Low surface tension cosmetic copolymers

Details Low surface tension cosmetic copolymers Low surface tension cosmetic copolymers

1999-11-03

2001-07-24

Page, Thurman K. (Department: 1615)

Drug, bio-affecting and body treating compositions

Topical body preparation containing solid synthetic organic...

Skin cosmetic coating

C424S400000, C424S401000, C424S484000, C424S487000, C524S544000, C514S772300

Reexamination Certificate

active

06264934

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to copolymers comprising silicone macromers. More specifically, the present invention relates to copolymers providing low surface tension that are useful in cosmetic compositions.
BACKGROUND OF THE INVENTION
Polysiloxane grafted acid containing (meth)acrylate copolymers for cosmetic use are the subject of several patent applications and patents, some of which are listed below. None disclose polymers with acidic monomer contents in the 0.05 to 3% range in their examples nor do they recognize the ability of such polymers to greatly reduce interfacial tension between a basic aqueous phase and a volatile methylsiloxane fluid phase in their specifications.
U.S. Pat. Nos. 4,981,903 and 5,021,477; J. E. Garbe and S. Mitra to 3M disclose a composition and hair compositions, respectively, comprising a copolymer of 0.01 to 50% silicone macromer, 0.1 to 99.9% acrylic or methacrylic monomer, and 0.1 to 99.9% highly polar monomer where said highly polar monomer has at least one hydroxyl, amino, or ionic group including quaternary ammonium, carboxylate salt, and sulfonic acid salt.
U.S. Pat. No. 4,981,902; S. Mitra and J. E. Garbe to 3M disclose non-pressure sensitive adhesive compositions comprising copolymers with a Tg of at least 20° C. having at least 30% methacrylic monomer, 3 to 30% polar monomer, and 3 to 30% silicone macromer.
U.S. Pat. Nos. 4,972,037 and 5,209,924; J. E. Garbe, S. S. Kantner, K. Kumar, and S. Mitra to 3M disclose polymer compositions of >0.1% fluorocarbon monomer, 0.01 to 30% polar monomer, 0.01 to 50% silicone macromer, and the balance acrylate or methacrylate monomer and their use in topical medical compositions.
U.S. Pat. No. 5,667,771; J. A. Carballada, L. A. Thaman, and M. P. Clariziato Procter & Gamble disclose a rinse-off hair care composition with a copolymer dissolved in a hydrophobic volatile solvent dispersed in a carrier. The copolymer has 45 to 85% hydrophobic vinyl monomer, 0 to 5% hydrophilic reinforcing monomer, and 25 to 50% silicone macromer. Examples disclose a 700,000 molecular weight 67/3/30 t-butyl acrylate/acrylic acid/11,000 molecular weight silicone macromer terpolymer.
U.S. Pat. No. 5,229,435; Y. Sakai and I. Saitoh to Shionogi & Co. and Nissin Chemical Industry disclose a skin-protecting composition comprising an uncrosslinked silicone-acrylic copolymer having 1 to 15% silicone macromer, 30 to 70% of an alkyl acrylate, 0 to 30% of an alkyl methacrylate, and 5 to 45% of a carboxyl containing monomer.
U.S. Pat. No. 5,061,481; K. Suzuki, T. Shimizu; M. Yamazoe, and T. Sugisaki to Kobayashi Kose disclose cosmetic compositions comprising an acryl-silicone graft copolymer having 5 to 66% silicone macromer with the balance being acrylate or methacrylate monomers with other compounds, including (meth)acrylic acid, optionally included.
U.S. Pat. Nos. 5,166,267 and 5,480,634; K. Hayama, K. Narazaki, and S. Kawaguchi to Mitsubishi Chemical disclose polymers for hair care products with 15 to 99.9% hydrophilic ethylenically unsaturated monomer, 0.1 to 85% silicone macromer, and 0 to 84.9% hydrophobic ethylenically unsaturated monomer.
SUMMARY OF THE INVENTION
The present invention provides a vinylic copolymer comprising repeat units of A, B and C. A is is derived from one or more ethylenically unsaturated monomers containing an acid and is present in an amount to provide an acid content of 0.015 to 0.50 milliequivalents per gram of copolymer. B is 47-97.95% of the copolymer, and is derived from one or more ethylenically unsaturated monomers optionally containing modifying groups in an amount that does not substantially interfere with the solubility of the copolymer in non-water miscible organic solvents. C is 2-50% of the copolymer, and is derived from one or more ethylenically unsaturated organosiloxane chains.
