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US3855140A - Cleansing compositions - Google Patents

Cleansing compositions Download PDF

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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
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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
Application number
US00253102A
Inventor
M Billany
A Longworth
J Shatwell
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Imperial Chemical Industries Ltd
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Imperial Chemical Industries Ltd
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Filing date
Publication date
Priority to GB2876471A priority Critical patent/GB1338003A/en
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to US00253102A priority patent/US3855140A/en
Priority to CA142,903A priority patent/CA969442A/en
Priority to AU42746/72A priority patent/AU459343B2/en
Priority to NL7208128A priority patent/NL167852C/en
Priority to FR7221907A priority patent/FR2161882B1/fr
Priority to DE2229549A priority patent/DE2229549C3/en
Priority to US05/512,483 priority patent/US3960745A/en
Application granted granted Critical
Publication of US3855140A publication Critical patent/US3855140A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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.

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  • 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)
  • Cosmetics (AREA)
  • Detergent Compositions (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The disclosure relates to cleansing compositions containing a soluble salt of chlorhexidine, a polyoxyethylenepolyoxypropylene block co-polymer and an inert diluent or carrier.

Description

United States Patent [191 Billany et al.
[ Dec.'17, 1974 I CLEANSING COMPOSITIONS [75] Inventors: Michael Royston Billany; Arthur 1 Raymond Longworth; John Shatwell, all of Macclesfield, England [73] Assignee: Imperial Chemical Industries Limited, London, England [22] Filed: May 15, 1972 [21] Appl. No.: 253,102
[30] Foreign Application Priority Data June 18, 1971 Great Britain 28764/71 [52] US. Cl 252/106, 252/547, 424/326 [51] Int. Cl. .L. Clld 1/72, Cl 1d 3/48 [58] Field of Search 252/106, 107, 547:
[56] 1 References Cited UNITED STATES PATENTS 6,145 1/1967 Findland et a1. 252/106 4.183 6/1967 Priestley 260/584 FOREIGN PATENTS OR APPLICATIONS 815,925 7/1959 Great Britain 1,202,496 8/1970 Great Britain 993,044 5/1965 Great Britain 745,064 2/1956 Great Britain 159,111 9/1954 Australia 815,800 7/1959 Great Britain OTHER PUBLICATIONS Aromox AmineoxidesNew Products,-Applications,.
Opportunities, Armour & C0,, February 1964, pp. 1, 2, 4, 5, 6, 7.
Primary Examiner-Mayer Weinblatt Assistant Examiner-P. E. Willis Attorney, Agent, or Firm-Cushman, Darby & Cushman 57 ABSTRACT The disclosure relates to cleansing compositions con-- taining a soluble salt of chlorhexidine, a polyoxyethylenepolyoxypropylene block co-polymer and .an inert diluent or carrier.
6 Claims, N0 Drawings be used routinely by hospital ward staff.
The essential constituents of such a composition are a suitable salt of chlorhexidine and a surfactant. Very many common surfactants are, however, incompatible with chlorhexidine. Thus, 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. Thus, for example, of 13 amphoteric surfactants examined as aqueous solutions containing 20 percent w/v of surfactant and 2 percent v/v of chlorhexidine gluconate (provided as a 20 percent w/v solution in water) the best combination possessed only 14 percent of the antibacterial activity of a 2 percent solution of chlorhexidine gluconate alone.
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. Of 17 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. However, from the results of comparative tests, we have found that not all Pluronics are equally suitable for the present purpose.
Thus, according to the invention there is provided a 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).
Preferred 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.
Preferred 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.
For user acceptability, 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
with other Pluronics it is necessary, in order to obtain a sufficiently foaming composition, to increase the quantity of foaming agent incorporated, and to increase also the quantity of chlorhexidine in order to overcome the deactivating effect of the additional foaming agent.
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.
An especially preferred group of compositions of the inventioncomprises 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.
The 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.
The invention is illustrated but not limited by the following Examples in which the parts are by weight:
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.
What we claim is:
l. 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-
lected from the group consisting of the gluconate, isethionate, fonnat'e, acetate, glutamate, succinamate, mono-diglycollate, di-methanesulphonate, lactate, di-' isobutyrate and glucoheptonate salt, a polyoxyethylene-polyoxypropylene block copolymer of the formula HO-(CHz'CH2-0).;(CH-CH O) (CH -CHrOhH Hz b wherein a, b and c are integers, such that said copolymer consists of 70 percent of polyoxyethylene and wherein the molecular weight of the polyoxypropylene content is about 2250, and water.
2. The composition of claim 1 which contains be tween 10 and 30 percent of copolymer.
3. The composition of claim 1 which contains from 0.5 to 5.0 percent of chlorhexidine gluconate.
4. The 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.
5. A composition according to claim 1 wherein gluconolactone is included to provide a pH between 5 and 7.
6. The 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.

