Thermally-transferable fluorescent europium complexes

• US 5,006,503 A
• Filed: 03/13/1990
• Issued: 04/09/1991
• Est. Priority Date: 03/13/1990
• Status: Expired due to Term

• Current Assignee: Eastman Kodak Company
• Original Assignee: Eastman Kodak Company
• Inventors: Byers, Gary W., Chapman, Derek D.
• Primary Examiner(s): Hess, Bruce H.
• Application Number:
  US07/493,076
• Time in Patent Office: 392 Days
• Field of Search: 8/471, 428/195, 428/480, 428/913, 428/914, 428/690, 503/227
• US Class Current: 503/227
• CPC Class Codes: B41M 3/144 using fluorescent, luminescent or iridescent effects
• CPC Class Codes: B41M 5/392 Additives, other than colour forming substances, dyes or pigments, e.g. sensitisers, transfer promoting agents
• 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: Y10T 428/31786 Of polyester [e.g., alkyd, etc.]

Abstract

A donor element for thermal transfer comprising a support having on one side thereof a fluorescent europium complex dispersed in a polymeric binder. In a preferred embodiment, the complex has the formula: ##STR1## wherein: D is a substituted or unsubstituted, aromatic, 5- or 6-membered carbocyclic or heterocyclic moiety; and

J is --CF₃, --CH₃, --CH₂ F or --CHF₂.

In another preferred embodiment, the europium atom may also have attached thereto at least one monodentate ligand with an electron-donating oxygen or nitrogen atom or at least one bidentate ligand with two electron-donating oxygen, nitrogen or sulfur atoms atoms capable of forming a 5- or 6-membered ring with the europium atom.

Claims

1. A donor element for thermal transfer comprising a support having on one side thereof a fluorescent europium complex dispersed in a polymeric binder, said complex having the formula:

##STR41## wherein;

D is a substituted or unsubstituted, aromatic, 5- or 6-membered carbocyclic or heterocyclic moiety; and

J is --CF₃, --CH₃, --CH₂ F or --CHF₂.

2. The element of claim 1 wherein D represents phenyl, 2-thienyl, 2-furyl or 3-pyridyl.

3. The element of claim 1 wherein said complex has the formula:

##STR42## wherein;

D is a substituted or unsubstituted, aromatic, 5- or 6-membered carbocyclic or heterocyclic moiety;

J is --CF₃, --CH₃, --CH₂ F or --CHF₂ ; and

B represents at least one monodentate ligand with an electron-donating oxygen or nitrogen atom or at least one bidentate ligand with two electron-donating oxygen, nitrogen or sulfur atoms capable of forming a 5- or 6-membered ring with the europium atom.

4. The element of claim 3 wherein B represents tri-n-octylphosphine oxide, pyridine-N-oxide or triphenylphosphine oxide.

5. The element of claim 3 wherein B represents 2,2'"'"'-bipyridine, 1,10-phenanthroline, ethylene diamine or 1,2-diaminobutane.

6. The element of claim 3 wherein D represents phenyl, 2-thienyl, 2-furyl or 3-pyridyl.

7. The element of claim 1 wherein said donor element comprises sequential repeating areas of magenta, yellow and cyan dye, and said fluorescent complex.

8. In a process of forming a transfer image comprising imagewise-heating a donor element comprising a support having on one side thereof a layer comprising a material dispersed in a polymeric binder, and transferring an image to a receiving element to form said transfer image, the improvement wherein said material is a fluorescent europium complex, said complex having the formula:

##STR43## wherein;

D is a substituted or unsubstituted, aromatic, 5- or 6-membered carbocyclic or heterocyclic moiety; and

J is --CF₃, --CH₃, --CH₂ F or --CHF₂.

9. The process of claim 8 wherein said complex has the formula:

##STR44## wherein;

D is a substituted or unsubstituted, aromatic, 5- or 6-membered carbocyclic or heterocyclic moiety;

J is --CF₃, --CH₃, --CH₂ F or --CHF₂ ; and

B represents at least one monodentate ligand with an electron-donating oxygen or nitrogen atom or at least one bidentate ligand with two electron-donating oxygen, nitrogen or sulfur atoms capable of forming a 5- or 6-membered ring with the europium atom.

10. The process of claim 8 wherein said support is poly(ethylene terephthalate) which is coated with sequential repeating areas of magenta, yellow and cyan dye, and said fluorescent complex, and said process steps are sequentially performed for each color to obtain a visible three-color dye transfer image and a fluorescent image.

11. In a thermal transfer assemblage comprising:

(a) a donor element comprising a support having on one side thereof a layer comprising a material dispersed in a polymeric binder, and

(b) a receiving element comprising a support having thereon an image-receiving layer,

said receiving element being in a superposed relationship with said donor element so that said material layer is in contact with said image-receiving layer, the improvement wherein said material is a fluorescent europium complex, said complex having the formula;

##STR45## wherein;

D is a substituted or unsubstituted, aromatic, 5- or 6-membered carbocyclic or heterocyclic moiety; and

J is --CF₃, --CH₃, --CH₂ F or --CHF₂.

12. The assemblage of claim 11 wherein D represents phenyl, 2-thienyl, 2-furyl or 3-pyridyl.

13. The assemblage of claim 11 wherein said complex has the formula:

##STR46## wherein;

D is a substituted or unsubstituted, aromatic, 5- or 6-membered carbocyclic or heterocyclic moiety;

J is --CF₃, --CH₃, --CH₂ F or --CHF₂ ; and

B represents at least one monodentate ligand with an electron-donating oxygen or nitrogen atom or at least one bidentate ligand with two electron-donating oxygen, nitrogen or sulfur atoms capable of forming a 5- or 6-membered ring with the europium atom.

14. The assemblage of claim 13 wherein B represents tri-n-octylphosphine oxide, pyridine-N-oxide or triphenylphosphine oxide.

15. The assemblage of claim 13 wherein B represents 2,2'"'"'-bipyridine, 1,10-phenanthroline, ethylene diamine or 1,2-diaminobutane.

16. The assemblage of claim 13 wherein D represents phenyl, 2-thienyl, 2-furyl or 3-pyridyl.

17. The assemblage of claim 11 wherein said support of said donor element is poly(ethylene terephthalate) which is coated with sequential repeating areas of magenta, yellow and cyan dye, and said fluorescent complex.