Patents Represented by Attorney Sybil A. Campbell
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Patent number: 4186001Abstract: The present invention is concerned with photographic products and processes, particularly diffusion transfer products and processes employing as a colored light-screening dye(s), a 3,3-disubstituted sulfam(na)phthalein wherein one of the 3-substituents is a 4'-hydroxy-1'-naphthyl moiety substituted in the 3'-position with a perhalomethylcarbinol group and the other of the 3-substituents is a phenyl moiety substituted with an electron-donating group and wherein the N atom of the sulfam(na)phthalein ring is substituted with a carbonyl moiety possessing a ##STR1## group bonded to the N atom of said sulfam(na)phthalein ring, which carbonyl moiety undergoes an irreversible cleavage reaction in alkaline solution above a predetermined alkaline pH to form a new compound which is colorless and non-reversible to said light-screening dye.Type: GrantFiled: November 2, 1978Date of Patent: January 29, 1980Assignee: Polaroid CorporationInventor: James W. Foley
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Patent number: 4182912Abstract: This invention is concerned with a method of preparing 5-bromopyrogallol 1,3-dimethyl ether by reacting equimolar amounts of pyrogallol 1,3-dimethyl ether and N-bromosuccinimide in a halogenated hydrocarbon solvent in the presence of monohydric alkyl alcohols, i.e., monohydric alkanols.Type: GrantFiled: September 14, 1978Date of Patent: January 8, 1980Assignee: Polaroid CorporationInventor: James W. Foley
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Patent number: 4181660Abstract: This invention relates to 3-(phenyl/naphthyl)-benz[d]isothiazole-1,1-dioxides wherein the 3-phenyl or the 3-naphthyl group is substituted in the para position with hydroxy blocked with certain protecting groups. These compounds are useful as intermediates in the synthesis of certain 3,3-disubstituted-2,3-dihydrobenz[d]isothiazole-1,1-dioxide dyes which find utility, for example, as photographic optical filter agents and filter agent precursors.Type: GrantFiled: September 23, 1977Date of Patent: January 1, 1980Assignee: Polaroid CorporationInventors: Alan L. Borror, Louis Cincotta, Ernest W. Ellis, James W. Foley, Marcis M. Kampe
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Patent number: 4178446Abstract: This invention relates to phenol sulfam(na)phthaleins possessing a ##STR1## group wherein Y represents an electron-withdrawing group substituted on the N atom of the sulfam(na)phthalein ring, which compounds find utility as photographic optical filter agents and filter agent precursors.Type: GrantFiled: September 23, 1977Date of Patent: December 11, 1979Assignee: Polaroid CorporationInventors: Stanley M. Bloom, Alan L. Borror, James W. Foley
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Patent number: 4178447Abstract: This invention relates to a method of synthesizing certain 3-(carbocyclic aryl)-3-(4'-OP-carbocyclic aryl)-2,3-dihydrobenz[d]isothiazole-1,1-dioxides (and -2,3-dihydronaphtho[1,8-de]-1,2-thiazine-1,1-dioxides) by reacting (a) a 4-OP-carbocyclic aryllithium compound wherein P is a protecting group and (b) a 3-(carbocyclic aryl)benz[d]isothiazole-1,1-dioxide wherein said 3-(carbocyclic aryl) moiety is other than a 3-(4'-OP-carbocyclic aryl) moiety to give (c) the corresponding 3-carbocyclic aryl)-3-(4'-OP-carbocyclic aryl)-2,3-dihydrobenz[d]isothiazole-1,1-dioxide. The -2,3-dihydronaphtho[1,8-de]-1,2-thiazine-1,1-dioxides are prepared in the same manner by reacting a 3-(carbocyclic aryl)naphtho[1,8-de]-1,2-thiazine-1,1-dioxide with said 4'-OP-carbocyclic aryllithium compound.Type: GrantFiled: September 23, 1977Date of Patent: December 11, 1979Assignee: Polaroid CorporationInventors: Alan L. Borror, James W. Foley, Marcis M. Kampe, John W. Lee, Jr.
