GB597612A - Colour photography - Google Patents
Colour photographyInfo
- Publication number
- GB597612A GB597612A GB21630/45A GB2163045A GB597612A GB 597612 A GB597612 A GB 597612A GB 21630/45 A GB21630/45 A GB 21630/45A GB 2163045 A GB2163045 A GB 2163045A GB 597612 A GB597612 A GB 597612A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- iodide
- isopropylidenedioxybenzene
- diethyl
- methyl
- 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
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 12
- -1 methylene dioxy ring Chemical group 0.000 abstract 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 abstract 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 5
- VRZVPALEJCLXPR-UHFFFAOYSA-N ethyl 4-methylbenzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=C(C)C=C1 VRZVPALEJCLXPR-UHFFFAOYSA-N 0.000 abstract 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 abstract 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 3
- 239000005864 Sulphur Substances 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- HPQMGPYRBVWFRP-UHFFFAOYSA-N [1,3]dioxolo[4,5-g][1,3]benzoselenazole Chemical compound C1OC2=C(C3=C(N=C[Se]3)C=C2)O1 HPQMGPYRBVWFRP-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 235000019441 ethanol Nutrition 0.000 abstract 3
- 238000010992 reflux Methods 0.000 abstract 3
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 abstract 3
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 abstract 2
- AIGNCQCMONAWOL-UHFFFAOYSA-N 1,3-benzoselenazole Chemical group C1=CC=C2[se]C=NC2=C1 AIGNCQCMONAWOL-UHFFFAOYSA-N 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- SOLMCBVQLTZNML-UHFFFAOYSA-N C1OC2=C(C3=C(N=CS3)C=C2)O1 Chemical compound C1OC2=C(C3=C(N=CS3)C=C2)O1 SOLMCBVQLTZNML-UHFFFAOYSA-N 0.000 abstract 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 2
- 125000005427 anthranyl group Chemical group 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract 2
- 238000009835 boiling Methods 0.000 abstract 2
- 239000000975 dye Substances 0.000 abstract 2
- 239000011876 fused mixture Substances 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine group Chemical group N1=CCC2=CC=CC=C12 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 2
- 125000001624 naphthyl group Chemical group 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 abstract 2
- ODIRBFFBCSTPTO-UHFFFAOYSA-N 1,3-selenazole Chemical group C1=C[se]C=N1 ODIRBFFBCSTPTO-UHFFFAOYSA-N 0.000 abstract 1
- ZVJAKZBKJYHUIH-UHFFFAOYSA-N 2,2-dinitro-1,3-benzodioxole Chemical compound C1=CC=C2OC([N+](=O)[O-])([N+]([O-])=O)OC2=C1 ZVJAKZBKJYHUIH-UHFFFAOYSA-N 0.000 abstract 1
- MIECVJDZXBUVSN-UHFFFAOYSA-N 2,4-diphenyl-1,3-thiazole Chemical compound C=1SC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 MIECVJDZXBUVSN-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 125000002723 alicyclic group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 150000003997 cyclic ketones Chemical class 0.000 abstract 1
- FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 abstract 1
- PWAPCRSSMCLZHG-UHFFFAOYSA-N cyclopentylidene Chemical group [C]1CCCC1 PWAPCRSSMCLZHG-UHFFFAOYSA-N 0.000 abstract 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- XXTISPYPIAPDGY-UHFFFAOYSA-N n,n-diphenylmethanimidamide Chemical compound C=1C=CC=CC=1N(C=N)C1=CC=CC=C1 XXTISPYPIAPDGY-UHFFFAOYSA-N 0.000 abstract 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 230000000802 nitrating effect Effects 0.000 abstract 1
- 229910017604 nitric acid Inorganic materials 0.000 abstract 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 1
- 229910052711 selenium Inorganic materials 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 150000003557 thiazoles Chemical class 0.000 abstract 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 abstract 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
