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WO1999009944A1 - Dispersions aqueuses de lustre nacre - Google Patents

Dispersions aqueuses de lustre nacre Download PDF

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Publication number
WO1999009944A1
WO1999009944A1 PCT/EP1998/005187 EP9805187W WO9909944A1 WO 1999009944 A1 WO1999009944 A1 WO 1999009944A1 EP 9805187 W EP9805187 W EP 9805187W WO 9909944 A1 WO9909944 A1 WO 9909944A1
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WIPO (PCT)
Prior art keywords
acid
fatty
carbon atoms
pearlescent
alcohol
Prior art date
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PCT/EP1998/005187
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German (de)
English (en)
Inventor
Achim Ansmann
Rolf Kawa
Bernd Fabry
Hermann Hensen
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Cognis Deutschland Gmbh
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
Priority claimed from DE19736906A external-priority patent/DE19736906A1/de
Priority claimed from DE19741911A external-priority patent/DE19741911C1/de
Priority claimed from DE19810888A external-priority patent/DE19810888A1/de
Application filed by Cognis Deutschland Gmbh filed Critical Cognis Deutschland Gmbh
Publication of WO1999009944A1 publication Critical patent/WO1999009944A1/fr

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    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005Other compounding ingredients characterised by their effect
    • C11D3/0089Pearlescent compositions; Opacifying agents
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/24Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran
    • C07C67/26Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran with an oxirane ring
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    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2603Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
    • C08G65/2615Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen the other compounds containing carboxylic acid, ester or anhydride groups
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    • C08G65/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2642Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
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    • C11D1/52Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/523Carboxylic alkylolamides, or dialkylolamides, or hydroxycarboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain one hydroxy group per alkyl group
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    • C11D1/52Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/525Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain two or more hydroxy groups per alkyl group, e.g. R3 being a reducing sugar rest
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    • C11D1/88Ampholytes; Electroneutral compounds
    • C11D1/90Betaines

Definitions

  • the invention relates to aqueous pearlescent concentrates containing fatty acid polyglycol ester sulfates, pearlescent waxes and optionally further emulsifiers and / or polyols, a process for their preparation, a further process for producing pearlescent surface-active preparations using the concentrates and the use of the fatty acid polyglycol ester sulfates as Emulsifiers for the production of pearlescent concentrates.
  • the prior art knows a large number of formulations which give surface-active agents the desired pearlescence.
  • pearlescent concentrates in the form of flowable aqueous dispersions which contain 15 to 40% by weight of pearlescent components, 5 to 55% by weight of emulsifiers and 0.1 to Contain 5 or 15 to 40 wt .-% polyols.
  • the pearlescent waxes are acylated polyalkylene glycols, monoalkanolamides, linear, saturated fatty acids or ketosulfones.
  • European patent application EP 0205922 A2 (Henkel) relates to flowable pearlescent concentrates which contain 5 to 15% by weight of acylated polyglycols, 1 to 6% by weight of fatty acid monoethanolamides and 1 to 5% by weight of nonionic emulsifiers.
  • nonionic, flowable pearlescent dispersions can also be obtained by preparing mixtures of 5 to 30% by weight of acylated polyglycols and 0.1 to 20% by weight of selected nonionic surfactants.
  • European patent application EP 0581193 A1 Hoechst
  • preservative-free pearlescent dispersions which contain acylated polyglycol ethers, betaines, anionic surfactants and glycerol.
  • polyglycerol esters as crystallization aids for the production of pearlescent concentrates is proposed in European patent application EP 0684302 A1 (Th.Goldschmidt).
  • the invention relates to aqueous pearlescent concentrates containing - based on the nonaqueous fraction -
  • anionic emulsifiers allow the production of concentrates which are excellent pearlescent Have properties and distinguish themselves from the products of the prior art by a higher brilliance with a lower amount, special fine-particle structure and storage stability.
  • the anionic emulsifiers are readily biodegradable, thin in a concentrated form and also allow problematic ingredients such as silicones to be incorporated into cosmetic preparations.
  • Fatty acid polyglycol ester sulfates which are contained in the concentrates as anionic emulsifiers (a) preferably follow the formula (I),
  • R 1 CO is a linear or branched, saturated or unsaturated acyl radical having 6 to 22 carbon atoms
  • x is an average of 1 to 3
  • AO is a CH2CH2O-, CH 2 CH (CH 3 ) 0- and / or CH ( CH 3 ) CH 2 0 radical
  • X is an alkali and / or alkaline earth metal, ammonium, alkylammonium, alkanolammonium or glucammonium and are prepared by sulfating the corresponding fatty acid polyglycol esters.
  • ethylene oxide, propylene oxide or a mixture thereof - in random or block distribution - is added to the corresponding fatty acids, this reaction being acid-catalyzed, but preferably in the presence of bases, such as, for example, sodium methylate or calcined hydrotalcite.
  • bases such as, for example, sodium methylate or calcined hydrotalcite.
  • the intermediates can also be prepared by esterifying the fatty acids with an appropriate alkylene glycol.
  • the sulfation of the fatty acid polyglycol esters can be carried out in a manner known per se using chlorosulfonic acid or preferably gaseous sulfur trioxide, the molar ratio between fatty acid polyglycol ester and sulfating agent being in the range from 1: 0.95 to 1: 1, 2, preferably 1: 1 to 1: 1 , 1 and the reaction temperature can be 30 to 80 and preferably 50 to 60 ° C. It is also possible to undersulfate the fatty acid polyglycol esters, ie to use significantly fewer sulfating agents than would be stoichiometrically required for complete conversion.
