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WO1992018100A1 - Nettoyant liquide, doux, antibacterien pour la peau - Google Patents

Nettoyant liquide, doux, antibacterien pour la peau Download PDF

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Publication number
WO1992018100A1
WO1992018100A1 PCT/US1992/002847 US9202847W WO9218100A1 WO 1992018100 A1 WO1992018100 A1 WO 1992018100A1 US 9202847 W US9202847 W US 9202847W WO 9218100 A1 WO9218100 A1 WO 9218100A1
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WIPO (PCT)
Prior art keywords
cationic
ethoxylated
group
surfactant
level
Prior art date
Application number
PCT/US1992/002847
Other languages
English (en)
Inventor
Arthur Edwin Keegan, Jr.
Richard Marc Dahlgren
Diane Grob Schmidt
Original Assignee
The Procter & Gamble Company
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.)
Filing date
Publication date
Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to JP4510260A priority Critical patent/JPH06506938A/ja
Priority to FI934541A priority patent/FI934541A0/fi
Priority to BR9205895A priority patent/BR9205895A/pt
Publication of WO1992018100A1 publication Critical patent/WO1992018100A1/fr
Priority to NO933675A priority patent/NO933675L/no

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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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/347—Phenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/442—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof substituted by amido group(s)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/731—Cellulose; Quaternized cellulose derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/737—Galactomannans, e.g. guar; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005—Antimicrobial preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/54—Polymers characterized by specific structures/properties
    • A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
    • A61K2800/5426—Polymers characterized by specific structures/properties characterized by the charge cationic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/596—Mixtures of surface active compounds

