GB592267A - Improvements in the manufacture of polymethin dyes and in photographic emulsions containing the same - Google Patents
Improvements in the manufacture of polymethin dyes and in photographic emulsions containing the sameInfo
- Publication number
- GB592267A GB592267A GB1633544A GB1633544A GB592267A GB 592267 A GB592267 A GB 592267A GB 1633544 A GB1633544 A GB 1633544A GB 1633544 A GB1633544 A GB 1633544A GB 592267 A GB592267 A GB 592267A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- group
- ethyl
- dimethyl
- 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
- 239000000975 dye Substances 0.000 title abstract 2
- 239000000839 emulsion Substances 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 10
- VLTRZXGMWDSKGL-UHFFFAOYSA-M Perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 abstract 8
- 238000010438 heat treatment Methods 0.000 abstract 7
- 229910052757 nitrogen Inorganic materials 0.000 abstract 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N Benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract 5
- BCMCBBGGLRIHSE-UHFFFAOYSA-N Benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 abstract 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 abstract 5
- -1 m - toloxy Chemical group 0.000 abstract 5
- 150000002829 nitrogen Chemical group 0.000 abstract 5
- 238000010992 reflux Methods 0.000 abstract 5
- AIGNCQCMONAWOL-UHFFFAOYSA-N 1,3-benzoselenazole Chemical compound C1=CC=C2[se]C=NC2=C1 AIGNCQCMONAWOL-UHFFFAOYSA-N 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 4
- 150000002790 naphthalenes Chemical class 0.000 abstract 4
- 150000003839 salts Chemical group 0.000 abstract 4
- 239000011780 sodium chloride Substances 0.000 abstract 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 4
- UVYFAHWMIBGHMU-UHFFFAOYSA-N 2-(phenoxymethyl)-1,3-benzothiazole Chemical compound N=1C2=CC=CC=C2SC=1COC1=CC=CC=C1 UVYFAHWMIBGHMU-UHFFFAOYSA-N 0.000 abstract 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M Potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- 239000001187 sodium carbonate Substances 0.000 abstract 3
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 3
- JVXJGLIGBHCEDP-UHFFFAOYSA-N 2-(4-methoxyphenoxy)acetyl chloride Chemical compound COC1=CC=C(OCC(Cl)=O)C=C1 JVXJGLIGBHCEDP-UHFFFAOYSA-N 0.000 abstract 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-Aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 abstract 2
- WDLGHHHEXTWURD-UHFFFAOYSA-N COC1=CC=C(OCC=2OC3=C(N2)C=CC=C3)C=C1 Chemical compound COC1=CC=C(OCC=2OC3=C(N2)C=CC=C3)C=C1 WDLGHHHEXTWURD-UHFFFAOYSA-N 0.000 abstract 2
- XYOUEIKDWFKWER-UHFFFAOYSA-N N-(2-hydroxyphenyl)-2-(4-methoxyphenoxy)acetamide Chemical compound C1=CC(OC)=CC=C1OCC(=O)NC1=CC=CC=C1O XYOUEIKDWFKWER-UHFFFAOYSA-N 0.000 abstract 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N Phosphorus pentoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- 125000004849 alkoxymethyl group Chemical group 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- PROCECBQSRMMBV-UHFFFAOYSA-N 2-(3-methylphenoxy)acetyl chloride Chemical compound CC1=CC=CC(OCC(Cl)=O)=C1 PROCECBQSRMMBV-UHFFFAOYSA-N 0.000 abstract 1
- BHFSBJHPPFJCOS-UHFFFAOYSA-N 2-(4-methoxyphenoxy)acetic acid Chemical compound COC1=CC=C(OCC(O)=O)C=C1 BHFSBJHPPFJCOS-UHFFFAOYSA-N 0.000 abstract 1
- JMKFJZRSWHKKKB-UHFFFAOYSA-N 2-(ethoxymethyl)-1,3-benzothiazole Chemical compound C1=CC=C2SC(COCC)=NC2=C1 JMKFJZRSWHKKKB-UHFFFAOYSA-N 0.000 abstract 1
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-Methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 abstract 1
- MQBFELLBNOYLMK-UHFFFAOYSA-N 2-[(3-methylphenoxy)methyl]-1,3-benzothiazole Chemical compound CC1=CC=CC(OCC=2SC3=CC=CC=C3N=2)=C1 MQBFELLBNOYLMK-UHFFFAOYSA-N 0.000 abstract 1
