EP3187576A1 - Seifenstück mit kationischem wirkstoff - Google Patents

Seifenstück mit kationischem wirkstoff Download PDF

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Publication number
EP3187576A1
EP3187576A1 EP16203650.3A EP16203650A EP3187576A1 EP 3187576 A1 EP3187576 A1 EP 3187576A1 EP 16203650 A EP16203650 A EP 16203650A EP 3187576 A1 EP3187576 A1 EP 3187576A1
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EP
European Patent Office
Prior art keywords
soap
cationic
composition
approximately
bar
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP16203650.3A
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English (en)
French (fr)
Inventor
Jesus Macias
Mary J. Conway
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel IP and Holding GmbH
Original Assignee
Dial Corp
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 Dial Corp filed Critical Dial Corp
Publication of EP3187576A1 publication Critical patent/EP3187576A1/de
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D10/00—Compositions of detergents, not provided for by one single preceding group
    • C11D10/04—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap
    • C11D10/047—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap based on cationic surface-active compounds and soap
    • 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
    • C11D9/00—Compositions of detergents based essentially on soap
    • C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
    • 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
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds

Definitions

  • the present invention generally relates to solid bar soaps, and more particularly relates to solid bar soaps that contain anionic soap and a cationic active component.
  • Bar soaps are usually formulated with a variety of additives to provide benefits that are not inherent in the soap itself. Additives may be employed to, for example, enhance the lathering of the soap, to enhance the mildness of the soap, or to enhance its antibacterial properties.
  • bar soaps comprise at least one "soaps," which, for purposes of describing this component of the compositions of the present invention, have the meaning as normally understood in the art, namely, monovalent salts of monocarboxylic fatty acids.
  • the counter ions of the salts generally include sodium, potassium, ammonium and alkanol ammonium ions, but may include other suitable ions known in the art.
  • the bar soaps may also include adjuvant ingredients such as moisturizers, humectants, antibacterials, water, fillers, polymers, dyes, and fragrances.
  • the soap components in conventional bar soaps comprise salts of long chain fatty acids.
  • the alkyl group of the fatty acids from about 8 carbon atoms, to about 20 carbon atoms in length.
  • the particular length of the alkyl chain of the soaps is selected for various reasons including cleansing capability, lather capability, and cost.
  • Bar soaps often contain soap or fatty acids.
  • Fatty acids have a carboxylic acid group coupled to an alkane, often a linear alkane. Soaps are salts of fatty acids.
  • the alkane portion of the fatty acid or soap is hydrophobic and non-polar, allowing it to interact with greases, waxes, oils, proteins, and similar hydrophobic materials.
  • the carboxylic portion of the fatty acid or soap is polar and interacts with polar materials, including water.
  • Soaps and fatty acids act as surfactants.
  • Surfactants are defined as materials that lower the surface tension (or interfacial tension) between two liquids or between a liquid and a solid.
  • most surfactants include a polar region, informally called the "head” and a non-polar region, informally called the "tail.”
  • Different surfactants have different numbers of heads and tails. For instance, some surfactants have a single head and a single tails. Other surfactants have a single head and two or more tail. Some surfactants have multiple heads and multiple tails. Proteins for instance, may act as surfactants with a large number of both polar and non-polar regions on a single molecule.
  • Surfactants are divided into four principle groups: anionic, non-ionic, cationic, and zwitterionic (also called amphoteric). The groupings are based on the chemical groups in the polar region of the surfactant.
  • Anionic surfactants include an anionic group in the polar region. Examples of anionic groups include: sulfate, sulfonate, phosphate, and carboxylate groups.
  • Cationic surfactants include a cationic group in the polar region. Examples of cationic groups include: primary, secondary, and tertiary amines and quaternary ammonium cations.
