US938614A - Non-odorous phenol salve and ointment. - Google Patents
Non-odorous phenol salve and ointment. Download PDFInfo
- Publication number
- US938614A US938614A US48842509A US1909488425A US938614A US 938614 A US938614 A US 938614A US 48842509 A US48842509 A US 48842509A US 1909488425 A US1909488425 A US 1909488425A US 938614 A US938614 A US 938614A
- Authority
- US
- United States
- Prior art keywords
- phenol
- salve
- odorous
- acid
- mixture
- 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
- 239000002674 ointment Substances 0.000 title description 37
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title description 25
- 235000014113 dietary fatty acids Nutrition 0.000 description 14
- 239000000194 fatty acid Substances 0.000 description 14
- 229930195729 fatty acid Natural products 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 12
- 230000002421 anti-septic effect Effects 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- -1 fatty acid esters Chemical class 0.000 description 8
- 150000004665 fatty acids Chemical class 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000002131 composite material Substances 0.000 description 6
- 239000002085 irritant Substances 0.000 description 6
- 231100000021 irritant Toxicity 0.000 description 6
- 150000002989 phenols Chemical class 0.000 description 6
- 235000021355 Stearic acid Nutrition 0.000 description 5
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
- NUMNZKICGJJSHN-UHFFFAOYSA-N phenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC1=CC=CC=C1 NUMNZKICGJJSHN-UHFFFAOYSA-N 0.000 description 4
- 239000011369 resultant mixture Substances 0.000 description 4
- 239000008117 stearic acid Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000004166 Lanolin Substances 0.000 description 3
- 230000036760 body temperature Effects 0.000 description 3
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical compound OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 description 3
- 229940039717 lanolin Drugs 0.000 description 3
- 235000019388 lanolin Nutrition 0.000 description 3
- ODFKDYBAQKFTOU-KTKRTIGZSA-N phenyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC1=CC=CC=C1 ODFKDYBAQKFTOU-KTKRTIGZSA-N 0.000 description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000001896 cresols Chemical class 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- OWNRRUFOJXFKCU-UHFFFAOYSA-N Bromadiolone Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1C(O)CC(C=1C(OC2=CC=CC=C2C=1O)=O)C1=CC=CC=C1 OWNRRUFOJXFKCU-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- MCYTYTUNNNZWOK-LCLOTLQISA-N penetratin Chemical compound C([C@H](NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CCCNC(N)=N)[C@@H](C)CC)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(N)=O)C1=CC=CC=C1 MCYTYTUNNNZWOK-LCLOTLQISA-N 0.000 description 1
- 108010043655 penetratin Proteins 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003871 white petrolatum Substances 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
Definitions
- Phenyl-stearate can be obtained by heatmg together five hundred gr. of dried stearic acid with 100 gr. phosphorus trichlorid for several hours at from 80 to 90 degrees C.
- the stearic acid chlorid, freed from the excess of the phosphorus trichlorid and from phosphoric acid is then brought into reaction with about 200 gr. phenol and after the "spontaneous evolution of hydrochloric acid hasceased, is heated for 3 to 4 hrs. to 85 to 90 degrees C.
- the product carefully washed and dried is ready for use.
- Phenyl oleate can be prepared in similar mannerzIn one case 600 gr. of dried oleic acid were heated together'for 5.130 6 hrs. with 110 gr.
- melti g n rally a (firearms) ature was raised to about 139 degrees C. for
- henylstearate' I can melt together about equal parts of phenylstearate and liquidpetrola tum (or benzoinated lard or lanolin or white Vaseline).
- the phenol esters made from the crude or commercialacids may be emloyed in making these salves and ointments. uch salves and ointments may also contain there for about 5 hrs.
- the temperi mixtures of fatty acid esters madevfrom a mixture of phenols (for instance, when such esters are made from mixtures of cresols).
- a non-odorous non-irritant antiseptic salve of the nature disclosed for medical and pharmaceutical use composed of a comparatively hard ester of a phenol and a fatty-acid in mixture with a suflicient quantit of a suitable unguent to impart to the resu tant mixture a melting point of approximately body-temperature; said phenol having t e capacity of formin with stearic acid an ester melting at not ess than about 40 C. and said fatty-acid containing. more .than 12 atoms of carbon.
- a non-odorous non-irritant composite antiseptic salve of the nature disclosed for pharmaceutical and medical use composed of an ester of a phenol and a fatty-acid havin more than twelve atoms of carbon, in mixture with a sufiicient quantity of a suitable unguent to impart to the resultant mixture a melting point of a proximately body-temperature whereby sai mixture may have a salve-like consistency enabling it to be readily smeared on the skin; said phenol being mono-hydric and having the capacity of forming with stearic acid anester melting at not less than about 40 C.
- a non-odorous non-irritant composite of being antiseptic salve of the nature disclosed for pharmaceutical and medical use composed of an ester of a mono-hydric phenol and a fatty-acid having more than twelve atoms of carbon, saidesten having a melting point of not less than about 40 0., in mixture with a lowerrmelting suitable unguent in such proportions as will"'impart to the resultant'mixturea salve-like consistency enabling it to'be readily smeared on the skin and be absorbed thereby.
