US2108765A - Preserving and disinfecting media - Google Patents

Preserving and disinfecting media Download PDF

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US2108765A
US2108765A US2108765DA US2108765A US 2108765 A US2108765 A US 2108765A US 2108765D A US2108765D A US 2108765DA US 2108765 A US2108765 A US 2108765A
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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
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/12—Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/62—Quaternary ammonium compounds
    • C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/69—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to carbon-to-carbon double or triple bonds

Definitions

  • This invention relates to preserving and disinfecting media.
  • quaternary ammonium compounds display considerable bactericidal and fungicidal properties if they contain at least one higher molecular aliphatically bound hydrocarbon radical as substituent of the nitrogen atom. Such quaternary ammonium compounds, therefore, may be used as disinfecting and preserving agents as such or in admixture with each other or with other active or inert ingredients.
  • the higher molecular aliphatically bound hydrocarbon radical referred to above contains eight or more carbon atoms and may contain further substituents, such as halogen atoms, hydroxyl, alkoxy and amino group, and it may be interrupted by other atoms, for instance, by ether-like bound oxygenor sulfur atoms or by amino groups.
  • quaternary ammonium compounds may be mentioned by wayof example as being suitable as preserving and disinfecting! media:
  • salts mentioned above for instance, the nitrates, sulfates, alkyi sulfates, phosphates, or the salts with organic acids, for instance, the formiates, acetates, lactates, tartrates, citrates, benzene or toluene sulfonates, benzoates, salicylates, etc. may be em- In Switzerland April 13, 1933 ployed.
  • those quaternary ammonium compounds in which the higher molecular aliphatic hydrocarbon radical contains from 8 to 18 carbon atoms are used for preserving and disinfecting purposes.
  • they contain as a further substituent an aliphatically bound phenyl group.
  • the a dodecyloxy 3 hydroxypropyl diethylbenzyl-ammoniumchloride in the concentration 1:50000 kills colibacteria within 10 minutes, staphyloccoci within 15 minutes, dodecyl-diethylbenzyl-ammoniumchloride kills in the same concentration colibacteria after 10 minutes, staphyloccoci after 2 minutes.
  • the quaternary ammonium compounds specified are in part crystalline, in part liquid substances.
  • the salts of the quaternary ammoni- -um bases may be dissolved in water to stable solutions. Since the said quaternary ammonium compounds are practically odorless and relatively non-toxic for man they have proved suitable for the most various preserving and disinfecting purposes. For instance, they may be employed for the disinfection of all kinds of table utensils, storage utensils. They are further advantageously used for disinfecting purposes in the medical practice, for instance, for disinfecting medical instruments, all articles used in dressing wounds, for disinfecting laundry, furthermore, for cosmetics, for instance, face powder, or media for hyperidrosis. disinfected by means of the said quaternary ammonium compounds.
  • foodstuffs such as fruits, vegetables, meat, etc. may be preserved or disinfected by the quaternary ammonium compounds specified. They are further suitable for the preservation, that is exclusion of bacterial and autolytic decomposition processes of animal material, such as skins, blood, glands and other organs, etc.
  • My new disinfecting media may also be used in dilution with hard water without diminution of their activity. In the concentration necessary for disinfection they do not injure the skin and therefore may also be used for the disinfection of the skin, particularly the hands.
  • the quaternary ammonium compounds specified may be used in substance as well as in so- Floors and walls may likewise be lution or emulsion or in admixture with each other and/or with other activev or inert substances, such as powders, ointment bases, creams, etc.
  • Advantageously such mixture of quaternary ammonium compounds may be used which contains at the nitrogen atom the higher molecular aliphatic hydrocarbon radicals derived from the components of the fatty acid mixtures as obtained from their natural initial material, such .asfats or resins, for instance, palm oil, coconut oil, colophony, and the like.
  • a preserving and disinfecting medium comprising as an active preserving and disinfecting ingredient a non-acylated quaternary ammonium compound at least once substituted by a higher molecular aliphatic radical selected from the group consisting of higher alkyl, hydroxyalkyl, halogenalkyl, alkoxyalkyl, alkylmercaptoalkyl, aminoalkyl and alkylaminoalkyl radicals.
