US2949359A - Process for developing silver halide emulsions - Google Patents

Process for developing silver halide emulsions Download PDF

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Publication number
US2949359A
US2949359A US680405A US68040557A US2949359A US 2949359 A US2949359 A US 2949359A US 680405 A US680405 A US 680405A US 68040557 A US68040557 A US 68040557A US 2949359 A US2949359 A US 2949359A
Authority
US
United States
Prior art keywords
silver halide
group
halide emulsions
developing
compounds
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US680405A
Other languages
English (en)
Inventor
Elkan R Blout
Green Milton
Myron S Simon
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Polaroid Corp
Original Assignee
Polaroid Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to BE570596D priority Critical patent/BE570596A/xx
Application filed by Polaroid Corp filed Critical Polaroid Corp
Priority to US680437A priority patent/US3047386A/en
Priority to US680405A priority patent/US2949359A/en
Priority to DEI15224A priority patent/DE1111936B/de
Priority to GB26188/58A priority patent/GB891767A/en
Priority to FR1210863D priority patent/FR1210863A/fr
Application granted granted Critical
Publication of US2949359A publication Critical patent/US2949359A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16Amino-anthraquinones
    • C09B1/20Preparation from starting materials already containing the anthracene nucleus
    • C09B1/26Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/28Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C5/00Photographic processes or agents therefor; Regeneration of such processing agents
    • G03C5/26Processes using silver-salt-containing photosensitive materials or agents therefor
    • G03C5/29Development processes or agents therefor
    • G03C5/30Developers
    • G03C5/3021Developers with oxydisable hydroxyl or amine groups linked to an aromatic ring
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C8/00Diffusion transfer processes or agents therefor; Photosensitive materials for such processes
    • G03C8/02Photosensitive materials characterised by the image-forming section
    • G03C8/04Photosensitive materials characterised by the image-forming section the substances transferred by diffusion consisting of inorganic or organo-metallic compounds derived from photosensitive noble metals
    • G03C8/06Silver salt diffusion transfer
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C8/00Diffusion transfer processes or agents therefor; Photosensitive materials for such processes
    • G03C8/02Photosensitive materials characterised by the image-forming section
    • G03C8/08Photosensitive materials characterised by the image-forming section the substances transferred by diffusion consisting of organic compounds
    • G03C8/10Photosensitive materials characterised by the image-forming section the substances transferred by diffusion consisting of organic compounds of dyes or their precursors
    • G03C8/12Photosensitive materials characterised by the image-forming section the substances transferred by diffusion consisting of organic compounds of dyes or their precursors characterised by the releasing mechanism
    • G03C8/14Oxidation of the chromogenic substances
    • G03C8/16Oxidation of the chromogenic substances initially diffusible in alkaline environment
    • G03C8/18Dye developers

