US2865859A - Solubilizing of mineral, vegetable, animal oils for cosmetic, pharmaceutical and industrial purposes - Google Patents

Solubilizing of mineral, vegetable, animal oils for cosmetic, pharmaceutical and industrial purposes Download PDF

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US2865859A
US2865859A US62121056A US2865859A US 2865859 A US2865859 A US 2865859A US 62121056 A US62121056 A US 62121056A US 2865859 A US2865859 A US 2865859A
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alcohol
oil
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carbon atoms
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Irwin I Lubowe
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Irwin I Lubowe
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/008Preparations for oily hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/14Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37Esters of carboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/92Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/92Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/925Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of animal origin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/0012Galenical forms characterised by the site of application
    • A61K9/0014Skin, i.e. galenical aspects of topical compositions
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q13/00Formulations or additives for perfume preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q15/00Anti-perspirants or body deodorants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q17/00Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/02Barrier 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 containing insect repellants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q17/00Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/006Antidandruff preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/06Preparations for styling the hair, e.g. by temporary shaping or colouring
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q7/00Preparations for affecting hair growth

Description

United States Patent Irwin I. Lubowe, Scarsdale, N. Y.

Application November 9, 1956 Serial No. 621,210

6 Claims. (Cl. 252-56) No Drawing.

The present invention relates to solubilizing of mineral, vegetable, and animal oils for cosmetic, pharmaceutical and industrial purposes in low molecular weight alcohols, such as ethyl, isopropyl and methyl alcohols.

It has been quite impossible to prepare effective c0smetic and industrial oil solutions which will carry large quantities of either an animal, vegetable or mineral oil and which at the same time will also carry other cosmetic ingredients such as a low molecular water soluble aliphatic alcohol.

It has been found that such compositions cannot be prepared commercially and the alcohol and the oil will promptly separate into distinct layers.

It is among the objects of the present invention to provide a novel process of solubilizing mineral and vegetable oils in low molecule weight alcohols for cosmetic and industrial purposes.

Another object is to provide novel solubilized vegetable and mineral oils which may contain relatively large proportions of low molecular weight water soluble aliphatic alcohols, such as methyl, ethyl or isopropyl alcohol.

Still further objects and advantages will appear in the more detailed description set forth below, it being understood, however, that this more detailed description is given by way of illustration and explanation only and not by way of limitation, since various changes therein may be made by those skilled in the art Without departing from the scope and spirit of the present invention.

In accomplishing the above objects, it has been found satisfactory to solubilize mixtures of low alcohols (1 to 5 carbon atoms) and oils (14 to 100 carbon atoms) by addition of minor proportions of esters of water soluble aliphatic alcohols having from 1 to 6 carbons and fatty acids having from 10 to 24 carbons. There may also be used minor proportions of fatty alcohols having 10 to 24 carbon atoms. The combination of the ester with or without fatty alcohol is used as a solubilizing agent in a proportion less than the low alcohol and oil taken singly or combined. Isopropyl, butyl, ethyl, and amyl palmitates, myristates, and linoleates, are quite satisfactory.

In the preferred embodiment, it is desirable to provide a mixture of a major proportion of an animal, mineral or vegetable oil and a low molecular weight aliphatic alcohol in the presence of one of the following miscibility inducing combinations:

EXAMPLE A 50% isopropyl palmitate 50% isopropyl myristate EXAMPLE B 50% butyl laurate 50% butyl myristate EXAMPLE C 50% ethyl palmitate- 50% ethyl laurate 2,865,859 Patented Dec. 23, 1958 ICC 2 EXAMPLE D amyl palmitate 40% amyl myristate In general, the above solubilizing combinations may include low molecular weight aliphatic alcohols having 1 to 8 carbon atoms and desirably 1 to 5 carbon atoms, such as ethyl, propyl, isopropyl, butyl, amyl and less preferably methyl allyl, benzyl cyclo-hexyl alcohols having 1 to 6 carbon atoms esterified with high molecular weight water insoluble fatty acids, such as lauric, oleic, myristic, palmitic, stearic, linoleic, linolenic, ricinoleic, and less preferably acids such as erucic, eleostearic, behenic, arachidonic, and clupadonic having 12 to 24 carbon atoms.

