Infrared absorbing N-alkylsulfate cyanine compounds
View Patent ↗Infrared absorbing N-alkylsulfate cyanine compounds and imageable compositions containing the compounds are disclosed. The compounds have the structure I: in which: R is hydrogen, or R is one or more alkyl, substituted or unsubstituted aralkyl, alkoxy, carboxyl, nitro, cyano, trifluoromethyl, acyl, alkyl sulfonyl, aryl sulfonyl, or halogen groups, or R is the atoms necessary to form a substituted or unsubstituted benzo group; A is (CH 2 ) n ; where n is 1–5; preferably 2–4; Y is O, S, NR′, or C(R′) 2 , where R′ is hydrogen or alkyl; preferably methyl; Z is hydrogen, halogen, alkyl, substituted or unsubstituted aralkyl; substituted or unsubstituted aroxyl, substituted or unsubstituted thioaroxyl, or substituted or unsubstituted diphenylamino; m is zero or one; and X is a cation, preferably sodium, potassium, lithium, ammonium, or substituted ammonium.
1. An imageable composition comprising a binder that is a negatively-charged sulfated polymer and an infrared absorbing cyanine compound having the structure:
in which:
R is hydrogen, or R is one or more alkyl, substituted or unsubstituted aralkyl, alkoxy, carboxyl, nitro, cyano, trifluoromethyl, acyl, alkyl sulfonyl, aryl sulfonyl, or halogen groups, or R is the atoms necessary to form a substituted or unsubstituted benzo group;
A is (CH 2 ) n ; where n is 1–5;
Y is C(R′) 2 , where R′ is hydrogen or alkyl;
Z is hydrogen, halogen, alkyl, substituted or unsubstituted aralkyl; substituted or unsubstituted aryloxy, substituted or unsubstituted thioaryloxy, or substituted or unsubstituted diphenylamino;
m is zero or one; and
X is a cation.
2. The composition of claim 1 in which Y is C(CH 3 ) 2 .
3. The composition of claim 2 in which Z is chloro, phenoxyl, thiophenoxyl, or diphenylamino.
4. The composition of claim 3 in which R is hydrogen.
5. The composition of claim 1 in which n is 2, 3, or 4.
6. The composition of claim 1 in which Z is chloro.
7. The composition of claim 1 in which R represents the atoms necessary to form an unsubstituted benzo group.
8. The composition of claim 1 in which X is sodium, potassium, lithium, ammonium, or substituted animonium containing one to sixteen carbon atoms.
9. The composition of claim 1 wherein said sulfated polymer is a sulfated novolac or sulfated addition copolymer.
10. An imageable composition comprising a binder that is a negatively-charged sulfated polymer and an infrared absorbing cyanine compound having the structure:
in which:
R is hydrogen, or R is one or more alkyl, substituted or unsubstituted aralkyl, alkoxy, carboxyl, nitro, cyano, trifluoromethyl, acyl, alkyl sulfonyl, aryl sulfonyl, or halogen groups, or R is the atoms necessary to form a substituted or unsubstituted benzo group;
A is (CH 2 ) n ; where n is 1–5;
Y is O, S, or NR′, where R′ is hydrogen or alkyl;
Z is hydrogen, halogen, alkyl, substituted or unsubstituted aralkyl; substituted or unsubstituted aryloxy, substituted or unsubstituted thioaryloxy, or substituted or unsubstituted diphenylamino;
m is zero or one; and
X is a cation.
11. The composition of claim 10 in which Y is O or NCH 3 .
12. The composition of claim 11 in which Z is chloro, phenoxyl, thiophenoxyl, or diphenylamino.
13. The composition of claim 12 in which R is hydrogen.
14. The composition of claim 10 in which Y is S.
15. The composition of claim 14 in which Z is chloro, phenoxy, thiophenoxy, or diphenylamino.
16. The composition of claim 15 in which R is hydrogen.
17. The composition of claim 16 in which n is 2, 3, or 4.