EP1102836A1 - Emulsion eau dans l'huile pour fournir des caracteristiques cosmetiques a une composition de base d'un produit assouplissant - Google Patents

Emulsion eau dans l'huile pour fournir des caracteristiques cosmetiques a une composition de base d'un produit assouplissant

Info

Publication number
EP1102836A1
EP1102836A1 EP99937670A EP99937670A EP1102836A1 EP 1102836 A1 EP1102836 A1 EP 1102836A1 EP 99937670 A EP99937670 A EP 99937670A EP 99937670 A EP99937670 A EP 99937670A EP 1102836 A1 EP1102836 A1 EP 1102836A1
Authority
EP
European Patent Office
Prior art keywords
microemulsion
perfume
water
ether
composition
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.)
Granted
Application number
EP99937670A
Other languages
German (de)
English (en)
Other versions
EP1102836B1 (fr
Inventor
Eric Ewbank
Dominique Tummers
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Colgate Palmolive Co
Original Assignee
Colgate Palmolive Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Colgate Palmolive Co filed Critical Colgate Palmolive Co
Priority to DK99937670T priority Critical patent/DK1102836T3/da
Publication of EP1102836A1 publication Critical patent/EP1102836A1/fr
Application granted granted Critical
Publication of EP1102836B1 publication Critical patent/EP1102836B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0008—Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
    • C11D17/0017—Multi-phase liquid compositions
    • C11D17/0021—Aqueous microemulsions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • C11D3/0015—Softening compositions liquid
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2068—Ethers
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/43—Solvents
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes

Definitions

  • This invention relates to a composition and method for "post-adding" cosmetic attributes to a fabric softening base composition at the final stage of its manufacture. More particularly it relates to a water-in-oil microemulsion which is suitable for containing adjuvants such as perfume or colorant and which can be readily mixed with a fabric softening base composition with only a minimum amount of shear and without adversely affecting its physical stability.
  • perfumes and colorants are routinely introduced into liquid fabric softening compositions to provide appealing cosmetic attributes for the consumer.
  • the introduction of perfume, for example, to a liquid softening composition is meant to leave a pleasant and lasting fragrance on the treated fabrics.
  • the colorant is intended to provide a visually pleasing product as well as convey to the consumer an overall impression of softness and quality.
  • perfumes and colorants are attributes which allow the formulator a degree of flexibility to provide product variety for a given softening technology or for a fixed fabric softening base composition.
  • perfume on a weight basis, is invariably a very minor component of a commercial fabric softener composition
  • its introduction into the composition in an efficient manner is a subject of much concern in the formulation art. This is particularly true for concentrated fabric softeners containing more than about 10% by weight of active softening ingredients insofar as the aqueous softener base compositions tend to gel in the presence of water-immiscible perfume. This tendency of gel formation is particularly problematic when the water-immiscible perfume is poorly dispersed in the aqueous emulsion which constitutes the softening base composition.
  • Undesirable thickening or gelation of a softener base composition has significant drawbacks: it reduces the effective shelf life of the final product and adversely affects consumer acceptance for a softener product which upon use has thickened to an unexpectedly viscous mass instead of meeting the consumers expectation of being essentially free-flowing.
  • the prior art has addressed itself to overcoming the pervasive problems of gelation and the formation of high viscosity liquids which accompany the introduction of water-insoluble perfumes into aqueous fabric softener base compositions.
  • U.S. Patent 5,447,644 to International Flavors & Fragrances describes a method to avoid gelation of the softening composition resulting from the introduction of increased levels of perfume into a softener base composition.
  • this method there is first formed an aqueous microemulsion by mixing the perfume with a defined nonionic surfactant under conditions of high shear to uniformly disperse the perfume in the surfactant/water mixture.
  • the perfume-containing microemulsion is then mixed with a fabric softener base formulation to form the final fabric softener composition.
  • a high shear mixer is required for this mixing operation.
  • a perfume-containing water-in-oil microemulsion capable of being mixed with a perfume-free fabric softener base composition which is in the form of an aqueous emulsion so as to disperse perfume in said aqueous emulsion under conditions of low shear while avoiding any problem of gelation to thereby provide a physically stable perfume-containing liquid fabric softening composition
  • said water-in-oil microemulsion comprising:
  • A is independently C (O) O - R' or - O (O) C - R';
  • R is a lower alkyl group having 1 to about 4 carbon atoms;
  • R' is an alkyl or alkenyl group having 8 to about 22 carbon atoms;
  • R" is independently a lower alkyl radical having 1 to about 6 carbon atoms or hydroxyl alkyl group or H;
  • n is an integer having a value of 1 to about 3;
  • X " is a softener compatible anion
  • R ⁇ is a lower alkyl radical having 1 to about
  • R is an alkylene radical having 2 to about 4 carbon atoms;
  • microemulsion from about 0.5% to about 30%, by weight, of water; said microemulsion being free of an anionic surfactant, and having a weight ratio of said oily phase to water of from about 3:1 to about 200:1 , the percentages of components (a), (b) and (c) and the value of said weight ratio being selected so that the resulting composition forms a water-in-oil microemulsion.
  • Danielsson and Lindman "The definition of Microemulsion", Colloids and Surfaces, 3 (1981 ), 391-392, Elsevier Scientific Publishing Company, have defined a "microemulsion” as 'a system of water, oil and amphiphile which is a single optically isotropic and thermo-dynamically stable liquid solution'. This definition of microemulsion is used herein in describing the present invention.
  • a microemulsion has the following characteristics/properties: i) Clear ii) It is free of lyotropic liquid crystalline system (i.e. it is isotropic) iii) It has relatively low viscosity iv) It is formed spontaneously by simple mixture/agitation of all components (i.e. it is thermodynamically stable)
  • the present invention also provides a method for introducing a perfume into a perfume-free fabric softener base composition which is in the form of an aqueous emulsion under conditions of low shear and without adversely affecting its physical stability comprising the steps of:
  • the water-in-oil microemulsion compositions of the invention are predominantly comprised of the oily phase as defined above, namely, the cationic surfactant fabric softener, the organic solvent and the water-insoluble perfume.
  • the amount of water should generally be no greater than about 30%, by weight, and preferably, from about 5% to about 25%, by weight.
  • the preferred diester quaternary ammonium surfactants for use herein are the dioleyl diester "quats" represented by equation (1 ). Particularly preferred is methyl bis-
  • the present invention is predicated on the discovery that cosmetic attributes such as perfume and colorant can be readily "post-added” to an aqueous fabric softening base composition at the final stage of its manufacture by using a water-in-oil microemulsion as herein defined as the vehicle to be added to and mixed with the aqueous emulsion to form the finished product.
  • the water-in-oil microemulsion is incorporated into the softening base composition under conditions of gentle agitation or low shear, using a sufficient amount to provide the desired level of perfume to the finished product.
  • the microemulsion undergoes an inversion upon dilution in the aqueous emulsion which serves to efficiently disperse the perfume or colorant throughout the composition without concomitant problems of gelation or product instability.
  • the present invention provides important advantages from the standpoint of manufacturing a softening product composition as well as in insuring the integrity of the final product itself.
  • the essence of the present invention is an oil in water microemulsion which can be readily formed at room temperature with no need for high shear forces or elaborate mixing equipment. And with regard to the finished product, it is clear that the introduction of cosmetic attributes into a softening base composition is accomplished without adversely compromising the rheology or physical stability of the resulting product.
  • Diester quaternary ammonium surfactant fabric softeners represented by equation (1 ) are preferred for use herein and are commercially available from Stepan Co. as Stepantex and from KAO Corp. as Tetranyl but can also be synthesized by the reaction of two moles of a fatty acid with a trialkanolamine, preferably, triethanolamine followed by methylation with dimethyl sulfate or an alkyl halide such as, methyl iodide. In a preferred mode the fatty acid is oleic acid.
  • Soya fatty acids are a practical source for this purpose consisting of about 3% myristic acid, about 5% palmitic acid, about 5% palmitoleic acid, 1.5% stearic acid, 72.5% oleic acid and about 13% linoleic acid.
  • Other sources of useful fatty acids are those obtained from the saponification of beef tallow, butter, corn oil, cottonseed oil, lard, olive oil, palm oil, peanut oil, cod liver oil, coconut oil and the like.
  • a preferred diester quaternary ammonium surfactant fabric softener is methyl bis[ethyl(oleyl)]-2-hydroxyethyl ammonium methyl sulfate.
  • diesters useful in the practice of this invention include: methyl bis-[ethyl(coconut)]-2-hydroxyethyl ammonium methyl sulfate methyl bis-[ethyl(decyl)]-2-hydroxyethyl ammonium methyl sulfate methyl bis-[ethyl(dodecyl)]-2-hydroxyethyl ammonium methyl sulfate methyl bis-[ethyl(lauryl)]-2-hydroxyethyl ammonium methyl sulfate methyl bis-[ethyl(palmityl)]-2-hydroxyethyl ammonium methyl sulfate methyl bis-[ethyl(soft-tallow)]-2-hydroxyethyl am
  • coconut and soft-tallow indicate mixtures of esters corresponding to the fatty acid source.
  • a certain amount of the triester homolog may be produced as an impurity.
  • perfume is used herein in its ordinary sense to refer to and include any non water-soluble fragrant substance or mixture of substances including natural (i.e., obtained by extraction of flower, herb, blossom or plant), artificial (i.e., a mixture of natural oils or oil constituents) and synthetic (i.e., a single or mixture of synthetically produced substance) odoriferous substances.
  • perfumes are complex mixtures of blends of various organic compounds, such as, esters, ketones, hydrocarbons, lactones, alcohols, aldehydes, ethers, aromatic compounds and varying amounts of essential oils (e.g., terpenes) such as from about 0% to about 80%, usually from about 10% to 70% by weight, the essential oils themselves being volatile odoriferous compounds and also serving to dissolve the other components of the perfume.
  • essential oils e.g., terpenes
  • the precise composition of the perfume has no particular effect on fabric softening so long as it meets the criteria of water immiscibility and pleasant odor.
  • Organic solvents suitable for use in this invention include: aliphatic alcohols having 1 to about 6 carbon atoms, such as, ethanol, propanol, isopropanol, n-butanol, isobutanol, t-butanol, n-pentanol, isopentanol, sec-pentanol, n-hexanol, isohexanol, other isomers and the like; aliphatic polyalcohols, such as, ethylene glycol, propylene glycol, butylene glycol, diethylene glycol, dipropylene glycol, 1 ,4-butanediol, 2-methyl- pentanediol, hexane triol, tripropylene glycol, pentaerythritol, glycerol, sorbitol, and the like; aliphatic ethers, such as, ethylene glycol monobutyl ether(EGMBE), diethylene glyco
  • DPM dipropylene glycol methyl ether
  • DnB dipropylene glycol monobutyl ether
  • EGMBE ethylene glycol monobutyl ether
  • the weight range of cationic surfactant is generally from about 5% to about 80%, and preferably from about 10% to about 60%, by weight;
  • the weight range of the organic solvent is generally from about 2% to about 50%, and preferably from about 4% to about 40%, by weight;
  • the weight range of the water-immiscible perfume is generally from about 5% to about 80%, and preferably from about 10% to about 70%, by weight.
  • the water content is generally from about 0.5% to about 30%, and preferably from about 5% to about 25%, by weight.
  • the weight ratio of the defined oily phase to water is generally from about 3:1 to about 200:1 , preferably from about 5:1 to 50: 1 , and most preferably from about 5: 1 to about 20: 1.
  • the microemulsions of the invention have a particle size between 10 and 100 nanometers. At particle sizes below about 50 nanometers, the microemulsions are generally clear.
  • the microemulsions are formed by simply combining the above- described components of the composition under gentle agitation or low shear. Conventional mixing equipment known to those skilled in the art is sufficient for this purpose. All of the components described herein, both required and optional, must be normally liquid, namely, liquid at ambient room temperatures. Accordingly, there is no need for heating during the preparation of the microemulsions.
  • the invention is further described in the examples which follow. All parts and percentages are by weight unless otherwise specified.
  • Microemulsion compositions/area in a pseudo-ternary phase diagram were basically determined on a clear/turbid criteria basis by mixing three of the components and titrating with incremental amounts of the fourth component.
  • a mixture consisting of organic solvent (or mixture of), water- immiscible perfume and water were introduced in a suitable/fixed ratio, and then titrated with DODEQ (dioleyl diesterquat).
  • DODEQ dioleyl diesterquat
  • Samples were mixed at RT using a magnetic stirrer operating at 100-150 rpm after which they were allowed to stand for few minutes before visual examination for clarity/tubidity. Clear samples were further examined under a polarizing microscope to check that the liquids were isotropic.
  • estimated regions for microemulsion compositions were located on pseudo-ternary phase diagrams. Some compositions located inside these microemulsion areas were selected to illustrate the present invention.
  • DODEQ dioleyl diester quat
  • R1 and R2 are C 7H34, unsaturated alkyl chains from oleic acid.
  • DODEQ is commercially available from KAO as Tetranyl or from Stepan Co. as Stepantex. It is synthesized by the reaction of two moles of oleic acid with triethanolamine followed by methylation with dimethyl sulfate.
  • oleic acid may be replaced by olive fatty acids in the synthesis of DODEQ, such olive fatty acids comprising 14% palmitic acid, 2% palmitoleic acid, 2% stearic acid, 64% oleic acid, 16% linoleic acid and 2% linolenic acid.
  • Such material is available from KAO under the name Tetranyl AO-2.
  • the water-soluble dyes used in the examples are marketed under the names Liquitint Royal Blue, Liquitint Yellow LP and Liquitint Nature Green, by Milliken Chemical company.
  • the fabric softening base compositions contain two principal softening compounds:
  • dialkyl esterquat sold as Tetranyl AT175 by KAO.
  • the dialkyl amidoamine compounds have the general structural formula as follows: O H H O n i ! i n
  • n is an integer of from 1 to 3;
  • R is an alkylene radical having 2 to 4
  • R' is an alkyl or alkenyl group having 8 to about 22 carbon atoms
  • R1 is
  • X " is a softener compatible anion.
  • the softening ingredients are each melted, mixed together with stirring and maintained at about 60 to 70°C.
  • the mixture of molten softening active compounds is added to heated (60-70°C) deionized water with stirring using a 4-pitched blade impeller.
  • the hot water mixture is stirred for 10 to 15 min at about 400 rpm in order to emulsify the molten actives.
  • the stirring speed is increased to 700-800 rpm as the viscosity of the emulsion increases.
  • hydrochloric acid is first introduced separately in the water prior to the addition of the molten softening ingredients.
  • the emulsion is allowed to cool down to 30°C while stirring it at 300-400 rpm.
  • the particle size distribution of the emulsion is further reduced, subjecting the product to high pressure homogenization. This step reduces the viscosity of the composition.
  • Calcium chloride, preservative, sequestering agent and other optional ingredients such as the thickener, are all introduced sequentially with stirring into the cooled product.
  • compositions 1 through 6 were prepared following the procedures described above, each composition having varying weight percentages of the four principal components: cationic surfactant; organic solvent; perfume; and water.
  • the ratio of perfume to organic solvent was kept constant at 60:40.
  • Table 1 The compositions are shown in Table 1 along with observations concerning the appearance of the resulting composition and whether it is within the invention, namely, it formed a water in oil microemulsion, or outside the invention, by forming an emulsion.
  • DPM refers to dipropylene glycol methyl ether
  • compositions 1-4 are w/o microemulsions within the invention; compositions 5 and 6 are emulsions.
  • EXAMPLE 2 PREPARATION OF W/O MICROEMULSION CONTAINING PERFUME
  • compositions 7 through 9 were prepared containing a fixed level of perfume and a varying amount of colorant. The compositions are shown below in Table 2 along with observations concerning the physical appearance of the resulting composition.
  • composition clear(1 ) clear(1 ) clear(1 ) Microemulsion (M)/Emulsion (E) M M M
  • compositions 5, 6, 10, 11 and 12 were prepared wherein the weight ratio of fragrance to organic solvent was varied. The compositions are shown in Table 3 along with observations concerning the appearance of the resulting composition. TABLE 3 COMPONENT 5 10 11 6 12
  • compositions 5 and 6 are two compositions from Example 1 , which are outside of the invention but are included in Table 3 as comparative compositions.
  • Table 3 demonstrates that by changing the ratio of Perfume to organic solvent, it is possible to convert a turbid emulsion into a clear fragrance microemulsion suitable for the present invention.
  • composition 11 a clear w/o microemulsion
  • compositions 5 and 10 which are outside the invention underscores the criticality of the perfume to organic solvent ratio.
  • compositions 6 and 12 demonstrates that by properly adjusting the ratio of perfume to organic solvent, a composition which is outside the invention (composition 6), can be reformulated to provide a clear w/o microemulsion (composition 12).
  • compositions 13 through 18 were prepared to demonstrate the ability to prepare microemulsions in accordance with the invention using organic solvents from the following classes: ethers, esters, glycols and alkanols.
  • organic solvents from the following classes: ethers, esters, glycols and alkanols.
  • the compositions are shown in Table 4 below along with observations concerning the appearance of the resulting composition. TABLE 4
  • the dispersion properties of a perfume-containing microemulsion in accordance with the invention were demonstrated using two different softening base compositions and comparing same with dispersion into 100% water.
  • the perfume micromemulsion composition was comprised of the following: 39% perfume; 26% EGMBE organic solvent; 25% DODEQ; 0.48% Liquitint Royal Blue colorant (4% solution); and balance water.
  • a first softening base composition (“AA/EstQ" base) was comprised of the following: 2.74% amidoamine (Rewopal V3340); 1.64% Esterquat (Tetranyl AT1 -75);
  • the second softening base composition (“EstQ/FA” base) was comprised of the following: 3.9% Esterquat (Tetranyl AT1-75); 0.83% C-16-18 fatty alcohol; 0.2% alcohol
  • lactic/lactate buffer solution 0.20% polyacrylate thickener; and balance water.
  • the perfume microemulsion was introduced into each of the above-described softening base compositions at a level of 1.28%, by weight, under very low shear conditions. Mixing was achieved with an Oscell-12 shaker operating for 12 seconds at 700 oscillations per minute. Particle size of the softening base compositions was measured before and after the addition of the perfume microemulsion. For purposes of comparison, dispersion "as is" was measured by post-adding pure perfume to each softening base.
  • microemulsion composition was comprised of the following:
  • the softening base composition was comprised of the following: (a) 9.2%, by weight, amidoamine (Rewopal V3340); (b) 4.5% Esterquat (Tetranyl AT1 -75);

