US2298443A - Nondiffusing sulphonamide coupler for color photography - Google Patents

Nondiffusing sulphonamide coupler for color photography Download PDF

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Publication number
US2298443A
US2298443A US353669A US35366940A US2298443A US 2298443 A US2298443 A US 2298443A US 353669 A US353669 A US 353669A US 35366940 A US35366940 A US 35366940A US 2298443 A US2298443 A US 2298443A
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coupler
group
sulphonamide
reactive
photographic
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US353669A
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Weissberger Arnold
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Eastman Kodak Co
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Eastman Kodak Co
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Priority to US441278A priority Critical patent/US2338677A/en
Priority to US453854A priority patent/US2350138A/en
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/32—Colour coupling substances
    • G03C7/34—Couplers containing phenols
    • G03C7/344—Naphtholic couplers
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/32—Colour coupling substances
    • G03C7/3212—Couplers characterised by a group not in coupling site, e.g. ballast group, as far as the coupling rest is not specific

Definitions

  • Patentemfict. 1942 ED STATES. PATENT-ferries "2.29am v 7' NDNDIFFUSING SULPHONAMIDE COUPLER FOB PHOTOGRAPHY Arnold Weissberger, Rochester, N. Y., assignor to Eastman Kodak Company, Rochester, N. Y., a corporation or New'Jersey No Drawing. Application. August 22, 1940, Serial No. 353,669. 151 Great 31-min August 24, 1939 8 Claims. (01. 95-6)
  • This invention relates to photographic color forming compounds and particularly to non-diffusing coupler compounds containing sulphonamide groups for incorporation in photographic emulsion layers.
  • Color forming compounds which react with the development product of aromatic amino developing agents to form colored images on photographic development have been the subject of numerous prior patents.
  • the dyes formed in this way are insoluble in water and in the ordi-' nary photographic developing and fixing baths although the silver images formed simultaneously with them duringthe photographic development may be removed from the photographic layer to leave pure dye images in the layer.
  • a coupling component or coupler Such a compound which is employed in conjunction with the developing agent for the silver and which couples with the development product of the developer during photographic development is referred to herein as a coupling component or coupler. ,When these coupling components are incorporated in the photo-.
  • R is an aryl radical such as phenyl or naphthyl which may be substituted but which, may not be a hydroxy substituted aryl radical
  • X is an alkyl or phenyl substituted alkyl which may be substituted and Y is an organic substitu- 1 ent such as alkyl or arylradicals.
  • the coupler must also contain a group reactive with the oxidation product of the developer
  • This group is the reactive methylene orethenol group characteristicof couapler compounds and wil1.be more specifically referred to hereinafter.
  • a reac-. tive methylene group it may be contained in the portion' oi the molecule attached either to the sulphur or to the nitrogen atom of the sulphonamide group.
  • the reactive ethenol group this group may not be attached directly to the sulphur atom of the sulphonamide but may be attached to the nitrogen atom or to one of the groups attached to the nitrogen atom oi the sulphonamide radical.
  • onus-car o -r r-crm couplers according Compound -I is a coupler capable of producing a yellow dye image and is of the type described in Vittum, Peterson and Porter U. 8. Patent No.
  • My invention resides in the discovery b-lN-(benryl)-a-naphthalene-sulpbonylaminol-l-naphthol I Ill ' that, by the substitution of'this i'ree hydrogen atom of the sulphonamide group with suitable organic radicals, the valuable properties of the I on- 2,4-dichloro-6-[N-(benzyn-p-nlphthaleno-sulphonylaminol-lnlphthol on.
  • These compounds are usually used in the salt form, such as the hydrochloride or the sulphate, which are more stable than the amines themselves.
  • Suitable compounds are diethyl-p-phenylenediamine hydrochloride, men-- omethyl-p-phenylenediaminehydrochloride, dimethyl p phenylenediaminehydrochloride a n d dimethyl-p-phenylenediamine sulphate.