Claims (6)

1. 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, SELECTED FROM THE GROUP CONSISTING OF THE GLUCONATE, ISETHIONATE, FORMATE, ACETATE, GLUTAMATE, SUCCINAMATE, MONO-DIGLYCOLLATE, DI-METHANESULPHONATE, LACTATE, DI-ISOBUTYRATE AND GLUCOHEPTONATE SALT, A POLYOXYETHYLENE-POLYOXYPROPYLENE BLOCK COPOLYMER OF THE FORMULA
2. The composition of claim 1 which contains between 10 and 30 percent of copolymer.
3. The composition of claim 1 which contains from 0.5 to 5.0 percent of chlorhexidine gluconate.
4. The 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.
5. A composition according to claim 1 wherein gluconolactone is included to provide a pH between 5 and 7.
6. The 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.
US00253102A 1971-06-18 1972-05-15 Cleansing compositions Expired - Lifetime US3855140A (en)

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 (en) 1971-06-18 1972-06-14 METHOD FOR PREPARING A LIQUID CLEANER
FR7221907A FR2161882B1 (en) 1971-06-18 1972-06-16
DE2229549A DE2229549C3 (en) 1971-06-18 1972-06-16 Disinfectant detergent
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

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US05/512,483 Continuation US3960745A (en) 1971-06-18 1974-10-04 Cleansing compositions

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US05/512,483 Expired - Lifetime US3960745A (en) 1971-06-18 1974-10-04 Cleansing compositions

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AU (1) AU459343B2 (en)
CA (1) CA969442A (en)
DE (1) DE2229549C3 (en)
FR (1) FR2161882B1 (en)
GB (1) GB1338003A (en)
NL (1) NL167852C (en)

Cited By (20)

* Cited by examiner, † Cited by third party
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 (en) * 1979-04-26 1980-11-06 Bristol Myers Co ANTIBACTERIAL COMPOUNDS, METHOD FOR THEIR PRODUCTION AND MEANS PRODUCED 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
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 (26)

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Publication number Priority date Publication date Assignee Title
DE2808865A1 (en) * 1978-03-02 1979-09-13 Hoechst Ag MICROBIOCIDES BASED ON ALKYL DI GUANIDINIUM SALT
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
EP0079185B1 (en) * 1981-11-06 1986-02-12 Smith and Nephew Associated Companies p.l.c. Cleaning solution
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 (en) * 1990-06-15 1999-10-12 丸石製薬株式会社 Composition for skin disinfection
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
DE69533724T2 (en) * 1994-03-28 2005-10-27 The Trustees Of Columbia University In The City Of New York COMPOSITION FOR INACTIVATING SWEETENERS IN LIQUIDS
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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 (en) * 1979-04-26 1980-11-06 Bristol Myers Co ANTIBACTERIAL COMPOUNDS, METHOD FOR THEIR PRODUCTION AND MEANS PRODUCED THEREOF
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
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US5719113A (en) * 1994-05-20 1998-02-17 Gojo Industries, Inc. Antimicrobial cleansing composition containing chlorhexidine, an amphoteric surfactant, and an alkyl polyglucoside
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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
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Also Published As

Publication number Publication date
FR2161882A1 (en) 1973-07-13
NL167852B (en) 1981-09-16
CA969442A (en) 1975-06-17
NL167852C (en) 1981-09-16
US3960745A (en) 1976-06-01
DE2229549A1 (en) 1972-12-21
AU4274672A (en) 1973-11-29
FR2161882B1 (en) 1976-08-06
NL7208128A (en) 1972-12-20
AU459343B2 (en) 1975-03-20
DE2229549C3 (en) 1981-03-19
DE2229549B2 (en) 1980-08-07
GB1338003A (en) 1973-11-21

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