Claims
- 1. A process of forming thiazine-indigo compounds of formula (I) (cis-isomers) and of formula (II) (trans-isomers) whereinR1 and R2 independently represent the atoms necessary to complete the formation of a substituted or unsubstituted aromatic or aliphatic carbocyclic or heterocyclic ring system, and R3 is hydrogen, C1-12alkyl or phenyl, comprising reacting in the presence of an aqueous system comprising water or water and a further component selected from the group consisting of acidic catalysts and basic catalysts; compounds of formulae (IIIa) and (IIIb) whereinR4 and R′4 independently are H or a metallic ion selected from Na+, K+, or Zn2+with a compound of formula (IV) (bans isomers) or (V) (cis-isomers) whereinHal is Cl or Br, both R5 independently are a leaving group commonly used in substitution reactions at carbonyl carbon atoms.
- 2. The process according to claim 1 wherein R5 is selected from the group consisting of Cl, C1-5alkoxy, and OH.
- 3. The process according to claim 1 wherein the acidic catalyst is a carboxylic acid or an inorganic acid or salts thereof.
- 4. The process according to claim 2 wherein the carboxylic acid is acetic acid.
- 5. The process according to claim 2 wherein the inorganic acid is sulphuric or hydrochloric acid or phosphoric acid.
- 6. The process according to claim 1, wherein the basic catalyst is selected from the group consisting of sodium hydroxide, potassium hydroxide and triethylamine.
- 7. The process according to claim 1, wherein the aqueous system consists of 0 to 95% by weight of an acidic catalyst and 95 to 5% by weight of water.
- 8. The process according to claim 7, wherein the aqueous system consists of 10% by weight of an acidic catalyst and 90% by weight of water.
- 9. The process according to claim 1, wherein the molar ratio of the compounds (IIIa) to (IIIb) to (IV) or (V) is 1:1:1.
- 10. The process of converting a cis-thiazine indigo compound of formula (I) according to claim 1 into the trans-thiazine-indigo pigment of formula (II) according to claim 1 by thermal treatment in an inert polar solvent, optionally in the presence of an acidic catalyst wherein the solvent is selected from the group consisting of dimethylformamide, dimethylacetamide and N-methylpyrrolidone (NMP).
- 11. The process according to claim 10, wherein the thermal treatment comprises temperatures of from 100 to 250° C.
- 12. The process according to claim 11, wherein the thermal treatment comprises temperatures of from 100 to 180° C.
- 13. The process according to claim 12, wherein the thermal treatment comprises temperatures of from 130 to 160° C.
- 14. The process according to claim 10, wherein the acidic catalyst is a carboxylic acid.
- 15. The process according to claim 14, wherein the carboxylic acid is acetic acid.
- 16. The process according to claim 10, wherein the acidic catalyst is selected from the group consisting of trifluoromethane sulfonic acid and para-toluene sulfonic acid.
- 17. The process according to claim 10, wherein the inert polar solvent is selected from the group consisting of chlorobenzene, nitrobenzene, dimethylformamide, dimethylacetamide, N-methylpyrrolidone, ethylene glycol and dipropylene glycol methyl ether.
Priority Claims (1)
Number |
Date |
Country |
Kind |
9806220 |
Mar 1998 |
GB |
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CROSS-REFERENCE TO RELATED APPLICATIONS
This application is a continuation of U.S. application Ser. No. 09/275,533, filed on Mar. 24, 1999.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
3803139 |
Kaul |
Apr 1974 |
A |
Foreign Referenced Citations (1)
Number |
Date |
Country |
1 358 574 |
Jul 1974 |
GB |
Non-Patent Literature Citations (1)
Entry |
Article, “Studies on Heterocyclic Colouring Matters” by B.L. Kaul, Helvetica Chemica Acta, vol. 57 (8), 1974, pp. 2264-2678. |
Continuations (1)
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Number |
Date |
Country |
Parent |
09/275533 |
Mar 1999 |
US |
Child |
09/620271 |
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US |