US3063895A - Disinfectant compositions - Google Patents
Disinfectant compositions Download PDFInfo
- Publication number
- US3063895A US3063895A US4170A US417060A US3063895A US 3063895 A US3063895 A US 3063895A US 4170 A US4170 A US 4170A US 417060 A US417060 A US 417060A US 3063895 A US3063895 A US 3063895A
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- United States
- Prior art keywords
- composition
- alkali metal
- phenolic compound
- group
- disinfectant
- 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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Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
Definitions
- disinfectant compositions are now well-known, the great majority of which are aqueous solutions or emulsions of phenolic compounds.
- known disinfectants suffer from a variety of drawbacks, among which may be mentioned selective action against only certain organisms, reduction in efficiency by organic matter or some specific inhibitor, high tom'city, corrosive action on the skin or mucous membrane, production of scum when diluted in hard or brackish waters or reduction of efficiency therein and immiscibility with sea water.
- the disinfectant compositions according to the invention are aqueous solutions essentially containing the following phenols in the proportions by weight stated:
- compositions according to the invention further preferable contain alkali-metal or ammonium ions to increase the solubility of the phenols present.
- the pH of the compositions preferably does not exceed 11.
- a convenient quantity of alkali metal (preferably sodium) or ammonium ions is from 02-29% by weight (calculated as alkali metal or ammonium hydroxide).
- a preferred composition according to the invention comprises an aqueous solution, having a phenol content equivalent to 16% of p-chlor-m-cresol, 0.55% of ophenyl phenol, 0.55% of an alkali metal salt, preferably sodium salt of o-phenyl phenol, 0.55% of o-benzyl-pchlorphenol and from 15% of an alkali metal salt, preferably sodium salt of a polychlorphenol.
- compositions according to the invention have a range of action against gram positive and gram negative bacteria, fungi and fungal and bacterial spores substantially greater than disinfectant compositions hitherto proposed.
- known disinfectant compositions whilst active against certain organisms, have failed against other important organisms.
- the compositions according to the invention have, however, been found to be very effective against most, if not all, of the micro-orgam isms which it is desired to combat, for example, in hospitals.
- compositions according to the invention besides being active against such common organisms as Staphylococcus aureus, Streptococcus pyo genes and Pseudomorms pyocyaneus, are highly effective against Mycobacterium tuberculosis and various sporulating organisms as well as many pathogenic fungi. tshould ice be pointed out that, in the compositions according to the invention, both the nature of the phenolic ingredients used different proportions do not possess the same wide range of action as do the compositions according to the invention.
- the compositions according to the invention are'also generally effective in the presence of various kinds of organic matter.
- compositions according to the invention preferably also contain from '0.55% of p-chlor-m-xylenol, which component has been found to enhance the biocidal-activity of the composition, particularly against gram negative bacteria.
- compositions according to the invention further preferably contain a water-miscible (or partially watermiscible) alcohol for the purpose of further aiding the solubility of the phenols thereby reducing risk of precipitation on dilution with, for example, hard or brackish water.
- a water-miscible (or partially watermiscible) alcohol for the purpose of further aiding the solubility of the phenols thereby reducing risk of precipitation on dilution with, for example, hard or brackish water.
- Alcohols containing from 1-4 carbon atoms are very satisfactory, examples of which are methanol, ethanol, propanol, iso-propanol, iso-butanol, etc; a concentration of from 5-25 of alcohol has been found to be advantageous.
- compositions according to the invention further preferably contain a compatible surface. active agent.
- Anionic surface active agents are particularly useful and examples of such substances are alkyl sulphate salts, such as sodium lauryl sulphate, mixed alkyl aryl sulphatesalts and various sulphonated oils, e.g. sulphonated castor oil.
- the detergents sold as Teepol, Comprox and Iranapol have been found to be very satisfactory.
- the preferred polychlorphenols for use in the compositions according to the invention are tri-, tetraand pentachlorphenol.
- compositions according to the invention may be formulated in any convenient way.
