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US 2003/0061671 A1Published application
Thioxanthone dyes with improved solubility and a method of preparing 2-oxybenzanthrones as intermediate materials for making of these dyes
Assignee3M Innovative Properties Company
InventorsViktor Mihailovich Shershukov, Alexander Nikolayevich Artukhov
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Abstract
The invention relates to new thioxanthone compounds having utility as fluorescent dyes and processes for their manufacture.
Claims17
A compound of the thioxanthone series with improved solubility of the general formula
- 13
- wherein
- R1 is a straight chain alkyl group having from 6 to 22 carbon atoms;
- R2, R3 and R4 are each, independently, hydrogen or alkyl having from 1 to 4 carbon atoms.
1 more element
A compound, being 6-(n-octyloxy)-14H-anthra(2,1,9-mna)thio-xanthene-14-one.
A process for preparing 2-oxybenzanthrone compound of the formula
- 14
- wherein R is hydrogen or alkyl having from 1 to 4 carbon atom comprising:
- (a) reacting a compound of the formula
- 15
- with an alkali metal nitrite in the presence of an acid to form a diazonium acid salt;
- (b) reacting the diazonium salt with isopropenyl acetate and a catalytic amount of a cuprous halide (I) in a solvent comprising acetonitrile and waterto form a compound of the formula
- 16
- (c) reacting the compound of the formula of step (b) with a base in an alcohol solvent at the reflux temperature of the solvent;
- subsequently adding a sufficient amount of acid to render the pH between about 4 and 5 and collecting the desired compound.
6 more elements
A process for preparing a compound of the formula
- 17
- wherein R2 is hydrogen or alkyl having 1 to 4 carbon atoms, comprising reacting a compound of the formula
- 18
- wherein X− is an anion, with isopropenyl acetate and a catalytic amount of a cuprous halide in a solvent having about the same solubility parameters as a mixture of about 1:1 volume ratio of acetonitrile and water.
1 more element
Dependencies are inferred from the claim text.