  • Typical examples of suitable starting materials are the addition products of 1 to 3 mol of ethylene oxide and / or propylene oxide, but preferably the adducts with 1 mol of ethylene oxide or 1 mol of propylene oxide with caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid Acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, elaeostearic acid, arachic acid, gadoleic acid, behenic acid and erucic acid and their technical mixtures, which are then sulfated and neutralized as described above.
  • Fatty acid polyglycol ester sulfates of the formula (I) are preferably used in which R 1 CO stands for an acyl radical having 12 to 18 carbon atoms, x for an average of 1 or 2, AO for a CH2CH2 ⁇ group and X for sodium or ammonium, such as lauric acid + 1 EO sulfate sodium salt, lauric acid + 1 EO sulfate ammonium salt, coconut fatty acid + 1 EO sulfate sodium salt, coconut fatty acid + 1 EO sulfate ammonium salt, tallow fatty acid + 1 EO sulfate sodium salt, tallow fatty acid + 1 EO sulfate Ammonium salt and mixtures thereof.
  • R 1 CO stands for an acyl radical having 12 to 18 carbon atoms
  • x for an average of 1 or 2
  • AO for a CH2CH2 ⁇ group
  • X for sodium or ammonium, such as lauric acid + 1 EO s
  • the pearlescent concentrates according to the invention can contain nonionic surfactants from at least one of the following groups as further emulsifiers:
  • Glycerin (b3) Glycerol mono- and diesters and sorbitan mono- and diesters of saturated and unsaturated
  • polysiloxane-polyalkyl-polyether copolymers or corresponding derivatives (b12) mixed esters of pentaerythritol, fatty acids, citric acid and fatty alcohol according to DE-PS 1165574 and (b13) polyalkylene glycols.
  • adducts of ethylene oxide and / or of propylene oxide with fatty alcohols, fatty acids, alkylphenols, glycone mono- and diesters as well as sorbitan mono- and diesters of fatty acids or with castor oil are known, commercially available products. These are mixtures of homologs whose average degree of alkoxylation corresponds to the ratio of the amounts of ethylene oxide and / or propylene oxide and substrate with which the addition reaction is carried out.
  • Ci2 / i8 fatty acid monoesters and diesters of adducts of ethylene oxide with glycerol are known from DE 2024051 PS as refatting agents for cosmetic preparations.
  • C ⁇ / i ⁇ alkyl mono- and oligoglycosides their preparation and their use are known from the prior art. They are produced in particular by reacting glucose or oligosaccharides with primary alcohols with 8 to 18 carbon atoms.
  • glycoside residue both monoglycosides in which a cyclic sugar residue is glycosidically bonded to the fatty alcohol and oiigomeric glycosides with a degree of oligomerization of up to preferably about 8 are suitable.
  • the degree of oligomerization is a statistical mean value which is based on a homolog distribution customary for such technical products.
  • alkyl ether sulfates which follow the formula (II) are used as further anionic emulsifiers,
  • R 2 is a linear or branched alkyl and / or alkenyl radical having 6 to 22 carbon atoms
  • n is a number from 1 to 10
  • X is an alkali metal and / or alkaline earth metal, ammonium, alkylammonium, alkanolammonium or glucammonium.
  • Typical examples are the sulfates of addition products with an average of 1 to 10 and in particular 2 to 5 moles of ethylene oxide with capron alcohol, caprylic alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, oleostyl alcohol, isostyl alcohol Elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol and brassidyl alcohol and their technical mixtures, in the form of their sodium and / or magnesium salts.
  • the ether sulfates can have both a conventional and a narrow homolog distribution. It is particularly preferred to use ether sulfates based on adducts of an average of 2 to 3 mol ethylene oxide with technical C12 / 14 or C12 / 18 coconut oil alcohol fractions in the form of their sodium and / or magnesium salts.
  • zwitterionic surfactants can be used as additional emulsifiers.
  • Zwitterionic surfactants are those surface-active compounds in the molecule carry at least one quaternary ammonium group and at least one carboxylate and one sulfonate group.
  • Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethyl-ammonium glycinate, for example the cocoalkyldimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinate, for example the cocoacylaminopropyldimethylammonium 2-glycinate, and -Alkyl-3-carboxylmethyl-3-hydroxyethylimidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
  • betaines such as the N-alkyl-N, N-dimethyl-ammonium glycinate, for example the cocoalkyldimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium g
  • Suitable emulsifiers are ampholytic surfactants.
  • Ampholytic surfactants are surface-active compounds which, in addition to a C ⁇ m-alkyl or -acyl group, contain at least one free amino group and at least one -COOH or -S ⁇ 3H group in the molecule and are capable of forming internal salts.
  • ampholytic surfactants are N-alkylglycine, N-alkylpropionic acid, N-alkylaminobutyric acid, N-alkylimino dipropionic acid, N-hydroxyethyl-N-alkylamidopropylglycine, N-alkyltaurine, N-alkyl sarcosine, 2-alkylaminopropionic acid and alkylaminoacetic acid each with about 8 to 18 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and Ci2 / i8-acylsarcosine.
  • quaternary emulsifiers are also suitable, those of the ester quat type, preferably methyl-quaternized difatty acid triethanolamine ester salts, being particularly preferred.
  • the pearlescent concentrates according to the invention can contain the further emulsifiers in amounts of 0.1 to 90, preferably 5 to 50 and in particular 10 to 40% by weight.
