US3655407A - Method of coating dilute aqueous emulsions - Google Patents
Method of coating dilute aqueous emulsions Download PDFInfo
- Publication number
- US3655407A US3655407A US805788A US3655407DA US3655407A US 3655407 A US3655407 A US 3655407A US 805788 A US805788 A US 805788A US 3655407D A US3655407D A US 3655407DA US 3655407 A US3655407 A US 3655407A
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- United States
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- units
- copolymer
- acrylic acid
- per cent
- weight
- 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
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- 239000000839 emulsion Substances 0.000 title claims abstract description 29
- 238000000034 method Methods 0.000 title claims description 13
- 238000000576 coating method Methods 0.000 title description 16
- 239000011248 coating agent Substances 0.000 title description 14
- 229920001577 copolymer Polymers 0.000 claims abstract description 34
- 239000000203 mixture Substances 0.000 claims abstract description 30
- 239000000084 colloidal system Substances 0.000 claims abstract description 29
- -1 silver halide Chemical class 0.000 claims abstract description 29
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229910052709 silver Inorganic materials 0.000 claims abstract description 17
- 239000004332 silver Substances 0.000 claims abstract description 17
- 125000005250 alkyl acrylate group Chemical group 0.000 claims abstract description 12
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 9
- 108010010803 Gelatin Proteins 0.000 claims description 21
- 229920000159 gelatin Polymers 0.000 claims description 21
- 235000019322 gelatine Nutrition 0.000 claims description 21
- 235000011852 gelatine desserts Nutrition 0.000 claims description 21
- 239000008273 gelatin Substances 0.000 claims description 19
- 239000010410 layer Substances 0.000 description 33
- 238000007792 addition Methods 0.000 description 8
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical group COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- 229920000800 acrylic rubber Polymers 0.000 description 6
- 239000007787 solid Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- MYSWGNHLJGOCPT-UHFFFAOYSA-N methyl prop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(=O)C=C MYSWGNHLJGOCPT-UHFFFAOYSA-N 0.000 description 4
- 239000011324 bead Substances 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000004848 polyfunctional curative Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229920002678 cellulose Chemical class 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- IONFARCGGIOTGH-UHFFFAOYSA-N 2-methylprop-2-enoic acid;propyl prop-2-enoate Chemical compound CC(=C)C(O)=O.CCCOC(=O)C=C IONFARCGGIOTGH-UHFFFAOYSA-N 0.000 description 1
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-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
- 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
- 150000007513 acids Chemical class 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 239000001913 cellulose Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000007765 extrusion coating Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- IWVKTOUOPHGZRX-UHFFFAOYSA-N methyl 2-methylprop-2-enoate;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.COC(=O)C(C)=C IWVKTOUOPHGZRX-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 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
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000012224 working solution Substances 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
- G03C1/04—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with macromolecular additives; with layer-forming substances
Definitions
- aqueous composition of a hydrophilic colloid wherein said colloid comprises from about .1 to about 6 per cent by weight of said solution, is given increased viscosity by the low-level addition of a copolymer comprising: (1) at least 50 mole per cent of units of an acrylic acid and (2) up to 50 mole per cent of units of an alkyl acrylate.
- the copolymer is added at a concentration in the range of about 0.01 to about 1 per cent by weight of the aqueous composition.
- Aqueous compositions of hydrophilic colloids such as, for example, silver halide photographic emulsions, are thickened as described and can be coated on a wide variety of supports in singleor multi-layer photographic elements.
- Silver halide photographic emulsions improved as described can be incorporated as integral layers in photographic elements. They can be chemically sensitized, e.g., with noble metal sensitizers alone or in combination with sulfur or selenium sensitizers. They can also contain spectral sensitizers, incorporated color-forming couplers, incorporated developing agents, antifoggants, plasticizers, coating aids and other suitable photographic addenda, such as described in US Pat. No. 3,297,446 (columns 4-9).
- This invention relates to the use of viscosity-increasing materials or thickening agents in dilute aqueous compositions of hydrophilic colloids.
- this invention relates to the incorporation of acrylic acid-alkyl acrylate copolymers as thickening agents in dilute gelatin photographic emulsions to improve the coatability thereof.
- photographic emulsions contain gelatin. It is also known that low gelatin concentrations permit coating of thin layers.
- Various thickening agents which facilitate the coating of dilute photographic emulsions include: carboxy-methylated carbohydrates, cellulose derivatives, carrageenans and alginic acid. Many of these materials exhibit problems producing haze, coagulation, brittleness, etc.
- Various acrylic acid polymers have also been used as a gelatin replacement.
- improved silver halide emulsions having low gelatin content and increased viscosity are desired in order to coat improved thin layers in photographic elements without substantially affecting the other physical and photographic properties of the element.
- a dilute aqueous composition of a hydrophilic colloid of low concentrations of an acrylic acid-alkyl acrylate copolymer in which the acid units comprise at least 50 mole per cent significantly increases the viscosity of said composition.
- improved coatability of a dilute silver halide emulsion is achieved by the addition to said emulsion of an acrylic acid-methyl acrylate copolymer consisting of 90 mole per cent acid units and mole per cent acrylate umts.
- Another embodiment of this invention comprises a dilute aqueous composition of a hydrophilic colloid thickened by the addition at low concentrations of an acrylic acid-alkyl acrylate copolymer comprising at least 50 mole per cent acid units and up to 50 mole per cent acrylate units.
- acrylic acid units include substituted acrylic acid units such as methacrylic acid and that the alkyl acrylate units include substituted alkyl acrylates such as alkyl methacrylates and the like.
- Another embodiment is a silver halide photographic emulsion containing less than 6 per cent gelatin by weight, thickened by the addition of a copolymer comprising 90 mole per cent acrylic acid units and 10 mole per cent methyl acrylate units.
- Still another embodiment is an improved method for bead coating thin layers in a photographic element.
- the practice of the invention as herein disclosed is a useful method of improving coating quality and versatility.
- the use of the acrylic acid-alkyl acrylate copolymers of the invention permits bead coating of more concentrated integral layers in photographic elements by the elimination of some of the gelatin vehicle without decreasing viscosity.
- the practice of the invention results in photographic elements of increased sharpness and faster processing characteristics without loss of coating uniformity.
- the compositions of the invention permit the combination of more layers into single multiple-hopper packs. They also facilitate the replacement of gelatin by other hydrophilic colloids, such as, for example, synthetic polymers where desired for faster drying, flexibility, improved covering power and dimensional stability, said polymers normally contributing too low a viscosity when used alone to allow good coating quality. They do not require the use of special hardeners to improve emulsion characteristics since conventional hydrophilic colloid hardeners such as gelatin hardeners can be used to harden the emulsions.
- the colloidal materials whose properties are improved by mixing with an acrylic acid-alkyl acrylate copolymer are those whose aqueous dispersions are recognized as useful as vehicles in integral layer photographic elements. Included are gelatins, glues, pigmented gelatins, gelatin derivatives and other colloidal materials such as, for example, poly(acrylamide), poly(vinyl alcohol), poly(vinyl pyrrolidone), and the like. In one embodiment, the preferred hydrophilic colloid is gelatin.
- the alkyl acrylate-acrylic acid copolymers generally useful in this invention comprise at least 50 mole per cent of units of an acrylic acid and up to about 50 mole per cent of units of an alkyl acrylate.
- the copolymer consists essentially of units of the monomers above in the specified ratios.
- the copolymer comprises from about to about mole per cent of units of an acrylic acid.
- Suitable alkyl acrylate units include any of those in which the alkyl radical contains from about one to about 10 carbon atoms, e.g., methyl, ethyl, propyl, hexyl, decyl, etc.
- suitable alkyl acrylate units include methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, propyl acrylate, and the like, though methyl acrylate is preferred.
- copolymer additions in the range of about 0.01 to about 1, preferably about 0.1 to about 0.5, per cent by weight of said aqueous coating composition are sufficient.
- the coating compositions contain from 1 to 5 per cent of said copolymer based on the weight of the hydrophilic colloid.
- the practice of this invention is most effective in aqueous compositions wherein the concentrations of the hydrophilic colloids are in the range of about 0.1 to about 6, preferably about 0.1 to about 4, per cent by weight.
- Dilute aqueous compositions thickened as described can be coated on a wide variety of supports in singleor multi-layer photographic elements, for example, as disclosed in Russell, US. Pat. No. 2,761,791, issued Sept. 4, 1966.
- the compositions of this invention can also be coated by dip-coating methods or methods where high viscosity is quite advantageous such as in extrusion coating, curtain coating and doctor knife coating.
- suitable supports include cellulose nitrate film, cellulose ester film, polyvinyl acetal film, polystyrene film, poly(ethylene terephthalate) film and related films or resinous materials as well as glass, paper, metal and the like.
- Supports such as paper which are coated with a-olefin polymers, particularly polymers of a-olefins containing two or more carbon atoms, e.g., polyethylene, polypropylene and ethylene butene copolymers, can also be employed.
- a-olefin polymers particularly polymers of a-olefins containing two or more carbon atoms, e.g., polyethylene, polypropylene and ethylene butene copolymers, can also be employed.
- Photographic elements can be produced comprising a support and integral layers in which at least one layer comprises a silver halide emulsion, for example, the improved viscosity compositions can be used to coat interlayers, silver halide emulsion layers, dye mordant layers, receiving layers and the like.
- the compositions of the invention improved as described can be coated in thin, uniform layers thereby permitting a combination of more of said layers into a thin photographic element.
- Silver halide photographic emulsions and elements of the invention can be used in various kinds of photographic systems, e.g., monochromatic, orthochromatic, panchromatic, infrared, X-ray and other non-optically sensitized systems.
- Silver halide photographic emulsions and elements improved as described can be used in color photography, e.g., emulsions containing color-forming couplers or emulsions to be developed by solutions incorporating couplers or other colorgenerating maierials.
- the integral layers of a photographic element can be chemically sensitized, e.g., with noble metal sensitizers alone or in combination with sulfur or selenium sensitizers. They can contain spectral sensitizers such as, for example, the cyanines, merocyanines, complex (trinuclear) cyanines, complex merocyanines, styryls and hemicyanines. Sensitizing dyes useful in such integral layers aredescribed, for example, in U.S. Pat. Nos. 2,526,632 and 2,503,776.
- the integral layers of a photographic element can also contain development modifiers such as .polymeric thioethers, onium" salts, polyalkylene glycols, etc. They can contain antifoggants and stabilizers, examples of which include seleninic acids, tetraazaindenes,'oxypentamidines, etc. i
- EXAMPLE 1 A commonly obtained copolymer comprising 90 mole per cent acrylic acid units and mole per cent methyl acrylate units, herein abbreviated as copolymer (90:10), contains about 10 per cent solids at pH 3.0. This very viscous solution (50,000-l,000,000 cps) is impractical for handling and coating. A working solution is prepared by diluting the copolymer to a 2 per cent solids solution without adjusting the pH. The
- Acrylic acid-methyl acrylate (90:10) in the cyan and magenta layers of a photographic element, as above, increases the viscosity and decreases silver halide grain sedimentation. Gelatin increases these layers to accomplish the same purpose are unacceptable since they greatly decrease the maximum density of the final color transfer print.
- Acrylic acid-methyl acrylate copolymer (90:10) has no adverse effect on the sensitometric properties of the emulsion layers of either fresh or incubated (120 F. for one week) coatings.
- a composition of matter comprising an aqueous composition of (A) a silver halide photographic emulsion comprising hydrophilic colloid wherein said colloid comprises from about 0.1 to about 6 percent by weight of said composition and (B) a copolymer comprising: (1) from at least 50 to 95 mole percent of units of an acrylic acid and (2) from 5 up to about 50 mole percent of alkyl acrylate, wherein said copolymer comprises from about 0.1 to ab0ut 5 percent by weight of said colloid.
- a photographic element comprising a support and integral layers, at least one layer comprising a silver halide emul-.
- said integral layers contain the composition of matter comprising an aqueous composition of (A) a hydrophilic colloid wherein said colloid comprises from about 0.1 to about 6 percent by weight of said solution and (B) a copolymer comprising: (1) from at least about 50 to 95 mole percent of units of an acrylic acid and (2) from 5 up to about 50 mole percent of units of an alkyl acrylate, wherein said copolymer comprises from about 0.1 to about 5 percent by weight of said colloid.
- A a hydrophilic colloid wherein said colloid comprises from about 0.1 to about 6 percent by weight of said solution
- B a copolymer comprising: (1) from at least about 50 to 95 mole percent of units of an acrylic acid and (2) from 5 up to about 50 mole percent of units of an alkyl acrylate, wherein said copolymer comprises from about 0.1 to about 5 percent by weight of said colloid.
- a method for increasing the viscosity of an aqueous composition of a silver halide photographic emulsion containing a hydrophilic colloid in an amount from about 0.1 to about 6.0 percent by weight of said composition the improvement which comprises incorporating therein a copolymer comprising 1) from at least 50 to 95 mole percent of units of an acrylic acid and (2) from 5 up to about 50 mole percent of units of alkyl acrylate, wherein said copolymer comprises from about 0.1 to about 5 percent by weight of said colloid.
- copolymer comprises from about to about mole percent acrylic acid units.
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)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80578869A | 1969-03-10 | 1969-03-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3655407A true US3655407A (en) | 1972-04-11 |
Family
ID=25192514
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US805788A Expired - Lifetime US3655407A (en) | 1969-03-10 | 1969-03-10 | Method of coating dilute aqueous emulsions |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3655407A (enrdf_load_stackoverflow) |
| BE (1) | BE747156A (enrdf_load_stackoverflow) |
| CA (1) | CA941215A (enrdf_load_stackoverflow) |
| FR (1) | FR2037855A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1287971A (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4056396A (en) * | 1973-02-12 | 1977-11-01 | Fuji Photo Film Co., Ltd. | Layers used to prevent reticulation in photographic elements |
| US4131471A (en) * | 1975-12-08 | 1978-12-26 | Polaroid Corporation | Synthetic polymeric silver halide peptizer |
| US5393571A (en) * | 1989-10-31 | 1995-02-28 | Fuji Photo Film Co., Ltd. | Curtain coating method for eliminating sagging at high flow rates |
| US5589322A (en) * | 1995-12-12 | 1996-12-31 | Eastman Kodak Company | Process for making a direct dispersion of a photographically useful material |
| US5827452A (en) * | 1995-09-02 | 1998-10-27 | Eastman Kodak Company | Method of forming photographic dispersion |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2123456C2 (de) * | 1971-05-12 | 1982-04-08 | Agfa-Gevaert Ag, 5090 Leverkusen | Lichtempfindliches, farbphotographisches Aufzeichnungsmaterial |
| US4138380A (en) | 1977-02-18 | 1979-02-06 | Gaf Corporation | Preparation of copolymer emulsions of an α,β-unsaturated carboxylic acid and methyl acrylate |
| DE2800466C3 (de) * | 1978-01-05 | 1981-12-03 | Agfa-Gevaert Ag, 5090 Leverkusen | Photographisches Material |
Citations (9)
| 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 |
| US2603565A (en) * | 1947-01-15 | 1952-07-15 | Polaroid Corp | Photographic film forming image transfer composition |
| US2761791A (en) * | 1955-02-23 | 1956-09-04 | Eastman Kodak Co | Method of multiple coating |
| US2772163A (en) * | 1953-04-17 | 1956-11-27 | Eastman Kodak Co | Photographic emulsions containing couplers and hydrosols |
| US3062674A (en) * | 1959-01-12 | 1962-11-06 | Eastman Kodak Co | Photographic product having layer containing bisepoxy ether crosslinked ethyl acrylate-acrylic acid copolymer |
| US3220844A (en) * | 1961-09-19 | 1965-11-30 | Eastman Kodak Co | Photographic products |
| US3287289A (en) * | 1962-06-11 | 1966-11-22 | Eastman Kodak Co | Plasticizers for radiation sensitive systems |
| US3297446A (en) * | 1964-02-10 | 1967-01-10 | Eastman Kodak Co | Synergistic sensitization of photographic systems with labile selenium and a noble metal |
| US3493379A (en) * | 1966-12-22 | 1970-02-03 | Du Pont | Silver halide emulsion containing amphoteric coating aid |
-
1969
- 1969-03-10 US US805788A patent/US3655407A/en not_active Expired - Lifetime
-
1970
- 1970-02-05 CA CA074,062A patent/CA941215A/en not_active Expired
- 1970-03-04 GB GB1037170A patent/GB1287971A/en not_active Expired
- 1970-03-10 FR FR7008441A patent/FR2037855A5/fr not_active Expired
- 1970-03-10 BE BE747156D patent/BE747156A/xx unknown
Patent Citations (9)
| 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 |
| US2603565A (en) * | 1947-01-15 | 1952-07-15 | Polaroid Corp | Photographic film forming image transfer composition |
| US2772163A (en) * | 1953-04-17 | 1956-11-27 | Eastman Kodak Co | Photographic emulsions containing couplers and hydrosols |
| US2761791A (en) * | 1955-02-23 | 1956-09-04 | Eastman Kodak Co | Method of multiple coating |
| US3062674A (en) * | 1959-01-12 | 1962-11-06 | Eastman Kodak Co | Photographic product having layer containing bisepoxy ether crosslinked ethyl acrylate-acrylic acid copolymer |
| US3220844A (en) * | 1961-09-19 | 1965-11-30 | Eastman Kodak Co | Photographic products |
| US3287289A (en) * | 1962-06-11 | 1966-11-22 | Eastman Kodak Co | Plasticizers for radiation sensitive systems |
| US3297446A (en) * | 1964-02-10 | 1967-01-10 | Eastman Kodak Co | Synergistic sensitization of photographic systems with labile selenium and a noble metal |
| US3493379A (en) * | 1966-12-22 | 1970-02-03 | Du Pont | Silver halide emulsion containing amphoteric coating aid |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4056396A (en) * | 1973-02-12 | 1977-11-01 | Fuji Photo Film Co., Ltd. | Layers used to prevent reticulation in photographic elements |
| US4131471A (en) * | 1975-12-08 | 1978-12-26 | Polaroid Corporation | Synthetic polymeric silver halide peptizer |
| US5393571A (en) * | 1989-10-31 | 1995-02-28 | Fuji Photo Film Co., Ltd. | Curtain coating method for eliminating sagging at high flow rates |
| US5827452A (en) * | 1995-09-02 | 1998-10-27 | Eastman Kodak Company | Method of forming photographic dispersion |
| US5589322A (en) * | 1995-12-12 | 1996-12-31 | Eastman Kodak Company | Process for making a direct dispersion of a photographically useful material |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2037855A5 (enrdf_load_stackoverflow) | 1970-12-31 |
| CA941215A (en) | 1974-02-05 |
| BE747156A (fr) | 1970-08-17 |
| GB1287971A (enrdf_load_stackoverflow) | 1972-09-06 |
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