PROCESS FOR PREPARING 9-ARYLOXYCARBOCYANINE COMPOUNDS
First Claim
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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.
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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.
4 Citations
24 Claims
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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.
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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.
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4. A process in accordance with claim 1 wherein the reaction is carried out at the reflux temperature of the reaction mixture.
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5. A process in accordance with claim 2 wherein the reaction is carried out at the reflux temperature of the reaction mixture.
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6. A process in accordance with claim 3 wherein the reaction is carried out at the reflux temperature of the reaction mixture.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
- 4'"'"''"'"',5'"'"''"'"'-dibenzothiacarbocyanine ethylsulfate which comprises reacting 3,3'"'"''"'"'-diethyl-9-ethylthio-4,5;
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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.
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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.
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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.
- 4'"'"''"'"',5'"'"''"'"'-dibenzothiacarbocyanine p-toluenesulfonate which comprises reacting 3,3'"'"''"'"'-dimethyl-9-methylthio4,5;
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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.
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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.
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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.
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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.
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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.
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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.
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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.
Specification