  • Pearlescent waxes which form component (c) include, for example: alkylene glycol esters; Fatty acid alkanolamides; Partial glycerides; Esters of polyvalent, optionally hydroxy-substituted carboxylic acids with fatty alcohols having 6 to 22 carbon atoms; Fatty substances, such as, for example, fatty alcohols, fatty ketones, fatty aldehydes, fatty ethers and fatty carbonates, which have a total of at least 24 carbon atoms; Ring opening products of olefin epoxides with 12 to 22 carbon atoms with fatty alcohols with 12 to 22 carbon atoms, fatty acids and / or polyols with 2 to 15 carbon atoms and 2 to 10 hydroxyl groups and mixtures thereof.
  • alkylene glycol ester • alkylene glycol ester.
  • the alkylene glycol esters are usually mono- and / or diesters of alkylene glycols which follow the formula (III)
  • R 3 CO is a linear or branched, saturated or unsaturated acyl radical having 6 to 22 carbon atoms
  • R 4 is hydrogen or R 5 CO
  • A is a linear or branched alkylene radical having 2 to 4 carbon atoms and n is a number from 1 to 5 stands.
  • Typical examples are mono- and / or diesters of ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol or tetraethylene glycol with fatty acids with 6 to 22, preferably 12 to 18, carbon atoms as there are: caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid , Isotridecanoic acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, elaeostearic acid, arachic acid, gadoleic acid, behenic acid and erucic acid and their technical mixtures.
  • the use of ethylene glycol mono- and / or distearate is particularly preferred.
  • Fatty acid alkanolamides which can be used as pearlescent waxes follow the formula (IV),
  • R 5 CO for a linear or branched, saturated or unsaturated acyl radical with 6 to 22 carbon atoms
  • R 6 for hydrogen or an optionally hydroxy-substituted alkyl radical with 1 to 4 carbon atoms
  • B for a linear or branched alkylene group with 1 to 4 carbon atoms stands.
  • Typical examples are condensation products of ethanolamine, methylethanolamine, diethanolamine, propanolamine, methylpropanolamine and dipropanolamine and their mixtures with caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, oleostic acid, oleostic acid Petroselinic acid, linoleic acid, linolenic acid, elaeostearic acid, arachic acid, gadoleic acid, behenic acid and erucic acid and their technical mixtures.
  • the use of stearic acid ethanolamide is particularly preferred.
  • Partial glycerides which have pearlescent properties are mono- and / or diesters of glycerol with fatty acids, namely, for example, caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid, oleic acid, elaalic acid , Linoleic acid, linolenic acid, elaeostearic acid, arachic acid, gadoleic acid, behenic acid and erucic acid and their technical mixtures. They follow the formula (V),
  • R 7 CO for a linear or branched acyl radical having 6 to 22 carbon atoms
  • R 7 and R 9 independently of one another for hydrogen or R 7 CO, x, y and z in total for 0 or for numbers from 1 to 30
  • X for is an alkali or alkaline earth metal with the proviso that at least one of the two radicals R 8 and R 9 is hydrogen.
  • Typical examples are lauric acid, lauric, coconut fatty, coconut fatty acid triglyceride, glyceride palmitic acid, Palmitinklaretriglycerid, oleic, stearic acid diglyceride, isostearic acid monoglyceride, Isostearinklaigiycerid, oleic acid diglyceride, monoglyceride monoglyceride tallow, Talgfettklarediglycerid, behenic acid, Behenkladrediglycerid, erucic caklakladoglycerid, Erucaklakladrediglycerid and technical mixtures which may still contain small amounts of triglyceride from the manufacturing process.
  • ⁇ Polyvalent carboxylic acid and hydroxycarboxylic acid esters are Pearlescent waxes which can also be esters of polyvalent, optionally hydroxy-substituted carboxylic acids with fatty alcohols having 6 to 22 carbon atoms.
  • suitable acid components of these esters are malonic acid, maleic acid, fumaric acid, adipic acid, sebacic acid, azelaic acid, dodecanedioic acid, phthalic acid, isophthalic acid and in particular succinic acid and malic acid, citric acid and in particular tartaric acid and mixtures thereof.
  • the fatty alcohols contain 6 to 22, preferably 12 to 18 and in particular 16 to 18 carbon atoms in the alkyl chain.
  • Typical examples are caprone alcohol, capryl alcohol, 2-ethylhexyl alcohol, caprinal alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyla alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolenyl alcohol alcohol, linolenyl alcohol alcohol, linolenyl alcohol alcohol, linolenyl alcohol alcohol, linolenyl alcohol alcohol, linolenyl alcohol alcohol, linolenyl alcohol alcohol, linolenyl alcohol alcohol, linolenyl alcohol alcohol, linolenyl alcohol alcohol, linoleyl alcohol alcohol , Erucyl alcohol and brassidyl alcohol and their technical mixtures.
  • the esters can be present as full or partial esters, preferably mono- and especially diesters of carboxylic or hydroxycarboxylic acids.
  • Typical examples are succinic acid mono- and -dilauryl esters, succinic acid mono- and -dicetearly esters, succinic acid mono- and -distearyl esters, tartaric acid mono- and -dilauryl esters, tartaric acid mono- and dicocoalkyl esters, tartaric acid mono- and -dicetearyl esters, citric acid and mono- trilaury esters, citric acid mono-, di- and tricocoalkyl esters as well as citric acid mono-, di- and tricetearyl esters.
