US2255128A - Pseudocyanine dye - Google Patents

Pseudocyanine dye Download PDF

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Publication number
US2255128A
US2255128A US194838A US19483838A US2255128A US 2255128 A US2255128 A US 2255128A US 194838 A US194838 A US 194838A US 19483838 A US19483838 A US 19483838A US 2255128 A US2255128 A US 2255128A
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Prior art keywords
pseudocyanine
dye
alkyl
sensitizing
pseudocyanine dye
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Expired - Lifetime
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US194838A
Inventor
Riester Oskar
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GAF Chemicals Corp
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General Aniline and Film Corp
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    • 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
    • C09B23/04—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
    • C09B23/14—Styryl dyes
    • C09B23/145—Styryl dyes the ethylene chain carrying an heterocyclic residue, e.g. heterocycle-CH=CH-C6H5

Definitions

  • My present invention relates to new dyes of i the pseudocyanine series.
  • This invention is based on the discovery that the benzoxocyanines substituted in the 5-position by a phenyl group havea superior sensitizing effect in the greenor the blue-green portion of the spectrum.
  • the quinoline nucleus in the pseudocyanine dyestuii may be substituted by known substituents for example by alkyl, oxalkyl.
  • the 5-phenylbenzoxazole serving as the parent material may be produced as follows:
  • Para-oxydiphenyl is nitrated, whereby the nitro-group enters into ortho-position relatively to the oxy-group.
  • the nitro-compound may be separated from dye-products by distillation with steam.
  • the nitro-compound is reduced, for instance with sodium hydrosulphite in alkaline solution.
  • the amino-compound is then converted into the oxazole by distillation with acetic anhydride.
  • the quaternary salt may be converted by known methods into the pseudocyaninesl' Instead of 5-phenyl-2-alkylbenzoxazole there may be used. a 5-pheny1-2-alkylbenzoxazole containing as a substituent in the 6-position a methyl or oXalkyl-group.
  • Example 3 A pseudo'cyanine produced by condensing the 5-phenyl 2 methyl benzoxazole methyliodide with N-ethylthio-7-ethoxy-quinoline ethyliodide in pyridine corresponds with the following formula:
  • Example 4 A pseudocyanine produced by condensing the 5-pheny1-2-methyl-benzoxazole propyliodide with N-propy1thio-6-methoxy-quinoline-ethyliodide in pyridine corresponds with the following formula:
  • these dyes have sharply limited regions of sensitizing effect and are therefore very suitable for various special purposes, especially for color photography and in the particular for processes in which multi-layer color sensitized material is used. They have also the advantage that they are. insensitive to dyestufi components such as are used in the emulsion in various multilayer processes. 7
  • sensitizing photographic silver halide emulsions with these dyes is conducted in the usual manner by adding the dyestufi to the emulsion at any stage of its production or by bathing the layer of emulsion in a solution of the dyestufi diluted to the usual extent.
  • a pseudocyanine dye having the following structure:
  • a pseudocyanine dye having the following structure:

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Description

Patented Sept. 9, 1941 UNlT rrrs 2,255,128 PSEUDOCYANINE DYE Uskar Riester, Dessau, Germany, assignor, by mesne assignments, to General Aniline & Film Corporation, New York, N. Y., a corporation of Delaware No Drawing.
Application March 9, 1938, Serial N0. 194,838.v In Germany March 13,1937
4 Claims.
My present invention relates to new dyes of i the pseudocyanine series.
It is already known to sensitize silver halide emulsions by means of oxopseudocyanines. An object of the present invention is the provision of substituted benzoxopseudocyanines. Further objects will be seen from the detailed specification following hereinafter. i
This invention is based on the discovery that the benzoxocyanines substituted in the 5-position by a phenyl group havea superior sensitizing effect in the greenor the blue-green portion of the spectrum.
The quinoline nucleus in the pseudocyanine dyestuii may be substituted by known substituents for example by alkyl, oxalkyl. The 5-phenylbenzoxazole serving as the parent material may be produced as follows:
Para-oxydiphenyl is nitrated, whereby the nitro-group enters into ortho-position relatively to the oxy-group. By the formation of the oxazole the position of the nitro-group is generally settled (compare Annalen 207, page 351, Annalen 209, page 348). The nitro-compound may be separated from dye-products by distillation with steam. For making the amino-compound the nitro-compound is reduced, for instance with sodium hydrosulphite in alkaline solution. The amino-compound is then converted into the oxazole by distillation with acetic anhydride.
thereof is converted into the quaternary ammonium salt in the usual manner by heating it Furthermore, it is possible with alkyl iodide or another alkyl ester. The quaternary salt may be converted by known methods into the pseudocyaninesl' Instead of 5-phenyl-2-alkylbenzoxazole there may be used. a 5-pheny1-2-alkylbenzoxazole containing as a substituent in the 6-position a methyl or oXalkyl-group.
The following examples illustrate the present invention, but they are not intended to limit it thereto: r Example 1 0 with N-ethylthio-G-methoxy-quinoline ethylio dide in pyridine corresponds with the following formula:
7 O OCH:
sensitizing maximum, 5000 A. E.
Example 3 A pseudo'cyanine produced by condensing the 5-phenyl 2 methyl benzoxazole methyliodide with N-ethylthio-7-ethoxy-quinoline ethyliodide in pyridine corresponds with the following formula:
sensitizing maximum, 4950 E.
Example 4 A pseudocyanine produced by condensing the 5-pheny1-2-methyl-benzoxazole propyliodide with N-propy1thio-6-methoxy-quinoline-ethyliodide in pyridine corresponds with the following formula:
(II-CH- N f O OCH:
sensitizing maximum, 5100 A. E.
Example 5 sensitizing maximum, 5050 A. E.
Moreover these dyes have sharply limited regions of sensitizing effect and are therefore very suitable for various special purposes, especially for color photography and in the particular for processes in which multi-layer color sensitized material is used. They have also the advantage that they are. insensitive to dyestufi components such as are used in the emulsion in various multilayer processes. 7
The operation of sensitizing photographic silver halide emulsions with these dyes is conducted in the usual manner by adding the dyestufi to the emulsion at any stage of its production or by bathing the layer of emulsion in a solution of the dyestufi diluted to the usual extent.
I claim:
1. A pseudocyanine dye having the following structure:
2. A pseudocyanine dye having the following structure:
3. A pseudocyanine dye having the following structure:
4. A cyanine dye salt of the formula i X N N/ alkyl alkyl anion wherein X is selected from the class consisting of hydrogen, alkyl and alkoxy, one X always being hydrogen.
OSKAR RIES'IER.
US194838A 1937-03-13 1938-03-09 Pseudocyanine dye Expired - Lifetime US2255128A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE512494X 1937-03-13

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BE (1) BE426909A (en)
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GB (1) GB512494A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2515913A (en) * 1946-11-22 1950-07-18 Eastman Kodak Co 2-methyl-5-phenylbenzothiazole and quaternary salts thereof
US4002635A (en) * 1972-12-04 1977-01-11 Ciba-Geigy Corporation Isoindolinone compounds useful in preparing heavy metal containing pigments

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE944027C (en) * 1952-08-05 1956-06-07 Bayer Ag Process for the preparation of polymethine or styryl dyes substituted in the methine chain

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2515913A (en) * 1946-11-22 1950-07-18 Eastman Kodak Co 2-methyl-5-phenylbenzothiazole and quaternary salts thereof
US4002635A (en) * 1972-12-04 1977-01-11 Ciba-Geigy Corporation Isoindolinone compounds useful in preparing heavy metal containing pigments

Also Published As

Publication number Publication date
BE426909A (en)
GB512494A (en) 1939-09-18
FR835134A (en) 1938-12-13

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