Polaroid Corporation

Polaroid Corporation, Patent Dept.

Myron S Simon

David P Waller

Marcis M Kampe

David C Whritenour

Charles E Jandrue, Sr

Stanley M Bloom

Elbert M Idelson

J Michael Grasshoff

Paul T MacGregor

A novel class of bridged indicator dyes is disclosed which possess absorption in the infrared region of the electromagnetic spectrum. These bridged indicator dyes are useful as light-absorbing, pH-sensitive optical filter agents in diffusion transfer photographic processes adapted to be performed in the presence of ambient light and to diffusion transfer products useful in such processes. These indicator dyes will also find utility in titrations and other analytical techniques and products where pH-sensitive indicator dyes are employed and absorption of infrared is useful.

Photographic products and processes

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.

N-substituted triarylmethane sulfonamides and method of preparation

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. 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.

Reversible redox-controlled imaging method

Reversible redox-controlled imaging methods

This invention relates to diffusion transfer photographic processes adapted to be performed in the presence of ambient light and to diffusion transfer products useful in such processes wherein unexpectedly enhanced opacification in the red and near infrared region of the visible spectrum is achieved by employing phenanthrol/carboxynaphthol phthaleins as the light-absorbing, pH-sensitive optical filter agent for the longer wavelength region of the visible spectrum.

Copolymeric mordants coatable from water into copolymeric mordant layers for photographic products and processes are disclosed. The copolymeric mordants comprise polymerized repeating units from first and second polymerizable vinylbenzyl quaternary ammonium compounds (the first polymerizable compound, if homopolymerized, providing a water-soluble homopolymer and the second polymerizable compound being a micelle-forming compound which, if homopolymerized, forms a water-insoluble homopolymer). The copolymeric mordants are coatable to image-receiving layers for the mordanting of dyes in photographic products and processes.

Copolymeric mordants and photographic products and processes containing

There are disclosed certain aminoethanethiols, and salts thereof, and certain thiazolidines which are made therefrom. The compounds are useful as intermediates in the synthesis of photographic image dye-providing materials.

Aminoethanethiol and thiazolidine compounds

There are disclosed certain aminoether compounds which are useful as intermediates in the preparation of photographic image dye providing materials. The aminoethers are represented either by the formula ##STR1## wherein R is hydrogen or an alcohol protecting group and R.sub.1 is hydrogen, alkyl or aralkyl such as benzyl or phenethyl; or the formula ##STR2## wherein R.sub.2 and R.sub.3 are alkyl having from 1 to 6 carbon atoms or R.sub.2 and R.sub.3 together represent the carbon atoms necessary to form, together with the oxygen atoms to which they are bonded and &gt;CH, a five or six member saturated heterocyclic moiety which may include substituted rings and fused rings.

Aminoether compounds

Photographic products and processes for the imagewise generation of a dye from a color shifted dye precursor of a preformed image dye, said precursor having at least one ##STR1## group, wherein R is hydrogen, alkyl, provided that the .alpha.-carbon does not have a hydrogen atom attached thereto, aryl such as phenyl or substituted phenyl, e.g. p-nitrophenyl, or heterocyclic such as pyridine; R.sub.1 -R.sub.6 are hydrogen, alkyl, preferably having from 1 to 6 carbon atoms, or aryl; n is 0 or 1; and T is a moiety containing a thiazolidin-2-yl group which upon silver-assisted cleavage of said thiazolidin-2-yl group results in the formation of a ##STR2## group, which may be protonated under the reaction conditions, followed by cleavage of said ##STR3## which cleavage is anchimerically assisted or accelerated by said ##STR4## to provide after protonation, an ##STR5## group in a dye chromophore. In a preferred embodiment the precursor is a substantially colorless compound.

Photographic products and processes for the imagewise generation of a dye from a color shifted dye precursor of a preformed image dye, said precursor having at least one ##STR1## group, wherein R is hydrogen, alkyl, provided that the .alpha.- carbon does not have a hydrogen atom attached thereto, aryl such as phenyl or substituted phenyl, e.g. p-nitrophenyl, or heterocyclic such as pyridine; R.sub.1 -R.sub.6 are hydrogen, alkyl, preferably having from 1 to 6 carbon atoms, or aryl; n is 0 or 1; and T is a moiety containing a thiazolidin-2-yl group which upon silver-assisted cleavage of said thiazolidin-2-yl group results in the formation of a ##STR2## group, which may be protonated under the reaction conditions, followed by cleavage of said ##STR3## which cleavage is anchimerically assisted or accelerated by said ##STR4## to provide after protonation, an ##STR5## group in a dye chromophore. In a preferred embodiment the precursor is a substantially colorless compound.

Photographic products and processes with color shifted dye

This invention is concerned with certain 3-(thiazolidin-2'-yl)-substituted phenyl sulfonyl chlorides which find utility as intermediates in the preparation of photographic image dye-providing materials.

Thiazolidine-substituted phenyl sulfonyl chlorides

This invention relates to a class of phthalein indicator dyes useful as optical filter agents in photographic processes to protect a selectively exposed photosensitive material from further exposure during processing in the presence of incident light. Such dyes comprise 3,3-disubstituted phthalides and 3,3-disubstituted naphthalides wherein the 3,3 substituents are p-hydroxy carbocyclic aryl radicals wherein one or both of the radicals possess a --CH.sub.2 --NRR' group ortho to the p-hydroxy group and the --CH.sub.2 --NRR' group(s) is capable of rendering the indicator dye substantially non-diffusible in aqueous solution.

Growing community of inventors

West Newton, MA, United States of America

Myron S Simon