US3552972A - Antistatic layer for photographic materials - Google Patents
Antistatic layer for photographic materials Download PDFInfo
- Publication number
- US3552972A US3552972A US681094A US3552972DA US3552972A US 3552972 A US3552972 A US 3552972A US 681094 A US681094 A US 681094A US 3552972D A US3552972D A US 3552972DA US 3552972 A US3552972 A US 3552972A
- Authority
- US
- United States
- Prior art keywords
- antistatic
- gelatin
- layer
- layers
- solution
- 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
- 239000000463 material Substances 0.000 title description 7
- 108010010803 Gelatin Proteins 0.000 abstract description 21
- 229920000159 gelatin Polymers 0.000 abstract description 21
- 239000008273 gelatin Substances 0.000 abstract description 21
- 235000019322 gelatine Nutrition 0.000 abstract description 21
- 235000011852 gelatine desserts Nutrition 0.000 abstract description 21
- 239000002216 antistatic agent Substances 0.000 abstract description 20
- -1 PHENYL GROUP Chemical group 0.000 abstract description 8
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 229920000151 polyglycol Polymers 0.000 abstract description 2
- 239000010695 polyglycol Substances 0.000 abstract description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 33
- 150000001875 compounds Chemical class 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- 239000000839 emulsion Substances 0.000 description 11
- 239000000654 additive Substances 0.000 description 9
- 239000011241 protective layer Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000005266 casting Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 4
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 4
- 230000003068 static effect Effects 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000011253 protective coating Substances 0.000 description 3
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229930182490 saponin Natural products 0.000 description 3
- 150000007949 saponins Chemical class 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 3
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 238000004378 air conditioning Methods 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 230000001143 conditioned effect Effects 0.000 description 2
- 238000007786 electrostatic charging Methods 0.000 description 2
- 238000004945 emulsification Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- LUMLZKVIXLWTCI-NSCUHMNNSA-N (e)-2,3-dichloro-4-oxobut-2-enoic acid Chemical compound OC(=O)C(\Cl)=C(/Cl)C=O LUMLZKVIXLWTCI-NSCUHMNNSA-N 0.000 description 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- NNOHXABAQAGKRZ-UHFFFAOYSA-N 3,5-dinitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC(C(Cl)=O)=CC([N+]([O-])=O)=C1 NNOHXABAQAGKRZ-UHFFFAOYSA-N 0.000 description 1
- AXDJCCTWPBKUKL-UHFFFAOYSA-N 4-[(4-aminophenyl)-(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]aniline;hydron;chloride Chemical compound Cl.C1=CC(=N)C(C)=CC1=C(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 AXDJCCTWPBKUKL-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 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
- 229920013820 alkyl cellulose Polymers 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- OIDPCXKPHYRNKH-UHFFFAOYSA-J chrome alum Chemical compound [K]OS(=O)(=O)O[Cr]1OS(=O)(=O)O1 OIDPCXKPHYRNKH-UHFFFAOYSA-J 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- ZAKLKBFCSHJIRI-UHFFFAOYSA-N mucochloric acid Natural products OC1OC(=O)C(Cl)=C1Cl ZAKLKBFCSHJIRI-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical class CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000080 wetting agent 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
- G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
- G03C1/85—Photosensitive materials characterised by the base or auxiliary layers characterised by antistatic additives or coatings
- G03C1/89—Macromolecular substances therefor
- G03C1/895—Polyalkylene oxides
Definitions
- R is an alkyl having- 6l8 carbon atoms, a phenyl group including a substituted phenyl group;
- X is 0 or an imino group
- R is a y-valent organic group of the phenyl or naphthyl series
- n or n is an integer from 4 to 8;
- n 0 or 1 and y is 1, 2, or 3.
- Electrostatic charging of the film surface can be reduced by adding matting agents to the protective layers to diminish the adhesion between two surfaces of the photographic material which are in contact with each other.
- the formation of electrostatic charges can also be avoided by the addition of electrically conductive materials to an outermost layer.
- quaternary salts cannot be used in photographic materials because they cause fogging.
- Hygroscopic materials such as glycerol, potassium acetate or lithium chloride cause the layers to adhere to each other and are ineffective at low humidities.
- High molecular carboxylic or sulfonic acids such as sodium salts of polystyrene sulfonic acid and polyvinylsulfonic acid have agood antistatic effect when applied direct to a hydrophobic layer support, but this effect is greatly reduced when used in gelatin or emulsion layers. Chromium complexes react with gelatin and therefore can only be used under certain conditions.
