Method for producing compound having colorant structure at main chain terminal of polymer, and pigment dispersant, pigment composition, pigment dispersion and toner containing compound obtained by the production method

Patent metadata

Field	Value
Publication number	US-9556290-B2
Application number	US-201514673858-A
Country	US
Kind code	B2
Filing date	Mar 30, 2015
Priority date	Apr 1, 2014
Publication date	Jan 31, 2017
Grant date	Jan 31, 2017

Abstract

To provide a method for producing a compound that enhances dispersibility of a pigment of respective colors in a water-insoluble solvent, as well as a pigment dispersant, and a pigment composition, a pigment dispersion and a toner having a good tinting power. A method for producing a compound, including the following:
(i): subjecting a polymerizable monomer forming a monomer unit represented by formula (1) to radical polymerization in the presence of a radical polymerization initiator and an iodine molecule to provide a polymer; and
(ii): binding a colorant to a terminal of a main chain of the polymer:

wherein

R 1 represents a hydrogen atom and an alkyl group, and

R 2 represents a phenyl group, a carboxyl group, an alkoxycarbonyl group or a carboxamide group.

First claim

What is claimed is:

1. A method for producing a compound, comprising the following (i) to (ii):
(i): subjecting a polymerizable monomer represented by formula (A) to radical polymerization in the presence of a radical polymerization initiator and an iodine molecule to provide a polymer; and
(ii): binding a colorant to a terminal of a main chain of the polymer:

wherein
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.

2. The method for producing a compound according to claim 1 , wherein the colorant is an azo compound.

3. The method for producing a compound according to claim 1 , wherein the colorant is bound to the terminal of the main chain of the polymer via an amide bond.

4. The method for producing a compound according to claim 1 , wherein the compound is represented by the following formula (2):

wherein
at least one of Ar and R 3 to R 8 is bound to the polymer via a linking group,
Ar, when not bound to the polymer, represents an aryl group, or an aryl group having a substituent,
the substituent of the aryl group having a substituent is a functional group selected from the group consisting of an alkyl group, an alkoxy group, a hydroxyl group, a cyano group, a halogen atom, a trifluoromethyl group, an alkoxycarbonyl group, a carboxamide group, a sulfonamide group, an alkoxysulfonyl group, a sulfonic acid group, a urea group and a thiourea group, and the urea group optionally forms a 5-membered heterocyclic ring together with two adjacent carbon atoms of Ar that can be substituted,
R 3 , when not bound to the polymer, represents an alkyl group, an alkyl group having a substituent, a phenyl group, a phenyl group having a substituent, an alkoxy group or an amino group,
R 4 to R 8 , when not bound to the polymer, each independently represent a hydrogen atom, an alkyl group, an alkoxy group, a hydroxyl group, a cyano group, a halogen atom, a trifluoromethyl group, an alkoxycarbonyl group, a carboxamide group, a sulfonamide group, an alkoxysulfonyl group, a sulfonic acid group, a urea group, a thiourea group or the following formula (3), and the urea group optionally forms a 5-membered heterocyclic ring together with two adjacent carbon atoms of R 4 to R 8 ,
Ar, when bound to the polymer, represents a group formed by leaving of a hydrogen atom from the functional group that can be represented by Ar not bound to the polymer,
any of R 3 to R 8 , when bound to the polymer, represents a group formed by leaving of a hydrogen atom from the functional group that can be represented by R 3 to R 8 not bound to the polymer;

wherein
Ar and R 3 have the same meanings as Ar and R 3 in the formula (2).

5. The method for producing a compound according to claim 4 , wherein the compound is represented by the following formula (4):

wherein
at least one R 3 to R 13 is bound to the polymer via a linking group,
R 3 to R 8 have the same meanings as R 3 to R 8 in the formula (2),
R 9 to R 13 , when not bound to the polymer, represent a hydrogen atom, an alkyl group, an alkoxy group, a hydroxyl group, a cyano group, a halogen atom, a trifluoromethyl group, an alkoxycarbonyl group, a carboxamide group, a sulfonamide group, an alkoxysulfonyl group, a sulfonic acid group, a urea group, a thiourea group and the following formula (5), and the urea group optionally forms a 5-membered heterocyclic ring together with two adjacent carbon atoms of R 9 to R 13 , and
any of R 9 to R 13 , when bound to the polymer, represents a group formed by leaving of a hydrogen atom from the functional group that can be represented by R 9 to R 13 not bound to the polymer;

wherein
R 3 has the same meanings as R 3 in the formula (2), and
R 9 to R 13 have the same meanings as R 9 to R 13 in the formula (4).

6. The method for producing a compound according to claim 1 , wherein the polymerizable monomer represented by the formula (A) is styrene or acrylic acid ester.

7. The method for producing a compound according to claim 1 , wherein the radical polymerization initiator has a carboxy group or an alkoxycarbonyl group.

8. The method for producing a compound according to claim 4 , wherein the linking group is represented by any of the following formulae (6) to (10):

wherein
“**” represents a binding position to the polymer,
“***” represents a binding position to the colorant,
A represents a carboxylic acid amide bond, a carboxylic acid ester bond, a sulfonic acid amide bond, a sulfonic acid ester bond or an ether bond,
L represents a single bond or an alkylene group, and
R 14 to R 20 represent a hydrogen atom or an alkyl group.

9. The method for producing a compound according to claim 8 , wherein A in the formulae (6) to (10) is a carboxylic acid amide bond.

10. The method for producing a compound according to claim 8 , wherein the linking group is represented by the formula (6).

Assignees

• Canon Kk

Inventors

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

Classifications

• C09B69/106

  containing an azo dye · CPC title

• C09B68/41

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

• C08L25/14

  with unsaturated esters · CPC title

• G03G9/08726

  Polymers of unsaturated acids or derivatives thereof · CPC title

• C09B67/0033

  Blends of pigments; Mixtured crystals; Solid solutions · CPC title