  • the paminophenols and their substitution products may also be used where the amino group is unsubstituted. All of these compounds have an unsubstituted amino group which enables the oxidation products of the developer to couple with I the color forming compounds to form a dye image.
  • the other substituent onthe nitrogen atom is limited to alkyl, phenyl substituted alkyl or benzyl radicals.- This is the substituent which controls the solubility of the coupler and produces the property of non-diffusibility ingelatin.
  • This substituent may be a simple-methyl or ethyl radical or a phenyl substituted alkyl radical such as benzyl or v-phenylpropyl. These radicals obviously may be considered phenyl substituted alkyl radicals, benzyl being a phenylvsubstituted methyl radical and q-phenylpropyl being a phenyl substituted propyl radical.
  • the coupler must contain the functional or reactive group common to color forming compounds which react with primary aromatic amino developing-agents.
  • This reactive group takes the form of a reactive methylene or reactive etlrenol group.
  • reactive methylene we mean a CH: group which is reactive in the coupling proces's.j
  • the cm group is usually present betweentwo negative centers as in'the groups or -CO-CH2-CN.
  • the aromatic amino developing agents used; with the coupler compounds of my invention 111* 1' clude the mono-, diand tri-aminoaryl compounds and their derivativesformed by substitu-
  • the following examples are illustrative of developing solutions which may be used to develop emulsion layers containing the couplers
  • the couplers used according to my invention may be incorporated in silver halide emulsion alcohol and add this to the emulsion.
  • '3 grams of coupler may be dissolved or suspended in cc. of ethyl alcohol and sodium hydroxide added in the amount of 1 /2 equivalent weights of the coupler.
  • the sodium'hydroxide maybe added as solid or as a concentrate solugenerated in a solution of 50 cc.'of alcohol and this solution is addedto 1 liter of a gelatin silver then be adjusted if desired by adding a suitable acid such as acetic or sulphuric acid to neutralize all or part of the sodium hydroxide used to form the sodium salt of the coupler.
  • a suitable acid such as acetic or sulphuric acid
  • the coupling components may be incorporated either in gelatin or in other colloidal materials such as collodion, organic esters of cellulose or synthetic resins.
  • the emulsion may be carried by a transparent medium such as glass, cellulose esters, or synthetic resin or a non-transparent reflecting medium such as paper or an opaque cellulose ester.
  • the emulsion may be coated'as a single layer on the support or superposed layers containing the couplers may be coated on one or both sides of the support.
  • the superposed layers may be differentially. sensitized for the formation of anatural colorimage in the well known mane ner.' v
  • a photographic emulsion for forming colored images comprising a colloidal carrier 6 containing a Sensitive silver halide and a coupler compound having the formula:
  • R is an aryl radical other than a hydro substituted aryl radical
  • x is a phenyl substituted alkyl radical
  • Y is selected from the class consisting of alkyl and aryl radicals, said coupler compound'containing at least one group selected from the class consisting of. methylene and ethenol which is reactive with primary aromatic amino developers.
  • a photographic emulsion for forming colored images comprising a colloidal carrier containing a sensitive silver halide and acoupler compound having the formula:
  • R-SOz-N Y where R is an aryl radical other than a hydroxy substituted aryl radical and Y- is selected from the class consisting of alkyl and aryl radicals, said coupler compound containing at least one .group selected from theclass consisting of methylene and ethenol which is reactive with 1 I aromatic amino developers.
  • a photographic emulsion for forming colored images comprising a colloidal carrier containing a sensitive silver halide and a coupler 7 compound having the formula: 1
  • a photographic emulsion for forming colored images comprising a colloidal carriercontaining a sensitive silver halide and acoupler compound having the formula: t i
  • R-SQr-N where R is an aryl radical other than a hydroxy substituted aryl radical, X is selected from the class consisting of alkyl and phenyl substituted alkyl radicals andZ is anaphthol residue, said coupler compound containing at least one group selected from the class consisting of methylene and ethenol which is reactive with primary aromatic photographic developers.
