US3855140A - Cleansing compositions - Google Patents
Cleansing compositions Download PDFInfo
- Publication number
- US3855140A US3855140A US00253102A US25310272A US3855140A US 3855140 A US3855140 A US 3855140A US 00253102 A US00253102 A US 00253102A US 25310272 A US25310272 A US 25310272A US 3855140 A US3855140 A US 3855140A
- Authority
- US
- United States
- Prior art keywords
- percent
- oxide
- composition
- chlorhexidine
- polyoxyethylene
- 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 abstract description 29
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229960003260 chlorhexidine Drugs 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 229920001400 block copolymer Polymers 0.000 claims abstract description 6
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 claims abstract description 6
- -1 polyoxyethylene Polymers 0.000 claims description 17
- 239000004088 foaming agent Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 229960003333 chlorhexidine gluconate Drugs 0.000 claims description 10
- YZIYKJHYYHPJIB-UUPCJSQJSA-N chlorhexidine gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.C1=CC(Cl)=CC=C1NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NC1=CC=C(Cl)C=C1 YZIYKJHYYHPJIB-UUPCJSQJSA-N 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 8
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 7
- 229920001577 copolymer Polymers 0.000 claims description 7
- IBOBFGGLRNWLIL-UHFFFAOYSA-N n,n-dimethylhexadecan-1-amine oxide Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)[O-] IBOBFGGLRNWLIL-UHFFFAOYSA-N 0.000 claims description 6
- 229920001451 polypropylene glycol Polymers 0.000 claims description 6
- SYELZBGXAIXKHU-UHFFFAOYSA-N dodecyldimethylamine N-oxide Chemical compound CCCCCCCCCCCC[N+](C)(C)[O-] SYELZBGXAIXKHU-UHFFFAOYSA-N 0.000 claims description 5
- XOMORPAQODCYDK-UHFFFAOYSA-N 14-methylpentadecyl(oxido)azanium Chemical compound CC(C)CCCCCCCCCCCCC[NH2+][O-] XOMORPAQODCYDK-UHFFFAOYSA-N 0.000 claims description 4
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 claims description 4
- 229940050410 gluconate Drugs 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- PHOQVHQSTUBQQK-SQOUGZDYSA-N D-glucono-1,5-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O PHOQVHQSTUBQQK-SQOUGZDYSA-N 0.000 claims description 3
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 3
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 3
- FATUQANACHZLRT-KMRXSBRUSA-L calcium glucoheptonate Chemical class [Ca+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O FATUQANACHZLRT-KMRXSBRUSA-L 0.000 claims description 3
- 235000012209 glucono delta-lactone Nutrition 0.000 claims description 3
- 229960003681 gluconolactone Drugs 0.000 claims description 3
- 229930195712 glutamate Natural products 0.000 claims description 3
- JDVPQXZIJDEHAN-UHFFFAOYSA-M succinamate Chemical compound NC(=O)CCC([O-])=O JDVPQXZIJDEHAN-UHFFFAOYSA-M 0.000 claims description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 claims description 2
- 239000003701 inert diluent Substances 0.000 abstract description 4
- 229920001983 poloxamer Polymers 0.000 description 8
- 238000005187 foaming Methods 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229920002023 Pluronic® F 87 Polymers 0.000 description 2
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical group C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 2
- 239000002280 amphoteric surfactant Substances 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 230000009849 deactivation Effects 0.000 description 2
- QKRMFCXDTFLKKT-UHFFFAOYSA-N 2-hydroxyethanesulfonic acid Chemical compound OCCS(O)(=O)=O.OCCS(O)(=O)=O QKRMFCXDTFLKKT-UHFFFAOYSA-N 0.000 description 1
- 239000004150 EU approved colour Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- YSVBPNGJESBVRM-UHFFFAOYSA-L disodium;4-[(1-oxido-4-sulfonaphthalen-2-yl)diazenyl]naphthalene-1-sulfonate Chemical compound [Na+].[Na+].C1=CC=C2C(N=NC3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)O)=CC=C(S([O-])(=O)=O)C2=C1 YSVBPNGJESBVRM-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/722—Ethers of polyoxyalkylene glycols having mixed oxyalkylene groups; Polyalkoxylated fatty alcohols or polyalkoxylated alkylaryl alcohols with mixed oxyalkylele groups
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3707—Polyethers, e.g. polyalkyleneoxides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S206/00—Special receptacle or package
- Y10S206/812—Packaged towel
Definitions
- the disclosure relates to cleansing compositions con-- taining a soluble salt of chlorhexidine, a polyoxyethylenepolyoxypropylene block co-polymer and .an inert diluent or carrier.
