EP0609391A1 - Alkylpolyglykosidderivate, Verfahren zu deren Herstellung, diese enthaltende Zusammensetzungen und Verwendung als Oberflächenaktivmittel - Google Patents

Alkylpolyglykosidderivate, Verfahren zu deren Herstellung, diese enthaltende Zusammensetzungen und Verwendung als Oberflächenaktivmittel

Info

Publication number
EP0609391A1
EP0609391A1 EP92923842A EP92923842A EP0609391A1 EP 0609391 A1 EP0609391 A1 EP 0609391A1 EP 92923842 A EP92923842 A EP 92923842A EP 92923842 A EP92923842 A EP 92923842A EP 0609391 A1 EP0609391 A1 EP 0609391A1
Authority
EP
European Patent Office
Prior art keywords
formula
alkylpolyoside
carbon atoms
fatty alcohol
alkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP92923842A
Other languages
English (en)
French (fr)
Inventor
Jean-Pierre Boiteux
Bernard Brancq
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Societe dExploitation de Produits pour les Industries Chimiques SEPPIC SA
Original Assignee
Societe dExploitation de Produits pour les Industries Chimiques SEPPIC SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Societe dExploitation de Produits pour les Industries Chimiques SEPPIC SA filed Critical Societe dExploitation de Produits pour les Industries Chimiques SEPPIC SA
Publication of EP0609391A1 publication Critical patent/EP0609391A1/de
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/604—Alkylpolyglycosides; Derivatives thereof, e.g. esters
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
    • 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
    • A61Q19/10—Washing or bathing preparations
    • 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
    • A61Q5/02—Preparations for cleaning the hair
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/123—Sulfonic acids or sulfuric acid esters; Salts thereof derived from carboxylic acids, e.g. sulfosuccinates

