CA2094935A1 - Oil-in-water emulsions - Google Patents
Oil-in-water emulsionsInfo
- Publication number
- CA2094935A1 CA2094935A1 CA002094935A CA2094935A CA2094935A1 CA 2094935 A1 CA2094935 A1 CA 2094935A1 CA 002094935 A CA002094935 A CA 002094935A CA 2094935 A CA2094935 A CA 2094935A CA 2094935 A1 CA2094935 A1 CA 2094935A1
- Authority
- CA
- Canada
- Prior art keywords
- weight
- alkyl
- emulsions
- oil
- 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
Links
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
- A61K8/062—Oil-in-water emulsions
-
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
- A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
-
- 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
Abstract
Oil-in-water emulsions with one or more water-insoluble oil bodies, water and one or more alkyl glucosides as emulsifiers and an additional content of a fatty acid partial glyceride as a crystallisation inhibitor are distinguished by good storage life. It is furthermore possible, on the basis of alkyl glucosides and fatty acid partial glycerides to formulate emulsifier concentrates which are suitable for the production of long-storage-life oil-in-water emulsions.
Description
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~O 92/075~3 PCT/BP91/01966 Oil-in-wat2r emulsions This invention relates to storable oil-in-~at~r emulsions, hereinafter referred to as o/l/ emulsions, containing alkyl glucosides and a partial glyceride with ~`~ a monoglyceride content of 60 to 95% by .reight ar.d to emulsifier concentrates containing alkyl glucosides, a partial glyceride with a monoglyceride content of 50 to 95% by weight and a long-chain alcohol.
The use of alkyl glucosides in the rield or `~ cosmetics is known from the literature. Thus, in their TRITON CG 110 pamphlet, Rohm & Haas recommend the use of an alkyl glucoside based on octanol/decanol ~50:50) as an auxiliary emulsifier for cosmetic emulsions, for example for skin creams and lotions. Japanese patent application JP 89/203 036 (Shiseido) describes cosmetic emulsions containing a Ca24 glucoside together with a polyol containing at least three hydroxyl groups, for example glycerol, and an oil component. Finally, JP
86/5005 (Yoshitomi Pharm.) Ind. describes the use of alkyl (C8~8) gIucosides as moisturizers, for example in cosmetic creams.
Alkyl glucosides are suitable as emulsifiers for the production of o/w emulsions. It has been found that the alkyl glucosides present in such emulsions have a pronounced tendency to crystallize which cannot be suppressed even by-nonionic, anionic or cationic co-emulsifiers. Macroscopically, crystal growth is reflec-ted in a deterioration in structure. Crystal structures such as these destroy the homogeneous droplet distribu-tion which results in unwanted destabilization and, finally, in breaking of the emulsions. Accordingly, the problem addressed by the present invention was to . .
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~O 92/075~3 PCT/BP91/01966 Oil-in-wat2r emulsions This invention relates to storable oil-in-~at~r emulsions, hereinafter referred to as o/l/ emulsions, containing alkyl glucosides and a partial glyceride with ~`~ a monoglyceride content of 60 to 95% by .reight ar.d to emulsifier concentrates containing alkyl glucosides, a partial glyceride with a monoglyceride content of 50 to 95% by weight and a long-chain alcohol.
The use of alkyl glucosides in the rield or `~ cosmetics is known from the literature. Thus, in their TRITON CG 110 pamphlet, Rohm & Haas recommend the use of an alkyl glucoside based on octanol/decanol ~50:50) as an auxiliary emulsifier for cosmetic emulsions, for example for skin creams and lotions. Japanese patent application JP 89/203 036 (Shiseido) describes cosmetic emulsions containing a Ca24 glucoside together with a polyol containing at least three hydroxyl groups, for example glycerol, and an oil component. Finally, JP
86/5005 (Yoshitomi Pharm.) Ind. describes the use of alkyl (C8~8) gIucosides as moisturizers, for example in cosmetic creams.
Alkyl glucosides are suitable as emulsifiers for the production of o/w emulsions. It has been found that the alkyl glucosides present in such emulsions have a pronounced tendency to crystallize which cannot be suppressed even by-nonionic, anionic or cationic co-emulsifiers. Macroscopically, crystal growth is reflec-ted in a deterioration in structure. Crystal structures such as these destroy the homogeneous droplet distribu-tion which results in unwanted destabilization and, finally, in breaking of the emulsions. Accordingly, the problem addressed by the present invention was to . .
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~O 92/07S~3 2 ~c~/Epsl/ol966 provide storable o/w emulsions containing alkyl glucosi-des.
According to the invention, this problem has been ~; solved by oil-in-water emulsions containing alkyl glucosides, characterized in that they contain (A) one or more water-insoluble oils, (B) as emulsirier, one o-r more alXyl glucosides `l corresponding to the general formula RO(G)X, in which - R is a linear saturated C322 al~yl radical - G is a glucose unit - is a number of 1 to 10, characteri~ed in that thev contain ; 15 (C) a fatty acid partial glyceride with a monoglycer-ide content of 60 to 95% by weight as crystal-lization inhibitor.
In one preferred embodiment of the invention, the emulsions according to the invention contain the water-` insoluble oil (A) in a quantity of 5 to 30% by weight, the alkyl glucoside (B) in a quantity of 2 to 15% by weight and the fatty acid partial glyceride (C) in a quantity of 2 to 20~ by weight.
The o/w emulsions according to the invention show no crystals of alkyl glucosides under a light micro-scope, even with 400x magnification. The emulsions are homogeneous and stable in storage.
Basically, any water-insoluble, linear or branch-ed, physiologically safe aliphat~c hydrocarbons, ethers or esters liquid at room temperature (20~C) may be used ~; as the oil(s) (A). However,, solid or relatively high ; melting paraffins, esters, waxes or fats may also be used.
Particularly suitable oils from the group of , ~.~
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~0 92/07543 3 PCT/~P91/01966 aliphatic hydrocar~ons are, for example, squalane, : squalene, dioctyl cyclohecans, Paraffinum perliquidum and Paraffinum subliquidum and isohexadecane (hydrogena-.~ ted polybutylene~.
Other particularly suitable oils are esters of :; trihydric and more -~han trihydric alcohols, more par-.~ ticularly vPgetable triglycerides, for example olive ` oil, almond oil, peanui oil, sunrlower oil, or even the esters of pen-taerythritol, for example ~ith pelargonic acid or oleic acid.
Other par~icularly suitable oils are monoesters and diesters correspondiny to general formulae Ij II and III
.
(I) ~1-COOR2 (II) R2_ooc-R3-COOR2 -~: (III? Rl_coo-R3-OOC-Rl in which R1 is a C822 alkyl group, RZ is a C32~ alkyl group and R3 represents C216 alkylene groups. These monoesters and diesters contain at least 11 and at most 40 carbon atoms.
