US 5,399,709 A · N-substituted triarylmethane sulfonamides and method of preparation

Abstract

A novel class of N-substituted triarylmethane sulfonamides is provided which undergo reversible oxidation into colored form and reversible reduction of the oxidized form into colorless form. The N-substituted triarylmethane sulfonamides can be represented by the formulae: ##STR1## wherein B is a carbocyclic ring or rings; T is a 5- or 6-membered ring; Y is a moiety selected from ##STR2## wherein E, positioned ortho or para to said --OH group, is selected from --OH, --NH.sub.2, --NHR', --NR'R" and --NHSO.sub.2 R' wherein R' and R" each are lower alkyl groups having 1 to 6 carbon atoms or aralkyl wherein the aryl portion may be substituted with alkyl groups having 1 to 24 carbon atoms, and E' is hydrogen or a monovalent group that is substituted on one of the remaining carbon atoms; G and G' each are hydroxy or methoxy, provided one is hydroxy and the other is methoxy; and Z and Z' taken individually represent the moieties to complete the chromophoric system of a triarylmethane dye when said N-containing ring, T, is open and Z and Z' taken together represent the bridged moieties to complete the chromophoric system of a bridged triarylmethane dye when said N-containing ring, T, is open; and Y' represents the quinoid form of Y. Preferred embodiments comprise xanthene sulfonamides having N-aryl substituents, e.g., hydroquinone substituents. These compounds possess redox potentials ranging between about +200 to -500 millivolts and thus are useful as dyes for producing photographic, photothermographic, thermal, and pressure-induced images, as well as being useful as redox indicators in a wide variety of biological and chemical reactions.

A triarylmethane dye compound represented by the formula:

##STR41## wherein B is a carbocyclic aryl ring or rings;
Y is a moiety selected from ##STR42## wherein E, positioned ortho or para to said --OH group, is selected from --OH, --NH.sub.2, --NHR', --NR'R", and --NHSO.sub.2 R' wherein R' and R" each are lower alkyl groups having 1 to 6 carbon atoms or aralkyl wherein the aryl portion may be substituted with alkyl groups having 1-24 carbon atoms, and E' is hydrogen or a monovalent group selected from the group consisting of:
alkyl, alkoxy, (monoalkyl)amino or (dialkyl)amino wherein said alkyl consist of 1 to 6 carbon atoms, cyano, dialkyl sulfamoyl, methylsulfonyl, phenylsulfonyl, p-tolysulfonyl, carboxy, acetyl, carbomethoxy, carbamyl, isothiocyano, benzoyl, trifluoromethyl and halo, that is substituted on one of the remaining carbon atoms;
G and G' each are hydroxy or methoxy, provided one is hydroxy and the other is methoxy;
and Z and Z' taken together represent the bridge moieties to complete the chromophoric system of a bridged-form of said triarylmethane dye and represent groups selected from:
##STR43## wherein A and A', the same or different, each represent an auxochromic substituent selected from the group consisting of:
(a) --OR.sub.1 wherein R.sub.1 is selected from the group consisting of:
hydrogen, alkyl having 1 to 6 carbon atoms, aralkyl having 7 to 15 carbon atoms, alkaryl having 7 to 15 carbon atoms, and carbocyclic aryl having 6 to 12 carbon atoms;
(b) --SR.sub.2 wherein R.sub.2 has the same meaning given for R.sub.1 ;
(c) --NR.sub.3 R.sub.4 wherein R.sub.3 and R.sub.4 each represent groups selected from the following:
1) hydrogen;
2) alkyl having 1 to 6 carbon atoms;
3) cycloalkyl having 5 to 7 carbon atoms;
4) aralkyl having 7 to 15 carbon atoms;
5) alkaryl having 7 to 15 carbon atoms;
6) a group represented by the formula:
##STR44## wherein R.sub.5 and R.sub.6 are each selected from the group consisting of:
hydrogen;
alkyl having 1 to 6 carbon atoms;
halo;
nitro;
cyano;
alkoxycarbonyl wherein said alkoxy has 1 to 6 carbon atoms;
sulfonamido (--NHSO.sub.2 R.sub.0), sulfamoyl (--SO.sub.2 NHR.sub.0), sulfonyl (--SO.sub.2 R.sub.0), acyl (--COR.sub.0), or carbamyl (--CONR.sub.0) wherein R.sub.0 is alkyl having 1 to 6 carbon atoms, benzyl or phenyl;
7) when taken together R.sub.3 and R.sub.4 represent the atoms necessary to complete a heterocyclic ring selected from the group of:
piperidino, pyrrolidino, N-methylpiperidino, morpholino or ##STR45## wherein q is an integer 2 to 5 and R.sub.7 has the same meaning as R.sub.5 ;
(d) a group represented by the formula:
##STR46## wherein R.sub.8 and R.sub.9 are selected from the group consisting of:
hydrogen, alkyl having 1 to 6 carbon atoms, and a group represented by the formula:
##STR47## wherein R.sub.11 and R.sub.12 are defined as R.sub.5 and R.sub.6 and R.sub.10 is selected from the group consisting of:
--COR.sub.13, --CSR.sub.13, and --SO.sub.2 R.sub.13 wherein R.sub.13 is selected from the group consisting of:
hydrogen, alkyl having 1 to 6 carbon atoms, phenyl, --NH.sub.2, --NHR.sub.14, --N(R.sub.14).sub.2 and --OR.sub.14 wherein R.sub.14 is selected from the group consisting of:
hydrogen, alkyl having 1 to 6 carbon atoms and phenyl.

30 more elements

Facts

Application

08/076,213Filed 11 Jun 1993 · division

Priority

31 May 1991

Granted

21 Mar 1995

Term ends

Not estimatedThe source records don’t support an estimate.

Classification13 codes

G03C 8/16
Oxidation of the chromogenic substances: initially diffusible in alkaline environment
B41M 5/136
Chemical colour-forming components; Additives or binders therefor: organic colour formers, e.g. leuco dyes
B41M 5/323
Using chemical colour formers: organic colour formers, e.g. leuco dyes
C07D 513/10
In which the condensed system contains two hetero rings: spiro-condensed systems

N-substituted triarylmethane sulfonamides and method of preparation

Life of this patent

N-substituted triarylmethane sulfonamides and method of preparation

Life of this patent

Abstract

Claims5