US2872379A - Aerosol antiperspirant composition preparation - Google Patents
Aerosol antiperspirant composition preparation Download PDFInfo
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- US2872379A US2872379A US556430A US55643055A US2872379A US 2872379 A US2872379 A US 2872379A US 556430 A US556430 A US 556430A US 55643055 A US55643055 A US 55643055A US 2872379 A US2872379 A US 2872379A
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- aluminum
- astringent
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- perspiration
- antiperspirant
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q15/00—Anti-perspirants or body deodorants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/26—Aluminium; Compounds 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
Definitions
- This invention relates to a perspiration inhibiting and astringent preparation, and more particularly to a perspiration inhibiting and astringent preparation containing an aluminum compound as active ingredient, and to a process of combating excessive perspiration therewith.
- astringents and antiperspirants are most effective when applied in the form of. their solutions.
- the particularly effective compounds such as aluminum chloride, AlCl -6H O, aluminum sulfate, Al (SO.,) -18H O, and aluminum oxychloride
- aluminum chloride, AlCl -6H O, aluminum sulfate, Al (SO.,) -18H O, and aluminum oxychloride can be employed in the required concentration only when in aqueous solution or in lotions and creams containing suflicient amounts of water to carry the astringent in solution. Therefore their possibilities of application are rather limited. They cannot be incorporated in dissolved form into wax sticks, ointments, oils, or alcoholic solutions of high concentration, and uniform distribution of these astringent materials in power bases is very ditficult.
- One of the objects of our invention is to provide new astringent and.antiperspirantaluminum compounds which.
- alcohols such as, for instance, ethanol,
- Another object of our invention is to provide new and highly effective astringent and antiperspirant preparations which can be applied not only in the form of aqueous and alcoholic solutions but also in the form of ointments, creams, skin lotions, aerosols, powders, wax.sticks, and the like.
- a further. object of the invention is to provide: a processof combating excessive perspiration by means of such new and highly efiective astringent and antiperspirant preparations.
- the new and highly effective astringent and antiperspirant aluminum compounds according to our invention are alkoxy aluminum chlorides, i. e., complex compounds of aluminum alcoholates and aluminum chloride, of the general formula A1,(RO),,CI, wherein R indicates analkyl-radical with 1 to 18 carbon atoms x represents the numerals l or 2 y represents the numerals 1, 2 or 5, and v z represents thenumerals 1 or 2 In the above formula, when x is 1, y and z together mustbe 3, and when x is 2, y, and z together must be 6.
- R indicates an alkyl radical with 1 to 18' carbon atoms.
- These compounds possess not only excellent astringent properties, but they are also readily soluble tions of said alkoxy aluminum chlorideshave amore orv less strongly acid pH value depending upon their chlorine 3 content. Their pH value is considerably higher than that of the corresponding aluminum chloride solutions as is evident from Table II given hereinafter.
- the perspiration inhibiting effect was tested in practical ap lications and according to the Manuila test [L. Manuila and H. Isler, Dermatologica 100,'p. 302 (l950), and Dermatologica 102, page 304 (1951)], whereby the sweat glands were incited by pilocarpine iontophoresis.
- a single application of alkoxy aluminum chlorides according to our invention caused an inhibition of sweat secretion of about 40% and repeated application inhibited sweat secretion to about 70% to 80%.
- a further advantage of said alkoxy aluminum chlorides when used as antiperspirants according to our invention is that they permit the pre aration of completely anhydrous, highly effective astringent and perspiration inhibiting preparations based on the use, as diluents and carriers of alcohols, fats, waxes, oils, agents keeping the preparation moist, such as glycerol, sorbitol and the like, or of mixtures thereof. as Well as the preparation of aerosols containing propellent gases. It is, therefore, possible to prepare effective astringent and perspiration inhibiting agents to be applied in a new and more suitable and corrifortable form.
- anhydrous antiperspirant preparation and preparations which contain only small amounts of water can be prepared. which preparations are of particular interest because, by their use,
- a further advantage of the astringent and antiperspirant preparations according to our invention is that the alkoxy aluminum chlorides, in contrast to the other aluminum salts heretofore employed, have only a slight tendency to crvstallize. Thus thev do not crystallize on the treated body areas after application and after volatilization of the solvent, but form a flexible film which guarantees a prolonged and better antiperspirant effect than the heretofore used agents possessing pronounced crystalline properties.