- the essential constituents of such a composition are a suitable salt of chlorhexidine and a surfactant.
- a surfactant very many common surfactants are, however, incompatible with chlorhexidine.
- anionic surfactants are known to destroy the antibacterial activity of chlorhexidine solutions by complexing with the cationic chlorhexidine, and cationic surfactants are not preferred be-' cause of their irritancy, and because in combination with a soluble chlorhexidine salt double decomposition can occur, with the formation of insoluble chlorhexidine salts and consequent loss of antibacterial activity.
- Amphoteric surfactants with contain either anionic or cationic centres depending upon pH, suffer from the above described disadvantages of anionic and cationic surfactants, and are therefore equally unsuitable for the present purpose.
- Non-ionic surfactants were therefore examined in combination with chlorhexidine gluconate (20 percent w/v of surfactant and 2 percent v/v of chlorhexidine gluconate provided as a 20 percent w/v solution) in water.
- tion-ionic surfactants of various types which were investigated, only four possessed 70 percent or more of the antibacterial activity of a 2 percent solu-- wherein a, b and c are integers, having molecular weights between 1,000 and 16,000, and in which the terminal polyoxyethylene chains represent 10-80 percent of the molecule, which copolymers are available commercially under the trade name Pluronic.
- Pluronic is available commercially under the trade name
- composition comprising from 0.5 to 10.0 percent w/v of a salt of chlorhexidine which is soluble to the extent of at least 0.5 percent w/v in water at ambient temperature, and a polyoxyethylene-polyoxypropylene block copolymer consisting of 20-80 percent of polyoxyethylene, and wherein the polyoxypropylene part of. the polymer molecule has a molecular weight of between 1,000 and 2,750, together with an inert diluent or carner.
- Suitable salts of chlorhexidine which are soluble in water at ambient temperature to the extent of at least 0.5 percent w/v are, for example, the gluconate, isethionate (2-hydroxyethanesulphonate), formate, acetate,
- glutamate succinamate, monodiglycollate, dimethanesulphonate, lactate, di-isobutyrate and glucoheptonate, and of these, the gluconate is particularly preferred.
- Particular polyoxyethylene-polyoxypropylene block copolymers which are useful in the compositions of the invention are those known as Pluronics, and having the following designations, (wherein the figures in parentheses following the designation indicate the typical molecular weight of the polyoxypropylene part of the molecule, and the precentage of polyoxyethylene in the molecule, respectively):-
- L44 (12,00 40), L62 (1750, 20), 1200, 63 (1750, 30), L64 (1750, 40),. P65 (1750, 50), F68 (1750, P75 (2050,50), F77 (2050, 70), P84 (2250, 40), P85 (2250, 50) and F87 (2250, 70).
- Pluronics are those comprising 40 to 70 percent of polyoxyethylene, and wherein the typical molecular weight of polyoxypropylene is between about 2,000 and about'2,500.
- Particularly preferred ,Pluronics are those with a polyoxypropylene typical molecular weight of about 2,250, and containing 40 to 70 percent of polyoxyethylene, that is Pluronic"s P84, P85 and F87, which possess the optimum combination of foaming ability, mild detergency, viscosity, water solubility and non-irritancy.
