US543197A - John h - Google Patents
John h Download PDFInfo
- Publication number
- US543197A US543197A US543197DA US543197A US 543197 A US543197 A US 543197A US 543197D A US543197D A US 543197DA US 543197 A US543197 A US 543197A
- Authority
- US
- United States
- Prior art keywords
- pyroxyline
- camphor
- naphthalene
- liquid
- solvent
- 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
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 92
- 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 class 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 60
- 229920001220 nitrocellulos Polymers 0.000 description 54
- 150000001875 compounds Chemical class 0.000 description 52
- 239000002904 solvent Substances 0.000 description 52
- DSSYKIVIOFKYAU-UHFFFAOYSA-N Camphor Chemical compound C1CC2(C)C(=O)CC1C2(C)C DSSYKIVIOFKYAU-UHFFFAOYSA-N 0.000 description 50
- 229960000846 Camphor Drugs 0.000 description 50
- 241000723346 Cinnamomum camphora Species 0.000 description 50
- 229930007890 camphor Natural products 0.000 description 50
- 239000007788 liquid Substances 0.000 description 50
- 229940075566 Naphthalene Drugs 0.000 description 44
- 239000000203 mixture Substances 0.000 description 28
- 239000007787 solid Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 6
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- WKHQSKREGKYGPW-UHFFFAOYSA-N naphthalene;4,7,7-trimethylbicyclo[2.2.1]heptan-3-one Chemical compound C1=CC=CC2=CC=CC=C21.C1CC2(C)C(=O)CC1C2(C)C WKHQSKREGKYGPW-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 229960004756 ethanol Drugs 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000006193 liquid solution Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- -1 pyroxyline compound Chemical class 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- 241000702021 Aridarum minimum Species 0.000 description 2
- 240000004499 Cinnamomum aromaticum Species 0.000 description 2
- 235000014489 Cinnamomum aromaticum Nutrition 0.000 description 2
- SKYSRIRYMSLOIN-UHFFFAOYSA-N Cyclopentolate Chemical compound C1CCCC1(O)C(C(=O)OCCN(C)C)C1=CC=CC=C1 SKYSRIRYMSLOIN-UHFFFAOYSA-N 0.000 description 2
- 229940075144 Cylate Drugs 0.000 description 2
- 206010013786 Dry skin Diseases 0.000 description 2
- 206010040003 Sensation of pressure Diseases 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 230000003247 decreasing Effects 0.000 description 2
- 230000002939 deleterious Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 235000011194 food seasoning agent Nutrition 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 230000018984 mastication Effects 0.000 description 2
- 238000010077 mastication Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 101700052672 mix-1 Proteins 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 239000005445 natural product Substances 0.000 description 2
- 230000035943 smell Effects 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 239000000341 volatile oil Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 230000003313 weakening Effects 0.000 description 2
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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
Definitions
- the present invention enables the operator to avail himself of all the valuable properties of camphor in these compounds, and at the same time avoid the difficulties'incident to known crystalline su lstance naphthalene (naphtalin).
- My invention is base upon the discovery that naphthalene, whil not a solvent of py-- roxyline in itself, forms a powerful solvent of pyroxyline when combined with camphor, preferably in equal proportion by weight, and that a compound composed of pyroxyline,
- My new compound when in a solid or liquid condition can be seasoned or dried by theevaporatiug of the wood alcohol orother volatile solvent, according to the usual method,
- the compound can be thoroughly deprived of all wood alcohol or othersolvent without impairment of its plasticity.
- camphor-naphthalene combination any large increase in theproportion of camphor acts to make a material more resistant to molding or working by heat and pressure, and any increase in the naphthalene acts in the same way, but toa less degree.
- the increase ofnaphthalene also weakens the plastic prop erty, and it carried too far the beneficial effects of the cam'phor-naphthalene combination are lost.
- 269,340, 269,34E1, 269,344, and 269,345, can j be employed, in which case the solvent action 1 will not be interfered with, but rather aided iby means of these useful menstrua.
- lproportion or kind ofi odoriferous substance i to. be used will depend on the strength or persistency of its odor and the individual taste 5 of the operator or user of the goods.
- oil I recommend oil of cassia.
- I recommend such substances as aceta-te of amyl or sali'cylate of methyl, in the proportions and can be varied.
- I desire less pl'as- '1 ticity I prefer to decrease the amount or propresence of some liquid solvent, especially The 7 such proportion of liquid as is insufficientin itself to give plasticity to the product, does not matter.