  • a preserving and disinfecting medium comprising as an active preserving and disinfecting ingredient a non-acylated quaternary ammonium compound at least once substituted by a higher molecular aliphatic radical selected from the group consisting of higher alkyl, hydroxyalkyl, haiogenalkyl, alkoxyalkyl, alkylmercaptoalkyl, aminoalkyl and alkylaminoalkyl radicals and further substituted by an aliphatically bound phenyl radical.
  • a preserving and disinfecting medium comprising as an active preserving and disinfecting ingredient a non-acylated quaternary ammonium compound at least once substituted by a higher molecular aliphatic radical containing 8 to 18 carbon atoms, which radical is selected from the group consisting of higher alkyl, hydroxyalkyl, halogenalkyl, alkoxyalkyl, alkylmercaptoalkyl, aminoalkyl and alkylaminoalkyl radicals.
  • a preserving and disinfecting medium comprising as an active preserving and disinfecting ingredient a non-acylated quaternary ammonium compound at least once substituted by a higher molecular aliphatic radical containing 8 to 18 carbon atoms, which radical is selected from the group consisting of higher alkyl, hydroxyalkyl, halogenalkyl, alkoxyalkyl, alkylmercaptoalkyl, aminoalkyl and alkylaminoalkyl radicals and further substituted by an aliphatically bound phenyl radical.
  • a preserving and disinfecting medium comprising as an active preserving and disinfecting ingredient a quaternary ammonium compound substituted by two lower alkyl groups, an aliphatically bound phenyl group and a higher molecular aliphatic radical selected from the group consisting of higher alkyl, hydroxyalkyl, halogenalkyl, alkoxyalkyl, alkylmercaptoalkyl, aminoalkyl and alkylaminoalkyl radicals.
  • a preserving and disinfecting medium comprising as an active preserving and disinfecting ingredient a quaternaryammonium compound substituted by two lower alkyl groups, an allphatically bound phenyl group and a higher molecular aliphatic radical containing 8 to 18 car-- bon atoms, which radical is selected from the group consisting of higher alkyl, hydroxyalkyl, halogenalkyl', alkoxyalkyl, alkylmercaptoalkyl, aminoalkyl and alkylaminoalkyl radicals.
  • a preserving and disinfecting medium comprising as an active preserving and disinfecting ingredient a quaternary ammonium compound substituted by two lower alkyl groups, an aliphatically bound phenyl group and a higher molecular aliphatic radical selected from the group consisting of higher alkyl, hydroxyalkyl, halogenalkyl, alkoxyalkyl, alkylmercaptoalkyl, aminoalkyl and alkylaminoalkyl radicals, which compound is in the form of a mineral acid salt.
  • a preserving and disinfecting medium comprising as an active preserving and disinfecting ingredient a quaternary ammonium halide substituted by two lower alkyl groups, one benzyl group and a higher molecular aliphatic radical selected from the group consisting of higher alkyl, hydroxyalkyl, halogenalkyl, alkoxyalkyl, alkylmercaptoalkyl, aminoalkyl and alkylaminoalkyl radicals.
  • a preserving and disinfecting medium com prising as an activepreserving and disinfecting ingredient a quaternary ammonium halide substituted by two lower alkyl groups, one benzyl group and a. higher'molecular aliphatic radical containing 8 to 18 carbon atoms, which radical is selected from the. group consisting of higher alkyl, hydroxyalkyl, halogenalkyl, alkoxyalkyL.
  • alkylmercaptoalkyl, aminoalkyl and alkylaminoalkyl radicals are alkylmercaptoalkyl, aminoalkyl and alkylaminoalkyl radicals.
  • a preserving and disinfecting medium comprising as an active preserving and disinfecting ingredient a quaternary ammonium halide substituted by two lower alkyl groups, one benzyl group and the dodecyl radical.
  • a preserving and disinfecting medium comprising as an active preserving and disinfect ing ingredient a quaternary ammonium halide substituted by two alkyl groups of at most 2 carbon atoms, the benzyl and the dodecyl group.
  • a preserving and disinfecting medium comprising as an active preserving and disinfecting ingredient a quaternary ammonium halide substituted by two alkyl groups of at most two carbon atoms, a benzyl group and a higher molecular aliphatic hydrocarbon radical derived from the components of the fatty acid mixtures.
