US2246524A - Germicide - Google Patents
Germicide Download PDFInfo
- Publication number
- US2246524A US2246524A US224116A US22411638A US2246524A US 2246524 A US2246524 A US 2246524A US 224116 A US224116 A US 224116A US 22411638 A US22411638 A US 22411638A US 2246524 A US2246524 A US 2246524A
- Authority
- US
- United States
- Prior art keywords
- solutions
- compounds
- alkyl
- alkylene polyamines
- ethylene diamine
- 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
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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
Definitions
- the present invention relates to agents for the control of micro-organisms, that is, germicides, antiseptics, bactericides, etc., and to compositions containing such agents.
- the invention relates particularly to a class of N-alkylated alkylene polyamines and their salts which have been found to be eminently suitable for such purposes.
- germicide is to be understood to have a broad significance and to include such terms as antiseptics, bactericides, disinfectants, preservatives, etc., which are commonly employed to designate agents for the control of bacteria.
- a wide variety of. germicides are in common use today. These materials can for the most part be classified into three groups, viz., phenols and substituted phenols, halogens and halogen-engendering compounds, and mercury and heavy metal compounds.
- the germicides of the present invention belong to none of these groups, and lack many of the objectionable characteristics of each of the groups.
- the phenolic germicides in general have a destructive or caustic action on tissue which makes it impossible to keep them in contact with tissue at any great concentration for long periods of time. Furthermore, phenols in general have a low solubility in water.
- phenols are used in emulsified form with soaps or the like, for example, in disinfectants of the lysol" .type.
- the halogens of which iodine, chlorine, and compounds which liberate chlorine are the outstanding examples, also have a caustic action on tissue Iodine is not water-soluble and solvents such as alcohol or aqueous potassium iodide solutions must be used to prepare compositions of germicidal efiectiveness.
- the mercury and heavy metal compounds have uniformly high germicidal power toward a are, in general, expensive, and although they have a high specificity towardparticular organisms they have only a limited range of usefulness in controlling certain other specific organisms.
- mercurial germicides often exhibit bacteriostatic action, that is, they prevent growth of micro-organisms but do not destroy them completely. In the presence of serum many germicidal materials, especially oxidizing agents, are rendered ineffective.
- N-alkylated alkylene polyamines and their salts with acids are remarkably effective germicides which are characterized by a wide range of usefulness for a wide variety of micro-organisms.
- These N-alkylated alkylene polyamines are substantially free from objectionable odor and have no substantial corrosive or caustic action on tissue when used in dilute solution. Many of the products are soluble in water and such solutions have exceptionally low surface tensions. In the presence of serum, these germicidal materials exhibit a loss of germicidal power but this reduction of effectiveness is only of the order of 50%.
- These N-alkylated alkylene polyamines are non-staining and have detergent properties which together with their lack of caustic action on tissue make them eminently suitable for washing textiles, rubber goods, walls and floors and especially for washing hands and skin.
- the compounds for use according to the present invention consist of N-alkylated alkylene polyamines and their salts with acids. Dodecyl diethylene triamine,
- the compounds which are suitable are alkylene polyamines substituted in one or more of the amino groups by one or more alkyl groups containing 8 or more carbon atoms and salts of these amines with acids. Best effects are obtained, however, when the alkylene polyamine contains only one long-chain substituent in one amino nitrogen atom, and the amino nitrogen atom in which the alkyl group is substituted is a terminal nitrogen atom.
- the most active agents of the class are those containing from 8 to 18 carbon atoms, inclusive, in the alkyl group.
- alkylene polyamines which are suitable for alkylation to obtain useful agents according to the invention are those having not more than 6 nitrogen atoms per molecule which may be obtained'by the reaction of ammonia with dihalogenated ethane or propane having the halogens on different carbon atoms, that is, having not more than one halogen on any single carbon atom.
- alkylene polyamines include ethylene diamine and propylene diamine, diethylene triamine, triethylene tetramines, dipropylene triamines, and the like. Only those polyalkylene polyamines having not more than one amino group attached to any single carbon atom are preferred. Such alkylene polyamines may also be obtained by other known methods of synthesis.
