EP1863825A1 - Nouveaux tensioactifs et nouveaux emulsifiants a base de disaccharides - Google Patents

Nouveaux tensioactifs et nouveaux emulsifiants a base de disaccharides

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Publication number
EP1863825A1
EP1863825A1 EP06723701A EP06723701A EP1863825A1 EP 1863825 A1 EP1863825 A1 EP 1863825A1 EP 06723701 A EP06723701 A EP 06723701A EP 06723701 A EP06723701 A EP 06723701A EP 1863825 A1 EP1863825 A1 EP 1863825A1
Authority
EP
European Patent Office
Prior art keywords
lac
glucopyranoside
galactopyranosyl
sodium
surfactant
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.)
Ceased
Application number
EP06723701A
Other languages
German (de)
English (en)
Inventor
Joerg Schreiber
Goetz Milkereit
Sven Gerber
Volkmar Vill
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.)
Beiersdorf AG
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Beiersdorf AG
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Filing date
Publication date
Application filed by Beiersdorf AG filed Critical Beiersdorf AG
Priority to EP08012073A priority Critical patent/EP1980567A1/fr
Publication of EP1863825A1 publication Critical patent/EP1863825A1/fr
Ceased legal-status Critical Current

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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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0208—Tissues; Wipes; Patches
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/10—Foods or foodstuffs containing additives; Preparation or treatment thereof containing emulsifiers
    • 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
    • A61K8/602—Glycosides, e.g. rutin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/14—Preparations for removing make-up
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q9/00—Preparations for removing hair or for aiding hair removal
    • A61Q9/02—Shaving preparations
    • 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
    • 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
    • C07H15/08—Polyoxyalkylene derivatives
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/017—Mixtures of compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/662—Carbohydrates or derivatives
    • 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
    • C11D1/66—Non-ionic compounds
    • C11D1/83—Mixtures of non-ionic with anionic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/22—Carbohydrates or derivatives thereof
    • C11D3/221—Mono, di- or trisaccharides or derivatives thereof
    • 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
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/146—Sulfuric acid esters
    • 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
    • C11D1/29—Sulfates of polyoxyalkylene ethers

Definitions

  • the present invention relates to novel surfactants and emulsifiers based on disaccharides. These are characterized in particular by a special foaming behavior and a special mildness when applied to the skin. In addition, a subgroup is suitable as a gelling agent.
  • ionic surfactants such as lauryl ether sulfate, lauryl sulfate. These are the standard surfactants used in personal care products. They are characterized by high use concentration (of 8-20 wt.%) And are only slightly friendly to the skin, so their properties are optimized by blending, for example with cosurfactants such as cocamidopropyl betaine and cocoamphoacetate. To obtain a hand-foaming preparation usually 10-15 wt.% Of lauryl ether sulfate are used. Furthermore, lauryl ether sulfate or lauryl sulfate is an anionic surfactant.
  • cationic surfactants are often a major problem due to precipitate formation in aqueous systems (opposite charge of anion and cationic surfactant). Furthermore, cationic polymers for corresponding anionic surfactants are often problematic for the same reason.
  • nonionic surfactants such as alkylpolyglycosides (APG) are also used.
  • APG is the standard surfactant for detergents and cosmetic preparations.
  • the composition of this surfactant mixture is extremely inhomogeneous. Its properties can not therefore be attributed to a single compound.
  • a known APG Planten 2000 UP, Cognis contains, for example, 1% by weight of C 6 -glucosides, 33-40% by weight of C ⁇ -glucosides, 21-28% by weight of C 10 -glucosides, 27-32% by weight.
  • the preparation of the hydrophilic component of the APG takes place a) by hydrolysis of starch or dextrose syrup or b) of anhydrous glucose (or glucose monohydrate). This hydrophilic component is converted in the starch hydrolysis route with butanol in the corresponding glycoside and then umacetalinstrument with the long-chain fatty alcohol.
  • the synthetic route via the anhydrous glucose uses the direct acetalization with the long-chain fatty alcohol in the corresponding glycoside.
  • Disaccharide-based surfactants have hitherto been of lesser importance in cosmetics, as detergents or in the food industry.
  • Alkyl glycosides with disaccharide carbohydrate head groups have also been described in the literature, for example maltosides, lactosides or melibiosides having alkyl chain lengths of 10-20 carbon atoms.
