US2071462A - Film - Google Patents
Film Download PDFInfo
- Publication number
- US2071462A US2071462A US713770A US71377034A US2071462A US 2071462 A US2071462 A US 2071462A US 713770 A US713770 A US 713770A US 71377034 A US71377034 A US 71377034A US 2071462 A US2071462 A US 2071462A
- Authority
- US
- United States
- Prior art keywords
- film
- cellulose
- mixture
- alcohols
- grams
- 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
- 235000019441 ethanol Nutrition 0.000 description 17
- 239000000203 mixture Substances 0.000 description 15
- 229920002678 cellulose Polymers 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 235000014113 dietary fatty acids Nutrition 0.000 description 12
- 229930195729 fatty acid Natural products 0.000 description 12
- 239000000194 fatty acid Substances 0.000 description 12
- 150000004665 fatty acids Chemical class 0.000 description 12
- 239000004902 Softening Agent Substances 0.000 description 11
- 150000001298 alcohols Chemical class 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 239000010466 nut oil Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 244000060011 Cocos nucifera Species 0.000 description 9
- 235000013162 Cocos nucifera Nutrition 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000001913 cellulose Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- -1 diisoamylbutylphosphate Chemical compound 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 244000147568 Laurus nobilis Species 0.000 description 4
- 235000017858 Laurus nobilis Nutrition 0.000 description 4
- 239000000020 Nitrocellulose Substances 0.000 description 4
- 235000005212 Terminalia tomentosa Nutrition 0.000 description 4
- 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 4
- 229940081735 acetylcellulose Drugs 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229940073584 methylene chloride Drugs 0.000 description 4
- 229920001220 nitrocellulos Polymers 0.000 description 4
- 238000007127 saponification reaction Methods 0.000 description 4
- 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 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 3
- 229920002301 cellulose acetate Polymers 0.000 description 3
- 239000012084 conversion product Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 description 2
- 125000005456 glyceride group Chemical group 0.000 description 2
- 238000009863 impact test Methods 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- YEVQZPWSVWZAOB-UHFFFAOYSA-N 2-(bromomethyl)-1-iodo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(I)C(CBr)=C1 YEVQZPWSVWZAOB-UHFFFAOYSA-N 0.000 description 1
- ZAMLGGRVTAXBHI-UHFFFAOYSA-N 3-(4-bromophenyl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(CC(O)=O)C1=CC=C(Br)C=C1 ZAMLGGRVTAXBHI-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241001479434 Agfa Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002160 Celluloid Polymers 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 229920000875 Dissolving pulp Polymers 0.000 description 1
- 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 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 229920001727 cellulose butyrate Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- UZQPWASKVYDSRV-UHFFFAOYSA-N dodecoxymethylbenzene Chemical compound CCCCCCCCCCCCOCC1=CC=CC=C1 UZQPWASKVYDSRV-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- JCZMXVGQBBATMY-UHFFFAOYSA-N nitro acetate Chemical compound CC(=O)O[N+]([O-])=O JCZMXVGQBBATMY-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000019488 nut oil Nutrition 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil 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
- G03C1/795—Photosensitive materials characterised by the base or auxiliary layers the base being of macromolecular substances
Definitions
- Our present invention relates to photographic film and more particularly to such a film with an improved support.
- phosphoric acid esters of an alcohol which is derived from a fatty acid such as trioctylphosphate, diisoamylbutylphosphate, diethylphosphate, or butylphosphate
- softening agents have no dissolving action on cellulose derivatives and in contradistinction to the softening agents having a dissolving action on cellulose have a more favorable influence on the mechanical properties of the films made from cellulose derivatives.
- softening agents having no dissolving action on cellulose ester and which are derived from vegetable oils containing the glycerides of fatty acids having from 8 tol l carbon atoms are particularly suited as softening agents for cellulose esters for the manufacture of supports of photographic films.
- oils are, for'instance, cocoa nut oil, palm nut oil, and laurel-oil.
- esters of the mixture of fatty acids obtained by saponification of the glycerides with a monovalent alcohol the esters of the alcohols obtained from the oils by simultaneous saponification and hydrogenation with aliphatic acids, or aromatic acids, or halogen hydracids, or phosphoric acid; the ethers of the aforesaid alcohols.