Although one of these esters may be employed in the amounts up to 15% to 35% of combined equal proportions of the oil and the alcohol, it is usually desirable to use combinations of 2 to 3 esters with or without the addition of a fatty alcohol having 10 to 24 carbons, in an amount ranging from 5 to 15% of the oil-alcohol mixture.

The preferred alcohols are cetyl, palmityl, myristyl, lauryl, oleyl, linoleyl, linolenyl, stearyl, decyl, riconoleyl, behenyl, arachindyl and eurcyl fatty alcohols.

The esterified fatty acids, as well as the free fatty alcohols, should contain 10 to 24 carbon atoms and more preferably 14 to 18 carbon atoms and they should constitute 100% of the solubilizing combination in proportions ranging from 100% of the ester and 0% of the fatty alcohol to 50% of the fatty alcohol and 50% of the ester.

Preferably the solubilized combination contains from 20 to 50% of the animal, vegetable or mineral oils, and 20 to 50% of the low alcohol and from 5 to 20% of the ester with or without added fatty alcohol 10 to 24 carbon atoms).

The resultant compound contains from 20 to 5 0% of a low molecular weight water soluble aliphatic alcohol, such as ethyl or isopropyl alcohol. Methyl alcohol may be used in industrial products, instead of ethyl or isopropyl alcohol.

As additional solubilizing or miscibility inducing combinations, it is possible to use:

40% isopropyl palmitate EXAMPLE E 25% butyl myristate 25% oleyl alcohol 50% butyl laurate EXAMPLE F 40% ethyl myristate 40% ethyl laurate 20% myristyl alcohol Among the other fatty alcohol combinations which may be used are the following:

Example G H I .T

(All parts by weight.)

These alcohols may be used in amounts ranging from 0 to 50% of the ester.

Instead of myristyl, oleyl or lauryl alcohols it is possible to use other saturated or unsaturated or hydroxylated fatty alcohols having from 10 to 20 carbon atoms.

In the preferred composition there is employed about 5 to 20% of the above Solubilizing combinations.

The preferred mineral oil which is used in about 20 to 60% proportion is light or heavy petrolatum.

The preferred vegetable oil is sesame oil or cottonseed oil, or corn oil, which is used in the amount of 20 to 60%.

Sweet almond oil, apricot oil, sunflower oil, peach kernel oil, olive oil, Wheat germ oil, rice bran oil, corn oil, and peanut oil may also be employed.

Animals oils which may be used are lanolin, Neats foot oil,-borie oil, sperm oil, cod liver oil and the like.

To give specific examples:

Example I Parts by weight Light petrolatum oil s 20 to 60 Alcohol ethyl or isopropyl 40 Solubilizing combination 15 Example II Cottonseed oil 20 to 40 Alcohol ethyl or isopropyl 40 Solubilizing combination v Example III Sesame oil 40 Alcohol ethyl or isopropyl 40 Solubilizing combination Example IV Percent Neats foot oil 10 to 50 Ethyl alcohol 10 to 50 Solubilizing combination 5 to 10 The products produced are stable, clear, translucent solubilized oil.

The above compositions may be used in cosmetics, polishes, abrasive and buffing suspensions, paints and waxes, dry cleaning compounds, hydraulic fluids, de-

The above compositions are particularly useful in cosmetics in that they will be highly stable over a wide range of temperatures for long periods of time Without separation.

All the compositions are miscible with methyl, ethyl or isopropyl alcohol in any proportions.

The freezing point of the composition is depressedand better lubricating properties are obtained in machinery bearings, as well as in cutting oil used in metal working industries.

It is possible to include amounts of essential oil in the range from 2 to in the above compositions.

