US2251934A - Germicidal soap - Google Patents
Germicidal soap Download PDFInfo
- Publication number
- US2251934A US2251934A US101787A US10178736A US2251934A US 2251934 A US2251934 A US 2251934A US 101787 A US101787 A US 101787A US 10178736 A US10178736 A US 10178736A US 2251934 A US2251934 A US 2251934A
- Authority
- US
- United States
- Prior art keywords
- soap
- germicidal
- phenol
- detergent
- composition
- 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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- 239000000344 soap Substances 0.000 title description 59
- 230000002070 germicidal effect Effects 0.000 title description 33
- 239000000203 mixture Substances 0.000 description 33
- -1 alkyl phenol Chemical compound 0.000 description 22
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 21
- 239000003599 detergent Substances 0.000 description 21
- 230000002421 anti-septic effect Effects 0.000 description 12
- 229930003836 cresol Natural products 0.000 description 11
- 150000002989 phenols Chemical class 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 235000003441 saturated fatty acids Nutrition 0.000 description 6
- 150000004671 saturated fatty acids Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 235000021588 free fatty acids Nutrition 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 4
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- WHRZCXAVMTUTDD-UHFFFAOYSA-N 1h-furo[2,3-d]pyrimidin-2-one Chemical compound N1C(=O)N=C2OC=CC2=C1 WHRZCXAVMTUTDD-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- AOHAPDDBNAPPIN-UHFFFAOYSA-N 3-Methoxy-4,5-methylenedioxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC2=C1OCO2 AOHAPDDBNAPPIN-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- 229930188104 Alkylresorcinol Natural products 0.000 description 2
- 244000073231 Larrea tridentata Species 0.000 description 2
- 235000006173 Larrea tridentata Nutrition 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 244000223014 Syzygium aromaticum Species 0.000 description 2
- 235000016639 Syzygium aromaticum Nutrition 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229960002126 creosote Drugs 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 2
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- 235000021360 Myristic acid Nutrition 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960000411 camphor oil Drugs 0.000 description 1
- 239000010624 camphor oil Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 1
- 239000001941 cymbopogon citratus dc and cymbopogon flexuosus oil Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000000249 desinfective effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 229960001867 guaiacol Drugs 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 230000007935 neutral effect Effects 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229940095696 soap product Drugs 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000002641 tar oil Substances 0.000 description 1
- 239000010678 thyme oil Substances 0.000 description 1
- BJIOGJUNALELMI-ONEGZZNKSA-N trans-isoeugenol Chemical compound COC1=CC(\C=C\C)=CC=C1O BJIOGJUNALELMI-ONEGZZNKSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
Definitions
- This invention relates to germicidal soap; and more particularly to such soaps, either solid or liquid, which contain a phenol and which retain the detergent properties of the soap and the germicidal or antiseptic properties of the phenol.
- the amount of phenol used in the new soaps of the present invention is relatively small, so that the soaps retain their detergent properties and when used in a concentration such that the concentration of phenol is such as to give effective germicidal action are effective detergents or washing agents.
- compositions containing soap and phenols of one type or another have pre viously been suggested and used as antiseptic compositions; the soap having frequently been used or proposed for use as a solubilizing agent for the phenols, many of which are not sufliciently soluble in water to produce an antiseptic solution unless some other agent is included in the solution to increase their solubility or dispersion.
- soaps are produced from saturated fatty acids with the stoichiometric quantity of caustic soda or caustic potash required to produce a neutral soap, i. e. a soap which has no free fatty acid, or a slight excess of the caustic may be used to insure that the resulting soap has no free fatty acid.
- the fatty acids used are the saturated fatty acids of the soap-forming series, such as lauric, myristic, palmitic, or stearic acid, and, while it is not necessary that the fatty acids be pure, it is necessary that they contain 'no substantial amount of unsaturated fatty acids, and that they continue no substantial amount of unsaponifiable material.
