AU6331899A - Cosmetic preparations - Google Patents

Cosmetic preparations Download PDF

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Publication number
AU6331899A
AU6331899A AU63318/99A AU6331899A AU6331899A AU 6331899 A AU6331899 A AU 6331899A AU 63318/99 A AU63318/99 A AU 63318/99A AU 6331899 A AU6331899 A AU 6331899A AU 6331899 A AU6331899 A AU 6331899A
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AU
Australia
Prior art keywords
alcohols
carbon atoms
esters
fatty
acid
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
AU63318/99A
Inventor
Corinne Chazaly
Thomas Otto Gassenmeier
Bettina Jackwerth
Esther Prat Queralt
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BASF Personal Care and Nutrition GmbH
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Cognis Deutschland GmbH and Co KG
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Filing date
Publication date
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Publication of AU6331899A publication Critical patent/AU6331899A/en
Abandoned legal-status Critical Current

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    • 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • 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
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • 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
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/45Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • A61K8/92Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • 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
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/02Preparations for cleaning the hair

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)

Description

WO 00/21502 1 PCT/EP99/07273 Cosmetic Preparations Field of the Invention This invention relates generally to cationic surfactants and, more particularly, to oil-containing cosmetic preparations containing special esterquats and lower alcohols. 5 Prior Art Cationic surfactants of the esterquat type have been used for some time for hair conditioning cosmetics. By virtue of their favourable sensorial properties, these compounds are also being increasingly used in skin 10 cosmetics. However, cosmetic emulsions containing known esterquats as conditioning agents or cationic emulsifiers, are not entirely satisfactory from the performance point of view. For example consumers complain that the emulsions leave an oily residue behind, do not spread quickly enough and should be absorbed more quickly. 15 Reference is made in this connection to German patent DE-C1 4308794 (Henkel) which describes a process for the production of solid esterquats in which the quaternization of triethanolamine esters is carried out in the presence of suitable dispersants, preferably fatty alcohols. In addition, according to DE-C1 4335782 (Henkel), the quaternization of 20 triethanolamine fatty acid esters is carried out in the presence of polyols, for example glycerol, ethylene glycol, partial glycerides and the like, in order to avoid the use of inflammable isopropyl alcohol as solvent. Accordingly, the problem addressed by the present invention was to provide oil-containing cosmetic preparations containing cationic surfactants 25 of the esterquat type which would be distinguished by improved sensorial properties and, in particular, by quick spreading and rapid residue-free absorption.
WO 00/21502 2 PCT/EP99/07273 Description of the Invention The present invention relates to cosmetic preparations containing (a) esterquats of which the ester groups derive from C 8 -1 8 cocofatty acids, 5 (b) oil components and (c) alcohols containing 1 to 6 carbon atoms. It has surprisingly been found that oil-containing cosmetic preparations, more especially skin-care and hair-care emulsions, which 10 contain esterquats based on technical cocofatty acids together with lower alcohols, preferably propylene glycol, provide the skin and the hair with a particularly pleasant feel, do not leave any residues behind, spread quickly and are rapidly absorbed. Accordingly, these preparations are clearly superior to preparations containing conventional esterquats which are 15 produced mainly from relatively long-chain palm oil and tallow fatty acids. Esterquats "Esterquats" are generally understood to be quaternized fatty acid triethanolamine ester salts. These are known substances which may be 20 obtained by the relevant methods of preparative organic chemistry, cf. International patent application WO 91101295 (Henkel). According to this document, triethanolamine is partly esterified with fatty acids in the presence of hypophosphorous acid, air is passed through and the reaction product is quaternized with dimethyl sulfate or ethylene oxide. Overviews 25 on this subject have been published, for example, by R. Puchta et al. in Tens. Surf. Det., 30, 186 (1993), by M. Brock in Tens. Surf, Det. 30, 394 (1993), by R. Lagerman et al. in J. Am. Oil. Chem. Soc., 71, 97 (1994) and by I. Shapiro in Cosm. Toil, 109, 77 (1994). The esterquats which form component (a) correspond, for example, 30 to formula (1): WO 00/21502 3 PCT/EP99/07273 R 4
[R
1
CO-(OCH
2
CH
2 )mOCH 2
CH
2
-N*-CH
2
CH
2 0-(CH 2
CH
2 0)nR2]X- (1) 5 CH 2
CH
2
O(CH
2
CH
2
O),R
3 in which R 1 CO is a cocoacyl group containing 8 to 18 carbon atoms and preferably 12 to 18 carbon atoms, R 2 and R 3 independently of one another represent hydrogen or have the same meaning as R'CO, R 4 is an alkyl 10 group containing 1 to 4 carbon atoms or a (CH 2
CH
2 O)qH group, m, n and p together stand for 0 or numbers of 1 to 12, q is a number of 1 to 12 and X is halide, alkyl sulfate or alkyl phosphate. To produce the quaternized esters, the cocofatty acids and the triethanolamine may be used in a molar ratio of 1.1:1 to 3:1. With the performance properties of the esterquats in 15 mind, a ratio of 1.2:1 to 2.2:1 and preferably 1.5:1 to 1.9:1 has proved to be particularly advantageous. The preferred esterquats are technical mixtures of mono-, di- and triesters with an average degree of esterification of 1.5 to 1.9 and are derived from technical C 1 2 18 cocofatty acid (iodine value 0 to 40). In performance terms, quaternized fatty acid triethanolamine ester 20 salts corresponding to formula (1), in which R 1 CO is a cocoacyl group containing 12 to 18 carbon atoms, R 2 has the same meaning as R'CO, R 3 is hydrogen, R 4 is a methyl group, m, n and p stand for 0 and X stands for methyl sulfate, have proved to be particularly advantageous. Another group of suitable esterquats are quaternized ester salts of 25 cocofatty acids with diethanolalkyamines corresponding to formula (II): WO 00/21502 4 PCT/EP99/07273 R 4
[R
1
CO-(OCH
2
CH
2 )mOCH 2
CH
2
-N*-CH
2
CH
2 0-(CH 2
CH
2 O)nR 2 ]X- (Il) 5 R in which R 1 CO is a cocoacyl group containing 8 to 18 carbon atoms and preferably 12 to 18 carbon atoms, R 2 is hydrogen or has the same meaning as R 1 CO, R 4 and R 5 independently of one another are alkyl groups 10 containing 1 to 4 carbon atoms, m and n together stand for 0 or numbers of I to 12 and X stands for halide, alkyl sulfate or alkyl phosphate. Finally, another group of suitable esterquats are the quaternized ester salts of cocofatty acids with 1,2-dihydroxypropyl dialkylamines corresponding to formula (Ill): 15
R
6 0-(CH 2
CH
2 O)mOCR' I I
[R
4
-N*-CH
2
CHCH
2 0-(CH 2
CH
2 0)nR2]X- (Ill) 20 R7 in which R 1 CO is a cocoacyl group containing 8 to 18 carbon atoms and preferably 12 to 18 carbon atoms, R 2 is hydrogen or has the same meaning as R 1 CO, R 4 , R 6 and R 7 independently of one another are alkyl groups 25 containing 1 to 4 carbon atoms, m and n together stand for 0 or numbers of 1 to 12 and X stands for halide, alkyl sulfate or alkyl phosphate. So far as the choice of the optimum degree of esterification is concerned, the examples mentioned in regard to (1) also apply to the esterquats of formulae (II) and (Ill). 30 Oil components Suitable oil components are, for example, Guerbet alcohols based on fatty alcohols containing 6 to 18 and preferably 8 to 10 carbon atoms, WO 00/21502 5 PCT/EP99/07273 esters of linear C 6
-
22 fatty acids with linear C 6 -22 fatty alcohols, esters of branched C- 1 3 carboxylic acids with linear Co- 22 fatty alcohols, esters of linear C,-22 fatty acids with branched alcohols, more particularly 2-ethyl hexanol, esters of hydroxycarboxylic acids with linear or branched Cr- 2 2 5 fatty alcohols, more especially Dioctyl Malate, esters of linear and/or branched fatty acids with polyhydric alcohols (for example propylene glycol, dimer diol or trimer triol) and/or Guerbet alcohols, triglycerides based on C 6 10 fatty acids, liquid mono-/di-/triglyceride mixtures based on Co.
