JPS609710B2 - ビニル基含有化合物類、その製法および使用法 - Google Patents
ビニル基含有化合物類、その製法および使用法Info
- Publication number
- JPS609710B2 JPS609710B2 JP52004067A JP406777A JPS609710B2 JP S609710 B2 JPS609710 B2 JP S609710B2 JP 52004067 A JP52004067 A JP 52004067A JP 406777 A JP406777 A JP 406777A JP S609710 B2 JPS609710 B2 JP S609710B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- gelatin
- compound
- compounds
- cross
- 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
- 150000001875 compounds Chemical class 0.000 title description 43
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title description 21
- 238000004519 manufacturing process Methods 0.000 title description 5
- 239000000084 colloidal system Substances 0.000 claims description 24
- -1 vinyl compound Chemical class 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 15
- 238000004132 cross linking Methods 0.000 claims description 13
- 229920002554 vinyl polymer Polymers 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 31
- 239000008273 gelatin Substances 0.000 description 29
- 229920000159 gelatin Polymers 0.000 description 29
- 108010010803 Gelatin Proteins 0.000 description 28
- 235000019322 gelatine Nutrition 0.000 description 28
- 235000011852 gelatine desserts Nutrition 0.000 description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 239000003795 chemical substances by application Substances 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- 238000002844 melting Methods 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000000463 material Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000004848 polyfunctional curative Substances 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000004971 Cross linker Substances 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- JEIWZOOQUZYRFS-UHFFFAOYSA-N 2-ethenylsulfanylethanamine Chemical compound NCCSC=C JEIWZOOQUZYRFS-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 238000006298 dechlorination reaction Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 150000003462 sulfoxides Chemical class 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical class C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- HQSMEHLVLOGBCK-UHFFFAOYSA-N 1-ethenylsulfinylethene Chemical class C=CS(=O)C=C HQSMEHLVLOGBCK-UHFFFAOYSA-N 0.000 description 1
- JMAANYRUHQYUPE-UHFFFAOYSA-N 3-(2-chloroethylsulfonyl)-n-(2-ethenylsulfanylethyl)propanamide Chemical compound ClCCS(=O)(=O)CCC(=O)NCCSC=C JMAANYRUHQYUPE-UHFFFAOYSA-N 0.000 description 1
- NRAWOTLTKBQAIF-UHFFFAOYSA-N 3-(2-chloroethylsulfonyl)-n-(2-ethenylsulfinylethyl)propanamide Chemical compound ClCCS(=O)(=O)CCC(=O)NCCS(=O)C=C NRAWOTLTKBQAIF-UHFFFAOYSA-N 0.000 description 1
- CWVXSNVYQRIBBX-UHFFFAOYSA-N 3-(2-chloroethylsulfonyl)-n-(2-ethenylsulfonylethyl)propanamide Chemical compound ClCCS(=O)(=O)CCC(=O)NCCS(=O)(=O)C=C CWVXSNVYQRIBBX-UHFFFAOYSA-N 0.000 description 1
- IVZRGWJFRCJKDM-UHFFFAOYSA-N 3-(2-chloroethylsulfonyl)-n-(3-ethenylsulfonylpropyl)propanamide Chemical compound ClCCS(=O)(=O)CCC(=O)NCCCS(=O)(=O)C=C IVZRGWJFRCJKDM-UHFFFAOYSA-N 0.000 description 1
- LDJOLXACQPQCDE-UHFFFAOYSA-N 3-chloro-n-(2-ethenylsulfinylethylcarbamoyl)propanamide Chemical compound ClCCC(=O)NC(=O)NCCS(=O)C=C LDJOLXACQPQCDE-UHFFFAOYSA-N 0.000 description 1
- AEGSQDCWNQVSDS-UHFFFAOYSA-N 3-chloro-n-(2-ethenylsulfonylethylcarbamoyl)propanamide Chemical compound ClCCC(=O)NC(=O)NCCS(=O)(=O)C=C AEGSQDCWNQVSDS-UHFFFAOYSA-N 0.000 description 1
- FXDWBFSKZZSAHO-UHFFFAOYSA-N 3-chloropropanoyl isocyanate Chemical compound ClCCC(=O)N=C=O FXDWBFSKZZSAHO-UHFFFAOYSA-N 0.000 description 1
- 235000008753 Papaver somniferum Nutrition 0.000 description 1
- 240000001090 Papaver somniferum Species 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000007571 dilatometry Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- CDMSCFMEESJTCS-UHFFFAOYSA-N n-(2-ethenylsulfinylethyl)-3-ethenylsulfonylpropanamide Chemical compound C=CS(=O)CCNC(=O)CCS(=O)(=O)C=C CDMSCFMEESJTCS-UHFFFAOYSA-N 0.000 description 1
- KCOXZBBERDZGIF-UHFFFAOYSA-N n-(2-ethenylsulfinylethylcarbamoyl)prop-2-enamide Chemical compound C=CC(=O)NC(=O)NCCS(=O)C=C KCOXZBBERDZGIF-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
- C07C317/38—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atom of at least one amino group being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfones
- C07C317/42—Y being a hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
- C07C275/48—Y being a hydrogen or a carbon atom
- C07C275/50—Y being a hydrogen or an acyclic carbon atom
-
- 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
- G03C1/30—Hardeners
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Separation Of Suspended Particles By Flocculating Agents (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4281/76 | 1976-02-04 | ||
| GB764281A GB1542462A (en) | 1976-02-04 | 1976-02-04 | N-vinyl sulphonyl-or sulphinylalkyl amides ureas and sulphoxylureas and their use as cross-linking agents for hydrophilic colloids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5295611A JPS5295611A (en) | 1977-08-11 |
| JPS609710B2 true JPS609710B2 (ja) | 1985-03-12 |
Family
ID=9774174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP52004067A Expired JPS609710B2 (ja) | 1976-02-04 | 1977-01-19 | ビニル基含有化合物類、その製法および使用法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4120898A (OSRAM) |
| JP (1) | JPS609710B2 (OSRAM) |
| BE (1) | BE851032A (OSRAM) |
| CH (1) | CH628445A5 (OSRAM) |
| DE (1) | DE2704363A1 (OSRAM) |
| FR (1) | FR2354318A1 (OSRAM) |
| GB (1) | GB1542462A (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2856384C3 (de) * | 1978-12-27 | 1981-11-19 | Chemische Fabrik Stockhausen & Cie, 4150 Krefeld | Quartäre Ammoniumgruppen enthaltende Acrylyl- bzw. Methacrylylharnstoffe und Verfahren zu ihrer Herstellung |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE686440A (OSRAM) * | 1965-09-20 | 1967-02-15 | ||
| CH473887A (de) * | 1966-04-12 | 1969-06-15 | Ciba Geigy | Verfahren zum Härten von Gelatine |
| US3551159A (en) * | 1966-05-25 | 1970-12-29 | Ciba Ltd | Process for hardening gelatine |
| DE1595680A1 (de) * | 1966-09-16 | 1970-04-23 | Bayer Ag | Sulfonsaeuregruppen enthaltende Polymerisate |
| CH474085A (de) * | 1966-10-27 | 1969-06-15 | Ciba Geigy | Verfahren zur Empfindlichkeitssteigerung von photographischem Material |
| ZA6800017B (OSRAM) * | 1967-01-05 | |||
| CH501724A (de) * | 1967-09-27 | 1971-01-15 | Ciba Geigy Ag | Verwendung von carbonsäureamidgruppenhaltigen Verbindungen zum Härten von Gelatine |
| CA960694A (en) * | 1967-11-13 | 1975-01-07 | Hyman L. Cohen | Non-wandering hardening compounds and their use |
| US3989842A (en) * | 1970-05-15 | 1976-11-02 | U.S. Philips Corporation | Certain substituted benzoyl urea insecticides |
| JPS5035807B2 (OSRAM) * | 1971-12-30 | 1975-11-19 | ||
| BE795839A (fr) * | 1972-02-25 | 1973-08-23 | Ciba Geigy | Procede de retification de colloides hydrophiles |
| US3841872A (en) * | 1972-09-29 | 1974-10-15 | Eastman Kodak Co | Hydrophilic-colloid silver halide emulsion hardened with a bisvinylsulfonyl compound |
| GB1470178A (en) * | 1973-03-12 | 1977-04-14 | Konishiroku Photo Ind | Gelating hardening process |
| CH582896A5 (OSRAM) * | 1973-05-07 | 1976-12-15 | Ciba Geigy Ag | |
| CH592700A5 (OSRAM) * | 1974-01-31 | 1977-11-15 | Ciba Geigy Ag | |
| US4011201A (en) * | 1974-08-15 | 1977-03-08 | Eastman Kodak Company | Polymers of monomers containing active methylene groups and other ethylenically unsaturated monomers |
| DE2447680C3 (de) * | 1974-10-07 | 1981-10-29 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung eines Formkörpers, der aus chemisch modifiziertem Eiweiß besteht, und seine Verwendung |
| JPS51126124A (en) * | 1975-04-25 | 1976-11-04 | Fuji Photo Film Co Ltd | Gelatin setting method |
-
1976
- 1976-02-04 GB GB764281A patent/GB1542462A/en not_active Expired
-
1977
- 1977-01-18 US US05/760,291 patent/US4120898A/en not_active Expired - Lifetime
- 1977-01-19 JP JP52004067A patent/JPS609710B2/ja not_active Expired
- 1977-01-21 CH CH74177A patent/CH628445A5/de not_active IP Right Cessation
- 1977-02-02 FR FR7702830A patent/FR2354318A1/fr active Granted
- 1977-02-02 DE DE19772704363 patent/DE2704363A1/de not_active Ceased
- 1977-02-03 BE BE174610A patent/BE851032A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2354318A1 (fr) | 1978-01-06 |
| BE851032A (fr) | 1977-08-03 |
| GB1542462A (en) | 1979-03-21 |
| FR2354318B1 (OSRAM) | 1980-10-03 |
| JPS5295611A (en) | 1977-08-11 |
| DE2704363A1 (de) | 1977-08-18 |
| CH628445A5 (de) | 1982-02-26 |
| US4120898A (en) | 1978-10-17 |
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