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
- Authority
- US
- 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
Links
- 239000000203 mixture Substances 0.000 title claims description 48
- 239000000645 desinfectant Substances 0.000 title claims description 13
- 229910052783 alkali metal Inorganic materials 0.000 claims description 18
- 150000002989 phenols Chemical class 0.000 claims description 17
- 150000001340 alkali metals Chemical class 0.000 claims description 14
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 claims description 12
- 150000003863 ammonium salts Chemical class 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 235000010292 orthophenyl phenol Nutrition 0.000 claims description 6
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 claims description 5
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 claims description 4
- -1 ammonium ions Chemical class 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 239000012895 dilution Substances 0.000 description 5
- 238000010790 dilution Methods 0.000 description 5
- 230000002070 germicidal effect Effects 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- NCKMMSIFQUPKCK-UHFFFAOYSA-N 2-benzyl-4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1CC1=CC=CC=C1 NCKMMSIFQUPKCK-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229960004592 isopropanol Drugs 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- LYOFHYLVYHTGBK-UHFFFAOYSA-N 4-chloro-1,5-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=C(Cl)C=CC(C)(O)C1 LYOFHYLVYHTGBK-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 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 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- KSQXVLVXUFHGJQ-UHFFFAOYSA-M Sodium ortho-phenylphenate Chemical compound [Na+].[O-]C1=CC=CC=C1C1=CC=CC=C1 KSQXVLVXUFHGJQ-UHFFFAOYSA-M 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000011280 coal tar Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000008233 hard water Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000000944 linseed oil Substances 0.000 description 2
- 235000021388 linseed oil Nutrition 0.000 description 2
- 210000004400 mucous membrane Anatomy 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000005416 organic matter Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- HCJLVWUMMKIQIM-UHFFFAOYSA-N sodium;2,3,4,5,6-pentachlorophenol Chemical compound [Na+].OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl HCJLVWUMMKIQIM-UHFFFAOYSA-N 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 1
- 241000588767 Proteus vulgaris Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000193996 Streptococcus pyogenes Species 0.000 description 1
- 241000224527 Trichomonas vaginalis Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 210000004666 bacterial spore Anatomy 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229940007042 proteus vulgaris Drugs 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 235000020183 skimmed milk Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 235000010294 sodium orthophenyl phenol Nutrition 0.000 description 1
- 210000004215 spore Anatomy 0.000 description 1
- 230000003330 sporicidal effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 229940076156 streptococcus pyogenes Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 239000002641 tar oil Substances 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 208000010484 vulvovaginitis Diseases 0.000 description 1
Classifications
-
- 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.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
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 (fr) |
| FR (1) | FR337M (fr) |
| GB (1) | GB872900A (fr) |
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 (fr) * | 1995-11-13 | 1997-05-22 | The Trustees Of Columbia University Of The City Of New York | Triple composition antimicrobienne |
| US6503952B2 (en) | 1995-11-13 | 2003-01-07 | The Trustees Of Columbia University In The City Of New York | Triple antimicrobial composition |
| WO2007009606A3 (fr) * | 2005-07-19 | 2007-05-24 | Bayer Healthcare Ag | Agent desinfectant |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE28778E (en) * | 1969-12-23 | 1976-04-20 | West Laboratories, Inc. | Phenolic synthetic detergent-disinfectant |
| DE19859136A1 (de) * | 1998-12-21 | 2000-06-29 | Pluss Stauffer Ag | Phenol und/oder Phenolderivate enthaltende Formulierung mit tiefem Gefrierpunkt |
| RU2410121C2 (ru) * | 2008-10-06 | 2011-01-27 | Федеральное Государственное Учреждение 33 Центральный Научно-Исследовательский Институт Мо Рф | Хлорактивное средство и способ его получения на основе n, n-дихлорарилсульфамидов |
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/fr 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 (17)
| 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 (fr) * | 1995-11-13 | 1997-05-22 | The Trustees Of Columbia University Of The City Of New York | Triple composition antimicrobienne |
| 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 |
| WO2007009606A3 (fr) * | 2005-07-19 | 2007-05-24 | Bayer Healthcare Ag | Agent desinfectant |
| US20080221222A1 (en) * | 2005-07-19 | 2008-09-11 | Bayer Healthcare Llc | Disinfectant |
| CN101267734B (zh) * | 2005-07-19 | 2012-05-30 | 拜耳动物保健有限责任公司 | 包含杀生物酚和角质分离剂的组合的消毒剂 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB872900A (en) | 1961-07-12 |
| FR337M (fr) | 1961-03-27 |
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