- the compounds may be more complex than those represented, for example, they may be a complex amine such as mine.
- Propylene diamine NH2-C Hr-GH (N Hid-CH a Since the nomenclature of the alkylene polyamines having more than two nitrogen atoms is rather complex, I have, as in the above list, grouped together all thevarious isomeric compounds as dipropylene triamines, tripropylene tetramines, etc. and refer-to them throughout this specification in that manner.
- the alkylated alkylene polyamine base be soluble in water, however, since the compounds may be used in the form of emulsions. Either the free amine or its salts with acids may be used. The salts are in general more soluble than the free amines.
- the compound N,N'-didodecyl ethylene diamine is not soluble in water to the extent of 1 part in 20,000 parts of water. However, N,N'-didodecyl ethylamine diamine that is emulsified in water containing alcohol gives a composition of effective germicidal strength as is indicated in the results which are giverij-inthe table hereinafter. a
- Triethylene tetramine or tripropylene tetramine derivatives in which one of the nitroproducts of alkylene polyby a decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl or octadecyl radical.
- nitrogen atom substituted by an alkyl group is to be understood tomean that one of the hydrogens attached to the nitrogen atom is replaced by an alkyl group, according to the common use of the term substitution" as applied to aromatic or acyclic compounds.
- N-octyl ethylene diamine N -2-ethylhexyl ethylene diamine
- N-decyl ethylene diamine N-tetradecyl ethylene diamine
- N,N'-didodecyl ethylene diamine N-dodecyl diethylene triamine
- N-tetradecyl diethylene triamine N-hexadecyl triethylene tetramine
- N-octyl trimethylene diamine etc.
- Mixtures of such compounds consisting either of compounds derived from the same alkylene polyamine with different alkyl substituents, such as would result on treating ethylene diamine with mixed alkyl dichlorides, or mixtures of varying degrees of alkylatlon or mixtures containing compounds derived from difierent alkylene polyamines with the same or difierent or mixed alkyl substituents are also contemplated for use herein.
- a preferred mixture consists of that resulting from alkylation of ethylene diamine, diethylene triamine, or triethylene triamine with alkyl halides having from 10 to 14 carbon atoms, which may be obtained by reacting with thionyl chloride the alcohol fraction resulting from the hydrogenation of cocoanut fatty acids.
- a preferred may be obtained by treating long-chain alcohols with an agent such as thionyl chloride.
- Lauryl (dodecyl) chloride for example, can be obtained by treating with thionyl chloride the lauryl alcohol fraction derived from the hydrogenation of cocoanut fatty acids.
- Mixtures of alcohols containing alcohols having from 10 to 16 carbon atoms consisting predominantly of even-numbered carbon-atom alcohols may be used for obtaining corresponding mixed alkyl chlorides and alkylatecl alkylene polyamines. These mixed alkylated alkylene polyamines are for some purposes as suitable for use in the invention as the compounds derived from a single isomer or homologue.
- alkyl chlorides methods, for example, of alcohols with dry chloride as a catalyst.
- the alkylene polyamine is alkylated by heating with the alkyl chloride even without pressure;
- the reaction mixture on cooling, separates into two layers; The upper layer contains the desired reaction product and is distilled under vacuum to separate the unreacted triethylene tetramine.
- the resulting hexadecyl triethylene tetramine was purified by distillation under vacuum. Its boiling point is approximately 230 to 250 C. at a pressure of 2 to 3 mm. and is a viscous oil which dissolves in water with a most persistent foam.
- N-alkylated alkylene polyamines may be prepared from corresponding alkylene polyamines and alkyl chlo- Y rides.
