GB759409A - Improvements in photographic emulsions containing colour couplers - Google Patents
Improvements in photographic emulsions containing colour couplersInfo
- Publication number
- GB759409A GB759409A GB11365/54A GB1136554A GB759409A GB 759409 A GB759409 A GB 759409A GB 11365/54 A GB11365/54 A GB 11365/54A GB 1136554 A GB1136554 A GB 1136554A GB 759409 A GB759409 A GB 759409A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tert
- amylphenoxy
- acid
- benzamido
- chloride
- 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 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 20
- -1 aliphatic alcohols Chemical class 0.000 abstract 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 10
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 10
- 229960000583 acetic acid Drugs 0.000 abstract 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 6
- 150000001412 amines Chemical class 0.000 abstract 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 229940040526 anhydrous sodium acetate Drugs 0.000 abstract 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 abstract 3
- 229920001577 copolymer Polymers 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 3
- 229910052742 iron Inorganic materials 0.000 abstract 3
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 abstract 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 239000007868 Raney catalyst Substances 0.000 abstract 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 2
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- VTPNYMSKBPZSTF-UHFFFAOYSA-N 1-ethenyl-2-ethylbenzene Chemical compound CCC1=CC=CC=C1C=C VTPNYMSKBPZSTF-UHFFFAOYSA-N 0.000 abstract 1
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 abstract 1
- JPSKCQCQZUGWNM-UHFFFAOYSA-N 2,7-Oxepanedione Chemical compound O=C1CCCCC(=O)O1 JPSKCQCQZUGWNM-UHFFFAOYSA-N 0.000 abstract 1
- VTULJCFJIIAAIS-UHFFFAOYSA-N 2-(2-sulfobenzoyl)oxycarbonylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1S(O)(=O)=O VTULJCFJIIAAIS-UHFFFAOYSA-N 0.000 abstract 1
- CSEWAUGPAQPMDC-UHFFFAOYSA-N 2-(4-aminophenyl)acetic acid Chemical compound NC1=CC=C(CC(O)=O)C=C1 CSEWAUGPAQPMDC-UHFFFAOYSA-N 0.000 abstract 1
- IOXOZOPLBFXYLM-UHFFFAOYSA-N 2-(4-nitrophenyl)ethanamine Chemical compound NCCC1=CC=C([N+]([O-])=O)C=C1 IOXOZOPLBFXYLM-UHFFFAOYSA-N 0.000 abstract 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 abstract 1
- CGGYSTYVGGSXEO-UHFFFAOYSA-N 2-carbonochloridoyl-6-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=C(Cl)C=CC=C1C(Cl)=O CGGYSTYVGGSXEO-UHFFFAOYSA-N 0.000 abstract 1
- JRMAQQQTXDJDNC-UHFFFAOYSA-M 2-ethoxy-2-oxoacetate Chemical compound CCOC(=O)C([O-])=O JRMAQQQTXDJDNC-UHFFFAOYSA-M 0.000 abstract 1
- CXYMDAXGGAITQP-UHFFFAOYSA-N 2-hydroxy-n-phenylnaphthalene-1-carboxamide Chemical compound OC1=CC=C2C=CC=CC2=C1C(=O)NC1=CC=CC=C1 CXYMDAXGGAITQP-UHFFFAOYSA-N 0.000 abstract 1
- MEEKGULDSDXFCN-UHFFFAOYSA-N 2-pentylphenol Chemical compound CCCCCC1=CC=CC=C1O MEEKGULDSDXFCN-UHFFFAOYSA-N 0.000 abstract 1
- QUEKGYQTRJVEQC-UHFFFAOYSA-N 2516-96-3 Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1Cl QUEKGYQTRJVEQC-UHFFFAOYSA-N 0.000 abstract 1
- NNGHWPIQPQHOKQ-UHFFFAOYSA-N 3-nitro-n-(5-oxo-1-phenyl-4h-pyrazol-3-yl)benzamide Chemical compound [O-][N+](=O)C1=CC=CC(C(=O)NC=2CC(=O)N(N=2)C=2C=CC=CC=2)=C1 NNGHWPIQPQHOKQ-UHFFFAOYSA-N 0.000 abstract 1
- NXTNASSYJUXJDV-UHFFFAOYSA-N 3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C(Cl)=O)=C1 NXTNASSYJUXJDV-UHFFFAOYSA-N 0.000 abstract 1
- LAKMXGZYUWSTOT-UHFFFAOYSA-N 4-chloro-1-hydroxy-N-[2-(4-nitrophenyl)ethyl]naphthalene-2-carboxamide Chemical compound OC1=C(C=C(C2=CC=CC=C12)Cl)C(=O)NCCC1=CC=C(C=C1)[N+](=O)[O-] LAKMXGZYUWSTOT-UHFFFAOYSA-N 0.000 abstract 1
