Thermal recording materials
View Patent ↗A thermal recording material having a heat-sensitive color-forming layer that contains a phosphate modifier in addition to an activator and lueco dye can provide good imaging. The phosphate modifier such as unsubstituted dibenzyl phosphate can be paired with an activator such 3-(4-hydroxyphenyl)propionic acid to provide an environmentally friendly thermal recording material.
1. A thermal recording material, which comprises a substrate having provided thereon a heat-sensitive color-forming layer; said color-forming layer comprising a binder having dispersed therein, and in a substantially contiguous relationship, a leuco dye, an activator, and a phosphate modifier; wherein said phosphate modifier is selected from one or more compounds of Formula I:
wherein each R is independently selected from an alkyl group or an alkoxy group; and n is an integer from 0 to 3.
2. The thermal recording material according to claim 1 , wherein R is selected from a C1-C6 alkyl group or a C1-C6 alkoxy group.
3. The thermal recording material according to claim 1 , wherein n is 0.
4. The thermal recording material according to claim 1 , wherein said activator is selected from the group consisting of benzoic acid, 3,4-dihydroxyphenyl acetic acid, citric acid, salicylic acid, ascorbic acid, and tryptophan.
5. The thermal recording material according to claim 1 , wherein said activator is one or more compounds of formula II:
wherein R 1 is hydroxyl or an alkoxy group; R 2 is hydrogen, hydroxyl, or amino; R 3 is a C1 to C4 hydrocarbon linking group; and m is an integer of 1 to 3.
6. The thermal recording material according to claim 5 , wherein R 3 is methylene.
7. The thermal recording material according to claim 1 , wherein R 1 is hydroxyl and m is 1.
8. The thermal recording material according to claim 7 , wherein said activator is 3-(4-hydroxyphenyl)propionic acid.
9. The thermal recording material according to claim 8 , wherein said phosphate modifier is a compound of formula I wherein n is 0.
10. The thermal recording material according to claim 1 , wherein the weight ratio of said activator to said leuco dye is within the range of about 0.5:1 to 10:1.
11. The thermal recording material according to claim 1 , wherein the weight ratio of said phosphate modifier to said leuco dye is within the range of about 0.5:1 to 10:1.
12. The thermal recording material according to claim 1 , wherein said heat-sensitive color-forming layer is a single coated layer.
13. The thermal recording material according to claim 1 , wherein said heat-sensitive color-forming layer is comprised of two sub-layers; a first sub-layer containing said leuco dye and a second sub-layer containing said activator and said phosphate modifier.
14. The thermal recording material according to claim 1 , wherein said leuco dye is substantially colorless prior to reacting with said activator.
15. The thermal recording material according to claim 1 , wherein said leuco dye is an electron-donating dye precursor selected from the group consisting of phthalides, leucoauramines, fluorans, spirodipyrans, pyridines, and pyrazines.
16. The thermal recording material according to claim 1 , wherein said leuco dye is selected from the group consisting of (3,3-bis(4-dimethylaminophenyl)-6-dimethylaminophthalide; 3-diethylamino-6-methyl-7-anilino-flouran; 3-dibutylamino-6-methyl-7-anilino-fluoran; 3-dibutylamino-7-(2-chloroanilino) fluoran; 3-(N-ethyl-N-tetrahydrofurfurylamino)-6-methyl-7-3,5′6-tris(dimethylamino)spiro[9H-fluorene-9,1′(3′H)-isobenzofuran]-3′-one; 7-(1-ethyl-2-methylindole-3-yl)-7-(4-diethylamino-2-ethoxyphenyl)-5,7-dihydrofuro[3,4-b]pyridin-5-one; 3-diethylamino-7-(2-chloroanilino)fluoran; 3-(N-methylcyclohexylamino)-6-methyl-7-anilinofluoran; 7-(1-octyl-2-methylindole-3-yl)-7-(4-diethylamino-2-ethoxyphenyl)-5,7-dihydrofuro[3,4-b]pyridin-5-one; 3-diethylamino-7,8-benzofluoran; 3,3-bis(1-ethyl-2-methylindole-3-yl)phthalide; 3-diethylamino-7-anilinofluoran; 3-diethylamino-7-benzylaminofluoran; 3′-phenyl-7-dibenzylamino-2,2′-spirodi-[2H-1-benzopyran]; and mixtures of two or more thereof.
17. The thermal recording material according to claim 1 , wherein said binder comprises polyvinyl alcohol.
18. The thermal recording material according to claim 17 , wherein said binder further comprises styrene-butadiene.
19. The thermal recording material according to claim 1 , which further comprises at least one additive selected from the group consisting of pigments, waxes, lubricants, wetting agents, defoamers, and anti-oxidants.
20. A thermal recording material, which comprises a substrate having provided thereon a heat-sensitive color-forming layer that comprises a leuco dye, 3-(4-hydroxyphenyl)propionic acid and dibenzyl phosphate dispersed in a binder and in substantially contiguous relationship.