US3454424A - Process for making photographic films - Google Patents
Process for making photographic films Download PDFInfo
- Publication number
- US3454424A US3454424A US559082A US3454424DA US3454424A US 3454424 A US3454424 A US 3454424A US 559082 A US559082 A US 559082A US 3454424D A US3454424D A US 3454424DA US 3454424 A US3454424 A US 3454424A
- Authority
- US
- United States
- Prior art keywords
- film
- dimensional stability
- processing
- cellulose
- photographic
- 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
- 238000000034 method Methods 0.000 title description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 229920002284 Cellulose triacetate Polymers 0.000 description 16
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 16
- 239000000758 substrate Substances 0.000 description 16
- 229920001577 copolymer Polymers 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 229920002678 cellulose Polymers 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 108010010803 Gelatin Proteins 0.000 description 7
- 229920000159 gelatin Polymers 0.000 description 7
- 239000008273 gelatin Substances 0.000 description 7
- 235000019322 gelatine Nutrition 0.000 description 7
- 235000011852 gelatine desserts Nutrition 0.000 description 7
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 4
- 229920002301 cellulose acetate Polymers 0.000 description 4
- -1 silver halide Chemical class 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229920001727 cellulose butyrate Polymers 0.000 description 2
- 229920006218 cellulose propionate Polymers 0.000 description 2
- XJELOQYISYPGDX-UHFFFAOYSA-N ethenyl 2-chloroacetate Chemical compound ClCC(=O)OC=C XJELOQYISYPGDX-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- DQEFEBPAPFSJLV-UHFFFAOYSA-N Cellulose propionate Chemical compound CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 DQEFEBPAPFSJLV-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- COTNUBDHGSIOTA-UHFFFAOYSA-N meoh methanol Chemical compound OC.OC COTNUBDHGSIOTA-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920006289 polycarbonate film Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 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
- G03C1/91—Photosensitive materials characterised by the base or auxiliary layers characterised by subbing layers or subbing means
- G03C1/93—Macromolecular substances therefor
-
- 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
- G03C1/795—Photosensitive materials characterised by the base or auxiliary layers the base being of macromolecular substances
Definitions
- This invention pertains to a process for making dimensionally stable photographic films having a support composed of organic cellulose esters.
- the film base itself is the controlling factor for the dimensional stability of the coated photographic films.
- the photosensitive layer has some influence, especially on dimensional changes which occur during processing of the coated film. As applicants have been able to demonstrate, this is particularly true of the type of film supporting treatment, the solvent employed in applying the film support having in particular a substantial influence.
- Efforts have been made to improve dimensional stability of photographic films by using strongly hydrophobic plastic film base. In this respect, the best dimensional stability is obtained with hydrophobic film base made from polyesters of terephthalic acid with ethylene glycol, and by polystyrene or polycarbonate films.
- Table II shows the improvement in dimensional stability to processing in finished, emulsion-coated films obtained in accordance with this invention.
- substrate layers made in accordance with this invention are excellent adhesive agents between the film support and the photosensitive emulsion, and in 3 other respects also they meet all requirements which these layers must satisfy.
- the optimum adhesive effect and dimensional stability is attained in general when use is made of a solvent blend of 5080% ethyl acetate and 50-20% isopropanol.
- Suitable copolymers for carrying out the process as disclosed are chiefly those made from maleic anhydride and vinyl acetate, the two components being employed preferably in approximately equivalent quantities. There are, however, other copolymers, e.g. those made from maleic anhydride and vinylmethyl ether or styrene, or also, more especially, from vinyl chloroacetate or ethene or the like, which are well suited.
- the copolymers can be made by known processes. For example, the monomer mixture of maleic anhydride and vinyl acetate in the mole ratio 1:1 may be polymerized at 80 C. in benzene solution, using peroxide catalysts, e.g. benzoyl peroxide. The reaction product precipitates in finely powdered form. If desired, there may be added to the batch, after polymerization is complete, a precipitating agent such as diethyl ether, and the polymer may be separated from the solvent by filtering. Usually no further purification is needed.
- the copolymers are applied to the film support in the customary manner from solutions containing 0.5 to 3.0% of the respective copolymers, and may be dried and wound up by the usual method. Film bases pretreated in this way may then be coated with a photosensitive emulsion by any of the customary methods.
- a second specimen of the cellulose triacetate foil designated above is treated with a substrate solution from the prior art, having the composition:
- Both film supports are then coated on one side with an antihalation layer of gelatin and a suitable antihalation dye, and on the other side with a photosensitive gelatinsilver halide emulsion layer having the following properties:
- the material prepared in accordance with this invention undergoes substantially no dimensional change during its processing in the photographic baths, unlike the material made with a film base treated for substrate according to the prior art.
- a process for making dimensionally stable organic cellulose monocarboxylic acid ester photographic film base which comprises applying to the film base an adhesive sublayer from a solution of a copolymer of one mole of maleic anhydride with one mole of a difierent addition polymerizable ethylenically unsaturated monomer containing a vinyl group not substituted at the a-carbon atom of the vinyl group in a solvent blend of 50%-80% ethyl acetate and 50%20% isopropanol, by weight and drying the treated film base.
