# US 5,326,666 A · Dye-donor element for use in thermal dye sublimation transfer

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- Number: US 5,326,666 A
- Document ID: US5326666A
- Status: Granted
- Kind: A
- Application number: 08/040,610
- Filed: 1993-03-31
- Granted: 1994-07-05
- Earliest claimed: 1992-04-21
- Assignees: Agfa-Gevaert
- Inventors: Luc Vanmaele; Wilhelmus Janssens
- Web page: https://patentgrep.com/patent/US5326666A

## CPC

- B41M 5/465: {Infrared radiation-absorbing materials, e.g. dyes, metals, silicates, C black}
- B41M 5/39: Dyes containing one or more carbon-to-nitrogen double bonds, e.g. azomethine
- C09B 53/02: Indamines; Indophenols
- Y10S 430/145: Infrared
- Y10S 430/165: Thermal imaging composition
- 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)
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

Dye-donor element for use according to thermal dye sublimation transfer, said dye-donor element comprising a support provided with a dye layer containing a dye dispersed in a polymeric binder, characterized in that said dye corresponds to the following formula (I) ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 independently represent hydrogen, halogen, nitro, an alkyl group, a cycloalkyl group, an aryl group, an alkoxy group, an aryloxy group, a alkylthio group, a arylthio group, an acylamino group, a sulfamoyl group, a carbamoyl group, which groups may be substituted, or R.sup.2 and R.sup.3 together can form a saturated or aromatic or heterocyclic ring fused-on the cyclohexadiene ring, which ring may be substituted; B represents ##STR2## wherein R.sup.4 -R.sup.11 are defined in the specification; K represents ##STR3## wherein: R.sup.12 and R.sup.13 (independently) represent hydrogen, an alkyl group, an aryl group, a heterocyclic group, which groups may be substituted, or R.sup.12 and R.sup.13 together represent the necessary atoms to close a heterocyclic ring, which ring may be substituted, or R.sup.12 and/or R.sup.13 together with R.sup.14 and/or R.sup.17 represent the necessary atoms to close a ring fused-on the benzene ring, which ring may be substituted; R.sup.14, R.sup.15, R.sup.16 and R.sup.17 are defined in the specification.

## Claims

### Claim 1

Dye-donor element for use according to thermal dye sublimation transfer, said dye-donor element comprising a support provided with a dye layer containing a dye dispersed in a polymeric binder, characterized in that said dye corresponds to the following formula (I) ##STR17## wherein R.sup.1, R.sup.2 and R.sup.3 independently represent hydrogen, an alkyl group, a cycloalkyl group, an aryl group, an alkoxy group, an aryloxy group, a alkylthio group, a arylthio group, an acylamino group, a sulfamoyl group, a carbamoyl group, which groups may be substituted, or R.sup.2 and R.sup.3 together can form a saturated or aromatic or heterocyclic ring fused-on the cyclohexadiene ring, which ring may be substituted;
B represents ##STR18## wherein R.sup.4 represents hydrogen, an alkyl group, a cycloalkyl group, an aryl group, which groups may be substituted, SO.sub.2 R.sup.10, COR.sup.10, POR.sup.10 R.sup.11 ;
R.sup.5 represents hydrogen, halogen, nitro, cyano, an alkyl group, an aryl group, an alkoxy group, an alkylthio group, which groups may be substituted;
R.sup.6 and R.sup.6' independently represent an alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an aryl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an amino group or a heterocyclic group, which groups may be substituted, or R.sup.6 and R.sup.6' together form a 5- or 6-membered ring, which ring may be substituted;
R.sup.7 represents an alkyl group, an aryl group, a cycloalkyl group, which groups may be substituted;
R.sup.8 and R.sup.9 independently represent hydrogen, an alkyl group, an aryl group, a cycloalkyl group, which groups may be substituted, or R.sup.8 and R.sup.9 together can form a heterocyclic ring, which ring may be substituted;
R.sup.10 and R.sup.11 independently represent an alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an aryl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an amino group or a heterocyclic group, which groups may be substituted, or R.sup.10 and R.sup.11 together form a 5- or 6-membered ring, which ring may be substituted;
K represents ##STR19## wherein: R.sup.12 and R.sup.13 independently represent hydrogen, an alkyl group, an aryl group, a heterocyclic group, which groups may be substituted, or R.sup.12 and R.sup.13 together represent the necessary atoms to close a heterocyclic ring, which ring may be substituted, or R.sup.12 and/or R.sup.13 together with R.sup.14 and/or R.sup.17 represent the necessary atoms to close a ring fused-on the benzene ring, which ring may be substituted;
R.sup.14, R.sup.15, R.sup.16 and R.sup.17 independently represent hydrogen, hydroxy, halogen, an alkyl group, a cycloalkyl group, an aryl group, an alkyloxy group, an aryloxy group, a carbamoyl group, a sulfamoyl group, which groups may be substituted, NH-SO.sub.2 R.sup.18, NH-COR.sup.18, O-SO.sub.2 R.sup.18, O-COR.sup.18, or R.sup.14 and R.sup.15 together and/or R.sup.16 and R.sup.17 together represent the necessary atoms to close (a) ring(s) fused-on the benzene ring or R.sup.14 and/or R.sup.17 together with R.sup.12 and/or R.sup.13 represent the necessary atoms to close a heterocyclic ring fused-on the benzene ring, which groups may be substituted;
R.sup.18 represents an alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an aryl group, an alkyloxy group, an aryloxy group, an alkylthio group, an arylthio group, an amino group, a heterocyclic group, which groups may be substituted.

