# US 5,350,731 A · Thermally transferable fluorine-containing AZO dyes

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 5,350,731 A
- Document ID: US5350731A
- Status: Granted
- Kind: A
- Application number: 08/163,375
- Filed: 1993-12-07
- Granted: 1994-09-27
- Earliest claimed: 1993-12-07
- Assignees: Minnesota Mining and Manufacturing Company
- Inventors: Linda K. Williams; Prakob Kitipichai; Cecil V. Francis; Ramaiah Muthyala
- Web page: https://patentgrep.com/patent/US5350731A

## CPC

- B41M 5/388: Azo dyes
- C09B 29/0003: {from diazotized anilines}
- C09B 29/0813: {substituted by OH, O-C(=X)-R, O-C(=X)-X-R, O-R (X being O,S,NR; R being hydrocarbonyl)}
- C09B 69/106: {containing an azo dye}
- Y10S 428/913: Material designed to be responsive to temperature, light, moisture
- Y10S 428/914: Transfer or decalcomania
- 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

The present invention provides fluorine-containing arylazoanaline dyes that are useful in thermal transfer systems. Specifically, the present invention provides thermal transfer donor sheets containing dyes of the following formula: ##STR1## wherein: R.sup.1 is a (C.sub.1-20)alkyl or hydroxy(C.sub.1-20)alkyl group; R.sup.2 is a hydroxy(C.sub.1-20)alkyl or (C.sub.1-20)alkylene--OC(O)NH--(C.sub.1-20)alkylene--OC(O)--R.sup.4 wherein R.sup.4 is a (C.sub.1-20)alkenyl group or a polymerized alkenyl group; and R.sup.3 is F or CF.sub.3. Useful dyes of this formulation are stable under ambient conditions for at least about 6 months.

## Claims

### Claim 1

A thermal transfer donor sheet comprising a flexible substrate having coated thereon a dye donor layer containing a dye of the formula (Formula I): ##STR17## wherein: (a) R.sup.1 =a (C.sub.1-20)alkyl or hydroxy(C.sub.1-20)alkyl group;
(b) R.sup.2 =a hydroxy(C.sub.1-20)alkyl or (C.sub.1-20)alkylene--OC(O)NH--(C.sub.1-20)alkylene--OC(O)--R.sup.4 wherein R.sup.4 is a (C.sub.2-20)alkenyl group or a polymerized alkenyl group;
(c) R.sup.3 =F or CF.sub.3 ; and
(d) said dye is stable under ambient conditions for at least about 6 months.

### Claim 2 (depends on 1)

The thermal transfer donor sheet of claim 1 wherein the dye donor layer further comprises a binder.

### Claim 3 (depends on 1)

The thermal transfer donor sheet of claim 1 wherein:
(a) R.sup.1 =a (C.sub.2-8)alkyl or hydroxy(C.sub.2-8)alkyl group;
(b) R.sup.2 =a hydroxy(C.sub.2-8)alkyl or (C.sub.2-8)alkylene--OC(O)NH--(C.sub.2-8)alkylene--OC(O)--R.sup.4 wherein R.sup.4 is a (C.sub.2-8)alkenyl group or a polymerized alkenyl group; and
(c) R.sup.3 =F or CF.sub.3.

### Claim 4 (depends on 3)

The thermal transfer donor sheet of claim 3 wherein:
(a) R.sup.1 =a (C.sub.2-4)alkyl or hydroxy(C.sub.2-4)alkyl group;
(b) R.sup.2 =a hydroxy(C.sub.2-4)alkyl or (C.sub.2-4)alkylene--OC(O)NH--(C.sub.2-4)alkylene--OC(O)--R.sup.4 wherein R.sup.4 is --(CH.sub.3)C.dbd.CH.sub.2 or a polymerized --(CH.sub.3)C.dbd.CH.sub.2 group; and
(c) R.sup.3 =F or CF.sub.3.

### Claim 5 (depends on 4)

The thermal transfer donor sheet of claim 4 wherein:
(a) R.sup.1 =--CH.sub.2 CH.sub.3 or --CH.sub.2 CH.sub.2 OH;
(b) R.sup.2 =--CH.sub.2 CH.sub.2 OC(O)NHCH.sub.2 CH.sub.2 OC(O)--R.sup.4 wherein R.sup.4 is --(CH.sub.3)C.dbd.CH.sub.2 or ##STR18## wherein n=2-100.

