GB783021A - Improvements in cyanine dyes, processes of preparing them and photographic emulsionscontaining them - Google Patents

Improvements in cyanine dyes, processes of preparing them and photographic emulsionscontaining them

Info

Publication number
GB783021A
GB783021A GB23659/55A GB2365955A GB783021A GB 783021 A GB783021 A GB 783021A GB 23659/55 A GB23659/55 A GB 23659/55A GB 2365955 A GB2365955 A GB 2365955A GB 783021 A GB783021 A GB 783021A
Authority
GB
United Kingdom
Prior art keywords
methyl
formula
nucleus
benzothiazole
completes
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
GB23659/55A
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.)
Kodak Ltd
Original Assignee
Kodak 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
Application filed by Kodak Ltd filed Critical Kodak Ltd
Publication of GB783021A publication Critical patent/GB783021A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • 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
    • 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
    • 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
    • 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

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)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Dyes of the general formul <FORM:0783021/IV (b)/1> and <FORM:0783021/IV (b)/2> wherein R and R1 are alkyl or substituted alkyl groups, X is an acid radical, n is 0 or 1, d is 1 or 2, Z completes a benzothiazole or quinoline nucleus and Z1 and Q complete heterocyclic nuclei, are prepared by condensing a quaternary salt of the formula <FORM:0783021/IV (b)/3> with a compound of the formula <FORM:0783021/IV (b)/4> wherein R2 is an acyl group, R3 is an aryl group and X1 is an acid radical, or with a compound of the general formula <FORM:0783021/IV (b)/5> The nucleus completed by Z may contain chlorine, bromine, iodine, methoxy, ethoxy, methyl, ethyl or phenyl substituents. Substituted alkyl groups which R or R1 may represent are allyl, b -hydroxyethyl and benzyl. Lists of nuclei which Z1 and Q may complete are given. In the examples, Z1 completes a benzothiazole, benzoxazole, benzselenazole, naphthothiazole or thiazoline nucleus and Q completes a rhodanine nucleus. Specification 670,038 and U.S.A. Specification 2,073,600 are referred to.ALSO:Compounds of the formula: <FORM:0783021/IV (a)/1> where Z completes a benzthiazole or quinoline nucleus (which may be substituted by halogen atoms, alkyl, alkoxy or phenyl groups) are prepared by condensing a compound of formula: <FORM:0783021/IV (a)/2> with acetic anhydride in the presence of a strong acid such as glacial acetic or phosphoric acid. Preferably the hydrazine group is first acylated, and the crystallized product treated with fresh acetic anhydride and strong acid to effect ring closure. The bases produced may be quaternized by heating them with a compound RX (R = alkyl, allyl, b -hydroxyethyl or benzyl and X is an anion) such as ethyl iodide, methyl iodide, diethyl sulphate and methyl paratoluenesulphonate. The preparation of the following unquaternated compounds is described: 1 - methyl - s - triazolo [4,3 - a] quinoline, 1 - methyl - s - triazolo [3,4 - b] benzothiazole and 6 - methoxy - 1 - methyl - s-thiazolo [3,4 - b] benzothiazole. The preparation of quaternary derivatives of the latter compounds is also described. 2 - Acetylhydrazinobenzothiazole is prepared by refluxing 2-hydrazinobenzothiazole with acetic anhydride. Specification 670,038, [Group IV (c)], and U.S.A. Specification 2,073,600 are referred to.
GB23659/55A 1956-06-25 1955-08-17 Improvements in cyanine dyes, processes of preparing them and photographic emulsionscontaining them Expired GB783021A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US852955XA 1956-06-25 1956-06-25

Publications (1)

Publication Number Publication Date
GB783021A true GB783021A (en) 1957-09-18

Family

ID=22190666

Family Applications (2)

Application Number Title Priority Date Filing Date
GB23659/55A Expired GB783021A (en) 1956-06-25 1955-08-17 Improvements in cyanine dyes, processes of preparing them and photographic emulsionscontaining them
GB17500/57A Expired GB852955A (en) 1956-06-25 1957-06-03 New merocyanine dye, processes of preparing it and photographic emulsions containing it

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB17500/57A Expired GB852955A (en) 1956-06-25 1957-06-03 New merocyanine dye, processes of preparing it and photographic emulsions containing it

Country Status (3)

Country Link
BE (2) BE540630A (en)
FR (1) FR1138331A (en)
GB (2) GB783021A (en)

Also Published As

Publication number Publication date
BE558627A (en)
FR1138331A (en) 1957-06-12
GB852955A (en) 1960-11-02
BE540630A (en)

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