- the surfactant of choice is Pluronic F87.
- compositions contain from 10 to 30 per cent of Pluronic F87, ideally about 25 percent, and from 0.5 to 5.0 percent of chlorhexidine gluconate.
- the compositions should preferably possess ,moderate foaming properties, and to achieve this it is necessary to include'a foaming agent.
- Most foaming agents deactivate chlorhexidine to a large extent, but with amine oxide foaming agents the deactivation is kept to a minimum. Nevertheless, some deactivation is unavoidable, so it is preferable to use a surfactant having maximum foaming properties, so that the quantity of deactivating foaming agent is kept to a minimum.
- Pluronics P84, P85 and F87 have the greatest foaming ability and with these, the addition of 3.75 percent of an amine oxide foaming agent gives a composition having acceptable foaming properties, but
- Suitable amine oxide foaming agents are, for example, cetyldimethylamine oxide, lauryldimethylamine oxide, cetylmethylmyristylamine, oxide and dimethylmyristylarnine oxide, and of these, cetyldimethylamine oxide is preferred as being the most stable and the least deactivating as a constituent of the composition of this invention.
- compositions of the invention comprises those compositions containing 0.5 to 5.0 percent of chlorhexidine gluconate, about 25 percent of a copolymer as described above containing 40 to 70 percent of poloxyethylene, and witha polyoxypropylene typical molecular weight of about 2,250, and about 3.75 percent of an amine oxide foaming an inert diluent or carrier.
- compositions may also optionally contain perfumes, colouring agents and preservatives, forexample isopropyl alcohol, ethyl alcohol, methyl phydroxybenzoate or propyl p-hydroxybenzoate. It is also advantageous to adjust the pH of the composition to between and 7, preferably to about 5.5, to minimise the precipitation of insoluble chlorhexidine salts on storage.
- a suitable agent for adjusting the pH of the compositions is, for example, gluconolactone, or the acid from which the anion of the chlorhexidine salt in use is derived.
- EXAMPLE 1 EXAMPLE 2 The process described in Example 1 is repeated, using 0.05 percent w/v of Edicol Supra Ponceau 4R8 in place of Edicol Supra Carmoisine W.S., and adjusting the water content in proportion.
- a skin-cleansing composition which consists essentially of from 0.5 to 10.0 percent w/v of a salt of chlorhexidine which is soluble to the extent of at least 0.5 percent w/v in water at ambient temperature, se-
- composition of claim 1 which contains be tween 10 and 30 percent of copolymer.
- composition of claim 1 which contains from 0.5 to 5.0 percent of chlorhexidine gluconate.
- composition of claim 1 which additionally contains an amine oxide foaming agent selected from the group consisting of cetyldimethylamine oxide, lauryldimethylamine oxide, cetylmethylmyristylamine oxide and dimethylmyristylamine oxide.
- an amine oxide foaming agent selected from the group consisting of cetyldimethylamine oxide, lauryldimethylamine oxide, cetylmethylmyristylamine oxide and dimethylmyristylamine oxide.
