% or less,
The sieve residue amount on the sieve with a mesh of 2.8 mm is 5.0 wt% or more and 25.0 wt% or less,
The amount of the screen residue on the screen having a mesh size of 2.0 mm is 25.0 wt% or more and 35.0 wt% or less,
A granular ultraviolet absorber satisfying the particle size distribution in which the amount of the screen residue on the screen having an opening of 1.0 mm is 35.0 wt% or more and 55.0 wt% or less.
(Procedure for measuring the amount of screen residue)
A predetermined amount (g) of the granular ultraviolet absorber is sieved in this order using a mesh opening of 4.0 mm, a mesh opening of 2.8 mm, a mesh opening of 2.0 mm and a mesh opening of 1.0 mm. Then, the residual weight (g) of the granular ultraviolet absorbent remaining on each sieve is measured, and the weight ratio (wt%) of the residual weight to the predetermined amount is calculated as the residual amount of sieve.
2. 1. A granular ultraviolet absorber according to,
A granular ultraviolet absorber, wherein the triazine-based compound contains the compound represented by the general formula (I).
[In the above general formula (I),
R ¹ is 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, or 7 carbon atoms. To an alkylaryl group having 20 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 general formula (II),
R ² and R ³ each independently represent a hydrogen atom, a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms, or —O—R, and R is substituted or unsubstituted. A substituted, 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 represents 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 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted, straight-chain or branched carbon atom. Represents an alkyl group having 1 to 8 atoms or a linear or branched alkenyl group having 2 to 8 carbon atoms,
R ¹³ and R ¹⁴ each independently represent a hydrogen atom or a hydroxy group.
However, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms represented by R ¹ , R ² , R ^3, and R, R ⁴ , R ⁵ , R ⁶ , R ⁷ , and R. The methylene group in the substituted or unsubstituted linear or branched alkyl group having 1 to 8 carbon atoms represented by ⁸ , R ⁹ , R ¹⁰ , R ¹¹ and R ¹² is an oxygen atom, a sulfur atom or a carbon atom. - carbon double bond, -CO -, - CO-O -, - OC-O -, - CO-NH -, - NH-CO -, - CR 01 = N- and -N = ^{CR 02} - is selected from At least one structure may be substituted, and R ⁰¹ and R ⁰² in the above structure each independently represent 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 represent a hydrogen atom, a substituted or unsubstituted, straight-chain or branched alkyl group having 1 to 20 carbon atoms, or —O—R; Unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, cycloalkyl group having 3 to 20 carbon atoms, aryl group having 6 to 20 carbon atoms, alkylaryl group having 7 to 20 carbon atoms Or represents 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 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted linear or branched carbon atom. Represents an alkyl group having 1 to 8 atoms, or a linear or branched alkenyl group having 2 to 8 carbon atoms,
R ³² and R ³³ each independently represent a hydrogen atom or a hydroxy group,
X ¹ represents a substituted or unsubstituted, linear or branched alkylene group having 8 or more and 30 or less carbon atoms,
Y ¹ and ^{Y 2} each ^{independently, -CO-O -, - O} -CO -, - L 1 -, - O-L 1 O -, - O-L 1 -, - L 1 -O-CO ^{-, - L 1 -CO-O} -, - CO-CH = CH -, - CH = CH-CO -, - CH = CH-CO-O -, - CH = CH-O-CO -, - CO- Represents 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,
* Represents a bond with an oxygen atom linked to R ¹ in formula (I) .
However, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms represented by R ²¹ , R ²² and R, R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ²⁷ , R. ²⁸ , R ²⁹ , R ³⁰ and R ³¹ , the substituted or unsubstituted linear or branched alkyl group having 1 to 8 carbon atoms and the linear or branched carbon atom represented by X ^1. The methylene group in the alkylene group of 8 or more and 30 or less 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} - may be substituted with at least one or more structure selected ^{from, R 03} and ^{R 04} is independently a linear or branched It represents an alkyl group having 1 to 8 carbon atoms. ]
3. 1. Or 2. A granular ultraviolet absorber according to,
A granular ultraviolet absorber, wherein the triazine-based compound contains a compound represented by the general formula (A).
(In the above general formula (A),
