CA2120335A1 - Antimicrobial composition - Google Patents

Antimicrobial composition

Info

Publication number: CA2120335A1
Authority: CA; Canada
Prior art keywords: blend; compound; composition according; quaternary ammonium; weight
Prior art date: 1991-10-07
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.): Abandoned

Application number

CA 2120335

Other languages

English (en)

French (fr)

Inventor

John J. Merianos

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

ISP Investments LLC

Original Assignee

Individual

Priority date (The priority date 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 date listed.)

1991-10-07

Filing date

1992-08-12

Publication date

1993-04-15

1991-10-07 Priority claimed from US07/772,182 external-priority patent/US5196135A/en

1991-10-07 Priority claimed from US07/772,409 external-priority patent/US5216030A/en

1991-10-25 Priority claimed from US07/783,017 external-priority patent/US5242684A/en

1992-08-12 Application filed by Individual filed Critical Individual

1993-04-15 Publication of CA2120335A1 publication Critical patent/CA2120335A1/en

Status Abandoned legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 134
230000000845 anti-microbial effect Effects 0.000 title claims abstract description 12
229920000036 polyvinylpyrrolidone Polymers 0.000 claims abstract description 22
235000013855 polyvinylpyrrolidone Nutrition 0.000 claims abstract description 19
239000001267 polyvinylpyrrolidone Substances 0.000 claims abstract description 14
229920001577 copolymer Polymers 0.000 claims abstract description 12
239000000178 monomer Substances 0.000 claims abstract description 10
229940083122 ganglion-blocking antiandrenergic bisquaternary ammonium compound Drugs 0.000 claims abstract description 7
-1 acrylamido Chemical group 0.000 claims abstract description 6
229920002554 vinyl polymer Polymers 0.000 claims abstract description 5
231100000053 low toxicity Toxicity 0.000 claims abstract description 4
239000004599 antimicrobial Substances 0.000 claims abstract 2
231100000344 non-irritating Toxicity 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 41
229910052794 bromium Inorganic materials 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
229910052740 iodine Inorganic materials 0.000 claims description 4
125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical group 0.000 claims description 2
SMLXICHDYHVTSX-UHFFFAOYSA-N 1-phenylprop-2-enylazanium;chloride Chemical compound Cl.C=CC(N)C1=CC=CC=C1 SMLXICHDYHVTSX-UHFFFAOYSA-N 0.000 claims 1
OSNAXXTYZROTTR-UHFFFAOYSA-N dodecyl(dimethyl)azanium 2-methyl-N-propylprop-2-enimidate Chemical group CCCN=C([O-])C(C)=C.CCCCCCCCCCCC[NH+](C)C OSNAXXTYZROTTR-UHFFFAOYSA-N 0.000 claims 1
WZZXVTWYTQUAGA-UHFFFAOYSA-M dodecyl-dimethyl-(1-phenylprop-2-enyl)azanium;chloride Chemical group [Cl-].CCCCCCCCCCCC[N+](C)(C)C(C=C)C1=CC=CC=C1 WZZXVTWYTQUAGA-UHFFFAOYSA-M 0.000 claims 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
IJESQWNJAWCXMI-UHFFFAOYSA-N prop-2-enamide;hydrobromide Chemical compound Br.NC(=O)C=C IJESQWNJAWCXMI-UHFFFAOYSA-N 0.000 claims 1
UZNHKBFIBYXPDV-UHFFFAOYSA-N trimethyl-[3-(2-methylprop-2-enoylamino)propyl]azanium;chloride Chemical group [Cl-].CC(=C)C(=O)NCCC[N+](C)(C)C UZNHKBFIBYXPDV-UHFFFAOYSA-N 0.000 claims 1
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 abstract description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
239000002904 solvent Substances 0.000 description 7
230000007794 irritation Effects 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
SFBHPFQSSDCYSL-UHFFFAOYSA-N n,n-dimethyltetradecan-1-amine Chemical compound CCCCCCCCCCCCCCN(C)C SFBHPFQSSDCYSL-UHFFFAOYSA-N 0.000 description 4
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 4
231100000419 toxicity Toxicity 0.000 description 4
230000001988 toxicity Effects 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
230000000844 anti-bacterial effect Effects 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
230000002349 favourable effect Effects 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
244000005700 microbiome Species 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 3
239000007787 solid Substances 0.000 description 3
WAROVFJVCBYVHY-UHFFFAOYSA-N 1-ethenylpyrrolidin-2-one;trimethyl-[3-(2-methylprop-2-enoylamino)propyl]azanium;chloride Chemical compound [Cl-].C=CN1CCCC1=O.CC(=C)C(=O)NCCC[N+](C)(C)C WAROVFJVCBYVHY-UHFFFAOYSA-N 0.000 description 2
125000006012 2-chloroethoxy group Chemical group 0.000 description 2
229940126062 Compound A Drugs 0.000 description 2
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000000654 additive Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
150000004694 iodide salts Chemical class 0.000 description 2
239000006210 lotion Substances 0.000 description 2
YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000008107 starch Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 1
MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 description 1
WXZQWZXRMBKDCT-UHFFFAOYSA-N CCCNC(C=C)=O.Br Chemical compound CCCNC(C=C)=O.Br WXZQWZXRMBKDCT-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
241001527806 Iti Species 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229910001508 alkali metal halide Inorganic materials 0.000 description 1
150000008045 alkali metal halides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
238000000975 co-precipitation Methods 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
XZLUKDKHSFSBSQ-UHFFFAOYSA-N dodecyl(dimethyl)azanium;2-methyl-n-propylprop-2-enamide;bromide Chemical compound [Br-].CCCNC(=O)C(C)=C.CCCCCCCCCCCC[NH+](C)C XZLUKDKHSFSBSQ-UHFFFAOYSA-N 0.000 description 1
230000002500 effect on skin Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000010528 free radical solution polymerization reaction Methods 0.000 description 1
150000004820 halides Chemical group 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
239000000463 material Substances 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/38—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
- 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
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/19—Quaternary ammonium compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Pest Control & Pesticides (AREA)
Dentistry (AREA)
Medicinal Chemistry (AREA)
Agronomy & Crop Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Plant Pathology (AREA)
Engineering & Computer Science (AREA)
Polymers & Plastics (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA 2120335 1991-10-07 1992-08-12 Antimicrobial composition Abandoned CA2120335A1 (en)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US772,182		1991-10-07
US07/772,182 US5196135A (en)	1991-10-07	1991-10-07	Antimicrobial, low toxicity, blend composition of bis-quaternary ammonium compounds
US07/772,409 US5216030A (en)	1991-10-07	1991-10-07	Antimicrobial, low toxicity, blend composition of bis-quaternary ammonium compounds and polyvinylpyrrolidone
US772,409		1991-10-07
US783,017		1991-10-25
US07/783,017 US5242684A (en)	1991-10-25	1991-10-25	Antimicrobial, low toxicity, non-irritating composition comprising a blend of bis-quaternary ammonium compounds coprecipitated with a copolymer of vinylpyrrolidone and an acrylamido or vinyl quaternary ammonium monomer