- composition of claim 1 which consists essentially of from 0.5 to 5.0 percent of chlorhexidine gluconate, 25 percent of the copolymer containing 70 percent of polyoxyethylene and with a polyoxypropylene molecular weight of about 2250, and about 3.75 percent of an amine oxide foaming agent selected from the group consisting of cetyldimethylamine oxide, lauryldimethylamine oxide, cetylmethylmyristylamine oxde and dimethylmyristylamine oxide, together with said water.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2876471A GB1338003A (en) | 1971-06-18 | 1971-06-18 | Cleaning compositions |
| US00253102A US3855140A (en) | 1971-06-18 | 1972-05-15 | Cleansing compositions |
| CA142,903A CA969442A (en) | 1971-06-18 | 1972-05-24 | Cleansing compositions |
| AU42746/72A AU459343B2 (en) | 1971-06-18 | 1972-05-25 | Cleansing compositions |
| NL7208128A NL167852C (nl) | 1971-06-18 | 1972-06-14 | Werkwijze ter bereiding van een vloeibaar reinigingsmiddel. |
| FR7221907A FR2161882B1 (enrdf_load_stackoverflow) | 1971-06-18 | 1972-06-16 | |
| DE2229549A DE2229549C3 (de) | 1971-06-18 | 1972-06-16 | Desinfizierendes Reinigungsmittel |
| US05/512,483 US3960745A (en) | 1971-06-18 | 1974-10-04 | Cleansing compositions |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2876471 | 1971-06-18 | ||
| US00253102A US3855140A (en) | 1971-06-18 | 1972-05-15 | Cleansing compositions |
| US05/512,483 US3960745A (en) | 1971-06-18 | 1974-10-04 | Cleansing compositions |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/512,483 Continuation US3960745A (en) | 1971-06-18 | 1974-10-04 | Cleansing compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3855140A true US3855140A (en) | 1974-12-17 |
Family
ID=27258749
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00253102A Expired - Lifetime US3855140A (en) | 1971-06-18 | 1972-05-15 | Cleansing compositions |
| US05/512,483 Expired - Lifetime US3960745A (en) | 1971-06-18 | 1974-10-04 | Cleansing compositions |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/512,483 Expired - Lifetime US3960745A (en) | 1971-06-18 | 1974-10-04 | Cleansing compositions |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US3855140A (enrdf_load_stackoverflow) |
| AU (1) | AU459343B2 (enrdf_load_stackoverflow) |
| CA (1) | CA969442A (enrdf_load_stackoverflow) |
| DE (1) | DE2229549C3 (enrdf_load_stackoverflow) |
| FR (1) | FR2161882B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1338003A (enrdf_load_stackoverflow) |
| NL (1) | NL167852C (enrdf_load_stackoverflow) |
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3960745A (en) * | 1971-06-18 | 1976-06-01 | Imperial Chemical Industries Limited | Cleansing compositions |
| US3997458A (en) * | 1974-04-12 | 1976-12-14 | Deknatel, Incorporated | Method of cleansing contaminated wounds and surgical scrub solutions for same |
| US4066566A (en) * | 1976-03-31 | 1978-01-03 | Lafant Research Company | Denture cleaner |
| DE3016110A1 (de) * | 1979-04-26 | 1980-11-06 | Bristol Myers Co | Antibakterielle verbindungen, verfahren zu ihrer herstellung und daraus hergestellte mittel |
| US4326977A (en) * | 1980-11-10 | 1982-04-27 | Basf Wyandotte Corporation | Liquid antiseptic cleaners with improved foaming properties |
| US4390442A (en) * | 1981-04-27 | 1983-06-28 | Plough, Inc. | Non-stinging eye make-up remover composition |
| US4420484A (en) * | 1979-08-13 | 1983-12-13 | Sterling Drug Inc. | Basic amino or ammonium antimicrobial agent-polyethylene glycol ester surfactant-betaine and/or amine oxide surfactant compositions and method of use therof |
