WO2019071994A1 - Composition détergente antimicrobienne de blanchisserie - Google Patents

Composition détergente antimicrobienne de blanchisserie Download PDF

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Publication number
WO2019071994A1
WO2019071994A1 PCT/CN2018/097326 CN2018097326W WO2019071994A1 WO 2019071994 A1 WO2019071994 A1 WO 2019071994A1 CN 2018097326 W CN2018097326 W CN 2018097326W WO 2019071994 A1 WO2019071994 A1 WO 2019071994A1
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WIPO (PCT)
Prior art keywords
laundry detergent
microbial
composition
surfactant
detergent composition
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Application number
PCT/CN2018/097326
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English (en)
Inventor
Haiyan Song
Li LV
Mai NIKI
Xiujun Xu
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 JP2018190773A priority Critical patent/JP6749378B2/ja
Priority to CN201811184984.8A priority patent/CN109652230B/zh
Publication of WO2019071994A1 publication Critical patent/WO2019071994A1/fr

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    • 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
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/94—Mixtures with anionic, cationic or non-ionic compounds
    • 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
    • C11D1/83—Mixtures of non-ionic with anionic compounds
    • 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
    • C11D3/02—Inorganic compounds ; Elemental compounds
    • C11D3/04—Water-soluble compounds
    • C11D3/042—Acids
    • 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
    • C11D3/02—Inorganic compounds ; Elemental compounds
    • C11D3/04—Water-soluble compounds
    • C11D3/044—Hydroxides or bases
    • 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
    • C11D3/02—Inorganic compounds ; Elemental compounds
    • C11D3/04—Water-soluble compounds
    • C11D3/046—Salts
    • 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
    • C11D3/162—Organic compounds containing Si
    • 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
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2003—Alcohols; Phenols
    • C11D3/2006—Monohydric alcohols
    • C11D3/201—Monohydric alcohols linear
    • 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
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2003—Alcohols; Phenols
    • C11D3/2041—Dihydric alcohols
    • C11D3/2044—Dihydric alcohols linear
    • 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
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2068—Ethers
    • 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
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2075—Carboxylic acids-salts thereof
    • C11D3/2079—Monocarboxylic acids-salts thereof
    • 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
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2075—Carboxylic acids-salts thereof
    • C11D3/2086—Hydroxy carboxylic acids-salts thereof
    • 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
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/30—Amines; Substituted amines ; Quaternized amines
    • 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
    • C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3749—Polyolefins; Halogenated polyolefins; Natural or synthetic rubber; Polyarylolefins or halogenated polyarylolefins
    • 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
    • C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3769—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines
    • C11D3/3773—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines in liquid 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/38—Products with no well-defined composition, e.g. natural products
    • C11D3/382—Vegetable products, e.g. soya meal, wood flour, sawdust
    • 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
    • C11D3/38—Products with no well-defined composition, e.g. natural products
    • C11D3/386—Preparations containing enzymes, e.g. protease or amylase
    • C11D3/38618—Protease or amylase in liquid compositions only
    • 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
    • C11D3/40—Dyes ; Pigments
    • 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
    • C11D3/40—Dyes ; Pigments
    • C11D3/42—Brightening agents ; Blueing agents
    • 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/146—Sulfuric acid esters
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds
    • 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
    • C11D1/75—Amino oxides
    • 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
    • C11D1/88—Ampholytes; Electroneutral compounds
    • 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
    • C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
    • C11D2111/10—Objects to be cleaned
    • C11D2111/12—Soft surfaces, e.g. textile

Definitions

  • the present invention relates to an anti-microbial laundry detergent composition.
  • an anti-microbial laundry detergent product is desired by users as it cleans fabrics whilst having an anti-microbial benefit on fabrics.
  • various anti-microbial agents e.g., diphenyl ethers, are known for use in consumer product formulations to deliver an anti-microbial effect.
  • an anti-microbial laundry detergent composition comprising:
  • composition from about 0.05%to about 3%by weight of the composition, of an anti-microbial agent selected from the group consisting of diphenyl ethers and combinations thereof;
  • an amphoteric surfactant selected from the group consisting of C 6 -C 20 alkyldimethyl amine oxides (AO) and combinations thereof;
  • anionic surfactant selected from the group consisting of C 6 -C 20 linear alkylbenzene sulfonates (LAS) and combinations thereof, while such anionic surfactant is present as the main surfactant of the composition.
