Stabilization of terpenoids in cosmetic compositions

• US 20030185867A1
• Filed: 03/11/2003
• Published: 10/02/2003
• Est. Priority Date: 03/22/2002
• Status: Active Grant

• Current Assignee: Unilever Home & Personal Care USA (Unilever PLC)
• Original Assignee: Unilever Home & Personal Care USA (Unilever PLC)
• Inventors: Barratt, Michael James, Kerschner, Judith Lynne, Love, Arthur Ray
• Granted Patent: US 6,858,217 B2
• Time in Patent Office: Days
• US Class Current: 424/401
• CPC Class Codes: A61K 2800/52 Stabilizers
• CPC Class Codes: A61K 8/31 Hydrocarbons
• CPC Class Codes: A61K 8/342 Alcohols having more than seven atoms in an unbroken chain
• CPC Class Codes: A61K 8/347 Phenols
• CPC Class Codes: A61K 8/671 Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin

Abstract

Cosmetic compositions containing terpenoids along with a 4-substituted resorcinol derivative exhibit improved storage stability and oxidative stability.

Claims

1. A personal care composition comprising:

a. about 0.000001 to about 10% of an unsaturated terpenoid;

b. about 0.000001 to about 10% of a 4-substituted resorcinol derivative of the general formula (I);

 

wherein each R₁ and R₂ independently is selected from the group consisting of a hydrogen atom, —

CO—

R, —

COO—

R, and CONHR;

wherein R represents a C₁-C₁₈ hydrocarbon;

 

R₃ represents a C₁-C₁₈ hydrocarbon or has a general formula (II);

 

wherein X represents hydrogen;

OR¹, wherein R¹ represents hydrogen, (C₁-C₆)alkyl or aryl-(C₁-C₆)alkyl;

OCOR² wherein R² represents (C₁-C₆)alkyl, aryl-(C₁-C₆)alkyl or phenyl;

halogen;

(C₁-C₆)alkyl;

aryl-(C₁-C₆)alkyl, or aryl-(C₁-C₆)alkyl;

or NHR¹ wherein R¹ is defined as above;

 

n is 0 to 3; and

 

the dashed line indicates an optional double bond; and

c. a cosmetically acceptable vehicle.

2. The composition of claim 1, wherein said terpenoid is selected from the group consisting of acyclic terpenoids, cyclic terpenoids, cycloaliphatic compounds that are structurally related to terpenoids, and mixtures thereof.

3. The composition of claim 2 wherein said terpenoids comprise terpenes and terpene derivatives selected from the group consisting of alcohols, aldehydes, acetals, ketones, acids, esters, and terpene compounds that contain heteroatoms selected from the group consisting of nitrogen or sulfur, and mixtures thereof.

4. The composition of claim 2 wherein said acyclic terpenoids are selected from the group consisting of Myrcene, Ocimene, beta-Farnesene, Dihydromyrcenol, Geraniol, Nerol, Linalool, Myrcenol, Lavandulol, Citronellol, Trans-trans-Farnesol, Trans-Nerolidol, Citral, Citral diethyl acetal, Citronellal, Citronellyloxyacetaldehyde, 2,6,10-Trimethyl-9-undecenal, Tagetone, Solanone, Geranylacetone, Cis-Geranic acid Citronellic acid, Geranyl formate, Geranyl acetate, Geranyl propionate, Geranyl isobutyrate, Geranyl isovalerate, Neryl acetate, Lynalyl formate, Linalyl acetate, Linalyl propionate, Linalyl butyrate, Linalyl isobutyrate, Lavendulyl aetate, Citronellyl formate, Citronellyl acetate, Citronellyl propionate, Citronellyl isobutyrate, Citronellyl isovalerate, Citronellyl tiglate, Cis-Geranic acid nitrile, Citronellic acid nitrile, and mixtures thereof.

