CA2197111A1 - Aqueous preparations, comprising alkyl polyglycosides and a polymer - Google Patents

Aqueous preparations, comprising alkyl polyglycosides and a polymer

Info

Publication number
CA2197111A1
CA2197111A1 CA002197111A CA2197111A CA2197111A1 CA 2197111 A1 CA2197111 A1 CA 2197111A1 CA 002197111 A CA002197111 A CA 002197111A CA 2197111 A CA2197111 A CA 2197111A CA 2197111 A1 CA2197111 A1 CA 2197111A1
Authority
CA
Canada
Prior art keywords
alkyl
preparation
formula
alkyl polyglycosides
atoms
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.)
Abandoned
Application number
CA002197111A
Other languages
French (fr)
Inventor
Knut Oppenlander
Gunter Oetter
Hans-Ulrich Wekel
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Publication of CA2197111A1 publication Critical patent/CA2197111A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/10Washing or bathing preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60Sugars; Derivatives thereof
    • A61K8/604Alkylpolyglycosides; Derivatives thereof, e.g. esters
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/87Polyurethanes
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/02Preparations for cleaning the hair

Abstract

Aqueous preparations comprising an alkyl polyglycoside and a polyethylene glycol ether derivative of the formula I

(see fig. I) where R1 is alkyl having 8-22 carbon atoms, A is a divalent radical derived from a diisocyanate and n is 20 - 400 are described.

Description

~ 21971 1 1 Aqueous preparations, comprising alkyl polyglycosides and a polymer 5 The present invention relates to aqueous preparations which comprise alkyl polyglycosides and polyethylene glycol ether derivatives.

The compositions according to the invention are, in particular, 10 cosmetic compositions.

Cosmetic compositions which contain alkyl polyglycosides and polymers are known from the prior art (SOFW Journal, 121st year, 8/95, pages 598-611). It is mentioned that polymers such as, for 15 example, xanthan gum and alginates are used in alkyl polyglycoside formulations as viscosity-regulating additives (see p. 607, 1st column).

EP 511 566 A1 discloses aqueous surfactant preparations having 20 increased viscosity which, beside base surfactants, contain alkyl polyglycosides and a polymer, derivatives of a]koxylated polyhydric alcohols being mentioned as polymers.

EP 408 965 and EP 388 810 disclose detergent compositions which 25 contain alkyl glycosides.

DE 42 17 673 Al discloses electrolyte-thickenable surfactant combinations which contain alkyl polyglycosides, carboxymethylated alkanol ethoxylate and monoalkyl sulfosuccinate 30 in very specific quantitative ratios.

Hydrophobically modified urethane ethoxylate thickeners of the formula alkyl-NHCO~En-DI)2-En-OCONH-alkyl where E=ethylene oxide 35 and DI=diisocyanate are known for use in paints from Colloids and Surfaces A: Physicochemical and Engineering Aspects, 82 (1994) 263-277.

DE 22 04 841 and DE 20 54 885 describe pigment printing pastes 40 which contain polyethylene glycol ether derivatives as thickeners.

It is an object of the present invention to make available aqueous preparations which contain alkyl polyglycosides, ie. a 45 constituent based on renewable raw materials which is advantageous from toxicological, ecological and physiological points of view. At the same time, the preparation should have a . ~ - 2 ~ high viscosity without relatively large concentrations of electrolytes (such as, for example, ~aCl~ being necessary.

We have found that this object is achieved by aqueous 5 preparations which, beside alkyl polyglycosides, contain polyethylene glycol ether derivatives of the formula I

Rl ~~--CH2--CH2--Ot--nA~--o--CH2--CH2t o--R
10 where Rl is alkyl having 8-22 carbon atoms, A is a divalent radical derived from a diisocyanate and n is 20 - 400.

These preparations are preferably cosmetic compositions, in particular hair treatment compositions, shower baths, shower 20 gels, but also facial cleansers, handwashing pastes and lotions.
~air treatment composition~ which may be menkioned are: shampoos, hair rinses, styl~ng gels and waving composi.tions.