- PVKNQGWSRAGMNM-UHFFFAOYSA-N 5-amino-2-phenyl-1h-pyrazol-3-one Chemical compound N1C(N)=CC(=O)N1C1=CC=CC=C1 PVKNQGWSRAGMNM-UHFFFAOYSA-N 0.000 abstract 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 abstract 1
- 239000005711 Benzoic acid Substances 0.000 abstract 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 abstract 1
- 239000004141 Sodium laurylsulphate Substances 0.000 abstract 1
- 150000003926 acrylamides Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 235000010233 benzoic acid Nutrition 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 239000002270 dispersing agent Substances 0.000 abstract 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical class CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 150000002825 nitriles Chemical group 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000008188 pellet Substances 0.000 abstract 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 abstract 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 abstract 1
- QHDYIMWKSCJTIM-UHFFFAOYSA-N phenyl 1-hydroxynaphthalene-2-carboxylate Chemical compound C1=CC2=CC=CC=C2C(O)=C1C(=O)OC1=CC=CC=C1 QHDYIMWKSCJTIM-UHFFFAOYSA-N 0.000 abstract 1
- PRPJEXLNOGLBCN-UHFFFAOYSA-N phenyl 4-chloro-1-hydroxynaphthalene-2-carboxylate Chemical compound C1=C(Cl)C2=CC=CC=C2C(O)=C1C(=O)OC1=CC=CC=C1 PRPJEXLNOGLBCN-UHFFFAOYSA-N 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 239000001632 sodium acetate Substances 0.000 abstract 1
- 235000017281 sodium acetate Nutrition 0.000 abstract 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 abstract 1
- 150000003440 styrenes Chemical class 0.000 abstract 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical group ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 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
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/388—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor
- G03C7/3882—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor characterised by the use of a specific polymer or latex
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Abstract
A mixture of 58.8 per cent n-butyl acrylate, 25.2 per cent styrene and 16 per cent methacrylamide is emulsion polymerized using a persulphate catalyst and sodium lauryl sulphate as the dispersing agent to give a hydrosol. Reference is made also to copolymers of acrylic or methacrylic acid esters of aliphatic alcohols having up to 10 carbon atoms (e.g. methyl, ethyl, n-propyl, iso-propyl and n-butyl acrylates and methyl and ethyl methacrylates) with acrylonitrile, or styrene or substituted styrene such as o-methyl styrene, 2 : 4-dimethyl styrene, 2 : 4 : 5-trimethyl styrene or o-ethyl styrene, and to three component copolymers of acrylic or methacrylic acid esters with nitriles or styrene and acrylamide or methacrylamide or alkyl substituted derivatives of acrylamide or methacrylamide. Copolymers containing 70 per cent butyl acrylate and 30 per cent styrene or 70 per cent ethyl acrylate and 30 per cent acrylonitrile are specified. Specifications 2562/13, [Class 98 (ii)], 524,154, 524,554, 524,555, 541,589, 547,064, 562,205, 733,119, 745,545 and 757,368, [all in Group XX], are referred to. Reference has been directed by the Comptroller to Specification 674,752, [Group XX].ALSO:1 - Hydroxy - [21 - (211,411 - di - tert amylphenoxy) - 51 - carboxy] - 2 - naphthanilide is prepared by heating phenyl 1-hydroxy-2-naphthoate with 3-amino-4-(21,41-di-tert. amylphenoxy) benzoic acid. 1 - Hydroxy - 4 - [411 - (carboxymethyl)phenylazo] - [21 - (2111,4111 - di - tert. amylphenoxy - 5- carboxy] - 2 - naphthanilide is prepared by coupling the above hydroxynaphthanilide with diazotized