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WO2009083131A2 - Compositions cosmétiques, pharmaceutiques ou dermatologiques présentant une teneur élevée en composants de soin hydrosolubles - Google Patents

Compositions cosmétiques, pharmaceutiques ou dermatologiques présentant une teneur élevée en composants de soin hydrosolubles Download PDF

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Publication number
WO2009083131A2
WO2009083131A2 PCT/EP2008/010678 EP2008010678W WO2009083131A2 WO 2009083131 A2 WO2009083131 A2 WO 2009083131A2 EP 2008010678 W EP2008010678 W EP 2008010678W WO 2009083131 A2 WO2009083131 A2 WO 2009083131A2
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acid
composition according
salts
component
weight
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German (de)
English (en)
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WO2009083131A3 (fr
Inventor
Matthias Loeffler
Thomas Lindner
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Clariant International Ltd
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Clariant International Ltd
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/007—Preparations for dry skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A61K8/8182—Copolymers of vinyl-pyrrolidones. Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions

Definitions

  • Cosmetic, pharmaceutical or dermatological compositions containing a high content of water-soluble care components containing a high content of water-soluble care components
  • the present invention relates to cosmetic, pharmaceutical or dermatological compositions
  • cosmetic, pharmaceutical or dermatological compositions comprising crosslinked water-soluble or water-swellable copolymers based on acrylamidoalkylsulfonic acids and / or salts thereof, characterized by a crosslinker content of more than 0.5% by weight based on the copolymer and at least one or more water-soluble care components in amounts by weight of at least 10%, based on the finished cosmetic, pharmaceutical or dermatological compositions, as well as their use for cosmetic and medical purposes.
  • the cosmetic, pharmaceutical or dermatological compositions according to the invention are distinguished by a markedly improved moisturizing effect, good skin sensory properties and excellent theological behavior.
  • the aim of skin care is to compensate for the loss of fat and water caused by daily washing of the skin, to protect the skin from environmental influences, especially from sun and wind, to create a barrier against dirt, chemicals and microorganisms, the loss of endogenous substances ( For example, water, natural fats, electrolytes) counteract or compensate for this and delay the aging of the skin.
  • endogenous substances For example, water, natural fats, electrolytes
  • cosmetic skin care products should have a clear appearance and favorable theological behavior, be toxicologically and ecotoxicologically harmless and produce a pleasant skin feel.
  • Water- or solvent-containing multicomponent systems such as emulsions or suspensions are often made for economic reasons For technical reasons or reasons of stability adjusted to higher viscosities or thickened.
  • the high viscosity of such preparations also offers further advantages in the production, packaging, filling and storage as well as during transport.
  • polyvinyl alcohols polyacrylamides, polyacrylic acid and various salts of polyacrylic acid, polyvinylpyrrolidone, polyvinyl methyl ether, polyethylene oxides, copolymers of maleic anhydride and vinyl methyl ether, as well as various mixtures and copolymers of the abovementioned compounds.
  • the compounds mentioned show a variety of disadvantages in the application. So z.
  • the cellulose derivatives or generally based on natural raw materials and the resulting formulations very susceptible to bacteria. From an application point of view, they are usually due to the formation of unpleasant, "stringy" gels.
  • Fatty acid polyethylene glycol esters tend to hydrolyze in the presence of water, the resulting insoluble fatty acids cause undesirable turbidity.
  • Thickening agents of natural origin eg agar-agar or tragacanth
  • DE 100 65 047 and DE 100 65 046 describe cosmetic or dermatological gel creams of the oil-in-water type or emulsions of the oil-in-water type containing ammonium acryloyldimethyltaurate / vinylpyrrolidone copolymers.
  • hydrophobically modified comb polymers based on acryloyldimethyltaurine (AMPS ®) - suitable for use both as a thickener, bodying agent, emulsifier, solubilizer, dispersant, lubricant, adhesive, conditioner and / or stabilizer - excellent for the formulation of cosmetic, pharmaceutical and dermatological compositions are suitable.
  • WO 2004/032894 discloses cosmetic oil-in-water emulsions which comprise water-soluble copolymers based on monomers selected from (meth) acrylic acid, acrylamide, (meth) acrylic acid ester, N-vinylpyrrolidone with a crosslinker fraction of 0.005 to 0.5% by weight. %, based on the copolymer, and more than 10% by weight of a skin care component, in particular glycerol, based on the emulsion.
  • Some common skincare components as well as Giycerin have the disadvantage, especially at use concentrations above 5 wt .-%, based on the finished skin care products, to cause a sticky skin feel.
  • the copolymers used according to the invention preferably have a molecular weight of from 10 3 to 10 9 g / mol, more preferably from 10 4 to 10 7 g / mol, particularly preferably from 5 * 10 4 to 5 * 10 6 g / mol.
  • acrylamidoalkylsulfonic acids 2-acrylamido-2-methylpropanesulfonic acid is preferred.
  • Li + are preferred 1 " , wherein R 1 , R 2 and R 3 are the same or different and are hydrogen, a linear or branched alkyl group having 1 to 22 carbon atoms, a linear or branched, mono- or polyunsaturated alkenyl group having 2 to
  • the acrylamidoalkylsulfonic acids and / or their salts of component A) are selected from 2-acrylamido-2-methylpropanesulfonic acid and inorganic or organic salts of 2-acrylamido-2-methylpropanesulfonic acid, preferably from the latter Li + , Na + , K + , Mg ++ , Ca ++ , Al +++ , NhV salts, quaternary ammonium salts [HNR 1 R 2 R 3 I + , wherein R 1 , R 2 and R 3 are independently the same or different and are hydrogen, a linear or branched alkyl group having 1 to 22 carbon atoms, a linear or branched mono- or polyunsaturated alkenyl group having 2 to 22 carbon atoms, a linear or branched mono-hydroxyalkyl group having 2 to 10 Carbon atoms, preferably a mono-hydroxyethyl or a linear or branched monohydroxypropyl group
  • Mixtures of two or more of the abovementioned representatives, ie mixtures of different acrylamidoalkylsulfonic acids or of different salts of one or more acrylamidoalkylsulfonic acids, are also within the meaning of the invention.
