US2353735A - Germicidal soap - Google Patents
Germicidal soap Download PDFInfo
- Publication number
- US2353735A US2353735A US380074A US38007441A US2353735A US 2353735 A US2353735 A US 2353735A US 380074 A US380074 A US 380074A US 38007441 A US38007441 A US 38007441A US 2353735 A US2353735 A US 2353735A
- Authority
- US
- United States
- Prior art keywords
- soap
- germicidal
- soaps
- agents
- agent
- 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
- 239000000344 soap Substances 0.000 title description 42
- 230000002070 germicidal effect Effects 0.000 title description 18
- 239000003795 chemical substances by application Substances 0.000 description 18
- 238000012360 testing method Methods 0.000 description 7
- 241000191967 Staphylococcus aureus Species 0.000 description 5
- 239000003599 detergent Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 3
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical class C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229940095696 soap product Drugs 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KDPQJVLEWUMQRM-UHFFFAOYSA-N 1,2,3-trichloro-4-(2,3,4-trichlorophenyl)sulfanylbenzene Chemical compound ClC1=C(Cl)C(Cl)=CC=C1SC1=CC=C(Cl)C(Cl)=C1Cl KDPQJVLEWUMQRM-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000003568 Sodium, potassium and calcium salts of fatty acids Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XOMKZKJEJBZBJJ-UHFFFAOYSA-N 1,2-dichloro-3-phenylbenzene Chemical group ClC1=CC=CC(C=2C=CC=CC=2)=C1Cl XOMKZKJEJBZBJJ-UHFFFAOYSA-N 0.000 description 1
- LAXBNTIAOJWAOP-UHFFFAOYSA-N 2-chlorobiphenyl Chemical group ClC1=CC=CC=C1C1=CC=CC=C1 LAXBNTIAOJWAOP-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 238000009631 Broth culture Methods 0.000 description 1
- 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 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- KSZVHVUMUSIKTC-UHFFFAOYSA-N acetic acid;propan-2-one Chemical compound CC(C)=O.CC(O)=O KSZVHVUMUSIKTC-UHFFFAOYSA-N 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000001309 chloro group Chemical class Cl* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- -1 for example Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 235000013966 potassium salts of fatty acid Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000013875 sodium salts of fatty acid Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000009827 uniform distribution Methods 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 soaps and has particular reference to soaps which possess germicidal properties.
- R is halogen and n is an integer from '1 to 4 inclusive.
- the invention may be practiced by adding the agents to the soap in any suitable manner during the crutching or milling or similar operation. Care should be taken to obtain a uniform distribution of the agents throughout the soap. They may be dissolved in a small amount of a suitable solvent, for example, acetone or alcohol. If desired, however, the agents may be added directly to the soap without dissolving them previously. In the case of frame" soaps, it is preferred to add the agents to the soap during the crutching operation. With milled soaps, it is preferred to make the addition during the milling operation. In the case of liquid soaps, it is preferred to effect the addition while the agent is in solution. In general, any method which results in the agent being uniformly incorporated into the final soap product is satisfactory.
- A refers to the neutral soap plus the added agent, except'in the case of the soap blank where A refers to the soap iteslf.
- I A/1.5 means that 1 part by weight of material A was diluted with 1.5 parts of water. Similarly, All refers to a mixtur of 1 part of A and 4 parts of water. etc.
- soap as used herein is employed in its popular or ordinary meaning.
- the term refers to cleansing agents, made usually by the action of alkali on fat or fatty acids and consisting essentially of sodium or potassium salts of fatty acids.
- germicidal soap for the purposes of this patent application refers to those soaps which are effective against Staphylococcus aureus of standard resistance. For example, if a soap is not effective against Staphylococcus aureus, it is not considered to be germicidal, whether or not it is effective against other types of bacteria. On the other hand, if a soap is effective against Staphylococcus aureus, the soap is considered to be germicidal, whether or not it is effective against any other types of bacteria.
- a germicidal soap consisting of a detergent soap and 2,2'-dihydroxy 3,5,63,5',6' hexachloro diphenyl sulfide.
- a germicidal soap comprising a detergent soap and from 1% to 3% by weight of 2,2- 1(%ihydroxy-3,5,6-3,5',6'-hexachloro diphenyl sul- ERIC C. KUNZ.