p-aminophenylacetic acid. 2;4 - Dichloro - 3 - methyl - 6 - [31 - nitro - 61- (211;411 - di - tert. amylphenoxy)benzamido] phenol is prepared by heating a mixture of 2- amino - 4;6 - dichloro - 5 - methylphenol hydrochloride and 2-(21;41-di-tert. amylphenoxy)-5-nitrobenzoyl chloride in acetic acid with anhydrous sodium acetate. This is then reduced to the corresponding amino compound with iron and acetic acid. The resulting amine is added to 3;5-dichlorosulphonylbenzoyl chloride in dioxane to give 2;4 - dichloro - 3 - methyl - 6- {21 - [211;411 - di - tert. amylphenoxy] - 51 - [3111;5111 - (dichlorosulphonyl) benzamido]benzamido} phenol or the amine is stirred in a mixture of glacial acetic acid and anhydrous sodium acetate and 3;5-dicarbomethoxyphenylcarbamylvaleryl chloride added to give 2;4-dichloro3 - methyl - 6 - {21 - (211;411 - di - tert. amylphenoxy) - 51 - [o - (3111;5111 - dicarbomethoxy phenylcarbamyl)valerylamido]benzamido}phenol. 3;5 - Dicarbomethoxyphenylcarbamylvaleric acid is prepared by refluxing a mixture of 5-amino-iso-phthalate and adipic anhydride in benzene. The corresponding acid chloride is made by treating the acid with thionyl chloride. 1 - Hydroxy - N - (p - nitro phenethyl) - 4- chloro - 2 - naphthamide is prepared by condensing p-nitro phenethylamine with phenyl 1- hydroxy - 4 - chloro - 2 - naphthoate. It is reduced with hydrogen and Raney nickel to the corresponding amine, which is then condensed in acetic acid and sodium acetate with 2-(21;41-di-tert. amyl phenoxy)-5-nitro benzoyl chloride to yield 1 - hydroxy - N - {41 - [211 - (2111;4111 - di-tert. amylphenoxy) - 511 - nitrobenzamido] phenethyl} - 4 - chloro - 2 - naphthamide. This is reduced with hydrogen and Raney nickel to the corresponding amine which is then condensed either with 3;5-dichlorosulphobenzoyl chloride to yield 1 - hydroxy - 4 - chloro - N - {p - [51- 311;511 - dichlorosulphobenzamido) - 21 -(2111;4111- di - tert. amylphenoxy)benzamido]phenethyl} - 2- 2 - naphthamide or with 3 - chlorosulphobenzoyl chloride to yield 1 - hydroxy - 4 - chloro - N- {p - [51 - (311 - chlorosulphobenzamido) - 21 - (2111; 4111 - di - tert. amylphenoxy)benzamido]phenethyl} - 2 - naphthamide. 1 - Phenyl - 3 - {31[211 - (2111;4111 - di - tert.- amylphenoxy) - 511 - (21111 - sulphobenzamido) benzamido]benzamido} - 5 - pyrazolone is prepared by reacting o-sulphobenzoic anhydride with 1 - phenyl - 3 - {31 - [211 - (2111;4111 - ditert. amylphenoxy) - 511 - aminobenzamido] benzamido}-5-pyrazolone in hot dry xylene. 1 - Phenyl - 3 - {31 - [211 - (2111;4111 - di - tert. amylphenoxy) - 511 - nitrobenzamido]benzamido}-5-pyrazolone is prepared by reacting 2-(21;41-di-tert. amylphenoxy) - 5 - nitrobenzoyl chloride with 1 - phenyl - 3 - (31 - aminobenzamido) - 5-pyrazolone in acetic acid and anhydrous sodium acetate. The product may be reduced to the corresponding amine using iron and acetic acid. 1 - Phenyl - 3 - m - nitrobenzamido - 5 - pyrazolone is prepared by heating 1-phenyl-3-amino-5-pyrazolone with m-nitrobenzoyl chloride and ethyl oxalate on the steam bath. The nitrogroup is reduced to an amino group using iron and acetic acid. 2 - (21;41 - Di - tert. amylphenoxy) - 5 - nitrobenzoic acid is prepared by reacting 2-chloro-5-nitrobenzoic acid with di-tert. amylphenol and potassium hydroxide pellets, and acidifying the reaction mixture with hydrochloric acid. The acid chloride is obtained by treating the acid with thionyl chloride. Specifications 2562/13, [Class 98 (ii)], 524,154, 524,554, 524,555, 541,589, 547,064, 562,205, [all in Group XX], 733,119, 745,545 and 757,368 are referred to. Reference has been directed by the Comptroller to Specification 674,752, [Group XX].