  • Zwitterionic surfactants include both an anion group and a cation group in the polar region. Non-ionic surfactants have neither an anion group nor a cation group in the polar region. Examples of non-ionic hydrophilic groups include alcohols and ethers.
  • fatty acids contain a carboxylic acid group attached to an alkane region, they (and the corresponding soaps) are anionic surfactants.
  • the head of the fatty acid has a negative charge.
  • the negative charge may be balanced with a positive charge, for example sodium, potassium, ammonium, and/or similar positively charged species.
  • the fatty acid and/or soaps in bar soap formulations dissolve into polar solutions (e.g. water) and aid in the stabilization of non-polar molecules or parts of molecules in the solution. This reduces the energy to dissolve these molecules and also helps keep them from precipitating out of the solution.
  • polar solutions e.g. water
  • the soap In order for the soap to have this function, however, it needs to maintain its hydrophilic and hydrophobic regions available to interact with other molecules. This has meant that cationic agents were not used with anionic soaps in soap formulations because the positive charge of the cationic species and the negative charge of the anionic soap would attract and form a stable complex with just the hydrophobic portions exposed. These hydrophobic complexes then precipitate out of the polar solution.
  • the cationic agent and the anionic surfactants tend to neutralize each other with the result being that neither component performs its purpose as part of the soap.
  • An example of this is an Esterquat or other fatty quaternary ammonium salts and a liquid soap formulation which produces a cloudy precipitate which resists dissolution under agitation or heat.
  • the cationic active agent appears to remain functional despite long term storage mixed with the anionic soap. Specifically, two month storage (aging test) at 40C and subsequent testing of the bar soap shows that the soap continues to exhibit both the desired soap properties as well as the anti-bacterially properties from the cationic agent.
  • one example according to this disclosure is a bar soap comprising: about 0.001 to about 1.0 wt. % cetylpyridinium chloride (CPC); about 40 to about 90 wt. % anionic surfactant; about 0.05 to about 10 wt. % Humectants and/or solvents, e.g. (PEG-6 methyl ether, PEG-8, PEG-12, glycerin and/or similar; and about 0.1 to about 3.0 wt. % fragrance and other additives.
  • CPC cetylpyridinium chloride
  • anionic surfactant e.g. (PEG-6 methyl ether, PEG-8, PEG-12, glycerin and/or similar
  • solvents e.g. (PEG-6 methyl ether, PEG-8, PEG-12, glycerin and/or similar
  • fragrance and other additives e.g. (PEG-6 methyl ether, PEG-8, PEG-12, glycerin and
  • An example according to this disclosure is a bar soap comprising: 70 to 80 wt. % anionic soap; 10 to 20 wt. % water; and 0.001 to 1.0 wt. % of a cationic antibacterial agent.
  • the cationic antibacterial agent includes an amine.
  • the cationic antibacterial agent may be CPC.
  • the antibacterial agent may be benzalkonium chloride (BAC) and/or benzethonium chloride (BZC).
  • the soaps may include sodium tallowate, sodium cocoate, sodium palm kernelate, sodium palmate, and/or similar soaps including soaps with non-sodium cations.
  • Another example according to this disclosure is a bar soap comprising: 65 to 85 wt. % anionic soaps; 8 to 20 wt. % water; 0 to 10 wt. % talc; 0 to 10 wt. % fatty acid; 0 to 10 wt. % glycerin; 0.2 to 2.0 wt. % sodium chloride; 0.02 to 0.20 wt. % chelating agents; 0.3 to 2.5 wt. % PEG-6 Methyl Ether; 0.01 to 1.0 wt. % cationic antibacterial agent; and colorants and dyes (up to 4 wt. %).
  • the 0.02 wt. % CPC bar test sample showed significant reduction in total aerobic bacteria compared with the baseline.
  • the baseline was 5.70 and the after treatment mean value of 5.30, with a p-value of 0.003.
  • the water control showed a much smaller reduction with a baseline of 5.89 and an after treatment average of 5.81, with a p-value of 0.56.
  • the measurement of diphtheroids similarly showed a reduction with the 0.02 wt. % CPC bar test sample compared with baseline.
  • the baseline mean value was 3.92 and the after treatment mean value was 3.18, with a p-value of 0.046.
  • the water control had a baseline of 3.99 and an after treatment mean value of 4.13, with a p-value of 0.65.
  • the cationic antibacterial agent reduces the number of odor causing bacteria producing a resulting decrease in odor.
  • the test bar contained the following components: 0.06 wt. % cetylpyridinium chloride; with a bar soap base as previously described.
  • the control for this test was a water wash.
  • the test protocol was conducted according to ASTM E1207-02, Standard Guide for Sensory Evaluation of Axillary Deodorancy.
