Magenta dye-donor element used in thermal dye transfer

• US 4,698,651 A
• Filed: 10/27/1986
• Issued: 10/06/1987
• Est. Priority Date: 12/24/1985
• Status: Expired

• Current Assignee: Eastman Kodak Company
• Original Assignee: Eastman Kodak Company
• Inventors: Moore, William H., Lum, Kin K., Weaver, Max A.
• Primary Examiner(s): Hess, Bruce H.
• Application Number:
  US06/923,444
• Time in Patent Office: 344 Days
• Field of Search: 8/470, 8/471, 428/195, 428/207, 428/484, 428/488.1, 428/488.4, 428/913, 428/914, 428/411.1, 428/480, 430/945, 346/227, 427/146, 427/256
• US Class Current: 503/227
• CPC Class Codes: B41M 5/388 Azo dyes
• CPC Class Codes: Y10S 428/913 Material designed to be responsive to temperature, light, moisture
• CPC Class Codes: Y10S 428/914 Transfer or decalcomania
• CPC Class Codes: Y10S 430/146 Laser beam
• CPC Class Codes: Y10T 428/24901 including coloring matter
• CPC Class Codes: Y10T 428/31504 Composite [nonstructural laminate]
• CPC Class Codes: Y10T 428/31786 Of polyester [e.g., alkyd, etc.]

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 R¹ and R² may each independently be hydrogen, alkyl, allyl, cycloalkyl or aryl; or R¹ and R² may be taken together to form a ring; or R¹ or R² may be part of a 5- or 6-membered heterocyclic ring;

R³ 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.

Claims

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 R¹ and R² 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 R¹ and R² may be taken together to form a ring;

or a 5- or 6-membered heterocyclic ring may be formed with R¹ or R², the nitrogen to which R¹ or R² is attached, and either carbon atom ortho to the carbon attached to said nitrogen atom;

R³ 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 R³ is methyl and Q is CN.

3. The element of claim 1 wherein J is --NHCOCH₃.

4. The element of claim 1 wherein R¹ is C₂ H₅ and R² is CH₂ C₆ H₅, cyclohexyl or CH₂ CH₂ O₂ CCH₃.

5. The element of claim 1 wherein R¹ and R² are each n--C₃ H₇ or C₂ H₅.

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 R¹ and R² 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 R¹ and R² may be taken together to form a ring;

or a 5- or 6-membered heterocyclic ring may be formed with R¹ or R², the nitrogen to which R¹ or R² is attached, and either carbon atom ortho to the carbon attached to said nitrogen atom;

R³ 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 R¹ and R² 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 R¹ and R² may be taken together to form a ring;

or a 5- or 6-membered heterocyclic ring may be formed with R¹ or R², the nitrogen to which R¹ or R² is attached, and either carbon atom ortho to the carbon attached to said nitrogen atom;

R³ 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 R³ is methyl and Q is CN.

14. The assemblage of claim 12 wherein J is --NHCOCH₃.

15. The assemblage of claim 12 wherein R¹ is C₂ H₅ and R² is CH₂ C₆ H₅, cyclohexyl or CH₂ CH₂ O₂ CCH₃.

16. The assemblage of claim 12 wherein R¹ and R² are each n--C₃ H₇ or C₂ H₅.

17. The assemblage of claim 12 wherein said support of the dye-donor element comprises poly(ethylene terephthalate).