US889171A - Formic-aldehyde preparation and process of making same. - Google Patents
Formic-aldehyde preparation and process of making same. Download PDFInfo
- Publication number
- US889171A US889171A US374578A US1907374578A US889171A US 889171 A US889171 A US 889171A US 374578 A US374578 A US 374578A US 1907374578 A US1907374578 A US 1907374578A US 889171 A US889171 A US 889171A
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- US
- United States
- Prior art keywords
- formic
- methyl
- ester
- aldehyde
- matter
- 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
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 title description 53
- 238000000034 method Methods 0.000 title description 5
- 238000002360 preparation method Methods 0.000 title description 4
- 150000004702 methyl esters Chemical class 0.000 description 36
- 239000000203 mixture Substances 0.000 description 32
- 150000002148 esters Chemical class 0.000 description 24
- 239000002253 acid Substances 0.000 description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 20
- 239000003085 diluting agent Substances 0.000 description 12
- 229960000411 camphor oil Drugs 0.000 description 7
- 239000010624 camphor oil Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000012530 fluid Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000645 desinfectant Substances 0.000 description 4
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XJRIDJAGAYGJCK-UHFFFAOYSA-N (1-acetyl-5-bromoindol-3-yl) acetate Chemical compound C1=C(Br)C=C2C(OC(=O)C)=CN(C(C)=O)C2=C1 XJRIDJAGAYGJCK-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000002421 anti-septic effect Effects 0.000 description 2
- 230000002542 deteriorative effect Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000002070 germicidal effect Effects 0.000 description 2
- 235000019645 odor Nutrition 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000009637 wintergreen oil Substances 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- 108010068370 Glutens Proteins 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- RHKZVMUBMXGOLL-UHFFFAOYSA-N cyclopentolate hydrochloride Chemical compound Cl.C1CCCC1(O)C(C(=O)OCCN(C)C)C1=CC=CC=C1 RHKZVMUBMXGOLL-UHFFFAOYSA-N 0.000 description 1
- 229940075144 cylate Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000249 desinfective effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000010696 ester oil Substances 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 235000021312 gluten Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- -1 methyl-benzoic ester Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/60—Salicylic acid; Derivatives thereof
Definitions
- This invention relates to a new article of manufacture or com osition of matter for disinfecting, germicitfie, antiseptic, and -medicinal purposes, and consists of a mixture, compound, or solution, of formic aldehyde or its olymerids in a methyl ester, such as methyl-benzoic ester, methyl-salicylic ester,
- compositions containmg methyl esters
- the polymerids of formic aldehyde such as paraformaldehyde or trioxymethylene, may be dissolved in the ester, preferably by the action of heat, producin compounds not departing from the spirit ofmy invention, as, upon heating in the formation of the composition, formic aldehyde is generated in the presence of the methyl ester and absorbed thereby; and the composition is'found to have a like disinfectant, germicide, antiseptic, and medicinal property, and to all intents and purposes may be considered, and is herein included, as an equivalent composition in accordance with my invention.
- a vehicle such as cam hor oil
- methyl oxy-acid esters which, having characteristic odors, serve to disguise the formic aldehyde when applied, without deteriorating or destroying its effectiveness as a disinfectant.
- the methyl oxy-acid esters not only act as a solvent of the formic aldehyde, or its merids, but may be em loyed as a carrier or solvent agent to introtfilce formic aldehyde into other vehicles in which it is less soluble, and in which event solutions of formic aldehyde in methyl esters per se, which may be of expensive manufacture, may be employed with economical advantage by adding there? to a less expensive diluent without deteriorating the efiectiveness of the disinfectant formic aldehyde or the odorizing or solvent methyl ester.
- my invention relates to a solution of formic aldehyde or its polymerids in a methyl ester, such as methyl oxy-acid ester of aromatic character, either per se or with other diluents, but is not confined to methyl testers of salicylic acid, as herein specifically described, as I may employ any practical methyl ester or methyl oxy-acid esters, or methyl substitution product of an acid or oxy acid. It may be noted also that the methyl esters, as a rule, are practically incompatible with water or non-miscible with or repellent thereto.
- methyl ester to what may be termed a methyl salt or methyl substitution product of an acid or oxy-acid, i. e., a hydrogen acid or an acid containing oxygen, which methyl esters may be either obtained from nature or artificially or synthetically prepared.
