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    公开号:AU2005299029A1
    申请号:U2005299029
    申请日:2005-10-07
    公开日:2006-05-04
    发明作者:Bijan Harichian；Richard Loren Mcmanus；Jose Guillermo Rosa
    申请人:Unilever PLC；
    IPC主号:A61K8-41
    专利说明:
    WO 2006/045427 PCT/EP2005/010905 -1 PERSONAL CARE PRODUCTS WHICH INCLUDE DIHYDROXYPROPYLTRI (C 1
    -C
    3 ALKYL) AMMONIUM SALTS Technical Field of the Invention 5 The invention concerns personal care compositions providing moisturization both in high and low relative humidity environments. Background of the Invention 10 Dry skin is a problem in varying degree to most humans. This condition is particularly evident in winter. Personal care products such as skin creams/lotions, shampoos/conditioners, toilette bars/shower gels and antiperspirant/deodorants are normally formulated with at least one material to address dry 15 skin. Symptoms such as itching, flaking and a visually displeasing dermal appearance can all to some extent be modulated. There are three classes of materials employed against the problem. Occlusives such as petrolatum or silicone oils serve to 20 inhibit loss of natural moisture. They form a barrier between the epidermis and the environment. Another approach is the use of keratolytic agents to enhance rate of dermal exfoliation. Alpha hydroxy acids are the most common agents for achieving exfoliation. 25 A third approach to dry skin is topical application of humectants. Hydroxylated monomeric and polymeric organic substances are generally used for this purpose. Glycerin known also as glycerol is one of the most effective humectants.
    WO 2006/045427 PCT/EP2005/010905 -2 There are several shortcomings in the performance of known humectants. Even the best such as glycerin requires to be formulated at relatively high levels to achieve good moisturization. Secondly, known humectants perform well in high 5 relative humidity environments; however, hardly any of these substances provide effectiveness at low relative humidity (i.e. less than 20% moisture at 20 0 C). Average indoor relative humidity during winter is approximately 13% in areas such as the north-east U.S. It is quite evident that a real need exists for 10 an improved moisturization technology. A moisturizer known as Honeyquat 50 with INCI name of Hydroxypropyltrimonium Honey has been reported to be a better humectant than glycerin (see the Arch/Brooks brochure titled "Cosmetic Ingredients & Ideas*", Issue No. 2, August 2001). 15 Honeyquat 50 is described as being derived from the reaction of pendent hydroxyl groups~ (on the disaccharide) of a "light" deodorized grade of honey with a chlorohydroxytrimethyl ammonium derivative. Although this substance has excellent humectancy, moisturization at low relative humidity still remains to be 20 conquered. Accordingly, the present invention seeks to identify humectants which are operative not only at high but also low relative humidity, for application in personal care products.
    WO 2006/045427 PCT/EP2005/010905 -3 Summary of the Invention A personal care product is provided which includes: (A) a personal care composition including: (i) from 0.1 to 30% by weight of 5 dihydroxypropyltri(Ci-C 3 alkyl) ammonium salt; (ii) a cosmetically acceptable carrier; (B) a package for delivering the composition to a consumer; and (C) instructions printed on or associated with the package 10 indicating topical use of the composition on skin. Detailed Description of the Invention Now it has been found that hydroxypropyltri(C-C 3 alkyl) ammonium salts are excellent moisturizers providing humectancy at both 15 high and low relative humidity environments. These salts may be obtained in a variety of synthetic procedures, most particularly by hydrolysis of chlorohydroxypropyltri(C-C 3 alkyl) ammonium salts. A most preferred salt is 1,2-dihydroxypropyltrimonium chloride, wherein the C 1
    -C
    3 alkyl is a methyl group. Amounts of 20 the salt may range from 0.1 to 30%, preferably from 0.5 to 20%, optimally from 1% to 12% by weight of the composition. Ordinarily the C 1
    -C