  • subjects Following a 10 day conditioning period and 24 hours after a control wash, subjects participated in a baseline odor evaluation. Subjects were required to have an average odor intensity score ⁇ 4.0 and ⁇ 8.0 in each axilla to remain in the study. Subjects could not have more than a 3 point difference in average right and left scores to remain in the study. Qualified subjects were then assigned a final subject number and randomly assigned to the product distribution.
  • the baseline (before wash) values for the test group had a mean of 6.28 and the control group had a mean of 6.28 with a p-value of 0.995.
  • the bar soap group had a value of 4.06 and the water control group had a mean value of 4.93, with a p-value of ⁇ 0.001 (which is below the 0.05 threshold usually used for statistical significance).
  • the test group had a mean value of 3.92 and the control group had a mean value 4.61, with a p-value of ⁇ 0.001.
  • BAC benzalkonium chloride
  • BZC benzethonium chloride
  • BAC Benzalkonium chloride
  • the cationic agent is a conditioner for hair and/or skin.
  • suitable cationic agents that function as conditioners include polyquatermnium-7, polyquaternium-10, guar hydroxypropyl trimonium chloride, and cocamidopropyl PG-dimonium chloride phosphate.
  • bar soap typically involves the use of water-soluble soap from a fat charge that is capable of providing a combination of individual soaps of fatty acids suitable for the formation of a solid bar.
  • Individual soap compounds may be alkali metal, ammonium or substituted ammonium salts, preferably sodium or potassium salts, of long-chain fatty acids.
  • Such fatty acids may be straight chain saturated or unsaturated fatty acids of from 8 to 24 carbon atoms, preferably from 14 to 18 carbon atoms.
  • Suitable fatty acids are those of tallow, groundnut, cottonseed, palm, palm kernel, babassu, and coconut oils, for instance lauric, myristic, palmitic, oleic, and stearic acids and the acids of dehydrated hardened castor oil; or erucic and behenic acids.
  • Some preferred soaps include, but are not limited to, sodium tallowate, sodium cocoate, sodium palm kernelate, and sodium palmate.
  • surfactants may be added to the form the bar soap. These surfactants may include anionic, cationic, non-ionic, and/or zwitterionic surfactants, as well as combinations of these classes.
  • Suitable anionic surfactants include, but are not limited to, compounds in the classes known as alkyl sulfates, alkyl ether sulfates, alkyl ether sulfonates, sulfate esters of an alkylphenoxy polyoxyethylene ethanol, alpha-olefin sulfonates, beta-alkoxy alkane sulfonates, alkylaryl sulfonates, alkyl monoglyceride sulfates, alkyl monoglyceride sulfonates, alkyl carbonates, alkyl ether carboxylates, fatty acids, sulfosuccinates, sarcosinates, oxtoxynol or nonoxynol phosphates, taurates, fatty taurides, fatty acid amide polyoxyethylene sulfates, isethionates, or mixtures thereof.
  • anionic surfactants are listed in McCutcheon's Emulsifiers and Detergents, 1993 Annuals, (hereafter McCutcheon's), McCutcheon Division, MC Publishing Co., Glen Rock, N.J., pp. 263-266 , incorporated herein by reference. Numerous other anionic surfactants, and classes of anionic surfactants, are disclosed in Laughlin et al. U.S. Pat. No. 3,929,678 , incorporated herein by reference.
  • the bar soaps of the present disclosure also may contain nonionic surfactants.
  • a nonionic surfactant has a hydrophobic base, such as a long chain alkyl group or an alkylated aryl group, and a hydrophilic chain comprising a sufficient number (i.e., 1 to about 30) of ethoxy and/or propoxy moieties.
  • nonionic surfactants examples include ethoxylated alkylphenols, ethoxylated and propoxylated fatty alcohols, polyethylene glycol ethers of methyl glucose, polyethylene glycol ethers of sorbitol, ethylene oxide-propylene oxide block copolymers, ethoxylated esters of fatty (C8-C18) acids, condensation products of ethylene oxide with long chain amines or amides, and mixtures thereof.
  • nonionic surfactants include, but are not limited to, methyl gluceth-10, PEG-20 methyl glucose distearate, PEG-20 methyl glucose sesquistearate, C11-15 pareth-20, ceteth-8, ceteth-12, dodoxynol-12, laureth-15, PEG-20 castor oil, polysorbate 20, steareth-20, polyoxyethylene-10 cetyl ether, polyoxyethylene-10 stearyl ether, polyoxyethylene-20 cetyl ether, polyoxyethylene-10 oleyl ether, polyoxyethylene-20 oleyl ether, an ethoxylated nonylphenol, ethoxylated octylphenol, ethoxylated dodecylphenol, or ethoxylated fatty (C6-C22) alcohol, including 3 to 20 ethylene oxide moieties, polyoxyethylene-20 isohexadecyl ether, polyoxyethylene-23 glycerol laurate, polyoxy-ethylene-20 glyceryl