- Tables I and II show the solubility of alkoxy aluminum chlorides used according to the present invention and especially the solubility of isopropyloxy aluminum chlorides of the formula Al(C3HqO)2Cl and Al (C H O) Cl in various solvents and the pH values of their aqueous solutions in comparison with a commercially available aluminum oxychloride.
- Table I indicates that the compound is soluble, and that it is insoluble in the respective solvent.
- alkoxy aluminum chlorides which we prefer to use are those whose aqueous solutions have a pH value between 1.0 and 5.0, and preferably a pH value between 3.0 and 4.0.
- the antiperspirant preparations according to our invention are produced by incorporating the alkoxy aluminum chlorides in a concentration between about 5% and about 20% and preferably in a concentration of about 8% to 10%, and for astringent preparations, also in lower amounts, into alcoholic solutions, aerosols, ointments, creams, powders, emulsions, lotions, oils, Waxes, powder sticks, polyhydric alcohols, and into small pieces of cloth, pads, and the like.
- Bactericidal and fungicidal activity can also be imparted to such antiperspirant and astringent preparations according to our invention by the addition of suitable bactericidal and/or fungicidal agents.
- such preparations may contain perfumes, ethereal oils, and/ or cosmetics and other skin cleansing and protecting agents.
- Example 1 An alcoholic solution of the following composition is prepared:
- any humectant such as glycerol, sorbitol, or other 'glycols may be used.
- oleyl alcohol In place of oleyl alcohol, other monohydric alcohols having from 1 to 18 carbon atoms in the molecule may be used.
- Example 2 An aerosol spray of the following composition is prepared:
- Example 3 An ointment of the following composition is prepared:
- Example 4 A glycerol of the following composition is prepared:
- Example 5 A powder of the following composition is prepared:
- Example 6 An astringent solution of mild astringent activity, having the following composition, is prepared:
- line 36 may be used.
- other moisture-holding materials su'ch'as glycerol, sorbitol and other glycols may be used.
- oleyl, cetyl and ethyl alcohol other monohydricalcohols having from 1 to 1-8 carbon atoms in the molecule may be used, and other compatible disinfecting and perfuming and other solvent materials may be used.
- alkoxy aluminum chloride compounds which have been found suitable for use in antiperspirant preparations are ethoxy aluminum dichloride, di-methoxy aluminum chloride, n-propoxy aluminum dichloride, isopropoxy aluminum dichloride, penta-isobutoxy dialuminum chloride, di-hexyloxy aluminum chloride, decyloxy aluminum dichloride, di-dodecyloxy aluminum chloride, octadecyloxy aluminum dichloride, and the like.
- the said alkoxy aluminum chlorides can be prepared for example according to the method described by H. Ulich and W. Nespital, Z. Physic. Chemie, Abt. Al65/294-310 (1933), and Chem. Abstr., vol. 27, page 5232 (1933).
- An antiperspirant anhydrous aerosol composition comprising from about 5 to about 20% by weight of an alkoxy aluminum chloride having the formula wherein R is an alkyl radical with 1 to 3 carbon atoms, x is an integer from 1 to 2, y is an integer selected from the group consisting of 1, 2 and 5 and z is an integer from 1 to 2, the sum of y and 2 'being 3 when x is 1, and the sum of y and 2: being 6 when x is 2, an anhydrous propellant gas selected from the group consisting of diiluoro-dichloro-methane and tetrafiuoro-dichloro-ethane in an amount sufiicient to produce an aerosol spray.
- An antiperspirant anhydrous aerosol composition comprising from about 5 to about 20% by weight of an alkoxy aluminum chloride having the formula Al( OR) C1 wherein R is an alkyl radical with l to 3 carbon atoms, and an anhydrous propellant gas selected from the group consisting of difluoro-dichlormmethane and tetrafluorodichloro-ethane in an amount suflicient to produce an aerosol spray.