  • the degree of neutralization of acrylamidoalkylsulfonic acids can be between 0 and 100%. Preference is given to a degree of neutralization of above 80%.
  • the content of acrylamido-alkylsulfonic acids or sulfonates is at least 0.1% by weight, preferably from 20 to 99.49% by weight, particularly preferably from 50 to 98% by weight.
  • comonomers B it is possible to use all olefinically unsaturated, noncationic monomers whose reaction parameters permit copolymerization with acrylamidoalkylsulfonic acids or their salts in the respective reaction media.
  • the degree of neutralization of the carboxylic acids can be between 0 and 100%.
  • N-vinylamides preferably N-vinylformamide (VIFA), N-vinylmethylformamide, N-vinylmethylacetamide (VIMA) and N-vinylacetamide; cyclic N-vinylamides (N-vinyllactams) having a ring size of 3 to 9, preferably N-vinylpyrrolidone (NVP) and N-vinylcaprolactam; Amides of acrylic and methacrylic acid, preferably acrylamide, methacrylamide, N, N-dimethylacrylamide, N, N-diethylacrylamide and N, N-diisopropylacrylamide; alkoxylated acrylic and methacrylamides, preferably hydroxymethylmethacrylamide, hydroxyethylmethacrylamide, hydroxypropylmethacrylamide; Succinic mono [2- (methacryloyloxy) ethyl ester], N, N-dimethylamin
  • Preferred as counter ions of the salts of the comonomers B), for example the salts of the unsaturated carboxylic acids, are Li + , Na + , K + , Mg ++ , Ca ++ , Al +++ , NH 4 + , quaternary ammonium ions [HNR 1 R 2 R 3 ] "1" , wherein R 1 , R 2 and R 3 are independently the same or different and are hydrogen, a linear or branched alkyl group having 1 to 22 carbon atoms, a linear or branched, mono- or polyunsaturated alkenyl group having 2 to 22 carbon atoms, a linear or branched mono-hydroxyalkyl group having 2 to 10 carbon atoms, preferably a mono-hydroxyethyl or a linear or branched mono-hydroxypropyl group, a linear or branched di-hydroxyalkyl group having 3 to 10 carbon atoms, or (EO) n ( PO) m H, where EO is
  • ammonium counterions of the salts of the comonomers B it may thus in turn z.
  • B. be monoalkylammonium, dialkylammonium or trialkylammonium counterions, wherein the alkyl groups independently z.
  • B. (C- ⁇ -C 22 ) alkyl radicals may be.
  • the (CrC 2 2) -alkyl radicals z. B. by (C 2 -Ci 0 ) -Hydroxyalkylreste be replaced or it may be in the ammonium counterions z.
  • B. also be monosubstituted to trisubstituted ethoxylated ammonium compounds with different degrees of ethoxylation.
  • the comonomers of component B) do not comprise the acrylamidoalkylsulfonic acids or their salts listed under component A).
  • the Comonomers of component B) to discrete molecular weight compounds.
  • the proportion by weight of comonomers B), based on the total mass of the copolymers, can be from 0 to 99.39% by weight and is preferably from 0.5 to 80% by weight, more preferably from 2 to 50% by weight.
  • the macromonomers C) are at least monoolefinically functionalized polymers having one or more discrete repeating units and a number average molecular weight greater than or equal to 200 g / mol. In the copolymerization, it is also possible to use mixtures of chemically different macromonomers C).
  • the macromonomers are polymeric structures which are composed of one or more repeating unit (s) and have a characteristic molecular weight distribution for polymers.
  • Preferred as macromonomers C) are compounds according to formula (1)
  • R 1 , R 2 , R 3 and R 4 independently of one another denote hydrogen or n-aliphatic, iso-aliphatic, olefinic, cycloaliphatic, arylaliphatic or aromatic (CrC 3 o) -hydrocarbon radicals
  • Y represents O, S, NH, PH
  • v and w are the stoichiometric coefficients concerning the ethylene oxide units (EO) and propylene oxide units (PO), where v and w independently represent a number from 0 to 500, preferably 0 to 30, and the sum of v and w averages ⁇ 1 must be and the distribution of EO and PO units can be random, block, alternating or gradient across the macromonomer chain.
  • the macromonomers of component C) are particularly preferably selected from one or more compounds of the formula (1) in which
  • component C) selected from one or more compounds of the formula (1) in which R 1 , R 2 and R 3 independently of one another are hydrogen or methyl, R 4 is a linear or branched, saturated or unsaturated aliphatic hydrocarbon radical with 8 to 22 carbon atoms, YO, S, NH or PH 1 is preferably O, and v is a number from 1 to 50, preferably from 2 to 30, and w is the number 0.
  • macromonomers C are esters of acrylic acid or methacrylic acid with
  • the molecular weight of the macromonomers C) is preferably from 200 to 10 6 g / mol, more preferably from 200 to 10 4 g / mol, and more preferably from 200 to 5,000 g / mol.
  • suitable macromonomers C) in amounts up to 99.39 wt .-% can be used.
  • the ranges find 0.5 to 30 wt .-% and the ranges of 70 to 99.39 wt .-% application.
  • Particularly preferred are the ranges of 1 to 20 wt .-% and 75 to 95 wt .-%.
  • the one or more copolymers of component I) which are contained in the compositions according to the invention have been obtained by free-radical copolymerization in the presence of at least one polymeric additive of component D).
  • the polymeric additives of component D) differ from the monomers of components A), B) and C) and the crosslinkers of
  • Component E) in that, in contrast to the monomers or crosslinkers mentioned, they do not have polymerizable double bonds and are therefore incorporated via another mechanism into the copolymers present in the compositions according to the invention. For this reason, they are not referred to in the context of the present invention as “monomers”, but as polymeric "additives”.