Definitions

  • One object of this invention is to provide novel chemical compounds and suitable syntheses for their preparation.
  • Another object of this invention is to provide novel chemical compounds useful as photographic developing agents and as intermediates.
  • the invention accordingly comprises the several steps and the relation and order of one or more of such steps with respect to each of the others, and the product possessing the features, properties and the relation of elements which are exemplified in the following detailed disclosure, and the scope of the application of which will be indicated in the claims.
  • novel compounds of this invention may be represented by the formula:
  • each Y may be an unsubstituted, an alkyl-substituted or a halogen-substituted ortho or para dihydroxyfp'heinyl group;
  • R is a hydrogen, methyl or ethyl group;
  • R is a hydrogen or alkyl group and preferably an alkyl group containing no more than 5 carbon atoms such "as'a methyl, ethyl, propyl, etc.
  • R is an alkyljefne group and preferably an alkylene group containing inn more than 5 carbon atoms, such as i methylene 'CH ethylene -CH CH propylene CH CH CH isopropylene on, 3n
  • each Y is a p-dihydroxyphenyl group.
  • Such compounds may be represented by the formula:
  • novel compounds of this invention may be prepared by condensing an amine of the structure:
  • CHzCHzNHz OHs may be made of:
  • Example 1 19 gms. of 2,5-dimethoxyphenethylamine and 23 gms.
  • novel compounds of this invention are useful as photographic developing agents.
  • a suitable developing composition utilizing one of the novel compounds of this invention mention may be made of thefollowing composition:
  • composition it will be understood that it is within the scope of this invention to vary the above composition to suit particular needs.
  • the percentage of materials may be varied and additional materials useful in photographic processes may be added. If the composition is to be spread on a silver halide emulsion, a film-forming thickening agent such, for example, as sodium carboxymethyl cellulose, may be added.
  • novel compounds of this invention are useful as developing agents in diffusion transfer processes, both dye and silver transfer, and are especially useful in such photographic processes wherein it is desired to eliminate or minimize the need for washing or stabilizing operations in liquid baths subsequent to the formation of the silver print. Examples of such processes are disclosed in US. Patent No. 2,647,056 to Edwin H. Land.
  • the utility of the developers of this invention is by no means limited to diffusion transfer reversal processes, for they may be satisfactorily employed in conventional multistage multibath photographic processes in black-andwhite or color photography. Where the herein disclosed compounds are employed in dilfusion transfer processes of the type disclosed in the said patent to Edwin H.
  • the novel developer composition may have incorporated therein as a further ingredient a silver halide solvent such as sodium tlhiosulfate.
  • a silver halide solvent such as sodium tlhiosulfate.
  • novel compounds of this invention are again useful as intermediates.
  • novel compounds of this invention are further useful as antioxidants in petroleum products, etc.
  • a process for developing a photosensitive silver halide emulsion which comprises treating an exposed silver halide emulsion with an aqeuous alkaline solution of a compound of the formula:
  • Y is selected from the group consisting of unsubstituted, alkyl-substituted and halogen-substituted ortho and para dihydroxyphenyl groups; R is selected from the group consisting of hydrogen, methyl and ethyl groups; R is selected from the group consisting of hydrogen and alkyl groups; and R is an alkylene group, for a sufiicient time to develop the latent image to silver.
  • each Y is a p-dihydroxyphenyl group.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Coloring (AREA)
US680405A 1957-08-26 1957-08-26 Process for developing silver halide emulsions Expired - Lifetime US2949359A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
BE570596D BE570596A (ru) 1957-08-26
US680437A US3047386A (en) 1957-08-26 1957-08-26 Anthraquinone dye developers
US680405A US2949359A (en) 1957-08-26 1957-08-26 Process for developing silver halide emulsions
DEI15224A DE1111936B (de) 1957-08-26 1958-08-12 Verfahren zur Herstellung ein- und mehrfarbiger UEbertragungsbilder nach dem Diffusionsuebertragungsverfahren
GB26188/58A GB891767A (en) 1957-08-26 1958-08-14 Improvements in or relating to photographic dye-developers of the anthraquinone series
FR1210863D FR1210863A (fr) 1957-08-26 1958-08-25 Nouveaux procédés, produits et compositions photographiques

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US680405A US2949359A (en) 1957-08-26 1957-08-26 Process for developing silver halide emulsions
US68061957A 1957-08-27 1957-08-27

Publications (1)

Publication Number Publication Date
US2949359A true US2949359A (en) 1960-08-16

Family

ID=27102453

Family Applications (1)

Application Number Title Priority Date Filing Date
US680405A Expired - Lifetime US2949359A (en) 1957-08-26 1957-08-26 Process for developing silver halide emulsions

Country Status (5)

Country Link
US (1) US2949359A (ru)
BE (1) BE570596A (ru)
DE (1) DE1111936B (ru)
FR (1) FR1210863A (ru)
GB (1) GB891767A (ru)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3194837A (en) * 1960-11-12 1965-07-13 Hoechst Ag N-arylalkyl-phenylalkyl amines
US3496181A (en) * 1966-10-24 1970-02-17 Upjohn Co 2 - aminocycloalkyl hydroquinones,esters,ethers and n-oxides thereof,and a process for preparing the same
US3992449A (en) * 1973-11-16 1976-11-16 Fuji Photo Film Co., Ltd. 2-(γ-Aminopropyl)hydroquinones and process for producing the same
US4704407A (en) * 1984-12-20 1987-11-03 Eli Lilly And Company Soluble dobutamine salts
US5981599A (en) * 1996-05-01 1999-11-09 Nps Pharmaceuticals, Inc. Inorganic ion receptor active compounds
US6001884A (en) * 1991-08-23 1999-12-14 Nps Pharmaceuticals, Inc. Calcium receptor-active molecules
US6011068A (en) * 1991-08-23 2000-01-04 Nps Pharmaceuticals, Inc. Calcium receptor-active molecules
US6211244B1 (en) 1994-10-21 2001-04-03 Nps Pharmaceuticals, Inc. Calcium receptor-active compounds
US6313146B1 (en) 1991-08-23 2001-11-06 Nps Pharmaceuticals, Inc. Calcium receptor-active molecules
US6479198B2 (en) * 2000-02-01 2002-11-12 Fuji Photo Film Co., Ltd. Silver halide light-sensitive material containing tanning developing agent

