US3850639A - Hydrophilic colloid silver halide emulsion hardened with a bis(vinyl-sulfonylmethyl) ether and an acrylic compound - Google Patents
Hydrophilic colloid silver halide emulsion hardened with a bis(vinyl-sulfonylmethyl) ether and an acrylic compound Download PDFInfo
- Publication number
- US3850639A US3850639A US00357975A US35797573A US3850639A US 3850639 A US3850639 A US 3850639A US 00357975 A US00357975 A US 00357975A US 35797573 A US35797573 A US 35797573A US 3850639 A US3850639 A US 3850639A
- Authority
- US
- United States
- Prior art keywords
- hardener
- photographic
- hydrophilic colloid
- gelatin
- bis
- 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 - Lifetime
Links
- 239000000839 emulsion Substances 0.000 title claims abstract description 30
- KAMCBFNNGGVPPW-UHFFFAOYSA-N 1-(ethenylsulfonylmethoxymethylsulfonyl)ethene Chemical compound C=CS(=O)(=O)COCS(=O)(=O)C=C KAMCBFNNGGVPPW-UHFFFAOYSA-N 0.000 title claims abstract description 10
- -1 silver halide Chemical class 0.000 title claims description 25
- 239000000084 colloidal system Substances 0.000 title claims description 24
- 229910052709 silver Inorganic materials 0.000 title claims description 17
- 239000004332 silver Substances 0.000 title claims description 17
- 239000004848 polyfunctional curative Substances 0.000 claims abstract description 59
- 239000000203 mixture Substances 0.000 claims abstract description 51
- 108010010803 Gelatin Proteins 0.000 claims abstract description 27
- 239000008273 gelatin Substances 0.000 claims abstract description 27
- 229920000159 gelatin Polymers 0.000 claims abstract description 27
- 235000019322 gelatine Nutrition 0.000 claims abstract description 27
- 235000011852 gelatine desserts Nutrition 0.000 claims abstract description 27
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 11
- CHDKQNHKDMEASZ-UHFFFAOYSA-N n-prop-2-enoylprop-2-enamide Chemical compound C=CC(=O)NC(=O)C=C CHDKQNHKDMEASZ-UHFFFAOYSA-N 0.000 claims description 9
- 238000002844 melting Methods 0.000 claims description 7
- 230000008018 melting Effects 0.000 claims description 7
- MVWQZIKQYNDOLK-UHFFFAOYSA-N 2-methyl-n-prop-2-enoylprop-2-enamide Chemical compound CC(=C)C(=O)NC(=O)C=C MVWQZIKQYNDOLK-UHFFFAOYSA-N 0.000 claims description 5
- 230000006872 improvement Effects 0.000 claims description 5
- QPNIKQOMMMOUGM-UHFFFAOYSA-N CC=CC(=O)NC(C=C)=O Chemical group CC=CC(=O)NC(C=C)=O QPNIKQOMMMOUGM-UHFFFAOYSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 11
- 238000000034 method Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000011161 development Methods 0.000 description 4
- LKGZVGKQDZDRGT-UHFFFAOYSA-N n-(prop-2-enoylcarbamoyl)prop-2-enamide Chemical compound C=CC(=O)NC(=O)NC(=O)C=C LKGZVGKQDZDRGT-UHFFFAOYSA-N 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000009792 diffusion process Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920001059 synthetic polymer Polymers 0.000 description 3
- OYTMCDCWKVWQET-UHFFFAOYSA-N 1-ethenylsulfonyl-2-(2-ethenylsulfonylethoxy)ethane Chemical compound C=CS(=O)(=O)CCOCCS(=O)(=O)C=C OYTMCDCWKVWQET-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000001627 detrimental effect Effects 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 229920005615 natural polymer Polymers 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- JKFYKCYQEWQPTM-UHFFFAOYSA-N 2-azaniumyl-2-(4-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-UHFFFAOYSA-N 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 241001163743 Perlodes Species 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 229910021612 Silver iodide Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 1
- HOLVRJRSWZOAJU-UHFFFAOYSA-N [Ag].ICl Chemical compound [Ag].ICl HOLVRJRSWZOAJU-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 1
- 229940045105 silver iodide Drugs 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000011885 synergistic combination Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 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
- G03C1/30—Hardeners
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/139—Defect coating
Definitions
- compositions containing hydrophilic colloids such as gelatin which have been chemically hardened to photographic emulsions containing such chemically hardened colloids, and to colloid/hardener admixtures useful in the manufacture of such hardened compositions. More particularly, this invention is directed to gelatin-containing compositions which have been hardened with a mixture of chemical hardeners, which mixture causes better afterhardening characteristics (in the hardened compositions) than can be obtained by use of either of the individual hardeners alone.