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
- G03C1/14—Methine and polymethine dyes with an odd number of CH groups
- G03C1/18—Methine and polymethine dyes with an odd number of CH groups with three CH groups
Abstract
Cyanine dyes of the general formula <FORM:0597612/IV/1> wherein R and R1 each represent H or alkyl or aryl groups or together represent the atoms necessary to complete a hydrogenated ring system R2 and R3 are alkyl groups, X is an acid group, Y is S or Se, and Z represents the atoms necessary to complete a heterocyclic ring are prepared by condensing quaternary ammonium salts of thiazoles or selenazoles containing the substituted methylene dioxy ring as part of the nucleus with any of the known cyanine dye intermediates. R and R1 may be methyl, ethyl, propyl, butyl, amyl, hexyl, heptyl, octyl, decyl, phenyl, naphthyl, anthranyl, cyclopentylidene or cyclohexylidene and Z may complete an indolenine, thiazole, benzthiazole or benzselenazole ring, which may be substituted by alkyl, alkoxy, phenyl, naphthyl, anthranyl, alicyclic, dioxyalkyl or dioxycycloalkyl substituents. Z may complete isopropylidenedioxy-, methylenedioxy-, dimethyl-, cyclopentylidenedioxy-, or cyclohexylidenedioxy-benzthiazole or benzselenazole rings or methylphenyl- or diphenyl-thiazole or p selenazole rings. 3 : 31-Diethyl-5 : 6 : 51 : 61-diisopropylidenedioxybenzthiacarbocyanine iodide is prepared by refluxing together 2-methyl-5 : 6-isopropylidenedioxybenzthiazole ethyl p - toluenesulphonate and ethyl orthoformate in pyridine, and adding aqueous potassium iodide solution. 3 : 31-Diethyl-5 : 6 : 51 : 61-diisopropylidenedioxybenzselenacarbocyanine iodide, 3 : 31-diethyl-5 : 6 : 51 : 61-dicyclohexylidenedioxybenzthiacarbocyanine iodide, 3 : 31 - diethyl - 5 : 6 : 51 : 61-dimethylenedioxybenzthiacarbocyanine iodide, and 3 : 31-diethyl-5 : 6 : 51 : 61-dicyclopentylidenedioxybenzthiacarbocyanine iodide are similarly prepared. 3 : 31-Diethyl-5 : 6 - methylenedioxy - 51 : 61-dimethylbenzselenabenzthiacarbocyanine iodide is prepared by refluxing together in pyridine containing triethylamine 2 - (b - acetanilidovinyl) - 5 : 6 - methylenedioxybenzselenazole ethiodide and 2-methyl-5 : 6-dimethylbenzthiazole ethyl p - toluenesulphonate, and adding aqueous potassium iodide to an alcohol solution of the precipitated dye. 3 : 31-Diethyl-5 : 6-methylenedioxy-41-phenyl-51 -methylbenzselenathiazolocarbocyanine iodide, 3 : 31 -diethyl-5 : 6-methylenedioxy-51 : 61-cyclohexylidenedioxybenzthiacarbocyanine iodide, 3 : 31-diethyl-5 : 6-methylenedioxy - 51 : 61-cyclohexylidenedioxybenzselenzbenzthiacarbocyanine iodide, 3 : 31-diethyl-5 : 6-methylenedioxy-41 : 51-diphenylbenzthiathiazolocarbocyanine iodide, 3 : 31-diethyl-5 : 6 -cyclohexylidenedioxy-61 : 71-benzbenzthiacarbocyanine iodide, and 3 : 31-di-ethyl - 5 : 6 - cyclohexylidenedioxy - 51 : 61 - di - methoxybenzthiacarbocyanine iodide are similarly prepared. Alkylidenedioxybenzenes and cycloalkylidenedioxybenzenes are prepared by reacting catechol with an aliphatic aldehyde or ketone or a cyclic ketone. Isopropylidenedioxybenzene is prepared by dissolving catechol in hot anhydrous acetone and treating with excess phosphorus pentoxide. Cyclohexylidenedioxybenzene and cyclopentylidenedioxybenzene are similarly prepared. 2 - Brom - 4 : 5 - isopropylidenedioxybenzene is prepared by adding bromine to a carbon disulphide solution of isopropylidenedioxybenzene. 2 - Bromo - 4 : 5 - cyclohexylidenedioxybenzene and 2 - bromo - 4 : 5 - cyclopentylidenedioxybenzene are similarly prepared. 