PROCESS FOR PREPARING 9-ARYLOXYCARBOCYANINE COMPOUNDS

• US 3,725,398 A
• Filed: 04/21/1971
• Issued: 04/03/1973
• Est. Priority Date: 04/21/1971
• Status: Expired due to Term

• Current Assignee: Frank G. Webster, Robert C. Taber
• Original Assignee: Frank G. Webster, Robert C. Taber
• Inventors: Webster, Frank G., Taber, Robert C.
• Primary Examiner(s): Randolph, John D.
• Application Number:
  US05/136,177
• Time in Patent Office: 713 Days
• Field of Search: 260/240.6,240.65
• US Class Current: 548/121
• CPC Class Codes: C09B 23/0025 the substituent being bound through an oxygen atom
• CPC Class Codes: G03C 1/18 with three CH groups
• CPC Class Codes: Y10S 430/127 Spectral sensitizer containing

Abstract

Process for preparing 9-aryloxycarbocyanine dye compounds which comprises reacting a 9-alkylthiocarbocyanine dye compound in the presence of a basic medium with a phenol. The 9aryloxycarbocyanine dye compounds obtained are useful for the spectral sensitization of silver halide photographic emulsions.

Claims

2. A process in accordance with claim 1 wherein the molar proportion of the phenol is about 20 to about 75 times that of the 9-alkylthiocarbocyanine compound.

3. A process in accordance with claim 1 wherein the molar proportion of the phenol is about 30 to 55 times that of the 9-alkylthiocarbocyanine compound.

4. A process in accordance with claim 1 wherein the reaction is carried out at the reflux temperature of the reaction mixture.

5. A process in accordance with claim 2 wherein the reaction is carried out at the reflux temperature of the reaction mixture.

6. A process in accordance with claim 3 wherein the reaction is carried out at the reflux temperature of the reaction mixture.

7. A process in accordance with claim 1 wherein the reaction is carried out in a heat conductive reaction vessel in which at least a portion of the reaction vessel which is in contact with the reaction mixture is heated until the external surface temperature thereof is in the range of about 235*C. to about 245*C.

8. A process in accordance with claim 2 wherein the reaction is carried out in a heat conductive reaction vessel in which at least a portion of the reaction vessel which is in contact with the reaction mixture is heated until the external surface temperature thereof is in the range of about 235*C. to about 245*C.

9. A process in accordance with claim 3 wherein the reaction is carried out in a heat conductive reaction vessel in which at least a portion of the reaction vessel which is in contact with the reaction mixture is heated until the external surface temperature thereof is in the range of about 235*C. to about 245*C.

10. A process in accordance with claim 1 for preparing 3,3'"'"''"'"'-diethyl-9-phenoxythiacarbocyanine iodide which comprises reacting 3,3'"'"''"'"'-diethyl-9-ethylthiothiacarbocyanine iodide with a molar excess of phenol in the presence of a basic condensing agent at an elevated temperature.

11. A process in accordance with claim 10 wherein the molar proportion of phenol is about 20 to about 75 times that of the 9-ethylthiothiacarbocyanine compound.

12. A process in accordance with claim 10 wherein the molar proportion of phenol is about 30 to about 55 times that of the 9-ethylthiothiacarbocyanine compound.

13. A process in accordance with claim 1 for preparing 3,3'"'"''"'"'-diethyl-9-phenoxy-4,5;

4'"'"''"'"',5'"'"''"'"'-dibenzothiacarbocyanine ethylsulfate which comprises reacting 3,3'"'"''"'"'-diethyl-9-ethylthio-4,5;

4'"'"''"'"',5'"'"''"'"'-dibenzothiacarbocyanine Ethylsulfate with a molar excess of phenol in the presence of base condensing agent at an elevated temperature.

14. A process in accordance with claim 13 wherein the molar proportion of phenol is about 20 to about 75 times that of the dibenzothiacarbocyanine compound.

15. A process in accordance with claim 13 wherein the molar proportion of phenol is about 30 to about 55 times that of the dibenzothiacarbocyanine compound.

16. A process in accordance with claim 1 for preparing 3,3'"'"''"'"'-dimethyl-9-phenoxy-4,5;

4'"'"''"'"',5'"'"''"'"'-dibenzothiacarbocyanine p-toluenesulfonate which comprises reacting 3,3'"'"''"'"'-dimethyl-9-methylthio4,5;

4'"'"''"'"',5'"'"''"'"'-dibenzothiacarbocyanine p-toluenesulfonate with a molar excess of phenol in the presence of a basic condensing agent at an elevated temperature.

17. A process in accordance with claim 16 wherein the molar proportion of phenol is about 20 to about 75 times that of the dibenzothiacarbocyanine compound.

18. A process in accordance with claim 16 wherein the molar proportion of phenol is about 30 to about 55 times that of the dibenzothiacarbocyanine compound.

19. A process in accordance with claim 1 for preparing 3,3'"'"''"'"'-diethyl-9-phenoxy-4,5-benzothiacarbocyanine iodide which comprises reacting 3,3'"'"''"'"'-diethyl-9-ethylthio-4,5-benzothiacarbocyanine iodide with a molar excess of phenol in the presence of a basic condensing agent at an elevated temperature.

20. A process in accordance with claim 19 wherein the molar proportion of phenol is about 20 to about 75 times that of the benzothiacarbocyanine compound.

21. A process in accordance with claim 19 wherein the molar proportion of phenol is about 30 to about 55 times that of the benzothiacarbocyanine compound.

22. A process in accordance with claim 1 for preparing 3,3'"'"''"'"'-diethyl-9-phenoxyselenathiacarbocyanine iodide which comprises reacting 3,3'"'"''"'"'-diethyl-9-ethylthioselenathiacarbocyanine iodide with a molar excess of phenol in the presence of a basic condensing agent at an elevated temperature.

24. A process in accordance with claim 22 wherein the molar proportion of phenol is about 30 to about 55 times that of the 9-ethylthioselenathiacarbocyanine compound.