US1309981A - Hans t - Google Patents
Hans t Download PDFInfo
- Publication number
- US1309981A US1309981A US1309981DA US1309981A US 1309981 A US1309981 A US 1309981A US 1309981D A US1309981D A US 1309981DA US 1309981 A US1309981 A US 1309981A
- Authority
- US
- United States
- Prior art keywords
- composition
- cellulose nitrate
- parts
- matter
- oxalate
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 15
- 239000000020 Nitrocellulose Substances 0.000 description 13
- 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 13
- 229920001220 nitrocellulos Polymers 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- JKRZOJADNVOXPM-UHFFFAOYSA-N Oxalic acid dibutyl ester Chemical compound CCCCOC(=O)C(=O)OCCCC JKRZOJADNVOXPM-UHFFFAOYSA-N 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 5
- -1 alkyl oxalates Chemical class 0.000 description 4
- 235000006408 oxalic acid Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 150000003901 oxalic acid esters Chemical class 0.000 description 2
- 239000002966 varnish Substances 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
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 1
- AIDFJGKWTOULTC-UHFFFAOYSA-N 1-butylsulfonylbutane Chemical compound CCCCS(=O)(=O)CCCC AIDFJGKWTOULTC-UHFFFAOYSA-N 0.000 description 1
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- XAHVPYNDLCTDTE-UHFFFAOYSA-N dipentyl oxalate Chemical compound CCCCCOC(=O)C(=O)OCCCCC XAHVPYNDLCTDTE-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000003860 storage Methods 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
Definitions
- This invention relates to a new composition of matter and a method of making the same, in which cellulose nitrate is combined or mixed with other substances, so that the resulting product can be advantageously used in the plastic and analogous arts, such, for instance, as sheet or film manufacture and varnish manufacture.
- One object is to produce a composition which may be made into permanently transparent, strong and flexible sheets or film of.
- Another object of my invention is to produce a composition of matter capable of easy manipulation in the plastic and manufacture, storage, or use.
- Still another object of my invention is to provide a process course
- composition of matter having the desirable qualities hereinabove enumerated can be obtained by mixing or compounding cellulose nitrate with simple alkyl oxalates which are only slightly volatile or non-volatile at ordinary temperatures.
- simple alkyl oxalates I mean substances of the type indicated by 'the following formulae in which A and B represent alkyl groups containing 4 to 5 carbon atoms:
- CO-OA CO-OA (iO-OA do-oB) CO-OA (iO-OA do-oB).
- dibutyl oxalate and diamyl oxalate may, of be mixed as well as used singly, and the degree of purity will depend upon the purposes to which the plastic composition is to be put.
- These oxalates have high boiling points and are very stable. The'com- Specification of Letters Patent.
- pounding is best performed by using a solvent common to both the cellulose nitrate and the oxalate. 1
- the normal dibutyl oxalate is selected. It is a colorless liquid boiling under atmospheric pressure at about 243 C., and at 113 C. when under 10 mm. pressure. It has a very faint characteristic odor, and is practically insoluble in water.
- I incorporate in 65 parts of acetone or methyl alcohol, or any mixture of the two in any proportion, 10 parts of cellulose nitrate and 2 parts of butyl oxalate.
- the ingredients are mixed to form a homogeneous solution or fiowable mass and are filtered if desired.
- High boiling auxiliary softeners may be added if desired in small amounts, preferably four parts of any of the. higher aliphatic alcohols or their esters, such asfusel oil, amyl acetate, butyl acetate, ethyl propionate, ethyl butyrate, etc.
- softeners as urea, castor oil, camphor, triphenyl phosphate,
- mixture of the two may be present in from present in from 1 to 10 parts, the higher aliphatic alcohols in from 1 to 10 parts, and the solvents last mentioned in from 1 to 10 parts.
- the solution either with or without the additional high boiling softener, is sufficiently thick and viscous to be properly flowed during sheet or film manufacture, the acetone and methyl alcohol volatilizing, but not too rapidly to impair the product.
- composition of matter comprising cellulose nitrate and a dialkyl ester of oxalic acid in which each of the alkyl groups convent common to both.
- a composition of matter comprising cellulose nitrate, a dialkyl ester of oxalic acid in which each of the alkyl groups contains from 4 to 5 carbon atoms and a solvent containing acetone and methyl alcohol.