R ^A1 is 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, or 6 to 6 carbon atoms. An aryl group having 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, which} may be the same or different from each other, are 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. Represents
R ^A4 , R ^A7 and R ^{A10, which} may be the same or different, are each a hydrogen atom, a linear or branched alkyl group having 1 to 8 carbon atoms, or a linear or branched alkenyl having 3 to 8 carbon atoms. Represents a group,
R ^A13 and R ^A17 may be the same as or different from each other and represent a hydrogen atom or a hydroxy group.
Provided that a linear or branched alkyl group having 1 to 12 carbon atoms represented by R ^A1 , R ^A2 and R ^A3 or a linear or branched alkyl group having 1 to 12 carbon atoms represented by R ^A2 and R ^A3 . The methylene group in the alkoxy group is an oxygen atom, a sulfur atom, a carbon-carbon double bond, -CO-, -CO-O-, -OC-O-, -CO-NH-, -NH-CO-,-. It may be substituted with at least one structure selected from CR ⁰⁵ = N- and -N = CR ^06- , and R ⁰⁵ and R ⁰⁶ in the structure are each independently a linear or branched carbon. It represents an alkyl group having 1 to 8 atoms. )
4. 1. Or 2. A granular ultraviolet absorber according to,
The triazine-based compound is the above compound No. 1A to compound No. 8A, a granular ultraviolet absorber containing one or more compounds represented by any of 8A.
5. 1. Or 2. A granular ultraviolet absorber according to,
A granular ultraviolet absorber, wherein the triazine-based compound contains a compound represented by the general formula (B).
(In the general formula (B), R ^B4 , R ^B5 , R ^{B7 to} R ^B9 , R ^{B10 to} R ^B12 , R ^B23 , R ^B24 , R ^{B26 to} R ^B28 , and R ^{B29 to} R ^B31 are each independently. , 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, and an aryl group having 6 to 20 carbon atoms. And n represents an integer of 8 to 14. However, the para position of two benzene rings among the three benzene rings connected to the triazine ring is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or the number of carbon atoms. 1-20 alkoxy groups are shown, and one of the ortho positions is a hydrogen atom or a hydroxy group.)
6. 5. A granular ultraviolet absorber according to,
The triazine-based compound is the above compound No. 1B to compound No. 4B, a granular UV absorber containing one or more compounds represented by any of 4B.
(In the above compound 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 may be a hydrogen atom or a direct atom. It represents a chain or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched alkoxy group having 1 to 4 carbon atoms.)
7. 1. ~ 6. A granular UV absorber according to any one of
A granular ultraviolet absorber, wherein the amount of the non-passage when the granular ultraviolet absorber is passed through a 5.0 mm mesh screen is 0 wt%.
8. 1. ~ 7. A granular UV absorber according to any one of
The granular ultraviolet absorbent, wherein the amount of the granular ultraviolet absorbent passing through the 1.0 mm sieve is 1.0 wt% or more and 15.0 wt% or less when the procedure for measuring the residual amount of the sieve is performed.
9. 2. ~ 4. A granular UV absorber according to any one of
The granular UV absorber, wherein the triazine-based compound has a maximum peak within a range of a diffraction angle 2θ of 5.00 ° to 6.50 ° in a powder X-ray diffraction analysis pattern.
10. 9. A granular ultraviolet absorber according to,
A granular ultraviolet absorber, wherein the half-value width of the maximum peak of the triazine-based compound is 0.05 ° or more and 0.20 ° or less.
11. 9. Or 10. A granular ultraviolet absorber according to,
When the relative intensity of the maximum peak of the triazine-based compound is set to 100, the diffraction peak having the relative intensity of 30 or more and 60 or less does not exist within the range of the diffraction angle 2θ of 3.0 ° or more and 45.0 ° or less. Characteristic granular UV absorber.
12. 9. ~ 11. A granular UV absorber according to any one of
When the relative intensity of the maximum peak of the triazine-based compound is 100, the diffraction peak having the relative intensity of 1 or more and 5 or less does not exist within the range of the diffraction angle 2θ of more than 45.0 ° and 60.0 ° or less. A granular ultraviolet absorber characterized by:
13. 1. ~ 12. A resin composition containing the granular ultraviolet absorber according to any one of 1.
14. 13. A resin composition according to claim 1, which contains a synthetic resin.

Claims (14)

A granular ultraviolet absorber containing a triazine-based compound,
Calculated based on the following procedure for measuring the sieve residue,
The amount of the sieve residue on the sieve having an opening of 4.0 mm is 0.3 wt% or more and 1.5 wt% or less,
The sieve residue amount on the sieve with a mesh of 2.8 mm is 5.0 wt% or more and 25.0 wt% or less,
The amount of the screen residue on the screen having a mesh size of 2.0 mm is 25.0 wt% or more and 35.0 wt% or less,
A granular ultraviolet absorber satisfying the particle size distribution in which the amount of the screen residue on the screen having an opening of 1.0 mm is 35.0 wt% or more and 55.0 wt% or less.
(Procedure for measuring the amount of screen residue)
A predetermined amount (g) of the granular ultraviolet absorber is sieved in this order using a mesh opening of 4.0 mm, a mesh opening of 2.8 mm, a mesh opening of 2.0 mm and a mesh opening of 1.0 mm. Then, the residual weight (g) of the granular ultraviolet absorbent remaining on each sieve is measured, and the weight ratio (wt%) of the residual weight to the predetermined amount is calculated as the residual amount of sieve. The granular ultraviolet absorber according to claim 1,
A granular ultraviolet absorber, wherein the triazine-based compound contains a compound represented by the following general formula (I).

[In the above general formula (I),
R ¹ is 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, and 7 carbon atoms. To an alkylaryl group having 20 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 represent a hydrogen atom, a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms, or —O—R, and R is substituted or unsubstituted. A substituted, 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 represents 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 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted, straight-chain or branched carbon atom. Represents an alkyl group having 1 to 8 atoms or a linear or branched alkenyl group having 2 to 8 carbon atoms,
R ¹³ and R ¹⁴ each independently represent a hydrogen atom or a hydroxy group.
However, the substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms represented by R ¹ , R ² , R ^3, and R, R ⁴ , R ⁵ , R ⁶ , R ⁷ , and R. The methylene group in the substituted or unsubstituted linear or branched alkyl group having 1 to 8 carbon atoms represented by ⁸ , R ⁹ , R ¹⁰ , R ¹¹ and R ¹² is an oxygen atom, a sulfur atom or a carbon atom. - carbon double bond, -CO -, - CO-O -, - OC-O -, - CO-NH -, - NH-CO -, - CR 01 = N- and -N = ^{CR 02} - is selected from At least one structure may be substituted, and R ⁰¹ and R ⁰² in the above structure each independently represent 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 represent a hydrogen atom, a substituted or unsubstituted, straight-chain or branched alkyl group having 1 to 20 carbon atoms, or —O—R; Unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, cycloalkyl group having 3 to 20 carbon atoms, aryl group having 6 to 20 carbon atoms, alkylaryl group having 7 to 20 carbon atoms Or represents 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 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted linear or branched carbon atom. Represents an alkyl group having 1 to 8 atoms, or a linear or branched alkenyl group having 2 to 8 carbon atoms,
R ³² and R ³³ each independently represent a hydrogen atom or a hydroxy group,
X ¹ represents a substituted or unsubstituted, linear or branched alkylene group having 8 or more and 30 or less carbon atoms,
Y ¹ and ^{Y 2} each ^{independently, -CO-O -, - O} -CO -, - L 1 -, - O-L 1 O -, - O-L 1 -, - L 1 -O-CO ^{-, - L 1 -CO-O} -, - CO-CH = CH -, - CH = CH-CO -, - CH = CH-CO-O -, - CH = CH-O-CO -, - CO- Represents 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,
* Represents a bond with an oxygen atom linked to R ¹ in formula (I).
However, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms represented by R ²¹ , R ²² and R, R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ²⁷ , R. ²⁸ , R ²⁹ , R ³⁰ and R ³¹ , the substituted or unsubstituted linear or branched alkyl group having 1 to 8 carbon atoms and the linear or branched carbon atom represented by X ^1. The methylene group in the alkylene group of 8 or more and 30 or less 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} - may be substituted with at least one or more structure selected ^{from, R 03} and ^{R 04} is independently a linear or branched It represents an alkyl group having 1 to 8 carbon atoms. ] The granular ultraviolet absorber according to claim 1 or 2, wherein
A granular ultraviolet absorber, wherein the triazine-based compound contains a compound represented by the following general formula (A).