  • a disadvantage of these compounds is their poor water solubility due to a high Krafft temperature. They are therefore not suitable as surfactants.
  • alkyl glycosides such as APGs
  • APGs alkyl glycosides
  • B is a polyhydric alcohol having 2 to 4 C atoms or its derivative
  • C is a branched or unbranched, saturated or unsaturated fatty alcohol radical having 8 to 22, particularly preferably 10 to 14 or 14 to 22, very particularly preferably up to 20
  • C atoms is glycosidically linked to B in position 1,
  • B is etherified with C and x has the value 1 to 50, eliminated.
  • Such compounds have the following advantages: they are very good foaming agents at room temperature and also at higher temperature, for example at 50 ° C., they form very stable foams, they form a large amount of foam at low use concentrations, They allow a very good foaming also for mixtures due to the manufacturing process, they are easy to produce, certain compounds allow gelation, they are miscible with cosurfactants, they are good to very well tolerated.
  • a known method to improve the solubility of amphiphiles is the ethoxylation of hydroxy groups.
  • US3640998 the preparation of ethoxylated alkyl polyglucosides in which all free hydroxy groups are ethoxylated.
  • Targeted ethoxylation in the form of ethoxylated alkyl disaccharides has rarely been disclosed.
  • ethylene glycol as a spacer between the alkyl chain of a fatty alcohol and the carbohydrate head group at the anomeric center has hitherto been known only for a few compounds and the properties were investigated only with regard to a possible medical application (Bendas, G., Wilhelm, F., Richter , W., Nuhn, P., Eur. J. Pharm. Sci., 4, 1996, 211ff .; Nuhn, P., Pfaff, T., Bendas, G., Wilhelm, F., Chatterjee, SK, Arch Pharm., 327, 1994, 429ff.).
  • the spacers serve in this case to increase the distance of the carbohydrate head group to the surface of the liposome.
  • phospholipids are used here with the substituted sugars for liposome formation.
  • the advantages of a targeted ethoxylation in the form of ethoxylated alkyl disaccharides based on lactose, maltose, mellibiose without phospholipids is not known.
  • About foaming, gelation or their suitability as a surfactant is not known.
  • a fine foam can be achieved by blending with cosurfactants.
  • the compounds are better tolerated in terms of their skin tolerance than the standard surfactants lauryl sulfate and lauryl ether sulfate.
  • a lower use concentration depending on the selected disaccharide alkyl glycoside about 1-5
  • unit A are glycosidically linked disaccharides and z.T. glycoside
  • lactosides with melibiosides Mixtures of lactosides with melibiosides, mixtures of lactosides with maltosides and / or mixtures of meliosides and maltosides, in each case pure or as anomer mixtures.
  • 125 lactose can be purchased from Sigma, Fucka, Biolac (Aria Food Corporation, 31097 Harbansen). Furthermore, the monolydrate of lactose (Variolac 99 edible, Biolac) can also be used in addition to anhydrous lactose.
  • Particularly suitable for use as surfactants or emulsifiers disaccharide 130 units are lactose, melibiose and maltose and cellobiose:
  • both their monohydrates and the anhydrous compounds can be used, particularly preferably the monohydrates.
  • Suitable units B include ethylene glycol (EG) 1, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol (PG), dipropylene glycol, glycerol, butylene glycol, pentaerythritol.
  • EG ethylene glycol
  • PG propylene glycol
  • dipropylene glycol glycerol
  • butylene glycol pentaerythritol
  • ethylene glycol diethylene glycol, triethylene glycol, tetraethylene glycol, propane-1,2-diol, propane-1,3-diol, dipropylene glycol, glycerol, butanediol, pentaerythritol.
  • Particularly suitable units C for use as a surfactant are generally alkyl chains having 8-14 C atoms, which may be linear, saturated, branched or unsaturated. Especially preferred for surfactants are linear and saturated alkyl chains having 8-12 carbon atoms. Particularly preferred gel formers are as unit C linear, saturated alkyl chains having 150 12 C-atoms and particularly preferably those having a unit B which has on average one in the form of a single EO unit. Products of lactose and the fatty alcohol narrow range ethoxylates such as Berol 260 or Berol 266 (Akzo) can be used with particular preference as gel-forming products according to the invention. Preferred for use as emulsifiers are compounds having chain lengths of 12-155 22 C atoms. Particularly preferred are then C16 to C18 alkyl chains.