Oils of the mono and diester type corresponding : to formulae (I), (II) and (III) are knoT~n as cosmetic and pharmaceutical oil components and as lubricant : components. Among the monoesters and diesters of this type, the products liquid at room temperature (20C) are the most important. Monoesters (I) suitable as oils are, for example, the isopropyl esters of C1222 fatty acids such as, for example, isopropyl myristate, isopro-pyl palmitate, isopropyl stearate, isopropyl oleate.
Other suitable monoesters. are, for example, n-butyl ~; stearate, n-hexyl laurate, n-decyl oleate, isooctyl stearate, isononyl palmitate, isononyl isononanoate, 2-~ 35 ethylhexyl palmitate, 2-ethylhexyl laurate, 2-hexyldecyl ; ~ ' , .
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~0 92/07543 4 PCT/EP91/01966 .
stearate, 2-octyl dodecyl palmitate, oleyl oleate, oleyl erucate, erucyl oleate and esters obtainable from technical allphatic alcohol mixtures and technical aliphatic carboxylic acids, for example esters of saturat2d and unsaturated C12zz fatty alcohols and i saturated and unsaturated C1222 ~atty acids WhiCh are ; obtainable from animal and vegetable fats. Naturally occurring monoester or wax ester mixtures, as present for example in jojoba oil or sperm oil, are also suit-lo able.
Suitable dicarboxylic acid esters (II) are, for example, di-n-butyl adipate, di-n-butyl sebacate, di-(2-ethylhexyl)-adipate, di-(2-hexyldecyl)-succinate and di-~ isotrldecyl azelate. Suitable diol esters (III) are, i~ 15 for example, ethylene glycol dioleate, ethylene glycol diisotridecanoate, propylene glycol di-(2-ethylhexano-ate), propylene glycol diisostearate, propylene glycol dipelargonat~, butanediol diisostearate and neopentyl glycol dicaprylate.
Other suitable oils are branched primary alcohols of the type known as Guerbet alcohols (seer for example, A.J. O~Lenick ~r., R.E. Bilbo, Soap Cosm. Chem. 8pec.
1987, 52), for example 2-hexyl decanol or 2-octyl dodecanol, and esters of Guerbet alcohols with long-chain aliphatic carboxylic acids, for example with stearic acid.
The oils are used in the o/w emulsions according to the invention in a quantity of 5 to 30% by weight ~` and, more particularly, 10 to 20% by welght.
Suitable alkyl glucosides (B) are glucosides . ~
containing a C8z2 alkyl radical. They are normally prepared by reaction of glucose or starch or starch ` ~ syrup with the corresponding long-chain alcohols. The ....
~` alcohols have to be used in excess. On completion of the reaction, the unreacted alcohol is largely distilled ~, .i ~i .
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~0 92/07543 5 2CT/~P91/01966 off, so that the alkyl glucoside used in accordance with i the invention generally has residual alcohol contents of approximately 1% by weight.
Alkyl glucosides are characterized by the general formula ~O(G)~, in which:
- R is a linear saturated C8~2 alkyl radical - G is a glucose unit - x is a number of 1 to 10.
The index x is the degree of oligomerization and repre-sents a mean value for the distribut,ion of monogluco-; sides and oligoglucosides. As a calculated quantity, ; ~he degree of oligomerization says something of the distribution of the chemical individuals present in a technical oligomer mixture which differ from one another in the number of glucose units present per molecule alkyl glucoside. The average degree of oligomerization x should be a value of 1.1 to 1.6.
In another preferred embodiment of the invention, the alkyl radical of the alkyl glucoside has a chain length of 12 to 18 carbon atoms and more particularly 16 to 18 carbon atoms. - Alkyl glucosides containing at least 85% by weight C~6 are particularly suitable. The alXyl glucosides used in accordance with the invention are species of which the alkyl radicals have the prefer-red chain lengths mentioned. However, they may also contain small quantities of species where the alkyl ,, radicals have shorter and/or longer chain lengths, as present for example in the alkyl radicals of fatty alcohols of vegetable and animal origin.
In a particularly preferred embodiment, alkyl glucosides having a degree of oligomerization x of 1.1 to 1.3 are used.
Another preferred embodiment of the present ~:
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invention is characterized in that, in addition to the components described above, it also contains a consis-t~ncy regulator. Consistency regulators are substances which determine or maintain the consistency of cosmetic preparations, for example emulsions (cf. ~. Fey~ I.
Ot~o, ~IWorterbuch dar ~osme~iX", S~uttgar~ 1sa~). Long-chain alcohols, carboxymethyl cellulose or salts of polyacrylic acids, for example, may be used as consis-tency regulators in the o/w emulsions according to the invention. Alcohols containing 14 to 22 carbon atoms and, more particularly, 16 to 18 carbon atoms are par-ticularly suitable as consistency regulators. The con-sistency regulators may advantageously be introduced in the form of the alcohol which is present in the alkyl glucoside after partial removal of the unreacted alcohol by distillation.
The temperatures to which the alkyl glucosides are exposed during removal of the unreacted alcohol by distillation can readily result in unwanted brownish ; 20 discoloration which necessitates a bleaching process.
Accordingly, it can be of advantage not to remove too much of the reacted alcohol, particularly when the long-chain alcohol is in any case to be used as consistency regulator in the o/w emulsion. Accordingly, another embodiment of the present invention is characterized by the use of a crude alkyl glucoside containing 1 to 20%
by weight and preferably 2.5 to S% by weight unreacted alcohol.
The alkyl glucosides are used in the o/w emul-; 30 sions according to the invention in a quantity of 2 to 15% by weight and, more particularly, in a quantity of 2 to 7% by weight.
;~ Fatty acid partial glycerides (C) of saturated or ~` unsaturated C1020 fatty acids are technical mixtures of fatty acid mono-, di- and triglycerides which are .
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RO 92/075~3 7 PCT/EP91/019S6 obtained by esterification of 1 mol glycerol with 1 to 2 mol of a (C1020) fatty acid or by transesterificatlon of 1 mol of a (Cl0-2c) fatty acid triylyceride, for example beef tallow, lard, palm oil, sunflower oil or soybean oil, with 0.5 to ~ mol glycerol.
Two types of partial glycerides are commercially obtainable. Partial glycerides of type I contain 35 to 60% monoglycerides, 35 to 50% diglycerides and 1 to 20%
triglycerides. Partial glycerides OL typ~ II ar~
prepared by molecular distillation from those of type I
and contain 90 to 95% monoglycerides, 1 to 5% diglycer-ides and less than 1% triglycerides (cf.: a) G. 8chustar and W. ~dams: Zeitschrift fur Lebensmitteltechnologie, 1979, Yol. 30 ~61, pagss 256-264; b) G. Schuster ~d.~
"Emulgatoren fur Lebansmittel", Springer-~eralg, 1935).