- the parent phenols may be conveniently mixed with water, alcohol and surface active agent, and the necessary quantity of alkali metal or ammonium hydroxide may be added to give the desired proportion of alkali metal or ammonium ions.
- one or more of the phenols may be added as their salts.
- compositions according to the invention are those equivalent to the following composition.
- composition according to the above-mentioned example has the following properties:
- Germicidal Test Results Using E. coli, Ps. pyocyaneus, Proteus vulgaris and S. aureus in a series of suspension tests conducted at 18 C., a 0.5 soln. of the composition in hard water killed all the test organisms in less than 2 /2 mins. Similar tests performed in the presence of 20% blood serum, 20% skimmed milk or 1% linseed oil soap soln. again showed complete destruction of the organisms by a 2% dilution in less than 2 /2 mins.
- Linen strips infected with the dried test organisms are sterilised in 30 mins. at 18 C. by a 3% soln. of the composition, even in the presence of 1% linseed oil soap soln.
- Trichomonas vaginalis a solution of 1 part of the composition of the example in 700 parts of water destroyed the parasite, in organic medium, within 5 minutes at 36.
- Tests were performed in distilled water (W) and blood serum (S) by the Rideal-Walker (R.W.) (B.S.S. 541:1934) and Food and Drug Administration of the United States (F.D.A.) methods.
- T uberculocidal Tests Concentration required to kill M. tuberculosis (human strain) in less than 5 mins.
- F ungieidal Tests Concentration required to kill T rich. inderdigitale in less than 5 mins.
- Composition A Composition B p-chlor-m-cresol o-phenyl-phenol 1 sodium o-phenylphenate o-benzyl-p-ehlorphenol p-chlor-rn-xylenoL 1 5 sodium pentachlorphenate 2.0% 4.0%.
- compositions A and B as shown in the above table are conveniently prepared by dissolving the parent phenols the required amount of water, alcohol and surface active agent, followed by the addition of the necessary quantity of caustic soda equivalent to the sodium salts referred to.
- a disinfectant composition comprising an aqueous solution containing from 16% by weight of a first phenolic compound selected from the group consisting of p-chlor-m-cresol and its alkali metal and ammonium salts, from 0.540% of a second phenolic compound selected from the group consisting of o-phenyl-phenol and its alkali metal and ammonium salts, from 0.55% of a third phenolic compound selected from the group consisting of o-benzyl-p-chlorphenol and its alkali metal and ammonium salts and from l5% of a fourth phenolic compound selected from the group consisting of pentachlorphenol and alkali metal and ammonium salts of said fourth phenolic compound.
- composition of claim 1 which is a clear solution having a pH not exceeding 11.
- a composition as claimed in claim 1 which contains from 0.22% by weight calculated as the corresponding hydroxide of at least one ion selected from the group consisting of alkali metal and ammonium ions.
- composition as claimed in claim 3 in which all of said ions are sodium ions.
- composition as claimed in claim 1 which also contains a lower alkanol containing from 1-4 carbon atoms.
- composition as claimed in claim 5 in which said lower alkanol is selected from the group consisting of methanol, propanol, butanol.
- composition as claimed in claim 1 which also contains a compatible surface active agent.
- composition as claimed in claim 7 in which said surface active agent is selected from the group consisting of an alkyl sulphate salt, a mixed alkyl aryl sulphate salt and a sulphonated oil.
- a disinfectant composition comprising an aqueous solution containing from 1-6% by weight of p-chlor-mcresol, from 0.5-5% by weight of o-phenyl-phenol, from 0.5-5% by weight of an alkali metal salt of o-phenylphenol, from 0.5-5 by weight of o-benzyl-p-chlorphenol and from 1-5 by weight of an alkali metal salt of pentachlorphenol.
Description
United States 3,063,895 DISINFECTANT COMPOSITIGNS- Charles Arthur Pearson and James William Gibson, Hull. England, and Wilhelm Barthels, Hamburg, Germany, assignors' to William Pearson Limited, London, England, a British company No Drawing. Filed Jan. 25, 196i Ser. No. 4,170 Claims priority, application Great Britain Jan. 29, W59 2 9 Claims. c1. 167--3l) This invention is concerned with improvements in or relating to disinfectant compositions.
