Ink composition and ink jet recording method

1. An aqueous ink composition comprising:

a color microparticle dispersion comprising an oil-soluble dye;

a hydrophilic organic solvent; and

a fluorine t surfactant represented by Formula (1) or Formula (2):

R—(CF 2 ) m —(CH 2 ) n —Y 1 -L 1 -Z  Formula (1)

wherein R represents a hydrogen atom or a fluorine atom; m denotes a number of 3 to 8; n denotes a number of 0 to 6; Y 1 represents a connecting group selected from the group consisting of —O—, —S—, —SO 2 — and —SO—; L 1 represents a constitutional divalent group having 2 or more carbon atoms; and Z represents an anionic group or its salt, or

wherein R represents a hydrogen atom or a fluorine atom; m denotes a number of 3 to 8; n denotes a number of 0 to 6; Y 2 represents a connecting group selected from the group consisting of —O—, —S—, —SO 2 — and —SO—; L 2 represents a constitutional divalent group having 2 or more carbon atoms; and Z represents an anionic group or its salt.

2. An aqueous ink composition according to claim 1 , wherein the oil-soluble dye includes at least one selected from the group consisting of compounds represented by the following general formulae (I), (II), (Y-I), (M-I) and (C-I):

wherein R 1 , R 2 , R 3 and R 4 each independently represents a hydrogen atom, a halogen atom, an aliphatic group, an aromatic group, a heterocyclic group, a cyano group, a hydroxy group, a nitro group, an amino group, an alkylamino group, an alkoxy group, an aryloxy group, an amido group, an arylamino group, a ureide group, a sulfamoylamino group, an alkylthio group, an arylthio group, an alkoxycarbonylamino group, a sulfonamido group, a carbamoyl group, a sulfamoyl group, a sulfonyl group, an alkoxycarbonyl group, a heterocyclic oxy group, an azo group, an acyloxy group, a carbamoyloxy group, a silyloxy group, an aryloxycarbonyl group, an aryloxycarbonylamino group, an imide group, a heterocyclic thio group, a sulfinyl group, a phosphoryl group, an acyl group, a carboxyl group or a sulfo group; A represents —NR 5 R 6 or a hydroxy group; R 5 and R 6 each independently represents a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group and may be bonded with each other to form an aromatic ring or a hetero ring; B 1 represents ═C(R 3 )— or ═N—; B 2 represents —C(R 4 )═ or —N═, at least one of R 1 and R 5 , R 3 and R 6 , and R 1 and R 2 may be respectively bonded with each other to form an aromatic ring or hetero ring;

A-N═N-B  General formula (Y-I)

wherein A and B each independently represents a heterocyclic group which may be substituted;

wherein A represents a substituent comprising a five-membered hetero ring; B 1 represents ═CR 1 — and B 2 represents —CR 2 ═, or one of B 1 and B 2 represents a nitrogen atom and the other of B 1 and B 2 represents ═CR 1 — or —CR 2 ═; R 5 and R 6 each independently represents a hydrogen atom, an aliphatic group, an aromatic group, a heterocyclic group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, an alkylsulfonyl group, an arylsulfonyl group or a sulfamoyl group where each group may further have a substituent; G, R 1 and R 2 each independently represents a hydrogen atom, a halogen atom, an aliphatic group, an aromatic group, a heterocyclic group, a cyano group, a carboxyl group, a carbamoyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyl group, a hydroxy group, an alkoxy group, an aryloxy group, a silyloxy group, an acyloxy group, a carbamoyloxy group, a heterocyclic oxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group substituted with an alkyl group, an aryl group or a heterocyclic group, an acylamino group, a ureide group, a sulfamoylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, an alkylarylsulfonylamino group, an arylsulfonylamino group, an aryloxycarbonylamino group, a nitro group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an arylsulfinyl group, a sulfamoyl group, a sulfo group or a heterocyclic thio group where each group may be further substituted; and R 1 and R 5 or R 5 and R 6 may be bonded to form a five- or six-membered ring;