; The fatty acid partial glycerides used in accord-ance with the invention should contain 60 to 95% mono-glycerides, l to 35~ diglycérides and 0.1 to 5% trigly-cerides. A preferred embodiment of the invention is characterized by the use of fatty acid partial glycer-ides containing 90 to 95% by weight monoglyceride.
Fatty acid partial glycerides of which the fatty acid components contain 16 to 18 carbon atoms are particular-ly favorable.
The fatty acid partial glycerides are used in the o/w emulsions according to the invention in a quantity of 2 to 20% by weight and, more particularly, in a quantity of 4 to 10~ by weight.
In addition, the o/w emulsions according to the invention may contain additional components or auxili-aries known from the prior art. The most important are:
~:, ; a) co-emulsifiers, for example anionic surfactants ;~ containing carboxylate, sulfonate, sulfate or phosphate groups, such as soaps, alkyl and aryl ~: .
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~O 92/~7543 8 PC~/~P91/01966 ether sulfates, fatty amines, quaternary ammonium and pyridinium compounds, nonionic emulsifiers, such as ethylene oxide adducts ~ith alcohols, carboxylic acids, partial glycerides and sorbitan esters, amphoteric emulsifiers, such as imidazo-line derivatives, betaines or sulfobetaines and, for example, fatty acid esters and sorbitan fatty acid esters (cf., for example, 7~ UmDacn ~Bd.3, ~Rosmetik-EntwicXlung, Xerstallung und ~n~2ndung 10 ` ~osmetischer ~ittel", pag2s a~-37, ~tuttgar!-1988).
b) Humectants, for example glycerol, polyylycerols, sorbitol, propane-1,2-diol, butane-1,2,3-triol, polyethylene glycols, glucose, mannitol, ~vlitol.
c) Antimicrobial agents as preservatives, for example benzoic acid, salicylic acid, sorbic acid and esters and salts thereof.
d) Perfume oils, for example natural fragrances obtained by distillation, extraction or pressing from plants and synthetic fragrances (cf., for example, ~. Aebi, ~. Baumgartner, H.P. Fiedler, ~' G. Ohloff, "Rosmetika, Riechstoffe und Le~ens-~ittelzu~atzstoffe", Stuttgart 1978).
e) Antioxidants, for example tocopherols, lecithin, 2S guaiacol, butyl cresol, 4-methyl-2,6-ditert.butyl phenol (BHT), 4-methoxy-2(3)-tert.butyl phenol (BHA) f) Dyes of the type listed for cosmetics, for example, by the Farbstoff Kommission der Deut-; 30 schen Forschungsgemeinschaft ("Farbemittel fur ~osmetika", Mitteilung 3, ~iesbaden 1968).
~. ' ~` To prepare the emulsions, the alkyl glucosides ;;~ are dissolved either in the hot water phase or fatty ~ 35 phase. The water phase is preferably added to the oil : .
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phase with stirring at 60 to 80'C. The dispersions thus obtained are subsequently cooled to 30C. If desired, the structure of the emulsion may be improved during cooling by units opera~ing on the rotor/stator prin-ciple, for example Ultra-Turrax T50 (I1ca-~er'ce).
The o/w emulsions according to ~he invention may also be prepared in the absence of heat by virtue of the solubility of the alkyl glucosides in ~ater, particular-ly those containing C1216 alkyl radicals. Rich liquid or creamv cosmetic emulsions can be rormulated in this way, particularly in combination with hydrophilic or hydro-phobic emulsifiers and oils liquid at room temperature, using polymeric thickeners.
; The present invention relates to emulsifier 15 concentrates for the production of o/w emulsions accord-ing to the invention containing ` (D) 24 to 75% by weight of one or more alkyl gluco-sides corresponding to the general formula RO(G)~, in which - R is a linear saturated C822 alkyl radical - G is a glucose unit - x is a number of 1 to 10 (E) 24 to 75% by weight of a fatty acid partial glyceride containing 60 to 95% by weight monogly-ceride (F) 0.1 to 50% by weight of a linear saturated alcohol containing 14 to 22 carbon atoms and, ~; more particularly, 16 to 18 carbon atoms.
For the reasons mentioned above, the emulsifier concentrates may also be prepared using alkyl glucosides ::
in whose case unreacted alcohol was distilled off only partly, if at all, during the production process. Ac-35 cordingly, a preferred embodiment of the present inven-:
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~O 92/07~3 10 PCT/BP91/01966 tion is characterized in that the emulsifier concentra-tes are preparsd using alkyl glucosides containing from 3 to 90~ by weight and preferably from 3 to 40% by weight unreacted alcohol. In cases such as these, the alkyl glucosides may be mixed ~/ith the fatty acid partial glycerides immedia~ely after the reaction between glucose and long-chain alcohols and, if desired, partial removal of the unreacted alcohol by distillation at temperatures of around 100C. It is possible in this way to produce self-e~Lulslfying emulsion bases with which cosmetically sophisticated creams and lotions can be formulated.
In addition, the emulsifier concentrates accord-ing to th~ lnvention may contain additional components or auxiliaries or ~he type described above, for example oils, co-emulsifiers, hu~ectants, preservatives, perfume oils, antioxidants, dyes.
The ollowing Examples are intended to illustrate the invention.
i E x a m p 1 e .
1. Substances used 1.1 Oil (A) Cetiol V: oleic acid decyl ester (Henkel KGaA, Dusseldorf); Mvritol 318: caprylic/capric acid triglyceride (Henkel KGaA, Dusseldorf) 1.2 Alkyl ~lucosides (B) ~` 30 The alkyl glucosides used were C14~ C1B and C18 alkyl glucosides (abbreviated to AG C14, AG C16 and AG C18) having degrees of oligomerization x of 1.2 to 1.4. The corresponding Cl4, C16 and C18 fatty alcohols were used to prepare the C14, C16 and C18 alkyl glucosides (C chain distribution .
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~O 92~07543 11 PC~/~P91/01966 according to GC: a) for Cl4 fatty alcohol: 2~ Cl2;
96% Cl4; 2% C16; b) for C~6 fatty alcohol: 2% C14;
95~ Cl8; 2% Cl~; c) for Cl~ fatty alcohol: 2% Cl6;
9~-~ Cl3; 2% C20).
, 1.3 Fattv acid partial glYcerides (C) Cu-~ina ~D: fatty acid partial glyceride based on hydrog2nated palm oil with a monoglyceride con-tent of 42% by weight (Grunau, Illertissen);
.lonomuls 60-35: fatty acid partial glyceride based on hydrogenated palm oil with a monoglycer-ide content of 60% by weight (Grunau, Illertis-sen); Monomuls 90-35: fatty acid partial glycer-ide bas2d on hydrogenated palm oil with a mono-glyceride content OL 90% by weight (Grunau, Illertissen) ' 1.4 Other components Lanet~e O: cetyl/stearyl alcohol [50:50] (Henkel KGaA, Dusseldorf); Lanette E: cetyl/stearyl alcohol sulfate, Na salt [50:50] (Henkel KGaA, Dusseldorf); Cutina E-24: polyoxyethylene-24-glycerol monostearate (Henkel KGaA, Dusseldorf).