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Cosmetics (AREA)
  • Detergent Compositions (AREA)
  • Colloid Chemistry (AREA)
  • Fats And Perfumes (AREA)

Abstract

L'invention concerne un parfum contenant une microémulsion d'eau dans l'huile qui peut être mélangée à une composition de base aqueuse d'un produit assouplissant pour tissus pour conférer un parfum à ce dernier. L'utilisation de la microémulsion définie permet d'ajouter des parfums ainsi que d'autres caractéristiques cosmétiques à une composition de base aqueuse dans des conditions de faible cisaillement tout en évitant tout problème de gélification ou d'instabilité physique dans le produit assouplissant fini.
EP99937670A 1998-07-30 1999-07-29 Emulsion eau dans l'huile pour fournir des caracteristiques cosmetiques a une composition de base d'un produit assouplissant Expired - Lifetime EP1102836B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DK99937670T DK1102836T3 (da) 1998-07-30 1999-07-29 Vand-i-olie-mikroemulsion til opnåelse af kosmetiske egenskaber for sammensætninger baseret på stofblödgörere

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US12630898A 1998-07-30 1998-07-30
US126308 1998-07-30
PCT/US1999/017319 WO2000006690A1 (fr) 1998-07-30 1999-07-29 Emulsion eau dans l'huile pour fournir des caracteristiques cosmetiques a une composition de base d'un produit assouplissant

Publications (2)

Publication Number Publication Date
EP1102836A1 true EP1102836A1 (fr) 2001-05-30
EP1102836B1 EP1102836B1 (fr) 2004-09-22

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EP99937670A Expired - Lifetime EP1102836B1 (fr) 1998-07-30 1999-07-29 Emulsion eau dans l'huile pour fournir des caracteristiques cosmetiques a une composition de base d'un produit assouplissant

Country Status (17)

Country Link
EP (1) EP1102836B1 (fr)
CN (1) CN1168816C (fr)
AT (1) ATE277165T1 (fr)
AU (1) AU774872B2 (fr)
BR (1) BR9912573A (fr)
CA (1) CA2338372A1 (fr)
DE (1) DE69920480T2 (fr)
DK (1) DK1102836T3 (fr)
HU (1) HUP0103066A3 (fr)
IL (1) IL140880A0 (fr)
NO (1) NO20010491D0 (fr)
PL (1) PL345700A1 (fr)
RU (1) RU2232185C2 (fr)
TR (1) TR200100233T2 (fr)
WO (1) WO2000006690A1 (fr)
YU (1) YU6201A (fr)
ZA (1) ZA200100581B (fr)

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Title
See references of WO0006690A1 *

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AU774872B2 (en) 2004-07-08
PL345700A1 (en) 2002-01-02
IL140880A0 (en) 2002-02-10
EP1102836B1 (fr) 2004-09-22
HUP0103066A2 (hu) 2002-02-28
NO20010491L (no) 2001-01-29
AU5245899A (en) 2000-02-21
ZA200100581B (en) 2002-01-21
DE69920480T2 (de) 2005-10-13
TR200100233T2 (tr) 2001-05-21
NO20010491D0 (no) 2001-01-29
RU2232185C2 (ru) 2004-07-10
CA2338372A1 (fr) 2000-02-10
YU6201A (sh) 2003-01-31
CN1311814A (zh) 2001-09-05
HUP0103066A3 (en) 2003-04-28
ATE277165T1 (de) 2004-10-15
WO2000006690A1 (fr) 2000-02-10
BR9912573A (pt) 2001-05-02
DK1102836T3 (da) 2005-01-31
CN1168816C (zh) 2004-09-29
DE69920480D1 (de) 2004-10-28

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