  • Particularly preferred compounds are in particular as foaming compounds:
  • lactosides of technical fatty alcohol ethoxylates in particular the following compounds 13 to 16:
  • Lactoside Lac-EG 3 C10 and Lac- ⁇ -EG 3 C10
  • Lactoside Lac-EG 4 C9 and Lac- ⁇ -EG 4 C9 Lactoside: Lac-EG 4 C10 and Lac- ⁇ -EG 4 C10 Lactoside: Lac-EG 4 C11 and Lac- ⁇ -EG 4 C11
  • Lactoside Lac-EG 2 -C11 and Lac- ⁇ -EG 2 -C11
  • Particularly suitable gelling agents are ⁇ -, 4-linked saccharides, e.g.
  • the surfactant forms a gel here and foams in addition.
  • Particularly suitable gelling agents are the ⁇ -anomers of Lac-EG-C12 or
  • lactosides the technical narrow-range ethoxylates such as Berol® 260
  • Lac-EG-C12, 395 Mal-EG-C12 and Mel-EG-C12 are distinguished as good foaming agents.
  • the mixtures are those from the reaction of lactose or lactose monohydrate with short-chain, ethoxylated fatty alcohols such as laureth-2 and laureth-3 (Lac-Laureth-2 or Lac-Laureth-3 or Lac-EG2C12 and Lac-EG3C12 ), particularly good foaming agents.
  • Short-chain fatty alcohol ethoxylates such as laureth-2 and laureth-3, are available from Sasol (Marlipal) and from Akzo Nobel (Berol 260, 266, 533, 532, 840), (Ethylan 405 1005) and from BASF (Lutensol ON 30).
  • Lutensol ON 30 represents decyl alcohol with 3 EO units in a technical mixture. Therefore, there are also molecules with higher and lower numbers of EO units.
  • the fatty alcohol can also be partially or completely present as an iso-fatty alcohol. The same applies to all technical EO-fatty alcohols adducts.
  • Berol 260, 266, 840 and Ethylan 1005 belong to the "narrow-range" fatty alcohol ethoxylates, which are characterized by a particularly narrow distribution of ethoxylation, for example Berol 260 is linked on average to four ethyleneoxy units and the distribution curve is narrower to standard ethoxylates, however, in the Berol 260 compounds with 1 to 16 Be contained ethyleneoxy units. More details can be found in the product data sheet "Berol 260, 415 266, 840, Ethylan 1005" of the manufacturer Akzo Nobel from September 2005.
  • disaccharide e.g., lactose
  • x degree of ethoxylation
  • lactoside “Lac-Laureth-2” or “Lac-Laureth-3” as the reaction product of technical laureth-2 or laureth-3 with lactose should be understood to mean that shorter or longer-chain fatty alcohols ethoxylated here can.
  • pure fatty alcohol ethoxylates can also be used for the reaction with the particular disaccharide.
  • the surfactants according to the invention are interesting as preparations for a hot bubble bath.
  • the inventively substituted disaccharides can also be reacted with glycerol as a spacer and a hydrophobic group.
  • the corresponding maltoside can be prepared from maltose and ethylhexylglycerol (see later section Foam behavior on hair).
  • the maltosides can be advantageously mixed with lactosides, for example WIaI-EHG with Lac-PG-C12.
  • lactosides for example WIaI-EHG with Lac-PG-C12.
  • lactosides for example WIaI-EHG with Lac-PG-C12.
  • lactosides for example WIaI-EHG with Lac-PG-C12.
  • lactosides for example WIaI-EHG with Lac-PG-C12.
  • Further compounds of the invention are (2'-hexadecyloxy-ethyl) 4-O- ( ⁇ -D-
  • a surfactant or emulsifier system is also composed of (a) alkyl ether sulfate, for example sodium, ammonium, magnesium, MIPA, TIPA,
  • alkyl sulfates for example sodium, ammonium and TEA lauryl sulfate
  • sodium alkyl sulfates such as sodium cetearyl sulfate and at least one compound according to the invention, particularly preferably from lauryl ether sulfate. and / or lauryl sulfate and at least one compound of the invention.