wherein X 1 , X 2 , X 3 and X 4 each independently represents —SO-Z 1 , —SO 2 -Z 1 or —SO 2 NR 21 R 22 ; Z 1 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group; R 21 and R 22 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group; R 2 and R 22 are not both hydrogen atoms at the same time; Y 1 , Y 2 , Y 3 and Y 4 each independently represents a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an aryl group, a heterocyclic group, a cyano group, a hydroxyl group, a nitro group, an amino group, an alkylamino group, an alkoxy group, an aryloxy group, an amido group, an arylamino group, a ureide group, a sulfamoylamino group, an alkylthio group, an arylthio group, an alkoxycarbonylamino group, a sulfonamido group, a carbamoyl group, a sulfamoyl group, a sulfonyl group, an alkoxycarbonyl group, a heterocyclic oxy group, an azo group, an acyloxy group, a carbamoyloxy group, a silyloxy group, an aryloxycarbonyl group, an aryloxycarbonylamino group, an imide group, a heterocyclic thio group, a phosphoryl group, an acyl group, a carboxyl group or a sulfo group where each group may further have a substituent; a 1 and b 1 each independently denotes an integer from 0 to 4 and satisfy the relationship: a 1 +b 1 =4, a 2 and b 2 each independently denotes an integer from 0 to 4 and satisfy the relationship: a 2 +b 2 =4, a 3 and b 3 each independently denotes an integer from 0 to 4 and satisfy the relationship: a 3 +b 3 =4; a 4 and b 4 each independently denotes an integer from 0 to 4 and satisfy the relationship: a 4 +b 4 =4; the sum of a 1 to a 4 is 2 or more; and when any of a 1 to a 4 and b 1 to b 4 denote an integer of 2 or more; corresponding pluralities of any of X 1 to X 4 and Y 1 to Y 4 may each independently be the same or different and M represents a hydrogen atom; a metal element, an oxide, hydroxide or halide of a metal element.

3. An aqueous ink composition according to claim 1 , wherein the vapor pressure of the hydrophilic organic solvent is lower than that of water.

4. An aqueous ink composition according to claim 1 , wherein the fluorine type surfactant is an anionic compound.

5. An aqueous ink composition according to claim 1 , wherein the fluorine type surfactant is contained in the aqueous ink composition in an amount of 0.2 to 4% by mass.

6. An aqueous ink composition according to claim 1 , the composition further comprising at least one compound selected from the group consisting of a neutralizing agent, a hydrophobic high-boiling point organic solvent, a dispersant and a dispersion stabilizer.

7. An aqueous ink composition according to claim 1 , wherein the color microparticle dispersion further contains an oil-soluble polymer.

8. An aqueous ink composition according to claim 7 , wherein the amount of the hydrophilic organic solvent to be used is 10 to 2000 parts by mass based on 100 parts by mass of the oil-soluble polymer.

9. An aqueous ink composition according to claim 8 , wherein an amount of the oil-soluble polymer to be used is 10 to 1000 parts by mass based on 100 parts by mass of the oil-soluble dye.

10. An aqueous ink composition according to claim 1 , wherein the oil-soluble dye is the following compound:

11. An ink jet recording method for recording an image comprising:

supplying an aqueous ink jet recording ink to an ink recording system, and

jetting the ink from the ink jet recording system and applying the ink to a surface for receiving the image,

wherein the aqueous ink composition comprises a color microparticle dispersion comprising an oil-soluble dye, a hydrophilic organic solvent and a fluorine surfactant represented by Formula (1) or Formula (2):

R—(CF 2 ) m —(CH 2 ) n —Y 1 -L 1 -Z  Formula (1)

wherein R represents a hydrogen atom or a fluorine atom; m denotes a number of 3 to 8; n denotes a number of 0 to 6; Y 1 represents a connecting group selected from the group consisting of —O—, —S—, —SO 2 — and —SO—; L 1 represents a constitutional divalent group having 2 or more carbon atoms; and Z represents an anionic group or its salt, or

wherein R represents a hydrogen atom or a fluorine atom; m denotes a number of 3 to 8; n denotes a number of 0 to 6; Y 2 represents a connecting group selected from the group consisting of —O—, —S—, —SO 2 — and —SO—; L 2 represents a constitutional divalent group having 2 or more carbon atoms; and Z represents an anionic group or its salt.

12. An ink jet recording method according to claim 11 , wherein the oil-soluble dye includes at least one selected from the group consisting of compounds represented by the general formulae (I), (II), (Y-I), (M-I) and (C-I):

wherein R 1 , R 2 , R 3 and R 4 each independently represents a hydrogen atom, a halogen atom, an aliphatic group, an aromatic group, a heterocyclic group, a cyano group, a hydroxy group, a nitro group, an amino group, an alkylamino group, an alkoxy group, an aryloxy group, an amido group, an arylamino group, a ureide group, a sulfamoylamino group, an alkylthio group, an arylthio group, an alkoxycarbonylamino group, a sulfonamido group, a carbamoyl group, a sulfamoyl group, a sulfonyl group, an alkoxycarbonyl group, a heterocyclic oxy group, an azo group, an acyloxy group, a carbamoyloxy group, a silyloxy group, an aryloxycarbonyl group, an aryloxycarbonylamino group, an imide group, a heterocyclic thio group, a sulfinyl group, a phosphoryl group, an acyl group, a carboxyl group or a sulfo group; A represents —NR 5 R 6 or a hydroxy group, R 5 and R 6 each independently represents a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group and may be bonded with each other to form an aromatic ring or a hetero ring; B 1 represents ═C(R 3 )— or ═N—; B 2 represents —C(R 4 )═ or —N═; and at least one of R 1 and R 5 , R 3 and R 6 , and R 1 and R 2 may be respectively bonded with each other to form an aromatic ring or hetero ring;