  • BSOIN accen s whereR is an aryl radical'other than ahydroxy substituted aryl radical, x is a phenyl substituted alkyl radical and Y is selected from the class consisting of alkyl and aryl radicals, said coupler compound containing at least one group selected from the class vconsisting of methylene and ethenol which is reactive with primary aromaticamino developers with a developer containing a primary aromatic amino developing agent.
  • R is an aryl radical other than a hydroxy substituted aryl radical and Y is selected from the class consisting of alkyl and-aryl radicals, said coupler compound containing at least one group selected from the class consisting of methylerie and ethenol which is reactive with primary aromatic amino developers, with a developing solution containing a primary aromatic ami-.
  • R is an aryl radical other than a hydroxy substituted aryl radical and Y is selected from the class consisting of alltyl and aryl radicals
  • said coupler compound containing at least one group selected from the class consisting of methylene and ethenol which is reactive with primary am
  • R is an aryl radical other than a hydroxy substituted aryl radical
  • X is selectedirom the class consisting of alkyl and phenyl substituted alkyl radicals
  • Z is a. naphthol residue
  • said coupler compound containing at least one group selected from the class consisting of methylene and ethenol which is reactive with primary aromatic amino developers, with a developing solution containing a primary aromatic amino developing agent.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Patentemfict. 1942 ED STATES. PATENT-ferries "2.29am v 7' NDNDIFFUSING SULPHONAMIDE COUPLER FOB PHOTOGRAPHY Arnold Weissberger, Rochester, N. Y., assignor to Eastman Kodak Company, Rochester, N. Y., a corporation or New'Jersey No Drawing. Application. August 22, 1940, Serial No. 353,669. 151 Great 31-min August 24, 1939 8 Claims. (01. 95-6) This invention relates to photographic color forming compounds and particularly to non-diffusing coupler compounds containing sulphonamide groups for incorporation in photographic emulsion layers. a v
Color forming compounds which react with the development product of aromatic amino developing agents to form colored images on photographic development have been the subject of numerous prior patents. The dyes formed in this way are insoluble in water and in the ordi-' nary photographic developing and fixing baths although the silver images formed simultaneously with them duringthe photographic development may be removed from the photographic layer to leave pure dye images in the layer. Such a compound which is employed in conjunction with the developing agent for the silver and which couples with the development product of the developer during photographic development is referred to herein as a coupling component or coupler. ,When these coupling components are incorporated in the photo-.
. graphic layer prior tofexposure', they do not af- 3 In Vittum, Peterson and Porter U. S. Patent N0. 2,271,238, granted January 27, 194 2, coupling components are described which contain sulphonamide groups. Such couplers are desirable by reason of their. solubility characteristics and the improved properties of the dyes formed from them. The couplers described in theVittmn,
Peterson andPorter'application-main general,
soluble in the developing solution and not suitable for use in the emulsion layer because of 40 their'tendency to fiuse from the layer. The dyes formed fromt ese couplers, however, have better light transmission characteristics and are more stable tolleat and light than the dyes produced from PIEY1OIIS1Y known coupling compo- 45 nents It is an object of the present invention to provide coupling components which have the desirable properties oi couplers containing the sulphonamidekroup but which may b mm o. 50 rim-oo-cm-co-mm rated in photogfaphicjemulsion layers as nondiflusing compounds. A further object is tov provide novel photographic couplers having desizable properties with respect to heat and light stability. .A still further object is to provide 55 photographic couplers which form image dyes having desirable light transmission characteris to form a dye.
tics. Other objects will appear from the following description of my invention.