Many disinfectant compositions are now well-known, the great majority of which are aqueous solutions or emulsions of phenolic compounds. However, known disinfectants suffer from a variety of drawbacks, among which may be mentioned selective action against only certain organisms, reduction in efficiency by organic matter or some specific inhibitor, high tom'city, corrosive action on the skin or mucous membrane, production of scum when diluted in hard or brackish waters or reduction of efficiency therein and immiscibility with sea water.
It is an object of the present invention to provide a new and improved disinfectant composition.
The disinfectant compositions according to the invention are aqueous solutions essentially containing the following phenols in the proportions by weight stated:
Percent p-Chlor-m-cresol 1-6 The compositions according to the invention further preferable contain alkali-metal or ammonium ions to increase the solubility of the phenols present. The pH of the compositions preferably does not exceed 11. A convenient quantity of alkali metal (preferably sodium) or ammonium ions is from 02-29% by weight (calculated as alkali metal or ammonium hydroxide).
A preferred composition according to the invention comprises an aqueous solution, having a phenol content equivalent to 16% of p-chlor-m-cresol, 0.55% of ophenyl phenol, 0.55% of an alkali metal salt, preferably sodium salt of o-phenyl phenol, 0.55% of o-benzyl-pchlorphenol and from 15% of an alkali metal salt, preferably sodium salt of a polychlorphenol.
We have found that the compositions according to the inventionhave a range of action against gram positive and gram negative bacteria, fungi and fungal and bacterial spores substantially greater than disinfectant compositions hitherto proposed. Thus, known disinfectant compositions, whilst active against certain organisms, have failed against other important organisms. The compositions according to the invention have, however, been found to be very effective against most, if not all, of the micro-orgam isms which it is desired to combat, for example, in hospitals. In particular, the compositions according to the invention, besides being active against such common organisms as Staphylococcus aureus, Streptococcus pyo genes and Pseudomorms pyocyaneus, are highly effective against Mycobacterium tuberculosis and various sporulating organisms as well as many pathogenic fungi. tshould ice be pointed out that, in the compositions according to the invention, both the nature of the phenolic ingredients used different proportions do not possess the same wide range of action as do the compositions according to the invention. The compositions according to the invention are'also generally effective in the presence of various kinds of organic matter.
The compositions according to the invention preferably also contain from '0.55% of p-chlor-m-xylenol, which component has been found to enhance the biocidal-activity of the composition, particularly against gram negative bacteria.
The compositions according to the invention further preferably contain a water-miscible (or partially watermiscible) alcohol for the purpose of further aiding the solubility of the phenols thereby reducing risk of precipitation on dilution with, for example, hard or brackish water. Alcohols containing from 1-4 carbon atoms are very satisfactory, examples of which are methanol, ethanol, propanol, iso-propanol, iso-butanol, etc; a concentration of from 5-25 of alcohol has been found to be advantageous.
The compositions according to the invention further preferably contain a compatible surface. active agent. Anionic surface active agents are particularly useful and examples of such substances are alkyl sulphate salts, such as sodium lauryl sulphate, mixed alkyl aryl sulphatesalts and various sulphonated oils, e.g. sulphonated castor oil. The detergents sold as Teepol, Comprox and Iranapol have been found to be very satisfactory.
The preferred polychlorphenols for use in the compositions according to the invention are tri-, tetraand pentachlorphenol.
The compositions according to the invention may be formulated in any convenient way. Thus, for example, the parent phenols may be conveniently mixed with water, alcohol and surface active agent, and the necessary quantity of alkali metal or ammonium hydroxide may be added to give the desired proportion of alkali metal or ammonium ions. Alternatively one or more of the phenols may be added as their salts.
Particularly useful compositions according to the invention are those equivalent to the following composition.
