US3711611A - Composition of matter with low cholesterol content and containing wool grease alcohols as major component and method - Google Patents

Composition of matter with low cholesterol content and containing wool grease alcohols as major component and method Download PDF

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Publication number
US3711611A
US3711611A US00137028A US3711611DA US3711611A US 3711611 A US3711611 A US 3711611A US 00137028 A US00137028 A US 00137028A US 3711611D A US3711611D A US 3711611DA US 3711611 A US3711611 A US 3711611A
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Prior art keywords
cholesterol
wool wax
alcohols
wax alcohols
sitosterol
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US00137028A
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P Julian
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BECKER BENJAMIN M TRUSTEE UNDER WILL OF PERCY L JULIAN DEC'D
JULIAN ANNA J TRUSTEE UNDER WILL OF PERCY L JULIAN DEC'D
First National Bank of Chicago
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P Julian
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Assigned to FIRST NATIONAL BANK OF CHICAGO THE, TRUSTEE UNDER THE WILL OF PERCY L. JULIAN, DEC'D., JULIAN, ANNA J. TRUSTEE UNDER THE WILL OF PERCY L. JULIAN, DEC'D., BECKER, BENJAMIN M. TRUSTEE UNDER THE WILL OF PERCY L. JULIAN, DEC'D. reassignment FIRST NATIONAL BANK OF CHICAGO THE, TRUSTEE UNDER THE WILL OF PERCY L. JULIAN, DEC'D. ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: DIAMOND SHAMROCK CORPORATION A CORP. OF DE
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
    • 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
    • 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
    • A61K8/064—Water-in-oil emulsions, e.g. Water-in-silicone 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
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/63—Steroids; Derivatives thereof
    • 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
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/925—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of animal origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/38—Alcohols, e.g. oxidation products of paraffins

