Ink composition and ink jet recording method

• US 7,041,162 B2
• Filed: 08/07/2003
• Issued: 05/09/2006
• Est. Priority Date: 08/15/2002
• Status: Expired due to Fees

• Current Assignee: Fujifilm Corporation (Fujifilm Holdings Corporation)
• Original Assignee: Fuji Photo Film Co Limited (Fujifilm Holdings Corporation)
• Inventors: Ishizuka, Takahiro, Ikeda, Kenji
• Primary Examiner(s): KLEMANSKI, HELENE G
• Application Number:
  US10/635,575
• Publication Number:
  US 20040035322A1
• Time in Patent Office: 1,006 Days
• Field of Search: 106/31.59, 106/31.51, 106/31.48, 106/31.5, 106/31.47, 106/31.49, 347/100
• US Class Current: 106/31.59
• CPC Class Codes: C09D 11/328 characterised by dyes
• CPC Class Codes: C09D 11/38 characterised by non-macromolecular additives other than solvents, pigments or dyes

Abstract

The present invention provides an aqueous ink composition comprising a color microparticle dispersion including an oil-soluble dye, a hydrophilic organic solvent and a perfluoroalkylenesulfonic acid or a fluorine type surfactant other than derivatives thereof, and an ink jet method for recording an image by using this aqueous ink composition.

Claims

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—

(CF₂)_m—

(CH₂)_n—

Y¹-L¹-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;

Y¹ represents a connecting group selected from the group consisting of —

O—

, —

S—

, —

SO₂— and

—

SO—

;

L¹ 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;

Y² represents a connecting group selected from the group consisting of —

O—

, —

S—

, —

SO₂— and

—

SO—

;

L² 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 R¹, R², R³ and R⁴ 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 —

NR⁵R⁶ or a hydroxy group;

R⁵ and R⁶ 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;

B¹ represents ═

C(R³)—

or ═

N—

;

B² represents —

C(R⁴)═

or —

N═

, at least one of R¹ and R⁵, R³ and R⁶, and R¹ and R² 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;

B¹ represents ═

CR¹— and

B² represents —

CR²═

, or one of B¹ and B² represents a nitrogen atom and the other of B¹ and B² represents ═

CR¹—

or —

CR²═

;

R⁵ and R⁶ 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, R¹ and R² 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

R¹ and R⁵ or R⁵ and R⁶ may be bonded to form a five- or six-membered ring;

wherein X¹, X², X³ and X⁴ each independently represents —

SO-Z¹, —

SO₂-Z¹ or —

SO₂NR²¹R²²;

Z¹ 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;

R²¹ and R²² 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;

R² and R²² are not both hydrogen atoms at the same time;

Y¹, Y², Y³ and Y⁴ 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;

a¹ and b¹ each independently denotes an integer from 0 to 4 and satisfy the relationship;

a¹+b¹=4, a² and b² each independently denotes an integer from 0 to 4 and satisfy the relationship;

a²+b²=4, a³ and b³ each independently denotes an integer from 0 to 4 and satisfy the relationship;

a³+b³=4;

a⁴ and b⁴ each independently denotes an integer from 0 to 4 and satisfy the relationship;

a⁴+b⁴=4;

the sum of a¹ to a⁴ is 2 or more; and

when any of a¹ to a⁴ and b¹ to b⁴ denote an integer of 2 or more;

corresponding pluralities of any of X¹ to X⁴ and Y¹ to Y⁴ 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—

(CF₂)_m—

(CH₂)_n—

Y¹-L¹-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;

Y¹ represents a connecting group selected from the group consisting of —

O—

, —

S—

, —

SO₂— and

—

SO—

;

L¹ 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;

Y² represents a connecting group selected from the group consisting of —

O—

, —

S—

, —

SO₂— and

—

SO—

;

L² 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 R¹, R², R³ and R⁴ 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 —

NR⁵R⁶ or a hydroxy group, R⁵ and R⁶ 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;

B¹ represents ═

C(R³)—

or ═

N—

;

B² represents —

C(R⁴)═

or —

N═

; and

at least one of R¹ and R⁵, R³ and R⁶, and R¹ and R² 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;

B¹ represents ═

CR¹—

and B² represents —

CR²═

, or one of B¹ and B² represents a nitrogen atom and the other of B¹ and B² represents ═

CR¹—

or —

CR²═

;

R¹ and R⁶ 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, R¹ and R² 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

R¹ and R⁵ or R⁵ and R⁶ may be bonded to form a five- or six-membered ring;

wherein X¹, X², X³ and X⁴ each independently represents —

SO-Z¹, —

SO₂-Z¹ or —

SO₂NR²¹R²²;

Z¹ 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;

R²¹ and R²² 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;

R²¹ and R²² are not both hydrogen atoms at the same time;

Y¹, Y², Y³ and Y⁴ 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;

a¹ and b¹ each independently denotes an integer from 0 to 4 and satisfy the relationship;

a¹+b¹=4;

a² and b² each independently denotes an integer from 0 to 4 and satisfy the relationship;

a²+b²=4, a³ and b³ each independently denotes an integer from 0 to 4 and satisfy the relationship;

a³+b³=4;

a⁴ and b⁴ each independently denotes an integer from 0 to 4 and satisfy the relationship;

a⁴+b⁴=4;

the sum of a¹ to a⁴ is 2 or more; and

when any of a¹ to a⁴ and b¹ to b⁴ denote an integer of 2 or more, corresponding pluralities of any of X¹ to X⁴ and Y¹ to Y⁴ 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.