IP Library Granted Patent US 9,517,651
Granted Patent B2
US 9,517,651 · App. 14/865,405 · Granted Dec 13, 2016

Developer for thermal recording media and thermal composition media using the same

Inventor: Ronald Q. Ruffer, Jr. (Sinking Spring, PA)
Assignees: Performance Chemicals, Inc.; Marubeni Specialty Chemicals, Inc.
B41M5/3335B41M5/3275B41M5/3336B41M5/3372B41M5/3375B41M5/3377C07C275/36B41M2205/04B41M2205/28
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Quick Facts
Patent No.
US 9,517,651
App. No.
14/865,405
Granted
Dec 13, 2016
Kind
B2
Abstract

The subject invention more specifically discloses compounds which are particularly useful as a developer for thermal recording media. These compounds include p-(p-{3-[p-(p-hydroxyphenoxy)phenyl]ureido}phenoxy)phenol, m-(p-{3-[p-(p-hydroxyphenoxy)phenyl]ureido}phenoxy)phenol, o-(p-{3-[p-(p-hydroxyphenoxy)phenyl]ureido}phenoxy)phenol, p-(p-{3-[m-(p-hydroxyphenoxy)phenyl]ureido}phenoxy)phenol, and p-(m-{3-[o-(p-hydroxyphenoxy)phenyl]ureido}phenoxy)phenol. The present invention also reveals a thermal recording sheet having a thermal recording layer containing a colorless or pale colored dye precursor and a color developer reactable with said dye precursor upon heating to develop a color, wherein said color developer is a compound selected from the group consisting of p-(p-{3-[p-(p-hydroxyphenoxy)phenyl]ureido}phenoxy)phenol, m-(p-{3-[p-(p-hydroxyphenoxy)phenyl]ureido}phenoxy)phenol, o-(p-{3-[p-(p-hydroxyphenoxy)phenyl]ureido}phenoxy)phenol, p-(p-{3-[m-(p-hydroxyphenoxy)phenyl]ureido}phenoxy)phenol, and p-(m-{3-[o-(p-hydroxyphenoxy)phenyl]ureido}phenoxy)phenol.

Claims (34)

1. A compound which is particularly useful as a developer for thermal recording media, said compound being selected from the group consisting of p-(p-{3-[p-(p-hydroxyphenoxy)phenyl]ureido}phenoxy)phenol, m-(p-{3-[p-(p-hydroxyphenoxy)phenyl]ureido}phenoxy)phenol, o-(p-{3-[p-(p-hydroxyphenoxy)phenyl]ureido}phenoxy)phenol, p-(p-{3-[m-(p-hydroxyphenoxy)phenyl]ureido}phenoxy)phenol, and p-(m-{3-[o-(p-hydroxyphenoxy)phenyl]ureido}phenoxy)phenol.

2. The compound of claim 1 wherein said compound is p-(p-{3-[p-(p-hydroxyphenoxy)phenyl]ureido}phenoxy)phenol.

3. The compound of claim 1 wherein said compound is m-(p-{3-[p-(p-hydroxyphenoxy)phenyl]ureido}phenoxy)phenol.

4. The compound of claim 1 wherein said compound is o-(p-{3-[p-(p-hydroxyphenoxy)phenyl]ureido}phenoxy)phenol.

5. The compound of claim 1 wherein said compound is p-(p-{3-[m-(p-hydroxyphenoxy)phenyl]ureido}phenoxy)phenol.

6. The compound of claim 1 wherein said compound is p-(m-{3-[o-(p-hydroxyphenoxy)phenyl]ureido}phenoxy)phenol.

7. A thermal recording sheet having a thermal recording layer containing a colorless or pale colored dye precursor and a color developer reactable with said dye precursor upon heating to develop a color, wherein said color developer is a compound selected from the group consisting of p-(p-{3-[p-(p-hydroxyphenoxy)phenyl]ureido}phenoxy)phenol, m-(p-{3-[p-(p-hydroxyphenoxy)phenyl]ureido}phenoxy)phenol, o-(p-{3-[p-(p-hydroxyphenoxy)phenyl]ureido}phenoxy)phenol, p-(p-{3-[m-(p-hydroxyphenoxy)phenyl]ureido}phenoxy)phenol, and p-(m-{3-[o-(p-hydroxyphenoxy)phenyl]ureido}phenoxy)phenol.

8. The thermal recording sheet of claim 7 which is further comprised of an electron accepting material selected from the group consisting of 2,4′-Dihydroxydiphenylsulfone (CAS#5397-34-2), 4,4′-Dihydroxydiphenylsulfone (CAS#80-90-1), Bis-(3-allyl-4-hydroxyphenyl)sulfone (CAS#41481-66-7), 4-[4′-[(1′-methylethyloxy)phenyl]sulfonyl]phenol (CAS#191680-83-8), 4-hydroxyphenyl 4-isoprooxyphenylsulfone (CAS#95235-30-6), N-(p-Toluenesulfonyl)-N′-(3-p-toluenesulfonyloxyphenyl)urea (CAS#232938-43-1), Phenol, 4-[[4-(2-propen-1yloxy)phenyl]sulfonyl (CAS#97042-18-7), 4-Hydroxy-4′benzyloxydiphenylsulfone (CAS#63134-33-8), and 4,4′bis(N-carbamoyl-4-methylbenzenesulfonamide)diphenylmethane (CAS#151882-81-4).