  • the copolymerization is preferably carried out in the presence of at least one polymeric additive D) in such a way that the additive D) is added completely or partially dissolved to the polymerization medium before the actual copolymerization.
  • the use of several additives D) is also erf ⁇ ndungshield.
  • Crosslinked additives D) can also be used.
  • the additives D) or mixtures thereof need only be completely or partially soluble in the chosen polymerization medium.
  • the additive D) has several functions. On the one hand, it prevents the formation of overcrosslinked polymer components in the forming copolymer in the actual polymerization step and, on the other hand, the additive D) is statistically attacked by active radicals in accordance with the generally known mechanism of graft copolymerization. As a result, depending on the additive D), more or less large portions thereof are incorporated into the copolymers.
  • suitable additives D) have the property of changing the solution parameters of the copolymers which form during the free-radical polymerization reaction in such a way that the average molecular weights are shifted to higher values. Compared with analogous copolymers prepared without the addition of additives D), those prepared with the addition of additives D) advantageously show a significantly higher viscosity in aqueous solution.
  • Preferred as additives D) are in water and / or alcohols, preferably in t-butanol, soluble homo- and copolymers.
  • Copolymers are to be understood as meaning those with more than two different monomer types.
  • additives D are homopolymers and copolymers of N-vinylformamide, N-vinylacetamide, N-vinylpyrrolidone, ethylene oxide, propylene oxide, acryloyldimethyltaurine, N-vinylcaprolactam, N-vinylmethylacetamide, acrylamide, acrylic acid, methacrylic acid, N-vinylmorpholide, hydroxyethyl methacrylate, Diallyldimethylammonium chloride (DADMAC), [2- (methacryloyloxy) ethyl] trimethylammonium chloride, acrylamidopropyltrimethylammonium chloride (APTAC), Methacrylamidopropyltrimethylammoniumchloricl (MAPTAC); Polyalkylene glycols and / or alkyl polyglycols.
  • DADMAC Diallyldimethylammonium chloride
  • ATAC acrylamidopropyltrimethylammonium chlor
  • Particularly preferred additives D) are polyvinylpyrrolidones (z. B. Luviskol K15 ®, ® K20 and K30 ® from BASF), poly (N-vinylformamides), poly (N-
  • Vinylcaprolactame and copolymers of N-vinylpyrrolidone, N-vinylformamide and / or acrylic acid, which may also be partially or completely saponified.
  • the molecular weight of the additives D) is preferably from 10 2 to 10 7 g / mol, more preferably from 0.2 * 10 4 to 10 6 g / mol.
  • the amount used of the polymeric additive D based on the total mass of the copolymer, 0 to 90 wt .-%, preferably 1 to 20 wt .-% and particularly preferably 1, 5 to 10 wt .-%.
  • the one or more copolymers of component I) contained in the compositions of the invention have been obtained by free radical copolymerization in the absence of a polymeric additive of component D).
  • the crosslinkers of component E) contain 2 or more free-radically polymerizable double bonds.
  • Preferred crosslinkers E) are methylenebisacrylamide; methylenebismethacrylamide; Esters of unsaturated mono- and polycarboxylic acids with polyols, preferred
  • Diacrylates, triacrylates, dimethacrylates and trimethacrylates more preferably butanediol diacrylate, ethylene glycol diacrylate, butanediol dimethacrylate and ethylene glycol dimethacrylate, trimethylolpropane triacrylate (TMPTA) and trimethylolpropane trimethacrylate (TMPTMA); Allyl compounds, preferably allyl acrylate, allyl methacrylate, triallyl cyanurate, maleic acid diallyl ester,
  • TMPTA trimethylolpropane triacrylate
  • MCA methylenebisacrylamide
  • the amount of crosslinker E) used based on the total mass of the copolymer, 0.51 to 5 wt .-%, preferably 1 to 2.5 wt .-%, particularly preferably 1.2 to 2 wt .-%.
  • compositions according to the invention are particularly preferred.
  • R 5 is hydrogen, methyl or ethyl
  • Z is Ci-C ⁇ -alkylene
  • R 6 , R 7 and R 8 may be the same or different and are hydrogen, a linear or branched alkyl group having in each case 1 to 30, preferably 1 to 20, particularly preferably 1 to 12 C atoms, or a linear or branched mono- or polyunsaturated alkenyl group having in each case 2 to 30, preferably 2 to 20, particularly preferably 2 to 12, C atoms, and
  • compositions according to the invention are particularly preferred.
  • compositions according to the invention containing I) at least one copolymer obtainable by copolymerization of A) from 0.1 to 99.39% by weight, preferably from 49.49 to 95.39% by weight, especially preferably 69.49 to 90.39% by weight, of one or more acrylamidoalkylsulfonic acids and / or their salts,
  • the cosmetic, pharmaceutical and dermatological compositions of the invention contain the crosslinked copolymers of component I) in amounts of preferably 0.05 to 10 wt .-%, particularly preferably 0.1 to 5 wt .-%, particularly preferably 0.5 to 2 wt .-%, based on the finished compositions.
  • the preparation of the copolymers used according to the invention can be carried out in the manner described in WO 02/43689 and in EP 1 116 733.