  • R 10 represents a linear alkyl radical having 24 to 48, preferably 32 to 36, carbon atoms.
  • the substances mentioned are generally long-chain oxidation products Paraffins.
  • Fat ketones which are suitable as component (a) preferably follow the formula (VII),
  • R 11 and R 12 independently of one another represent alkyl and / or alkenyl radicals having 1 to 22 carbon atoms, with the proviso that they have a total of at least 24 and preferably 32 to 48 carbon atoms.
  • the ketones can be prepared by methods known in the art, for example by pyrolysis of the corresponding fatty acid magnesium salts.
  • the ketones can be symmetrical or asymmetrical, but the two radicals R 11 and R 12 preferably differ only by one carbon atom and are derived from fatty acids having 16 to 22 carbon atoms. Stearon is characterized by particularly advantageous pearlescent properties.
  • Fatty aldehydes Fatty aldehydes suitable as pearlescent waxes correspond to the formula (VIII)
  • R 13 CO represents a linear or branched acyl radical having 24 to 48, preferably 28 to 32, carbon atoms.
  • Fatty ether also suitable as pearlescent waxes are fatty ethers of the formula (IX)
  • R 14 and R 15 independently of one another represent alkyl and / or alkenyl radicals having 1 to 22 carbon atoms, with the proviso that they have a total of at least 24 and preferably 32 to 48 carbon atoms.
  • Fat ethers of the type mentioned are usually prepared by acidic condensation of the corresponding fatty alcohols. Fat ethers with particularly advantageous pearlescent properties are obtained by condensation of fatty alcohols having 16 to 22 carbon atoms, such as, for example, cetyl alcohol, cetearyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, behenyl alcohol and / or erucyl alcohol.
  • Fatty carbonates are also suitable as component (a),
  • RI6O-CO-OR1 7 in which R 16 and R 17 independently of one another represent alkyl and / or alkenyl radicals having 1 to 22 carbon atoms, with the proviso that they have a total of at least 24 and preferably 32 to 48 carbon atoms.
  • the substances are obtained by transesterifying, for example, dimethyl or diethyl carbonate with the corresponding fatty alcohols in a manner known per se. Accordingly, the fatty carbonates can be constructed symmetrically or asymmetrically. However, carbonates are preferably used in which R 16 and R 17 are identical and represent alkyl radicals having 16 to 22 carbon atoms.
  • Transesterification products of dimethyl or diethyl carbonate with cetyl alcohol, cetearyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, behenyl alcohol and / or erucyl alcohol in the form of their mono- and diesters or their technical mixtures are particularly preferred.
  • ⁇ fatty acids Aliphatic, optionally hydroxy-substituted carboxylic acids with 16 to 30 carbons, such as, for example, stearic acid, cetylstearic acid, hydroxystearic acid and behenic acid and their technical mixtures, are suitable for this purpose.
  • the ring opening products are known substances which are usually produced by acid-catalyzed reaction of terminal or internal olefin epoxides with aliphatic alcohols.
  • the reaction products preferably follow the formula (XI)
  • R 18 and R 19 represent hydrogen or an alkyl radical having 10 to 20 carbon atoms, with the proviso that the sum of the carbon atoms of R 18 and R 19 is in the range from 10 to 20 and R 20 represents an alkyl and / or alkenyl radical having 12 to 22 carbon atoms and / or the radical of a polyol having 2 to 15 carbon atoms and 2 to 10 hydroxyl groups.
  • Typical examples are ring opening products of ⁇ -dodecene epoxide, ⁇ -hexadecene epoxide, ⁇ -octadecene epoxide, ⁇ -eicosenepoxide, ⁇ -docosenepoxide, i-dodecenepoxide, i-hexadecenepoxide, i-octadecene epoxide, i-eicosenepoxide and / or i-docosenepoxide with lauryl alcohol, coconut oil alcohol, myristyl alcohol, cetyl alcohol, cetearyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolyl alcohol, linolenyl alcohol, behenyl alcohol and / or erucyl alcohol.
  • Ring opening products of hexa- and / or octadecene epoxides with fatty alcohols having 16 to 18 carbon atoms are preferably used.
  • polyols are used for the ring opening, the following substances are involved: glycerin; Alkylene glycols, such as, for example, ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexyl lenglycol and polyethylene glycols with an average molecular weight of 100 to 1,000 daltons; technical oligoglycerol mixtures with a degree of self-condensation of 1.5 to 10 such as technical diglycerol mixtures with a diglycerol content of 40 to 50% by weight; Methyl compounds, such as in particular trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol; Lower alkyl giucoside
  • Polyols which are considered as component (d) in the context of the invention preferably have 2 to 15 carbon atoms and at least two hydroxyl groups. Typical examples are
  • Alkylene glycols such as, for example, ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol and polyethylene glycols with an average molecular weight of 100 to 1,000 daltons;
  • Methyl compounds such as in particular trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol;
  • Lower alkyl giucosides in particular those with 1 to 8 carbons in the alkyl radical, such as methyl and butyl glucoside;
  • Sugar alcohols with 5 to 12 carbon atoms such as sorbitol or mannitol,
  • Aminosugars such as glucamine.
  • the pearlescent concentrates according to the invention can contain the polyols, preferably glycerol, propylene glycol, butylene glycol, hexylene glycol and polyethylene glycols with an average molecular weight in the range from 100 to 10000 in amounts of 0.1 to 40, preferably 0.5 to 15 and in particular 1 to 5% by weight. % contain.
