EP1807044A1 - Melanges de tensioactifs quaternaires et non-ioniques - Google Patents

Melanges de tensioactifs quaternaires et non-ioniques

Info

Publication number
EP1807044A1
EP1807044A1 EP05800392A EP05800392A EP1807044A1 EP 1807044 A1 EP1807044 A1 EP 1807044A1 EP 05800392 A EP05800392 A EP 05800392A EP 05800392 A EP05800392 A EP 05800392A EP 1807044 A1 EP1807044 A1 EP 1807044A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
alkenyl
formula
carbon atoms
sup
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Withdrawn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
EP05800392A
Other languages
German (de)
English (en)
Inventor
Ansgar Behler
Frank Clasen
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.)
Cognis IP Management GmbH
Original Assignee
Cognis IP Management GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cognis IP Management GmbH filed Critical Cognis IP Management GmbH
Publication of EP1807044A1 publication Critical patent/EP1807044A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • 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
    • 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
    • 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
    • C11D1/66—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
    • C11D1/835—Mixtures of non-ionic with cationic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/596—Mixtures of surface active compounds

Definitions

  • the invention is in the field of cationically substituted glycoside surfactants, as well as a process for the preparation thereof and their use in the field of cosmetics and detergents.
  • cationic derivatives of alkylpolyglycosides are the subject of WO 90/15809. According to WO 90/15809, these quaternary surfactants are prepared by alkylation of quaternized saccharides, since the quaternization of alkyl polyglycosides does not work.
  • Alkyl polyglycosides are a common and commonly used class of surfactants, which could therefore be readily used as the starting material for derivatization. Unreacted educt could then remain in the product and contribute to its surfactant properties.
  • the object of the present invention in the simple preparation of cationic Alkylpolyglycosidderivaten, in which no harmful by-products anfal ⁇ len, which would have to be removed. Furthermore, a surfactant mixture based on very skin-friendly sugar surfactants should be found which has improved foaming and emulsifying properties. Description of the invention
  • the present application relates to preparations containing
  • R 2 is -O- [G] X -Z y (II) in which R 2 is a linear or branched alkyl and / or alkenyl radical having 4 to 22 carbon atoms, G is a sugar radical having 5 or 6 carbon atoms, x is Zah L is from 1 to 10 and y is a number from 1 to 4 and Z is an -OCH 2 - (CH (B)) V - (CH (A)) W -N + (R 3 R 4 R 5 )
  • X is a group in which A and B independently of one another represent hydrogen or a hydroxyl group, v and w independently of one another are numbers from 1 to 18, X is an anion which is selected from the group which formed is chloride, bromide, iodide, fluoride, NO 3 " , SO 4 2 ' and PO 4 3" , and R 3 , R 4 and R 5 independently of one another are hydrogen or alkyl and / or alkenyl groups having 1 to
  • This preparation is characterized by a high mildness to skin and hair, while they have excellent foam properties and cleaning effect.
  • the two components (a) and (b) are preferably present in a weight ratio of 10:90 to 90:10, more preferably in a weight ratio of 40:60 to 60:40.
  • component (b) used are compounds of the formula (II) in which B is hydrogen, A is a hydroxyl group, w and v are 1, R 3 and R 4 are each methyl, R 5 is a methyl group or lauryl and X "represent chloride.
  • xyolitic wherein B is hydrogen, a is a Hydro ⁇ , w and v is 1, R 3, R 4 and R 5 are a methyl radical and X "is chloride.
  • Another object of the present invention is a method for Preparation of cationic alkyl and / or alkenyl oligoglycoside derivatives of the formula