- formic aldehyde which is a gas, unites or combines more readily with the methyl esters and becomes more readily assimilated, or retained, or occluded therein in a more permanent manner and in a larger percentage without danger of polymerization than is the case with aqueous solutions.
- methyl esters have the property of transforming or occluding gaseous formic aldehyde into a liquid condition with such avidity and ermanenc that solutions even u to 80% ormicalde yde have been produce without polymerizatmn into solid products, at the same time the valuable dislnfectant and germicide roperties of the formic aldehyde have not een deteriorated, but in fact seem to be enhanced b its union or composition with the methyfester solvent or ve- 'hicle.
- e my invention is particularly applicable to the employment of methyl esters of oxy-acids of the aromatic series, such as which methyl esters are volatile, aromatic, and water-repellent, still I do not confine myself to methyl ester as cation and claims,
- a new composition of matter comprising amethyl ester, formic aldehyde, and a d' uent.
- a new composition of matter comprising a methyl ester, formic aldehyde, and camphor oil.
- a new composition of matter compris-' ing a methyl oxy-acid ester and formic aldehyde.
- a new composition of matter comprising a methyl oxy-acid ester, formic aldehyde, and a diluent.
- a new composition of matter comprisi an anhydrous methyl ester and formic al ehyde.
- a new composition of matter comprising an anhydrous methyl ester, formic aldehyde, and a diluent.
- a new composition of matter comprising an anhydrous methyl ester, formic aldehyde and camphor oil.
- a new composition of matter comprising an anhydrous methyl oxy-acid ester, and formic aldehyde.
- a new composition of matter comprisan anhydrous methyl oxy-acid ester, formic aldehyde and a diluent. 12. A new composition of matter comprismg an anhydrous methyl oXy-acid ester, formic aldehyde, and camphor oil.
- a new composition of matter comprising a volatile methyl ester and formic aldehyde.
- a new com osition-of matter comprising a volatile met yl ester, and a diluent.
- a new complosition of matter comprising a volatile met yl ester, formic aldehyde, and camphor oil.
- a new composition of matter comprisilpgda volatile oxy-acid ester and formic aldematter compris- 17.
- a new composition of matter comprisfor formic alde yde or,
- a new composition of matter comprisehyde, and cam hor oil.
- a new 'fluid composition of matter comprising formic aldehyde, a methyl ester, and camp or oil.
- new fluid com comprising formic alde salicylic ester.
- a new fluid composition of matter comprising formic aldehyde, methyl salicylic '20 ester,.and a diluent.
- a new fluid com comprising formic alde cylate, and camphor oil.
- a Volatile methyl oxy-acid ester, formic a 25 The process of making the new composition of matter herein set forth, which 25 consists in dissolving formic aldehyde in a methyl ester under super-atmospheric pressure.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
UNITED STATES HENRY SPENCER BLACKMORE,
OF MOUNT VERNON, NEW YORK.
FORMIC-ALDEHYDE PREPARATION AND PROCESS OF MAKING SAME.
Specification of Letters Patent.
Original application filed April 18, 1903, Serial No. 153,330. Divided Serial No. 374,578.
Patented May 2c, 1908.
and this application filed May 20, 1907. (Specimena) To all whom it may concern:
Be it known that I, Haney SPENCER BLAoKMoRE, a citizen ofthe United States, residing at Mount Vernon, in the county of Westchester and State of New York, have invented certain new and useful Improvements in Formic-Aldehyde Preparations and Processes of Making Same, of which the following is a specification, being a division of Serial No. 153,330, filed April 18, 1903.
This invention relates to a new article of manufacture or com osition of matter for disinfecting, germicitfie, antiseptic, and -medicinal purposes, and consists of a mixture, compound, or solution, of formic aldehyde or its olymerids in a methyl ester, such as methyl-benzoic ester, methyl-salicylic ester,
eto., orcompositions containmg methyl esters,
which compounds or compositions may or may not be associated with other vehicles or medicatin agents, the object bein to produce a soTutmn of formic aldehy e or its polymerids, which will be of permanent nature in relation to s ontaneous decomosition and ,which, in fffiidj condition, may he readily utilized without producing disagreeable efiects. 1
As a specific illustration of my new composition of matter and the manner in which the same is made, I will take for example the production of a solution of formic aldehyde in methyl-salicylic ester (methylsalicylate). The manner in which I prefer to produce this solution of formic aldehyde or its polymerids is to place the desired methyl ester, such as met yl-salicylic ester, in a propercontainer and expose it to the presence of formic aldehyde under increased pressure at the same time agitating it, whereby the formic aldehyde becomes absorbed, occluded, or retained therein. When the ester has become saturated with formic aldehyde it is removed, the formic aldehyde content ascertained by test, and the composition diluted with more ester, or other diluent, to obtain the ercentage content of the formic aldehyde esired. The polymerids of formic aldehyde, such as paraformaldehyde or trioxymethylene, may be dissolved in the ester, preferably by the action of heat, producin compounds not departing from the spirit ofmy invention, as, upon heating in the formation of the composition, formic aldehyde is generated in the presence of the methyl ester and absorbed thereby; and the composition is'found to have a like disinfectant, germicide, antiseptic, and medicinal property, and to all intents and purposes may be considered, and is herein included, as an equivalent composition in accordance with my invention.
