sign in sign up
<<
Home , Cetyl alcohol, Fatty alcohol, Oleyl alcohol

2,942,008

United States Patent Office Patented June 21, 1960

2 permanent mixtures are obtained without separation in the absence of water. 2,942,008 Although unsaturated fatty are preferred, it SOLUBILIZING OF MINERAL, VEGETABLE, AND is also possible to utilize saturated fatty alcohols or even ANIMAL, OLS FOR COSMETIC, PHARMACEU 5 hydroxylated fatty alcohols as for example in amounts TICAL, AND INDUSTRAL PURPOSES from 10% to 25% of the saturated fatty by it self or in the mixer combination. Irwin I. Lubowe, Scarsdale, N.Y. The preferred amount of fatty alcohols is 20% of the (667 Madison Ave., New York 21, N.Y.) total mixture. 10 No Drawing. Filed Dec. 10, 1956, Ser. No. 627,112 following:Among the fatty alcohols which may be used are the 6 Claims. (C. 252-364) Lauryl alcohol Myristyl alcohol The present invention relates to solubilizing of mineral, 15 vegetable and animal oils in low molecular weight water miscible or water soluble alcohols, such as methyl, ethyl Palmity alcohol and . - It has not been readily possible to prepare clear non Linoleyl alcohol separating solutions of high molecular weight vegetable 20 Linolenyl alcohol or mineral oils with low molecular weight aliphatic Ricinoley alcohol alcohols. Arachadecyl alcohol Normally mixtures of low molecular weight alcohols Another satisfactory combination is a mixture of and high molecular weight oils of mineral, vegetable or lauryl alcohol and myristyl alcohol in proportions of animal origin will readily separate, and if prepared as 25 three of the former to one of the latter. will have diminished pharmaceutical and thera In the preferred embodiment, it is desirable to provide peutic effectiveness, cosmetic consumer acceptance, in a mixture of a major proportion of an animal, mineral dustrial applicability and efficiency. or and a low molecular weight aliphatic It is the primary object of the present invention to pro alcohol in the presence of 5 to 20% of one of the follow vide a novel solubilized mineral, vegetable and animal oil 30 ing miscibility inducing combinations: composition in which such oils will be dispersed in low molecular weight alcohols and which product may be Mixture A used as a base for cosmetic preparations such as hair Percent tonics, handlotions, sun screening preparations, and after Lauryl alcohol ------62 shave , as well as, facial astringents, anti-perspirant 35 Myristyl alcohol ------25 preparations, and anti-dandruff preparations. Cetyl alcohol ------13 Still further objects and advantages will appear in the - Mixture B more detailed description set forth below, it being under stood, however, that this more detailed description is Lauryl alcohol ------70 given by way of illustration and explanation only and not 40 Oley alcohol ------30 by way of limitation, since various changes therein may be Mixture C - made by those skilled in the art without departing from the scope and spirit of the present invention. Oleyl alcohol ------60 In accomplishing the above objects, it has been found Myristyl alcohol ------40 satisfactory to solubilize mixtures of low alcohols (1 to 45 Mixture D 3 atoms) and oils (24 to 100 carbon atoms) in major proportion (50 to 100%) by addition of minor Oley alcohol ------50 proportions of fatty alcohols having 10 to 24 carbon Linoley alcohol ------50 atOmS. Mixture E The solubilizing combination is used as a solubilizing Lauryl alcohol ------70 agent in a proportion less than the low alcohol (1 to 3 50 Ricinoley alcohol ------30 carbon atoms) and oil (24 to 100 carbon atoms). In general the above solubilizing combinations may in The most satisfactory mixer or additive combinations clude low molecular weight aliphatic alcohols having 1 are those which include saturated fatty alcohols having to 3 carbon atoms, such as ethyl, propyl, isopropyl and from 10 to 24 carbon atoms, and desirably from 12 to 55 methyl. 