- phenols are incorporated in the composition in proportions ranging from about 1% to about 10% by weight, based on the soap; a somewhat higher proportion of the phenol be ing used in the production of liquid soap compositions than is used in the production of solid soap compositions or bar soaps, and the more active phenols being used in smaller proportions than the less active phenols.
- a phenol such as secondary or tertiary hexyl cresol may be used in proportions ranging from about 1% to about 10% based upon the weight of the soap used.
- soap from unsaturated fatty acids in substantial amounts, or the presence of unsaponifiable or unsaponifide material, other than the phenol, inthe soap product has a marked inhibiting effect upon the germicidal or antiseptic activity of the composition.
- the activity of the composition may be reduced by as much as two-thirds; and the presence of a small amount of free fatty acid, or a small amount of unsaponified or unsaponifiable material, such as free oil or fat, or other unsaponifiable'material, may reduce the germicidal or antiseptic activity of the composition by as much as
- the soap compositions may also contain a small amount of a suitable material to mask the odor of the composition, or to impart a desirable odor to the composition. Any perfuming ingredients used should in general be of a more or less phenolic character.
- Example I An aqueous liquid soap containing about 10% of the sodium soap of one or more saturated fatty acids, such as lauric, myristic, palmitic and stearic acids, is -ma.de and to the resulting liquid soap is added 1% of secondary or tertiary hexyl cresol.
- the resulting liquid soap is a good detergent, and is an effective germicide when used in solution in water in the same manner as liquid soap is ordinarily used.
- the resulting soap has a detergent or washing action similar to that of ordinary bar soap, and is an effective germicide when used as such soaps are ordinarily used.
- Phenols such as alkyl resorcinols, catechols, etc., may also be used advantageously.
- a soap composition containing the sodium or potassium soaps of one or more satu-rated soapforming fatty acids in admixture with a suitable phenol, advantageously an alkyl phenol or cresol or resorcinol or other highly active phenol,
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Patented Aug. 12, 1941 UNITED STATES PATENT OFFICE Sharp & Dohme, Incorporated, Philadelphia, Pa., a corporation of Maryland No Drawing.
Application September 21, 1936,
Serial No. 101,787
Claims.
This invention relates to germicidal soap; and more particularly to such soaps, either solid or liquid, which contain a phenol and which retain the detergent properties of the soap and the germicidal or antiseptic properties of the phenol. The amount of phenol used in the new soaps of the present invention is relatively small, so that the soaps retain their detergent properties and when used in a concentration such that the concentration of phenol is such as to give effective germicidal action are effective detergents or washing agents.
A great number of compositions containing soap and phenols of one type or another have pre viously been suggested and used as antiseptic compositions; the soap having frequently been used or proposed for use as a solubilizing agent for the phenols, many of which are not sufliciently soluble in water to produce an antiseptic solution unless some other agent is included in the solution to increase their solubility or dispersion.
Such compositions in general have used the soap in about equal proportions with the phenol, or have used the phenol in greater amounts than the soap, so that in any concentration of the mixture in water which is effective and usable as an antiseptic or germicide, theamount of soap present is too small to have any effective detergent or washing action and the solutions are disinfecting or germicidal solutions rather than detel-gent solutions. Such compositions, whether solid or liquid, have not been available for use as germicidal soaps, because the proportion of phenol which they contain is so great that their detergent action is not comparable to the detergent action of ordinary soap.
It is accordingly the object of the present invention to provide a soap which is germicidal or antiseptic, and which may be used as an ordinary soap, that is, as a detergent or washing agent, and which combines with its detergent or washing properties the property of serving as a germicide or antiseptic.
In accordance with the present invention, soaps are produced from saturated fatty acids with the stoichiometric quantity of caustic soda or caustic potash required to produce a neutral soap, i. e. a soap which has no free fatty acid, or a slight excess of the caustic may be used to insure that the resulting soap has no free fatty acid. The fatty acids used are the saturated fatty acids of the soap-forming series, such as lauric, myristic, palmitic, or stearic acid, and, while it is not necessary that the fatty acids be pure, it is necessary that they contain 'no substantial amount of unsaturated fatty acids, and that they continue no substantial amount of unsaponifiable material.