I have found it of advantage to employ compositions containing methyl esters and formic aldehyde diluted with a vehicle, such as cam hor oil, in which case it is found to act witl fsatisfaction as an aerial disinfectant, inasmuch as the camphor oil and methyl ester is volatile at ordinary atmospheric pressure and temperature and saturates the air coming in contact therewith with formic aldehyde and the methyl ester, which, having a pleasant characteristic odor, perfumes the air and obviates the disagreeable pungent effect, which usually accompanies the application of formic aldehyde per 86.
I have found that formic aldehyde and its 'polymerids may be readily assimilated with the methyl oxy-acid esters, which, having characteristic odors, serve to disguise the formic aldehyde when applied, without deteriorating or destroying its effectiveness as a disinfectant. l have also found that the methyl oxy-acid esters not only act as a solvent of the formic aldehyde, or its merids, but may be em loyed as a carrier or solvent agent to introtfilce formic aldehyde into other vehicles in which it is less soluble, and in which event solutions of formic aldehyde in methyl esters per se, which may be of expensive manufacture, may be employed with economical advantage by adding there? to a less expensive diluent without deteriorating the efiectiveness of the disinfectant formic aldehyde or the odorizing or solvent methyl ester.
Specifically my invention relates to a solution of formic aldehyde or its polymerids in a methyl ester, such as methyl oxy-acid ester of aromatic character, either per se or with other diluents, but is not confined to methyl testers of salicylic acid, as herein specifically described, as I may employ any practical methyl ester or methyl oxy-acid esters, or methyl substitution product of an acid or oxy acid. It may be noted also that the methyl esters, as a rule, are practically incompatible with water or non-miscible with or repellent thereto.
The term formic aldehyde throughout this specification and claims is employed intended to include its polymerids, or equivalents,= such as para-formaldehyde or trioxmethylene, and mtermediate olymerization roducts as well as formic afdehyde per se, and the term methyl ester to what may be termed a methyl salt or methyl substitution product of an acid or oxy-acid, i. e., a hydrogen acid or an acid containing oxygen, which methyl esters may be either obtained from nature or artificially or synthetically prepared.
I am aware that oil of Wintergreen has been added to compounds formed by the action of formic aldehyde on gluten and glelatin for the purpose of perfuming it, also t at oil of Wintergreen has been added to dental preparations containing caustic alkali and ormicaldehyde, whereby it is transformed into alkali salicylate and methyl alcohol, but in neither of these cases does the resultant roduct comprise formic aldehyde and a methyl ester, as herein described, but consists only of decomposition products of either, or both, of the essential in redients of my composition, viz., formic al ehyde and methyl ester.
It may be noted that formic aldehyde, which is a gas, unites or combines more readily with the methyl esters and becomes more readily assimilated, or retained, or occluded therein in a more permanent manner and in a larger percentage without danger of polymerization than is the case with aqueous solutions.
The largest percentage of formicaldehyde obtained under ordinary conditions 111 aquebenzoic, salicylic, cinnamic, etc.,
one solution does not exceed 40%, whereas methyl esters have the property of transforming or occluding gaseous formic aldehyde into a liquid condition with such avidity and ermanenc that solutions even u to 80% ormicalde yde have been produce without polymerizatmn into solid products, at the same time the valuable dislnfectant and germicide roperties of the formic aldehyde have not een deteriorated, but in fact seem to be enhanced b its union or composition with the methyfester solvent or ve- 'hicle.
The term containin em loyed in this spec' wit aldehyde has reference to methyl esters per se, or inert diluent containing the same in any desired pro ortion, and the term inert as employ'e' herein is intended to imply a diluent inert with reference to the formic aldehyde and methyl ester content of the com osition. q
e my invention is particularly applicable to the employment of methyl esters of oxy-acids of the aromatic series, such as which methyl esters are volatile, aromatic, and water-repellent, still I do not confine myself to methyl ester as cation and claims,
reference to the vehicle for the formic this specific class of methyl oxy-acid esters, but reserve the right to employ any methyl ester, be it either fluid or solid, as a solvent or vehicle, either per se or in com osition with other diluents, its olymerids.
here reference herein is made to dissolving formic aldehyde in methyl esters it is intended to imply and does imply that formic aldehyde gas is transformed, converted, condensed, or reduced, from a gaseous to a li uid or liquefied condition, by the action 0 or by its assimilation or its association with, methyl esters.
Having now described my invention, what I claim as new and desire to secure by Letters Patent is:-
1. A new composition of matter com risa methyl ester and formic aldehy e.
2. A new composition of matter comprisamethyl ester, formic aldehyde, and a d' uent.
A new composition of matter comprising a methyl ester, formic aldehyde, and camphor oil.
4. A new composition of matter compris-' ing a methyl oxy-acid ester and formic aldehyde.
5. A new composition of matter comprising a methyl oxy-acid ester, formic aldehyde, and a diluent.
6. A new composition of ing a methyl oxy-acid ester, and camphor oil.
7. A new composition of matter comprisi an anhydrous methyl ester and formic al ehyde.
8. A new composition of matter comprising an anhydrous methyl ester, formic aldehyde, and a diluent.
9. A new composition of matter comprising an anhydrous methyl ester, formic aldehyde and camphor oil.
10. A new composition of matter comprising an anhydrous methyl oxy-acid ester, and formic aldehyde.
11. A new composition of matter comprisan anhydrous methyl oxy-acid ester, formic aldehyde and a diluent. 12. A new composition of matter comprismg an anhydrous methyl oXy-acid ester, formic aldehyde, and camphor oil.
13. A new composition of matter comprising a volatile methyl ester and formic aldehyde.
14. A new com osition-of matter comprising a volatile met yl ester, and a diluent.
15. A new complosition of matter comprising a volatile met yl ester, formic aldehyde, and camphor oil.
16. A new composition of matter comprisilpgda volatile oxy-acid ester and formic aldematter compris- 17. A new composition of matter comprisfor formic alde yde or,
formic aldehyde,
formic aldehyde I l ehyde, and a diluent.
18. A new composition of matter comprisehyde, and cam hor oil. 9.A new fiui composition of matter comprising formic aldehyde and a methyl ester. a 20. A new fluid composition of matter, 10 comprising formic aldehyde, a methyl ester,
and a diluent. 21. A new 'fluid composition of matter comprising formic aldehyde, a methyl ester, and camp or oil.
new fluid com comprising formic alde salicylic ester.
23. A new fluid composition of matter, comprising formic aldehyde, methyl salicylic '20 ester,.and a diluent.
osition of matter,
mg a Volatile methyl oxy-acid ester, formic a yde, and methylosition of matter, yde, methyl sali- 24. A new fluid com comprising formic alde cylate, and camphor oil. a Volatile methyl oxy-acid ester, formic a 25. The process of making the new composition of matter herein set forth, which 25 consists in dissolving formic aldehyde in a methyl ester under super-atmospheric pressure.
26. The process of making the new composition of matter methyl salicylic ester under super-atmospheric pressure.
In testimony whereof I afiix my signature in presence of two witnesses.
HENRY SPENCER BLACKMORE.
herein set forth, which 36, consists in dissolving formic aldehyde in
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US374578A US889171A (en) | 1903-04-18 | 1907-05-20 | Formic-aldehyde preparation and process of making same. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15333003A US854452A (en) | 1903-04-18 | 1903-04-18 | Formaldehyde preparation. |
| US374578A US889171A (en) | 1903-04-18 | 1907-05-20 | Formic-aldehyde preparation and process of making same. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US889171A true US889171A (en) | 1908-05-26 |
Family
ID=2957602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US374578A Expired - Lifetime US889171A (en) | 1903-04-18 | 1907-05-20 | Formic-aldehyde preparation and process of making same. |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US889171A (en) |
-
1907
- 1907-05-20 US US374578A patent/US889171A/en not_active Expired - Lifetime
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