### Claim 6 (depends on 5)

The thermal transfer donor sheet of claim 5 wherein R.sup.3 =F and n=3-50.

### Claim 7 (depends on 5)

The thermal transfer donor sheet of claim 5 wherein the dye is a compound of the formula: ##STR19##

### Claim 8 (depends on 5)

The thermal transfer donor sheet of claim 5 wherein the dye is a compound of the formula: ##STR20## wherein n=3-10.

### Claim 9 (depends on 3)

The thermal transfer donor sheet of claim 3 wherein the dye is a mixture of ortho, meta, and para isomers of the compound of Formula I wherein:
(a) R.sup.1 =--CH.sub.2 CH.sub.2 OH;
(b) R.sup.2 =--CH.sub.2 CH.sub.2 OH; and
(c) R.sup.3 =CF.sub.3 ;
wherein said dye mixture is stable under ambient conditions for at least about 6 months.

### Claim 10

A process for providing an image by a thermal transfer process comprising:
(a) providing a thermal transfer donor sheet and a thermal transfer receptor sheet in a facing relationship; and
(b) applying heat in an imagewise distributed manner to the donor sheet to cause material on the donor sheet to transfer to the receptor sheet;
wherein the donor sheet comprises a flexible substrate having coated thereon a dye donor layer containing a dye of the formula (Formula I): ##STR21## wherein: (i) R.sup.1 =a (C.sub.1-20)alkyl or hydroxy(C.sub.1-20)alkyl group;
(ii) R.sup.2 =a hydroxy(C.sub.1-20)alkyl or (C.sub.1-20)alkylene--OC(O)NH--(C.sub.1-20)alkylene--OC(O)--R.sup.4 wherein R.sup.4 is a (C.sub.2-20)alkenyl group or a polymerized alkenyl group;
(iii) R.sup.3 =F or CF.sub.3 ; and
(iv) said dye is stable under ambient conditions for at least about 6 months.

### Claim 11 (depends on 10)

The process of claim 10 wherein:
(a) R.sup.1 =a (C.sub.2-8)alkyl or hydroxy(C.sub.2-8)alkyl group;
(b) R.sup.2 =a hydroxy(C.sub.2-8)alkyl or (C.sub.2-8)alkylene--OC(O)NH--(C.sub.2-8)alkylene--OC(O)--R.sup.4 wherein R.sup.4 is a (C.sub.2-8)alkenyl group or a polymerized alkenyl group; and
(c) R.sup.3 =F or CF.sub.3.

### Claim 12 (depends on 11)

The thermal transfer donor sheet of claim 11 wherein:
(a) R.sup.1 =a (C.sub.2-4)alkyl or hydroxy(C.sub.2-4)alkyl group;
(b) R.sup.2 =a hydroxy(C.sub.2-4)alkyl or (C.sub.2-4)alkylene--OC(O)NH--(C.sub.2-4)alkylene--OC(O)--R.sup.4 wherein R.sup.4 is --(CH.sub.3)C.dbd.CH.sub.2 or a polymerized --(CH.sub.3)C.dbd.CH.sub.2 group; an
(c) R.sup.3 =F or CF.sub.3.

### Claim 13 (depends on 12)

The thermal transfer donor sheet of claim 12 wherein:
(a) R.sup.1 =--CH.sub.2 CH.sub.3 or --CH.sub.2 CH.sub.2 OH;
(b) R.sup.2 =--CH.sub.2 CH.sub.2 OC(O)NHCH.sub.2 CH.sub.2 OC(O)--R.sup.4 wherein R.sup.4 is --(CH.sub.3)C.dbd.CH.sub.2 or ##STR22## wherein n=2-100.

### Claim 14 (depends on 13)

The process of claim 13 wherein R.sup.3 is F and n=3-50.

### Claim 15 (depends on 13)

The process of claim 13 wherein the dye is a compound of the formula: ##STR23##

### Claim 16 (depends on 13)

The thermal transfer donor sheet of claim 13 wherein the dye is a compound of the formula: ##STR24## wherein n=3-10.

### Claim 17 (depends on 12)

The process of claim 12 wherein the dye is a mixture of ortho, meta, and para isomers of the compound of Formula I wherein:
(a) R.sup.1 =--CH.sub.2 CH.sub.2 OH;
(b) R.sup.2 =--CH.sub.2 CH.sub.2 OH; and
(c) R.sup.3 =CF.sub.3 ;
wherein said dye mixture is stable under ambient conditions for at least about 6 months.