Sodium pentachlorphenatel5%. C C alcohols 525%. Surface active agent l040%. Water To%,
An example of a formulation according to the invention which has proved especially effective is given as follows, for the purpose of illustration only.
4% p-chlor-m-cresol 1.5% o-phenyl phenol 1.5% sodium o-phen-ylphenolate 1% o-benzyl-p-chlorphenol 1% p-chlor-m-xylenol 3% sodium pentachlorphenate 10% iso-propanol 28% Teepol 514 Water to 100% The composition according to the above-mentioned example has the following properties:
It is a clear amber fluid, stable to both heat and cold. Refluxing at 100 C. for 4 hours does not destroy its germicidal activity, whilst, if held at C. for several weeks, it does not crystallise out or deposit.
It is only mildly alkaline, 1%, 2% and dilutions in tap water having pH values of 8.2, 8.4 and 8.6 respectively.
In the recommended dilutions, it is non-corrosive to skin at 1% and mucous membrane at 0.5% as evidenced by its successful application in cases of acute vulvo vaginitis.
All dilutions in distilled or hard water are crystal clear to slightly opalcscent, and free from deposit or scum, an advantage particularly applicable to instrument sterilisation. It is miscible with sea and brackish waters. forming clear to opalescent solutions. Germicidal tests were carried out upon the composition according to the abovementioned example with the following results:
Germicidal Test Results Using E. coli, Ps. pyocyaneus, Proteus vulgaris and S. aureus in a series of suspension tests conducted at 18 C., a 0.5 soln. of the composition in hard water killed all the test organisms in less than 2 /2 mins. Similar tests performed in the presence of 20% blood serum, 20% skimmed milk or 1% linseed oil soap soln. again showed complete destruction of the organisms by a 2% dilution in less than 2 /2 mins.
Linen strips infected with the dried test organisms are sterilised in 30 mins. at 18 C. by a 3% soln. of the composition, even in the presence of 1% linseed oil soap soln.
Fungicidal properties are demonstrated by the destruction of Trich. inderdigitale, Trich. acumz'naziwn and Candida albicans in 30 mins. by a 2% soln. of the composition at 18 C.
Against Trichomonas vaginalis, a solution of 1 part of the composition of the example in 700 parts of water destroyed the parasite, in organic medium, within 5 minutes at 36.
Comparative Results For comparison several well-known types of disinfectant were tested; these were Liquor chlorxylenolis B.P. (L.C.X.), Liquor cresolis saponatus B.P. (L.C.S.) and a disinfectant of the coal tar-oil type according to British Standard Specification No. 2462.
The results obtained compared with the composition of the above example show the advantages of the latter in germicidal eiiiciency.
Tests were performed in distilled water (W) and blood serum (S) by the Rideal-Walker (R.W.) (B.S.S. 541:1934) and Food and Drug Administration of the United States (F.D.A.) methods.
til
T uberculocidal Tests Concentration required to kill M. tuberculosis (human strain) in less than 5 mins.
Percent Composition of example 1 L.C.X. 2 L.C.S. 1 Coal Tar product 5 Sporicidal Tests Concentration required to kill the spores of B. subtilis in less than 5 mins.
F ungieidal Tests Concentration required to kill T rich. inderdigitale in less than 5 mins.
Percent Composition of example 2 L.C.X., greater than 10 L.C.S., greater than 5 Coal tar product 10 The following table gives two further examples of representative compositions (A and B) according to the invention.
Composition A Composition B p-chlor-m-cresol o-phenyl-phenol 1 sodium o-phenylphenate o-benzyl-p-ehlorphenol p-chlor-rn-xylenoL 1 5 sodium pentachlorphenate 2.0% 4.0%.
plus: ethanol, 20%; lus: iso-butanol, 25%;
Gomprox, 35%; Sodium dodecyl hen- Water to zene sulphonate,
20%; Water to 100%.
The compositions A and B as shown in the above table are conveniently prepared by dissolving the parent phenols the required amount of water, alcohol and surface active agent, followed by the addition of the necessary quantity of caustic soda equivalent to the sodium salts referred to.