- An antiperspirant anhydrous aerosol composition comprising from about 5 to about 20% by weight of an alkoxy aluminum chloride having the formula wherein R is an alkyl radical with 1 to 3 carbon atoms, dissolved in an anhydrous alkanol with l to 3 carbon atoms, and an anhydrous propellant gas selected from the group consisting of difiuoro-dichloro-methane and tetrafluoro-dichloro-ethane in an amount sufiicient to produce an aerosol spray.
Description
AERQSOL ANTIPERSPIRAN T COMPOSITION PREPARATION Giinther Neumann and August Kottler, Biberach (Riss),
Germany, assignors to Dr. Karl Thomae' G. 111. h. H,
Biberach (Kiss), Germany, a corporation of Germany Application December 30, 1955' Serial No. 556,430
Claims priority, application Germany April 22, 1955 3 Claims. (Cl. 167-.-90)
No Drawing.
This invention relates to a perspiration inhibiting and astringent preparation, and more particularly to a perspiration inhibiting and astringent preparation containing an aluminum compound as active ingredient, and to a process of combating excessive perspiration therewith.
It is known that sweat is a secretion of excretory and apocrine sweat glands which are situated in very large numbers in the skin and are irregularly distributed over the entire skin surface. Normal perspiration serves primarily for automatic regulation of the body heat. Many persons sulfer from excessive sweat secretion, sometimes due to emotional stress. Such hyperhidrosis is very annoying and disagreeable. Ordinarily excessive perspiration is localized in specific areas of the body, such as axillas, feet, hands, forehand, abdomen, and particularly palms, soles, inframammary regions and groin. ,The exudate is almost always malodorous. To combat such increased perspiration and to reduce the disagreeable odor to a tolerable degree, the involved body areas are treated with astringents.
Heretofore local hyperhidrosis has been treated with natural and synthetic tanning agents, with acid reacting metal salts, such as chlorides, sulfates, acetates, lactates, borates, sulfamates, phenol sulfonates and similar salts, and more particularly with the corresponding acid aluminum salts. The aluminum salts of stronger acids, such as aluminum sulfate containing Water of crystallization, aluminum chloride and aluminum oxychloride, which have attained increasing importance in the United States, have proved to be the most effective antiperspirants.
These compounds are quite soluble in water. (They have the disadvantage, however, that they are insoluble in agents which are capable of keeping them moist, such as glycerol, glycols, sorbitols, and the like, and are also insoluble in fats and oils, waxes, ointment bases, and alcohols of higher concentration which could otherwise serve as convenient application media for these antiperspirants.
The above-mentioned astringents and antiperspirants are most effective when applied in the form of. their solutions. However, the particularly effective compounds; such as aluminum chloride, AlCl -6H O, aluminum sulfate, Al (SO.,) -18H O, and aluminum oxychloride, can be employed in the required concentration only when in aqueous solution or in lotions and creams containing suflicient amounts of water to carry the astringent in solution. Therefore their possibilities of application are rather limited. They cannot be incorporated in dissolved form into wax sticks, ointments, oils, or alcoholic solutions of high concentration, and uniform distribution of these astringent materials in power bases is very ditficult.
These heretofore known perspiration inhibitingagents, suchas aluminum chloride, aluminumsulfate, aluminumoxychloride and the like, are also. completely unsuitable for use as aerosol preparations containing alcohol and propellent gas since, only small amounts. of water, or none at. all, can. be added. to such. aerosol. preparations and, since. these stringents are insoluble. in the mixture. of alcohol and propellent gas, such as chloro fiuoro hydro-- carbons, they cannot be used in conjunction therewith.
One of the objects of our invention is to provide new astringent and.antiperspirantaluminum compounds which.
notonly possess excellent astringent properties, but which are also readily soluble in-v more or lesshighly concentrated monohydric. alcohols such as, for instance, ethanol,
as well as in glycerol, glycols, sorbitols, variousfatsand oils, ointment bases and in chlorofiuoro hydrocarbons used asaerosol propellents.
Another object of our invention is to provide new and highly effective astringent and antiperspirant preparations which can be applied not only in the form of aqueous and alcoholic solutions but also in the form of ointments, creams, skin lotions, aerosols, powders, wax.sticks, and the like.