- Metallic salts for instance, such as those of chromium, aluminum, and zirconium tend to react with and harden gelatin so very quickly that their addition, before shaping of the gelatin, in quantities required to achieve the desired hardening, involves the risk of premature coagulation of the gelatin solution.
- Aldehydes such as formaldehyde are partly volatilized when materials containing them are dried, so that an accurate dosage is difficult to realize.
- Certain other simple organic hardeners require a high molecular weight ballast in order to render them nondiffusible which often causes adverse physical characteristics in the photographic emulsion. Also, such hardeners usually contain an undesirably low ratio of active hardening groups to ballast groups.
- compositions containing hardened-hydrophilic colloid which compositions have been chemically hardened by a synergistic combination of hardeners for the purpose of improving the afterhardening effect of such hardeners.
- hardener mixtures described in this application can be used most advantageously with natural or synthetic polymers used as vehicles or binders in preparing photographic elements.
- Specific materials which can be hardened according to the practice of this invention include hardenable materials such as polymers, for example, gelatin, colloidal albumin, proteins, dispersed polymerized vinyl compounds, particularly those which increase the dimensional stability of photographic materials as exemplified by amine-containing polymers of alkyl acrylates, methacrylates, acrylic acid, sulfoalkyl acrylates or methacrylates, maleic acid, and the like.
- hardenable hydrophilic colloids useful in the practice of this invention are those generally known in the photographic art which can be hardened by formaldehyde.
- hardenable hydrophilic colloids are materials such as gelatin which have melting points below about 65C, and preferably between about 27C. and about 50C. Typical examples of such materials can be found in the aforementioned US. patents.
- the hardening mixtures described herein can be used in various kinds of photographic emulsions. In addition to being useful in orthochromatic, panchromatic, and infrared emulsions, they are also useful in x-ray and other nonspectrally sensitized emulsions. They can be added to the emulsions before or after the addition of any spectral sensitizing dyes which may be used. They are effective in sulfur and gold sensitized silver halide emulsions.
- the mixtures of hardeners of this invention possess good hardening properties when they are blended with hardenable materials in any useful form such as in solution, emulsion or layer form.
- the mixtures can be used in any suitable hardening concentration which results in an increase in the melting point of the hardenable hydrophilic colloid of at least about 5C, including for example concentrations of from about 0.5 to about weight percent, based upon the dried weight of the hardenable material, and preferably within the range of from about 0.7 to 3 weight percent.
- These mixtures of hardeners are particularly useful in hardening hardenable photographic light sensitive emulsion layers; more particularly, those which contain gelatin and photographic silver halide.
- the mixtures of hardeners can be combined directly with the emulsion during its preparation, either as a mixture or as the individual components of the mixture. Then the treated emulsion can coated in layer form onto a substrate via conventional coating techniques and subsequently dried. The bulk of the hardening reaction (wherein the hardeners react with the hydrophilic colloid in the coated layer) preferably takes place during the drying step in such processes.
- the resulting dried, chemically hardened photographic elements can then be subjected to relatively higher processing (developing, fixing, etc.) temperature conditions than could otherwise similar, but unhardened, photographic elements without being physically degraded due to the higher temperature.