; 25 2. Production and characterization of the disPer-sions To prepare the emulsions, the alkyl glucosides were dissolved in either the hot water phase or fatty phase. The water phase was preferably added with stirring to the oil phase at 60 to 80C. The disper-sions obtained were then cooled to 30 C.
After 24 hours, the viscosities were measured at . .
; 23C with a Brookfield viscositmeter using spindle E at ; 4 r.p.m. The emulsions were then stored for 2 weeks at ~' 35 -5 C, 20C and 40C and exami.. ed visually and under a ~ .
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microscope (400x magnification). The results are shown in Table 1 according to the composition of the emul-sions.
In every case where Monomuls 90-35 or Monomuls 6--~ 5 35 (monoglycsride content: 90~ or 60~ as used as the partial glyceride, the emulsions obtained were homogen-eous ~oth immediately after preparation and after storage under the conditions described above (Table 1, columns Bl to B~). By contrast, the emulsion obtained using Cutina ~ID, a partial glyceride containing 42%
monoglyceride, was either homogeneous immediately after ` its preparation, but showed distinctly crystalline con-stituents under a light microscope (400x magnification) - and separated lnto two phases at 40OC (Table 1, columns C1 and C2), or was macroscopically inhomogeneous im-mediately after its preparation (Table l, column C3).
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~O 92/07S~3 2 ~c~/Epsl/ol966 provide storable o/w emulsions containing alkyl glucosi-des.
According to the invention, this problem has been ~; solved by oil-in-water emulsions containing alkyl glucosides, characterized in that they contain (A) one or more water-insoluble oils, (B) as emulsirier, one o-r more alXyl glucosides `l corresponding to the general formula RO(G)X, in which - R is a linear saturated C322 al~yl radical - G is a glucose unit - is a number of 1 to 10, characteri~ed in that thev contain ; 15 (C) a fatty acid partial glyceride with a monoglycer-ide content of 60 to 95% by weight as crystal-lization inhibitor.
In one preferred embodiment of the invention, the emulsions according to the invention contain the water-` insoluble oil (A) in a quantity of 5 to 30% by weight, the alkyl glucoside (B) in a quantity of 2 to 15% by weight and the fatty acid partial glyceride (C) in a quantity of 2 to 20~ by weight.
The o/w emulsions according to the invention show no crystals of alkyl glucosides under a light micro-scope, even with 400x magnification. The emulsions are homogeneous and stable in storage.
Basically, any water-insoluble, linear or branch-ed, physiologically safe aliphat~c hydrocarbons, ethers or esters liquid at room temperature (20~C) may be used ~; as the oil(s) (A). However,, solid or relatively high ; melting paraffins, esters, waxes or fats may also be used.
Particularly suitable oils from the group of , ~.~
. . .
.
: .
: ' ' .
~ ~ 9 ~ ~ 2~j~
~0 92/07543 3 PCT/~P91/01966 aliphatic hydrocar~ons are, for example, squalane, : squalene, dioctyl cyclohecans, Paraffinum perliquidum and Paraffinum subliquidum and isohexadecane (hydrogena-.~ ted polybutylene~.
Other particularly suitable oils are esters of :; trihydric and more -~han trihydric alcohols, more par-.~ ticularly vPgetable triglycerides, for example olive ` oil, almond oil, peanui oil, sunrlower oil, or even the esters of pen-taerythritol, for example ~ith pelargonic acid or oleic acid.
Other par~icularly suitable oils are monoesters and diesters correspondiny to general formulae Ij II and III
.
(I) ~1-COOR2 (II) R2_ooc-R3-COOR2 -~: (III? Rl_coo-R3-OOC-Rl in which R1 is a C822 alkyl group, RZ is a C32~ alkyl group and R3 represents C216 alkylene groups. These monoesters and diesters contain at least 11 and at most 40 carbon atoms.
Oils of the mono and diester type corresponding : to formulae (I), (II) and (III) are knoT~n as cosmetic and pharmaceutical oil components and as lubricant : components. Among the monoesters and diesters of this type, the products liquid at room temperature (20C) are the most important. Monoesters (I) suitable as oils are, for example, the isopropyl esters of C1222 fatty acids such as, for example, isopropyl myristate, isopro-pyl palmitate, isopropyl stearate, isopropyl oleate.
Other suitable monoesters. are, for example, n-butyl ~; stearate, n-hexyl laurate, n-decyl oleate, isooctyl stearate, isononyl palmitate, isononyl isononanoate, 2-~ 35 ethylhexyl palmitate, 2-ethylhexyl laurate, 2-hexyldecyl ; ~ ' , .
"
:
2 ~ ~ ~ 9 3 ~
~0 92/07543 4 PCT/EP91/01966 .
stearate, 2-octyl dodecyl palmitate, oleyl oleate, oleyl erucate, erucyl oleate and esters obtainable from technical allphatic alcohol mixtures and technical aliphatic carboxylic acids, for example esters of saturat2d and unsaturated C12zz fatty alcohols and i saturated and unsaturated C1222 ~atty acids WhiCh are ; obtainable from animal and vegetable fats. Naturally occurring monoester or wax ester mixtures, as present for example in jojoba oil or sperm oil, are also suit-lo able.
Suitable dicarboxylic acid esters (II) are, for example, di-n-butyl adipate, di-n-butyl sebacate, di-(2-ethylhexyl)-adipate, di-(2-hexyldecyl)-succinate and di-~ isotrldecyl azelate. Suitable diol esters (III) are, i~ 15 for example, ethylene glycol dioleate, ethylene glycol diisotridecanoate, propylene glycol di-(2-ethylhexano-ate), propylene glycol diisostearate, propylene glycol dipelargonat~, butanediol diisostearate and neopentyl glycol dicaprylate.
Other suitable oils are branched primary alcohols of the type known as Guerbet alcohols (seer for example, A.J. O~Lenick ~r., R.E. Bilbo, Soap Cosm. Chem. 8pec.
1987, 52), for example 2-hexyl decanol or 2-octyl dodecanol, and esters of Guerbet alcohols with long-chain aliphatic carboxylic acids, for example with stearic acid.
The oils are used in the o/w emulsions according to the invention in a quantity of 5 to 30% by weight ~` and, more particularly, 10 to 20% by welght.
