GB1209813A - Improved photographic silver halide material - Google Patents
Improved photographic silver halide materialInfo
- Publication number
- GB1209813A GB1209813A GB8652/68A GB865268A GB1209813A GB 1209813 A GB1209813 A GB 1209813A GB 8652/68 A GB8652/68 A GB 8652/68A GB 865268 A GB865268 A GB 865268A GB 1209813 A GB1209813 A GB 1209813A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- sulphobenzimidazole
- acid
- refluxing
- benzimidazole
- 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
- -1 silver halide Chemical class 0.000 title abstract 5
- 239000000463 material Substances 0.000 title 1
- 229910052709 silver Inorganic materials 0.000 title 1
- 239000004332 silver Substances 0.000 title 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 9
- 238000010992 reflux Methods 0.000 abstract 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 6
- 239000000243 solution Substances 0.000 abstract 5
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 abstract 4
- XGIDEUICZZXBFQ-UHFFFAOYSA-N 1h-benzimidazol-2-ylmethanethiol Chemical compound C1=CC=C2NC(CS)=NC2=C1 XGIDEUICZZXBFQ-UHFFFAOYSA-N 0.000 abstract 3
- FKSRSWQTEJTBMI-UHFFFAOYSA-N 3,4-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1N FKSRSWQTEJTBMI-UHFFFAOYSA-N 0.000 abstract 3
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 3
- GBNVXYXIRHSYEG-UHFFFAOYSA-N 1-chloro-2-ethylsulfanylethane Chemical compound CCSCCCl GBNVXYXIRHSYEG-UHFFFAOYSA-N 0.000 abstract 2
- JWOOBCSOBNSNHY-UHFFFAOYSA-N 2-[3-[3-(1H-benzimidazol-2-yl)propyldisulfanyl]propyl]-1H-benzimidazole Chemical compound N1=C(NC2=C1C=CC=C2)CCCSSCCCC=2NC1=C(N2)C=CC=C1 JWOOBCSOBNSNHY-UHFFFAOYSA-N 0.000 abstract 2
- QACHEAFEHPVJER-UHFFFAOYSA-N 3,4-diaminobenzoic acid;hydrochloride Chemical compound Cl.NC1=CC=C(C(O)=O)C=C1N QACHEAFEHPVJER-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- 239000000725 suspension Substances 0.000 abstract 2
- DETWFIUAXSWCIK-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-1-ylazanium;chloride Chemical compound [Cl-].C1=CC=C2C([NH3+])CCCC2=C1 DETWFIUAXSWCIK-UHFFFAOYSA-N 0.000 abstract 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 abstract 1
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 abstract 1
- PTBGZESVAJXTHX-UHFFFAOYSA-N 1h-benzimidazole;hydrate Chemical compound O.C1=CC=C2NC=NC2=C1 PTBGZESVAJXTHX-UHFFFAOYSA-N 0.000 abstract 1
- BLUMZAJRPJMXSA-UHFFFAOYSA-N 2-(1h-benzimidazol-2-ylmethylsulfanyl)acetic acid Chemical compound C1=CC=C2NC(CSCC(=O)O)=NC2=C1 BLUMZAJRPJMXSA-UHFFFAOYSA-N 0.000 abstract 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 abstract 1
- UHPCPLNAEJYLTQ-UHFFFAOYSA-N 2-methyl-3-methylsulfanyl-1H-1,2,4-triazole-5-thione Chemical compound CSC1=NC(=NN1C)S UHPCPLNAEJYLTQ-UHFFFAOYSA-N 0.000 abstract 1
- OWXCYFUNGFTAMS-UHFFFAOYSA-N 2-methylsulfanylacetyl chloride Chemical compound CSCC(Cl)=O OWXCYFUNGFTAMS-UHFFFAOYSA-N 0.000 abstract 1
- LWJQGKJCZOGGPJ-UHFFFAOYSA-N 2-methylsulfanylbenzoic acid Chemical compound CSC1=CC=CC=C1C(O)=O LWJQGKJCZOGGPJ-UHFFFAOYSA-N 0.000 abstract 1
- CWWSIJWEKCSVRO-UHFFFAOYSA-N 3,3,5-trimethyloxathiolane 2,2-dioxide Chemical compound CC1CC(C)(C)S(=O)(=O)O1 CWWSIJWEKCSVRO-UHFFFAOYSA-N 0.000 abstract 1