- Hardening can also be accomplished by contacting layer(s) of hardenable hydrophilic colloid material with an aqueous solution of one of the present hardener mixtures for a time, and at a temperature, which is sufficient to result in the desired degree of hardening (which can also take place during a subsequent drying step if desired).
- tion can be coated on a wide variety of supports.
- Typical supports include those generally employed for photographic elements, as exemplified by cellulose nitrate film, cellulose acetate film, polyvinyl acetal film, polystyrene film, polyethylene terephthalate film, and related films of resinous materials as well as glass, paper, metal, wood and the like.
- Supports such as paper that are caoted with a-olefin polymers, particularly polymers of a-olefins containing 2-10 carbon atoms (for example, polyethylene, polypropylene, ethylene butene copolymers, and the like) can also be employed.
- photographic emulsions and elements can also contain other additives, particularly those known to be beneficial in photographic emulsions, as exemplified by spectral sensitizers, speed-increasing material, other hardeners, plasticizers, and the like.
- the emulsions hardened by the mixtures of this invention can be used in photograph elements intended for color photography and thus may contain colorforming couplers. They may be used as emulsions to be developed by solutions containing such couplers or other color-generating materials, or they may be used as emulsions of the mixed-packet type.
- the silver halides employed in the photographic emulsions include any of the photosensitive silver halides as exemplified by silver bromide, silver iodide, silver chloride, silver chlorobromide, silver chloroiodide, and the like.
- the silver halides used can be those which form latent images predominantly on the surface of the silver halide grains or those which form latent images inside the silver halide grains.
- Hardened emulsions obtained in accordance with this invention employing gelatin or other hardenable hydrophilic colloids may be used in diffusion transfer materials.
- the undeveloped silver halide is complexed in nonimage areas of the negative to form a water-soluble compound which is permitted to diffuse to a receiving layer in which said compound precipitates out as a positive metallic silver image.
- the final image is produced by diffusion of the developer, oxidized developer, coupler or dye, from the exposed and developed light-sensitive layer to a second layer in close proximity thereto. It is particularly advantageous to employ the hardener mixtures of this invention with hardenable substances or in systems comprising photographic emulsions, layers or solutions of hardenable matter where very little afterhardening is advantageous.
- EXAMPLE I The hardeners which were tested were the following: Three layer photographic elements were prepared by I coating in a conventional manner on a cellulose acetate I diacrylamide photographic support the following layers: 11 his(vinylsulfonylmethyl)ether Ill bis(vinylsulfonylethyl)ether l a gelatm SuPlayer contammg 162 g gelatm per IV l,7-dichloro-3,3,5,5tctruoxo-3,S-dithiuhcptunc Square V Nmethacryloylucrylumitle 2.
- a photographic element comprising a support and at least one layer comprising photosensitive silver halide and at least one layer comprising a reaction product of i. at least one hardenable hydrophilic colloid, and
- a hardener composition in a concentration sufficient to increase the melting point of said hydrophilic colloid at least about 5C; the improvement which comprises using as a hardener composition a combination of a. bis(vinylsulfonylmethyl)ether and b. an acrylic hardener selected from the group consisting of diacrylamide, N-methacryloylacrylamide and N,N'-diacryloylurea; the weight ratio of (a) to (b) in said hardener composition being from about 5:1 to about 1:5.
- a photographic element as in claim 1, wherein said hardenable hydrophilic colloid is gelatin.
- a photographic emulsion composition containing at least one hardenable hydrophilic colloid, at least one photosensitive silver halide, and a hardener composition in an amount sufficient to increase the melting point of said hydrophilic colloid at least about 5C; the improvement which comprises using as said hardener composition a combination of a. bis(vinylsulfonylmethyl)ether and b. an acrylic hardener selected from the group consisting of diacrylamide, N-methacryloylacrylamide and N,N'-diacryloylurea; the weight ratio of (a) to (b) in said hardener composition being from about 5:1 to about 1:5.