Example VIII To give an example of a sun-screening compound:

Parts by weight Paraminobenzoic acid 15 Isopropyl palmitate 10 Oleyl alcohol 10 Light petrolatum 40 Isopropyl alcohol 25 Example IX SILICONE HAND LOTION Low viscosity silicone oil, 1,000 cs 15 Soy bean oil 15 Isopropyl palr nitate l0 Isopropyl alcohol 40 Lauryl alcohol 10 Example X HAIR SPRAY Isopropyl ester of lanolin 10 Isopropyl alcohol 20 Silicone oil, viscosity 1-,000 cs 1O Polyvinyl pyrrolidine 10 Isopropyl myristatee 5 Freon 25 Example XI INSECTICIDE SOLUTION Mineral oil (light) 3O Isopropyl alcohol 30 Butyl laurate 10 Butyl myristate 10 Insecticide: I

2-4 hexandiol 5 Dime'thyl phthalate 5 Example XII ANTI-SEBORRHEIC HAIR LOTION Estrogenic hormon Isopropyl ester of lanolin 30 Isopropyl palmi a 10 Isopropyl myristate 10 81601101 1.; Acetyl methioiiine c aue 5 Example XIII ANTI-PERSEIRANT Aluminum sulfate 25 Sesame oil 20 Butyl myristate 15 Butyl laurate 15 Hexachlorophene 2 Ethyl alcohol 45 Example XIV AFTER SHAVE LOTION Peanut oil l5 Ethyl laurate l5 Ethyl myristate 15 Ethyl alcohol 55 Example XV HAIR LACQUER Silicone oil (alcohol soluble) 5 Isopropyl lanolin r 15 Protein hydrolysates 5 Polyvinyl pyrollidine 5 Isopropyl palmitate 10 Oleyl alcohol nan- 10 Example XVI PERMANENT W-AVING SOLUTION Thioglycollic acid 15 Ammonium thioglycollate 15 Olive oil 7 1O Lauryl alcohol 10 Isopropyl palmitate 10 Isopropyl alcohol 40 Example XVII Parts b wei t SOLID COLOGNE y gh Sodium stearate 10 Zinc sulfocarbolate 10 Sesame oil Ethyl laurate 10 Ethyl myristate 1O Ethyl alcohol 45 Example XVIII TRANSPARENT SOAP Sodium stearate 40 Peanut oil 10 Glycerol 10 Butyl stearate 10 Butyl Iaurate -I. "1. 7' 10 V Ethyl alcohol Example XIX SCALP STIMULATING LOTION Resorcinol mono-acetate 5 Tincture of capsicum 5 Zinc phenol sulfonate 5 Cottonseed oil 20 Isopropyl palmitate 10 Lauryl alcohol 10 Ethyl alcohol 45 Where lauryl and myn'styl compounds are used together whether as high molecular weight fatty alcohols or low molecular Weight aliphatic alcohol esters of high molecular weight fatty acids the proportion of lauryl should be 2 to 4 times the proportion of myristyl compounds.

Generally it is preferred to have the solubilizing agent consist of 50 to 100% of the low molecular weight aliphatic alcohol (1 to 5 carbon atoms) ester of the high molecular weight fatty acid (14 to 18 carbon atoms) with the balance being fatty alcohol (12 to 24 carbon atoms) and with this solubilizing agent constituting 5 to 25% or as much as of the oil-low molecular weight alcohol (1 to 3 carbon atoms) mixture.

It is apparent that many variations may be made in the formulae.

In the examples above set forth, the specific ingredients described may be widely varied.

To summarize the present invention, it provides novel water clear, non-aqueous mineral, vegetable and animal oils dissolved in low molecular weight alcohols which will be highly effective in silicone protective lotions to give effective cutaneous protection against soaps, detergents, alkalies, sensitizers, solvents, plasticizers and allergens as well as in various aerosol preparations which are used in the cosmetic field, as, for example, for hair and nail lacquers and which will be useful for the dispersion of cutting oils, drying oils, solvent oils, insect repellants, insecticides, and pigments in the paint industry.

The solubilizing agents are preferably mixtures of:

(1) Propyl or isopropyl laurates, myristates, oleates, linoleatcs or ricinoleates.

(2) Butyl laurates, myristates, oleates, linoleates, stearates, ricinoleates.

(3) Ethyl laurates, myristates, oleates, linoleates, ricinoleates.

(4) Amyl laurates, myristates, oleates, linoleates, ricinoleates.

It is the primary object of the present invention to provide a novel solubilized mineral, vegetable and animal oil composition in which such oils will be dispersed in low molecular weight alcohols and which may be the product used as a base for cosmetic preparations such as hair tonics, hand lotions, sun screening preparations, and after-shave lotions, as well as facial astringents,

6 anti-perspirant preparations, and anti-dandruff preparations.