Suitable alkyl glucosides (B) are glucosides . ~
containing a C8z2 alkyl radical. They are normally prepared by reaction of glucose or starch or starch ` ~ syrup with the corresponding long-chain alcohols. The ....
~` alcohols have to be used in excess. On completion of the reaction, the unreacted alcohol is largely distilled ~, .i ~i .
~`
. ~ .
:
: .
.
- :': ': ,- .
i , 2 ~
~0 92/07543 5 2CT/~P91/01966 off, so that the alkyl glucoside used in accordance with i the invention generally has residual alcohol contents of approximately 1% by weight.
Alkyl glucosides are characterized by the general formula ~O(G)~, in which:
- R is a linear saturated C8~2 alkyl radical - G is a glucose unit - x is a number of 1 to 10.
The index x is the degree of oligomerization and repre-sents a mean value for the distribut,ion of monogluco-; sides and oligoglucosides. As a calculated quantity, ; ~he degree of oligomerization says something of the distribution of the chemical individuals present in a technical oligomer mixture which differ from one another in the number of glucose units present per molecule alkyl glucoside. The average degree of oligomerization x should be a value of 1.1 to 1.6.
In another preferred embodiment of the invention, the alkyl radical of the alkyl glucoside has a chain length of 12 to 18 carbon atoms and more particularly 16 to 18 carbon atoms. - Alkyl glucosides containing at least 85% by weight C~6 are particularly suitable. The alXyl glucosides used in accordance with the invention are species of which the alkyl radicals have the prefer-red chain lengths mentioned. However, they may also contain small quantities of species where the alkyl ,, radicals have shorter and/or longer chain lengths, as present for example in the alkyl radicals of fatty alcohols of vegetable and animal origin.
In a particularly preferred embodiment, alkyl glucosides having a degree of oligomerization x of 1.1 to 1.3 are used.
Another preferred embodiment of the present ~:
:
.
. , :
- ~: ' ' ' ' ' .
- 2 `J ~ .~c '.~ 3 .. , ~O 9~jo75~3 6 PCT/EP91/0196~
invention is characterized in that, in addition to the components described above, it also contains a consis-t~ncy regulator. Consistency regulators are substances which determine or maintain the consistency of cosmetic preparations, for example emulsions (cf. ~. Fey~ I.
Ot~o, ~IWorterbuch dar ~osme~iX", S~uttgar~ 1sa~). Long-chain alcohols, carboxymethyl cellulose or salts of polyacrylic acids, for example, may be used as consis-tency regulators in the o/w emulsions according to the invention. Alcohols containing 14 to 22 carbon atoms and, more particularly, 16 to 18 carbon atoms are par-ticularly suitable as consistency regulators. The con-sistency regulators may advantageously be introduced in the form of the alcohol which is present in the alkyl glucoside after partial removal of the unreacted alcohol by distillation.
The temperatures to which the alkyl glucosides are exposed during removal of the unreacted alcohol by distillation can readily result in unwanted brownish ; 20 discoloration which necessitates a bleaching process.
Accordingly, it can be of advantage not to remove too much of the reacted alcohol, particularly when the long-chain alcohol is in any case to be used as consistency regulator in the o/w emulsion. Accordingly, another embodiment of the present invention is characterized by the use of a crude alkyl glucoside containing 1 to 20%
by weight and preferably 2.5 to S% by weight unreacted alcohol.
The alkyl glucosides are used in the o/w emul-; 30 sions according to the invention in a quantity of 2 to 15% by weight and, more particularly, in a quantity of 2 to 7% by weight.
;~ Fatty acid partial glycerides (C) of saturated or ~` unsaturated C1020 fatty acids are technical mixtures of fatty acid mono-, di- and triglycerides which are .
.
~' ' ' .
:::
~ .
.
- :
~ , .. . .
~,19~
RO 92/075~3 7 PCT/EP91/019S6 obtained by esterification of 1 mol glycerol with 1 to 2 mol of a (C1020) fatty acid or by transesterificatlon of 1 mol of a (Cl0-2c) fatty acid triylyceride, for example beef tallow, lard, palm oil, sunflower oil or soybean oil, with 0.5 to ~ mol glycerol.
Two types of partial glycerides are commercially obtainable. Partial glycerides of type I contain 35 to 60% monoglycerides, 35 to 50% diglycerides and 1 to 20%
triglycerides. Partial glycerides OL typ~ II ar~
prepared by molecular distillation from those of type I
and contain 90 to 95% monoglycerides, 1 to 5% diglycer-ides and less than 1% triglycerides (cf.: a) G. 8chustar and W. ~dams: Zeitschrift fur Lebensmitteltechnologie, 1979, Yol. 30 ~61, pagss 256-264; b) G. Schuster ~d.~
"Emulgatoren fur Lebansmittel", Springer-~eralg, 1935).
; The fatty acid partial glycerides used in accord-ance with the invention should contain 60 to 95% mono-glycerides, l to 35~ diglycérides and 0.1 to 5% trigly-cerides. A preferred embodiment of the invention is characterized by the use of fatty acid partial glycer-ides containing 90 to 95% by weight monoglyceride.
Fatty acid partial glycerides of which the fatty acid components contain 16 to 18 carbon atoms are particular-ly favorable.
The fatty acid partial glycerides are used in the o/w emulsions according to the invention in a quantity of 2 to 20% by weight and, more particularly, in a quantity of 4 to 10~ by weight.
In addition, the o/w emulsions according to the invention may contain additional components or auxili-aries known from the prior art. The most important are:
~:, ; a) co-emulsifiers, for example anionic surfactants ;~ containing carboxylate, sulfonate, sulfate or phosphate groups, such as soaps, alkyl and aryl ~: .
' :~
,: , ., :
, . . .
:
2~3~
.j :,.
~O 92/~7543 8 PC~/~P91/01966 ether sulfates, fatty amines, quaternary ammonium and pyridinium compounds, nonionic emulsifiers, such as ethylene oxide adducts ~ith alcohols, carboxylic acids, partial glycerides and sorbitan esters, amphoteric emulsifiers, such as imidazo-line derivatives, betaines or sulfobetaines and, for example, fatty acid esters and sorbitan fatty acid esters (cf., for example, 7~ UmDacn ~Bd.3, ~Rosmetik-EntwicXlung, Xerstallung und ~n~2ndung 10 ` ~osmetischer ~ittel", pag2s a~-37, ~tuttgar!-1988).
b) Humectants, for example glycerol, polyylycerols, sorbitol, propane-1,2-diol, butane-1,2,3-triol, polyethylene glycols, glucose, mannitol, ~vlitol.
c) Antimicrobial agents as preservatives, for example benzoic acid, salicylic acid, sorbic acid and esters and salts thereof.
d) Perfume oils, for example natural fragrances obtained by distillation, extraction or pressing from plants and synthetic fragrances (cf., for example, ~. Aebi, ~. Baumgartner, H.P. Fiedler, ~' G. Ohloff, "Rosmetika, Riechstoffe und Le~ens-~ittelzu~atzstoffe", Stuttgart 1978).
e) Antioxidants, for example tocopherols, lecithin, 2S guaiacol, butyl cresol, 4-methyl-2,6-ditert.butyl phenol (BHT), 4-methoxy-2(3)-tert.butyl phenol (BHA) f) Dyes of the type listed for cosmetics, for example, by the Farbstoff Kommission der Deut-; 30 schen Forschungsgemeinschaft ("Farbemittel fur ~osmetika", Mitteilung 3, ~iesbaden 1968).