Definitions

  • the present invention relates to new alkylpolyoside derivatives, compositions containing them, their preparation process and applications as surfactants.
  • alkylpolyosides are nonionic surfactants already used in a wide range of industrial applications.
  • the present invention aims to cover new alkyl polyiside hemisulfosuccinates, corresponding to the general formula:
  • R represents an alkenyl radical or, preferably, a straight or branched chain alkyl radical having from 6 to 32 carbon atoms,
  • S represents the remainder of a sugar
  • M represents an alkali metal
  • one of Ri represents a SO3M group in which M represents an alkali metal
  • the other represents a hydrogen atom
  • x represents an integer included between 1 and 10, preferably between 1 and 4.
  • the term "residue of a sugar” means a bivalent radical resulting from the removal from a sugar molecule, on the one hand of an atom of hydrogen on a hydroxyl group, and on the other hand of the anomeric hydroxyl group.
  • the sugar is for example chosen from the following compounds: glucose or dextrose, sucrose, fructose, galactose, maltose, maltotriose, lactose, cellobiose, mannose, ribose, dextran, talose, allose, xylose, levoglucosane, cellulose and starch.
  • glucose, dextrose, fructose and maltose are particularly preferred.
  • An alkali metal is for example sodium or potassium. It has been found, quite surprisingly, that the new products thus defined have particularly advantageous properties as surfactants.
  • the derivatives according to the invention will advantageously replace in their applications the polyoxyethylated functional surfactants, the preparation of which leads to toxic impurities, which limits their use. These derivatives will therefore find application in many fields ranging from cosmetics (soaps, toilet bars) and parapharmacy to household detergents, via the textile industry, or paper.
  • the alkylpolyoside derivatives in accordance with the invention can be used alone or as a mixture with hemi-sulfosuccinates fatty alcohols of formula ROCO-CHR1-CHR2-CO2M (II) and optionally alkylpolyosides of formula RO- (S) x -H; R, RI, R2, M, S and x being as defined above, R 'representing an alkenyl group or, preferably, an alkyl group, with straight or branched chain having from 6 to 32 carbon atoms.
  • the present invention covers a composition which can usually comprise, expressed as a percentage by weight:
  • compositions can be obtained by simple mixing of its constituents, but will preferably be prepared by reaction of maleic anhydride on a mixture comprising a polysaccharide of formula RO- (S) x -H and a fatty alcohol of formula R'OH , in which R 1 represents an alkenyl group or, preferably, an alkyl group, with a straight or branched chain having from 6 to 32 carbon atoms in the molar proportions indicated above and sulfitation of the product thus obtained in an alkaline medium.
  • R 1 represents an alkenyl group or, preferably, an alkyl group, with a straight or branched chain having from 6 to 32 carbon atoms in the molar proportions indicated above and sulfitation of the product thus obtained in an alkaline medium.
  • the fatty alcohols that can be used for the preparation of this composition will generally be linear or branched alcohols, of natural origin such as, for example, alcohols from plant materials (copra, palm kernel, palm) or animal materials (tallow), or even synthetic; and whose chain length is between 6 and 32 carbon atoms, preferably between 8 and 14 carbon atoms and more preferably between 10 and 12 carbon atoms.
  • the fatty alcohol will have a chain identical to the alkyl chain of the alkylpolyoside hemisulfosuccinate.
  • the above-mentioned alkylpolyoside may be commercial or prepared by any method known to those skilled in the art.
  • Triton CG 110 Triton BG 10, Triton DG 210; Oramix CG 110, Oramix NS 10 and Plantaren APG 600.
  • the first route comprises the reaction, in an acid medium between a fatty alcohol and a sugar having an anomeric hydroxyl group, preferably glucose or dextrose.
  • the second way consists: - in a first step, to prepare an alkylpolyoside with a light alcohol such as for example methanol or butanol by etherification of a sugar, preferably glucose, to obtain products such as methylglucoside or pentylglucoside; then
  • the reaction with heavy fatty alcohol is generally incomplete; one can then proceed, if necessary, to a distillation of the excess fatty alcohol.
  • acid catalysts which can be used for the preparation of the abovementioned alkylpolyosides are sulfuric, phosphoric, hydrochloric, hypophosphorous acids and their mixtures.
  • the amount of acid catalyst used will generally be about 0.001 to 0.05 moles per mole of sugar.
  • the reaction temperature will generally be between 90 and 120 ° C, and the reaction time between 3 and 6 hours.
  • the present invention covers a process for the preparation of the alkylpolyoside hemi-sulfosuccinates of the above-mentioned formula (I) or of a composition as defined above, in a container characterized in that it comprises: a- maleic anhydride on an alkylpolyoside of formula RO- (S) xH, in which R, S and x are as defined above; or a ⁇ - the reaction of maleic anhydride on a mixture comprising an alkylpolyoside of formula R-0- (S) x -H, in which R, S and x are as defined above and a fatty alcohol of formula R'OH wherein R 'represents an' alkenyl or, preferably, straight or branched chain alkyl having from 6 to 32 carbon atoms; b- sulphitation in an alkaline medium of the product thus obtained at the end of step a or a r
  • R 'OH represents an' alkenyl or,
  • the fatty alcohol can come from the synthesis of the alkylpolyoside, or be additive to an alkylpolyoside.