To the hair lotion preparations can be added the solubilizing compounds, lanolin derivatives, antiseptic rubefacients, estrogenic hormones, methyl sulfoxide, dithiocarbamates, methoxychloracetic acid, and solubilized amino acids.

To the anti-perspirant preparations can be added the solubilizing compounds aluminum, zinc, or zirconium salts, and deodorants as hexachlorophene, and silicones.

To the silicone protective preparations can be added the solubilizing compounds, alcohol, soluble silicones, lanolin derivatives, and antiseptics.

To the after-shaving lotions can be added these antiseptics, astringents, as aluminum, zinc or zirconium salts, and also antibiotics as tyrothricin, neomycin, and bacitracin.

To the acne preparations can be added sulfur, polysulfides, resorcin, vitamins A and D, antibiotics as tyrothricin, neomycin, and bacitracin.

To the fungicidal preparations can be added salicyclic acids, benzoic acid, the fatty acids, as propionic and thioglycolic acids, undecylinic acids, and their salts.

To the anti-dandruff lotions can be added sulfur, resorcinol, salicyl'ates, organic sulfides, dithiocarbamates, oxy-acetamides, and oxy-acetic acids.

To the hair lacquer preparations can be added silicones, casein, protein hydrolysates and lanolin derivatives.

To the permanent waving solutions can be added the thioglycollic derivatives, polyvinylpyrrolidine and casein or protein hydrolysates.

These added components will not effect the solubilizing effect of the above esters.

Normally mixtures of low molecular weight alcohols and high molecular weight oils of mineral, vegetable or animal origin with 5 to 15% of the above esters will not separate, and will have high pharmaceutical and therapeutic effectiveness, cosmetic consumer acceptance, industrial applicability and efiiciency.

Having now particularly described and ascertained the nature of the invention, and in What manner the same is to be performed, what is claimed is:

1. A clear, non-aqueous solubilized liquid composition consisting of a low molecular weight aliphatic alcohol and an oil normally immiscible in said low molecular weight aliphatic alcohol and said oil and alcohol being made miscible and solubilized in each other by inclusion of a mixer composition including a low molecular weight aliphatic alcohol ester of a high molecular weight fatty acid, said first mentioned low molecular weight alcohol containing l-5 carbon atoms and said oil containing 14-100 carbon atoms and said mixer composition including an ester of an aliphatic alcohol containing l-6 carbon atoms and a fatty acid containing 10-24 carbon atoms and said ester constituting 5-35% of the amount of the mixture of the first mentioned low molecular weight alcohol and oil, and said solubilized composition consisting essentially of 20-50% of the oil, 20-50% of the low molecular weight aliphatic alcohol and 5-20% of the ester, by weight.

2. The composition of claim 1, in which the low molecular weight fatty alcohol is selected from the group consisting of methyl alcohol, ethyl alcohol and isopropyl' alcohol and in which the high molecular weight fatty acid ester has from 12 to 24 carbon atoms and constitutes between 25 to of the mixer composition and 5% to 30% of the solubilized composition.

3. The composition of claim 1, in which the mixer composition consists of esters of lauric acid and myristic acid and in which the mixer composition constitutes between 10% to 25% of the solubilized composition with the balance consisting of equal parts of an oil selected from the group consisting of animal, vegetable and mineral oils and an alcohol selected from the group consisting of methyl, ethyl and isopropyl alcohol.

4,. A clear, non-aqueous solubilized liquid composition consisting of a low molecular weight aliphatic alcohol and an oil normally immiscible in said low molecular weight aliphatic alcohol and said oil and alcohol being made miscible and solubilized in each other by inclusion of a mixer composition including a low molecular weight aliphatic alcohol ester of a high molecular weight fatty acid and a high molecular weight fatty aliphatic alcohol, said first mentioned low molecular weight alcohol containing 1-5 carbon atoms and said oil containing 14-100 carbon atoms and said mixer composition including an ester of an aliphatic alcohol containing 1-6 carbon atoms and a fatty acid containing 10-24 carbon atoms and said ester constituting 5-35% of the amount of the mixture of the first mentioned low molecular weight alcohol and oil, and said solubilized composition consisting essentially of 20-50% of the oil, 20-50% of the low molecular weight aliphatic alcohol and 5-20% of the ester, by weight.