  • a preserving and disinfecting medium comprising as an active preserving and disinfecting ingredient a quaternary ammonium halide substituted by two lower alkyl groups, one benzyl group, and a higher molecular alkyl radical.
  • a preserving and disinfecting medium comprising as an active preserving and disinfecting ingredient a quaternary ammonium halide substituted by two lower alkyl groups, one benzyl group, and a higher molecular alkyl radical of 8 to 18 carbon atoms.

Description

Patented Feb. 15, 1938 PRESERVING AND DISINFEOTING MEDIA Gerhard Domagk, Wuppertal-Elberfeld, Germany, assignor, by mesne assignments, to Alba Pharmaceutical Company, Inc., New York, N. Y., a corporation of New York No Drawing. Application April I, 1934, Serial 14 Claims.
This invention relates to preserving and disinfecting media.
I have found that quaternary ammonium compounds display considerable bactericidal and fungicidal properties if they contain at least one higher molecular aliphatically bound hydrocarbon radical as substituent of the nitrogen atom. Such quaternary ammonium compounds, therefore, may be used as disinfecting and preserving agents as such or in admixture with each other or with other active or inert ingredients.
The higher molecular aliphatically bound hydrocarbon radical referred to above contains eight or more carbon atoms and may contain further substituents, such as halogen atoms, hydroxyl, alkoxy and amino group, and it may be interrupted by other atoms, for instance, by ether-like bound oxygenor sulfur atoms or by amino groups.
The following quaternary ammonium compounds may be mentioned by wayof example as being suitable as preserving and disinfecting! media:
Dimethyl-decyl-benzyl-ammoniumchloride, diethyl dodecyl benzyl ammoniumbromide, trimethyldodecyl-ammoniumbromide, allyl-dibutyldodecylammoniumbromide, methyl diallyl-dodecylammoniumiodide, diethyl-acetonyl-dodecylammoniumchloride, triethyl-dodecyloxymethylammoniumchloride, 'dibenzyl-hydroxyethyl-dodecyloxymethyl-ammoniumchloride, diethyl-(phydroxy-vbutyloxypropyl) dodecyloxymethylammoniumchloride, diethyl-benzylthioethyl-glycidoammoniumchloride, diethyl-dodecyl-geranylthioethyl-ammoniumbromide, diethyl-benzy'l-dodecylthioethyl-ammoniumchloride, diethyl-benzyl-geranylammoniumchloride, dibutyl-allyl-dodecyloxymethyl ammoniumchloride, dimethylgeranyl-dodecyl-ammoniumchloride, dimethyl-pnitrobenzyl-dodecylammoniumchloride, diethylcyclohexyl-dodecy1oxymethyl-ammoniumchloride, -trihydroxyethyl dodecylammoniumbromide, diethyl benzyl -dodecyloxy-fi-hydroxypropyl) ammoniumchloride, trimethyldodecylammoniumrhodanide, dimethyl-benzyl-dodecyl-ammoniumcyanide, dimethyl tridecyl benzylammoniumchloride, diethYl-pentadecyl benzyl-ammoniumbromide, dipropyl-phenylethyl-dodecylammoniumbromide.
Instead of the salts mentioned above other salts, for instance, the nitrates, sulfates, alkyi sulfates, phosphates, or the salts with organic acids, for instance, the formiates, acetates, lactates, tartrates, citrates, benzene or toluene sulfonates, benzoates, salicylates, etc. may be em- In Switzerland April 13, 1933 ployed. Preferably those quaternary ammonium compounds in which the higher molecular aliphatic hydrocarbon radical contains from 8 to 18 carbon atoms are used for preserving and disinfecting purposes. Advantageously they contain as a further substituent an aliphatically bound phenyl group.
The preserving and disinfecting activity of the quaternary ammonium compounds specified may be demonstrated as follows:-
The a dodecyloxy 3 hydroxypropyl diethylbenzyl-ammoniumchloride in the concentration 1:50000 kills colibacteria within 10 minutes, staphyloccoci within 15 minutes, dodecyl-diethylbenzyl-ammoniumchloride kills in the same concentration colibacteria after 10 minutes, staphyloccoci after 2 minutes.
The other quaternary ammonium compounds defined above display a similar batericidal and fungicidal action as the compounds mentioned before.