  • the anti-microbial agent is a hydroxyl diphenyl ether of formula (I) :
  • each Y is independently selected from chlorine, bromine, or fluorine
  • each Z is independently selected from SO 2 H, NO 2 , or C 1 -C 4 alkyl,
  • r 0, 1, 2, or 3
  • o 0, 1, 2, or 3
  • p 0, 1, or 2
  • n 1 or 2
  • n 0 or 1.
  • the anti-microbial agent is selected from the group consisting of 4-4’-dichloro-2-hydroxy diphenyl ether, 2, 4, 4’-trichloro-2’-hydroxy diphenyl ether, and a combination thereof. Most preferably, the anti-microbial agent is 4-4’-dichloro-2-hydroxy diphenyl ether.
  • the anti-microbial agent can be present in the anti-microbial laundry detergent composition of the present invention at an amount ranging from about 0.05%to about 1%, preferably from about 0.07%to about 0.5%, by weight of the composition.
  • amphoteric surfactant useful for practice of the present invention can be readily selected from the group consisting of C 10 -C 16 alkyldimethyl amine oxides and combinations thereof.
  • the amphoteric surfactant is selected from the group consisting of dodecyldimethyl amine oxide, tetradecyldimethyl amino oxide, and a combination thereof. More preferably, the amphoteric surfactant is dodecyldimethyl amine oxide.
  • amphoteric surfactant can be present in the anti-microbial laundry detergent composition of the present invention at an amount ranging from about 0.1%to about 5%, preferably from about 0.2%to about 2%, by weight of the composition.
  • the anionic surfactant suitable for use in the present invention can be selected from the group consisting of C 10 -C 16 linear alkylbenzene sulfonates and combinations thereof.
  • such anionic surfactant is selected from the group consisting of C 12 -C 14 linear alkylbenzene sulfonates and a combination thereof.
  • the anionic surfactant can be present in the anti-microbial laundry detergent composition of the present invention at an amount ranging from about 6%to about 30%, preferably from about 8%to about 20%, by weight of the composition. More preferably, such anionic surfactant is present as the majority surfactant in the anti-microbial laundry detergent composition of the present invention.
  • the anti-microbial laundry detergent composition comprises:
  • anionic surfactant which is a C 12 linear alkylbenzene sulfonate, while such anionic surfactant is present as the majority surfactant in the composition.
  • the present invention relates to a method of pretreating or treating a soiled fabric comprising contacting the soiled fabric with the anti-microbial laundry detergent composition as mentioned hereinabove.
  • the terms “comprise” , “comprises” , “comprising” , “include” , “includes” , “including” , “contain” , “contains” , and “containing” are meant to be non-limiting, i.e., other steps and other ingredients which do not affect the end of result can be added.
  • the above terms encompass the terms “consisting of” and “consisting essentially of” .
  • composition is “substantially free” of a specific ingredient, it is meant that the composition comprises less than a trace amount, alternatively less than 0.1%, alternatively less than 0.01%, alternatively less than 0.001%, by weight of the composition, of the specific ingredient.
  • the term “laundry detergent composition” means a composition for cleaning soiled materials, including fabrics. Such compositions may be used as a pre-laundering treatment, a post-laundering treatment, or may be added during the rinse or wash cycle of the laundering operation.
  • the laundry detergent composition compositions may have a form selected from liquid, powder, single-phase or multi-phase unit dose, pouch, tablet, gel, paste, bar, or flake.
  • the laundry detergent composition is a liquid.
  • liquid laundry detergent composition herein refers to compositions that are in a form selected from the group consisting of pourable liquid, gel, cream, and combinations thereof.
  • the liquid laundry detergent composition may be either aqueous or non-aqueous, and may be anisotropic, isotropic, or combinations thereof.
  • anti-microbial agent refers to a chemical compound of which the principle intended function is to kill bacteria or to prevent their growth or reproduction.
  • Traditional anti-microbial agents include cationic anti-microbial agents (e.g., certain ammonium chlorides) , nonionic anti-microbial agents, etc.
  • Diphenyl ether compounds that are used in the present invention are nonionic anti-microbial agents.
  • main surfactant refers to a surfactant that is present in a composition at an amount that is greater than any other surfactant contained by such composition.
  • major surfactant refers to a surfactant that is present in a composition at an amount that is at least 50%by weight of the total surfactant content in such composition.