- YXTQYVCASSUOCC-UHFFFAOYSA-N 2-[(4-chlorophenoxy)methyl]-1,3-benzothiazole Chemical compound C1=CC(Cl)=CC=C1OCC1=NC2=CC=CC=C2S1 YXTQYVCASSUOCC-UHFFFAOYSA-N 0.000 abstract 1
- BZEUTAWPVLRXPV-UHFFFAOYSA-N 2-[(4-chlorophenoxy)methyl]-1,3-benzoxazole Chemical compound C1=CC(Cl)=CC=C1OCC1=NC2=CC=CC=C2O1 BZEUTAWPVLRXPV-UHFFFAOYSA-N 0.000 abstract 1
- VKOIPGVGFOEALT-UHFFFAOYSA-N 2-ethoxy-N-(2-hydroxyphenyl)acetamide Chemical compound CCOCC(=O)NC1=CC=CC=C1O VKOIPGVGFOEALT-UHFFFAOYSA-N 0.000 abstract 1
- ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 2-ethoxyacetyl chloride Chemical compound CCOCC(Cl)=O ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 0.000 abstract 1
- PKUPAJQAJXVUEK-UHFFFAOYSA-N 2-phenoxyacetyl chloride Chemical compound ClC(=O)COC1=CC=CC=C1 PKUPAJQAJXVUEK-UHFFFAOYSA-N 0.000 abstract 1
- ORJKZOUEJKDANQ-UHFFFAOYSA-N 5-chloro-2-(phenoxymethyl)-1,3-benzoxazole Chemical compound N=1C2=CC(Cl)=CC=C2OC=1COC1=CC=CC=C1 ORJKZOUEJKDANQ-UHFFFAOYSA-N 0.000 abstract 1
- DQMSNGVJXKQCQF-UHFFFAOYSA-N C(C)(=O)C(=C1SC2=C(N1C)C=CC=C2)OC2=CC=CC=C2 Chemical compound C(C)(=O)C(=C1SC2=C(N1C)C=CC=C2)OC2=CC=CC=C2 DQMSNGVJXKQCQF-UHFFFAOYSA-N 0.000 abstract 1
- QTGFJUJOVDLTLN-UHFFFAOYSA-N C(C)OCC=1OC2=C(N1)C=CC=C2 Chemical compound C(C)OCC=1OC2=C(N1)C=CC=C2 QTGFJUJOVDLTLN-UHFFFAOYSA-N 0.000 abstract 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M CHEMBL593252 Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 abstract 1
- ZQUVDXMUKIVNOW-UHFFFAOYSA-N N,N'-diphenylmethanimidamide Chemical compound C=1C=CC=CC=1NC=NC1=CC=CC=C1 ZQUVDXMUKIVNOW-UHFFFAOYSA-N 0.000 abstract 1
- IIDOFGSUHJULIN-UHFFFAOYSA-N O(C1=CC=CC=C1)C=1SC2=C(N1)C(=CC=C2)C Chemical compound O(C1=CC=CC=C1)C=1SC2=C(N1)C(=CC=C2)C IIDOFGSUHJULIN-UHFFFAOYSA-N 0.000 abstract 1
- QMGVVNAWYGLFEM-UHFFFAOYSA-N O(C1=CC=CC=C1)CC=1OC2=C(N1)C=C(C=C2)C2=CC=CC=C2 Chemical compound O(C1=CC=CC=C1)CC=1OC2=C(N1)C=C(C=C2)C2=CC=CC=C2 QMGVVNAWYGLFEM-UHFFFAOYSA-N 0.000 abstract 1
- GXGHCLCDKGBNOA-UHFFFAOYSA-N O(C1=CC=CC=C1)CC=1[Se]C2=C(N1)C=CC=C2 Chemical compound O(C1=CC=CC=C1)CC=1[Se]C2=C(N1)C=CC=C2 GXGHCLCDKGBNOA-UHFFFAOYSA-N 0.000 abstract 1
- CYQAYERJWZKYML-UHFFFAOYSA-N Phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 abstract 1
- BAZAXWOYCMUHIX-UHFFFAOYSA-M Sodium perchlorate Chemical compound [Na+].[O-]Cl(=O)(=O)=O BAZAXWOYCMUHIX-UHFFFAOYSA-M 0.000 abstract 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 125000004429 atoms Chemical group 0.000 abstract 1
- 125000004432 carbon atoms Chemical group C* 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 abstract 1
- 150000002905 orthoesters Chemical class 0.000 abstract 1
- 230000001590 oxidative Effects 0.000 abstract 1
- MIMJFNVDBPUTPB-UHFFFAOYSA-N potassium hexacyanoferrate(3-) Chemical compound [K+].[K+].[K+].N#C[Fe-3](C#N)(C#N)(C#N)(C#N)C#N MIMJFNVDBPUTPB-UHFFFAOYSA-N 0.000 abstract 1
- GKGFTIKPKGWMOW-UHFFFAOYSA-N propane-1,1,1-triolate Chemical compound CCC([O-])([O-])[O-] GKGFTIKPKGWMOW-UHFFFAOYSA-N 0.000 abstract 1
- 229910001488 sodium perchlorate Inorganic materials 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
- 239000011592 zinc chloride Substances 0.000 abstract 1
- 235000005074 zinc chloride Nutrition 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