  • Water-soluble care components according to component II) in the sense of the invention are preferably:
  • Vitamins preferably selected from niacin, biotin, vitamin B2, vitamin B3, vitamin B6, vitamin B3 derivatives (salts, acids, esters, amides, alcohols), vitamin C, vitamin C derivatives (salts, acids, esters, amides, alcohols), preferably as the sodium salt of the monophosphoric acid ester of ascorbic acid or as the magnesium salt of the phosphoric acid ester of ascorbic acid, tocopherol and tocopherol acetate;
  • Polyols preferably selected from glycols, polyalkylene polyols, alkylene polyols, propylene glycol, dipropylene glycol, polypropylene glycol, polyethylene glycol, hexylene glycol, butylene glycol, neopentyl glycol, sorbitol, hydroxypropyl sorbitol, erythritol, threitol, pentaerythritol, xylitol, glucitol, mannitol, triols such as 1, 2,6-hexanetriol , Trimethylolpropane;
  • Glycerol glycerin derivatives preferably selected from glycerol, ethoxylated glycerin, propoxylated glycerol and mixtures thereof;
  • Amino acids preferably selected from L-isomers of serine, alanine, proline, hydroxyproline and D and L isomers of naturally occurring amino acids;
  • Moisturizing agents preferably selected from the sodium salt of 2-pyrrolidone-5-carboxylate (NaPCA), guanidine; Glycolic acid and its salts, lactic acid and its salts, glucosamines and their salts, lactamide monoethanolamine, Acetamide monoethanolamine, urea, hydroxy acids, preferably ⁇ - and ⁇ -hydroxy acids, more preferably ⁇ -hydroxy acids, panthenol and derivatives thereof, preferably D-panthenol (R-2,4-dihydroxy-N- (3-hydroxypropyl) -3,3- dimethylbutamide), DL-panthenol, calcium pantothenate, panthetin, pantotheine, panthenylethyl ether;
  • Biogenic agents preferably selected from plant extracts, in particular Aloe Vera, local anesthetics, antibiotics, antiphlogistics, antiallergics, corticosteroids, sebostatics, bisabolol ®, ® allantoin, phytantriol ® and proteins;
  • Polycationic compounds preferably selected from cationic polymers known by the INCI name "Polyquaternium” and in particular Polyquaternium-31, Polyquaternium-16, Polyquaternium-24, Polyquaternium-7, Polyquaternium-22, Polyquaternium-39, Polyquaternium-28, Polyquaternium -2, Polyquaternium-10, Polyquaternium-11, Polyquaternium 37 (and) mineral oil (and) PPG trideceth (Salcare ® SC95), PVP dimethylaminoethyl methacrylate copolymer, Guarhydroxypropyltriammoniumchlorid, and calcium alginate and ammonium alginate contained.
  • Polyquaternium Polyquaternium-31, Polyquaternium-16, Polyquaternium-24, Polyquaternium-7, Polyquaternium-22, Polyquaternium-39, Polyquaternium-28, Polyquaternium -2, Polyquaternium-10, Polyquaternium-11, Polyquaternium 37 (and) mineral oil (and) P
  • compositions according to the invention comprising one or more water-soluble care components for the skin and / or the hair of component II) selected from glycerol, sorbitol, urea, niacinamides, panthenol, tocopherol acetate, propylene glycol, erythritol and dipropylene glycol.
  • component II selected from glycerol, sorbitol, urea, niacinamides, panthenol, tocopherol acetate, propylene glycol, erythritol and dipropylene glycol.
  • the cosmetic, pharmaceutical and dermatological compositions according to the invention comprise the abovementioned water-soluble skin care components and / or hairs of component II), preferably in amounts of from 10 to 40% by weight, more preferably from 12 to 30% by weight and particularly preferably from 15 to 25 wt .-%, based on the finished compositions.
  • the cosmetic, pharmaceutical and dermatological compositions according to the invention have viscosities in the range of 500 to 300,000 mPa.s, preferably in the range of 1,000 to 250,000 mPa.s and more preferably in the range of 2,000 to 150,000 mPa.s and exceptionally preferably in the range of 3,000 to 100,000 mPa.s (25 0 C, Brookfield RVT, TC spindle at 5 rpm).
  • compositions according to the invention are fluids, gels, oils, foams, sprays, lotions, gel creams and creams.
  • compositions according to the invention are preferably present on an aqueous basis, on an aqueous-alcoholic basis or as an oil-in-water emulsion. With particular preference they are present as emulsions of the oil-in-water type.
  • compositions according to the invention are present as emulsions of the oil-in-water type, preferably as cosmetic or dermatological emulsions of the oil-in-water type, and contain up to 89.95% by weight, based on the total weight of the composition a) .-%, preferably 60 to 89.95 Gew. -%, particularly prefers 70 to 87.75 Gew. -%, in particular prefers 75 to
  • compositions according to the invention are present as oil-in-water gel creams, preferably as oil-in-water cosmetic or dermatological gel creams, and contain up to 89.95% by weight, based on the total weight of the composition a). %, preferably 50 to 89.95% by weight, particularly preferably 70 to 87.95% by weight, particularly preferably 75 to 84.95% by weight of a water phase, b) up to 60% by weight, preferably 1 to 30 wt .-%, more preferably
  • Suitable aqueous-alcoholic or alcoholic compositions according to the invention are all monohydric or polyhydric alcohols.
  • Alcohols having 1 to 4 carbon atoms such as ethanol, propanol, isopropanol, n-butanol, i-butanol, t-butanol or glycerol and alkylene glycols, in particular propylene, butylene or hexylene glycol, and mixtures of the alcohols mentioned are preferred.
  • Further preferred alcohols are polyethylene glycols having a molecular weight below 2,000. In particular, use of polyethylene glycol having a molecular weight of between 200 and 600 and of polyethylene glycol having a molecular weight of between 400 and 600 is preferred.
  • the oil-in-water emulsions according to the invention may preferably contain as oil phase:
  • Hydrocarbon oils with linear or branched, saturated or unsaturated C 7 -C 4 o-carbon chains for example dodecane, isododecane, cholesterol, hydrogenated polyisobutylenes, docosans, hexadecane, isohexadecane, paraffins and isoparaffins, but also triglycerides of animal and vegetable origin, for example beef tallow, lard , Goose fat, perhydrosqualene, lanolin, sunflower, corn, soybean, rice, jojoba, babussu, pumpkin, grapeseed, sesame, walnut, apricot, macadamia, avocado, sweet almond, meadowfoam -, castor oil, olive oil, peanut oil, rapeseed oil and coconut oil and synthetic oils such as Purcellinöl, linear and / or branched fatty alcohols and fatty acid esters, preferably Guerbet alcohols having 6 to 18, preferably 8 to 10, carbon atoms; Esters of
  • Paraffin wax or microwaxes optionally in combination with hydrophilic waxes, such as. Cetylstearyl alcohol; Fluorinated and perfluorinated oils; Monoglycerides of C 1 -C 3 o-carboxylic acids, diglycerides of C 1 -C 3 -carboxylic acids, triglycerides of C 1 -C 3 o-carboxylic acids, for example triglycerides of caprylic / capric acids, ethylene glycol monoesters of CrC 3 o-carboxylic acids,
  • Ethylene glycol diesters of Ci-C 3 o-carboxylic acids propylene glycol monoesters of C- ⁇ -C 30 carboxylic acids, propylene glycol diesters of Ci-C 30 carboxylic acids, and propoxylated and ethoxylated derivatives of the above-mentioned classes of compounds.