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Patent number: 4172083Abstract: This invention relates to carbocyclic aryl compounds substituted with a tetrahydro-2H,4H-1,3,6-dioxazocino moiety and to the preparation thereof. These compounds are useful as intermediates in the synthesis of certain 3,3-disubstituted-2,3-dihydrobenz[d]isothiazole-1,1-dioxide dyes which find utility as, for example, photographic optical filter agents and filter agent precursors.Type: GrantFiled: September 23, 1977Date of Patent: October 23, 1979Assignee: Polaroid CorporationInventors: Louis Cincotta, James W. Foley, Marcis M. Kampe
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Patent number: 4154611Abstract: The present invention relates to novel bicyclic compounds useful as photographic silver halide developing agents, to the preparation of these compounds and to photographic products, processes and compositions employing the same. The subject compounds may be represented by the formula ##STR1## wherein R.sub.1 and R.sub.2, the same or different, each represents hydrogen, a hydrocarbon moiety, preferably an alkyl group, --COOH or --COOR.sup.1 wherein R.sup.1 is an alkyl group; R.sub.3 and R.sub.4, the same or different, each represent hydrogen or an alkyl group, R.sub.5 represents hydrogen or --COR.sup.2 wherein R.sup.2 is an alkyl group; R.sub.6 represents hydrogen when R.sub.5 is hydrogen and represents hydrogen or --OCOR.sup.3 wherein R.sup.3 is an alkyl group the same as R.sup.2 when R.sub.5 represents --COR.sup.2 ; X represents --OH, --NH.sub.2 or --NHCOR.sup.4 wherein R.sup.4 represents an alkyl group the same as R.sup.2 ; Y represents --OH or --OCOR.sup.5 wherein R.sup.Type: GrantFiled: February 27, 1978Date of Patent: May 15, 1979Assignee: Polaroid CorporationInventors: James R. Bartels-Keith, Eva R. Karger
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Patent number: 4151174Abstract: This invention relates to derivatives of phthalaldehydic and naphthalaldehydic acid useful as intermediates in the preparation of pH-sensitive phthalide and naphthalide indicator dyes.A class of intermediates provided by the present invention comprises compounds of the formula: ##STR1## wherein A represents 4'-hydroxy-1'-naphthyl; B represents 4'-hydroxy-1'-naphthyl or indol-3-yl and C represents a 2-carboxy-1-phenyl radical or an 8-carboxy-1-naphthyl radical and preferably is 8-carboxy-1-naphthyl.Type: GrantFiled: June 22, 1977Date of Patent: April 24, 1979Assignee: Polaroid CorporationInventors: Eva R. Karger, Paul T. MacGregor
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Patent number: 4150228Abstract: The present invention is concerned with novel compounds useful as photographic silver halide complexing agents and with their photographic use. The subject compounds are represented by the formulas ##STR1## wherein one of R.sup.1 and R.sup.2 is --CH.sub.2).sub.x SR.sup.3 and the other of said R.sup.1 and R.sup.2 is --CH.sub.2).sub.y SR.sup.3 wherein R.sup.3 is alkyl, x is a whole number 0 or 1 and y is a whole number from 0 to 5.Type: GrantFiled: June 30, 1977Date of Patent: April 17, 1979Assignee: Polaroid CorporationInventor: Richard B. Greenwald
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Patent number: 4140689Abstract: This invention relates to 3-(julolidinyl)-benz[d]-isothiazole-1,1-dioxide useful as an intermediate in the synthesis of certain 3,3-disubstituted-2,3-dihydrobenz[d]-isothiazole-1,1-dioxide dyes which find utility as, for example, photographic optical filter agents and filter agent precursors.Type: GrantFiled: September 23, 1977Date of Patent: February 20, 1979Assignee: Polaroid CorporationInventors: James W. Foley, John W. Lee, Jr.