Compositions that provide these copolymers in easily handled forms, and cosmetic compositions comprising the copolymer are also provided.
DETAILED DESCRIPTION
Volatile methylsiloxane (VMS) fluids, including cyclomethicones (hexamethylcyclotrisiloxane or D
3
, octamethylcyclotetrasiloxane or D
4
, decamethylcyclopentasiloxane or D
5
, and dodecamethylcyclohexasiloxane or D
6
) and linear dimethicones (hexamethyl disiloxane and oligomers containing up to four dimethylsiloxane units), are widely used in cosmetic formulations. Due to their low heat of vaporization, they evaporate without producing a cooling or stinging effect, hence find use in antiperspirants and deodorants, lipsticks, and skin care lotions. They provide silky, non-oily emolliency and improved application, spreading, and rub-in to skin care, sun care, and color cosmetics. And they provide transient conditioning, easing wet combing and speeding drying while reducing tack in hair care applications.
Silicone (meth)acrylate copolymers also provide unique benefits in cosmetic formulations which compliment those of the VMS fluids in many cases. Structurally these are vinyl polymeric backbones grafted with polydimethylsiloxane moieties and hence combine the characteristics of acrylic resins and high molecular weight dimethicones. They are film forming agents which impart faster drying times; long lasting water repellency; a soft, smooth feel; and transfer resistance to cosmetic formulations.
It is desirable to incorporate both VMS fluids and silicone (meth)acrylate copolymers into cosmetic formulations. Unfortunately, many of the silicone (meth)acrylate copolymers disclosed in the prior art have high (10 to 25%) acidic monomer content which limits their solubility in VMS fluids, requiring the use of more polar phenyl or chloro substituted silicone fluids (see for example EP 412,704; R. E. Bolich, Jr. and P. M. Torgerson to Procter & Gamble and U.S. Pat. No. 5,753,216; S. H. Leitch, L. J. Bartz; and K. B. Fish to Procter & Gamble) which are more expensive, of lower volatility, and are diminished in the attractive properties of the VMS fluids due to their higher polarity. At somewhat lower (3 to 5%) acidic monomer content, the viscosity of the VMS/silicone (meth)acrylate solution can be unacceptably high at desirable loading levels, perhaps due to hydrogen bond or dipole-dipole interactions between the carboxylic acid moieties which the non-polar VMS solvent can't break up. Addition of a polar co-solvent, such as ethanol, can improve solubility and reduce viscosity of these polar monomer containing polymers. However, such polar co-solvents can eliminate the non-sting and lack of cooling advantages of the VMS fluid and will tend to preferentially partition into the aqueous phase when used in emulsions. Addition of polar solvents also tend to disrupt emulsion stability. An alternative is to increase the hydrophilicity of the vinyl polymeric backbone to the point where it is soluble in the polar phase with the silicone grafts remaining soluble in the non-polar phase as taught in U.S. Pat. No. 5,565,193; S. Midha, P. M. Torgerson, and C. Hall to Procter & Gamble. However this can lead to a viscous aqueous phase and will impart undesirable hydrophilicity that prolongs drying, imparts tack, and increases humidity and moisture sensitivity. Prior art silicone (meth)acrylates with only non-polar monomer content in the backbone have good solubility in VMS fluids and the relationship between polar monomer content and the polarity of the solvent required to dissolve it is understood (see for example EP 412,707; P. M. Torgerson, R. E. Bolich, Jr., and J. E. Garbe to Procter & Gamble and 3M).
Many cosmetics including foundation, skin lotion, mascara, and conditioners are supplied as water-in-oil or oil-in-water emulsions. With increasing concern about and regulation of volatile organic compounds (VOCs), the interest in including water in other formulations such as hair fixatives has also increased. When used in these emulsions, VMS fluids, which aren't miscible with water, are present in the non-polar phase. In order to obtain an emulsion that doesn't separate during storage addition of an ionic or nonionic surfactant or a thickene

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