Definitions

  • ABSTRACT A new and useful dispersing and emulsifying agent derived from wool grease made by separating cholesterol from the unsaponifiables and replacing the cholesterol with Bsitosterol', to form an improved essentially wool wax alcohol product.
  • Lanolin a wool grease freed from dirt; deodorized and sometimes bleached.
  • Lanolin has become a sine qua non for the cosmetic industry, primarily because of its capacity to absorb water with the formation of emulsions with light minerals oils, and heavy petrolatum, such as Vaseline, etc.
  • Wool wax is composed, for the most part, of esters, compounds of alcohols with a variety of fatty acids. Prominent among these alcohols is another useful product, cholesterol, which constitutes as high as 25 to 32 percent of the alcohol fraction of wool grease. Alongside cholesterol, there are other alcohols, such as lanosterol, and lower molecular weight alcohols, some of which are glycols. The alcohol fraction is separated by saponification of the wool grease, and separation of the alcohols from the saponification mixture of free fatty acids and wool wax alcohols.
  • Cholesterol has one use for which no other product has been able to supplant it, namely, the synthesis of Vitamin D a vitamin absolutely essential to the life and well-being of all two-footed animals.
  • Still another object of this invention is to replace the cholesterol in wool grease by another sterol, equal in stability and contributing essentially the same emulsifying, emollient and other significant properties to the wool wax alcohols as does cholesterol.
  • Still a further object of the invention bearing in mind the important emollient characteristics of wool wax alcohol creams, and possible absorption of certain ingredients into the blood stream, thus possibly upsetting dangerously the maximum cholesterol allowance in the blood stream is to replace cholesterol in wool wax alcohols with another sterol which is nonirritating, non-toxic and non-controversial from a health point of view, yet retaining essentially the same emulsifying, emollient and other desirable properties as unaltered natural wool wax alcohols.
  • Yet another object of the invention is to reduce mar kedly the amount of cholesterol present in wool wax alcohols.
  • Still another object of this invention is to replace cholesterol in wool wax alcohols, wholly or in part, with a sterol similar in structure, but much less expensive than cholesterol, yet extending to the wool wax alcohols essentially the same, or even enhanced, desirable characteristics as are em bodied in the intact" wool wax alcohols.
  • Yet a valuable object of this invention is to improve the economics of cholesterol manufacture, via extraction from wool wax alcohols, by almost doubling the present financial return from wool wax alcohols, and thus enhancing the prospects of cholesterol production on a scale to meet indispensible human and animal health needs and the presently growing demand.
  • Still a final object of this invention is to find satisfactory methods for incorporating into spent" wool wax alcohols (wool wax alcohols from which cholesterol has been extracted substantially wholly or in part) a sterol which enhances and/or equals the desirable characteristics hitherto attributed to cholesterol.
  • sitosterol is replaced by replacing the cholesterol in wool wax alcohols by Sitosterol" from soybean oil, or from other sources such as Tallol, or sometimes called Tall Oil (from waste paper pulping liquors), cottonseed oil, etc.
  • Sitosterol is replaced by replacing the cholesterol in wool wax alcohols by Sitosterol" from soybean oil, or from other sources such as Tallol, or sometimes called Tall Oil (from waste paper pulping liquors), cottonseed oil, etc.
  • sitosterol I include B-sitosterol and other naturally occurring products that may be extracted along from soya oil, Tall oil, and cottonseed oil and generally termed sitosterol.
  • EXAMPLE I The essentially solvent-free mixture of soaps and wool grease alcohols resulting from the saponification of wool grease, is treated with a suitable solvent, which dissolves the wool grease alcohols and leaves the solid metallic salts of the fatty acids. The latter are separated from the solution by filtration, or centrifuging. The solvent is distilled from the solution of the wool wax alcohols, and the cholesterol is removed from the wool wax alcohols by conventional methods such as those described in Truters' Wool Wax (loc. cit.), pp. -194 (62 references on the Isolation of Cholesterol); J. Th. hackmann, Rec. Trav. Chim. 69, 433 (1950); British Patent 622,725 (1949); H. W. Knol, U.S. Pat. No. 2,536,753 (1951).
  • the crude soya, tallol, or cottonseed sitosterols may be separated by methodssuch as are described by P. L. Julian in U.S. Pat. Nos. 2,218,97l (1940); 2,273,045 (I942) and 2,273,046 (1942); also by Overhoff and Ralphmann, Canadian Patent. 519,754 (1955), and Greiner and Fevig, Ind. & Eng. Chem. 53, 949 (1961).
  • the crude sitosterols may be refined by crystallization or by separating them from resins, etc., as described in' kg. modified wool wax alcohols, m.p. in the range of 89-90 C.
  • EXAMPLE 2 Still another 80 kg. of modified and greatly improved wool wax alcohols, were prepared as follows: A solution of wool wax alcohols, from which the cholesterol had been essentially removed, was concentrated, whereupon an average of 60 percent of the higher melting alcohols crystallized as an almost colorless product. The latter was separated from the supernatant liquors, which liquors on freeing from low-boiling solvent, were subjected to molecular distillation, yielding an almost colorless distillate of relatively lower boiling wool wax alcohols in essentially quantitative yield. This latter fraction was added to the crystals and to this mixture 25 kg. of highly-purified sitosterol was added.