1 8 fatty acids, esters of C 6
-
22 fatty alcohols and/or Guerbet alcohols with aromatic 10 carboxylic acids, more particularly benzoic acid, esters of C 2
-
1 2 dicarboxylic acids with linear or branched alcohols containing 1 to 22 carbon atoms or polyols containing 2 to 10 carbon atoms and 2 to 6 hydroxyl groups, vegetable oils, branched primary alcohols, substituted cyclohexanes, linear and branched C 6
-
22 fatty alcohol carbonates, Guerbet carbonates, esters of 15 benzoic acid with linear and/or branched C6- 22 alcohols (for example Finsolv@ TN), linear or branched, symmetrical or nonsymmetrical dialkyl ethers containing 6 to 22 carbon atoms per alkyl group, ring opening products of epoxidized fatty acid esters with polyols, silicone oils and/or aliphatic or naphthenic hydrocarbons. 20 Alcohols The choice of the alcohols is governed by their compatibility in cosmetic preparations. Accordingly, ethanol, ethylene glycol and, in particular, propylene glycol are preferably used. In one preferred 25 embodiment of the invention, technical mixtures of the cocoesterquats with the alcohols are used. To this end, alkanolamine fatty acid esters are reacted with alkylating agents in the presence of such quantities of ethanol, ethylene glycol, propylene glycol, glycerol or mixtures thereof that a ratio by weight of esterquat to solvent of 95:5 to 75:25 and preferably 90:10 to 30 80:20 is obtained. From the applicational point of view, it is preferred to WO 00/21502 6 PCT/EP99/07273 use propylene glycol and mixtures of ethanol and propylene glycol in a ratio by weight of 10:90 to 90:10 and, more particularly, 75:25 to 25:75. The esterification and quaternization may be carried out in known manner, as fully described, for example, in DE-C1 4308794 and DE-C1 4335782 5 (Henkel). The particular advantage of using such mixtures is that they are crystal-clear, even in concentrated form, and can be incorporated cold. Cosmetic preparations As mentioned at the beginning, the cosmetic preparations according 10 to the present invention are normally emulsions which may be both w/o and o/w emulsions; multiple emulsions of the w/o/w or o/w/o type are also suitable. In one preferred embodiment of the invention, the preparations may have the following composition: 15 (a) 0.1 to 25, preferably 5 to 15% by weight of cocoesterquats, (b) 0.5 to 90, preferably 5 to 50% by weight of oil components and (c) 0.01 to 10, preferably 0.1 to 1% by weight of alcohols, with the proviso that the quantities shown add up to 100% by weight with 20 water and optionally other ingredients. In one particularly preferred embodiment, components (a) and (b) are used in a ratio by weight of 80:20 to 90:10. Commercial Applications 25 The preparations according to the invention, for example hair aftertreatments, hair conditioners, hair coloring emulsions, body washes and body-care products, sun protection crreams, lotions and ointments and make-up and other decorative cosmetic products, may also contain mild surfactants, emulsifiers, superfatting agents, pearlescing waxes, stabilizers, 30 consistency factors, thickeners, polymers, silicone compounds, biogenic WO 00/21502 7 PCT/EP99/07273 agents, deodorants, antidandruff agents, film farmers, preservatives, hydrotropes, solubilizers, UV protection factors, antioxidants, insect repellents, self-tanning agents, perfume oils, dyes and the like as further auxiliaries and additives. 5 Typical examples of suitable mild, i.e. particularly dermatologically compatible, surfactants are fatty alcohol polyglycol ether sulfates, monoglyceride sulfates, mono- and/or dialkyl sulfosuccinates, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, fatty acid glutamates, ether carboxylic acids, alkyl oligoglucosides, fatty acid 10 glucamides and/or protein fatty acid condensates, preferably based on wheat proteins. Suitable emulsifiers are, for example, nonionic surfactants from at least one of the following groups: 15 (1) products of the addition of 2 to 30 mol of ethylene oxide and/or 0 to 5 mol of propylene oxide onto linear fatty alcohols containing 8 to 22 carbon atoms, onto fatty acids containing 12 to 22 carbon atoms and onto alkylphenols containing 8 to 15 carbon atoms in the alkyl group; (2) C12/18 fatty acid monoesters and diesters of products of the addition of 20 1 to 30 mol of ethylene oxide onto glycerol; (3) glycerol monoesters and diesters and sorbitan monoesters and diesters of saturated and unsaturated fatty acids containing 6 to 22 carbon atoms and ethylene oxide adducts thereof; (4) alkyl mono- and oligoglycosides containing 8 to 22 carbon atoms in 25 the alkyl group and ethoxylated analogs thereof; (5) adducts of 15 to 60 mol of ethylene oxide with castor oil and/or hydrogenated castor oil; (6) polyol esters and, in particular, polyglycerol esters such as, for example, polyglycerol polyricinoleate, polyglycerol poly-1 2-hydroxy 30 stearate and polyglycerol dimerate. Mixtures of compounds from WO 00/21502 8 PCT/EP99/07273 several of these classes are also suitable; (7) products of the addition of 2 to 15 mol of ethylene oxide onto castor oil and/or hydrogenated castor oil; (8) partial esters based on linear, branched, unsaturated or saturated 5 C 6
/
22 fatty acids, ricinoleic acid and 12-hydroxystearic acid and glycerol, polyglycerol, pentaerythritol, dipentaerythritol, sugar alcohols (for example sorbitol), alkyl glucosides (for example methyl glucoside, butyl glucoside, lauryl glucoside) and polyglucosides (for example cellulose); 10 (9) mono-, di- and trialkyl phosphates and mono-, di- and/or tri-PEG-alkyl phosphates and salts thereof; (10) wool wax alcohols; (11) polysiloxane/polyakyl polyether copolymers and corresponding derivatives; 15 (12) mixed esters of pentaerythritol, fatty acids, citric acid and fatty alcohol according to DE-PS 1165574 and/or mixed esters of fatty acids containing 6 to 22 carbon atoms, methyl glucose and polyols, preferably glycerol or polyglycerol, and (13) polyalkylene glycols. 20 The addition products of ethylene oxide and/or propylene oxide with fatty alcohols, fatty acids, glycerol monoesters and diesters and sorbitan monoesters and diesters of fatty acids or with castor oil are known commercially available products. They are homolog mixtures of which the 25 average degree of alkoxylation corresponds to the ratio between the quantities of ethylene oxide and/or propylene oxide and substrate with which the addition reaction is carried out. C 1 2/ 1 s fatty acid monoesters and diesters of adducts of ethylene oxide with glycerol are known as refatting agents for cosmetic formulations from DE-PS 20 24 051. 