GB867592A - Improvements in or relating to photographic emulsions and elements containing the same - Google Patents
Improvements in or relating to photographic emulsions and elements containing the sameInfo
- Publication number
- GB867592A GB867592A GB1967558A GB1967558A GB867592A GB 867592 A GB867592 A GB 867592A GB 1967558 A GB1967558 A GB 1967558A GB 1967558 A GB1967558 A GB 1967558A GB 867592 A GB867592 A GB 867592A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- carbethoxy
- diethylamino
- hydroxy
- coumarin
- 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
- 239000000839 emulsion Substances 0.000 title 1
- -1 amino, substituted amino Chemical group 0.000 abstract 3
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 abstract 2
- WZUODJNEIXSNEU-UHFFFAOYSA-N 2-Hydroxy-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(O)=C1 WZUODJNEIXSNEU-UHFFFAOYSA-N 0.000 abstract 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 abstract 2
- XFVZSRRZZNLWBW-UHFFFAOYSA-N 4-(Diethylamino)salicylaldehyde Chemical compound CCN(CC)C1=CC=C(C=O)C(O)=C1 XFVZSRRZZNLWBW-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- OQQYMAOGIWMABG-UHFFFAOYSA-N ethyl 2-quinolin-2-ylacetate Chemical compound C1=CC=CC2=NC(CC(=O)OCC)=CC=C21 OQQYMAOGIWMABG-UHFFFAOYSA-N 0.000 abstract 2
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 abstract 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 abstract 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 abstract 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 abstract 1
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 abstract 1
- RPKCLSMBVQLWIN-UHFFFAOYSA-N 2-n-methylbenzene-1,2-diamine Chemical compound CNC1=CC=CC=C1N RPKCLSMBVQLWIN-UHFFFAOYSA-N 0.000 abstract 1
- IETDBZQIWIJQJG-UHFFFAOYSA-N 7-hydroxy-2-oxo-chromene-3-carboxylic acid ethyl ester Chemical compound C1=C(O)C=C2OC(=O)C(C(=O)OCC)=CC2=C1 IETDBZQIWIJQJG-UHFFFAOYSA-N 0.000 abstract 1
- FWFVXBZXJKTVGL-UHFFFAOYSA-N 7-methoxy-2-oxo-1-benzopyran-3-carboxylic acid ethyl ester Chemical compound C1=C(OC)C=C2OC(=O)C(C(=O)OCC)=CC2=C1 FWFVXBZXJKTVGL-UHFFFAOYSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- XKHPEMKBJGUYCM-UHFFFAOYSA-N ethyl 2-oxochromene-3-carboxylate Chemical compound C1=CC=C2OC(=O)C(C(=O)OCC)=CC2=C1 XKHPEMKBJGUYCM-UHFFFAOYSA-N 0.000 abstract 1
- MSOLGAJLRIINNF-UHFFFAOYSA-N ethyl 7-(diethylamino)-2-oxochromene-3-carboxylate Chemical compound C1=C(N(CC)CC)C=C2OC(=O)C(C(=O)OCC)=CC2=C1 MSOLGAJLRIINNF-UHFFFAOYSA-N 0.000 abstract 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/02—Coumarine 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
- C09B23/10—The polymethine chain containing an even number of >CH- groups
- C09B23/102—The polymethine chain containing an even number of >CH- groups two heterocyclic rings linked carbon-to-carbon
-
- 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
- G03C1/102—Organic substances dyes other than methine dyes
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)
Abstract
2-Carbethoxymethyl-quinoline is prepared by reacting quinaldine with ethyl chloroformate in anhydrous ether in the presence of lithium and bromobenzene. 3-Carbethoxy-7-diethylamino-coumarin is prepared by refluxing 4-diethylamino-2-hydroxybenzaldehyde and diethylmalonate in ethanol in the presence of piperidine. 3-Carbethoxy-7-hydroxy-coumarin and 3-carbethoxy-7-methoxycoumarin are similarly prepared from resorcylaldehyde or 2-hydroxy-4-methoxybenzaldehyde respectively and diethyl malonate. German Specification 105,103 is referred to.ALSO:Dyestuffs of the general formula:- <FORM:0867592/IV(c)/1> wherein n is 0 or 1, D completes a 5- or 6-membered ring and Z is hydrogen or one or more alkyl, aralkyl, aryl, hydroxy, alkoxy, amino, substituted amino or halogen substituents, are prepared by reacting a salicylaldehyde with a compound of the formula:- <FORM:0867592/IV(c)/2> wherein R1 is an alkyl group. An example is given of the reaction of 4-diethylamino-2-hydroxybenzaldehyde with 2-ethoxycarbonylmethyl-quinoline. The dyes wherein D is a benzthiazole, benzoxazole or benzimidazole nucleus may be prepared by reacting a 3-carbalkoxycoumarin with a compound of the formula:- <FORM:0867592/IV(c)/3> wherein X is O, S, -NH- or substituted -NH-. Examples are given of the reaction of 3-carbethoxy-coumarin having in the 7-position a hydroxy, methoxy or diethylamino substituent with o-aminophenol, o-aminothiophenol, o-phenylene-diamine or o-amino-N-methylaniline. German Specification 105,103 is referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1967558A GB867592A (en) | 1958-06-19 | 1958-06-19 | Improvements in or relating to photographic emulsions and elements containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1967558A GB867592A (en) | 1958-06-19 | 1958-06-19 | Improvements in or relating to photographic emulsions and elements containing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB867592A true GB867592A (en) | 1961-05-10 |
Family
ID=10133318
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1967558A Expired GB867592A (en) | 1958-06-19 | 1958-06-19 | Improvements in or relating to photographic emulsions and elements containing the same |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB867592A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4764622A (en) * | 1979-08-27 | 1988-08-16 | Bayer Aktiengesellschaft | Light-collecting coumarin derivatives |
-
1958
- 1958-06-19 GB GB1967558A patent/GB867592A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4764622A (en) * | 1979-08-27 | 1988-08-16 | Bayer Aktiengesellschaft | Light-collecting coumarin derivatives |
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