The quaternary ammonium compounds specified are in part crystalline, in part liquid substances. The salts of the quaternary ammoni- -um bases may be dissolved in water to stable solutions. Since the said quaternary ammonium compounds are practically odorless and relatively non-toxic for man they have proved suitable for the most various preserving and disinfecting purposes. For instance, they may be employed for the disinfection of all kinds of table utensils, storage utensils. They are further advantageously used for disinfecting purposes in the medical practice, for instance, for disinfecting medical instruments, all articles used in dressing wounds, for disinfecting laundry, furthermore, for cosmetics, for instance, face powder, or media for hyperidrosis. disinfected by means of the said quaternary ammonium compounds. Also foodstuffs, such as fruits, vegetables, meat, etc. may be preserved or disinfected by the quaternary ammonium compounds specified. They are further suitable for the preservation, that is exclusion of bacterial and autolytic decomposition processes of animal material, such as skins, blood, glands and other organs, etc.
My new disinfecting media may also be used in dilution with hard water without diminution of their activity. In the concentration necessary for disinfection they do not injure the skin and therefore may also be used for the disinfection of the skin, particularly the hands.
The quaternary ammonium compounds specified may be used in substance as well as in so- Floors and walls may likewise be lution or emulsion or in admixture with each other and/or with other activev or inert substances, such as powders, ointment bases, creams, etc. Advantageously such mixture of quaternary ammonium compounds may be used which contains at the nitrogen atom the higher molecular aliphatic hydrocarbon radicals derived from the components of the fatty acid mixtures as obtained from their natural initial material, such .asfats or resins, for instance, palm oil, coconut oil, colophony, and the like.
I claim:
1. A preserving and disinfecting medium comprising as an active preserving and disinfecting ingredient a non-acylated quaternary ammonium compound at least once substituted by a higher molecular aliphatic radical selected from the group consisting of higher alkyl, hydroxyalkyl, halogenalkyl, alkoxyalkyl, alkylmercaptoalkyl, aminoalkyl and alkylaminoalkyl radicals.
2. A preserving and disinfecting medium comprising as an active preserving and disinfecting ingredient a non-acylated quaternary ammonium compound at least once substituted by a higher molecular aliphatic radical selected from the group consisting of higher alkyl, hydroxyalkyl, haiogenalkyl, alkoxyalkyl, alkylmercaptoalkyl, aminoalkyl and alkylaminoalkyl radicals and further substituted by an aliphatically bound phenyl radical.
3. A preserving and disinfecting medium comprising as an active preserving and disinfecting ingredient a non-acylated quaternary ammonium compound at least once substituted by a higher molecular aliphatic radical containing 8 to 18 carbon atoms, which radical is selected from the group consisting of higher alkyl, hydroxyalkyl, halogenalkyl, alkoxyalkyl, alkylmercaptoalkyl, aminoalkyl and alkylaminoalkyl radicals.
4. A preserving and disinfecting medium comprising as an active preserving and disinfecting ingredient a non-acylated quaternary ammonium compound at least once substituted by a higher molecular aliphatic radical containing 8 to 18 carbon atoms, which radical is selected from the group consisting of higher alkyl, hydroxyalkyl, halogenalkyl, alkoxyalkyl, alkylmercaptoalkyl, aminoalkyl and alkylaminoalkyl radicals and further substituted by an aliphatically bound phenyl radical.
5. A preserving and disinfecting medium comprising as an active preserving and disinfecting ingredient a quaternary ammonium compound substituted by two lower alkyl groups, an aliphatically bound phenyl group and a higher molecular aliphatic radical selected from the group consisting of higher alkyl, hydroxyalkyl, halogenalkyl, alkoxyalkyl, alkylmercaptoalkyl, aminoalkyl and alkylaminoalkyl radicals.
6. A preserving and disinfecting medium comprising as an active preserving and disinfecting ingredient a quaternaryammonium compound substituted by two lower alkyl groups, an allphatically bound phenyl group and a higher molecular aliphatic radical containing 8 to 18 car-- bon atoms, which radical is selected from the group consisting of higher alkyl, hydroxyalkyl, halogenalkyl', alkoxyalkyl, alkylmercaptoalkyl, aminoalkyl and alkylaminoalkyl radicals.
