WO2019120572A1 - Émulsions contenant des mélanges de 1,2-hexanediol et de 1,2-octanediol - Google Patents

Émulsions contenant des mélanges de 1,2-hexanediol et de 1,2-octanediol Download PDF

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Publication number
WO2019120572A1
WO2019120572A1 PCT/EP2017/084472 EP2017084472W WO2019120572A1 WO 2019120572 A1 WO2019120572 A1 WO 2019120572A1 EP 2017084472 W EP2017084472 W EP 2017084472W WO 2019120572 A1 WO2019120572 A1 WO 2019120572A1
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Prior art keywords
octanediol
emulsion
hexanediol
oil
phase
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PCT/EP2017/084472
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German (de)
English (en)
Inventor
Manuel PESARO
Jan Peter EBBECKE
Sabine Lange
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Symrise Ag
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Priority to PCT/EP2017/084472 priority Critical patent/WO2019120572A1/fr
Publication of WO2019120572A1 publication Critical patent/WO2019120572A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/062—Oil-in-water emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/068—Microemulsions
    • 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
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/596—Mixtures of surface active compounds

Definitions

  • the skin is an important but at the same time sensitive human organ whose care is indispensable for the physical and mental well-being. For this reason, numerous skin care products and cosmetics have already been developed, which are available, for example, as creams, lotions, oils, sprays or gels and contain various specific skincare active ingredients.
  • Emulsions are heterogeneous systems of at least two normally immiscible liquids (phases), with one liquid (phase) forming small droplets distributed in the other liquid (phase).
  • phases normally immiscible liquids
  • the phase that forms droplets is called the disperse phase.
  • the phase in which the droplets are present is called the continuous phase.
  • O / W oil-in-water
  • W / O water-in-oil
  • O / W emulsions have water as the continuous phase and an oil as the disperse phase.
  • W / O emulsions have an oil as a continuous phase and water as a disperse phase.
  • the basic character of an O / W emulsion is characterized by the water.
  • the basic character of a W / O emulsion is characterized by the oil.
  • an oil is understood to mean an organic liquid which under normal circumstances can not be mixed with water.
  • deionized water also known as demineralized water, distilled water or ultrapure water
  • the undesirable phase separation is due to the thermodynamic instability of an emulsion, which is a consequence of a normally high inter-phase interfacial tension, which, in turn, is due to the different intramolecular attractive forces within the respective phases.
  • Emulsions therefore show a general tendency to have the smallest possible interface between the individual phases (which are immiscible under normal circumstances) and thus after separation of the phases.
  • Emulsifiers are molecules with a polar, hydrophilic (ie water-loving) structural element and a non-polar lipophilic (ie oil-loving) structural element. Due to their amphiphilic character, the individual emulsifier molecules accumulate at the interfaces and thus reduce the interfacial tension. Together with an entry of mechanical work and, if necessary, thermal energy, this results in a finely dispersed system in which one phase is finely distributed in the other phase in the form of droplets.
  • 1,2-alkanediols are also referred to as wetting agents. Although these reduce the interfacial tension between the aqueous phase and the oil phase, they are not able to form stable emulsions alone. Therefore, 1, 2-alkanediols according to the HLB concept of Griffin (see Griffin, W.C .: Classification of surface active agents by HLB, J. Soc., Cosmet., Chem., 1, 1949) are not assigned to the emulsifying substances (emulsifiers).
  • 1,2-alkanediols are also said to have other positive properties, such as moisturizing or antimicrobial properties.
  • EP 2 589 291 discloses the use of 1, 2-decanediol, 1, 2-octanediol, 1, 2-hexanediol and 1, 2-pentanediol in cosmetically or dermatologically active mixtures.
  • a cosmetic emulsion which contains polyglycerol-3-methylglucose distearate, silica dimethyl silylates and acrylates / C10-C30 alkyl acrylate crosspolymer.
  • EP 1 946 742 discloses a cosmetic water-in-silica oil emulsion containing 1,2-decanediol.
  • EP 1 426 029 A1 discloses a long-term stable emulsion which comprises 1,2-alkanediols.
  • EP 2 589 291 discloses the use of a ternary mixture of 2-phenoxyethanol and two different 1,2-alkanediols to synergistically enhance the antimicrobial efficacy of mixtures of at least two of the 1,2-alkanediols.
  • WO 2003/069994 discloses the use of various 1,2-alkanediol mixtures for the synergistic enhancement of the antimicrobial activity.
  • US 2016/0206571 discloses the use of a mixture of 1,2-hexanediol and 1,2-octanediol to synergistically enhance antimicrobial activity and reduce droplet size.
  • WO 2006/069953 discloses the use of various 1,2-alkanediol mixtures for synergistically influencing skin moisture regulation.
  • the present invention solves the aforementioned problem of the need for substances which lower the surface or interfacial tension of a (cosmetic) emulsion, in particular for substances which reduce the surface or interfacial tension of a (cosmetic) emulsion, are easy to handle and have no negative influence on other properties (such as viscosity and yield point) of the emulsion.
  • the present invention solves this and other problems and in one aspect relates to a cosmetic emulsion comprising 1, 2-hexanediol and 1, 2-octanediol, in a second aspect the use of a mixture of 1, 2-hexanediol and 1, 2 Octanediol for reducing the surface and / or surface tension of a cosmetic emulsion and in a third aspect, a method for producing a cosmetic emulsion according to the invention.
  • the present invention provides a cosmetic emulsion comprising a continuous water phase, oil droplets, 1, 2-hexanediol and 1, 2-octanediol dispersed throughout the continuous water phase.
  • the emulsion according to the invention is therefore an O / W emulsion.
  • the weight ratio of 1, 2-hexanediol to 1, 2-octanediol is 3: 1 to 1: 3, preferably 2: 1 to 1: 2, more preferably about 1: 1 and the total amount of 1, 2-hexanediol and 1, 2-octanediol is up to 2.0 wt .-%, preferably up to 1, 5 wt .-%, more preferably up to 1, 0 wt .-%, more preferably up to 0.5 wt .-% , is based on the total weight of the emulsion.
  • the present oil droplets dispersed in the aqueous phase have a diameter d volumenbezoge- NEN v 0, 5 1, 0 to 10.0 miti, preferably 3.0 to 9.0 miti, more preferably 3.0 to 7.0 gm, at Rushzugtesten 3.5 to 6.0 gm.
  • d volumenbezoge- NEN v 0, 5 1, 0 to 10.0 miti, preferably 3.0 to 9.0 miti, more preferably 3.0 to 7.0 gm, at Rushzugtesten 3.5 to 6.0 gm.
  • 1-hexanediol has an HLB value of 5.8
  • 2-octanediol has an HLB value of 4.7.
  • the HLB value of a 1: 1 (wt) mixture of 1, 2-hexanediol and 1, 2-octanediol is about 5.2 and thus in the middle between the values for 1, 2-hexanediol and 1, 2-octanediol.
  • the average volume-related diameter was preferably determined by means of the principle of laser diffraction spectroscopy.
  • Corresponding devices for determining the average volume-related diameter are, for example, Malvern Insruments GmbH and Malvern Instruments Ltd. distributed. Unless otherwise stated below, the average volume diameter was determined using a Malvern "Mastersizer 3000" instrument.
  • d v o, 5 XY means that 50% of the oil droplets in the emulsion have a volume-related diameter that is less than XY.
  • d v 0 , 5 20 gm means that 50% of the oil droplets in the emulsion have a volume-related diameter that is less than 20 gm.
  • d v 0, i XY means that 10% of the oil droplets in the emulsion have a volume-related diameter that is less than XY.
  • d v 0, i 20 gm means that 10% of the oil droplets in the emulsion have a volume-related diameter that is less than 20 gm.
  • D v 0.9 XY means that 90% of the oil droplets in the emulsion have a have a volume-related diameter that is smaller than XY.
  • d v 0 , 9 20 gm means that 90% of the oil droplets in the emulsion have a volume-related diameter that is less than 20 gm.
  • deionized water is used.
  • ordinary tap water can also be used.
  • the specialist can choose the type of water to be used according to his specialist knowledge. It is preferred that the emulsion according to the invention in addition to 1, 2-hexanediol and 1, 2-octanediol no further 1, 2-alkanediols.
  • the cosmetic emulsion does not contain 2-phenoxyethanol.
  • the emulsion according to the invention is preferably a two-phase system of a cosmetic oil in water.
  • a cosmetic oil is understood to mean an oil which is tolerated by the skin and / or has a positive cosmetic effect.
  • the oil used in the cosmetic emulsion according to the invention is preferably selected from the group consisting of
  • the oil used in the cosmetic emulsion of the invention i.e., the oil phase
  • the oil phase is selected from the group consisting of myristyl myristate,
  • esters of straight-chain C 6 -C 22 -fatty acids with branched alcohols in particular 2-ethylhexanol
  • Esters of C 18 -C 38 -alkylhydroxycarboxylic acids with straight-chain or branched C 6 -C 22 fatty alcohols in particular dioctylmalate
  • Esters of straight-chain or branched fatty acids with polyhydric alcohols for example propylene glycol, dimerdiol or trimer triol
  • Guerbet alcohols for example propylene glycol, dimerdiol or trimer triol
  • triglycerides based on C 6 -C 10 -fatty acids and / or liquid mono- / di- / triglyceride mixtures based on C 6 -C 18- fatty acids
  • Esters of aromatic carboxylic acids especially benzoic acid, with C 6 -C 22 fatty alcohols and / or Guerbet alcohols,
  • Esters of benzoic acid with linear and / or branched C 6 -C 22 alcohols such as Finsolv ® TN
  • silicone oils cyclomethicones, silicone methicones, etc.
  • aliphatic or naphthenic hydrocarbons for example squalans, squalene or dialkylcyclohexanes
  • a silicone oil is understood as meaning an oil which has the structural unit [R 1 R 2 SiO] n , in which R 1 and R 2 are, for example, organic radicals and n is an integer.
  • the choice of the components of the oil phase and the mass composition of the oil phase are largely responsible for the spreadability of the cosmetic emulsion on the skin, which in turn significantly affects the skin feel.
  • the oil phase comprises ethylhexyl isononanoate, caprylic / capric triglyceride, and prunus amygdalus dulcis (Sweet Almond) oil.
  • the oil phase consists of these components. It has been found that this combination of low, medium and high-spreading substances of the formulation gives a good spreadability on the skin surface and ensures a pleasant skin feel.
  • the oil phase preferably comprises from 20 to 80% by weight, more preferably from 30 to 70% by weight, more preferably from 40 to 60% by weight, particularly preferably from 45 to 55% by weight, in particular about 50% by weight. %, Ethylhexylisononanoat, based on the total weight of the oil phase.
  • the oil phase is 10 to 60 wt .-%, more preferably 20 to 50 wt .-%, more preferably 30 to 40 wt .-%, particularly preferably 32 to 38 wt .-%, in particular about 35 wt .-%, Caprylic / Capric triglyceride, based on the total weight of the oil phase.
  • the oil phase comprises
  • Prunus Amygdalus Dulcis (Sweet Almond) oil based on the total weight of the oil phase.
  • the oil phase comprises from 45 to 55% by weight, in particular about 50% by weight, ethylhexyl isononanoate, 32 to 38% by weight, in particular about 35% by weight, caprylic / capric triglyceride and 12 to 17 wt .-%, in particular about 15 wt .-% Prunus Amygdalus Dulcis (Sweet Almond) oil, based on the total weight of the oil phase.
  • the oil phase comprises or consists of caprylic / capric triglyceride and cetearylethylhexanoate, wherein the weight ratio is preferably 2: 1.
  • the oil phase comprises Caprylic / capric triglyceride and cetearyl ethylhexanoate in a total amount of 1.0 to 50.0 wt.%, Preferably 3.0 to 30.0 wt.%, More preferably 5.0 to 20.0 wt.% preferably 8.0 to 15.0% by weight, most preferably 10.0 to 13.0% by weight, or consists thereof, based on the total weight of the emulsion.
  • the oil phase comprises caprylic / capric triglyceride in an amount of 2.0 to 15.0% by weight, preferably 4.0 to 12.0% by weight, more preferably 5.0 to 10.0 Wt .-%, most preferably 7.0 to 9.0 wt .-%, and / or Cetearylethylhexanoat in an amount of 1, 0 to 10.0 wt .-%, preferably 2.0 to 8.0 wt .-% , more preferably 3.0 to 5.0 wt .-%, or consists thereof, in each case based on the total weight of the emulsion.
  • the oily phase comprises or consists of caprylic / capric triglyceride in an amount of 7.0 to 9.0% by weight and cetearylethylhexanoate in an amount of 3.0 to 5.0% by weight, respectively based on the total weight of the emulsion.
  • the emulsion according to the invention preferably contains one or more of 1, 2-hexanediol and 1, 2-octanediol different emulsifier (s).
  • the one or more emulsifiers have / have an HLB value in the range of 8 to 18, more preferably 8 to 16.
  • 1, 2-hexanediol and 1, 2-octanediol are different emulsifier (s) selected from the group consisting of PEG-100 stearate, cetearyl glucoside, distearyldimonium chloride,
  • Palmitamidopropyltrimoniumchlorid glyceryl stearate, glyceryl oleate, polyglyceryl (3) methylglucose, cetearyl alcohol, potassium cetyl phosphate, Natriumcetylphosphat, acrylate / C-io-C 3 o alkyl acrylate cross polymer, ammonium acryloyldimethyltaurate / Beheneth- 25 methacrylate crosspolymer, polyglyceryl-4 caprate, polyglyceryl 4-caprylate / caprate, cetyl PEG / PPG-10/1 dimethicone, polyglyceryl-6 dioleate, polyglyceryl-2-stearate, PEG-30 dipolyhydroxystearate, sodium stearoyl lactylate, PEG-40 hydrogenated castor oil, hydrogenated palm glycerides (INCI nomenclature: hydrogenated palm glycerides) or a mixture thereof.
  • the one or more of 1, 2-hexanediol and 1, 2-octanediol is / are different emulsifier (s) selected from the group consisting of Cetearyl alcohol, glyceryl stearate citrate, polyglyceryl (3) methyl glucose distearate, potassium cetyl phosphate, hydrogenated palm glycerides and a mixture thereof.
  • emulsifier selected from the group consisting of Cetearyl alcohol, glyceryl stearate citrate, polyglyceryl (3) methyl glucose distearate, potassium cetyl phosphate, hydrogenated palm glycerides and a mixture thereof.
  • the one or more of 1, 2-hexanediol and 1, 2-octanediol are various emulsifiers selected from the group consisting of glyceryl stearate citrate, polyglyceryl (3) -methyl glucose distearate, potassium cetyl phosphate, hydrogenated palm glycerides, and the like Mix of it.
  • the emulsifier other than 1, 2-hexanediol and 1, 2-octanediol is a mixture of cetearyl alcohol and a member of the group consisting of (i) a mixture of potassium cetyl phosphate and hydrogenated palm glycerides (preferably in the weight ratio in the range of 1: 1 to 7: 3, especially about 6: 4 (potassium cetyl phosphate to hydrogenated palm glycerides)), (ii) glyceryl stearate citrate and (iii) polyglyceryl (3) methyl glucose distearate.
  • the emulsifier other than 1, 2-hexanediol and 1, 2-octanediol is a mixture of cetearyl alcohol and a mixture of potassium cetyl phosphate and hydrogenated palm glycerides.
  • the weight ratio of potassium cetyl phosphate to hydrogenated palm glycerides in the mixture of potassium cetyl phosphate and hydrogenated palm glycerides is 1: 1 to 7: 3, especially about 6: 4.
  • the emulsifier other than 1, 2-hexanediol and 1, 2-octanediol is a mixture of cetearyl alcohol and
  • the emulsifier other than 1,2-hexanediol and 1,2-octanediol is a mixture of cetearyl alcohol and polyglyceryl (3) -methyl glucose distearate.
  • the emulsifier other than 1,2-hexanediol and 1,2-octanediol is a mixture of potassium cetyl phosphate and hydrogenated palm glycerides.
  • the emulsifier other than 1, 2-hexanediol and 1, 2-octanediol is polyglyceryl (3) -methylglucose distearate.
  • the oil droplets present in the water phase have an average volume-related diameter d v 0, i of 1, 0 to 10.0 miti, preferably 1, 0 to 8.0 miti, more preferably 1, 0 to 6.0 gm, more preferably 1.0 to 4.0 gm, more preferably 1.0 to 3.0 gm, more preferably 1.0 to 2.5 gm, further preferably 1.5 to 2.0 gm, also preferably determined by means of laser diffraction spectroscopy.
  • the emulsion of the invention has an interfacial tension of 10 to 30 mN / m, preferably 15 to 25 mN / m, more preferably 19 to 24 mN / m, particularly preferably 20 to 24 mN / m, determined by means of drop volume Method at an interface age of about 4 to about 636 s.
  • the interfacial tension was determined by the following relationship: y
  • n is the interfacial tension
  • V Tr is the volume of the droplet
  • p Tr is the density of the droplet
  • p M is the density of the medium surrounding the droplet
  • g is the acceleration due to gravity
  • r K is the radius of the capillary.
  • the droplet dissolves from the capillary. This is detected by means of a light barrier and the tear-off volume is measured. From the volume and density difference of the medium surrounding the droplet, the interfacial tension is calculated according to the above formula.
  • the emulsion according to the invention preferably has a surface tension of 10 to 80 mN / m. More preferably, the emulsion according to the invention has a surface tension of 20 to 60 mN / m, more preferably 20 to 50 mN / m, more preferably 20 to 40 mN / m, most preferably 20 to 30 mN / m.
  • the surface tension was determined by drop-volume method (static measurement). For this purpose, a device of the type LAUDA TVT2 was used.
  • the emulsion of the invention may further contain other useful ingredients such as preservatives, antimicrobials such as other antibacterial or fungicidal agents, abrasives, antiacne agents, skin aging agents, anti-cellulite agents, anti-dandruff agents, anti-inflammatory agents, anti-irritants, anti-irritants, anti-oxidants, astringents, antiperspirants, antiseptics, antistatic agents, binders, buffers, carrier materials, chelating agents, cell stimulants, cleansing agents, skin care agents, depilatories, surface-active substances, deodorants, antiperspirants, emollients, emulsifiers, enzymes, essential oils, Fibers, film formers, fixatives, foaming agents, foam stabilizers, foaming inhibitors, foam boosters, gelling agents, gelling agents, hair care preparations, hair styling agents, hair straighteners, moisturizers, moisturisers tending substances, moisturizing substances, bleaching agents, restorers
  • the cosmetic emulsion according to the invention may also contain antiperspirant active substances (antiperspirants) and be used, for example, as a deodorant for controlling body odor.
  • antiperspirant active ingredients are mainly aluminum salts such as aluminum chloride, aluminum chlorohydrate, nitrate, sulfate, acetate, etc. are used.
  • zinc, magnesium and zirconium compounds may be advantageous.
  • the aluminum salts and, to a lesser extent, aluminum / zirconium salt combinations have proven to be of great value. Noteworthy are the partially neutralized and thus better skin-friendly, but not quite as effective Aluminiumhydroxychloride.
  • the emulsion of the invention additionally acts as a sunscreen.
  • the emulsion according to the invention preferably contains at least one UVA filter and / or at least one UVB filter and / or at least one broadband filter and / or at least one inorganic pigment.
  • the emulsion according to the invention preferably contains at least one UVA filter and / or at least one UVB filter and / or at least one broadband filter and / or at least one inorganic pigment in a total amount of from 0.01% by weight to 40% by weight, preferably 0.1% to 10 wt .-%, in particular 1, 0 to 5.0 wt .-%, based on the total weight of the emulsion.
  • VITAMINS VITAMINS
  • the emulsion according to the invention preferably contains vitamins and / or vitamin precursors, it being possible to use all vitamins or vitamin precursors which are suitable or customary for cosmetic and / or dermatological applications.
  • vitamins and vitamin precursors such as tocopherols, vitamin A, niacic acid and niacinamide, other vitamins of the B complex, in particular biotin and vitamin C, panthenol and its derivatives, especially the esters and ethers of panthenol and cationically derivatized panthenols such as Panthenol triacetate, panthenol monoethyl ether and its monoacetate, as well as cationic panthenol derivatives.
  • vitamins and vitamin precursors such as tocopherols, vitamin A, niacic acid and niacinamide
  • other vitamins of the B complex in particular biotin and vitamin C, panthenol and its derivatives, especially the esters and ethers of panthenol and cationically
  • the cosmetic emulsion according to the invention also particularly preferably contains one or more rheological additives.
  • rheological additives is meant additives which in the cosmetic emulsion have a rheological effect, e.g. an increase in viscosity, exercise.
  • Suitable rheological additives are, for example, polymeric compounds such as those of Aerosil ® -type (hydrophilic silica), polysaccharides, preferably xanthan gum, guar gum, agar-agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, polyethylene glycol Monoester and diesters of fatty acids relatively high molecular weight, polyacrylates (for example, Carbomer, Carbopol ® [Goodrich] or Synthalens ® [Sigma]), polyacrylamides, polyvinyl alcohol, and
  • Polyvinylpyrrolidone such as ethoxylated fatty acid glycerides, esters of fatty acids with polyols, for example pentaerythritol or trimethylolpropane, narrow-band fatty alcohol ethoxylates, and electrolytes such as sodium chloride and ammonium chloride, or a mixture thereof.
  • surfactants such as ethoxylated fatty acid glycerides, esters of fatty acids with polyols, for example pentaerythritol or trimethylolpropane, narrow-band fatty alcohol ethoxylates, and electrolytes such as sodium chloride and ammonium chloride, or a mixture thereof.
  • Carbomer and / or xanthan gum are preferably used as rheological additives. They belong to the hydrophilic gels and form a coherent three-dimensional network, which binds liquid. Carbomer and xanthan gum thicken the continuous phase of the emulsion of the invention, further increasing the (physical) stability of the emulsion.
  • carbomer this is an acrylic acid polymer
  • the emulsion of the invention preferably has a pH in the range of 5 to 11, more preferably 5 to 10, most preferably 5.5 to 6.5. Because the viscosity resulting from the carbomer in addition to the use concentration of the set pH depends, the maximum viscosity is achieved at a pH of 6 to 10.
  • the emulsion according to the invention is preferably free of cationic substances and / or electrolytes and / or polyvalent metal ions.
  • an aqueous sodium hydroxide solution preferably 10% (by mass).
  • the rheological additive (s) are preferably each in a concentration of 0.01 to 3.0% by weight, preferably 0.01 to 2.0% by weight, more preferably 0.01 to 1.0% by weight %, more preferably 0.01 to 0.5% by weight, more preferably 0.05 to 0.15% by weight, most preferably about 0.1% by weight, present in the emulsion of the invention on the total weight of the emulsion.
  • the emulsion according to the invention particularly preferably comprises carbomer and xanthan gum in a concentration of 0.1% by weight, based on the total weight of the emulsion.
  • the emulsion according to the invention is preferably a skin care agent, hair care product or sunscreen.
  • the invention is in the form of a cream, a lotion, a spray, an ointment or a gel.
  • the emulsion according to the invention is particularly preferably a skin cream, a shampoo, a shower gel, an antiperspirant, a deodorant or a soap.
  • the present invention relates to the use of a mixture comprising or consisting of 1, 2-hexanediol and 1, 2-octanediol for reducing the surface tension and / or the interfacial tension of a cosmetic emulsion.
  • the cosmetic emulsion is preferably a cosmetic emulsion as described above.
  • the present invention relates to the use of a mixture comprising or consisting of 1, 2-hexanediol and 1, 2-octanediol for the synergistic lowering of the surface tension and / or the interfacial tension of a cosmetic emulsion.
  • the cosmetic emulsion is preferably a previously described cosmetic emulsion.
  • Synergistically lowering the surface and / or interfacial tension means that a mixture of 1,2-hexanediol and 1,2-octanediol reduces the surface and / or interfacial tension more than expected due to the lowering of surface tension by the individual components , Namely, it is expected that a mixture of 1, 2-hexanediol and 1, 2-octanediol the surface and / or interfacial tension in comparison to independently (ie individually) used 1, 2-hexanediol and 1, 2-octanediol according to Trustsver- ratio of 1, 2-hexanediol and 1, 2-octanediol lowers.
  • HLB value of a 1: 1 mixture of 1,2-hexanediol and 1,2-octanediol lies between the HLB values of 1, 2-hexanediol and 1, 2-octanediol.
  • this expected behavior with respect to surface and surface-reducing properties does not occur, but that the surface and / or interfacial tension of a cosmetic emulsion comprising a mixture of 1, 2-hexanediol and 1, 2-octanediol clearly towards the surface tension of a cosmetic emulsion comprising 1, 2-octanediol is shifted.
  • the weight ratio of 1,2-hexanediol to 1,2-octanediol is preferably 3: 1 to 1: 3, preferably 2: 1 to 1: 2, more preferably about 1: 1, and / or the total amount 1, 2-hexanediol and 1, 2-octanediol in the emulsion up to 2.0 wt .-%, preferably up to 1, 5 wt .-%, more preferably up to 1, 0 wt .-%, more preferably up to 0.5% by weight, based on the total weight of the emulsion.
  • the cosmetic emulsion comprises a continuous water phase and dispersed oil droplets in the continuous water phase.
  • the present invention thus preferably relates to the use of a mixture comprising or consisting of 1, 2-hexanediol and 1, 2-octanediol for reducing the surface tension and / or the interfacial tension of a cosmetic O / W emulsion.
  • the cosmetic O / W emulsion is particularly preferably a two-phase system of a cosmetic oil in water.
  • a mixture comprising or consisting of 1, 2-hexanediol and 1, 2-octanediol for reducing the surface and / or interfacial tension of a cosmetic emulsion is used, so that in the water phase dispersed oil droplets of the cosmetic emulsion have a volume-related diameter d v 0 , 5 from 1, 0 to 10.0 miti, preferably 3.0 to 9.0 miti, more preferably 3.0 to 7.0 gm, most preferably 3.5 to 6.0 gm, and / or an average volume-related diameter d v 0, i of 1, 0 to 10.0 gm, preferably 1, 0 to 8.0 miti, more preferably 1, 0 to 6.0 miti, more preferably 1, 0 to 4.0 miti, more preferably 1, 0 to 3.0 miti, further preferably 1, 0 to 2 , 5 miti, more preferably 1, 5 to 2.0 miti, determined preferably by means of laser
  • a mixture comprising or consisting of 1, 2-hexanediol and 1, 2-octanediol for lowering the surface and / or surface tension of a cosmetic emulsion is used, so that the emulsion has an interfacial tension of 10 to 30 mN / m, preferably 15 to 25 mN / m, more preferably 19 to 24 mN / m, particularly preferably 20 to 24 mN / m (determined by the drop-volume method) and / or a surface tension of 10 up to 80 mN / m, preferably 20 to 60 mN / m, more preferably 20 to 50 mN / m, more preferably 20 to 40 mN / m, most preferably 20 to 40 mN / m (determined by means of the drop volume Method).
  • the mixture comprising or consisting of 1, 2-hexanediol and 1, 2-octanediol no further 1, 2-alkanediols used. It is thus preferred that the mixture and / or the emulsion contains no 1,2-alkanediols other than 1,2-hexanediol and 1,2-octanediol. It is further preferred that the mixture and / or the emulsion in this aspect does not contain 2-phenoxyethanol.
  • the cosmetic emulsion comprises an oil which is preferably selected from the group consisting of
  • the oil used in the cosmetic emulsion of the invention is selected from the group consisting of myristyl myristate, myristyl palmitate, myristyl stearate, myristyl isostearate, myristyl oleate, myristyl behenate, myristyl erucate, cetyl myristate, cetyl palmitate, cetyl stearate, cetyl isostearate, cetyl oleate, cetyl behenate, cetyl erucate, stearyl myristate , Stearyl palmitate, stearyl stearate, stearyl isostearate, stearyl oleate, stearyl behenate, stearyl erucate, isostearyl myristate, isostearyl palmitate, isostearyl stearate, isostearyl isostearate, isostearyl myristate, isostearyl
  • esters of straight-chain C 6 -C 2 2-fatty acids with branched alcohols in particular 2-ethylhexanol
  • Esters of straight-chain or branched fatty acids with polyhydric alcohols for example propylene glycol, dimerdiol or trimer triol
  • Guerbet alcohols for example propylene glycol, dimerdiol or trimer triol
  • triglycerides based on C 6 -C 10 -fatty acids and / or liquid mono- / di- / triglyceride mixtures based on C 6 -C 18- fatty acids
  • Esters of aromatic carboxylic acids especially benzoic acid, with C 6 -C 22 fatty alcohols and / or Guerbet alcohols,
  • C 6 -C 22 -fatty alcohol carbonates straight and branched C 6 -C 22 -fatty alcohol carbonates, for example dicaprylyl carbonate (Cetiol ® CC),
  • Esters of benzoic acid with linear and / or branched C 6 -C 22 alcohols such as Finsolv ® TN
  • caprylic / capric triglyceride also known as neutral oil
  • cetearyl ethyl hexanoate particularly suitable are caprylic / capric triglyceride (also known as neutral oil) and cetearyl ethyl hexanoate.
  • silicone oils cyclomethicone, silicone methicone, etc.
  • aliphatic or naphthenic hydrocarbons for example squalane, squalene or Dialkylcyclohexanes
  • a silicone oil is understood as meaning an oil which has the structural unit [R 1 R 2 SiO] n in which R 1 and R 2 are, for example, organic radicals.
  • the oil phase comprises ethylhexyl isononanoate, caprylic / capric triglyceride, and prunus amygdalus dulcis (Sweet Almond) oil.
  • the oil phase consists of these components. It has been found that this combination of low, medium and high-spreading substances of the formulation gives a good spreadability on the skin surface and ensures a pleasant skin feel.
  • the oil phase preferably comprises from 20 to 80% by weight, more preferably from 30 to 70% by weight, more preferably from 40 to 60% by weight, particularly preferably from 45 to 55% by weight, in particular about 50% by weight, Ethylhexylisononanoate, based on the total weight of the oil phase.
  • the oil phase is 10 to 60 wt .-%, more preferably 20 to 50 wt .-%, more preferably 30 to 40 wt .-%, particularly preferably 32 to 38 wt .-%, in particular about 35 wt .-%, Caprylic / Capric triglyceride, based on the total weight of the oil phase.
  • the oil phase comprises
  • caprylic / capric triglyceride From 32 to 38% by weight, in particular about 35% by weight, of caprylic / capric triglyceride and 12 to 17% by weight, in particular about 15% by weight of Prunus Amygdalus Dulcis (Sweet Almond) oil, based on the total weight of oil phase.
  • the oil phase comprises from 45 to 55% by weight, in particular about 50% by weight, ethylhexyl isononanoate, 32 to 38% by weight, in particular about 35% by weight, caprylic / capric triglyceride and 12 to 17 wt .-%, in particular about 15 wt .-% Prunus Amygdalus Dulcis (Sweet Almond) oil, based on the total weight of the oil phase.
  • the oil phase comprises or consists of caprylic / capric triglyceride and cetearylethylhexanoate.
  • the weight ratio is particularly preferably 2: 1.
  • the oil phase comprises caprylic / capric triglyceride and cetearyl ethylhexanoate in a total amount of from 1.0 to 50.0 wt%, preferably 3.0 to 30.0 wt%, more preferably 5.0 to 20.0 Wt .-%, more preferably 8.0 to 15.0 wt .-%, most preferably 10.0 to 13.0 wt .-%, or consists thereof, based on the total weight of the emulsion.
  • the oil phase comprises caprylic / capric triglyceride in an amount of 2.0 to 15.0% by weight, preferably 4.0 to 12.0% by weight, more preferably 5.0 to 10.0 Wt .-%, most preferably 7.0 to 9.0 wt .-%, and / or cetearyl ethylhexanoate in an amount of 1, 0 to 10.0 wt .-%, preferably 2.0 to 8.0 wt. %, more preferably 3.0 to 5.0 wt .-%, or consists thereof, each based on the total weight of the emulsion.
  • the oil phase comprises caprylic / capric triglyceride in an amount of 7.0 to 9.0 wt.%, And cetearyl ethylhexanoate in an amount of 3.0 to 5.0 wt. in each case based on the total weight of the emulsion.
  • the emulsion further comprises one or more emulsifiers other than 1,2-hexanediol and 1,2-octanediol.
  • the one or more emulsifiers have an HLB value in the range of 8 to 18, more preferably 8 to 16.
  • these emulsifier (s) are selected from the group consisting of PEG-100 stearate, cetearyl glucoside, distearyldimonium chloride, Palmitamidopropyltrimoniumchlorid, glyceryl stearate, glyceryl oleate, polyglyceryl (3) methylglucose, cetearyl alcohol, potassium cetyl phosphate, Natriumcetylphosphat, acrylate / C-io-C 3 o-alkyl acrylate quickerpolynner, ammonium acryloyldimethyltaurate / Beheneth- 25 methacrylate crosspolymer, Polyglyceryl-4 Caprate, polyglyceryl-4-caprylate / caprate,
  • / are the one or more of 1, 2-hexanediol and 1, 2-octanediol different / n emulsifier / s in this aspect also selected from the group consisting of cetearyl alcohol, glyceryl stearate citrate, polyglyceryl (3) - methyl glucose distearate, Potassium cetyl phosphate, hydrogenated palm glycerides and a mixture thereof.
  • the one or more of 1, 2-hexanediol and 1, 2-octanediol are various emulsifiers selected from the group consisting of glyceryl stearate citrate, polyglyceryl (3) -methyl glucose distearate, potassium cetyl phosphate, hydrogenated palm glycerides, and the like Mix of it.
  • the emulsifier other than 1, 2-hexanediol and 1, 2-octanediol is a mixture of cetearyl alcohol and a member of the group consisting of (i) a mixture of potassium cetyl phosphate and hydrogenated palm glycerides (preferably in the weight ratio in the range of 1: 1 to 7: 3, especially about 6: 4 (potassium cetyl phosphate to hydrogenated palm glycerides)), (ii) glyceryl stearate citrate and (iii) polyglyceryl (3) methyl glucose distearate.
  • the emulsifier other than 1,2-hexanediol and 1,2-octanediol is preferably a mixture of cetearyl alcohol and a mixture of potassium cetyl phosphate and hydrogenated palm glycerides, a mixture with the weight ratio in the range of 1 preferably being used as the mixture of potassium cetyl phosphate and hydrogenated palm glycerides. 1 to 7: 3, especially about 6: 4 (potassium cetyl phosphate: hydrogenated palm glycerides) is used.
  • the emulsifier other than 1, 2-hexanediol and 1, 2-octanediol is a mixture of cetearyl alcohol and glyceryl stearate citrate.
  • the emulsifier other than 1,2-hexanediol and 1,2-octanediol is a mixture of cetearyl alcohol and polyglyceryl (3) -methyl glucose distearate.
  • the emulsifier other than 1,2-hexanediol and 1,2-octanediol is a mixture of potassium cetyl phosphate and hydrogenated palm glycerides, the weight ratio of potassium cetyl phosphate to hydrogenated palm glycerides in the mixture of potassium cetyl phosphate and hydrogenated palm glycerides being more preferably 1: 1 to 7: 3, in particular about 6: 4, is. Also preferred is the different from 1, 2-hexanediol and 1, 2-octanediol emulsifier glyceryl stearate citrate. Further preferably, the emulsifier other than 1, 2-hexanediol and 1, 2-octanediol is polyglyceryl (3) -methylglucose distearate.
  • the cosmetic emulsion also in this aspect further contains other useful ingredients which are described in the first aspect and to which reference is hereby made.
  • the present invention relates to a process for the preparation of a cosmetic emulsion according to any one of the preceding aspects.
  • the process according to the invention consists of or comprises the following steps: a) providing an aqueous phase; b) providing an oil phase; c) combining the aqueous phase and the oil phase, wherein the aqueous phase and / or the oil phase comprises 1, 2-hexanediol and / or 1, 2-octanediol.
  • the aqueous phase comprises 1, 2-hexanediol and 1, 2-octanediol.
  • the oil phase comprises 1, 2-hexanediol and 1, 2-octanediol.
  • the aqueous phase and the oil phase comprise 1, 2-hexanediol and 1, 2-octanediol.
  • the aqueous phase comprises 1, 2-hexanediol and the oil phase comprises 1, 2-octanediol.
  • the aqueous phase comprises 1, 2-octanediol and the oil phase 1, 2-hexanediol.
  • the aqueous phase and / or the oil phase is / are preferably heated before step c), which leads to a good homogenization of the phases.
  • the phases are heated to a temperature of 50 to 100 ° C., in particular when the aqueous phase is at a temperature in the range of 70 to 90 ° C., preferably to about 80 ° G, and when the oil phase is heated to a temperature in the range of 80 to 100 ° G, preferably to about 90 ° G. Therefore, the phases are preferably heated to a temperature of 50 to 100 ° C.
  • the aqueous phase is heated to a temperature in the range of 70 to 90 ° C, preferably to about 80 ° C, and the oil phase is heated to a temperature in the range of 80 to 100 ° C, preferably at about 90 ° C , This led to the best results.
  • the emulsion of the invention comprises one or more rheological additives
  • the phases combined in step c) are preferably homogenized.
  • a forthcoming Trains t Zahnkranzdispergier unit (IKA ® ULTRA TURRAX T25 digital ®) is used.
  • the homogenization is carried out for 3 minutes at 6000 rev / min.
  • the emulsion obtained can be adjusted to the desired pH with stirring, preferably by means of a paddle stirrer, more preferably at 150 rpm, with a sodium hydroxide solution, preferably 10% strength.
  • a sodium hydroxide solution preferably 10% strength.
  • carbomer is used as a rheological additive
  • the resulting emulsion is preferably adjusted to a pH in the range of 5-11, preferably 5-10, more preferably 5.5 to 6.5. This pH also has the advantage that the acid mantle of the skin is not attacked, resulting in good skin compatibility.
  • the emulsion is cooled, preferably gently, with stirring for 10 minutes at 150 rpm, for 10 minutes at 100 rpm and for 5 minutes at 50 rpm until, after completion of the stirring operation Temperature of about 43 ° C.
  • the interfacial tension was determined by the drop-volume method (dynamic method). A device of the type "Krüss DVT50" was used.
  • a water droplet (demineralized) was produced by means of a capillary (diameter 0.2540 mm) and metered into a model oil phase. The capillary thus protruded into the model oil phase.
  • the detachment of the drop was detected by means of a light barrier and the drop volume was calculated from the volume flow. All measurements were performed in duplicate, with each single measurement being the mean of the three falling drop readings. The final value used for the evaluation is calculated by averaging the double determination.
  • Solution 2 Model oil phase + 1, 2-hexanediol (0.5% by weight)
  • Solution 3 Model oil phase + 1,2-octanediol (0.5% by weight)
  • Solution 4 Model oil phase + 1: 1 mixture of 1, 2-hexanediol and 1, 2-octanediol (0.5
  • the wt .-% refer to the total weight of the oil phase (model oil phase + 1, 2-alkanediol). The results are shown in Table 1.
  • the interfacial tension between the model oil phase and water (deionized) in the absence of emulsifiers is about 33 mN / m.
  • the addition of 1,2-alkanediols reduces this interfacial tension.
  • Solution 2 (addition of 1,2-hexanediol) shows an interfacial tension of about 28 mN / m, the interfacial tension decreasing slightly with increasing interfacial age (from 28.8 mN / m at 5.5 s to 25.4 mN / m) 494.8 s).
  • Solution 3 (addition of 1,2-octanediol) has an interfacial tension of about 20 mN / m, the interfacial tension decreasing slightly with increasing interfacial age (from 21.3 mN / m at 4.0 s to 18.4 mN / m at 572.5 s).
  • the interfacial tension of solution 4 (addition of
  • the mixture is present as a liquid (1,2-octanediol is a solid), so that the mixture can be metered particularly easily in the preparation of emulsions.
  • composition is shown in the following table:
  • phase B to phase A and emulsify (Homo Rex, 3 min, 6000 rpm).
  • phase C and stir with the help of a paddle stirrer.
  • the surface tension of deionized water was determined by the drop-volume method (static method).
  • a device of the type LAUDA TVT2 was used.
  • water droplets demineralized
  • the detachment of the drop was detected by means of a light barrier and the drop volume was calculated from the volume flow. All measurements were performed in triplicate, with each single measurement being the average of the five falling drop readings. The final value used for the evaluation is calculated by averaging the triple determination.

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Abstract

La présente invention concerne de nouvelles émulsions cosmétiques contenant du 1,2-hexanediol et du 1,2-octanediol, des utilisations avantageuses de celles-ci et des procédés pour leur production.
PCT/EP2017/084472 2017-12-22 2017-12-22 Émulsions contenant des mélanges de 1,2-hexanediol et de 1,2-octanediol WO2019120572A1 (fr)

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