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Patent number: 4139381Abstract: This invention is concerned with photographic products, particularly diffusion transfer photographic film units, useful in photographic processes conducted outside of a camera wherein post-exposure fogging by ambient light is prevented by a compound initially present as a substantially colorless compound which is activated by base to provide a light-absorbing reagent or colored optical filter agent which is capable of being irreversibly discharged without a change in pH. The colorless compound or filter agent precursor is initially disposed in a layer of the film unit, for example, in a layer coated over the photosensitive element. Subsequent to imagewise exposure of the photosensitive element, the colored optical filter agent is generated by contacting the colorless precursor with a basic processing composition.Type: GrantFiled: September 23, 1977Date of Patent: February 13, 1979Assignee: Polaroid CorporationInventors: Stanley M. Bloom, Alan L. Borror, James W. Foley
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Patent number: 4139704Abstract: This invention relates to 3-(phenyl/naphthyl)benz[d]isothiazole-1,1-dioxides wherein the phenyl or naphthyl substituent possesses an N-heterocyclic moiety in the para position. These compounds are useful as intermediates in the synthesis of certain 3,3-disubstituted-2,3-dihydrobenz[d]isothiazole-1,1-dioxide dyes which find utility as, for example, photographic optical filter agents and filter agent precursors.Type: GrantFiled: September 23, 1977Date of Patent: February 13, 1979Assignee: Polaroid CorporationInventors: Alan L. Borror, James W. Foley, John W. Lee, Jr.
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Patent number: 4126459Abstract: Difunctional compounds wherein one of said functions is a hard or soft atom that ionizes to the corresponding anion in alkaline solution to combine with silver cation and the other of said functions is a non-ionizable soft base that additionally combines with said silver cation are employed as silver halide complexing agents in photography. In a preferred embodiment, the difunctional compounds possess (a) an O, N or C atom that ionizes to the corresponding O.sup..crclbar., N.sup..crclbar. or C.sup..crclbar. anion in basic solution and (b) an --S-- containing moiety excluding --SH and moieties that form --S.sup..crclbar. in basic solution wherein the --S-- of said moiety is positioned alpha, beta, gamma, delta, epsilon or zeta to said anion.Type: GrantFiled: September 30, 1976Date of Patent: November 21, 1978Assignee: Polaroid CorporationInventor: Richard B. Greenwald
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Patent number: 4124592Abstract: This invention relates to indole phthalein indicator dyes including phthalides and naphthalides wherein one of the indol-3-yl radicals is substituted with a hydrogen-bonding group on a carbon atom adjacent to the nitrogen atom of the indole ring. In a preferred embodiment, one of the indol-3-yl radicals is substituted with a hydrogen-bonding group and the other indol-3-yl radical is substituted with a hydrogen-bonding group or with an electron-withdrawing group. These indicator dyes, especially those of the preferred embodiment, possess a relatively high pKa and a relatively broad absorption spectrum in the visible range.Type: GrantFiled: October 23, 1973Date of Patent: November 7, 1978Assignee: Polaroid CorporationInventors: Stanley M. Bloom, Alan L. Borror, Paul S. Huyffer
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Patent number: 4113738Abstract: This application is directed to a novel cleavage reaction whereby N-tosylsulfoximides of the following formula are converted to the corresponding sulfoximines. The relevant sulfoximides are represented by the formula: ##STR1## wherein R.sup.1 and R.sup.2 when taken individually (1) each represent an alkyl moiety containing up to 20 carbon atoms, unsubstituted with an alkali-stable group or (2) R.sup.1 is an alkyl moiety containing up to 20 carbon atoms and R.sup.2 is --(CH.sub.2).sub.n --S--R.sup.3 wherein n is greater than or equal to 2 and R.sup.3 is an alkyl moiety containing up to 20 carbon atoms and R.sup.1 and R.sup.2 when taken together represents (a) an alkylene moiety having 5 or 6 carbon atoms unsubstituted or substituted with an alkali-stable group; (b) --CH.sub.2 --.sub.x SO.sub.2 --CH.sub.2 -- wherein x is 3 or 4; or (c) --CHR--SO.sub.2 --CH.sub.2 CR'R"CH.sub.Type: GrantFiled: April 5, 1977Date of Patent: September 12, 1978Assignee: Polaroid CorporationInventors: David H. Evans, Richard B. Greenwald