With a soap from one of these fatty acids or' a mixture of them, is combined a relatively small amount of a phenol, preferably an alkyl phenol having a high germicidal or antiseptic property. The phenols which are advantageously used are the higher and more active phenols such as the alkyl phenols, the alkyl cresols, the alkyl resorcinols, etc., such highly active phenols as secondary and tertiary butyl, amyl and hexyl cresols being particularly advantageous both from the point of view of germicidal activity and stability. These phenols are incorporated in the composition in proportions ranging from about 1% to about 10% by weight, based on the soap; a somewhat higher proportion of the phenol be ing used in the production of liquid soap compositions than is used in the production of solid soap compositions or bar soaps, and the more active phenols being used in smaller proportions than the less active phenols. For example, a phenol such as secondary or tertiary hexyl cresol may be used in proportions ranging from about 1% to about 10% based upon the weight of the soap used.
The presence'of soap from unsaturated fatty acids in substantial amounts, or the presence of unsaponifiable or unsaponifide material, other than the phenol, inthe soap product has a marked inhibiting effect upon the germicidal or antiseptic activity of the composition. For example, if a few percent of a soap from oleic acid be incorporated in such a composition, the activity of the composition may be reduced by as much as two-thirds; and the presence of a small amount of free fatty acid, or a small amount of unsaponified or unsaponifiable material, such as free oil or fat, or other unsaponifiable'material, may reduce the germicidal or antiseptic activity of the composition by as much as The soap compositions may also contain a small amount of a suitable material to mask the odor of the composition, or to impart a desirable odor to the composition. Any perfuming ingredients used should in general be of a more or less phenolic character. Such aromatic compositions as oil of cloves or creosote may be used with advantage. Oil of cloves contains eugenol, which is a propenyl guaiacol, and creosote contains cresol and guaiacol. Other perfuming agents, such as lemon grass oil, bergamot oil, camphor oil, thyme oil, and tar oil, which are non-phenolic in character, exhibit a marked in- .hibiting action upon the germicidal or antiseptic properties of the composition, and even when usedin small amounts-may reduce the activity by about two-thirds, more or less.
Excess free fatty acid, or free fat or oil, such as olive oil, reduces the activity of the composition in a similar manner. For example, if to a germicidal soap composition made up of the soap of one or more saturated fatty acids and a small proportion'of secondary hexyl cresol is added about 1% of caprioic acid, with the resulting liberation of some of the higher fatty acids, the germicidal or antiseptic activity of the composition is greatly reduced.
In a similar manner, the addition of a soap of an unsaturated fatty acid, such as oleic acid, to the germicidal detergent compositions markedly reduces the germicidal activity of them. For example, if to an active soap composition made from sodium stearate and containing, as the phenol, secondary hexyl cresol, is added a relatively small proportion of sodium oleate, the
which is an efiective germicide and which retains the detergent or washing properties of the soap despite the incorporation of the phenol in amounts sufficient to make detergent solutions of the composition germicidal.
I claim:
1. A germicidal and detergent soap composition ponifiable and unsaponified material other than I phenol.
germicidal activity is greatly decreased. If
of the sodium stearate is. replaced by an equal molecular proportion of sodium oleate, the germicidal activity of the composition is reduced by approvimately two-thirds.
Both the potassium soaps and the sodium soaps of the saturated soap-forming fatty acids behave in a similar manner, forming antiseptic or germicidal detergent compositions when admixed with a suitable phenol.
The invention will be further illustrated by the following examples, but it is not limited thereto.
