Compositions containing an organo-silicon compound

A cosmetic of pharmaceutical composition containing an oily phase has as the said oily phase one comprising at least one organo-silicon compound of the formula ##STR1## wherein R.sub.1 and R.sub.2 each independently represent a saturated linear alkyl containing 8-16 carbon atoms; Z represents ##STR2## equal 0 or 1. The organo-silicon compound can be present in the composition in an amount ranging from 1 to 100 percent by weight based on the total weight of the composition. When cosmetic or pharmaceutical active components are present in the composition, they are homogeneously distributed therein and such compositions have excellent spreading and feel characteristics. The compositions are usefully employed in topically applied formulations such as milks, creams, oils and lotions.

The present invention relates to cosmetic or pharmaceutical compositions 
containing an "oily phase" which comprises certain organo-silicon 
compounds. By "oily phase" is meant, hereafter, in the general acceptation 
of the term, a fatty phase which is liquid or not at ambient temperature. 
The use of silicon derivatives, particularly polymethylsiloxanes, in 
pharmaceutical or cosmetic compositions such as lotions, creams, lip 
rouges, hair lacquers and the like is known. 
These silicon derivatives are generally employed in relatively weak 
concentrations, to facilitate spreading the composition on the skin or to 
avoid foam formation or to take advantage of their water repelling 
properties. 
However, these silicon derivatives have often been found to be 
inconvenient, especially since they cannot be used in significant amounts. 
Thus their use as a principal or only component in the oily phase of such 
compositions has been discouraged because of the difficulty of emulsifying 
them, or because of their limited compatibility with conventional fatty 
bodies and emulsifying agents, or because of their disagreeable feel or 
touch. 
The present invention which overcomes these drawbacks relates to a 
composition whose oily phase comprises, totally or partially, at least one 
organo-silicon compound of the formula 
##STR3## 
wherein R.sub.1 and R.sub.2 each independently represent a saturated 
linear alkyl containing 8-17 carbon atoms; 
Z represents a bivalent radical selected from 
##STR4## 
m and n represent 0 or 1. 
In one preferred embodiment of the present invention, R.sub.1 and R.sub.2 
in formula (I) above each independently represent a saturated linear alkyl 
containing 8-16 carbon atoms. In yet another preferred embodiment of the 
present invention R.sub.1 and R.sub.2 in formula (I) above each 
independently represent a saturated linear alkyl containing 8-14 carbon 
atoms. 
These organo-silicon compounds of formula (I) exhibit good compatibility 
with conventional fatty bodies such as lipids and hydrocarbon oils, as 
well as with conventionally employed emulsifying agents, and they possess 
very good spreading properties on the skin and have a non-oily feel or 
touch. 
The organo-silicon compounds of formula (I) can be provided in the form of 
a liquid, a powder or a wax depending on the values of R.sub.1, R.sub.2 
and Z radicals, as well as on the values of the m and n parameters 
selected. 
The organo-silicon compounds employed in the present invention are 
colorless or only slightly colored; they exhibit the advantage of being 
thermally and chemically stable; and they are characterized by a weak 
polarity, their dielectric constant being generally between 1.8 and 3 (at 
a frequency of 1 KHZ). 
Another essential property of the organo-silicon compounds employed in the 
present invention, as concerns their cosmetic or pharmaceutical use, is 
their very weak aggressiveness towards the skin. 
The organo-silicon compounds of formula (I) constitute a family of 
compounds which impart the above mentioned properties to compositions 
comprising them, totally or partially. 
The judicious selection of values for R.sub.1, R.sub.2 and Z as well as 
values for the m and n parameters, permits the introduction of these 
organo-silicon compounds into various compositions such as milks or 
creams, in oil-in-water emulsions or in water-in-oil emulsions for the 
grooming or care of the skin, in make-up products such as lip rouge, eye 
shadow and eye-liners, in bath compositions, and in compositions for 
protection against actinic rays, such as solar oils. 
The compositions of the present invention can contain the organo-silicon 
compounds of formula (I) either as the only component of the oily phase or 
in admixture with other fatty bodies principally those such as natural or 
synthetic oils and waxes, non-ionic, anionic, cationic or amphoteric 
surface active agents and principally alkyl ethers and esters of 
polyethylene glycol, sorbitol and polyglycerol, such as oxyethylenated 
fatty alcohols, oxyethylenated fatty acids, oxyethylenated sorbitan esters 
and soaps such as triethanolamine stearate, pigments, filters, solvents, 
thickening agents, preservatives, perfumes, dyes, sequestering agents, 
bases or acids, and also active cosmetic or pharmaceutical products. 
In the compositions of the present invention, the organo-silicon compounds 
are generally employed in an amount, varying within large limits and 
depending upon the type of formulation containing the same. This 
concentration ranges from 1 to 100 percent, more preferably from 1 to 99.5 
percent, and preferably from 3.5 to 60 percent by weight relative to the 
total weight of the composition. 
