Resorcinol derivatives for skin

• US 7,468,464 B2
• Filed: 02/06/2008
• Issued: 12/23/2008
• Est. Priority Date: 03/18/2005
• Status: Active Grant

• Current Assignee: Unilever Home & Personal Care USA (Unilever PLC)
• Original Assignee: Unilever Home & Personal Care USA (Unilever PLC)
• Inventors: Rosa, Jose Guillermo, Harichian, Bijan
• Primary Examiner(s): Price; Elvis O
• Application Number:
  US12/026,933
• Publication Number:
  US 20080131382A1
• Time in Patent Office: 321 Days
• Field of Search: 568/716, 568/763
• US Class Current: 568/716
• CPC Class Codes: C07C 2601/14 The ring being saturated
• CPC Class Codes: C07C 39/17 containing other rings in addition to the six-membered aromatic rings , e.g. cyclohexylphenol
• CPC Class Codes: C07C 69/017 Esters of hydroxy compounds having the esterified hydroxy group bound to a carbon atom of a six-membered aromatic ring

Abstract

New 4-substituted resorcinol derivatives of general formula I and/or B and process for synthesizing same, cosmetic compositions and methods of using same, particularly for skin lightening:

Wherein
X₁ and/or X₂ represents hydrogen (H), linear or branched, saturated or unsaturated C₁-C₁₂ alkyl, alkenyl, or acyl groups. Preferably, X₁ and/or X₂ represents hydrogen (H); linear or branched, saturated or unsaturated C₁-C₁₂ alkyl or acyl groups;
R₁ represents hydrogen (H), linear or branched, cyclic or acyclic, saturated or unsaturated C₁-C₁₂ alkyl, alkenyl, cycloalkyl, or cycloalkenyl group. Preferably, R₁ represents hydrogen (H) or a C₁ alkyl group (i.e, methyl group). More preferably, R₁ represents hydrogen;
n represents 0, 1. When n=0, the ring is a cyclopentyl with or without one heteroatom from O, N or S and/or with or without one double bond. When n=1, the ring is a cyclohexyl with or without one heteroatom from O, N or S and/or with or without one double bond; and
m represents an integer between 1 and 6.

Claims

1. A cosmetic method of skin lightening comprising applying to the skin a composition comprising:

(a) a compound comprising the formula;

2. The method of claim 1 wherein the composition further comprises an organic sunscreen selected from the group consisting of Benzophenone-3, Benzophenone-4,Benzophenone-8,DEA, Methoxycinnamate, Ethyl dihydroxypropyl-PABA, Glyceryl PABA, Homosalate, Methyl anthranilate, Octocrylene, Octyl dimethyl PABA, Octyl methoxycinnamate (PARSOL MCX), Octyl salicylate, PABA, 2-Phenylbenzimidazole-5-sulphonic acid, TEA salicylate, 3-(4-methylbenzylidene)-camphor, Benzophenone-1,Benzophenone-2, Benzophenone-6,Benzophenone-12, 4-Isopropyl dibenzoyl methane, Butyl methoxy dibenzoyl methane (PARSOL 1789), Etocrylene, and mixtures thereof.

3. The method of claim 1 wherein the compound is present in an amount from about 0.1 wt. % to about 5 wt. %.

4. The method of claim 1 wherein the compound is 4-cyclopentyl methyl resorcinol, 4 cyclohexyl methyl resorcinol or a mixture thereof.

5. The method of claim 1 wherein the composition further comprises a skin benefit agent selected from the group consisting of alpha-hydroxy acids and esters, beta-hydroxy acids and esters, polyhydroxy acids and esters, kojic acid and esters, ferulic acid and ferulate derivatives, vanillic acid and esters, dioic acids and esters, retinol, retinal, retinyl esters, hydroquinone, t-butyi hydroquinone, mulberry extract, licorice extract, resorcinol derivatives, and mixtures thereof.

6. The method of claim 2 wherein the organic sunscreen is present in an amount of about 1 wt % to about 10 wt % of said composition;

and

wherein the weight ratio of said organic sunscreen to said compound is about 10000;

1 to about 1;

10000.

7. The method of claim 5 wherein the skin benefit agent is selected from the group consisting of aipha-hydroxy acids, beta-hydroxy acids, polyhydroxy acids, hydroquinone, t-butyl hydroquinone, 4-substituted resorcinol derivatives, and mixtures thereof.