  • alkyl means a hydrocarbyl moiety which is branched or unbranched, substituted or unsubstituted. Included in the term “alkyl” is the alkyl portion of acyl groups.
  • washing solution refers to the typical amount of aqueous solution used for one cycle of laundry washing, preferably from 1 L to 50 L, alternatively from 1 L to 20 L for hand washing and from 20 L to 50 L for machine washing.
  • oiled fabric is used non-specifically and may refer to any type of natural or artificial fibers, including natural, artificial, and synthetic fibers, such as, but not limited to, cotton, linen, wool, polyester, nylon, silk, acrylic, and the like, as well as various blends and combinations.
  • the anti-microbial laundry detergent composition of the present invention comprises an anti-microbial agent of diphenyl ether in a specific surfactant system, which comprises an amphoteric surfactant (preferably AO) and an anionic surfactant (preferably LAS) , while preferably the anionic surfactant is present as the main surfactant, more preferably as the majority surfactant, in such composition.
  • a specific surfactant system which comprises an amphoteric surfactant (preferably AO) and an anionic surfactant (preferably LAS)
  • preferably the anionic surfactant is present as the main surfactant, more preferably as the majority surfactant, in such composition.
  • the anti-microbial agent is present from about 0.05%to about 3%, more preferably from about 0.05%to about 1%, most preferably from about 0.07%to about 0.5%, by weight of the composition.
  • the amphoteric AO surfactant is preferably present in the composition at an amount ranging from about 0.05%to about 10%, more preferably from about 0.1%to about 5%, most preferably from about 0.2%to about 2%, by weight of the composition.
  • the anionic LAS surfactant is preferably present in the composition at an amount ranging from about 5%to about 50%, more preferably from about 6%to about 30%, most preferably from about 8%to about 20%, by weight of the composition.
  • the anionic LAS surfactant is present as the main surfactant of the composition, or preferably as the majority surfactant of the composition, e.g., at no less than about 40%, preferably no less than about 50%, more preferably no less than about 55%, most preferably no less than 60%, and up to about 99%, preferably up to about 95%, more preferably up to about 90%, by weight of the total surfactant content of the composition.
  • the laundry detergent composition is preferably capable of delivering the anti-microbial agent at a level from about 0.01 ppm to about 5 ppm, more preferably from about 0.05 ppm to about 3 ppm, more preferably from about 0.1 ppm to about 1 ppm.
  • the laundry detergent composition herein provides anti-microbial benefits against both Gram positive bacteria (e.g., Staphylococcus aureus) and Gram negative bacteria (e.g., Klebsiella pneumoniae) .
  • the composition preferably provides residual anti-microbial benefits to the fabrics treated by the composition, i.e., the nonionic anti-microbial agent therein deposits onto the fabrics during a washing cycle and subsequently the deposited (i.e., residual) antimicrobial-agent prevents bacteria growth onto the fabrics during drying or storage or wear.
  • the laundry detergent composition provides a Bacteriostatic Activity Value of at least a log 2.2 reduction, preferably a log 2.5 reduction, against both Gram positive bacteria and Gram negative bacteria, to treated fabrics versus non-treated fabrics.
  • the composition provides at least a log 2.2 reduction, preferably a log 2.5 reduction, against Staphylococcus aureus and/or Klebsiella pneumoniae after a 10 minutes contact time in a 1055 ppm aqueous solution as determined by the JISL 1902 method (that is described below) . More preferably, the composition provides at least a log 3.0 reduction, preferably a log 3.5 reduction, against Staphylococcus aureus. It is worth noting that Staphylococcus aureus is frequently found on human skin and therefore fabrics (particularly wearing fabrics) are in particular need of anti-microbial effects against Staphylococcus aureus.
  • the laundry detergent composition herein may be acidic or alkali or pH neutral, depending on the ingredients incorporated in the composition.
  • the pH range of the laundry detergent composition is preferably from about 4 to about 12, more preferably from about 6 to about 11, even more preferably from about 7 to about 10.
  • the laundry detergent composition can have any suitable viscosity depending on factors such as formulated ingredients and purpose of the composition.
  • the composition has a high shear viscosity value, at a shear rate of 20/sec and a temperature of 21°C, of about 200 to about 3,000 cP, alternatively about 300 to about 2,000 cP, alternatively about 500 to about 1,000 cP, and a low shear viscosity value, at a shear rate of 1/sec and a temperature of 21°C, of about 500 to about 100,000 cP, alternatively about 1000 to about 10,000 cP, alternatively about 1,500 to about 5,000 cP.