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US349348A US2772163A (en) | 1953-04-17 | 1953-04-17 | Photographic emulsions containing couplers and hydrosols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB759409A true GB759409A (en) | 1956-10-17 |
Family
ID=23372005
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB11365/54A Expired GB759409A (en) | 1953-04-17 | 1954-04-20 | Improvements in photographic emulsions containing colour couplers |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2772163A (en) |
| BE (1) | BE528163A (en) |
| DE (1) | DE965616C (en) |
| FR (1) | FR1110268A (en) |
| GB (1) | GB759409A (en) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL218321A (en) * | 1956-06-22 | |||
| BE565490A (en) * | 1957-03-08 | |||
| US3165407A (en) * | 1962-06-08 | 1965-01-12 | Eastman Kodak Co | Process for improving color developability of reversal photograph films |
| US3271152A (en) * | 1962-09-04 | 1966-09-06 | Eastman Kodak Co | Light-sensitive elements for color photography and process therefor |
| US3655407A (en) * | 1969-03-10 | 1972-04-11 | Eastman Kodak Co | Method of coating dilute aqueous emulsions |
| JPS4842732A (en) * | 1971-09-30 | 1973-06-21 | ||
| JPS5139853B2 (en) * | 1972-11-16 | 1976-10-30 | ||
| US3985565A (en) * | 1974-07-12 | 1976-10-12 | Eastman Kodak Company | Photothermographic, composition using a phenolic leuco dye as a reducing agent |
| BE833512A (en) * | 1974-09-17 | 1976-03-17 | NEW COMPOSITION OF LATEX LOADED WITH A HYDROPHOBIC COMPOUND, ITS PREPARATION AND ITS PHOTOGRAPHIC APPLICATION | |
| US4304769A (en) * | 1974-09-17 | 1981-12-08 | Eastman Kodak Company | Process for achieving uniform, efficient distribution of hydrophobic materials through hydrophilic colloid layers and loaded latex compositions |
| GB1504949A (en) * | 1974-09-17 | 1978-03-22 | Eastman Kodak Co | Aqueous polymer latexes containing hydrophobic materials |
| US4512969A (en) * | 1974-09-17 | 1985-04-23 | Eastman Kodak Company | Compositions containing hydrophobic addenda uniformly loaded in latex polymer particles |
| JPS52102722A (en) * | 1976-02-24 | 1977-08-29 | Fuji Photo Film Co Ltd | Photosensitive material for color photography |
| US4197127A (en) * | 1976-10-08 | 1980-04-08 | Eastman Kodak Company | Photographic silver halide composition and element containing sulfonate copolymers |
| US4203716A (en) * | 1976-11-24 | 1980-05-20 | Eastman Kodak Company | Photographic elements having hydrophilic colloid layers containing hydrophobic addenda uniformly loaded in latex polymer particles |
| US4133687A (en) * | 1977-07-08 | 1979-01-09 | Eastman Kodak Company | Photographic elements having hydrophilic colloid layers containing compounds having activator precursors and hydrophobic developing agents uniformly loaded in latex polymer particles |
| JPS5432552A (en) * | 1977-08-17 | 1979-03-09 | Konishiroku Photo Ind | Method of making impregnating polymer latex composition |
| US4214047A (en) * | 1979-05-04 | 1980-07-22 | Eastman Kodak Company | Photographic elements having hydrophilic colloid layers containing hydrophobic addenda uniformly loaded in latex polymer particles |
| US4247627A (en) * | 1979-10-10 | 1981-01-27 | Eastman Kodak Company | Photographic elements having hydrophilic colloid layers containing hydrophobic ultraviolet absorbers uniformly loaded in latex polymer particles |
| US5091296A (en) * | 1990-06-26 | 1992-02-25 | Eastman Kodak Company | Polymer co-precipitated coupler dispersion |