We claim:
1. A disinfectant composition comprising an aqueous solution containing from 16% by weight of a first phenolic compound selected from the group consisting of p-chlor-m-cresol and its alkali metal and ammonium salts, from 0.540% of a second phenolic compound selected from the group consisting of o-phenyl-phenol and its alkali metal and ammonium salts, from 0.55% of a third phenolic compound selected from the group consisting of o-benzyl-p-chlorphenol and its alkali metal and ammonium salts and from l5% of a fourth phenolic compound selected from the group consisting of pentachlorphenol and alkali metal and ammonium salts of said fourth phenolic compound.
2. The composition of claim 1 which is a clear solution having a pH not exceeding 11.
3. A composition as claimed in claim 1 which contains from 0.22% by weight calculated as the corresponding hydroxide of at least one ion selected from the group consisting of alkali metal and ammonium ions.
4. A composition as claimed in claim 3 in which all of said ions are sodium ions.
5. A composition as claimed in claim 1 which also contains a lower alkanol containing from 1-4 carbon atoms.
6. A composition as claimed in claim 5 in which said lower alkanol is selected from the group consisting of methanol, propanol, butanol.
7. A composition as claimed in claim 1 which also contains a compatible surface active agent.
8. A composition as claimed in claim 7 in which said surface active agent is selected from the group consisting of an alkyl sulphate salt, a mixed alkyl aryl sulphate salt and a sulphonated oil.
9. A disinfectant composition comprising an aqueous solution containing from 1-6% by weight of p-chlor-mcresol, from 0.5-5% by weight of o-phenyl-phenol, from 0.5-5% by weight of an alkali metal salt of o-phenylphenol, from 0.5-5 by weight of o-benzyl-p-chlorphenol and from 1-5 by weight of an alkali metal salt of pentachlorphenol.
ethanol, iso-propanol and iso- References Cited in the file of this patent UNITED STATES PATENTS Haertel July 4, 1911 Flemming Nov. 30, 1915 Moore Nov. 19, 1940 Badertscher July 14, 1942 Endress Aug. 17, 1943 Ballman May 22, 1945 Dierick May 30, 1950 Gates Sept. 11, 1951 Hammer Dec. 18, 1951 Benignus Mar. 4, 1952 FOREIGN PATENTS Great Britain Ian. 8, 1935
Claims (1)
1. A DISINFECTANT COMPOSITION COMPRISING AN AQUEOUS SOLUTION CONTAINING FROM 1-6% BY WEIGHT OF A FIRST PHENOLIC COMPOUND SELECTED FROM THE GROUP CONSISTING OF P-CHLOR-M-CRESOL AND ITS ALKALI METAL AND AMMONIUM SALTS, FROM 0.5-10% OF A SECOND PHENOLIC COMPOUND SELECTED FROM THE GROUP CONSISTING OF O-PHENYL-PHENOL AND ITS ALKALI METAL AND AMMONIUM SALTS, FROM 0.5-5% OF A THIRD PHENOLIC COMPOUND SELECTED FROM THE GROUP CONSISTING OF O-BENZYL-P-CHLORPHENOL AND ITS ALKALI METAL AND AMMONIUM SALTS AND FROM 1-5% OF A FOURTH PHENOLIC COMPOUND SELECTED FROM THE GROUP CONSISTING OF PENTACHLORPHENOL AND ALKALI METAL AND AMMONIUM SALTS OF SAID FOURTH PHENOLIC COMPOUND.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3249/59A GB872900A (en) | 1959-01-29 | 1959-01-29 | Disinfectant compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3063895A true US3063895A (en) | 1962-11-13 |
Family
ID=9754769
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US4170A Expired - Lifetime US3063895A (en) | 1959-01-29 | 1960-01-25 | Disinfectant compositions |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3063895A (en) |
| FR (1) | FR337M (en) |