7. A preserving and disinfecting medium comprising as an active preserving and disinfecting ingredient a quaternary ammonium compound substituted by two lower alkyl groups, an aliphatically bound phenyl group and a higher molecular aliphatic radical selected from the group consisting of higher alkyl, hydroxyalkyl, halogenalkyl, alkoxyalkyl, alkylmercaptoalkyl, aminoalkyl and alkylaminoalkyl radicals, which compound is in the form of a mineral acid salt.
8. A preserving and disinfecting medium comprising as an active preserving and disinfecting ingredient a quaternary ammonium halide substituted by two lower alkyl groups, one benzyl group and a higher molecular aliphatic radical selected from the group consisting of higher alkyl, hydroxyalkyl, halogenalkyl, alkoxyalkyl, alkylmercaptoalkyl, aminoalkyl and alkylaminoalkyl radicals.
9. A preserving and disinfecting medium com prising as an activepreserving and disinfecting ingredient a quaternary ammonium halide substituted by two lower alkyl groups, one benzyl group and a. higher'molecular aliphatic radical containing 8 to 18 carbon atoms, which radical is selected from the. group consisting of higher alkyl, hydroxyalkyl, halogenalkyl, alkoxyalkyL.
alkylmercaptoalkyl, aminoalkyl and alkylaminoalkyl radicals.
10. A preserving and disinfecting medium comprising as an active preserving and disinfecting ingredient a quaternary ammonium halide substituted by two lower alkyl groups, one benzyl group and the dodecyl radical.
11. A preserving and disinfecting medium comprising as an active preserving and disinfect ing ingredient a quaternary ammonium halide substituted by two alkyl groups of at most 2 carbon atoms, the benzyl and the dodecyl group.
12. A preserving and disinfecting medium comprising as an active preserving and disinfecting ingredient a quaternary ammonium halide substituted by two alkyl groups of at most two carbon atoms, a benzyl group and a higher molecular aliphatic hydrocarbon radical derived from the components of the fatty acid mixtures.
as obtained from their natural initial material.
13. A preserving and disinfecting medium comprising as an active preserving and disinfecting ingredient a quaternary ammonium halide substituted by two lower alkyl groups, one benzyl group, and a higher molecular alkyl radical.
14. A preserving and disinfecting medium comprising as an active preserving and disinfecting ingredient a quaternary ammonium halide substituted by two lower alkyl groups, one benzyl group, and a higher molecular alkyl radical of 8 to 18 carbon atoms.
GERHARD DOMAGK.
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Cited By (42)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2422951A (en) * 1942-04-11 1947-06-24 Jr Goldsmith Hall Conant Cold sterilizing solutions
US2437833A (en) * 1946-06-29 1948-03-16 Joseph B Niederl Nu-benzyl-nu-myristyl morpholinium halides
US2487707A (en) * 1943-07-30 1949-11-08 Ciba Pharmaceutical Products Beta-(5.7-dichloroquinolyl-(8)-oxy)-ethyl]-dimethyl-dodecyl ammonium bromide
US2494941A (en) * 1946-07-27 1950-01-17 Nuodex Products Co Inc Pest control agents
US2520275A (en) * 1946-12-28 1950-08-29 Onyx Oil & Chemical Company Aromatic diquaternary ammonium compounds
US2548679A (en) * 1948-07-10 1951-04-10 Sharples Chemicals Inc Preparation of alkylthiohydroxypropyl quaternary ammonium halides
US2548898A (en) * 1945-11-16 1951-04-17 Monsanto Chemicals Quaternary thenyl compounds
US2555504A (en) * 1947-01-10 1951-06-05 Ralph M Hibbs Embalming materials
US2599127A (en) * 1946-03-28 1952-06-03 Ind And Commercial Detergents Sterilizing detergent composition and method of use
US2609393A (en) * 1951-02-02 1952-09-02 Sharp & Dohme Inc Dodecyl, dimethyl, -cinnamylammonium halides
US2647130A (en) * 1951-11-20 1953-07-28 Winthrop Stearns Inc Nu-(nu-tetradecyl)-nu-(3, 4-methylenedioxybenzyl)-nu, nu-dimethylammonium chloride and preparation thereof
US2658873A (en) * 1947-05-21 1953-11-10 Armour & Co Germicidal detergent composition
US2664444A (en) * 1951-11-20 1953-12-29 Winthrop Stearns Inc N-(n-dodecyl)-n-(3,4-dichlorophenethyl)-n, n-dimethyl-ammonium compounds
US2689790A (en) * 1951-09-26 1954-09-21 Monsanto Chemicals Nitrogenous compound herbicides
US2692264A (en) * 1950-05-02 1954-10-19 Hooker Electrochemical Co Quaternary ammonium containing compounds containing fluoroalkyl monocyclic aromatic hydrocarbon groups
US2786797A (en) * 1954-05-18 1957-03-26 Hollingshead Corp Corrosion-inhibited quaternary ammonium compositions
US3205169A (en) * 1961-07-14 1965-09-07 Nalco Chemical Co Compositions for breaking emulsions or inhibiting formation thereof and processes utilizing same
US3361792A (en) * 1964-04-03 1968-01-02 Millimaster Onyx Corp Microbiologically active quaternary ammonium compounds
US3361795A (en) * 1964-04-13 1968-01-02 Millmaster Onyx Corp Microbiologically active quaternary ammonium compounds
US3361793A (en) * 1964-02-10 1968-01-02 Millmaster Onyx Corp Microbiologically active quaternary ammonium compounds
US3361794A (en) * 1964-04-03 1968-01-02 Millmaster Onyx Corp Microbiologically active quaternary ammonium compounds
US3366673A (en) * 1964-04-03 1968-01-30 Millmaster Onyx Corp Microbiologically active quaternary ammonium compounds
US3366672A (en) * 1964-04-03 1968-01-30 Millmaster Onyx Corp Microbiologically active quaternary ammonium compounds
US3519631A (en) * 1965-08-18 1970-07-07 Boehringer Sohn Ingelheim Quaternary derivatives of 1,2,3,4-tetra-hydro-9-amino-acridine
DE2340914A1 (en) * 1973-08-13 1975-02-27 Degussa PROCESS FOR PREPARING STABLE 2,2-DIMETHYL-4-OXYMETHYL-1,3-DIOXOLANIC DRUG EXTRACTS
WO1984002467A1 (en) * 1982-12-23 1984-07-05 Research Corp Orally administered biologically active peptides and proteins
US4721511A (en) * 1984-10-05 1988-01-26 W. R. Grace & Co. Leach resistant antimicrobial fabric
US4804492A (en) * 1986-11-07 1989-02-14 Sterling Drug Inc. Liquid sanitizing and cleaning compositions with diminished skin irritancy
WO1990004918A2 (en) * 1988-10-25 1990-05-17 Wake Forest University Quaternary amine containing ether or ester lipid derivatives and therapeutic compositions
US5645823A (en) * 1995-07-07 1997-07-08 Thrall; Bernice Eileen Keratinous tissue conditioner
US5770584A (en) * 1993-06-10 1998-06-23 Wake Forest University Method of treating hepatitis virus infections
EP0927516A1 (en) * 1997-12-08 1999-07-07 Bernardo Birnbaum Disinfectant composition
US5962437A (en) * 1994-08-29 1999-10-05 Wake Forest University Lipid analogs for treating viral infections
US20020082242A1 (en) * 2000-10-19 2002-06-27 Kucera Louis S. Compositions and methods of double-targeting virus infections and cancer cells
US20040115249A1 (en) * 2002-12-12 2004-06-17 Raczek Nico N. Ionic compounds of quaternary ammonium cations with anions of preservation acids, preparation thereof, and use thereof for preservation
US20040149809A1 (en) * 2001-05-29 2004-08-05 Weekamp Johannus Wilhelmus Metal-ceramic bond
US20040233811A1 (en) * 2001-08-31 2004-11-25 Duffield David Jay Sequence counter for an audio visual stream
US20040259845A1 (en) * 1995-08-07 2004-12-23 Wake Forest University Lipid analogs for treating viral infections
US20050187191A1 (en) * 2004-02-20 2005-08-25 Kucera Louis S. Methods and compositions for the treatment of respiratory syncytial virus