A further. object of the invention is to provide: a processof combating excessive perspiration by means of such new and highly efiective astringent and antiperspirant preparations.
Other objects and advantages of. our invention will become apparentas this description proceeds.
in principle, the new and highly effective astringent and antiperspirant aluminum compounds according to our invention are alkoxy aluminum chlorides, i. e., complex compounds of aluminum alcoholates and aluminum chloride, of the general formula A1,(RO),,CI,, wherein R indicates analkyl-radical with 1 to 18 carbon atoms x represents the numerals l or 2 y represents the numerals 1, 2 or 5, and v z represents thenumerals 1 or 2 In the above formula, when x is 1, y and z together mustbe 3, and when x is 2, y, and z together must be 6. The
preferred aluminum compounds of this type correspond to the following formulas:
AI'(RO) C15 Al(RO) Cl and Al (RO) C1 or mixtures of said compounds wherein R, as stated above, indicates an alkyl radical with 1 to 18' carbon atoms. These compounds possess not only excellent astringent properties, but they are also readily soluble tions of said alkoxy aluminum chlorideshave amore orv less strongly acid pH value depending upon their chlorine 3 content. Their pH value is considerably higher than that of the corresponding aluminum chloride solutions as is evident from Table II given hereinafter.
These compounds are compatible with the skin and have proved to be extremely effective agents in inhibiting perspiration and in astringent preparations. In addition to being more effective than the known antiperspirants, they are more comfortable to apply and more comfortable when applied than antiperspirants which must be applied in aqueous solution and which adhere to the skin by drying of the solution and crystallization from the applying solution.
The astringent properties of our new antiperspirants were measured by precipitation of a casein solution according to the method of Jenkins [6. L. Jenkins and I E. Christian, Amer. Perfumer Essent. Orl. Rev. 57, 107 (1951)], and by application to mucous membranes.
The perspiration inhibiting effect was tested in practical ap lications and according to the Manuila test [L. Manuila and H. Isler, Dermatologica 100,'p. 302 (l950), and Dermatologica 102, page 304 (1951)], whereby the sweat glands were incited by pilocarpine iontophoresis. A single application of alkoxy aluminum chlorides according to our invention caused an inhibition of sweat secretion of about 40% and repeated application inhibited sweat secretion to about 70% to 80%.
A further advantage of said alkoxy aluminum chlorides when used as antiperspirants according to our invention is that they permit the pre aration of completely anhydrous, highly effective astringent and perspiration inhibiting preparations based on the use, as diluents and carriers of alcohols, fats, waxes, oils, agents keeping the preparation moist, such as glycerol, sorbitol and the like, or of mixtures thereof. as Well as the preparation of aerosols containing propellent gases. It is, therefore, possible to prepare effective astringent and perspiration inhibiting agents to be applied in a new and more suitable and corrifortable form. In addition to powders, anhydrous antiperspirant preparation and preparations which contain only small amounts of water can be prepared. which preparations are of particular interest because, by their use,
the goal of effective perspiration inhibition is achieved, namely to provide a dry mazeration-preventing treatment of the skin. They replace the heretofore used water-containing preparations which are, for instance, unsuitable for the treatment of excessive perspiration of hands and palms in various professions, such as the metal-working industry.
A further advantage of the astringent and antiperspirant preparations according to our invention is that the alkoxy aluminum chlorides, in contrast to the other aluminum salts heretofore employed, have only a slight tendency to crvstallize. Thus thev do not crystallize on the treated body areas after application and after volatilization of the solvent, but form a flexible film which guarantees a prolonged and better antiperspirant effect than the heretofore used agents possessing pronounced crystalline properties. The high solubility of the alkoxy aluminum chlorides in agents which keep them moist and in fats and oils, at the same time, permits the use of such agents, for instance, in alcoholic solutions thereby aiding the abovedescribed film formation and simultaneously overcoming the desiccating effect which Washeretofore encountered in every effective treatment of hyperhidrosis and which is evidenced by the skin becoming lacerated and chapped.