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Laminated Bodies (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEA0049885 | 1965-07-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3454424A true US3454424A (en) | 1969-07-08 |
Family
ID=6937111
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US559082A Expired - Lifetime US3454424A (en) | 1965-07-30 | 1966-06-21 | Process for making photographic films |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3454424A (pm) |
| BE (1) | BE684866A (pm) |
| CH (1) | CH472052A (pm) |
| DE (1) | DE1472771A1 (pm) |
| GB (1) | GB1114799A (pm) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3892573A (en) * | 1970-12-24 | 1975-07-01 | Fuji Photo Film Co Ltd | Method of improving the surface of a high molecular weight support |
| US4093458A (en) * | 1972-11-20 | 1978-06-06 | Imperial Chemical Industries Limited | Polyurethane-polyanhydride subbing layer for photo sensitive elements |
| US4120724A (en) * | 1972-10-02 | 1978-10-17 | Fuji Photo Film Co., Ltd. | Subbing material for styrene bases used in photographic elements |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2067706A (en) * | 1932-12-10 | 1937-01-12 | Ig Farbenindustrie Ag | Artificial compositions |
| US2562853A (en) * | 1948-08-14 | 1951-07-31 | Monsanto Chemicals | Insolubilization of water-soluble copolymers |
| US2637712A (en) * | 1949-01-21 | 1953-05-05 | Nat Starch Products Inc | Copolymers of vinyl acetate with derivatives of alpha, beta-unsaturated dicarboxylic acids |
| US2756163A (en) * | 1952-01-04 | 1956-07-24 | Gen Aniline & Film Corp | Resinous layers having a selected degree of water sensitivity and method of making same |
| US2772972A (en) * | 1954-08-20 | 1956-12-04 | Gen Aniline & Film Corp | Positive diazotype printing plates |
| US3072482A (en) * | 1958-01-10 | 1963-01-08 | Keuffel & Esser Co | Subbed photographically sensitive film element |
| US3130051A (en) * | 1958-12-10 | 1964-04-21 | Gen Aniline & Film Corp | Process for producing negative working offset diazo printing plates |
| US3227555A (en) * | 1961-10-02 | 1966-01-04 | Eastman Kodak Co | Raw striping process for sonotrack dispersions |
| US3228768A (en) * | 1960-12-13 | 1966-01-11 | Gen Aniline & Film Corp | Process of diffusion printing and a structure for use therein |
-
1965
- 1965-07-30 DE DE19651472771 patent/DE1472771A1/de active Pending
-
1966
- 1966-06-21 US US559082A patent/US3454424A/en not_active Expired - Lifetime
- 1966-07-06 CH CH979066A patent/CH472052A/de not_active IP Right Cessation
- 1966-07-27 GB GB33746/66A patent/GB1114799A/en not_active Expired
- 1966-07-29 BE BE684866D patent/BE684866A/xx unknown
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2067706A (en) * | 1932-12-10 | 1937-01-12 | Ig Farbenindustrie Ag | Artificial compositions |
| US2562853A (en) * | 1948-08-14 | 1951-07-31 | Monsanto Chemicals | Insolubilization of water-soluble copolymers |
| US2637712A (en) * | 1949-01-21 | 1953-05-05 | Nat Starch Products Inc | Copolymers of vinyl acetate with derivatives of alpha, beta-unsaturated dicarboxylic acids |
| US2756163A (en) * | 1952-01-04 | 1956-07-24 | Gen Aniline & Film Corp | Resinous layers having a selected degree of water sensitivity and method of making same |
| US2772972A (en) * | 1954-08-20 | 1956-12-04 | Gen Aniline & Film Corp | Positive diazotype printing plates |
| US3072482A (en) * | 1958-01-10 | 1963-01-08 | Keuffel & Esser Co | Subbed photographically sensitive film element |
| US3130051A (en) * | 1958-12-10 | 1964-04-21 | Gen Aniline & Film Corp | Process for producing negative working offset diazo printing plates |
| US3228768A (en) * | 1960-12-13 | 1966-01-11 | Gen Aniline & Film Corp | Process of diffusion printing and a structure for use therein |
| US3227555A (en) * | 1961-10-02 | 1966-01-04 | Eastman Kodak Co | Raw striping process for sonotrack dispersions |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3892573A (en) * | 1970-12-24 | 1975-07-01 | Fuji Photo Film Co Ltd | Method of improving the surface of a high molecular weight support |
| US4120724A (en) * | 1972-10-02 | 1978-10-17 | Fuji Photo Film Co., Ltd. | Subbing material for styrene bases used in photographic elements |
| US4093458A (en) * | 1972-11-20 | 1978-06-06 | Imperial Chemical Industries Limited | Polyurethane-polyanhydride subbing layer for photo sensitive elements |
Also Published As
| Publication number | Publication date |
|---|---|
| CH472052A (de) | 1969-04-30 |
| BE684866A (pm) | 1967-01-30 |
| DE1472771A1 (de) | 1969-01-02 |
| GB1114799A (en) | 1968-05-22 |
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