- a composition of matter comprising cellulose nitrate, dibutyl oxalate and a solventcontaining acetone and methyl alcohol.
- a composition of matter comprising cellulose nitrate, a dialkyl ester of oxalic acid in which each of the alkyl groups contains from 4' to 5 carbon atoms and a solvent common to both, and an organic body of only slight volatility which enhances the plasticity and flexibility of the composition.
- cellulose nitrate 10 parts a mixture of acetone and methyl alcohol -10 to 100 parts, diubuty'l oxalate 1 to 10 parts.
- composition of matter comprising
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Description
No Drawing.
HANS T. CLARKE, OF ROCHESTER, NEW YORK, ASSIGNOR TO EASTMAN KODAK COMPANY, OF ROCHESTER, NEW YORK, A CORPORATION OF NEW YORK.
CELLULOSE-NITRATE COMPOSITION.
LSOQQSI.
To all whom it may concern Be it known that I, HANS T. CLARKE, a subject of the King of Great Britain, residing at Rochester, in the county of Monroe and State of New York, have invented certain new and useful Improvements in Cellulose-\ itrate Composition, of which the following is a full, clear, and exact specification.
This invention relates to a new composition of matter and a method of making the same, in which cellulose nitrate is combined or mixed with other substances, so that the resulting product can be advantageously used in the plastic and analogous arts, such, for instance, as sheet or film manufacture and varnish manufacture. I
One object is to produce a composition which may be made into permanently transparent, strong and flexible sheets or film of.
desired thinness that are substantially waterproof, are unaffected by ordinary photographic fluids and possess the desired properties of a support for sensitive photographic coatings. Another object of my invention is to produce a composition of matter capable of easy manipulation in the plastic and manufacture, storage, or use.
. film' making or varnish making arts; which "willnot injure or injuredby the substanceswith which it isassociated during Still another object of my invention is to provide a process course,
for compounding such composition of matter. Further objects will hereinafter appear.
I have discovered that a composition of matter having the desirable qualities hereinabove enumerated can be obtained by mixing or compounding cellulose nitrate with simple alkyl oxalates which are only slightly volatile or non-volatile at ordinary temperatures. By simple alkyl oxalates I mean substances of the type indicated by 'the following formulae in which A and B represent alkyl groups containing 4 to 5 carbon atoms:
CO-OA CO-OA (iO-OA do-oB There may be noted particularly dibutyl oxalate and diamyl oxalate. These may, of be mixed as well as used singly, and the degree of purity will depend upon the purposes to which the plastic composition is to be put. These oxalates have high boiling points and are very stable. The'com- Specification of Letters Patent.
. Patented July 15, 1919.
Application filed April 26. 1919. Serial No. 293.006.
pounding is best performed by using a solvent common to both the cellulose nitrate and the oxalate. 1
As a typical useful example of the dialkyl oxalates which may be employed in carrying out my invention, the normal dibutyl oxalate is selected. It is a colorless liquid boiling under atmospheric pressure at about 243 C., and at 113 C. when under 10 mm. pressure. It has a very faint characteristic odor, and is practically insoluble in water.
In carrying out one illustration of my invention, I incorporate in 65 parts of acetone or methyl alcohol, or any mixture of the two in any proportion, 10 parts of cellulose nitrate and 2 parts of butyl oxalate. The ingredients are mixed to form a homogeneous solution or fiowable mass and are filtered if desired. High boiling auxiliary softeners may be added if desired in small amounts, preferably four parts of any of the. higher aliphatic alcohols or their esters, such asfusel oil, amyl acetate, butyl acetate, ethyl propionate, ethyl butyrate, etc. There maybe further added, if desired, either'in additlon to the above mentioned high boilers or without them, such softeners as urea, castor oil, camphor, triphenyl phosphate,
dibutyl sulfone, and monochlornaphthalene,
'2 parts of any of these ingredients, or mixture of them, being used. The proportions of the various ingredients mentioned may be varied within certain limits. For instance, the 'acetone r methyl alcohol or a.
mixture of the two may be present in from present in from 1 to 10 parts, the higher aliphatic alcohols in from 1 to 10 parts, and the solvents last mentioned in from 1 to 10 parts. r
The solution, either with or without the additional high boiling softener, is sufficiently thick and viscous to be properly flowed during sheet or film manufacture, the acetone and methyl alcohol volatilizing, but not too rapidly to impair the product. The resulting film containing the cellulose nitrate and oxalate, together with the additional high boiling softener, if the latter is used, is very flexible, transparent, and uniform, so that it can be used for any usual or preferred purpose. It is practically waterproof and unaffected by ordinary photographic chemicals. I
While I have hereinabove disclosed certain compositions and processes by Wayof example, my invention is not limited thereto nor to the proportions given thereln, as the proportions may be varied from those given and equivalent substances may be substituted without departing from the principle of my claims.