    3 alkyl constituent on the quaternized ammonium (quat) group will be methyl, ethyl, n-propyl, isopropyl or hydroxyethyl and mixtures thereof. Particularly preferred is 25 a trimethyl ammonium group known through INCI nomenclature as a "trimonium" group. Any anion can be used in the quat salt. The anion may be organic or inorganic with the proviso that the material is cosmetically acceptable. Typical inorganic anions are halides, sulfates, phosphates, nitrates and borates. Most 30 preferred are the halides, especially chloride. Organic anionic WO 2006/045427 PCT/EP2005/010905 -4 counter ions include methosulfate, toluoyl sulfate, acetate, citrate, tartrate, lactate, gluconate, and benzenesulfonate. By the term personal care composition is meant any substance applied to a human body for improving appearance, cleansing, odor 5 control or general aesthetics. Non-limiting examples of personal care compositions include leave-on skin lotions and creams, shampoos, hair conditioners, shower gels, toilet bars, antiperspirants, deodorants, dental products, shave creams, depilatories, lipsticks, foundations, mascara, sunless tanners 10 and sunscreen lotions. Compositions of this invention will also include a cosmetically acceptable carrier. Amounts of the carrier may range from 1 to 99.9%, preferably from 70 to 95%, optimally from 80 to 90% by weight of the composition. Among the useful carriers are water, 15 emollients, fatty acids, fatty alcohols, thickeners and combinations thereof. The carrier may be aqueous, anhydrous or an emulsion. Preferably the compositions are aqueous, especially water and oil emulsions of the W/O or O/W or triplex W/0/W variety. Water when present may be in amounts ranging from 5 to 20 95%, preferably from 20 to 70%, optimally from 35 to 60% by weight of the composition. Emollient materials may serve as cosmetically acceptable carriers. These may be in the form of silicone oils, natural or synthetic esters and hydrocarbons. Amounts of the 25 emollients may range anywhere from 0.1 to 95%, preferably between 1 and 50% by weight of the composition. Silicone oils may be divided into the volatile and non-volatile variety. The term "volatile" as used herein refers to those materials which have a measurable vapor pressure at ambient WO 2006/045427 PCT/EP2005/010905 -5 temperature. Volatile silicone oils are preferably chosen from cyclic (cyclomethicone) or linear polydimethylsiloxanes containing from 3 to 9, preferably from 4 to 5, silicon atoms. Non-volatile silicone 'oils useful as an emollient material 5 include polyalkyl siloxanes, polyalkylaryl siloxanes and polyether siloxane copolymers. The essentially non-volatile polyalkyl siloxanes useful herein include, for example, polydimethyl siloxanes with viscosities of from 5 x 10~6 to 0.1 m 2 /s at 25 0 C. Among the preferred non-volatile emollients useful 10 in the present compositions are the polydimethyl siloxanes having viscosities from 1 x 10~5 to 4 x 10-4 m 2 /s at 25 0 C. Another class of non-volatile silicones are emulsifying and non emulsifying silicone elastomers. Representative of this category is dimethicone/vinyl dimethicone crosspolymer available as Dow 15 Corning 9040, General Electric SFE 839, and Shin-Etsu KSG-18. Silicone waxes such as Silwax WS-L (dimethicone copolyol laurate) may also be useful. Among the ester emollients are: a) Alkyl esters of saturated fatty acids having 10 to 24 20 carbon atoms. Examples thereof include behenyl neopentanoate, isononyl isonanonoate, isopropyl myristate and octyl stearate. b) Ether-esters such as fatty acid esters of ethoxylated saturated fatty alcohols. 25 c) Polyhydric alcohol esters such as ethylene glycol mono and di-fatty acid esters, diethylene glycol mono- and di-fatty acid esters, polyethylene glycol (200-6000) mono- and di- WO 2006/045427 PCT/EP2005/010905 -6 fatty acid esters, propylene glycol mono- and di-fatty acid esters, polypropylene glycol 2000 monostearate, ethoxylated propylene glycol monostearate, glyceryl mono- and di-fatty acid esters, polyglycerol poly-fatty esters, ethoxylated 5 glyceryl mono-stearate, 1,3-butylene glycol monostearate, 1,3-butylene glycol distearate, polyoxyethylene polyol fatty acid ester, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters are satisfactory. Particularly useful are pentaerythritol, trimethylolpropane and neopentyl 10 glycol esters of C 1
    -C
