IP Library Granted Patent US 7,193,080
Granted Patent B2
US 7,193,080 · App. 10/679,495 · Granted Mar 20, 2007

Dye-forming coupler, silver halide photographic light-sensitive material and azomethine dye compound

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Quick Facts
Patent No.
US 7,193,080
App. No.
10/679,495
Granted
Mar 20, 2007
Kind
B2
Abstract

A dye-forming coupler and compound of formula (I): wherein Q represents a residue that forms, together with —N—C═N—, a nitrogen-containing 6-membered ring; R A represents an aryl, heterocyclic, or —(R 1 ) r —(R 4 ) m group; X represents an aryl group; Y represents a hydrogen atom, or a group capable of being split-off upon a coupling reaction with an oxidized product of a developing agent: wherein, when R A represents an —(R 1 ) r —(R 4 ) m group, R 1 represents a methylene group, a methine group, or a carbon atom; r is 1 to 30; R 4 represents a substituent except for a hydrogen atom; m is 1 to 30; and the —(R 1 ) r —(R 4 ) m group does not represent a straight-chain alkyl group.

Claims (27)

1. An azomethine dye compound represented by formula (II):

wherein Q represents a residue that forms, together with the —N—C═N— moiety, a nitrogen-containing 6-membered ring; R A represents an aryl group, a heterocyclic group, or an —(R 1 ) r —(R 4 ) m group; X represents an aryl group;

wherein,

when R A represents an —(R 1 ) r —(R 4 ) m group, R 1 represents a methylene group, a methine group, or a carbon atom; r represents an integer of 1 to 30, and R 1 s may be the same or different independently, when r is 2 or more; R 4 represents a substituent except for a hydrogen atom; m represents an integer of 1 to 30, and R 4 s may be the same or different independently, or R 4 s may be combine together to form a multiple bond, or alternatively R 4 s may bond with each other to form a ring, when m is 2 or more; and the —(R 1 ) r —(R 4 ) m group does not represent a straight-chain alkyl group; R 5 and R 6 each represent a hydrogen atom or a substituent, or R 5 and R 6 may bond with each other to form a ring; R 7 represents a hydrogen atom or a substituent; n represents 0 (zero) or an integer of 1 to 4, with the proviso that R 7 s may be the same or different independently, or R 7 s may bond with each other to form a condensed ring, n is 2 or more; or R 7 may bond with R 5 or R 6 to form a condensed ring, n is 1 or more.

2. The azomethine dye compound as claimed in claim 1 , wherein the azomethine dye compound represented by formula (II) is represented by formula (IIA):

wherein Q represents a residue that forms, together with the —N—C═N— moiety, a nitrogen-containing 6-membered ring; R 11 represents an aryl group or a heterocyclic group; X represents an aryl group; R 5 and R 6 each represent a hydrogen atom or a substituent, or R 5 and R 6 may bond with each other to form a ring; R 7 represents a hydrogen atom or a substituent; n represents 0 (zero) or an integer of 1 to 4, with the proviso that R 7 s may be the same or different independently, or R 7 s may bond with each other to form a condensed ring, when n is 2 or more; or R 7 may bond with R 5 or R 6 to form a condensed ring, when n is 1 or more.

3. The azomethine dye compound as claimed in claim 2 , wherein, in the azomethine dye compound represented by formula (IIA), Q is a residue that forms, together with the —N—C═N— moiety, a 4-pyrimidone ring.

4. The azomethine dye compound as claimed in claim 1 , wherein the azomethine dye compound represented by formula (II) is represented by formula (IIB):

wherein Q represents a residue that forms, together with the —N—C═N— moiety, a nitrogen-containing 6-membered ring; R 1 represents a methylene group, a methine group, or a carbon atom; r represents an integer of 1 to 30, and R 1 s may be the same or different independently, when r is 2 or more; R 4 represents a substituent except for a hydrogen atom; m represents an integer of 1 to 30, and R 4 s may be the same or different independently, or R 4 s may be combined together to form a multiple bond, or alternatively —R 4 s- may bond with each other to form a ring, when m is 2 or more; X represents an aryl group; and the —(R 1 ) r —(R 4 ) m group does not represent a straight-chain alkyl group; R 5 and R 6 each represent a hydrogen atom or a substituent, or R 5 and R 6 may bond with each other to form a ring; R 7 represents a hydrogen atom or a substituent; n represents 0 (zero) or an integer of 1 to 4, with the proviso that R 7 s may be the same or different independently, or R 7 s may bond with each other to form a condensed ring, when n is 2 or more; or R 7 may bond with R 5 or R 6 to form a condensed ring, when n is 1 or more.