  • the diphenyl ether-based anti-microbial agent of the present invention is a nonionic compound.
  • the anti-microbial agent of the present invention allows for a stable liquid anti-microbial laundry detergent composition.
  • cationic anti-microbial agents are typically not compatible with anionic surfactants present in the laundry detergent compositions.
  • the anti-microbial agent is a hydroxyl diphenyl ether.
  • the anti-microbial agent herein can be either halogenated or non-halogenated, but preferably is halogenated.
  • the anti-microbial agent is a hydroxyl diphenyl ether of formula (I) :
  • each Y is independently selected from chlorine, bromine, or fluorine, preferably is chlorine or bromine, more preferably is chlorine,
  • each Z is independently selected from SO 2 H, NO 2 , or C 1 -C 4 alkyl,
  • r is 0, 1, 2, or 3, preferably is 1 or 2
  • o is 0, 1, 2, or 3, preferably is 0, 1 or 2
  • p is 0, 1, or 2, preferably is 0,
  • n 1 or 2, preferably is 1, and
  • n 0 or 1, preferably is 0.
  • 0 means nil.
  • p when p is 0, then there is no Z in formula (I) .
  • Each Y and each Z could be the same or different.
  • o is 1, r is 2, and Y is chlorine or bromine.
  • This embodiment could be: one chlorine atom bonds to a benzene ring while the bromine atom and the other chlorine atom bond to the other benzene ring; or the bromine atom bonds to a benzene ring while the two chlorine atoms bond to the other benzene ring.
  • the anti-microbial agent is selected from the group consisting of 4-4’-dichloro-2-hydroxy diphenyl ether ( “Diclosan” ) , 2, 4, 4’-trichloro-2’-hydroxy diphenyl ether ( “Triclosan” ) , and a combination thereof.
  • the anti-microbial agent is 4-4’-dichloro-2-hydroxy diphenyl ether, commercially available from BASF, under the trademark name
  • anti-microbial agents may also be present, provided that these are not present at a level which causes instability in the formulation.
  • useful further antimicrobial agents are chelating agents, which are particularly useful in reducing the resistance of Gram negative microbes in hard water.
  • Acid biocides may also be present.
  • amphoteric surfactant suitable for use in the present invention can be selected from the group consisting of C 6 -C 20 alkyldimethyl amine oxides (AO) and combinations thereof.
  • the amine oxide surfactant is characterized by the following structure:
  • R 1 is a C 6-20 alkyl, a C 6-20 hydroxyalkyl, or a C 6-20 alkyl phenyl group
  • each R 2 is a C 2-5 alkylene, or a C 2-5 hydroxyalkylene group
  • x is from 0 to about 3
  • each R 3 is a C 1-3 alkyl, a C 1-3 hydroxyalkyl, or a polyethylene oxide containing from about 1 to about 3 ethoxylene (EO) units.
  • the amine oxide surfactant may be a C 8-18 alkyldimethyl amine oxide, preferably a C 10-16 alkyldimethyl amine oxide.
  • the amphoteric surfactant is selected from the group consisting of dodecyldimethyl amine oxide, tetradecyldimethyl amino oxide, and a combination thereof. More preferably, the amphoteric surfactant contains dodecyldimethyl amino oxide having the following formula (II) :
  • Such a compound is also referred to as lauryldimethyl amine oxide or dodecydimethyl amine-N-oxide (DDAO) . It is commercially available from Huntsman under the tradename LO.
  • a relatively small amount of the AO surfactant e.g., from about 0.05%to about 10%, or from about 0.1%to about 5%, or from about 0.2%to about 2%, in the laundry detergent composition can significantly improves the deposition rate of the diphenyl ether anti-microbial agent onto washed fabrics.
  • the AO surfactant may modify the micelle structure in the washing solution formed by the laundry detergent composition of the present invention, thereby to drive deeper penetration of the diphenyl ether anti-microbial agent into the fabrics and to improve the overall deposition rate of such ant-microbial agent on washed fabrics.
  • the C 6 -C 20 linear alkylbenzene sulfonate surfactant is a required surfactant for the laundry detergent composition of the present invention.
  • LAS is C 10 -C 16 LAS, preferably C 12 -C 14 LAS.
  • the LAS is normally prepared by sulfonation (using SO 2 or SO 3 ) of alkylbenzenes followed by neutralization.
