CA1328408C - Deodorant gel stick - Google Patents
Deodorant gel stickInfo
- Publication number
- CA1328408C CA1328408C CA000583572A CA583572A CA1328408C CA 1328408 C CA1328408 C CA 1328408C CA 000583572 A CA000583572 A CA 000583572A CA 583572 A CA583572 A CA 583572A CA 1328408 C CA1328408 C CA 1328408C
- Authority
- CA
- Canada
- Prior art keywords
- deodorant
- glycol
- mixtures
- deodorant gel
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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Classifications
-
- 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
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/0216—Solid or semisolid forms
- A61K8/0229—Sticks
-
- 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
- A61K8/042—Gels
-
- 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
- A61K8/37—Esters of carboxylic acids
-
- 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
- A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
-
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
-
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/05—Stick
Abstract
ABSTRACT
Disclosed are deodorant gel stick compositions comprising from about 0.1 to about 10.0% of a deodorant active, from about 7% to about 35% of intermediate polarity emollients, from about 2%
to about 8% of a benzylidene sorbitol, from about 7% to about 75%
of a polar solvent, and from about 5% to about 40% of a coupling agent. These deodorant gel sticks provide very stable deodorant compositions with good efficacy as well as excellent cosmetics which are further characterized by their ease of manufacture.
Disclosed are deodorant gel stick compositions comprising from about 0.1 to about 10.0% of a deodorant active, from about 7% to about 35% of intermediate polarity emollients, from about 2%
to about 8% of a benzylidene sorbitol, from about 7% to about 75%
of a polar solvent, and from about 5% to about 40% of a coupling agent. These deodorant gel sticks provide very stable deodorant compositions with good efficacy as well as excellent cosmetics which are further characterized by their ease of manufacture.
Description
1~28408 DEODORANT GEL STICK
The present invention relates to stick-type deodorant compositions. More particularly it relates to improved gel-type deodorant sticks, and also to methods for treating or preventing malodor associated with human underarm perspiration.
10There are three main types of such stick formulations:
compressed powder sticks, gel sticks, and wax sticks. While each of these formulation types may have advantages in certain use situations, each also has disadvantages. For example, com-pressed powder sticks are often brittle and hard, and leave a 15cosmetically-unacceptable dust upon application. Wax-based formulations can also yield cosmetically-unacceptable products due to such factors such as hardness, greasiness, and stickiness.
The opacity of such wax sticks, and the residue created in their use, may also be aesthetically undesirable.
20Gel based sticks have several advantages over both corn-pressed powder and wax sticks such as leaving little or no residue or dust. ~iel sticks also provide a vehicle which glides easily over the skin surface.
I n general soap-based gel-based sticks contain sodium 25stearate along with relatively high levels of either propylene glycol or ethanol. References disclosing such soap-type gel sticks include in U.S. Patent 4,154,816 to Roehl et al., issued May 15, 1979; U.S. Patent 4,226,889 to Yukas, issued October 2, 1980; and U.S. Patent 4,268,498 to Gedeon et al., issued May 19, 301981.
Such soap-based sticks which contain high levels of propylene glycol tend to be sticky both during and after application thereby imparting relatively poor cosmetics. Other soap-based sticks may contain high levels of ethanol which leads 13284~8 to skin irritation. High levels of ethanol also leads to shrinkage and also weight loss of the packaged deodorant gel stick due to the voiatility of ethanol.
Many stick formulations have been described in the literature which attempt to maintain the desirable cosmetic and aesthetic attributes of gel sticks, while minimizing their disadvantages. For example, antiperspirant gel sticks, using dibenzaldehyde monosor-bitol acetal (herein DBMSA ) as a gelling agent, are described in U.S. Patent 4,154,816, Roehl, et al., issued May 15, 1979, U.S.
Patent 4,346,079, Roehl, issued August 24, 1982, and U.S. Patent 4,518,582, Schamper, et al., issued Mlay 21, 1985. Deodorant sticks using DBMSA are described in Japanese Patent 50/52,007, published April 8, 1975. Nevertheless, it has been found that such DBMSA sticks, while avoiding the use of soaps, may produce products with aesthetically unacceptable stickiness. The solid gel sticks of the present invention provide very stable deodorant gel stick compositions with good efficacy as well as excellent cosmetics and aesthetics which are further characterized by their ease of manufacture .
It is therefore an object of the present invention to provide deodGrant gel sticks which have good deodorant efficacy as well as improved cosmetics. It is still a further object to provide optically clear or translucent gel sticks which are cosmetically acceptable. A still further object of the present invention is to provide gel sticks which are stable and easy to formulate and manufacture. A still further object is to provide gel sticks which are non-sticky. A still further object is to provide gel sticks which contain relatively low levels of ethanol and propylene glycol to minimize skin irritation, stinging and burning.
These and other objects of the present invention will become readily apparent from the detailed description which follows.
All percentages and ratios used herein are by weight unless o~herwise specified.
SUMMARY OF THE INVENTION
These gel sticks comprise:
(a) from about 0.1% to about 10% of a deodorant active;
(b) from about 7% to about 70% of intermediate polarity emollients selected from the group consisting of ethyl, isopropyl, and n-butyl diesters of adipic, phalic and sebacic acids, and mixtures thereot;
(c) from about 2% to about 8% of a benzylidene sorbitol;
(d) from about 5% to about 75% of a polar solvent; and (e) from about 5% to about 40% of a coupling agent selected from the group consisting of polypropylene glycol ethers of C4-C20 fatty alcohols, C6-C,7fatty alcohols, ethoxylated derivatives of C~-C" fatty alcohols, polyethylene glycols having a molecular weight of less than about 400, dimethyl isosorbide and mixtures thereof.