  • the carboxylic acids may contain linear or branched alkyl groups or aromatic groups. Examples include diisopropyl sebacate,
  • Glyceryl Glyceryldipalmitat Ci-Cso-Carbonklader and polyesters of sugars, for example glucose tetraoleate, Glucosetetraester of soybean oil fatty acid, mannose tetraesters of soybean oil fatty acid, galactose tetraesters of oleic acid, arabinose tetraesters of linoleic acid, xylose tetralinoleate, galactose pentaoleate, sorbitol tetraoleate, sorbitol hexaesters of unsaturated soybean oil fatty acid, xylitol pentaoleate, Sucrosetetraoleat, Sucrosepentaoleat, Sucrose hexaoleate, sucrose heptaoleate, sucrose oleate.
  • sugars for example glucose tetraoleate, Glucosetetraester of soybean oil fatty
  • silicone oils are preferably available dimethylpolysiloxanes and cyclomethicones, polydialkylsiloxanes R 3 SiO (RaSiO) x SiRa, where R is methyl or ethyl, particularly preferably methyl, and x is a number from 2 to 500, for example those under the trade name VICASIL (General Electric Company), DOW CORNING 200, DOW CORNING 225, DOW CORNING 200 (Dow Corning Corporation), dimethicones available, trimethylsiloxysilicate [(CH 2 ) SSiO) 1 Z 2 ] X [SiO 2 ] Y , where x is a number from 1 to 500 and y is a number from 1 to 500, dimethiconols R 3 SiO [R 2 SiO] x SiR 2 OH and
  • the cosmetic compositions according to the invention may contain, as further auxiliaries and additives, surfactants, emulsifiers, cationic polymers, further thickeners, film formers, antimicrobial agents, astringents, antioxidants, UV light protection filters, pigments / micropigments, gelling agents and other additives customary in cosmetics, such as As superfatting agents, silicones, stabilizers, conditioning agents, preservatives, pearlescing agents, dyes, fragrance and perfume oils, solvents, opacifiers, fatty alcohols, substances with keratolytic and keratoplastic effect or anti-dandruff agent included.
  • anionic detergent-active substances i. anionic surfactants, may be mentioned preferably:
  • These compounds and their mixtures are used in the form of their water-soluble or water-dispersible salts, for example the sodium, potassium, magnesium, ammonium, mono-, di- and triethanolammonium and analogous alkylammonium salts.
  • the amount of anionic surfactants is preferably 1 to 30 wt .-%, particularly preferably 5 to 25 wt .-%, particularly preferably 10 to 22 wt .-%, based on the finished compositions.
  • Suitable cationic surfactants are, for example, quaternary ammonium salts, such as di (C 10 -C 24 -alkyl) dimethyl ammonium chloride or bromide, preferably di (C 12 -C 18 -alkyl) dimethyl ammonium chloride or bromide; Ci -C 24 alkyl O-dimethyl- ethylammonium chloride or bromide; C 10 -C 10 -alkyl-trimethyl-ammonium chloride or bromide, preferably cetyltrimethylammonium chloride or bromide and C 2 -C 22 -alkyltrimethylammonium chloride or bromide; C- ⁇ o-C 24 alkyl dimethylbenzyl ammonium chloride or bromide, preferably C 12 -C 8 alkyl dimethylbenzyl ammonium chloride; N- (Cio-Ci 8 alkyl) pyridinium chiorid or bromide, preferably N- (C
  • the amount of cationic surfactants is preferably 0.1 to 10 wt .-%, particularly preferably 0.2 to 7 wt .-%, particularly preferably 0.5 to 5 wt .-% based on the finished compositions.
  • Suitable nonionic surfactants which can be used as detergent substances are preferably fatty alcohol ethoxylates (alkylpolyethylene glycols); Alkylphenolpolyethylenglykole; Alkyl mercaptan polyethylene glycols; Fatty amine ethoxylates (alkylaminopolyethylene glycols);
  • Fatty acid ethoxylates (acyl polyethylene glycols); Polypropylenglykolethoxylate (Pluronics ®); Fettchureamidpolyethylenglykole; N-alkyl, N-alkoxy poly-hydroxy fatty acid amides, in particular fatty acid N-methylglucamides; Saccharoseester; polyglykolether; alkylpolyglycosides; Phosphoric acid esters (mono-, di- and triphosphoric esters ethoxylated and non-ethoxylated).
  • the amount of nonionic surfactants in the compositions of the invention is preferably in the Range from 1 to 20 wt .-%, particularly preferably from 2 to 10 wt .-%, particularly preferably from 3 to 7 wt .-% based on the finished compositions.
  • amphoteric surfactants or amphoteric surfactants are: N- (C 2 -C 8 alkyl) -S-S- aminopropionates and N- (C 2 -C 8 alkyl) -ß-iminodipropionates as alkali metal and mono-, di- and trialkylammonium salts; N-acylaminoalkyl-N, N-dimethyl-acetobetaine, preferably N- (C 8 -C 18 -acyl) aminopropyl-N, N-dimethylacetobetaine; C-
  • the amount of amphoteric surfactants is preferably from 0.5 to 20 wt .-%, particularly preferably from 1 to 10 wt .-%, based on the finished composition.