  • Suitable alkylbenzene feedstocks can be made from olefins, paraffins or mixtures thereof using any suitable alkylation scheme, including sulfuric and HF-based processes.
  • the precise alkylation catalyst it is possible to widely vary the position of covalent attachment of benzene to an aliphatic hydrocarbon chain. Accordingly, the LAS herein can vary widely in 2-phenyl isomer and/or internal isomer content.
  • the level of LAS is preferably higher than that of any other surfactant contained by such composition, i.e., the LAS is the main surfactant in such composition. More preferably, the LAS is present at an amount that is at least about 50%, or at least about 55%, by weight of the total surfactant content in such composition.
  • Such a LAS-rich or LAS-dominant surfactant system further boosts deposition of the diphenyl ether anti-microbial agent onto washed fabrics, in comparison with other surfactant systems enriched by or dominated by other surfactants, such as C 6 -C 20 alkyl alkoxy sulfates (AE x S) and nonionic surfactants, as discussed hereinafter.
  • the laundry detergent composition of the present invention may comprise one or more other surfactants, such as other anionic surfactants (i.e., other than LAS) , nonionic surfactants, other amphoteric surfactants (i.e., other than AO) , cationic surfactants, and zwitterionic surfactants, provided that the content of each of such other surfactants is lower than that of the LAS surfactant.
  • the total content of all other surfactants is lower than that of the LAS surfactant.
  • the laundry detergent composition may contain a C 6 -C 20 alkyl alkoxy sulfates (AE x S) , wherein x is about 1-30, preferably about 1-15, more preferably about 1-10, most preferably x is about 1-3.
  • AE x S alkyl alkoxy sulfates
  • the alkyl chain in such AE x S can be either linear or branched, with mid-chain branched AE x S surfactants being particularly preferred.
  • a preferred group of AE x S include C 12 -C 14 alkyl alkoxy sulfates with x of about 1-3.
  • the amount of AE x S surfactant (s) in the laundry detergent composition of the present invention may range from about 0.05%to about 30%, preferably from about 0.1%to about 20%, more preferably from about 0.5% to about 15%, most preferably from about 1%to about 5%, by weight of the composition. Without being bound by any theory, it is believed that a higher level of AE x S may not help, but may actually have an adverse impact on, the deposition of the anti-microbial agent onto washed fabrics, so it is desirable to keep the AE x S content in the laundry detergent composition of the present invention relatively low.
  • the laundry detergent composition may contain an alkoxylated nonionic surfactant.
  • alkoxylated nonionic surfactants suitable for use herein include: C 12 -C 18 alkyl ethoxylates, such as nonionic surfactants available from Shell; C 6 -C 12 alkyl phenol alkoxylates wherein the alkoxylate units are a mixture of ethyleneoxy and propyleneoxy units; C 12 -C 18 alcohol and C 6 -C 12 alkyl phenol condensates with ethylene oxide/propylene oxide block alkyl polyamine ethoxylates such as available from BASF; C 14 -C 22 mid-chain branched alkyl alkoxylates, BAEx, wherein x is from about 1 to about 30; alkylpolysaccharides, specifically alkylpolyglycosides; polyhydroxy fatty acid amides; and ether capped poly (oxyalkylated) alcohol surfactants.
  • alkoxylated ester surfactants such as those having the formula R 1 C (O) O (R 2 O) nR 3 wherein R 1 is selected from linear and branched C 6 -C 22 alkyl or alkylene moieties; R 2 is selected from C 2 H 4 and C 3 H 6 moieties and R 3 is selected from H, CH 3 , C 2 H 5 and C 3 H 7 moieties; and n has a value between about 1 and about 20.
  • alkoxylated ester surfactants include the fatty methyl ester ethoxylates (MEE) and are well-known in the art.
  • the alkoxylated nonionic surfactant contained by the laundry detergent composition of the present invention is a C 6 -C 20 alkoxylated alcohol, preferably C 8 -C 18 alkoxylated alcohol, more preferably C 10 -C 16 alkoxylated alcohol.
  • the C 6 -C 20 alkoxylated alcohol is preferably an alkyl alkoxylated alcohol with an average degree of alkoxylation of from about 1 to about 50, preferably from about 3 to about 30, more preferably from about 5 to about 20, even more preferably from about 5 to about 9.
  • the alkoxylation herein may be ethoxylation, propoxylation, or a mixture thereof, but preferably is ethoxylation.