| US4456543A (en) * | 1982-06-17 | 1984-06-26 | The Buckeye Cellulose Corporation | Bisbiguanide based antibacterial cleansing products |
| US4478821A (en) * | 1982-01-26 | 1984-10-23 | The Gillette Company | Inhibition of body odor |
| US4496322A (en) * | 1983-05-11 | 1985-01-29 | University Of Toronto Innovations Foundation | Benzoin antimicrobial dental varnishes |
| WO1986002090A1 (en) * | 1984-09-26 | 1986-04-10 | Gluck Bruno A | Antiseptic cleansing compositions |
| USRE32300E (en) * | 1979-08-13 | 1986-12-02 | Sterling Drug Inc. | Basic amino or ammonium antimicrobial agent-polyethylene glycol ester surfactant-betaine and/or amine oxide surfactant compositions and method of use thereof |
| US4642234A (en) * | 1983-09-15 | 1987-02-10 | University Of Bath | Disinfection of contact lenses |
| US5000867A (en) * | 1986-10-20 | 1991-03-19 | Lever Brothers Company | Disinfectant compositions |
| US5719113A (en) * | 1994-05-20 | 1998-02-17 | Gojo Industries, Inc. | Antimicrobial cleansing composition containing chlorhexidine, an amphoteric surfactant, and an alkyl polyglucoside |
| US5763412A (en) * | 1997-04-08 | 1998-06-09 | Becton Dickinson And Company | Film-forming composition containing chlorhexidine gluconate |
| US20100040657A1 (en) * | 2008-08-15 | 2010-02-18 | Kevin Scott Creevy | Gentle, non-irritating, non-alcoholic skin disinfectant |
| US20140378550A1 (en) * | 2013-06-19 | 2014-12-25 | Coloplast A/S | Antimicrobial cleanser |
| US11135184B2 (en) * | 2013-07-25 | 2021-10-05 | Claridei Laboratories, Inc. | Formulations for epidermal repair |
| US11369549B2 (en) | 2017-10-12 | 2022-06-28 | Medline Industries, Lp | Antiseptic wipes |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2808865A1 (de) * | 1978-03-02 | 1979-09-13 | Hoechst Ag | Mikrobiozide mittel auf der basis von alkyl-di-guanidinium-salzen |
| US4496576A (en) * | 1980-10-23 | 1985-01-29 | Mallinckrodt, Inc. | Compositions of p-hydroxybenzoic acid esters and methods of preparation and use |
| US4504405A (en) * | 1980-12-18 | 1985-03-12 | Smith And Nephew Associated Companies P.L.C. | Method of cleaning soft contact lenses |
| ATE17952T1 (de) * | 1981-11-06 | 1986-02-15 | Smith & Nephew Ass | Reinigungsloesung. |
| GB8630823D0 (en) * | 1986-01-16 | 1987-02-04 | Ici Plc | Antiseptic compositions |
| NZ230308A (en) * | 1988-08-22 | 1991-03-26 | Becton Dickinson Co | Antimicrobial cleansing composition comprising chlorhexidine and a nonionic surfactant |
| JP2961556B2 (ja) * | 1990-06-15 | 1999-10-12 | 丸石製薬株式会社 | 皮膚消毒用組成物 |
| NZ241579A (en) * | 1991-03-25 | 1994-04-27 | Becton Dickinson Co | Antimicrobial formulations for treating the skin |
| US5164107A (en) * | 1991-04-25 | 1992-11-17 | Becton, Dickinson And Company | Chlorhexidine composition useful in a surgical scrub |
| US5339988A (en) | 1992-10-19 | 1994-08-23 | Ballard Medical Products | Disposable tray sump foamer, assembly and methods |
| JP3981151B2 (ja) * | 1994-03-28 | 2007-09-26 | ザ トラスティーズ オブ コロンビア ユニバーシティー イン ザ シティー オブ ニューヨーク | 液体中の刺激物を不活化するための組成物 |
| US5668084A (en) * | 1995-08-01 | 1997-09-16 | Zeneca Inc. | Polyhexamethylene biguanide and surfactant composition and method for preventing waterline residue |
| US5985918A (en) * | 1996-12-04 | 1999-11-16 | The Trustees Of Columbia University In The City Of New York | Zinc-based antiirritant creams |
