Skin lightening compositions

Details Skin lightening compositions Skin lightening compositions

1998-12-22

2001-07-10

Page, Thurman K. (Department: 1615)

Drug, bio-affecting and body treating compositions

Bleach for live hair or skin

C424S401000

Reexamination Certificate

active

06258344

ABSTRACT:

TECHNICAL FIELD
The subject invention relates to the field of skin lightening. Specifically, the subject invention relates to novel water-in-silicone gel compositions which enhance skin penetration effect of specific hydroquinone derivatives for skin lightening.
BACKGROUND OF THE INVENTION
The specific hydroquinone as shown in formula (I) is known as a skin lightening compound. See WO9523780.
wherein Z is oxygen or sulfur.
The combination of the specific hydroquinone derivatives and penetration enhancers is disclosed in WO9523780.
WO9523780 describes that penetration enhancers are disclosed in U.S. Pat. No. 4,537,776, Cooper, issued Aug. 27, 1985; U.S. Pat. No. 4,552,872, Cooper et al., issued Nov. 12, 1985; U.S. Pat. No. 4,557,934, Cooper, issued Dec. 10, 1985; U.S. Pat. No. 4,130,667, Smith, issued Dec. 19, 1978; U.S. Pat. No. 3,989,816, Rhaadhyaksha, issued Nov. 2, 1976; U.S. Pat. No. 4,017,641, DiGiulio, issued Apr. 12, 1977; and U.S. Pat. No. 4,954,487, Cooper, Loomans & Wickett, issued Sep. 4, 1990, and additional penetration enhancers are disclosed in Cooper, E. R., “Effect of Decylmethylsulfoxide on Skin Penetration”,
Solution Behavior of Surfactants,
Vol. 2 (Mittal and Fendler, eds.), Plenum Publishing Corp., 1982, pp. 1505-1516; Mahjour, M., B. Mauser, Z. Rashidbaigi & M. B. Fawzi, “Effect of Egg Yolk Lecithins and Commercial Soybean Lecithins on In Vitro Skin Permeation of Drugs”,
Journal of Controlled Release,
Vol. 14 (1990), pp. 243-252; Wong, O., J. Huntington, R. Konishi, J. H. Rytting & T. Higuchi, “Unsaturated Cyclic Ureas as New Nontoxic Biodegradable Transdermal Penetration Enhancers I: Synthesis”,
Journal of Pharmaceutical Sciences,
Vol. 77, No. 11 (November 1988), pp. 967-971; Williams, A. C. & B. W. Barry, “Terpenes and the Lipid-Protein-Partitioning Theory of Skin Penetration Enhancement”,
Pharmaceutical Research,
Vol. 8, No. 1 (1991), pp. 17-24; and Wong, O., J. Huntington, T. Nishihata & J. H. Rytting, “New Alkyl N,N-Dialkyl-Substituted Amino Acetates as Transdermal Penetration Enhancers”,
Pharmaceutical Research,
Vol. 6, No. 4 (1989), pp. 286-295.
Water-in-silicone composition are disclosed in GB patent publication No. 2079300A and U.S. Pat. No. 5,216,033A, but there are no description of the combination of the specific hydroquinone derivatives of formula(I) and the water-in-silicone composition, which works for enhancing penetration.
It is an object of the present invention to provide compositions for lightening mammalian skin which has a good penetration effect, so that the specific hydroquinone derivatives which are skin lightening actives can penetrate effectively and work effectively.
SUMMARY OF THE INVENTION
The subject invention relates to a water-in-silicone gel composition for skin lightening comprising
(a) a safe and effective amount of a compound of the formula (I) formula (I):
 wherein Z is oxygen or sulfur,
(b) a mixture of dimethicone copolyol surfactant and cyclomethicone
(c) a cosmetically-acceptable carrier for said compound of formula(I) and said mixture.
DETAILED DESCRIPTION OF THE INVENTION
The compound of the formula(I) have a good skin lightening effect in mammals, however it is expected to strengthen the penetration effect of the compound of formula (I) to mammal's skin. It has been unexpectedly found that the subject composition achieve good penetration in mammal's skin of the compounds of formula (I).
In order to achieve a good penetration effect, the composition of the present invention must form a water-in-silicone gel.
As used herein, “topical application” means directly laying on or spreading on outer skin.
As used herein, “skin lightening” means decreasing melanin in skin, including one or more of overall lightening of basal skin tone, lightening of hyperpigmented lesions including age spots, melasma, chloasma, freckles, post inflammatory hyperpigmentation or sun-induced pigmented blemishes.
As used herein, all percentages are by weight unless otherwise specified.
As used herein, “dimethicone copolyol” means “polymer of dimethylsiloxane with polyoxyethylene and/or polyoxypropylene side chains”.
As used herein “cyclomethicone” means “cyclic dimethyl polysiloxane”.
The weight ratio of said compound of formula(I): the mixture of dimethicone copolyol surfactant and cyclomethicone: the cosmetically acceptable carrier should be 0.001-10:10-30:89.999-60.
The typical examples of the compound of formula(I) is as follows.
4-[(tetrahydro-2H-pyran-2-yl)oxy]phenol (hereinafter called THPOP)
4-[(tetrahydro-2H-thiopyran-2-yl)oxy]phenol.
These compounds are produced by the method described in WO9523780.
A skin lightening composition of the present invention preferably comprises from about 0.001% to about 10% of a compound of the formula(I) in a topical composition, more preferably from about 0.01% to about 8%, still more preferably from about 0.1% to about 5%, most preferably from about 0.5% to about 3% of a compound of the formula(I).
Use of subject compositions comprising over 3% of an active is preferred for lightening of hyperpigmented lesions and other areas where substantial lightening is desired.
Mixture of dimethicone copolyol surfactant and cyclomethicone
The weight ratio of dimethicone copolyol surfactant: cyclomethicone is typically 5:95-25:75, preferably 5:95-18:85, more preferably 5:95-10:90. The mixture has good effect for imparting a preferred skin feel. Generally such silicones of the mixture have a low molecular weight. The suitable mixture of dimethicone copolyol surfactant and cyclomethicone include Dow Corning Q2-3225C, which are available from the Dow Corning Corp. of Midland, Mich.
A skin lightening composition of the present invention comprises preferably from 10% to about 30%, more preferably from about 15% to about 20%, of a mixture of dimethicone copolyol surfactant and cyclomethicone.
Cosmetically Acceptable Carrier for said compound of formula(I) and said mixture
The phrase “cosmetically acceptable carrier”, as used herein, means one or more compatible solid or liquid fillers, diluents, extenders and the like, which are cosmetically acceptable as defined herein. The term “compatible”, as used herein, means that the components of the compositions of this invention are capable of being commingled with the primary actives of the present invention, and with each other, in a manner such that there is no interaction which would substantially reduce the efficacy of the composition under ordinary use situations. The type of carrier utilized in the present invention depends on the type of product desired. The topical compositions useful in the subject invention may be made into a wide variety of product types. These include, but are not limited to, lotions, gels, sprays, ointments, and mousses. These product types may comprise several types of carriers including, but not limited to solutions, aerosols and gels.
Solutions according to the subject invention typically include a cosmetically acceptable aqueous or organic solvent which is capable of having the primary actives dispersed or dissolved therein. In order to dissolve the compound of formula(I), since the compounds of formula(I) are molecules of average polarity (the “solubility parameters” are around 9.5) being neither soluble in very polar solvents nor very non polar solvents, it is necessary to be dissolved in an average polarity solvents. The average polarity solvents could preferably be solvents which have solubility parameter of 7 to 11, more preferably be solvents which have solubility parameter of 8 to 10. The average polarity solvents include water soluble glycol ether; mono lower alcohol such as ethanol; polyhydric alcohol; triglyceride such as capric/caprylic triglyceride; neopentyl glycol dioctoanate (Trade name: Cosmol, manufactured by Nisshin Oil Mills (LTD.); octyl methoxy cinnamate; and ether of polyoxypropylene or polyoxyethylene and aliphatic alcohol such as polyoxypropylene 15 stearyl ether and polypropylene glycol-14 butyl ether.
The above mentioned water soluble ether can be characterized by the

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