### Claim 2 (depends on 1)

Dye-donor element according to claim 1, wherein R.sup.1 represents hydrogen, R.sup.2 represents hydrogen or an alkyl group or an alkylcarbamoyl group, R.sup.3 represents hydrogen or halogen, R.sup.4 represents an alkyl group, R.sup.5 represents hydrogen, R.sup.6 and R.sup.6' both represent an alkoxy group, R.sup.7 represents an alkyl group, R.sup.8 and R.sup.9 together represent the necessary atoms to form a 6-membered ring, R.sup.12 and R.sup.13 both represent an alkyl group, R.sup.14 represents hydrogen, R.sup.15 represents hydrogen or an alkyl group, R.sup.16 represents hydrogen or an alkyl group and R.sup.17 represents hydrogen.

### Claim 3 (depends on 1)

Dye-donor element according to claim 1, wherein the dye has an absorption maximum above 700 nm.

### Claim 4 (depends on 1)

Dye-donor element according to claim 1, wherein the binder is costyrene-acrylonitrile.

### Claim 5 (depends on 1)

Dye-donor element according to claim 1, wherein the support is polyethylene terephthalate.

### Claim 6

Thermal dye sublimation transfer method comprising the step of imagewise heating a dye donor element in face-to-face relation with a receiving element, said donor element comprising a support provided with a dye layer containing a dye dispersed in a polymeric binder, characterized in that said dye corresponds to the following formula (I) ##STR20## wherein R.sup.1, R.sup.2 and R.sup.3 independently represent hydrogen, halogen, nitro, an alkyl group, a cycloalkyl group, an aryl group, an alkoxy group, an aryloxy group, a alkylthio group, a arylthio group, an acylamino group, a sulfamoyl group, a carbamoyl group, which groups may be substituted, or R.sup.2 and R.sup.3 together can form a saturated or aromatic or heterocyclic ring fused-on the cyclohexadiene ring, which ring may be substituted;
B represents ##STR21## wherein R.sup.4 represents hydrogen, an alkyl group, a cycloalkyl group, an aryl group, which groups may be substituted, SO.sub.2 R.sup.10, COR.sup.10, POR.sup.10 R.sup.11 ;
R.sup.5 represents hydrogen, halogen, nitro, cyano, an alkyl group, an aryl group, an alkoxy group, an alkylthio group, which groups may be substituted;
R.sup.6 and R.sup.6' independently represent an alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an aryl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an amino group or a heterocyclic group, which groups may be substituted, or R.sup.6 and R.sup.6' together form a 5- or 6-membered ring, which ring may be substituted;
R.sup.7 represents an alkyl group, an aryl group, a cycloalkyl group, which groups may be substituted;
R.sup.8 and R.sup.9 independently represent hydrogen, an alkyl group, an aryl group, a cycloalkyl group, which groups may be substituted, or R.sup.8 and R.sup.9 together can form a heterocyclic ring, which ring may be substituted;
R.sup.10 and R.sup.11 independently represent an alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an aryl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an amino group or a heterocyclic group, which groups may be substituted, or R.sup.10 and R.sup.11 together form a 5- or 6-membered ring, which ring may be substituted;
K represents ##STR22## wherein: R.sup.12 and R.sup.13 (independently) represent hydrogen, an alkyl group, an aryl group, a heterocyclic group, which groups may be substituted, or R.sup.12 and R.sup.13 together represent the necessary atoms to close a heterocyclic ring, which ring may be substituted, or R.sup.12 and/or R.sup.13 together with R.sup.14 and/or R.sup.17 represent the necessary atoms to close a ring fused-on the benzene ring, which ring may be substituted;
R.sup.14, R.sup.15, R.sup.16 and R.sup.17 (independently) represent hydrogen, hydroxy, halogen, an alkyl group, a cycloalkyl group, an aryl group, an alkyloxy group, an aryloxy group, a carbamoyl group, a sulfamoyl group, which groups may be subsituted, NH--SO.sub.2 R.sup.18, NH--COR.sup.18, O--SO.sub.2 R.sup.18, O--COR.sup.18, or R.sup.14 and R.sup.15 together and/or R.sup.16 and R.sup.17 together represent the necessary atoms to close (a) ring(s) fused-on the benzene ring or R.sup.14 and/or R.sup.17 together with R.sup.12 and/or R.sup.13 represent the necessary atoms to close a heterocyclic ring fused-on the benzene ring, which groups may be substituted;
R.sup.18 represents an alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an aryl group, an alkyloxy group, an aryloxy group, an alkylthio group, an arylthio group, an amino group, a heterocyclic group, which groups may be substituted.

### Claim 7 (depends on 6)

Thermal dye sublimation transfer method according to claim 6, wherein said dye has an absorption maximum above 700 nm.