~. ' ~` To prepare the emulsions, the alkyl glucosides ;;~ are dissolved either in the hot water phase or fatty ~ 35 phase. The water phase is preferably added to the oil : .
:
, .
. ~ : - -.
2 ~ J ~:~f 'J
phase with stirring at 60 to 80'C. The dispersions thus obtained are subsequently cooled to 30C. If desired, the structure of the emulsion may be improved during cooling by units opera~ing on the rotor/stator prin-ciple, for example Ultra-Turrax T50 (I1ca-~er'ce).
The o/w emulsions according to ~he invention may also be prepared in the absence of heat by virtue of the solubility of the alkyl glucosides in ~ater, particular-ly those containing C1216 alkyl radicals. Rich liquid or creamv cosmetic emulsions can be rormulated in this way, particularly in combination with hydrophilic or hydro-phobic emulsifiers and oils liquid at room temperature, using polymeric thickeners.
; The present invention relates to emulsifier 15 concentrates for the production of o/w emulsions accord-ing to the invention containing ` (D) 24 to 75% by weight of one or more alkyl gluco-sides corresponding to the general formula RO(G)~, in which - R is a linear saturated C822 alkyl radical - G is a glucose unit - x is a number of 1 to 10 (E) 24 to 75% by weight of a fatty acid partial glyceride containing 60 to 95% by weight monogly-ceride (F) 0.1 to 50% by weight of a linear saturated alcohol containing 14 to 22 carbon atoms and, ~; more particularly, 16 to 18 carbon atoms.
For the reasons mentioned above, the emulsifier concentrates may also be prepared using alkyl glucosides ::
in whose case unreacted alcohol was distilled off only partly, if at all, during the production process. Ac-35 cordingly, a preferred embodiment of the present inven-:
~,` ' `
; .
, :
~O 92/07~3 10 PCT/BP91/01966 tion is characterized in that the emulsifier concentra-tes are preparsd using alkyl glucosides containing from 3 to 90~ by weight and preferably from 3 to 40% by weight unreacted alcohol. In cases such as these, the alkyl glucosides may be mixed ~/ith the fatty acid partial glycerides immedia~ely after the reaction between glucose and long-chain alcohols and, if desired, partial removal of the unreacted alcohol by distillation at temperatures of around 100C. It is possible in this way to produce self-e~Lulslfying emulsion bases with which cosmetically sophisticated creams and lotions can be formulated.
In addition, the emulsifier concentrates accord-ing to th~ lnvention may contain additional components or auxiliaries or ~he type described above, for example oils, co-emulsifiers, hu~ectants, preservatives, perfume oils, antioxidants, dyes.
The ollowing Examples are intended to illustrate the invention.
i E x a m p 1 e .
1. Substances used 1.1 Oil (A) Cetiol V: oleic acid decyl ester (Henkel KGaA, Dusseldorf); Mvritol 318: caprylic/capric acid triglyceride (Henkel KGaA, Dusseldorf) 1.2 Alkyl ~lucosides (B) ~` 30 The alkyl glucosides used were C14~ C1B and C18 alkyl glucosides (abbreviated to AG C14, AG C16 and AG C18) having degrees of oligomerization x of 1.2 to 1.4. The corresponding Cl4, C16 and C18 fatty alcohols were used to prepare the C14, C16 and C18 alkyl glucosides (C chain distribution .
. ....................................................................... .
. . .
2 ~
~O 92~07543 11 PC~/~P91/01966 according to GC: a) for Cl4 fatty alcohol: 2~ Cl2;
96% Cl4; 2% C16; b) for C~6 fatty alcohol: 2% C14;
95~ Cl8; 2% Cl~; c) for Cl~ fatty alcohol: 2% Cl6;
9~-~ Cl3; 2% C20).
, 1.3 Fattv acid partial glYcerides (C) Cu-~ina ~D: fatty acid partial glyceride based on hydrog2nated palm oil with a monoglyceride con-tent of 42% by weight (Grunau, Illertissen);
.lonomuls 60-35: fatty acid partial glyceride based on hydrogenated palm oil with a monoglycer-ide content of 60% by weight (Grunau, Illertis-sen); Monomuls 90-35: fatty acid partial glycer-ide bas2d on hydrogenated palm oil with a mono-glyceride content OL 90% by weight (Grunau, Illertissen) ' 1.4 Other components Lanet~e O: cetyl/stearyl alcohol [50:50] (Henkel KGaA, Dusseldorf); Lanette E: cetyl/stearyl alcohol sulfate, Na salt [50:50] (Henkel KGaA, Dusseldorf); Cutina E-24: polyoxyethylene-24-glycerol monostearate (Henkel KGaA, Dusseldorf).
; 25 2. Production and characterization of the disPer-sions To prepare the emulsions, the alkyl glucosides were dissolved in either the hot water phase or fatty phase. The water phase was preferably added with stirring to the oil phase at 60 to 80C. The disper-sions obtained were then cooled to 30 C.
After 24 hours, the viscosities were measured at . .
; 23C with a Brookfield viscositmeter using spindle E at ; 4 r.p.m. The emulsions were then stored for 2 weeks at ~' 35 -5 C, 20C and 40C and exami.. ed visually and under a ~ .
::
: ~ . . .: . , , ~ .
- ~ ~3 ~ 3~
microscope (400x magnification). The results are shown in Table 1 according to the composition of the emul-sions.
In every case where Monomuls 90-35 or Monomuls 6--~ 5 35 (monoglycsride content: 90~ or 60~ as used as the partial glyceride, the emulsions obtained were homogen-eous ~oth immediately after preparation and after storage under the conditions described above (Table 1, columns Bl to B~). By contrast, the emulsion obtained using Cutina ~ID, a partial glyceride containing 42%
monoglyceride, was either homogeneous immediately after ` its preparation, but showed distinctly crystalline con-stituents under a light microscope (400x magnification) - and separated lnto two phases at 40OC (Table 1, columns C1 and C2), or was macroscopically inhomogeneous im-mediately after its preparation (Table l, column C3).
., . .
