Pigment-dispersed composition

• US 5,922,122 A
• Filed: 07/29/1997
• Issued: 07/13/1999
• Est. Priority Date: 07/31/1996
• Status: Expired due to Fees

• Current Assignee: Fuji Photo Film Co Limited (Fujifilm Holdings Corporation)
• Original Assignee: Fuji Photo Film Co Limited (Fujifilm Holdings Corporation)
• Inventors: Takeda, Akihiko, Sugiyama, Takekatsu
• Primary Examiner(s): Bell, Mark L.
• Assistant Examiner(s): Hertzog, Scott L.
• Application Number:
  US08/902,628
• Time in Patent Office: 714 Days
• Field of Search: 106/413, 106/493, 106/496, 106/497, 106/498, 544/180, 544/194, 544/196, 544/197, 544/198, 544/204, 544/208, 544/209, 544/211, 544/212
• US Class Current: 106/493
• CPC Class Codes: C09B 57/02 Coumarine dyes
• CPC Class Codes: C09B 67/0033 Blends of pigments; Mixtured crystals; Solid solutions
• CPC Class Codes: C09B 67/0085 Non common dispersing agents

Abstract

A composition containing an organic pigment and a compound having the formula (I): ##STR1## in which R¹ is a group having the formula (II): ##STR2## in which R⁴ and R⁵ represent hydrogen or alkyl, or R⁴ and R⁵ are bonded to each other to form a ring together with a nitrogen atom, X represents alkylene or alkyleneoxyalkylene, and Y represents --O--, --S-- or a group represented by --NR⁶ -- wherein R⁶ is hydrogen or lower alkyl; and R² and R³ represent a group having the formula (II), alkyl, aralkyl, aryl, alkoxy, aralkyloxy, aryloxy, alkylamino, arylamino or a halogen atom. A photosensitive colored composition is made of the composition, a polymer having acidic group, a photopolymerizable monomer and a photopolymerization initiator.

Claims

1. A composition containing an organic pigment and a compound having the formula (I) in an amount of 0.1 to 200 weight % of the pigment:

##STR14## in which R¹ is a group having the formula (II);

##STR15## in which each of R⁴ and R⁵ independently represents a hydrogen atom, an alkyl group, a hydroxyalkyl group or an alkoxyalkyl group, or R⁴ and R⁵ are bonded to each other to form a ring together with a nitrogen atom, X represents an alkylene group or an alkyleneoxyalkylene group, and Y represents --O-- --S-- or a group represented by --NR⁶ -- wherein R⁶ is a hydrogen atom or a lower alkyl group; and

each of R² and R³ independently represents a group having the formula (II), an alkyl group, an aralkyl group, an aryl group, an aryl group substituted with alkyl, an alkoxy group, an alkoxy group substituted with alkoxy or aryloxy, an aralkyloxy group, an aryloxy group, an alkylamino group, an alkylamino group substituted with aryl, an arylamino group, an arylamino group substituted with alkyl or aryl, an amino group substituted with heterocyclic group, an amino group substituted with heterocyclic group having alkyl or aryl, or a halogen atom.

2. The composition of claim 1, wherein each of R⁴ and R⁵ independently represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms, a hydroxyalkyl group of 1 to 5 carbon atoms or an alkoxyalkyl group of 2 to 5 carbon atoms, or R⁴ and R⁵ are bonded to each other to form a ring together with a nitrogen atom, X represents an alkylene group of 2 to 5 carbon atoms or an alkyleneoxyalkylene group of 2 to 5 carbon atoms, and Y represents --O-- or NR⁶.

3. The composition of claim 1, wherein each of R² and R³ independently represents an alkoxy group of 1 to 5 carbon atoms, an alkoxy group of 2 to 6 carbon atoms substituted with alkyl, an alkylamino group of 1 to 5 carbon atoms, an alkylamino group of 7 to 11 carbon atoms substituted with aryl, an aralkyloxy group of 6 to 30 carbon atoms, an aryloxy group of 6 to 30 carbon atoms, an arylamino group of 6 to 30 carbon atoms, an amino group of 5 to 30 carbon atoms substituted with heterocyclic group, an amino group of 6 to 30 carbon atoms substituted with heterocyclic group having alkyl or aryl.

