Method for producing halogenated organic pigment, halogenated organic pigment obtained by the production method, and colored composition comprising the same
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.
1. A method for producing a halogenated organic pigment, the method comprising halogenating an organic pigment with a halogenating agent in the presence of a solvent comprising a strong acid,
wherein:
the halogenating agent comprises at least one N-haloimide compound selected from the group consisting of trichloroisocyanuric acid, a metal salt of dichloroisocyanuric acid, tribromoisocyanuric acid, and a metal salt of dibromoisocyanuric acid; and
the strong acid comprises at least one selected from the group consisting of sulfuric acid, fuming sulfuric acid, chlorosulfonic acid, polyphosphoric acid, and methanesulfonic acid.
2. The method according to claim 1 , wherein the N-haloimide compound comprises at least one selected from the group consisting of trichloroisocyanuric acid and sodium dichloroisocyanurate.
3. The method according to claim 1 , wherein the solvent further comprises an eutectic salt.
4. The method according to claim 3 , wherein the eutectic salt comprises aluminum chloride and sodium chloride.
5. 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.
6. The method according to claim 5 , 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.