A-N═N-B  General formula (Y-I)

wherein A and B each independently represents a heterocyclic group which may be substituted;

wherein A represents a substituent comprising a five-membered hetero ring; B 1 represents ═CR 1 —and B 2 represents —CR 2 ═, or one of B 1 and B 2 represents a nitrogen atom and the other of B 1 and B 2 represents ═CR 1 — or —CR 2 ═; R 1 and R 6 each independently represents a hydrogen atom, an aliphatic group, an aromatic group, a heterocyclic group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, an alkylsulfonyl group, an arylsulfonyl group or a sulfamoyl group where each group may further have a substituent; G, R 1 and R 2 each independently represents a hydrogen atom, a halogen atom, an aliphatic group, an aromatic group, a heterocyclic group, a cyano group, a carboxyl group, a carbamoyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyl group, a hydroxy group, an alkoxy group, an aryloxy group, a silyloxy group, an acyloxy group, a carbamoyloxy group, a heterocyclic oxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group substituted with an alkyl group, an aryl group or a heterocyclic group, an acylamino group, a ureide group, a sulfamoylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, an alkylarylsulfonylamino group, an arylsulfonylamino group, an aryloxycarbonylamino group, a nitro group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, an alkylsulfinyl group, an arylsulfinyl group, a sulfamoyl group, a sulfo group or a heterocyclic thio group where each group may be further substituted; and R 1 and R 5 or R 5 and R 6 may be bonded to form a five- or six-membered ring;

wherein X 1 , X 2 , X 3 and X 4 each independently represents —SO-Z 1 , —SO 2 -Z 1 or —SO 2 NR 21 R 22 ; Z 1 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group; R 21 and R 22 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group; R 21 and R 22 are not both hydrogen atoms at the same time; Y 1 , Y 2 , Y 3 and Y 4 each independently represents a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an aryl group, a heterocyclic group, a cyano group, a hydroxy group, a nitro group, an amino group, an alkylamino group, an alkoxy group, an aryloxy group, an amido group, an arylamino group, a ureide group, a sulfamoylamino group, an alkylthio group, an arylthio group, an alkoxycarbonylamino group, a sulfonamido group, a carbamoyl group, a sulfamoyl group, a sulfonyl group, an alkoxycarbonyl group, a heterocyclic oxy group, an azo group, an acyloxy group, a carbamoyloxy group, a silyloxy group, an aryloxycarbonyl group, an aryloxycarbonylamino group, an imide group, a heterocyclic thio group, a phosphoryl group, an acyl group, a carboxyl group or a sulfo group where each group may further have a substituent; a 1 and b 1 each independently denotes an integer from 0 to 4 and satisfy the relationship: a 1 +b 1 =4; a 2 and b 2 each independently denotes an integer from 0 to 4 and satisfy the relationship: a 2 +b 2 =4, a 3 and b 3 each independently denotes an integer from 0 to 4 and satisfy the relationship: a 3 +b 3 =4; a 4 and b 4 each independently denotes an integer from 0 to 4 and satisfy the relationship: a 4 +b 4 =4; the sum of a 1 to a 4 is 2 or more; and when any of a 1 to a 4 and b 1 to b 4 denote an integer of 2 or more, corresponding pluralities of any of X 1 to X 4 and Y 1 to Y 4 may each independently be the same or different; and M represents a hydrogen atom, a metal element or an oxide, hydroxide, halide of a metal element.

13. An ink jet recording method according to claim 11 , wherein a vapor pressure of the hydrophilic organic solvent is lower than that of water.

14. An ink jet recording method according to claim 11 , wherein the fluorine type surfactant is an anionic compound.

15. An ink jet recording method according to claim 11 , wherein the fluorine surfactant is contained in the aqueous ink composition in an amount of 0.2 to 4% by mass.

16. An ink jet recording method according to claim 11 , wherein the aqueous ink composition further comprises at least one compound selected from the group consisting of a neutralizing agent, a hydrophobic high-boiling point organic solvent, a dispersant and a dispersion stabilizer.

17. An ink jet recording method according to claim 11 , wherein the color microparticle dispersion further contains an oil-soluble polymer.

18. An ink jet recording method according to claim 17 , wherein the amount of the hydrophilic organic solvent to be used is 10 to 2000 parts by mass based on 100 parts by mass of the oil-soluble polymer.

19. An ink jet recording method according to claim 17 , wherein an amount of the oil-soluble polymer to be used is 10 to 1000 parts by mass based on 100 parts by mass of the oil-soluble dye.

20. An ink jet recording method according to claim 11 , wherein the oil-soluble dye is the following compound:

21. An aqueous ink composition comprising:

a color microparticle dispersion comprising an oil-soluble dye;

a hydrophilic organic solvent: and

a fluorine surfactant selected from the group consisting of the following compounds;

wherein X represents a hydrogen atom or a cation.