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Patent number: 4107176Abstract: This application is directed to cycloalkanes containing the moiety --SO.sub.2 --CH.sub.2 --X-- wherein X represents ##STR1## wherein R is hydrogen or alkyl and R' is alkyl and to the preparation of these compounds which find utility as silver halide complexing agents. This application is also concerned with cycloalkanes containing the moiety ##STR2## useful as intermediates in the preparation of the aforementioned compounds. Also included within the confines of this disclosure are the 2-thioether-substituted derivatives of certain of the above-identified cycloalkanes and with the synthesis of all of these compounds.Type: GrantFiled: February 2, 1977Date of Patent: August 15, 1978Assignee: Polaroid CorporationInventors: David H. Evans, Richard B. Greenwald
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Patent number: 4102684Abstract: Certain 4-hydroxypyrazoles are employed as silver halide developing agents which find particular utility in diffusion transfer photographic processes.Type: GrantFiled: August 1, 1977Date of Patent: July 25, 1978Assignee: Polaroid CorporationInventor: Richard B. Greenwald
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Patent number: 4098783Abstract: This invention relates to color providing compounds useful as dye image-forming materials in color photographic processes. These compounds comprise a complete dye, i.e., a dye radical comprising the chromophoric system of a dye, such as, an azo, anthraquinone, azomethine or phthalocyanine dye and a cyclic moiety capable of undergoing cleavage in the presence of silver ion and/or soluble silver complex containing the group ##STR1## wherein said C atom common to said S and N atoms is a tetrahedral carbon atom possessing 4 single covalent bonds. Preferred compounds comprise the radical of an organic dye substituted with [(L).sub.m-1 -Y] wherein L is a divalent organic linking group containing at least one carbon atom, m is a positive integer 1 or 2, and Y is a cyclic moiety selected from ##STR2## WHEREIN R.sup.1 is hydrogen or a monovalent organic radical; R.sup.Type: GrantFiled: April 29, 1976Date of Patent: July 4, 1978Assignee: Polaroid CorporationInventors: Ronald F. W. Cieciuch, Roberta R. Luhowy, Frank A. Meneghini, Howard G. Rogers
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Patent number: 4067872Abstract: In one embodiment, the present invention relates to novel heterocyclic compounds as represented in the following formula ##STR1## wherein R and R' each are hydrogen or alkyl, Y is .dbd.O or .dbd.NH and n is a positive integer from 1 to 7.In another embodiment, the present invention is directed to the use of the above-denoted class of heterocyclic compounds as photographic silver halide developing agents and to photographic processes, products and compositions employing the same.Type: GrantFiled: September 9, 1976Date of Patent: January 10, 1978Assignee: Polaroid CorporationInventor: Stanley M. Bloom
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Patent number: 4067871Abstract: This invention relates to N-nitroso compounds having the formula ##STR1## wherein R and R' each are selected from hydrogen and alkyl, Z is --CN or --COOR" wherein R" is alkyl and n is a positive integer from 1 to 7. These compounds are useful as intermediates in the preparation of photographic silver halide developing agents.Type: GrantFiled: September 9, 1976Date of Patent: January 10, 1978Assignee: Polaroid CorporationInventors: James R. Bartles-Keith, Mary T. Burgess, Jean B. Rogers