EP0955355A2 - Antioxydants pour stabiliser des formulations contenant des agents tensioactifs - Google Patents

Antioxydants pour stabiliser des formulations contenant des agents tensioactifs Download PDF

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Publication number
EP0955355A2
EP0955355A2 EP99810327A EP99810327A EP0955355A2 EP 0955355 A2 EP0955355 A2 EP 0955355A2 EP 99810327 A EP99810327 A EP 99810327A EP 99810327 A EP99810327 A EP 99810327A EP 0955355 A2 EP0955355 A2 EP 0955355A2
Authority
EP
European Patent Office
Prior art keywords
formula
composition according
alkyl
independently
another
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Withdrawn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
EP99810327A
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German (de)
English (en)
Other versions
EP0955355A3 (fr
Inventor
Dietmar Hüglin
Erich Kramer
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.)
BASF Schweiz AG
Original Assignee
Ciba Spezialitaetenchemie Holding AG
Ciba SC Holding AG
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 Ciba Spezialitaetenchemie Holding AG, Ciba SC Holding AG filed Critical Ciba Spezialitaetenchemie Holding AG
Priority to EP99810327A priority Critical patent/EP0955355A3/fr
Publication of EP0955355A2 publication Critical patent/EP0955355A2/fr
Publication of EP0955355A3 publication Critical patent/EP0955355A3/fr
Withdrawn legal-status Critical Current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
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0084—Antioxidants; Free-radical scavengers
    • 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
    • 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
    • C11D3/2034—Monohydric alcohols aromatic
    • 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
    • C11D3/2093—Esters; Carbonates
    • 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
    • C11D3/2096—Heterocyclic 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
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/28—Heterocyclic compounds containing nitrogen in the ring