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Cyanine dyes of the general formula <FORM:0592267/IV/1> wherein R and R1 each represent a methyl or an ethyl group, R2 represents an alkyl group or an aryl group of the benzene or naphthalene series, R3 represents H or a methyl or an ethyl group, Q represents H, an alkoxy group, or an aryloxy group of the benzene or naphthalene series, Z and Z1 each represent the non-metallic atoms to complete a benzthiazole, benzoxazole, benzolenazole, a - or b -naphthathiazole, or a - or b -naphthoxazole nucleus, and X represents an anion are prepared (a) by condensing with an orthoester, a benzthiazole, benzoxazole, benzselenazole, a - or b -naphthathiazole, or a - or b -naphthoxazole quaternary salt having in the a -position to the quaternary nitrogen atom an alkoxymethyl or aryloxymethyl group of the benzene or naphthalene series, (b) by condensing a benzthiazole, benzoxazole, benzselenazole, a - or b -naphthathiazole, or a - or b -naphthoxazole quaternary salt having in the a - or g -position to the quaternary nitrogen atom a b -arylaminovinyl (including an acylated b -arylaminovinyl) group with a benzthiazole, benzoxazole, benzselenazole, a - or b -naphthathiazole, or a - or b -naphthoxazole quaternary salt having in the a -position to the quaternary nitrogen atom an alkoxymethyl group or an aryloxymethyl group of the benzene or naphthalene series, or (c) condensing a benzthiazoline, benzoxazoline, benzselenazoline, a -or b -naphthathiazoline, or a - or b -naphthoxazoline having in the a -position to the nuclear nitrogen atom an acylated alkoxymethylene or aryloxymethylene group with a quaternary salt of a heterocyclic nitrogen base having a methyl group in the a - or g -position to the quaternary nitrogen atom. 8 : 10-Di-(p-methoxyphenoxy)-3 : 31-dimethyloxacarbocyanine perchlorate is prepared by heating together 2 - (p - methoxyphenoxymethyl) - benzoxazole and methyl p-toluenesulphonate, adding dry pyridine and ethyl orthoformate and refluxing, and adding hot aqueous sodium perchlorate. 3 : 31 - Dimethyl - 8 : 10 - diphenoxy-5 : 51-diphenyloxacarbocyanine perchlorate, 8 : 10-diethoxy - 3 : 31 - dimethyloxacarbocyanine per - chlorate, 3 : 31 - dimethyl - 8 : 10 - di - (m - toloxy) - thicarbocyanine bromide, 8 : 10 - di - (p - chloro - phenoxy) - 3 : 31 - dimethylthiacarbocyanine p-toluenesulphonate, 3 : 31 - dimethyl - 8 : 10 - di - (b -naphthoxy) - thiacarbocyanine iodide, 8 : 10 - di - ethoxy - 3 : 31 - dimethylthiacarbocyanine iodide, 3 : 31-dimethyl-8 : 10-diphenoxy-4 : 5 : 41 : 51 dibenzoxacarbocyanine iodide, 3 : 31 - dimethyl - 8 : 10-diphenoxy-6 : 7 : p 61 : 71-dibenzoxacarbocyanine methylsulphate, 3 : 31-dimethyl-8 : 10-diphenoxyselenacarbocyanine bromide, 3 : 31-dimethyl-8 : 10-diphenoxy-6 : 6 : 61 : 71-dibenzthiacarbocyanine bromide, and 3 : 31 - dimethyl-8 : 10-diphenoxy-4 : 5 : 41 : 51-dibenzthiacarbocyanine bromide are similarly prepared. 31-Ethyl-3-methyl-8-phenoxythiacarbocyanine iodide is prepared by heating together 2-phenoxymethylbenzthiazole and methyl p-toluenesulphonate, and adding dry pyridine, 2-(b -acetanilidovinyl)-benzthiazole ethiodide, and triethylamine, and refluxing. 3 : 31-Diethyl-10-phenoxyoxathiacarbocyanine perchlorate is similarly prepared. 31-Ethyl-3 : 9-dimethyl-8-phenoxythiacarbocyanine iodide is prepared by refluxing together 2-(acetylphenoxymethylene)-3 - methylbenzthiazoline, 2 - methylbenzthiazole etho-p-toluenesulphonate, and acetic anhydride, and adding hot aqueous potassium iodide. b -(m-Toloxy)-ethylidenerhodanine, 3-ethyl-5-(3 - ethyl - 2 - benzthiazolylidane) - b - (m - toloxy) - ethylidene - 2 - thio - 2 : 4 - oxazoledione, 3 - ethyl - 5 - (3 - methyl - 2 - benzoxazolylidene) - b - (p - chloro - phenoxy) - ethylidenerhodanine, 3 - ethyl - 5 - (5 - chloro-3-methyl-2-benzoxazolylidene) -b -phenoxyethylidene-2-thio-2 : 4-oxazoledione, and 5 - (4 - ethyl-2-benzthiazolylidene)-b -methoxyethylidene) -3-phenylrhodanine are similarly prepared. 2 - (p - Methoxyphenoxymethyl) - benzoxazole is prepared by heating together 2-(p-methoxyphenoxyacetylamino)-phenol and phosphorus pentoxide and pouring into aqueous sodium carbonate. 