5. The composition of claim 2 wherein said cyclic terpenoids are selected from the group consisting of Limonene, Alpha-Terpinene, Gamma-Terpinene, Terpinolene, Alpha-Phellandrene, Beta-Phellandrene, Alpha-Pinene, Beta-Pinene, Camphene, 3-Carene, Caryophyllene, (+)-Valencene, Thujopsene, Alpha-Cedrene, Beta-Cedrene, Longifolene, (+)-Neoiso-isopulegol, Isopulegol, Alpha-Terpineol, Beta-Terpineol, Gamma-Terpineol, Delta-Terpineol, 1-Terpinen-4-ol, Carvone, Alpha-lonone, Beta-lonone, Gamma-lonone, Alpha-Irone, beta-Irone, gamma-Irone, alpha-n-Methylionone, beta-n-Methylionone, gamma-n-Methylionone, alpha-Isomethylionone, beta-Isomethylionone, gamma-Isomethylionone, Allylionone, Pseudoionone, n-Methylpseudoionone, Isomethylpseudoionone, Damascones, beta-Damascenone, Nootkatone, Cedryl methyl ketone, Alpha-Terpinyl acetate, Nopyl acetate, Khusymil acetate, and mixtures thereof.

6. The composition of claim 2 wherein said cycloaliphatic compounds that are structurally related to terpenoids are selected from the group consisting of 5-(2,2,3-Trimethyl-3-cyclopenten-1-yl)-3-methylpentan-2-ol, 2,4-Dimethyl-3-cyclohexene carboxaldehyde, 4-(4-Methyl-3-penten-1-yl)-3-cyclohexene carboxaldehyde, 4-(4-Hydroxy-4-methypentyl)-3-cyclohexene carboxaldehyde,Civetone, Dihydrojasmone, Cis-Jasmone, 5-Cyclohexadecen-1-one, 2,3,8,8-Tetramethyl-1,2,3,4,5,6,7,8-octahydro-2-napthalenyl methyl ketone, 3-methyl-2-cyclopenten-2-ol-1-one, 4,7-Methano-3a,4,5,6,7,7a-hexahydro-5-(or 6)-indenyl acetate,

Allyl 3-cyclohexylpropionate,

Methyl dihydrojasmonate methyl (3-oxo-2-pentylcyclopentyl)acetate,

and mixtures thereof.

7. The composition of claim 1, wherein said 4-substituted resorcinol derivative is present in at least an effective amount to inhibit oxidation of said unsaturated terpenoid.

8. The composition of claim 1, wherein the 4-substituted resorcinol is selected from the group consisting of 4-linear alkyl resorcinols, 4-branched alkyl resorcinols, 4-cycloalkyl resorcinols, and mixtures thereof.

9. The composition of claim 1, wherein the wherein the 4-substituted resorcinol is selected from the group consisting of 4-methyl resorcinol, 4-ethyl resorcinol, 4-propyl resorcinol, and 4-butyl resorcinol, 4-pentyl resorcinol, 4-hexyl resorcinol, 4-heptyl resorcinol, 4-octyl resorcinol, 4-nonyl resorcinol, 4-decyl resorcinol, 4 cyclopentyl resorcinol, 4-cyclohexyl resorcinol, 4-cycloheptyl resorcinol, 4-cyclooctyl resorcinol, and mixtures thereof.

10. The cosmetic composition of claim 1, further comprising 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-butyl hydroquinone, resorcinol derivatives, and mixtures thereof.

11. A cosmetic composition comprising:

a. an unsaturated terpenoid stabilized by a 4-substituted resorcinol derivative;

b. a skin benefit agent; and

c. a cosmetically acceptable vehicle;

wherein said terpenoid is present in an amount of about 0.0001 wt % to about 5 wt % of said cosmetic composition; and

wherein the weight ratio of said terpenoid to said 4-substituted resorcinol derivative is about 10,000;

1 to about 1;

100,000.