Method of producing a compound having a colorant structure, and toner containing a compound obtained by the production method

Patent metadata

Field	Value
Publication number	US-9715187-B2
Application number	US-201514673860-A
Country	US
Kind code	B2
Filing date	Mar 30, 2015
Priority date	Apr 1, 2014
Publication date	Jul 25, 2017
Grant date	Jul 25, 2017

Abstract

Provided are a method of producing a compound having a colorant structure suitable for a pigment dispersant, and a pigment dispersant, a pigment composition, a pigment dispersion, and a toner each containing the compound. The production method is a method of producing a compound in which a polymer portion and a colorant portion are bonded to each other through a linking group, the method including the steps of: (a) polymerizing a vinyl-based polymerizable monomer represented by the formula (A) with a radical initiator having a protective group by living radical polymerization to provide a polymer having the protective group at a terminal thereof; (b) hydrolyzing the protective group of the polymer having the protective group at a terminal thereof obtained by the step (a) to deprotect the polymer; and (c) bonding the deprotected polymer obtained by the step (b) and a colorant to each other through a covalent bond.

First claim

What is claimed is:

1. A method of producing a compound represented by formula (1), comprising the steps of:
(a) polymerizing a vinyl-based polymerizable monomer represented by the formula (A) with a radical initiator having a protective group by living radical polymerization to provide a polymer having the protective group at a terminal thereof;
(b) hydrolyzing the protective group of the polymer having the protective group at a terminal thereof obtained by the step (a) to deprotect the polymer; and
(c) bonding the deprotected polymer obtained by the step (b) and a colorant to each other through a covalent bond:
X-L-Y  (1)

in which X represents a polymer portion having a monomer unit derived from the vinyl-based polymerizable monomer represented by formula (A), L represents a linking group, and Y represents a colorant portion; and

in which R 1 represents a hydrogen atom or an alkyl group, and R 2 represents a phenyl group, a phenyl group having a substituent, a carboxy group, an alkoxycarbonyl group, or a carboxamide group,
wherein the vinyl-based polymerizable monomer comprises one of styrene and an acrylic acid ester.

2. The production method according to claim 1 , wherein the living radical polymerization comprises one of atom transfer radical polymerization (ATRP) and reversible addition-fragmentation chain transfer (RAFT) polymerization.

3. The production method according to claim 1 , wherein the protective group comprises one of a tert-butoxycarbonyl group and a benzoxycarbonyl group.

4. The production method according to claim 1 , wherein the linking group L has one of a carboxylic acid ester bond and a carboxylic acid amide bond.

5. The production method according to claim 1 , wherein the colorant comprises an azo colorant.

6. The production method according to claim 1 , wherein a moiety -L-Y in which the colorant portion Y and the linking group L are bonded to each other is represented by formula (3):

in which at least one of R 3 , R 4 , and Ar represents a functional group having bonded thereto the linking group L;
R 3 and R 4 when the linking group L is not bonded thereto each independently represent an alkyl group, an alkyl group having a substituent, a phenyl group, a phenyl group having a substituent, an OR 5 group, or an NR 6 R 7 group, and R 5 to R 7 each independently represent a hydrogen atom, an alkyl group, a phenyl group, or an aralkyl group;
Ar when the linking group L is not bonded thereto represents an aryl group or an aryl group having a substituent;
when the linking group L is bonded to R 3 , R 3 represents a group formed by removal of a hydrogen atom from the functional group that R 3 to which the linking group L is not bonded represents;
when the linking group L is bonded to R 4 , R 4 represents a group formed by removal of a hydrogen atom from the functional group that R 4 to which the linking group L is not bonded represents; and
when the linking group L is bonded to Ar, Ar represents a group formed by removal of a hydrogen atom from the functional group that Ar to which the linking group L is not bonded represents.

7. The production method according to claim 6 , wherein the moiety -L-Y in which the colorant portion Y and the linking group L are bonded to each other is represented by formula (4):

in which R 3 represents an alkyl group or a phenyl group;
R 8 to R 12 and R 13 to R 17 satisfy at least one of the following condition (i) and (ii):
(i) at least one of R 8 to R 12 represents the linking group L; or
(ii) at least one of R 13 to R 17 represents the linking group L; and
when R 8 to R 12 and R 13 to R 17 do not represent the linking group L, R 8 to R 12 and R 13 to R 17 each independently represent a group represented by a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a hydroxyl group, a cyano group, a trifluoromethyl group, a carboxy group, an alkoxycarbonyl group, an alkoxysulfonyl group, a sulfonate group, a carboxamide group, a sulofonamide group, a urea group, or a thiourea group, provided that the urea group may form a ring with two adjacent carbon atoms of R 8 to R 12 and R 13 to R 17 to provide a five-membered heterocycle.

8. A toner, comprising toner particles each containing a binder resin, a pigment and a compound, wherein the toner particles are produced by one of a suspension polymerization method and a suspension granulation method, and
the compound is represented by formula (1) produced by the method of claim 1 .

Assignees

• Canon Kk

Inventors

• Mukumoto Kosuke
• Murai Yasuaki
• Hasegawa Yuki
• Toyoda Takayuki
• Mashida Ayano
• Hasegawa Waka
• Nishiura Chiaki
• Seki Masanori
• Hirose Masashi

Classifications

• C08F112/08

  Styrene · CPC title

• G03G9/0906

  Organic dyes · CPC title

• C09B67/0041

  mixtures containing one azo dye · CPC title

• C09B68/41

  Polymers attached to the pigment surface (C09B68/444, C09B68/446 take precedence) · CPC title

• G03G9/0924 Primary

  Dyes characterised by specific substituents · CPC title