  • foam-enhancing cosurfactants from the group consisting of alkylbetaines, alkylamidobetaines, aminopropionates, aminoglycinates, imidazoliniumbetaines and sulfobetaines,
  • Amine oxides and fatty acid or polyhydroxyamides are used.
  • Preferred surfactants in the compositions according to the invention are alkyl ether sulfates, alkyl sulfates, in particular lauryl sulfate, alkylbetaines, in particular cocoamidopropylbetaine, amphoacetates, acylglutamates, in particular sodium cocoylglutamate, alkylethersulfosuccinates, in particular di-sodium laureth-sulfosuccinate and coconut fatty acid diethanolamide.
  • the amount of surfactants used in the compositions according to the invention is preferably from 1 to 70 wt .-%, particularly preferably from 10 to 40 wt .-%, particularly preferably from 12 to 35 wt .-%, based on the finished compositions.
  • Compositions according to the invention which are present as emulsions can be produced without further emulsifier or else contain one or more emulsifiers.
  • compositions according to the invention are therefore free of emulsifiers. In another preferred embodiment of the invention, however, the compositions according to the invention contain one or more emulsifiers.
  • emulsifiers can be selected from the group of nonionic, anionic, cationic or amphoteric emulsifiers.
  • Suitable nonionic co-emulsifiers are preferably addition products of from 0 to 30 mol of ethylene oxide and / or from 0 to 5 mol
  • anionic co-emulsifiers such as mono-, di- or tri-phosphoric acid esters, soaps (eg., Sodium stearate),
  • Fatty alcohol sulfates but also cationic emulsifiers such as mono-, di- and tri-alkyl quats and their polymeric derivatives.
  • amphoteric emulsifiers are preferably available Alkylaminoalkylcarbonklaren, betaines, sulfobetaines and imidazoline derivatives.
  • emulsifiers among which beeswax, wool wax, lecithin and sterols are preferred, can be used.
  • fatty alcohol ethoxylates are selected from the group consisting of ethoxylated stearyl alcohols, cetyl alcohols, cetylstearyl alcohols, especially polyethylene glycol (13) stearyl ether, polyethylene glycol (14) stearyl ether, polyethylene glycol (15) stearyl ether, polyethylene glycol (16) stearyl ether, polyethylene glycol (17) stearyl ether, polyethylene glycol (18).
  • polyethylene glycol (30) cholesteryl ether is advantageous. Also preferred is polyethylene glycol (25) sojasterol.
  • sorbitan esters particularly suitable are polyethylene glycol (20) sorbitan monolaurate, polyethylene glycol (20) sorbitan monostearate, polyethylene glycol (20) sorbitan monoisostearate, polyethylene glycol (20) sorbitan monopalmitate, polyethylene glycol (20) sorbitan monooleate.
  • compositions of the invention may contain film formers, which are selected depending on the application of salts of
  • Phenylbenzimidazole sulfonic acid for example, Phenylbenzimidazole sulfonic acid, water-soluble polyurethanes, for example
  • Vinylpyrrolidone / vinyl acetate copolymer water-soluble acrylic acid polymers / copolymers or their esters or salts, for example
  • Fatty alcohols such as acrylate / steareth-20-methacrylate copolymer, water-soluble
  • Cellulose for example hydroxymethylcellulose, hydroxyethylcellulose, Hydroxypropyl cellulose, water-soluble Quatemiums, polyquaterniums, carboxyvinyl polymers, such as carbomers and salts thereof, polysaccharides, for example polydextrose and glucan, vinyl acetate / crotonate, available for example under the trade name Aristoflex ® A 60 (Clariant), and polymeric amine oxides, for example, under the trade names Diaformer Z-711, 712, 731, 651, 632 available representatives.
  • the desired viscosity of the compositions can be adjusted by adding further thickening agents.
  • Cellulose ethers and other cellulose derivatives for example carboxymethylcellulose, hydroxyethylcellulose), gelatin, starch and starch derivatives, sodium alginates, fatty acid polyethylene glycol esters, agar-agar, tragacanth or dextrin derivatives, in particular dextrin esters, are preferably suitable.
  • Metal salts of fatty acids preferably having 12 to 22 carbon atoms, for example sodium stearate, sodium palmitate, sodium laurate, sodium arachidates, sodium behenate, potassium stearate, potassium palmitate, sodium myristate, aluminum monostearate, hydroxyfatty acids, for example 12-hydroxystearic acid, 16-hydroxyhexadecanoic acid; fatty acid amides; fatty acid; Dibenzal sorbitol and alcohol-soluble polyamides and polyacrylamides or mixtures thereof.
  • compositions according to the invention preferably contain 0.01 to 20% by weight, more preferably 0.1 to 10% by weight, particularly preferably 1 to 8% by weight and most preferably 3 to 7% by weight of gelling agents.
  • astringents are oxides, preferably magnesium oxide, aluminum oxide, titanium dioxide, zirconium dioxide and zinc oxide, oxide hydrates, preferably aluminum oxide hydrate (boehmite) and hydroxides, preferably of calcium, magnesium, aluminum, titanium, zirconium or zinc.
  • the compositions according to the invention contain the astringent active ingredients preferably in amounts of from 0 to 50% by weight, more preferably in amounts of from 0.01 to 10% by weight and especially preferably in amounts of from 0.1 to 10% by weight.
  • Preferred antioxidants are selected from amino acids (eg glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (eg.