    3 0 alcohols. d) Wax esters such as beeswax, spermaceti wax and tribehenin wax. e) Sugar ester of fatty acids such as sucrose polybehenate and sucrose polycottonseedate. Natural ester emollients principally are based upon mono-, di and tri- glycerides. Representative glycerides include sunflower 15 seed oil, cottonseed oil,. borage oil, borage seed oil, primrose oil, castor and hydrogenated castor oils, rice bran oil, soybean oil, olive oil, safflower oil, shea butter, jojoba oil and combinations thereof. Animal derived emollients are represented by lanolin oil and lanolin derivatives. Amounts of the natural 20 esters may range from 0.1 to 20% by weight of the compositions. Hydrocarbons which are suitable cosmetically acceptable carriers include petrolatum, mineral oil, C 11
    -C
    1 3 isoparaffins, polybutenes, and especially isohexadecane, available commercially as Permethyl 101A from Presperse Inc. 25 Fatty acids having from 10 to 30 carbon atoms may also be suitable as cosmetically acceptable carriers. Illustrative of WO 2006/045427 PCT/EP2005/010905 -7 this category are pelargonic, lauric, myristic, palmitic, stearic, isostearic, oleic, linoleic, linolenic, hydroxystearic and behenic acids. Fatty alcohols having from 10 to 30 carbon atoms are another 5 useful category of cosmetically acceptable carrier. Illustrative of this category are stearyl alcohol, lauryl alcohol, myristyl alcohol, oleyl alcohol and cetyl alcohol. Thickeners can be utilized as part of the cosmetically acceptable carrier of compositions according to the present invention. 10 Typical thickeners include crosslinked acrylates (e.g. Carbopol 982*), hydrophobically-modified acrylates (e.g. Carbopol 1382*), polyacrylamides (e.g. Sepigel 305*), acryloylmethylpropane sulfonic acid/salt polymers and copolymers (e.g. Aristoflex HMB* and AVC*), cellulosic derivatives and natural gums. Among useful 15 cellulosic derivatives are sodium carboxymethylcellulose, hydroxypropyl methocellulose, hydroxypropyl cellulose, hydroxyethyl cellulose, ethyl cellulose and hydroxymethyl cellulose. Natural gums suitable for the present invention include guar, xanthan, sclerotium, carrageenan, pectin and 20 combinations of these gums. Inorganics may also be utilized as thickeners, particularly clays such as bentonites and hectorites, fumed silicas, talc, calcium carbonate and silicates such as magnesium aluminum silicate (Veegum*). Amounts of the thickener may range from 0.0001 to 10%, usually from 0.001 to 1%, optimally 25 from 0.01 to 0.5% by weight of the composition. Adjunct humectants may be employed in the present invention. These are generally polyhydric alcohol-type materials. Typical polyhydric alcohols include glycerol, propylene glycol, dipropylene glycol, polypropylene glycol, polyethylene glycol, 30 sorbitol, hydroxypropyl sorbitol, hexylene glycol, 1,3-butylene WO 2006/045427 PCT/EP2005/010905 -8 glycol, isoprene glycol, 1,2,6-hexanetriol, ethoxylated glycerol, propoxylated glycerol and mixtures thereof. The amount of adjunct humectant may range anywhere from 0.5 to 50%, preferably between 1 and 15% by weight of the composition. 5 Personal care compositions of the present invention may be in any form. These forms may include lotions, creams, roll-on formulations, sticks, mousses, aerosol and non-aerosol sprays and fabric (e.g. non-woven textile) -applied formulations. Surfactants may also be present in compositions of the present 10 invention. Total concentration of the surfactant when present may range from 0.1 to 90%, preferably from 1 to 40%, optimally from 1 to 20% by weight of the composition, and is highly dependent upon the type of personal care product. The surfactant may be selected from the group consisting of anionic, nonionic, 15 cationic and amphoteric actives. Particularly preferred nonionic surfactants are those with a C 1 0
    -C
    2 0 fatty alcohol or acid hydrophobe condensed with from 2 to 100 moles of ethylene oxide or propylene oxide per mole of hydrophobe; C 2 -Cio alkyl phenols condensed with from 2 to 20 moles of alkylene oxide; mono- and 20 di-fatty acid esters of ethylene glycol; fatty acid monoglyceride; sorbitan, mono- and di- C 8
    -C
    20 fatty acids; and polyoxyethylene sorbitan as well as combinations thereof. Alkyl polyglycosides and saccharide fatty amides (e.g. methyl gluconamides) and trialkylamine oxides are also suitable nonionic 25 surfactants. Preferred anionic surfactants include soap, alkyl ether sulfates and sulfonates, alkyl sulfates and sulfonates, alkylbenzene sulfonates, alkyl and dialkyl sulfosuccinates, C3-C 20 acyl isethionates, C 8
    -C
    20 alkyl ether phosphates, C 8
    -C
    2 0 sarcosinates, 30 C3-C 20 acyl lactylates, sulfoacetates and combinations thereof.