These objects are acegmplished by replacing the free hydrogen atom of the sulphonamide group otcouplers containing such group with A radicals having the property of rendering the couplers non-diffusing'in gelatin or other col:
loidal media. a
The color forming or coupling compounds which I have-found to be suitable for incorporastructure where R is an aryl radical such as phenyl or naphthyl which may be substituted but which, may not be a hydroxy substituted aryl radical,
X is an alkyl or phenyl substituted alkyl which may be substituted and Y is an organic substitu- 1 ent such as alkyl or arylradicals.
The coupler must also contain a group reactive with the oxidation product of the developer This group is the reactive methylene orethenol group characteristicof couapler compounds and wil1.be more specifically referred to hereinafter. In the case of a reac-. tive methylene group it may be contained in the portion' oi the molecule attached either to the sulphur or to the nitrogen atom of the sulphonamide group. In the case of the reactive ethenol group this group may not be attached directly to the sulphur atom of the sulphonamide but may be attached to the nitrogen atom or to one of the groups attached to the nitrogen atom oi the sulphonamide radical. As pointed out in the Vittum, Peterson and Porter Patent nol group attached to the-sulphur atom of the sulphonamide produce dyes which are less sta-= ble to heat and light than compounds having the ethenol group attached to the nitrogenatom of the sulphonamide group or having a reactive methylene group attached .either to the sulphur atom or to the nitrogen atom.
My invention may be illustrated by reference to the following compounds I and n. I
un-co-cm-oo-cgr,
cm r
onus-car o -r r-crm couplers according Compound -I is a coupler capable of producing a yellow dye image and is of the type described in Vittum, Peterson and Porter U. 8. Patent No.
2,271,238. It'is soluble in photographic develop-' ing solutions. Compound II is identical with compound 1 except that the free hydrogen atom of the sulphonamide group has been replaced with a methyl radical. Compound II also produces a yellow dye upon development with the proper photographic developing agent. How ever, because of the replacement of the hydrogen atom oi the sulphonated group witha suitable radical, the oouplerisno longer soluble in the developer but maybe incorporated in .a photographic emulsion layer as a non-diffusing 'compound. My invention resides in the discovery b-lN-(benryl)-a-naphthalene-sulpbonylaminol-l-naphthol I Ill ' that, by the substitution of'this i'ree hydrogen atom of the sulphonamide group with suitable organic radicals, the valuable properties of the I on- 2,4-dichloro-6-[N-(benzyn-p-nlphthaleno-sulphonylaminol-lnlphthol on.
hHn I t-amyldiplienylothei'siflpbonylamino-l-naphthol 2,4-dibromo-6-[N-(benzylyfi-nzphthalenc-sulphonyleminol-lm tho! z-monochlorwlN-(bonzylgpr i: lghalen o-sulphonylaminol-l- .411" I B-lN (p any prom-mphw phanygaminoh naphthol tmcm i-mmnmm .o-cmcm cm y N-O: v NHooomcoOocm t-CtHu N-(p-anisoylacetaminobenzenesul honyD-N-(' -pbenylpropyl)-pm tert.-amy
be attached to the sulphur atom of the sulphonamide group but only to the nitrogen atom as illustrated, for example, by compounds 1 to- 11. if the reactive portion of the coupler is of the tion of the molecule attached to the sulphur atom of the sulphonamide group as illustrated, for example; by compounds 12. to 37 or in the portion of the molecule attached to the nitrogen atom of the sulphonamide group as illustrated by com-' pound as. I c I One of the substituents on the nitrogen atom tion in the amino group as well as in the ring, such as 'alkylphenylenediamines and aliwltoluaylenediamines. These compounds are usually used in the salt form, such as the hydrochloride or the sulphate, which are more stable than the amines themselves. Suitable compounds are diethyl-p-phenylenediamine hydrochloride, men-- omethyl-p-phenylenediaminehydrochloride, dimethyl p phenylenediaminehydrochloride a n d dimethyl-p-phenylenediamine sulphate. The paminophenols and their substitution products may also be used where the amino group is unsubstituted. All of these compounds have an unsubstituted amino group which enables the oxidation products of the developer to couple with I the color forming compounds to form a dye image.