Definitions

  • Solid and liquid soaps have been used for cleaning human skin for a long time.
  • the stability of the soap composition is an important criterion for problem-free use or a long shelf life.
  • Free radical reactions adversely affect the stability of a soap composition.
  • Free radicals initiate chain reactions which effect the decomposition of the long-chain hydrocarbon chains of the soaps, free acids or synthetic surfactants and the like in cleaning compositions. Such reactions can also bring about other negative effects, such as, for example, discoloration and rancidification.
  • Degradation of the long hydrocarbon chains can be prevented in cleaning compositions by adding antioxidants, such as, for example, butylated hydroxytoluene (BHT), which either prevent the catalysis of certain free radical mechanisms or, as free radicals, terminate the free radical chain reaction.
  • antioxidants such as, for example, butylated hydroxytoluene (BHT), which either prevent the catalysis of certain free radical mechanisms or, as free radicals, terminate the free radical chain reaction.
  • BHT causes stability problems in the soap compositions, such as, for example, decoloration, or yellow-brown by-products form.
  • WO 97/27839 discloses soap compositions in which the stabilizers used are specific phenolic antioxidants. However, these compounds have poor solubility and can only be incorporated with difficulty.
  • the object of the invention was thus to find phenolic antioxidants which have better solubility in soap formulations and can be incorporated without problem into the corresponding soap compositions.
  • the present invention thus provides a cleaning composition
  • a cleaning composition comprising
  • C 1 -C 22 -Alkyl are straight-chain or branched alkyl radicals, such as, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, amyl, isoamyl or tert-amyl, heptyl, octyl, isooctyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl or eicosyl.
  • alkyl radicals such as, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, amyl, isoamyl or tert-
  • C 1 -C 22 -Alkylthio are straight-chain or branched alkylthio radicals, such as, for example, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, sec-butylthio, tert-butylthio, amylthio, heptylthio, octylthio, isooctylthio, nonylthio, decylthio, undecylthio, dodecylthio, tetradecylthio, pentadecylthio, hexadecylthio, heptadecylthio, octadecylthio or eicosylthio.
  • alkylthio radicals such as, for example, methylthio, ethylthio, n-propylthio, is
  • C 2 -C 18 -Alkenyl is, for examply, allyl, methallyl, isopropenyl, 2-butenyl, 3-butenyl, isobutenyl, n-penta-2,4-dienyl, 3-methyl-but-2-enyl, n-oct-2-enyl, n-dodec-2-enyl, isododecenyl, n-dodec-2-enyl or n-octadec-4-enyl.
  • C 5 -C 7 -Cycloalkyl is cyclopentyl, cycloheptyl or, in particular, cyclohexyl.
  • C 7 -C 9 -Phenylalkyl is phenylpropyl, phenylethyl and, in particular, benzyl.
  • V in formula (1) is -O-.
  • component (a 1 ) is preferably a compound of the formula in which
  • component (a 1 ) is preferably a compound of the formula in which
  • Component (a 1 ) is preferably also a compound of the formula in which
  • antioxidants corresponding to component (a 1 ) and (a 2 ) can be used in the novel cleaning composition either as individual components or as a mixture of several individual compounds.
  • Component (a) is generally present in the novel cleaning composition in a concentration of from 50 to 1000 ppm.
  • the antioxidants used according to the invention have excellent reactivity and can thus be used advantageously at low temperatures. Furthermore, they display better stability to hydrolysis, particularly in an alkaline medium. Because of their good solubility, they can be easily incorporated into soap formulations.
  • novel compositions thus show high stability towards colour changes and chemical decomposition. This is to be attributed to the effectiveness, colour stability, ease of incorporation and stability to hydrolysis of the antioxidants used.
  • Component (b) in the novel cleaning composition may be any surfactant which removes dirt from the skin and is at the same time sensitive to the oxidative degradation which leads to decoloration and/or unpleasant odours.
  • Suitable examples are anionic, nonionic or zwitterionic and amphoteric synthetic, detersive substances.
  • Suitable anionic detersive substances are
  • anionic surfactants used are fatty acid methyl taurides, alkylisethionates, fatty acid polypeptide condensates and fatty alcohol phosphoric esters.
  • the alkyl radicals in these compounds preferably have from 8 to 24 carbon atoms.