| GB (1) | GB872900A (en) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3200036A (en) * | 1962-08-17 | 1965-08-10 | Talb Ind Inc | Oiled dust cloth composition |
| US3375199A (en) * | 1963-11-29 | 1968-03-26 | Colgate Palmolive Co | Cleaner-disinfectant composition |
| US3538217A (en) * | 1969-04-02 | 1970-11-03 | Grace W R & Co | Phenolic germicidal compositions |
| US3933671A (en) * | 1974-02-27 | 1976-01-20 | The Procter & Gamble Company | Germicidal cleaning composition and method |
| US3987007A (en) * | 1974-10-18 | 1976-10-19 | Kalogris Theodore P | Antimicrobial resin compositions containing ortho-benzyl-para-chlorophenol |
| US4097395A (en) * | 1976-09-07 | 1978-06-27 | Chempro Corporation | Mold and mildew removal composition and method of manufacture |
| US4257907A (en) * | 1979-05-21 | 1981-03-24 | Monsanto Company | Disinfectant cleaning compositions |
| US4589994A (en) * | 1984-12-17 | 1986-05-20 | Moseman Roger E | Liquid foot treatment composition |
| US4632772A (en) * | 1982-02-22 | 1986-12-30 | Dexide, Inc. | Mild antimicrobial detergent composition |
| US4668419A (en) * | 1984-12-17 | 1987-05-26 | Moseman Roger E | Liquid foot treatment composition |
| WO1997017849A1 (en) * | 1995-11-13 | 1997-05-22 | The Trustees Of Columbia University Of The City Of New York | Triple antimicrobial composition |
| US6503952B2 (en) | 1995-11-13 | 2003-01-07 | The Trustees Of Columbia University In The City Of New York | Triple antimicrobial composition |
| WO2007009606A2 (en) * | 2005-07-19 | 2007-01-25 | Bayer Healthcare Ag | Disinfecting agent containing a combination of biocidal phenols and a keratolytic |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE28778E (en) * | 1969-12-23 | 1976-04-20 | West Laboratories, Inc. | Phenolic synthetic detergent-disinfectant |
| DE19859136A1 (en) | 1998-12-21 | 2000-06-29 | Pluss Stauffer Ag | Deep freezing formulation containing phenol and / or phenol derivatives |
Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US996759A (en) * | 1910-02-01 | 1911-07-04 | Firm Of F Hoffmann La Roche And Company | Disinfectant. |
| US1162152A (en) * | 1914-01-26 | 1915-11-30 | Paul Flemming | Disinfectant. |
| GB422219A (en) * | 1932-08-10 | 1935-01-08 | Lehn & Fink Inc | Improvements in or relating to germicidal preparations and methods of producing the same |
| US2222486A (en) * | 1937-06-09 | 1940-11-19 | American Cyanamid Co | Composition for combating insect pests |
| US2289476A (en) * | 1941-03-24 | 1942-07-14 | Mccormick And Company Inc | Disinfectant emulsion |
| US2326933A (en) * | 1938-03-02 | 1943-08-17 | Endres Gunther | Method of increasing the solubility of halogenated phenols in soap solutions |
| US2376650A (en) * | 1941-12-26 | 1945-05-22 | Dow Chemical Co | Fungicidal and bactericidal compositions |
| US2509764A (en) * | 1946-02-20 | 1950-05-30 | Shell Dev | Insecticide composition |
| US2567200A (en) * | 1949-01-10 | 1951-09-11 | Gates Marshall | Insect repellent |
| US2579430A (en) * | 1949-06-11 | 1951-12-18 | Dow Chemical Co | Dormant parasiticide compositions |
| US2588318A (en) * | 1949-02-07 | 1952-03-04 | Monsanto Chemicals | Water emulsifiable soil-poison concentrate |
-
1959
- 1959-01-29 GB GB3249/59A patent/GB872900A/en not_active Expired
-
1960
- 1960-01-25 US US4170A patent/US3063895A/en not_active Expired - Lifetime
- 1960-08-24 FR FR836659A patent/FR337M/en active Active
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US996759A (en) * | 1910-02-01 | 1911-07-04 | Firm Of F Hoffmann La Roche And Company | Disinfectant. |