9. The thermal recording sheet of claim 7 wherein the colorless or pale colored dye precursor is selected from the group consisting of 2-anilino-3-methyl-6-diethylaminofluorane, 2-anilino-3-methyl-6-dibutylaminofluorane, 2-anilino-3-methyl-6-(N-ethyl-N-isoamylamino)fluorine, 2-anilino-3-methyl-6-(N-ethyl-N-propylamino)fluorane, 2-anilino-3-methyl-6-di-n-amylaminofluorane, 2-anilino-3-methyl-6-(N-ethyl-N-p-tolylamino)fluorane, 2-anilino-3-methyl-6-N-ethyl-N-sec-butylaminofluorane, 3-di-(n-pentylamino)-6-methyl-7-anilinofluorane, 3-(N-isoamyl-N-ethylamino)-6-methyl-7-anilinofluorane, 3-(N-n-hexyl-N-ethylamino)-6-methyl-7-anilinofluorane, 3-[N-(3-ethoxypropyl)-N-ethylamino]-6-methyl-7-anilinofluorane, 3-di-(n-butylamino)-7-2-chloroanilino)fluorane, 3-diethylamino-7-(2-chloroanilino)fluorane, and 3-(N-cyclohexyl-N-methylamino)-6-methyl-7-anilinofluorane.

10. The thermal recording sheet of claim 7 which is further comprised of a sensitizer.

11. The thermal recording sheet of claim 10 wherein the sensitizer is selected from the group consisting of stearamide, N-hydroxymethylstearamide, N-stearylstearamide, ethylenebisstearamide, N-stearylstearamide, ethylenebisstearamide, N-stearylurea, benzyl-2-naphthyl ether, m-terpphenyl, 4-benzylbiphenyl, 4-acetylbiphenyl, 4-(4-methylphenoxy)biphenyl, 1,2-bis(3-methylphenoxy) ethane, 1,2-diphenoxyethane, 2,2′-bis(4-methoxyphenoxy)diethyl ether, diphenoxyxylene, bis(4-methoxyphenyl)ether, diphenyl adipate, dibenzyl oxalate, di(4-methylbenzyl)oxalate, di(4-chlorobenzyl)oxalate, dimethyl terephthalate, dibenzyl terephthalate, phenyl benzene sulfonic ester, diphenylsulfone, bis(4-allyloxyphenyl) sulfone, 4-acetylacetophenone, acetoacetic acid anilides, and fatty acid aniliides.

12. The thermal recording medium of claim 7 which is further comprised of a sensitizer.

13. The thermal recording sheet of claim 12 wherein the sensitizer is selected from the group consisting of stearamide, N-hydroxymethylstearamide, N-stearylstearamide, ethylenebisstearamide, N-stearylstearamide, ethylenebisstearamide, N-stearylurea, benzyl-2-naphthyl ether, m-terpphenyl, 4-benzylbiphenyl, 4-acetylbiphenyl, 4-(4-methylphenoxy)biphenyl, 1,2-bis(3-methylphenoxy) ethane, 1,2-diphenoxyethane, 2,2′-bis(4-methoxyphenoxy)diethyl ether, diphenoxyxylene, bis(4-methoxyphenyl)ether, diphenyl adipate, dibenzyl oxalate, di(4-methylbenzyl)oxalate, di(4-chlorobenzyl)oxalate, dimethyl terephthalate, dibenzyl terephthalate, phenyl benzene sulfonic ester, diphenylsulfone, bis(4-allyloxyphenyl) sulfone, 4-acetylacetophenone, acetoacetic acid anilides, and fatty acid anilides.

14. The thermal recording sheet of claim 7 which is further comprised of a binder.

15. The thermal recording sheet as specified in claim 14 wherein the binder is a polyvinyl alcohol.

16. The thermal recording sheet as specified in claim 14 wherein the binder is selected from the group consisting of acrylic emulsions, styrene copolymer emulsions, butadiene copolymer emulsions, acrylonitrile copolymers and terpolymer emulsions, polyvinyl acetate emulsions, vinyl acetate ethylene emulsions, polyurethane emulsions, starches, and hydroxymethyl cellulose.

17. The thermal recording sheet of claim 7 which is further comprised of a filler.

18. The thermal recording sheet of claim 17 wherein the filler is selected from the group consisting of titanium dioxide, silica, aluminum tri-hydrate, clay, mica, calcium carbonate, talc, magnesium hydroxide, magnesium oxide, hollow plastic spheres, and polystyrene.

19. The thermal recording sheet of claim 7 which is further comprised of a slip agent.

20. The thermal recording sheet of claim 19 wherein the slip agent is selected from the group consisting of zinc stearate, calcium stearate, stearamide, and polyethylene wax.