  • the anionic surfactants are generally in the form of their water-soluble salts, such as the alkali metal salts, ammonium salts or amine salts.
  • examples of such salts are lithium, sodium, potassium, ammonium, triethylamine, ethanolamine, diethanolamine or triethanolamine salts.
  • the sodium, potassium or ammonium (NR 1 R 2 R 3 ) salts are used, in which R 1 , R 2 and R 3 independently of one another are hydrogen, C 1 -C 4 alkyl or C 1 -C 4 hydroxyalkyl.
  • Very particularly preferred anionic surfactants in the novel composition are monoethanolamine lauryl sulfate or the alkali metal salts of fatty alcohol sulfates, in particular sodium lauryl sulfate and the product of the reaction between from 2 to 4 mol of ethylene oxide and sodium lauryl ether sulfate.
  • Suitable zwitterionic and amphoteric surfactants are C 8 -C 18 betaines, C 8 -C 18 sulfobetaines, C 8 -C 24 alkylamido-C 1 -C 4 alkylenebetaines, imidazoline carboxylates, alkylamphocarboxy-carboxylic acids, alkylamphocarboxylic acids (e.g. lauroamphoglycinate) and N-alkyl-b-aminopropionates or -iminodipropionates, the C 10 -C 20 alkylamido-C 1 -C 4 alkylenebetaines and, in particular, coconut fatty acid amidopropylbetaine being preferred.
  • nonionogenic surfactants are derivatives of the adducts of propylene oxide/ethylene oxide having a molecular weight of from 1000 to 15,000, fatty alcohol ethoxylates (1-50 EO), alkylphenol polyglycol ethers (1-50 EO), ethoxylated carbohydrates, fatty acid glycol partial esters, such as, for example, diethylene glycol monostearate, fatty acid alkanolamides and dialkanolamides, fatty acid alkanolamide ethoxylates and fatty amine oxides.
  • component (b) may be the salts of saturated and unsaturated C 8 -C 22 fatty acids either alone, as a mixture with one another or as a mixture with the other detersive substances mentioned as component (b).
  • these fatty acids are capric, lauric, myristic, palmitic, stearic, arachidic, behenic, caproleic, dodecenoic, tetradecenoic, octadecenoic, oleic, eicosenoic and erucic acid, and the technical-grade mixtures of such acids, such as, for example, coconut fatty acid.
  • acids are in the form of salts, suitable cations being alkali metal cations, such as sodium and potassium cations, metal atoms, such as zinc and aluminium atoms, or sufficiently alkaline, nitrogen-containing organic compounds, such as amines or ethoxylated amines.
  • suitable cations being alkali metal cations, such as sodium and potassium cations, metal atoms, such as zinc and aluminium atoms, or sufficiently alkaline, nitrogen-containing organic compounds, such as amines or ethoxylated amines.
  • suitable cations being alkali metal cations, such as sodium and potassium cations, metal atoms, such as zinc and aluminium atoms, or sufficiently alkaline, nitrogen-containing organic compounds, such as amines or ethoxylated amines.
  • Component (b) in the novel composition is preferably a soap, i.e. a branched or unbranched long-chain alkyl- or alkenyl-carboxylic acid salt, such as, for example, the sodium, potassium, ammonium or substituted ammonium salt.
  • a soap i.e. a branched or unbranched long-chain alkyl- or alkenyl-carboxylic acid salt, such as, for example, the sodium, potassium, ammonium or substituted ammonium salt.
  • the novel composition may comprise, as component (c), a light protection agent of the sterically hindered amine type.
  • This is preferably a 2,2,6,6-tetraalkylpiperidine derivative which contains at least one group of the formula in which G is hydrogen or methyl, in particular hydrogen.
  • tetraalkylpiperidine derivatives are particularly advantageously used: bis(2,2,6,6-tetramethylpiperidin-4-yl) sebacate, bis(2,2,6,6-tetramethylpiperidin-4-yl) succinate, bis(1,2,2,6,6-pentamethylpiperidin-4-yl) sebacate, bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, bis(1,2,2,6,6-pentamethylpiperidyl) n-butyl 3,5-di-tert-butyl-4-hydroxybenzylmalonate, the condensate of 1-hydroxyethyl-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid, the condensate of N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4-tert-octylamino-2,6-dichloro
  • the novel composition can be in the form of a solid, gel, syndet or liquid soap. It can be prepared by the usual methods.
  • the soaps (solid soaps, syndets, liquid soaps) are prepared by processes which are generally customary in the soaps industry for these products and described in the literature (see, for example, L. Spitz (Ed.), Soaps and Detergents, A Theoretical and Practical Review, AOCS Press, Champaign, III., USA (1996)).