'25 methylene type, it may be contained in the por'-' made according to my invention;
Errample 1 p-Aminodiethylaniline sulphategrams 2.5 Sodium sulphite anhydrous do-. 2 Sodium carbonatev anhydrous do-. :20 Potassium brom de d 1 Water t HYPIZ- 1 Example 2 p-Aminodiethylaniline hydrochloride grams" 2 Sodium sulphite anhydrous ..do 5 Sodium carbonate anhydrous do.. 20 Potassium bromide do- 2 Water to liter 1 of the sulphonamide group, that is, Y in the general formula above, may be any organic substituent such as an alkyl or an aryl radical. This substituent may or may not be a phenolic hydroxyl radical. The other substituent onthe nitrogen atom, that is, X in the general formula above, is limited to alkyl, phenyl substituted alkyl or benzyl radicals.- This is the substituent which controls the solubility of the coupler and produces the property of non-diffusibility ingelatin. This substituent may be a simple-methyl or ethyl radical or a phenyl substituted alkyl radical such as benzyl or v-phenylpropyl. These radicals obviously may be considered phenyl substituted alkyl radicals, benzyl being a phenylvsubstituted methyl radical and q-phenylpropyl being a phenyl substituted propyl radical.
As stated above the coupler must contain the functional or reactive group common to color forming compounds which react with primary aromatic amino developing-agents. This reactive group takes the form of a reactive methylene or reactive etlrenol group. By reactive methylene we mean a CH: group which is reactive in the coupling proces's.j The cm group is usually present betweentwo negative centers as in'the groups or -CO-CH2-CN.
One of the hydrogen atoms of the methylene.
position of the hydroxyl group.-
The aromatic amino developing agents used; with the coupler compounds of my invention 111* 1' clude the mono-, diand tri-aminoaryl compounds and their derivativesformed by substitu- The following examples are illustrative of developing solutions which may be used to develop emulsion layers containing the couplers The couplers used according to my invention may be incorporated in silver halide emulsion alcohol and add this to the emulsion. For example, '3 grams of coupler may be dissolved or suspended in cc. of ethyl alcohol and sodium hydroxide added in the amount of 1 /2 equivalent weights of the coupler. The sodium'hydroxide maybe added as solid or as a concentrate solugenerated in a solution of 50 cc.'of alcohol and this solution is addedto 1 liter of a gelatin silver then be adjusted if desired by adding a suitable acid such as acetic or sulphuric acid to neutralize all or part of the sodium hydroxide used to form the sodium salt of the coupler.
' The coupling components may be incorporated either in gelatin or in other colloidal materials such as collodion, organic esters of cellulose or synthetic resins. The emulsion may be carried by a transparent medium such as glass, cellulose esters, or synthetic resin or a non-transparent reflecting medium such as paper or an opaque cellulose ester. The emulsion may be coated'as a single layer on the support or superposed layers containing the couplers may be coated on one or both sides of the support. The superposed layers may be differentially. sensitized for the formation of anatural colorimage in the well known mane ner.' v
The examples and compounds set forth in the present specification are illustrative only audit is to be understood that my invention is to be taken as limited only by the scope of' the ap-' .pended claims.
I claim: 1. A photographic emulsion for forming colored images comprising a colloidal carrier 6 containing a Sensitive silver halide and a coupler compound having the formula:
, I x 'n-soi-N where R is an aryl radical other than a hydro substituted aryl radical, x is a phenyl substituted alkyl radical and Y is selected from the class consisting of alkyl and aryl radicals, said coupler compound'containing at least one group selected from the class consisting of. methylene and ethenol which is reactive with primary aromatic amino developers.