The aqueous preparations according to the invention preferably 25 contain an additional surfactant. This surfactant can be surfactants customary in aqueous, in particular cosmetic preparations, such a~, for example, fatty alcohol ether sulfates, fatty alcohol sulfates, carbo.xym0thylat.ed fatty alcohol ethoxylates, fatty alcohol ether sulfosuccinates, 30 alkanesulfonates, fatty a~.-id salts, a].kyl.betaines, ampholytes, fatty alcohol ethoxylates, fatty acid sorbitan esters, ethoxylated sorbitan esters~ suyar esters and their mixtures count as base surfactants, the chain length of the saturated or unsaturated, straight-chain or branched alkyl chain in each case 35 being 8 to 22, preferably 10 to 20 carbon atoms, and the cations of the anionic surfactants being Na, R, NH4, C2-C3-alkanolammonium or Mg. The degrees of ethoxylation in the case of the fatty alcohol ether sulfates are from 1 to 5 (preferably from 2 to 4)t in the case of the carboxylated ethoxylates from 2 to 15 ~3 to 40 10), in the case of the fatty alcohol ether sulfosuccinates from 1 to 6 (2 to 4) and in the case of the fatty alcohol ethoxylates from 2 to 25 (2 to 15) mol of ethylene oxide/mole.

The alkyl polyglycosides contained in the preparations according 45 to the invention preferably corresond to the formula II

...

R2-O-Gm II

where 5 R2 is a linear or branched alkyl radical having 8 to 18, preferably 10-16 C atoms, G is a polyglycosyl radical and 10 m is 1.1 - 5, preferably 1.1 - 2.5.

In the above formula I, R1 is preferably an alkyl radical having 10-20 C atoms, A is preferably the divalent radical derived from an aromatic diisocyanate and n is preferably 60-300.
The preparations according to the invention preferably contain 1-20% by weight of alkyl polyglycoside and 0.05-1, in particular 0.1-0.5, % by weight of polyethylene glycol ether derivatives of the formula I.
If, beside the alkyl polyglycosides and the customary base surfactants, the polyethylene glycol derivatives of the formula I
according to the invention are employed, then even with additions of from 0.2 to 0.8% by weight a thickening of 4000-18,000 mPa-s is 25 achieved.

The preparation of the polyethylene glycol ether derivatives is given in detail in DE 22 04 841, which is expressly referred to.

30 The alkyl polyglycosides employed according to the invention are commercially available, which is pointed out in the SOFW Journal, 121st year, 8/95, page 598. They can be prepared in a known manner on the basis of renewable raw materials, see, for example, EP 511 466 Al, column 3. It is indicated there that, for example, 35 dextrose can be reacted with n-butanol in the presence of an acidic catalyst to give butyl polyglycoside mixtures which can likewise be transglycosidated with long-chain alcohols, likewise in the presence of an acidic catalyst, to give the desired alkyl polyglycoside mixtures.
The structure of the products can be varied within certain limits. The alkyl radical R2 is fixed by the choice of the long-chain alcohol. The surfactant alcohols having 10 to 18 C
atomq accessible on the large industrial scale, in particular 45 native fatty alcohols from the hydrogenation of fatty acids or ~ 21971 1 1 fatty acid derivatives, are convenient for economic reasons.
Ziegler alcohol or oxo alcohols can also be used.

The polyglycosyl radical Gm is fixed on the one hand by the choice 5 of the carbohydrate and on the other hand by the setting of the mean degree of polymerization n, eg. according to DE-OS 19 43 689. In principle, as is known, polysaccharides, eg.
starch, maltodextrins, dextrose, galactose, mannose, xylose etc.
can be employed. The carbohydrates of starch, maltodextrins and 10 particularly dextrose available on the large industrial scale are preferred. As the alkyl polyglycoside syntheses, which are of economic interest, do not proceed regio- and stereoselectively, the alkyl polyglycosides are always mixtures of oligomers which in turn are mixtures of various isomeric forms. They are present 15 together with a- and ~-glycosidic bonds in pyranose and furanose form. The sites of linkage between two saccharide residues are also different.

Alkyl polyglycosides employed according to the invention can also 20 be prepared by mixing alkyl polyglycosides with alkyl monoglycosides. The latter can be recovered or concentrated from alkyl polyglycosides, for example, according to EP-A ~ 092 355 by means of polar solvents, such as acetone.