  • a cosmetic preparation such as shampoo, hair conditioner, styling agent, dentifrice, shower gel, shower foam, bath foam, Syndet 1:1, hair dye, facial cleanser, liquid hand detergent, liquid soap, shaving aid (gel or foam), make-up remover, impregnation medium for wipes and / or tissue containing a compound of the invention or
  • According to the invention is also a cleaning agent for the household or for technical purposes such as household cleaners, window cleaners, liquid detergents for textiles, washing powder for textiles, Textilwaschpulveragglomerat or -pellet, machine dishwashing detergents, hand dishwashing detergents containing an inventive
  • the invention also provides a food preparation such as beer, drink, food, tofu containing a compound according to the invention or containing a surfactant system according to the invention. Also according to the invention is a foam-like or foamable preparation
  • the use concentration of the compound according to the invention is 0.3 to 25% by weight.
  • the use concentration of the compound according to the invention is also a use of a compound of the invention or
  • a surfactant system as detergent or cosurfactant in a household cleaner, window cleaner, laundry detergent for textiles, washing powder for textiles, textile washing powder agglomerate or pellet, machine dishwashing detergent, hand dishwashing detergent, hair shampoo, hair conditioner, styling agent, dentifrice, shower gel, shower foam, bath foam, syndet, hair dye,
  • the invention also provides a use of a compound of the invention or of a surfactant system according to the invention for the preparation of a medicament.
  • According to the invention is also a use of a compound according to the invention or of a surfactant system according to the invention for improving the foamability of a water-containing preparation.
  • Surfactant or emulsifier systems according to the invention may additionally contain alkylamidopropylbetaines (for example cocamidopropylbetaine), cocoamphoacetate, lauryl ether sulphate,
  • compositions according to the invention can additionally comprise polymers, where the polymer (s) can be nonionic, cationic, anionic or amphoteric.
  • the invention also encompasses the use of ((2'-dodecyloxyethyl) 4-O- ( ⁇ -D-)
  • the invention also encompasses a process for preparing a compound of the invention by reacting a ⁇ -peracetate of component A with a Lewis
  • the invention also encompasses the preparation of the compounds according to the invention by reacting a ⁇ -peracetate with boron trifluoride-diethyl ether complex as Lewis acid, 2Ü
  • Example 1 particularly preferably with an ⁇ -peracetate and an extended one
  • the invention also encompasses a process for the preparation of a novel composition
  • the invention also encompasses the preparation of the compounds according to the invention by way of direct Fischer glycosylation and the preparation of the compounds according to the invention from glycosyl halides, from glycosylimidates,
  • Orthoestheses n-pentenyl glycosides, thioglycosides, allyl glycosides, and the like. known
  • the invention also includes laureth-2-lactoside, laureth-3-lactoside, laureth-2-maltoside, 560 laureth-3-maltoside as well as products of the reaction of a disaccharide with a
  • Glycerol ethers and / or a diglycerol ether and / or a triglycerol ether the
  • Laurylglycerinether the reaction of maltose with ethylhexylglycerol and the
  • Components according to the invention may furthermore contain surfactants.
  • acylamino acids and their salts, such as
  • acylglutamates for example, disodium acylglutamate, sodium acylglutamate and sodium caprylic / capric glutamate,
  • Acyl peptides for example palmitoyl-hydrolyzed milk protein, sodium cocoyl-hydrolysed soy protein and sodium / potassium cocoyl-hydrolyzed collagen, N-cocoyl-hydrolyzed wheat protein, N-cocoyl
  • sarcosinates for example myristoyl sarcosine, TEA-lauroyl sarcosinate, sodium lauroyl sarcosinate and sodium cocoyl sarcosinate,
  • taurates for example sodium lauroyl taurate and sodium methyl cocoyl taurate
  • acyl lactylates for example, lauroyl lactylate, caproyl lactylate, 580, 6-alaninates,
  • Arginates for example N-lauroyl arginate
  • valinates for example N-lauroyl valinate
  • Prolinates for example N-lauroyl prolinate
  • Glycinate for example N-lauroyl glycinate, cocoamphopolycarboxyglycinate, 585 11.
