Guerbet wax esters in personal care applications

Details Guerbet wax esters in personal care applications Guerbet wax esters in personal care applications

2002-01-08

2003-10-07

Venkat, Jyothsna (Department: 1615)

Drug, bio-affecting and body treating compositions

Live hair or scalp treating compositions

C424S064000, C424S401000

Reexamination Certificate

active

06630134

ABSTRACT:

TECHNICAL FIELD
The present invention relates to use of certain guerbet wax esters, prepared by the reaction of a guerbet alcohol and a natural high molecular wax ester selected from the group consisting of beeswax, candelillia, and carnauba wax in personal care applications. These materials are useful in preparation of cosmetic products where their ability to make custom chosen melting point waxes, and custom chosen softness of a wax for particular applications is desired. One major area for the use of these materials is in lipsticks and skin cremes where the melting point effects skin spreadability.
BACKGROUND OF THE INVENTION
The present invention relates to compositions that result from the transesterification of a wax ester and any compound that is a guerbet alcohol. Waxy esters derived from the reaction of a fatty acid and hydroxy silicone are known. U.S. Pat. No. 5,180,843 to O'Lenick, (January 1992) teaches that fatty acids, and triglycerides can be reacted with hydroxy containing silicone compounds to form esters. The products of the referenced O'Lenick patent are different in several regards than the compounds of the present invention.
Specifically, the O'Lenick patented products are made from silicone. The by-product of such a reaction is water, glycerin, or methanol respectively. As will become clear from reading the disclosure of the present invention, the compounds of the present invention are made by reacting a specific type wax ester which has a long chain acyl moiety, and a long chain alcohol moiety in the ester. The reaction of such a material with a guerbet alcohol is indicated by the following reaction:
R
1
—C(O)—OR
2
+R
3
—OH→R
1
—C(O)—O—R
2
+R
2
OH.
We have surprisingly found that the guerbet branched ester in presence of the R
2
OH in the reaction mixture, results in enhanced solubility, compatibility and gives a product with altered melting point and skin feel.
OBJECT OF THE INVENTION
It is the object of the present invention to provide unique cosmetic compositions that can be made to a variety of melting points and hardness for specific applications. These waxy materials are applied to the skin and hair to provide softening and conditioning effects. These materials are applied to the skin and hair in an effective conditioning concentration. The concentration ranges from 0.1% to 85% by weight of the cosmetic product.
DETAILED DESCRIPTION OF THE INVENTION
Beeswax, carnauba wax and candelilla wax contain natural esters, which conform to the following structure:
R
1
C(O)O—R
2
wherein:
R
1
is alkyl having 19 to 37 carbon atoms,
R
2
is alkyl having 20 to 38 carbon atoms.
The relatively high number of carbon atoms in the compounds is one factor that makes these waxes somewhat unique, compared to oils like tallow, coconut oil, and soybean oil. This higher molecular weight and the fact that it causes the product to be solid, and quite hard. This hardness limits the area into which the waxes can be placed. Reaction with guerbet alcohols results in softer waxes that are more aestethically appealing on the skin. This invention relates to a particular group of highly branched esters made by the reaction of a guerbet alcohol and a wax.
Guerbet Alcohols
Guerbet Alcohols are regiospecifically beta branched alcohols. They have been known since the 1890's when Marcel Guerbet first synthesized them. (M. Guerbet, C. R. Acad. Sci. Paris, 128, 511; 1002 (1899)). These materials are high in molecular weight and are liquid to very low temperatures. The guerbet reaction gives very specific branching in the alcohol as shown;
As can be seen by the above reaction the molecules have substitution on the second carbon from the hydroxyl group. This branching has been found to be critical to the preparation of a product having the desired lubrication and oxidative stability properties. If the branching were on the same carbon as the hydroxyl group, the hydroxyl group would be a secondary one and would be very hindered and has low reactivity. As one moves the branch position away from the beta carbon, the liquidity, lubricity and metal substantivity decreases. If the branch is lower alkyl like methyl in some oxo alcohols, there is little increase in the liquidity, lubricity and metal substantivity over normal alcohols having the same number of carbons. Additionally, the oxo process gives only some beta branching (between 1 and 28%) the guerbet process gives essentially 100% product. Guerbet alcohols that are the reaction product of one specific raw material alcohol will result in a so-called “homo-guerbet”. In this case R and R′ are identical. If the starting alcohols used in the guerbet reaction are of differing molecular weights a so-called “hetero-guerbet” results. This type of guerbet has a mixed distribution of all possible combinations of alcohols. For this reason R and R′ in the generic formula may be the same or different.
Guerbet alcohols are available commercially from Sassol Corporation, formerly called Condea Vista.
Guerbet alcohols conform to the following structure:
Wherein;
a in an integer ranging from 3 to 11;
b in an integer ranging from 5 to 19.
It should be clear from the reaction sequence that the Guerbet alcohol is reacted into the ester, making a new-branched ester and leaving a free alkyl alcohol (the R
2
OH), reacted from the starting wax. The resulting composition contains a branched ester and an alcohol that is derived from the original wax. The selection of the guerbet and wax determines the melting point and the degree of hardness of the wax. This is very important in a variety of applications, like automotive polishes, and personal care products like lipsticks.
The compositions of the present invention when applied to the hair and skin and provide softening and conditioning effects and have a soothing feel on the skin. The present invention relates to a process for conditioning hair and skin, which comprises contacting the hair or skin with an effective conditioning concentration of a composition which comprises:
a) An ester conforming to the following structure:
R
1
C(O)O—R
3
R
1
is alkyl having 19 to 37 carbon atoms,
R
3
is:
a in an integer ranging from 3 to 11;
b in an integer ranging from 5 to 19.
b) a hydroxy compound conforming to the following structure:
R
2
—OH
 wherein;
R
2
is alkyl having 20 to 38 carbon atoms.
In a preferred embodiment the concentration of the hydroxy compound ranges from 1 to 10% by weight.
In another preferred embodiment the concentration of the hydroxy compound ranges from 5 to 10% by weight.
In another preferred embodiment a is an integer ranging from 3 to 11.
In another preferred embodiment b is an integer ranging from 5 to 19.
In a preferred embodiment a is 3 b is 5.
In a preferred embodiment a is 5 b is 7.
In a preferred embodiment a is 7 b is 9.
In a preferred embodiment a is 9 b is 11.
In a preferred embodiment a is 13 b is 15.
In a preferred embodiment a is 15 b is 17.
In a preferred embodiment a is 11 b is 19.
In a preferred embodiment the concentration ranges from 0.1% to 85% by weight of the cosmetic product.
The products are applied to the skin or skin by rubbing. The products may be used as is or formulated into an emulsion with a surfactant and water using emulsification techniques known to those skilled in the art. Vitamins, fragrances, sunscreens and the like can also be added.
Waxes
The waxes useful as raw materials in the preparation of the compositions of the present invention are commercially available Koster Kuennen Corporation.
Beeswax
Beeswax, which is also known as white wax, is an insect wax cultured worldwide; it is found on all continents of the globe. The chemical composition of the wax varies slightly depending upon the specie of the bee producing the wax. To extract the beeswax for use the honeycomb is melted or boiled with water and the crude wax is skimmed off the top. The color of the crude material is dependent upon the type of flower producing the pollen and the age of the hive. Natural waxes of animal origin are complex in structur

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