30 C 8 /18 alkyl mono- and oligoglycosides, their production and their use WO 00/21502 9 PCT/EP99/07273 are known from the prior art. They are produced in particular by reacting glucose or oligosaccharides with primary alcohols containing 8 to 18 carbon atoms. So far as the glucoside unit is concerned, both monoglycosides in which a cyclic sugar unit is attached to the fatty alcohol 5 by a glycoside bond and oligomeric glycosides with a degree of oligomerization of preferably up to about 8 are suitable. The degree of oligomerization is a statistical mean value on which the homolog distribution typical of such technical products is based. Other suitable emulsifiers are zwitterionic surfactants. Zwitterionic 10 surfactants are surface-active compounds which contain at least one quaternary ammonium group and at least one carboxylate and one sulfonate group in the molecule. Particularly suitable zwitterionic surfactants are the so-called betaines, such as the N-alkyl-N,N-dimethyl ammonium glycinates, for example cocoalkyl dimethyl ammonium 15 glycinate, N-acylaminopropyl-N,N-dimethyl ammonium glycinates, for example cocoacylaminopropyl dimethyl ammonium glycinate, and 2-alkyl 3-carboxymethyl-3-hydroxyethyl imidazolines containing 8 to 18 carbon atoms in the alkyl or acyl group and cocoacylaminoethyl hydroxyethyl carboxymethyl glycinate. The fatty acid amide derivative known under the 20 CTFA name of Cocamidopropyl Betaine is particularly preferred. Ampholytic surfactants are also suitable emulsifiers. Ampholytic surfac tants are surface-active compounds which, in addition to a C 8 /1 8 alkyl or acyl group, contain at least one free amino group and at least one -COOH or -SO 3 H- group in the molecule and which are capable of forming inner 25 salts. Examples of suitable ampholytic surfactants are N-alkyl glycines, N alkyl propionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropy glycines, N-alkyl taurines, N-alkyl sarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids containing around 8 to 18 carbon atoms in the alkyl group. Particularly 30 preferred ampholytic surfactants are N-cocoalkylaminopropionate, WO 00/21502 10 PCT/EP99/07273 cocoacylaminoethyl aminopropionate and C 1 2 18 acyl sarcosine. Besides ampholytic emulsifiers, quaternary emlsifiers may also be used, those of the esterquat type, preferably methyl-quaternized difatty acid triethanolamine ester salts, being particularly preferred. 5 Superfatting agents may be selected from such substances as, for example, lanolin and lecithin and also polyethoxylated or acylated lanolin and lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides, the fatty acid alkanolamides also serving as foam stabilizers. 10 Suitable pearlescing waxes are, for example, alkylene glycol esters, especially ethylene glycol distearate; fatty acid alkanolamides, especially cocofatty acid diethanolamide; partial glycerides, especially stearic acid monoglyceride; esters of polybasic, optionally hydroxy substituted carboxylic acids with fatty alcohols containing 6 to 22 carbon 15 atoms, especially long-chain esters of tartaric acid; fatty compounds, such as for example fatty alcohols, fatty ketones, fatty aldehydes, fatty ethers and fatty carbonates which contain in all at least 24 carbon atoms, especially laurone and distearylether; fatty acids, such as stearic acid, hydroxystearic acid or behenic acid, ring opening products of olefin 20 epoxides containing 12 to 22 carbon atoms with fatty alcohols containing 12 to 22 carbon atoms and/or polyols containing 2 to 15 carbon atoms and 2 to 10 hydroxyl groups and mixtures thereof. The consistency factors mainly used are fatty alcohols or hydroxyfatty alcohols containing 12 to 22 and preferably 16 to 18 carbon 25 atoms and also partial glycerides, fatty acids or hydroxyfatty acids. A combination of these substances with alkyl oligoglucosides and/or fatty acid N-methyl glucamides of the same chain length and/or polyglycerol poly-12-hydroxystearates is preferably used. Suitable thickeners are, for example, polysaccharides, more especially xanthan gum, guar-guar, agar 30 agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl WO 00/21502 11 PCT/EP99/07273 cellulose, also relatively high molecular weight polyethylene glycol mono esters and diesters of fatty acids, polyacrylates (for example Carbopols@ [Goodrich] or Synthalens@ [Sigma]), polyacrylamides, polyvinyl alcohol and polyvinyl pyrrolidone, surfactants such as, for example, ethoxylated fatty 5 acid glycerides, esters of fatty acids with polyols, for example pentaerythritol or trimethylol propane, narrow-range fatty alcohol ethox ylates or alkyl oligoglucosides and electrolytes, such as sodium chloride and ammonium chloride. Suitable cationic polymers are, for example, cationic cellulose 10 derivatives such as, for example, the quaternized hydroxyethyl cellulose obtainable from Amerchol under the name of Polymer JR 400@, cationic starch, copolymers of diallyl ammonium salts and acrylamides, quaternized vinyl pyrrolidone/vinyl imidazole polymers such as, for example, Luviquat@ (BASF), condensation products of polyglycols and amines, quaternized 15 collagen polypeptides such as, for example, Lauryldimonium Hy droxypropyl Hydrolyzed Collagen (Lamequat@ L, Granau), quatemized wheat polypeptides, polyethyleneimine, cationic silicone polymers such as, for example, Amodimethicone, copolymers of adipic acid and dimethyl aminohydroxypropyl diethylenetriamine (Cartaretine@, Sandoz), copoly 20 mers of acrylic acid with dimethyl diallyl ammonium chloride (Merquat@ 550, Chemviron), polyaminopolyamides as described, for example, in FR-A 2 252 840 and crosslinked water-soluble polymers thereof, cationic chitin derivatives such as, for example, quaternized chitosan, optionally in micro crystalline distribution, condensation products of dihaloalkyls, for example 25 dibromobutane, with bis-dialkylamines, for example bis-dimethylamino-1,3 propane, cationic guar gum such as, for example, Jaguar@CBS, Jaguar@C-17, Jaguar@C-16 of Celanese, quaternized ammonium salt polymers such as, for example, Mirapol@ A-15, Mirapol@ AD-1, Mirapol@ AZ-1 of Miranol. 30 Suitable anionic, zwitterionic, amphoteric and nonionic WO 00/21502 12 PCT/EP99/07273 polymers are, for example, vinyl acetate/crotonic acid copolymers, vinyl pyrrolidone/vinyl acrylate copolymers, vinyl acetate/butyl maleate/isobornyl acrylate copolymers, methyl vinylether/maleic anhydride copolymers and esters thereof, uncrosslinked and polyol-crosslinked polyacrylic acids, 5 acrylamidopropyl trimethylammonium chloride/acrylate copolymers, octylacrylamide/methyl methacrylate/tert.-butylaminoethy methacrylate/2 hydroxypropyl methacrylate copolymers, polyvinyl pyrrolidone, vinyl pyrrolidone/vinyl acetate copolymers, vinyl pyrrolidone/dimethylaminoethyl methacrylate/vinyl caprolactam terpolymers and optionally derivatized 10 cellulose ethers and silicones. Suitable silicone compounds are, for example, dimethyl polysilox anes, methylphenyl polysiloxanes, cyclic silicones and amino-, fatty acid-, alcohol-, polyether-, epoxy-, fluorine-, glycoside- and/or alkyl-modified silicone compounds which may be both liquid and resin-like at room 15 temperature. A detailed overview of suitable volatile silicones can be found in Todd et al. in Cosm. Toil. 91, 27 (1976). Typical examples of fats are glycerides while suitable waxes are inter alia beeswax, camauba wax, candelilla wax, montan wax, paraffin wax or microwaxes, optionally in combination with hydrophilic waxes, for 20 example cetyl stearyl alcohol or partial glycerides. Metal salts of fatty acids such as, for example, magnesium, aluminium and/or zinc stearate or ricinoleate may be used as stabilizers. In the context of the invention, biogenic agents are, for example, tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, 25 deoxyribonucleic acid, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides, pseudoceramides, essential oils, plant extracts and vitamin complexes. Suitable deodorizers are, for example, antiperspirants, such as aluminium chlorohydrates. These antiperspirants are colorless 30 hygroscopic crystals which readily deliquesce in air and which accumulate WO 00/21502 13 PCT/EP99/07273 when aqueous aluminium chloride solutions are concentrated by evaporation. Aluminium chlorohydrate is used for the production of perspiration-inhibiting and deodorizing formulations and probably acts by partially blocking the sweat glands through the precipitation of proteins 5 and/or polysaccharides [cf. J. Soc. Cosm. Chem. 24, 281 (1973)]. For example, an aluminium chlorohydrate which corresponds to the formula [Al 2