1 - Nitro - 2 - bromo - 4 : 5 - isopropylidenedioxybenzene is prepared by nitrating 2-bromo-4 : 5-isopropylidenedioxybenzene with nitric acid. Bis-(1-nitro-4 : 5-isopropylidenedioxybenzene)-2 : 21-disulphide is prepared by treating a boiling ethyl alcohol solution of 1-nitro-2-bromo-4 : 5-isopropylidenedioxybenzene with a fused mixture of sodium sulphide and sulphur. Bis-(1-nitro-4 : 5-isopropylidenedioxybenzene)-2 : 21-diselenide is similarly prepared. Bis-(1-nitro - 4 : 5 - cyclohexylidenedioxybenzene) - 2 : 21 - disulphide and bis-(1-nitro-4 : 5-cyclopentylidenedioxybenze) - 2 : 21 - disulphide are prepared by treating a boiling ethyl alcohol solution of 1 : 2-dinitro - 4 : 5 - cyclohexylidenedioxybenzene or of 1 : 2 - dinitro - 4 : 5 - cyclopentylidenedioxy - benzene with a fused mixture of sodium sulphide and sulphur. 1 : 2-Dinitro-4 : 5 -isopropylidenedioxybenzene is prepared by treating isopropylidenedioxybenzene with a mixture of glacial acetic and fuming nitric acids. 1 : 2-Dinitro-4 : 5-cyclohexylidenedioxybenzene, 1 : 2-dinitro-4 : 5-cyclopentylidenedioxybenzene and 1 : 2-dinitro-4 : 5-methylenedioxybenzene are prepared similarly. 2-Methyl-5 : 6-isopropylidenedioxybenzthiazole is prepared by heating together bis-(1-nitro-4 : 5-isopropylidenedioxybenzene) - 2 : 21 - disulphide, acetic anhydride, glacial acetic acid and zinc. The ethyl p-toluenesulphonate is prepared by heating with ethyl p-toluenesulphonate. 2-Methyl - 5 : 6 - cyclohexylidenedioxybenzthiazole, 2-methyl-5 : 6-cyclopentylidenedioxybenzthiazole, 2-methyl-5 : 6-isopropylidenedioxybenzselenazole, 2-methyl-5 : 6 - methylenedioxybenzthiazole and the corresponding ethyl p-toluenesulphonates are similarly prepared. Bis - (1 - nitro - 4 : 5 - methylenedioxybenzene) - 2 : 21-disulphide is prepared by treating 4 : 5-dinitromethylenedioxybenzene with an alcoholic solution of sodium sulphide and sulphur. 2 - (b - Acetanilidovinyl) - 5 : 6 - methylenedioxy - benzselenazole ethiodide is prepared by refluxing together a mixture of 2-methyl-5 : 6-methylenedioxybenzselenazole ethiodide, diphenylformamidine and acetic anhydride. 2-(b -Acetanilidovinyl) - 5 : 6 - methylenedioxybenzthiazole ethiodide and 2-(b -acetanilidovinyl)-5 : 6-cyclohexylidenedioxybenzthiazole ethiodide are similarly prepared. Specifications 458,400, 464,398, 465,823, [all in Group XX], 468,946, 479,838, [Group XX], 483,000 and 484,698 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US549788A US2429574A (en) | 1944-08-16 | 1944-08-16 | Carbocyanines from alicyclicdioxy azoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB597612A true GB597612A (en) | 1948-01-29 |
Family
ID=24194384
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21630/45A Expired GB597612A (en) | 1944-08-16 | 1945-08-23 | Colour photography |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US2423217A (en) |
| GB (1) | GB597612A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2892838A (en) * | 1955-08-22 | 1959-06-30 | Sperry Rand Corp | Photographic sensitizing dyes derived from 2-alkyl-6, 7-dihydro-4-h-thiopyrano(4, 3d) thiazole |
| US2892836A (en) * | 1955-08-22 | 1959-06-30 | Sperry Rand Corp | Cyanine dyes |
| US2920962A (en) * | 1958-01-10 | 1960-01-12 | Du Pont | Photographic elements |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2126078A (en) * | 1932-04-26 | 1938-08-09 | Agfa Ansco Corp | Sensitizing photographic emulsion |
| BE398585A (en) * | 1932-09-14 | |||
| US2104855A (en) * | 1932-09-23 | 1938-01-11 | Agfa Ansco Corp | Polymethine dyes |
-
1944
- 1944-08-16 US US549790A patent/US2423217A/en not_active Expired - Lifetime
-
1945
- 1945-08-23 GB GB21630/45A patent/GB597612A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US2423217A (en) | 1947-07-01 |
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