GB778613A - New sensitisers for photographic emulsions - Google Patents

New sensitisers for photographic emulsions

Info

Publication number
GB778613A
GB778613A GB3191154A GB3191154A GB778613A GB 778613 A GB778613 A GB 778613A GB 3191154 A GB3191154 A GB 3191154A GB 3191154 A GB3191154 A GB 3191154A GB 778613 A GB778613 A GB 778613A
Authority
GB
United Kingdom
Prior art keywords
ethyl
cyano
phenyl
formula
acetanilide
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
Application number
GB3191154A
Inventor
George De Winter Anderson
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 BE542526D priority Critical patent/BE542526A/xx
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB3191154A priority patent/GB778613A/en
Priority to DEI10857A priority patent/DE1060073B/en
Priority to FR1134647D priority patent/FR1134647A/en
Publication of GB778613A publication Critical patent/GB778613A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
    • C07D231/26—1-Phenyl-3-methyl-5- pyrazolones, unsubstituted or substituted on the phenyl ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/86—Oxygen and sulfur atoms, e.g. thiohydantoin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/46—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/0091—Methine or polymethine dyes, e.g. cyanine dyes having only one heterocyclic ring at one end of the methine chain, e.g. hemicyamines, hemioxonol
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/14—Styryl dyes
    • C09B23/143—Styryl dyes the ethylene chain carrying a COOH or a functionally modified derivative, e.g.-CN, -COR, -COOR, -CON=, C6H5-CH=C-CN
    • 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
    • G03C1/00—Photosensitive materials
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/08—Sensitivity-increasing substances
    • G03C1/10—Organic substances
    • G03C1/12—Methine and polymethine dyes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)

Abstract

Compounds of the formula: <FORM:0778613/IV(b)/1> wherein X completes a 5- or 6-membered heterocyclic ring, n is 0, 1 or 2 and Ar is an aryl radical, are prepared by condensing a ketomethylene compound of the formula: <FORM:0778613/IV(b)/2> with diphenyl-formamidine, g -anilino-acraldehyde anil hydrochloride or glutaconic aldehyde dianilide hydrochloride. 4 - Anilinomethylene-1 - phenyl - 3 - methyl - 5 - pyrazolone, 3 - ethyl-5 - anilinomethylene - rhodanine, 3 - ethyl - 1-phenyl - 5 - (g - anilino - allylidene) - 2 - thiohydration and 3 - ethyl - 5 - (g - anilino - allylidene) - rhodanine are referred to. Compounds of the general formula: <FORM:0778613/IV(b)/3> wherein Ar is an aryl radical, Ac is an acyl radical, n is 0, 1 or 2 and R is cyano or carboxylic acid (or salt thereof) or, where n = 1 or 2 R may be carboxylic ester, are prepared by acylating the products obtained by condensing malonic dinitrile, cyanacetic acid or a cyanacetic ester with diphenyl-formamidine, g -anilino-acralaniline or glutaconic aldehyde dianil. Reference is made to N-(2 : 2-dicyano-ethenyl - 1) - acetanilide, N - (6 : 6 - dicyano-1 : 3 : 5 - hexatrienyl - 1) acetanilide and N-(4 : 4 - dicyano - or N(4 - cyano - 4 - carboethoxy - 1 : 3 - butadienyl - 1) acetanilides.ALSO:Dyes of the general formula:-<FORM:0778613/IV(b)/1> wherein X completes a 5- or 6-membered heterocyclic ring, M is hydrogen or an alkali metal or ammonium radical, n is O, 1 or 2 and R is a cyano or carboxylic acid group or salt thereof, or, when n is 1 or 2 R may be carboxylic ester, are prepared by condensing a compound of the formula: <FORM:0778613/IV(b)/2> (Ar = an aryl radical) or an N - acyl derivative thereof, with malonic dinitrile or cyanacetic acid, or, when n = 1 or 2 with a cyanacetic ester, or they may be prepared by condensing a compound of the formula:- <FORM:0778613/IV(b)/3> (Ac = an acyl radical) with a heterocyclic compound of the formula:- <FORM:0778613/IV(b)/4> In the first method the starting material may be 4 - anilinomethylene - 1 - phenyl-3 - methyl - 5 - pyrazolone, 3 - ethyl - 5-anilinomethylene - rhodanine, 3 - ethyl-1 - phenyl - 5 - (g - anilinoallylidine) - 2-thiohydantoin, or 3 - ethyl - 5 - (g - anilinoallylidene) - rhodanine, while in the second method 1 - phenyl - 3 - methyl - 5 - pyrazolone, 3 - ethyl - 1 - phenyl - 2 - thiohydantoin or 3 - ethyl - oxazolid - 4 - one - 2 - thione may be used, together with N - (2 : 2 - dicyanoethenyl - 1) acetanilide, N - (6 : 6 - di - cyano - 1 : 3 : 5 - hexatrienyl - 1)acetanilide or N - (4 - cyano-4 - carboethoxy (or cyano) - 1 : 3 - butadienyl - 1) acetanilide. The condensations may be carried out in ethanol in the presence of KOH or NaOCH3 (yielding the K or Na salts). According to the Provisional Specification, n may be 3 and R may be carboxylic ester for any value of n.
GB3191154A 1954-11-04 1954-11-04 New sensitisers for photographic emulsions Expired GB778613A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
BE542526D BE542526A (en) 1954-11-04
GB3191154A GB778613A (en) 1954-11-04 1954-11-04 New sensitisers for photographic emulsions
DEI10857A DE1060073B (en) 1954-11-04 1955-11-02 Process for the preparation of sensitizing dyes
FR1134647D FR1134647A (en) 1954-11-04 1955-11-04 New sensitizers for photographic emulsions

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3191154A GB778613A (en) 1954-11-04 1954-11-04 New sensitisers for photographic emulsions

Publications (1)

Publication Number Publication Date
GB778613A true GB778613A (en) 1957-07-10

Family

ID=10330230

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3191154A Expired GB778613A (en) 1954-11-04 1954-11-04 New sensitisers for photographic emulsions

Country Status (4)

Country Link
BE (1) BE542526A (en)
DE (1) DE1060073B (en)
FR (1) FR1134647A (en)
GB (1) GB778613A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3121008A (en) * 1959-04-09 1964-02-11 Eastman Kodak Co Photoconductive zinc oxide compositions comprising oxonol, hemioxonol, or benzylidene dyes
US3395017A (en) * 1964-07-02 1968-07-30 Eastman Kodak Co Silver halide photographic element containing acidic polymethine dyes and holopolar cyanines

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB610569A (en) * 1946-04-01 1948-10-18 John David Kendall Improvements in or relating to the production of dyes and the sensitisation of photographic emulsions
DE893289C (en) * 1948-10-02 1953-10-15 Ilford Ltd Sensitized silver halide emulsion
DE821524C (en) * 1949-11-01 1951-11-19 Bayer Ag Process for the preparation of benzimidazole netrocyanines

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3121008A (en) * 1959-04-09 1964-02-11 Eastman Kodak Co Photoconductive zinc oxide compositions comprising oxonol, hemioxonol, or benzylidene dyes
US3395017A (en) * 1964-07-02 1968-07-30 Eastman Kodak Co Silver halide photographic element containing acidic polymethine dyes and holopolar cyanines

Also Published As

Publication number Publication date
BE542526A (en)
FR1134647A (en) 1957-04-15
DE1060073B (en) 1959-06-25

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