  • the alkoxylated nonionic surfactant is C 6 -C 20 ethoxylated alcohol, preferably C 8 -C 18 alcohol ethoxylated with an average of about 5 to about 20 moles of ethylene oxides, more preferably C 10 -C 16 alcohol ethoxylated with an average of about 5 to about 9 moles of ethylene oxides.
  • the most preferred alkoxylated nonionic surfactant is C 12 -C 15 alcohol ethoxylated with an average of about 7 moles of ethylene oxide, e.g., commercially available from Shell.
  • the amount of nonionic surfactant (s) in the laundry detergent composition of the present invention may range from about 0.1%to about 30%, preferably from about 0.5%to about 25%, more preferably from about 1%to about 20%, most preferably from about 5%to about 10%, by weight of the composition.
  • the anti-microbial laundry detergent composition of the present invention comprises:
  • composition LAS from about 8%to about 20%by weight of the composition, of the anionic surfactant, which is a C 12 -C 14 LAS and which is present as the majority surfactant of such composition LAS;
  • a nonionic surfactant which is a C 12 -C 15 alcohol ethoxylated with an average of about 7 moles of ethylene oxide.
  • the weight ratio of LAS to AE x S is preferably at least 2: 1, preferably at least 3: 1, more preferably at least 5: 1, most preferably at least 7: 1.
  • the weight ratio of LAS to NI may be at least 1.25: 1, preferably at least 1.5: 1, more preferably at least 1.6: 1.
  • the laundry detergent composition of the present invention may further comprise a cationic surfactant.
  • cationic surfactants include: quaternary ammonium surfactants, which can have up to 26 carbon atoms include: alkoxylate quaternary ammonium (AQA) surfactants; dimethyl hydroxyethyl quaternary ammonium; dimethyl hydroxyethyl lauryl ammonium chloride; polyamine cationic surfactants; and amino surfactants, specifically amido propyldimethyl amine (APA) .
  • AQA alkoxylate quaternary ammonium
  • APA amino surfactants
  • the laundry detergent composition of the present invention may further comprise another amphoteric surfactant (i.e., besides AO) .
  • amphoteric surfactants include: derivatives of secondary and tertiary amines, derivatives of heterocyclic secondary and tertiary amines, or derivatives of quaternary ammonium, quaternary phosphonium or tertiary sulfonium compounds.
  • Preferred examples include: betaine, including alkyl dimethyl betaine and cocodimethyl amidopropyl betaine, sulfo and hydroxy betaines, such as N-alkyl-N, N-dimethylammino-1-propane sulfonate where the alkyl group can be C 8 -C 18 or C 10 -C 14 .
  • adjunct ingredients include but are not limited to: builders, chelating agents, rheology modifiers, dye transfer inhibiting agents, dispersants, enzymes, and enzyme stabilizers, catalytic materials, bleach activators, hydrogen peroxide, sources of hydrogen peroxide, preformed peracids, polymeric dispersing agents, clay soil removal/anti-redeposition agents, brighteners, suds suppressors, dyes, photobleaches, perfumes, perfume microcapsules, structure elasticizing agents, fabric softeners, carriers, hydrotropes, processing aids, solvents, hueing agents, structurants and/or pigments.
  • the precise nature of these adjunct ingredients and the levels thereof in the laundry detergent composition will depend on the physical form of the composition and the nature of the cleaning operation for which it is to be used.
  • the composition herein comprises a rheology modifier (also referred to as a “structurant” in certain situations) , which functions to suspend and stabilize certain particulate ingredients and to adjust the viscosity of the composition so as to be more applicable to the packaging assembly.
  • the rheology modifier herein can be any known ingredient that is capable of suspending particles and/or adjusting rheology to a liquid composition.
  • the rheology modifier is selected from the group consisting of hydroxy-containing crystalline material, polyacrylate, polysaccharide, polycarboxylate, alkali metal salt, alkaline earth metal salt, ammonium salt, alkanolammonium salt, C 12 -C 20 fatty alcohol, di-benzylidene polyol acetal derivative (DBPA) , di-amido gallant, a cationic polymer comprising a first structural unit derived from methacrylamide and a second structural unit derived from diallyl dimethyl ammonium chloride, and a combination thereof.