2 - Phenoxymethyl - 5 - phenylbenz - oxazole, 5 - chloro - 2 - phenoxymethylbenzoxazole, 2 - (p-chlorophenoxymethyl)-benzoxazole, 2-phen - oxymethyl-b -naphthoxazole, 2-phenoxymethyl-a -naphthoxazole, and 2-ethoxymethylbenzoxazole are similarly prepared. 2-(p-Methoxyphenoxyacetylamino)-phenol is prepared by adding p-methoxyphenoxyacetyl chloride slowly to a solution of o-aminophenol in pyridine and pouring into aqueous sodium carbonate. p-Methoxyphenoxyacetyl chloride is prepared by heating together p-methoxyphenoxyacetic acid and thionyl chloride. 2-Ethoxyacetylaminophenol is prepared by adding ethoxyacetyl chloride slowly to a solution of o-aminophenol in pyridine and pouring into aqueous sodium carbonate. m-Toloxymethylbenzthiazole is prepared by adding a solution of m-toloxyacetyl chloride in dry benzene to a suspension of zinc o-aminophenylmercaptide and zinc chloride in dry benzene, and refluxing. 2-Ethoxymethylbenzthiazole, 2 - (b - naphthoxymethyl) - benzthiazole, p - chlorophenoxymethylbenzthiazole, 2 - phenoxy - methylbenzthiazole, and 2 - phenoxymethylbenz - selenazole are similarly prepared. 2-Phenoxymethyl-a -naphthathiazole is prepared by adding phosphorus pentasulphide to a heated solution of phenoxyacetyl-b -naphthylamine in dry pyridine and oxidizing the phenoxythioacetyl-b -naphthylamine obtained with aqueous potassium ferricyanide. Phenoxythioacetyl-a -naphthylamine and 2 - phenoxymethyl - b - naphtha - thiazole are similarly obtained. Phenoxyacetyl-a -naphthylamine is prepared by heating together a -naphthylamine and phenoxyacetyl chloride. Phenoxyacetyl-b -naphthylamine is similarly obtained. 2 - (b - Acetanilido - a - phenoxyvinylbenzthiazole methiodide is prepared by heating together 2-phenoxymethylbenzthiazole methiodide and diphenylformamidine. 2 - (Acetylphenoxymethylene)-3-methylbenzthia - zoline is prepared by heating together 2-phenoxymethylbenzthiazole and methyl p-toluenesulphonate, adding acetic anhydride and triethylamine, and refluxing. According to the Provisional Specification, R and R1 may represent alkyl groups having from one to four carbon atoms and R3 may represent H or an alkyl or cycloalkyl group.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB592267A true GB592267A (en) | 1947-09-12 |
Family
ID=1732235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1633544A Expired GB592267A (en) | 1944-08-28 | Improvements in the manufacture of polymethin dyes and in photographic emulsions containing the same |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB592267A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0443466A1 (en) * | 1990-02-22 | 1991-08-28 | Fuji Photo Film Co., Ltd. | Silver halide emulsion and heptamethine cyanine dye |
| EP0647878A2 (en) * | 1990-08-23 | 1995-04-12 | Fuji Photo Film Co., Ltd. | Silver halide photographic material |
| US5491057A (en) * | 1991-08-14 | 1996-02-13 | Fuji Photo Film Co., Ltd. | Silver halide emulsion |
-
1944
- 1944-08-28 GB GB1633544A patent/GB592267A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0443466A1 (en) * | 1990-02-22 | 1991-08-28 | Fuji Photo Film Co., Ltd. | Silver halide emulsion and heptamethine cyanine dye |
| US5429920A (en) * | 1990-02-22 | 1995-07-04 | Fuji Photo Film Co., Ltd. | Silver halide emulsion |
| EP0647878A2 (en) * | 1990-08-23 | 1995-04-12 | Fuji Photo Film Co., Ltd. | Silver halide photographic material |
| EP0647878A3 (en) * | 1990-08-23 | 1997-07-30 | Fuji Photo Film Co Ltd | Silver halide photographic material. |
| US5491057A (en) * | 1991-08-14 | 1996-02-13 | Fuji Photo Film Co., Ltd. | Silver halide emulsion |
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