Magenta dye-donor element used in thermal dye transfer

Abstract

A magenta dye-donor element for thermal dye transfer comprises a support having thereon a magenta dye dispersed in a polymeric binder, the magenta dye comprising a substituted 5-arylazoisothiazole. In a preferred embodiment, the magenta dye has the formula ##STR1## wherein R 1 and R 2 may each independently be hydrogen, alkyl, allyl, cycloalkyl or aryl; or R 1 and R 2 may be taken together to form a ring; or R 1 or R 2 may be part of a 5- or 6-membered heterocyclic ring; R 3 may be hydrogen, alkyl, aryl, alkylthio or halogen; J may be alkyl, aryl or NHA, where A is an acyl or sulfonyl radical; and Q may be cyano, thiocyanato, alkylthio or alkoxycarbonyl.

What is claimed is: 
     
       1. A magenta dye-donor element for thermal dye transfer comprising a support having thereon a dye layer comprising a magenta dye dispersed in a polymeric binder, said magenta dye having the formula: ##STR31## wherein R 1  and R 2  may each independently be hydrogen, substituted or unsubstituted alkyl or allyl of from 1 to about 6 carbon atoms, substituted or unsubstituted cycloalkyl of from about 5 to about 7 carbon atoms, substituted or unsubstituted aryl of from about 5 to about 10 carbon atoms; or R 1  and R 2  may be taken together to form a ring; or a 5- or 6-membered heterocyclic ring may be formed with R 1  or R 2 , the nitrogen to which R 1  or R 2  is attached, and either carbon atom ortho to the carbon attached to said nitrogen atom; R 3  may be hydrogen, substituted or unsubstituted alkyl of from 1 to about 6 carbon atoms, substituted or unsubstituted aryl of from about 5 to about 10 carbon atoms, alkylthio or halogen;   J may be substituted or unsubstituted alkyl of from 1 to about 6 carbon atoms, substituted or unsubstituted aryl of from about 5 to about 10 carbon atoms or NHA, where A is an acyl or sulfonyl radical; and   Q may be cyano, thicyanato, alkylthio or alkoxycarbonyl.   
     
     
       2. The element of claim 1 wherein R 3  is methyl and Q is CN. 
     
     
       3. The element of claim 1 wherein J is --NHCOCH 3 . 
     
     
       4. The element of claim 1 wherein R 1  is C 2  H 5  and R 2  is CH 2  C 6  H 5 , cyclohexyl or CH 2  CH 2  O 2  CCH 3 . 
     
     
       5. The element of claim 1 wherein R 1  and R 2  are each n--C 3  H 7  or C 2  H 5 . 
     
     
       6. The element of claim 1 wherein a dye-barrier layer is located between said dye layer and said support. 
     
     
       7. The element of claim 1 wherein the side of the support opposite the side bearing said dye layer is coated with a slipping layer comprising a lubricating material. 
     
     
       8. The element of claim 1 wherein said support comprises poly(ethylene terephthalate). 
     
     
       9. The element of claim 1 wherein said dye layer comprises sequential repeating areas of cyan, yellow and said magenta dye. 
     
     
       10. In a process of forming a magenta dye transfer image comprising imagewise-heating a dye-donor element comprising a support bearing a dye layer comprising a magenta dye dispersed in a polymeric binder and transferring a magenta dye image to a dye-receiving element to form said magenta dye transfer image, the improvement wherein said magenta dye comprises a substituted 5-arylazoisothiazole having the formula: ##STR32## wherein R 1  and R 2  may each independently be hydrogen, substituted or unsubstituted alkyl or allyl of from 1 to about 6 carbon atoms, substituted or unsubstituted cycloalkyl of from about 5 to about 7 carbon atoms, substituted or unsubstituted aryl of from about 5 to about 10 carbon atoms; or R 1  and R 2  may be taken together to form a ring; or a 5- or 6-membered heterocyclic ring may be formed with R 1  or R 2 , the nitrogen to which R 1  or R 2  is attached, and either carbon atom ortho to the carbon attached to said nitrogen atom; R 3  may be hydrogen, substituted or unsubstituted alkyl of from 1 to about 6 carbon atoms, substituted or unsubstituted aryl of from about 5 to about 10 carbon atoms, alkylthio or halogen;   J may be substituted or unsubstituted alkyl of from 1 to about 6 carbon atoms, substituted or unsubstituted aryl of from about 5 to about 10 carbon atoms or NHA, where A is an acyl or sulfonyl radical; and   Q may be cyano, thiocyanato, alkylthio or alkoxycarbonyl.   
     
     
       11. The process of claim 10 wherein said support is poly(ethylene terephthalate) which is coated with sequential repeating areas of cyan, yellow and said magenta dye, and said process steps are sequentially performed for each color to obtain a three-color dye transfer image. 
     