US7309696B2 (en) 2000-10-19 2007-12-18 Wake Forest University Compositions and methods for targeting cancer cells
WO2011140451A2 (en) 2010-05-07 2011-11-10 Resource Development L.L.C. Solvent-free organosilane quaternary ammonium compositions, method of making and use
US8735618B2 (en) 2010-05-07 2014-05-27 Resource Development L.L.C. Solvent-free organosilane quaternary ammonium compositions, method of making and use

Cited By (63)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2422951A (en) * 1942-04-11 1947-06-24 Jr Goldsmith Hall Conant Cold sterilizing solutions
US2487707A (en) * 1943-07-30 1949-11-08 Ciba Pharmaceutical Products Beta-(5.7-dichloroquinolyl-(8)-oxy)-ethyl]-dimethyl-dodecyl ammonium bromide
US2548898A (en) * 1945-11-16 1951-04-17 Monsanto Chemicals Quaternary thenyl compounds
US2599127A (en) * 1946-03-28 1952-06-03 Ind And Commercial Detergents Sterilizing detergent composition and method of use
US2437833A (en) * 1946-06-29 1948-03-16 Joseph B Niederl Nu-benzyl-nu-myristyl morpholinium halides
US2494941A (en) * 1946-07-27 1950-01-17 Nuodex Products Co Inc Pest control agents
US2520275A (en) * 1946-12-28 1950-08-29 Onyx Oil & Chemical Company Aromatic diquaternary ammonium compounds
US2555504A (en) * 1947-01-10 1951-06-05 Ralph M Hibbs Embalming materials
US2658873A (en) * 1947-05-21 1953-11-10 Armour & Co Germicidal detergent composition
US2548679A (en) * 1948-07-10 1951-04-10 Sharples Chemicals Inc Preparation of alkylthiohydroxypropyl quaternary ammonium halides
US2692264A (en) * 1950-05-02 1954-10-19 Hooker Electrochemical Co Quaternary ammonium containing compounds containing fluoroalkyl monocyclic aromatic hydrocarbon groups
US2609393A (en) * 1951-02-02 1952-09-02 Sharp & Dohme Inc Dodecyl, dimethyl, -cinnamylammonium halides
US2689790A (en) * 1951-09-26 1954-09-21 Monsanto Chemicals Nitrogenous compound herbicides
US2647130A (en) * 1951-11-20 1953-07-28 Winthrop Stearns Inc Nu-(nu-tetradecyl)-nu-(3, 4-methylenedioxybenzyl)-nu, nu-dimethylammonium chloride and preparation thereof
US2664444A (en) * 1951-11-20 1953-12-29 Winthrop Stearns Inc N-(n-dodecyl)-n-(3,4-dichlorophenethyl)-n, n-dimethyl-ammonium compounds
US2786797A (en) * 1954-05-18 1957-03-26 Hollingshead Corp Corrosion-inhibited quaternary ammonium compositions
US3205169A (en) * 1961-07-14 1965-09-07 Nalco Chemical Co Compositions for breaking emulsions or inhibiting formation thereof and processes utilizing same
US3361793A (en) * 1964-02-10 1968-01-02 Millmaster Onyx Corp Microbiologically active quaternary ammonium compounds
US3361792A (en) * 1964-04-03 1968-01-02 Millimaster Onyx Corp Microbiologically active quaternary ammonium compounds
US3361794A (en) * 1964-04-03 1968-01-02 Millmaster Onyx Corp Microbiologically active quaternary ammonium compounds
US3366673A (en) * 1964-04-03 1968-01-30 Millmaster Onyx Corp Microbiologically active quaternary ammonium compounds
US3366672A (en) * 1964-04-03 1968-01-30 Millmaster Onyx Corp Microbiologically active quaternary ammonium compounds
US3361795A (en) * 1964-04-13 1968-01-02 Millmaster Onyx Corp Microbiologically active quaternary ammonium compounds
US3519631A (en) * 1965-08-18 1970-07-07 Boehringer Sohn Ingelheim Quaternary derivatives of 1,2,3,4-tetra-hydro-9-amino-acridine
DE2340914A1 (en) * 1973-08-13 1975-02-27 Degussa PROCESS FOR PREPARING STABLE 2,2-DIMETHYL-4-OXYMETHYL-1,3-DIOXOLANIC DRUG EXTRACTS
WO1984002467A1 (en) * 1982-12-23 1984-07-05 Research Corp Orally administered biologically active peptides and proteins
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US4721511A (en) * 1984-10-05 1988-01-26 W. R. Grace & Co. Leach resistant antimicrobial fabric
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