- An antiseptic non-irritant composite salve of the nature disclosed for ceutical and medical use compose ester of a henol and a fatty acid in mixture with'a su cient quantity of a suitable un guent to impart to the resultant mixture a melting point of approximately body.-tem-" perature enablingit to normall possess a salve-like consistency and have .t e capacity fatty acid having more than twelve atoms of carbon and said phenol bein such as will form with stearic acid a soli at not'less thanabout 40 C.-
- An antiseptic non-irritant composite salve of the nature-disclosed for pharmaceutical and medical use composed of a solid ester of a mono-hydric phenol and a fatty acid having more than twelve atoms of carbon, in mixture with a sufiicient quantity of a suitable unguent toimpart to the harmaof an.
- ester melting v resultant mixture a melting point of about-1 body temperature.
- An antiseptic non-irritant non-odorous composite salve of the nature disclosed for pharmaceutical and medical use composed of an ester of a monohydric phenol and a fatty tion of a suitable unguent as will suflice to impart a salve-like. consistency to the resultant mixture and enable it'to be readily smeared on the skin.
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- Health & Medical Sciences (AREA)
- Emergency Medicine (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)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
PATENT OFF C NATHAN sunznnnena, or new max, 1;. ,r.
non ononous rnnnon snnvr. arm orntr tnnr.
10 Drawing.
T 0 all whom it may concern:
Be it known that I, NATHAN Sonznnncnn, a citizen of the United States of America, residing at No. 34 West Seventh-first street, New York city, in the county of New York and State of New York, have invented new 1, anduseful Improvements in Making N on}; Odorous Phenol Salves and Ointments, of which the following is a specification.
The well established valuable antiseptic and anal esic qualities of the phenols (carbolic acid, cresols, etc. and derivatives of same) and their mixtures are offset detrimentally to their more general use by their objectionable and very penetratin odor, which oftentimes clings to the skin even after the salve has-been removed and washed off. This objection reveals itself most par ticularly when the 'phenolsare used in form of salvesand .ointments since in this articular form the phenols are mostly use externally on sores and wounds of the skin.
It has now been found that salves and I ointments, etc. still possessing the antiseptic and analgesic action of the henols can be prepared to take the place 0? all such ointments, etc. heretofore manufactured with the strong smelling phenol compounds themselves by their odorless higher fatty acid esters, such as for instance, the phenol esters of palmitic and stearic acids (and their mixtures).
Phenyl-stearate can be obtained by heatmg together five hundred gr. of dried stearic acid with 100 gr. phosphorus trichlorid for several hours at from 80 to 90 degrees C. The stearic acid chlorid, freed from the excess of the phosphorus trichlorid and from phosphoric acid is then brought into reaction with about 200 gr. phenol and after the "spontaneous evolution of hydrochloric acid hasceased, is heated for 3 to 4 hrs. to 85 to 90 degrees C. The product carefully washed and dried is ready for use. Phenyl oleate can be prepared in similar mannerzIn one case 600 gr. of dried oleic acid were heated together'for 5.130 6 hrs. with 110 gr. phoshorus trichlorid in a flask with reflux conenser, The chlorid freed from the excess of phosphorus trichlorid and from the formed phosphoric acid was brou ht into reaction with 220 phenol and a er the evolution of 'hydroc loric acid had ceased at ordnary temperature, the temperature was gradually raised to about 85 to 95 degrees C. and kept Specification of Letters Patent. Application filed April 7, 1909. Serial no. 488425.
:"manner. 11,6 8
melti g n rally a (firearms) ature was raised to about 139 degrees C. for
about @1 1, 1 611 when .fii 'ishfiii est r 'YiieS carefully washed an driedf-Derivativ "of these phenol fatty acid esters, which also be ed n maki g th el ilid ments, can be made andpreparedfin salve end as as $1 ntain g arg r o sm ler amounts of these esters, will not turn v if These d rl s no t nt sters" thbiie'h too hi h a d gjiel if ak the r mp o m in "the pu e state (p yl t era e me i g t 2 degree "0-, ph nylpel ita ing M 4 @168 as salves and ointments for the skin resyncbeing mixed with larger or sirabIe, by 7 smaller percentages of animal, vegetable or mineral fats and oils (such as for instance, lanolin, Vaseline, etc.) canbeused in making salves and ointments of any desired'softness and consistency. Into such salves and oint ments can also be mixed a great number of chemicals of phermaceutical'value, if so de slred, since these fatty acid esters do not interfere with the action of a great many of these bodies. For example, to obtain a 53 of proper consistency containing henylstearate' I can melt together about equal parts of phenylstearate and liquidpetrola tum (or benzoinated lard or lanolin or white Vaseline). To obtain a salve containing some chemical substance besides, I cite'for instance the following formula for aborax slave; 40 parts phenylstearate 30 parts liquid petrolatum, 10 parts white 'wax' and '20 parts of an a ueous saturated solution of borax. These saves are all white bodies unless colored through the addition of foreign matter. They may be perfumed wherever desired. Ssilvesv can also be made by mixin liquid phenol oleates with the solid fatty acid esters. These latter need contain 'no foreign fat or oil at all and therefore consist of much greater percentages of phenol. In making a salve with the liquid phenyl oleate the following formula can be used: 40 parts. phenyl oleate, 20 parts wax and. 40 parts lanolin.
