UST889016I4 - Defensive publication - Google Patents

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Publication number
UST889016I4
UST889016I4 US889016DH UST889016I4 US T889016 I4 UST889016 I4 US T889016I4 US 889016D H US889016D H US 889016DH US T889016 I4 UST889016 I4 US T889016I4
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United States
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nucleus
dyes
group
nitrogen
atoms
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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
    • 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
    • C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
    • 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
    • C09B23/08—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines
    • C09B23/083—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines five >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
    • C09B23/14—Styryl dyes
    • 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
    • C09B23/145—Styryl dyes the ethylene chain carrying an heterocyclic residue, e.g. heterocycle-CH=CH-C6H5
    • 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

Definitions

  • This disclosure relates to novel dyes and photographic materials.
  • it relates to photographic silver halide emulsions spectrally sensitized with cyanine and hemicyanine dyes having a tertiary aminoalkyl group substituted on the heterocyclic nitrogen atom of the basic nucleus.
  • unsymmetrical cyanine dyes comprising first and second nuclei joined by a linkage selected from a trimethine linkage and a pentamethine linkage; the first nucleus being a nitrogen-containing basic heterocyclic nucleus of the type used in cyanine dyes, said hetero-nitrogen atom having attached thereto a tertiary aminoalkyl group; and the second nucleus being a nitrogen-containing basic heterocyclic nucleus of the type used in cyanine dyes, said heteronitrogen atom having attached thereto an alkyl group.
  • Highly useful photographic spectral sensitizing symmetrical cyanines and hemicyanines are also provided. Typical useful dyes have one of the following formulas:
  • n 1 to 3, k and 1' each represents 1 or 2; Z and Z each represents the non-metallic atoms required to complete a 5- to 6-membered nitrogen-containing basic heterocyclic nucleus;
  • R represents an alkylene group containing from 2 to 6 carbon atoms;
  • R and R each represents a member of the group consisting of alkyl, aryl and, R or R taken together, represent the atoms to complete, With the nitrogen atom to which they are attached, a heterocyclic nucleus containing from 5 to 6 atoms;
  • R represents an alkyl group or an aryl group;
  • R represents halogen, nitro, cyano or amino;
  • Z represents the atoms required to complete a basic heterocyclic nucleus; and
  • X represents an acid anion.
  • a typical useful dye is S-chloro-1,3'-diethyl-3-(2 morpholinoethyl)benzimidazolothiacarbocyanine io

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)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

THIS DISCLOSURE RELATES TO NOVEL DYES AND PHOTOGRAPHIC MATERIALS. IN ONE ASPECT IT RELATES TO PHOTOGRAPHIC SILVER HALIDE EMULSIONS SPECTRALLY SENSITIZED WITH CYANINE AND HEMICYANINE DYES HAVING A TERTIARY AMINOALKYL GROUP SUBSTITUTED ON THE HETEROCYCLIC NITROGEN ATOM OF THE BASIC NUCLEUS. IN ONE PREFERRED EMBODIMENT, UNSYMMETRICAL CYANINE DYES ARE PROVIDED COMPRISING FIRST AND SECOND NUCLEI JOINED BY A LINKAGE SELECTED FROM A TRIMETHINE LINKAGE AND A PENTAMETHINE LINKAGE; THE FIRST NUCLEUS BEING A NITROGEN-CONTAINING BASIC HETEROCYCLIC NUCLEUS OF THE TYPE USED IN CYANINE DYES, SAID HETERO-NITROGEN ATOM HAVING ATTACHED THERETO A TERTIARY AMINOALKYL GROUP; AND THE SECOND NEUCLEUS BEING A NITROGEN-CONTAINING BASIC HETEROCYCLIC NUCLEUS OF THE TYPE USED IN CYANINE DYES, SAID HETERONITROGEN ATOM HAVING ATTACHED THERETO AN ALKYL GROUP. HIGHLY USEFUL PHOTOGRAPHIC SPECTRAL SENSITIZING SYMMETRICAL CYANINES AND HEMICYANINES ARE ALSO PROVIDED. TYPICAL USEFUL DYES HAVE ONE OF THE FOLLOWING FORMULAS:

WHEREIN N REPRESENTS 1 TO 3, K AND J EACH REPRESENTS 1 OR 2; Z1 AND Z2 EACH REPRESENTS THE NON-METALLIC ATOMS REQUIRED TO COMPLETE A 5- TO 6-MEMBERED NITROGEN-CONTAINING BASIC HETEROCYCLIC NUCLEUS; R1 REPRESENTS AN ALKYLENE GROUP CONTAINING FROM 2 TO 6 CARBON ATOMS; R2 AND R3 EACH REPRESENTS A MEMBER OF THE GROUP CONSISTING OF ALKYL, ARYL AND, R2 OR R3 TAKEN TOGETHER, REPRESENT THE ATOMS TO COMPLETE, WITH THE NITROGEN ATOM TO WHICH THEY ARE ATTACHED, A HETEROCYCLIC NUCLEUS CONTAINING FROM 5 TO 6 ATOMS; R4 REPRESENTS AN ALKYL GROUP OR AR ARYL GROUP; R5 REPRESENTS HALOGEN, NITRO, CYANO OR AMINO; Z REPRESENTS THE ATOMS REQUIRED TO COMPLETE A BASIC HETEROCYCLIC NUCLEUS; AND X REPRESENTS AN ACID ANION. A TYPICAL USEFUL DYE IS 5-CHLORO-1,3''-DIETHYL-3-(2-MORPHOLINOETHYL) BENZIMIDAZOLOTHIACARBOCYANINE IODIDE.

Description

UNITED STATES PATENT OFFICE Published at the request of the applicant or owner in accordance with the Notice of Dec. 16, 1969, 869 0.6. 687. The abstracts of Defensive Publication applications are identified by distinctly numbered series and are arranged chronologically. The heading of each abstract indicates the number of pages of specification. including claims and sheets of drawings contained in the application as originally filed. The files of these applications are available to the public for inspection and reproduction may be purchased for 30 cents a sheet.
Defensive Publication applications have not been examined as to the merits of alleged invention. The Patent Oflice makes '10 assertion us to the novelty of the disclosed subject matter.
PUBLISHED AUGUST 31, 1971 T889,016 PHOTOGRAPHIC MATERIALS Earl J. Van Lare, Rochester, and Arthur Fumia, Jr., Hilton, N.Y. (both of Kodak Park, Rochester, NY. 14650) Filed Sept. 25, 1970, Ser. No. 75,786 lint. Cl. G03c 1/14 U.S. Cl. 96-127 No Drawing. 39 Pages Specification This disclosure relates to novel dyes and photographic materials. In one aspect it relates to photographic silver halide emulsions spectrally sensitized with cyanine and hemicyanine dyes having a tertiary aminoalkyl group substituted on the heterocyclic nitrogen atom of the basic nucleus. In one preferred embodiment, unsymmetrical cyanine dyes are provided comprising first and second nuclei joined by a linkage selected from a trimethine linkage and a pentamethine linkage; the first nucleus being a nitrogen-containing basic heterocyclic nucleus of the type used in cyanine dyes, said hetero-nitrogen atom having attached thereto a tertiary aminoalkyl group; and the second nucleus being a nitrogen-containing basic heterocyclic nucleus of the type used in cyanine dyes, said heteronitrogen atom having attached thereto an alkyl group. Highly useful photographic spectral sensitizing symmetrical cyanines and hemicyanines are also provided. Typical useful dyes have one of the following formulas:
wherein n represents 1 to 3, k and 1' each represents 1 or 2; Z and Z each represents the non-metallic atoms required to complete a 5- to 6-membered nitrogen-containing basic heterocyclic nucleus; R represents an alkylene group containing from 2 to 6 carbon atoms; R and R each represents a member of the group consisting of alkyl, aryl and, R or R taken together, represent the atoms to complete, With the nitrogen atom to which they are attached, a heterocyclic nucleus containing from 5 to 6 atoms; R represents an alkyl group or an aryl group; R represents halogen, nitro, cyano or amino; Z represents the atoms required to complete a basic heterocyclic nucleus; and X represents an acid anion. A typical useful dye is S-chloro-1,3'-diethyl-3-(2 morpholinoethyl)benzimidazolothiacarbocyanine iodide.
US889016D 1970-09-25 1970-09-25 Defensive publication Pending UST889016I4 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US7578670A 1970-09-25 1970-09-25

Publications (1)

Publication Number Publication Date
UST889016I4 true UST889016I4 (en) 1971-08-31

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Family Applications (1)

Application Number Title Priority Date Filing Date
US889016D Pending UST889016I4 (en) 1970-09-25 1970-09-25 Defensive publication

Country Status (3)

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US (1) UST889016I4 (en)
CA (1) CA970372A (en)
FR (1) FR2108592A5 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4138551A (en) 1975-03-18 1979-02-06 Ciba-Geigy Ag Spectral sensitization of photographic material and new spectral sensitizers

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105131645B (en) * 2014-06-02 2018-02-09 响水县嘉禾纺织制衣有限公司 A kind of cotton reactive fluorescent dye, preparation and application

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4138551A (en) 1975-03-18 1979-02-06 Ciba-Geigy Ag Spectral sensitization of photographic material and new spectral sensitizers

Also Published As

Publication number Publication date
FR2108592A5 (en) 1972-05-19
CA970372A (en) 1975-07-01

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