Definitions

  • This invention relates to mild liquid skin cleansers. More particularly, this invention relates to antibacterial liquid skin cleansers.
  • one object of this invention is the development of liquid skin cleaning compositions which exhibit improved mildness, good cleaning and lathering, and good degerming properties.
  • Another object of the present invention is the development of low cost liquid skin cleansers.
  • a liquid skin cleanser composition with improved mildness and degerming characteristics comprising:
  • antibacterial agent preferably selected from the group of halogenated aromatic anti ⁇ bacterial agents and octopirox, and mixtures thereof;
  • This invention relates to mild ethoxylated surfactant liquid skin cleaning compositions with optimum degerming and preferably optimum lather performance.
  • Cosurfactant preferably one with good suds boosting power, typically a harsh surfactant, is used with said mild ethoxylated surfactant to provide improved lather.
  • Antibacterial agents are compatible with cosurfactant, e.g.. alkyl sulfates, but are not so compatible with mild ethoxylate surfactants. This invention, however, further enhances combi ⁇ nation of the two types of surfactants with antibacterial.
  • a liquid skin cleanser composition with improved mildness and degerming characteristics comprising: (A) 0.5-5.75% of mild, ethoxylated surfactant selected from the group consisting of anionic; nonionics, and mixtures thereof, preferably anionic alkyl ethoxy sulfate having from 1 to 20 ethoxy groups;
  • antibacterial agent preferably selected from the group of halogenated aromatic antibacterial agents and octopirox, and mixtures thereof, and more preferably Triclosan (TCS);
  • the total level of (A) and (B) is at least about 4% and sufficient to keep the composition stable.
  • Some preferred cosurfactant blends are:
  • An essential ingredient is an ethoxylated (or propoxylated) surfactant which is mild to the skin.
  • Propoxylated surfactants are essentially equivalents to ethoxylated surfactants as defined herein.
  • the preferred mild, ethoxylated (propoxylated) sur- factants have Relative Barrier Destruction Index Values (mildness) of about 50 or less, as defined hereinbelow.
  • the mild ethoxylated surfactant, ammonium laureth-3-carboxylate (AE3C-NH4OH at pH 6.5), has an "Index Value" of about 50.
  • a "harsh” surfactant is any surfactant or cosurfactant with an Index Value of more than 50.
  • the ethoxylated mild surfactant is used conveniently to improve mildness of the liquid composition.
  • the level can be from about 0.5% to about 5.8%, preferably from about 2% to about 5%.
  • the ethoxylated mild surfactant diminishes antibacterial effectiveness of the composition.
  • the preferred surfactants are alkali metal and ammonium salts of the sulfuric acid esters of the reaction product of 1 mole of a C8-C22 alcohol (e.g., tallow or coconut oil alcohols) and about 1 to 20, preferably 1 to 13, more preferably 2 to 6, moles of ethylene oxide (ethoxy groups).
  • Diethanol amines are not ethoxylated surfactants.
  • the CTFA names of some preferred ethoxylated surfactants are: Anionics Ammonium Laureth Sulfate, CAS #32612-48-9 (generic)
  • PEG-8 Stearate, CAS #9004-99-3 (generic)
  • the in vitro skin barrier penetration test (mildness) performed similar to the procedure described in U.S. Pat. No. 4,812,253, Small et al., issued Mar. 14, 1989, said patent being incorporated herein by reference, can be used to assess the relative irritancy of surfactants.
  • the essential, mild ethoxy- lated surfactant is preferably selected to have a mildness Index Value at or below 50.
  • Cosurfactant Another essential component of the liquid skin cleanser composition herein is one or more non-ethoxylated "cosurfactant" which is preferably selected for its cleaning, lathering, cost or antibacterial compatibility. So the selection of the cosurfactant and the term "cosurfactant” should be given a broad interpreta ⁇ tion. Preferred are the higher lathering surfactants which are known in the art, or can be tested. The rule, as far as lather or cleaning are concerned, is that the cosurfactant should add to the lather or cleaning power of the liquid cleanser.
  • the cosurfactant can also be selected for its mildness, as well as its cleaning or lather boosting properties. However, such cosurfactants are typically harsh (e.g., Index Value >50).
  • compositions that provide the best balance of properties have a ratio of harsh cosurfactant to mild ethoxylated surfactant of from about 20:1 to about 1:5.8, preferably from about 5:1 to about 1:2, more prefer ⁇ ably from about 2:1 to about 1:1.
  • Some preferred cosurfactant blends are set out after Table 1.
  • cosurfactant as used herein is intended to denote any non-ethoxylated surfactant used in the liquid compositions of the present invention.
  • the cosurfactant includes all non-ethoxy ⁇ lated surface active agents, especially those which lather and clean well and which are compatible with the antibacterial, i.e., more compatible than the ethoxylated surfactant.
  • the preferred cosurfactants of this invention are the alkali metal (e.g., sodium or potassium) and ammonium, alkyl sulfates derived by sulfation of c 8" c 22 alcohols, either synthetically derived or produced by reduction of glycerides, or other esters, of tallow or coconut oil fatty acid combined with similarly derived alkyl betaines (zwit- terionics) and alkyl amides (nonionics).
  • alkali metal e.g., sodium or potassium
  • ammonium alkyl sulfates derived by sulfation of c 8" c 22 alcohols, either synthetically derived or produced by reduction of glycerides, or other esters, of tallow or coconut oil fatty acid combined with similarly derived alkyl betaines (zwit- terionics) and alkyl amides (nonionics).
  • the preferred cosurfactant referred to herein is alkyl sulfate (AS).
  • the preferred ethoxylated surfactant is alkyl ether sulfate (AE n S).
  • AE n S alkyl ether sulfate
  • the antibacterial agent can be present at a level of from about 0.01% to about 4%, typically from about 0.1% to about 2%, and preferably from about 0.5% to about 1%. The level is selected to provide the desired level of antibacterial activity and can be modified as desired.
  • the preferred antibacterial agent is 2-hydroxy-4,2',4'-trichlorodiphenylether (TCS).
  • TCS 2-hydroxy-4,2',4'-trichlorodiphenylether
  • Other halogenated antibacterial agents are set out below. Many antibacterial agents, known to those skilled in the art and disclosed in, e.g., U.S. Pat. Nos. 3,835,057 and 4,714,563, both incorporated here ⁇ inbefore by reference, may be used.
  • Suitable antibacterial agents include: 2-hydroxy-4,2',4'-trichlorodiphenylether (TCS); 2,6-dimethyl-4-hydroxychlorobenzene (PCMX); 3,4,4'-trichlorocarbanilide (TCC);
  • TFC 3-trif1uoromethyl-4,4'-dichlorocarbani1ide
  • TFC 2,2'-dihydroxy-3,3',5,5',6,6'-hexachlorodiphenylmethane
  • 2-hydroxy-4,4'-dichlorodiphenylether 2,2'-dihydroxy-3,3',5,5',6,6'-hexachlorodiphenylmethane