| US1162152A (en) * | 1914-01-26 | 1915-11-30 | Paul Flemming | Disinfectant. |
| GB422219A (en) * | 1932-08-10 | 1935-01-08 | Lehn & Fink Inc | Improvements in or relating to germicidal preparations and methods of producing the same |
| US2222486A (en) * | 1937-06-09 | 1940-11-19 | American Cyanamid Co | Composition for combating insect pests |
| US2326933A (en) * | 1938-03-02 | 1943-08-17 | Endres Gunther | Method of increasing the solubility of halogenated phenols in soap solutions |
| US2289476A (en) * | 1941-03-24 | 1942-07-14 | Mccormick And Company Inc | Disinfectant emulsion |
| US2376650A (en) * | 1941-12-26 | 1945-05-22 | Dow Chemical Co | Fungicidal and bactericidal compositions |
| US2509764A (en) * | 1946-02-20 | 1950-05-30 | Shell Dev | Insecticide composition |
| US2567200A (en) * | 1949-01-10 | 1951-09-11 | Gates Marshall | Insect repellent |
| US2588318A (en) * | 1949-02-07 | 1952-03-04 | Monsanto Chemicals | Water emulsifiable soil-poison concentrate |
| US2579430A (en) * | 1949-06-11 | 1951-12-18 | Dow Chemical Co | Dormant parasiticide compositions |
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3200036A (en) * | 1962-08-17 | 1965-08-10 | Talb Ind Inc | Oiled dust cloth composition |
| US3375199A (en) * | 1963-11-29 | 1968-03-26 | Colgate Palmolive Co | Cleaner-disinfectant composition |
| US3538217A (en) * | 1969-04-02 | 1970-11-03 | Grace W R & Co | Phenolic germicidal compositions |
| US3933671A (en) * | 1974-02-27 | 1976-01-20 | The Procter & Gamble Company | Germicidal cleaning composition and method |
| US3987007A (en) * | 1974-10-18 | 1976-10-19 | Kalogris Theodore P | Antimicrobial resin compositions containing ortho-benzyl-para-chlorophenol |
| US4097395A (en) * | 1976-09-07 | 1978-06-27 | Chempro Corporation | Mold and mildew removal composition and method of manufacture |
| US4257907A (en) * | 1979-05-21 | 1981-03-24 | Monsanto Company | Disinfectant cleaning compositions |
| US4632772A (en) * | 1982-02-22 | 1986-12-30 | Dexide, Inc. | Mild antimicrobial detergent composition |
| 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 |
| WO1997017849A1 (en) * | 1995-11-13 | 1997-05-22 | The Trustees Of Columbia University Of The City Of New York | Triple antimicrobial composition |
| US5705532A (en) * | 1995-11-13 | 1998-01-06 | The Trustees Of Columbia University Of The City Of New York | Triple antimicrobial composition |
| US5985931A (en) * | 1995-11-13 | 1999-11-16 | The Trustees Of Columbia University In The City Of New York | Triple antimicrobial composition |
| US6503952B2 (en) | 1995-11-13 | 2003-01-07 | The Trustees Of Columbia University In The City Of New York | Triple antimicrobial composition |
| WO2007009606A2 (en) * | 2005-07-19 | 2007-01-25 | Bayer Healthcare Ag | Disinfecting agent containing a combination of biocidal phenols and a keratolytic |
| WO2007009606A3 (en) * | 2005-07-19 | 2007-05-24 | Bayer Healthcare Ag | Disinfecting agent containing a combination of biocidal phenols and a keratolytic |
| US20080221222A1 (en) * | 2005-07-19 | 2008-09-11 | Bayer Healthcare Llc | Disinfectant |
| CN101267734B (en) * | 2005-07-19 | 2012-05-30 | 拜耳动物保健有限责任公司 | Disinfecting agent containing a combination of biocidal phenols and a keratolytic |
Also Published As
| Publication number | Publication date |
|---|---|
| FR337M (en) | 1961-03-27 |
| GB872900A (en) | 1961-07-12 |
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