# US 5,344,933 A · Pyrrole ring-or condensed pyrrole ring-containing azomethine dye

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- Number: US 5,344,933 A
- Document ID: US5344933A
- Status: Granted
- Kind: A
- Application number: 07/942,835
- Filed: 1992-09-10
- Granted: 1994-09-06
- Earliest claimed: 1991-09-11
- Assignees: Fuji Photo Film Co., Ltd.
- Inventors: Hisashi Mikoshiba; Katsuyoshi Yamakawa; Kozo Sato; Koushin Matsuoka
- Web page: https://patentgrep.com/patent/US5344933A

## CPC

- B41M 5/39: Dyes containing one or more carbon-to-nitrogen double bonds, e.g. azomethine
- C09B 55/009: {Azomethine dyes, the C-atom of the group -C=N- being part of a ring (Image)}
- G03C 1/83: Organic dyestuffs therefor {(polymeric dyes G03C1/835)}
- B41M: PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING, (correction of typographical errors B41J; processes for applying transfer pictures or the like B44C1/16; fluid media for correction of typographical errors by coating C09D10/00; printing textiles D06P)
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- G03C: PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES (for photomechanical purposes G03F); PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY (photographic processes characterised by the use or manipulation of apparatus classifiable per se in subclass G03B, see G03B; photomechanical production of textured or patterned surfaces G03F; electrophotography, magnetography G03G)

## Abstract

An azomethine dye is disclosed, represented by the general formula (I), (II) or (III): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each independently represents a hydrogen atom or nonmetallic atom group; X represents --OH or --NR.sup.5 R.sup.6 ; R.sup.5 and R.sup.6 each independently represents a hydrogen atom, alkyl group, aryl group or heterocyclic group; R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, R.sup.12 and R.sup.13 each independently represents a hydrogen atom or nonmetallic atom group; and R.sup.1 and R.sup.2, and/or R.sup.2 and R.sup.5, and/or R.sup.5 and R.sup.6, and/or R.sup.6 and R.sup.3, and/or R.sup.3 and R.sup.4, and/or R.sup.7 and R.sup.8, and/or R.sup.9 and R.sup.10, and/or R.sup.11 and R.sup.12, and/or R.sup.12 and R.sup.13 may be connected to each other to form a cyclic structure. A heat transfer dye providing material is also disclosed, comprising a support having thereon a dye providing layer containing a heat migrating dye, the dye providing layer comprising at least one azomethine dye represented by the general formula (I), (II) or (III).

## Claims

### Claim 1

An azomethine dye represented by the formula (I), (II) or (III): ##STR25## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each independently represents hydrogen or nonmetallic atom; X represents --OH or --NR.sup.5 R.sup.6 ; R.sup.5 and R.sup.6 each independently represents hydrogen, alkyl, aryl or heterocyclic, wherein the heterocyclic is selected from the group consisting of ##STR26## and R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, R.sup.12 and R.sup.13 each independently represents hydrogen or nonmetallic atom.

### Claim 2

An azomethine dye represented by the following formula (I) or (II): ##STR27## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each independently represents hydrogen or nonmetallic atom; X represents --OH or --NR.sup.5 R.sup.6 in which R.sup.5 and R.sup.6 each independently represents hydrogen, alkyl, aryl or heterocyclic, wherein the heterocyclic is selected from the group consisting of ##STR28## and R.sup.7, R.sup.8, R.sup.9 and R.sup.10 each independently represents hydrogen or nonmetallic atom, with the proviso that at least one of R.sup.7 and R.sup.8 is an electrophile having a Hammett's substituent constant .sigma.p value in the range of 0.15 to 0.78.

### Claim 3

A near infrared absorbing azomethine dye represented by the following formula (I) or (II): ##STR29## wherein R.sup.1 represents alkyl, --OR.sup.21 or --NR.sup.22 --CO--R23, wherein R.sup.21 represents alkyl, aryl or heterocyclic, wherein the heterocyclic is selected from the group consisting of ##STR30## R.sup.22 represents hydrogen or alkyl, R.sup.23 represents alkyl, aryl or heterocyclic, wherein the heterocyclic is selected from the group consisting of ##STR31## --OR.sup.21, --NR.sup.22 R.sup.24, and R.sup.24 represent a substituent which is attached to the nitrogen; R.sup.2, R.sup.3 and R.sup.4 each represents hydrogen or nonmetallic atom; X represents --OH or --NR.sup.5 R.sup.6, wherein R.sup.5 and R.sup.6 each independently represents hydrogen, alkyl, aryl or heterocyclic, wherein the heterocyclic is selected from the group consisting of ##STR32## and R.sup.7, R.sup.8, R.sup.9 and R.sup.10 each independently represents hydrogen or nonmetallic atom, with the proviso that at least one of R.sup.7 and R.sup.8 is an electrophile having a Hammett's substituent constant .sigma.p value in the range of 0.15 to 0.78.