Landscapes
- 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 July 18, 1944 GERMICIDAU SOAP Eric C. Kunz, Montclair, Max Luthy, Ridgewood, and William S. Gump, Nutley, N. J., assignors to Burton T. Bush, Inc., New York, N. Y., a corporation of New Jersey No Drawing. Application February 21, 1941, Serial No. 380,074
3 Claims.
This invention relates to soaps and has particular reference to soaps which possess germicidal properties.
An object of this invention is to provide a germicidal soap by incorporatingcertain substances, hereinafter mentioned, into washing, toilet or so-called liquid soaps.
A further object of this invention is the provision of new compositions of matter.
Other objects will be apparent to persons skilled in the art from a reading of the following description.
According to the present invention, washing soaps, toilet soaps and liquid soaps may be rendered germicidal by incorporating therein a 2,2'-dihydroxy halogenated diphenyl sulfide.
The 2,2'-dihydroxy halogenated diphenyl sulfides of this invention may be represented according to their chemical structure as follows:
H OH
where R is halogen and n is an integer from '1 to 4 inclusive.
As examples of specific members of the foregoing class of compounds in the chlorine series may be mentioned:
OH on on on and on on 01 s on Solubility (room Melting temperature) point Quite insoluble in water. Easily soluble in alcohol, ether, acetic acid acetone and 2, 2' dihydroxy 5, 5 dichloro diphenyl sulfide.
alkaiies. 2, 2 dihydroxy 3, 5 3, 5 tetra- 188 Do.
chloro diphenyl sulfide. 2,2 dihydroxy 3,5,6 3, ,5, 6- 163 Do.
hexachloro diphenyl sulfide.
For purposes of this application, the 2,2'-dihydroxy halogenated. diphenyl sulfides are termed germicidal agents, and are hereinafter sometimes referred to as such, and sometimes referred to merely as agents,
Relatively small amounts of the germicidal agents of the invention are sumcient to render soap germicidal. Amounts as low as /2 of 1% of the germicidal agent, based on the weight of the soap content of the final soap product, have proved satisfactory in some cases. However, it is preferred to use amounts of the order of 1 to 3% on the same basis. The upper limit of the amount of agent which may be used is deterlmined by practical considerations. As a general rule, increasing the concentration of agent in the soap increases the germicidal activity of the resulting soap. However, the cost of the agent relative to the cost of the soap itself mitigates against the use of too large an amount of the agent in soap. Moreover, large amounts of the agent in soap are to be avoided if it is desired to obtain a resulting soap product with satisfactory detergent properties. Soaps containing as much as 10% of the agents of this invention were found to be satisfactory in this regard.
The invention may be practiced by adding the agents to the soap in any suitable manner during the crutching or milling or similar operation. Care should be taken to obtain a uniform distribution of the agents throughout the soap. They may be dissolved in a small amount of a suitable solvent, for example, acetone or alcohol. If desired, however, the agents may be added directly to the soap without dissolving them previously. In the case of frame" soaps, it is preferred to add the agents to the soap during the crutching operation. With milled soaps, it is preferred to make the addition during the milling operation. In the case of liquid soaps, it is preferred to effect the addition while the agent is in solution. In general, any method which results in the agent being uniformly incorporated into the final soap product is satisfactory.
The method employed to test the germicidal properties of the soaps of this invention is a modification of the U. S. Food and Drug Administration method (Circular 198, December 1931). A standard 24 hour broth culture of Staphylococcus aureus, contact time of minutes, and temperature of 37 C. were used in the tests. Instead of transferring the loopful of material containing the test sample and culture to the broth at the end of the contact time as in the official F. D. A. test method, the loopful was transferred to a tube of liquid agar, maintained at approximately 42 C. The contents were thoroughly mixed and then poured into a petri dish and allowed to solidify at room temperature, followed by an incubation period of 40-48 hours at 37 C.
The number of colonies present after this treatment were counted. It is this "plate count which the numbers given in the accompanying table represent. The number zero (0) represents absence of colonies and hence indicates that the sample tested destroyed all of the bacteria. In other words, germicidal power is inversely related to the number given as the plate count.
In order to check the organisms, Staphylococcus aureus, for proper resistance, a plate count was run on phenol of dilution of 1:80 and 1:90 and only those cultures having proper resistance were employed in the test.
The following table gives data obtained by testing a neutral milled soap alone and by testing the same soap containing 2% of certain of the germicidal agents. The data given in the table are intended as illustrative of specific embodhnents of theinvention and are not to be considered as limiting the scope of the invention.