5. The azomethine dye compound as claimed in claim 4 , wherein, in the azomethine dye compound represented by formula (IIB), Q is a residue that forms, together with the —N—C═N— moiety, a 4-pyrimidone ring; and R 4 is a group selected from the group consisting of an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, a halogen atom, an amino group, a hydroxyl group, a carboxyl group, a sulfo group, an acylamino group, an alkyl- or aryl-sulfonylamino group, a carbamoyl group, a sulfamoyl group, an acyl group, a sulfonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an alkylthio group, an arylthio group, a cyano group, an alkoxy group and an aryloxy group.

6. The azomethine dye compound as claimed in claim 4 , wherein, in the azomethine dye compound represented by formula (IIB), at least one —R 4 — bonds with a carbon atom at at least one α- to δ-positions in the (R) r .

7. The azomethine dye compound as claimed in claim 1 , wherein Q represents a residue that forms, together with the —N—C═N moiety, a nitrogen-containing 6-membered ring, wherein the members of the nitrogen-containing 6-membered ring are selected from the group consisting of nitrogen and carbon.

8. A compound represented by formula (I):

wherein Q represents a residue that forms, together with the —N—C═N— moiety, a nitrogen-containing 6-membered ring; R A represents a heterocyclic group, or an —(R 1 ) r —(R 4 ) m group; X represents an aryl group; Y represents a hydrogen atom, or a group that is capable of being split-off upon a coupling reaction with an oxidized product of a developing agent:

wherein,

when R A represents an —(R 1 ) r —(R 4 ) m group, R 1 represents a methylene group, a methine group, or a carbon atom; r represents an integer of 1 to 30, and R 1 s may be the same or different independently, when r is 2 or more; R 4 represents a substituent except for a hydrogen atom; m represents an integer of 1 to 30, and R 4 s may be the same or different independently, or R 4 s may be combined together to form

a multiple bond, or alternatively R 4 s may bond with each other to form a ring, when m is 2 or more; and the —(R 1 ) r —(R 4 ) m group does not represent a straight-chain alkyl group.

9. The compound represented by formula (IA):

wherein Q represents a residue that forms, together with the —N—C═N— moiety, a nitrogen-containing 6-membered ring; R 11 represents an aryl group X represents an aryl group; Y represents a group that is capable of being split-off upon a coupling reaction with an oxidized product of a developing agent.

10. The compound as claimed in claim 9 , wherein, in the compound represented by formula (IA), Q is a residue that forms, together with the —N—C═N moiety, a 4-pyrimidone ring.

11. The compound as claimed in claim 8 , wherein the compound represented by formula (I) is represented by formula (IB):

wherein Q represents a residue that forms, together with the —N—C═N— moiety, a nitrogen-containing 6-membered ring; R 1 represents a methylene group, a methine group, or a carbon atom; r represents an integer of 1 to 30, and R 1 s may be the same or different independently, when r is 2 or more; R 4 represents a substituent except for a hydrogen atom; m represents an integer of 1 to 30, and R 4 s may be the same or different independently, or R 4 s may be combined together to form a multiple bond, or alternatively R 4 s may bond with each other to form a ring, when m is 2 or more; X represents an aryl group; Y represents a hydrogen atom, or a group that is capable of being split-off upon a coupling reaction with an oxidized product of a developing agent; and the —(R 1 ) r —(R 4 ) m group does not represent a straight-chain alkyl group.

12. The compound as claimed in claim 11 , wherein, in the compound represented by formula (IB), Q is a residue that forms, together with the —N—C═N— moiety, a 4-pyrimidone ring; and R 4 is a group selected from the group consisting of an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, a halogen atom, an amino group, a hydroxyl group, a carboxyl group, a sulfo group, an acylamino group, an alkyl- or aryl-sulfonylamino group, a carbamoyl group, a sulfamoyl group, an acyl group, a sulfonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an alkylthio group, an arylthio group, a cyano group, an alkoxy group and an aryloxy group.

13. The compound as claimed in claim 11 , wherein, in the compound represented by formula (IB), at least one R 4 bonds with a carbon atom at at least one α- to δ-positions in the (R 1 ) r .

14. The compound as claimed in claim 8 , wherein Q represents a residue that forms, together with the —N—C═N moiety, a nitrogen-containing 6-membered ring, wherein the members of the nitrogen-containing 6-membered ring are selected from the group consisting of nitrogen and carbon.

15. A compound represented by formula (IA)′:

wherein Q′ represents —C(—R 2 )═C(—R 3 )—CO—, in which R 2 and R 3 form a 5- to 7-membered ring together with the —C═C— moiety, or R 2 and R 3 each independently represent a hydrogen atom or a substituent, and * indicates the position where Q′ bonds to the nitrogen atom of the N—R 11 moiety; R 11 represents an aryl group; and Y′ represents a hydrogen atom.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 26, 2007
From: FUJIFILM HOLDINGS CORPORATION
To: FUJIFILM CORPORATION
Reel/Frame 018934/0001 →
CHANGE OF NAME Recorded Feb 15, 2007
From: FUJI PHOTO FILM CO., LTD.
To: FUJIFILM HOLDINGS CORPORATION
Reel/Frame 018898/0872 →