  • Aspartates for example N-lauroyl aspartates, di-TEA-palmitoyl aspartate,
  • Carboxylic acids and derivatives such as
  • Carboxylic acids and their alkali and alkaline earth salts, triethanolamine salts, or zinc salts for example lauric acid, sodium, potassium, magnesium
  • Ester carboxylic acids for example calcium stearoyl lactylate, laureth-6-citrate and sodium PEG-4-lauramide carboxylate,
  • Ether carboxylic acids for example sodium laureth-13-carboxylate and sodium PEG-6-cocamide carboxylate,
  • Phosphoric acid esters and salts such as, for example, DEA-oleth-10-phosphate and dilaureth-4-phosphate,
  • alkylsulfonates for example Natriumcocosmo ⁇ oglyceridsulfat, sodium C-12 olefin sulfonate 14, sodium lauryl sulfoacetate and magnesium PEG-3
  • Sulfosuccinates for example dioctyl sodium sulphosuccinate, disodium laureth sulphosuccinate, disodium lauryl sulphosuccinate and disodium undecylenamido MEA sulphosuccinate, and also 610 sulfuric acid esters, such as
  • alkyl ether sulfate for example sodium, ammonium, magnesium
  • Alkyl sulfates for example sodium, ammonium and TEA lauryl sulfate, 615 3.
  • Sodium alkyl sulfates such as sodium cetearyl sulfate.
  • Quaternary surfactants contain at least one N-atom, which with 4 alkyl and / or
  • quaternary surfactants are alkyl betaine, alkyl amido propyl betaine and alkyl amidopropyl hydroxysulfain.
  • Cationic surfactants can furthermore preferably be selected for the purposes of the present invention from the group of the quaternary ammonium compounds, in particular
  • alkylammonium chlorides or bromides such as, for example, benzyldimethylstearylammonium chloride, furthermore alkylthalkylammonium salts, for example cetyltrimethylammonium chloride or bromide, alkyldimethylhydroxyethylammonium chlorides or bromides, dialkyldimethylammonium chlorides or bromides, dialkyl ethoxylate dimethylammonium chlorides or bromides such as, for example,
  • Cetyltrimethylammonium salts are particularly advantageous to use.
  • acyldialkylethylenediamine for example sodium acylamphoacetate, disodium acylamphodipropionate, disodium alkylamphodiacetate,
  • N-alkylamino acids for example aminopropylalkylglutamide, alkylamino-650-propionic acid, sodium alkylimidodipropionate and lauroamphocarboxyglycinate.
  • Polyquaternium 10 Polyquater ⁇ ium 24 is preferred.
  • guar hydroxypropyltrimonium chloride Preferably, for example, guar hydroxypropyltrimonium chloride and
  • DMDAAC Dimethyl Diallyammonium Chloride
  • polyquaternium 4 and 6 and 7 are preferred.
  • AETAC acryloyloxy ethyl trimethyl ammonium 675 chloride
  • polyquaternium 33 is preferred.
  • polyquaternium 5 and polyquaternium 11 and 680 polyquaternium 14 and polyquaternium 15 and polyquaternium 36 and are preferred
  • hydroxyalkylcelluloses starches, hydroxyalkyl starches, polymers based on arabinose monomers, polymers derived from xylose, fucose, fructose, galacturonic acid and glucuronic acid, galactosamine and glucosamine, acetylglucosamine, galactose, mannose.
  • hydroxypropyl trimethyl ammonium chloride are preferred
  • starch 690 derivatives of starch, which may be from corn, potato, rice, tapioaca, wheat and the like.
  • Block copolymers (PEG / PPG).
  • Compositions according to the present invention may also contain moisturizers such as glycerine, chitosan, fucogel, lactic acid, propylene glycol, dipropylene glycol, butylene glycol, mannitol, sodium pyrollocarboxylic acid, hyaluronic acid and its salts, amino acids such as glycine, urea, sodium and potassium salts.
  • moisturizers such as glycerine, chitosan, fucogel, lactic acid, propylene glycol, dipropylene glycol, butylene glycol, mannitol, sodium pyrollocarboxylic acid, hyaluronic acid and its salts, amino acids such as glycine, urea, sodium and potassium salts.
  • salts for the alkyl glycosides according to the invention are calcium chloride, magnesium sulfate, sodium sulfate, KCl, magnesium chloride and sodium chloride. It is also particularly advantageous to add water-soluble active ingredients.
  • the preparation processes for components according to the invention are basically known (ViII, V., Böcker, T., Thiem, J., Fischer, F., Liq. Cryst., 6, 1989, 349 et seq., V. Minden, HM, Brandenburg , K., Seydel, U., Koch, MHJ, Garamus, VM, Willumeit, R., ViII, V.
  • ⁇ -anomer 740 describe the ⁇ -anomer.
  • the representation of the ⁇ -anomer can be carried out similarly only as Lewis acid stannic chloride used in equimolar amount and the reaction time increases to at least 48 hours, the yield is in the case of Laurylethylenglycolglycoside between 25 and 30%.
  • the use of polyhydric alcohols or mixtures of alcohols leads to
  • butyl, propyl, ethyl or methyl glycosides to be preferred.
  • Reaction of a short chain glycoside provides the desired products under milder reaction conditions 770.
  • lactosides are ⁇ / ß mixtures.
  • the following lactosides were prepared 785:
  • Example 4 The product is a mixture of the ⁇ - and ⁇ -anomers where the ⁇ -portion predominates.
  • the product distribution depends on the used
  • Lactosides from fatty alcohol ethoxylates and lactose [Lutensol ® ON 30 (C10-alcohol +3 EO); Berol 260 (C9-C11 alcohol ethoxylate (4)); Berol 532 (C11 alcohol ethoxylate (2)); Berol 533 (C11 alcohol ethoxylate (3))]:
  • the peracetylated lactosides were each treated with about 8O mL of anhydrous methanol and
  • the Lutensol ® ON 30 (C10-alcohol +3 EO) was purchased from BASF Ludwigshafen, 67056 Germany. A mixture of Lac-EG 3 C10 and Lac- ⁇ -EG 3 CIO 930 is obtained
  • Lactoside Lac-EG 4 C9 and Lac- ⁇ -EG 4 C9 Lactoside: Lac-EG 4 C10 and Lac- ⁇ -EG 4 C10 Lactoside: Lac-EG 4 C11 and Lac- ⁇ -EG 4 C11 965
  • the Berol 260 (C11 Alcohol Ethoxylate (4) was obtained from Akzo Nobel Surface Chemistry AB SE 44485 Stenungsund, Sweden, Mainly a 970 blend of Lac-EG 4 C 9, Lac- ⁇ -EG 4 C 9, Lac-EG 4 C10, Lac- ⁇ -EG 4 C10, Lac-EG 4 C11 and Lac- ⁇ -EG 4 C11.
  • Lactoside Lac-EG 2 -C11 and Lac- ⁇ -EG 2 -C11
  • the Berol 532 (C11 alcohol ethoxylate (2)) was purchased from Akzo Nobel Surface Chemistry AB SE 44485 Stenungsund, Sweden. Mainly a mixture of Lac-EG 2 -C11 and Lac- ⁇ -EG 2 -C 11 is obtained.
  • Lactoside Lac-EG 3 -C11 and Lac- ⁇ -EG 3 -C11
  • the Berol 533 (C11 alcohol ethoxylate (3)) was purchased from Akzo Nobel Surface Chemistry AB SE 44485 Stenungsund, Sweden. Mainly a mixture of Lac-EG 3 -C11 and Lac- ⁇ -EG 3 -C 11 is obtained.
  • Figure 1 shows the foam immediately after shaking. Shown are lactosides from lactose and corresponding ethoxylated fatty alcohol.
  • 1) Lutensol ON 30 ® CIO alcohol +3 EO
  • 2.) Berol 533 C1 1 alcohol ethoxylate (3)
  • 3.) Berol 260 C9-C11 alcohol ethoxylate 1020 (4)
  • 4. ) Berol 532 C 11 Alcohol ethoxylate (2)
  • Figure 2 shows the foam after 20 minutes. Shown are lactosides from lactose and corresponding ethoxylated fatty alcohol. 1.) Lutensol ON 30 ® (C10-alcohol + 3 EO), 2.) Berol 533 (C11 alcohol ethoxylate (3)), 3.) Berol 260 (C9-C11 alcohol ethoxylate 1025 (4)), 4.) Berol 532 (C1 1 alcohol ethoxylate (2))
  • the lactosides 1-4 show very good foaming properties at this concentration.
  • the foaming power is very good in all.
  • the foam is optically fine-pored. After 20 minutes, hardly any changes in the foam pattern, this indicates a pronounced foam stability.
  • the starting materials used were the following substances:
  • the disaccharide used was the lactose monohydrate Variolac 99 edible G800 from Biolac GmbH & Co. KG, 31097 Harbamsen.
  • Lactose monohydrate or anhydrous lactose can be used to prepare the compounds.
  • Gel formation by surfactants according to the invention :
  • Lac-EG-C12 forms a gel at a concentration of 0.1% by weight up to a transition temperature of 43 ° C. and Lac-PG-C12 at 0.1% by weight to 41 ° C. Above this transition temperature, the gel becomes liquid.
