Production process for self-dispersible pigment, self-dispersible pigment, ink, ink cartridge and ink jet recording method

Patent metadata

Field	Value
Publication number	US-9441128-B2
Application number	US-201514748697-A
Country	US
Kind code	B2
Filing date	Jun 24, 2015
Priority date	Jun 30, 2014
Publication date	Sep 13, 2016
Grant date	Sep 13, 2016

Abstract

The invention provides a production process for a self-dispersible pigment, comprising a step of bonding a functional group containing a hydrophilic group to a particle surface of a pigment by causing at least one treatment agent selected from the group consisting of a compound represented by the following general formula (1), a compound represented by the following general formula (2) and a compound represented by the following general formula (3) to react with the particle surface of the pigment.

First claim

What is claimed is:

1. A production process for a self-dispersible pigment, the process comprising a step of bonding a functional group containing a hydrophilic group to a particle surface of a pigment by causing at least one treatment agent selected from the group consisting of a compound represented by the following general formula (1), a compound represented by the following general formula (2), and a compound represented by the following general formula (3) to react with the particle surface of the pigment:
R 1 —N═N—R 2   (1)

wherein R 1 is (1) a cyano group or (2) an atomic group, the atomic group having (i) at least one group selected from the group consisting of an ester group, an ether group, a thioether group, a ketone group, and a sulfonyl group, and (ii) a group having at least one of an aliphatic group and an aromatic group, and the at least one group (i) is bonded to an azo group and the group (ii) is bonded to the at least one group (i), such that the group (ii) is bonded through the at least one group (i) to the azo group, and R 2 is a group (a) having at least one of an aliphatic group and an aromatic group, and (b) being substituted with at least one hydrophilic group selected from the group consisting of a carboxylic acid group, a sulfonic acid group, a phosphoric acid group, and a phosphonic acid group;

wherein R 3 is a cyano group or an atomic group having (i) at least one group selected from the group consisting of an ester group, an ether group, a thioether group, a ketone group, and a sulfonyl group, and (ii) a group having at least one of an aliphatic group and an aromatic group, and R 4 is a group (a) having at least one of an aliphatic group and an aromatic group and (b) being substituted with at least one hydrophilic group selected from the group consisting of a carboxylic acid group, a sulfonic acid group, a phosphoric acid group, and a phosphonic acid group; and

wherein R 5 is a group (a) having at least one of an aliphatic group and an aromatic group and (b) being substituted with at least one hydrophilic group selected from the group consisting of a carboxylic acid group, a sulfonic acid group, a phosphoric acid group, and a phosphonic acid group.

2. The production process according to claim 1 , wherein R 2 of the compound represented by the general formula (1), R 4 of the compound represented by the general formula (2), and R 5 of the compound represented by the general formula (3) have at least one of (a) a structure containing an arylene group and plural carboxylic acid groups and (b) a structure containing an amide bond and a phosphonic acid group.

3. The production process according to claim 1 , wherein R 1 of the compound represented by the general formula (1) and R 3 of the compound represented by the general formula (2) have a cyano group or an atomic group having (i) at least one group selected from the group consisting of an ester group, an ether group, and a sulfonyl group, and (ii) a group having at least one of an aliphatic group and an aromatic group.

4. The production process according to claim 1 , wherein the step is conducted in an aqueous system.

5. A self-dispersible pigment produced by the production process according to claim 1 .

6. An ink comprising a self-dispersible pigment, wherein the self-dispersible pigment is the self-dispersible pigment according to claim 5 .

7. An ink cartridge comprising an ink and an ink storage portion storing the ink, wherein the ink comprises the ink according to claim 6 .

8. An ink jet recording method comprising ejecting an ink from a recording head of an ink jet system to record an image on a recording medium, wherein the ink comprises the ink according to claim 6 .

9. The production process according to claim 1 , wherein the least one of an aliphatic group and an aromatic group of R 3 in the general formula (2) is bonded to an azoxy group through at least one group selected from the group consisting of an ester group, an ether group, a thioether group, a ketone group, and a sulfonyl group.

10. The production process according to claim 1 , wherein the step is conducted in a liquid medium.

11. The production process according to claim 1 , wherein the process is conducted in the presence of an oxidizing agent.

12. The production process according to claim 1 , wherein the process is conducted at a pH of 1 or more to 13 or less.

13. The production process according to claim 1 , wherein the pigment constituting the self-dispersible pigment is at least one of an inorganic pigment and an organic pigment.

14. The production process according to claim 1 , wherein the pigment constituting the self-dispersible pigment is a carbon black.

15. A preparation process for an ink, comprising a step of producing a self-dispersible pigment and a step of preparing an ink by mixing components including the self-dispersible pigment, wherein the step of producing the self-dispersible pigment is the production process according to claim 1 .

Assignees

• Canon Kk

Inventors

• Higashi Ryuji
• Watanabe Taiki
• Suzuki Koichi

Classifications

• C07C303/02

  of sulfonic acids or halides thereof · CPC title

• C09D11/326 Primary

  characterised by the pigment dispersant · CPC title

• C07F9/3873 Primary

  containing nitrogen substituent, e.g. N.....H or N-hydrocarbon group which can be substituted by halogen or nitro(so), N.....O, N.....S, N.....C(=X)- (X =O, S), N.....N, N...C(=X)...N (X =O, S) · CPC title

• C07C63/15

  all carboxyl groups bound to carbon atoms of the six-membered aromatic ring · CPC title

• C07F9/65312

  having the two nitrogen atoms in positions 1 and 2 · CPC title