Drug – bio-affecting and body treating compositions – Preparations characterized by special physical form – Cosmetic – antiperspirant – dentifrice
Reexamination Certificate
1998-12-08
2001-01-30
Page, Thurman K. (Department: 1615)
Drug, bio-affecting and body treating compositions
Preparations characterized by special physical form
Cosmetic, antiperspirant, dentifrice
C424S078020, C514S804000, C514S547000
Reexamination Certificate
active
06180120
ABSTRACT:
FIELD OF THE INVENTION
Cosmetic methods and compositions for skin care by topical application to the skin of cosmetic compositions containing an alpha hydroxy acid linoleate.
BACKGROUND OF THE INVENTION
Alpha hydroxy acids and esters thereof and linoleic acid esters are well known in the cosmetic art. The compounds employed in the present invention are different at least in that an ester linkage is between the carboxyl group of linoleic acid and the hydroxy group of the hydroxy acid. Alpha carboxylic acids are also known as 2-hydroxy carboxylic acids; thus, the compounds of the present invention may also be called “2-hydroxy carboxylic acid ester of linoleic acid.” It has been found, as part of the present invention, that such compounds have a variety of cosmetically beneficial effects on the skin. Specifically, some of these compounds control sebum secretion on the skin, even though, when employed separately, linoleic acid and the hydroxy acid do not achieve the same effect. In addition, alpha hydroxy acid linoleates increase collagen production by skin cells, which is typically associated with skin anti-aging benefits.
SUMMARY OF THE INVENTION
The present invention includes a cosmetic skin care composition comprising:
(a) from 0.0001 to 20 wt. % of 2-hydroxy carboxylic acid ester of linoleic acid of Formula I:
wherein R is a hydrocarbon chain containing from 1 to 20 carbon atoms; and
(b) a cosmetically acceptable vehicle.
The inventive compositions provide control of sebum secretion from sebocytes, improved oil control and improved skin feel, prevent shine and stickiness, and provide increased collagen production by skin cells. These effects are associated with reduced appearance of wrinkles and aged skin, improved skin color, treatment of photoaged skin, improvement in skin's radiance and clarity and finish, and an overall healthy and youthful appearance of the skin.
DETAILED DESCRIPTION OF THE INVENTION
Except in the operating and comparative examples, or where otherwise explicitly indicated, all numbers in this description indicating amounts or ratios of material or conditions of reaction, physical properties of materials and/or use are to be understood as modified by the word “about.” All amounts are by weight of the final composition, unless otherwise specified.
The term “skin” as used herein includes the skin on the face, neck, chest, back, arms, legs, hands and scalp.
The terms “2-hydroxy carboxylic acid ester of linoleic acid” and “alpha hydroxy carboxylic acid ester of linoleic acid” and “alpha hydroxy carboxylic acid linoleate” and the abbreviation “AHAL” are used interchangeably herein and all refer to the following structural formula:
wherein R is a hydrocarbon chain containing from 1 to 20 carbon atoms.
AHAL compounds may be prepared by the following general procedure:
Into a round bottomed flask, alpha hydroxy carboxylic acid is mixed with pyridine (molar ratio in the general range of from 1:1 to 1:2) in an anhydrous, typically non-polar, solvent. Linoleic acid halide, most preferably chloride, is added at a temperature range of 20 to 45° C. The molar range of alpha hydroxy carboxylic acid to linoleic acid halide is typically 1:1 to 1:2. The reaction mixture typically stirs for 2 to 24 hours at a temperature range of 20 to 45° C. The reaction mixture is extracted three times with water before the organic layer is isolated, dried over magnesium sulfate, filtered and concentrated under reduced pressure. Product is purified by column chromatography.
AHAL is incorporated in the inventive compositions in an amount of from 0.0001 to 20%, preferably in order to maximize benefits at a minimum cost, in an amount of from 0.01 to 12%, most preferably from 0.1 to 8%.