18 carbon atoms. - It is usually desirable to use combinations of 2 to 3 These high molecular weight fatty alcohols may be of the fatty alcohols having 14 to 24 , in an used singly or in combination, and should preferably amount ranging from 5 to 15% of the oil and low alcohol constitute 50 to 100% of the additive combination and Xture. - between 5% to 20% of the final combination containing 60 Cetyl, palmityl, myristyl, lauryl, oleyl, linoleyl, lino the mineral, animal or vegetable oil and the low molecu lenyl, stearyl, decyl, ricinoleyl, behenyl, arachindyl and lar weight water soluble . These combina erucyl fatty alcohols may be substitluted in or added to tions are utilized in non-aqueous compositions. Examples A to E. In mixing to form water clear non-cloudy permanent Preferably the solubilized combination contains from liquid mixture for storage and shipment, the amount of 20 to 50% of the animal, vegetable or mineral oils, and water present should always be kept less than 10% and 20 to 50% of the low alcohol and from 5 to 20% of the if possible less than 1% or 1% since most effective fatty alcohol (12 to 24 carbon atoms). - 2,942,008 3 " . . . . . 4. The resultant compound contains from 20 to 50% of EXAMPLE VI a low molecular weight water soluble aliphatic alcohol, Oleyl alcohol ------15 such as ethyl or isopropyl alcohol. Methyl alcohol may Mineral oil ------15 be used in industrial products, instead of ethyl or iso Peanut oil ------50 propyl alcohol. 5 Isopropyl alcohol ------;was no me man - - m - - - - 40 Among the other fatty alcohol combinations which The above compositions are particularly useful in cos may be used are the following: metics in that they will be highly stable over a wide range of temperatures for long periods of time without sepa Examples F G H ration. All the compositions are miscible with methyl, ethyl Decyl- - - - - 5 5 1% ------prisopropyl alcohol in any proportions. Laury - - - - 5 70 60 ------Myristyl-l- ---- 20 25 25 30 The freezing point of the composition is depressed Cetyl------40 2 5 30 and better lubricating properties are obtained in ma Stearyl------(all20 parts2 by weight) 40 chinery bearings, as well as in cutting oil used in metal 5 working industries. Instead of myristyl, oley or lauryl alcohols, it is pos It is possible to include amounts of essential oil in the sible to use other saturated or unsaturated or hydroxyl range from 2 to 20% in the above compositions. ated fatty alcohols having from 12 to 24 carbon atoms. EXAMPLE VIII In the preferred composition there is employed about 20 5 to 20% of the above solubilizing combinations. To give an example of a sun-screening compound: The preferred mineral oil which is used in about 20 Parts by weight to 40% proportion is light or heavy petrolatum. Digalloyl oleate ------5 The preferred vegetable oil is sesame oil, soya bean Isopropyl alcohol ------15 oil, cottonseed oil or corn oil, which is used in the 25 Myristyl alcohol ------15 amount of 20 to 60%. Light petrolatum ------40 Sweet almond oil, apricot kernel oil, sunflower seed oil, Ethyl alcohol ------30 peach kernel oil, safflower oil, tung oil, avocado oil, linseed oil, pine oil, , , EXAMPLE X oil, rice bran oil, corn oil, rosin oil, and peanut oil may 30 Silicone hand also be employed. Animal oils which may be used are lanolin, Neat's Low silicone oil, 1,000 cs. ------15 foot oil, , bone oil, , codliver oil and Neat's foot oil ------15 the like. Isopropyl alcohol ------40 To give specific examples: 35 Lauryl alcohol ------10 EXAMPLE I Parts by weight EXAMPLE X Light petrolatum oil ------20 to 60 Hair spray Alcohol ethyl or isopropyl ------40 Isopropyl of lanolin ------10 Solubilizing combination ------10 40 Isopropyl alcohol ------20 EXAMPLE Silicone oil viscosity 1,000 cs. ------10 Cottonseed oil ------20 to 40 Polyvinyl pyrrolidine ------10 Alcohol ethyl or isopropyl ------40 Oleyl alcohol ------5 Solubilizing combination ------15 Freon ------25 45 Dichloro tetra fluoroethane EXAMPLE II Sesame oil ------40 EXAMPLE X Alcohol ethyl or isopropyl ------40 Solubilizing combination ------10 Insecticide solution 50 - EXAMPLE IV Mineral