  • n Position of the pearlescent concentrates by preparing a mixture of components (a), (b) and (c), heated to a temperature which is 1 to 30 ° C above the melting point of the mixture, with the required amount of water about the same Temperature mixes and then cools to room temperature. It is also possible to provide a concentrated aqueous (anion) surfactant paste, stir in the pearlescent wax while hot and then dilute the mixture to the desired concentration with further water, or to mix in the presence of polymeric hydrophilic thickeners, such as hydroxypropyl celluloses, xanthan gum or To carry out polymers of the carbomer type.
  • a concentrated aqueous (anion) surfactant paste stir in the pearlescent wax while hot and then dilute the mixture to the desired concentration with further water, or to mix in the presence of polymeric hydrophilic thickeners, such as hydroxypropyl celluloses, xanthan gum or To carry out polymers of the carbomer type.
  • the pearlescent concentrates according to the invention are suitable for adjusting turbidity in surface-active preparations, for example hair shampoos or manual dishwashing detergents.
  • Another object of the invention therefore relates to a process for the preparation of cloudy and pearlescent liquid, aqueous preparations of water-soluble surface-active substances, in which the pearlescent concentrates in an amount of 0.5 to 40, preferably 1 to, the clear aqueous preparations at 0 to 40 ° C. 20% by weight of the preparation is added and distributed therein with stirring.
  • the surface-active preparations which generally have a non-aqueous content in the range from 1 to 50 and preferably 5 to 35% by weight, can contain nonionic, anionic, cationic and / or amphoteric or amphoteric surfactants, the proportion of which in the Average is usually about 50 to 99 and preferably 70 to 90 wt .-%.
  • anionic surfactants are soaps, alkylbenzenesulfonates, alkanesulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether sulfonates, ⁇ -methyl ester sulfonates, sulfo fatty acids, alkyl sulfates, glycerol ether sulfates, fatty acid monoglyceride (ether) sulfate, hydroxyl sulfate amate sulfate, fatty acid sulfate amide sulfate, fatty acid sulfate amate sulfate, hydroxymate sulfate amate sulfate, hydroxymic acid sulfate, fatty acid sulfate amate sulfate, fatty acid sulfate amate sulfate, hydroxymate sulfate, fatty acid sulfate,
  • anionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution.
  • Typical examples of nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, mixed ethers or mixed formals, alk (en) yl oligoglycosides, fatty acid N-alkyl glucamides, protein drolysates (especially vegetable products based on wheat), polyol fatty acid esters, sugar esters, sorbitan esters, polysorbates and amine oxides.
  • nonionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution.
  • Typical examples of cationic surfactants are quaternary ammonium compounds and ester quats, in particular quaternized fatty acid trialkanolamine ester salts.
  • Typical examples of amphoteric or zwitterionic surfactants are alkyl betaines, alkyl amido betaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines. The surfactants mentioned are exclusively known compounds.
  • the surface-active preparations, to which the pearlescent concentrates according to the invention are added can contain further auxiliaries and additives, such as, for example, oil bodies, superfatting agents, stabilizers, waxes, consistency agents, thickeners, polymers, silicone compounds, biogenic active ingredients, antidandruff agents, film formers, preservatives, hydrotropes, solubilizers, UV adsorber, dyes and fragrances.
  • auxiliaries and additives such as, for example, oil bodies, superfatting agents, stabilizers, waxes, consistency agents, thickeners, polymers, silicone compounds, biogenic active ingredients, antidandruff agents, film formers, preservatives, hydrotropes, solubilizers, UV adsorber, dyes and fragrances.
  • TN linear or branched, symmetrical or unsymmetrical dialkyl ethers with 6 to 22 carbon atoms per alkyl group, ring opening products of epoxidized fatty acid esters with polyols, silicone oils and / or aliphatic or naphthenic hydrocarbons.
  • Substances such as, for example, lanolin and lecithin and polyethoxylated or acylated lanolin and lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides can be used as superfatting agents, the latter simultaneously serving as foam stabilizers.
  • Suitable consistency agents are primarily fatty alcohols or hydroxy fatty alcohols with 12 to 22 and preferably 16 to 18 carbon atoms and, in addition, partial glycerides, fatty acids or hydroxy fatty acids.
  • a combination of these substances with alkyl oligoglucosides and / or fatty acid N-methylglucamides of the same chain length and / or polyglycerol poly-12-hydroxystearates is preferred.
  • Suitable thickeners are, for example, polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, and also higher molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates, (for example Carbopole® from Goodrich or Synthalene® from Sigma), polyacrylamides, polyvinyl alcohol and polyvinyl pyrrolidone, surfactants such as, for example, ethoxylated fatty acid glycerides, esters of fatty acids with polyols such as, for example, pentaerythritol or trimethylolpropane, fatty alcohol ethoxylates with a narrow homolog distribution or alkyl oligoglucosides, and electrolytes such as sodium chloride and ammonium chloride.
  • polysaccharides in particular xanthan gum, guar gu
  • Suitable cationic polymers are, for example, cationic cellulose derivatives, e.g. a quaternized hydroxyethyl cellulose available under the name Polymer JR 400® from Amerchol, cationic starch, copolymers of diallyl ammonium salts and acrylamides, quaternized vinyl pyrrolidone / vinyl imidazole polymers such as e.g.