These gel stick compositions have good deodorant efEicacy as well as excellent cosmetics and aesthetics.
DETAILED DESCRIPTION OF THE INVENTION
Deodorant Active Suitabie deodorants include bacteriostatic quaternary ammonium compounds such as cetyl-trimethylammonium bromide, cetyl pyridinium chloride, benzethonium chloride, diisobutyl phenoxy ethoxy ethyl dimethyl benzyl ammonium chloride, sodium N-lauryl sarcosine, sodium N-palmethyl sarcosine, lauroyl sarco-si~Se, N-myristoyl glycine, potassium N-lauryl sarcosine, stearyl, ~rimethyl ammonium chloride, sodium aluminum chlorohydroxy lactate, tricetylmethyl ammonium chloride, 2,4,4'-trichloro-2'-hydroxy diphenyl ether, and zinc salts such as zinc citrate, zinc salicylate, and mixtures thereof. The preferred deodorant material is 2,4,4'-trichloro-2'-hydroxydiphenyl ether. These deodorants comprise from about 0 .196 to about 10 . 0% of the composition .
Intermediate Polarity Emollients The compositions of the present invention contain from about 7% to about 70% of one or more intermediate polarity emollient.
Useful intermediate polarity emollients include the ethyl, isopropyl and n-butyl diesters of adipic, phthalic and sebacic acids.
Preferred ;ntermediate polarity emollients of the present invention include di-n-butyl phtalate, diethyl sebacate, di-isopropyl adipate and ethyl ethyl carbomethyl phthalate, all of which are disclosed in U.S. Patent 4,045,548 to Luedders et al, issued August 30, 1977. The most preferre~1 intermediate polarity emollient is di-isopropyl adipate.
A
-. .
~ 4 ~ 1 3 284 0 8 Emollients among those useful herein are described in 1 Cosmetics, Science and Technology 27-104 (M . Balsam and E .
Sagarin, Ed.: 1972), and U.S. Patent 4,202,879, to Shelton, issued May 13, 1980.
The compositions of the present invention can further comprise from about 1% to about 40%, preferably from about 4% to about 20% of optional non-polar emollients. Useful non-polar emollients also include volatile silicone oils, non-polar non-volatile emollients, and mixtures thereof. The term "volatile", as used herein, refers to those materials which have a measurable vapor pressure at ambient temperature.
Volatile silicone oils useful in the cosmetic stick compositions of the present invention are preferably cyclic or linear poly-dimethylsiloxanes containing from about 3 to about 9, preferably from about 4 to about 5, silicon atoms. The following formula illustrates cyclic volatile polydimethylsiloxanes useful in the cosmetic stick compositions disclosed herein:
[~
wherein n equals about 3 to about 7. Linear polydimethyl-siloxanes contain from about 3 to about 9 silicon atoms per molecule and have the following general formula:
(CH3)3Si-O-lSi(CH3)2-O]n-Si(CH3)3 wherein n equals about 1 to about 7. Linear volatile silicone materials generally have viscosities of less than about 5 centi-stokes at 25C while cyclic materials typically have viscosities of Iess than about 10 centistokes. A description of various volatile silicone oils is found in Todd, et al., "Volatile Silicone Fluids for Cosmetics", Cosmetics ~ Toiletries, 91, pages 27-32 (1976)~
Examples of preferred volatile silicone oils useful herein include: Dow Corning 344, Dow Corning 345, and Dow Corning 200 (manufactured by the Dow Corning Corp. ~; Silicone 7207 and ~ 5 ~ 1 3 2 8~ ~ 8 Silicone 7158 (manufactured by the Union Carbide Corp.); SF
1202 (manufactured by General Electric): and SWS-03314 (manu-factured by SWS Silicones, Inc. ) .
Non-volatile silicone oils useful as an emollient material include polyalkylsiloxanes, polyalkylarylsiloxanes, and polyether-siloxane copolymers. The essentially non-volatile polyalkyl silo-xanes useful herein include, for example, polydimethyl siloxanes with viscosities of from about 5 to about 100,000 centitokes at 25C. Among the preferred non-volatile emollients useful in the present compositions are the polydimethyl siloxanes having vis-cosities from about 2 to about 400 centistokes at 25C. Such polyalkyl siloxanes include the Vicasil series (sold by General Electric Company) and the Dow Corning 200 series (sold by Dow Corning Corporation). Polyalkylaryl siloxanes include poly methyl-phenyl siloxanes having viscosities of from about 15 to about 65 centistokes at 25C. These are available, for example, as SF
1075 methylphenyl fluid lsold by General Electric Company) and 556 Cosmetic Grade Fluid (sold by Dow Corning Corporation).
Useful polyether siloxane copolymers include, for example, a polyoxyalkylene et~er copolymer having a viscosity of about 1200 to 1500 centistokes at 25C. Such a fluid is available as SF-1066 organosilicone surfactant tsold by General Electric Company).
Polysiloxane ethylene glycol ether copolymers are preferred copoly-mers for use in the present compositions.
Benzylidene Sorbitol The compositions of this invention also include from about 2 to about 8%, preferably from about 4% to about 6% of a benzy-Iidene sorbitol, which serves as a gelling agent for the deodorant stick. The level of these agents are chosen so as to provide the appropriate stick hardness and the appropriate level of product transfer to the skin upon application. Such materials are generally disclosed in British Patent Specification 1,291,819, published October 4, 1972 and in U.S. Patent 4,518,582 to Schamper et al ., issued May 28, 1985.
A
A preferred benzylidene sorbitol for use in the present compositions is dibenzylidene monosorbitol acetal ~DBMSA). This material is commercially available, such as Gell-AII-D (manufac-tured by New Japan Chemical Co., Ltd . ) and Millithix 925 (manufac-tured by l\/lilliken Chemical, Division of Milliken ~ Company).
Polar Solvent The polar solvent comprises from about 7% to about 75~, preferably from about 50% to about 70~ of the total composition.
Useful polar solvents include propylene carbonate, water, methanol, ethanol, n-propanol, n-butanol, 2-methoxyethanol, 2-ethoxyethanol; ethylene glycol, 1,2--propylene glycol, 1,3-propylene glycol, 1,4-butylene glycol, 1,2-butylene glycol, diethylene glycol, isopropanol, isobutanol, diethylene glycol monomethylether, diethylene glycol monoethyl ether, 1,3-butylene glycol, 2,3-butylene glycol, dipropylene glycol, 2,4-dihydroxy-2-methylpentane, and the like and mixtures thereof.
These solvents are fully described in the above-referenced U.S. Patent 4,518,582 to Schamper et al., issued May 21, 1985.
The preferred polar solvents are propylene carbonate, ethanol, propylene glycol, 1,3-butylene glycol and 2,4-dihydroxy-2-methyl-pentane (sometimes referred to as hexylene glycol) and mixtures thereof. Even more preferred solvents are propylene carbonate (2-10% preferred), ethanol (15-25% preferred), propylene glycol (2-10% preferred) and dipropylene glycol (20-40% preferred).
Coupling Agents The compositions of the present invention also essentially comprise at least one coupling agent. The term "coupling agent", as used herein, means any compound, composition, or combination thereof which acts to bring the polar, intermediate polarity and non-polar components of the present invention into a homogeneous stick composition. Preferred coupling agents for use herein are polypropylene glycol ("PPG") ethers of C4-C22 (preferably C1 0-C20) fatty alcohols. Examples of such materials are:
PPG-5-ceteth-20, PPG-4 myristyl ether, PPG-4 lauryl ether, PPG-10 cetyl ether, PPG-3 myristyl ether, and mixtures thereof.
Additional examples are found in CTFA Cosmetic Ingredient ~. ,' .
132~408 Dictionary, Third Edition (Estrin et al., Editors; The Cosmetic, Toiletry and Fragrance Association, Inc.; 1982), pages 252-260 and 494-500.
Other useful coupling agents include C6-C22 fatty alcohols, ethoxylated S derivatives of C4-C7, fatty alcohols, propoxylated derivatives of C4-C.. fattyalcohols, polyethylene glycols with a molecular weight of less than about 400, dimethyl isosorbide and mixtures thereof as described, for example, in ~g & Cosmetic Industrv, 138 (2), p. 40 (1986). More preferred are ethoxylated derivatives of Cl0-C~o fatty alcohols, propoxylated derivatives of Cl0-C~o fatty10 alcohols, and mixtures thereo The coupling agent typically comprises from about 5% to about 405~o, preferably from about 10% to about 30%, and most preferably from about 15% to about 25%, of the compositions of the prevent invention.
Optional Components The compositions of this invention can also contain optional components which modify the physical characteristics of the gel sticks. Such components include hardeners, strengtheners, colorants, perfumes, emulsifiers, and fillers. Optional components, useful herein, are disclosed in the following patent documents: U.S. Patent 3,255,082, Barton, issued June 7, 1966; U.S.
20 Patent 4,137,306, Rubino, et al., issued January 30, 1979; U.S. Patent 4,279,658, Hooper, et al., issued July 14, 1981; and European Patent Specification 117,070, May, published August 29, 1984.
The instant cosmetic sticks can also contain from about 0.1% to about 10% (by weight) of an inert filler material. Suitable filler materials include 25 talc, colloidal silica (such as Cab-O-Sil~, sold by Cabot Corp.)~ clays (such as bentonite), and mixtures thereof. The use of such fillers as stabilizing agents in cosmetic sticks is disclosed in U.S. Patent 4,126,679, Davy et al., issued November 21, 1978.
A
The compositions of the present invention can further comprise from about 0.5% to about 10% of a buffering/pH adjust-ment agent. Suitable agents are generally disclosed in U.S.
Patent 4,346,079 to Roehl, issued August 29, 1982 and in Euro-pean Patent Application 175,074 of Schamper et al, published March 26, 1986, Suitable buffering agents include coconut monoethanolamide, sodium hydroxide, stearamide monoethanolamide, acetamide MEA, zinc acetate, zinc stearate, aluminum oxide, calcium acetate, zinc oxide, magnesium oxide, calcium carbonate, calcium hydroxide, sodium carbonate, magnesium carbonate, zinc carbonate, butyro-lactone, calcium oxide, and mixtures thereof.
Method of Manufacture Compositions of the present invention are made by art recognized methods. For example, the components can be combined and mixed thoroughly and then heated to between approximately 170F (77C) and 300F (149Cl under agitation for from about 5 to about 120 minutes. The solution is then poured into stick form.
Methods for Preventing Malodor The present invention also provides methods for treating or preventing malodor associated with human underarm perspiration.
These methods comprise applying to the skin of a human a safe and effective amount of the deodorant gel of the present inven-tion. The term "a safe and effective amount", as used herein, is an amount which is effective in eliminating or substantially reduclng malodor associated with human underarm perspiration while being safe for human use at a reasonable risk/benefit ratio.
The following examples further describe and demonstrate embodiments within the scope of the present invention. These examples are solely for the purpose of illustration and are not to be construed as limitations of the present invention as many variations are possible without depa!ting from the spirit or scope thereof.