- SNNLTRLHBHHUPZ-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)propane-1-thiol Chemical compound C1=CC=C2NC(CCCS)=NC2=C1 SNNLTRLHBHHUPZ-UHFFFAOYSA-N 0.000 abstract 1
- CDLNRAKSASRRLF-UHFFFAOYSA-N 3-(1h-benzimidazol-2-ylmethylsulfanyl)propane-1-sulfonic acid Chemical compound C1=CC=C2NC(CSCCCS(=O)(=O)O)=NC2=C1 CDLNRAKSASRRLF-UHFFFAOYSA-N 0.000 abstract 1
- QQRJUYOHJODBBO-UHFFFAOYSA-N 3-[2-(1h-benzimidazol-2-yl)ethylsulfanyl]propane-1-sulfonic acid Chemical compound C1=CC=C2NC(CCSCCCS(=O)(=O)O)=NC2=C1 QQRJUYOHJODBBO-UHFFFAOYSA-N 0.000 abstract 1
- SGJUXHAIVAQHBO-UHFFFAOYSA-N 3-[3-(1h-benzimidazol-2-yl)propylsulfanyl]propane-1-sulfonic acid Chemical compound C1=CC=C2NC(CCCSCCCS(=O)(=O)O)=NC2=C1 SGJUXHAIVAQHBO-UHFFFAOYSA-N 0.000 abstract 1
- PPNLUYUKLWXBFP-UHFFFAOYSA-N 3-[[5-(2-ethylsulfanylethylsulfanyl)-1h-1,2,4-triazol-3-yl]sulfanyl]propane-1-sulfonic acid Chemical compound CCSCCSC1=NC(SCCCS(O)(=O)=O)=NN1 PPNLUYUKLWXBFP-UHFFFAOYSA-N 0.000 abstract 1
- DFRYPXBYVKLWKI-UHFFFAOYSA-N 3-[[5-(methylsulfanylmethyl)-1h-1,2,4-triazol-3-yl]sulfanyl]propane-1-sulfonic acid Chemical compound CSCC1=NC(SCCCS(O)(=O)=O)=NN1 DFRYPXBYVKLWKI-UHFFFAOYSA-N 0.000 abstract 1
- YYSCJLLOWOUSHH-UHFFFAOYSA-N 4,4'-disulfanyldibutanoic acid Chemical compound OC(=O)CCCSSCCCC(O)=O YYSCJLLOWOUSHH-UHFFFAOYSA-N 0.000 abstract 1
- YXAYZDANCOBCIS-UHFFFAOYSA-N 4-(1h-benzimidazol-2-ylmethylsulfanyl)-2-methylpentane-2-sulfonic acid Chemical compound C1=CC=C2NC(CSC(CC(C)(C)S(O)(=O)=O)C)=NC2=C1 YXAYZDANCOBCIS-UHFFFAOYSA-N 0.000 abstract 1
- FPTFJACJZQAZKH-UHFFFAOYSA-N 4-(1h-benzimidazol-2-ylmethylsulfanyl)butane-1-sulfonic acid Chemical compound C1=CC=C2NC(CSCCCCS(=O)(=O)O)=NC2=C1 FPTFJACJZQAZKH-UHFFFAOYSA-N 0.000 abstract 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- QQWGVQWAEANRTK-UHFFFAOYSA-N bromosuccinic acid Chemical compound OC(=O)CC(Br)C(O)=O QQWGVQWAEANRTK-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 abstract 1
- MHYFEEDKONKGEB-UHFFFAOYSA-N oxathiane 2,2-dioxide Chemical compound O=S1(=O)CCCCO1 MHYFEEDKONKGEB-UHFFFAOYSA-N 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 abstract 1
- KOODSCBKXPPKHE-UHFFFAOYSA-N propanethioic s-acid Chemical compound CCC(S)=O KOODSCBKXPPKHE-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- VJBZMEKLDZXKHC-UHFFFAOYSA-M sodium 3-[(5-sulfanylidene-1,2-dihydro-1,2,4-triazol-3-yl)sulfanyl]propane-1-sulfonate Chemical compound [Na+].S(=O)(=O)([O-])CCCSC1=NNC(=N1)S VJBZMEKLDZXKHC-UHFFFAOYSA-M 0.000 abstract 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 abstract 1
- 150000003568 thioethers Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/28—Sulfur atoms
-
- 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
- G03C1/34—Fog-inhibitors; Stabilisers; Agents inhibiting latent image regression
- G03C1/346—Organic derivatives of bivalent sulfur, selenium or tellurium
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)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8652/68A GB1209813A (en) | 1968-02-22 | 1968-02-22 | Improved photographic silver halide material |
| FR6903541A FR2002378A1 (enrdf_load_stackoverflow) | 1968-02-22 | 1969-02-12 | |
| US799097A US3667957A (en) | 1968-02-22 | 1969-02-13 | Photographic material with a stabilizer antifoggant bidentate compound |