  • the esterification of the alkylpolyoside (step a or a will generally be carried out using a functional anhydride of the maleic type, possibly in the presence of an acid catalyst such as for example sulfuric acid. Generally, 0.7 is used. at approximately 1.8 equivalent of said functional anhydride for an equivalent of primary hydroxide
  • the esterification can be carried out in an appropriate solvent, in an aqueous medium or, preferably, in the absence of any solvent.
  • the esterification can be carried out at a temperature of between approximately 60 and 130 ° C., preferably between 70 and approximately 100 ° C., for a period of approximately 1 to 15 hours and preferably from 1 hour 30 to 3 hours.
  • step b it is possible to use any known sulphitizing agent and in particular Na2S2O5, Na2SO3 or even SO2 in the gaseous state, preferably Na 2 S 2 O 5 .
  • the amount of said sulphitating agent used can advantageously be of an equivalent for 1 to 2 equivalents of functional anhydride of the maleic type present in the reaction mixture.
  • the sulfitation reaction is preferably carried out in an aqueous medium, at a pH of between about 4 and 7, preferably between 5.5 and 6.5. This sulfitation reaction can be carried out at a temperature between 60 and
  • the present invention also aims to cover the use of the alkylpolyoside derivatives defined above or of a composition containing them, as surfactants, in particular as foaming or wetting products.
  • Example 1 Step a: Esterification At 420 g of commercial alkyl glucoside (Oramix CG 110-100%) melted at 420 g.
  • the commercial product Oramix CG 110-100% is a product with 100% of active material obtained by etherification in acid catalysis of glucose by an excess of alcohol (Cg-Gjrj) and elimination of the excess alcohol by distillation on an evaporator to film.
  • 485 g of the maleic ester obtained in step a are sulfites with 96 g of sodium metabisulfite in the presence of 37 g of sodium hydroxide, at 95-100 ° C. in an aqueous medium (500 g of water) for 3 hours.
  • Step a 2 Esterification
  • Example 3 Example a ⁇ : Esterification
  • the whole is kept at approximately 100 ° C. with stirring for 11 hours.
  • the medium is then cooled to 40 ° C., then neutralized and diluted with a 10% sodium hydroxide solution.
  • VCS coloring about 7 pH at 10% 6.3 Dry extract 40.5%
  • the ester-alkaline solution mixture is maintained at 95-100 # C with stirring for 4 hours.
  • the product obtained has the following characteristics:
  • Example 4 Step a ⁇ : Esterification From a cut of C12-C14-C16 alcohols, an alylpolyglucoside containing 80% of active material is diluted in alcohol. The residual alcohol contents are 14% in C12 alcohol, 5% in C14 alcohol and 1% in C16 alcohol.
  • the maleic ester obtained in stage a 1 is sulphite with 4.55 kg of sodium metabisulphite, presented with 2.1 kg of soda, at 90 ° C. in an aqueous medium (27 kg) for 3 hours.
  • the foaming power was measured by the volume of foam generated 1% of product (dry matter) in water at 30 ° F of calcium hardness, in the presence of a soil type at 40 ° C, according to standard AFNOR 73403.
  • the wetting power was measured according to AFNOR standard NFT 73406 of 0.1% of the product expressed in dry extract at 25 ° C. It is expressed as a wetting time of the textile disc.
  • Examples 1 and 2 are classified as very mildly irritant, while the corresponding ethoxylated derivative is moderately irritant, and the reference alkylpolyoside is also moderately irritant.
  • the derivatives in accordance with the invention therefore exhibit remarkable surfactant properties, superior to those of their known ethoxylated counterparts.
  • the compounds according to the invention can be used to replace these known products in a wide range of applications, in particular in cosmetics, parapharmacy and household detergency.
  • the compounds of the invention will preferably be used in shampoos, shower gels, bubble baths, to which they impart a creamy foam and which does not attack the skin and scalp during iterative applications.
  • Example 1 For example, the following mild shampoo is formulated with the product of Example 1 according to:
  • Preservative agent KATHON R CG
  • Demineralized water qs 100% whose pH is adjusted to 6 with citric acid.
  • the shampoo is crystal clear.
  • the viscosity obtained is 850 mPas at 20 ° C.
  • a shampoo formulated under the same conditions with sodium alkyl (Cg-C j ) ethoxy (3) hemisulfosuccinate, in place of the product of Example 1, has a cloudy, non-limpid and fluid appearance without viscosity
  • an antiseptic cleansing liquid for medical skin use has been formulated according to:
  • Example 2 Antimicrobial agent 0.5% Demineralized water qs 100%
  • the antimicrobial agent chosen is peracetic acid.
  • composition containing 1% phenoxyethanol as an antimicrobial agent is also effective in removing pathogenic germs from the skin without irritating it.
  • the products according to the invention can also be used from 10 to 50% as a mild cleaning agent in syndets, soaps and toilet bars.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Toxicology (AREA)
  • Dentistry (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)
EP92923842A 1991-10-17 1992-10-16 Alkylpolyglykosidderivate, Verfahren zu deren Herstellung, diese enthaltende Zusammensetzungen und Verwendung als Oberflächenaktivmittel Withdrawn EP0609391A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9112841A FR2682679B1 (fr) 1991-10-17 1991-10-17 Nouveaux derives d'alkylpolyosides, leurs procedes de preparation et applications comme agents de surface.
FR9112841 1991-10-17
PCT/FR1992/000980 WO1993008204A1 (fr) 1991-10-17 1992-10-16 Nouveaux derives d'alkylpolyosides, compositions en contenant, leurs procede de preparation et applications comme agents de surface