     
       12. In a thermal dye transfer assemblage comprising: (a) a magenta dye-donor element comprising a support having thereon a dye layer comprising a magenta dye dispersed in a polymeric binder, and   (b) a dye receiving element comprising a support having thereon a dye image-receiving layer, said dye-receiving element being in a superposed relationship with said magenta dye-donor element so that said dye layer is in contact with said dye image-receiving layer, the improvement wherein said magenta dye has the formula: ##STR33## wherein R 1  and R 2  may each independently be hydrogen, substituted or unsubstituted alkyl or allyl of from 1 to about 6 carbon atoms, substituted or unsubstituted cycloalkyl of from about 5 to about 7 carbon atoms, substituted or unsubstituted aryl of from about 5 to about 10 carbon atoms; or R 1  and R 2  may be taken together to form a ring; or a 5- or 6-membered heterocyclic ring may be formed with R 1  or R 2 , the nitrogen to which R 1  or R 2  is attached, and either carbon atom ortho to the carbon attached to said nitrogen atom;     R 3  may be hydrogen, substituted or unsubstituted alkyl of from 1 to about 6 carbon atoms, substituted or unsubstituted aryl of from about 5 to about 10 carbon atoms, alkylthio or halogen;   J may be substituted or unsubstituted alkyl of from 1 to about 6 carbon atoms, substituted or unsubstituted aryl of from about 5 to about 10 carbon atoms or NHA, where A is an acyl or sulfonyl radical; and   Q may be cyano, thiocyanato, alkylthio or alkoxycarbonyl.   
     
     
       13. The assemblage of claim 12 wherein R 3  is methyl and Q is CN. 
     
     
       14. The assemblage of claim 12 wherein J is --NH--COCH 3 . 
     
     
       15. The assemblage of claim 12 wherein R 1  is C 2  H 5  and R 2  is CH 2  C 6  H 5 , cyclohexyl or CH 2  CH 2  O 2  CCH 3 . 
     
     
       16. The assemblage of claim 12 wherein R 1  and R 2  are each n--C 3  H 7  or C 2  H 5 . 
     
     
       17. The assemblage of claim 12 wherein said support of the dye-donor element comprises poly(ethylene terephthalate). .Iadd. 
     
     
       18.  A thermal transfer printing sheet comprising a support having thereon a dye layer comprising a magenta azo dye dispersed in a polymeric binder, said magenta azo dye having the formula:   A--N═N--E     wherein:   A is isothiazol-5-yl substituted in the 3-position by hydrogen, substituted or unsubstituted alkyl of from 1 to about 6 carbon atoms, substituted or unsubstituted aryl of from about 5 to about 10 carbon atoms, alkylthio or halogen, and substituted in the 4-position by cyano, thiocyanato, alkylthio or alkoxycarbonyl; and   E is a group of the formula: ##STR34## wherein J may be substituted or unsubstituted alkyl of from 1 to about 6 carbon atoms, substituted or unsubstited aryl of from about 5 to about 10 carbon atoms or NHA, where A is an acyl or sulfonyl radical; and R 1  and R 2  may each independently be hydrogen; substituted or unsubstituted alkyl or allyl of from 1 to about 6 carbon atoms; substituted or unsubstituted cycloalkyl of from about 5 to about 7 carbon atoms, substituted or unsubstituted aryl of from about 5 to about 10 carbon atoms; or R 1  and R 2  may be taken together to form a ring; or a 5- or 6-membered heterocyclic ring may be formed with R 1  or R 2 , the nitrogen to which R 1  or R 2  is attached, and either carbon atom ortho to the carbon attached to said nitrogen atom. .Iaddend. .Iadd.     
     
     
       19.  A thermal transfer printing sheet according to claim 18 wherein A is selected from 4-cyanoisothiazol-5-yl and 3-methyl-4-cyanoisothiazol-5-yl. .Iaddend. .Iadd.20. A transfer printing sheet according to claim 18 wherein the azo dye conforms to the formula: ##STR35## wherein A is selected from 4-cyanoisothiazol-5-yl and 3-methyl-4-cyanoisothiazol-5-yl; J is selected from unsubstituted alkyl of from 1 to about 6 carbon atoms and NHA, where A is an acyl radical; and   R 1  and R 2  are each independently selected from hydrogen; unsubstituted alkyl of from 1 to about 6 carbon atoms; or alkyl of from 1 to about 6 carbon atoms substituted by a group selected from alkoxy,   
     