- R alkyl having preferably 6-18 carbon atoms, aryl, preferably phenyl, aralkyl such as benzyl or phenylethyl or cycloalkyl such as cyclohexyl; the above substituents, especially the phenyl groups, may be further substituted in any way desired;
- X a simple chemical bond or a bivalent imino group
- R is a y-valent organic group of the kind defined under R;
- n, and 11 are integers from 4 to 8 inclusive;
- y 1, 2 or 3.
- the compounds to be used in accordance with the invention are generally highly viscous, syrupy substances. When used for photographic purposes, they are dissolved in a photographically inert solvent, preferably a low molecular weight aliphatic alcohol, and this solution is emulsified into the casting solution of the protective layer. In the final layer the antistatic agents are substantially heterogeneously distributed in the layer in the form of fine particles.
- a photographically inert solvent preferably a low molecular weight aliphatic alcohol
- the compounds according to the invention are employed in quantities of 0.03 to 0.20 g., preferably 0.05 to 0.075 per g. of the binding agent. They may be used alone or in combination with surface active substances such as anionic or non-ionic wetting agents or in combination with anti-Newton additives such as polystyrene, polymethacrylic acid esters or urea formaldehyde polymers.
- surface active substances such as anionic or non-ionic wetting agents or in combination with anti-Newton additives such as polystyrene, polymethacrylic acid esters or urea formaldehyde polymers.
- anti-Newton additives such as polystyrene, polymethacrylic acid esters or urea formaldehyde polymers.
- the last mentioned additives are also present in the final layer in the form of heterogeneously distributed particles having a size of 1-3 microns. Smooth layers that have an excellent antistatic effect are thereby obtained.
- binding agents for the antistatic layer there can be used the hydrophilic and water-permeable film-forming compounds customarily employed for photographic layers, for example proteins preferably gelatin, cellulose derivatives such as alkyl cellulose for instance hydroxyethyl cellulose or carboxyl methyl cellulose, alginic acid and derivatives thereof, polyvinyl alcohols, polyvinyl pyrrolidone and the like.
- proteins preferably gelatin
- cellulose derivatives such as alkyl cellulose for instance hydroxyethyl cellulose or carboxyl methyl cellulose
- alginic acid and derivatives thereof alginic acid and derivatives thereof
- polyvinyl alcohols polyvinyl pyrrolidone and the like.
- the compounds to be used according to the invention can be used in light-sensitive silver halide emulsion layers, antihalation layers and NC-layers for black-white or color-photographic films. They do not cause fogging, do not accelerate development, do not migrate from the layers or cause sticking of the layers.
- the antistatic agents are sparingly soluble in water and are photographically inert.
- they have preferably at the most a total of 8 ethylene oxide units.
- the groups R are strongly hydrophobic, the compounds contain preferably more than 8 ethylene oxide units so that they are more readily capable of being emulsified.
- Suitable compounds include those of the following formulae:
- a I A (VII) (VIII) The compounds to be used according to the invention are prepared by known methods. The preparation of compounds 1 and 7 is described in detail below. The other compounds are prepared in a similar manner.
- COMPOUND l moved in a rotary evaporator.
- the oily, yellow brown product is again filtered at to C.
- COMPOUND VII A solution of 9.9 g. of 3,5-dinitrobenzoyl chloride in ml. of benzene is added dropwise to a mixture of 42 g. of n-dodecylphenol which has been hydroxyalkylated in a manner analogous to Compound 1, 20 ml. of benzene and 5 g. of pyridine, and the reaction mixture is stirred at room temperature for 5 hours and at 50 C. for one hour. After cooling, the reaction mixture is poured on ice, acidified with 2 N H 50 treated with saturated sodium chloride solution, and extracted several times with methylene dichloride. The combined extracts are freed from solvent after drying over K in a vacuum.
- the 10% methanolic solution of the antistatic agent is emulsified into the casting composition at temperatures between 30 and 40 C. with stirring.
- the pH of the casting solution which is to form the protective coating is adjusted to 6.5 with sodium hydroxide solution.
- the protective coating is applied by usual methods after the emulsion layer has solidified or simultaneously with the application of the emulsion layer -by the vacuum air brush process.
- the antistatic effect is tested after air conditioning the sample strips for 2 days, the electrostatic charging in volts per cm. (v./cm.) is determined by means of the rotating field strength measuring instrument according to Schwenkhagen. The intensity of charge was measured at 60% relative humidity.
- v./cm.(60% humidity) 45 ml. of a 10% methanolic solution of one of the above mentioned antistatic materials is incorporated by emulsification as described in Example 1 into a gelatin solution of the following composition:
- the casting solution is applied onto the rear side of a transparent support of cellulose acetate and dried.
- the layer serves as a non-curling layer.
- the other side of the support is coated with a silver halide gelatin emulsion layer.