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL86359C (ru) *
US2006114A (en) * 1931-04-27 1935-06-25 Rosenmund Karl Wilhelm Aliphatic-aromatic amine and process of making same
US2276619A (en) * 1942-03-17 N-phentlaliphatic-dihtoroxyphentnl
US2604399A (en) * 1949-07-07 1952-07-22 Eastman Kodak Co Photographic developers comprising bis-(di-hydroxyalkyl aminomethyl)-hydroquinones
US2647929A (en) * 1951-04-26 1953-08-04 Upjohn Co Separation of the diastereoisomeric bis [beta-(ortho-methoxyphenyl) isopropyl] amines
US2653977A (en) * 1953-09-29 Chxnx
US2688625A (en) * 1953-04-29 1954-09-07 Eastman Kodak Co 2, 2'-alkylidenebis (4-alkoxy-6-vinylphenols), derivatives thereof, and compositionsstabilized therewith
US2698244A (en) * 1946-10-08 1954-12-28 Polaroid Corp Photographic transfer process utilizing a primary color developer for producing a colored photographic transfer image
US2797242A (en) * 1953-08-11 1957-06-25 Parke Davis & Co Substituted alpha-benzylphenethylamines and methods for producing the same

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE954391C (de) * 1953-06-05 1956-12-13 Agfa Ag Fuer Photofabrikation Entwicklersubstanzen enthaltende Halogensilberschichten
BE536578A (ru) * 1954-03-18

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL86359C (ru) *
US2276619A (en) * 1942-03-17 N-phentlaliphatic-dihtoroxyphentnl
US2653977A (en) * 1953-09-29 Chxnx
US2006114A (en) * 1931-04-27 1935-06-25 Rosenmund Karl Wilhelm Aliphatic-aromatic amine and process of making same
US2698244A (en) * 1946-10-08 1954-12-28 Polaroid Corp Photographic transfer process utilizing a primary color developer for producing a colored photographic transfer image
US2604399A (en) * 1949-07-07 1952-07-22 Eastman Kodak Co Photographic developers comprising bis-(di-hydroxyalkyl aminomethyl)-hydroquinones
US2647929A (en) * 1951-04-26 1953-08-04 Upjohn Co Separation of the diastereoisomeric bis [beta-(ortho-methoxyphenyl) isopropyl] amines
US2688625A (en) * 1953-04-29 1954-09-07 Eastman Kodak Co 2, 2'-alkylidenebis (4-alkoxy-6-vinylphenols), derivatives thereof, and compositionsstabilized therewith
US2797242A (en) * 1953-08-11 1957-06-25 Parke Davis & Co Substituted alpha-benzylphenethylamines and methods for producing the same

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3194837A (en) * 1960-11-12 1965-07-13 Hoechst Ag N-arylalkyl-phenylalkyl amines
US3496181A (en) * 1966-10-24 1970-02-17 Upjohn Co 2 - aminocycloalkyl hydroquinones,esters,ethers and n-oxides thereof,and a process for preparing the same
US3992449A (en) * 1973-11-16 1976-11-16 Fuji Photo Film Co., Ltd. 2-(γ-Aminopropyl)hydroquinones and process for producing the same
US4704407A (en) * 1984-12-20 1987-11-03 Eli Lilly And Company Soluble dobutamine salts
US6001884A (en) * 1991-08-23 1999-12-14 Nps Pharmaceuticals, Inc. Calcium receptor-active molecules
US6011068A (en) * 1991-08-23 2000-01-04 Nps Pharmaceuticals, Inc. Calcium receptor-active molecules
US6313146B1 (en) 1991-08-23 2001-11-06 Nps Pharmaceuticals, Inc. Calcium receptor-active molecules
US6211244B1 (en) 1994-10-21 2001-04-03 Nps Pharmaceuticals, Inc. Calcium receptor-active compounds
US5981599A (en) * 1996-05-01 1999-11-09 Nps Pharmaceuticals, Inc. Inorganic ion receptor active compounds
US6342532B1 (en) 1996-05-01 2002-01-29 Nps Pharmaceuticals, Inc. Inorganic ion receptor active compounds
US6710088B2 (en) 1996-05-01 2004-03-23 Nps Pharmaceuticals, Inc. Inorganic ion receptor-active compounds
US6479198B2 (en) * 2000-02-01 2002-11-12 Fuji Photo Film Co., Ltd. Silver halide light-sensitive material containing tanning developing agent

Also Published As

Publication number Publication date
FR1210863A (fr) 1960-03-11
GB891767A (en) 1962-03-21
DE1111936B (de) 1961-07-27
BE570596A (ru)

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