(OH)
5 Cl]-2.5H 2 0 and which is particularly preferred for the purposes of the invention is commercially available under the name of Locron@ from Hoechst AG of Frankfurt, FRG [cf. J. Pharm. Pharmcol. 26, 531 (1975)]. 10 Besides the chlorohydrates, aluminium hydroxylactates and acidic aluminium/zirconium salts may also be used. Other suitable deodorizers are esterase inhibitors, preferably trialkyl citrates, such as trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate and, in particular, triethyl citrate (Hydagen@ CAT, Henkel KGaA, Dusseldorf, FRG). Esterase 15 inhibitors inhibit enzyme activity and thus reduce odor formation. The free acid is probably released through the cleavage of the citric acid ester, reducing the pH value of the skin to such an extent that the enzymes are inhibited. Other esterase inhibitors are dicarboxylic acids and esters thereof, for example glutaric acid, glutaric acid monoethyl ester, glutaric 20 acid diethyl ester, adipic acid, adipic acid monoethyl ester, adipic acid diethyl ester, malonic acid and malonic acid diethyl ester, hydroxycarboxylic acids and esters thereof, for example citric acid, malic acid, tartaric acid or tartaric acid diethyl ester. Antibacterial agents which influence the germ flora and destroy or inhibit the growth of perspiration 25 decomposing bacteria, may also be present in stick products. Examples of such antibacterial agents are chitosan, phenoxyethanol and chlorhexidine gluconate. 5-Chloro-2-(2,4-dichlorophenoxy)-phenol, which is marketed under the name of Irgasan@ by Ciba-Geigy of Basel, Switzerland, has also proved to be particularly effective. 30 Suitable antidandruff agents are climbazol, octopirox and zinc WO 00/21502 14 PCT/EP99/07273 pyrithione. Standard film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinyl pyrrolidone, vinyl pyrrolidone/vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, collagen, hyaluronic acid and salts thereof 5 and similar compounds. Suitable swelling agents for aqueous phases are montmorillonites, clays minerals, Pemulen and alkyl-modified Carbopol types (Goodrich). Other suitable polymers and swelling agents can be found in R. Lochhead's review in Cosm. Toil. 108, 95 (1993). UV protection factors in the context of the invention are, for 10 example, organic substances (UV filters) which are liquid or crystalline at room temperature and which are capable of absorbing ultraviolet radiation and of releasing the energy absorbed in the form of longer-wave radiation, for example heat. UV-B filters can be oil-soluble or water-soluble. The following are examples of oil-soluble substances: 15 " 3-benzylidene camphor or 3-benzylidene norcamphor and derivatives thereof, for example 3-(4-methylbenzylidene)-camphor as described in EP-B1 0693471; " 4-aminobenzoic acid derivatives, preferably 4-(dimethylamino)-benzoic 20 acid-2-ethylhexyl ester, 4-(dimethylamino)-benzoic acid-2-octyl ester and 4-(dimethylamino)-benzoic acid amyl ester; " esters of cinnamic acid, preferably 4-methoxycinnamic acid-2-ethylhexyl ester, 4-methoxycinnamic acid propyl ester, 4-methoxycinnamic acid isoamyl ester, 2-cyano-3,3-phenylcinnamic acid-2-ethylhexyl ester 25 (Octocrylene); " esters of salicylic acid, preferably salicylic acid-2-ethylhexyl ester, salicylic acid-4-isopropylbenzyl ester, salicylic acid homomenthyl ester; * derivatives of benzophenone, preferably 2-hydroxy-4-methoxybenzo phenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy 30 4-methoxybenzophenone; WO 00/21502 15 PCT/EP99/07273 " esters of benzalmalonic acid, preferably 4-methoxybenzalmalonic acid di-2-ethylhexyl ester; " triazine derivatives such as, for example, 2,4,6-trianilino-(p-carbo-2' ethyl-1'-hexyloxy)-1,3,5-triazine and Octyl Triazone as described in EP 5 Al 0818450; * propane-1,3-diones such as, for example, 1-(4-tert.butylphenyl)-3-(4' methoxyphenyl)-propane-1,3-dione; " ketotricyclo(5.2.1.0)decane derivatives as described in EP-B1 0694521. 10 Suitable water-soluble substances are * 2-phenylbenzimidazole-5-sulfonic acid and alkali metal, alkaline earth metal, ammonium, alkylammonium, alkanolammonium and glucammonium salts thereof; 15 * sulfonic acid derivatives of benzophenones, preferably 2-hydroxy-4 methoxybenzophenone-5-sulfonic acid and salts thereof; " sulfonic acid derivatives of 3-benzylidene camphor such as, for example, 4-(2-oxo-3-bornylidenemethyl)-benzene sulfonic acid and 2 methyl-5-(2-oxo-3-bornylidene)-sulfonic acid and salts thereof. 20 Typical UV-A filters are, in particular, derivatives of benzoyl methane such as, for example 1-(4'-tert.butylphenyl)-3-(4'-methoxyphenyl)-propane 1,3-dione, 4-tert.butyl-4'-methoxydibenzoy methane (Parsol 1789) or 1 phenyl-3-(4'-isopropylphenyl)-propane-1,3-dione. The UV-A and UV-B 25 filters may of course also be used in the form of mixtures. Besides the soluble substances mentioned, insoluble light-blocking pigments, i.e. finely dispersed metal oxides or salts, for example titanium dioxide, zinc oxide, iron oxide, aluminium oxide, cerium oxide, zirconium oxide, silicates (talcum), barium sulfate and zinc stearate, may also be used for this 30 purpose. The particles should have a mean diameter of less than 100 nm, WO 00/21502 16 PCT/EP99/07273 preferably between 5 and 50 nm and more preferably between 15 and 30 nm. They may be spherical in shape although ellipsoidal particles or other non-spherical particles may also be used. Other suitable UV filters can be found in P. Finkel's review in SOFW-Journal 122, 543 (1996). 5 Besides the two groups of primary sun protection factors mentioned above, secondary sun protection factors of the antioxidant type may also be used. Secondary sun protection factors of the antioxidant type interrupt the photochemical reaction chain which is initiated when UV rays penetrate into the skin. Typical examples are amino acids (for example glycine, 10 histidine, tyrosine, tryptophane) and derivatives thereof, imidazoles (for example urocanic acid) and derivatives thereof, peptides, such as D,L carnosine, D-carnosine, L-carnosine and derivatives thereof (for example anserine), carotinoids, carotenes (for example a-carotene, p-carotene, lycopene) and derivatives thereof, chlorogenic acid and derivatives thereof, 15 liponic acid and derivatives thereof (for example dihydroliponic acid), aurothioglucose, propylthiouracil and other thiols (for example thioredoxine, glutathione, cysteine, cystine, cystamine and glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, y-linoleyl, cholesteryl and glyceryl esters thereof) and their salts, dilaurylthiodipropionate, 20 distearylthiodipropionate, thiodipropionic acid and derivatives thereof (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) and sulfoximine compounds (for example butionine sulfoximines, homocysteine sulfoximine, butionine sulfones, penta-, hexa- and hepta-thionine sulfoximine) in very small compatible dosages (for example pmole to 25 pmole/kg) also (metal) chelators (for example a-hydroxyfatty acids, palmitic acid, phytic acid, lactoferrine), a-hydroxy acids (for example citric acid, lactic acid, malic acid), humic acid, bile acid, bile extracts, bilirubin, biliverdin, EDTA, EGTA and derivatives thereof, unsaturated fatty acids and derivatives thereof (for example y-linolenic acid, linoleic acid, oleic 30 acid), folic acid and derivatives thereof, ubiquinone and ubiquinol and WO 00/21502 17 PCT/EP99/07273 derivatives thereof, vitamin C and derivatives thereof (for example ascorbyl palmitate, Mg ascorbyl phosphate, ascorbyl acetate), tocopherols and derivatives (for example vitamin E acetate), vitamin A and derivatives (vitamin A palmitate) and coniferyl benzoate of benzoin resin, rutinic acid 5 and derivatives thereof, a-glycosyl rutin, ferulic acid, furfurylidene glucitol, carnosine, butyl hydroxytoluene, butyl hydroxyanisole, nordihydroguaiac resin acid, nordihydroguaiaretic acid, trihydroxybutyrophenone, uric acid and derivatives thereof, mannose and derivatives thereof, Superoxid Dismutase, zinc and derivatives thereof (for example ZnO, ZnSO 4 ), 10 selenium and derivatives thereof (for example selenium methionine), stilbenes and derivatives thereof (for example stilbene oxide, trans-stilbene oxide) and derivatives of these active substances suitable for the purposes of the invention (salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids). 15 In addition, hydrotropes, for example ethanol, isopropyl alcohol or polyols, may be used to improve flow behavior. Suitable polyols preferably contain 2 to 15 carbon atoms and at least two hydroxyl groups. Typical examples are e glycerol; 20 * alkylene glycols such as, for example, ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol and poly ethylene glycols with an average molecular weight of 100 to 1000 dalton; * technical oligoglycerol mixtures with a degree of self-condensation of 25 1.5 to 10 such as, for example, technical diglycerol mixtures with a diglycerol content of 40 to 50% by weight; a methylol compounds such as, in particular, trimethylol ethane, trimethylol propane, trimethylol butane, pentaerythritol and dipentaerythritol; 30 * lower alkyl glucosides, particularly those containing 1 to 8 carbon atoms WO 00/21502 18 PCT/EP99/07273 in the alkyl group, for example methyl and butyl glucoside; " sugar alcohols containing 5 to 12 carbon atoms, for example sorbitol or mannitol, " sugars containing 5 to 12 carbon atoms, for example glucose or 5 sucrose; * aminosugars, for example glucamine. Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid and the other 10 classes of compounds listed in Appendix 6, Parts A and B of the Kosmetikverordnung ("Cosmetics Directive"). Suitable insect repellents are N,N-diethyl-m-toluamide, pentane-1,2-diol or Insect Repellent 3535. A suitable self-tanning agent is dihydroxyacetone. Suitable perfume oils are mixtures of natural and synthetic 15 fragrances. Natural fragrances include the extracts of blossoms (lily, lavender, rose, jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, petitgrain), fruits (anise, coriander, caraway, juniper), fruit peel (bergamot, lemon, orange), roots (nutmeg, angelica, celery, cardamon, costus, iris, calmus), woods (pinewood, sandalwood, guaiac wood, 20 cedarwood, rosewood), herbs and grasses (tarragon, lemon grass, sage, thyme), needles and branches (spruce, fir, pine, dwarf pine), resins and balsams (galbanum, elemi, benzoin, myrrh, olibanum, opoponax). Animal raw materials, for example civet and beaver, may also be used. Typical synthetic perfume compounds are products of the ester, ether, aldehyde, 25 ketone, alcohol and hydrocarbon type. Examples of perfume compounds of the ester type are benzyl acetate, phenoxyethyl isobutyrate, p-tert.butyl cyclohexylacetate, linalyl acetate, dimethyl benzyl carbinyl acetate, phenyl ethyl acetate, linalyl benzoate, benzyl formate, ethylmethyl phenyl glycinate, allyl cyclohexyl propionate, styrallyl propionate and benzyl 30 salicylate. Ethers include, for example, benzyl ethyl ether while aldehydes WO 00/21502 19 PCT/EP99/07273 include, for example, the linear alkanals containing 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamen aldehyde, hydroxycitronellal, lilial and bourgeonal. Examples of suitable ketones are the ionones, a-isomethylionone and methyl cedryl ketone. Suitable 5 alcohols are anethol, citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethyl alcohol and terpineol. The hydrocarbons mainly include the terpenes and balsams. However, it is preferred to use mixtures of different perfume compounds which, together, produce an agreeable fragrance. Other suitable perfume oils are essential oils of relatively low volatility 10 which are mostly used as aroma components. Examples are sage oil, camomile oil, clove oil, melissa oil, mint oil, cinnamon leaf oil, lime-blossom oil, juniper berry oil, vetiver oil, olibanum oil, galbanum oil, labolanum oil and lavendin oil. The following are preferably used either individually or in the form of mixtures: bergamot oil, dihydromyrcenol, lilial, lyral, citronellol, 15 phenylethyl alcohol, at-hexylcinnamaldehyde, geraniol, benzyl acetone, cyclamen aldehyde, linalool, Boisambrene Forte, Ambroxan, indole, hedione, sandelice, citrus oil, mandarin oil, orange oil, allylamyl glycolate, cyclovertal, lavendin oil, clary oil, p-damascone, geranium oil bourbon, cyclohexyl salicylate, Vertofix Coeur, Iso-E-Super, Fixolide NP, evernyl, 20 iraldein gamma, phenylacetic acid, geranyl acetate, benzyl acetate, rose oxide, romillate, irotyl and floramate. Suitable dyes are any of the substances suitable and approved for cosmetic purposes as listed, for example, in the publication "Kosmetische FArbemittel" of the Farbstoffkommission der Deutschen Forschungs 25 gemeinschaft, Verlag Chemie, Weinheim, 1984, pages 81 to 106. These dyes are normally used in concentrations of 0.001 to 0.1% by weight, based on the mixture as a whole. The total percentage content of auxiliaries and additives may be from 1 to 50% by weight and is preferably from 5 to 40% by weight, based 30 on the particular composition. The compositions may be produced by WO 00/21502 20 PCT/EP99/07273 standard cold and hot methods and are preferably produced by the phase inversion tempeature method. Examples 5 Production Example 1. 828 g (4 mol) of cocofatty acid and 1.2 g of hypophosphoric acid (50% by weight) were introduced into and heated to 70'C in a 1.5-liter three-necked flask equipped with a stirrer, dropping funnel and distillation head. 363 g (2.4 mol) of triethanolamine were added 10 dropwise in portions at a reduced pressure of 30 mbar and, at the same time, the temperature was increased to 160 0 C. After the addition, the reaction mixture was stirred for 2 h at 2 mbar until no more water of reaction was separated and the acid number had fallen below 5 mg KOH/g. 400 g (0.86 mol) of the ester thus produced were transferred to a second 15 three-necked flask and dissolved in 126 g of propylene glycol at 50 0 C. 104 g (0.83 mol) of dimethyl sulfate were then added dropwise in portions and the mixture was stirred for 4 h at 65 0 C. A low-viscosity solution clear at 20*C containing 80% by weight of esterquat and 20% by weight of propylene glycol was obtained 20 Table 1 below contains a number of formulation examples. Dehyquart L 80 is the mixture obtained in accordance with Production Example H1.