25 The degree of glycosidation is expediently determined by means of 1H-NMR.

In comparison with the surfactants employed in cosmetic cleansing compositions, the alkyl polyglycosides count as extremely 30 environmentally tolerable. Thus the degree of biodegradability for the alkyl polyglycosides according to the invention determined by means of purification plants simulation model/DOC
analysis iB 96 + 3%. This figure is to be seen from the background that in this test method (total degradation) a degree 35 of degradation of >70~ means that the substance counts as readily degradable.

Even the acute oral toxicity LD 50 (rats) and the aquatic toxicity LC 50 (golden orfe) and EC 50 (daphnia) values of 40 >10,000 mg/kg, 12 and 30 mg/l are more favorable by a factor of 3 to 5 than the corresponding values for the most important surfactants today. The same applies to the skin and mucous membrane tolerability, which is particularly important in cosmetic formulations.
g5 - 219?11 1 Salts such as, for example, alkali metal, ammonium and/or alkaline earth metal halides, sulfates or phosphates can additionally be added in small amounts to the preparations according to the invention.

The preparations according to the invention surprisingly also have a good viscosity when no anionic surfactants are added.

In a known manner, the aqueous preparations according to the 10 invention can contain further component8 which are important for the particular intended u8e. Those suitable are 8ilicone surfactants, protein hydrolyzates, fragrances, opacifying and pearl luster agents, refatting agents, silicone oils, moisturizing agents, pre~ervatives, skin cosmetic active 15 ingredients, plant extracts, buffer substances, complexing agents, etc.

Examples 20 Example 1 Thickening of a shampoo base with sodium lauryl ether sulfate (containing about 2 mol of EO, about 28% active substance in H2O) (Texapon~ N 28) and lauryl polyglucose (based on Cl2-Cl6-fatty 25 alcohol, having a value for m of 1.4-1.45) (Plantaren~ 1200) Recipe (% by weight):
22.0 Texapon~ N 28 16.0 Plantaren~ 1200 0.62 citric acid 10%
0.5 thickener of the formula III
water to 100.0 N- C t ~ - C2H4 t O - Cl8H37 Cl8H37 - ~t-C2H4 - ~ t C - N - ~ CH3 (Lut xal~ HVW) Appearance; pH; Viscosity (Haake VT 02, spindle 2) clear, highly viscous; pH: 6.06; 1500 mPa s - 21q?111 ~ "

Example 2 Thickening of a shampoo base without Texapon~ N 28 5 Recipe ( % by weight ):
30 . O Setacin 103 special (disodium laureth sulfosuccinate) 18 . 0 Plantaren 1200 3 . O amphotenside B 4 ( Cocoamidopropyl betain ) thickener as indicated below 10 Water to 100 . 0 Thickener Appearance; pH; Viscosity (Haake VT 02; spindle 1) + 2% Lutexal HVW clear, highly viscous pH: 5.52 7000 mPa s 15 + 2.0% NaCl clear, liquid; pH: 5.38 400 mPa s (too thin) Example 3 Shampoo base thickened with Lutexal HVW - concentration series Recipe ( % by weight):
2 2 . 0 Texapon0 N 2 8 16 . 0 Plantaren0 1200 0 . 62 citric acid 10%
thickener as indicated below Water to 10 0 . 0 Thickener Ap~,cal~nce; pH; Viscosity (Haake VT 02; spindle 1) after ~ pa.alion: after 24 h RT after 4 days RT
30 + 0.35% Lutexal HVW clear, pH: 6.01, 1400 mPa s clear, 1700 mPa s clear, 1800 mPa s + 0.40~o Lutexal HVW cle~, pH 6.017 2100 rnP~ ~ cleaI, 25~ûQ mPa c clear, 2800 mPa s + 0.50% Lutexal I~VW clear, pH[: 5.94, 4200 mPa s clear, 5000 mPa s clear, 5000 mPa s + 0.60% Lutexal HVW clear, pH: 5.97, 8500 mPa s clear, 9500 mPa s clear, 9500 mPa s

Claims (8)

1. An aqueous preparation, comprising an alkyl polyglycoside and a polyethylene glycol ether derivative of the formula I
I
where R1 is alkyl having 8-22 carbon atoms A is a divalent radical derived from a diisocyanate and n is 20 - 400.
2. A preparation as claimed in claim 1, wherein the preparations are cosmetic compositions.
3. A preparation as claimed in claim 2, wherein the cosmetic compositions are hair treatment compositions, shower baths or shower gels.
4. A preparation as claimed in claim 1, which additionally comprises a surfactant.
5. A preparation as claimed in claim 1, which additionally comprises alkyl polyglycosides of the following formula II