  • An important factor in the preparation of solid soaps is the intensive mixing of the soap composition prior to extrusion to achieve a homogeneous distribution of the ingredients, in particular of the antioxidant.
  • the antioxidant is usually added to the soap composition directly or, if appropriate, predissolved in perfume, homogeneously distributed therein by mixing (for example in a guide-beam mixer) and kneading (for example in an intensive kneader), before the composition is extruded or moulded.
  • Liquid soaps are likewise produced by homogenization of the constituents in suitable mixing devices (for example Sulzer mixers, Erestat mixers or DAT mixers from Pfaudler), uniform distribution of the antioxidant generally being achieved more quickly than in the case of solid soaps as a result of the lower viscosity of the formulation.
  • An alternative procedure involves incorporating the antioxidant into the basic soap composition (flakes, ribbons), if necessary with the application of heat (melting).
  • the soap base (A) is thoroughly mixed, and the water (B) is added at 20°C.
  • the viscous paste is homogenized using a rotor-stator, and then the components (C) are added in the order given with vigorous mixing.
  • the mixture is homogenized for a further 15 minutes and extruded in a bench extruder.
  • the soap bars are produced by pressing (bench press).
  • Preparation The ingredients are initially introduced in the order given and mixed with water. The pH is adjusted to 5.5-6.5 using citric acid. The mixture is then homogenized for 10 minutes at 20°C and the resulting liquid soap is poured into bottles.
  • the soap base (A) is thoroughly mixed, and water (B) is added at 20°C.
  • the paste is homogenized using a rotor-stator, and then components (C) are added in the order given with vigorous mixing.
  • the mixture is homogenized for a further 15 minutes and extruded in a bench extruder.
  • the soap bars are produced by pressing (bench press).
  • Example 4 Test as regards discoloration in soaps in an oxidative environment
  • Antioxidants tested compounds of the formulae (11), (15), (16), (25), (32) and (33).
  • 500 ppm of the respective antioxidant to be tested are, together with 500 ppm of benzoyl peroxide and 0.2% of titanium dioxide, homogeneously distributed in a customary soap base (mixture of tallow fat, coconut and palm kernel soaps) by vigorous mixing and kneading in a bench mixer. The mixing process is repeated several times to ensure homogeneous distribution of the antioxidant in the soap.
  • a customary soap base mixture of tallow fat, coconut and palm kernel soaps
  • the mixture is extruded using a bench extruder, producing test soap bars weighing approximately 1 g. These soaps are stored in a drying cabinet at 40°C for two months, individual test soap bars being checked for their discoloration after each week. This is carried out by quantitative colorimetry, the reflectance spectroscopic method advantageously being used. This method is described in detail in the literature (see, for example, Colorimetry, Second Edition, International Commission on Illumination (CIE), CIE publication 15.2 (1986)). Comparison of the colorimetric results of the test preparations with those of the standard (freshly prepared sample having the same composition) is a measure of the colour stability of the antioxidant used.
  • CIE International Commission on Illumination
  • Antioxidants tested compounds of the formulae (11), (15), (16), (21), (23), (24), (32) and (33).
  • Antioxidants tested compounds of the formulae (11), (14), (15), (16), (17), (21), (22), (24), (28), (32) and (33).
  • the stability of antioxidants in alkali can be tested quickly using a simple test.
  • 0.05% of each of the antioxidants is mixed, in a bench mixer, into conventional soap flakes which customarily contain 10-15% of moisture and 0.02-0.1% of free alkali (as Na 2 O) (overall values, % by weight).
  • the mixing process should be repeated several times to ensure homogeneous distribution of the antioxidant in the soap.
  • the samples are stored for 2 months in a drying cabinet at 40°C, and then the relative content of unchanged antioxidant is determined using HPLC analysis.
  • the reference used (100% values) is the HPLC signals (heights or areas) of the respective antioxidants in freshly prepared soap formulations.
  • the antioxidants tested have good stability in soap formulations. Their content in alkaline soaps, as determined by HPLC, is virtually unchanged after storage for 2 months in accordance with the above test.
  • novel compositions thus have good stability to colour changes and chemical decomposition.