| US5258407A (en) * | 1991-12-31 | 1993-11-02 | Sterling Winthrop Inc. | 3,4-disubstituted phenols-immunomodulating agents |
| US5254592A (en) * | 1991-12-31 | 1993-10-19 | Sterling Drug Inc. | Multiply substituted anilines, phenols and pyridines-immunomodulating agents |
| US5594047A (en) * | 1995-02-17 | 1997-01-14 | Eastman Kodak Company | Method for forming photographic dispersions comprising loaded latex polymers |
| US5582960A (en) * | 1995-02-17 | 1996-12-10 | Eastman Kodak Company | Photographic print material |
| KR101075946B1 (en) | 2003-10-23 | 2011-10-21 | 후지필름 가부시키가이샤 | Black ink for inkjet recording |
| JP5866150B2 (en) | 2010-07-30 | 2016-02-17 | 富士フイルム株式会社 | Novel azo compound, aqueous solution, ink composition, ink for ink jet recording, ink jet recording method, ink cartridge for ink jet recording, and ink jet recorded matter |
| JP5785799B2 (en) | 2010-07-30 | 2015-09-30 | 富士フイルム株式会社 | Novel azo compound, aqueous solution, ink composition, ink for ink jet recording, ink jet recording method, ink cartridge for ink jet recording, and ink jet recorded matter |
| JP2014198816A (en) | 2012-09-26 | 2014-10-23 | 富士フイルム株式会社 | Azo compound, aqueous solution, ink composition, ink for inkjet recording, inkjet recording method, ink cartridge for inkjet recording, and inkjet recorded matter |
| TW201920081A (en) | 2017-07-11 | 2019-06-01 | 美商維泰克斯製藥公司 | Carboxamide as a sodium channel regulator |
| WO2020146612A1 (en) | 2019-01-10 | 2020-07-16 | Vertex Pharmaceuticals Incorporated | Esters and carbamates as modulators of sodium channels |
| US12441703B2 (en) | 2019-01-10 | 2025-10-14 | Vertex Pharmaceuticals Incorporated | Carboxamides as modulators of sodium channels |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1981102A (en) * | 1932-08-10 | 1934-11-20 | Agfa Ansco Corp | Photographic material and process of making the same |
| BE416898A (en) * | 1935-08-07 | |||
| GB505834A (en) * | 1937-10-05 | 1939-05-18 | Michele Martinez | Improvements in or relating to colour photography |
| BE440854A (en) * | 1939-01-23 | |||
| GB524555A (en) * | 1939-01-23 | 1940-08-08 | Kodak Ltd | Improvements in colour photographic materials |
| US2289803A (en) * | 1939-05-22 | 1942-07-14 | Eastman Kodak Co | Photographic element and method of producing the same |
| US2361936A (en) * | 1939-07-20 | 1944-11-07 | Chromogen Inc | Photographic materials and process of manufacturing same |
| BE470936A (en) * | 1940-02-24 | |||
| US2376005A (en) * | 1943-04-10 | 1945-05-15 | Defender Photo Supply Co Inc | Photographic emulsion and process of making same |
| US2478400A (en) * | 1945-08-17 | 1949-08-09 | Eastman Kodak Co | Silver halide photographic emulsion with developer and color coupler dispersed therein |
| FR961836A (en) * | 1946-12-11 | 1950-05-23 | ||
| US2544903A (en) * | 1947-05-03 | 1951-03-13 | Eastman Kodak Co | Photosensitive coating containing dyes |
| US2500052A (en) * | 1948-06-02 | 1950-03-07 | Eastman Kodak Co | Photographic reversal copying process |
-
0
- BE BE528163D patent/BE528163A/xx unknown
-
1953
- 1953-04-17 US US349348A patent/US2772163A/en not_active Expired - Lifetime
-
1954
- 1954-04-11 DE DEE8851A patent/DE965616C/en not_active Expired
- 1954-04-16 FR FR1110268D patent/FR1110268A/en not_active Expired
- 1954-04-20 GB GB11365/54A patent/GB759409A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US2772163A (en) | 1956-11-27 |
| DE965616C (en) | 1957-06-13 |
| FR1110268A (en) | 1956-02-10 |
| BE528163A (en) |
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