2. A photographic emulsion for forming colored images comprising a colloidal carrier containing a sensitive silver halide and acoupler compound having the formula:
I olk- 0H;
R-SOz-N Y where R is an aryl radical other than a hydroxy substituted aryl radical and Y- is selected from the class consisting of alkyl and aryl radicals, said coupler compound containing at least one .group selected from theclass consisting of methylene and ethenol which is reactive with 1 I aromatic amino developers.
3. A photographic emulsion for forming colored images comprising a colloidal carrier containing a sensitive silver halide and a coupler 7 compound having the formula: 1
I where R is an aryl radicalother than a hydroxy substituted aryl radical and Y is selected from the class consisting of alkyl and aryl radicals, said coupler compound containing at least one group selected from the class consisting of methylene'and ethenol which is reactive with aromatic amino developers. 4. A photographic emulsion for forming colored images comprising a colloidal carriercontaining a sensitive silver halide and acoupler compound having the formula: t i
R-SQr-N where R is an aryl radical other than a hydroxy substituted aryl radical, X is selected from the class consisting of alkyl and phenyl substituted alkyl radicals andZ is anaphthol residue, said coupler compound containing at least one group selected from the class consisting of methylene and ethenol which is reactive with primary aromatic photographic developers.
5. In-the method of producing a colored photographic image in a gelatino silver halide emulsion layer, the step which comprises treating the exposed layer containing a coupler compound having the formula:
BSOIN accen s whereR is an aryl radical'other than ahydroxy substituted aryl radical, x is a phenyl substituted alkyl radical and Y is selected from the class consisting of alkyl and aryl radicals, said coupler compound containing at least one group selected from the class vconsisting of methylene and ethenol which is reactive with primary aromaticamino developers with a developer containing a primary aromatic amino developing agent.
6. In the method of producing a colored pho-' tographic image in a gelatino silver halide emulsion layer, the step which comprises treating the exposed layer containing a coupler compound having the formula:
CHi-CcHs R-so,-N
where R is an aryl radical other than a hydroxy substituted aryl radical and Y is selected from the class consisting of alkyl and-aryl radicals, said coupler compound containing at least one group selected from the class consisting of methylerie and ethenol which is reactive with primary aromatic amino developers, with a developing solution containing a primary aromatic ami-.
no developing agent,
7. In the method. of producing'a colored photographic image in a gelatino silver halide emulsion layer, the step which comprises treating the exposed layer containing a coupler compound having the formula: I
' CaHc-CsHn R-SOa-N where R is an aryl radical other than a hydroxy substituted aryl radical and Y is selected from the class consisting of alltyl and aryl radicals, said coupler compound containing at least one group selected from the class consisting of methylene and ethenol which is reactive with primary amwhere R is an aryl radical other than a hydroxy substituted aryl radical, X is selectedirom the class consisting of alkyl and phenyl substituted alkyl radicals and Z is a. naphthol residue, said coupler compound containing at least one group selected from the class consisting of methylene and ethenol which is reactive with primary aromatic amino developers, with a developing solution containing a primary aromatic amino developing agent. v
' ARNOLD WEISSBERGER.