  • Luviquat® condensation products of polyglycols and amines, quaternized collagen polypeptides, such as lauryldimonium hydroxypropyl hydrolyzed coilagen (Lamequat®L / Grünau), quaternized wheat polypeptides, polyethyleneimine, cationic silicone polymers, such as e.g. Amidomethicones, copolymers of adipic acid and dimethylaminohydroxypropyldiethylenethamine (Cartaretine® / Sandoz), copolymers of acrylic acid with dimethyldiallylammonium chloride (Merquat® 550 / Chemviron), polyaminopolyamides, e.g.
  • cationic chitin derivatives such as quaternized chitosan, optionally microcrystalline, condensation products from dihaloalkylene, such as e.g. Dibromobutane with bisdialkylamines, e.g. Bis-dimethylamino-1,3-propane, cationic guar gum, such as e.g. Jaguar® CBS, Jaguar® C-17, Jaguar® C-16 from Celanese, quaternized ammonium salt polymers such as e.g. Mirapol® A-15, Mirapol® AD-1, Mirapol® AZ-1 from Miranol.
  • dihaloalkylene such as e.g. Dibromobutane with bisdialkylamines, e.g. Bis-dimethylamino-1,3-propane
  • cationic guar gum such as e.g. Jaguar® CBS, Jaguar® C-17, Jaguar® C-16 from Celanese
  • quaternized ammonium salt polymers such as
  • Ais anionic, zwitterionic, amphoteric and nonionic polymers are, for example, vinyl acetate / crotonic acid copolymers, vinylpyrrolidone / vinyl acrylate copolymers, vinyl acetate / butyl maleate / isobornyl acrylate copolymers, methyl vinyl ether / maleic anhydride copolymers and esters thereof, uncrosslinked and polyol-crosslinked polyacrylic acids, acrylamidopropyl / Acrylate copolymers, octylacrylamide / methyl methacrylate / tert-butylaminoethyl methacrylate / 2-hydroxypropyl methacrylate copolymers, polyvinylpyrrolidone, vinylpyrrolidone / vinyl acetate copolymers, vinylpyrrolidone / dimethylaminoethyl methacrylate / vinylcaprolactam-terpolymers and optionally de
  • Suitable silicone compounds are, for example, dimethylpolysiloxanes, methylphenylpolysiloxanes, cyclic silicones and amino, fatty acid, alcohol, polyether, epoxy, fluorine, glycoside and / or alkyl-modified silicone compounds, which can be both liquid and resinous at room temperature.
  • Typical examples of fats are glycerides, waxes include Beeswax, carnauba wax, candelilla wax, montan wax, paraffin wax or micro waxes, optionally in combination with hydrophilic waxes, e.g. Cetylstearyl alcohol or partial glycerides in question.
  • Metal salts of fatty acids such as e.g.
  • Biogenic active substances are, for example, tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, deoxyribonucleic acid, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides, pseudoceramides, essential oils, plant extracts and vitamins.
  • Climbazole, octopirox and zinc pyrethione can be used as antidandruff agents.
  • Common film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinyl pyrrolidone, vinyl pyrrolidone / vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, collagen, hyaluronic acid or its salts and similar compounds.
  • Montmorillonites, clay minerals, pemulene and alkyl-modified carbopol types can serve as swelling agents for aqueous phases.
  • UV light protection filters are organic substances which are able to absorb ultraviolet rays and the absorbed energy in the form of longer-wave radiation, e.g. To give off heat again.
  • UVB filters can be oil-soluble or water-soluble. As oil-soluble substances e.g. to call:
  • 4-aminobenzoic acid derivatives preferably 2-ethylhexyl 4- (dimethylamino) benzoate, 2-octyl 4- (dimethylamino) benzoate and amyl 4- (dimethylamino) benzoate;
  • esters of cinnamic acid preferably 2-ethylhexyl 4-methoxycinnamate, isopentyl 4-methoxycinnamate, 2-ethylhexyl 2-cyano-3-phenylcinnamate (octocrylene);
  • esters of salicylic acid preferably 2-ethylhexyl salicylate, 4-isopropylbenzyl salicylate, homomethyl salicylic acid;
  • benzophenone preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone;
  • Esters of benzalmalonic acid preferably di-2-ethylhexyl 4-methoxybenzmalonate; • Triazine derivatives, such as 2,4,6-trianilino- (p-carbo-2'-ethyl-1'-hexyloxy) -1, 3,5-triazine and octyltriazone.
  • Propane-1,3-dione e.g. 1- (4-tert-butylphenyl) -3- (4'methoxyphenyl) propane-1,3-dione;
  • Sulfonic acid derivatives of 3-benzylidene camphor e.g. 4- (2-oxo-3-bornylidene methyl) benzenesulfonic acid and 2-methyl-5- (2-oxo-3-bornylidene) sulfonic acid and their salts.
  • UV-A filters such as 1- (4'-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-1, 3-dione or 1-phenyl-3-
  • UV-A filters 4'-isopropylphenyl) propane-1,3-dione.
  • the UV-A and UV-B filters can of course also be used in mixtures.
  • insoluble pigments namely finely dispersed metal oxides or salts, such as, for example, titanium dioxide, zinc oxide, iron oxide, aluminum oxide, cerium oxide, zirconium oxide, silicates (talc), barium sulfate and zinc stearate are also suitable for this purpose.
  • the particles should have an average diameter of less than 100 nm, preferably between 5 and 50 nm and in particular between 15 and 30 nm. They can have a spherical shape, but it is also possible to use particles which have an ellipsoidal shape or shape which differs from the spherical shape in some other way.