WO 00/21502 21 PCT/EP99/07273 Table 1 Cosmetic preparations (water, preservative to 100% by weight) Texapon@- - - - - 38.0 38.0 25.0 Sodium Laureth Sulfate Texapon@ SB 3 - - - - - - - - 10.0 Disodium Laureth Sulfosuccinate Plantacare@D 818 2.0 - - - - - 7.0 7.0 6.0 Coco Glucosides Plantacare@ PS 10 - - - - - - - - - 16.0 Sodium Laureth Sulfate (and) Coco Glucosides Dehyquart@ L80 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 Dicocoyl Methyl Triethanolammonium Methosulfate (and) Propylene Glycol Dehyton@PK 45 - 10.0 Cocamidopropyl Betaine Emulgade@ PL 68/50 4.0 Cetearyl Glucoside (and) Cetearyl Alcohol Eumulgin@ B2 - 0.8 - 0.8 - 1.0 - - - Ceteareth-20 Eumulgin@VL75 - - 0.8 - 0.8 - - - - Lauryl Glucoside (and) Polyglyceryl-2 Polyhydroxystearate (and) Glycerin Lanette@ O - 2.5 2.5 2.5 3.0 2.5 - - - Cetearyl Alcohol Lameform@O 1.0 - - 1.0 - - - - - Polyglyceryl-3 Isostearate Dehymuls@ PGPH - - - - 1.0 - - - - Polyglyceryl-2 Dipolyhydroxystearate Cutina@ GMS 0.5 0.5 0.5 0.5 0.5 1.0 - - - Glyceryl Stearate Cetlol@ HE - - - - - - - - 1.0 PEG-7 Glyceryl Cocoate Cetiol@ J 600 - - - - - - - - - Oleyl Erucate Cetiol@ OE - 1.0 - - - - - - - Dicaprylyl Ether Cetiol@ PGL - - - - 1.0 - - - - Hexyldecanol (and) Hexyldecyl laurate Cetiol@V 1.0 - - 1.0 - - - - - Decyl Oleate Eutanol@ G - - 1.0 - - 1.0 - - - Octyldodecanol I II Nutrilan@ I 2.3 - - 2.0 - - - - - Hydrolyzed Collagen Lamesoft@ LMG - - - - - - 3.0 2.0 4.0 Glyceryl Laurate (and) Potassium Cocoyl Hydrolyzed Collagen Gluadin@WK 1.0 1.0 1.0 1.0 1.0 1.5 0.5 0.5 0.5 0.5 Sodium Cocoyl Hydrolyzed Wheat Protein Euperlan@ PK 3000 AM - - - - - - - 3.0 5.0 5.0 Glycol Distearate (and) Laureth-4 (and) Cocamidopropyl Betaine Generol@ 122 N - - - - 1.0 1.0 - - - Soja Sterol Copherol@ 12250 - - 0.1 0.1 - - - - - Tocopherol Acetate Arlypon@ F 3.0 3.0 1.0 Laureth-2 Sodium Chloride - - - - - - - 1.5 1.5 WO 00/21502 22 PCT/EP99/07273 Table 1 Cosmetic preparations (water, preservative to 100% by weight) Texapon@ NSO 20.0 20.0 12.4 - 25.0 11.0 - - - Sodium Laureth Sulfate Texpon@ K 14 S - - - - - 11.0 23.0 Sodium Myreth Sulfate Texapon@ SB 3 - - - 7.0 - Disodium Laureth Sulfosuccinate Plantacare@ 818 5.0 5.0 4.0 - - - - - 6.0 4.0 Coco Glucosides Plantacare@ 2000 - - - - 5.0 4.0 - - - Decyl Glucoside Plantacar@ PS 10 - - - 40.0 - - 16.0 17.0 - Sodium Laureth Sulfate (and) Coco Glucosides Dehyquar@ L80 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 Dicocoyl Methyl Triethanolammonium Methosulfate (and) Propylene Glycol Dehyton@PK 45 20.0 20.0 - 8.0 - - - - - 7.0 Cocamidopropyl Betaine Emulgade@ PL 68/50 - - - - - - - - - Cetearyl Glucoside (and) Cetearyl Alcohol Eumulgin@BI - - - - 1.0 - - - - Ceteareth-12 Eumulgin@ B2 - - - 1.0 - - - - - Ceteareth-20 Lameform@ TGI - - - 4.0 - - - - - Polyglyceryl-3 Isostearate Dehymuls@PGPH - - 1.0 - - - - - - Polyglyceryl-2 Dipolyhydroxystearate Monomuls@90-L 12 - - - - - - - - - 1.0 Glyceryl Laurate Cutina@ GMS - - - - - - - - 1.0 Glyceryl Stearate Cetiol@ HE - 0.2 - - - - - - - PEG-7 Glyceryl Cocoate Eutanol@ G - - - 3.0 - - - - - Octyldodecano Nutrilan@ Keratin W - - - - - - - - 2.0 2.0 Hydrolyzed Keratin Nutrilan@ID 1.0 - - - - 2.0 - 2.0 - Hydrolyzed Collagen Lamesoft@ LMG - - - - - - - - 1.0 Glyceryl Laurate (and) Potassium Cocoyl Hydrolyzed Collagen Lamesoft@ 156 - - - - - - - - - 5.0 Hydrogenated Tallow Glyceride (and) Potassium Cocoyl Hydrolyzed Collagen Gluadin@ WK 1.0 1.5 4.0 1.0 3.0 1.0 2.0 2.0 2.0 Sodium Cocoyl Hydrolyzed Wheat Protein Euperlan@ PK 3000 AM 5.0 3.0 4.0 - - - - 3.0 3.0 Glycol Distearate (and) Laureth-4 (and) Cocamidopropyl Betaine Panthenol - - 1.0 - - - - - - Arlypon@ F 2.6 1.6 - 1.0 1.5 - - - - Laureth-2 Sodium Chloride - - - - - 1.6 2.0 2.2 - 3.0 GlycerIn (86% by weight) - 5.0 - - - - - 1.0 3.0 - WO 00/21502 23 PCT/EP99/07273 Table 1 Cosmetic preparations (water, preservative to 100% by weight) Texapon@ NSO 30.0 - 25.0 Sodium Laureth Sulfate Plantacare@ 818 - 10.0 30.0 - 20.0 - - - - Coco Glucosides Plantacare@ PS 10 22.0 - - 22.0 - Sodium Laureth Sulfate (and) Coco Glucosides Dehyquart@ L80 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 Dicocoyl Methyl Triethanolammonium Methosulfate (and) Propyleneglycol Dehyton@PK 45 15.0 10.0 10.0 15.0 20.0 - - - - Cocamidopropyl Betaine Emulgade@ SE - - - - - 5.0 5.0 - 5.0 Glyceryl Stearate (and) Ceteareth 12/20 (and) Cetearyl Alcohol (and) Cetyl Palmitate Eumulgin@ B1 - - 15.0 - - - - - - Ceteareth-12 Eumulgin@ HRE 60 - - - - 5.0 - - - - PEG 60 Hydrogenated Castor Oil Lameform@ TGI - - - - - - - 4.0 Polyglyceryl-3 Isostearate Dehymuls@ PGPH - - 3.8 - - - - - - 4.0 Polyglyceryl-2 Dipolyhydroxystearate Monomuls@90-0 