- Example 1 The antistatic test of the resulting layer are preformed as in Example 1:
- This solution is applied as protective layer onto the light-sensitive silver halide gelatin emulsion layers of a multi-layered color photographic material and dried.
- a photographic material comprising a silver iodobromide gelatin emulsion layer and an uppermost protective layer which does not contain an antistatic agent is treated with 0.01 to 0.25% solutions of the antistatic agents mentioned hereinafter (a) in water or (b) in methylene dichloride.
- the electrostatic charge of the air conditioned samples is measured at 60% humidity. Comparison measurements are carried out on samples of photographic material which have been treated only with water or methylene dichloride but have otherwise the same composition.
- the antistatic agents are incorporated into a protective gelatin layer which is applied onto a silver iodobromide gelatin emulsion layer according to Example 1.
- This layer contains, either alone or in combination, as will be seen from the following tables, based on the dry weight of gelatin, 20% by weight of polystyrene sulfonic acid (PSS), 6% by weight of alkali metal salt or 6% by weight of the antistatic agent according to the invention.
- PSS polystyrene sulfonic acid
- the surface resistivity is determined with a measuring instrument which has two comb electrodes cm. in length arranged parallel to each other at a distance of 2 cm., and the samples which have been adequately air conditioned, are pressed at a constant pressure against these electrodes.
- the resistivity is registered with a teraohmmeter connected to the instrument.
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Laminated Bodies (AREA)
- Polyethers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1966A0054080 DE1522408B2 (de) | 1966-11-15 | 1966-11-15 | Photographisches material mit einer antistatischen schicht |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3552972A true US3552972A (en) | 1971-01-05 |
Family
ID=6939294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US681094A Expired - Lifetime US3552972A (en) | 1966-11-15 | 1967-11-07 | Antistatic layer for photographic materials |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3552972A (de) |
| BE (1) | BE706563A (de) |
| CH (1) | CH504024A (de) |
| DE (1) | DE1522408B2 (de) |
| FR (1) | FR1549600A (de) |
| GB (1) | GB1167559A (de) |
| NL (1) | NL6715513A (de) |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3769022A (en) * | 1969-12-31 | 1973-10-30 | Agfa Gevaert Nv | Photosensitive silver halide emulsions comprising coating aids |
| US3850642A (en) * | 1971-07-16 | 1974-11-26 | Eastman Kodak Co | Multilayer radiation sensitive element having controlled triboelectric charging characteristics |
| US3888678A (en) * | 1971-07-16 | 1975-06-10 | Eastman Kodak Co | Method for adjusting triboelectric charging characteristics of materials |
| US4196001A (en) * | 1974-07-24 | 1980-04-01 | Eastman Kodak Company | Antistatic layer for photographic elements |
| US4221861A (en) * | 1978-04-06 | 1980-09-09 | The Dow Chemical Company | Backside antistatic coated film bearing a light sensitive emulsion |
| US4272616A (en) * | 1978-06-07 | 1981-06-09 | Fuji Photo Film Co., Ltd. | Photographic radiation-sensitive materials having improved antistatic property |
| DE3436622A1 (de) * | 1983-10-07 | 1985-04-25 | Fuji Photo Film Co., Ltd., Minami-Ashigara, Kanagawa | Photographisches silberhalogenidmaterial |
| EP0180668A1 (de) * | 1984-11-09 | 1986-05-14 | Agfa-Gevaert N.V. | Photographische Elemente, die Schutzschichten mit Antistatikmitteln enthalten |
| US4624913A (en) * | 1984-02-09 | 1986-11-25 | Fuji Photo Film Co., Ltd. | Silver halide photographic light-sensitive materials |
| US5011739A (en) * | 1989-10-02 | 1991-04-30 | Eastman Kodak Company | Moisture stable biasable transfer members and method for making same |
| US5156915A (en) * | 1991-11-26 | 1992-10-20 | Eastman Kodak Company | Moisture stable polyurethane biasable members |