- the boiling points of several of these substantially pure N-alkylated alkylene polyamines prepared in this manner are as follows:
- the effectiveness of the germicides of this invention is shown by the phenol coefficients of N-Z-ethylhexyl ethylene diamine 108-110 C./12 N-n-decyl ethylene diamine 140-145 C./ 9 N-n-tetradec'yl ethylene dii a amine l87-l91 C./ 9 N,N-di-(n-buty1) ethylene diamine 110-115 C./15 N-n-dodecyl diethylene triamine 204-206 C./ 8
- alkylated alkylene polyamine was added to water to make a 0.1% solution (1 gram per liter ofwater) and sufllcient hydrochloric acid was added to make a clear solution and to attain the desired pH value.
- sufllcient hydrochloric acid was added to make a clear solution and to attain the desired pH value.
- the pH did not change substantially on dilution but changes of pH did occur when the solutions were added to the different culture media.
- the polyamines were present as hydrochlorides in the solution except in those cases which are indicated where- .which occur on adding in the free base was used or the acetic acid saltwas used instead of the hydrochloric acid salt.
- the phenol coeflicients were as follows:
- N-n-octyl ethylene diamine hydrochloride N-n-dodecyl ethylene diamine hydrochloride N-n-tetradecyl ethylene diamine hydrochloride N-n-hexadccyl ethylene diamine hydrochloride 166 N-n-octsdecyl ethylen iamine diacetate '4. 4 77 66 N-n-dodecyl diethylene triamine base 9. 7 100 50 N-n-dodecyl diethylene triamine 82 ig hydrochloride 5 78 40 N-n-tetradecyl diethylene triamine hydrochloride. 1 4.
- solutions having an acidity greater or less than this can be used but, in either case, correspondingly larger proportions of the alklated alkylene polyamine constituent will be'required to attain the same phenol coefliciento
- Substantially neutral or slightly alkaline dilute solutions of the alkylated alkylene polyamines have substantially no irritating effect on the skin or mucous membranes. They are somewhat astringent in action, however, and have a bitter taste anda soapy feel.
- salts for instance, nitrates, sulfates, alkyl sulfates, phosphates, or salts with organic acids, for-instancaformates, lactates, tartrates, citrates, benzene or toluene suli'onates, benzoates, salicylates, etc.
- organic acids for-instancaformates, lactates, tartrates, citrates, benzene or toluene suli'onates, benzoates, salicylates, etc.
- water-soluble alkylated alkylene polyamines in which the alkyl radical contains 8 to 18 carbon atoms or mixtures of these are used because of their water solubility.
- compositions may be prepared by the use of a wide variety of other solvents.
- the alkylated alkylene polyamines are soluble in alcohols such as ethyl alcohol and isoamyl alcohol; hydrocarbons such xylene, mineral oil, and kerosene; vegetable and as benzene,
- An agent for the control of bacteria which comprises a compound selected from the group consisting of N-alkylated alkylene polyamines and salts thereof with acids, said N-alkylated alkylene polyamines corresponding to the general formula animal oils such as cottonseed oil and linseed oil; 0
- the alkylated alkylene polyamines have proved suitable for the most various preserving and disinfecting purposes.
- they may be employed for the disinfection of all kinds of table utensils, surgical instruments, etc.
- They are further advantageously used for disinfecting purposes in medical practice, for instance, for articles used in dressing woun'ols, for rubber goods, for disinfecting laundry and for the scrubbing of hands; furthermore. for cosmetics, for instance, face powder, hand lotions and media for hyperidrosis.
- Floors and walls may likewise be disinfected.
- Dilute solutions may be used for irrigation of body cavities, bladder lavages, urethral irrigations and vaginal douches. Foodstuils such as fruits, vegetables, meat, etc.
- germicides may be preserved or disinfected by these germicides, which are easily washed therefrom. They are also further suitable for preservation of animal materials such as skins, blood, glands and other organs, etc. In some instances a germicidal composition which leaves a stain to indicate its presence on tissue, etc. is desirable and this result may be obtained by tinting solutions of the alkylated allwlene polyamines by means of known dyestufis.
- My new disinfecting media ma'y be diluted with hard water without diminution of their activity or precipitation of insoluble salts.
- Solutions of the compounds in water have a penetrating action as a result of their low surface tension.
- Water at C. has a surface tension of about 72.8 dynes per centimeter.
- Solutions of the alkylated alkylene polyamines in the table hereinbelow have the surface tensions at the concentrations indicated at 25 C.
- R is an alkylene radical selected from the group consisting of ethylene, propylene and trimethylene radicals, 11! is a number from 0 to 4
- X and Y are selected from the group consisting of hydrogen and alkyl radicals at least an alkyl radical having not less than 12 and not more than 16 carbon atoms.
- An agent for the control of bacteria which comprises a compound selected from the group consisting of alkylene polyamines and salts thereof with acids, said allwlene polyamines having more than 2 and less than 6 amino radicals per molecule, the different amino radicals of which are separated from one another by an the group conalkyl radical having not less than 12 and not more than 16 carbon atoms.
- An agent for the control of bacteria which comprises a compound selected from the group consisting of alkylated diethylene triamines and salts thereof with acids in which the alkylation has been effected at a terminal nitrogen atom with an alkyl radical containing not less than 12 and not more than 16 carbon atoms, said agent being characterized by an improved resistance to loss of activity in the presence of organic matter.
- An agent for the comprises a compound selected from the group consisting of N-dodecyl diethylene triamine and salts thereof with acids, in which the dodecyl radical is attached to a terminal nitrogen atom.
- An agent for the control of bacteria which comprises a compound selected from the group consisting of N-tetradecyl diethylene triamine and salts thereof with acids, in which the tetradecyl radical is attached to a terminal nitrogen atom.
- An agent for the control of bacteria which comprises a compound selected from the group consisting of N-hexadecyl triethylene tetramine and salts thereof with acids, in which the heaxadecyl radical is attached to a terminal nitrogen atom.
- An agent for the control of bacteria which comprises N-dodecyl diethylene triamine, in
- An agent for the control of bacteria which 7 comprises N-tetradecyl diethylene triamine, in which the tetradecyl radical is attached to a terminal nitrogen atom.
- An agent for the control of bacteria which comprises N-hexadecyl trlethylene tetramine, in which the hexadecyl radical is attached to a terminal nitrogen atom.
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)
Description
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US224116A US2246524A (en) | 1938-08-10 | 1938-08-10 | Germicide |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US224116A US2246524A (en) | 1938-08-10 | 1938-08-10 | Germicide |
Publications (1)
Publication Number | Publication Date |
---|---|
US2246524A true US2246524A (en) | 1941-06-24 |
Family
ID=22839337
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US224116A Expired - Lifetime US2246524A (en) | 1938-08-10 | 1938-08-10 | Germicide |
Country Status (1)
Country | Link |
---|---|
US (1) | US2246524A (en) |
Cited By (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2623831A (en) * | 1948-11-23 | 1952-12-30 | Standard Oil Dev Co | Antistripping agents for asphalts |
US2684946A (en) * | 1948-10-01 | 1954-07-27 | Goldschmidt Ag Th | Washing and disinfecting composition |
US2716616A (en) * | 1949-05-23 | 1955-08-30 | Minnesota Mining & Mfg | Treated bituminous and aggregate compositions |
DE1034330B (en) * | 1955-01-31 | 1958-07-17 | Givaudan & Cie Sa | Germicide |
US2970939A (en) * | 1958-09-05 | 1961-02-07 | Fmc Corp | Control of nematodes employing nu-nitroso-nu, nu-dimethylamine |
US2979434A (en) * | 1953-12-07 | 1961-04-11 | Monsanto Chemicals | Polyamine nematocides |
US3004885A (en) * | 1956-10-16 | 1961-10-17 | Monsanto Chemicals | Salts of alkanethiols |
US3008993A (en) * | 1957-02-14 | 1961-11-14 | Monsanto Chemicals | Alkenyl polyamines |
US3024190A (en) * | 1958-10-03 | 1962-03-06 | Commercial Solvents Corp | Process for the control of bacteria in a flooding process for the recovery of petroleum oil |
US3069225A (en) * | 1960-01-27 | 1962-12-18 | Gen Mills Inc | Method of inhibiting corrosion |
US3083143A (en) * | 1957-07-13 | 1963-03-26 | Gaba Ag | Fluorides of organic bases as well as of amphoteric compounds, a method for their preparation, including the application of such new compounds in the caries prophylaxis, new dentifrices and mouth washes as well as a method for their preparation |
US3108036A (en) * | 1959-11-12 | 1963-10-22 | Fine Organics Inc | Germicidal compositions |
US3164552A (en) * | 1958-12-24 | 1965-01-05 | Nalco Chemical Co | Process for controlling the growth and reproduction of microorganisms |
US3231403A (en) * | 1962-05-17 | 1966-01-25 | Commercial Solvents Corp | Triamine stabilized adhesive compositions |
US3248245A (en) * | 1962-05-17 | 1966-04-26 | Commerical Solvents Corp | Diamine-stabilized adhesive compositions |
US3719458A (en) * | 1971-04-27 | 1973-03-06 | Texaco Inc | Fuel composition |
FR2211449A1 (en) * | 1972-12-20 | 1974-07-19 | Goldschmidt Ag Th | N-alkylated tripropylene-tetramine compsns - having bactericidal, fungicidal, algicidal and sporicidal activity |
US3949086A (en) * | 1965-05-11 | 1976-04-06 | Nalco Chemical Company | Antifungal or antibacterial composition and method |
US4089942A (en) * | 1976-01-29 | 1978-05-16 | L'oreal | Deodorant composition and process |
US4120979A (en) * | 1976-09-17 | 1978-10-17 | Th. Goldschmidt Ag | Alkylated polyamines, their preparation and use as microbiocides |
US4196217A (en) * | 1976-02-17 | 1980-04-01 | Laboratoires Pharmascience | Hydroxylated amines with bacteriostatic activity |
US4304590A (en) * | 1979-02-09 | 1981-12-08 | Ciba-Geigy Corporation | Methods and compositions for the control of harmful organisms containing aliphatic primary diamines |
DE3147990A1 (en) * | 1981-12-04 | 1983-06-16 | Henkel Kgaa | Use of N-alkyl-N'-polyhydroxyalkylalkylenediamines as antimicrobial active substances |
EP0212866A1 (en) * | 1985-07-29 | 1987-03-04 | Minnesota Mining And Manufacturing Company | Nonirritating teat dip |
US4650671A (en) * | 1981-07-17 | 1987-03-17 | Claus Riemann & Co. Aps | Antiperspirant kit and method for controlling perspiration |
US4719101A (en) * | 1986-11-28 | 1988-01-12 | Keith Morrison | Deodorant composition to protect against the development of body odor |
FR2602955A1 (en) * | 1986-08-19 | 1988-02-26 | Henkel France | Composition for cleaning and disinfecting milking equipment |
WO1990011015A1 (en) * | 1989-03-21 | 1990-10-04 | Hygienico Limited | Process for preparing bactericidal matrices |
US4967008A (en) * | 1990-01-12 | 1990-10-30 | Sherex Chemical Company, Inc. | Polyamines and their preparation |
US20050154065A1 (en) * | 2003-12-09 | 2005-07-14 | Alcon, Inc. | Use of bis-amines to enhance the antimicrobial activity of aqueous compositions |
-
1938
- 1938-08-10 US US224116A patent/US2246524A/en not_active Expired - Lifetime
Cited By (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2684946A (en) * | 1948-10-01 | 1954-07-27 | Goldschmidt Ag Th | Washing and disinfecting composition |
US2623831A (en) * | 1948-11-23 | 1952-12-30 | Standard Oil Dev Co | Antistripping agents for asphalts |
US2716616A (en) * | 1949-05-23 | 1955-08-30 | Minnesota Mining & Mfg | Treated bituminous and aggregate compositions |
US2979434A (en) * | 1953-12-07 | 1961-04-11 | Monsanto Chemicals | Polyamine nematocides |
DE1034330B (en) * | 1955-01-31 | 1958-07-17 | Givaudan & Cie Sa | Germicide |
US3004885A (en) * | 1956-10-16 | 1961-10-17 | Monsanto Chemicals | Salts of alkanethiols |
US3008993A (en) * | 1957-02-14 | 1961-11-14 | Monsanto Chemicals | Alkenyl polyamines |
US3083143A (en) * | 1957-07-13 | 1963-03-26 | Gaba Ag | Fluorides of organic bases as well as of amphoteric compounds, a method for their preparation, including the application of such new compounds in the caries prophylaxis, new dentifrices and mouth washes as well as a method for their preparation |
US2970939A (en) * | 1958-09-05 | 1961-02-07 | Fmc Corp | Control of nematodes employing nu-nitroso-nu, nu-dimethylamine |
US3024190A (en) * | 1958-10-03 | 1962-03-06 | Commercial Solvents Corp | Process for the control of bacteria in a flooding process for the recovery of petroleum oil |
US3164552A (en) * | 1958-12-24 | 1965-01-05 | Nalco Chemical Co | Process for controlling the growth and reproduction of microorganisms |
US3108036A (en) * | 1959-11-12 | 1963-10-22 | Fine Organics Inc | Germicidal compositions |
US3069225A (en) * | 1960-01-27 | 1962-12-18 | Gen Mills Inc | Method of inhibiting corrosion |
US3231403A (en) * | 1962-05-17 | 1966-01-25 | Commercial Solvents Corp | Triamine stabilized adhesive compositions |
US3248245A (en) * | 1962-05-17 | 1966-04-26 | Commerical Solvents Corp | Diamine-stabilized adhesive compositions |
US3949086A (en) * | 1965-05-11 | 1976-04-06 | Nalco Chemical Company | Antifungal or antibacterial composition and method |
US3719458A (en) * | 1971-04-27 | 1973-03-06 | Texaco Inc | Fuel composition |
FR2211449A1 (en) * | 1972-12-20 | 1974-07-19 | Goldschmidt Ag Th | N-alkylated tripropylene-tetramine compsns - having bactericidal, fungicidal, algicidal and sporicidal activity |
US4089942A (en) * | 1976-01-29 | 1978-05-16 | L'oreal | Deodorant composition and process |
US4196217A (en) * | 1976-02-17 | 1980-04-01 | Laboratoires Pharmascience | Hydroxylated amines with bacteriostatic activity |
US4120979A (en) * | 1976-09-17 | 1978-10-17 | Th. Goldschmidt Ag | Alkylated polyamines, their preparation and use as microbiocides |
US4304590A (en) * | 1979-02-09 | 1981-12-08 | Ciba-Geigy Corporation | Methods and compositions for the control of harmful organisms containing aliphatic primary diamines |
US4650671A (en) * | 1981-07-17 | 1987-03-17 | Claus Riemann & Co. Aps | Antiperspirant kit and method for controlling perspiration |
DE3147990A1 (en) * | 1981-12-04 | 1983-06-16 | Henkel Kgaa | Use of N-alkyl-N'-polyhydroxyalkylalkylenediamines as antimicrobial active substances |
EP0212866A1 (en) * | 1985-07-29 | 1987-03-04 | Minnesota Mining And Manufacturing Company | Nonirritating teat dip |
FR2602955A1 (en) * | 1986-08-19 | 1988-02-26 | Henkel France | Composition for cleaning and disinfecting milking equipment |
US4719101A (en) * | 1986-11-28 | 1988-01-12 | Keith Morrison | Deodorant composition to protect against the development of body odor |
WO1990011015A1 (en) * | 1989-03-21 | 1990-10-04 | Hygienico Limited | Process for preparing bactericidal matrices |
US4967008A (en) * | 1990-01-12 | 1990-10-30 | Sherex Chemical Company, Inc. | Polyamines and their preparation |
US20050154065A1 (en) * | 2003-12-09 | 2005-07-14 | Alcon, Inc. | Use of bis-amines to enhance the antimicrobial activity of aqueous compositions |
US7445771B2 (en) * | 2003-12-09 | 2008-11-04 | Alcon, Inc. | Use of bis-amines to enhance the antimicrobial activity of aqueous compositions |
US20090030085A1 (en) * | 2003-12-09 | 2009-01-29 | Alcon, Inc. | Use of bis-amines to enhance the antimicrobial activity of aqueous compositions |
AU2004297269B2 (en) * | 2003-12-09 | 2010-11-18 | Alcon Inc. | Use of bis-amines to enhance the antimicrobial activity of aqueous compositions |
US7871602B2 (en) | 2003-12-09 | 2011-01-18 | Alcon, Inc. | Use of bis-amines to enhance the antimicrobial activity of aqueous compositions |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US2246524A (en) | Germicide | |
US2295504A (en) | Cetyl quaternary ammonium compound | |
US2108765A (en) | Preserving and disinfecting media | |
US3539520A (en) | Compositions comprising quaternary ammonium germicides and nonionic surfactants | |
US3041236A (en) | Germicides containing trifluoromethyl halogenated salicylanilides | |
US3256200A (en) | Anti-bacterial detergent composition | |
EP0651048A2 (en) | Foaming antibacterial liquid formulation for cleaning kitchen surfaces | |
US3592932A (en) | N-2-ethylhexyl-n'-aryl ureas as antibacterial agents | |
US3697220A (en) | Bacteria growth inhibiting textiles and dry cleaning and disinfecting compositions and processes | |
US3755448A (en) | N-(pentachlorobiphenyl)-diethylene triamine | |
US3646199A (en) | Salicyclic acid o-hydroxyphenylamides for combating bacteria and fungi | |
US3435039A (en) | Quaternary ammonium salts of alcohol ether sulfates | |
US3932655A (en) | Surgical skin scrub | |
US2304830A (en) | Amides of heterocyclic carboxylic acids | |
US2666009A (en) | Quaternary ammonium germicide compositions | |
US2406902A (en) | Soap-like preparations | |
US2918402A (en) | Bactericidal-fungicidal compositions | |
US3369046A (en) | 2-hydroxy-alkyl-benzyl quaternary ammonium compounds | |
US3565927A (en) | Quaternary ammonium compounds having a branched chain aliphatic acid anion | |
US4607036A (en) | Preservative compositions employing anti-microbial morpholine derivatives | |
US3493660A (en) | Bactericidal quaternary ammonium compositions | |
JPH08770B2 (en) | Ophthalmic composition | |
US3813350A (en) | Mildness additive | |
US3280137A (en) | Quaternary ammonium menaphthyl saccharinates | |
US3485919A (en) | Antibacterial composition |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: GREEN MOUNTAIN CAPITAL, L.P., VERMONT Free format text: SECURITY INTEREST;ASSIGNOR:NORTHERN ELASTOMERIC, INC., (A NEW HAMPSHIRE CORPORATION);REEL/FRAME:010052/0410 Effective date: 19990621 Owner name: SOPER, TAYLOR, NEW HAMPSHIRE Free format text: SECURITY INTEREST;ASSIGNOR:NORTHERN ELASTOMERIC, INC., (A NEW HAMPSHIRE CORPORATION);REEL/FRAME:010052/0410 Effective date: 19990621 Owner name: THALHEIMER, WILLIAM, NEW HAMPSHIRE Free format text: SECURITY INTEREST;ASSIGNOR:NORTHERN ELASTOMERIC, INC., (A NEW HAMPSHIRE CORPORATION);REEL/FRAME:010052/0410 Effective date: 19990621 |
|
AS | Assignment |
Owner name: NORTHEN ELASTOMERIC, INC., NH CORPORATION, NEW HAM Free format text: TERMINATION OF SECURITY AGREEMENT;ASSIGNORS:GREEN MOUNTAIN CAPITAL, L.P. (VT LIMITED PARTNERSHIP);THALHEIMER, WILLIAM;SOPER, TAYLOR;REEL/FRAME:010909/0476 Effective date: 20000330 |