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)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00357975A US3850639A (en) | 1973-05-07 | 1973-05-07 | Hydrophilic colloid silver halide emulsion hardened with a bis(vinyl-sulfonylmethyl) ether and an acrylic compound |
| CA197,319A CA1019617A (en) | 1973-05-07 | 1974-04-10 | Controlling after-hardening in hardenable hydrophilic colloids |
| DE19742420414 DE2420414A1 (de) | 1973-05-07 | 1974-04-26 | Photographisches material |
| FR7415173A FR2229079B1 (enrdf_load_stackoverflow) | 1973-05-07 | 1974-05-02 | |
| GB2006374A GB1443386A (en) | 1973-05-07 | 1974-05-07 | Photographic element |
| JP49049843A JPS5019424A (enrdf_load_stackoverflow) | 1973-05-07 | 1974-05-07 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00357975A US3850639A (en) | 1973-05-07 | 1973-05-07 | Hydrophilic colloid silver halide emulsion hardened with a bis(vinyl-sulfonylmethyl) ether and an acrylic compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3850639A true US3850639A (en) | 1974-11-26 |
Family
ID=23407800
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00357975A Expired - Lifetime US3850639A (en) | 1973-05-07 | 1973-05-07 | Hydrophilic colloid silver halide emulsion hardened with a bis(vinyl-sulfonylmethyl) ether and an acrylic compound |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3850639A (enrdf_load_stackoverflow) |
| JP (1) | JPS5019424A (enrdf_load_stackoverflow) |
| CA (1) | CA1019617A (enrdf_load_stackoverflow) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4057538A (en) * | 1974-02-13 | 1977-11-08 | Konishiroku Photo Industry Co., Ltd. | Method for hardening gelatin |
| US4161407A (en) * | 1977-10-06 | 1979-07-17 | Eastman Kodak Company | Crosslinkable polymers having vinylsulfonyl groups or styrylsulfonyl groups and their use as hardeners for gelatin |
| US5187259A (en) * | 1990-11-14 | 1993-02-16 | Eastman Kodak Company | Chain extended gelatin |
| US5318889A (en) * | 1992-12-21 | 1994-06-07 | Eastman Kodak Company | Use of chain-extended acid processed ossein gelatin in the preparation of photographic elements |
| US5378598A (en) * | 1992-12-21 | 1995-01-03 | Eastman Kodak Company | Use of acid processed ossein gelatin and chain-extened acid processed ossein gelatin as peptizers in the preparation of photographic emulsions |
| US5800977A (en) * | 1996-07-24 | 1998-09-01 | Eastman Kodak Company | Hardening a hydrophilic colloid composition |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5612854B2 (enrdf_load_stackoverflow) * | 1973-10-08 | 1981-03-25 | ||
| JPH01311601A (ja) * | 1988-06-09 | 1989-12-15 | Fuji Elelctrochem Co Ltd | 偏波面切換器 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3539644A (en) * | 1967-11-13 | 1970-11-10 | Eastman Kodak Co | Bis(vinylsulfonylmethyl) ether |
| GB1234839A (en) * | 1967-08-22 | 1971-06-09 | Ciba Geigy | Process for hardening colloid layers in photographic material |
| US3635718A (en) * | 1967-03-06 | 1972-01-18 | Ciba Geigy Ag | Process for hardening water-soluble polymers |
| US3640720A (en) * | 1967-11-13 | 1972-02-08 | Eastman Kodak Co | Nonwandering hardening compounds and their use |
| US3642486A (en) * | 1970-03-19 | 1972-02-15 | Eastman Kodak Co | Vinylsulfonyl-containing compounds as hardening agents |
-
1973
- 1973-05-07 US US00357975A patent/US3850639A/en not_active Expired - Lifetime
-
1974
- 1974-04-10 CA CA197,319A patent/CA1019617A/en not_active Expired
- 1974-05-07 JP JP49049843A patent/JPS5019424A/ja active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3635718A (en) * | 1967-03-06 | 1972-01-18 | Ciba Geigy Ag | Process for hardening water-soluble polymers |
| GB1234839A (en) * | 1967-08-22 | 1971-06-09 | Ciba Geigy | Process for hardening colloid layers in photographic material |
