GB432969A - Process for sensitising photographic silver halide emulsions and manufacture of sensitising dyes therefor - Google Patents
Process for sensitising photographic silver halide emulsions and manufacture of sensitising dyes thereforInfo
- Publication number
- GB432969A GB432969A GB4031/34A GB403134A GB432969A GB 432969 A GB432969 A GB 432969A GB 4031/34 A GB4031/34 A GB 4031/34A GB 403134 A GB403134 A GB 403134A GB 432969 A GB432969 A GB 432969A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- naphthoxazole
- dyes
- prepared
- salt
- 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
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
Abstract
Photographic silver halide emulsions are sensitized by incorporating therein a dye of the cyanine, pseudocyanine, isocyanine, carbocyanine, or styryl series containing an unsubstituted or substituted b -b <1>-naphthoxazole nucleus. The dyes are derived from a quaternary ammonium salt of 2-methyl-b .b <1>-naphthoxazole or a substitution product thereof, reference being made to alkyl, aryl, unsubstituted and substituted amino and halogen as suitable substituents; thus pseudocyanine and cyanine dyes are prepared by condensing such a salt with a quaternary ammonium salt of a 2-iodo derivative of a quinoline base or with a derivative of a quinoline or other heterocyclic base having in the 2-position a bivalent polyatomic grouping of which the atom linked to the 2-position is different from carbon, such as the group = <FORM:0432969/IV/1> (cf. Specification 423,792); isocyanine dyes are prepared by condensing such a salt with a quaternary ammonium salt of quinoline or of a substitution product thereof in presence of an alkali alcoholate; styryl dyes are prepared by condensing such a salt with a p-dialkylaminobenzaldehyde or a substitution product thereof; carbocyanine dyes are prepared by condensing such a salt with a trialkyl ester of an orthocarboxylic acid or with an alkyl ester of a thioimidic acid (in this latter case unsymmetrical carbocyanines can also be obtained by reacting the specified salt with the thioimidic acid ester and with a quaternary ammonium salt of another hetero-cyclic base having a reactive methyl group according to the process of Specification 412,309). The following preparations are described in examples: (1) 2-methyl-b -b <1>-naphthoxazole dimethylsulphate is condensed with triethyl orthoformate, triethylorthoacetate, triethylorthopropionate in pyridine, in each case the dyes being precipitated as the bromides by adding potassium bromide; (2) 2-methyl-b -b <1>-naphthoxazole dimethylsulphate is condensed with N-ethyltoluthioquinolone ethiodide in pyridine in presence of piperidine to give 1.6<1> - dimethyl - 1<1> - ethyl - b .b <1> - naphthoxo-pseudocyanine iodide; (3) 2-methyl-b .b <1>-naphthoxazole dimethylsulphate is condensed with p-toluquinoline ethiodide in alcohol containing sodium alcoholate to give 1.6<1>-dimethyl-1<1>-ethyl - b .b <1> - naphthoxoisocyanine iodide; (4) 2-methyl-b .b <1>-naphthoxazole dimethylsulphate is condensed with p-dimethylaminobenzaldehyde in pyridine and in presence of piperidine. Samples have been furnished under Sect. 2 (5) of dyes prepared as follows: (a) 2-methyl-b .b <1>-naphthoxazole dimethylsulphate is condensed with ethylisothioacetanilide and the dye precipitated out by adding potassium iodide; (b) 2-methyl-b .b <1>-naphthoxazole dimethylsulphate is condensed with N - methylthiothiazolone ethiodide in pyridine and in presence of piperidine. 2-Methyl-b -b -naphthoxazoles are prepared by splitting off water from 2 - acetylamino - 3 - naphthol and substitution products thereof. The quaternary ammonium salts thereof are formed in the usual manner. In an example, 2-methyl-b .b -naphthoxazole is prepared by heating 2-acetylamino-3-naphthol to about 180 DEG C.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE432969X | 1933-02-07 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB432969A true GB432969A (en) | 1935-08-07 |
Family
ID=6496705
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB4031/34A Expired GB432969A (en) | 1933-02-07 | 1934-02-07 | Process for sensitising photographic silver halide emulsions and manufacture of sensitising dyes therefor |
Country Status (3)
Country | Link |
---|---|
BE (1) | BE401235A (en) |
FR (1) | FR768047A (en) |
GB (1) | GB432969A (en) |
-
0
- BE BE401235D patent/BE401235A/xx unknown
-
1934
- 1934-02-01 FR FR768047D patent/FR768047A/en not_active Expired
- 1934-02-07 GB GB4031/34A patent/GB432969A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
BE401235A (en) | |
FR768047A (en) | 1934-07-30 |
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