  • DBPA di-benzylidene polyol acetal derivative
  • the rheology modifier is a hydroxy-containing crystalline material generally characterized as crystalline, hydroxyl-containing fatty acids, fatty esters and fatty waxes, such as castor oil and castor oil derivatives. More preferably the rheology modifier is a hydrogenated castor oil (HCO) .
  • HCO hydrogenated castor oil
  • the laundry detergent composition of the present invention is generally prepared by conventional methods such as those known in the art of making laundry detergent compositions. Such methods typically involve mixing the essential and optional ingredients in any desired order to a relatively uniform state, with or without heating, cooling, application of vacuum, and the like, thereby providing laundry detergent compositions containing ingredients in the requisite concentrations.
  • Another aspect of the present invention is directed to a method of using the laundry detergent composition to treat a fabric with an anti-microbial benefit.
  • the method comprises the step of administering from 5 g to 120 g of the above-mentioned laundry detergent composition into a laundry washing basin comprising water to form a washing solution.
  • the washing solution in a laundry washing basin herein preferably has a volume from 1 L to 50 L, alternatively from 1 L to 20 L for hand washing and from 20 L to 50 L for machine washing.
  • the anti-microbial benefit herein is determined by the JISL 1902 method.
  • the temperatures of the laundry washing solution preferably range from 5°C to 60°C.
  • the dosing amount in the method herein may be different depending on the washing type.
  • the method comprises administering from about 5 g to about 60 g of the laundry detergent composition into a hand washing basin (e.g., about 2-4 L) .
  • the method comprises administering from about 5 g to about 100 g, preferably from about 10 g to about 65 g of the laundry detergent composition into a washing machine (e.g., about 30-45 L) .
  • the method herein further comprises the step of contacting a soiled fabric with the washing solution.
  • a soiled fabric with the washing solution For example, the presence of Gram positive bacteria and/or Gram negative bacteria is suspected on the fabric.
  • the step of contacting the soiled fabric with the washing solution is preferably after the step of administering the laundry detergent composition in a laundry washing basin.
  • the method may further comprise the step of contacting a fabric with the laundry detergent composition prior to the step of administering the laundry detergent composition in a laundry washing basin, i.e., pre-treat the fabric with the laundry detergent composition for certain time, preferably from 1 minute to 10 minutes.
  • Test 1 Fabric Deposition Test for Anti-Microbial Agents
  • Anti-microbial agents are extracted from treated fabrics by using the methanol-based Accelerated Solvent Extraction (ASE) method described hereinafter.
  • ASE Accelerated Solvent Extraction
  • HPLC gradient reversed-phase high performance liquid chromatographic
  • MS/MS tandem mass spectrometry
  • MRM multiple reaction monitoring
  • a first step about three (3) grams of the treated fabrics is accurately weighed and then filled into a steel ASE tube.
  • the extraction protocol is run for about five (5) minutes using methanol as the extraction solvent at an elevated temperature of about 100°C and a pressure of about 2000 pound per square inch (psi) .
  • the resulting extract is collected and transferred into a 25-ml flask, which is then filled to its full volume with methanol.
  • the resulting solution is then diluted by about twenty-five (25) fold by using a mixture of methanol and water at a 50: 50 ratio, which is used as an injection sample for the subsequent LC-MS/MS analysis.
  • spiked matrix standards in the range of 0.5mg/ml to 500ng/ml are injected for creation of a calibration curve.
  • Concentration of the anti-microbial agent, for example in the injection sample is determined by extrapolation using weighted (1/x 2 ) quadratic regression of the calibration curve.
  • Test 2 Anti-Microbial Efficacy Test (JISL 1902)
  • the anti-microbial efficacy for laundry detergent compositions is determined by the method as defined in the JISL 1902 method and described hereinafter.
  • the solution is prepared by 2.5 g of a nonionic soaked agent, 2.5 g of sodium carbonate, and 5000 mL of distilled water.
  • the nonionic soaked agent is prepared by 5.0 g of alkylphenol ethoxylate, 5 g of sodium carbonate, and 1000 mL of distilled water.
  • One fabric strip serves as a test fabric strip for following steps 2B –2I, and the other fabric strip is used as control (without experiencing steps 2B –2I) .
  • step B Fix one end of the test fabric strip obtained from step 2A onto a stainless steel spindle at an outer position along the horizontal extension of the stainless steel spindle.