Publications (1)

Publication Number	Publication Date
CA2120335A1 true CA2120335A1 (en)	1993-04-15

Family

ID=27419681

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2120335 Abandoned CA2120335A1 (en)	1991-10-07	1992-08-12	Antimicrobial composition

Country Status (4)

Country	Link
EP (1)	EP0607162A4 (de)
AU (1)	AU2461892A (de)
CA (1)	CA2120335A1 (de)
WO (1)	WO1993007251A1 (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5536494A (en) *	1994-10-04	1996-07-16	Alcon Laboratories, Inc.	Polyethylene oxide-containing quaternary ammunium polymers and pharmaceutical compositions containing an antimicrobial amount of same
US5783502A (en) *	1995-06-07	1998-07-21	Bsi Corporation	Virus inactivating coatings

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2194906A (en) *	1936-04-11	1940-03-26	Ig Farbenindustrie Ag	Nitrogenous condensation product and process of producing same
US2933529A (en) *	1956-01-09	1960-04-19	Rohm & Haas	Symmetrical diquaternary ammonium compounds
CH409985A (de) *	1961-11-03	1966-03-31	Robapharm Ag	Verfahren zur Herstellung von neuen heterocyclischen Ammoniumverbindungen
US3525793A (en) *	1969-06-30	1970-08-25	Millmaster Onyx Corp	Microbiocidal quaternary ammonium compounds containing synergistic blends of alkyl groups
FR2654617B1 (fr) *	1989-11-20	1993-10-08	Oreal	Composition cosmetique reductrice pour permanente contenant, en tant qu'agent reducteur, de l'aletheine ou l'un de ses sels, et son utilisation dans un procede de deformation permanente des cheveux.

