Silicone polyester polymers as durable humectants

The invention discloses novel series of silicone polyesters which are useful as humectants for softening, conditioning and lubricating hair and skin. Compounds of the invention by are prepared by the esterification of (a) a hydroxyl containing silicone compound selected from silanol and dimethicone copolyol (b) a diacid and (c) a poly-hydroxy compound selected from the group consisting of glycerine, methyl glucoside, sorbitol and their alkoxylates and (d) optionally a fatty acid. The polyesters of the present invention allow for the formulation of personal care products in which the humectant is substantive to the hair and skin by virtue of the structure of the polyester and can be formulated into a variety of products for delivery to hair and skin.

BACKGROUND OF THE INVENTION 
1. Field of the Invention 
The invention discloses novel series of silicone polyesters which are as 
additives to personal care products, giving unique skin and hair 
conditioning properties. Compounds of the invention by are prepared by the 
esterification of (a) a hydroxyl containing silicone compound selected 
from silanol and dimethicone copolyol (b) a diacid and (c) a polyhydroxyl 
compound selected from the group consisting of glycerine, methyl 
glucoside, sorbitol and their alkoxylates and (d) optionally a fatty acid. 
The polyesters of the present invention allow for the formulation of 
personal care products in which outstanding humectant properties, 
conditioning and gloss can be formulated into a variety of products 
ranging from water soluble shampoos, to oil based skin care products. The 
incorporation of the poly-hydroxy compounds into the compound results in 
the desired humectant properties, the desired emmoiency and the desired 
antistatic properties, the incorporation of the silicone portion results 
in extended durability of the compound to the hair making it substantive 
to the hair for multiple washings. In a preferred embodiment, a fatty acid 
is incorporated into the molecule to provide improved wet combability. 
2. Arts and Practices 
The personal care market is a very diverse market segment which includes a 
number of products designed to be used on hair, skin, lips, and nails. 
These products include shampoos, bubble baths, pomades, conditioners, make 
up, hand cream, make up remover, hair relaxer, lipstick, nail polish, and 
many others. Some of these products are water based like shampoo others 
are mineral oil based like make up remover. 
In addition to performing the specific cosmetic function in each type of 
product, there is a general need in each product type to incorporate 
ingredients which will help improve the condition of the hair, skin nails 
and lips. The desirable functions include but are not limited to; barrier 
properties, re-moisturization, softening, and conditioning. 
One of the most important function of human skin is the protection against 
adverse environmental factors. Environmental factors like exposure of the 
skin to sun, cold or heat adversely effects the skin and minimizes the 
barrier property of the skin. Additionally, the application of many 
cosmetic products or use of soap on the skin removes the fatty layer of 
the skin. It is therefore highly desirable to replace the barrier 
properties which are removed from the skin. Lipids and other oily 
materials added to the skin improve the natural barrier properties of the 
skin and hair the skin retain moisture and feel soft. The addition of a 
methyl glucoside silicone polyester to the hair and skin results in 
moisturizing and barrier properties, which are highly desirable for 
personal care products. 
We have discovered that the incorporation of a compound selected from the 
group consisting of glycerine, methyl glucoside, sorbitol and their 
alkoxylates into a silicone polyester in relatively low concentrations 
results in polyesters which can be made soluble in many different solvents 
and which give the beneficial properties of the glycerine, methyl 
glucoside, sorbitol and their alkoxylates and is durable to the hair and 
skin. In addition outstanding gloss can be provided. In short, low 
concentrations of these polyesters by virtue of their substantivity to 
hair and skin will provide outstanding re-moisturization properties in 
many varied personal care formulations. 
U.S. Pat. No. 5,051,489 issued September 1991 to O'Lenick teaches that 
silicone waxes can be prepared via esterification of silanol compounds. 
These materials contain no actives. 
U.S. Pat. No. 5,100,956 issued March 1992 to O'Lenick teaches that silicone 
compounds can be linked to proteins or amino acids through a phosphate 
group. This invention shows the desirability of incorporating the active 
protein into a molecule containing silicone, which is one of the 
objectives of the current invention. The O'Lenick ('956) technology is not 
applicable to actives which do not have nitrogen in the molecule. 
THE INVENTION 
Object of the Invention 
It is the object of the present invention to provide a series of novel 
silicone polyesters which contain within the molecule an humectant 
functionality in a polyester. The selection of the proper silicone portion 
results in the ability to prepare products which have solubility in a wide 
range of solvents. 