| BE728387D BE728387A (enrdf_load_stackoverflow) | 1968-02-22 | 1969-02-14 | |
| DE1908217A DE1908217C2 (de) | 1968-02-22 | 1969-02-19 | Photographisches Aufzeichnungsmaterial |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8652/68A GB1209813A (en) | 1968-02-22 | 1968-02-22 | Improved photographic silver halide material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1209813A true GB1209813A (en) | 1970-10-21 |
Family
ID=9856615
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8652/68A Expired GB1209813A (en) | 1968-02-22 | 1968-02-22 | Improved photographic silver halide material |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3667957A (enrdf_load_stackoverflow) |
| BE (1) | BE728387A (enrdf_load_stackoverflow) |
| DE (1) | DE1908217C2 (enrdf_load_stackoverflow) |
| FR (1) | FR2002378A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1209813A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4420554A (en) * | 1981-02-17 | 1983-12-13 | Mitsubishi Paper Mills, Ltd. | Silver halide photosensitive materials |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4057425A (en) * | 1975-07-16 | 1977-11-08 | Polaroid Corporation | 2-Substituted benzimidazoles in multicolor diffusion transfer |
| US4503139A (en) * | 1983-05-09 | 1985-03-05 | Polaroid Corporation | Photographic products and processes and novel compounds |
| US4847383A (en) * | 1983-05-09 | 1989-07-11 | Polaroid Corporation | Photographic reagent tetrazoles |
| EP1484323B1 (en) * | 2003-06-06 | 2009-09-30 | Agfa HealthCare NV | 2-thiosubstituted benzimidazole derivatives as surfactants for photographic application |
| FR3108191B1 (fr) | 2020-03-10 | 2023-05-19 | Psa Automobiles Sa | Procédé et dispositif de mise à jour d’un logiciel comportant des adresses physiques vers la mémoire d’un calculateur embarqué d’un véhicule |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE621606A (enrdf_load_stackoverflow) * | 1961-08-25 | |||
| US3202512A (en) * | 1962-02-23 | 1965-08-24 | Eastman Kodak Co | Photographic silver halide emulsions stabilized with tetrazaindene compounds |
| US3255202A (en) * | 1963-08-23 | 1966-06-07 | Union Carbide Corp | Process for the preparation of 2-(acylamidoalkyl)benzimidazoles |
-
1968
- 1968-02-22 GB GB8652/68A patent/GB1209813A/en not_active Expired
-
1969
- 1969-02-12 FR FR6903541A patent/FR2002378A1/fr not_active Withdrawn
- 1969-02-13 US US799097A patent/US3667957A/en not_active Expired - Lifetime
- 1969-02-14 BE BE728387D patent/BE728387A/xx unknown
- 1969-02-19 DE DE1908217A patent/DE1908217C2/de not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4420554A (en) * | 1981-02-17 | 1983-12-13 | Mitsubishi Paper Mills, Ltd. | Silver halide photosensitive materials |
Also Published As
| Publication number | Publication date |
|---|---|
| US3667957A (en) | 1972-06-06 |
| FR2002378A1 (enrdf_load_stackoverflow) | 1969-10-17 |
| BE728387A (enrdf_load_stackoverflow) | 1969-08-14 |
| DE1908217A1 (de) | 1969-09-11 |
| DE1908217C2 (de) | 1983-12-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 435 | Patent endorsed 'licences of right' on the date specified (sect. 35/1949) | ||
| PCNP | Patent ceased through non-payment of renewal fee |