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Methine dye synthesis
| Details |
Inventors: Frishberg, Mark D.;
Assignee: Eastman Kodak Company (Rochester, NY)
Primary Examiner: Randolph; John D.
Assistant Examiner:
Attorney, Agent or Firm: Spurrell; Donald W., Reece, III; Daniel B.
A process for the preparation of a disperse methine dye containing at least one dicyanomethylidene group comprising the steps of (A) preparing an anhydrous solution of an aldehyde formed by contacting an aromatic amine, 1,2,3,4-tetrahydroquinoline or benzomorpholine compound capable of undergoing the Vilsmeier-Haack reaction with POCl.sub.3 and a N,N-di-alkylformamide wherein the alkyl moiety is 1-4 carbon atoms; (B) subsequently adding to said solution at least one equivalent of cyanoacetamide based on the equivalents of aldehyde formed in (A), thereby forming a reaction mixture of aldehyde and in situ generated malononitrile; and (C) adjusting the pH of the solution to a point sufficient for the condensation of the aldehyde and in situ generated malononitrile to occur thereby producing a disperse methine dye. |
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DETAILED DESCRIPTION I claim: 1.
Process for the preparation of a disperse methine dye containing at least one dicyanomethylidene group comprising the steps of (A) preparing an anhydrous solution of an aldehyde formed by contacting an aromatic amine, 1,2,3,4-tetrahydroquinoline or benzomorpholine compound capable of undergoing the Vilsmeier-Haack reaction with POCl.
sub.
3 and a dialkylformamide wherein the alkyl moiety is 1-4 carbon atoms; (B) subsequently adding to said solution at about 15.
degree.
C.
to about 40.
degree.
C.
, at least one equivalent of cyanoacetamide based on the equivalents of aldehyde formed in (A), thereby forming a reaction mixture of aldehyde and in situ generated malonitrile; and (C) adjusting the pH of the solution to a point sufficient for the condensation of the aldehyde and in situ generated malononitrile to occur thereby producing a disperse methine dye.
2.
Process of claim 1 wherein the aldehyde is formed from an aromatic amine.
3.
Process of claim 1 wherein the aldehyde is formed from a 1,2,3,4-tetrahydroquinoline compound.
4.
Process of claim 1 wherein the aldehyde is formed from a benzomorpholine compound.
5.
Process of claim 1 wherein the dialkylformamide is dimethylformamide.
6.
Process of claim 2 wherein the dialkylformamide is dimethylformamide.
7.
Process of claim 3 wherein the dialkylformamide is dimethylformamide.
8.
Process of claim 4 wherein the dialkylformamide is dimethylformamide.
Description:
This invention relates to a novel process for making methine dyes containing a dicyanomethylidene group.
This process involves the dehydration of cyanoacetamide to malononitrile with a dialkylamide and phosphorous oxychloride in the presence of an aldehyde (the term "aldehyde" as used throughout this specification and claims to describe the invention includes Vilsmeier adduct complex), prepared from an aromatic amine, 1,2,3,4-tetra-hydroquinoline or benzomorpholine compound capable of undergoing the Vilsmeier-Haack reaction, followed by a pH adjustment sufficient to allow the reaction of methine dye formation
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