GB825965A - Optical sensitisation of direct positive photographic emulsions - Google Patents

Optical sensitisation of direct positive photographic emulsions

Info

Publication number
GB825965A
GB825965A GB8996/57A GB899657A GB825965A GB 825965 A GB825965 A GB 825965A GB 8996/57 A GB8996/57 A GB 8996/57A GB 899657 A GB899657 A GB 899657A GB 825965 A GB825965 A GB 825965A
Authority
GB
United Kingdom
Prior art keywords
methyl
indole
methoxyphenyl
phenyl
prepared
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
GB8996/57A
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.)
Agfa Gevaert NV
Original Assignee
Agfa AG
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
Application filed by Agfa AG filed Critical Agfa AG
Publication of GB825965A publication Critical patent/GB825965A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/06—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups three >CH- groups, e.g. carbocyanines
    • 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
    • G03C1/14—Methine and polymethine dyes with an odd number of CH groups
    • G03C1/18—Methine and polymethine dyes with an odd number of CH groups with three CH groups
    • 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
    • G03C1/485—Direct positive emulsions
    • G03C1/48515—Direct positive emulsions prefogged
    • G03C1/48523—Direct positive emulsions prefogged characterised by the desensitiser
    • G03C1/4853—Direct positive emulsions prefogged characterised by the desensitiser polymethine dyes
    • 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
    • G03C1/485—Direct positive emulsions
    • G03C1/48538—Direct positive emulsions non-prefogged, i.e. fogged after imagewise exposure
    • G03C1/48584—Direct positive emulsions non-prefogged, i.e. fogged after imagewise exposure spectrally sensitised

Landscapes

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

Abstract

Indole derivatives of the general formula <FORM:0825965/IV (b)/1> in which R is methyl, R11 is thienyl, phenyl, or p-methoxyphenyl and R111 is H, methyl or methoxy, are prepared by reacting the corresponding ketones having a -CO.R11 group in the 3-position with a Grignard reagent such as that from magnesium and methyl iodide in ether, and mixing with iced water and sulphuric acid. 1 - Methyl - 2 - phenyl - 3 - benzoyl - indole is prepared by heating 1-methyl-2-phenyl-indole, benzanilide and phosphorus oxychloride at 110 DEG C. and pouring into dilute hydrochloric acid. The 2-(p-methoxyphenyl) derivative is similarly made. By using p-methoxybenzanilide, 1 - methyl - 2 - phenyl - 3 - (p - methoxy-benzoyl)-indole may be obtained. [1-Methyl-2-(p-methoxyphenyl) - indolyl - 3] - a - thienyl ketone is similarly prepared from thiophene-a -carboxylic acid anilide, 1-methyl-2-(p-methoxyphenyl)-indole and phosphorus oxychloride. 1 - Methyl - 2 - (p - methoxyphenyl) - indole is prepared by melting the N-methyl-phenylhydrazone of p-methoxyacetophenone with zinc chloride. 1 - Methyl - 2 - (p - methoxyphenyl) - 3 - formylindole is prepared by mixing N-methyl-formylaniline and phosphorus oxychloride and leaving to stand for 2 hours, then adding o-dichloro-benzene and 1-methyl-2-(p-methoxyphenyl)indole at 50 DEG C., leaving to stand for 20 hours, and decomposing with ice and sodium hydroxide solution. The corresponding 2-(p-chlorophenyl)-derivative is similarly made. Specifications 405,642 and 443,245, [both in Group XX], are referred to.ALSO:The Specification describes dyes of the general formula <FORM:0825965/IV(c)/1> wherein R is an alkyl group, R1 and R111 each are H, halogen, alkyl or alkoxy, R11 is H or an alkyl, cycloalkyl, thienyl or R1-C6H4 radical and X is an anion. Symmetrical dyes wherein R11 is H may be prepared by reacting the appropriate indole such as 1-methyl-2-phenyl indole or N-methyl-2-(p- or o-methylphenyl) indole with b -ethoxy-acrolein acetal for example in the presence of HBr to give the bromide. Unsymmetrical dyes wherein R11 is other than H may be prepared by reacting ketones such as 1-methyl - 2 - phenyl - 3 - benzoyl indole, 1-methyl - 2 - (p - methoxyphenyl - 3 - benzoyl indole, 1 - methyl - 2 - phenyl - 3 - (p - methoxybenzoyl) indole or [1 - methyl - 2 - (p - methoxyphenyl) - indolyl - 3] - a - thienyl ketone with a Grignard agent to give a compound of formula <FORM:0825965/IV(c)/2> and reacting this with a 3-formyl indole such as 1 - methyl - 2 - phenyl - 3 - formyl - indole and the corresponding 2 - (p - methoxyphenyl) - or 2 - (p - chlorophenyl) - derivatives; for example in the presence of glacial acetic acid and HBr. Specifications 405,642 and 443,245, [both in Group XX], are referred to.
GB8996/57A 1956-03-19 1957-03-19 Optical sensitisation of direct positive photographic emulsions Expired GB825965A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEA24514A DE1008118B (en) 1956-03-19 1956-03-19 Process for the sensitization of direct-positive emulsions containing color formers

Publications (1)

Publication Number Publication Date
GB825965A true GB825965A (en) 1959-12-23

Family

ID=6925685

Family Applications (1)

Application Number Title Priority Date Filing Date
GB8996/57A Expired GB825965A (en) 1956-03-19 1957-03-19 Optical sensitisation of direct positive photographic emulsions

Country Status (6)

Country Link
US (1) US2930694A (en)
BE (1) BE555921A (en)
CH (1) CH355026A (en)
DE (1) DE1008118B (en)
FR (1) FR1177726A (en)
GB (1) GB825965A (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE566164A (en) * 1957-03-28
BE636671A (en) * 1960-05-13
US3501310A (en) * 1966-03-11 1970-03-17 Eastman Kodak Co Direct positive silver halide emulsions containing compounds which accept electrons and spectrally sensitize the emulsion
US3510348A (en) * 1966-03-11 1970-05-05 Eastman Kodak Co Direct positive recording film
CH482782A (en) * 1967-10-19 1969-12-15 Eastman Kodak Co Process for the manufacture of trimethine cyanines with indole rings
US3541089A (en) * 1967-10-19 1970-11-17 Eastman Kodak Co Method of preparing chain-substituted trimethine indole dyestuffs
US3501312A (en) * 1968-07-22 1970-03-17 Eastman Kodak Co Direct positive silver halide emulsions containing trimethine cyanine dyes
GB1456243A (en) * 1973-01-25 1976-11-24 Agfa Gevaert Directpositive silver halide elements
IT988269B (en) * 1973-06-18 1975-04-10 Minnesota Mining & Mfg CYANINE DYES AND THEIR USE AS SPECTRAL SENSITIZERS IN DIRECT POSITIVE PHOTOGRAPHIC MATERIALS OF THE SPECTRALLY SENSITIZED HERSCHEL EFFECT TYPE

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2126078A (en) * 1932-04-26 1938-08-09 Agfa Ansco Corp Sensitizing photographic emulsion
BE484580A (en) * 1947-08-29
BE529197A (en) * 1953-05-28

Also Published As

Publication number Publication date
BE555921A (en)
US2930694A (en) 1960-03-29
DE1008118B (en) 1957-05-09
FR1177726A (en) 1959-04-29
CH355026A (en) 1961-06-15

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