  • R 2 is -O- [G] X -Z y (II) in which R 2 is a linear or branched alkyl and / or alkenyl radical having 4 to 22 carbon atoms, G is a sugar radical having 5 or 6 carbon atoms, x is a number from 1 to 10 and y represents numbers from 1 to 4 and wherein Z is an -OCH 2 - (CH (B)) V - (CH (A)) W -N + (R 3 R 4 R 5 ) X " Group in which A and B independently of one another represent hydrogen or a hydroxyl group, v and w independently of one another represent numbers from 1 to 18, X "is an anion which is selected from the group which forms is chloride, bromide, iodide, fluoride, NO 3 " , SO 4 2" and PO 4 3 " , and R 3 , R 4 and R 5 are independently hydrogen or alkyl and / or alkenyl groups having 1 to 22 carbon atoms and at least
  • the starting materials used are preferably alkyl and / or alkenyl oligoglycosides of the formula (I),
  • R'-O- [G] P (I) in the R 1 is a linear or branched alkyl and / or alkenyl radical having 4 to 22 carbon atoms, G is a sugar radical having 5 or 6 carbon atoms and p is a number from 1 to 10 stands.
  • Preferred quaternizing agent according to formula (III) are compounds in which B is hydrogen, A is a hydroxy group, w and v are 1, R 3 , R 4 and R 5 is a methyl radical and X "is chloride.
  • Alkyl and alkenyl oligoglycosides are known nonionic surfactants which follow the formula (I),
  • R 1 is an alkyl and / or alkenyl radical having 4 to 22 carbon atoms
  • G is a sugar radical having 5 or 6 carbon atoms
  • p is a number from 1 to 10. she can be obtained by the relevant methods of preparative organic chemistry.
  • the alkyl and / or alkenyl oligoglycosides can be derived from aldoses or ketoses having 5 or 6 carbon atoms, preferably glucose.
  • the preferred alkyl and / or alkenyl oligoglycosides are thus alkyl and / or alkenyl oligoglucosides.
  • the index number p in the general formula (I) indicates the degree of oligomerization (DP), ie the distribution of mono- and oligoglycosides, and stands for a number between 1 and 10.
  • the value p for a given alkyloligoglycoside is an analytically determined arithmetic quantity which usually represents a fractional number. Preference is given to using alkyl and / or alkenyl oligoglycosides having an average degree of oligomerization p of from 1.1 to 3.0. From an application point of view, those alkyl and / or alkenyl oligoglycosides whose degree of oligomerization is less than 1.7 and in particular between 1.2 and 1.5 are preferred.
  • the alkyl or alkenyl radical R 1 can be derived from primary alcohols having 4 to 11, preferably 8 to 10 carbon atoms. Typical examples are butanol, caproic alcohol, caprylic alcohol, capric alcohol and undecyl alcohol, and technical mixtures thereof, as are obtained, for example, in the hydrogenation of technical fatty acid methyl esters or in the hydrogenation of aldehydes from Roelen's oxosynthesis.
  • the alkyl or alkenyl radical R 1 can also be derived from primary alcohols having 12 to 22, preferably 12 to 14 carbon atoms.
  • Typical examples are lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, olefin alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, brassidyl alcohol and technical mixtures thereof which can be obtained as described above.
  • Alkyl oligoglucosides based on hydrogenated C 2 / i 4 coconut alcohol with a DP of 1 to 3 are preferred.
  • the process is characterized in that the alkyl and / or alkenyl oligoglycosides and the quaternizing reagents of the formula (III) are used in a molar ratio of 1: 0.5 to 1: 4, particularly preferably 1 : 1 to 1: 1.5. Particularly good yields are obtained when the reaction is carried out at temperatures of 20 to 100 0 C and most preferably at temperatures of 40 to 80 ° C is orientalge.
  • the surfactant formulations obtained by this process which comprise a mixture of alkyl- and / or alkenyl oligoglycosides of the formula (I) in combination with cationic alkyl and / or alkenyl oligoglycoside derivatives of the formula (II), may be used in combination with other conventional ingredients , such as other surfactants, emulsifiers, oil bodies, active ingredients, silicones, fats and waxes, etc. in cosmetic preparations such as shampoos and shower-baths or in cleaning preparations.
  • the preparations according to the invention can also be applied to cleaning wipes directly or after processing to cosmetic preparations by adding further customary ingredients.
  • we speak of dry or wet wipes. These wipes can then be used either directly or after moistening to cleanse or condition skin and hair.
  • Dry residue 38.7% by weight of which Plantacare 1200: 13.5% by weight QUAB 188 ⁇ 0.1% by weight