18 - - - - - - - 2.0 - 2.0 Glyceryl Oleate CetioI@ HE 2.0 - - 2.0 5.0 - - - - PEG-7 Glyceryl Cocoate Cetiol@ OE - - - - - - - 5.0 5.0 Dicaprylyl Ether Cetiol@ PGL - - - - - - - 10.0 3.0 10.0 Hexyldecanol (and) Hexyldecyl Laurate Cetio@ SN - - - - - 3.0 3.0 - - Cetearyl Isononanoate Cetiol@V - - - - - 3.0 3.0 - 3.0 Decyl Oleate Myritol@ 318 - - - - - - - 5.0 - 5.0 Coco Caprylate Caprate Melissa oil - - 5.0 - - - - - - Bees Wax - - - - - - - 7.0 - 7.0 Nutrilan@ Keratin W - - - 40.0 60.0 - 60.0 Hydrolyzed Keratin Lamesoft ILMG - 4.0 - - 2.0 - - - - Glyceryl Laurate (and) Potassium Cocoyl Hydrolyzed Collagen Gluadin@ AGP 0.5 0.5 - - - - - - - Hydrolyzed Wheat Gluten Gluadin@ WK 2.0 2.0 4.0 2.0 5.0 - - 5.0 - 5.0 Sodium Cocoyl Hydrolyzed Wheat Protein Euperlan@ PK 3000 AM 5.0 - - 5.0 - - - - - Glycol Distearate (and) Laureth-4 (and) Cocamidopropyl Betaine Arlypon@ F - - 1.5 - - - - - - Laureth-2 Glycerin (86% by weight) - - - - - 3.0 3.0 5.0 3.0 5.0 WO 00/21502 24 PCT/EP99/07273 Table 1 Cosmetic preparations (water, preservative to 100% by weight) Dehymuls@ PGPH 2.0 3.0 - 5.0 Polyglyceryl-2 Dipolyhydroxystearate LameformO TOI 4.0 1.0 - Polyglyceryl-3 Diisostearate Emulgade@ PL 68/50 - - - - 4.0 3.0 Cetearyl Glucoside (and) Cetearyl Alcohol Eumulgin@ B2 - - - - - 2.0 Ceteareth-20 Tegocare@ PS - - - - - - 4.0 - - Polyglyceryl-3 Methylglucose Distearate Eumulgin VIL 75 - - - - - 3.5 - - 2.5 Polyglyceryl-2 Dipolyhydroxystearate (and) Lauryl Glucoside (and) Glycerin Bees Wax 3.0 2.0 5.0 2.0 - - - - Cutina@ GMS - - - - - 2.0 4.0 - - 4.0 Glyceryl Stearate Lanette@O - - 2.0 - 2.0 4.0 2.0 4.0 4.0 1.0 Cetearyl Alcohol Plantaren@ 818 5.0 - 10.0 - 8.0 6.0 6.0 - 5.0 5.0 Cocoglycerides Dehyquart@g L80 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 Dicocoyl Methyl Triethanolammonium Methosulfate (and) Propylene Glycol Finsolv@ TN - 6.0 - 2.0 - - 3.0 - - 2.0 C12/15 Alkyl Benzoate Dioctyl Carbonate 5.0 4.0 6.0 8.0 6.0 5.0 4.0 3.0 4.0 6.0 Cetlol@ J 600 2.0 - 3.0 5.0 4.0 3.0 3.0 - 5.0 4.0 Oleyl Erucate Cetlol@OE 3.0 - - - - 1.0 - - - Dicapryly Ether Mineral Oil - 4.0 - 4.0 - 2.0 - 1.0 - Cetiol@ PGL - 7.0 3.0 7.0 4.0 - - - 1.0 Hexadecanol (and) Hexyldecyl Laurate Panthenol/Bisabolol 1.2 1.2 1.2 1.2 1.2 1.2 1.2 1.2 1.2 1.2 Copherol@ F 1300 0.5 1.0 1.0 2.0 1.0 1.0 1.0 2.0 0.5 2.0 Tocopherol / Tocopheryl Acetate Neo Hellopan@ Hydro 3.0 - - 3.0 - - 2.0 - 2.0 Sodium Phenylbenzimidazole Sulfonate Neo Heliopan@ 303 - 5.0 - - - 4.0 5.0 - - 10.0 Octocrylene I Neo HeliopanI@BB 1.5 - - 2.0 1.5 - - - 2.0 Benzophenone-3 Neo Heliopan@ E 1000 5.0 - 4.0 - 2.0 2.0 4.0 10.0 - Isoamyl p-Methoxycinnamate Neo Heliopan@ AV 4.0 - 4.0 3.0 2.0 3.0 4.0 - 10.0 2.0 Octyl Methoxycinnamate Uvinol@ T 150 2.0 4.0 3.0 1.0 1.0 1.0 4.0 3.0 3.0 3.0 Octyl Triazone Zinc Oxide - 6.0 6.0 - 4.0 - - - - 5.0 Titanium Dioxide - - - - - - - 5.0 - Glycerin (86% by weight) 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 (1-4) hair rinse, (5-6) conditioner, (7-8) shower bath, (9) shower gel, (10) wash lotion, (11-14) "two-in-one" shower bath, (15-20) shampoo, (21-25) foam bath, (26) soft cream, (27,29) moisturizing emulsion, (28,30) night cream, (31) w/o sun protection cream, (32-34) w/o sun protection lotion, (35,38,40) o/w sun protection lotion, (36,37,39) o/w sun protection cream

Claims (9)

1. Cosmetic preparations containing (a) esterquats of which the ester groups derive from CB.1 8 cocofatty acids, 5 (b) oil components and (c) alcohols containing 1 to 6 carbon atoms.
2. Preparations as claimed in claim 1, characterized in that they contain esterquats corresponding to formula (1): 10 R 4 [R'CO-(OCH 2 CH 2 )mOCH 2 CH 2 -N*-CH 2 CH 2 0-(CH 2 CH 2 O)nR 2 ]X- (I) 15 CH 2 CH 2 O(CH 2 CH 2 0)pR 3 in which R 1 CO is a cocoacyl group containing 8 to 18 carbon atoms, R 2 and R 3 independently of one another represent hydrogen or have the same meaning as R'CO, R 4 is an alkyl group containing 1 to 4 carbon atoms or a 20 (CH 2 CH 2 0)qH group, m, n and p together stand for 0 or numbers of 1 to 12, q is a number of 1 to 12 and X is halide, alkyl sulfate or alkyl phosphate.
3. Preparations as claimed in claim 1, characterized in that they contain esterquats corresponding to formula (II): 25 R4 [RlCO-(OCH 2 CH 2 )mOCH 2 CH 2 -N*-CH 2 CH 2 0-(CH 2 CH 2 O)nR 2 ]X- (II) R 5 30 in which R 1 CO is a cocoacyl group containing 8 to 18 carbon atoms, R 2 is hydrogen or has the same meaning as R'CO, R 4 and R 5 independently of one another are alkyl groups containing 1 to 4 carbon atoms, m and n WO 00/21502 26 PCT/EP99/07273 together stand for 0 or numbers of 1 to 12 and X stands for halide, alkyl sulfate or alkyl phosphate.