It is another objective of the current invention to provide a method of 
treating hair and skin with these polyesters. The process for treating the 
hair and skin comprises the contacting of the hair or skin with an 
effective conditioning amount of the silicone polyester. The silicone 
portion of the molecule is substantive to the substrate, hair and skin and 
binds there. The beneficial effect of the methyl glucoside is enhanced 
since the silicone delivers the active to the surface of the hair or skin. 
This prolonged intimate contact allows for enhanced performance by the 
active. 
Summary of the Invention The present invention relates to a series of novel 
silicone polyester compounds. The compounds by virtue of the glycerine, 
methyl glucoside, sorbitol and their alkoxylates present in the molecule 
form effective skin and hair modifiers, providing refatting, 
moisturization, conditioning and softening. The compounds of the present 
invention are substantive to hair, skin and textile fibers. 
The polyester compounds of the invention by are prepared by the 
esterification of (a) a hydroxyl containing silicone compound selected 
from silanol and dimethicone copolyol (b) a diacid and (c) a poly-hydroxyl 
compound selected from the group consisting of glycerine, methyl 
glucoside, sorbitol and their alkoxylates and (d) optionality a fatty 
acid. 
Polyester compounds are created by the esterification reaction with the 
hydroxyl groups in the poly-hydroxy compound, resulting in a polymer. 
It will be clearly understood that (a) the silicone compounds contain a 
plurality of hydroxyl groups, (b) the diacid contains two organic acid 
groups and (c) the poly hydroxy compound selected from the group 
consisting of glycerine, methyl glucoside, sorbitol and their alkoxylates 
contain a plurality of hydroxyl groups so that the resulting polymer is 
very highly branched and very high in molecular weight. These properties 
prevent the molecule from penetrating the skin or hair, resulting in 
surface modification without and irritation to the skin or eyes. 
As stated the polyester compounds of the invention by are prepared by the 
esterification of (a) a hydroxyl containing silicone compound selected 
from 
1. Dimethicone copolyols conforming to the following structure; 
##STR1## 
wherein; Me is methyl; 
a is an integer ranging from 2 to 20; 
b is an integer ranging from 0 to 200; 
R.sup.1 is selected from the group consisting of methyl and phenyl; 
R.sup.2 is (CH.sub.2).sub.3 --O--(CH.sub.2 --CH.sub.2 --O).sub.x 
--(CH.sub.2 (CH.sub.3)CH.sub.2 --O).sub.y --(CH.sub.2 --CH.sub.2 
--O).sub.z --H 
x, y, and z are independently integers ranging from 0 to 20; 
2. Terminal Dimethicone copolyols conforming to the following structure; 
##STR2## 
wherein; Me is methyl; 
c is an integer ranging from 1 to 200; 
R.sup.1 is selected from the group consisting of methyl and phenyl; 
R.sup.3 is --(CH.sub.2).sub.3 --O--(CH.sub.2 --CH.sub.2 --O).sub.x 
--(CH.sub.2 (CH.sub.3)CH.sub.2 --O).sub.y --(CH.sub.2 --CH.sub.2 
--O).sub.z --H 
and 
3. Silanol compounds conforming to the following structure; 
##STR3## 
wherein; Me is methyl; 
d is an integer ranging from 10 to 1200; 
R.sup.1 is selected from the group consisting of methyl and phenyl; 
R.sup.4 is OH; 
(b) a diacid selected the group consisting of; 
HO--C(O)--(CH.sub.2).sub.q --C(O)--OH, 
HO--C(O)--(CH.sub.2).sub.r --CH.dbd.CH--(CH.sub.2).sub.s --C(O)--OH; 
q is an integer from 2 to 10; 
r is an integer from 2 to 10; 
s in an integer from 2 to 10; 
dimer acid and hydrogenated dimer acid; 
(c) a poly hydroxy compound selected from the group consisting of 
glycerine, methyl glucoside, sorbitol and their alkoxylates. 
Examples of polyhydroxy compounds useful in the practice of the invention 
include: 
Glycerine and it's alkoxylates are items of commerce and conforms to the 
following structure: 
##STR4## 
t, u and v are independently integers ranging from 0 to 20; 
Methyl glucoside and it's alkoxylates are known materials marketed by a 
variety of manufacturers including Amerchol Corporation in Edison, N.J.. 