  • Urocanic acid and its derivatives, peptides such as DL-carnosine, D-camosine, L-carnosine and their derivatives (eg anserine), carotenoids, carotenes (eg ⁇ -carotene, ⁇ -carotene, lycopene) and their derivatives Derivatives, chlorogenic acid and its derivatives, lipoic acid and its derivatives (eg dihydrolipoic acid), aurothioglucose, propylthiouracil and other thiols (eg thioredoxin,
  • peptides such as DL-carnosine, D-camosine, L-carnosine and their derivatives (eg anserine), carotenoids, carotenes (eg ⁇ -carotene, ⁇ -carotene, lycopene) and their derivatives Derivatives, chlorogenic acid and its derivatives, lipoic acid and its derivatives (eg dihydrolipoic
  • Biliverdin, EDTA, EGTA and their derivatives unsaturated fatty acids and their derivatives (eg ⁇ -linolenic acid, linoleic acid, oleic acid), folic acid and its derivatives, ubiquinone and ubiquinol and derivatives thereof, vitamin C and derivatives (eg ascorbyl palmitate , Mg ascorbyl phosphate, ascorbyl acetate), tocopherols and derivatives (eg, vitamin E acetate), vitamin A and derivatives (vitamin A palmitate), as well as coniferyl benzoate of benzoin, rutinic acid and derivatives thereof, ⁇ -glycosyl rutin, ferulic acid, furfurylidene glucitol, Camosin, butylhydroxytoluene, butylhydroxyanisole, nordihydroguaiakolic acid, nordihydroguiaretic acid, Trihydroxybutyrophenone, uric acid and its derivatives,
  • the antioxidants can protect the skin and hair from oxidative stress.
  • Preferred antioxidants are vitamin E and its derivatives as well as vitamin A and its derivatives.
  • the amount of the one or more antioxidants in the compositions of the invention is preferably from 0.001 to 30% by weight, more preferably from 0.05 to 20% by weight, and most preferably from 1 to 10% by weight, based on the total weight of the composition ,
  • vitamin E and / or its derivatives represent the antioxidant (s)
  • vitamin A or vitamin A derivatives, or carotenes or derivatives thereof constitute the antioxidant (s)
  • their respective concentrations are in the range from 0.001 to 10% by weight, based on the total weight of the compositions to choose.
  • Terephthalylidenedicampheresulfonic acid 2,4,6-tris [4,2-ethylhexyloxycarbonyl) anilino] -1, 3,5-triazine, methyl bis (trimethylsiloxy) silyl-isopentyltrimethoxycinnamic acid, amyl p-dimethylaminobenzoate, amyl p-dimethylaminobenzoate, 2-ethylhexyl-p-dimethylaminobenzoate, isopropyl-p-methoxycinnamic acid / diisopropyl cinnamic acid ester, 2-ethylhexyl-p-methoxycinnamic acid, 2-hydroxy-4-methoxybenzophenone,
  • additives may be silicone compounds, preferably
  • Dimethylpolysiloxane, methylphenyl polysiloxanes, cyclic silicones and amino-, fatty acid-, alcohol-, polyether-, epoxy-, fluorine- and / or alkyl-modified silicone compounds for example alkylsilicones SilCare ® Silicone 41 M10, SilCare ® Silicone 41 M15, SilCare ® Silicone 41 M20, SilCare ® Silicone 41 M30 (Clariant), Alkyltrimethicone SilCare ® 31 M30, SilCare ® 31 M40, SilCare ® 31 M50, SilCare ® 31M60 (Clariant), phenyltrimethicones SilCare ® 15M30, SilCare ® 15M40, SilCare ® 15M50, SilCare ® 15M60 (Clariant), polyalkylaryl siloxanes and polyethersiloxane copolymers.
  • alkylsilicones SilCare
  • compositions according to the invention may preferably contain the abovementioned silicone compounds in the amounts by weight of from 0.1 to 20% by weight, more preferably from 0.2 to 15% by weight, particularly preferably from 0.5 to 10% by weight, based on the finished product Contain compositions.
  • compositions of the invention contain the antimicrobial agents preferably in amounts of up to 50 wt .-%, particularly preferably in amounts of 0.01 to 10 wt .-%, particularly preferably in amounts of 0.1 to 10 wt .-%, based on the finished compositions.
  • fungicidal active ingredients may preferably ketoconazole, oxiconazole, terbinafine, bifonazoles, butoconazole, cloconazole, clotrimazole, econazole, enilconazole, fenticonazole, isoconazole, miconazole, sulconazole, tioconazole fluconazole, itraconazole, terconazole, naftifine and terbinafine, Zn-pyrithione and Octopirox ® in the Weight amounts of 0.05 to 5 wt .-%, preferably 0.1 to 3 wt .-%, particularly preferably 0.2 to 2 wt .-%, based on the finished compositions.
  • Suitable preservatives are preferably phenoxyethanol, parabens, pentanediol or sorbic acid. They are preferably used in amounts of 0.001 to 5 wt .-%, particularly preferably from 0.01 to 3 wt .-%, particularly preferably from 0.1 to 2 wt .-%, based on the finished compositions.
  • Lanolin and lecithin, nonethoxylated and polyethoxylated or acylated lanolin and lecithin derivatives, polyol fatty acid esters, mono-, di- and triglycerides and / or fatty acid alkanolamides may preferably be used as superfatting agents.
  • Dyes which may be used are the substances suitable and approved for cosmetic and pharmaceutical purposes.
  • fragrance or perfume oils can individual fragrance compounds, eg.
  • ethers, aldehydes, ketones, alcohols and hydrocarbons are used.
  • Fragrance compounds of the ester type are e.g. Benzyl acetate, phenoxyethyl isobutyrate, p-tert-butylcyclohexyl acetate, linalyl acetate, dimethylbenzylcarbinylacetate, phenylethylacetate, linalylbenzoate, benzylformate, ethyl-methylphenylglycinate, allylcyclohexylpropionate, styrallylpropionate and benzylsalicylate.
  • the ethers include, for example, benzyl ethyl ether to the aldehydes z.
  • the linear alkanals having 8 to 18 carbon atoms citral, citronellal, citronellyloxyacetaldehyde, cycloalanine, Hydroxycitronellal, Lilial and Bourgeonal, to the ketones z.
  • the alcohols include anethole, citronellol, eugenol, geraniol, linalol, phenylethyl alcohol and terpineol
  • the hydrocarbons include mainly the terpenes and balsams.
  • mixtures of different fragrances are used, which together produce an attractive fragrance.