Cosmetically Acceptable Vehicle
The composition according to the invention also comprises a cosmetically acceptable vehicle to act as a dilutant, dispersant or carrier for AHAL in the composition, so as to facilitate its distribution when the composition is applied to the skin.
Vehicles other than or in addition to water can include liquid or solid emollients, solvents, humectants, thickeners and powders. An especially preferred nonaqueous carrier is a polydimethyl siloxane and/or a polydimethyl phenyl siloxane. Silicones of this invention may be those with viscosities ranging anywhere from about 10 to 10,000,000 mm
2
/s (centistokes) at 25° C. Especially desirable are mixtures of low and high viscosity silicones. These silicones are available from the General Electric Company under trademarks Vicasil, SE and SF and from the Dow Corning Company under the 200 and 550 Series, Amounts of silicone which can be utilized in the compositions of this invention range anywhere from 5% to 95%, preferably from 25% to 90% by weight of the composition.
The cosmetically acceptable vehicle will usually form from 5% to 99.9%, preferably from 25% to 80% by weight of the composition, and can, in the absence of other cosmetic adjuncts, form the balance of the composition. Preferably, the vehicle is at least 80 wt. % water, by weight of the vehicle. Preferably, the amount of water is at least 50 wt. % of the inventive composition, most preferably from 60 to 80 wt. %, by weight of the composition. The preferred compositions are oil-in-water emulsions, containing at least 60%, preferably at least 80% water.
Optional Skin Benefit Materials and Cosmetic Adjuncts
The inventive compositions preferably include sunscreens to lower skin's exposure to harmful UV rays.
Sunscreens include those materials commonly employed to block ultraviolet light. Illustrative compounds are the derivatives of PABA, cinnamate and derivatives of salicylate (other than ferulyl salicylate). For example, octyl methoxycinnamate and 2-hydroxy-4-methoxy benzophenone (also known as oxybenzone) can be used. Octyl methoxycinnamate and 2-hydroxy-4-methoxy benzophenone are commercially available under the trademarks, Parsol MCX and Benzophenone-3, respectively. The exact amount of sunscreen employed in the emulsions can vary depending upon the degree of protection desired from the sun's UV radiation.
An oil or oily material may be present, together with an emollient to provide either a water-in-oil emulsion or an oil-in-water emulsion, depending largely on the average hydrophilic-lipophilic balance (HLB) of the emollient employed. Levels of such emollients may range from about 0.5% to about 50%, preferably between about 5% and 30% by weight of the total composition. Emollients may be classified under such general chemical categories as esters, fatty acids and alcohols, polyols and hydrocarbons.
Esters may be mono- or di-esters. Acceptable examples of fatty di-esters include dibutyl adipate, diethyl sebacate, diisopropyl dimerate, and dioctyl succinate. Acceptable branched chain fatty esters include 2-ethyl-hexyl myristate, isopropyl stearate and isostearyl palmitate. Acceptable tribasic acid esters include triisopropyl trilinoleate and trilauryl citrate. Acceptable straight chain fatty esters include lauryl palmitate, myristyl lactate, oleyl eurcate and stearyl oleate. Preferred esters include coco-caprylate/caprate (a blend of coco-caprylate and coco-caprate), propylene glycol myristyl ether acetate, diisopropyl adipate and cetyl octanoate.
Suitable fatty alcohols and acids include those compounds having from 10 to 20 carbon atoms. Especially preferred are such compounds such as cetyl, myristyl, palmitic and stearyl alcohols and acids.
Among the polyols which may serve as emollients are linear and branched chain alkyl polyhydroxyl compounds. For example, propylene glycol, sorbitol and glycerin are preferred. Also useful may be polymeric polyols such as poly-propylene glycol and polyethylene glycol. Butylene and propylene glycol are also especially preferred as penetration enhancers.
Exemplary hydrocarbons which may serve as emollients are those having hydrocarbon chains anywhere from 12 to 30 carbon atoms. Specific examples include mineral oil, petroleum jelly, squalene and isoparaffins.
Another category of functional ingredients within the cosmetic c
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