R2-O-Gm II

where R2 is a linear or branched alkyl radical having 8 to 18 C
atoms or mixtures thereof, G is a polyglycosyl radical and m is 1.1 - 5.
6. A preparation as claimed in claim 1, wherein, in formula I

R1 is alkyl having 10-20 C atoms, A is a divalent radical derived from an aromatic diisocyanate and n is 60 - 300.
7. A preparation as claimed in claim 5, wherein, in formula II

R2 is a linear alkyl radical having 10-16 C atoms and n is 1.1 to 2.5.
8. A preparation as claimed in claim 1, which comprises 1 to 20% by weight of alkyl polyglycoside and 0.05 to 1% by weight of polyethylene glycol ether derivative of the formula I.
CA002197111A 1996-02-08 1997-02-07 Aqueous preparations, comprising alkyl polyglycosides and a polymer Abandoned CA2197111A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19604466.9 1996-02-08
DE19604466A DE19604466A1 (en) 1996-02-08 1996-02-08 Aqueous preparations containing alkyl polyglycosides and a polymer

Publications (1)

Publication Number Publication Date
CA2197111A1 true CA2197111A1 (en) 1997-08-09

Family

ID=7784776

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002197111A Abandoned CA2197111A1 (en) 1996-02-08 1997-02-07 Aqueous preparations, comprising alkyl polyglycosides and a polymer

Country Status (5)

Country Link
US (1) US5756078A (en)
EP (1) EP0787486A1 (en)
JP (1) JPH09227335A (en)
CA (1) CA2197111A1 (en)
DE (1) DE19604466A1 (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19859911A1 (en) 1998-12-23 2000-06-29 Basf Ag Process for the preparation of surfactant alcohols and surfactant alcohol ethers, the products produced and their use
DE19910370A1 (en) * 1999-03-09 2000-09-14 Basf Ag Process for the preparation of surfactant alcohols and surfactant alcohol ethers, the products produced and their use
DE19912418A1 (en) 1999-03-19 2000-09-21 Basf Ag Process for the preparation of surfactant alcohols and surfactant alcohol ethers, the products produced and their use
DK1294478T3 (en) * 2000-06-05 2006-05-15 Syngenta Ltd New emulsions
US6998372B2 (en) * 2001-08-16 2006-02-14 J&J Consumer Companies, Inc. Moisturizing detergent compositions
DE102004031786A1 (en) 2004-07-01 2006-01-26 Cognis Deutschland Gmbh & Co. Kg Polyurethane-based thickener
US8933134B2 (en) 2010-06-09 2015-01-13 L'oreal Compositions containing agar and a softening agent

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2054885B2 (en) * 1970-11-07 1976-05-13 Basf Ag, 6700 Ludwigshafen PIGMENT PRINTING PASTE
ES2084591T3 (en) * 1988-08-04 1996-05-16 Kao Corp DETERGENT COMPOSITION.
DE4114141A1 (en) * 1991-04-30 1992-11-05 Huels Chemische Werke Ag AQUEOUS SURFACTANT PREPARATIONS WITH INCREASED VISCOSITY
DE4114220A1 (en) * 1991-05-01 1992-11-05 Bayer Ag MOISTURIZABLE, NCO POLYURETHANE MELT ADHESIVE COMPOSITION
DE9110351U1 (en) * 1991-08-22 1992-12-24 Goldwell Ag, 6100 Darmstadt, De
FR2687069B1 (en) * 1992-02-07 1995-06-09 Oreal COSMETIC COMPOSITION CONTAINING AT LEAST ONE SURFACTANT AGENT OF THE ALKYLPOLYGLYCOSIDE AND / OR POLYGLYCEROLE TYPE AND AT LEAST ONE URETHANE POLYETHER.
CA2161431A1 (en) * 1993-05-21 1994-12-08 Barry A. Salka Mild shampoo composition

Also Published As

Publication number Publication date
DE19604466A1 (en) 1997-08-14
EP0787486A1 (en) 1997-08-06
US5756078A (en) 1998-05-26
JPH09227335A (en) 1997-09-02

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Legal Events

Date Code Title Description
FZDE Discontinued