:
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. . ~ . ~ O O O
m ~ o I ~ ~ r ~ .u~
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o ~o 03 o o ~ ~ ~ o U~ o ~
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~ ~ - o ~ ~ ~
-- o _ ,~ ~ ~ h O O O O O e ~ e , . ~t . . ~ ~ O O O
~,~ NI I ~ I In I I rl I I ~ I ~'t I I (1;~ ~ ,S: S S O e a) I
,~ ~ . o ~0 ~0 ~0 a~
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o ~ . oo O O e e e _, ~I . . ~ O ~ ss m ~
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~1 N ~ ~ ~ ~ e e N
.
. o O ~D O~ 0 0 '( Oe e Qt ~ ~ e ~o N d' ~ C~O O al O O O N
d~ I i I II 1~) ~1 1 ¦ ¦ O 0 ¦ I (~ ~1 S S Ul (~ ~ ~) O ~ ~ O ~ Q~
O ~1~1 .
o ~ ~ O Oe e Qt 5~ 0 U~
~ S 0 O O ~ ~ U .3 ~ O
I ~ I I I I ~ I I I o ~ a ~ s .c ul D~ ~ O ~t t.) ~ a1 . ~ Rt ~ o-~
O O 0 ~ ~ ~0 ~ 0 U
O ~ U~ ~n O O 3~1 a) h O ~
~1 ~`7 d' ~ t'l S ~I h ~d ~ I ~ c U~ t~ al S 0 ~. I I O 0 0\ ~ 4 t~ t~ q) O Q, ~
~1 ~1 ~1 ~1 0 0 C~ U ,~ u~ t .. a~ h ~ al-~l ~1 I h ~ a~ ~ _ O U~
o ,~ ,1~ a) o cJ ~ ~ a) Qt~l 11 e Q-~l ~ ~ ~ V C~ 0 ~1 0 ::~ O h ~ ~ ' e c) o e ~
~ ~D ~1 ~1 ~ ~i ~ e s:: o ~ h ~h O 0 1~ 0 Q,S 0 ~
O ~ u ~) o o -~l 0 ~ O u a) h X ~ O a) ~: X ~
~ ~ Qt O ~ ~ S U~
O ~ ~ ~ ~ t~ o o ~1 ~ a) 0 ~ 1 Qt IJ
B E~ ~ (.) 3 :~
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Claims (6)
1. Oil-in-water emulsions containing alkyl gluco-sides, characterized in that they contain (A) one or more water-insoluble oils, (B) as emulsifier, one or more alkyl glucosides corresponding to the general formula RO(G)x, in which - R is a linear saturated C8-22 alkyl radical - G is a glucose unit - is a number of 1 to 10, characterized in that they contain (C) a fatty acid partial glyceride with a monoglycer-ide content of 60 to 95% by weight as crystal-lization inhibitor.
2. Emulsions as claimed in claim 1, characterized in that the water-insoluble oil (A) is present in a quan-tity of 5 to 30% by weight, the alkyl glucoside (B) is present in a quantity of 2 to 15% by weight and the fatty acid partial glyceride (C) is present in a quan-tity of 2 to 20% by weight.
3. Emulsions as claimed in claim 1 or 2, charac-terized in that the alkyl radical of the alkyl glucoside (B) has a chain length of 16 to 18 carbon atoms.
4. Emulsions as claimed in at least one of claims 1 to 3, characterized in that the degree of oligomeriza-tion x of the alkyl glucoside (B) is 1.1 to 1.6.
5. Emulsions as claimed in at least one of claims 1 to 4, characterized in that they additionally contain a C14-22 and, more particularly, C16-18 alcohol as consistency regulator.
6. Emulsifier concentrates for the production of the storable oil-in-water emulsions claimed in at least one of claims 1 to 5, characterized in that they contain (D) 24 to 75% by weight of one or more alkyl gluco-sides corresponding to the general formula RO(G)x, in which - R is a linear saturated C8-22 alkyl radical - G is a glucose unit - x is a number of 1 to 10 (E) 24 to 75% by weight of a fatty acid partial glyceride containing 60 to 95% by weight monogly-ceride (F) 0.1 to 50% by weight of a linear saturated alcohol containing 14 to 22 carbon atoms and, more particularly, 16 to 18 carbon atoms.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4033928A DE4033928A1 (en) | 1990-10-25 | 1990-10-25 | OIL IN WATER EMULSIONS |
| DEP4033928.9 | 1990-10-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2094935A1 true CA2094935A1 (en) | 1992-04-26 |
Family
ID=6417021
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002094935A Abandoned CA2094935A1 (en) | 1990-10-25 | 1991-10-16 | Oil-in-water emulsions |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5494938A (en) |
| EP (1) | EP0554292B1 (en) |
| JP (1) | JP3043410B2 (en) |
| CA (1) | CA2094935A1 (en) |
| DE (2) | DE4033928A1 (en) |
| ES (1) | ES2066481T3 (en) |
| WO (1) | WO1992007543A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6998372B2 (en) | 2001-08-16 | 2006-02-14 | J&J Consumer Companies, Inc. | Moisturizing detergent compositions |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4110506A1 (en) * | 1991-03-30 | 1992-10-01 | Huels Chemische Werke Ag | EMULSIFIERS FOR THE PRODUCTION OF OIL-IN-WATER EMULSIONS OF ETHERIC OILS USED IN COSMETICS OR MEDICINE |
| DE4230504A1 (en) * | 1992-09-15 | 1994-03-17 | Beiersdorf Ag | Stable cosmetic products |
| WO1994016677A1 (en) * | 1993-01-23 | 1994-08-04 | Henkel Kommanditgesellschaft Auf Aktien | Detergent mixtures with improved brightening properties |
| DE4301820C2 (en) * | 1993-01-23 | 1996-04-25 | Henkel Kgaa | Foaming emulsions, processes for their preparation and their use |
| DE4317089A1 (en) * | 1993-05-21 | 1994-11-24 | Henkel Kgaa | Nonionic emulsifiers |
| FR2706299B1 (en) † | 1993-06-10 | 1995-09-01 | Oreal | Cosmetic or dermatological oil-in-water emulsion containing a self-emulsifiable composition based on a fatty alcohol and an alkylpolyoside and a co-emulsifier. |
| GB9315501D0 (en) * | 1993-07-27 | 1993-09-08 | Ici Plc | Surfactant compositions |
| DE4335045A1 (en) * | 1993-10-14 | 1995-04-20 | Henkel Kgaa | Flowable emulsion concentrate |
| US5575990A (en) * | 1993-10-28 | 1996-11-19 | Bristol-Myers Squibb Company | Antiperspirant roll-on compositions |
| FR2712595B1 (en) * | 1993-11-19 | 1995-12-22 | Seppic Sa | A concentrate comprising alkyl glycosides and its uses. |
