Production process for self-dispersible pigment, self-dispersible pigment, ink, ink cartridge and ink jet recording method
The invention provides a production process for a self-dispersible pigment, having 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) and a compound represented by the following general formula (2) to react with the particle surface of the pigment: wherein A 1 and A 2 are each a carboxylic acid group or the like.
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) and a compound represented by the following general formula (2) to react with the particle surface of the pigment:
wherein R 1 , R 2 and R 3 are, independently of one another, a hydrogen atom, a group having at least one of an aliphatic group and an aromatic group, a carboxylate ester group, or —S(═O) 2 —R 4 , with the proviso that R 1 , R 2 and R 3 are not hydrogen atoms at the same time, R 4 is a hydroxy group or a group having at least one of an aliphatic group and an aromatic group, and A 1 is selected from the group consisting of a carboxylic acid group, a sulfonic acid group, a phosphoric acid group, a phosphonic acid group, and 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 and R 6 are, independently of each other, a hydrogen atom, a group having at least one of an aliphatic group and an aromatic group, a halogen atom, a cyano group, a nitro group, an amino group, an alkoxy group, a thioalkoxy group, an acyl group, a carboxylate ester group, an aryloxy group, a carboxylic acid group, a sulfonic acid group, a phosphoric acid group, or a phosphonic acid group, with the proviso that R 5 and R 6 are not hydrogen atoms at the same time, R 7 is a hydrogen atom, a group having at least one of an aliphatic group and an aromatic group or a carboxylate ester group, and A 2 is selected from the group consisting of a carboxylic acid group, a sulfonic acid group, a phosphoric acid group, a phosphonic acid group, and 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 A 1 in the general formula (1) and A 2 in the general formula (2) 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 one or two of R 1 , R 2 and R 3 in the general formula (1) are methyl groups, and the total number of carbon atoms of R 1 , R 2 and R 3 is 2 or less.
4. The production process according to claim 1 , wherein at least one of R 1 , R 2 and R 3 in the general formula (1) is a t-butoxycarbonyl group.
5. The production process according to claim 1 , wherein at least one of R 1 , R 2 and R 3 in the general formula (1) is —S(═O) 2 —R 4 , and R 4 is selected from the group consisting of a methyl group, a 2-hydroxyethyl group, a phenyl group and a tolyl group.
6. The production process according to claim 1 , wherein the step is conducted in an aqueous system.
7. The production process according to claim 1 , wherein the step is conducted in a liquid medium.
8. The production process according to claim 1 , wherein the process is conducted in the presence of an oxidizing agent.
9. The production process according to claim 1 , wherein the process is conducted at a pH of 1 or more to 13 or less.
10. 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.
11. The production process according to claim 1 , wherein the pigment constituting the self-dispersible pigment is a carbon black.
12. A self-dispersible pigment produced by the production process according to claim 1 .
13. An ink comprising a self-dispersible pigment, wherein the self-dispersible pigment is the self-dispersible pigment according to claim 12 .
14. An ink cartridge comprising an ink and an ink storage portion storing the ink, wherein the ink comprises the ink according to claim 13 .
15. 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 13 .
16. 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 and an aqueous medium, wherein the step of producing the self-dispersible pigment is the production process according to claim 1 .
17. The production process according to claim 1 , wherein the treatment agent is the compound represented by the general formula (1).
18. The production process according to claim 17 , wherein A 1 in the general formula (1) has 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.
19. The production process according to claim 17 , wherein one or two of R 1 , R 2 and R 3 in the general formula (1) are methyl groups, and the total number of carbon atoms of R 1 , R 2 and R 3 is 2 or less.
20. The production process according to claim 17 , wherein at least one of R 1 , R 2 and R 3 in the general formula (1) is a t-butoxycarbonyl group.
21. The production process according to claim 17 , wherein at least one of R 1 , R 2 and R 3 in the general formula (1) is —S(═O) 2 =R 4 , and R 4 is selected from the group consisting of a methyl group, a 2-hydroxyethyl group, a phenyl group and a tolyl group.
22. The production process according to claim 17 , wherein the step is conducted in an aqueous system.
23. A self-dispersible pigment produced by the production process according to claim 17 .
24. An ink comprising a self-dispersible pigment, wherein the self-dispersible pigment is the self-dispersible pigment according to claim 23 .
25. An ink cartridge comprising an ink and an ink storage portion storing the ink, wherein the ink comprises the ink according to claim 24 .
26. 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 24 .
27. The production process according to claim 17 , wherein the step is conducted in a liquid medium.
28. The production process according to claim 17 , wherein the process is conducted in the presence of an oxidizing agent.
29. The production process according to claim 17 , wherein the process is conducted at a pH of 1 or more to 13 or less.
30. The production process according to claim 17 , wherein the pigment constituting the self-dispersible pigment is at least one of an inorganic pigment and an organic pigment.
31. The production process according to claim 17 , wherein the pigment constituting the self-dispersible pigment is a carbon black.
32. 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 and an aqueous medium, wherein the step of producing the self-dispersible pigment is the production process according to claim 17 .