Instead of using the pure fatty acid phenol esters, the phenol esters made from the crude or commercialacids (as such fatty acidsare for instance obtained by saponifyi'nganimal and vegetable fats and o ls) may be emloyed in making these salves and ointments. uch salves and ointments may also contain there for about 5 hrs. Finallythe temperi mixtures of fatty acid esters madevfrom a mixture of phenols (for instance, when such esters are made from mixtures of cresols). I claim: 7 1. A11 antiseptic salve of the'nature disclosed, composed of phenyl-stearate melting at about 52 C. and having mixed therewith some suitable unguent adapted to lower the melting-point of the phenyl-st'earate and to impart to the resultant compound a greaselike consistency.
- 2. A non-odorous non-irritant antiseptic salve of the nature disclosed for medical and pharmaceutical use, composed of a comparatively hard ester of a phenol and a fatty-acid in mixture with a suflicient quantit of a suitable unguent to impart to the resu tant mixture a melting point of approximately body-temperature; said phenol having t e capacity of formin with stearic acid an ester melting at not ess than about 40 C. and said fatty-acid containing. more .than 12 atoms of carbon.
3. A non-odorous antiseptic, composite 'salve of the nature disclosed formedical and pharmaceutical use, composed of an ester of a phenol and a. fatty-acid having more thantwelve atoms of carbon, said ester having a melting pomt of not lessthan about 40 (3., in mixture with a quantity of a lowermelting suitable unguent sufiicientto impart to the resultant =mixture 'a salve-like consistency enabling it to melt and liquefy when rubbed on the skin.
4. A non-odorous non-irritant composite antiseptic salve of the nature disclosed for pharmaceutical and medical use, composed of an ester of a phenol and a fatty-acid havin more than twelve atoms of carbon, in mixture with a sufiicient quantity of a suitable unguent to impart to the resultant mixture a melting point of a proximately body-temperature whereby sai mixture may have a salve-like consistency enabling it to be readily smeared on the skin; said phenol being mono-hydric and having the capacity of forming with stearic acid anester melting at not less than about 40 C.
5. A non-odorous non-irritant composite of being antiseptic salve of the nature disclosed for pharmaceutical and medical use, composed of an ester of a mono-hydric phenol and a fatty-acid having more than twelve atoms of carbon, saidesten having a melting point of not less than about 40 0., in mixture with a lowerrmelting suitable unguent in such proportions as will"'impart to the resultant'mixturea salve-like consistency enabling it to'be readily smeared on the skin and be absorbed thereby.
6. An antiseptic non-irritant composite salve of the nature disclosed for ceutical and medical use, compose ester of a henol and a fatty acid in mixture with'a su cient quantity of a suitable un guent to impart to the resultant mixture a melting point of approximately body.-tem-" perature enablingit to normall possess a salve-like consistency and have .t e capacity fatty acid having more than twelve atoms of carbon and said phenol bein such as will form with stearic acid a soli at not'less thanabout 40 C.-
7. An antiseptic non-irritant composite salve of the nature-disclosed for pharmaceutical and medical use, composed of a solid ester of a mono-hydric phenol and a fatty acid having more than twelve atoms of carbon, in mixture with a sufiicient quantity of a suitable unguent toimpart to the harmaof an.
readily smeared on the skin; said,
ester melting v resultant mixture a melting point of about-1 body temperature.
8. An antiseptic non-irritant non-odorous composite salve of the nature disclosed for pharmaceutical and medical use, composed of an ester of a monohydric phenol and a fatty tion of a suitable unguent as will suflice to impart a salve-like. consistency to the resultant mixture and enable it'to be readily smeared on the skin. V
' NATHAN SULZBERGER.
Witnesses BENJA IN Frsnrm, MICHAEL S. Loam,
acid, in mixture-with such a propor-
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48842509A US938614A (en) | 1909-04-07 | 1909-04-07 | Non-odorous phenol salve and ointment. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48842509A US938614A (en) | 1909-04-07 | 1909-04-07 | Non-odorous phenol salve and ointment. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US938614A true US938614A (en) | 1909-11-02 |
Family
ID=3007033
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US48842509A Expired - Lifetime US938614A (en) | 1909-04-07 | 1909-04-07 | Non-odorous phenol salve and ointment. |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US938614A (en) |
-
1909
- 1909-04-07 US US48842509A patent/US938614A/en not_active Expired - Lifetime
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