4. Preparations as claimed in claim 1, characterized in that they contain esterquats corresponding to formula (1ll): 5 R 6 O-(CH 2 CH 2 O)mOCR I I [R 4 -N*-CH 2 CHCH 2 0-(CH 2 CH 2 O)nR 2 ]X~ (Ill) 10 R7 in which R 1 CO is a cocoacyl group containing 8 to 18 carbon atoms, R 2 is hydrogen or has the same meaning as R 1 CO, R 4 , R 6 and R 7 independently of one another are alkyl groups containing 1 to 4 carbon atoms, m and n 15 together stand for 0 or numbers of 1 to 12 and X stands for halide, alkyl sulfate or alkyl phosphate.
5. Preparations as claimed in at least one of claims 1 to 4, characterized in that they contain oil components selected from the group consisting of Guerbet alcohols based on fatty alcohols containing 6 to 18 20 and preferably 8 to 10 carbon atoms, esters of linear C- 22 fatty acids with linear C 6 - 2 2 fatty alcohols, esters of branched C6- 13 carboxylic acids with linear C 6 - 2 2 fatty alcohols, esters of linear C- 2 2 fatty acids with branched alcohols, more particularly 2-ethyl hexanol, esters of hydroxycarboxylic acids with linear or branched C- 22 fatty alcohols, esters of linear and/or 25 branched fatty acids with polyhydric alcohols and/or Guerbet alcohols, triglycerides based on C6_ 1 0 fatty acids, liquid mono-/di-/triglyceride mixtures based on C6. 1 8 fatty acids, esters of Cr- 22 fatty alcohols and/or Guerbet alcohols with aromatic carboxylic acids, esters of C 2 - 1 2 dicarboxylic acids with linear or branched alcohols containing 1 to 22 carbon atoms or 30 polyols containing 2 to 10 carbon atoms and 2 to 6 hydroxyl groups, vegetable oils, branched primary alcohols, substituted cyclohexanes, linear WO 00/21502 27 PCT/EP99/07273 and branched C 6 - 22 fatty alcohol carbonates, Guerbet carbonates, esters of benzoic acid with linear and/or branched C-22 alcohols, linear or branched, symmetrical or nonsymmetrical dialkyl ethers containing 6 to 22 carbon atoms per alkyl group, ring opening products of epoxidized fatty acid esters 5 with polyols, silicone oils and/or aliphatic or naphthenic hydrocarbons.
6. Preparations as claimed in at least one of claims 1 to 5, characterized in that they contain ethanol, ethylene glycol, propylene glycol and/or glycerol as alcohols.
7. Preparations as claimed in at least one of claims 1 to 6, 10 characterized in that they contain mixtures of esterquats and alcohols directly obtained by alkylation of alkanolamine fatty acid esters in the alcohols.
8. Preparations as claimed in at least one of claims 1 to 7, characterized in that they contain 15 (a) 0.1 to 25% by weight of esterquats (b) 0.5 to 90% by weight of oil components and (c) 0.01 to 10% by weight of alcohols, 20 with the proviso that the quantities shown add up to 100% by weight with water and optionally other ingredients.
9. Preparations as claimed in at least one of claims 1 to 8, characterized in that they contain the esterquats and the alcohols in a ratio by weight of 80:20 to 90:10.
AU63318/99A 1998-10-10 1999-10-01 Cosmetic preparations Abandoned AU6331899A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19846773A DE19846773A1 (en) 1998-10-10 1998-10-10 Cosmetic compositions useful for preparing skin and hair care emulsions comprise a coco esterquat, oil and alcohol
DE19846773 1998-10-10
PCT/EP1999/007273 WO2000021502A1 (en) 1998-10-10 1999-10-01 Cosmetic preparations

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AU6331899A true AU6331899A (en) 2000-05-01

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JP (1) JP2002527373A (en)
KR (1) KR20010087368A (en)
CN (1) CN1323196A (en)
AU (1) AU6331899A (en)
DE (2) DE19846773A1 (en)
ES (1) ES2220119T3 (en)
WO (1) WO2000021502A1 (en)

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DE10021310A1 (en) * 2000-05-02 2001-11-15 Friedrich Schardt Aqueous hair lotion for controlling dandruff and alopecia, containing lactic acid, citric acid, (dex)panthenol, sodium selenite, zinc sulfate and optionally potassium iodate, silicic acid and ascorbic acid
US7152530B2 (en) 2002-12-19 2006-12-26 Heidelberger Druckmaschinen Ag Printing form and method for modifying its wetting properties
JP4756249B2 (en) * 2006-11-07 2011-08-24 山栄化学株式会社 Multi-agent hair cosmetic
DE102007037018A1 (en) 2007-08-06 2009-02-12 Clariant International Ltd. Composition, useful for treating or caring skin and hair, comprises nitro-carbonyl compound and further e.g. monoalcohol, polyol, diethanolamine, fatty acid, silicon substituted compound and nonionic emulsifier
DE102008015899A1 (en) 2008-03-27 2008-10-09 Clariant International Ltd. diethanol-methylamineComposition, useful e.g. as a cosmetic, dermatological or pharmaceutical composition and for treating or maintaining the skin or hair, comprises bis(ethyl-carboxyl)-dimethyl amine compounds
JP4657354B2 (en) 2009-05-28 2011-03-23 株式会社資生堂 Hair cosmetics
JP4627333B2 (en) * 2009-05-28 2011-02-09 株式会社資生堂 Hair cosmetics
CN112218611A (en) * 2018-05-30 2021-01-12 巴斯夫欧洲公司 Wax dispersions with conditioning properties
CN111821216A (en) * 2019-03-29 2020-10-27 阿普切姆有限公司 Liquid thickener composition comprising polyalkoxylated polyol polyester having Guerbet acid moieties
WO2022020332A1 (en) 2020-07-21 2022-01-27 Chembeau LLC Diester cosmetic formulations and uses thereof

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DE19541753C2 (en) * 1995-11-09 1998-07-16 Henkel Kgaa Cosmetic and / or pharmaceutical emulsions
DE19651447C1 (en) * 1996-12-11 1997-10-02 Henkel Kgaa Textile or hair conditioners having improved performance
DE19652300C2 (en) * 1996-12-16 1998-10-08 Henkel Kgaa Use of esterquats as emulsifiers for dihydroxyacetone
DE19652299C2 (en) * 1996-12-16 1998-10-08 Henkel Kgaa Use of ester quats
DE19652302C1 (en) * 1996-12-16 1998-03-26 Henkel Kgaa Stable, homogeneous cosmetic skin care preparation
DE19716070C2 (en) * 1997-04-17 2000-08-24 Cognis Deutschland Gmbh Sunscreen
DE19724868A1 (en) * 1997-06-12 1998-12-24 Henkel Kgaa Stable cosmetic or pharmaceutical preparation, e.g. cream
DE19732015C1 (en) * 1997-07-25 1998-07-23 Henkel Kgaa Self-emulsifying formulation useful in production of cosmetics, e.g. hair conditions
DE19738645C1 (en) * 1997-09-04 1999-07-08 Henkel Kgaa Water-miscible cationic surfactant concentrates
DE19805703C2 (en) * 1998-02-06 2001-05-03 Cognis Deutschland Gmbh Hair care products

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CN1323196A (en) 2001-11-21
EP1117377B1 (en) 2004-04-21
EP1117377A1 (en) 2001-07-25
DE19846773A1 (en) 2000-04-20
WO2000021502A1 (en) 2000-04-20
ES2220119T3 (en) 2004-12-01
KR20010087368A (en) 2001-09-15
JP2002527373A (en) 2002-08-27

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