  • EXAMPLE4 A 50 g. sample of a solution prepared by dissolving 6 g. modified wool wax alcohols (from Example 1) in 48 g. Protol, USP (white mineral oil of Sonneborn Division, Witco Chemical Company, having a specific gravity at 60 F. of 0.970-0.880, Saybolt viscosity at 100 F. 180-190, and Kinematic viscosity at 37.8 F. 38.6-40.9) was heated to ca. 60 C. To this solution was added water, heated to ca. 60 C., in approximately 10 ml. quantities at a time, while the mixture was beaten in a Sunbeam Mixmaster, Model MMZOOWS, at speed 4. Water was added at a rate so that the previous quantity was absorbed before the next quantity was added.
  • Emulsion stands firm several months. The emulsion in Example 4 is rated good.”
  • the sterols were isolated from Tall Oil as indicated in U.S. pat. Nos. 2,218,971, 2,273,045 and 2,273,046 and/or U.S. Pat. No. 2,536,753.
  • EXAMPLE 5 A 50 g. sample of solution as prepared in Example 4, except originating from modified wool wax alcohols as described in Example 2, was treated as in Example 4. The average total water absorption was 1,153 ml. to form an emulsion of excellent stability.
  • EXAMPLE 6 A 50 g. sample of solution as prepared in Example 4, except containing only wool wax alcohols commercially available from Takasago Perfumery Company, Ltd., Japan, m.p. 52 C., was treated as in Example 4. The average total water absorption was 676 ml. to give an emulsion of poor stability.
  • EXAMPLE 7 A 50 g. sample of solution as prepared in Example 4, except containing only wool wax alcohols commercially available from Takasago Perfumery Co., Ltd. (but which alcohols 1 had subjected to molecular distillation at 200/25-35 microns in percent yield), m.p. 61 C., was treated as in Example 4. The average total water absorption was 865 ml. to form an emulsion of fair stability.
  • EXAMPLE 8 A 50 g. sample of solution was prepared in Example 4, except containing only wool wax alcohols commercially available from Croda, Inc., New York, under the label Hartolan, m.p. 65 C., was treated as in Example 4. The average total water absorption was 993 ml. to give an emulsion of good stability.-
  • EXAMPLE 9 A 50 g. sample of solution as prepared in Example 4, except containing only wool wax alcohols commercially available from Croda, Inc., under the label Super Hartolan, m.p. 75 C., was treated as in Example 4. The average total water absorption was 1,187 ml. to form an emulsion of excellent stability.
  • EXAMPLE 10 A 50 g. sample of solution as prepared in Example 4, except containing only wool wax alcohols commercially available from Westbrook-Marriner, lnc., Lawrence, Mass. under the label Argowax, Standard, m.p. 64 C., was treated as in Example 4. The average water absorption was 858 ml. to give an emulsion of good stability.
  • EXAMPLE 1 1 A 50 g. sample ofsolution as prepared in Example 4, except containing only wool wax alcohols commercially available from Westbrook-Marriner, lnc., under the label Argowax, Distilled, m.p. 73 C., was treated as in Example 4. The average total water absorption was 1,028 ml. to form an emulsion of excellent stability.
  • EXAMPLE 12 A 5 g. sample of modified wool wax alcohols (Example 1) was dissolved in 45 g. Carnation, F.F. mineral oil (white mineral oil of Sonneborn Division, Witco Chemical Company, specific gravity at 60 F. 0.835-0.845, Saybolt viscosity at F. 65-75, Kinematic viscosity at 37.8 F. l l.7l4.4). This solution Average was heated to ca. 60 C. and water at 60 C. was added Pg lgf as in Example 1. The water absorption was l,l8l ml.
  • the average total water absorption was 0 precipitable steroids.
  • This new compositionof matter 1,630 ml. to give an emulsion of excellent stability. removes at least in large part the hazard of possible cholesterol absorption into the blood stream, particu- EXAMPLE 19 larly when such a material may be frequently applied to the skin.
  • the resultant product is enhanced 1,803 ml. to afford an emulsion f exc llent stability. by molecular distillation to give a color refinement and A comparison of pertinent characteristics is as folfreedom from resinous or polymeric and/or high-boillows: ing materials.
  • sitosterol Thus, under currentconditions, it is.
  • the refined composition may represent as high as 60-70 percent of the material subjected to distillation. Since the molecular distillation is an expensive process, particularly for high-boiling and heat sensitive products, this guarantees an economic advantage over present commercially distilled wool wax alcohols.
  • a new and useful cosmetic emollient water-absorbing mineral oil-emulsifying pale yellow crystallinelike solid mass composition of matter comprising spent wool wax alcohols which are poor emulsifiers when essentially freed of the cholesterol constituent which imparts emulsion forming ability thereto, and a sufficient quantity of a sterol consisting principally of sitosterol as to bring these spent wool wax alcohols up to the emulsifying capacity of the intact cholesterol-bearing wool wax alcohols.
  • a new composition of matter in accordance with claim 1 comprising wool wax alcohols from which cholesterol has been substantially removed and replaced entirely by sitosterol in sufficient quantities to represent substantially the emulsification equivalent of replaced cholesterol.
  • sitosterol represents from about 15 percent to about 35 percent of the weight of the wool wax alcohols.
  • a new composition according to claim 2 in combination with a mineral oil carrier said composition being characterized therein to absorb up to several hundred times its weight of water, forming stable emulsion, principally of the water-in-oil type, and useful in the production of a wide variety of cosmetic creams and lotions.
  • a new composition according to claim 2 in which about 0.01 percent to about 1 percent of an antioxidant has been added.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
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  • Medicinal Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
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  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Cosmetics (AREA)
  • Steroid Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Fats And Perfumes (AREA)
US00137028A 1971-04-23 1971-04-23 Composition of matter with low cholesterol content and containing wool grease alcohols as major component and method Expired - Lifetime US3711611A (en)