Publications (1)

Publication Number Publication Date
EP0609391A1 true EP0609391A1 (de) 1994-08-10

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ID=9418043

Family Applications (1)

Application Number Title Priority Date Filing Date
EP92923842A Withdrawn EP0609391A1 (de) 1991-10-17 1992-10-16 Alkylpolyglykosidderivate, Verfahren zu deren Herstellung, diese enthaltende Zusammensetzungen und Verwendung als Oberflächenaktivmittel

Country Status (3)

Country Link
EP (1) EP0609391A1 (de)
FR (1) FR2682679B1 (de)
WO (1) WO1993008204A1 (de)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2785795B1 (fr) * 1998-11-12 2002-11-29 Oreal Compositions cosmetiques contenant un tensioactif ester d'alkylpolyglycoside anionique et un ceramide et leurs utilisations
FR2785796B1 (fr) * 1998-11-12 2002-11-29 Oreal Compositions cosmetiques contenant un tensioactif ester d'alkylpolyglycoside anionique et une silicone organomodifiee et leurs utilisations
FR2785798B1 (fr) * 1998-11-12 2002-11-29 Oreal Compositions cosmetiques contenant un tensioactif ester d'alkylpolyglucoside anionique et une silicone et leurs utilisations
FR2785797B1 (fr) * 1998-11-12 2002-10-18 Oreal Compositions cosmetiques contenant un tensioactif ester d'alkylpolyglycoside anionique et un agent conditionneur liquide insoluble dans l'eau et leurs utilisations
FR2785794B1 (fr) * 1998-11-12 2002-11-29 Oreal Compositions cosmetiques contenant un tensioactif ester d'alkylpolyglycoside anionique et un polymere cationique et leurs utilisations
FR2810883B1 (fr) 2000-06-28 2006-07-28 Seppic Sa Nouveaux latex inverses autoinversibles sur des esters d'acides gras, compositions cosmetiques, dermocosmetiques, dermopharmaceutiques ou pharmaceutiques en comportant
FR2856691B1 (fr) 2003-06-26 2005-08-26 Seppic Sa Nouveau polymere en poudre, procede pour sa preparation et utilisation comme epaississant
FR2861397B1 (fr) 2003-10-22 2006-01-20 Soc Dexploitation De Produits Pour Les Industries Chimiques Seppic Nouveau latex inverse concentre, procede pour sa preparation et utilisation dans l'industrie
FR2879607B1 (fr) 2004-12-16 2007-03-30 Seppic Sa Nouveaux latex inverse concentre, procede pour sa preparation, et utilisation dans l'industrie
EP2070958A1 (de) 2007-12-11 2009-06-17 Societe D'exploitation De Produits Pour Les Industries Chimiques, S.E.P.P.I.C. Neues Verfahren zur Herstellung von inversem Latex aus acrylamidbasierten Polymeren und Zusammensetzung mit diesem Latex
FR2950060B1 (fr) 2009-09-11 2011-10-28 Soc Dexploitation De Produits Pour Les Industries Chimiques Seppic Nouveau polymere en poudre, procede pour sa preparation et utilisation comme epaississant
FR2959746B1 (fr) 2010-05-06 2012-06-15 Soc Dexploitation De Produits Pour Les Industries Chimiques Seppic Nouveau latex inverse auto-inversible, son utilisation comme agent epaississant dans une composition cosmetique
FR2986004B1 (fr) 2012-01-25 2014-03-14 Seppic Sa Nouveau polymere epaississant reduisant le caractere collant des formules cosmetiques a base de glycerine
FR2987361B1 (fr) 2012-02-29 2014-07-18 Soc Dexploitation De Produits Pour Les Industries Chimiques Seppic Nouveau polymere d'acrylate de silicone et de methacrylate de trifluoro-ethyle, preparation et utilisation en cosmetique
FR2987839B1 (fr) 2012-03-08 2014-05-09 Soc Dexploitation De Produits Pour Les Industries Chimiques Seppic Nouveau polymere d'acrylate de silicone et d'acide acrylique epaississant et reduisant le caractere collant des formules cosmetiques a base de glycerine
FR2992323B1 (fr) 2012-06-25 2015-07-03 Soc Dexploitation De Produits Pour Les Industries Chimiques Seppic Nouveau latex inverse auto-inversible exempt de tensioactif, son utilisation comme agent epaississant dans une composition cosmetique
CN104313205A (zh) * 2014-11-05 2015-01-28 陕西科技大学 琥珀酸酯磺酸化c16-c18醇表面活性剂及其制备方法

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DE2148279A1 (de) * 1970-09-30 1972-04-06 Unilever N V , Rotterdam (Nieder lande) Geruststoffe fur Detergensmittel
DE3706015A1 (de) * 1987-02-25 1988-11-17 Henkel Kgaa Fluessiges reinigungsmittel
JPH04211695A (ja) * 1990-04-27 1992-08-03 Kao Corp スルホコハク酸グリコシドエステル及びその製造方法
DE4110852A1 (de) * 1991-04-04 1992-10-08 Rewo Chemische Werke Gmbh Verwendung von alkylglycosidsulfosuccinaten zur herstellung von kosmetischen praeparaten und reinigungsmitteln

Non-Patent Citations (1)

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Also Published As

Publication number Publication date
FR2682679A1 (fr) 1993-04-23
FR2682679B1 (fr) 1995-06-16
WO1993008204A1 (fr) 1993-04-29

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