  • Amphoteric or Zwitterionic surfactants can be broadly described as derivatives of secondary and tertiary amines having aliphatic radicals that are straight chain or branched, and wherein one of the aliphatic substituents contains from about 8 to 18 carbon atoms and at least one of the aliphatic substituents contains an anionic water-solubilizing group, e.g., carboxy, sulfonate, or sulfate.
  • Examples of compounds falling within this description are sodium 3-(dodecylamino)propionate, sodium 3-(dodecylamino)-propane-1-sulfonate, sodium 2-(dodecylamino)ethyl sulfate, sodium 2-(dimethylamino) octadecanoate, disodium 3-(N-carboxymethyl-dodecylamino) propane-1-sulfonate, disodium octadecyliminodiacetate, sodium 1-carboxymethyl-2-undecylimidazole, sodium N,N-bis(2-hydroxyethyl)-2-sulfato-3-dodecoxypropylamine, sodium coconut N-methyl taurate, sodium oleyl N-methyl taurate, sodium tall oil acid N-methyl taurate, sodium palmitoyl N-methyl taurate, cocodimethylcarboxymethylbetaine, lauryldimethylcarboxymethylbetaine, lauryl
  • the bar soaps may also include up to about 35% by weight of a combination of water-soluble polyhydric solvent(s) having three or more hydroxyl groups (3+-OH).
  • Preferred water soluble organic polyols having two hydroxyl groups (2-OH) include propylene glycol, dipropylene glycol, butylene glycol, ethylene glycol, 1,7-heptanediol, monoethylene glycols, polyethylene glycols, polypropylene glycols of up to 8,000 molecular weight, mono-C1-4 alkyl ethers of any of the foregoing, and mixtures thereof.
  • Preferred water-soluble polyhydric solvents that have at least three hydroxyl groups (3+-OH) include glycerine, and any sugar alcohol, such as sorbitol.
  • suitable sugar alcohols include tetritols such as erythritol, threitol, D-threitol, L-threitol, and D,L-threitol; pentitols such as ribitol, arabinitol, D-arabinitol, L-arabinitol, D,L-arabinitol and xylitol, hexitols such as allitol, dulcitol (galacitol), glucitol, sorbitol, (D-glucitol), L-glucitol, D,L-glucitol, D-mannitol, L-mannitol, D,L-mannitol, altritol, D-altritol, L-altritol, D,L-altritol, iditol, D-iditol, and L-iditol; and disaccharide alcohols such as
  • the bar soaps of the present invention may optionally include monohydric alcohols. If present, such alcohols are provided at a concentration preferably no greater than about 4 percent by weight, and most preferably no greater than about 2 percent by weight.
  • the bar soaps of the present disclosure may contain optional ingredients well known to persons skilled in the art. Such optional ingredients typically are present, individually, from 0% to about 5%, by weight, of the composition, and, collectively, from 0% to about 20%, by weight, of the composition.
  • Classes of optional ingredients include, but are not limited to, dyes, fragrances, pH adjusters, thickeners, fillers, viscosity modifiers, buffering agents, foam stabilizers, antioxidants, foam enhancers, chelating agents (such as diethylene triamine pentaacetic acid (DTPA) and 1-hydroxyethane 1,1-diphosphonic acid (HEDP)), opacifiers, sanitizing agents, preservatives, polymers, silicones, vitamin E or other vitamins, herb extracts, encapsulated materials, exfoliating agents, and similar classes of optional ingredients known to persons skilled in the art.
  • chelating agents such as diethylene triamine pentaacetic acid (DTPA) and 1-hydroxyethane 1,1-diphosphonic acid (HEDP)
  • opacifiers such as diethylene triamine pentaacetic acid (DTPA) and 1-hydroxyethane 1,1-diphosphonic acid (HEDP)
  • opacifiers such as diethylene triamine pentaacetic acid (DT
  • alkanolamides as foam boosters and stabilizers
  • gums and polymers as thickening agents
  • inorganic phosphates, sulfates, and carbonates as buffering agents
  • EDTA and phosphates as chelating agents
  • acids and bases as pH adjusters.
  • Examples of preferred classes of basic pH adjusters are ammonia; mono-, di-, and tri-alkyl amines; mono-, di-, and tri-alkanolamines; alkali metal and alkaline earth metal hydroxides; and mixtures thereof.
  • identity of the basic pH adjuster is not limited and any basic pH adjuster known in the art can be used.
  • Specific, nonlimiting examples of basic pH adjusters are ammonia; sodium, potassium, and lithium hydroxide; monoethanolamine; triethylamine; isopropanolamine; diethanolamine; and triethanolamine.
  • Examples of preferred classes of acidic pH adjusters are the mineral acids and polycarboxylic acids.
  • Nonlimiting examples of mineral acids are hydrochloric acid, nitric acid, phosphoric acid, and sulfuric acid.
  • Nonlimiting examples of polycarboxylic acids are citric acid, glycolic acid, and lactic acid.
  • the identity of the acidic pH adjuster is not limited and any acidic pH adjuster known in the art, alone or in combination, can be used.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
EP16203650.3A 2015-12-29 2016-12-13 Seifenstück mit kationischem wirkstoff Withdrawn EP3187576A1 (de)