### Claim 4

An azomethine dye represented by the following formula (III): ##STR33## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each represents hydrogen or nonmetallic atom; X represents --OH or --NR.sup.5 R.sup.6, wherein R.sup.5 and R.sup.6 each independently represents hydrogen, alkyl, aryl or heterocyclic, wherein the heterocyclic is selected from the group consisting of ##STR34## and R.sup.11, R.sup.12 and R.sup.13 each represents hydrogen or nonmetallic atom, with the proviso that at least one of R.sup.11, R.sup.12 and R.sup.12 is an electrophile having a Hammett's substituent constant .sigma.p value in the range of 0.3 to 0.78.

### Claim 5 (depends on 4)

A dye as claimed in claim 4, wherein the sum of Hammett's substituent constant .sigma.p values of R.sup.11, R.sup.12 and R.sup.13 is from 1.0 to 2.50.

### Claim 6

A heat transfer dye proving material comprising a support having thereon a dye providing layer containing a heat migrating dye, said dye providing layer comprising at lest one azomethine dye represented by the following formula (I), (II) or (III): ##STR35## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each independently represents hydrogen or nonmetallic atom; X represents --OH or --NR.sup.5 R.sup.6 ; R.sup.5 and R.sup.6 each independently represents hydrogen, alkyl, aryl or heterocyclic, wherein the heterocyclic is selected from the group consisting of ##STR36## and R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, R.sup.12 and R.sup.13 each independently represents hydrogen or nonmetallic atom.

### Claim 7 (depends on 1)

The azomethine dye according to claim 1, wherein at least one of R.sup.1 and R.sup.2 ; R.sup.2 and R.sup.5 ; R.sup.5 and R.sup.6 ; R.sup.6 and R.sup.3 ; R.sup.3 and R.sup.4 ; R.sup.7 and R.sup.8 ; R.sup.9 and R.sup.10 ; R.sup.11 and R.sup.12 ; and R.sup.12 and R.sup.13 are bonded to each other to form a ring.

### Claim 8 (depends on 2)

The azomethine dye according to claim 2, wherein at least one of R.sup.1 and R.sup.2 ; R.sup.2 and R.sup.5 ; R.sup.5 and R.sup.6 ; R.sup.6 and R.sup.3 ; R.sup.3 and R.sup.4 ; R.sup.7 and R.sup.8 ; and R.sup.9 and R.sup.10 are bonded to each other to form a ring.

### Claim 9 (depends on 3)

The near infrared absorbing azomethine dye according to claim 3, wherein at least one of R.sup.1 and R.sup.2 ; R.sup.2 and R.sup.5 ; R.sup.5 and R.sup.6 ; R.sup.6 and R.sup.3 ; R.sup.3 and R.sup.4 ; R.sup.7 and R.sup.8 ; and R.sup.9 and R.sup.10 are bonded to each other to form a ring.

### Claim 10 (depends on 4)

The azomethine dye according to claim 4, wherein at least one of R.sup.1 and R.sup.2 ; R.sup.2 and R.sup.5 ; R.sup.5 and R.sup.6 ; R.sup.6 and R.sup.3 ; R.sup.3 and R.sup.4 ; R.sup.11 and R.sup.12 ; and R.sup.12 and R.sup.13 are bonded to each other to form a ring.

### Claim 11 (depends on 6)

The heat transfer dye proving material according to claim 6, wherein at least one of R.sup.1 and R.sup.2 ; R.sup.2 and R.sup.5 ; R.sup.5 and R.sup.6 ; R.sup.6 and R.sup.3 ; R.sup.3 and R.sup.4 ; R.sup.7 and R.sup.8 ; R.sup.9 and R.sup.10 ; R.sup.11 and R.sup.12 ; and R.sup.12 and R.sup.13 are bonded to each other to form a ring.