WO2004075868A1 - O/w-emulgator, sowie o/w-emulsionen enthaltend kalium-cetylphosphat und verfahren zu deren herstellung - Google Patents

O/w-emulgator, sowie o/w-emulsionen enthaltend kalium-cetylphosphat und verfahren zu deren herstellung Download PDF

Info

Publication number
WO2004075868A1
WO2004075868A1 PCT/EP2004/001865 EP2004001865W WO2004075868A1 WO 2004075868 A1 WO2004075868 A1 WO 2004075868A1 EP 2004001865 W EP2004001865 W EP 2004001865W WO 2004075868 A1 WO2004075868 A1 WO 2004075868A1
Authority
WO
WIPO (PCT)
Prior art keywords
emulsifier
weight
water
emulsion
cetyl phosphate
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.)
Ceased
Application number
PCT/EP2004/001865
Other languages
German (de)
English (en)
French (fr)
Inventor
Bernd Schröder
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.)
Symrise AG
Original Assignee
Symrise AG
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 Symrise AG filed Critical Symrise AG
Priority to JP2006501953A priority Critical patent/JP2006519686A/ja
Priority to US10/546,617 priority patent/US20060171913A1/en
Priority to EP04714278A priority patent/EP1599176A1/de
Publication of WO2004075868A1 publication Critical patent/WO2004075868A1/de
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04Dispersions; Emulsions
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04Dispersions; Emulsions
    • A61K8/06Emulsions
    • A61K8/062Oil-in-water emulsions
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37Esters of carboxylic acids
    • A61K8/375Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/55Phosphorus compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/017Mixtures of compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair

Definitions

  • Emulsions are usually formed from two liquid phases that are immiscible. When producing an emulsion, one phase is dispersed in finely divided form in the other phase.
  • emulsions There are two main types of emulsions, namely "water-in-oil” and "oil-in”
  • oil-in-water emulsion (O / W emulsion)
  • the oil is the inner phase, which is dispersed in the outer (water) phase.
  • the properties of the corresponding emulsion are essentially determined by the outer phase, so that water-in-oil emulsions (W / O emulsions) tend to look more like oils and oil-in-water emulsions (O / W emulsions)
  • the present invention relates to a multifunctional oil-in-water emulsifier (O / W emulsifier) for the production of O / W emulsions which is free of polyethylene glycol (PEG).
  • O / W emulsifier oil-in-water emulsifier
  • PEG polyethylene glycol
  • O / W emulsifier which requires only a low dosage, is universally suitable for the production of emulsions with different viscosities (for example lotions, milks and creams), in a wide pH range (from eg pH 3 to 11) can be used and has excellent skin tolerance.
  • the O / W emulsifier to be specified should preferably also be PEG-free.
  • the object is achieved by specifying an O / W emulsifier comprising: (a) hardened palm oil glycerides and (b) potassium cetyl phosphate, the proportion of potassium cetyl phosphate being in the range from 40 to 80% by weight .-%, based on the total mass of the emulsifier.
  • Potassium cetyl phosphate (CAS-No .: 19035-79-1) has the empirical formula C 16 H 34 0 4 PK and the structural formula
  • the invention is based on the surprising discovery that potassium cetyl phosphate, hardened at 'the simultaneous presence of palm oil glycerides (mono-, di- and triglycerides of fatty acids contained in palm oil, eg the mono-, di- and triglycerides of oleic acid, the Palmitic acid, stearic acid, myristic acid, lignoceric acid and palmitoleic acid) can be used at a low dosage to produce stable, skin-smoothing O / W emulsions.
  • palm oil glycerides mono-, di- and triglycerides of fatty acids contained in palm oil, eg the mono-, di- and triglycerides of oleic acid, the Palmitic acid, stearic acid, myristic acid, lignoceric acid and palmitoleic acid
  • the O / W emulsifier according to the invention preferably contains no polyethylene glycol (PEG) and / or no other glycol and / or no paraffin and / or no isoparaffin.
  • PEG polyethylene glycol
  • the O / W emulsifier according to the invention usually comprises (a) hardened palm oil glycerides, (b) potassium cetyl phosphate,
  • the cetyl alcohol can result from the production process for the potassium cetyl phosphate. This is because cetyl alcohol is first esterified with phosphoric acid and then neutralized (fully neutralized) with potassium hydroxide, i.e. one acidic proton per molecule is neutralized by potassium hydroxide and the resulting negative charge is neutralized by a potassium ion. If an excess of cetyl alcohol over phosphoric acid is used, cetyl alcohol remains in the product mixture after the esterification.
  • O / W emulsifiers which consist of:
  • the O / W emulsifier according to the invention in particular in its preferred configurations, enables thermostable emulsions even at low use concentrations ( ⁇ 10% by weight).
  • O / W emulsifiers according to the invention is versatile; in particular, they can be used for high-viscosity creams, medium-viscosity milks and lotions as well as low-viscosity, spray-resistant lotions.
  • O / W emulsifiers enables good dispersion of solids in the resulting emulsion systems.
  • the emulsions formulated with the aid of the O / W emulsifiers according to the invention are notable for their largely pH-independent behavior.
  • formulations can be prepared using polar and non-polar oils.
  • O / W emulsifiers according to the invention are compatible with hydrogel formers and hydrocolloids.
  • a combination of the O / W emulsifiers according to the invention with UV / A and UV / B filters is particularly advantageous.
  • the O / W emulsifier according to the invention has very good skin compatibility.
  • a particular advantage of the O / W emulsifier according to the invention in comparison with previously conventional O / W emulsifiers is that the emulsifier according to the invention can be in the form of a lozenge.
  • the pastille shape is also the preferred form of packaging the O / W emulsifier according to the invention.
  • O / W emulsifiers according to the invention Due to the chemical composition of the O / W emulsifiers according to the invention, their physical and chemical properties are largely determined, but certain variations are nonetheless possible. O / W emulsifiers according to the invention which have met one, more or preferably all of the following conditions have proven to be particularly advantageous:
  • the pH is in the range of 5.0 -
  • the saponification number with a saponification time of 1 hour is in the range of 125.0 -155.0 (test method 21 1)
  • the acid number when using the solvent system diethyl ether: ethanol: water 1: 1: 1 (v / v / v) is in the range of 50.0 - 80.0 mg KOH / g (test method 228).
  • the melting point of an O / W emulsifier according to the invention is preferably set so that it is in the range from 75 to 80 ° C.
  • the setting of the Melting point is controlled in particular by the content of cetyl alcohol in the O / W emulsifier.
  • incorporation of an O / W emulsifier according to the invention into an emulsion can optionally take place via the water phase or the oil phase; incorporation via the water phase is often preferred since this generally gives a better emulsion image (better visual assessment).
  • an O / W emulsion comprising:
  • a proportion of 0.25 to 0.50% by weight of the O / W emulsifier according to the invention is often sufficient to stabilize emulsions.
  • Use concentrations which are in the range from 0.5 to 3.0% by weight are typically used to prepare O / W emulsions.
  • O / W emulsifier according to the invention is frequently used for medium-viscosity lotions.
  • creams and hair gels between 1.0 and 15.0% by weight, but preferably between 2.0 and 3.0% by weight, are used as the O / W emulsifier according to the invention.
  • the O / W emulsifier according to the invention can be particularly practical to process the O / W emulsifier according to the invention in the water phase and at the same time to process propylene glycol and / or pentylene glycol (Hydrolite-5).
  • the Solution temperature of the O / W emulsifier according to the invention can be reduced in the water phase.
  • the O / W emulsifier according to the invention is preferably predissolved in the raw material (propylene glycol and / or pentylene glycol), the solution temperature being approximately 75 ° C.
  • the liquid phase consisting of the O / W emulsifier and raw material (solvent) is then preferably subsequently mixed with the other constituents of the water phase, it being sufficient to heat the entire water phase to approximately 65 ° C. (provided the other constituents of the water phase permit this) ,
  • propylene glycol and / or pentylene glycol can also be incorporated into the water phase beforehand, the O / W emulsifier according to the invention then being added to the resulting water phase.
  • the influence on the solution temperature of the O / W emulsifier is not so high; the solution temperature is then around 80-83 ° C.
  • the O / W emulsions according to the invention are distinguished, inter alia, by: good viscosity stability, high pH stability or pH-independent stability, good temperature stability, a very fine and homogeneous emulsion structure with a glossy finish
  • An O / W emulsion according to the invention advantageously comprises a water phase, an oil phase dispersed in the water phase and 0.25-15% by weight, preferably 1-15% by weight, of an O / W emulsifier according to the invention, the percentage by weight being based on the Total mass of the O / W emulsion is related.
  • preferred O / W emulsions additionally comprise 0.1-10% by weight of a stabilizing agent and / or 1-10% by weight of a co-emulsifier, the percentage by weight being based on the total mass of the O / W emulsion.
  • the pH of an O / W emulsion according to the invention can vary within wide limits.
  • the pH is advantageously set to a value between 3 and 11, preferably between 4 and 9, more preferably between 4 and 7.
  • co-emulsifiers e.g. Glycerol monostearates or other glycerol monoesters of fatty acids, steric acid or other fatty acids (unsaponified or partially saponified), waxes or fatty alcohols are used.
  • Hydrogel formers such as e.g. Carbomers, acrylate cross-polymers, xantans, alginates etc. can be used.
  • preferred O / W emulsions are free from ethylene glycol (PEG), other glycols, paraffin and / or isoparaffin.
  • the O / W emulsion according to the invention can comprise further constituents, in particular: dispersed solids and / or
  • emulsifiers according to the invention in the emulsions according to the invention with light protection filters (UV / A and / or UV / B filters), their distributability on the skin is improved and increased water resistance compared to other emulsions is achieved.
  • the emulsifier according to the invention has the following effect in an emulsion according to the invention, alone or together with other cosmetic auxiliaries:
  • UV filters UVA and / or UVB protection
  • Stabilization of UV filters improved photo stabilization
  • Improvement of the solubility and / or suspension of solid UV filters Increasing the water resistance of sun protection products; Support in the formation of a gel network structure; Increasing the effectiveness of active substances, e.g.
  • Formulation examples skin care cream (O / W), body lotion, sun protection cream (O / W), sun protection milk (O / W), sprayable sun milk (O / W), sensitive balm roll-on and cream (O / W), sprayable deodorant Lotion, antiperspirant lotion, hair conditioner, hair gel wax for men, hair cream, tinted day cream, mascara, care lotion for wet wipes.
  • the emulsifier according to the invention can be combined with the following raw materials:
  • the emulsifier according to the invention can be formulated together with light stabilizers.
  • Suitable light stabilizers are, for example, organic UV absorbers from the class of 4-aminobenzoic acid and derivatives, salicylic acid derivatives, benzophenone derivatives, dibenzoylmethane derivatives, diphenylacrylates, 3-imidazol-4-yl-acrylic acid and their esters, benzofuran derivatives, Benzylidene malonate derivatives, polymeric UV absorbers (containing one or more organic silicon residues), cinnamic acid derivatives, camphor derivatives, trianilino-s-triazine derivatives, 2-hydroxyphenylbenzotriazole derivatives, 2-
  • Phenylbenzimidazole-5-sulfonic acid and its salts Anthranilamidementhylester, benzotriazole derivatives.
  • the emulsifier according to the invention can also be incorporated into cosmetic and / or dermatological preparations which contain pigments, preferably finely divided pigments. These can be organic or inorganic pigments.
  • Preferred organic pigment is 2,2'-methylene-bis- [6- (2H-benzotriazol-2-yl) -4- (1, 1, 3,3tetramethylbutyl) phenol] (Tinosorb ® M).
  • Suitable inorganic pigments or micropigments based on metal oxides and / or other metal compounds which are sparingly soluble or insoluble in water are, in particular, oxides of titanium (Ti0 2 ), zinc (ZnO), iron (eg Fe 2 0 3 ), zirconium (Zr0 2 ), silicon (Si0 2 ), manganese (eg MnO), aluminum (Al 2 0 3 ), cerium (eg Ce 2 03), mixed oxides of the corresponding metals and mixtures of such oxides.
  • These pigments are X-ray amorphous or non-X-ray amorphous. Finely divided pigments based on Ti 0 2 and ZnO are particularly preferred.
  • the emulsifier according to the invention can also be incorporated into cosmetic and / or dermatological preparations (emulsions) which are composed as usual and the cosmetic and / or dermatological light protection, further for the treatment, care and cleaning of the skin and / or hair and as Make-up product used in decorative cosmetics.
  • preparations of this type depending on their structure, can be used, for example, as skin protection cream, cleansing milk, sunscreen lotion, nutritional cream, day or night cream, etc.
  • Such preparations (emulsions) can be present, for example, as a lotion, milk, cream, hydrodispersion gel, balm, spray, foam, hair shampoo, hair care product, hair conditioner, roll-on, stick or make-up.
  • the cosmetic and dermatological preparations mentioned by way of example are applied to the skin and / or the hair in a sufficient amount in the manner customary for cosmetics.
  • Mineral oils such as mineral waxes; - Oils, such as triglycerides of capric or caprylic acid, more natural
  • Oils such as Castor oil
  • Fats, waxes and other natural and synthetic fat bodies preferably esters of fatty acids with alcohols of low C number ( ⁇ 10), e.g. with isopropanol, propylene glycol or glycerin, or esters of fatty alcohols with low C number alkanoic acids ( ⁇ 10) or with fatty acids;
  • Silicone oils such as dimethylpolysiloxane, diethylpolysiloxane, diphenylpolysiloxane and mixed forms thereof.
  • the lipid phase of the emulsions, oleogels or hydrodispersions or lipodispersions within the meaning of the present publication are advantageously selected from the group of esters from saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 3 to 30 carbon atoms and saturated and / or unsaturated, branched and / or unbranched alcohols with a chain length of 3 to 30 carbon atoms, from the group of esters from aromatic carboxylic acids and saturated and / or unsaturated, branched and / or unbranched alcohols with a chain length of 3 to 30 carbon atoms. atoms.
  • ester oils can then advantageously be selected from the group of isopropyl myristate, palmitate, stearate, oleate, n-butyl stearate, n-hexyl laurate, n-decyl oleate, isooctyl stearate, isononyl stearate, isononyl isononateate, 2-ethylhexyl palateate, ethyl 2-hexylurate, ethyl 2-hexylurate, ethyl 2-ethyl-acrylate , 2-octyldodecyl palmitate, oleyl oleate, olerlerucate, erucyl oleate and synthetic, semisynthetic and natural mixtures of such esters, for example jojoba oil, 2-ethylhexyl-2-ethylhexanoate, cetearyl-2-ethylhex
  • the lipid phase can advantageously be selected from the group of branched and unbranched hydrocarbons and waxes, silicone oils, dialkyl ethers, the group of saturated or unsaturated, branched or unbranched alcohols, and also fatty acid triglycerides, especially the triglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 8 to 24, in particular 12 to 18, carbon atoms.
  • the fatty acid triglycerides can, for example, advantageously be selected from the group of synthetic, semisynthetic and natural oils, for example olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, almond oil, palm oil, coconut oil, palm kernel oil and the like.
  • Cyclomethicone (octamethylcyclotetrasiloxane) is advantageously used as the silicone oil to be used.
  • other silicone oils can also be used with similar advantages, for example hexamethylcyclotrisiloxane, polydimethylsiloxane, poly (methylphenylsiloxane).
  • Mixtures of cyclomethicone and isotridecyl isononanoate, of cyclomethicone and 2-ethylhexyl isostearate are also particularly advantageous.
  • aqueous phase of preparations in the sense of this publication optionally advantageously contains water-soluble plants extracts, alcohols, diols or polyols (lower alkyl), and their ethers, preferably ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or monobutyl ether,
  • alcohols lower alkyl
  • ethanol 1, 2-propanediol
  • glycerol in particular one or more thickeners
  • one or more can advantageously be selected from the group consisting of silicon dioxide, aluminum silicates, polysaccharides and the like Derivatives, for example
  • the cosmetic and dermatological preparations within the meaning of this text can contain cosmetic auxiliaries as are usually used in such preparations, e.g. Preservatives, antioxidants, vitamins, bactericides, perfumes, substances to prevent foaming, dyes, pigments that have a coloring effect, thickeners, surfactants, emollients, emulsifiers, moisturizing and / or moisturizing substances, moisturizers, fats, oils, waxes, plant extracts or other customary components of a cosmetic or dermatological formulation such as alcohols, lower alkyl alcohols, polyols, lower alkyl polyols, polymers, foam stabilizers, complexing agents, electrolytes, organic solvents, propellant gases, silicones or silicone derivatives.
  • cosmetic auxiliaries e.g. Preservatives, antioxidants, vitamins, bactericides, perfumes, substances to prevent foaming, dyes, pigments that have a coloring effect, thickeners, surfactants, emollients, emul
  • antioxidants which can be used are all antioxidants which are suitable or customary for cosmetic and / or dermatological applications.
  • the amount of the antioxidants (one or more compounds) in the preparations is preferably 0.001 to 30% by weight, particularly preferably 0.05 to 20% by weight, in particular 1 to 10% by weight, based on the total weight the preparation.
  • the antioxidants are advantageously chosen from the following group: amino acids (eg glycine, histidine, 3,4-dihydroxyphenylalanine, tyrosine, tryptophan) and their derivatives, imidazoles (eg urocanic acid) and their derivatives, peptides (D, L-camosine, D-carnosine, L-carnosine, anserine) and their derivatives, carotenoids, carotenes (e.g.
  • alpha-carotene, beta-carotene, lycopene and their derivatives, chlorogenic acid and their derivatives, lipoic acid and their derivatives, aurothioglucose, propylthiouracil and other thiols ( eg thioredoxin, Glutathione, cysteine, cystine, cystamine and their glycosyl 'and N-acyl derivatives or alkyl esters thereof) and also salts thereof, dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and derivatives thereof and Phenolklareamide phenolic benzylamines (eg Homovanillin Textre-, 3,4 Dihydroxyphenylessigklakladre-, Ferulaklaffeic acid, vanillomandelic acid or 3,4-dihydroxymandelic acid
  • vitamin E acetate vitamin E acetate
  • vitamin A and derivatives e.g. vitamin A palmitate
  • rutinic acid and its derivatives flavonoids (e.g. quercetin, alpha-glucosylrutin) and their derivatives
  • phenolic acids e.g. gallic acid, ferulic acid
  • propyl gallic acid, ethyl ester, octyl ester furfurylidene glucitol, dibutylhydroxytoluene, butylhydroxyanisole
  • uric acid and its derivatives mannose and its derivatives
  • zinc and its derivatives e.g. ZnO, ZnS0
  • selenium and its derivatives e.g. selenomethionine
  • stilbenes and their derivatives e.g. stilbene oxide, resveratrol
  • EP-A 900781 EP-A 1 029 849, EP-A 1 066 821, WO-A 01/43712, WO-A 01/70176, WO-A 01/98235 or also in WO A 01/98258.
  • vitamin E and / or its derivatives represent the antioxidant (s)
  • vitamin A or vitamin A derivatives or carotenes or their derivatives represent the antioxidant or antioxidants, it is advantageous to use their respective Concentrations from the range of 0.001 to 10 wt .-%, based on the total weight of the formulation to choose.
  • Example 1 Sun protection milk (O / W);
  • Example 2 Sun protection lotion (O / W);
  • Example 3 Face cream (O / W) with sun protection;
  • Example 4 Sunscreen milk
  • Part A Heat to approx. 85 ° C.
  • Part B Weigh raw materials without Carbopol and Keltrol. Disperse Carbopol and Keltrol with Ultra Turrax. Heat to approx. 85 ° C.
  • Part C Add immediately to A / B and then homogenize hot (Ultra Turrax). Let cool while stirring.
  • Part D Add and stir.
  • Part A Heat to approx. 85 ° C (without Keltrol and zinc oxide). Disperse Keltrol and zinc oxide with the Ultra Turrax in the hot lipid phase.
  • Part B Heat to approx. 85 ° C. Add B to A. Cool to 60 ° C while stirring and homogenize (Ultra Turrax). Then allow to cool to room temperature while stirring.
  • Part C Add and homogenize. Examples 1-4 are to be understood as standard formulations since, in the sense of this publication, other sun filters alone or as sun filter compositions also benefit from a combination with the emulsifier according to the invention.
  • Example (5) Hair gel wax for men- DGHST 0086/01;
  • Example (6) hair cream (O / W) DCHST 0087/00;
  • Example (7) Hair conditioner rinsing (O / W) with Dragoderm DLHCR 0088/00;
  • Example (8) Sensitive Balsam Roll-on (O / W) DRDEO 0089/00;
  • Example (9) care lotion for wet wipes (O / W) DDTSS 009 1/00;
  • phase A Mix all raw materials of phase A, heat to 80 ° C and homogenize with an Ultra Turrax. Stir cold with a blade stirrer, reducing the stirring speed as the temperature decreases. Add phase C at approx. 35 ° C. pH: approx. 5.9.
  • Examples 7, 8 and 9 above are formulation examples for low-viscosity and sprayable emulsions.
  • Another formulation example for a low viscosity, namely sprayable formulation, is given with Example 11 below.
  • Example 11 (DDSUN 0090/00) Sprayable sun milk
  • Example 12 (DCSUN 0093/00) sun protection cream (O / W)
  • Example 14 gives extracts from the technical product specification of a preferred emulsifier according to the invention, to which the name "Emulsiphos" has been assigned.
  • Emulsiphos is suitable for the production of creams and lotions in the pH range of 4 - 9.
  • Polar and non-polar oils can be processed with this emulsifier without any problems.
  • the incorporation can take place either over the water phase or oil phase.
  • Example 15 Test method 211 for determining the saponification number
  • the saponification number is calculated from the difference between the 0.5 N sulfuric acid consumed in the blind test and the main test.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Dispersion Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Dermatology (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Colloid Chemistry (AREA)
PCT/EP2004/001865 2003-02-25 2004-02-25 O/w-emulgator, sowie o/w-emulsionen enthaltend kalium-cetylphosphat und verfahren zu deren herstellung Ceased WO2004075868A1 (de)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2006501953A JP2006519686A (ja) 2003-02-25 2004-02-25 O/w乳化剤、o/wエマルジョンおよびこれらの製造方法
US10/546,617 US20060171913A1 (en) 2003-02-25 2004-02-25 O/w emulsifier and o/w emulsions containing potassium cetyl phosphate and method for the production thereof
EP04714278A EP1599176A1 (de) 2003-02-25 2004-02-25 O/w-emulgator, sowie o/w-emulsionen enthaltend kalium-cetylphosphat und verfahren zu deren herstellung

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10308565.3 2003-02-25
DE10308565A DE10308565A1 (de) 2003-02-25 2003-02-25 Universell einsetzbarer Emulgator vom Typ O/W basierend auf einem voll neutralisierten Phosphorsäureester und Palmglyceriden zur Herstellung von Cremes, Milchen und sehr niederviskosen, sprühfähigen Lotionen

Publications (1)

Publication Number Publication Date
WO2004075868A1 true WO2004075868A1 (de) 2004-09-10

Family

ID=32841982

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2004/001865 Ceased WO2004075868A1 (de) 2003-02-25 2004-02-25 O/w-emulgator, sowie o/w-emulsionen enthaltend kalium-cetylphosphat und verfahren zu deren herstellung

Country Status (7)

Country Link
US (1) US20060171913A1 (https=)
EP (1) EP1599176A1 (https=)
JP (1) JP2006519686A (https=)
KR (1) KR20050100653A (https=)
CN (1) CN100418507C (https=)
DE (1) DE10308565A1 (https=)
WO (1) WO2004075868A1 (https=)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10353030A1 (de) * 2003-11-13 2005-07-07 Beiersdorf Ag Konservierende Wirkstoffkombination
EP2286908A2 (de) 2010-11-19 2011-02-23 Symrise AG Lösungsvermittler für kosmetische Zubereitungen
EP3197427B1 (en) 2014-09-26 2021-02-24 DSM IP Assets B.V. O/w emulsions

Families Citing this family (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102007015282B4 (de) * 2007-03-29 2017-10-05 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Viskositätsregulator, Verfahren zu dessen Herstellung und dessen Verwendung
EP2205202B1 (de) 2007-09-19 2011-07-27 Symrise AG O/w-emulgator, o/w-emulsionen und verfahren zu deren herstellung
FR2924600B1 (fr) * 2007-12-06 2013-06-14 Oreal Composition cosmetique comprenant un derive hydrocarbone phosphate et un acide carboxylique
US20090155194A1 (en) * 2007-12-18 2009-06-18 Schering-Plough Healthcare Products, Inc. Enhanced photostability of avobenzone in the presence of zinc oxide using phosphate-based emulsifiers
FR2940117B1 (fr) * 2008-12-18 2011-02-18 Oreal Emulsion huile dans eau presentant un ph allant de 3 a 5,5
DE102010019506A1 (de) * 2010-05-06 2010-12-02 Clariant International Limited Zusammensetzungen enthaltend Phosphorsäurealkylester und Polyolester
JP6029822B2 (ja) * 2011-11-25 2016-11-24 ポーラ化成工業株式会社 水中油型乳化組成物
CA2920115A1 (en) * 2013-08-21 2015-02-26 Coty Inc. Gel volume mascara composition
JP2017528453A (ja) * 2014-09-26 2017-09-28 ディーエスエム アイピー アセッツ ビー.ブイ. O/wエマルジョン
KR102265979B1 (ko) * 2014-11-06 2021-06-15 주식회사 엘지생활건강 인-샤워 피부 보습용 조성물
US10709649B2 (en) * 2015-04-29 2020-07-14 Dsm Ip Assets B.V. Topical sunscreen emulsions
EP3389619A1 (de) * 2015-12-15 2018-10-24 Symrise AG Zubereitungen mit carnosinen
CN109414389B (zh) 2016-06-27 2022-05-24 帝斯曼知识产权资产管理有限公司 局部用组合物
CN109310609B (zh) * 2016-06-27 2022-06-28 帝斯曼知识产权资产管理有限公司 包含微颜料的组合物
WO2018064284A1 (en) 2016-09-30 2018-04-05 Novaflux, Inc. Compositions for cleaning and decontamination
CN110785161B (zh) 2017-06-23 2023-06-20 宝洁公司 用于改善皮肤外观的组合物和方法
CN107675552A (zh) * 2017-10-24 2018-02-09 苏州丰倍生物科技有限公司 一种可清洗的植物型纸制品防水防油剂及其制备方法
EP3727278A1 (de) * 2017-12-22 2020-10-28 Symrise AG Kosmetische emulsion, umfassend 1,2-decandiol
EP3775133B1 (en) 2018-04-03 2024-10-09 Novaflux, Inc. Cleaning composition with superabsorbent polymer
MX2020012266A (es) * 2018-05-14 2021-01-29 Johnson & Johnson Consumer Inc Crema y locion humectante.
KR102733166B1 (ko) * 2018-06-22 2024-11-25 존슨 앤드 존슨 컨수머 인코포레이티드 액정 구조체를 함유하는 에멀젼의 형성 방법
CN112437657A (zh) 2018-07-03 2021-03-02 宝洁公司 处理皮肤状况的方法
DE102018214478A1 (de) 2018-08-28 2020-03-05 Beiersdorf Ag Acrylatfreie kosmetische Emulsion
US12064495B2 (en) 2019-10-03 2024-08-20 Protegera, Inc. Oral cavity cleaning composition, method, and apparatus
WO2021067872A1 (en) 2019-10-03 2021-04-08 Novaflux, Inc. Oral cavity cleaning composition, method, and apparatus
CN111265434A (zh) * 2020-03-19 2020-06-12 猫头鹰(福州)日用品有限公司 一种植物来源乳化剂油包水膏霜及其制备方法
US10959933B1 (en) 2020-06-01 2021-03-30 The Procter & Gamble Company Low pH skin care composition and methods of using the same
JP7590462B2 (ja) 2020-06-01 2024-11-26 ザ プロクター アンド ギャンブル カンパニー ビタミンb3化合物の皮膚への浸透を改善する方法
US12571108B2 (en) * 2022-03-12 2026-03-10 Razor Keep, LLC Blade preserving products and methods for manufacturing
WO2023175129A1 (en) 2022-03-17 2023-09-21 Symrise Ag Additive for sunscreens
EP4245291A1 (en) 2022-03-17 2023-09-20 Symrise AG Additive for sunscreens
EP4245292A1 (en) * 2022-03-17 2023-09-20 Symrise AG Additive for sunscreens

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59161309A (ja) * 1984-02-16 1984-09-12 Kao Corp 乳化化粧料
JPS6215383A (ja) * 1985-07-10 1987-01-23 東洋紡績株式会社 けん切紡績用処理剤
EP0227012A1 (en) * 1985-12-23 1987-07-01 Kao Corporation Gel-like emulsion and O/W emulsions obtained from the gel-like emulsion
EP0251249A2 (de) * 1986-07-04 1988-01-07 Henkel Kommanditgesellschaft auf Aktien Alkyl-hydroxyalkyl-phosphorsäureester
EP0427411A2 (en) * 1989-10-27 1991-05-15 Richardson Vicks, Inc. Photoprotection compositions having improved substantivity
WO2002056843A2 (fr) * 2001-01-18 2002-07-25 L'oreal Nanoemulsion translucide, son procede de fabrication et ses utilisations dans les domaines cosmetique, dermatologique et/ou ophtamologique
EP1264632A1 (de) * 2001-06-08 2002-12-11 Cognis Iberia, S.L. Verwendung von Alkyl(ether)phosphaten(III)

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4536519A (en) * 1981-06-15 1985-08-20 Kao Soap Co., Ltd. Emulsifying agent and emulsified cosmetics
US5362418A (en) * 1985-12-23 1994-11-08 Kao Corporation Gel-like emulsion and O/W emulsion obtained from the gel-like emulsion
US5744062A (en) * 1996-08-29 1998-04-28 R.I.T.A. Corporation Balanced emulsifier blends for oil-in-water emulsions
AU774383B2 (en) * 1999-07-12 2004-06-24 Ciba Specialty Chemicals Holding Inc. Use of mixtures of micropigments for preventing tanning and for lightening skin and hair

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59161309A (ja) * 1984-02-16 1984-09-12 Kao Corp 乳化化粧料
JPS6215383A (ja) * 1985-07-10 1987-01-23 東洋紡績株式会社 けん切紡績用処理剤
EP0227012A1 (en) * 1985-12-23 1987-07-01 Kao Corporation Gel-like emulsion and O/W emulsions obtained from the gel-like emulsion
EP0251249A2 (de) * 1986-07-04 1988-01-07 Henkel Kommanditgesellschaft auf Aktien Alkyl-hydroxyalkyl-phosphorsäureester
EP0427411A2 (en) * 1989-10-27 1991-05-15 Richardson Vicks, Inc. Photoprotection compositions having improved substantivity
WO2002056843A2 (fr) * 2001-01-18 2002-07-25 L'oreal Nanoemulsion translucide, son procede de fabrication et ses utilisations dans les domaines cosmetique, dermatologique et/ou ophtamologique
EP1264632A1 (de) * 2001-06-08 2002-12-11 Cognis Iberia, S.L. Verwendung von Alkyl(ether)phosphaten(III)

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; "Cosmetic emulsions containing phosphates and monoglycerides", XP002283546, retrieved from STN Database accession no. 1985:12205 *
DATABASE WPI Section Ch Week 198709, Derwent World Patents Index; Class A87, AN 1987-060663, XP002285686 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10353030A1 (de) * 2003-11-13 2005-07-07 Beiersdorf Ag Konservierende Wirkstoffkombination
EP2286908A2 (de) 2010-11-19 2011-02-23 Symrise AG Lösungsvermittler für kosmetische Zubereitungen
EP2455157A1 (de) 2010-11-19 2012-05-23 Symrise AG Lösungsvermittler für kosmetische Zubereitungen
EP3197427B1 (en) 2014-09-26 2021-02-24 DSM IP Assets B.V. O/w emulsions

Also Published As

Publication number Publication date
US20060171913A1 (en) 2006-08-03
CN1753655A (zh) 2006-03-29
EP1599176A1 (de) 2005-11-30
JP2006519686A (ja) 2006-08-31
CN100418507C (zh) 2008-09-17
KR20050100653A (ko) 2005-10-19
DE10308565A1 (de) 2004-09-09

Similar Documents

Publication Publication Date Title
EP1599176A1 (de) O/w-emulgator, sowie o/w-emulsionen enthaltend kalium-cetylphosphat und verfahren zu deren herstellung
EP2205202B1 (de) O/w-emulgator, o/w-emulsionen und verfahren zu deren herstellung
DE60000235T2 (de) Zusammensetzung und insbesondere kosmetische Zusammensetzung, die ein Sapogenin enthält
EP1641904B1 (de) O/w-emulgator, o/w-emulsion und deren verwendungen
DE19726184A1 (de) Kosmetische und dermatologische Lichtschutzformulierungen in Form von Emulsionen, insbesondere O/W-Makroemulsionen, O/W-Mikroemulsionen oder O/W/O-Emulsionen, mit einem Gehalt an lichtschutzwirksamen Benzotriazolderivaten
EP0783882A2 (de) Kosmetische und dermatologische Lichtschutzformulierungen in Form von Emulsionen
DE69416091T2 (de) Benzophenonderivat und ein UV-Licht-Absorber und eine endermatische Salbe
EP0930866A1 (de) Kosmetische oder dermatologische gele auf der basis von mikroemulsionen
DE19651478A1 (de) Lichtschutzzubereitungen mit einem Gehalt an oberflächenaktiven Mono- bzw. Oligoglycerylverbindungen, wasselöslichen UV-Filtersubstanzen und ggf. anorganischen Mikropigmenten
EP2739137A1 (de) Verwendung von isosorbidmonoestern als verdicker
DE19949826A1 (de) Kosmetische und dermatologische Lichtschutzformulierungen in Form von O/W-Makroemulsionen oder O/W-Mikroemulsionen, mit einem Gehalt an Dihydroxyaceton
DE69519952T2 (de) Selbstbräunende kosmetische Mittel enthaltend Dihydroxyaceton
EP1356805A1 (de) O/W-Emulsion enthaltend eine glycosilierte Organosiliciumverbindung und ein Metalloxid
DE602005001478T2 (de) Oel-in-Wasser emulgierte Zusammensetzung
DE10047250A1 (de) Emulgatorfreie feindisperse Systeme vom Typ Wasser-in-Öl mit einem Gehalt an Ethylcellulose
EP0783881A2 (de) Kosmetische und dermatologische Lichtschutzformulierungen mit einem Gehalt an hydrophoben anorganischen Mikropigmenten
DE102010034389B4 (de) Stabilisierte W/O-Emulsionen
DE19726121A1 (de) Kosmetische und dermatologische Lichtschutzformulierungen in Form von Emulsionen, insbesondere O/W-Makroemulsionen, O/W-Mikroemulsionen oder O/W/O-Emulsionen, mit einem Gehalt an Bis-Resorcinyltriazinderivaten
EP0813861A2 (de) Sonnenschutzmittel in Form von O/W- Mikroemulsionen
EP1740528A1 (de) Emulgatorkonzentrat für kosmetische zusammensetzung
DE19548014A1 (de) Kosmetische und dermatologische Lichtschutzformulierungen in Form von Emulsionen, insbesondere O/W-Makroemulsionen, O/W-Mikroemulsionen oder O/W/O-Emulsionen, mit einem Gehalt an in fester, dispergierter Form vorliegenden, in Ölkomponenten schwerlöslichen oder unlöslichen UV-Filtersubstanzen
DE19952410A1 (de) Lichtschutzzubereitungen umfassend feste Lipidnanopartikel
DE10331760A1 (de) O/W-Emulgator, O/W-Emulsion und deren Verwendungen
KR100559691B1 (ko) 주름완화물질을 함유하는 유화형 고형 파운데이션 조성물
DE19950090A1 (de) Kosmetische und dermatologische Lichtschutzformulierungen in Form von O/W-Makroemulsionen oder O/W-Mikroemulsionen, mit einem Gehalt an einem oder mehreren Siliconemulgatoren

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): BW GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 2004714278

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 3292/DELNP/2005

Country of ref document: IN

WWE Wipo information: entry into national phase

Ref document number: 1020057014321

Country of ref document: KR

ENP Entry into the national phase

Ref document number: 2006171913

Country of ref document: US

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 10546617

Country of ref document: US

WWE Wipo information: entry into national phase

Ref document number: 20048051309

Country of ref document: CN

Ref document number: 2006501953

Country of ref document: JP

WWP Wipo information: published in national office

Ref document number: 1020057014321

Country of ref document: KR

WWP Wipo information: published in national office

Ref document number: 2004714278

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 10546617

Country of ref document: US