The following Tables I and II show the solubility of alkoxy aluminum chlorides used according to the present invention and especially the solubility of isopropyloxy aluminum chlorides of the formula Al(C3HqO)2Cl and Al (C H O) Cl in various solvents and the pH values of their aqueous solutions in comparison with a commercially available aluminum oxychloride. In Table I indicates that the compound is soluble, and that it is insoluble in the respective solvent.
TABLEI Solubility Solvent Al-oxychloride Glycerol 1,3-butylene gly- Lz-lpropylene col Octyl alcohol---" Dodeeyl alcohoL. hol
lllll ethan 021 4012 10% ethanol TABLE II.-pH values [The following figures indicate the pH values of 10% solutions of anhydrous diisopropyloxy aluminum chloride, penta-lsopropylo ry dialuminum chloride and aluminum chloride in ethanol and in aqueous ethanol of lower concentrations] The alkoxy aluminum chlorides which we prefer to use are those whose aqueous solutions have a pH value between 1.0 and 5.0, and preferably a pH value between 3.0 and 4.0.
The antiperspirant preparations according to our invention are produced by incorporating the alkoxy aluminum chlorides in a concentration between about 5% and about 20% and preferably in a concentration of about 8% to 10%, and for astringent preparations, also in lower amounts, into alcoholic solutions, aerosols, ointments, creams, powders, emulsions, lotions, oils, Waxes, powder sticks, polyhydric alcohols, and into small pieces of cloth, pads, and the like. Bactericidal and fungicidal activity can also be imparted to such antiperspirant and astringent preparations according to our invention by the addition of suitable bactericidal and/or fungicidal agents. Likewise, such preparations may contain perfumes, ethereal oils, and/ or cosmetics and other skin cleansing and protecting agents.
The following examples of astringent and perspiration inhibiting preparations serve to illustrate the invention without, however, limiting the same thereto.
Example 1 An alcoholic solution of the following composition is prepared:
Isopropyl alcohol, q. s. ad. 100.0 g.
In place of penta-ethoxy dialuminum chloride in the above formula, other alkoxy aluminum chlorides having the general, formula set forth in column 2, line 36, may be used,
In place of 1,2 p'ropyle'ne glycolin' the above formula, any humectant such as glycerol, sorbitol, or other 'glycols may be used.
In place of oleyl alcohol, other monohydric alcohols having from 1 to 18 carbon atoms in the molecule may be used.
In place" of 2,2'-methylen'e"bis (3',4,6-trichloro phenol) other compatible disinfecting and bactericidal agents may be used.
Example 2 An aerosol spray of the following composition is prepared:
G. Penta-isopropyloxy dialuminum chloride Al (C H O) Cl 8.0 1,3-butylene glycol 5.0 Eutanol G (a mixture of liquid monohydric alcohols, Cur-C1 5.0 Difiuoro dichloro methane 35.0 1,2-tetrafluoro dichloro ethane 20.0 Perfume 0.5 Ethanol, q. s. ad. 100.0 g.
Example 3 An ointment of the following composition is prepared:
G. Di-hexadecyloxy aluminum chloride,
(Al H O) C] a- 15.0 Oleyl alcohol 25.0 Sorbitol 5.0 Perfume 0.5 Wool fat, q. s. ad. 100.0 g.
Example 4 A glycerol of the following composition is prepared:
G. Di-isopropyloxy aluminum chloride,
Al(C3H7O) Cl 10.0 Wheat starch 8.0 Tragacanth 2.0 90% ethanol 5.0 Perfume 0.5 Bactericide 0.01 Sorbitol 20.0 Glycerol, q. s. ad. 100.0 g.
Example 5 A powder of the following composition is prepared:
Di-n-butyloxy aluminum chloride, Al(C H O) Cl 5.0
Wool fat 7.0 Cetyl alcohol 3.0 Aluminum stearate 5.0 Talc 20.0
.Perfume 0.5 .2,2-methylene bis-(3,4,6-trichloro phenol) (hexachlorophene) 0.5
vSilicie acid, q. s. ad. 100.0 g.
Example 6 An astringent solution of mild astringent activity, having the following composition, is prepared:
Penta-ethoxy dialuminum chloride, Al(C I-I O) Cl 1.0
'Disinfecting medium 0.01 Ethereal oil 10.0 -Glycerol 5.0
Ethanol, q. s. ad. 100.0 g.
