Patents Represented by Attorney Sybil A. Campbell
  • Patent number: 4290955
    Abstract: In one embodiment, the present invention is concerned with novel xanthene compounds of the formula ##STR1## wherein each R.sup.1 the same or different is hydrogen or alkyl, each R.sup.2 the same or different is alkyl or phenyl, R.sup.3 is phenyl or alkyl, Y is an electron-withdrawing group and A is an anion. In another embodiment, the present invention is concerned with photographic products and processes employing these xanthene compounds.
    Type: Grant
    Filed: May 30, 1980
    Date of Patent: September 22, 1981
    Assignee: Polaroid Corporation
    Inventors: Louis Cincotta, James W. Foley
  • Patent number: 4283538
    Abstract: In one embodiment, the present invention is concerned with novel triarylmethane compounds possessing in their triaryl structure a 4'-oxo-1'-naphthylidene (or a 4'-oxo-1'-phenylidene) moiety and a phenyl moiety substituted in the ortho-position to the central carbon atom with the group ##STR1## wherein R is an alkyl group or a phenyl group, unsubstituted or substituted with a solubilizing group; R' is selected from ##STR2## wherein R" is methyl, unsubstituted or substituted with one or two halo groups or substituted with a phenyl, alkoxy or phenoxy group and ##STR3## wherein Y is an electron-withdrawing group; and R and R' taken with said ##STR4## represents ##STR5## In another embodiment the present invention is concerned with a method of synthesizing the aforementioned compounds by reacting, e.g., a 2-R'-3-(4'-hydroxy-1'-phenyl/naphthyl)-3-(phenyl/naphthyl)-2,3-dihydrobenz [d]isothiazole-1,1-dioxide with an alkylation reagent in the presence of base.
    Type: Grant
    Filed: December 26, 1979
    Date of Patent: August 11, 1981
    Assignee: Polaroid Corporation
    Inventor: James W. Foley
  • Patent number: 4283537
    Abstract: In one embodiment, the present invention is concerned with 3,3-disubstituted sulfam(na)phthaleins wherein one of the 3-substituents is derived from a perhalomethylcarbinol-substituted phenol or 1-naphthol useful as intermediates in the preparation of certain N-acylated sulfam(na)phthalein compounds, which compounds find utility, e.g., as pH-sensitive indicator dyes or photographic light-screening dyes.In another embodiment, the present invention is concerned with a method of synthesizing said sulfam(na)phthalein intermediates by reacting certain 3-substituted-benz[d]isothiazole-1,1-dioxides (or 3-substituted-naphtho[1,8-de]-1,2-thiazine-1,1-dioxides) and a 4-OLi-naphthyllithium compound or a 4-OLi-phenyllithium compound substituted in the 3-position with a lithiated perhalomethylcarbinol group.
    Type: Grant
    Filed: November 2, 1978
    Date of Patent: August 11, 1981
    Assignee: Polaroid Corporation
    Inventors: Louis Cincotta, James W. Foley
  • Patent number: 4282160
    Abstract: The present invention is concerned with novel compounds useful in photographic products and processes comprising triarylmethane dyes possessing in their triaryl structure a 4'-oxo-1'-naphthylidene (or a 4'-oxo-1'-phenylidene) moiety and a phenyl moiety substituted in the ortho-position to the central carbon atom with the group ##STR1## wherein R is an alkyl group or a phenyl group, unsubstituted or substituted with a solubilizing group and Y is an electron-withdrawing group.
    Type: Grant
    Filed: May 22, 1980
    Date of Patent: August 4, 1981
    Assignee: Polaroid Corporation
    Inventor: James W. Foley
  • Patent number: 4277407
    Abstract: The present invention is concerned with novel triarylmethane dyes possessing in their triaryl structure a 4'-oxo-1'-naphthylidene (or a 4'-oxo-1'-phenylidene) moiety and a phenyl moiety substituted in the ortho-position to the central carbon atom with the group ##STR1## wherein R is hydrogen; alkyl, unsubstituted or substituted with halo, alkoxy, carboxy-substituted alkoxy, phenoxy or phenyl; or phenyl, unsubstituted or substituted with halo, alkoxy, nitro, dimethylamino or alkyl, which compounds find utility in photographic products and processes.
    Type: Grant
    Filed: December 26, 1979
    Date of Patent: July 7, 1981
    Assignee: Polaroid Corporation
    Inventor: James W. Foley
  • Patent number: 4277406
    Abstract: The present invention is concerned with novel triarylmethane dyes possessing in their triaryl structure a 4'-oxo-1'-naphthylidene (or a 4'-oxo-1'-phenylidene) moiety and a phenyl moiety substituted in the ortho-position to the central carbon atom with the group ##STR1## wherein R is alkyl, unsubstituted or substituted with a solubilizing group, and Y is an electron-withdrawing group, which compounds find utility in photographic products and processes.