  • the structure Lac-EG-C12 is above
  • Lac-EG-C12 can also be used in mixtures with other surfactants, e.g. Lauryl ether sulfate and cosurfactants, e.g. Cocoamphoacetate, cocamidoproyl betaine, cocoylglutamate is able to form gels.
  • surfactants e.g. Lauryl ether sulfate and cosurfactants, e.g. Cocoamphoacetate, cocamidoproyl betaine, cocoylglutamate is able to form gels.
  • anionic surfactants such as lauryl ether sulfate, thickeners are added because APGs in low concentrations have no thickening effect.
  • T ge ⁇ Phase transition temperatures from the gel to the isotropic solution for different concentrations of lipid (deviation ⁇ 0.5 0 C).
  • the compound forms a stable gel and above T ge ⁇ a clear solution.
  • T ge ⁇ is defined as the temperature at which the gel begins to dissolve. The temperature range of the transition is normally 2 to 5 0 C.
  • the lactoside from Berol 260 and lactose (product 14)) is capable of gelation.
  • the resulting gel is exceptionally clear, for example, at a level of 5% by weight in water 1090. See Figure 3.
  • Transition temperature makes them a clear solution.
  • T ge ⁇ is defined as the temperature at 1100 which the gel begins to dissolve.
  • the temperature range of the transition is in
  • Gel formation can also be reversed by admixing other compounds. This can be achieved by using mono-, di- and triethylene glycol alkyl ethers
  • Lactoside mixes with each other Lactoside mixes with each other.
  • the mixtures which are obtained by reacting laureth-2 or laureth-3 with lactose are particularly advantageous.
  • the ⁇ -anomer of Lac-EG-C12 is particularly preferred since it also does not form a gel.
  • Measurements are carried out in 100 ml_ measuring cylinders. Before use, the measuring cylinder is filled with concentrated nitrating acid and stored for 24 hours, then with
  • Foamability and foam stability of selected compounds at a surfactant concentration of 0.01 wt% and a temperature of 25 0 C and 50 0 C (Lac- 1160 EC C12: Laurylethylenglycol-ß-lactoside, time-EC C12: Laurylethylenglycol-.beta. Maltoside, MeI-EG-CI 2: lauryl ethylene glycol ⁇ -melibioside, SDS: sodium dodecyl sulfate, SLES: lauryl ether sulfate). See Figure 5.
  • the compounds according to the invention showed a comparable foam formation on the skin or the hair, such as, for example, lauryl ether sulfate, but in significantly lower use concentrations.
  • Lac-EG-C12 (Table 10)
  • scum formation 1175 is observed when triturating the surfactant.
  • 1% by weight of the substance according to the invention was dissolved in water in the presence of hair strands and rubbed in the hand.
  • the foam is much finer than comparable foams of lauryl ether sulfate.
  • the best foaming agent in the form of its individual component according to the invention was the ⁇ -anomeric Lac-EG-C12 or also Lac-Laureth-2 or Lac-Laureth-3. 1180
  • the foaming behavior of the other surfactants according to the invention can be described in terms of foaming power and fine-poredness of the foam by adding classical cosurfactants, such as, for example, Control lauryl ether sulfate, betaines, amphoacetates and acyl glutamates.
  • cosurfactants such as, for example, Control lauryl ether sulfate, betaines, amphoacetates and acyl glutamates.
  • a cosurfactant according to the invention is the maltose glycoside of ethylhexylglycerol.
  • some of the compounds of the invention are characterized by a significantly better skin compatibility and a significantly lower irritation of the mucous membrane compared to lauryl ether sulfate, lauryl sulfate and even APG.
  • the 1235 compatibility studies were carried out by methods known from the literature (Pape, W., Pfannenbecker, U., Hoppe, U .: Validation of the red blood cell test as an in vitro assay for the rapid screening of irritation potential of surfactants, Molecular Toxicology 1, 525 -536 1987)
  • the surfactant is suspended in water and heated until a clear solution is obtained, but not above 60 ° C. Subsequently, the 50 ° C. warm solution is adjusted to a pH of 5.5 with citric acid. Upon cooling, a gel is formed.
  • sugar surfactant is added and the mixture is heated until a clear solution is obtained, but not above 60 ° C.
  • the citric acid is then adjusted to a pH of 5.5 by adding the solution at 50 ° C. A gel forms on cooling
  • the surfactant mixture according to the invention is dissolved in water at room temperature and adjusted to pH 5.5 with citric acid.