| DE4341794C1 (en) * | 1993-12-08 | 1995-01-19 | Henkel Kgaa | Cosmetic and/or pharmaceutical compositions with improved skin feel |
| DE4417476A1 (en) * | 1994-05-19 | 1995-11-23 | Henkel Kgaa | Microemulsions |
| FR2733417B1 (en) * | 1995-04-25 | 1997-06-06 | Oreal | FOAMING OIL-IN-WATER EMULSION BASED ON NON-IONIC SURFACTANTS, A FATTY PHASE AND A CATIONIC OR ANIONIC POLYMER CROSS-LINKED AND USE IN TOPICAL APPLICATION |
| FR2734496B1 (en) * | 1995-05-24 | 1997-07-04 | Seppic Sa | EMULSIFYING COMPOSITION BASED ON ALKYLPOLYGLYCOSIDES, AND USES THEREOF |
| DE19529907A1 (en) * | 1995-08-15 | 1997-02-20 | Henkel Kgaa | Fine-particle emulsions containing sugar surfactants |
| DE19539877C2 (en) * | 1995-10-26 | 1998-07-23 | Henkel Kgaa | Cosmetic and pharmaceutical emulsions |
| DE19540831C2 (en) | 1995-11-02 | 1998-07-16 | Henkel Kgaa | Cosmetic and pharmaceutical emulsions |
| DE19540829C2 (en) * | 1995-11-02 | 1998-08-20 | Henkel Kgaa | Cosmetic and / or pharmaceutical emulsions |
| DE19541754C2 (en) | 1995-11-09 | 1998-07-30 | Henkel Kgaa | Cosmetic and / or pharmaceutical emulsions |
| DE19541753C2 (en) | 1995-11-09 | 1998-07-16 | Henkel Kgaa | Cosmetic and / or pharmaceutical emulsions |
| DE19542141C2 (en) | 1995-11-11 | 1998-07-30 | Henkel Kgaa | Cosmetic and / or pharmaceutical emulsions |
| DE19542139C2 (en) | 1995-11-11 | 1998-07-30 | Henkel Kgaa | Cosmetic and / or pharmaceutical emulsions |
| DE19542572C2 (en) * | 1995-11-15 | 1998-05-20 | Henkel Kgaa | Use of emulsifier mixtures |
| US5795978A (en) * | 1995-11-15 | 1998-08-18 | Henkel Kommanditgesellschaft Auf Aktien | Emulsifiers |
| DE19543633C2 (en) * | 1995-11-23 | 2000-08-17 | Cognis Deutschland Gmbh | Cosmetic and / or pharmaceutical preparations |
| DE19546416A1 (en) | 1995-12-12 | 1997-06-19 | Basf Ag | Oil emulsion |
| DE19547679A1 (en) * | 1995-12-20 | 1997-06-26 | Wella Ag | Hair care emulsion |
| DE19547986C1 (en) * | 1995-12-21 | 1997-07-10 | Henkel Kgaa | O / W microemulsions |
| DE19548345C2 (en) * | 1995-12-22 | 1998-10-15 | Henkel Kgaa | Use of mixtures of special emulsifiers and oil bodies |
| DE19615271A1 (en) * | 1996-04-18 | 1997-10-23 | Huels Chemische Werke Ag | Detergent containing detergents in the form of a microemulsion |
| DE19624455C2 (en) * | 1996-06-20 | 1998-08-27 | Henkel Kgaa | Sunscreen in the form of O / W microemulsions |
| US5837223A (en) * | 1996-08-12 | 1998-11-17 | Revlon Consumer Products Corporation | Transfer resistant high lustre cosmetic stick compositions |
| DE19637841A1 (en) * | 1996-09-17 | 1998-03-26 | Henkel Kgaa | Aqueous concrete release agents |
| DE19643063A1 (en) * | 1996-10-18 | 1998-04-23 | Henkel Kgaa | Eye or lip make=up salve |
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| US8920918B2 (en) * | 2005-10-31 | 2014-12-30 | Kee Action Sports Technology Holdings, Llc | Oil and polyethylene glycol fill material for use in paintball shells |
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| EP1891935A1 (en) * | 2006-08-14 | 2008-02-27 | Cognis IP Management GmbH | Emulsion concentrate |
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| EP2162112A2 (en) * | 2007-06-19 | 2010-03-17 | Cognis IP Management GmbH | Method for preparing finely divided emulsions |
| US20100064927A1 (en) * | 2008-09-17 | 2010-03-18 | Aldo Perrone | Starch-based paintball fill material |
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| BRPI1016067A2 (en) * | 2009-06-30 | 2019-09-24 | Cognis Ip Man Gmbh | esters and their uses. |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4400295A (en) * | 1979-03-24 | 1983-08-23 | Loire Cosmetics Co., Ltd. | Emulsifier composition |
| JPS615005A (en) * | 1984-06-19 | 1986-01-10 | Yoshitomi Pharmaceut Ind Ltd | Humectant |
| US4847078A (en) * | 1987-01-14 | 1989-07-11 | Arseco, Inc. | Storage stable topical composition having moisture control agent |
| JPH01115014A (en) * | 1987-10-28 | 1989-05-08 | Komatsu Ltd | Manufacture of superconducting thin film |
| JP2652395B2 (en) * | 1988-02-09 | 1997-09-10 | 株式会社資生堂 | Emulsion composition and emulsified cosmetic |
| JPH03157349A (en) * | 1989-11-14 | 1991-07-05 | Lion Corp | Emulsified composition |
-
1990
- 1990-10-25 DE DE4033928A patent/DE4033928A1/en not_active Withdrawn
-
1991
- 1991-10-16 WO PCT/EP1991/001966 patent/WO1992007543A1/en active IP Right Grant
- 1991-10-16 DE DE59104004T patent/DE59104004D1/en not_active Expired - Lifetime
- 1991-10-16 ES ES91918146T patent/ES2066481T3/en not_active Expired - Lifetime
- 1991-10-16 CA CA002094935A patent/CA2094935A1/en not_active Abandoned
- 1991-10-16 US US08/039,467 patent/US5494938A/en not_active Expired - Lifetime
- 1991-10-16 EP EP91918146A patent/EP0554292B1/en not_active Expired - Lifetime
- 1991-10-16 JP JP3516410A patent/JP3043410B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6998372B2 (en) | 2001-08-16 | 2006-02-14 | J&J Consumer Companies, Inc. | Moisturizing detergent compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0554292A1 (en) | 1993-08-11 |
| WO1992007543A1 (en) | 1992-05-14 |
| JPH06501942A (en) | 1994-03-03 |
| US5494938A (en) | 1996-02-27 |
| DE4033928A1 (en) | 1992-04-30 |
| JP3043410B2 (en) | 2000-05-22 |
| ES2066481T3 (en) | 1995-03-01 |
| DE59104004D1 (en) | 1995-02-02 |
| EP0554292B1 (en) | 1994-12-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |