CA2295533A1 - Decorative cosmetic o/w emulsion - Google Patents
Decorative cosmetic o/w emulsion Download PDFInfo
- Publication number
- CA2295533A1 CA2295533A1 CA002295533A CA2295533A CA2295533A1 CA 2295533 A1 CA2295533 A1 CA 2295533A1 CA 002295533 A CA002295533 A CA 002295533A CA 2295533 A CA2295533 A CA 2295533A CA 2295533 A1 CA2295533 A1 CA 2295533A1
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- Prior art keywords
- polyquaternium
- emulsion
- gel
- cosmetic
- emulsion according
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
-
- 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
- A61K8/18—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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/90—Block copolymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
- A61Q1/10—Preparations containing skin colorants, e.g. pigments for eyes, e.g. eyeliner, mascara
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier 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
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
Abstract
The invention relates to a decorative cosmetic O/W emulsion having lasting effect which adheres well to the skin, and which can be applied in all branches of decorative cosmetics. It is colour-stable and can contain high proportions of particle-shaped materials, while having very good humidity characteristics. This emulsion contains 0.1-3 %wt of a cationic gel or gel mixture which is then mixed with water, or with powdery components that are used for decorative purposes and are compatible with the gel, and optionally with other active agents, supporting materials or mixtures thereof. When so mixed, the emulsion acquires a positive zeta potential in the +5 to -+45mV range, for a pH value of 3.0 to 8.0. Furthermore, 5-30 %wt of an oil phase is stably dispersed in the aqueous gel phase of the emulsion, without addition of an emulsifier.
Description
DECORATIVE COSMETIC O/4~T EMULSION
The present invention relates to a cosmetic 0/W emulsion with a long-lasting effect and which is usable in all areas of decorati-ve cosmetics, especially for cosmetic foundations.
Generally, O/W emulsions for makeup products are produced with anionic, non-ionic or amphoteric emulsifiers. A wide variety l0 of emulsifiers is known for this purpose, such as hydrophile amphoteric block copolymers with cationic and anionic groups (US-A-5252692) and copolymers with monomers containing nitrile groups (EP-A-290166). Generally, such conventional emulsions containing emulsifiers often lead to irritations of the skin, especially in the event of frequent or long-term use.
US-A-4913743 deals with treating ceratinic material using a combination of an anionic and a cationic polymer in order to stabilize and support the fibre-like cell structures. US-A-5618522 discloses an 0/W emulsion having an oil phase of 3,000 cps and a thickener, which may be a polymethacrylate polymer, and an aqueous phase as well as an emulsifier which has to be contai-ned in at least one phase. W094/23693 relates to an 0/W emulsion for self-tanning comprising a cationic emulsifier besides DHA, a sunlight protecting agent and a cationic network polymer. EP-A-615741 describes an o/w emulsion comprising an amphiphile compo-nent and an agent being active on the surface together being able to form a gel, oil and water, wherein the total amount of the amphiphile component and the agent being active on the surface are located at the interface of the emulsion particles.
The invention is based on the objective to develop new decorative O/W emulsions with which the aforementioned disadvan-tages do not occur and which form long-lasting products having at the same time a sufficient capacity of accepting pigments in the emulsions.
According to the invention, the decorative cosmetic O/W
emulsion is characterised in that the emulsion comprises 0.1 to AMENDED SHEET
The present invention relates to a cosmetic 0/W emulsion with a long-lasting effect and which is usable in all areas of decorati-ve cosmetics, especially for cosmetic foundations.
Generally, O/W emulsions for makeup products are produced with anionic, non-ionic or amphoteric emulsifiers. A wide variety l0 of emulsifiers is known for this purpose, such as hydrophile amphoteric block copolymers with cationic and anionic groups (US-A-5252692) and copolymers with monomers containing nitrile groups (EP-A-290166). Generally, such conventional emulsions containing emulsifiers often lead to irritations of the skin, especially in the event of frequent or long-term use.
US-A-4913743 deals with treating ceratinic material using a combination of an anionic and a cationic polymer in order to stabilize and support the fibre-like cell structures. US-A-5618522 discloses an 0/W emulsion having an oil phase of 3,000 cps and a thickener, which may be a polymethacrylate polymer, and an aqueous phase as well as an emulsifier which has to be contai-ned in at least one phase. W094/23693 relates to an 0/W emulsion for self-tanning comprising a cationic emulsifier besides DHA, a sunlight protecting agent and a cationic network polymer. EP-A-615741 describes an o/w emulsion comprising an amphiphile compo-nent and an agent being active on the surface together being able to form a gel, oil and water, wherein the total amount of the amphiphile component and the agent being active on the surface are located at the interface of the emulsion particles.
The invention is based on the objective to develop new decorative O/W emulsions with which the aforementioned disadvan-tages do not occur and which form long-lasting products having at the same time a sufficient capacity of accepting pigments in the emulsions.
According to the invention, the decorative cosmetic O/W
emulsion is characterised in that the emulsion comprises 0.1 to AMENDED SHEET
3 % by weight of a cationic gel selected among polyquaternium-31, polyquaternium-16, polyquaternium-24, polyquaternium-7, polyqua-ternium-22, polyquaternium-39, polyquaternium-28, polyquaternium-2, polyquaternium-l0, polyquaternium-11, polyquaternium-37 &
mineral oil & PPG trideceth, PVP dimethylaminoethylmethacrylate copolymer, Guar hydroxypropyltriammonium chloride, calcium alginate, ammonium alginate, Chitosan PCA and mixtures thereof, which in case of being mixed with water and with 8 to 10 ~ by weight (in relation to the total weight of the emulsion) of gel-l0 compatible powdery components used for decorative purposes provi-des a positive zeta potential of the emulsion ranging from +5 to +45 mV at a pH value between 3.0 and 8.0; and that in the aqueous gel phase 5 to 30 ~ by weight of an oil phase are permanently dispersed without adding an emulsifier with the ~5 oil phase being selected among those triglycerides, fatty alco hols, linear and branched esters, esters of polyhydroxy alcohols, vegetable oils or mixtures thereof providing in a mixture with the cationic gel and the powdery components a positive zeta potential.
20 The emulsion may comprise other agents, carrier substances, or mixtures thereof wherein, depending upon the isoelectric point, the component ratios of all raw substances used are adap-ted towards each other in a way to provide an overall positive zeta potential.
25 The employment of 0.3 to 2.5 ~ by weight of gelatinising agent in the aqueous phase, which decisively contributes to the provision of a positive zeta potential in the emulsion, is parti-cularly advantageous. Especially preferred gels are polyquaterni-um-l0 and -37, Chitosan PCA, Guar hydroxypropyltriammonium chlo-30 ride alone or as a mixture of one or several of these substances.
At the same time, the gelatinising agents act as emulsifiers and thus are to be selected with a view to their own zeta poten tial as well as to their emulsifying properties, especially in decorative O/W emulsions.
35 The size of the particles of the emulsion- can be further reduced by adding ethoxylated glycol or polyethylene glycol ( PEG ) in the aqueous phase. Liponic EG1~ made by Lipo or Lutrol e400'°
AMENDED SHEET
made by BASF are suitable PEGS.
Suitable esters of polyols are esters of Coo-C~5 fatty acids and alcohols, esters of Coo-C~5 fatty acids and glycols, or esters of hydroxy fatty acids. Branched C~2-C~5 alkyl esters in con-s junction with other esters such as di- or tri-esters of polyols are particularly advantageous in the oil phase, with esters of linear-chain alcohols and branched acids being particularly favourable. All these suitable esters are derived from primary alcohols.
l0 Suitable substances for the oil phase include C~Z_~5 alkylma-late, neopentyl glycol diheptanoate, propylene glycol dicapryla-te, dioctyl adipate, diisopropyl dimer dilinoleate, diisostearyl dimer dilinoleate, C~2-~3 alkyl lactate, di-C~Z_~3 alkyl tartrate, tri-C~2_~3 alkyl citrate, Ci2_~5 alkyl lactate, PPG dioctanoate, 15 diethylene glycol dioctanoate, meadowfoam oil, babassu oil, jojoba oil, rice oil, C~2_~5 alkyl oleate, avocado oil, tridecyl neopentanoate, beeswax, cetearyl alcohol and polysorbate 60, candelilla wax, C~e_26 triglycerides, cetearyl alcohol & cetearyl glucoside, acetylated lanolin, glyceryl hydroxystearate, C~g_36 20 acid glycol ester, with substances such as C~8_36 triglycerides, glyceryl hydroxystearate, candelilla wax, and mixtures thereof being particularly preferred.
Also, polymers such as polyisobutene, synthetic wax, hydro genated polyisobutene, phytantriol, PVP/hexadecene copolymer may 25 be comprised therein.
The share of the oil phase is preferably within the range from l0 to 25~ by weight, based on the total mass of the emul-sion. The range between 15 to 25o by weight is particularly preferred.
30 The emulsion for use in decorative cosmetics according to the invention contains substances in a powder form selected from the group consisting of pigments such as metal oxides (iron oxides, TiOZ, ultramarine blue, chromium oxide, micaceous titani-um oxide, micaceous iron oxide, manganese purple, zinc oxide, 35 mixtures thereof), and of other powdery substances such as SiOZ, silica, kaolin, kaolin modified with SiOz (as per W096/17588), polytetrafluoroethylene, nylon°', talcum, mica, polymethylmeth-AMENDED SHEET
3a acrylate, polyethylene, natural organic compounds such as encapsulated and non-encapsulated grain starch, dulling means such as polymethacrylate and mixtures thereof.
The emulsion may also comprise large shares of active components which otherwise are difficult to stabilise in a formulation, such as octylmethoxycinnamate which is used as an organic sun protecting agent, or methyl lactate as a refresher.
The emulsion according to the present invention represents a colloidal system.
Depending upon the selected cationic gel or gel mixture, the emulsion according to the present invention may be of a visco-plastic type, e.g. using a Polyquaternium gel such as Polyquaternium 31. In this case, it has a medium yield point in the range from 15 to 40 Pa. The viscosity of this emulsion is lower than l0 Pa~s. The values were determined by means of a Physica US
200 rheometer on the basis of the Herschel-Buckley~equation.
The conus was MK23 (2°).
An essential characteristic of the present invention is the positive zeta potential of the emulsion. Zeta potential is the designation for the galvanic voltage in the diffuse sec tion of the electrochemical double layer at the interface of two non-miscible phases. The electrochemical double layer is known to consist of the Stern layer of firmly adsorbed ions l0 with their surface or Nernst potential (facing the inner par-ticles, in this case the oil droplets) and the Stern potential facing the diffuse layer (Gony-Chapman double layer) . The zeta potential is the potential externally effective for the elec-trokinetic appearance of the particles. When this potential equals zero, the isoelectric point has been reached.
The pH value of the emulsion according to the invention is preferably in the rage from 5.5 to 6.5.
It was found that o/W emulsions with positive zeta poten tial of a composition in accordance with the invention possess an excellent skin adhesion and thus may be processed into highly long-lasting cosmetic products without the fear of skin irritations due to the effects of emulsifiers: This is parti-cularly surprising as it may be deduced from J. Biomat. Appl. , Vol. 3, April 1989, p. 554, that hydrogels generally have a low propensity to adhere to tissues, etc. due to their non-specific absorption of proteins at the hydrogel surfaces, specifically due to the lack of protein absorption due to hydrophobic interactions. Excellent skin adhesion is one of the fundamental advantages of the invention.
Furthermore, the emulsions according to the invention provide a better colour stability than decorative emulsions already known, a fact that could not easily be deduced from their composition.
It was also found that the special gel phase of the emul sions in accordance with the invention can accept a high share of pigments or powdery substances, and that this viscoplastic emulsion thus is especially suited for use in decorative cos-metics. The preferred shares of pigments and/or powdery sub-stances range between 8 - 20 % by weight, preferably l0 - 20 % by weight, in particular 12 - 20 % by weight. It was also 5 found that even small amounts of cationic gelatinising agents with a positive zeta potential ranging from o.l to 0.8 % by weight form stable emulsions.
In order to obtain a generally positive zeta potential in the claimed range, it is necessary to use such raw materials l0 which contribute to the same accordingly. To this, end, the person skilled in the art has to determine the surface load, i.e. the isoelectric point of all raw materials used and to adjust the various shares of the components in a way providing an overall positive zeta potential.
Pigments, for example, slightly reduce the zeta potential as mineral substances often feature a negative load at the pH
values of the emulsion according to the present invention ranging between 5.5 and 6.5 while this pH value lies mostly near the isoelectric points of the pigments. Therefore, the 2o person skilled in the art has to select appropriate cationic gels together with the other agents and/or carrier substances in order to achieve an overall positive zeta potential. Struc-tural similarities between e. g. Polyquaternium-31 (quaternary ammonia salt comprising DMAPA acrylates/acrylic acid/acryloni-trogene copolymer, and diethyl sulphate) and an acrylate block copolymer can very well produce quite different zeta potenti-als in the emulsion, e. g. +38 mV in case of Polyquaternium-31 and -21 mV in case of an acrylate block copolymer.
Finally, it was found that the humidity characteristics of the emulsion according to the present invention are somewhat better than those of comparable emulsions containing additional humidity-keeping substances. Thus, CorneometerA
measurements of skin hydration indicated a value of 12 % 1 hour after applying the emulsion, compared with 11 % in case of the comparative emulsion which contained humidity-keeping substances. After 3 hours the emulsion of the invention indi-cated a value of 4, 5 % compared with 2 % of the comparative emulsion. The comparative emulsion was a so-called "no-tran-sfer foundation" . Significantly better results are expected in comparison with a so-called "transfer-proof foundation". Such emulsions are known to be dehydrating cosmetic substances.
The better humidity characteristics of the emulsion ac s cording to the present invention are probably due to the capa bility of the hydrogel to keep water within its network over.
a long period of time.
The particularly favourable long-lasting adhesion to be achieved by the invention may be documented by investigation, to e.g. of the colour change DE in a formulation in accordance with the invention containing pigments, which is applied onto one half of the face of a test person, in comparison to a formulation with the same composition but a negative zeta potential of the emulsion . While the DE value of approximately 15 22 drops to around 18 after 8 hours in the formulation with the negative zeta potential, the DE value of the emulsion with a positive zeta potential according to the invention applied onto one half of the face remains nearly constant at its in-itial level throughout the period. A feature of the long-la-2o sting effect characteristic for this invention is the skin adhesion without noticeable impairment of the colour or other conditions of the emulsion applied onto the skin over a mini-mum period of 3 hours.
A specific embodiment of the present invention comprises 25 a cosmetic emulsion in which the aqueous phase contains 0.1 to 0.8 ~ by weight of a cationic gel or gel mixture which, if mixed with water and with o .1 to 20 ~ by weight of powdery components and possibly other agents, carrier substances or mixtures thereof, produces a positive zeta potential of the 3o emulsion ranging between +5 and +45 mV at a pH value between 3.0 and 8.0, preferably 5.5 to 6.5, an wherein 5 to 30 ~ by weight of an oil phase are dispersed in a stable manner in the aqueous gel phase without adding an emulsifier.
The present invention is to be described in greater de 35 tail by the examples below. All amounts specified are in per cent by weight.
mineral oil & PPG trideceth, PVP dimethylaminoethylmethacrylate copolymer, Guar hydroxypropyltriammonium chloride, calcium alginate, ammonium alginate, Chitosan PCA and mixtures thereof, which in case of being mixed with water and with 8 to 10 ~ by weight (in relation to the total weight of the emulsion) of gel-l0 compatible powdery components used for decorative purposes provi-des a positive zeta potential of the emulsion ranging from +5 to +45 mV at a pH value between 3.0 and 8.0; and that in the aqueous gel phase 5 to 30 ~ by weight of an oil phase are permanently dispersed without adding an emulsifier with the ~5 oil phase being selected among those triglycerides, fatty alco hols, linear and branched esters, esters of polyhydroxy alcohols, vegetable oils or mixtures thereof providing in a mixture with the cationic gel and the powdery components a positive zeta potential.
20 The emulsion may comprise other agents, carrier substances, or mixtures thereof wherein, depending upon the isoelectric point, the component ratios of all raw substances used are adap-ted towards each other in a way to provide an overall positive zeta potential.
25 The employment of 0.3 to 2.5 ~ by weight of gelatinising agent in the aqueous phase, which decisively contributes to the provision of a positive zeta potential in the emulsion, is parti-cularly advantageous. Especially preferred gels are polyquaterni-um-l0 and -37, Chitosan PCA, Guar hydroxypropyltriammonium chlo-30 ride alone or as a mixture of one or several of these substances.
At the same time, the gelatinising agents act as emulsifiers and thus are to be selected with a view to their own zeta poten tial as well as to their emulsifying properties, especially in decorative O/W emulsions.
35 The size of the particles of the emulsion- can be further reduced by adding ethoxylated glycol or polyethylene glycol ( PEG ) in the aqueous phase. Liponic EG1~ made by Lipo or Lutrol e400'°
AMENDED SHEET
made by BASF are suitable PEGS.
Suitable esters of polyols are esters of Coo-C~5 fatty acids and alcohols, esters of Coo-C~5 fatty acids and glycols, or esters of hydroxy fatty acids. Branched C~2-C~5 alkyl esters in con-s junction with other esters such as di- or tri-esters of polyols are particularly advantageous in the oil phase, with esters of linear-chain alcohols and branched acids being particularly favourable. All these suitable esters are derived from primary alcohols.
l0 Suitable substances for the oil phase include C~Z_~5 alkylma-late, neopentyl glycol diheptanoate, propylene glycol dicapryla-te, dioctyl adipate, diisopropyl dimer dilinoleate, diisostearyl dimer dilinoleate, C~2-~3 alkyl lactate, di-C~Z_~3 alkyl tartrate, tri-C~2_~3 alkyl citrate, Ci2_~5 alkyl lactate, PPG dioctanoate, 15 diethylene glycol dioctanoate, meadowfoam oil, babassu oil, jojoba oil, rice oil, C~2_~5 alkyl oleate, avocado oil, tridecyl neopentanoate, beeswax, cetearyl alcohol and polysorbate 60, candelilla wax, C~e_26 triglycerides, cetearyl alcohol & cetearyl glucoside, acetylated lanolin, glyceryl hydroxystearate, C~g_36 20 acid glycol ester, with substances such as C~8_36 triglycerides, glyceryl hydroxystearate, candelilla wax, and mixtures thereof being particularly preferred.
Also, polymers such as polyisobutene, synthetic wax, hydro genated polyisobutene, phytantriol, PVP/hexadecene copolymer may 25 be comprised therein.
The share of the oil phase is preferably within the range from l0 to 25~ by weight, based on the total mass of the emul-sion. The range between 15 to 25o by weight is particularly preferred.
30 The emulsion for use in decorative cosmetics according to the invention contains substances in a powder form selected from the group consisting of pigments such as metal oxides (iron oxides, TiOZ, ultramarine blue, chromium oxide, micaceous titani-um oxide, micaceous iron oxide, manganese purple, zinc oxide, 35 mixtures thereof), and of other powdery substances such as SiOZ, silica, kaolin, kaolin modified with SiOz (as per W096/17588), polytetrafluoroethylene, nylon°', talcum, mica, polymethylmeth-AMENDED SHEET
3a acrylate, polyethylene, natural organic compounds such as encapsulated and non-encapsulated grain starch, dulling means such as polymethacrylate and mixtures thereof.
The emulsion may also comprise large shares of active components which otherwise are difficult to stabilise in a formulation, such as octylmethoxycinnamate which is used as an organic sun protecting agent, or methyl lactate as a refresher.
The emulsion according to the present invention represents a colloidal system.
Depending upon the selected cationic gel or gel mixture, the emulsion according to the present invention may be of a visco-plastic type, e.g. using a Polyquaternium gel such as Polyquaternium 31. In this case, it has a medium yield point in the range from 15 to 40 Pa. The viscosity of this emulsion is lower than l0 Pa~s. The values were determined by means of a Physica US
200 rheometer on the basis of the Herschel-Buckley~equation.
The conus was MK23 (2°).
An essential characteristic of the present invention is the positive zeta potential of the emulsion. Zeta potential is the designation for the galvanic voltage in the diffuse sec tion of the electrochemical double layer at the interface of two non-miscible phases. The electrochemical double layer is known to consist of the Stern layer of firmly adsorbed ions l0 with their surface or Nernst potential (facing the inner par-ticles, in this case the oil droplets) and the Stern potential facing the diffuse layer (Gony-Chapman double layer) . The zeta potential is the potential externally effective for the elec-trokinetic appearance of the particles. When this potential equals zero, the isoelectric point has been reached.
The pH value of the emulsion according to the invention is preferably in the rage from 5.5 to 6.5.
It was found that o/W emulsions with positive zeta poten tial of a composition in accordance with the invention possess an excellent skin adhesion and thus may be processed into highly long-lasting cosmetic products without the fear of skin irritations due to the effects of emulsifiers: This is parti-cularly surprising as it may be deduced from J. Biomat. Appl. , Vol. 3, April 1989, p. 554, that hydrogels generally have a low propensity to adhere to tissues, etc. due to their non-specific absorption of proteins at the hydrogel surfaces, specifically due to the lack of protein absorption due to hydrophobic interactions. Excellent skin adhesion is one of the fundamental advantages of the invention.
Furthermore, the emulsions according to the invention provide a better colour stability than decorative emulsions already known, a fact that could not easily be deduced from their composition.
It was also found that the special gel phase of the emul sions in accordance with the invention can accept a high share of pigments or powdery substances, and that this viscoplastic emulsion thus is especially suited for use in decorative cos-metics. The preferred shares of pigments and/or powdery sub-stances range between 8 - 20 % by weight, preferably l0 - 20 % by weight, in particular 12 - 20 % by weight. It was also 5 found that even small amounts of cationic gelatinising agents with a positive zeta potential ranging from o.l to 0.8 % by weight form stable emulsions.
In order to obtain a generally positive zeta potential in the claimed range, it is necessary to use such raw materials l0 which contribute to the same accordingly. To this, end, the person skilled in the art has to determine the surface load, i.e. the isoelectric point of all raw materials used and to adjust the various shares of the components in a way providing an overall positive zeta potential.
Pigments, for example, slightly reduce the zeta potential as mineral substances often feature a negative load at the pH
values of the emulsion according to the present invention ranging between 5.5 and 6.5 while this pH value lies mostly near the isoelectric points of the pigments. Therefore, the 2o person skilled in the art has to select appropriate cationic gels together with the other agents and/or carrier substances in order to achieve an overall positive zeta potential. Struc-tural similarities between e. g. Polyquaternium-31 (quaternary ammonia salt comprising DMAPA acrylates/acrylic acid/acryloni-trogene copolymer, and diethyl sulphate) and an acrylate block copolymer can very well produce quite different zeta potenti-als in the emulsion, e. g. +38 mV in case of Polyquaternium-31 and -21 mV in case of an acrylate block copolymer.
Finally, it was found that the humidity characteristics of the emulsion according to the present invention are somewhat better than those of comparable emulsions containing additional humidity-keeping substances. Thus, CorneometerA
measurements of skin hydration indicated a value of 12 % 1 hour after applying the emulsion, compared with 11 % in case of the comparative emulsion which contained humidity-keeping substances. After 3 hours the emulsion of the invention indi-cated a value of 4, 5 % compared with 2 % of the comparative emulsion. The comparative emulsion was a so-called "no-tran-sfer foundation" . Significantly better results are expected in comparison with a so-called "transfer-proof foundation". Such emulsions are known to be dehydrating cosmetic substances.
The better humidity characteristics of the emulsion ac s cording to the present invention are probably due to the capa bility of the hydrogel to keep water within its network over.
a long period of time.
The particularly favourable long-lasting adhesion to be achieved by the invention may be documented by investigation, to e.g. of the colour change DE in a formulation in accordance with the invention containing pigments, which is applied onto one half of the face of a test person, in comparison to a formulation with the same composition but a negative zeta potential of the emulsion . While the DE value of approximately 15 22 drops to around 18 after 8 hours in the formulation with the negative zeta potential, the DE value of the emulsion with a positive zeta potential according to the invention applied onto one half of the face remains nearly constant at its in-itial level throughout the period. A feature of the long-la-2o sting effect characteristic for this invention is the skin adhesion without noticeable impairment of the colour or other conditions of the emulsion applied onto the skin over a mini-mum period of 3 hours.
A specific embodiment of the present invention comprises 25 a cosmetic emulsion in which the aqueous phase contains 0.1 to 0.8 ~ by weight of a cationic gel or gel mixture which, if mixed with water and with o .1 to 20 ~ by weight of powdery components and possibly other agents, carrier substances or mixtures thereof, produces a positive zeta potential of the 3o emulsion ranging between +5 and +45 mV at a pH value between 3.0 and 8.0, preferably 5.5 to 6.5, an wherein 5 to 30 ~ by weight of an oil phase are dispersed in a stable manner in the aqueous gel phase without adding an emulsifier.
The present invention is to be described in greater de 35 tail by the examples below. All amounts specified are in per cent by weight.
Glycereth 26 or PEG 8 4.0 Polyquaternium 10 0.5 propylene glycol dicaprilate dicaprate o.3 PPG-1-Trideceth-6 tocopheryl acetate 0.2 C~z-C~3 alkyl malate 25.0 The emulsion was produced in the usual manner, i. e. by stirring and heating the water to reach 80 ° C and then adding Polyquaternium to to be homogenized at around 8,000 rpm. The oil phase was heated up to 80 °C, and the emulsification with a aqueous phase was carried out at 8,000 rpm. Finally, the resul-ting product was slowly stirred (at about 200 rpm), deaerated and cooled down.
The resulting emulsion had a zeta potential of +2B mV, a pH
value of 6 and a volume-related average particle size of 2.56 ~.m, with 90 % of the particles being smaller than 6.33 um.
The zeta potential was measured using a " Zeta Sizer 3" of Malvern Instruments Ltd., Worcs, Great Britain. The zeta potenti-al was determined on the basis of a laser Doppler microelectro-phoresis. According to this method, the thinned emulsion is injected into a measuring cell; then, a current having a known voltage is applied, and the speed of the particles in a fluid flow is measured by means of laser Doppler velocimetry (LDV) and determined according to the known formula taking into account the viscosity, the migration speed in the direct current field, the dielectric constant and the field strength.
The measurement of the particle sizes was carried out using a "Mastersizer" of Melvern Instruments Ltd.
Example 2: Cosmetic foundation with sun protector deionised water q.s. ad 100 preservative 0.5 ; titanium dioxide 5.0 PE 4.0 ; tocopheryl acetate 0.2 glycereth-25 4 . 0 i C~2-C13 alkyl octanoate 18 . 0 Polyquaternium l0 0.4 ; octylmethoxycinnamate 7.0 iron oxides 1.25 The emulsion was produced in a manner similar to that in Example 1, except that the pigments were added in Glycereth-25 or AMENDED SHEET
The resulting emulsion had a zeta potential of +2B mV, a pH
value of 6 and a volume-related average particle size of 2.56 ~.m, with 90 % of the particles being smaller than 6.33 um.
The zeta potential was measured using a " Zeta Sizer 3" of Malvern Instruments Ltd., Worcs, Great Britain. The zeta potenti-al was determined on the basis of a laser Doppler microelectro-phoresis. According to this method, the thinned emulsion is injected into a measuring cell; then, a current having a known voltage is applied, and the speed of the particles in a fluid flow is measured by means of laser Doppler velocimetry (LDV) and determined according to the known formula taking into account the viscosity, the migration speed in the direct current field, the dielectric constant and the field strength.
The measurement of the particle sizes was carried out using a "Mastersizer" of Melvern Instruments Ltd.
Example 2: Cosmetic foundation with sun protector deionised water q.s. ad 100 preservative 0.5 ; titanium dioxide 5.0 PE 4.0 ; tocopheryl acetate 0.2 glycereth-25 4 . 0 i C~2-C13 alkyl octanoate 18 . 0 Polyquaternium l0 0.4 ; octylmethoxycinnamate 7.0 iron oxides 1.25 The emulsion was produced in a manner similar to that in Example 1, except that the pigments were added in Glycereth-25 or AMENDED SHEET
PEG-8 prior to adding the aqueous phase. Octylmethoxycinnamate was added during the cooling-down phase at a temperature of about 60 C.
In vitro, the resulting emulsion had a sun protection factor (SPF) of 10 and a zeta potent ial of +35.8 mV 1.2 mV, with 80 %
of the particles having a par ticle size of less than 8.80 Vim.
Example 3: Cosmetic foundation deionised water q.s. ad 100 preservative 0.5 l0 kaolin modified with Sio2* 2.5 Polyquaternium l0 0.4 Chitosan PCA 1.5 Glycereth 26 4.0 silica l.o Di-Cj2-C~3-alkyl malate 11.0 iron oxides 1.25 titanium dioxide 5.0 neopentyl glycol diheptanoate 3.0 diethylene glycol dioctanoate / diisononanoate 3.5 tridecyl neopentanoate 2.0 tocopheryl acetate 0.2 myristyl lactate 2.0 cyclomethicone & dimethyconol 1.0 porphyridium cruentum extract 5.0 fragrance 0.4 The emulsion was produced in a manner similar to Example 2. The resulting emulsion had a zeta potential of +32.4 mV ~1.5 mV and a pH value of 6.
* White kaolin modified according to W096/17588 with 0.5 to 10 by weight of spherical Si02 having a particle size < 5 ~,m.
Example 4: Mascara (not pertaining to the invention) deionised water q.s. ad 100 preservative 0.7 PVP 4.0 Polyquaternium l0 0.2 AMENDED SHEET
In vitro, the resulting emulsion had a sun protection factor (SPF) of 10 and a zeta potent ial of +35.8 mV 1.2 mV, with 80 %
of the particles having a par ticle size of less than 8.80 Vim.
Example 3: Cosmetic foundation deionised water q.s. ad 100 preservative 0.5 l0 kaolin modified with Sio2* 2.5 Polyquaternium l0 0.4 Chitosan PCA 1.5 Glycereth 26 4.0 silica l.o Di-Cj2-C~3-alkyl malate 11.0 iron oxides 1.25 titanium dioxide 5.0 neopentyl glycol diheptanoate 3.0 diethylene glycol dioctanoate / diisononanoate 3.5 tridecyl neopentanoate 2.0 tocopheryl acetate 0.2 myristyl lactate 2.0 cyclomethicone & dimethyconol 1.0 porphyridium cruentum extract 5.0 fragrance 0.4 The emulsion was produced in a manner similar to Example 2. The resulting emulsion had a zeta potential of +32.4 mV ~1.5 mV and a pH value of 6.
* White kaolin modified according to W096/17588 with 0.5 to 10 by weight of spherical Si02 having a particle size < 5 ~,m.
Example 4: Mascara (not pertaining to the invention) deionised water q.s. ad 100 preservative 0.7 PVP 4.0 Polyquaternium l0 0.2 AMENDED SHEET
fragrance 0.4 The emulsion was produced in a manner similar to that in Example 2. The resulting emuls ion had a zeta potential of +32.4 mV 1.5 mV and a pH value of 6.
Example 4: Mascara deionised water q.s. ad 100 preservative 0.7 PVP 4.0 Polyquaternium 10 0.2 l0 Guar hydroxypropyltriammonium 0.9 chloride Glycereth 26 2.0 triethanolamine 99 g 2.4 magnesium aluminium silicate 1.0 talcum 1.0 wheat germ oil 1.0 PVP/eicosene copolymer 2.0 iron oxides 12.0 hydrogenated polyisobutene 0.2 cetearyl alcohol 0.1 stearic acid 7.0 carnauba 4.0 sorbitan sesquioleate 1.3 beeswax 4.0 C~8-36 acid triglycerides 8.5 lecithin 1.0 tocopheryl acetate 0.2 All gels and polymers were dispersed in the aqueous pha-se. Then, the pigments were dispersed.
The emulsion was com-pleted at 85 C.
The resulting emulsion had a zeta potential of 29.1 mV
1.6 mV; due to the high wax concentration, it contains an emulsifier.
Example 5: Eyeliner deionised water q.s. ad 100 The emulsion was produced in a manner similar to that in Example 2. The resulting emulsion had a zeta potential of +18.1 mV ~4.5 mV.
Example 6: Cosmetic foundation 5 This cosmetic foundation has the advantage of not being trans-ferred onto textiles.
deionised water q.s. ad 100 preservative 0.5 10 Glycereth 26 4.0 C12-C73-alkyl malate 4.2 iron oxides 10.5 Polyquaternium 31 0.4 diethylene glycol dioctanoate / diisononanoate 4.5 tocopheryl acetate 0.2 myristyl lactate 3.5 dicaprylyl ether 3.0 cetearyl alcohol 4.0 jojoba ester 1.5 polymethyl methacrylate 2.5 fragrance 0.4 The emulsion was produced in a manner similar to that in Example 2. At a pH value of 6, the resulting emulsion had a zeta potential of +35.8 mV ~1.2 mV.
Comparative Example 1:
An emulsion similar to that in Example 3 was produced with the following composition:
deionised water q.s. ad 100 preservative 0.5 kaolin modified with Si02 * 1.0 xanthan gum 0.3 silica 1.0 Di-C~Z-C~3-alkyl malate 11.0 propylene glycol 6.25 AMENDED SHEET
Example 4: Mascara deionised water q.s. ad 100 preservative 0.7 PVP 4.0 Polyquaternium 10 0.2 l0 Guar hydroxypropyltriammonium 0.9 chloride Glycereth 26 2.0 triethanolamine 99 g 2.4 magnesium aluminium silicate 1.0 talcum 1.0 wheat germ oil 1.0 PVP/eicosene copolymer 2.0 iron oxides 12.0 hydrogenated polyisobutene 0.2 cetearyl alcohol 0.1 stearic acid 7.0 carnauba 4.0 sorbitan sesquioleate 1.3 beeswax 4.0 C~8-36 acid triglycerides 8.5 lecithin 1.0 tocopheryl acetate 0.2 All gels and polymers were dispersed in the aqueous pha-se. Then, the pigments were dispersed.
The emulsion was com-pleted at 85 C.
The resulting emulsion had a zeta potential of 29.1 mV
1.6 mV; due to the high wax concentration, it contains an emulsifier.
Example 5: Eyeliner deionised water q.s. ad 100 The emulsion was produced in a manner similar to that in Example 2. The resulting emulsion had a zeta potential of +18.1 mV ~4.5 mV.
Example 6: Cosmetic foundation 5 This cosmetic foundation has the advantage of not being trans-ferred onto textiles.
deionised water q.s. ad 100 preservative 0.5 10 Glycereth 26 4.0 C12-C73-alkyl malate 4.2 iron oxides 10.5 Polyquaternium 31 0.4 diethylene glycol dioctanoate / diisononanoate 4.5 tocopheryl acetate 0.2 myristyl lactate 3.5 dicaprylyl ether 3.0 cetearyl alcohol 4.0 jojoba ester 1.5 polymethyl methacrylate 2.5 fragrance 0.4 The emulsion was produced in a manner similar to that in Example 2. At a pH value of 6, the resulting emulsion had a zeta potential of +35.8 mV ~1.2 mV.
Comparative Example 1:
An emulsion similar to that in Example 3 was produced with the following composition:
deionised water q.s. ad 100 preservative 0.5 kaolin modified with Si02 * 1.0 xanthan gum 0.3 silica 1.0 Di-C~Z-C~3-alkyl malate 11.0 propylene glycol 6.25 AMENDED SHEET
Example 2. At a pH value of 6, the resulting emulsion had a zeta potential of +35.8 mV 1.2 mV.
Comparative Example 1:
An emulsion similar to that in Example 3 was produced with the following composition:
deionised water q.s. ad 100 preservative 0.5 kaolin modified with Si02 * 1.0 xanthan gum 0.3 l0 silica 1.0 Di-C~2-C~3-alkyl malate 11.0 propylene glycol 6.25 iron oxides 1.25 titanium dioxide 5.0 neopentyl glycol diheptanoate 3.0 diethylene glycol dioctanoate / diisononanoate 3.5 tridecyl neopentanoate 2.0 acrylic acid / acrylonitrogen 3.4 copolymer myristyl lactate 2.0 cyclomethicone & dimethyconol 1.0 fragrance 0.4 * as per W096/17588 The emulsion was produced in a manner similar to that in Example 3. At a pH value of 5.5, the resulting emulsion had a zeta potential of -41.4 mV ~7.9 mV.
The emulsion of Example 3 and the Comparative Example 1 3o were subjected to a colour test to determine ~E over a period of 8 hours. The results described earlier were achieved.
Comparative Example 1:
An emulsion similar to that in Example 3 was produced with the following composition:
deionised water q.s. ad 100 preservative 0.5 kaolin modified with Si02 * 1.0 xanthan gum 0.3 l0 silica 1.0 Di-C~2-C~3-alkyl malate 11.0 propylene glycol 6.25 iron oxides 1.25 titanium dioxide 5.0 neopentyl glycol diheptanoate 3.0 diethylene glycol dioctanoate / diisononanoate 3.5 tridecyl neopentanoate 2.0 acrylic acid / acrylonitrogen 3.4 copolymer myristyl lactate 2.0 cyclomethicone & dimethyconol 1.0 fragrance 0.4 * as per W096/17588 The emulsion was produced in a manner similar to that in Example 3. At a pH value of 5.5, the resulting emulsion had a zeta potential of -41.4 mV ~7.9 mV.
The emulsion of Example 3 and the Comparative Example 1 3o were subjected to a colour test to determine ~E over a period of 8 hours. The results described earlier were achieved.
Claims (13)
1. Decorative cosmetic O/W emulsion, characterised in that said emulsion comprises 0.1 to 3 % by weight of a cationic gel selected among polyquaternium-31, polyquaternium-16, polyquaternium-24, polyquaternium-7, polyquaternium-22, polyquaternium-39, polyquaternium-28, polyquaternium-2, polyquaternium-10, polyquaternium-11, polyquaternium-37 & mineral oil & PPG trideceth, PVP
dimethylaminoethylmethacrylate copolymer, Guar hydroxypropyl-triammonium chloride, calcium alginate, ammonium alginate, Chitosan PCA and mixtures thereof, wherein the gel in a mixture with water and, related to the total amount of the emulsion, with 8 to 20 % by weight of gel-compatible powdery components for decorative purposes provides a positive zeta potential of the emulsion in the range of +5 to +45 mV at a pH value of 3.0 to 8.0, and in that 5 to 30 % by weight of an oil phase are dispersed in a stable manner in the aqueous gel phase without adding an emulsifier, with the oil phase being selected among those triglycerides, fatty alcohols, linear and branched esters, esters of polyhydroxy alcohols, vegetable oils or mixtures thereof providing in a mixture with the cationic gel and the powdery components a positive zeta potential, and in that the zeta potential is measured by measuring the velocity of the emulsion particles at a known voltage in a liquid flow via laser Doppler velocimetry and by determining the value depending upon viscosity, the travel speed in the direct current field, the dielectric constant and the field intensity.
dimethylaminoethylmethacrylate copolymer, Guar hydroxypropyl-triammonium chloride, calcium alginate, ammonium alginate, Chitosan PCA and mixtures thereof, wherein the gel in a mixture with water and, related to the total amount of the emulsion, with 8 to 20 % by weight of gel-compatible powdery components for decorative purposes provides a positive zeta potential of the emulsion in the range of +5 to +45 mV at a pH value of 3.0 to 8.0, and in that 5 to 30 % by weight of an oil phase are dispersed in a stable manner in the aqueous gel phase without adding an emulsifier, with the oil phase being selected among those triglycerides, fatty alcohols, linear and branched esters, esters of polyhydroxy alcohols, vegetable oils or mixtures thereof providing in a mixture with the cationic gel and the powdery components a positive zeta potential, and in that the zeta potential is measured by measuring the velocity of the emulsion particles at a known voltage in a liquid flow via laser Doppler velocimetry and by determining the value depending upon viscosity, the travel speed in the direct current field, the dielectric constant and the field intensity.
2. Cosmetic emulsion according to Claim 1, characterised in that it contains further agents, carrier substances or mixtures thereof wherein, depending upon the isoelectric point of all raw substances used, the component ratios are adapted towards each other in a way to provide an overall positive zeta potential.
3. Cosmetic emulsion according to Claim 2, characterised in that the aqueous phase contains a gelatinising agent at a ratio of 0.1 to 0.8 % by weight in the aqueous phase which results in a positive zeta potential in the emulsion.
4. Cosmetic emulsion according to Claim 1, characterised in that the gelatinising agent is polyquaternium-10, polyquaternium-37, Guar hydroxypropyltriammonium chloride or a mixture thereof.
5. Cosmetic emulsion according to Claim 1 or Claim 4, characterised in that the gelatinising agent is Chitosan PCA or a mixture with one of the gels polyquaternium-10, polyquaternium-37 or Guar hydroxypropyltriammonium chloride.
6. Cosmetic emulsion according to Claim 6, characterised in that said triglycerides comprise C18-36 acid triglycerides, glyceryl hydroxystearate, candelilla wax and mixtures thereof.
7. Cosmetic emulsion according to Claim 6, characterised in that said fatty alcohols comprise cetearyl alcohol and stearyl alcohol.
8. Cosmetic emulsion according to any one of claims 1 to 3, characterised in that the aqueous phase further contains a polyethylene glycol.
9. Cosmetic emulsion according to Claim 1, characterised in that the aqueous phase contains powdery substances selected from the group consisting of pigments on the basis of metal oxides such as iron oxides, TiO2, ultramarine blue, micaceous titanium oxide, micaceous iron oxides zinc oxide and mixtures thereof; other powdery substances such as silica, kaolin, kaolin modified with SiO2, polytetrafluoroethylene, nylon~, talcum, mica, polyethylene, natural organic compounds such as encapsulated or non-encapsulated grain starch; and mixtures thereof.
10. Cosmetic emulsion according to any one of claims 1 to 9, characterised in that the particle size in the emulsion is smaller than 15 µm.
11. Cosmetic emulsion according to claims 1 to 10, characterised in that the share of the oil phase is in the range of 10 to 20 by weight, based on the total amount of the emulsion.
12. Cosmetic emulsion according to Claim 1, characterised in that the pH value of the emulsion is in the range from 5.5 to 6.5.
13. Cosmetic emulsion according to any of Claims 1 to 5, characterised in that the aqueous phase contains 0.1 to 0.8 % by weight of a cationic gel or gel mixture.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19733625.6 | 1997-07-28 | ||
| DE19733625A DE19733625A1 (en) | 1997-07-28 | 1997-07-28 | Decorative cosmetic O / W emulsion |
| PCT/DE1998/002085 WO1999006010A2 (en) | 1997-07-28 | 1998-07-21 | Decorative cosmetic o/w emulsion without emulsifier |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2295533A1 true CA2295533A1 (en) | 1999-02-11 |
Family
ID=7837918
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002295533A Abandoned CA2295533A1 (en) | 1997-07-28 | 1998-07-21 | Decorative cosmetic o/w emulsion |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1001731B1 (en) |
| JP (1) | JP2001511434A (en) |
| CN (1) | CN1119981C (en) |
| CA (1) | CA2295533A1 (en) |
| DE (2) | DE19733625A1 (en) |
| ES (1) | ES2221202T3 (en) |
| PL (1) | PL193385B1 (en) |
| WO (1) | WO1999006010A2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019077258A1 (en) | 2017-10-16 | 2019-04-25 | Genialis Biotech | Oil-in-water emulsion based on essential oils, and formulated without surfactant |
| WO2019077259A1 (en) | 2017-10-16 | 2019-04-25 | Genialis Biotech | Oil-in-water emulsion based on vegetable oils, and formulated without surfactant |
| WO2019138190A1 (en) | 2018-01-10 | 2019-07-18 | Genialis Biotech | Stable emulsions based on plant oils and on essential oils formulated without surfactant |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19834821A1 (en) | 1998-08-01 | 2000-02-03 | Beiersdorf Ag | Emulsifier-free finely dispersed systems of the oil-in-water and water-in-oil type |
| GB0006866D0 (en) * | 2000-03-21 | 2000-05-10 | Unilever Plc | Low Ph high fatty acid vanishing cream |
| CN100350895C (en) * | 2003-05-09 | 2007-11-28 | 宝洁公司 | Wet skin treatment compositions comprising gel-networks |
| WO2005030155A1 (en) * | 2003-09-26 | 2005-04-07 | L'oréal | Continuous aqueous phase-based photoprotective composition containing a polymer comprising at least two blocks incompatible with each other and having different glass transition temperatures |
| FR2860155A1 (en) * | 2003-09-26 | 2005-04-01 | Oreal | Photoprotective composition, comprising light absorbers and segmented polymer, useful for protection of skin, where the polymer increases the light protection factor |
| CN103006468B (en) * | 2012-12-28 | 2014-07-16 | 纳润（厦门）科技有限公司 | Moisturizing milk and preparation method thereof |
| JP2020536885A (en) | 2017-10-10 | 2020-12-17 | ザ プロクター アンド ギャンブル カンパニーＴｈｅ Ｐｒｏｃｔｅｒ ＆ Ｇａｍｂｌｅ Ｃｏｍｐａｎｙ | Sulfate-free personal cleansing composition with low mineral salt content |
| FR3075054B1 (en) * | 2017-12-15 | 2020-12-25 | Lvmh Rech | COSMETIC COMPOSITION INCLUDING A PULLULAN DERIVATIVE |
| WO2021146273A1 (en) * | 2020-01-13 | 2021-07-22 | The Procter & Gamble Company | Personal care composition comprising aloe vera |
| JP7481470B2 (en) | 2020-02-27 | 2024-05-10 | ザ プロクター アンド ギャンブル カンパニー | Sulfur-containing anti-dandruff compositions with enhanced efficacy and aesthetics |
| KR102194279B1 (en) * | 2020-06-25 | 2020-12-22 | 코스맥스 주식회사 | Cationic cosmetic composition for enhancing makeup adhesion and preventing staining |
| CN116568263A (en) | 2020-12-04 | 2023-08-08 | 宝洁公司 | Hair care composition comprising malodor reduction materials |
| US11771635B2 (en) | 2021-05-14 | 2023-10-03 | The Procter & Gamble Company | Shampoo composition |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2077831B2 (en) * | 1970-02-17 | 1976-07-09 | Marcarian Jean | |
| IT1163973B (en) * | 1978-03-17 | 1987-04-08 | Shiseido Co Ltd | COMPOSITION OF GEL INCLUDING A CLAY MINERAL AND A LIQUID CRYSTAL, AND COSMETIC PREPARATION THAT CONTAINS IT |
| US4913743A (en) * | 1987-04-15 | 1990-04-03 | Biomatrix, Inc. | Processes for managing keratinous material using glycosaminoglycan and cationic polymer combinations |
| DE4015108A1 (en) * | 1990-05-11 | 1991-11-14 | Leopold Pharma Gmbh | STABLE EMULSION FOR APPLICATION OF PHARMACOLOGICALLY ACTIVE ACTIVE SUBSTANCES |
| AU1775592A (en) * | 1991-04-03 | 1992-11-02 | Richardson-Vicks Inc. | Stabilized emulsion compositions for imparting an artificial tan to human skin |
| IL101241A (en) * | 1992-03-16 | 1997-11-20 | Yissum Res Dev Co | Pharmaceutical or cosmetic composition comprising stabilized oil-in-water type emulsion as carrier |
| JP3398171B2 (en) * | 1993-03-15 | 2003-04-21 | 株式会社資生堂 | Oil-in-water emulsion composition |
| CA2160107C (en) * | 1993-04-16 | 1999-07-06 | George Endel Deckner | Compositions for imparting an artificial tan and protecting the skin from uv radiation |
| FR2720934B1 (en) * | 1994-06-14 | 1996-07-12 | Oreal | Oil-in-water cleaning emulsion with the appearance of milk. |
| FR2722116B1 (en) * | 1994-07-11 | 1996-08-23 | Oreal | OIL-IN-WATER EMULSION WITHOUT SURFACTANT, STABILIZED BY HOLLOW THERMOPLASTIC PARTICLES |
| DE4425268C2 (en) * | 1994-07-16 | 1998-05-28 | Beiersdorf Ag | Emulsifier-free, finely dispersed cosmetic or dermatological preparations of the oil-in-water type |
| US5618522A (en) * | 1995-01-20 | 1997-04-08 | The Procter & Gamble Company | Emulsion compositions |
| ES2093562B1 (en) * | 1995-05-26 | 1997-07-01 | Univ Santiago Compostela | STABILIZATION OF COLLOID SYSTEMS THROUGH FORMATION OF LIPIDO-POLISACARIDO IONIC COMPLEXES. |
| DE19638729B4 (en) * | 1996-09-13 | 2004-09-23 | Lancaster Group Gmbh | Stable multi-phase emulsion type 01 / W / O2, process for its preparation and its use |
-
1997
- 1997-07-28 DE DE19733625A patent/DE19733625A1/en not_active Ceased
-
1998
- 1998-07-21 CA CA002295533A patent/CA2295533A1/en not_active Abandoned
- 1998-07-21 DE DE59811391T patent/DE59811391D1/en not_active Expired - Lifetime
- 1998-07-21 WO PCT/DE1998/002085 patent/WO1999006010A2/en active IP Right Grant
- 1998-07-21 ES ES98947327T patent/ES2221202T3/en not_active Expired - Lifetime
- 1998-07-21 CN CN98807661A patent/CN1119981C/en not_active Expired - Fee Related
- 1998-07-21 JP JP2000504827A patent/JP2001511434A/en not_active Abandoned
- 1998-07-21 EP EP98947327A patent/EP1001731B1/en not_active Expired - Lifetime
- 1998-07-21 PL PL98338183A patent/PL193385B1/en not_active IP Right Cessation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019077258A1 (en) | 2017-10-16 | 2019-04-25 | Genialis Biotech | Oil-in-water emulsion based on essential oils, and formulated without surfactant |
| WO2019077259A1 (en) | 2017-10-16 | 2019-04-25 | Genialis Biotech | Oil-in-water emulsion based on vegetable oils, and formulated without surfactant |
| WO2019138190A1 (en) | 2018-01-10 | 2019-07-18 | Genialis Biotech | Stable emulsions based on plant oils and on essential oils formulated without surfactant |
Also Published As
| Publication number | Publication date |
|---|---|
| DE19733625A1 (en) | 1999-02-04 |
| PL193385B1 (en) | 2007-02-28 |
| JP2001511434A (en) | 2001-08-14 |
| CN1119981C (en) | 2003-09-03 |
| PL338183A1 (en) | 2000-10-09 |
| EP1001731B1 (en) | 2004-05-12 |
| EP1001731A2 (en) | 2000-05-24 |
| DE59811391D1 (en) | 2004-06-17 |
| ES2221202T3 (en) | 2004-12-16 |
| WO1999006010A3 (en) | 1999-06-10 |
| CN1265020A (en) | 2000-08-30 |
| WO1999006010A2 (en) | 1999-02-11 |
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