21. The thermal recording sheet of claim 7 which is further comprised of a UV absorber.

22. The thermal recording sheet of claim 7 which is further comprised of an optical brightener.

23. A thermal recording medium which is comprised of a substrate having thereon a recording layer containing a colorless or pale colored dye precursor and a color developer reactable with said dye precursor upon heating to develop a color, wherein said color developer is a compound selected from the group consisting of p-(p-{3-[p-(p-hydroxyphenoxy)phenyl]ureido}phenoxy)phenol, m-(p-{3-[p-(p-hydroxyphenoxy)phenyl]ureido}phenoxy)phenol, o-(p-{3-[p-(p-hydroxyphenoxy)phenyl]ureido}phenoxy)phenol, p-(p-{3-[m-(p-hydroxyphenoxy)phenyl]ureido}phenoxy)phenol, and p-(m-{3-[o-(p-hydroxyphenoxy)phenyl]ureido}phenoxy)phenol.

24. The thermal recording medium of claim 23 which is further comprised of an electron accepting material selected from the group consisting of 2,4′-Dihydroxydiphenylsulfone (CAS#5397-34-2), 4,4′-Dihydroxydiphenylsulfone (CAS#80-90-1), Bis-(3-allyl-4-hydroxyphenyl)sulfone (CAS#41481-66-7), 4-[4′-[(1′-methylethyloxy)phenyl]sulfonyl]phenol (CAS#191680-83-8), 4-hydroxyphenyl 4-isoprooxyphenylsulfone (CAS#95235-30-6), N-(p-Toluenesulfonyl)-N′-(3-p-toluenesulfonyloxyphenyl)urea (CAS#232938-43-1), Phenol, 4-[[4-(2-propen-1yloxy)phenyl]sulfonyl (CAS#97042-18-7), 4-Hydroxy-4′benzyloxydiphenylsulfone (CAS#63134-33-8), and 4,4′bis(N-carbamoyl-4-methylbenzenesulfonamide)diphenylmethane (CAS#151882-81-4).

25. The thermal recording medium of claim 23 wherein the colorless or pale colored dye precursor is selected from the group consisting of 2-anilino-3-methyl-6-diethylaminofluorane, 2-anilino-3-methyl-6-dibutylaminofluorane, 2-anilino-3-methyl-6-(N-ethyl-N-isoamylamino)fluorine, 2-anilino-3-methyl-6-(N-ethyl-N-propylamino)fluorane, 2-anilino-3-methyl-6-di-n-amylaminofluorane, 2-anilino-3-methyl-6-(N-ethyl-N-p-tolylamino)fluorane, 2-anilino-3-methyl-6-N-ethyl-N-sec-butylaminofluorane, 3-di-(n-pentylamino)-6-methyl-7-anilinofluorane, 3-(N-isoamyl-N-ethylamino)-6-methyl-7-anilinofluorane, 3-(N-n-hexyl-N-ethylamino)-6-methyl-7-anilinofluorane, 3-[N-(3-ethoxypropyl)-N-ethylamino]-6-methyl-7-anilinofluorane, 3-di-(n-butylamino)-7-2-chloroanilino)fluorane, 3-diethylamino-7-(2-chloroanilino)fluorane, and 3-(N-cyclohexyl-N-methylamino)-6-methyl-7-anilinofluorane.

26. The thermal recording medium of claim 23 which is further comprised of a binder.

27. The thermal recording medium as specified in claim 26 wherein the binder is a polyvinyl alcohol.

28. The thermal recording medium as specified in claim 27 wherein the binder is selected from the group consisting of acrylic emulsions, styrene copolymer emulsions, butadiene copolymer emulsions, acrylonitrile copolymers and terpolymer emulsions, polyvinyl acetate emulsions, vinyl acetate ethylene emulsions, polyurethane emulsions, starches, and hydroxymethyl cellulose.

29. The thermal recording medium of claim 23 which is further comprised of a filler.

30. The thermal recording sheet of claim 29 wherein the filler is selected from the group consisting of titanium dioxide, silica, aluminum tri-hydrate, clay, mica, calcium carbonate, talc, magnesium hydroxide, magnesium oxide, hollow plastic spheres, and polystyrene.

31. The thermal recording medium of claim 23 which is further comprised of a slip agent.

32. The thermal recording medium of claim 31 wherein the slip agent is selected from the group consisting of zinc stearate, calcium stearate, stearamide, and polyethylene wax.

33. The thermal recording medium of claim 23 which is further comprised of a UV absorber.

34. The thermal recording medium of claim 23 which is further comprised of an optical brightener.

Assignments (2)
MERGER Recorded Aug 13, 2020
From: MARUBENI SPECIALTY CHEMICALS, INC.
To: MARUBENI AMERICA CORPORATION
Reel/Frame 053487/0613 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 26, 2016
From: RUFFER, RONALD Q.
To: PERFORMANCE CHEMICALS, INC.; MARUBENI SPECIALTY CHEMICALS, INC.
Reel/Frame 040138/0035 →
Continuity (2)
Provisional Application 62055932 · Sep 26, 2015
Related Publication 20160089919A1 · Mar 31, 2016