- the softening agents are suitable for the ;manufacture of supports for photographic films they must not contain strongly smelling compounds. For this reason, for instance, the esters of the mixture of fatty acids from the above mentioned oils with methyl alcohol or ethyl al 3 cohol are not suitable.
- the esters of such a fatty acid and propyl alcohol or a higher alcohol preferably an alcohol having more than 5 carbon atoms.
- the separation of compounds of low molecular weight which yield strongly smelling constituents may be effected by distillation in the vacuum before or 7 after conversion of the oils into their derivatives. For the same reason the nitriles of fatty "acids are useless.
- softeners for nitrocellulose.
- the mixtures of softening agents are suitable for the preparation of films from cellulose nitrate and for films from organic cellulose ester, for instance, cellulose acetate; cellulose nitroacetate, cellulose acetobutyrate, cellulose butyrate and other technically useful cellulose esters. It is clear that not all of the products have the same action. A few experiments will be sufficient to ascertain which of the softeners suggested have the best effect for films made of a certain cellulose ester or a mixture of cellulose esters, to render it elastic and resistant to mechanical strain.
- the conversion products of fatty acids with more than 14 carbon atoms have no longer the same good properties as softeners than have the conversion products of fatty acids with a number of carbon atoms between 8 and 14. Mixtures, containing a large amount of such fatty acids should therefore not be employed for the purpose in question.
- the softeners for the manufacture of support for photographic films according to this invention can also be used in admixture with the softeners hitherto known for this purpose and even then an improved product will be obtained.
- Example 1 -20 parts of nitrocellulose containing 12.2 per cent of nitrogen are dissolved in 100 parts of a'mixture consisting of 8 parts of acetone and 2 parts of ethyl alcohol while adding 2 parts of amyl ester of the acids from laurel oil containing 8 to 14 carbon atoms.
- the solution is cast in known manner to form a film of 0.130 mm. thickness.
- the process'of manufacturing a support for photographic layers which comprises dissolving cellulose acetate containing 56 per cent of acetic acid in a mixture of methylene chloride, chloroform and amylalcohol; adding as a softening agent diphenylphosphate havingthe last hydrogen atom'esterified by the alcohols containing 8 to 14 carbon atoms obtainable from cocoa nut oil, and triphenylphosphate and casting the solution to form a film.
- a support for photographic layers comprising celluloseacetate containing 56 per cent of acetic acid and diphneylphosphate having the last hydrogen atom esterified by the alcohols containing 8 to 14 carbon atoms obtainable from cocoa nut oil. and triphenylphosphate.
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI46681D DE683061C (de) | 1933-03-04 | 1933-03-04 | Herstellung photographischer Schichttraeger aus Cellulosederivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2071462A true US2071462A (en) | 1937-02-23 |
Family
ID=6477131
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US713770A Expired - Lifetime US2071462A (en) | 1933-03-04 | 1934-03-02 | Film |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2071462A (enrdf_load_html_response) |
| BE (1) | BE401736A (enrdf_load_html_response) |
| DE (1) | DE683061C (enrdf_load_html_response) |
| FR (1) | FR769485A (enrdf_load_html_response) |
| GB (1) | GB426023A (enrdf_load_html_response) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2464784A (en) * | 1945-08-09 | 1949-03-22 | Gen Aniline & Film Corp | Film forming solution of cellulose acetate |
-
0
- BE BE401736D patent/BE401736A/xx unknown
-
1933
- 1933-03-04 DE DEI46681D patent/DE683061C/de not_active Expired
-
1934
- 1934-03-01 FR FR769485D patent/FR769485A/fr not_active Expired
- 1934-03-02 US US713770A patent/US2071462A/en not_active Expired - Lifetime
- 1934-03-05 GB GB6985/34A patent/GB426023A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB426023A (en) | 1935-03-26 |
| FR769485A (fr) | 1934-08-27 |
| BE401736A (enrdf_load_html_response) | |
| DE683061C (de) | 1939-10-28 |
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