    WO 2006/045427 PCT/EP2005/010905 -9 Useful amphoteric surfactants include cocoamidopropyl betaine,
    C
    12
    -C
    20 trialkyl betaines, sodium lauroamphoacetate, and sodium laurodiamphoacetate. Sunscreen agents may also be included in compositions of the 5 present invention. Particularly preferred are such materials as ethylhexyl p-methoxycinramate (Parsol MCX@), avobenzene (Parsol 1789*) and benzophenone-3 (also known as oxybenzone). Inorganic sunscreen actives may be employed such as microfine titanium dioxide and zinc oxide. Amounts of the sunscreen agents when 10 present may generally range from 0.1 to 30%, preferably from 2 to 20%, optimally from 4 to 10% by weight of the composition. Antiperspirants and deodorant compositions of the present invention ordinarily will contain astringent actives. Examples include aluminum chloride, aluminum chlorhydrex, aluminum 15 zirconium chlorhydrex glycine, aluminum sulfate, zinc sulfate, zirconium and aluminum chlorohydroglycinate, zirconium hydroxychloride, zirconium and aluminum lactate, zinc phenolsulfonate and combinations thereof. Amounts of the astringents may range anywhere from 0.5 to 50% by weight of the 20 composition. Dental products formulated according to the present invention will generally contain a fluoride source to prevent dental caries. Typical anti-caries actives include sodium fluoride, stannous fluoride and sodium monofluoro phosphate. Amounts of 25 these materials will be determined by the amount of fluoride releasable which should range between 500 to 8800 ppm of the composition. Other components of dentifrices can include desensitizing agents such as potassium nitrate and strontium nitrate, sweeteners such as sodium saccharine, aspartame, WO 2006/045427 PCT/EP2005/010905 - 10 sucralose, and potassium acesulfam. Thickeners, opacifying agents, abrasives and colorants will normally also be present. Preservatives can desirably be incorporated into the personal care compositions of this invention to protect against the growth 5 of potentially harmful microorganisms. Particularly preferred preservatives are phenoxyethanol, methyl paraben, propyl paraben, imidazolidinyl urea, dimethyloldimethylhydantoin, ethylenediaminetetraacetic acid salts (EDTA), sodium dehydroacetate, methylchloroisothiazolinone, 10 methylisothiazolinone, iodopropynbutylcarbamate and benzyl alcohol. The preservatives should be selected having regard for the use of the composition and possible incompatibilities between the preservatives and other ingredients. Preservatives are preferably employed in amounts ranging from 0.0001% to 2% by 15 weight of the composition. Compositions of the present invention may include vitamins. Illustrative vitamins are vitamin A (retinol), vitamin B 2 , vitamin B 3 (niacinamide), vitamin B 6 , vitamin C, vitamin E, folic acid and biotin. Derivatives of the vitamins may also be 20 employed. For instance, vitamin C derivatives include ascorbyl tetraisopalmitate, magnesium ascorbyl phosphate and ascorbyl glycoside. Derivatives of vitamin E include tocopheryl acetate, tocopheryl palmitate and tocopheryl linoleate. DL-panthenol and derivatives may also be employed. Total amount of vitamins when 25 present in compositions according to the present invention may range from 0.001 to 10%, preferably from 0.01% to 1%, optimally from 0.1 to 0.5% by weight of the composition. Another type of useful substance can be that of an enzyme such as amylases, oxidases, proteases, lipases and combinations.
    WO 2006/045427 PCT/EP2005/010905 - 11 Particularly preferred is superoxide dismutase, commercially available as Biocell SOD from the Brooks Company, USA. Skin lightening compounds may be included in the compositions of the invention. Illustrative substances are placental extract, 5 lactic acid, niacinamide, arbutin, kojic acid, ferulic acid, resorcinol and derivatives including 4-substituted resorcinols and combinations thereof. Amounts of these agents may range from 0.1 to 10%, preferably from 0.5 to 2% by weight of the composition. 10 Desquamation promoters may be present. Illustrative are the alpha-hydroxycarboxylic acids and beta-hydroxycarboxylic acids. The term "acid" is meant to include not only the free acid but also salts and Cl-C 30 alkyl or aryl esters thereof and lactones generated from removal of water to form cyclic or linear lactone 15 structures. Representative acids are glycolic, lactic and malic acids. Salicylic acid is representative of the beta hydroxycarboxylic acids. Amounts of these materials when present may range from 0.01 to 15% by weight of the composition. A variety of herbal extracts may optionally be included in 20 compositions of this invention. The extracts may either be water soluble or water-insoluble carried in a solvent which respectively is hydrophilic or hydrophobic. Water and ethanol are the preferred extract solvents. Illustrative extracts include those from green tea, chamomile, licorice, aloe vera, 25 grape seed, citrus unshui, willow bark, sage, thyme and rosemary. Also included may be such materials as lipoic acid, retinoxytrimethylsilane (available from Clariant Corp. under the Silcare 1M-75 trademark), dehydroepiandrosterone (DHEA) and combinations thereof. Ceramides (including Ceramide 1, Ceramide WO 2006/045427 PCT/EP2005/010905 - 12 3, Ceramide 3B and Ceramide 6) as well as pseudoceramides may also be useful. Amounts of these materials may range from 0.000001 to 10%, preferably from 0.0001 to 1% by weight of the composition. 5 Colorants, opacifiers and abrasives may also be included in compositions of the present invention. Each of these substances may range from 0.05 to 5%, preferably between 0.1 and 3% by weight of the composition. The compositions of the present invention can also be, 10 optionally, incorporated into an insoluble substrate for application to the skin such as in the form of a treated wipe. A wide variety of packaging can be employed to store and deliver the personal care compositions. Packaging is often dependent upon the type of personal care end-use. For instance, leave-on 15 skin lotions and creams, shampoos, hair conditioners and shower gels generally employ plastic containers with an opening at a dispensing end covered by a closure. Typical closures are screw caps, non-aerosol pumps and flip-top hinged lids. Packaging for antiperspirants, deodorants and depilatories may involve a 20 container with a roll-on ball on a dispensing end. Alternatively these types of personal care products may be delivered as a stick composition formulation in a container with a propel-repel mechanism where the stick moves on a platform towards a dispensing orifice. Metallic cans pressurized by a propellant 25 and having a spray nozzle serve as packaging for antiperspirants, shave creams and other sprayable personal care products. Toilette bars may have packaging constituted by a cellulosic or plastic wrapper or within a cardboard box or even encompassed by a shrink wrap plastic film. All of the aforementioned are 30 considered packaging within the context of the present invention.