oil (light) ------30 Neat's foot oil ------20 to 50 Isopropyl alcohol ------30 Ethyl alcohol ------20 to 50 Lauryl alcohol ------10 Solubilizing combination ------10 to 20 2-4 hexandiol ------as a mir------r ------5 The products produced are stable, clear, translucent 55 Insecticide (dimethyl phthalate) ------5 solubilized oil. The solubilizing combinations are selected from Exam EXAMPLE X ples A to E. The above compositions may be used in , Anti-seborrheic hair lotion pharmaceuticals, polishes, abrasive and buffing suspen 60 Parts by weight sions, paints and , dry cleaning compounds, hy Estrogenic hormone ------Ao draulic fluids, degreasing compounds, insecticides, weed Isopropyl ester of lanolin ------30 killers and special lubricants. Palmitic alcohol ------10 To give some additional examples: Ethyl alcohol ------50 EXAMPLE V 65 Acetyl methionine ------5 Parts by weight Genite (2-4 diphenyl ester sulfonic acid) --- 5 Ethyl alcohol ------50 EXAMPLE XII. Petrolatum ------20 Anti-perspirant Oleyl alcohol ------10 70 EXAMPLE VI Aluminum sulfate ------25 Isopropyl alcohol ------20 Sesame oil ------20 Light petrolatum ------20 Oley alcohol ------10 Virgin olive oil ------20 Hexachlorophene ------2 Lauryl alcohol ------.10 75 Ethyl alcohol ------45

2,942,008 5 6 EXAMPLE XTV EXAMPLE XXII After-shave lotion Solubilized peanut oil composition Peanut oil ------15 Oleyl alcohol ------5 Peanut oil ------20 Isopropyl alcohol ------60 Ethyl alcohol ------55 Lauryl alcohol ------10 . . . EXAMPLE XV Methyl alcohol ------3 Where lauryl and myristyl compounds are used to Hair Lacquer gether as high molecular weight fatty alcohols, the pro O portion of lauryl should be 2 to 4 times the proportion Silicone oil (alcohol soluble) ------5 of myristyl alcohol. Isopropyllanolin ------15 It is apparent that many variations may be made in Protein hydrolysates ------5 the formulae. Polyvinyl pyrollidine ------5 In the examples above set forth, the specific ingredients Oley alcohol ------10 15 described may be widely varied. Freon ------30 To summarize the present invention, it provides novel water clear, non-aqueous mineral, vegetable and animal EXAMPLE XVI oils dissolved in low molecular weight alcohols and solubilized by light molecular weight fatty alcohols, will Permanent waving solution 20 be highly effective in silicone protective lotions to give Thioglycolic acid ------15 effective cutaneous protection against Soaps, detergents, Ammonium thioglycollate ------15 alkalies, sensitizers, , plasticizers and allergens as Olive oil ------as a mass m ------a as a on was a wo 10 well as in various aerosol preparations which are used Lauryl alcohol ------10 in the cosmetic field, as, for example, for hair and nail 25 lacquers and which will be useful for the dispersion of EXAMPLEXVII cutting oils, drying oils, oils, insect repellants, in secticides, and pigments in the paint industry. Solid cologne It is the primary object of the present invention to Sodium stearate ------10 provide a novel solubilized mineral, vegetable and animal Zinc sulfocarbolate ------10. 30 oil composition in which such oils will be dispersed in Sesame oil ------25 low molecule weight alcohols and which may be the Lauryl alcohol ------15 product used as a base for cosmetic preparations such as Myristyl alcohol ------5 hair tonics, hand lotions, sunscreening preparations, and Ethyl alcohol ------45 after-shave lotions, as well as facial astringents, anti 35 perspirant preparations, and anti-dandruff preparations. EXAMPLE XVIII In the hair lotion preparations, there may be added lanolin derivatives, antiseptic rubefacients, estrogenic Y. . . Transparent soap hormones, methyl sulfoxide, dithiocarbamates, methoxy Sodium stearate ------50 chloracetic acid, solubilized amino acids. Peanut oil ------10 40 In the anti-perspirant preparations, there may be added ------10 aluminum, zinc, or zirconium salts, and deodorants as Cetyl alcohol ------10 hexachlorophene and silicones. Lauryl alcohol ------O In the silicone protective preparations, there