| US5212032A (en) * | 1991-11-26 | 1993-05-18 | Eastman Kodak Company | Moisture stable polyurethane biasable transfer members |
| US5217838A (en) * | 1991-11-26 | 1993-06-08 | Eastman Kodak Company | Moisture stable biasable transfer members |
| US5250357A (en) * | 1991-11-26 | 1993-10-05 | Eastman Kodak Company | Moisture stable elastomeric polyurethane biasable transfer members |
| JPH0610728B2 (ja) | 1986-05-28 | 1994-02-09 | コニカ株式会社 | 新規な界面活性剤を含有するハロゲン化銀写真感光材料 |
| JPH0648350B2 (ja) | 1987-03-20 | 1994-06-22 | 富士写真フイルム株式会社 | ハロゲン化銀写真感光材料 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2219557A1 (de) * | 1972-04-21 | 1973-10-31 | Bayer Ag | Neue antistatika |
| EP0014921A1 (de) * | 1979-02-16 | 1980-09-03 | EASTMAN KODAK COMPANY (a New Jersey corporation) | Beschichtungszusammensetzungen und Verfahren |
-
1966
- 1966-11-15 DE DE1966A0054080 patent/DE1522408B2/de active Granted
-
1967
- 1967-11-07 US US681094A patent/US3552972A/en not_active Expired - Lifetime
- 1967-11-15 FR FR1549600D patent/FR1549600A/fr not_active Expired
- 1967-11-15 CH CH1597767A patent/CH504024A/de not_active IP Right Cessation
- 1967-11-15 NL NL6715513A patent/NL6715513A/xx unknown
- 1967-11-15 GB GB51910/67A patent/GB1167559A/en not_active Expired
- 1967-11-16 BE BE706563D patent/BE706563A/xx unknown
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3769022A (en) * | 1969-12-31 | 1973-10-30 | Agfa Gevaert Nv | Photosensitive silver halide emulsions comprising coating aids |
| US3850642A (en) * | 1971-07-16 | 1974-11-26 | Eastman Kodak Co | Multilayer radiation sensitive element having controlled triboelectric charging characteristics |
| US3888678A (en) * | 1971-07-16 | 1975-06-10 | Eastman Kodak Co | Method for adjusting triboelectric charging characteristics of materials |
| US4196001A (en) * | 1974-07-24 | 1980-04-01 | Eastman Kodak Company | Antistatic layer for photographic elements |
| US4221861A (en) * | 1978-04-06 | 1980-09-09 | The Dow Chemical Company | Backside antistatic coated film bearing a light sensitive emulsion |
| US4272616A (en) * | 1978-06-07 | 1981-06-09 | Fuji Photo Film Co., Ltd. | Photographic radiation-sensitive materials having improved antistatic property |
| DE3436622A1 (de) * | 1983-10-07 | 1985-04-25 | Fuji Photo Film Co., Ltd., Minami-Ashigara, Kanagawa | Photographisches silberhalogenidmaterial |
| US4624913A (en) * | 1984-02-09 | 1986-11-25 | Fuji Photo Film Co., Ltd. | Silver halide photographic light-sensitive materials |
| JPS61118747A (ja) * | 1984-11-09 | 1986-06-06 | アグフア・ゲヴエルト・ナームロゼ・ベンノートチヤツプ | 静電防止剤を含有する保護層を有する写真素子 |
| EP0180668A1 (de) * | 1984-11-09 | 1986-05-14 | Agfa-Gevaert N.V. | Photographische Elemente, die Schutzschichten mit Antistatikmitteln enthalten |
| US4670376A (en) * | 1984-11-09 | 1987-06-02 | Agfa-Gavaert, N.V. | Process of making a photographic elements comprising protective layers containing antistats |
| JPH0656479B2 (ja) | 1984-11-09 | 1994-07-27 | アグフア・ゲヴエルト・ナームロゼ・ベンノートチヤツプ | 静電防止剤を含有する保護層を有する写真素子 |
| JPH0610728B2 (ja) | 1986-05-28 | 1994-02-09 | コニカ株式会社 | 新規な界面活性剤を含有するハロゲン化銀写真感光材料 |
| JPH0648350B2 (ja) | 1987-03-20 | 1994-06-22 | 富士写真フイルム株式会社 | ハロゲン化銀写真感光材料 |
| US5011739A (en) * | 1989-10-02 | 1991-04-30 | Eastman Kodak Company | Moisture stable biasable transfer members and method for making same |
| US5156915A (en) * | 1991-11-26 | 1992-10-20 | Eastman Kodak Company | Moisture stable polyurethane biasable members |
| US5212032A (en) * | 1991-11-26 | 1993-05-18 | Eastman Kodak Company | Moisture stable polyurethane biasable transfer members |
| US5217838A (en) * | 1991-11-26 | 1993-06-08 | Eastman Kodak Company | Moisture stable biasable transfer members |
| US5250357A (en) * | 1991-11-26 | 1993-10-05 | Eastman Kodak Company | Moisture stable elastomeric polyurethane biasable transfer members |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1522408A1 (de) | 1969-08-14 |
| CH504024A (de) | 1971-02-28 |
| GB1167559A (en) | 1969-10-15 |
| NL6715513A (de) | 1968-01-25 |
| FR1549600A (de) | 1968-12-13 |
| BE706563A (de) | 1968-04-01 |
| DE1522408B2 (de) | 1976-11-18 |
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