  • Perfume oils may also contain natural fragrance mixtures, such as those available from plant or animal sources, e.g. Pine, citrus, jasmine, lily, rose, or ylang-ylang oil. Also essential oils of lower volatility, which are mostly used as aroma components, are suitable as perfume oils, eg. B. sage oil, chamomile oil, clove oil, lemon balm oil, mint oil, cinnamon oil, lime blossom oil, juniper berry oil, vetiver oil, oliban oil, galbanum oil and ladanum oil.
  • perfume oils eg. B. sage oil, chamomile oil, clove oil, lemon balm oil, mint oil, cinnamon oil, lime blossom oil, juniper berry oil, vetiver oil, oliban oil, galbanum oil and ladanum oil.
  • acids or alkalis for pH adjustment preferably mineral acids, for example HCl, inorganic bases, for example NaOH, KOH and organic acids, preferably citric acid are used.
  • compositions are preferably adjusted to a pH in the range 2 to 12, more preferably pH 3 to 8.
  • a pH in the range 2 to 12 more preferably pH 3 to 8.
  • the described acryloyldimethyl- taurinklare-containing copolymers can be used without the concomitant use of an additional co-emulsifier and / or without the use of an additional bodying consistency.
  • Co-emulsifiers and / or consistency regulators is therefore not mandatory, but possible.
  • a combination with other known co-emulsifiers and / or bodying agents may be desirable for setting specific cosmetic profiles and exploiting synergistic effects.
  • the emulsions are creamy and ointment-free and do not have the gel-like or even gelatinous appearance of certain prior art emulsions in which the outer aqueous phase is thickened.
  • the cosmetic feel on the skin is very good: when applied, the emulsion gives a feeling of freshness and comfort, while at the same time acting rich and nourishing; she is soft and comfortable and in no way sticky.
  • compositions according to the invention comprising the described polymers based on acrylamido-alkylsulfonic acids and high levels of care components (Examples II and III) are more stable than compositions according to the prior art (Example I).
  • compositions according to the invention are also stable without further addition of emulsifiers or stabilizers (Example IV).
  • the compositions of the invention are characterized by a better skin feel and less stickiness.
  • Salcare ® SC91 Sodiumacrylates copolymer and Paraffinum Liquidum and PPG-1 Trideceth-6

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Abstract

L'invention concerne des compositions cosmétiques, pharmaceutiques ou dermatologiques contenant : I) au moins un copolymère, pouvant être obtenu par copolymérisation radicalaire de : A) un ou plusieurs acides acrylamidoalkylsulfoniques et/ou leurs sels, B) éventuellement un ou plusieurs autres comonomères oléfiniquement insaturés, non cationiques, éventuellement réticulants, présentant au moins un atome d'oxygène, d'azote, de soufre ou de phosphore et possédant une masse moléculaire inférieure à 500 g/mol, C) éventuellement un ou plusieurs macromonomères oléfiniquement mono-insaturés ou poly-insaturés, éventuellement réticulants, présentant chacun au moins un atome d'oxygène, d'azote, de soufre ou de phosphore et possédant une masse moléculaire moyenne en nombre supérieure ou égale à 200 g/mol, D) la copolymérisation ayant lieu éventuellement en présence d'au moins un additif polymère possédant une masse moléculaire moyenne en nombre comprise entre 200 g/mol et 109 g/mol, et E) > 0,5 % en poids d'un ou de plusieurs agents réticulants, par rapport au poids total du copolymère, et II) au moins 10 % en poids d'un ou de plusieurs composants hydrosolubles pour le soin de la peau et/ou des cheveux, par rapport à la composition cosmétique, pharmaceutique ou dermatologique finie.
PCT/EP2008/010678 2007-12-21 2008-12-16 Compositions cosmétiques, pharmaceutiques ou dermatologiques présentant une teneur élevée en composants de soin hydrosolubles Ceased WO2009083131A2 (fr)

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US9192562B2 (en) 2013-09-18 2015-11-24 L'oreal High color intensity and easily removable mascara
CN108864187A (zh) * 2018-08-06 2018-11-23 兰博尔开封科技有限公司 一种合成氧乐果重要中间体氧硫磷酯的新工艺
US20190307668A1 (en) * 2016-11-28 2019-10-10 Clariant International Ltd. Cosmetic composition comprising a cationic copolymer
US20190382686A1 (en) * 2016-11-28 2019-12-19 Clariant International Ltd. Copolymers And The Use Of Same In Cleaning Agent Compositions
US11692052B2 (en) 2016-11-28 2023-07-04 Clariant International Ltd Copolymers and use thereof in cleaning-agent compositions

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JP7412878B2 (ja) * 2017-11-28 2024-01-15 ロレアル 難水溶性活性化合物とビニルピロリドンコポリマーとを含む組成物

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US8857741B2 (en) 2012-04-27 2014-10-14 Conopco, Inc. Topical spray composition and system for delivering the same
US9751097B2 (en) 2012-04-27 2017-09-05 Conopco, Inc. Topical spray composition to benefit skin
US9192562B2 (en) 2013-09-18 2015-11-24 L'oreal High color intensity and easily removable mascara
US20190307668A1 (en) * 2016-11-28 2019-10-10 Clariant International Ltd. Cosmetic composition comprising a cationic copolymer
US20190382686A1 (en) * 2016-11-28 2019-12-19 Clariant International Ltd. Copolymers And The Use Of Same In Cleaning Agent Compositions
US11649310B2 (en) 2016-11-28 2023-05-16 Clariant International Ltd Copolymers and the use of same in cleaning agent compositions
US11692052B2 (en) 2016-11-28 2023-07-04 Clariant International Ltd Copolymers and use thereof in cleaning-agent compositions
CN108864187A (zh) * 2018-08-06 2018-11-23 兰博尔开封科技有限公司 一种合成氧乐果重要中间体氧硫磷酯的新工艺
CN108864187B (zh) * 2018-08-06 2020-12-25 兰博尔开封科技有限公司 一种合成氧乐果重要中间体氧硫磷酯的工艺

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