Having thus described my invention, What invention as defined in 'the appended I claim as new and desire to secure by Letters Patent is:
1. A composition of matter comprising cellulose nitrate and a dialkyl ester of oxalic acid in which each of the alkyl groups convent common to both.
5. A composition of matter comprising cellulose nitrate, a dialkyl ester of oxalic acid in which each of the alkyl groups contains from 4 to 5 carbon atoms and a solvent containing acetone and methyl alcohol.
6. A composition of matter comprising cellulose nitrate, dibutyl oxalate and a solventcontaining acetone and methyl alcohol.
7. A composition of matter comprising cellulose nitrate, a dialkyl ester of oxalic acid in which each of the alkyl groups contains from 4' to 5 carbon atoms and a solvent common to both, and an organic body of only slight volatility which enhances the plasticity and flexibility of the composition.
cellulose nitrate 10 parts, a mixture of acetone and methyl alcohol -10 to 100 parts, diubuty'l oxalate 1 to 10 parts.
9. As an article of manufacture, a sheet ofdeposited or flowed cellulose nitrate containing a dialkyl ester of oxclic acid in whicheach of the alkyl groups. contains from 4 to 5 carbon atoms.
10. As an article of manufacture, a sheet ofdepOsited or flowed cellulose nitrate containing dibutyl oxalate.
' 11. As an article of manufacture, a sheet of deposited or flowed cellulose nitrate containing a dialkyl ester of oxalic acid in which 'each of the alkyl groups contains from 4 to 5 carbon atoms, and an organic body of slight volatility which enhances the I flexibility of the sheet.
1 Signed at Rochester, New York, this 16th day of April, 1919.
HANS T. CLARKE.
8. A composition of matter comprising
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1309981A true US1309981A (en) | 1919-07-15 |
Family
ID=3377489
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US1309981D Expired - Lifetime US1309981A (en) | Hans t |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1309981A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2689187A (en) * | 1951-09-29 | 1954-09-14 | Rca Corp | Method and compositions for forming nitrocellulose films |
-
0
- US US1309981D patent/US1309981A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2689187A (en) * | 1951-09-29 | 1954-09-14 | Rca Corp | Method and compositions for forming nitrocellulose films |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US1309981A (en) | Hans t | |
| US1460097A (en) | Cellulose-ether film and composition for making the same | |
| US1836701A (en) | Cellulosic composition of matter containing trimethylene glycol | |
| US2000622A (en) | Cellulose acetate composition comprising a tertiary alcohol | |
| US1444333A (en) | Nitrocellulose composition | |
| US2021901A (en) | Cellulosic composition of matter containing an alkyl phosphate | |
| US1398939A (en) | Cellulose-ester composition | |
| US1281080A (en) | Plastic composition and method of making the same. | |
| US1342601A (en) | Cellulose-ester composition and method of making the same | |
| US1379596A (en) | Cellulose-nitrate composition | |
| US1548932A (en) | Cellulose-acetate composition | |
| US1354725A (en) | Cellulose-nitrate composition and process of making the same | |
| US1395905A (en) | Cellulose-ether composition | |
| US1467092A (en) | Cellulose-ether composition | |
| US1735157A (en) | Cellulose-ether composition | |
| US1884433A (en) | Cellulose acetate composition | |
| US1405491A (en) | Cellulose-ether composition | |
| US1552794A (en) | Cellulose-ether composition | |
| US1844714A (en) | Cellulosic composition of matter containing an amide or derivative thereof | |
| US1342603A (en) | Cellulose-acetate composition | |
| US1370879A (en) | Cellulose-ester composition | |
| US1548933A (en) | Cellulose-ether composition | |
| US1398949A (en) | Cellulose-acetate composition | |
| US1342602A (en) | Cellulose-nitrate composition | |
| US1370878A (en) | Cellulose-nitrate composition |