    WO 2006/045427 PCT/EP2005/010905 - 13 Another aspect of personal care products of this invention will be the inclusion of instructions attached to or otherwise associated with the packaging. The instructions indicate to a consumer topical use of the composition on skin, hair or oral 5 mucosae. Packaging itself will usually be printed with the instructions but sometimes a separate written insert within the package may serve to provide the instructions. Typical language includes phrases such as "apply a thin layer to the underarm", "apply regularly to hands", "apply to wet hair, lather and 10 rinse", "cleanse skin" and "pump a small amount onto the palm of your hand". The term "comprising" is meant not to be limiting to any subsequently stated elements but rather to encompass non specified elements of major or minor functional importance. In 15 other words the listed steps, elements or options need not be exhaustive. Whenever the words "including" or "having" are used, these terms are meant to be equivalent to "comprising" as defined above. The following examples will more fully illustrate the embodiments 20 of this invention. All parts, percentages and proportions referred to herein and in the appended claims are by weight unless otherwise illustrated.
    WO 2006/045427 PCT/EP2005/010905 - 14 EXAMPLE 1 A representative personal care composition of the present invention in the form of a cosmetic lotion is outlined under Table I. 5 TABLE I INGREDIENT WEIGHT % PHASE A Water Balance Disodium EDTA 0.05 Methyl paraben 0.15 Magnesium aluminum silicate 0.60 Triethanolamine 1.20 Dihydroxypropytrimonium chloride 1.00 PHASE B Xanthan gum 0.20 Natrosol® 250HHR (ethyl 0.50 cellulose) Butylene glycol 3.00 Glycerin 2.00 PHASE C Sodium stearoyl lactylate 0.10 Glycerol monostearate 1.50 Stearyl alcohol 1.50 Isostearyl palmitate 3.00 Silicone fluid 1.00 Cholesterol 0.25 Sorbitan stearate 1.00 Butylated hydroxy toluene 0.05 Vitamin E acetate 0.01 PEG-100 stearate 2.00 Stearic acid 3.00 Propyl paraben 0.10 Parsol MCX* 2.00 Caprylic/capric triglyceride 0.50 Hydroxycaprylic ac id 0.01 C12-15 alkyl octanoate 3.00 PHASE D Vitamin A palmitate- 0.10 Bisabolol 0.01 Vitamin A acetate 0.01 Fragrance 0.03 Retinol 50C 0.02 Conjugated linoleic acid 0.50 WO 2006/045427 PCT/EP2005/010905 - 15 EXAMPLE 2 A water-in-oil topical liquid make-up foundation according to invention is described in Table II below. 5 TABLE II INGREDIENT WEIGHT % PHASE A Cyclomethicone 9.25 Oleyl oleate 2.00 Dimethicone copolyol 20.00 PHASE B Talc 3.38 Pigment (iron oxides) 10. 51 Spheron L-1500 (silica) 0.50 PHASE C Synthetic wax Durachem 0602 0.10 Arachidyl behenate 0.30 PHASE D Cyclomethicone 1.00 Trihydroxystearin 0.30 PHASE E Laureth-7 0.50 Propyl paraben 0.25 PHASE F Fragrance 1 0.05 PHASE G Water balance Dihydroxypropytrimonium chloride 3.00 Methyl paraben 0.12 Propylene glycol 8.00 Niacinamide 4.00 Glycerin 3.00 Sodium chloride 2.00 Sodium dehydroacetate 0.30 WO 2006/045427 PCT/EP2005/010905 - 16 EXAMPLE 3 Illustrated herein is a skin cream incorporating a quat salt of the present invention. 5 TABLE III INGREDIENT WEIGHT % Glycerin 6.93 Niacinamide 5.00 Dihydroxypropytrimonium chloride 5.00 Permethyl' 101A' 3.00 Sepigelm 3052 2.50 Q2-1403 3 2.00 Linseed oil 1.33 Arlatonem 21214 1.00 Cetyl alcohol CO-1695 0.72 SEFA cottonate 5 0.67 Tocopherol acetate 0.50 Panthenol 0.50 Stearyl alcohol 0.48 Titanium dioxide 0.40 Disodium EDTA 0.10 Glydant' Plus' 0.10 PEG-100 stearate 0.10 Stearic acid 0.10 Purified water Balance 1 Isohexadecane (Presperse Inc., South Plainfield, NJ); 2 Polyacrylamide(and)C13-14 isoparaffin(and) laureth-7 (Seppic Corporation, Fairfield, NJ); 3 Dimethicone(and)dimethiconol (Dow Corning Corp. Midland, MI); 10 4 Sorbitan monostearate and sucrococoate (ICI Americas Inc., Wilmington, DE); s Sucrose ester of fatty acid; 6 DMDM Hydantoin (and) iodopropynyl butylcarbamate (Lonza Inc., Fairlawn, NJ).