US353669A 1939-08-24 1940-08-22 Nondiffusing sulphonamide coupler for color photography Expired - Lifetime US2298443A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US441278A US2338677A (en) 1940-08-22 1942-05-01 Nondiffusing sulphonamide coupler for color photography
US453854A US2350138A (en) 1940-08-22 1942-08-06 Nondiffusing acylacetyl sulphonamide coupler

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB24322/39A GB536939A (en) 1939-08-24 1939-08-24 Improvements in and relating to photographic colour development
GB319240A GB538914A (en) 1939-08-24 1940-02-20 Improvements in and relating to photographic colour development
GB694040 1940-04-17

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US2448939A (en) * 1944-06-10 1948-09-07 Eastman Kodak Co Thioglycolic amide couplers
US2450777A (en) * 1944-04-20 1948-10-05 Eastman Kodak Co Sulfamyl-2-mercaptobenzothiazoles
US3859095A (en) * 1969-12-13 1975-01-07 Agfa Gevaert Ag Color-photographic material with improved color reproduction
US4355169A (en) * 1981-03-02 1982-10-19 Polaroid Corporation Thiazolidinyl-substituted phenyl sulfonamides
US4356258A (en) * 1979-11-21 1982-10-26 Konishiroku Photo Industry Co., Ltd. Silver halide color photographic material containing yellow coupler
US4409323A (en) * 1980-02-15 1983-10-11 Konishiroku Photo Industry Co., Ltd. Silver halide photographic material
US4503141A (en) * 1983-03-28 1985-03-05 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive materials containing couplers with a hydroxyl substituted aromatic heterocyclic sulfonyl group in the ballast group
EP0200878A1 (en) 1982-02-24 1986-11-12 Konica Corporation Light-sensitive silver halide color photographic material
US5118599A (en) * 1991-02-07 1992-06-02 Eastman Kodak Company Yellow couplers for photographic elements and processes
EP0574090A1 (en) 1992-06-12 1993-12-15 Eastman Kodak Company One equivalent couplers and low pKa release dyes
US5360713A (en) * 1992-11-12 1994-11-01 Eastman Kodak Company Yellow dye-forming couplers and color photographic elements containing these couplers
US5427898A (en) * 1992-12-04 1995-06-27 Eastman Kodak Company Yellow couplers having an arloxy coupling-off group which contains an ortho polarizable functional group
EP0684515A1 (en) 1994-05-27 1995-11-29 Eastman Kodak Company Photographic element and process incorporating a high dye-yield image coupler providing improved granularity
EP0686873A1 (en) 1994-06-08 1995-12-13 Eastman Kodak Company Color photographic element containing new epoxy scavengers for residual magenta coupler
EP0695968A2 (en) 1994-08-01 1996-02-07 Eastman Kodak Company Viscosity reduction in a photographic melt
EP0698816A1 (en) 1994-08-26 1996-02-28 Eastman Kodak Company Photographic paper formed with low molecular weight polyvinyl alcohol having low oxygen permeability
US5571661A (en) * 1994-06-09 1996-11-05 Konica Corporation Silver halide light-sensitive color photographic material
EP0777151A2 (en) 1995-11-30 1997-06-04 Eastman Kodak Company Photographic element containing yellow dye-forming coupler comprising a dye light stability enhancing ballast and process
EP0779543A1 (en) 1995-12-11 1997-06-18 Eastman Kodak Company Photographic element containing an improved pyrazolotriazole coupler
EP0779544A1 (en) 1995-12-11 1997-06-18 Eastman Kodak Company Photographic element containing an improved pyrazolotriazole coupler
EP0779536A1 (en) 1995-12-04 1997-06-18 Konica Corporation Light-and heat-sensitive recording material and recording method by use thereof
US5939244A (en) * 1997-09-26 1999-08-17 Eastman Kodak Company Photographic coupler and element
US6083986A (en) * 1996-07-26 2000-07-04 Icagen, Inc. Potassium channel inhibitors
US6458794B2 (en) 1999-12-21 2002-10-01 Icagen, Inc. Potassium channel inhibitors
US6849634B2 (en) 2000-12-21 2005-02-01 Icagen Potassium channel inhibitors
WO2013032827A1 (en) 2011-08-31 2013-03-07 Eastman Kodak Company Motion picture films to provide archival images