  • the Water-Soluble Cationic Polymer The inclusion of an effective amount of a water-soluble cationic polymer to any liquid antibacterial composition should improve mildness, including systems which do not contain ethoxy ⁇ lated surfactant.
  • the water-soluble cationic polymeric skin conditioning agent essential in the present invention is selected from the group consisting of: (I) cationic polysaccharides;
  • the amount of hydrated cationic polymeric skin conditioners found useful in the composition of the present invention is from about 0.05% to about 5%, preferably from about 0.1% to about 2%, by weight of active polymer.
  • the liquid cleaning compositions containing these relatively small amounts of polymer deliver significantly improved clinical mildness relative to a composition without the polymer. The resultant mildness is unexpectedly and surprisingly superior to that of the synthetic surfactant-based liquid antibacterial skin cleansing products currently on the market.
  • the cationic polymers can also provide a desirable silky, soft, smooth in-use feeling.
  • the cationic polymers can be employed to achieve the mildness benefit while maintaining the highly acceptable and desirable in-use liquid cleansing product characteristics of good lather character, lather volume, cleaning, rinsing, skin feel, odor, degerming, etc. This is unexpected since cationic polymers, particularly when used at the higher levels typically necessary for a mildness improvement and when used without the hydration specified by the present invention, have a significant negative impact on in-use characteristics. For example, they can suppress lather volume and alter its character, result in poor rinsing, and have a negative impact on odor.
  • the cationic polysaccharide class encompasses those polymers based on 5 or 6 carbon sugars and derivatives which have been made cationic by engraphing of cationic moieties on the polysaccharide backbone. They may be composed of one type of sugar or of more than one type, i.e. copolymers of the above derivatives and cationic materials. The monomers may be in straight chain or branched chain geometric arrangements.
  • Cationic polysaccharide polymers include the following: cationic celluloses and hydroxy- ethylcelluloses; cationic starches and hydroxyalkyi starches; cationic polymers based on arabinose monomers such as those which could be derived from arabinose vegetable gums; cationic polymers derived from xylose polymers found in materials such as wood, straw, cottonseed hulls, and corn cobs; cationic polymers derived from fucose polymers found as a component of cell walls in sea ⁇ weed; cationic polymers derived from fructose polymers such as Inulin found in certain plants; cationic polymers based on acid- containing sugars such as galacturonic acid and glucuronic acid; cationic polymers based on amine sugars such as galactosamine and glucosamine; cationic polymers based on 5 and 6 membered ring polyalcohols; cationic polymers based on galactose monomers
  • members of the cationic polysaccaride class include the cationic hydroxyethyl cellulose JR 400 made by Union Carbide Corporation; the cationic starches Stalok® 100, 200, 300 and 400 made by Staley, Inc.; the cationic galactomannans based on guar gum of the Galactasol 800 series by Henkel , Inc., the Jaguar Series by Rh ⁇ ne-Poulenc (for example, Jaguar C-14-S and C162).
  • the cationic copolymers of saccharides and synthetic cationic monomers useful in the present invention encompass those contain ⁇ ing the following saccharides: glucose, galactose, mannose, arabinose, xylose, fucose, fructose, glucosamine, galactosamine, glucuronic acid, galacturonic acid, and 5 or 6 me bered ring polyalcohols. Also included are hydroxymethyl, hydroxyethyl and hydroxypropyl derivatives of the above sugars.
  • saccharides When saccharides are bonded to each other in the copolymers, they may be bonded via any of several arrangements, such as 1,4- ⁇ r; 1,4,-0; 1,3- ⁇ ; 1,3-0 and 1,6 linkages.
  • the synthetic cationic monomers for use in these copolymers can include dimethyldiall lammonium chloride, dimethylaminoethylmethyacrylate, diethyldiallylammonium chloride, N,N-diallyl,N-N-dialkyl ammonium halides, and the like.
  • a pre- ' ferred cationic polymer is Merquat 550 prepared with di ethyldi- allylammonium chloride and acrylamide monomers.
  • Examples of members of the cl ss of copolymers of saccharides and synthetic cationic monomers include those composed of cellu ⁇ lose derivatives (e.g., hydroxyethyl cellulose) and N,N- diallyl,N-N-dialkyl ammonium chloride available from National Starch Corporation under the trade name Celquat.
  • cellu ⁇ lose derivatives e.g., hydroxyethyl cellulose
  • N,N- diallyl,N-N-dialkyl ammonium chloride available from National Starch Corporation under the trade name Celquat.
  • the cationic synthetic polymers useful in the present in ⁇ vention are cationic polyalkylene imines, ethoxypolyalklene imines, and poly[N-[-3-(dimethylammonio)propyl]-N'-[3-(ethylene- oxyethylene dimethylammonio)propyl]urea dichloride] the latter of which is available from Miranol Chemical Company, Inc. under the trademark of Miranol A-15, CAS Reg. No. 68555-36-2.
  • Preferred cationic polymeric skin conditioning agents of the present invention are those cationic polysaccharides of the cationic guar gum class with molecular weights of 1,000 to 3,000,000. More prefered molecular weights are from 2,500 to 350,000. These polymers have a polysaccharide backbone comprised of galactomannan units and a degree of cationic substitution ranging from about 0.04 per anhydroglucose unit to about 0.80 per anhydroglucose unit with the substituent cationic group being the adduct of 2,3-epoxypropyltrimethyl ammonium chloride to the natural polysaccharide backbone.
  • Examples are Jaguar C-376-FA, C-14-S, C-15, C-17, C162, and ADMQ guar sold by Rh ⁇ ne-Poulenc.
  • Some preferred cationic guar gums have 1-2% aqueous solution viscosity of from about 125 cps to about 3500 ⁇ 500 cps at 25 * C, where said aqueous solution has a pH of about 9-11.
  • the cationic guar gum polymers useful in the present inven ⁇ tion have been found to be more effective skin conditioners than those cationic polymers based on hydroxyethyl cellulose (e.g., JR-400 commercially available from Union Carbide Corporation). Also useful in the present invention are cationic polymers re ⁇ ferred to in U.S. Pat. No. 3,761,418, to Parran, Jr., supra, in UK Patent Application GB 2094307A, and in commonly assigned U.S. Pat. Application Ser. No. 07/374,315, Bartolo and Wong, filed June 30, 1989, said patent and said patent applications incorporated herein by reference.
  • the skin cleansers herein are preferably in the form of liquids or creams in which water is the principal diluent.
  • the level of water in the compositions is typically from about 60% to about 93% by weight, preferably from about 75% to about 90%. Purified water is preferred.
  • pH Adjustment Agent The in use pH of the liquid skin cleanser compositions herein should lie in the range of about 4 to about 10, preferably in the range of about 5 to about 8, more preferably in the range of about 6 to about 7.