    WO 2006/045427 PCT/EP2005/010905 - 17 EXAMPLE 4 Illustrative of another cosmetic composition incorporating a quat salt according to the present invention is the formula of Table IV. 5 TABLE IV INGREDIENT WEIGHT % Polysilicone-11 29 Cyclomethicone 59 Petrolatum 11 Dihydroxypropytrimonium chloride 0.2 Dimethicone copolyol 0.5 Sunflowerseed oil 0.3 EXAMPLE 5 10 A relatively anhydrous composition and incorporating a quat salt of the present invention is reported in Table V. TABLE V INGREDIENT WEIGHT % Cyclomethicone 80.65 Dimethicone 9.60 Squalane 6.00 Isostearic acid 1.90 Borage seed oil 0.90 Dihydroxypropyt rimonium 0.50 chloride Retinyl palmitate 0.25 Ceramide 6 0.10 Tocopherol 0.10 15 WO 2006/045427 PCT/EP2005/010905 - 18 EXAMPLE 6 An aerosol packaged foaming cleanser with a quat salt suitable for the present invention is outlined in Table VI. 5 TABLE VI INGREDIENT WEIGHT % Sunflower seed oil 20.00 Maleated soybean oil 5.00 Silicone urethane 1.00 Polyglycero-4 oleate 1.00 Sodium C14-16 olefin sulfonate 15.00 Sodium lauryl ether sulphate (25% 15.00 active) Cocoamidopropylbetaine 15.00 DC 1784* (silicone emulsion 50%) 5.00 Polyquaternium-11 1.00 Dihydroxypropytrimonium chloride 1.00 Water Balance EXAMPLE 7 A disposable, single use personal care towelette product is described according to the present invention. A 70/30 10 polyester/rayon non-woven towelette is prepared with a weight of 1.8 grams and dimensions of 15 cm by 20 cm. Onto this towelette is impregnated a composition with a quaternary amonium salt as outlined in Table VII below. 15 TABLE VII INGREDIENT WEIGHT % Dihydroxypropytrimonium chloride 7.50 Glycerin 2.00 Hexylene glycol 2.00 Disodium capryl amphodiacetate 1.00 Gluconolactone 0.90 Silicone microemuls ion 0.85 Witch hazel 0.50 PEG-40 hydrogenated castor oil 0.50 Fragrance 0.20 Vitamin E acetate 0.001 Water Balance WO 2006/045427 PCT/EP2005/010905 - 19 EXAMPLE 8 A toilette bar illustrative of the present invention is outlined under Table VIII. TABLE VIII INGREDIENT WEIGHT % Sodium soap (85/15 tallow/coconut) 77.77 Dihydroxypropytrimonium chloride 3.50 Glycerin 2.50 Sodium chloride 0.77 Titanium dioxide 0.40 Fragrance 1.50 Disodium EDTA 0.02 Sodium etidronate 0.02 Fluorescer 0.024 Water Balance 5 EXAMPLE 9 A shampoo composition useful in the context of the present invention is described in Table IX below. TABLE IX Ingredient Weight % Ammonium laureth sulfate 12.00 Ammonium lauryl sulfate 2.00 Cocoamidopropyl betaine 2.00 Sodium lauroamphoacetate 2.00 Dihydroxypropytrimonium chloride 5.50 Ethylene glycol distearate 1.50 Cocomonoethanolamide 0.80 Cetyl alcohol 0.60 Polyquaternium-10 0.50 Dimethicone 1.00 Zinc pyridinethione 1.00 Sodium citrate 0.40 Citric acid 0.39 Sodium xylene sulfonate 1.00 Fragrance 0.40 Sodium benzoate 0.25 Kathon CG@ 0.0008 Benzyl alcohol 0.0225 Water Balance 10 WO 2006/045427 PCT/EP2005/010905 - 20 EXAMPLE 10 This Example illustrates an antiperspirant/deodorant formula incorporating the moisturizing actives according to the present invention. 5 TABLE X Ingredient Weight % Cyclopentasiloxane 44 Dimethicone 20 Aluminum zirconium trichlorohydrex 15 glycinate Dihydroxypropytrimonium chloride 5.0 Cis-C,, acid triglyceride 5.0 Microcrystalline wax 3.0 Glycerin 3.0 Silica 2.5 Dimethicone crosspolymer 1.0 Fragrance 0.5 Disodium EDTA 0.4 Butylated hydroxytoluene 0.3 Citric acid 0.3 EXAMPLE 11 A toothpaste according to the present invention can be formulated with the ingredients listed under Table XI. 10 TABLE XI Ingredients Weight % Zeodent 115@ 20.00 Glycerin 18.00 Xanthan gum 7.00 Sodium carboxymethyl cellulose 0.50 Sodium bicarbonate 2.50 Dihydroxypropytrimonium chloride 2.00 Sodium laurylsulfate 1.50 Sodium fluoride 1.10 Sodium saccharin 0.40 Titanium dioxide 1.00 Pluronic F-127@ 2.00 FD&C Blue No. 1 3.30 Menthol 0.80 Potassium nitrate 5.00 water Balance WO 2006/045427 PCT/EP2005/010905 - 21 EXAMPLE 12 This Example provides the results of moisturization efficacy tests. These tests involved evaluation on porcine epidermis utilized as a human skin model. The equipment and protocol are 5 outlined below. An environmental microbalance (Model MB-300W, VTI Corp., 2708 W 84th Street, Hialeah, FL 33016) was programmed to measure the change in weight of porcine skin as a function of relative humidity at a constant temperature and air flow. The porcine 10 skin was evaluated before and after treatment with aqueous solutions of humectants to determine the adsorption and retention of moisture. Sample preparation was done as follows: 1. Epidermal sections of porcine skin were cut to approximately 4 15 cm x 1 cm. 2. The skin was washed in a 10% detergent solution and dried in a dessicator to a constant- weight. This represents the untreated material. 