    Type: Grant
    Filed: December 26, 1979
    Date of Patent: July 7, 1981
    Assignee: Polaroid Corporation
    Inventor: James W. Foley
  • Patent number: 4259493
    Abstract: The present invention is concerned with novel 3,3-disubstituted-sulfam(na)phthaleins wherein one of the 3-substituents is derived from a 1-naphthol or a phenol substituted in the 2-position with a perhalomethylcarbinol group and wherein the N atom of the sulfam(na)phthalein ring is substituted with ##STR1## wherein R is alkyl or aryl or with ##STR2## wherein Y is hydrogen or an electron-withdrawing group, which compounds find utility, e.g., as pH-sensitive indicator dyes or as photographic light-screening dyes.
    Type: Grant
    Filed: November 2, 1978
    Date of Patent: March 31, 1981
    Assignee: Polaroid Corporation
    Inventor: James W. Foley
  • Patent number: 4259498
    Abstract: This invention relates to certain 3,3,-di(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) and to the preparation thereof by reacting (a) at least 2 equivalents of (i) a 4'-OP-carbocyclic aryllithium compound wherein P is a protecting group compatible with organometallic reagents or (ii) a 4'-OP-carbocyclic arylMgE compound wherein P is a protecting group compatible with organometallic reagents and E is chloro, bromo or iodo and (b) 1 equivalent of a compound selected from a 3-chlorobenz[d]isothiazole-1,1-dioxide and a 3-chloronaphtho[1,8-de]-1,2-thiazine-1,1-dioxide to give the corresponding 3,3-di(4'-OP-carbocyclic aryl)-2,3-dihydrobenz[d]isothiazole-1,1-dioxide or the corresponding 3,3-di(4'-OP-carbocyclic aryl)-2,3-dihydronaphtho[1,8-de]-1,2-thiazine-1,1-dioxide, which compounds are useful in the synthesis of phenol and 1-naphthol sulfam(na)-phthaleins employed, for example, as photographic optical filter agents and filter agent
    Type: Grant
    Filed: October 12, 1979
    Date of Patent: March 31, 1981
    Assignee: Polaroid Corporation
    Inventors: Stanley M. Bloom, Alan L. Borror, James W. Foley
  • Patent number: 4258118
    Abstract: In one embodiment, the present invention is concerned with novel xanthene compounds of the formula ##STR1## wherein R' is alkyl; Y is an electron-withdrawing group and A is an anion. In another embodiment, the present invention is concerned with photographic products and processes employing these xanthene compounds.
    Type: Grant
    Filed: December 26, 1979
    Date of Patent: March 24, 1981
    Assignee: Polaroid Corporation
    Inventors: James W. Foley, Louis Locatell, Jr., Charles M. Zepp
  • Patent number: 4258119
    Abstract: In one embodiment, the present invention is concerned with novel xanthene compounds of the formula ##STR1## wherein X is ##STR2## wherein R' is alkyl, Y is an electron-withdrawing group and n is 0 or 1. In another embodiment, the present invention is concerned with photographic products and processes employing these xanthene compounds.
    Type: Grant
    Filed: December 26, 1979
    Date of Patent: March 24, 1981
    Assignee: Polaroid Corporation
    Inventors: Richard L. Cournoyer, James W. Foley
  • Patent number: 4255578
    Abstract: The present invention is concerned with a method of synthesizing certain ##STR1## 3-disubstituted sulfam(na)phthalein compounds useful as pH-sensitive indicator dyes and with intermediates useful in the preparation of said compounds. The subject method comprises (1) reacting (a) a 3,3-disubstituted sulfam(na)phthalein wherein one of the 3-substituents is a 4'-hydroxy-1'-phenyl moiety or a 4'-hydroxy-1'-naphthyl moiety substituted in the 3'-position with a perhalomethylcarbinol group and (b) an acid halide, ##STR2## wherein R is alkyl or aryl to give (c) an acylated intermediate wherein the N atom of the sulfam(na)phthalein ring and the 4'-hydroxy and carbinol hydroxy groups are acylated with ##STR3## and (2) treating said compound (c) with alkali to selectively remove said ##STR4## from said hydroxy groups and yield the ##STR5## product. The intermediates of the present invention are the acylated compounds (c).
    Type: Grant
    Filed: November 2, 1978
    Date of Patent: March 10, 1981
    Assignee: Polaroid Corporation
    Inventors: Louis Cincotta, James W. Foley
  • Patent number: 4231929
    Abstract: This invention relates to phenol sulfam(na)phthaleins possessing a 2-(2'-halomethylbenzoyl) 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: Grant
    Filed: September 23, 1977
    Date of Patent: November 4, 1980
    Assignee: Polaroid Corporation
    Inventors: Stanley M. Bloom, Alan L. Borror, James W. Foley
  • Patent number: 4228075
    Abstract: This invention relates to phenol sulfam(na)phthaleins possessing a ##STR1## group wherein R is selected from lower alkyl and phenyl, unsubstituted or substituted with at least one electron-withdrawing group on the N atom of the sulfam(na)phthalein ring, which compounds find utility as photographic optical filter agents and filter agent precursors.
