GB1385030A - Merocyaninic dyes and their use in silver halides photographic emulsions containing the same - Google Patents

Merocyaninic dyes and their use in silver halides photographic emulsions containing the same

Info

Publication number
GB1385030A
GB1385030A GB1088272A GB1088272A GB1385030A GB 1385030 A GB1385030 A GB 1385030A GB 1088272 A GB1088272 A GB 1088272A GB 1088272 A GB1088272 A GB 1088272A GB 1385030 A GB1385030 A GB 1385030A
Authority
GB
United Kingdom
Prior art keywords
thff
reacted
thiohydantoin
propyl
ethyl ester
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
GB1088272A
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.)
3M Co
Original Assignee
Minnesota Mining and Manufacturing Co
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 Minnesota Mining and Manufacturing Co filed Critical Minnesota Mining and Manufacturing Co
Publication of GB1385030A publication Critical patent/GB1385030A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • G03C1/22—Methine and polymethine dyes with an even number of CH groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • 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
    • C09B23/0008—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain
    • C09B23/0025—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being bound through an oxygen atom
    • 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
    • C09B23/0008—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain
    • C09B23/0033—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being bound through a sulfur atom
    • 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
    • C09B23/10—The polymethine chain containing an even number of >CH- groups
    • 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
    • C09B23/10—The polymethine chain containing an even number of >CH- groups
    • C09B23/105—The polymethine chain containing an even number of >CH- groups two >CH- groups
    • 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
    • C09B23/10—The polymethine chain containing an even number of >CH- groups
    • C09B23/107—The polymethine chain containing an even number of >CH- groups four >CH- groups

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)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

1385030 Furan and tetrahydrofuran derivatives MINNESOTA'MINING & MFG CO 8 March 1972 [9 March 1971] 10882/72 Heading C2C [Also in Division C4] CS 2 is reacted with THFF- and FF-amines (in which THFF is α-tetrahydrofurfuryl and FF is α-furfuryl) to form (1), (2) THFF- and FF- isothiocyanates respectively. (1) is reacted (a) with sarcosine and acetic anhydride to form (3) 1-methyl-3-THFF-2-thiohydantoin- (b) with iminoacetic acid diethyl ester to form 1-carboxymethyl-3-THFF-2-thiohydantoin ethyl ester which is hydrolysed to (4) the free acid; (c) with thioglycolic acid to form (5) 3-THFF-rhodanine. (8) 3-FF-rhodanine is prepared similarly. FF amine is reacted with chloroacetamide to form (6) (FF-amino)acetamide.HCl which is reacted with propyl isothiocyanate or dimethylaminopropylisothiocyanate to form (9), (7) 1-FF-3-(propyl or dimethylaminopropyl)-2- thiohydantoin, respectively. (9) is reacted with diphenylformamide to form 5-anilinomethylene- 1-FF-3-propyl-2-thiohydantoin which is acylated to (17) 5-acetanilidomethylene-1-FF-3-propyl-2- thiohydantoin. FF-amine is reacted with ethylbromoaeetate to form (10) N-(FF) glycine ethyl ester which is reacted with carboethoxymethylisothiocyanate to form 1-FF-3-carboxymethyl-2-thiohydantoin ethyl ester which is hydrolysed to (11) the free acid. N-(THFF)-glycine ethyl ester is reacted with ethyl isocyanate to form (12) 1-THFF-3-ethyl-2- thiohydantoin. Acetamido-carbodithioloneglycolic acid is reacted with FF- or THFF-amine to form (13), (14) 3-(FF or THFF)-2-thio oxazolidone, respectively which are reacted with diphenylformamidine to form 5-anilino-methylene-3- (FF or THFF)-2-thiooxazolidone which is acetylated to (15), (16) 5-acetanilidomethylene-3-(FF or THFF)-2-thiooxazolidone.
GB1088272A 1971-03-09 1972-03-08 Merocyaninic dyes and their use in silver halides photographic emulsions containing the same Expired GB1385030A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT4891971 1971-03-09

Publications (1)

Publication Number Publication Date
GB1385030A true GB1385030A (en) 1975-02-26

Family

ID=11269033

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1088272A Expired GB1385030A (en) 1971-03-09 1972-03-08 Merocyaninic dyes and their use in silver halides photographic emulsions containing the same

Country Status (5)

Country Link
US (1) US3836370A (en)
BE (1) BE780443A (en)
DE (1) DE2211200A1 (en)
FR (1) FR2128737B1 (en)
GB (1) GB1385030A (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3976640A (en) * 1975-02-18 1976-08-24 Polaroid Corporation Bis-type quaternary salts including benzothiazole and benzimidazole rings and process for preparing dye therewith
DE69329964T2 (en) * 1992-11-19 2001-09-13 Eastman Kodak Co., Rochester Furan or pyrrole substituted dye compounds and photographic silver halide elements containing such dyes
JP3588160B2 (en) * 1994-05-18 2004-11-10 イーストマン コダック カンパニー Blue sensitizing dye having heterocyclic substituent

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB519895A (en) * 1938-10-06 1940-04-09 John David Kendall Improvements in or relating to the sensitizing of photographic emulsions
US3384486A (en) * 1964-05-04 1968-05-21 Eastman Kodak Co Merocyanine dyes for photographic elements containing an extracyclic tertiary amino group
JPS4824540B1 (en) * 1969-04-09 1973-07-21
US3718476A (en) * 1970-10-23 1973-02-27 Eastman Kodak Co Silver halide element containing merocyanine dyes with a 3-pyrrolinylalkyl group

Also Published As

Publication number Publication date
BE780443A (en) 1972-09-11
FR2128737B1 (en) 1978-03-03
FR2128737A1 (en) 1972-10-20
DE2211200A1 (en) 1973-03-22
US3836370A (en) 1974-09-17

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
732 Registration of transactions, instruments or events in the register (sect. 32/1977)
PCNP Patent ceased through non-payment of renewal fee