may be Ethyl alcohol ------30 added soluble silicones, lanolin derivatives, and anti 45 septics. EXAMPLE XIX In the after-shaving lotions, there may be added anti septics, astringents, as aluminum, zinc or zirconium. Scalp stimulating lotion salts, and also antibiotics as tyrothricin, neomycin, and bacitracin. Resorcinol mono-acetate ------5 50 In the acne preparations, there may be added sulfur, Tincture of capsicum ------5 polysulfides, resorcin, vitamins A and D, antibiotics as Zinc phenol sulfonate ------5 tyrothricin, neomycin, and bacitracin. Cottonseed oil ------20 In the fungicidal preparations, there may be added Lauryl alcohol ------10 salicylic acid, benzoic acid, acids, as propionic thio Ethyl alcohol ------45 55 glycollic and undecylinic acids, and their salts. In the anti-dandruff lotions, there may be added sul EXAMPLE XX fur, resorcinol, salicylates, organic sulfides, dithiocar bamates, oxy-acetamides, and oxy-acetic acids. Acne preparation In the hair lacquer preparations, there may be added Estrone ------2 60 silicones, casein, protein hydrolysates and lanolin deriva Resorcinol monoacetate ------5 tives. Salicylic acid ------3 In the permanent waving solutions, there may be added Peanut oil ------17 the thioglycollic derivatives, polyvinylpyrrolidine and Isopropyl alcohol ------50 casein or protein hydrolysates. Lauryl alcohol ------15 These added components will not effect the solubilizing Myristyl alcohol ------5 effect of the above high molecular weight fatty alcohols. Normally mixtures of low molecular weight alcohols EXAMPLE XXI and high molecular weight oils of mineral, vegetable or animal origin with 5 to 15% of the above fatty alcohols Solubilized olive oil composition 70 will not separate, and will have high pharmaceutical and therapeutic effectiveness, cosmetic consumer acceptance, Olive oil ------20 industrial applicability and efficiency. Isopropyl alcohol ------60 Surprisingly high molecular weight fatty alcohols con Lauryl alcohol ------10 taining 12 to 18 carbon atoms result in solubilizing of Myristy alcohol ------3 s mineral oils and vegetable oils on the one hand in ethyl 2,942,008 7 8 and isopropyl alcohol and on the other hand in a manner, plications Serial Number 349,311, filed April 16, 1953, which remarkably is not achieved when the corresponding now abandoned and Serial Number 465,443, filed Octo is used by itself in the same amounts or in com be 28, 1954, now abandoned." bination with the fatty alcohol...... Having now particularly described and ascertained the To illustrate this point, the -following combinations nature of the invention, and in what manner the same were made up in parts by weight: ...... is to1. beA clear,performed, non-aqueous what is solubilized claimed is: liquid composition consisting of a low molecular weight aliphatic alcohol ...... Examples having 1 to 3 carbon atoms and an oil containing 24 to Ingredients ------0. 100 carbon atoms, normally immiscible in said low molec ------xx III XXIV xxv, xxvi. xxvii. ular weight aliphatic alcohol, and said oil and alcohol Mineral oil...... 40 40 40 40 40 being made miscible and solubilized in each other by a Ethyl alcohol------40 40 40 40 40 high molecular weight fatty alcohol having 12 to 24 car Lauryl alcohol ------15 10 ------bon-atoms, said solubilized composition consisting essen Myristyl alcohol------5 i------10 Lauric acid--- 10 ------10. ------16 5 tially of 20.50% of the oil, 20.50% of the low molecular Myristic acid weight aliphatic alcohol and 5-20% of the high molec ular weight fatty alcohol, said percentages being by weight. In connection with the above composition, composi 2. The composition of claim 1, in which the low molec ular weight aliphatic alcohol is selected from the group. . . . tionXXIII immediately tends to produce a cloudiness and consisting of methyl alcohol, ethyl alcohol and isopropyl precipitationComposition and XXIV separation initially of tends the oil to andbe clear alcohol. but upon alcohol and in which the high molecular weight aliphatic ...... standing or shelving develops cloudiness; which slowly alcohol has from 12 to 24 carbon atoms and constitutes . . . . . increases with time and gives a precipitation...... 