3. The skin was soaked in a 1% by weight aqueous solution of the 20 test sample for 15 minutes, excess fluid was blotted off and the skin was dried to constant weight in a dessicator. This represents the treated material. The sequence of conditions for the microbalance was as follows: 25 1. 30 minutes at 0% relative humidity (ensures that sample is dry). 2. 90 minutes at 80% relative humidity (determines amount of water picked up). 3. 90 minutes at 20% relative humidity. (determines amount of 30 water retained).
    WO 2006/045427 PCT/EP2005/010905 - 22 The experiments were conducted as follows: 1. The weight of a piece of untreated skin was recorded continuously during the sequence. 5 2. The piece of untreated skin was treated with the test sample. 3. The weight of the treated piece of skin was recorded continuously during the sequence. 4. Data reduction consisted of calculating the percent weight change from the initial weight for the untreated and treated 10 pieces of skin. 5. The reported data was the difference between each treated piece and its corresponding untreated piece. Results are recorded in Table XII. 15 TABLE XII Sample* From 0 through 80% From 0 to 80 to 20% Relative Humidity Relative Humidity Dihydroxypropyl 2.20 3.50 trimonium Chloride Honeyquat® 0.31 0.70 Honey 0.24 0.02 Quat* 188 0.21 0.10 Glycerin 0.21 0.10 * All samples tested at 1% active material in water solution. Data points represent the difference in weight of treated skin minus untreated skin. 20 Evident from the results is that dihydroxypropyl trimonium chloride was not only effective for moisturizing at relatively high humidity but also exceptional at relatively low humidity. This contrasts with Quat* 188 (chlorohydroxypropyl trimonium chloride) which hardly showed any moisturization activity. These 25 results were especially significant relative to glycerin which is normally used for moisturization purposes in cosmetic formulations.
    WO 2006/045427 PCT/EP2005/010905 - 23 EXAMPLE 13 This example details the synthesis of 2,3-dihydroxypropyl trimethylammonium chloride (identified in Table XII as dihydroxypropyl trimonium chloride). A 125 ml Erlenmeyer flask 5 was charged with 16.7 ml (53 mmol) of 3-chloro-2-hydroxypropyl trimethylammonium chloride (employed as a 60% material in water known as Quat 1880). The flask was equipped with a dropping funnel and stirring bar. A solution of sodium hydroxide (55 ml, 55.0 mmol) was charged into the flask via the dropping funnel at 10 a rate to maintain room temperature (-20'C) of the reaction. Once addition was complete, the solution was stirred under ambient conditions for about 12 hours, followed by heating at 50 0 C for two hours. The progress of the reaction was monitored by thin layer 15 chromatography (TLC) . The product was spotted onto a 2.5 by 7.6 cm silica gel plate alongside the starting material and eluted with butanol: acetic acid: water (4:2:2) for approximately 50 minutes. Visualization was executed with ninhydrin stain and scorching on a hotplate. 20 The crude product solution was first acidified to pH of 7, and then concentrated to remove water. Ethanol (200 ml) was added to the crude product with stirring. Upon sitting, sodium chloride precipitated and was filtered off under vacuum. The filtrate was concentrated under vacuum on a Rotavap*, followed by additional 25 drying under high vacuum (0.05 mmHg). A cloudy gel was obtained yielding the final product in 97% yield. TLC analysis indicated a major spot at Rf = 0.27. A 60 MHz proton NMR (D 2 0 w/TSP) analysis was run on the final product. The spectra confirmed the final product structure. 30 Mass spectrum analysis in positive ion mode revealed a M' of 134 (minus chlorine).
