Method for producing halogenated organic pigment, halogenated organic pigment obtained by the production method, and colored composition comprising the same

Patent metadata

Field	Value
Publication number	US-2016177100-A1
Application number	US-201414910579-A
Country	US
Kind code	A1
Filing date	Mar 25, 2014
Priority date	Aug 5, 2013
Publication date	Jun 23, 2016
Grant date	—

Abstract

A method for producing a halogenated organic pigment comprising a halogenation step of halogenating an organic pigment with a halogenating agent, wherein the halogenating agent comprises one or more N-haloimide compounds selected from the group consisting of trichloroisocyanuric acid, a metal salt of dichloroisocyanuric acid, tribromoisocyanuric acid, and a metal salt of dibromoisocyanuric acid. According to the present invention, a method for producing a halogenated organic pigment which does not use high toxic raw materials, does not generate a large amount of unfavorable by-products such as hydrogen halide gas and succinimide, and is excellent in terms of safety and productivity can be provided.

First claim

1 . A method for producing a halogenated organic pigment, the method comprising halogenating an organic pigment with a halogenating agent, wherein the halogenating agent comprises one or more N-haloimide compounds selected from the group consisting of trichloroisocyanuric acid, a metal salt of dichloroisocyanuric acid, tribromoisocyanuric acid, and a metal salt of dibromoisocyanuric acid.

2 . The method according to claim 1 , wherein the N-haloimide compound comprises one or more N-chloroimide compounds selected from the group consisting of trichloroisocyanuric acid and sodium dichloroisocyanurate.

3 . The method according to claim 1 , wherein the halogenation occurs in the presence of a solvent comprising at least one of a strong acid and a eutectic salt.

4 . The method according to claim 3 , wherein the halogenation occurs in the presence of a strong acid comprising one or more selected from the group consisting of sulfuric acid, fuming sulfuric acid, chlorosulfonic acid, polyphosphoric acid, and methanesulfonic acid.

5 . The method according to claim 3 , wherein the halogenation occurs in the presence of a eutectic salt of aluminum chloride and sodium chloride.

6 . The method according to claim 1 , wherein the organic pigment comprises at least one selected from the group consisting of a quinacridone pigment, a phthalocyanine pigment, an anthraquinone pigment, a quinophthalone pigment, a perylene pigment, an isoindolinone pigment, a dioxazine pigment and an indanthrone pigment.

7 . The method according to claim 6 , wherein the organic pigment comprises a quinacridone compound represented by the following Formula (I):

wherein
R 1 to R 4 , R 6 , R 8 to R 11 , and R 13 each independently represent any one selected from the group consisting of a hydrogen atom, a chlorine atom, a bromine atom, a C1-C4 alkyl group, a C1-C4 alkoxy group, a phthalimidomethyl group, —CH 2 NHCOCH 2 Cl, —SO 2 Cl, —SO 3 M, and —X1-X2-N(X3) 2 ;
M represents a hydrogen atom or an alkali metal;
X1 represents —SO 2 NH— or —CH 2 NHCOCH 2 NH—;
X2 represents a C1-C4 alkylene group;
X3 represents a C1-C4 alkyl group optionally having a heteroatom, wherein X3 groups may be connected to each other to form a ring; and
at least one of R 1 to R 4 , R 6 , R 8 to R 11 , and R 13 is a hydrogen atom.

8 . A halogenated organic pigment obtained by the method of claim 1 .

9 . A colored composition, comprising the halogenated organic pigment according to claim 8 and a vehicle component.

10 . A color toner, comprising the colored composition according to claim 9 .

11 . An inkjet ink, comprising the colored composition according to claim 9 .

12 . A color filter resist ink, comprising the colored composition according to claim 9 .

13 . A printed article which is printed using the color toner according to claim 10 .

14 . A color filter, comprising a filter segment formed using the color filter resist ink according to claim 12 .

15 . A printed article, which is printed with the inkjet ink of claim 11 .

Assignees

• Toyo Ink Sc Holdings Co Ltd
• Toyocolor Co Ltd

Inventors

• Mochizuki Akimitsu
• Takahata Noriyoshi
• Hamada Naoki
• Kasuya Takashi

Classifications

• C09B67/0017

  Influencing the physical properties by treatment with an acid, H2SO4 · CPC title

• C09B47/14

  having alkyl radicals substituted by halogen atoms · CPC title

• G03G9/0922

  Formazane dyes; Nitro and Nitroso dyes; Quinone imides; Azomethine dyes · CPC title

• C09B1/00

  Dyes with anthracene nucleus not condensed with any other ring · CPC title

• C09B25/00

  Quinophthalones · CPC title