     
        acyloxy, cyano and halogen. .Iaddend. .Iadd.21.  A transfer printing process which comprises contacting a transfer sheet coated with a dye according to claim 18 with a receiver sheet, so that the dye is adjacent to the receiver sheet, and selectively heating areas of the transfer sheet to a temperature from 250°-400° C. for a period of from 0.5 to 8.3 msec whereby dye in the heated areas of the transfer sheet may be selectively transferred to the receiver sheet. .Iaddend. .Iadd.22. A thermal transfer printing sheet comprising a support having thereon a dye layer comprising a magenta azo dye dispersed in a polymeric binder, said magenta azo dye having the formula:   A--N═N--E     wherein:   A is isothiazol-5-yl substituted in the 3-position by hydrogen, halogen or substituted alkyl of from 1 to about 6 carbon atoms, and substituted in the 4-position by cyano, thiocyanato or alkoxycarbonyl; and   E is a group of the formula: ##STR36## wherein J may be unsubstituted alkyl of from 1 to about 6 carbon atoms or NHA, where A is an acyl radical; and   R 1  and R 2  may each independently be hydrogen; unsubstituted alkyl of from 1 to about 6 carbon atoms; or alkyl of from 1 to about 6 carbon atoms substituted by a group selected from aryl, halogen, cyano, alkoxy or   
     
     
        acyloxy. .Iaddend. .Iadd.23.  A thermal transfer printing sheet comprising a support having thereon a dye layer comprising a magenta azo dye dispersed in a polymeric binder, said magenta azo dye having the formula:   A--N═N--E     wherein:   A is isothiazol-5-yl substituted in the 3-position by hydrogen, halogen or substituted or unsubstituted alkyl of from 1 to about 6 carbon atoms, and substituted in the 4-position by cyano, thiocyanato or alkoxycarbonyl; and   E is a group of the formula: ##STR37## wherein J may be unsubstituted alkyl of from 1 to about 6 carbon atoms or NHA, where A is an acyl radical; and   R 1  and R 2  may each independently be hydrogen; unsubstituted alkyl of from 1 to about 6 carbon atoms; or alkyl of from 1 to about 6 carbon atoms substituted by a group selected from aryl, halogen, cyano, alkoxy or   
     
     
        acyloxy. .Iaddend. .Iadd.24.  A thermal transfer printing sheet comprising a support having thereon a dye layer comprising a magenta azo dye dispersed in a polymeric binder, said magenta azo dye having the formula:   A--N═N--E     wherein:   A is isothiazol-5-yl substituted in the 3-position by hydrogen, substituted or unsubstituted alkyl of from 1 to about 6 carbon atoms, substituted or unsubstituted aryl of from about 5 to about 10 carbon atoms, alkylthio or halogen, and substituted in the 4-position by cyano, thiocyanato, alkylthio or alkoxycarbonyl; and   E is a group of the formula: ##STR38## wherein   J may be substituted or unsubstituted alkyl of from 1 to about 6 carbon atoms, substituted or unsubstituted aryl of from about 5 to about 10 carbon atoms or NHA, where A is an acyl or sulfonyl radical; and   R 1  and R 2  may each independently be hydrogen; unsubstituted alkyl or allyl of from 1 to about 6 carbon atoms; alkyl or allyl of from 1 to about 6 carbon atoms substituted by a group selected from hydroxy, acyloxy, alkoxy, aryl, cyano, acylamido, or halogen; substituted or unsubstituted cycloalkyl of from about 5 to about 7 carbon atoms, substituted or unsubstituted aryl of from about 5 to about 10 carbon atoms; or R 1  and R 2  may be taken together to form a ring; or a 5- or 6-membered heterocyclic ring may be formed with R 1  or R 2 , the nitrogen to which R 1  or R 2  is attached, and either carbon atom ortho to the carbon attached to said nitrogen atom. .Iaddend.   
     
     
        .Iadd.  .  A thermal transfer printing sheet comprising a substrate having a coating comprising at least one azo dye of the formula:   A--N═N--E     wherein:   A is isothiazol-5-yl substituted in the 3-position by hydrogen, substituted or unsubstituted alkyl of from 1 to about 6 carbon atoms, substituted or unsubstituted aryl of from about 5 to about 10 carbon atoms, alkylthio or halogen, and substituted in the 4-position by cyano, thiocyanato, alkylthio or alkoxycarbonyl; and   E is a group of the formula: ##STR39## wherein J may be substituted or unsubstituted alkyl of from 1 to about 6 carbon atoms, substituted or unsubstituted aryl of from about 5 to about 10 carbon atoms or NHA, where A is an acyl or sulfonyl radical; and   R 1  and R 2  may each independently be hydrogen; substituted or unsubstituted alkyl or allyl of from 1 to about 6 carbon atoms; substituted or unsubstituted cycloalkyl of from about 5 to about 7 carbon atoms, substituted or unsubstituted aryl of from about 5 to about 10 carbon atoms; or R 1  and R 2  may be taken together to form a ring; or a 5- or 6-membered heterocyclic ring may be formed with R 1  or R 2 , the nitrogen to which R 1  or R 2  is attached to said   
     