  • secondary light stabilizers of the antioxidant type can also be used, which interrupt the photochemical reaction chain which is triggered when UV radiation penetrates the skin. Typical examples are superoxide dismutase, tocopherols (vitamin E) and ascorbic acid (vitamin C). Further suitable UV light protection filters can be found in the overview by P.Finkel in S ⁇ FW-Journal 122, 543 (1996).
  • Hydrotropes such as ethanol, isopropyl alcohol or polyols can also be used to improve the flow behavior.
  • Polyols that come into consideration here preferably have 2 to 15 carbon atoms and at least two hydroxyl groups. Typical examples are
  • Alkylene glycols such as, for example, ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol and polyethylene glycols with an average molecular weight of 100 to 1,000 daltons;
  • Lower alkyl giucosides in particular those with 1 to 8 carbons in the alkyl radical, such as methyl and butyl glucoside;
  • Sugar alcohols with 5 to 12 carbon atoms such as sorbitol or mannitol,
  • Aminosugars such as glucamine.
  • Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid and the other classes of substances listed in Appendix 6, Parts A and B of the Cosmetics Ordinance.
  • N, N-diethyl-m-touluamide, 1, 2-pentanediol or Insect repellent 3535 are suitable as insect repellents, and dihydroxyacetone is suitable as a self-tanner.
  • Perfume oils include mixtures of natural and synthetic fragrances. Natural fragrances are extracts of flowers (lily, lavender, roses, jasmine, neroli, yiang-ylang), stems and leaves (geranium, patchouli, petitgrain), fruits (anise, coriander, caraway, juniper), fruit peel (bergamot, lemon, Oranges), roots (mace, angelica, celery, cardamom, costus, iris, calmus), wood (pine, sandal, guaiac, cedar, rosewood), herbs and grasses (tarragon, lemongrass, sage, thyme), Needles and twigs (spruce, fir, pine, mountain pine), resins and balms (galbanum, elemi, benzoin, myrrh, olibanum, opoponax).
  • Typical synthetic fragrance compounds are products of the ester, ether, aldehyde, ketone, alcohol and hydrocarbon type. Fragrance compounds of the ester type are, for example, benzyl acetate, phenoxyethyl isobutyrate, p-tert-butylcyclohexyl acetate, linalyl acetate, dimethylbenzylcarbinylacetate, phenylethyl acetate, linalyl benzoate, benzyl formate, ethyl methyl phenyl glycinate, allyl cyclohexyl propylate pylate allylpropionate,
  • the ethers include, for example, benzylethyl ether, the aldehydes, for example, the linear alkanals having 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde,
  • fragrance oils of lower volatility which are mostly used as aroma components, are also suitable as perfume oils, e.g. sage oil, chamomile oil, clove oil, lemon balm oil, mint oil, cinnamon leaf oil, linden blossom oil, juniper berry oil, vetiver oil, oliban oil, galbanum oil, labolanum oil and lavandin oil.
  • the dyes which can be used are those substances which are suitable and approved for cosmetic purposes, as compiled, for example, in the publication "Cosmetic Dyes” by the Dye Commission of the German Research Foundation, Verlag Chemie, Weinheim, 1984, pp. 81-106. These dyes are usually used in concentrations of 0.001 to 0.1% by weight, based on the mixture as a whole.
  • the total proportion of auxiliaries and additives can be 1 to 50, preferably 5 to 40% by weight, based on the composition.
  • the agents can be produced by customary cold or hot processes; the phase inversion temperature method is preferably used.
  • Another object of the invention finally relates to the use of fatty acid polyglycol ester sulfates as anionic emulsifiers for the production of aqueous pearlescent concentrates.
  • the pearlescent concentrates 1 to 6 according to the invention and the comparative mixture V1 were stored at 40 ° C. for 14 days and the viscosity was determined using the Brookfield method in an RVT viscometer (23 ° C., 10 rpm, spindle 5).
  • Aqueous hair shampoo formulations were then prepared by mixing the starting materials at 20 ° C., each containing 2 g of pearlescent concentrate, 15 g of coconut oil alcohol + 2EO sulfate sodium salt, 3 g of dimethylpolysiloxane, 5 g of coconut alkyl glucoside and 1.5 g of esterquat (water ad 100 wt .-%) contained.

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Abstract

L'invention concerne de nouveaux concentrés aqueux de lustre nacré contenant (par rapport à la part non aqueuse) (a) entre 1 et 99 % en poids de sulfates d'ester de polyglycol d'acide gras; (b) entre 0 et 90 % en poids d'émulsifiants anioniques, non ioniques, cationiques ampholytiques et/ou zwitterioniques; (c) entre 1 et 50 % en poids de cires à lustre nacré, ainsi que (d) entre 0 et 40 % en poids de polyols, sous réserve que les quantités indiquées s'additionnent jusqu'à 100 % en poids.