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US (1) US3711611A (fr)
BE (1) BE788507A (fr)
FR (1) FR2197959B1 (fr)
NL (1) NL7212622A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5759584A (en) * 1994-10-28 1998-06-02 Beiersdorf Ag Method for treating skin afflicted with blemishes or acne with a composition comprising distilled wool wax acids and at least one monoglycerol monocarboxylic acid monoester

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2938656B2 (de) * 1979-09-25 1981-07-30 Beiersdorf Ag, 2000 Hamburg Verfahren zur Herstellung von Wollwachsalkoholen aus Wollwachssäuren oder Wollwachssäureestern niederer Alkohole
FR2568142B1 (fr) * 1984-07-26 1989-11-17 Oreal
EP1671679B1 (fr) 2004-12-06 2011-06-22 Sebapharma GmbH & Co. KG Composition cosmétique ou dermatologique sous la forme d'une émulsion eau-dans-huile comprenant des phytostéroles

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2676149A (en) * 1951-12-29 1954-04-20 Shell Dev Stabilized grease composition containing a sterol and a selenium compound
US2725334A (en) * 1951-11-20 1955-11-29 American Cholesterol Products Modified lanolin
US2900307A (en) * 1957-07-05 1959-08-18 Colgate Palmolive Co Clear liquid solubilized lanolin compositions
US3101300A (en) * 1960-06-30 1963-08-20 Bristol Myers Co Clear mineral oil in water emulsion for hair application
US3272851A (en) * 1963-07-24 1966-09-13 Malmstrom Chem Corp Purification of acylated lanolin products

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2725334A (en) * 1951-11-20 1955-11-29 American Cholesterol Products Modified lanolin
US2676149A (en) * 1951-12-29 1954-04-20 Shell Dev Stabilized grease composition containing a sterol and a selenium compound
US2900307A (en) * 1957-07-05 1959-08-18 Colgate Palmolive Co Clear liquid solubilized lanolin compositions
US3101300A (en) * 1960-06-30 1963-08-20 Bristol Myers Co Clear mineral oil in water emulsion for hair application
US3272851A (en) * 1963-07-24 1966-09-13 Malmstrom Chem Corp Purification of acylated lanolin products

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
Cockbain et al. Trans. Faraday Soc. 47; 322 330 (1951) Adsorbed Films at Oil Water Interfaces *
Feldman et al. Biochem. Biophys. Acta 125(1); 136 147 (1966) Phase Distribution of Sterols *
Karabinos et al. J. Am. Oil Chemists Soc. 31; 136 (1954) Synthesis and Comparative Detergency of Built Polyethenoxy Sitosterols *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5759584A (en) * 1994-10-28 1998-06-02 Beiersdorf Ag Method for treating skin afflicted with blemishes or acne with a composition comprising distilled wool wax acids and at least one monoglycerol monocarboxylic acid monoester

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DE2250340B2 (de) 1977-02-17
FR2197959B1 (fr) 1976-05-21
AU464122A (fr) 1975-08-14
NL7212622A (fr) 1974-03-20
BE788507A (fr) 1973-01-02
FR2197959A1 (fr) 1974-03-29
DE2250340A1 (de) 1974-04-25

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