EXAMPLE I
A deodorant composition of the present invention is made by combining the following:
Material Weight %
2,4,4'-Trichloro-2-Hydroxy Diphenyl ether 0.30 Propylene Glycol 3.80 Dipropylene Glycol 32.50 Propylene Carbonate 7.70 Ethanol 20.00 PPG-3 Myristyl Ether 9.60 Di-isopropyl Adipate1 9.60 Polyethylene Glycol-6 1 PEG-6) 9.60 Fragrance 2.00 Benzylidene Sorbitol2 4.90 100~
1 Schercemol~DlA by Scher Chemicals, Inc., Clifton, New Jersey 2 Millithix 925(~ manufactured by Milliken Chemical, Division of Milliken & Company The deodorant gel stick composition is prepared as follows. A
premix is made by combining the 2,4,4'-trichloro-2-hydroxy diphenyl ether, propylene glycol, dipropylene glycol, propylene carbonate, ethanol, PPG-3-myristyl ether, PEG-6, di-isopropyl adipate, and benzylidene monosorbitol. These components are heated to approximately 190F (88C). Once clear, the solution is then cooled to approximately 160F 171C), at which time the fragrance is added.
A uniform deodorant gel stick forms as the composition cools to room temperature. The resulting gel stick is optically clear with excellent efficacy as well as excellent nonsticky cosmetics and aesthetics.
The deodorant composition is applied to the underarm skin of - a human to effectively prevent underarm odor resulting from perspiration. The composition is relatively non-sticky and feels lubricious when applied to the skin.
A
- lo - I 32 ~ 4 0 8 , EXAMPLES ll - IV
These deodorant gel stick compositions are made as described above in Example 1.
Concentration (~ by weight) Material Name l l l l l IV
Benzylidene Sorbitol4.00 5.00 5.00 Propylene Carbonate2 . 0016 . 002 . 00 Propylene Glycol 5.00 16.00 2.00 Cyclomethicone 10 . 00 Di-Methyl Isosorbide20.00 16.00 10.00 Di-lsopropyl Adipate57.00 10.00 PPG-3 Myristyl Ether 10 . 00 Ethanol 13.00 19.00 Dipropylene Glycol 16.00 30.00 ~5 Polyethylene Glycol 16 . 00 10 . 00 Triclosan 0.30 0.30 0.30 2,4,4'-Trichloro-2-hydroxy Diphenyl ether 0.30 0.30 0.30 Perfume/Color qs qs qs Totals~ 100. 00100 . 00100. 00 WHAT IS CLAIMED IS:
The present invention relates to stick-type deodorant compositions. More particularly it relates to improved gel-type deodorant sticks, and also to methods for treating or preventing malodor associated with human underarm perspiration.
10There are three main types of such stick formulations:
compressed powder sticks, gel sticks, and wax sticks. While each of these formulation types may have advantages in certain use situations, each also has disadvantages. For example, com-pressed powder sticks are often brittle and hard, and leave a 15cosmetically-unacceptable dust upon application. Wax-based formulations can also yield cosmetically-unacceptable products due to such factors such as hardness, greasiness, and stickiness.
The opacity of such wax sticks, and the residue created in their use, may also be aesthetically undesirable.
20Gel based sticks have several advantages over both corn-pressed powder and wax sticks such as leaving little or no residue or dust. ~iel sticks also provide a vehicle which glides easily over the skin surface.
I n general soap-based gel-based sticks contain sodium 25stearate along with relatively high levels of either propylene glycol or ethanol. References disclosing such soap-type gel sticks include in U.S. Patent 4,154,816 to Roehl et al., issued May 15, 1979; U.S. Patent 4,226,889 to Yukas, issued October 2, 1980; and U.S. Patent 4,268,498 to Gedeon et al., issued May 19, 301981.
Such soap-based sticks which contain high levels of propylene glycol tend to be sticky both during and after application thereby imparting relatively poor cosmetics. Other soap-based sticks may contain high levels of ethanol which leads 13284~8 to skin irritation. High levels of ethanol also leads to shrinkage and also weight loss of the packaged deodorant gel stick due to the voiatility of ethanol.
Many stick formulations have been described in the literature which attempt to maintain the desirable cosmetic and aesthetic attributes of gel sticks, while minimizing their disadvantages. For example, antiperspirant gel sticks, using dibenzaldehyde monosor-bitol acetal (herein DBMSA ) as a gelling agent, are described in U.S. Patent 4,154,816, Roehl, et al., issued May 15, 1979, U.S.
Patent 4,346,079, Roehl, issued August 24, 1982, and U.S. Patent 4,518,582, Schamper, et al., issued Mlay 21, 1985. Deodorant sticks using DBMSA are described in Japanese Patent 50/52,007, published April 8, 1975. Nevertheless, it has been found that such DBMSA sticks, while avoiding the use of soaps, may produce products with aesthetically unacceptable stickiness. The solid gel sticks of the present invention provide very stable deodorant gel stick compositions with good efficacy as well as excellent cosmetics and aesthetics which are further characterized by their ease of manufacture .
It is therefore an object of the present invention to provide deodGrant gel sticks which have good deodorant efficacy as well as improved cosmetics. It is still a further object to provide optically clear or translucent gel sticks which are cosmetically acceptable. A still further object of the present invention is to provide gel sticks which are stable and easy to formulate and manufacture. A still further object is to provide gel sticks which are non-sticky. A still further object is to provide gel sticks which contain relatively low levels of ethanol and propylene glycol to minimize skin irritation, stinging and burning.
These and other objects of the present invention will become readily apparent from the detailed description which follows.
All percentages and ratios used herein are by weight unless o~herwise specified.
SUMMARY OF THE INVENTION
These gel sticks comprise:
(a) from about 0.1% to about 10% of a deodorant active;
(b) from about 7% to about 70% of intermediate polarity emollients selected from the group consisting of ethyl, isopropyl, and n-butyl diesters of adipic, phalic and sebacic acids, and mixtures thereot;
(c) from about 2% to about 8% of a benzylidene sorbitol;
(d) from about 5% to about 75% of a polar solvent; and (e) from about 5% to about 40% of a coupling agent selected from the group consisting of polypropylene glycol ethers of C4-C20 fatty alcohols, C6-C,7fatty alcohols, ethoxylated derivatives of C~-C" fatty alcohols, polyethylene glycols having a molecular weight of less than about 400, dimethyl isosorbide and mixtures thereof.
These gel stick compositions have good deodorant efEicacy as well as excellent cosmetics and aesthetics.
DETAILED DESCRIPTION OF THE INVENTION
Deodorant Active Suitabie deodorants include bacteriostatic quaternary ammonium compounds such as cetyl-trimethylammonium bromide, cetyl pyridinium chloride, benzethonium chloride, diisobutyl phenoxy ethoxy ethyl dimethyl benzyl ammonium chloride, sodium N-lauryl sarcosine, sodium N-palmethyl sarcosine, lauroyl sarco-si~Se, N-myristoyl glycine, potassium N-lauryl sarcosine, stearyl, ~rimethyl ammonium chloride, sodium aluminum chlorohydroxy lactate, tricetylmethyl ammonium chloride, 2,4,4'-trichloro-2'-hydroxy diphenyl ether, and zinc salts such as zinc citrate, zinc salicylate, and mixtures thereof. The preferred deodorant material is 2,4,4'-trichloro-2'-hydroxydiphenyl ether. These deodorants comprise from about 0 .196 to about 10 . 0% of the composition .
Intermediate Polarity Emollients The compositions of the present invention contain from about 7% to about 70% of one or more intermediate polarity emollient.
Useful intermediate polarity emollients include the ethyl, isopropyl and n-butyl diesters of adipic, phthalic and sebacic acids.
Preferred ;ntermediate polarity emollients of the present invention include di-n-butyl phtalate, diethyl sebacate, di-isopropyl adipate and ethyl ethyl carbomethyl phthalate, all of which are disclosed in U.S. Patent 4,045,548 to Luedders et al, issued August 30, 1977. The most preferre~1 intermediate polarity emollient is di-isopropyl adipate.
A
-. .
~ 4 ~ 1 3 284 0 8 Emollients among those useful herein are described in 1 Cosmetics, Science and Technology 27-104 (M . Balsam and E .
Sagarin, Ed.: 1972), and U.S. Patent 4,202,879, to Shelton, issued May 13, 1980.
The compositions of the present invention can further comprise from about 1% to about 40%, preferably from about 4% to about 20% of optional non-polar emollients. Useful non-polar emollients also include volatile silicone oils, non-polar non-volatile emollients, and mixtures thereof. The term "volatile", as used herein, refers to those materials which have a measurable vapor pressure at ambient temperature.
Volatile silicone oils useful in the cosmetic stick compositions of the present invention are preferably cyclic or linear poly-dimethylsiloxanes containing from about 3 to about 9, preferably from about 4 to about 5, silicon atoms. The following formula illustrates cyclic volatile polydimethylsiloxanes useful in the cosmetic stick compositions disclosed herein:
[~
wherein n equals about 3 to about 7. Linear polydimethyl-siloxanes contain from about 3 to about 9 silicon atoms per molecule and have the following general formula:
(CH3)3Si-O-lSi(CH3)2-O]n-Si(CH3)3 wherein n equals about 1 to about 7. Linear volatile silicone materials generally have viscosities of less than about 5 centi-stokes at 25C while cyclic materials typically have viscosities of Iess than about 10 centistokes. A description of various volatile silicone oils is found in Todd, et al., "Volatile Silicone Fluids for Cosmetics", Cosmetics ~ Toiletries, 91, pages 27-32 (1976)~
Examples of preferred volatile silicone oils useful herein include: Dow Corning 344, Dow Corning 345, and Dow Corning 200 (manufactured by the Dow Corning Corp. ~; Silicone 7207 and ~ 5 ~ 1 3 2 8~ ~ 8 Silicone 7158 (manufactured by the Union Carbide Corp.); SF
1202 (manufactured by General Electric): and SWS-03314 (manu-factured by SWS Silicones, Inc. ) .
Non-volatile silicone oils useful as an emollient material include polyalkylsiloxanes, polyalkylarylsiloxanes, and polyether-siloxane copolymers. The essentially non-volatile polyalkyl silo-xanes useful herein include, for example, polydimethyl siloxanes with viscosities of from about 5 to about 100,000 centitokes at 25C. Among the preferred non-volatile emollients useful in the present compositions are the polydimethyl siloxanes having vis-cosities from about 2 to about 400 centistokes at 25C. Such polyalkyl siloxanes include the Vicasil series (sold by General Electric Company) and the Dow Corning 200 series (sold by Dow Corning Corporation). Polyalkylaryl siloxanes include poly methyl-phenyl siloxanes having viscosities of from about 15 to about 65 centistokes at 25C. These are available, for example, as SF
1075 methylphenyl fluid lsold by General Electric Company) and 556 Cosmetic Grade Fluid (sold by Dow Corning Corporation).
Useful polyether siloxane copolymers include, for example, a polyoxyalkylene et~er copolymer having a viscosity of about 1200 to 1500 centistokes at 25C. Such a fluid is available as SF-1066 organosilicone surfactant tsold by General Electric Company).
Polysiloxane ethylene glycol ether copolymers are preferred copoly-mers for use in the present compositions.
Benzylidene Sorbitol The compositions of this invention also include from about 2 to about 8%, preferably from about 4% to about 6% of a benzy-Iidene sorbitol, which serves as a gelling agent for the deodorant stick. The level of these agents are chosen so as to provide the appropriate stick hardness and the appropriate level of product transfer to the skin upon application. Such materials are generally disclosed in British Patent Specification 1,291,819, published October 4, 1972 and in U.S. Patent 4,518,582 to Schamper et al ., issued May 28, 1985.
A
A preferred benzylidene sorbitol for use in the present compositions is dibenzylidene monosorbitol acetal ~DBMSA). This material is commercially available, such as Gell-AII-D (manufac-tured by New Japan Chemical Co., Ltd . ) and Millithix 925 (manufac-tured by l\/lilliken Chemical, Division of Milliken ~ Company).
Polar Solvent The polar solvent comprises from about 7% to about 75~, preferably from about 50% to about 70~ of the total composition.
Useful polar solvents include propylene carbonate, water, methanol, ethanol, n-propanol, n-butanol, 2-methoxyethanol, 2-ethoxyethanol; ethylene glycol, 1,2--propylene glycol, 1,3-propylene glycol, 1,4-butylene glycol, 1,2-butylene glycol, diethylene glycol, isopropanol, isobutanol, diethylene glycol monomethylether, diethylene glycol monoethyl ether, 1,3-butylene glycol, 2,3-butylene glycol, dipropylene glycol, 2,4-dihydroxy-2-methylpentane, and the like and mixtures thereof.
These solvents are fully described in the above-referenced U.S. Patent 4,518,582 to Schamper et al., issued May 21, 1985.
The preferred polar solvents are propylene carbonate, ethanol, propylene glycol, 1,3-butylene glycol and 2,4-dihydroxy-2-methyl-pentane (sometimes referred to as hexylene glycol) and mixtures thereof. Even more preferred solvents are propylene carbonate (2-10% preferred), ethanol (15-25% preferred), propylene glycol (2-10% preferred) and dipropylene glycol (20-40% preferred).
Coupling Agents The compositions of the present invention also essentially comprise at least one coupling agent. The term "coupling agent", as used herein, means any compound, composition, or combination thereof which acts to bring the polar, intermediate polarity and non-polar components of the present invention into a homogeneous stick composition. Preferred coupling agents for use herein are polypropylene glycol ("PPG") ethers of C4-C22 (preferably C1 0-C20) fatty alcohols. Examples of such materials are:
PPG-5-ceteth-20, PPG-4 myristyl ether, PPG-4 lauryl ether, PPG-10 cetyl ether, PPG-3 myristyl ether, and mixtures thereof.
Additional examples are found in CTFA Cosmetic Ingredient ~. ,' .
132~408 Dictionary, Third Edition (Estrin et al., Editors; The Cosmetic, Toiletry and Fragrance Association, Inc.; 1982), pages 252-260 and 494-500.
Other useful coupling agents include C6-C22 fatty alcohols, ethoxylated S derivatives of C4-C7, fatty alcohols, propoxylated derivatives of C4-C.. fattyalcohols, polyethylene glycols with a molecular weight of less than about 400, dimethyl isosorbide and mixtures thereof as described, for example, in ~g & Cosmetic Industrv, 138 (2), p. 40 (1986). More preferred are ethoxylated derivatives of Cl0-C~o fatty alcohols, propoxylated derivatives of Cl0-C~o fatty10 alcohols, and mixtures thereo The coupling agent typically comprises from about 5% to about 405~o, preferably from about 10% to about 30%, and most preferably from about 15% to about 25%, of the compositions of the prevent invention.
Optional Components The compositions of this invention can also contain optional components which modify the physical characteristics of the gel sticks. Such components include hardeners, strengtheners, colorants, perfumes, emulsifiers, and fillers. Optional components, useful herein, are disclosed in the following patent documents: U.S. Patent 3,255,082, Barton, issued June 7, 1966; U.S.
20 Patent 4,137,306, Rubino, et al., issued January 30, 1979; U.S. Patent 4,279,658, Hooper, et al., issued July 14, 1981; and European Patent Specification 117,070, May, published August 29, 1984.
The instant cosmetic sticks can also contain from about 0.1% to about 10% (by weight) of an inert filler material. Suitable filler materials include 25 talc, colloidal silica (such as Cab-O-Sil~, sold by Cabot Corp.)~ clays (such as bentonite), and mixtures thereof. The use of such fillers as stabilizing agents in cosmetic sticks is disclosed in U.S. Patent 4,126,679, Davy et al., issued November 21, 1978.
A
The compositions of the present invention can further comprise from about 0.5% to about 10% of a buffering/pH adjust-ment agent. Suitable agents are generally disclosed in U.S.
Patent 4,346,079 to Roehl, issued August 29, 1982 and in Euro-pean Patent Application 175,074 of Schamper et al, published March 26, 1986, Suitable buffering agents include coconut monoethanolamide, sodium hydroxide, stearamide monoethanolamide, acetamide MEA, zinc acetate, zinc stearate, aluminum oxide, calcium acetate, zinc oxide, magnesium oxide, calcium carbonate, calcium hydroxide, sodium carbonate, magnesium carbonate, zinc carbonate, butyro-lactone, calcium oxide, and mixtures thereof.
Method of Manufacture Compositions of the present invention are made by art recognized methods. For example, the components can be combined and mixed thoroughly and then heated to between approximately 170F (77C) and 300F (149Cl under agitation for from about 5 to about 120 minutes. The solution is then poured into stick form.
Methods for Preventing Malodor The present invention also provides methods for treating or preventing malodor associated with human underarm perspiration.
These methods comprise applying to the skin of a human a safe and effective amount of the deodorant gel of the present inven-tion. The term "a safe and effective amount", as used herein, is an amount which is effective in eliminating or substantially reduclng malodor associated with human underarm perspiration while being safe for human use at a reasonable risk/benefit ratio.
The following examples further describe and demonstrate embodiments within the scope of the present invention. These examples are solely for the purpose of illustration and are not to be construed as limitations of the present invention as many variations are possible without depa!ting from the spirit or scope thereof.
EXAMPLE I
A deodorant composition of the present invention is made by combining the following:
Material Weight %
2,4,4'-Trichloro-2-Hydroxy Diphenyl ether 0.30 Propylene Glycol 3.80 Dipropylene Glycol 32.50 Propylene Carbonate 7.70 Ethanol 20.00 PPG-3 Myristyl Ether 9.60 Di-isopropyl Adipate1 9.60 Polyethylene Glycol-6 1 PEG-6) 9.60 Fragrance 2.00 Benzylidene Sorbitol2 4.90 100~
1 Schercemol~DlA by Scher Chemicals, Inc., Clifton, New Jersey 2 Millithix 925(~ manufactured by Milliken Chemical, Division of Milliken & Company The deodorant gel stick composition is prepared as follows. A
premix is made by combining the 2,4,4'-trichloro-2-hydroxy diphenyl ether, propylene glycol, dipropylene glycol, propylene carbonate, ethanol, PPG-3-myristyl ether, PEG-6, di-isopropyl adipate, and benzylidene monosorbitol. These components are heated to approximately 190F (88C). Once clear, the solution is then cooled to approximately 160F 171C), at which time the fragrance is added.
A uniform deodorant gel stick forms as the composition cools to room temperature. The resulting gel stick is optically clear with excellent efficacy as well as excellent nonsticky cosmetics and aesthetics.
The deodorant composition is applied to the underarm skin of - a human to effectively prevent underarm odor resulting from perspiration. The composition is relatively non-sticky and feels lubricious when applied to the skin.
A
- lo - I 32 ~ 4 0 8 , EXAMPLES ll - IV
These deodorant gel stick compositions are made as described above in Example 1.
Concentration (~ by weight) Material Name l l l l l IV
Benzylidene Sorbitol4.00 5.00 5.00 Propylene Carbonate2 . 0016 . 002 . 00 Propylene Glycol 5.00 16.00 2.00 Cyclomethicone 10 . 00 Di-Methyl Isosorbide20.00 16.00 10.00 Di-lsopropyl Adipate57.00 10.00 PPG-3 Myristyl Ether 10 . 00 Ethanol 13.00 19.00 Dipropylene Glycol 16.00 30.00 ~5 Polyethylene Glycol 16 . 00 10 . 00 Triclosan 0.30 0.30 0.30 2,4,4'-Trichloro-2-hydroxy Diphenyl ether 0.30 0.30 0.30 Perfume/Color qs qs qs Totals~ 100. 00100 . 00100. 00 WHAT IS CLAIMED IS:
Claims (16)
1. A deodorant gel stick composition which comprises:
(a) from about 0.1% to about 10% of a deodorant active;
(b) from about 7% to about 70% of intermediate polarity emollients selected from the group consisting of ethyl, isopropyl, and n-butyl diesters of adipic, phalic and sebacic acids, and mixtures thereof;
(c) from about 2% to about 8% of a benzylidene sorbitol;
(d) from about 5% to about 75% of a polar solvent; and (e) from about 5% to about 40% of a coupling agent selected from the group consisting of polypropylene glycol ethers of C4-C20 fatty alcohols, C6-fatty alcohols, ethoxylated derivatives of C4-C22 fatty alcohols, polyethylene glycols having a molecular weight of less than about 400, dimethyl isosorbide and mixtures thereof.
(a) from about 0.1% to about 10% of a deodorant active;
(b) from about 7% to about 70% of intermediate polarity emollients selected from the group consisting of ethyl, isopropyl, and n-butyl diesters of adipic, phalic and sebacic acids, and mixtures thereof;
(c) from about 2% to about 8% of a benzylidene sorbitol;
(d) from about 5% to about 75% of a polar solvent; and (e) from about 5% to about 40% of a coupling agent selected from the group consisting of polypropylene glycol ethers of C4-C20 fatty alcohols, C6-fatty alcohols, ethoxylated derivatives of C4-C22 fatty alcohols, polyethylene glycols having a molecular weight of less than about 400, dimethyl isosorbide and mixtures thereof.
2. A deodorant gel according to claim 1 wherein the deodorant active component is selected from the group consisting of cetyl-trimethylammonium bromide, cetyl pyridinium chloride, benzethonium chloride, diisobutyl phenoxy ethoxy ethyl dimethyl benzyl ammonium chloride, sodium N-lauryl sarcosine, sodium N-palmethyl sarcosine, lauroyl sarcosine, N-myristoyl glycine, potassium N-lauryl sarcosine, stearyl, trimethyl ammonium chloride, 2,4,4'-trichloro-2'-hydroxy diphenyl ether, sodium aluminum chlorohydroxy lactate, zinc salicylate, and zinc citrate.
3. A deodorant gel according to claim 2 wherein the polar solvent is selected from the group consisting of monohydric alcohols, polyhydric alcohols, propylene carbonate, propylene glycol, dipropylene glycol, water and mixtures thereof.
4. A deodorant gel according to claim 3 wherein the polar solvent is selected from the group consisting of propylene carbonate, water, methanol, ethanol, n-propanol, n-butanol, 2-methoxyethanol, 2-ethoxyethanol, ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, 1,4-butylene glycol, 1,2-butylene glycol, diethylene glycol, isopropanol, isobutanol, monomethyl ether, diethylene glycol monoethyl ether, 1,3-butylene glycol, 2,3-butylene glycol, dipropylene glycyl, 2,4-dihydroxy-2-methylpentane, and mixtures thereof.
5. A deodorant gel according to claim 4 wherein the intermediate polarity emollient is selected from the group consisting of di-isopropyl adipate, di-n-butyl phthalate, diethyl sebacate, and ethyl ethyl carbomethyl phthalate, and mixtures thereof.
