Method of making dihydroperimidine squaraine compounds

A method to make squaraine dyes involves the reaction of 1,8-diaminonaphthalene with 1,3-dihydroxyacetone dimer in a first reaction mixture comprising the appropriate solvents to prepare a first intermediate. This first intermediate is then reacted with an organic acylating agent in the presence of...

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Bibliographic Details
Main Authors RAMSDEN WILLIAM D, VALENTE LOUIS F, BERNARD LORI S
Format Patent
LanguageEnglish
Published 19.02.2002
Edition7
Subjects
ADHESIVES
CHEMISTRY
DYES
HETEROCYCLIC COMPOUNDS
LAKES
METALLURGY
MISCELLANEOUS APPLICATIONS OF MATERIALS
MISCELLANEOUS COMPOSITIONS
MORDANTS
NATURAL RESINS
ORGANIC CHEMISTRY
ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES
PAINTS
POLISHES
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Summary:A method to make squaraine dyes involves the reaction of 1,8-diaminonaphthalene with 1,3-dihydroxyacetone dimer in a first reaction mixture comprising the appropriate solvents to prepare a first intermediate. This first intermediate is then reacted with an organic acylating agent in the presence of a suitable solvent to form a second intermediate. Lastly, after isolation, the second intermediate is reacted with squaric acid in a particular hydroxylic solvent/nonpolar solvent mixture that dissolves squaric acid and forms a ternary azeotrope with water and the water is at least partially removed. The resulting dyes have the following general structure wherein R is an organic radical derived from the organic acylating agent.
Bibliography:Application Number: US20000666234