Example I.-An aqueous liquid soap containing about 10% of the sodium soap of one or more saturated fatty acids, such as lauric, myristic, palmitic and stearic acids, is -ma.de and to the resulting liquid soap is added 1% of secondary or tertiary hexyl cresol. The resulting liquid soap is a good detergent, and is an effective germicide when used in solution in water in the same manner as liquid soap is ordinarily used.
Example lI.--To a solid soap containing 15% of water and 85% of the sodium soap of one or.
more saturated fatty acids is added from 1 to 10% of secondary or tertiary hexyl cresol. The resulting soap has a detergent or washing action similar to that of ordinary bar soap, and is an effective germicide when used as such soaps are ordinarily used.
Alkyl di-hydroxy. Phenols, such as alkyl resorcinols, catechols, etc., may also be used advantageously.
Thus by the present invention, I provide a soap composition, containing the sodium or potassium soaps of one or more satu-rated soapforming fatty acids in admixture with a suitable phenol, advantageously an alkyl phenol or cresol or resorcinol or other highly active phenol,
2. A germicidal and detergent soap composition as in claim 1, in which the alkyl phenol is an alkyl cresol.
3. A germicidal and detergent soap composition as in claim 1, in which the alkyl phenol is an alkyl cresol, in which the alkyl group has at least four but not more than six carbon atoms.
4. A germicidal and detergent soap as in claim 1, in which the phenol is an alkyl dy-hydroxy phenol.
5. A liquid aqueous soap composition which exhibits effective germicidal activity, possesses effective detergent and washing'properties, and which comprises from about 0.1% to about 1% of an alkyl phenol capable of acting as a germities which soap contains about 15% water and from about 1% to about 10 based on the soap, of an alkyl phenol capable of acting as a germicide, said soap being a water-soluble soap of saturated fatty acids and substantially free from unsaponified and unsaponifiable fatty material and from soap of unsaturated fatty acids.
9. A germicidal and detergent soap composition as in claim 8, in which the alkyl phenol is an alkyl cresol.
10. A germicidal and detergent soap composition as in claim 8, in which the alkyl phenol is an alkyl cresol, in which the alkyl group has at least four but not more than six carbon atoms.
WALTER H. HARTUNG.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US101787A US2251934A (en) | 1936-09-21 | 1936-09-21 | Germicidal soap |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US101787A US2251934A (en) | 1936-09-21 | 1936-09-21 | Germicidal soap |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2251934A true US2251934A (en) | 1941-08-12 |
Family
ID=22286407
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US101787A Expired - Lifetime US2251934A (en) | 1936-09-21 | 1936-09-21 | Germicidal soap |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2251934A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2535077A (en) * | 1940-03-15 | 1950-12-26 | Sindar Corp | Germicidal soaps containing halogenated dihydroxy diphenyl methanes |
| DK83375C (en) * | 1953-07-04 | 1957-08-26 | Benckiser Gmbh Joh A | Disinfectant cleaner. |
| US3312623A (en) * | 1963-12-23 | 1967-04-04 | Monsanto Co | Antiseptic detergent compositions |
| US4589994A (en) * | 1984-12-17 | 1986-05-20 | Moseman Roger E | Liquid foot treatment composition |
| US4668419A (en) * | 1984-12-17 | 1987-05-26 | Moseman Roger E | Liquid foot treatment composition |
-
1936
- 1936-09-21 US US101787A patent/US2251934A/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2535077A (en) * | 1940-03-15 | 1950-12-26 | Sindar Corp | Germicidal soaps containing halogenated dihydroxy diphenyl methanes |
| DK83375C (en) * | 1953-07-04 | 1957-08-26 | Benckiser Gmbh Joh A | Disinfectant cleaner. |
| US3312623A (en) * | 1963-12-23 | 1967-04-04 | Monsanto Co | Antiseptic detergent compositions |
| US4589994A (en) * | 1984-12-17 | 1986-05-20 | Moseman Roger E | Liquid foot treatment composition |
| US4668419A (en) * | 1984-12-17 | 1987-05-26 | Moseman Roger E | Liquid foot treatment composition |
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