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US2486440A (en) * 1946-01-10 1949-11-01 Gen Aniline & Film Corp Production of phenazonium dyestuff images
US2498466A (en) * 1946-05-09 1950-02-21 Gen Aniline & Film Corp Phenolic color formers
BE480525A (en) * 1947-03-13
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US2450777A (en) * 1944-04-20 1948-10-05 Eastman Kodak Co Sulfamyl-2-mercaptobenzothiazoles
US2448939A (en) * 1944-06-10 1948-09-07 Eastman Kodak Co Thioglycolic amide couplers
US3859095A (en) * 1969-12-13 1975-01-07 Agfa Gevaert Ag Color-photographic material with improved color reproduction
US4356258A (en) * 1979-11-21 1982-10-26 Konishiroku Photo Industry Co., Ltd. Silver halide color photographic material containing yellow coupler
US4409323A (en) * 1980-02-15 1983-10-11 Konishiroku Photo Industry Co., Ltd. Silver halide photographic material
US4355169A (en) * 1981-03-02 1982-10-19 Polaroid Corporation Thiazolidinyl-substituted phenyl sulfonamides
EP0200878A1 (en) 1982-02-24 1986-11-12 Konica Corporation Light-sensitive silver halide color photographic material
US4503141A (en) * 1983-03-28 1985-03-05 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive materials containing couplers with a hydroxyl substituted aromatic heterocyclic sulfonyl group in the ballast group
US5118599A (en) * 1991-02-07 1992-06-02 Eastman Kodak Company Yellow couplers for photographic elements and processes
EP0574090A1 (en) 1992-06-12 1993-12-15 Eastman Kodak Company One equivalent couplers and low pKa release dyes
US5360713A (en) * 1992-11-12 1994-11-01 Eastman Kodak Company Yellow dye-forming couplers and color photographic elements containing these couplers
US5427898A (en) * 1992-12-04 1995-06-27 Eastman Kodak Company Yellow couplers having an arloxy coupling-off group which contains an ortho polarizable functional group
EP0684515A1 (en) 1994-05-27 1995-11-29 Eastman Kodak Company Photographic element and process incorporating a high dye-yield image coupler providing improved granularity
EP0686873A1 (en) 1994-06-08 1995-12-13 Eastman Kodak Company Color photographic element containing new epoxy scavengers for residual magenta coupler
US5571661A (en) * 1994-06-09 1996-11-05 Konica Corporation Silver halide light-sensitive color photographic material
EP0695968A2 (en) 1994-08-01 1996-02-07 Eastman Kodak Company Viscosity reduction in a photographic melt
EP0698816A1 (en) 1994-08-26 1996-02-28 Eastman Kodak Company Photographic paper formed with low molecular weight polyvinyl alcohol having low oxygen permeability
EP0777151A2 (en) 1995-11-30 1997-06-04 Eastman Kodak Company Photographic element containing yellow dye-forming coupler comprising a dye light stability enhancing ballast and process
EP0779536A1 (en) 1995-12-04 1997-06-18 Konica Corporation Light-and heat-sensitive recording material and recording method by use thereof
EP0779543A1 (en) 1995-12-11 1997-06-18 Eastman Kodak Company Photographic element containing an improved pyrazolotriazole coupler
EP0779544A1 (en) 1995-12-11 1997-06-18 Eastman Kodak Company Photographic element containing an improved pyrazolotriazole coupler
US6083986A (en) * 1996-07-26 2000-07-04 Icagen, Inc. Potassium channel inhibitors
US5939244A (en) * 1997-09-26 1999-08-17 Eastman Kodak Company Photographic coupler and element
US6458794B2 (en) 1999-12-21 2002-10-01 Icagen, Inc. Potassium channel inhibitors
US20030013706A1 (en) * 1999-12-21 2003-01-16 Icagen Potassium channel inhibitors
US6858610B2 (en) 1999-12-21 2005-02-22 Icagen, Inc. Potassium channel inhibitors
US6849634B2 (en) 2000-12-21 2005-02-01 Icagen Potassium channel inhibitors
WO2013032827A1 (en) 2011-08-31 2013-03-07 Eastman Kodak Company Motion picture films to provide archival images

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FR932002A (en) 1948-03-10
GB536939A (en) 1941-06-03
US2313586A (en) 1943-03-09

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