| US6846846B2 (en) * | 2001-10-23 | 2005-01-25 | The Trustees Of Columbia University In The City Of New York | Gentle-acting skin disinfectants |
| CA2475224C (en) * | 2002-02-07 | 2011-11-01 | The Trustees Of Columbia University In The City Of New York | Zinc salt compositions for the prevention of mucosal irritation from spermicides and microbicides |
| US7879365B2 (en) * | 2002-02-07 | 2011-02-01 | The Trustees Of Columbia University In The City Of New York | Zinc salt compositions for the prevention of dermal and mucosal irritation |
| US7745425B2 (en) * | 2002-02-07 | 2010-06-29 | The Trustees Of Columbia University In The City Of New York | Non-irritating compositions containing zinc salts |
| US20060079143A1 (en) * | 2003-05-12 | 2006-04-13 | Sage Products, Inc. | Controlled dosing of fibrous materials |
| US20040228758A1 (en) * | 2003-05-12 | 2004-11-18 | Thomas Keaty | Disinfectant delivery system, and method of providing alcohol-free disinfection |
| BRPI0412675A (pt) * | 2003-07-17 | 2006-10-03 | Univ Columbia | composições antimicrobianas contendo combinações sinergìsticas de compostos de amÈnio quaternário e óleos essenciais e/ou constituintes |
| US7823727B2 (en) * | 2005-06-29 | 2010-11-02 | Sage Products, Inc. | Patient check system |
| WO2007079022A2 (en) * | 2005-12-30 | 2007-07-12 | The Dial Corporation | Antibacterial compositions comprising quaternary ammonium germicides and alkamine oxides having reduced irritation potential |
| US7759327B2 (en) * | 2006-01-06 | 2010-07-20 | The Trustees Of Columbia University In The City Of New York | Compositions containing zinc salts for coating medical articles |
| US20180077927A1 (en) * | 2015-03-20 | 2018-03-22 | Greena B.V. | Adjuvant composition, treatment composition and aqueous spray formulations suitable for agriculturally-related use |
| WO2019084134A1 (en) * | 2017-10-24 | 2019-05-02 | Saint Anthony Biomedical, LLC | COMPOSITIONS AND METHODS FOR REDUCING INFECTION IN WOUNDS AND SURGICAL SITES |
| GB2577111B (en) * | 2018-09-14 | 2022-07-13 | Tetrosyl I Tec Ltd | Screen wash |
| CA3148140C (en) * | 2019-07-22 | 2024-05-14 | Gojo Industries, Inc. | Antimicrobial cleansing compositions comprising bisbiguanide antimicrobial active |
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- 1972-05-24 CA CA142,903A patent/CA969442A/en not_active Expired
- 1972-05-25 AU AU42746/72A patent/AU459343B2/en not_active Expired
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- 1972-06-16 FR FR7221907A patent/FR2161882B1/fr not_active Expired
- 1972-06-16 DE DE2229549A patent/DE2229549C3/de not_active Expired
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| GB815925A (en) * | 1956-06-06 | 1959-07-01 | Ici Ltd | New biguanide salts |
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| US3324183A (en) * | 1960-05-05 | 1967-06-06 | Terg-o-tometee test results | |
| US3296145A (en) * | 1965-10-21 | 1967-01-03 | Millmaster Onyx Corp | Quaternary ammonium-tertiary amine oxide compositions |
| GB1202496A (en) * | 1967-05-26 | 1970-08-19 | Eastman Kodak Co | Photographic camera |
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Cited By (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3960745A (en) * | 1971-06-18 | 1976-06-01 | Imperial Chemical Industries Limited | Cleansing compositions |
| US3997458A (en) * | 1974-04-12 | 1976-12-14 | Deknatel, Incorporated | Method of cleansing contaminated wounds and surgical scrub solutions for same |
| USRE29909E (en) * | 1974-04-12 | 1979-02-13 | Deknatel Inc. | Method of cleansing contaminated wounds |