5. A clear, non-aqueous solubilized liquid composition of ethyl alcohol and a light petrolatum oil in major pro- References Cited in the file of this patent UNITED STATES PATENTS 2,115,354 Wasson Apr. 26, 1938 2,257,106, Christiansen Sept. 30, 1941 r 2,498,727 Verblen Feb. 28, 1950 2,524,017 Hance Sept. 26, 1950 OTHER REFERENCES Perfumery & Essential Oil Record, vol. 44, No. 3 (March 1953), pp. 84-90, and 101.

Claims (1)

1. A CLEAR, NON-AQUEOUS SOLUBILIZED LIQUID COMPOSITION CONSISTING OF A LOW MOLECULAR WEIGHT ALIPHATIC ALCOHOL AND AN OIL NORMALLY IMMISCIBLE IN SAID LOW MOLECULAR WEIGHT ALIPHATIC ALCOHOL AND SAID OIL AND ALCOHOL BEING MADE MISCIBLE AND SOLUBILIZED IN EACH OTHER BY INCLUSION OF A MIXER COMPOSITION INCLUDING A LOW MOLECULAR WEIGHT ALIPHATIC ALCOHOL ESTER OF A HIGH MOLECULAR WEIGHT FATTY ACID, SAID FIRST MENTIONED LOW MOLECULAR WEIGHT ALCOHOL CONTAINING 1-5 CARBON ATOMS AND SAID OIL CONTAINING 14-100 CARBON ATOMS AND SAID MIXER COMPOSITION INCLUDING AN ESTER OF AN ALIPHATIC ALCOHOL CONTAINING 1-6 CARBON ATOMS AND A FATTY ACID CONTAINING 10-24 CARBON ATOMS AND SAID ESTER CONSTITUTING 5-35% OF THE AMOUNT OF THE MIXTURE OF THE FIRST MENTIONED LOW MOLECULAR WEIGHT ALCOHOL AND OIL, AND SAID SOLUBILIZED COMPOSITION CONSISTING ESSENTIALLY OF 20-50% OF THE OIL, 20-50% OF THE LOW MOLECULAR WEIGHT ALIPHATIC ALCOHOL AND 5-20% OF THE ESTER, BY WEIGHT.
US2865859A 1956-11-09 1956-11-09 Solubilizing of mineral, vegetable, animal oils for cosmetic, pharmaceutical and industrial purposes Expired - Lifetime US2865859A (en)

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Cited By (17)

* Cited by examiner, † Cited by third party
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US3062745A (en) * 1958-12-02 1962-11-06 Standard Oil Co Glass grinding process employing a non-foaming oiliness agent
US3069358A (en) * 1958-03-26 1962-12-18 American Cyanamid Co Germicidal detergent composition
US3069359A (en) * 1958-03-26 1962-12-18 American Cyanamid Co Germicidal detergent composition
US3248333A (en) * 1963-04-03 1966-04-26 Hewitt Soap Co Inc Low ph detergent bar
US3326808A (en) * 1965-08-25 1967-06-20 Pfizer & Co C Antiseptic detergent composition
US3767431A (en) * 1971-12-23 1973-10-23 H Copeland Polishing composition
US4049792A (en) * 1973-06-26 1977-09-20 The Procter & Gamble Company Antiperspirant stick
FR2349326A1 (en) * 1976-04-29 1977-11-25 Procter & Gamble Creams anhydrous against perspiration
US4156719A (en) * 1977-02-28 1979-05-29 Yamanouchi Pharmaceutical Co., Ltd. Compositions for rectal use
US4223018A (en) * 1979-02-09 1980-09-16 Jimmie Belle Bath composition
US4224319A (en) * 1979-07-31 1980-09-23 Ernest Marcadet Antiseptic composition for topical application to the skin
US4990337A (en) * 1988-01-29 1991-02-05 Sankyo Company Limited Cyclosporin formulations of mono or diglyceride fatty acid
US5098694A (en) * 1990-09-25 1992-03-24 The Procter & Gamble Company Natural deodorant compositions
US5409694A (en) * 1991-07-18 1995-04-25 Procter & Gamble Liquid deodorant compositions
US5514672A (en) * 1981-02-17 1996-05-07 Bazzano; Gail S. Use of retinoids and compositions containing same for hair growth
US20040121944A1 (en) * 2002-12-20 2004-06-24 Michela Legora Cyclosporin-based pharmaceutical compositions
US20070179077A1 (en) * 2003-05-28 2007-08-02 Carl Formstone Antifoaming formulations