4. The composition of claim 1, wherein each of R⁴ and R⁵ independently represents a hydrogen atom, an alkyl group of 1 to 4 carbon atoms, an alkyl group of 1 to 4 carbon atoms substituted with hydroxy group or alkoxy at its terminal, or R⁴ and R⁵ are bonded to each other, to form a morphorin ring together with a nitrogen atom, X represents an alkylene group of 2 to 5 carbon atoms or an alkyleneoxyalkylene group of 2 to 5 carbon atoms, and Y represents --NH--.

5. The composition of claim 1, wherein R² represents a group having --NHR⁷ wherein R⁷ represents an aryl group of 6 to 10 carbon atoms, an aralkyl group of 7 to 8 carbon atoms or an alkyl group of 1 to 4 carbon atoms, a group having the formula (II) with proviso that each of R⁴ and R⁵ independently represents an alkyl group of 1 to 4 carbon atoms, X represents an alkylene group of 2 to 3 carbon atoms and Y represents --NH--, an alkyl group of 1 to 4 carbon atoms, an alarkyl group of 7 to 9 carbon atoms, an alkoxy group of 1 to 8 carbon atoms, an alkoxy group of 2 to 8 carbon atoms substituted with alkoxy or phenoxy, an aryloxy group of 6 to 10 carbon atoms, an aryl group of 6 to 10 carbon atoms or a halogen atom;

and

R³ represents a group having --NHR⁸ wherein R⁸ represents a coumarinyl group, a coumarinyl group substituted with phenyl or methyl, an aryl group of 6 to 12 carbon atoms, an aryl group of 7 to 12 carbon atoms substituted with alkyl, an aralkyl group of 7 to 11 carbon atoms, a quinolinyl group or an alkyl group of 1 to 4 carbon atoms, or an alkoxy group of 1 to 4 carbon atoms.

6. The composition of claim 1, which further contains a polymer having acidic group.

7. The composition of claim 1, wherein the organic pigment comprises a yellow organic pigment.

15. A photosensitive colored resin composition comprising the pigment-dispersed composition of claim 1 or 8, a polymer having acidic group, a photopolymerizable monomer having at least two ethylenically unsaturated double bonds and a photopolymerization initiator.

8. A composition containing an organic pigment, an organic solvent and a compound having the formula (I) in an amount of 0.1 to 200 weight % of the pigment:

##STR16## in which R¹ is a group having the formula (II);

##STR17## in which each of R⁴ and R⁵ independently represents a hydrogen atom, an alkyl group, a hydroxyalkyl group or an alkoxyalkyl group, or R⁴ and R⁵ are bonded to each other to form a ring together with a nitrogen atom, X represents an alkylene group or an alkyleneoxyalkylene group, and Y represents --O-- --S-- or a group represented by --NR⁶ -- wherein R⁶ is a hydrogen atom or a lower alkyl group; and

each of R² and R³ independently represents a group having the formula (II), an alkyl group, an aralkyl group, an aryl group, an aryl group substituted with alkyl, an alkoxy group, an alkoxy group substituted with alkoxy or aryloxy, an aralkyloxy group, an aryloxy group, an alkylamino group, an alkylamino group substituted with aryl, an arylamino group, an arylamino group substituted with alkyl or aryl, an amino group substituted with heterocyclic group, an amino group substituted with heterocyclic group having alkyl or aryl, or a halogen atom.

9. The composition of claim 8, wherein each of R⁴ and R⁵ independently represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms, a hydroxyalkyl group of 1 to 5 carbon atoms or an alkoxyalkyl group of 2 to 5 carbon atoms, or R⁴ and R⁵ are bonded to each other to form a ring together with a nitrogen atom, X represents an alkylene group of 2 to 5 carbon atoms or an alkyleneoxyalkylene group of 2 to 5 carbon atoms, and Y represents --O-- or NR⁶.

