Thermal imaging members and methods
View Patent ↗There are described thermal imaging members and thermal imaging methods utilizing unsymmetrical rhodamine compounds. The rhodamine color-forming compounds exhibit a first color when in a crystalline form and a second color, different from the first color, when in an amorphous form.
1. A thermal imaging member comprising a substrate carrying an image-forming layer comprising a compound represented by the formula
wherein:
R 1 , R 4 , R 5 , R 6 , R 7 , and R 8 are each independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, heterocycloalkyl, substituted heterocycloalkyl alkoxy, substituted alkoxy, substituted carbonyl, acylamino, halogen, aryl, substituted aryl, heteroaryl and substituted heteroaryl;
R 2 is a 2-alkylphenyl group;
R 3 is hydrogen;
R 9 is absent or selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, heterocycloalkyl, substituted heterocycloalkyl, alkoxy, substituted alkoxy, substituted carbonyl, halogen, aryl, substituted aryl, heteroaryl, substituted heteroaryl, amino, substituted amino, alkylamino, substituted alkylamino, arylamino and substituted arylamino;
R 10 , R 11 and R 12 are each independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, heterocycloalkyl, substituted heterocycloalkyl, alkoxy, substituted alkoxy, substituted carbonyl, halogen, aryl, substituted aryl, heteroaryl, substituted heteroaryl, amino, substituted amino, alkylamino, substituted alkylamino, arylamino and substituted arylamino;
R 13 is selected from the group consisting of alkyl, substituted alkyl, alkenyl, substituted alkenyl, heterocycloalkyl and substituted heterocycloalkyl;
R 14 is selected from the group consisting of alkyl, substituted alkyl, alkenyl, substituted alkenyl, heterocycloalkyl and substituted heterocycloalkyl;
R 15 , R 16 , R 17 and R 18 are each independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, heterocycloalkyl, substituted heterocycloalkyl, alkoxy, substituted alkoxy, substituted carbonyl, halogen, aryl, substituted aryl, heteroaryl, substituted heteroaryl, amino, substituted amino, alkylamino, substituted alkylamino, arylamino and substituted arylamino; and
X 1 is carbon or nitrogen;
wherein said compound is colorless in the crystalline form and magenta colored in the amorphous form.
2. The thermal imaging member as defined in claim 1 wherein said compound represented by formula I has a glass transition temperature of at least 50° C.
3. The thermal imaging member as defined in claim 1 wherein said image-forming layer further comprises at least one thermal solvent.
4. The thermal imaging member as defined in claim 3 wherein said thermal solvent is selected from the group consisting of diphenylsulfone, 4,4′-dimethyldiphenylsulfone, phenyl p-tolylsulfone, 4,4′-dichlorodiphenylsulfone, and mixtures thereof.
5. The thermal imaging member as defined in claim 1 wherein said image-forming layer further comprises at least one compound comprising a phenolic grouping.
6. The thermal imaging member as defined in claim 5 wherein said compound comprising a phenolic grouping is selected from the group consisting of 2,2′-methylenebis(6-tert-butyl-4-methylphenol), 2,2′-methylenebis(6-tert-Butyl-4-Ethyl-Phenol), 2,2′-ethylidenebis(4,6-di-tert-butylphenol), bis[2-hydroxy-5-methyl-3-(1-methylcyclohexyl)phenyl]-methane, 1,3,5-tris(2,6-dimethyl-3-hydroxy-4-tert-butylbenzyl)isocyanurate, 2,6-bis[[3-(1,1-dimethylethyl)-2-hydroxy-5-methylphenyl]methyl]-4-methyl-phenol, 2,6-butylidenebis[6-(1,1-dimethylethyl)-4-methyl-phenol, trimethylhexylidene)bis[4,6-dimethyl-phenol], 2,2′-methylenebis[4,6-bis(1,1-dimethylethyl)-phenol, 2,2′-(2-methylpropylidene)bis[4,6-dimethyl-phenol], 1,1,3-tris(2-methyl-4-hydroxy-5-t-butylphenyl)butane, tris(3,5-di-t-butyl-4-hydroxybenzyl)isocyanurate, 2,2′-thiobis(4-tert-octylphenol), and 3-tert-butyl-4-hydroxy-5-methylphenyl sulfide.
7. A thermal imaging method comprising
(a) providing an imaging member as defined in claim 1 ; and
(b) converting at least a portion of said compound to an amorphous form in an image-wise pattern
whereby an image is formed.
8. The thermal imaging method as defined in claim 7 wherein step (b) comprises applying an image-wise pattern of thermal energy to said imaging member, said thermal energy being sufficient to convert at least some of said compound to an amorphous form.
9. The thermal imaging member as defined in claim 1 wherein X 1 is carbon.
10. A thermal imaging member comprising a substrate carrying an image-forming layer comprising:
a) a compound represented by the formula
wherein:
R 1 , R 3 , R 4 -R 12 , and R 15 -R 18 are hydrogen;
R 2 is a 2-alkylaryl group;
R 13 is an alkyl group comprising at least two carbon atoms;
R 14 is an alkyl group; and
X 1 is carbon; and
b) a developer selected from the group consisting of 2,2′-methylenebis(6-tert-butyl-4-methylphenol), 2,2′-methylenebis(6-tert-butyl-4-ethyl-phenol), 2,2′-ethylidenebis(4,6-di-tert-butylphenol), bis[2-hydroxy-5-methyl-3-(1-methylcyclohexyl)phenyl]-methane, 2,6-bis[[3-(1,1-dimethylethyl)-2-hydroxy-5-methylphenyl]methyl]-4-methyl-phenol, 2,2′-butylidenebis[6-(1,1-dimethylethyl)-4-methyl-phenol, 2,2′-(3,5,5-trimethylhexylidene)bis[4,6-dimethyl-phenol], 2,2′-methylenebis[4,6-bis(1,1-dimethylethyl-phenol, 2,2′-(2-methylpropylidene)bis[4,6-dimethyl-phenol], 1,1,3-tris(2-methyl-4-hydroxy-5-t-butylphenyl)butane, tris(3,5-di-t-butyl-4-hydroxybenzyl)isocyanurate, 2,2′-thiobis(4-tert-octylphenol), and 3-tert-butyl-4-hydroxy-5-methylphenyl sulfide,
wherein said compound is colorless in the crystalline foam and magenta colored in the amorphous form.
11. The thermal imaging member of claim 10 , further comprising a stabilizer comprising 1,3,5-tris(2,6-dimethyl-3-hydroxy-4-tert-butylbenzyl)isocyanurate.