US 4,232,115 A · Bleachable photographic sensitizing dyes

Abstract

A novel group of photographic sensitizing dyes is prepared by reacting the 5,7-dimethyl-1,2-benzoxathian-4-one-2,2-dioxide sultone nucleus with other organic compounds capable of forming merocyanine, oxonol or styryl dyes therewith. The resulting dyes are particularly useful in the sensitization of silver halide emulsions and provide excellent speed and low after-processing dye stain.

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Claims10

Dependent claims

As a new composition of matter, a sensitizing or filter dye having one of the following general formulas:

##STR11## wherein Q represents sufficient carbon atoms to complete a benzo or naphto nucleus, or a substituted benzene or napthalene nucleus, R.sub.1, R.sub.2 and R.sub.3 each represent H or a C.sub.1 -C.sub.3 alkyl group, n=1, 2 or 3, and X represents sufficient nonmetallic atoms to complete a 5- or 6-membered heterocyclic or carbocyclic nucleus;
##STR12## wherein Q, R.sub.1, R.sub.2, R.sub.3 and n are the same as in formula A, and M is a mono-, di-, or trivalent metal;
##STR13## wherein Q, R.sub.1, R.sub.2 and n are the same as in formula A, R.sub.4 is a C.sub.1 -C.sub.12 alkyl, and Y represents sufficient nonmetallic atom to complete a 5- or 6-membered heterocyclic nucleus;
##STR14## wherein Q, R.sub.1, R.sub.2, n, R.sub.4, and Y are the same as in formula C;
and ##STR15## wherein Q, R.sub.1, R.sub.2, R.sub.3 and n are the same as in formula A and R.sub.5 can be H, a C.sub.1 -C.sub.12 alkyl group, an NO.sub.2 group, an alkyloxy or alkylthio group wherein the alkyl group contains 1-6 carbon atoms, or a dialkylamino group wherein each alkyl group contains 1-6 carbon atoms.

2 more elements

Dependencies are inferred from the claim text.

Description2,136 words

Summary566 words

#1. Technical Field

#This invention relates generally to photographic sensitizing dyes, and specifically to sensitizing dyes useful in silver halide emulsions, to methods for preparing such dyes, and to photographic silver halide emulsions containing these new dyes.

#2. Background Art

Detailed description1,570 words

#Synthesis of the dyes described above is shown in the following examples:

#3-[(3-Ethyl-2-(3H)-benzothiazolylidene)ethylidene]-5,7-dimethylbenzoxathian -4-one-2,2-dioxide (structure II, above) is prepared as follows:

#5,7-dimethylbenzoxathian-4-one-2,2-dioxide, 113 mg (0.5 mmoles) and 2-.beta.-acetanilidovinyl-3-ethylbenzothiazolium iodide, 225 mg (0.5 mmoles) are heated to 70.degree. C. in 5 ml absolute ethanol. Triethylamine (0.1 ml, 0.72 mmoles) is added and the mixture refluxed for 10 minutes, then cooled. The solid (160 mg) was collected and chromatographed on 10 g silica gel. Eluting with chloroform gave 106 mg (50%) dye mp 261.degree.-262.degree. C. .lambda.max(EtOH) 487 nm, .epsilon.=8.6.times.10.sup.4

Facts

Application

06/015,005Filed 22 Feb 1979 · continuation in part

Priority

27 Mar 1978

Granted

4 Nov 1980

Term ended

27 Mar 1998

Estimated · how

Pre-1995 term; greater of 17 years from grant or 20 years from filing when eligible. Maintenance-fee lapses, terminal disclaimers and statutory extensions have not been checked. The continuity chain may be incomplete; this is not an enforceability determination.

Classification3 codes

C07D 513/04
In which the condensed system contains two hetero rings: ortho-condensed systems
C07D 327/06
One oxygen atom and one sulfur atom: six-membered rings
C07D
Heterocyclic compounds

Bleachable photographic sensitizing dyes

Life of this patent

Bleachable photographic sensitizing dyes

Life of this patent

Life of this patent

Abstract

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Claims10

Description2,136 words

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Classification3 codes

Life of this patent

Description2,136 words