10. The composition of claim 8, wherein each of R² and R³ independently represents an alkoxy group of 1 to 5 carbon atoms, an alkoxy group of 2 to 6 carbon atoms substituted with alkyl, an alkylamino group of 1 to 5 carbon atoms, an alkylamino group of 7 to 11 carbon atoms substituted with aryl, an aralkyloxy group of 6 to 30 carbon atoms, an aryloxy group of 6 to 30 carbon atoms, an arylamino group of 6 to 30 carbon atoms, an amino group of 5 to 30 carbon atoms substituted with heterocyclic group, an amino group of 6 to 30 carbon atoms substituted with heterocyclic group having alkyl or aryl.

11. The composition of claim 8, wherein each of R⁴ and R⁵ independently represents a hydrogen atom, an alkyl group of 1 to 4 carbon atoms, an alkyl group of 1 to 4 carbon atoms substituted with hydroxy group or alkoxy at its terminal, or R⁴ and R⁵ are bonded to each other to form a morphorin ring together with a nitrogen atom, X represents an alkylene group of 2 to 5 carbon atoms or an alkyleneoxyalkylene group of 2 to 5 carbon atoms, and Y represents --NH--.

12. The composition of claim 8, wherein R² represents a group having --NHR⁷ wherein R⁷ represents an aryl group of 6 to 10 carbon atoms, an aralkyl group of 7 to 8 carbon atoms or an alkyl group of 1 to 4 carbon atoms, a group having the formula (II) with proviso that each of R⁴ and R⁵ independently represents an alkyl group of 1 to 4 carbon atoms, X represents an alkylene group of 2 to 3 carbon atoms and Y represents --NH--, an alkyl group of 1 to 4 carbon atoms, an alarkyl group of 7 to 9 carbon atoms, an alkoxy group of 1 to 8 carbon atoms, an alkoxy group of 2 to 8 carbon atoms substituted with alkoxy or phenoxy, an aryloxy group of 6 to 10 carbon atoms, an aryl group of 6 to 10 carbon atoms or a halogen atom;

and

R³ represents a group having --NHR⁸ wherein R⁸ represents a coumarinyl group, a coumarinyl group substituted with phenyl or methyl, an aryl group of 6 to 12 carbon atoms, an aryl group of 7 to 12 carbon atoms substituted with alkyl, an aralkyl group of 7 to 11 carbon atoms, a quinolinyl group or an alkyl group of 1 to 4 carbon atoms, or an alkoxy group of 1 to 4 carbon atoms.

13. The composition of claim 8, which further contains a polymer having acidic group.

14. The composition of claim 8, wherein the organic pigment comprises a yellow organic pigment.

16. A triazine compound having the formula (III):

##STR18## in which R¹¹ represents a group having the formula (IV);

##STR19## wherein each of R¹⁴ and R¹⁵ independently represents a hydrogen atom, an alkyl group of 1 to 4 carbon atoms, an alkyl group of 1 to 4 carbon atoms substituted with hydroxy group or alkoxy at its terminal, or R¹⁴ and R¹⁵ are bonded to each other to form a morphorin ring together with a nitrogen atom, X¹ represents an alkylene group of 2 to 5 carbon atoms or an alkyleneoxyalkylene group of 2 to 5 carbon atoms, and Y¹ represents --NH--;

R¹² represents a group having --NHR¹⁷ wherein R¹⁷ represents an aryl group of 6 to 10 carbon atoms, an aralkyl group of 7 to 8 carbon atoms or an alkyl group of 1 to 4 carbon atoms, a group of the formula (IV) with proviso that R¹⁴ and R¹⁵ represent each independently an alkyl group of 1 to 5-carbon atoms, X¹ represents an alkylene group of 2 to 3 carbon atoms and Y¹ represents --NH--, an alkyl group of 1 to 4 carbon atoms, an alarkyl group of 7 to 9 carbon atoms, an alkoxy group of 1 to 8 carbon atoms, an alkoxy group of 2 to 8 carbon atoms substituted with alkoxy or phenoxy, an aryloxy group of 6 to 10 carbon atoms, an aryl group of 6 to 10 carbon atoms or a halogen atom; and

R¹³ represents a group having --NHR¹⁸ wherein R¹⁸ represents an aryl group of 6 to 12 carbon atoms, an aryl group of 7 to 12 carbon atoms substituted with alkyl, an aralkyl group of 7 to 11 carbon atoms, a quinolinyl group or an alkyl group of 1 to 4 carbon atoms, or an alkoxy group of 1 to 4 carbon atoms.