| US3539644A (en) * | 1967-11-13 | 1970-11-10 | Eastman Kodak Co | Bis(vinylsulfonylmethyl) ether |
| US3640720A (en) * | 1967-11-13 | 1972-02-08 | Eastman Kodak Co | Nonwandering hardening compounds and their use |
| US3642486A (en) * | 1970-03-19 | 1972-02-15 | Eastman Kodak Co | Vinylsulfonyl-containing compounds as hardening agents |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4057538A (en) * | 1974-02-13 | 1977-11-08 | Konishiroku Photo Industry Co., Ltd. | Method for hardening gelatin |
| US4161407A (en) * | 1977-10-06 | 1979-07-17 | Eastman Kodak Company | Crosslinkable polymers having vinylsulfonyl groups or styrylsulfonyl groups and their use as hardeners for gelatin |
| US5187259A (en) * | 1990-11-14 | 1993-02-16 | Eastman Kodak Company | Chain extended gelatin |
| US5318889A (en) * | 1992-12-21 | 1994-06-07 | Eastman Kodak Company | Use of chain-extended acid processed ossein gelatin in the preparation of photographic elements |
| US5378598A (en) * | 1992-12-21 | 1995-01-03 | Eastman Kodak Company | Use of acid processed ossein gelatin and chain-extened acid processed ossein gelatin as peptizers in the preparation of photographic emulsions |
| US5536630A (en) * | 1992-12-21 | 1996-07-16 | Eastman Kodak Company | Use of acid processed ossein gelatin and chain-extended acid processed ossein gelatin as peptizers in the preparation of photographic elements |
| US5800977A (en) * | 1996-07-24 | 1998-09-01 | Eastman Kodak Company | Hardening a hydrophilic colloid composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5019424A (enrdf_load_stackoverflow) | 1975-02-28 |
| CA1019617A (en) | 1977-10-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3930867A (en) | Macrocyclic polyamines as sensitizers for silver halide emulsions | |
| US3206313A (en) | Chemically sensitized emulsions having low surface sensitivity and high internal sensitivity | |
| US3640720A (en) | Nonwandering hardening compounds and their use | |
| SU576977A3 (ru) | Способ получени изображени | |
| US2305693A (en) | Process of making photographs | |
| US3850639A (en) | Hydrophilic colloid silver halide emulsion hardened with a bis(vinyl-sulfonylmethyl) ether and an acrylic compound | |
| US3832181A (en) | Photosensitive silver halide material containing a hydrophilic colloid hardened with a combination of formaldehyde and bis(vinylsulfonyl-methyl)ether | |
| US3075841A (en) | Mordant treating process and elements containing same | |
| US2397866A (en) | Photographic elements | |
| JPS5943733B2 (ja) | 写真現像抑制剤スキャベンジャ− | |
| US3840370A (en) | Controlling after-hardening in hardenable hydrophilic colloids | |
| US3565625A (en) | Photographic elements having thiazolidine compounds in light-in-sensitive layers | |
| US4175970A (en) | Process for sensitizing photographic silver halide emulsions | |
| US3730726A (en) | Color photographic light-sensitive elements | |
| US3819379A (en) | Silver halide photographic material for use in color photography | |
| US3655407A (en) | Method of coating dilute aqueous emulsions | |
| US3764327A (en) | Color photographic light sensitive material | |
| US3663230A (en) | Light-sensitive silver halide photographic emulsions | |
| US3733196A (en) | Chemically hardened silver halide emulsions containing tempering concentrations of simple organic polyols | |
| US3877947A (en) | Photographic element | |
| US3123492A (en) | Maffet | |
| US3597215A (en) | Photographic silver halide and a poly (vinyl alcohol) binding agent | |
| US3561967A (en) | Photographic light-sensitive silver halide elements | |
| US3547650A (en) | Silver halide emulsion comprising a gelatin - polyvinyl compound dispersion | |
| US3533793A (en) | Process for preparing photographic elements |