These materials conform to the following structure; 
##STR5## 
R.sup.6 is --O--(CH.sub.2 --CH.sub.2 --O).sub.t --(CH(CH.sub.3)--CH.sub.2 
--O--).sub.u --(CH.sub.2 --CH.sub.2 --O).sub.v --H 
t, u and v are independently integers ranging from 0 to 20; 
Sorbitol and it's alkoxylates are commercially available materials and 
conform to the following structure; 
##STR6## 
R.sup.6 is --O--(CH.sub.2 --CH.sub.2 --O).sub.t --(CH(CH.sub.3)--CH.sub.2 
--O--).sub.u --(CH.sub.2 --CH.sub.2 --O).sub.v --H 
t, u and v are independently integers ranging from 0 to 20; 
and optionally 
(d) a mono functional fatty acid conforming to the following structure; 
EQU R.sup.5 --C(O)--OH 
R.sup.5 is selected from the group consisting of alkyl and alkylene and has 
from 6 to 20 carbon atoms. 
Preferred Embodiments 
In a preferred embodiment said hydroxy silicone conforms to the following 
structure; 
##STR7## 
wherein; Me is methyl; 
a is an integer ranging from 2 to 20; 
b is an integer ranging from 0 to 200; 
R.sup.1 is selected from the group consisting of methyl and phenyl; 
R.sup.2 is (CH.sub.2).sub.3 --O--(CH.sub.2 --CH.sub.2 --O).sub.x 
--(CH.sub.2 (CH.sub.3)CH.sub.2 --O).sub.y --(CH .sub.2 --CH.sub.2 
--O).sub.z --H 
x, y, and z are independently integers ranging from 0 to 20. 
In another preferred embodiment said hydroxy silicone conforms to the 
following structure; 
##STR8## 
wherein; Me is methyl; 
c is an integer ranging from 1 to 200; 
R.sup.1 is selected from the group consisting of methyl and phenyl; 
R.sup.3 is --(CH.sub.2).sub.3 --O--(CH.sub.2 --CH.sub.2 --O).sub.x 
--(CH.sub.2 (CH.sub.3)CH.sub.2 --O).sub.y --(CH.sub.2 --CH.sub.2 
--O).sub.z --H. 
In still another preferred embodiment said hydroxy silicone conforms to the 
following structure; 
##STR9## 
wherein; Me is methyl; 
d is an integer ranging from 10 to 1200; 
R.sup.1 is selected from the group consisting of methyl and phenyl; 
R.sup.4 is OH. 
In a preferred embodiment said poly hydroxy compound conforms to the 
following structure: 
##STR10## 
t, u and v are independently integers ranging from 0 to 20. 
In another preferred embodiment said poly hydroxy compound conforms to the 
following structure: 
##STR11## 
R.sup.6 --O--(CH.sub.2 --CH.sub.2 --O).sub.t --(CH(CH.sub.3)--CH.sub.2 
--O--).sub.u --(CH.sub.2 --CH.sub.2 --O).sub.v --H 
t, u and v are independently integers ranging from 0 to 20. 
In another preferred embodiment said poly hydroxy compound conforms to the 
following structure: 
##STR12## 
R.sup.6 is --O--(CH.sub.2 --CH.sub.2 --O).sub.t --(CH(CH.sub.3)--CH.sub.2 
--O--).sub.u --(CH.sub.2 --CH.sub.2 --O).sub.v --H 
t, u and v are independently integers ranging from 0 to 20. 
The mole ratios of Silicone:Diacid:poly hydroxy can be varied to give 
products of differing molecular weight. The range from 0.99:1.0:0.01 to 
1.5:2.0:1.0. In a preferred embodiment the ratio ranges from 0.90:1.00:0.1 
to 1.0:2.0:1.0. 
In preferred embodiment mono fatty acids are reacted into the polyester. 
Not only does this decrease water solubility, it results in a product 
which forms a hydrophobic non-occlusive film. 
The invention also teaches that the compounds of the present invention are 
useful in a process for treating hair and skin. The process contacts the 
hair or skin with an effective conditioning amount of the compound. In a 
preferred embodiment the concentration of the compound ranges from 0.05% 
to 25% and in a more preferred embodiment the concentration ranges from 1% 
to 10%. The compound can be delivered from water or a suitable solvent.