- camphor-naphthalene solvent can be employed in all the compounds of this class, and in combination with any of thesolvents he wishes to obtain, and also in varying proportions.
- camphor-naphthalene solvent can be dissolved in the liquid menstruum or liquid menstrua employed, and then added.
- liquid menstrua can be entirely dispensed with by using the process which involves intimately mixing the pyroxyline, cam phor, and naphthalene in the presence of water, then drying out the,
- heat and pressure as used by me include the manipulation of these materials in heated rolls, (whether the heat comes from steam orfriction during the mixing operatiou,) the heating of the compound in dies under pressure, or the heating or bending or twistingof these materials in hot water.
- camphor and naphthalene substantially as described.
- a pyroxyline compound consisting of pyroxyline, camphor, naphthalene, and a liquid menstruum or liquid menstrua, substantially as 95 described.
Description
UNITE STATES PATENT JOHN STEVENS, OF NEWARK, JERSEY, ASSIGNOR TO THE OELLU-LOID COMPANY, OF NEW YORK, N. Y.
COMPOUND OF P YROXYLl N.
S?ECIFICATIO N forming part of Letters Patent No. 543,197, dated July 23, 1895.
Application filed May 31, 1895. Serial No. 551,285. (No specimens.)
To all whom it mag concern:
Be it known that '1, JOHN H. STEVENS, of the city of Newark, county of Essex, and State of New Jersey, have invented certain new and useful Improvements in Pyroxylin Compounds, of which the following is a specifica- 1011.
The class of pyroxyline compounds to which my invention relates are known in commerce,
mainly, as imitations of natural substances, and are especially valuable by reason of their plasticity under heat when in a dried or seadesired. The most popular methods employed to form these compounds involve the use of a .minimum proportion of solvent, which will,
. by the aid of heat, pressure, and mastication,
solidmass of material. to evaporate down a liquid solution to form permit the pyroxyline to be converted into a Another method is thin films or sheets or masses built up by successive applications and dryings of liquid solutions. This method has a limited application, however, due'to the waste of solvent and incidentalimperfections. In allcases the value of the compound is in the final dried product, whether it be thin films or sheets or thick masses. Two classes of solvents are employed-liquid and solid. The liquid solvcuts are generally of a volatile nature, and during the curing or seasoning process evaporate and leave the compound in a hard condition. The solid solvents possess so little volatility that they practically remain in the final product combined with the pyroxyline,
and as they possess the power of dissolving pyroxyline when heated to their meltingpoints,-the compounds made with them are plasticthat is, they can be molded into various shapes under heat and pressure. The solid solvent commonly used is camphor,
which requires so high a degree of heat to melt it thatunless it is associated with some portlon of liquid solvent compounds made with it are only moldable at such high temperaturesas to need great care in their manipulation.
It is the object of the present invention to enable the operator to employ camphor as a solvent, with the avoidance of the difiiculties which have heretofore been incidental to its use, and at the same time produce these compounds at a'lower cost.
My experience has shown that many substances,'which, in view of their power of lowering the melting-point of camphor when mixed therewith, might be supposed to operate beneficially in pyroxyline combinations, have failed to form useful compounds with the cam phor and pyroxyline, because of a weakening effect on the solvent or some other deleterious action on the combination. For in stance, many substances which are colorless in themselves react with the pyroxyline to make a dark-colored or decomposed mass. A practical trial with numerous agents which promised good results in pyroxyline compounds has-caused me to appreciate the delicate and changeable character of pyroxyline when it is combined with other substances.
The present invention enables the operator to avail himself of all the valuable properties of camphor in these compounds, and at the same time avoid the difficulties'incident to known crystalline su lstance naphthalene (naphtalin). I
My invention is base upon the discovery that naphthalene, whil not a solvent of py-- roxyline in itself, forms a powerful solvent of pyroxyline when combined with camphor, preferably in equal proportion by weight, and that a compound composed of pyroxyline,
camphor, and naphthalene, as hereinafter connected withthe discovery of suitable sol-- vents, I' refer to my United States Patent No.
517,987, dated April 10, 1894.. a
In making the present compound,"I prefer to proceed in the usual well known-manner of making solid pyroxyline compounds, .which centig-rade, or even lower temperatures, es-' pecially when the camphor is slightly in excess involves grinding the solid solvent and pyroxyline together while in a hydrated condition, next removing the water by suitable means, and then adding a sufficient quantity of liquid solvent to allow the mixing to be completed, or the conversion into a solid homogeneous mass effected by means of mastioating-rolls and subsequent solidification instuffing machinery or presses or dies.