1 A, refers to the neutral soap plus the added agent, except'in the case of the soap blank where A refers to the soap iteslf.
I A/1.5, means that 1 part by weight of material A was diluted with 1.5 parts of water. Similarly, All refers to a mixtur of 1 part of A and 4 parts of water. etc. The figures under the des gnatlons A/Lb. etc., refer to the plate counts" obtained at the dilution indicated.
a Number 3 was found to give a zero count even at concentrations as low as A/29 under the test conditions.
4 Not tested.
The term soap" as used herein is employed in its popular or ordinary meaning. The term refers to cleansing agents, made usually by the action of alkali on fat or fatty acids and consisting essentially of sodium or potassium salts of fatty acids.
The term germicidal soap for the purposes of this patent application refers to those soaps which are effective against Staphylococcus aureus of standard resistance. For example, if a soap is not effective against Staphylococcus aureus, it is not considered to be germicidal, whether or not it is effective against other types of bacteria. On the other hand, if a soap is effective against Staphylococcus aureus, the soap is considered to be germicidal, whether or not it is effective against any other types of bacteria.
The foregoing illustrates the practice of our invention which, however, is not to be limited thereby but is to be construed as broadly as permissible in view of the prior art and limited solely by the appended claims.
What is claimed is:
1. A germicidal soap consisting of a detergent soap and 2,2'-dihydroxy 3,5,63,5',6' hexachloro diphenyl sulfide.
2. A germicidal soap comprising a detergent soap and not more than 5% by weight of 2,2- dihydroxy-3,5,6-3',5,6-hexachloro diphenyl sulfide.
3. A germicidal soap comprising a detergent soap and from 1% to 3% by weight of 2,2- 1(%ihydroxy-3,5,6-3,5',6'-hexachloro diphenyl sul- ERIC C. KUNZ.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US380074A US2353735A (en) | 1941-02-21 | 1941-02-21 | Germicidal soap |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US380074A US2353735A (en) | 1941-02-21 | 1941-02-21 | Germicidal soap |
Publications (1)
Publication Number | Publication Date |
---|---|
US2353735A true US2353735A (en) | 1944-07-18 |
Family
ID=23499798
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US380074A Expired - Lifetime US2353735A (en) | 1941-02-21 | 1941-02-21 | Germicidal soap |
Country Status (1)
Country | Link |
---|---|
US (1) | US2353735A (en) |
Cited By (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2692862A (en) * | 1951-09-05 | 1954-10-26 | Du Pont | Cleansing compositions having antibacterial properties |
US2695317A (en) * | 1952-04-10 | 1954-11-23 | Sterling Drug Inc | 2, 2'-dihydroxy-3, 5, 5'-trichlorodiphenyl sulfide and preparation thereof |
US2695881A (en) * | 1951-01-22 | 1954-11-30 | Monsanto Chemicals | Antiseptic soap composition |
US2760988A (en) * | 1953-05-06 | 1956-08-28 | Geigy Ag J R | Bis(2-hydroxy-4, 5-dichlorophenyl) sulfide |
DK83375C (en) * | 1953-07-04 | 1957-08-26 | Benckiser Gmbh Joh A | Disinfectant cleaner. |
DE966999C (en) * | 1953-05-06 | 1957-09-26 | Geigy Ag J R | Germicidal preparation |
US2814597A (en) * | 1953-03-12 | 1957-11-26 | Norda Essential Oil & Chemical | Germicidal soaps composition |
US2897235A (en) * | 1956-03-20 | 1959-07-28 | Monsanto Chemicals | Amine salts of 2,2'-thiobis |
US2937208A (en) * | 1955-05-18 | 1960-05-17 | Bayer Ag | Metasulfides of polyhalogenated phenols |
US2948684A (en) * | 1957-05-10 | 1960-08-09 | Lever Brothers Ltd | Disinfectant and deodorant soap composition |
US2965575A (en) * | 1957-05-27 | 1960-12-20 | Monsanto Chemicals | Antiseptic detergent compositions |