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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)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Biochemistry (AREA)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)
EP99810327A 1998-04-28 1999-04-20 Antioxydants pour stabiliser des formulations contenant des agents tensioactifs Withdrawn EP0955355A3 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP99810327A EP0955355A3 (fr) 1998-04-28 1999-04-20 Antioxydants pour stabiliser des formulations contenant des agents tensioactifs

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
EP98810374 1998-04-28
EP98810374 1998-04-28
CH214398 1998-10-23
CH214398 1998-10-23
EP99810327A EP0955355A3 (fr) 1998-04-28 1999-04-20 Antioxydants pour stabiliser des formulations contenant des agents tensioactifs

Publications (2)

Publication Number Publication Date
EP0955355A2 true EP0955355A2 (fr) 1999-11-10
EP0955355A3 EP0955355A3 (fr) 2000-08-02

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1808184A2 (fr) * 2000-10-24 2007-07-18 CIS bio international Stabilisation de compositions radiopharmaceutiques à l'aide de thioethers hydrophiles et de 6-hydroxychromanes hydrophiles
WO2012123313A1 (fr) * 2011-03-11 2012-09-20 Akzo Nobel Chemicals International B.V. Stabilisation de tensio-actifs contre une attaque oxydative
WO2022079276A1 (fr) * 2020-10-16 2022-04-21 L'oreal Composition cosmétique de nettoyage comprenant des tensioactifs

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1569498A (fr) * 1967-06-26 1969-05-30
GB2257141A (en) * 1991-07-01 1993-01-06 Ciba Geigy Ag Thiomethylated benzofuran-2-ones and their use as stabilizer for organic materials
WO1997027839A1 (fr) * 1996-01-30 1997-08-07 Colgate-Palmolive Company Composition de nettoyage comprenant un ou plusieurs stabilisants des couleurs et un ou plusieurs tensioactifs
WO1999005250A1 (fr) * 1997-07-22 1999-02-04 Henkel Corporation Composition de nettoyage antimicrobienne aqueuse contenant du triclosan et du tocopherol et procedes d'inhibition d'une degradation de ses couleurs

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU1604839A1 (ru) * 1989-01-12 1990-11-07 Масложиркомбинат "Краснодарский" Им.В.В.Куйбышева Туалетное мыло
KR930003761B1 (ko) * 1990-11-17 1993-05-10 주식회사 럭키 화장비누 조성물

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1569498A (fr) * 1967-06-26 1969-05-30
GB2257141A (en) * 1991-07-01 1993-01-06 Ciba Geigy Ag Thiomethylated benzofuran-2-ones and their use as stabilizer for organic materials
WO1997027839A1 (fr) * 1996-01-30 1997-08-07 Colgate-Palmolive Company Composition de nettoyage comprenant un ou plusieurs stabilisants des couleurs et un ou plusieurs tensioactifs
WO1999005250A1 (fr) * 1997-07-22 1999-02-04 Henkel Corporation Composition de nettoyage antimicrobienne aqueuse contenant du triclosan et du tocopherol et procedes d'inhibition d'une degradation de ses couleurs

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 9142 Derwent Publications Ltd., London, GB; AN 91-308256 XP002100947 & SU 1 604 839 A (KRASNODARSK OIL FAT, ET AL.), 7 November 1990 (1990-11-07) *
DATABASE WPI Week 9350 Derwent Publications Ltd., London, GB; AN 93-402031 XP002100946 & KR 9 303 761 B (LUCKY CO.), 10 May 1993 (1993-05-10) *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1808184A2 (fr) * 2000-10-24 2007-07-18 CIS bio international Stabilisation de compositions radiopharmaceutiques à l'aide de thioethers hydrophiles et de 6-hydroxychromanes hydrophiles
EP1808184A3 (fr) * 2000-10-24 2008-08-13 CIS bio international Stabilisation de compositions radiopharmaceutiques à l'aide de thioethers hydrophiles et de 6-hydroxychromanes hydrophiles
WO2012123313A1 (fr) * 2011-03-11 2012-09-20 Akzo Nobel Chemicals International B.V. Stabilisation de tensio-actifs contre une attaque oxydative
CN103429726A (zh) * 2011-03-11 2013-12-04 阿克佐诺贝尔化学国际公司 表面活性剂抗氧化侵袭的稳定化
WO2022079276A1 (fr) * 2020-10-16 2022-04-21 L'oreal Composition cosmétique de nettoyage comprenant des tensioactifs
FR3115197A1 (fr) * 2020-10-16 2022-04-22 L'oreal Composition cosmétique nettoyante comprenant des tensioactifs

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