    权利要求:
    Claims (8)
    [1] 1. A personal care product including: (A) a personal care composition including: 5 (i) from 0.1 to 30% by weight of dihydroxypropyltri (C 1 C 3 alkyl) ammonium salt; (ii) a cosmetically acceptable carrier; (B) a package for delivering the composition to a consumer; and 10 (C) instructions printed on or associated with the package indicating topical use of the composition on skin.
    [2] 2. The product according to claim 1 wherein the salt is present in an amount from 1.5 to 12% by weight of the 15 composition.
    [3] 3. The product according to claim 1 or claim 2 wherein the salt is dihydroxypropyl trimonium chloride.
    [4] 4. The product according to any preceding claim which is selected from the group consisting of leave-on skin lotions 20 and creams, shampoos, hair conditioners, shower gels, toilette bars, antiperspirants, deodorants, dental products, shave creams, depilatories, lipsticks, foundations, mascara, sunless tanner and sunscreen lotions.
    [5] 5. A method for moisturizing human body parts comprising 25 topically applying to the human body parts a personal care composition comprising from 0.1 to 30% by weight of dihydroxypropyltri(Cl-C 3 alkyl) ammonium salt in a cosmetically acceptable carrier. WO 2006/045427 PCT/EP2005/010905 - 25
    [6] 6. The method according to claim 5 wherein the salt is dihydroxypropyltrimonium chloride.
    [7] 7. Use of a dihydroxypropyltri(C-C 3 alkyl) ammonium salt as a moisturizer. 5
    [8] 8. Use according to claim 7 wherein the salt is dihydroxypropyltrimonium chloride.
    类似技术:
    公开号 | 公开日 | 专利标题
    AU2005299029B2|2008-07-10|Personal care products which include dihydroxypropyltri | ammonium salts
    AU2005298910B2|2008-05-29|Personal care compositions with glycerin and hydroxypropyl quaternary ammonium salts
    US7282471B2|2007-10-16|Personal care compositions with glycerin and hydroxypropyl quaternary ammonium salts
    EP1804762B1|2008-02-13|Personal care compositions with salts of dihydroxypropyltri| ammonium monosubsituted polyols
    CA2581047C|2013-06-11|Personal care compositions with silicones and dihydroxypropyl trialkyl ammonium salts
    EP1807041B1|2008-01-02|Personal care compositions with salts of hydroxypropyl trialkylammonium substituted mono-saccharide
    EP1991198B1|2014-11-19|Personal care compositions containing quaternary ammonium trihydroxy substituted dipropyl ether
    Harichian et al.2012|Method for moisturizing human skin using dihydroxypropyltri | ammonium salts
    同族专利:
    公开号 | 公开日
    ZA200703873B|2008-08-27|
    US8124063B2|2012-02-28|
    MX2007004813A|2007-07-09|
    CN101048199A|2007-10-03|
    ZA200702260B|2008-10-29|
    CN101083974B|2010-06-16|
    CN101048200B|2010-05-12|
    EP1809235B1|2008-04-02|
    EP1809235A1|2007-07-25|
    AT390910T|2008-04-15|
    CN101083974A|2007-12-05|
    AU2005299029B9|2008-11-27|
    ZA200702262B|2008-08-27|
    DE602005005847D1|2008-05-15|
    AU2005299029B2|2008-07-10|
    CA2583815C|2013-06-11|
    US20060088495A1|2006-04-27|
    TW200630110A|2006-09-01|
    ZA200703871B|2008-09-25|
    KR20070072537A|2007-07-04|
    ES2303282T3|2008-08-01|
    ES2367363T3|2011-11-02|
    BRPI0516884B8|2018-05-29|
    BRPI0516884B1|2018-02-14|
    AR051143A1|2006-12-20|
    KR101216244B1|2012-12-31|
    CA2583815A1|2006-05-04|
    RU2007119380A|2008-11-27|
    CN101048200A|2007-10-03|
    RU2400212C2|2010-09-27|
    DE602005005847T2|2009-05-07|
    WO2006045427A1|2006-05-04|
    JP2008517881A|2008-05-29|
    CN101048199B|2010-05-26|
    TWI367104B|2012-07-01|
    JP4871873B2|2012-02-08|
    BRPI0516884A|2008-09-23|
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    法律状态:
    2008-11-06| FGA| Letters patent sealed or granted (standard patent)|
    2008-11-27| SREP| Specification republished|
    2018-05-10| MK14| Patent ceased section 143(a) (annual fees not paid) or expired|
    优先权:
    申请号 | 申请日 | 专利标题
    US10/972,483||2004-10-25||
    US10/972,483|US8124063B2|2004-10-25|2004-10-25|Method for moisturizing human skin using dihydroxypropyltri ammonium salts|
    PCT/EP2005/010905|WO2006045427A1|2004-10-25|2005-10-07|Personal care products which include dihydroxypropyltriammonium salts|
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