5% to 20% of the solubilized composition. Compositions XXVI and XXVII also tend to cloud 25 3. The composition of claim 1, in which the high molec with time and give a precipitation, although the develop ular weight fatty alcohol consists of a mixture of lauryl al- . . . . ment of cloudiness and the precipitation is much slower cohol and myristyl alcohol and constitutes between 10% than in case of composition XXIV...... to 20% of the solubilized composition with the balance However, with composition XXIII, the separation and consisting of equal parts of an oil selected from the group . . . 30 consisting of animal, vegetable and mineral oils and an al cloudiness takes place immediately, whereas with com cohol selected from the group consisting of methyl, ethyl cloudinessposition XXIV, and precipitation there is considerable within 12 to development 24 weeks while of and isopropyl alcohol, the proportion of lauryl alcohol in compositions XXVI and XXVII: a similar develop. being 2 to 4 times the proportion of myristyl alcohol. ment of cloudiness and precipitation, as is true of composi 4.A clear non-aqueous solubilized liquid composition tion XXIV, would take about three to four weeks longer. 85 consisting of a low molecular weight aliphatic alcohol On the other hand, composition XXV remains bright containing 1 to 3 carbonatoms and an oil containing 24 and clear with a shelf life of twelve months and longer, to 100 carbon atoms, normally immiscible in said low without any appearance of cloudiness or precipitation and molecular weight aliphatic alcohol, and said oil and al it would appear from the experiments being carried on cohol being made miscible and solubilized in each other that either under winter or summer conditicins the com 40 by inclusion of a minor proportion of a high molecular position XXV remains clear and soluble indefinitely. weight aliphatic alcohol having 12 to 24 carbon atoms, It has been found that sudden changes in temperature said solubilized composition consisting essentially of 20 tend to catalyze the development of cloudiness, separa to 50% of mineral oil, 20 to 50% of ethyl alcohol and tion and precipitation in compositions XXIV, XXVI and 5-20% of the high molecular weight fatty alcohol, said XXVII whereas with composition XXV such catalyzing percentages being by weight. - ...... effect is altogether absent. 5. A clear, non-aqueous solubilized liquid composition Upon Substituting oleic and ricinoleic acid for lauric consisting of ethyl alcohol and petrolatum oil in equal and myristic acid, the same result was observed in respect parts constituting about 80-90% of the composition to cloudiness and precipitation after several weeks of which have been solubilized in each other by 5 to 20% of standing, particularly under sudden changes of tempera 50 a high molecular weight aliphatic alcohol having 12 to 24 ture. carbon atoms. It appears that the cloudiness and precipitation is due 6. The composition of claim 5 in which the high molec to the carboxyl group, which tends to activate any small ular weight aliphatic alcohol is included in an amount quantities of water which might be present or become ranging between 10% and 20%. adsorbed upon storage. 55 Initially the corresponding high molecular weight fatty References Cited in the file of this patent acids appear to give miscibility but such miscibility is not UNITED STATES PATENTS permanent. - - Clarkson et al.------Sept. 21, 1957 While there has been herein described a preferred form 2,093,863 of the invention, it should be understood that the same 60 OTHER REFERENCES may be altered in details and in relative arrangemnt of Bennett: The Chemical Formulary, vol. IX, p. 104 and parts within the scope of the appended claims. vol. X, p. 63. Chem. Pub. Co., Brooklyn, N.Y., 1951 The present application is a continuation-in-part of ap and 1957.