1992
- 1992-08-12 WO PCT/US1992/006695 patent/WO1993007251A1/en not_active Ceased
- 1992-08-12 CA CA 2120335 patent/CA2120335A1/en not_active Abandoned
- 1992-08-12 EP EP19920917984 patent/EP0607162A4/de not_active Withdrawn
- 1992-08-12 AU AU24618/92A patent/AU2461892A/en not_active Abandoned

Also Published As

Publication number	Publication date
EP0607162A1 (de)	1994-07-27
AU2461892A (en)	1993-05-03
EP0607162A4 (de)	1994-11-17
WO1993007251A1 (en)	1993-04-15

Legal Events

Date	Code	Title	Description
1996-02-12	FZDE	Dead

Publication	Publication Date	Title
US5242684A (en)	1993-09-07	Antimicrobial, low toxicity, non-irritating composition comprising a blend of bis-quaternary ammonium compounds coprecipitated with a copolymer of vinylpyrrolidone and an acrylamido or vinyl quaternary ammonium monomer
CN1105496C (zh)	2003-04-16	含一种紫罗烯聚合物及十二烷胺盐的协同抗微生物组合物及其使用方法
US4482680A (en)	1984-11-13	Quaternary ammonium group-containing polymers having antimicrobial activity
EP2325218A1 (de)	2011-05-25	Antimikrobielle Copolymere und ihre Verwendung
US4304894A (en)	1981-12-08	Quaternary ammonium terpolymers
DE69531285T2 (de)	2004-04-01	Verwendung von polyethylenoxid enthaltenden polymerisierten quaternären ammoniumverbindungen in pharmazeutischen präparaten
EP0641805A1 (de)	1995-03-08	Antimikrobielle Polymere und diese Polymere enthaltende Zusammensetzungen
EP2607430A1 (de)	2013-06-26	Antibakterielle dispersion
WO1995030425A1 (en)	1995-11-16	Poly(benzalkonium salt) as an anti-microbial agent for aqueous drug compositions
US20190313637A1 (en)	2019-10-17	Stabilization of particles coated with non-amphoteric, quaternizable and water-soluble polymers using a dispersing component
CA1106277A (en)	1981-08-04	Microbiocidal agents on the basis of alkyl- diguanidinium salts
EP0728414A2 (de)	1996-08-28	Mikroemulsionen von 3-Isothiazolonverbindungen
DE69705386T2 (de)	2002-05-16	Feinteilige vernetzte N-Vinylamid Harze
US5196135A (en)	1993-03-23	Antimicrobial, low toxicity, blend composition of bis-quaternary ammonium compounds
JPH03112904A (ja)	1991-05-14	抗菌剤
JP3176676B2 (ja)	2001-06-18	殺菌組成物
WO1993007251A1 (en)	1993-04-15	Antimicrobial composition
US4830851A (en)	1989-05-16	Polymeric halophors
EP1987716B1 (de)	2012-10-31	Wasserbasierte und antimikrobiell aktive Dispersionskonzentrate
CA2315760A1 (en)	1999-07-22	Tuberculocidal disinfectant
US4444750A (en)	1984-04-24	Method of conditioning hair
US20070015684A1 (en)	2007-01-18	Viscosity improvement in liquid fabric softeners
US5216030A (en)	1993-06-01	Antimicrobial, low toxicity, blend composition of bis-quaternary ammonium compounds and polyvinylpyrrolidone
DE69902197T2 (de)	2002-11-28	Verwendung einer Flüssigkeit zum Desinfizieren von Kontaktlinsen
US20020006888A1 (en)	2002-01-17	Novel quaternary ammonium salt and process for the preparation thereof