US3024163A (en) * | 1959-06-30 | 1962-03-06 | Vanderbilt Co R T | Bacteriostats |
US3081266A (en) * | 1955-09-27 | 1963-03-12 | Armour & Co | Antiseptic detergent compositions |
US3177115A (en) * | 1962-04-03 | 1965-04-06 | Armour & Co | Antiseptic compositions |
US3200135A (en) * | 1959-07-29 | 1965-08-10 | Sterling Drug Inc | Copper, cadmium, and zinc salts of halo-2, 2'-dihydroxydiphenyl sulfides and sulfoxides |
US3294681A (en) * | 1963-04-10 | 1966-12-27 | Nat Lead Co | Process of drilling a well with a drilling fluid containing a starch product |
US3445397A (en) * | 1962-04-20 | 1969-05-20 | Armour & Co | Synergistic combination of a halogenated bisphenol and a polyhalo-salicylanilide |
US4642383A (en) * | 1982-09-30 | 1987-02-10 | James River Graphics, Inc. | Fast coupling lemon-yellow phenolic couplers |
US20030162987A1 (en) * | 2002-02-25 | 2003-08-28 | Houser Eric J. | Functionalized small molecules for use in chemical sensors |
US10548911B2 (en) | 2014-06-16 | 2020-02-04 | University Of Rochester | Small molecule anti-scarring agents |
-
1941
- 1941-02-21 US US380074A patent/US2353735A/en not_active Expired - Lifetime
Cited By (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2695881A (en) * | 1951-01-22 | 1954-11-30 | Monsanto Chemicals | Antiseptic soap composition |
US2692862A (en) * | 1951-09-05 | 1954-10-26 | Du Pont | Cleansing compositions having antibacterial properties |
US2695317A (en) * | 1952-04-10 | 1954-11-23 | Sterling Drug Inc | 2, 2'-dihydroxy-3, 5, 5'-trichlorodiphenyl sulfide and preparation thereof |
US2814597A (en) * | 1953-03-12 | 1957-11-26 | Norda Essential Oil & Chemical | Germicidal soaps composition |
US2760988A (en) * | 1953-05-06 | 1956-08-28 | Geigy Ag J R | Bis(2-hydroxy-4, 5-dichlorophenyl) sulfide |
DE966999C (en) * | 1953-05-06 | 1957-09-26 | Geigy Ag J R | Germicidal preparation |
DK83375C (en) * | 1953-07-04 | 1957-08-26 | Benckiser Gmbh Joh A | Disinfectant cleaner. |
US2937208A (en) * | 1955-05-18 | 1960-05-17 | Bayer Ag | Metasulfides of polyhalogenated phenols |
US3081266A (en) * | 1955-09-27 | 1963-03-12 | Armour & Co | Antiseptic detergent compositions |
US2897235A (en) * | 1956-03-20 | 1959-07-28 | Monsanto Chemicals | Amine salts of 2,2'-thiobis |
US2948684A (en) * | 1957-05-10 | 1960-08-09 | Lever Brothers Ltd | Disinfectant and deodorant soap composition |
US2965575A (en) * | 1957-05-27 | 1960-12-20 | Monsanto Chemicals | Antiseptic detergent compositions |
US3024163A (en) * | 1959-06-30 | 1962-03-06 | Vanderbilt Co R T | Bacteriostats |
US3200135A (en) * | 1959-07-29 | 1965-08-10 | Sterling Drug Inc | Copper, cadmium, and zinc salts of halo-2, 2'-dihydroxydiphenyl sulfides and sulfoxides |
US3177115A (en) * | 1962-04-03 | 1965-04-06 | Armour & Co | Antiseptic compositions |
US3445397A (en) * | 1962-04-20 | 1969-05-20 | Armour & Co | Synergistic combination of a halogenated bisphenol and a polyhalo-salicylanilide |
US3294681A (en) * | 1963-04-10 | 1966-12-27 | Nat Lead Co | Process of drilling a well with a drilling fluid containing a starch product |
US4642383A (en) * | 1982-09-30 | 1987-02-10 | James River Graphics, Inc. | Fast coupling lemon-yellow phenolic couplers |
US20030162987A1 (en) * | 2002-02-25 | 2003-08-28 | Houser Eric J. | Functionalized small molecules for use in chemical sensors |
US7132294B2 (en) * | 2002-02-25 | 2006-11-07 | The United States Of America As Represented By The Secretary Of The Navy | Functionalized small molecules for use in chemical sensors |
US10548911B2 (en) | 2014-06-16 | 2020-02-04 | University Of Rochester | Small molecule anti-scarring agents |
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