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US201514982823A 2015-12-29 2015-12-29

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019125792A1 (en) * 2017-12-19 2019-06-27 Colgate-Palmolive Company Personal care compositions

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB970955A (en) * 1962-04-06 1964-09-23 Baker Chem Co J T Improved detergent compositions
US3580853A (en) * 1967-09-27 1971-05-25 Procter & Gamble Detergent compositions containing particle deposition enhancing agents
US3929678A (en) 1974-08-01 1975-12-30 Procter & Gamble Detergent composition having enhanced particulate soil removal performance
US6383999B1 (en) * 2000-02-10 2002-05-07 Unilever Home & Personal Care Usa. Division Of Conopco, Inc. Personal washing bar having adjacent emollient rich and emollient poor phases
JP2009138051A (ja) * 2007-12-04 2009-06-25 Lion Corp 固形石鹸組成物

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB970955A (en) * 1962-04-06 1964-09-23 Baker Chem Co J T Improved detergent compositions
US3580853A (en) * 1967-09-27 1971-05-25 Procter & Gamble Detergent compositions containing particle deposition enhancing agents
US3929678A (en) 1974-08-01 1975-12-30 Procter & Gamble Detergent composition having enhanced particulate soil removal performance
US6383999B1 (en) * 2000-02-10 2002-05-07 Unilever Home & Personal Care Usa. Division Of Conopco, Inc. Personal washing bar having adjacent emollient rich and emollient poor phases
JP2009138051A (ja) * 2007-12-04 2009-06-25 Lion Corp 固形石鹸組成物

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
"CTFA International Cosmetic Ingredient Dictionary", 1991, COSMETIC, TOILETRY AND FRAGRANCE ASSOCIATION, pages: 1 - 651
"Handbook of Detergents Part A: Properties", 1999, article "Anionic-Cationic Surfactant Mixtures"
"McCutcheon's Detergents and Emulsifiers", 1993, MCCUTCHEON DIVISION, MC PUBLISHING CO., pages: 1 - 246,266-
"McCutcheon's Emulsifiers and Detergents", 1993, MC PUBLISHING CO., article "McCutcheon Division", pages: 263 - 266
"the CTFA Handbook", pages: 86 - 94

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019125792A1 (en) * 2017-12-19 2019-06-27 Colgate-Palmolive Company Personal care compositions
CN111491602A (zh) * 2017-12-19 2020-08-04 高露洁-棕榄公司 个人护理组合物
US11690833B2 (en) 2017-12-19 2023-07-04 Colgate-Palmolive Company Personal care compositions

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