PCT/EP1998/005187 1997-08-25 1998-08-17 Dispersions aqueuses de lustre nacre WO1999009944A1 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
DE19736906.5 1997-08-25
DE19736906A DE19736906A1 (de) 1997-08-25 1997-08-25 Verfahren zur Herstellung von sulfatierten Fettsäurealkylenglykolestern
DE19741911.9 1997-09-25
DE19741911A DE19741911C1 (de) 1997-09-25 1997-09-25 Stark schäumende Detergensgemische
DE19810888.5 1998-03-13
DE19810888A DE19810888A1 (de) 1998-03-13 1998-03-13 Wäßrige Perlglanzdispersionen

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WO2001010403A1 (fr) * 1999-08-06 2001-02-15 Cognis Deutschland Gmbh Dispersions aqueuses de lustre perlaire contenant des esters d'acide carboxylique alcoxylee
WO2002030370A1 (fr) * 2000-10-13 2002-04-18 L'oreal Composition cosmetique comprenant un latex anionique, un ether a deux chaines grasses et un melange d'alcools gras
WO2002056839A2 (fr) * 2001-01-18 2002-07-25 Cognis Deutschland Gmbh & Co. Kg Agent de lustrage nacre
WO2003004594A1 (fr) * 2001-06-30 2003-01-16 Henkel Kommanditgesellschaft Auf Aktien Gel nettoyant a dissolution rapide
WO2003033634A1 (fr) * 2001-10-13 2003-04-24 Cognis Deutschland Gmbh & Co. Kg Opacifiants de faible viscosite, exempts de tensioactifs anioniques
EP1707180A1 (fr) * 2005-03-31 2006-10-04 L'oreal Compositions cosmétiques ou dermatologiques, comprenant du disulfure de sélénium, une base lavante et éventuellement au moins un éther à deux chaînes grasses, particulier, et procédés de traitement cosmétique
FR2883739A1 (fr) * 2005-03-31 2006-10-06 Oreal Composition comprenant du disulfure de selenium et presentant un temps de relaxation particulier
FR2883740A1 (fr) * 2005-03-31 2006-10-06 Oreal Composition cosmetique ou dermatologique, comprenant du disulfure de selenium et au moins un ether a deux chaines grasses particulier, et procede de traitement cosmetique
WO2008068222A1 (fr) * 2006-12-08 2008-06-12 Unilever Plc Compositions tensioactives concentrées
US7910535B2 (en) 2006-03-22 2011-03-22 The Procter & Gamble Company Liquid treatment composition comprising a pearlescent agent
WO2011023803A3 (fr) * 2009-08-27 2011-06-03 Otc Gmbh Concentré nacré et procédé de production
WO2014190130A1 (fr) * 2013-05-24 2014-11-27 The Procter & Gamble Company Composition de tensioactifs concentrée
US9267095B2 (en) 2013-05-24 2016-02-23 The Procter & Gamble Company Low pH detergent composition comprising nonionic surfactants
US10519400B2 (en) 2013-05-24 2019-12-31 The Procter & Gamble Company Low PH detergent composition
WO2020044235A1 (fr) * 2018-08-27 2020-03-05 Lonza Ltd Composition de tensioactif anionique liquide fluidifiable à concentration élevée

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WO2002056839A2 (fr) * 2001-01-18 2002-07-25 Cognis Deutschland Gmbh & Co. Kg Agent de lustrage nacre
WO2002056839A3 (fr) * 2001-01-18 2003-10-02 Cognis Deutschland Gmbh Agent de lustrage nacre
WO2003004594A1 (fr) * 2001-06-30 2003-01-16 Henkel Kommanditgesellschaft Auf Aktien Gel nettoyant a dissolution rapide
WO2003033634A1 (fr) * 2001-10-13 2003-04-24 Cognis Deutschland Gmbh & Co. Kg Opacifiants de faible viscosite, exempts de tensioactifs anioniques
EP1707180A1 (fr) * 2005-03-31 2006-10-04 L'oreal Compositions cosmétiques ou dermatologiques, comprenant du disulfure de sélénium, une base lavante et éventuellement au moins un éther à deux chaînes grasses, particulier, et procédés de traitement cosmétique
FR2883739A1 (fr) * 2005-03-31 2006-10-06 Oreal Composition comprenant du disulfure de selenium et presentant un temps de relaxation particulier
FR2883740A1 (fr) * 2005-03-31 2006-10-06 Oreal Composition cosmetique ou dermatologique, comprenant du disulfure de selenium et au moins un ether a deux chaines grasses particulier, et procede de traitement cosmetique
US7910535B2 (en) 2006-03-22 2011-03-22 The Procter & Gamble Company Liquid treatment composition comprising a pearlescent agent
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US8357648B2 (en) 2006-03-22 2013-01-22 The Procter & Gamble Company Liquid treatment unitized dose composition
WO2008068222A1 (fr) * 2006-12-08 2008-06-12 Unilever Plc Compositions tensioactives concentrées
AU2007328936B2 (en) * 2006-12-08 2010-09-02 Unilever Plc Concentrated surfactant compositions
WO2011023803A3 (fr) * 2009-08-27 2011-06-03 Otc Gmbh Concentré nacré et procédé de production
US8623809B2 (en) 2009-08-27 2014-01-07 Otc Gmbh Pearlescent concentrate and process for production
WO2014190130A1 (fr) * 2013-05-24 2014-11-27 The Procter & Gamble Company Composition de tensioactifs concentrée
CN105283530A (zh) * 2013-05-24 2016-01-27 宝洁公司 浓缩型表面活性剂组合物
US9267095B2 (en) 2013-05-24 2016-02-23 The Procter & Gamble Company Low pH detergent composition comprising nonionic surfactants
US9840681B2 (en) 2013-05-24 2017-12-12 The Procter & Gamble Company Concentrated surfactant composition
US10519400B2 (en) 2013-05-24 2019-12-31 The Procter & Gamble Company Low PH detergent composition
WO2020044235A1 (fr) * 2018-08-27 2020-03-05 Lonza Ltd Composition de tensioactif anionique liquide fluidifiable à concentration élevée
US11793740B2 (en) 2018-08-27 2023-10-24 Arxada Ag High-concentrate flowable liquid anionic surfactant composition

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