  • the stainless steel spindle has 3 horizontal stands that are connected to one another. Wrap the test fabric strip around the 3 horizontal stands of the stainless steel spindle with sufficient tension to obtain a fabric wrapped spindle having 12 laps of fabric. Fix the other end of the test fabric strip onto the outer lap of the 12 laps of fabric via a pin. Sterilize the fabric wrapped spindle with pressure steam at 121°C for 15 minutes.
  • step D Add sufficient amount of sample into 1L of the hard water solution obtained from step 2C to obtain a solution having a concentration of 1055 ppm. Mix the solution by a magnetic stirrer for 4 minutes. Distribute 250 mL of the mixed solution into an exposure chamber to obtain a washing solution. Place the exposure chamber in a water bath and achieve the test temperature of (25 ⁇ 1) °C.
  • step 1C Inoculate 0.2 mL of the working culture obtained from step 1C onto each dried specimen. Incubate the vials containing the inoculated specimens at 37°C for 18 hours.
  • CFU colony-forming units
  • steps 3A –3D use the fabric strip obtained from step 2A (that does not experience steps 2B –2I) as control. Take the log 10 value of CFU value as Ma.
  • a Bacteriostatic Activity Value of no less than 2.0 represents acceptable anti-microbial efficacy, of no less than 2.5 represents good anti-microbial efficacy, and of no less than 3.0 represents excellent anti-microbial efficacy. And a Bacteriostatic Activity Value of lower than 2.0 indicates unacceptable poor anti-microbial efficacy.
  • Example 1 Comparative Test Showing Improved Fabric Deposition of Anti-Microbial Agent by Laundry Detergent Composition Containing Both AO and A High Level of LAS
  • a is 4-4’-dichloro-2-hydroxy diphenyl ether, available from BASF
  • b is C 12 -C 15 alcohol ethoxylated with an average of 7 moles of ethylene oxide as a nonionic surfactant, available from Shell
  • Steps (A) to (I) three (3) times, while in the last repetition (i.e., the 4 th wash cycle) the fabric tracers are line-dried instead of machine-dried.
  • the anti-microbial deposition rate is the highest when the sample liquid laundry detergent composition contains AO with a high LAS content, while in the absence of AO the sample liquid laundry detergent composition with a high AES content has the highest anti-microbial deposition rate. This indicates that AO in a high-LAS laundry detergent composition is particularly effective in boosting anti-microbial deposition onto fabrics.
  • Example 2 Exemplary Formulations of Liquid Laundry Detergent Compositions
  • liquid laundry detergent compositions shown in Table 3 are made comprising the listed ingredients in the listed proportions (weight %) .
  • Example 3 Exemplary Formulations of Liquid Laundry Detergent Compositions
  • liquid laundry detergent compositions shown in Table 4 are made comprising the listed ingredients in the listed proportions (weight %) .
  • liquid laundry detergent compositions A-H in Examples 2 and 3 are prepared by the following steps:
  • step b) cooling down the temperature of the combination obtained in step b) to 25°C;

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Abstract

La présente invention concerne une composition détergente antimicrobienne de blanchisserie comprenant, en poids de la composition, un agent antimicrobien qui est un éther de diphényle, un tensioactif amphotère qui est un oxyde d'alkyldiméthyl amine en C6 à C20 (AO), et un tensioactif anionique qui est un sulfonate d'alkylbenzène linéaire en C6 à C20 (LAS), tandis que le LAS est présent comme tensioactif principal de la composition. La composition détergente de blanchisserie caractérisée par un tel système tensioactif avec de l'AO et une teneur élevée en LAS permet le dépôt amélioré d'un tel agent antimicrobien sur les tissus traités.
PCT/CN2018/097326 2017-10-12 2018-07-27 Composition détergente antimicrobienne de blanchisserie WO2019071994A1 (fr)

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CN109541069A (zh) * 2018-12-20 2019-03-29 上海开米科技有限公司 一种洗涤剂中4,4-二氯-2-羟基二苯醚含量的检测方法
WO2021082902A1 (fr) * 2019-10-31 2021-05-06 The Procter & Gamble Company Particules antimicrobiennes
TW202128967A (zh) * 2019-11-25 2021-08-01 日商花王股份有限公司 纖維製品用液體清潔劑組合物
WO2022115988A1 (fr) * 2020-12-01 2022-06-09 The Procter & Gamble Company Procédé d'élimination post-lavage de micro-organisme de vêtements
JP2023551822A (ja) * 2020-12-23 2023-12-13 ザ プロクター アンド ギャンブル カンパニー 抗菌液体洗剤組成物

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