Process for the preparation of thiazine-indigo compounds and of new intermediates therefor
AssigneeClariant Finance (BVI) Limited
InventorsTill Borchert, Bansi Lal Kaul, Bruno Piastra, Valérie Wolf
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Abstract
New heterocyclic compounds are disclosed which are used as intermediates for the preparation of trans-thiazine-indigo pigments which are in part new compounds and can be used for the mass pigmentation of organic substrates. Also disclosed are different environmentally friendly water-based processes for the preparation of the new heterocyclic compounds and the corresponding pigments.
Claims12
A process for the preparation of thiazine-indigo compounds according to the formula (Va) resp. (Vb), (VIa) resp. (VIb), (VIIa) resp. (VIb) and (VIIIa) resp. (VIIb)
- wherein R1 represents the atoms necessary to complete the formation of a substituted or unsubstituted aromatic or alicyclic or heterocyclic ring system, wherein the heterocyclic ring system is a 6-membered N-heteroaromatic ring with one or two N atoms, optionally bearing a fused benzene ring or a benzene ring bearing a fused 5- or 6-membered N-heterocyclic ring with two N atoms;
- R3 is hydrogen, C1-12alkyl or phenyl;
- R6, R′6, R7 and R′7 are independently an hydrogen, alkyl or aryl group
- comprising the step of reacting in the presence of an aqueous system a compound of formula (IXa) and/or (IXb)
- or a compound of formula (Xa) and/or (Xb)
- wherein R4 and R′4 independently are H or a metallic ion selected from Na+, K+ or Zn2+
- or a compound of formulae (IXa) or (Xa) and a compound of formula (IIb)
- with a compound of formula (IIIa) (cis-isomers) or (IIIb) (trans-isomers)
- wherein Hal is Cl or Br and R5 is a leaving group commonly used in substitution reactions at carbonyl carbon atoms, e.g. Cl or C1-5alkoxy or OH.
Thiazine-indigo compounds according to the formula (Va) resp. (Vb), (VIa) resp. (VIb), (VIIa) resp. (VIb) and (VIIIa) resp. (VIIb)
- wherein R1 represents the atoms necessary to complete the formation of a substituted or unsubstituted aromatic or alicyclic or heterocyclic ring system, wherein the heterocyclic ring system is a 6-membered N-heteroaromatic ring with one or two N atoms, optionally bearing a fused benzene ring or a benzene ring bearing a fused 5- or 6-membered N-heterocyclic ring with two N atoms;
- R3 is hydrogen, C1-12alkyl or phenyl;
- R6, R′6, R7 and R′7 are independently an hydrogen, alkyl or aryl group.
Cis-thiazine-indigo compounds according to the formula (XI)
- and trans-thiazine-indigo pigments according to the formula (XII)
- in which formulae R8 and R9 are independently H, C1-8alkyl, phenyl, naphthyl, C5-10cycloalkyl or
Dependencies are inferred from the claim text.