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CA985626A (en) * 1970-03-10 1976-03-16 E.R. Squibb And Sons Coating composition for moist surface
JPS6245204B2 (en) * 1983-06-07 1987-09-25 Kao Corp

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Publication number Priority date Publication date Assignee Title
US2115354A (en) * 1934-01-31 1938-04-26 Standard Oil Dev Co Blended oils
US2257106A (en) * 1938-02-26 1941-09-30 Squibb & Sons Inc Dermal lotion
US2498727A (en) * 1946-11-23 1950-02-28 Lanolin Plus Cosmetics Inc Isopropyl palmitate solution of lanolin cosmetic
US2524017A (en) * 1950-09-26 Metalworking lubricant

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2524017A (en) * 1950-09-26 Metalworking lubricant
US2115354A (en) * 1934-01-31 1938-04-26 Standard Oil Dev Co Blended oils
US2257106A (en) * 1938-02-26 1941-09-30 Squibb & Sons Inc Dermal lotion
US2498727A (en) * 1946-11-23 1950-02-28 Lanolin Plus Cosmetics Inc Isopropyl palmitate solution of lanolin cosmetic

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3069358A (en) * 1958-03-26 1962-12-18 American Cyanamid Co Germicidal detergent composition
US3069359A (en) * 1958-03-26 1962-12-18 American Cyanamid Co Germicidal detergent composition
US3062745A (en) * 1958-12-02 1962-11-06 Standard Oil Co Glass grinding process employing a non-foaming oiliness agent
US3248333A (en) * 1963-04-03 1966-04-26 Hewitt Soap Co Inc Low ph detergent bar
US3326808A (en) * 1965-08-25 1967-06-20 Pfizer & Co C Antiseptic detergent composition
US3767431A (en) * 1971-12-23 1973-10-23 H Copeland Polishing composition
US4049792A (en) * 1973-06-26 1977-09-20 The Procter & Gamble Company Antiperspirant stick
FR2349326A1 (en) * 1976-04-29 1977-11-25 Procter & Gamble Creams anhydrous against perspiration
US4083956A (en) * 1976-04-29 1978-04-11 The Procter & Gamble Company Anhydrous antiperspirant creams
US4156719A (en) * 1977-02-28 1979-05-29 Yamanouchi Pharmaceutical Co., Ltd. Compositions for rectal use
US4223018A (en) * 1979-02-09 1980-09-16 Jimmie Belle Bath composition
US4224319A (en) * 1979-07-31 1980-09-23 Ernest Marcadet Antiseptic composition for topical application to the skin
US5514672A (en) * 1981-02-17 1996-05-07 Bazzano; Gail S. Use of retinoids and compositions containing same for hair growth
US4990337A (en) * 1988-01-29 1991-02-05 Sankyo Company Limited Cyclosporin formulations of mono or diglyceride fatty acid
US5098694A (en) * 1990-09-25 1992-03-24 The Procter & Gamble Company Natural deodorant compositions
US5409694A (en) * 1991-07-18 1995-04-25 Procter & Gamble Liquid deodorant compositions
US20040121944A1 (en) * 2002-12-20 2004-06-24 Michela Legora Cyclosporin-based pharmaceutical compositions
US6979672B2 (en) 2002-12-20 2005-12-27 Polichem, S.A. Cyclosporin-based pharmaceutical compositions
US20070179077A1 (en) * 2003-05-28 2007-08-02 Carl Formstone Antifoaming formulations
US7994095B2 (en) * 2003-05-28 2011-08-09 Syngenta Crop Protection, Inc. Antifoaming formulations

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