I have found during my experiments in this field that while naphthalene is difficultly soluble in some of the ordinary liquid inen strua employed in making these compounds, it is easily dissolved in these menstrua in the presence of camphor. Thus, while naphthalene requires for solution without camphorin the following liquids about the proportions specified,viz: ninety-five per cent. grain alcohol, ten to eleven parts; absolute alcohol,
eight parts; wood spirit, six to seven parts; I
acetate of amyl for manufacturing purposes, two to two and a half partson the other hand a mass of undissolved naphthalene and wood alcohol becomes a clear solution when camphor is added to the mixture. A mixture of three parts of camphor and two partsnaphthalene is soluble in about three and onet'ourth parts ninety-five per cent. grain alcohol, two parts absolute alcohol, one and fourtenths parts wood spirit or one-halt part acetate of amyl for manufacturing purposes. All these proportions are for the ordinary temperature of the workroom. I use bypreference a refined grade of wood spirit.
My new compound when in a solid or liquid condition can be seasoned or dried by theevaporatiug of the wood alcohol orother volatile solvent, according to the usual method,
and as distinguished from the pyroxylinecamphor compounds made with wood alcohol or other solvent. The compound can be thoroughly deprived of all wood alcohol or othersolvent without impairment of its plasticity.
In forming a product which is easily plastic at temperatures below the boiling-point of water I usually employ the following proportions:- Four parts soluble pyroxyline, one part camphor, one part naphthalene, and a sufficient quantity of wood spirit. The dried product of this mixture is plastic, as before described, at low temperatures. Sheets made from it can be easily bent or stretched into shape in hot water, or, say, at about to of the naphthalene.
portion of naphthalene, and at the same time increase the proportion of camphor, so that the proportion of the total solid solventswill constitute about two parts to each four parts of pyroxyline, though of course. it is understood that by decreasing the proportion of solid solvents to the pyroxyline I can also re-' duce the plasticity. Although the: solvent composed of naphthalene andcamphor is still that of the eamphor, thereis a corresponding decrease in the plasticity. In other words,
.any large increase in theproportion of camphor acts to make a material more resistant to molding or working by heat and pressure, and any increase in the naphthalene acts in the same way, but toa less degree. The increase ofnaphthalene also weakens the plastic prop erty, and it carried too far the beneficial effects of the cam'phor-naphthalene combination are lost.
Inmy various experiments with naphtha lene as an ingredient in pyroxyline compounds I have paid particular-attention to the attempt to obviate or minimize its obnoxious ;odor, and after many experiments I finally i discovered that when a sufficiently-pure naphi thalene was employed it gave off very little smell in the final thoroughly-dried product, I the odor being most perceptible when the liq- :uid solvent was evaporating. Hence the proj' duct when it reaches the market, is not ob- {jectionable on account of odor; but, to produce the best results, I combine with my mix- 1 ture a small percentage of some volatile oil or odoriferous principle, such as the heavy f'ethers used in perfumery and flavor-lugs, so f as to substitute a pleasing odor for the trace iof naphthalene which might be detected in l these materials. Inthis connection the liquid solventsrecommended in several of my prior patents, especially my United States Patents j Nos. 269,340, 269,34E1, 269,344, and 269,345, can j be employed, in which case the solvent action 1 will not be interfered with, but rather aided iby means of these useful menstrua. lproportion or kind ofi odoriferous substance i to. be used will depend on the strength or persistency of its odor and the individual taste 5 of the operator or user of the goods. oil I recommend oil of cassia. As colorless As an ethers I recommend such substances as aceta-te of amyl or sali'cylate of methyl, in the proportions and can be varied. When I desire less pl'as- '1 ticity I prefer to decrease the amount or propresence of some liquid solvent, especially The 7 such proportion of liquid as is insufficientin itself to give plasticity to the product, does not matter.
' used .by the operator, according to the result VI find that, contrary to theinferences drawn from the known lack of harmony between naphthalene and the usual liquid solventsby which we might expect it to separate from the solvent and pyroxyline during the evaporating down of the'compound to produce afilm or sheet, the use of the mixture of naphthaline and camphor in suitable proportionsay one part of the mixture to each two parts of the pyroxyline-forms a useful solid solvent in liquid compounds, and, for instance, where acetone is employed as the liquid solvent I am enabled to produce a perfectly clearsolid film or sheet free from the blemishes which often accompany the employment of .this liquid process.
The camphor-naphthalene solvent can be employed in all the compounds of this class, and in combination with any of thesolvents he wishes to obtain, and also in varying proportions.
It is evident, also, that I am not confined to anyparticular process for effecting the combination of solid solventandpyroxyline. For instance, the camphor-naphthalene solvent can be dissolved in the liquid menstruum or liquid menstrua employed, and then added.
to and intimately mixed with the pyroxyline in a manner which is equivalent to first combining it with the pyroxyline by means of grinding operations. Again, the liquid menstrua can be entirely dispensed with by using the process which involves intimately mixing the pyroxyline, cam phor, and naphthalene in the presence of water, then drying out the,
Water and subjecting the dry hard compound to heat and pressure in order to bring into action the active or converting power of the so1vent,'and thus form a homogeneous mass in the dry way, or any other equivalent method can be employed.
The terms heat and pressure as used by me include the manipulation of these materials in heated rolls, (whether the heat comes from steam orfriction during the mixing operatiou,) the heating of the compound in dies under pressure, or the heating or bending or twistingof these materials in hot water.
I am aware that naphthalene hasbeen used in the household and for medicinal and other purposes as a substitute for camphor, and
that it has received such designations as naphthalene-camphor and a .substitute for camphor by reason of such use.
I believe that I am the first to make a mixture of camphor, naphthalene, and pyroxyline .and subject such mixture to the action of heat, by means of which the solvent action of the camphor and naphthalene is brought into play so as to obtain useful results in this art.
Having thus described the object and nature ofmyinvention, what I claim, and desire to secure by'Letters Patent, is-
1. The process of manufacturing compounds of pyroxyline which consists in intimately. mixing pyroxyline, camphor and napththalene, and subjecting the resulting compound to heat and pressure, substantially as set forth.
2. The process of forming compounds 'of 'pyroxyline which consists in mixingpyroxyline, camphor, naphthalene and a liquid men'- struum, or liquid menstrua, and then subjecting the resulting compound to heat and press ure, substantially as set forth.
3. The process for the manufacture'of compounds of pyroxyline which consists of the following steps: first, intimately mixing pyroxyline, camphor, naphthalene and a liquid menstruum or liquid Inenstrua; second, drying out the liquid menstruum or liquid menstrua; third, subjecting the dry compound to heat and pressure.
4:. As a new composition of matter, a pyroxyline compound consisting of pyroxyline,
camphor and naphthalene, substantially as described.
5. As a new composition. of matter, a pyroxyline compound consisting of pyroxyline, camphor, naphthalene, and a liquid menstruum or liquid menstrua, substantially as 95 described.
' JOHN H. STEVENS.
In presence of- -THEO. M. SAMMIs,
GEORGE O. GILLMORE.
Correction in Lette rs'Patent No. 543,197.
23, 1895, upon the application of John H. Stevens, \of Newark, New'Jer-sey, for an 7 Itis hereby certified that the assignee in Letters Patent No. 543,197, granted July improvement in Compounds of Pyroxylin, should have beendeseribed and specified as thec'elluloid Company, of Neiv York, N. Y., a corporation of New Jersey, instead of the Celluloid Company, of New York, Y. 5 and that the said Letters Patent should be read with this correction therein that the seine may conform to the record of the case in theIatent Oifioe.
Signed, countersigned, and sealedathis 30th day of July, A. D. 1895.
' JNO. M. REYNOLDS,
[SEA-n] 7 Assistant Secretary of the Interior.
Countersignedz.
VJ-OHN' S. SEYMOUR, Commissioner of Patents.
Publications (1)
Publication Number | Publication Date |
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US543197A true US543197A (en) | 1895-07-23 |
Family
ID=2611945
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US543197D Expired - Lifetime US543197A (en) | John h |
Country Status (1)
Country | Link |
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US (1) | US543197A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040007818A1 (en) * | 2000-10-30 | 2004-01-15 | Newman Michael Shane | Rebound-action sports board game |
-
0
- US US543197D patent/US543197A/en not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040007818A1 (en) * | 2000-10-30 | 2004-01-15 | Newman Michael Shane | Rebound-action sports board game |
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