6. A deodorant gel according to claim 5 wherein the coupling agent is selected from the group of PPG-3 myristyl ether, polyethylene glycol with a molecular weight of less than about 400, polypropylene glycols and mixtures thereof.
7. A deodorant gel according to claim 6 wherein the polar solvent comprises components selected from the group consisting of propylene carbonate present at from about 2% to about 10% of the gel composition, ethanol present at from about 15% to about 25% of the gel composition, propylene glycol present at from about 2% to about 10% of the gel composition, dipropylene glycol present at from about 20% to about 40% of the gel composition, and mixtures thereof.
8. A deodorant gel according to claim 7 wherein the benzylidene sorbitol is dibenzyl monosorbitol acetal.
9. A deodorant gel according to claim 8 which further comprises from 1% to 40% of a non-polar emollient.
10. A deodorant gel according to claim 9 wherein the non-polar emollient is selected from the group consisting of non-polar fatty acids, fatty alcohol esters, hydrocarbons, volatile and non-volatile silicones and mixtures thereof.
11. A deodorant gel according to claim 10 which further comprises from about 0.5% to about 10% of a buffering agent.
12. A deodorant gel according to claim 11 wherein the buffering agent is selected from the group consisting of sodium aluminum chlorohydroxylactate, coconut monoethanolamide, stearamide monoethanolamide and mixtures thereof.
13. A method for treating or preventing malodor associated with human underarm perspiration, said method comprising applying to the skin of a human a safe and effective amount of a deodorant gel stick composition according to claim 1.
14. A method for preventing malodor associated with human underarm perspiration, said method comprising applying to the skin of a human a safe and effective amount of a deodorant gel stick composition according to claim 4.
15. A method for treating or preventing malodor associated with human underarm perspiration, said method comprising applying to the skin of a human a safe and effective amount of a deodorant gel stick composition according to claim 9.
16. A method for treating or preventing malodor associated with human underarm perspiration, said method comprising applying to the skin of a human a safe and effective amount of a deodorant gel stick composition according to claim 11.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/123,090 US4816261A (en) | 1987-11-20 | 1987-11-20 | Deodorant gel stick |
US07/123,090 | 1987-11-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
CA1328408C true CA1328408C (en) | 1994-04-12 |
Family
ID=22406659
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA000583572A Expired - Fee Related CA1328408C (en) | 1987-11-20 | 1988-11-18 | Deodorant gel stick |
Country Status (3)
Country | Link |
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US (1) | US4816261A (en) |
EP (1) | EP0318206A1 (en) |
CA (1) | CA1328408C (en) |
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US9173824B2 (en) | 2011-05-17 | 2015-11-03 | The Procter & Gamble Company | Mascara and applicator |
WO2012166832A2 (en) | 2011-06-02 | 2012-12-06 | Milliken & Company | Porous, low density nanoclay composite |
WO2013025893A1 (en) | 2011-08-16 | 2013-02-21 | The Gillette Company | Personal care compositions comprising an anti-irritation agent |
US8668918B2 (en) | 2011-09-01 | 2014-03-11 | Milliken & Company | Bisurea gelling agents and compositions |
EP2574329A1 (en) * | 2011-09-28 | 2013-04-03 | ErlaCos GmbH | Deodorant comprising dimethyl isosorbide |
JP2015519954A (en) | 2012-05-15 | 2015-07-16 | ザ プロクター アンド ギャンブルカンパニー | A method for quantitatively determining eyelash aggregation |
DE102012223532A1 (en) * | 2012-12-18 | 2014-06-18 | Beiersdorf Ag | Improved protection against body odor |
EP3881823B1 (en) | 2013-12-25 | 2023-01-25 | Nissan Chemical Corporation | Solid base material containing lipid peptide compound |
US9968531B2 (en) | 2015-08-05 | 2018-05-15 | Dupont Tate & Lyle Bio Products Company, Llc | Deodorants containing 1,3-propanediol |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3255082A (en) * | 1962-04-16 | 1966-06-07 | Procter & Gamble | Method of preparing stable aluminum chlorhydrate-alkali metal- and alkaline earth metal salt complex antiperspirant stick |
US4137306A (en) * | 1973-06-05 | 1979-01-30 | Armour Pharmaceutical Company | Anhydrous antiperspirant stick compositions |
CA1075158A (en) * | 1976-02-05 | 1980-04-08 | Peter F. Davy | Siloxane with alcohol in antiperspirant stick |
NL7908149A (en) * | 1979-11-07 | 1981-06-01 | Naarden International Nv | SOLID ANTITRANSPIRATION AGENT, AND METHOD FOR PREPARING THE SAME |
US4617185A (en) * | 1984-07-13 | 1986-10-14 | The Procter & Gamble Company | Improved deodorant stick |
EP0175074A3 (en) * | 1984-09-21 | 1986-12-03 | American Cyanamid Company | Method for producing dibenzyl monosorbitol acetal gels at lower temperature |
US4722835A (en) * | 1984-09-21 | 1988-02-02 | American Cyanamid Company | Dibenzyl monosorbitol acetal gel antiperspirant stick compositions |
US4720381A (en) * | 1984-10-03 | 1988-01-19 | American Cyanamid Company | Acid stable monosorbitol acetal gels |
GB8620895D0 (en) * | 1986-08-29 | 1986-10-08 | Unilever Plc | Cosmetic stick |
-
1987
- 1987-11-20 US US07/123,090 patent/US4816261A/en not_active Expired - Fee Related
-
1988
- 1988-11-17 EP EP88310859A patent/EP0318206A1/en not_active Ceased
- 1988-11-18 CA CA000583572A patent/CA1328408C/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
US4816261A (en) | 1989-03-28 |
EP0318206A1 (en) | 1989-05-31 |
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