2, line 36, may be used. In place of'the specified humee' tant, other moisture-holding materials su'ch'as glycerol, sorbitol and other glycols may be used. In place of the oleyl, cetyl and ethyl alcohol, other monohydricalcohols having from 1 to 1-8 carbon atoms in the molecule may be used, and other compatible disinfecting and perfuming and other solvent materials may be used.
Other alkoxy aluminum chloride compounds which have been found suitable for use in antiperspirant preparations are ethoxy aluminum dichloride, di-methoxy aluminum chloride, n-propoxy aluminum dichloride, isopropoxy aluminum dichloride, penta-isobutoxy dialuminum chloride, di-hexyloxy aluminum chloride, decyloxy aluminum dichloride, di-dodecyloxy aluminum chloride, octadecyloxy aluminum dichloride, and the like.
The said alkoxy aluminum chlorides can be prepared for example according to the method described by H. Ulich and W. Nespital, Z. Physic. Chemie, Abt. Al65/294-310 (1933), and Chem. Abstr., vol. 27, page 5232 (1933).
While we have given certain formulas and illustrative examples of our invention, it will be understood that many changes and variations in the aluminum alcoholatechloride compounds specified, in their amounts in the antiperspirant and astringent preparations, in the other ingredients of such preparations and in the manner in which such preparations are compounded and used may be made by those skilled in the art in accordance with the principles set forth herein Within the scope of the following claims.
We claim:
1. An antiperspirant anhydrous aerosol composition comprising from about 5 to about 20% by weight of an alkoxy aluminum chloride having the formula wherein R is an alkyl radical with 1 to 3 carbon atoms, x is an integer from 1 to 2, y is an integer selected from the group consisting of 1, 2 and 5 and z is an integer from 1 to 2, the sum of y and 2 'being 3 when x is 1, and the sum of y and 2: being 6 when x is 2, an anhydrous propellant gas selected from the group consisting of diiluoro-dichloro-methane and tetrafiuoro-dichloro-ethane in an amount sufiicient to produce an aerosol spray.
2. An antiperspirant anhydrous aerosol composition comprising from about 5 to about 20% by weight of an alkoxy aluminum chloride having the formula Al( OR) C1 wherein R is an alkyl radical with l to 3 carbon atoms, and an anhydrous propellant gas selected from the group consisting of difluoro-dichlormmethane and tetrafluorodichloro-ethane in an amount suflicient to produce an aerosol spray.
3. An antiperspirant anhydrous aerosol composition comprising from about 5 to about 20% by weight of an alkoxy aluminum chloride having the formula wherein R is an alkyl radical with 1 to 3 carbon atoms, dissolved in an anhydrous alkanol with l to 3 carbon atoms, and an anhydrous propellant gas selected from the group consisting of difiuoro-dichloro-methane and tetrafluoro-dichloro-ethane in an amount sufiicient to produce an aerosol spray.
References Cited in the file of this patent UNITED STATES PATENTS 2,491,116 Kraus et al Dec. 13, 1949 2,492,085 Andersen Dec. 20, 1949 2,504,107 Christian Apr. 18, 1950 2,736,683 Apperson Feb. 28, 1956 (Other references on following page) 7 OTHER REFERENCES Christian: The Amer. Perf. and Ess. Oil Rev., February 1951, pp. 107-108.
Thomas: Anhydrous Aluminum Chloride in Organic 5 Chem, Reinhold Publ. Co., N. Y., 1941, pp. 617-618. Hilfer: Drug and Cos. Ind., May 1952, pp. 606, 607
and 697.
8 Reed: Proc. of-the- 38th Ann. Meeting, .Chem. Specialties Mfg'. Assn.,; pp. 37-41, December 1951.
'De Navarre: The Chem. and Mfg. of Cos., D. Van ,Nostrand Co., N. Y., 1941, page 261.
H Ulich: Zeitschrift fur Physikalische Chemie, Abt. A, Band 165, 1933, pp. 294, 310.