    Type: Grant
    Filed: September 23, 1977
    Date of Patent: October 14, 1980
    Assignee: Polaroid Corporation
    Inventors: Stanley M. Bloom, Alan L. Borror, James W. Foley
  • Patent number: 4211562
    Abstract: 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: Grant
    Filed: August 4, 1978
    Date of Patent: July 8, 1980
    Assignee: Polaroid Corporation
    Inventor: Richard B. Greenwald
  • Patent number: 4211559
    Abstract: 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.crclbar., N.crclbar. or C.crclbar. anion in basic solution and (b) an --S-- containing moiety excluding --SH and moieties that form --S.crclbar. in basic solution wherein the --S-- of said moiety is positioned alpha, beta, gamma, delta, epsilon or zeta to said anion.
    Type: Grant
    Filed: August 4, 1978
    Date of Patent: July 8, 1980
    Assignee: Texas Instruments Incorporated
    Inventor: Richard B. Greenwald
  • Patent number: 4210752
    Abstract: The present invention is concerned with synthesizing certain ##STR1## by reacting (a) a 3,3-disubstituted sulfam(na)phthalein wherein one of the 3-substituents is a 4'-hydroxy-1'-phenyl moiety or a 4'-hydroxy-1'-naphthyl moiety substituted in the 3'-position with a perhalomethylcarbinol group and (b) an acid halide, ##STR2## wherein W is chloro or bromo and Y is hydrogen or an electron-withdrawing group, preferably, in the presence of a zeolite molecular sieve or acid alumina to give (c) the corresponding ##STR3## The compounds produced are useful, for example, as pH-sensitive indicator dyes or as photographic light-screening dyes.
    Type: Grant
    Filed: November 2, 1978
    Date of Patent: July 1, 1980
    Assignee: Polaroid Corporation
    Inventors: Louis Cincotta, James W. Foley
  • Patent number: 4204061
    Abstract: This invention relates to phenol sulfam(na)phthaleins possessing a ##STR1## wherein R is selected from methyl, unsubstituted or substituted with one or two halo groups and phenyl, unsubstituted or substituted with alkyl, dimethylamino or nitro 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: Grant
    Filed: September 23, 1977
    Date of Patent: May 20, 1980
    Assignee: Polaroid Corporation
    Inventors: Stanley M. Bloom, Alan L. Borror, James W. Foley
  • Patent number: 4195180
    Abstract: This invention relates to 1-naphthol sulfam(na)phthaleins possessing a carbonyl moiety on the N atom of sulfam(na)phthalein ring, which compounds find utility, for example, as antihalation and filter dyes in photographic products and processes.
    Type: Grant
    Filed: September 23, 1977
    Date of Patent: March 25, 1980
    Assignee: Polaroid Corporation
    Inventors: Alan L. Borror, Louis Cincotta, Ernest W. Ellis, James W. Foley
  • Patent number: 4191689
    Abstract: This invention relates to certain 3,3-di(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) and to the preparation thereof by reacting (a) at least 2 equivalents of (i) a 4'-OP-carbocyclic aryllithium compound wherein P is a protecting group compatible with organometallic reagents or (ii) a 4'-OP-carbocyclic arylMgE compound wherein P is a protecting group compatible with organometallic reagents and E is chloro, bromo or iodo and (b) 1 equivalent of a compound selected from a 3-chlorobenz[d] isothiazole-1,1-dioxide and a 3-chloronaphtho[1,8-de]-1,2-thiazine-1,1-dioxide to give the corresponding 3,3-di(4'-OP-carbocyclic aryl)-2,3-dihydrobenz[d]isothiazole-1,1-dioxide or the corresponding 3,3-di(4'-OP-carbocyclic aryl)-2,3-dihydronaphtho[1,8-de]-1,2-thiazine-1,1-dioxide, which compounds are useful in the synthesis of phenol and 1-naphthol sulfam(na)-phthaleins employed, for example, as photographic optical filter agents and filter agent
    Type: Grant
    Filed: September 23, 1977
    Date of Patent: March 4, 1980
    Assignee: Polaroid Corporation
    Inventors: Stanley M. Bloom, Alan L. Borror, James W. Foley
  • Patent number: 4187225
    Abstract: In one embodiment, this application is directed to an improved method of synthesizing certain bis-pyrazolone oxonol compounds useful as antihalation dyes in photography which method comprises synthesizing a pyrazolone ethyl ester by reacting a p-N-alkylsulfonamidophenylhydrazine or its hydrochloride and sodium diethyl oxalacetate, hydrolyzing the pyrazolone ethyl ester thus formed to give the corresponding pyrazolonecarboxylic acid, esterifying the pyrazolonecarboxylic acid with a glycol to give the corresponding pyrazolone hydroxyalkyl ester and condensing said pyrazolone hydroxyalkyl ester with an aldehyde dianil hydrochloride to yield the dye product.
    Type: Grant
    Filed: March 3, 1978
    Date of Patent: February 5, 1980
    Assignee: Polaroid Corporation
    Inventors: Henry Bader, Michael H. Feingold