  • the pH is kept in the acidic range to maintain the stability of the antibacterial TCS and the cationic guar.
  • Suit ⁇ able pH adjustment agents include HC1, citric acid, phosphoric acid, succinic acid and a sodium citrate/citric acid combination, among many others.
  • Optional Components include HC1, citric acid, phosphoric acid, succinic acid and a sodium citrate/citric acid combination, among many others.
  • the skin cleansers herein can contain a variety of non- essential, optional ingredients suitable for improving such compositions in a variety of ways.
  • Such conventional, optional ingredients are well known to those skilled in the art, e.g., preservatives such as HMDM Hydantoin, benzyl alcohol, methyl paraben, propyl paraben, 3-isothiazolines (Kathon CG sold by Rohm and Haas), imidazolidinyl urea, methylchloroisothiazolinone, and methylisothiazolinone can be used in amounts of from 1 to 5,000 ppm; thickeners and viscosity modifiers such as sodium sulfate, polyethylene glycols, sodium chloride, ammonium chloride, car- boxy ethylcellulose, methylcellulose, polyvinyl alcohol, and ethyl alcohol; suspending agents such as magnesium/aluminum silicate; perfumes, dyes; opacifiers such as ethylene glycol diste
  • liquid skin cleanser compositions of the present inven ⁇ tion are made using mixing techniques disclosed herein.
  • a method of making the present invention is shown in the examples which follow.
  • a method which can be used to make the exemplary compositions of the present invention is as follows: 1.
  • the polymer is hydrated in the main mix tank by dispersing in purified water at ambient temperature, then lowering the solution pH to about 6 via addition of citric or other suitable acid, to aid hydration.
  • Sodium sulfate may also be added to reduce the potential for polymer/surfactant coacer- vate formation when the surfactants are mixed with the polymer.
  • a separate premix of the purified water, sodium alkyl sul ⁇ fate, cocoamidopropyl betaine, lauramide diethanol amine, and ethyleneglycol distearate is mixed at a temperature of about 76'C, then chilled to about 26° to 38'C to crystallize the ethyleneglycol distearate.
  • the crystallized ethyleneglycol distearate gives the final product a pearlized appearance.
  • step (3) The contents of the premix in step (2) are added to the hydrated polymer in the main mix.
  • the sodium laureth-3 sulfate is added to main mix.
  • the preservatives are added to the main mix.
  • Citric acid is added to adjust the pH of the finished product to about pH 6.0 to 6.5.
  • the TCS is predissolved in the perfume. This mix is then added to the main mix.
  • the present invention comprises a method of washing the skin by contacting the skin with an amount of the cleanser compositions herein which is effective to clean the skin and rinsing the excess cleanser from the skin.
  • An effective amount for any individual will depend upon variable factors such as amount of soil on the skin, type of soil on the skin, level of surfactant in the cleanser composition, etc. Generally, an effective amount will be from about 0.5 to about 5 grams per use.
  • Tables 3, 4, 6 and 7 cite degerming results obtained with the Minimum Inhibitory Concentration Disk Test, which procedure is set out below.
  • the degerming performance of the products was evaluated using the Minimum Inhibitory Concentration Disk Test ("MIC Test") for antimicrobial liquid soap products.
  • the MIC Test is a modifi ⁇ cation of a disk diffusion test method used by clinical labora ⁇ tories to determine the susceptibility of infectious organisms to antibiotics. In this method, 50 microliters of a 1% solution of the antimicrobial products is added to filter paper disks 13 mm in diameter. The disks are then applied to the surface of agar plates which have been inoculated with microorganisms. When a. disk is applied to an agar plate, the antimicrobial diffuses through the agar medium.
  • the result is a gradual changing gra ⁇ tower of antimicrobial concentration in the agar surrounding each disk.
  • the organisms that are not inhibited by the antimicrobial multiply on the agar plate forming a lawn of growth which can be visualized. No growth will occur in the area around the disk where the antimicrobial is present in inhibitory concentrations.
  • the more susceptible the microorganism and soluble the antimi ⁇ crobial the larger the zone of inhibition surrounding the disk.
  • the agar plates in the testing that follows were innoculated with Staohylococcus aureus and, in some cases, Escherichia coli. Products are typicallly tested in a random block design. The agar plates are incubated for 18 to 24 hours. The diameters of the circular zones of inhibition are then measured in two directions in millimeters and averaged to establish the zone of inhibition size reported. To account for the variability in zone size across MIC Tests for any given product, which can occur as a result of variations in the bacteria inoculated on the agar plates, products are only compared within the same test.
  • Example 1 shows comparable degerming to Compara ⁇ tive A, a leading commercially available antibacterial hand soap.
  • Example 2 is superior to "A" in degerming.
  • Example 2 has more TCS, 0.5% than Example I, 0.2%. This increase in degerming is unexpected and surprising in view of E4 of Table 7.
  • Example 5 in Table 4 is the more preferred execution of the present invention. TABLE 3 Degerming Examples 1. 2. vs. Comparative Com p osition A
  • E2 has too much ethoxylated surfactant, sodium laureth sulfate. E2 is lower in degerming via a lower zone of inhibition.
  • Example 1 demonstrates equivalent degerming to Comparative "A".
  • the liquid cleansing compositions of the present invention also demonstrate superior mildness to the skin as measured by a clinical mildness test, the results of which are set out in Paired Comparisons # 1 and #2, and Comparison #3. These significant improvements in degerming and mildness are unexpected and surprising in view of the higher ratio of harsher cosurfactant to mild ethoxylated surfactant.
  • the preferred executions are Examples 1, 2, and 5, which contain cationic polymer.
  • Paired Compari- son #1 demonstrates that the addition of 0.25% Jaguar C-14-S in the formula of Example 1 improves mildness over El, which is formulated with the same surfactant base but without polymer and opacifier.
  • Comparison #2 demonstrates that El has equal mildness performance to "A”.
  • Comparison #3 is a sta- tistical evaluation across Paired Comparisons #1 and #2 demon ⁇ strating that Example 1 (also appears as Example 6 in Table 5) is milder to the skin than "A”.
  • the cationic polymer also improves the antibacterial activity of the product. Referring to Table 4, it is shown with Example 3 and Example 4 that increasing the polymer level from 0.25% to 0.5% significantly increases the antibacterial activity at a constant 0.3% level of TCS.