     
        nitrogen atom. .Iaddend. .Iadd.26.  A thermal transfer printing sheet according to claim 25 wherein A is selected from 4-cyanoisothiazol-5-yl and 3-methyl-4-cyanoisothiazol-5-yl. .Iadd.27. A transfer printing sheet according to claim 25 wherein the azo dye conforms to the formula: ##STR40## wherein is selected from 4-cyanoisothiazol-5-yl and 3-methyl-4-cyanoisothiazol-5-yl; J is selected from unsubstituted alkyl of from 1 to about 6 carbon atoms and NHA, where A is an acyl radical; and   R 1  and R 2  are each independently selected from hydrogen-unsubstituted alkyl of from 1 to about 6 carbon atoms; or alkyl of from 1 to about 6 carbon atoms substituted by a group selected from   
     
     
        alkoxy, acyloxy, cyano and halogen. .Iaddend. .Iadd.28.  A transfer printing process which comprises contacting a transfer sheet coated with a dye according to claim 25 with a receiver sheet, so that the dye is adjacent to the receiver sheet, and selectively heating areas of the transfer sheet to a temperature from 250°-400° C. for a period of from 0.5 to 8.3 msec whereby dye in the heated areas of the transfer sheet may be selectively transferred to the receiver sheet. .Iaddend. .Iadd.29. A thermal transfer printing sheet comprising a substrate having a coating comprising at least one azo dye of the formula:   A--N═N--E     wherein:   A is isothiazol-5-yl substituted in the 3-position by hydrogen, halogen or substituted alkyl of from 1 to about 6 carbon atoms, and substituted in the 4-position by cyano, thiocyanato or alkoxycarbonyl; and   E is a group of the formula: ##STR41## wherein J may be unsubstituted alkyl of from 1 to about 6 carbon atoms or NHA, where A is an acyl radical; and   R 1  and R 2  may each independently by hydrogen; unsubstituted alkyl of from 1 to about 6 carbon atoms; or alkyl of from 1 to about 6 carbon atoms substituted by a group selected from aryl, halogen, cyano, alkoxy or   
     
     
        acyloxy. .Iaddend. .Iadd.30.  A thermal transfer printing sheet comprising a substrate having a coating comprising at least one azo dye of the formula:   A--N═N--E     wherein:   A is isothiazol-5-yl substituted in the 3-position by hydrogen, halogen or substituted or unsubstituted alkyl of from 1 to about 6 carbon atoms, and substituted in the 4-position by cyano, thiocyanato or alkoxycarbonyl; and   E is a group of the formula: ##STR42## wherein J may be unsubstituted alkyl of from 1 to about 6 carbon atoms or NHA, where A is an acyl radical; and   R 1  and R 2  may each independently be hydrogen; unsubstituted alkyl of from 1 to about 6 carbon atoms; or alkyl of from 1 to about 6 carbon atoms substituted by a group selected from aryl, halogen, cyano, alkoxy or   
     
     
        acyloxy. .Iaddend. .Iadd.31.  A thermal transfer printing sheet comprising a substrate having a coating comprising at least one azo dye of the formula:   A--N═N--E     wherein:   A is isothiazol-5-yl substituted in the 3-position by hydrogen, substituted or unsubstituted alkyl of from 1 to about 6 carbon atoms, substituted or unsubstituted aryl of from about 5 to about 10 carbon atoms, alkylthio or halogen, and substituted in the 4-position by cyano, thiocyanato, alkylthio or alkoxycarbonyl; and   E is a group of the formula: ##STR43## wherein J may be substituted or unsubstituted alkyl of from 1 to about 6 carbon atoms, substituted or unsubstituted aryl of from about 5 to about 10 carbon atoms or NHA, where A is an acyl or sulfonyl radical; and   R 1  and R 2  may each independently be hydrogen; unsubstituted alkyl or allyl of from 1 to about 6 carbon atoms; alkyl or allyl of from 1 to about 6 carbon atoms substituted by a group selected from hydroxy, acyloxy, alkoxy, aryl, cyano, acylamido, or halogen; substituted or unsubstituted cycloalkyl of from about 5 to about 7 carbon atoms, substituted or unsubstituted aryl of from about 5 to about 10 carbon atoms; or R 1  and R 2  may be taken together to form a ring; or a 5-or 6-membered heterocyclic ring may be formed with R 1  or R 2 , the nitrogen to which R 1  or R 2  is attached, and either carbon atom ortho to the carbon attached to said nitrogen atom.