US 12,384,920 B2
Azo iron complex dye, ink composition containing same, and method for producing azo iron complex dye
Masakazu Taniguchi, Neyagawa (JP); Keigo Kanbara, Neyagawa (JP); Hayato Inaba, Neyagawa (JP); and Kaori Sato, Neyagawa (JP)
Assigned to ORIENT CHEMICAL INDUSTRIES CO., LTD., Osaka (JP)
Appl. No. 18/272,520
Filed by ORIENT CHEMICAL INDUSTRIES CO., LTD., Osaka (JP)
PCT Filed Jan. 27, 2022, PCT No. PCT/JP2022/002988
§ 371(c)(1), (2) Date Jul. 14, 2023,
PCT Pub. No. WO2022/163736, PCT Pub. Date Aug. 4, 2022.
Claims priority of application No. 2021-013104 (JP), filed on Jan. 29, 2021.
Prior Publication US 2024/0409746 A1, Dec. 12, 2024
Int. Cl. C09D 11/328 (2014.01); B41M 5/00 (2006.01); C07C 245/08 (2006.01); C09B 45/12 (2006.01); C09B 45/32 (2006.01); C09B 67/22 (2006.01); C09D 11/037 (2014.01); C07F 15/02 (2006.01)
CPC C09B 45/12 (2013.01) [B41M 5/00 (2013.01); C07C 245/08 (2013.01); C09B 45/32 (2013.01); C09B 67/0047 (2013.01); C09D 11/037 (2013.01); C09D 11/328 (2013.01); C07F 15/02 (2013.01); C07F 15/025 (2013.01); C09B 67/0033 (2013.01)] 10 Claims
OG exemplary drawing
 
1. An azo iron complex dye comprising:
a disazo-monoazo iron complex represented by the following chemical formula (1):

OG Complex Work Unit Chemistry
wherein, in the chemical formula (1), R1 and R2 are each independently a straight or branched alkyl group having 3-10 carbon atoms, R3 is an electron-withdrawing group, R4 is a straight or branched alkyl group having 1-5 carbon atoms or a straight or branched alkoxy group having 1-5 carbon atoms, R5 is a nitro group, a sulfonamide group or a halogen atom, R6 is a hydrogen atom, a straight or branched alkyl group having 1-8 carbon atoms, a nitro group or a halogen atom, R7 is a hydrogen atom or a straight or branched alkyl group having 3-12 carbon atoms, and A+ is a monovalent cation.
 
9. A method for manufacturing an azo iron complex dye comprising:
a step for an iron-complexation for preparing an azo iron complex anion by heating
a disazo dye represented by the following chemical formula (5):

OG Complex Work Unit Chemistry
wherein, in the chemical formula (5), R1 and R2 are each independently a straight or branched alkyl group having 3-10 carbon atoms, R3 is an electron-withdrawing group, R4 is a straight or branched alkyl group having 1-5 carbon atoms or a straight or branched alkoxy group having 1-5 carbon atoms,
a monoazo dye represented by the following chemical formula (6):

OG Complex Work Unit Chemistry
wherein, in the chemical formula (6), R5 is a nitro group, a sulfonamide group or a halogen atom, R6 is a hydrogen atom, a straight or branched alkyl group having 1-8 carbon atoms, a nitro group or a halogen atom, R7 is a hydrogen atom or a straight or branched alkyl group having 3-12 carbon atoms, and
an ironizing agent,
in a solvent and,
a step for ion-exchanging by reacting the azo iron complex anion, and an alkali metal solution and/or an ammoniation agent to introduce a cation which is combined with the azo iron complex anion, for obtaining a disazo-monoazo iron complex represented by the following chemical formula (1):

OG Complex Work Unit Chemistry
wherein, in the chemical formula (1), R1-R4 are the same as ones of the chemical formula (5), R5-R7 are the same as ones of the chemical formula (6), and A+ is a monovalent cation.