(In the above general formula (A),
R ^A1 is 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, or 6 to 6 carbon atoms. An aryl group having 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, which} may be the same or different from each other, are 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. Represents
R ^A4 , R ^A7 and R ^{A10, which} may be the same or different, are each a hydrogen atom, a linear or branched alkyl group having 1 to 8 carbon atoms, or a linear or branched alkenyl having 3 to 8 carbon atoms. Represents a group,
R ^A13 and R ^A17 may be the same as or different from each other and represent a hydrogen atom or a hydroxy group.
However, a linear or branched alkyl group having 1 to 12 carbon atoms represented by R ^A1 , R ^A2 and R ^A3 , or a linear or branched alkyl group having 1 to 12 carbon atoms represented by R ^A2 and R ^A3 . The methylene group in the alkoxy group is an oxygen atom, a sulfur atom, a carbon-carbon double bond, -CO-, -CO-O-, -OC-O-, -CO-NH-, -NH-CO-,-. It may be substituted with at least one structure selected from CR ⁰⁵ = N- and -N = CR ^06- , and R ⁰⁵ and R ⁰⁶ in the structure are each independently a linear or branched carbon. It represents an alkyl group having 1 to 8 atoms. ) The granular ultraviolet absorber according to claim 1 or 2, wherein
The triazine-based compound is the following compound No. 1A to compound No. 8A, a granular ultraviolet absorber containing one or more compounds represented by any of 8A.

The granular ultraviolet absorber according to claim 1 or 2, wherein
A granular ultraviolet absorber, wherein the triazine-based compound contains a compound represented by the following general formula (B).

(In the general formula (B), R ^B4 , R ^B5 , R ^{B7 to} R ^B9 , R ^{B10 to} R ^B12 , R ^B23 , R ^B24 , R ^{B26 to} R ^B28 , R ^{B29 to} R ^B31 are each independently. , 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, and an aryl group having 6 to 20 carbon atoms. And n represents an integer of 8 to 14. However, the para position of two benzene rings among the three benzene rings connected to the triazine ring is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or the number of carbon atoms. 1-20 alkoxy groups are shown, and one of the ortho positions is a hydrogen atom or a hydroxy group.) The granular ultraviolet absorber according to claim 5,
The triazine-based compound is the following compound No. 1B to compound No. 4B, a granular UV absorber containing one or more compounds represented by any of 4B.

(In the compound No. 1B to the 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 from each other, and may be a hydrogen atom or a direct atom. It represents a chain or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched alkoxy group having 1 to 4 carbon atoms.) The granular ultraviolet absorber according to any one of claims 1 to 6,
A granular ultraviolet absorber, wherein the amount of the non-passage when the granular ultraviolet absorber is passed through a 5.0 mm sieve with an opening is 0 wt%. The granular ultraviolet absorber according to any one of claims 1 to 7,
The granular ultraviolet absorbent, wherein the amount of the granular ultraviolet absorbent passing through the 1.0 mm sieve is 1.0 wt% or more and 15.0 wt% or less when the procedure for measuring the residual amount of the sieve is performed. The granular ultraviolet absorber according to any one of claims 2 to 4,
A granular ultraviolet absorber, wherein the triazine-based compound has a maximum peak within a range of a diffraction angle 2θ of 5.00 ° to 6.50 ° in a powder X-ray diffraction analysis pattern. The granular ultraviolet absorber according to claim 9,
A granular ultraviolet absorber, wherein the half-value width of the maximum peak of the triazine-based compound is 0.05 ° or more and 0.20 ° or less. The granular ultraviolet absorber according to claim 9 or 10, wherein
When the relative intensity of the maximum peak of the triazine-based compound is set to 100, the diffraction peak having the relative intensity of 30 or more and 60 or less does not exist within the range of the diffraction angle 2θ of 3.0 ° or more and 45.0 ° or less. Characteristic granular UV absorber. The granular ultraviolet absorber according to any one of claims 9 to 11,
When the relative intensity of the maximum peak of the triazine-based compound is 100, the diffraction peak having the relative intensity of 1 or more and 5 or less does not exist within the range of the diffraction angle 2θ of more than 45.0 ° and 60.0 ° or less. A granular ultraviolet absorber characterized by:   A resin composition containing the granular ultraviolet absorber according to any one of claims 1 to 12.   The resin composition according to claim 13, wherein the resin composition contains a synthetic resin.

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