| US4066566A (en) * | 1976-03-31 | 1978-01-03 | Lafant Research Company | Denture cleaner |
| DE3016110A1 (de) * | 1979-04-26 | 1980-11-06 | Bristol Myers Co | Antibakterielle verbindungen, verfahren zu ihrer herstellung und daraus hergestellte mittel |
| JPS55149242A (en) * | 1979-04-26 | 1980-11-20 | Bristol Myers Co | Chlorhexidine salts and their composition |
| US4420484A (en) * | 1979-08-13 | 1983-12-13 | Sterling Drug Inc. | Basic amino or ammonium antimicrobial agent-polyethylene glycol ester surfactant-betaine and/or amine oxide surfactant compositions and method of use therof |
| USRE32300E (en) * | 1979-08-13 | 1986-12-02 | Sterling Drug Inc. | Basic amino or ammonium antimicrobial agent-polyethylene glycol ester surfactant-betaine and/or amine oxide surfactant compositions and method of use thereof |
| US4326977A (en) * | 1980-11-10 | 1982-04-27 | Basf Wyandotte Corporation | Liquid antiseptic cleaners with improved foaming properties |
| US4390442A (en) * | 1981-04-27 | 1983-06-28 | Plough, Inc. | Non-stinging eye make-up remover composition |
| US4478821A (en) * | 1982-01-26 | 1984-10-23 | The Gillette Company | Inhibition of body odor |
| US4456543A (en) * | 1982-06-17 | 1984-06-26 | The Buckeye Cellulose Corporation | Bisbiguanide based antibacterial cleansing products |
| US4496322A (en) * | 1983-05-11 | 1985-01-29 | University Of Toronto Innovations Foundation | Benzoin antimicrobial dental varnishes |
| US4642234A (en) * | 1983-09-15 | 1987-02-10 | University Of Bath | Disinfection of contact lenses |
| WO1986002090A1 (en) * | 1984-09-26 | 1986-04-10 | Gluck Bruno A | Antiseptic cleansing compositions |
| US5000867A (en) * | 1986-10-20 | 1991-03-19 | Lever Brothers Company | Disinfectant compositions |
| US5719113A (en) * | 1994-05-20 | 1998-02-17 | Gojo Industries, Inc. | Antimicrobial cleansing composition containing chlorhexidine, an amphoteric surfactant, and an alkyl polyglucoside |
| US5763412A (en) * | 1997-04-08 | 1998-06-09 | Becton Dickinson And Company | Film-forming composition containing chlorhexidine gluconate |
| US20100040657A1 (en) * | 2008-08-15 | 2010-02-18 | Kevin Scott Creevy | Gentle, non-irritating, non-alcoholic skin disinfectant |
| US8173147B2 (en) | 2008-08-15 | 2012-05-08 | Xttrium Laboratories, Inc. | Gentle, non-irritating, non-alcoholic skin disinfectant |
| US20140378550A1 (en) * | 2013-06-19 | 2014-12-25 | Coloplast A/S | Antimicrobial cleanser |
| US9636286B2 (en) * | 2013-06-19 | 2017-05-02 | Coloplast A/S | Antimicrobial cleanser |
| US11135184B2 (en) * | 2013-07-25 | 2021-10-05 | Claridei Laboratories, Inc. | Formulations for epidermal repair |
| US12233034B2 (en) | 2013-07-25 | 2025-02-25 | Claridei Laboratories, Inc. | Formulations for epidermal repair |
| US11369549B2 (en) | 2017-10-12 | 2022-06-28 | Medline Industries, Lp | Antiseptic wipes |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2229549B2 (enrdf_load_stackoverflow) | 1980-08-07 |
| NL167852C (nl) | 1981-09-16 |
| CA969442A (en) | 1975-06-17 |
| GB1338003A (en) | 1973-11-21 |
| NL7208128A (enrdf_load_stackoverflow) | 1972-12-20 |
| FR2161882A1 (enrdf_load_stackoverflow) | 1973-07-13 |
| US3960745A (en) | 1976-06-01 |
| AU4274672A (en) | 1973-11-29 |
| DE2229549A1 (de) | 1972-12-21 |
| DE2229549C3 (de) | 1981-03-19 |
| AU459343B2 (en) | 1975-03-20 |
| FR2161882B1 (enrdf_load_stackoverflow) | 1976-08-06 |
| NL167852B (nl) | 1981-09-16 |
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