U. S. Disp., J. B. Lippincott Co., Phi1a., 24th ed. 1947, pp; 32-34.
Claims (1)
1. AN ANTIPERSPIRANT ANHYDROUS AEROSOL COMPOSITION COMPRISING FROM ABOUT 5 TO ABOUT 20% BY WEIGHT OF AN ALKOXY ALUMINUM CHLORIDE HAVING THE FORMULA
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US3288681A (en) * | 1962-05-01 | 1966-11-29 | Lever Brothers Ltd | Anhydrous aluminum antiperspirant powder aerosol compositions and methods of preparation |
US3359169A (en) * | 1962-04-27 | 1967-12-19 | Revlon | Aluminum compounds |
US3444226A (en) * | 1966-05-02 | 1969-05-13 | Chattanooga Medicine Co | Heterocyclic aluminum compounds |
US3448189A (en) * | 1966-01-12 | 1969-06-03 | Int Playtex Corp | Organo-aluminum antiperspirant compositions and antiperspirant method |
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US3523153A (en) * | 1966-02-14 | 1970-08-04 | Chatten Drug & Chem Co | Trichloro hydroxy aluminum derivatives in aerosol antiperspirant compositions |
US3523129A (en) * | 1967-10-24 | 1970-08-04 | Chatten Drug & Chem Co | Method of making aluminum chlorohydroxide complexes |
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US4055634A (en) * | 1974-02-22 | 1977-10-25 | Hoffmann-La Roche, Inc. | Antiperspirants |
US4110428A (en) * | 1970-03-23 | 1978-08-29 | Lever Brothers Company | Antiperspirant composition |
EP0217012A1 (en) * | 1985-08-02 | 1987-04-08 | American Cyanamid Company | New Organo-aluminum antiperspirant compositions |
US5281409A (en) * | 1990-04-18 | 1994-01-25 | General Electric Company | Low-misting antiperspirant aerosol compositions |
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US3359169A (en) * | 1962-04-27 | 1967-12-19 | Revlon | Aluminum compounds |
US3288681A (en) * | 1962-05-01 | 1966-11-29 | Lever Brothers Ltd | Anhydrous aluminum antiperspirant powder aerosol compositions and methods of preparation |
US3523130A (en) * | 1965-07-16 | 1970-08-04 | Armour Pharma | Method of making alcohol-soluble complexes of aluminum |
US3520911A (en) * | 1965-07-16 | 1970-07-21 | Armour Pharma | Method of making alcohol-soluble complexes of aluminum |
US3448189A (en) * | 1966-01-12 | 1969-06-03 | Int Playtex Corp | Organo-aluminum antiperspirant compositions and antiperspirant method |
US3523153A (en) * | 1966-02-14 | 1970-08-04 | Chatten Drug & Chem Co | Trichloro hydroxy aluminum derivatives in aerosol antiperspirant compositions |
US3444226A (en) * | 1966-05-02 | 1969-05-13 | Chattanooga Medicine Co | Heterocyclic aluminum compounds |
US3523129A (en) * | 1967-10-24 | 1970-08-04 | Chatten Drug & Chem Co | Method of making aluminum chlorohydroxide complexes |
US3472929A (en) * | 1968-10-23 | 1969-10-14 | Armour Pharma | Method of making alcohol-soluble complexes of aluminum |
US3507896A (en) * | 1968-10-23 | 1970-04-21 | Armour Pharma | Method of making alcohol-soluble complexes of aluminum |
FR2035901A1 (en) * | 1969-03-26 | 1970-12-24 | Williams Co Inc | |
FR2039249A1 (en) * | 1969-04-17 | 1971-01-15 | Gillette Co | |
US4110428A (en) * | 1970-03-23 | 1978-08-29 | Lever Brothers Company | Antiperspirant composition |
US4055634A (en) * | 1974-02-22 | 1977-10-25 | Hoffmann-La Roche, Inc. | Antiperspirants |
EP0217012A1 (en) * | 1985-08-02 | 1987-04-08 | American Cyanamid Company | New Organo-aluminum antiperspirant compositions |
US5281409A (en) * | 1990-04-18 | 1994-01-25 | General Electric Company | Low-misting antiperspirant aerosol compositions |
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