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  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)

Abstract

Est décrite une composition de nettoyant liquide pour la peau présentant une douceur et un pouvoir désinfectant améliorés et comprenant: (A) 0,5 à 5,75 pour-cent en poids d'un surfactant doux éthoxylé; (B) 1 à 40 pour-cent en poids d'un cosurfactant sélectionné dans le groupe composé de surfactants anioniques, non ioniques, zwitterioniques et amphotériques non éthoxylés et de mélanges de ceux-ci; (C) 0,01 à 4 pour-cent en poids d'agent antibactérien; (D) 0,05 à 5 pour-cent en poids d'un polymère cationique soluble dans l'eau; et (E) 35 à 97 pour-cent en poids d'eau.
PCT/US1992/002847 1991-04-15 1992-04-03 Nettoyant liquide, doux, antibacterien pour la peau WO1992018100A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP4510260A JPH06506938A (ja) 1991-04-15 1992-04-03 抗菌性マイルド液体スキンクレンザー
FI934541A FI934541A0 (fi) 1991-04-15 1992-04-03 Antibakteriellt milt flytande hudrengoeringsmedel
BR9205895A BR9205895A (pt) 1991-04-15 1992-04-03 Limpador antibacteriano liquido suave para a pele.
NO933675A NO933675L (no) 1991-04-15 1993-10-12 Antibakterielt, mildt flytende hudrensermiddel

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US68533391A 1991-04-15 1991-04-15
US685,333 1991-04-15

Publications (1)

Publication Number Publication Date
WO1992018100A1 true WO1992018100A1 (fr) 1992-10-29

Family

ID=24751735

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1992/002847 WO1992018100A1 (fr) 1991-04-15 1992-04-03 Nettoyant liquide, doux, antibacterien pour la peau

Country Status (14)

Country Link
EP (1) EP0580814A1 (fr)
JP (1) JPH06506938A (fr)
CN (1) CN1066779A (fr)
AU (1) AU1881792A (fr)
BR (1) BR9205895A (fr)
CA (1) CA2107001A1 (fr)
FI (1) FI934541A0 (fr)
IE (1) IE921185A1 (fr)
MA (1) MA22506A1 (fr)
MX (1) MX9201733A (fr)
NO (1) NO933675L (fr)
PT (1) PT100360A (fr)
TW (1) TW198688B (fr)
WO (1) WO1992018100A1 (fr)

Cited By (44)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993015711A1 (fr) * 1992-02-10 1993-08-19 The Procter & Gamble Company Compositions de premelange de shampooing
FR2708277A1 (fr) * 1993-06-30 1995-02-03 Colgate Palmolive Co Composition aqueuse antibactérienne pour le nettoyage corporel.
WO1995032705A1 (fr) * 1994-06-01 1995-12-07 Unilever Plc Formulations nettoyantes liquides, antimicrobiennes et douces
WO1996021426A1 (fr) * 1995-01-09 1996-07-18 The Procter & Gamble Company Composition de nettoyage de la peau trois en un, liquide, antibacterienne, moussante, ultra douce
WO1996017592A3 (fr) * 1994-12-06 1996-09-06 Procter & Gamble Demaquillant liquide pour la peau stable en conservation avec un ester d'acide gras d'ethylene glycol cristallin; liquide et polymere formant gel
WO1996029049A1 (fr) * 1995-03-20 1996-09-26 Unilever Plc Formulations nettoyantes liquides
GB2303789A (en) * 1995-07-29 1997-03-05 Procter & Gamble Perfumed compositions containing formaldehyde generating preservatives
WO1997016066A1 (fr) * 1995-11-01 1997-05-09 Kimberly-Clark Worldwide, Inc. Compositions antimicrobiennes et serviettes humides les contenant
WO1997016065A1 (fr) * 1995-11-01 1997-05-09 Kimberly-Clark Worldwide, Inc. Procedes d'incorporation d'une substance hydrophobe dans une solution aqueuse
US5646100A (en) * 1994-02-14 1997-07-08 Colgate-Palmolive Company Mild, aqueous skin cleansing composition
WO1997026854A1 (fr) * 1996-01-29 1997-07-31 The Procter & Gamble Company Compositions pour shampooing permettant d'ameliorer l'apport d'agents antimicrobiens
WO1997048377A1 (fr) * 1996-06-15 1997-12-24 Smithkline Beecham Plc Compositions de nettoyage de la peau a base de triclocarban et de tensio-actifs
WO1998032416A1 (fr) * 1997-01-27 1998-07-30 The Procter & Gamble Company Procede de demaquillage de la peau
WO1998055097A1 (fr) * 1997-06-04 1998-12-10 The Procter & Gamble Company Composition nettoyante liquide antimicrobienne douce a rincer contenant de l'acide salicylique
WO1998055099A1 (fr) * 1997-06-04 1998-12-10 The Procter & Gamble Company Compositions nettoyantes antimicrobiennes liquides
WO1998055094A1 (fr) * 1997-06-04 1998-12-10 The Procter & Gamble Company Chiffons antimicrobiens doux
WO1998055092A1 (fr) * 1997-06-04 1998-12-10 The Procter & Gamble Company Composition nettoyante liquide antimicrobienne douce a rincer
WO1998055098A1 (fr) * 1997-06-04 1998-12-10 The Procter & Gamble Company Composition nettoyante liquide antimicrobienne douce a rincer contenant des tensio-actifs acides
WO1998055095A1 (fr) * 1997-06-04 1998-12-10 The Procter & Gamble Company Composition nettoyante liquide antimicrobienne adoucissante a rincer
WO1998055080A3 (fr) * 1997-06-04 1999-03-11 Procter & Gamble Compositions antimicrobiennes a conserver
WO1998055081A3 (fr) * 1997-06-04 1999-03-11 Procter & Gamble Composition nettoyante liquide antimicrobienne douce a conserver
US5968539A (en) * 1997-06-04 1999-10-19 Procter & Gamble Company Mild, rinse-off antimicrobial liquid cleansing compositions which provide residual benefit versus gram negative bacteria
US6034043A (en) * 1999-04-20 2000-03-07 Lever Brothers Company, Division Of Conopco, Inc. Mild antimicrobial liquid cleansing formulations comprising polyvalent cation or cations for improving an antimicrobial effectiveness
WO2000024367A1 (fr) * 1998-10-26 2000-05-04 Firmenich Sa Compositions parfumantes antimicrobiennes
US6126954A (en) * 1999-04-05 2000-10-03 Unilever Home & Personal Care Usa, Division Of Conopco Liquid compositions comprising stable emulsion of small particle skin benefit agent
WO2000066079A1 (fr) * 1999-04-30 2000-11-09 Colgate-Palmolive Company Compositions nettoyantes liquides antibacteriennes pour les mains
US6183757B1 (en) 1997-06-04 2001-02-06 Procter & Gamble Company Mild, rinse-off antimicrobial cleansing compositions which provide improved immediate germ reduction during washing
US6183763B1 (en) 1997-06-04 2001-02-06 Procter & Gamble Company Antimicrobial wipes which provide improved immediate germ reduction
US6190675B1 (en) 1997-06-04 2001-02-20 Procter & Gamble Company Mild, rinse-off antimicrobial liquid cleansing compositions which provide improved residual benefit versus gram positive bacteria
US6197315B1 (en) 1997-06-04 2001-03-06 Procter & Gamble Company Antimicrobial wipes which provide improved residual benefit versus gram negative bacteria
US6214363B1 (en) 1997-11-12 2001-04-10 The Procter & Gamble Company Liquid antimicrobial cleansing compositions which provide residual benefit versus gram negative bacteria
AU735419B2 (en) * 1997-06-04 2001-07-05 Procter & Gamble Company, The Antimicrobial wipes
US6284259B1 (en) 1997-11-12 2001-09-04 The Procter & Gamble Company Antimicrobial wipes which provide improved residual benefit versus Gram positive bacteria
US6287583B1 (en) 1997-11-12 2001-09-11 The Procter & Gamble Company Low-pH, acid-containing personal care compositions which exhibit reduced sting
US6287577B1 (en) 1997-11-12 2001-09-11 The Procter & Gamble Company Leave-on antimicrobial compositions which provide improved residual benefit versus gram positive bacteria
EP0987321A3 (fr) * 1998-09-18 2002-07-03 Unilever N.V. Compositions de nettoyage antibactéricides ultradouces pour usage fréquent
WO2004080176A3 (fr) * 2003-03-06 2004-12-09 Buckman Labor Inc Compositions microbicides comprenant un polymere d'ionene et de l'ether de 2,4,4'-trichloro-2'-hydroxydiphenyle, et leurs procedes d'utilisation
US6903057B1 (en) 2004-05-19 2005-06-07 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Personal product liquid cleansers stabilized with starch structuring system
US6906016B1 (en) 2004-05-19 2005-06-14 Unilever Home & Personal Care Usa, A Division Of Conopco, Inc. Personal product liquid cleansers comprising combined fatty acid and water soluble or water swellable starch structuring system
CN102475639A (zh) * 2010-11-29 2012-05-30 吴克 一种用于儿童洗澡的童趣沐浴露
CN102626375A (zh) * 2012-03-28 2012-08-08 福建省梦娇兰日用化学品有限公司 一种含有氨基酸型表面活性剂的清洁组合物
WO2014082854A2 (fr) 2012-11-29 2014-06-05 Unilever N.V. Compositions de nettoyage antibactériennes douces
CN112515996A (zh) * 2020-11-30 2021-03-19 明尼苏达矿业制造医用器材（上海）有限公司 抑菌洗手液及其制备方法
CN115975742A (zh) * 2022-11-18 2023-04-18 浙江传化日用品有限公司 一种抑菌易漂洗的洗涤剂及其制备方法

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US3761418A (en) * 1967-09-27 1973-09-25 Procter & Gamble Detergent compositions containing particle deposition enhancing agents
US4329336A (en) * 1980-11-10 1982-05-11 Colgate-Palmolive Company Nonionic based antimicrobial shampoo
EP0417501A1 (fr) * 1989-09-14 1991-03-20 Joh. A. Benckiser GmbH Composition gel de douche et shampooing pour cheveur extra douche à basse concentration de tensides
GB2242686A (en) * 1990-04-02 1991-10-09 Kao Corp Cleansing composition

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Publication number Priority date Publication date Assignee Title
US3761418A (en) * 1967-09-27 1973-09-25 Procter & Gamble Detergent compositions containing particle deposition enhancing agents
US4329336A (en) * 1980-11-10 1982-05-11 Colgate-Palmolive Company Nonionic based antimicrobial shampoo
EP0417501A1 (fr) * 1989-09-14 1991-03-20 Joh. A. Benckiser GmbH Composition gel de douche et shampooing pour cheveur extra douche à basse concentration de tensides
GB2242686A (en) * 1990-04-02 1991-10-09 Kao Corp Cleansing composition

Cited By (63)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993015711A1 (fr) * 1992-02-10 1993-08-19 The Procter & Gamble Company Compositions de premelange de shampooing
FR2708277A1 (fr) * 1993-06-30 1995-02-03 Colgate Palmolive Co Composition aqueuse antibactérienne pour le nettoyage corporel.
EP0670158A3 (fr) * 1994-02-14 1997-09-24 Colgate Palmolive Co Composition de nettoyage.
US5646100A (en) * 1994-02-14 1997-07-08 Colgate-Palmolive Company Mild, aqueous skin cleansing composition
WO1995032705A1 (fr) * 1994-06-01 1995-12-07 Unilever Plc Formulations nettoyantes liquides, antimicrobiennes et douces
CN1072928C (zh) * 1994-06-01 2001-10-17 尤尼利弗公司 温和的抗微生物液体洗涤制剂
EP0762868A1 (fr) 1994-06-01 1997-03-19 Unilever Plc Formulations nettoyantes liquides, antimicrobiennes et douces
EP1502584A1 (fr) * 1994-06-01 2005-02-02 Unilever Plc Formulations nettoyantes liquides, antimicrobiennes et douces
US5681802A (en) * 1994-06-01 1997-10-28 Lever Brothers Company, Division Of Conopco, Inc. Mild antimicrobial liquid cleansing formulations comprising buffering compound or compounds as potentiator of antimicrobial effectiveness
WO1996017592A3 (fr) * 1994-12-06 1996-09-06 Procter & Gamble Demaquillant liquide pour la peau stable en conservation avec un ester d'acide gras d'ethylene glycol cristallin; liquide et polymere formant gel
WO1996021426A1 (fr) * 1995-01-09 1996-07-18 The Procter & Gamble Company Composition de nettoyage de la peau trois en un, liquide, antibacterienne, moussante, ultra douce
US5883059A (en) * 1995-01-09 1999-03-16 The Procter & Gamble Company Three in one ultra mild lathering antibacterial liquid personal cleansing composition
WO1996029049A1 (fr) * 1995-03-20 1996-09-26 Unilever Plc Formulations nettoyantes liquides
GB2303789A (en) * 1995-07-29 1997-03-05 Procter & Gamble Perfumed compositions containing formaldehyde generating preservatives
US5700842A (en) * 1995-11-01 1997-12-23 Kimberly-Clark Worldwide, Inc. Methods of incorporating a hydrophobic substance into an aqueous solution
WO1997016065A1 (fr) * 1995-11-01 1997-05-09 Kimberly-Clark Worldwide, Inc. Procedes d'incorporation d'une substance hydrophobe dans une solution aqueuse
WO1997016066A1 (fr) * 1995-11-01 1997-05-09 Kimberly-Clark Worldwide, Inc. Compositions antimicrobiennes et serviettes humides les contenant
US5888524A (en) * 1995-11-01 1999-03-30 Kimberly-Clark Worldwide, Inc. Antimicrobial compositions and wet wipes including the same
WO1997026854A1 (fr) * 1996-01-29 1997-07-31 The Procter & Gamble Company Compositions pour shampooing permettant d'ameliorer l'apport d'agents antimicrobiens
WO1997048377A1 (fr) * 1996-06-15 1997-12-24 Smithkline Beecham Plc Compositions de nettoyage de la peau a base de triclocarban et de tensio-actifs
US6224886B1 (en) 1996-06-15 2001-05-01 Smithkline Beecham P.L.C. Skin wash compositions comprising triclocarban and surfactants
WO1998032416A1 (fr) * 1997-01-27 1998-07-30 The Procter & Gamble Company Procede de demaquillage de la peau
US5942238A (en) * 1997-01-27 1999-08-24 The Procter & Gamble Company Method for removing make-up from skin
AU745439B2 (en) * 1997-06-04 2002-03-21 Procter & Gamble Company, The Leave-on antimicrobial compositions
WO1998055097A1 (fr) * 1997-06-04 1998-12-10 The Procter & Gamble Company Composition nettoyante liquide antimicrobienne douce a rincer contenant de l'acide salicylique
WO1998055080A3 (fr) * 1997-06-04 1999-03-11 Procter & Gamble Compositions antimicrobiennes a conserver
WO1998055095A1 (fr) * 1997-06-04 1998-12-10 The Procter & Gamble Company Composition nettoyante liquide antimicrobienne adoucissante a rincer
WO1998055098A1 (fr) * 1997-06-04 1998-12-10 The Procter & Gamble Company Composition nettoyante liquide antimicrobienne douce a rincer contenant des tensio-actifs acides
US5968539A (en) * 1997-06-04 1999-10-19 Procter & Gamble Company Mild, rinse-off antimicrobial liquid cleansing compositions which provide residual benefit versus gram negative bacteria
WO1998055081A3 (fr) * 1997-06-04 1999-03-11 Procter & Gamble Composition nettoyante liquide antimicrobienne douce a conserver
AU745392B2 (en) * 1997-06-04 2002-03-21 Procter & Gamble Company, The Mild, leave-on antimicrobial compositions
WO1998055099A1 (fr) * 1997-06-04 1998-12-10 The Procter & Gamble Company Compositions nettoyantes antimicrobiennes liquides
WO1998055094A1 (fr) * 1997-06-04 1998-12-10 The Procter & Gamble Company Chiffons antimicrobiens doux
US6183757B1 (en) 1997-06-04 2001-02-06 Procter & Gamble Company Mild, rinse-off antimicrobial cleansing compositions which provide improved immediate germ reduction during washing
US6183763B1 (en) 1997-06-04 2001-02-06 Procter & Gamble Company Antimicrobial wipes which provide improved immediate germ reduction
US6190674B1 (en) 1997-06-04 2001-02-20 Procter & Gamble Company Liquid antimicrobial cleansing compositions
US6190675B1 (en) 1997-06-04 2001-02-20 Procter & Gamble Company Mild, rinse-off antimicrobial liquid cleansing compositions which provide improved residual benefit versus gram positive bacteria
US6197315B1 (en) 1997-06-04 2001-03-06 Procter & Gamble Company Antimicrobial wipes which provide improved residual benefit versus gram negative bacteria
US6210695B1 (en) 1997-06-04 2001-04-03 The Procter & Gamble Company Leave-on antimicrobial compositions
AU735419B2 (en) * 1997-06-04 2001-07-05 Procter & Gamble Company, The Antimicrobial wipes
WO1998055092A1 (fr) * 1997-06-04 1998-12-10 The Procter & Gamble Company Composition nettoyante liquide antimicrobienne douce a rincer
US6214363B1 (en) 1997-11-12 2001-04-10 The Procter & Gamble Company Liquid antimicrobial cleansing compositions which provide residual benefit versus gram negative bacteria
US6284259B1 (en) 1997-11-12 2001-09-04 The Procter & Gamble Company Antimicrobial wipes which provide improved residual benefit versus Gram positive bacteria
US6287583B1 (en) 1997-11-12 2001-09-11 The Procter & Gamble Company Low-pH, acid-containing personal care compositions which exhibit reduced sting
US6287577B1 (en) 1997-11-12 2001-09-11 The Procter & Gamble Company Leave-on antimicrobial compositions which provide improved residual benefit versus gram positive bacteria
EP0987321A3 (fr) * 1998-09-18 2002-07-03 Unilever N.V. Compositions de nettoyage antibactéricides ultradouces pour usage fréquent
WO2000024367A1 (fr) * 1998-10-26 2000-05-04 Firmenich Sa Compositions parfumantes antimicrobiennes
US6479456B1 (en) 1998-10-26 2002-11-12 Firmenich Sa Antimicrobial perfume compositions
EP1716844A1 (fr) 1999-04-05 2006-11-02 Unilever Plc Compositions liquides contenant un agent benefique pour la peau
US6126954A (en) * 1999-04-05 2000-10-03 Unilever Home & Personal Care Usa, Division Of Conopco Liquid compositions comprising stable emulsion of small particle skin benefit agent
US6034043A (en) * 1999-04-20 2000-03-07 Lever Brothers Company, Division Of Conopco, Inc. Mild antimicrobial liquid cleansing formulations comprising polyvalent cation or cations for improving an antimicrobial effectiveness
WO2000066079A1 (fr) * 1999-04-30 2000-11-09 Colgate-Palmolive Company Compositions nettoyantes liquides antibacteriennes pour les mains
WO2004080176A3 (fr) * 2003-03-06 2004-12-09 Buckman Labor Inc Compositions microbicides comprenant un polymere d'ionene et de l'ether de 2,4,4'-trichloro-2'-hydroxydiphenyle, et leurs procedes d'utilisation
US6903057B1 (en) 2004-05-19 2005-06-07 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Personal product liquid cleansers stabilized with starch structuring system
US6906016B1 (en) 2004-05-19 2005-06-14 Unilever Home & Personal Care Usa, A Division Of Conopco, Inc. Personal product liquid cleansers comprising combined fatty acid and water soluble or water swellable starch structuring system
CN102475639A (zh) * 2010-11-29 2012-05-30 吴克 一种用于儿童洗澡的童趣沐浴露
CN102626375A (zh) * 2012-03-28 2012-08-08 福建省梦娇兰日用化学品有限公司 一种含有氨基酸型表面活性剂的清洁组合物
WO2014082854A2 (fr) 2012-11-29 2014-06-05 Unilever N.V. Compositions de nettoyage antibactériennes douces
DE202013012381U1 (de) 2012-11-29 2016-08-03 Unilever N.V. Milde antibakterielle Reinigungszusammensetzungen
US9655866B2 (en) 2012-11-29 2017-05-23 Conopco, Inc. Mild antibacterial cleansing compositions
CN112515996A (zh) * 2020-11-30 2021-03-19 明尼苏达矿业制造医用器材（上海）有限公司 抑菌洗手液及其制备方法
CN112515996B (zh) * 2020-11-30 2023-09-01 明尼苏达矿业制造医用器材（上海）有限公司 抑菌洗手液及其制备方法
CN115975742A (zh) * 2022-11-18 2023-04-18 浙江传化日用品有限公司 一种抑菌易漂洗的洗涤剂及其制备方法

Also Published As

Publication number Publication date
CA2107001A1 (fr) 1992-10-16
IE921185A1 (en) 1992-10-21
EP0580814A1 (fr) 1994-02-02
NO933675D0 (no) 1993-10-12
FI934541L (fi) 1993-10-14
CN1066779A (zh) 1992-12-09
MA22506A1 (fr) 1992-12-31
JPH06506938A (ja) 1994-08-04
PT100360A (pt) 1993-06-30
TW198688B (fr) 1993-01-21
NO933675L (no) 1993-12-15
FI934541A0 (fi) 1993-10-14
AU1881792A (en) 1992-11-17
MX9201733A (es) 1992-10-01
BR9205895A (pt) 1994-09-27

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