  • the surfactant mixture according to the invention is dissolved at room temperature in a solution of lauryl ether sulfate and adjusted to pH 5.5 with citric acid.
  • the surfactant mixture according to the invention is dissolved at room temperature in a solution of
  • the surfactant Lac-PG-C12 according to the invention is added and heated until a clear solution is established, but not above 60 ° C.
  • the 50 0 C warm solution is adjusted to pH 5.5 with citric acid. Upon cooling, a gel forms.
  • the surfactant of the invention is dissolved in water at room temperature and adjusted to pH 5.5 with 1390 citric acid.
  • the surfactant of the invention is dissolved in a solution of the cosurfactant in water and adjusted to pH 5.5 with citric acid.

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Abstract

La présente invention concerne des composés de formule A-(B)x-C dans laquelle A est un di- ou trisaccharide réducteur, B est un alcool plurivalent comprenant de 2 à 4 atomes de carbone ou son dérivé, C est un radical alcool gras saturé ou insaturé, ramifié ou non ramifié comprenant de 8 à 22 atomes de carbone, de préférence de 8 à 14 ou de 14 à 22, en particulier de préférence jusqu'à 20 atomes de C, A est lié à B par liaison glyosidique en position 1, B est estérifié avec C, et x vaut de 1 à 50.
EP06723701A 2005-03-24 2006-03-24 Nouveaux tensioactifs et nouveaux emulsifiants a base de disaccharides Ceased EP1863825A1 (fr)

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DE102005014424A DE102005014424A1 (de) 2005-03-24 2005-03-24 Neue Tenside und neue Emulgatoren auf der Basis von Disacchariden
PCT/EP2006/002721 WO2006100091A1 (fr) 2005-03-24 2006-03-24 Nouveaux tensioactifs et nouveaux emulsifiants a base de disaccharides

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DE102008059904A1 (de) * 2008-12-02 2010-06-10 Beiersdorf Ag Schäumende oder schäumbare Zubereitungen mit einem Gehalt an Alkyl-Lactosiden
DE102008059905A1 (de) * 2008-12-02 2010-06-10 Beiersdorf Ag Gelförmige Zubereitungen auf der Basis von Alkyl-Lactosiden
CN102247779A (zh) * 2011-05-04 2011-11-23 上海大学 不对称两性离子型Gemini表面活性剂及其制备方法
FR2980694B1 (fr) * 2011-09-29 2013-09-27 Gattefosse Sas Agent emulsifiant, procede de fabrication, et utilisation
CN102872752B (zh) * 2012-09-21 2014-04-16 浙江大学 一种癸醇葡萄糖双子表面活性剂及其制备方法
CN102895914B (zh) * 2012-09-21 2014-03-12 浙江大学 一种十二醇葡萄糖双子表面活性剂及其制备方法
CN102875613B (zh) * 2012-09-21 2014-04-16 浙江大学 一种十六醇葡萄糖双子表面活性剂及其制备方法
CN102895915B (zh) * 2012-09-21 2014-03-12 浙江大学 一种十四醇葡萄糖双子表面活性剂及其制备方法
CN102861532B (zh) * 2012-09-21 2014-03-12 浙江大学 一种十八醇葡萄糖双子表面活性剂及其制备方法
CN105713052B (zh) * 2016-01-19 2019-01-04 威尔（福建）生物有限公司 一种聚醚糖苷磺酸盐及其制备方法、应用和一种除草剂
CN106883276A (zh) * 2017-02-24 2017-06-23 湘潭大学 新的1,2‑顺式木糖苷表面活性剂
CN106831890A (zh) * 2017-02-24 2017-06-13 湘潭大学 一种新型木糖苷表面活性剂
CN106831900A (zh) * 2017-02-24 2017-06-13 湘潭大学 一种糖苷类化合物
CN107011395B (zh) * 2017-05-27 2020-01-03 湘潭大学 一类n-乙酰氨基葡萄糖苷类化合物
BR112021010745A2 (pt) 2018-12-03 2021-08-31 Carbonet Nanotechnologies Inc. Nanorredes para remoção de contaminantes de soluções aquosas, kits para as mesmas e métodos para seu uso
CN111848704A (zh) * 2019-04-24 2020-10-30 湘潭大学 1,2-顺式醇醚木糖苷表面活性剂及制备方法

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