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Molecular Biology (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Genetics & Genomics (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Detergent Compositions (AREA)
  • Saccharide Compounds (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne des préparations contenant (a) des alkyloligoglucosides et/ou des alcényloligoglucosides de formule (I), R<SUP>1</SUP>O-[G]<SUB>p</SUB> (I), dans laquelle R<SUP>1</SUP> signifie un groupe alkyle et/ou alcényle linéaire ou ramifié avec 4 à 22 atomes de carbone, G désigne un groupe glucide avec 5 ou 6 atomes de carbone et p représente des nombres de 1 à 10, ainsi que (b) des dérivés alkyloligoglucoside et/ou alcényloligoglucoside cationiques de formule (II), R<SUP>2</SUP>-O-[G]<SUB>x</SUB>-Z<SUB>y </SUB>(II), dans laquelle R<SUP>2</SUP> signifie un groupe alkyle et/ou alcényle linéaire ou ramifié avec 4 à 22 atomes de carbone, G désigne un groupe glucide avec 5 ou 6 atomes de carbone, x représente des nombres de 1 à 10 et y des nombres de 1 à 4, et Z signifie un groupe -OCH<SUB>2</SUB>-(CH(B))<SUB>v</SUB>-(CH(A))<SUB>W </SUB>N<SUP>+</SUP>(R<SUP>3</SUP>R<SUP>4</SUP>R<SUP>5</SUP>)X, dans lequel A et B désignent indépendamment l'un de l'autre hydrogène ou un groupe hydroxyle, v et w représentent indépendamment l'un de l'autre des nombres de 1 à 18, X est un anion sélectionné dans le groupe comprenant chlorure, bromure, iodure, fluorure, NO<SUB>3</SUB> <SUP>-</SUP>
EP05800392A 2004-11-05 2005-10-27 Melanges de tensioactifs quaternaires et non-ioniques Withdrawn EP1807044A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004054035A DE102004054035A1 (de) 2004-11-05 2004-11-05 Mischungen von quaternären und nichtionischen Tensiden
PCT/EP2005/011482 WO2006048165A1 (fr) 2004-11-05 2005-10-27 Mélanges de tensioactifs quaternaires et non-ioniques

Publications (1)

Publication Number Publication Date
EP1807044A1 true EP1807044A1 (fr) 2007-07-18

Family

ID=35759154

Family Applications (1)

Application Number Title Priority Date Filing Date
EP05800392A Withdrawn EP1807044A1 (fr) 2004-11-05 2005-10-27 Melanges de tensioactifs quaternaires et non-ioniques

Country Status (6)

Country Link
US (1) US20080119414A1 (fr)
EP (1) EP1807044A1 (fr)
JP (1) JP2008518989A (fr)
CN (1) CN101052374A (fr)
DE (1) DE102004054035A1 (fr)
WO (1) WO2006048165A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120093753A1 (en) 2007-06-29 2012-04-19 Fevola Michael J Cationic polyglyceryl compositions and compounds
US8986665B2 (en) 2007-06-29 2015-03-24 Johnson & Johnson Consumer Companies, Inc. Cationic polyglyceryl compositions and compounds

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3804599A1 (de) * 1988-02-13 1989-08-24 Basf Ag Verfahren zur reinigung von langkettigen alkylglucosiden
WO1990015809A1 (fr) * 1989-06-16 1990-12-27 Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) Glycosides a substitution cationique
US5138043A (en) * 1989-12-07 1992-08-11 Union Carbide Chemicals & Plastics Technology Corporation Alkoxylated alkyl glucoside ether quaternaries useful in personal care
DE4413686C2 (de) * 1994-04-20 1996-10-24 Henkel Kgaa Kationische Zuckertenside, Verfahren zu ihrer Herstellung und deren Verwendung

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2006048165A1 *

Also Published As

Publication number Publication date
DE102004054035A1 (de) 2006-05-11
US20080119414A1 (en) 2008-05-22
CN101052374A (zh) 2007-10-10
JP2008518989A (ja) 2008-06-05
WO2006048165A1 (fr) 2006-05-11

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