Representative fatty bodies or material compatible with the organo-silicon 
compounds utilized in the compositions of the present invention which can 
comprise up to 90%, and preferably up to 70%, by weight of the total oily 
phase, include: mineral oils such as paraffin oil; treated animal oils 
such as cosbiol or synthetic oils such as Purcellin oil or other esters 
such as isopropyl palmitate or myristate; lanolin derivatives, lanolin, 
vegetable oils such as sweet almond oil, olive oil and avocado oil in 
amounts up to 5 weight percent of the total oily phase; or even synthetic 
triglycerides. 
When the composition of the present invention contains surface active or 
emulsifying agents, the ratio (total fatty products:emulsifying agents) 
varies from 60:40 to 90:10 and preferably from 70:30 to 80:20 in 
accordance with the water content, as indicated below: 
______________________________________ 
ratio 
(total fatty products):(emul- 
= 90:10 for 25-80% water 
sifying agent) 
ratio 
(total fatty products):(emul- 
= 80:20 for 38-80% water 
sifying agent) 
ratio 
(total fatty products):(emul- 
= 70:30 for 45-80% water 
sifying agent) 
ratio 
(total fatty products):(emul- 
60:40 for 55-80% water 
sifying agent) 
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The emulsions can also contain a wide variety of emulsifying agents 
including those which are particularly compatible with the organo-silicon 
compounds of formula (I) such as beeswax/borax mixtures and sorbitan 
oleate, as well as metallic soaps. 
The present invention also relates to a composition, free from all active 
products, the principal component of which is an organo-silicon compound 
of formula (I) or a mixture of these organo-silicon compounds. 
This composition which is useful as a carrier or an excipient in the 
cosmetic or pharmaceutical industry, can be provided in the form of an 
oily phase alone, or in an oil-alcohol mixture, or in an oil-in-water 
emulsion or in a water-in-oil emulsion. 
The components of this composition of the present invention, other than the 
organo-silicon compounds of formula (I), are principally water, lower 
alkanols such as ethanol, glycols such as propylene glycol, other fatty 
bodies or materials and emulsifying agents as well as, optionally, other 
conventionally employed cosmetic or pharmaceutically acceptable components 
or adjuvants. 
The composition of the present invention contains at least one 
organo-silicon compound of formula (I), and optionally other fatty 
products and/or emulsifying agents compatible with the organo-silicon 
compounds of formula (I), as well as water and solvents, in accordance 
with the proportions indicated above. 
Where the composition is provided in the form of an emulsion, it can 
contain the organo-silicon compound of formula (I) in an amount of 4.5 to 
70, and preferably 5 to 50, percent by weight; other fatty products 
compatible with the organo-silicon compounds of formula (I) in an amount 
of 0 to 50, and preferably 3 to 32, percent by weight; an emulsifying 
agent compatible with the organo-silicon compounds of formula (I) in an 
amount of 2 to 30, and preferably 5 to 15, percent by weight; and water in 
an amount up to about 80 percent by weight relative to the total weight of 
the composition. 
Where the composition of the present invention consists only of fatty 
materials, the organo-silicon compounds of formula (I) are present in an 
amount of 10 to 99.5, and preferably 10 to 60, percent by weight relative 
to the total weight of the composition. 
Where the composition is an oil-alcohol mixture, the amount of 
organo-silicon compounds of formula (I) in the total mixture is at least 5 
weight percent and the weight ratio, (alcohol/total composition) can vary 
from 30:100 to 80:100 and preferably 35:100 to 50:100. Preferably the 
alcohol is ethanol. 
The composition of the present invention advantageously provides for a 
perfectly homogeneous distribution of those cosmetic and pharmaceutical 
active components for which it serves as excipient and it also imparts to 
the resulting preparation easy spreading properties and an agreeable touch 
or feel which is particularly desirable for topically applied 
compositions. 
The composition of the present invention is advantageously employed as an 
excipient for pharmaceutical preparations for topical application to skin, 
as well as for cosmetic formulations, as indicated above. 
The organo-silicon compounds of formula (I) can be classified into three 
groups, i.e. 
(a) compounds wherein n=0, m=0 or 1; 
(b) compounds wherein n=1 and m=0; and 
(c) compounds wherein m and n=1. 
All are prepared in accordance with analogous procedures. 
The organo-silicon compounds of formula (I), wherein n=0 and m=0 or 1, can 
be prepared by reacting a dimethyl halogeno silane with an .alpha.-olefin. 
The resulting dimethyl alkyl halogeno silane is then reduced, for example, 
with tetra aluminum hydride and lithium. The resulting alkyl dimethyl 
silane is then reacted with an .alpha.-olefin or also with a diallylic 
derivative in the presence of chloroplatinic acid as a catalyst, yielding 
compounds of the formula: 
##STR5## 
wherein R.sub.1, R.sub.2, Z and m have the meanings given above. 
The organo-silicon compounds of formula (I) wherein n=1 and m=0, can be 
prepared by reacting a dimethyl halogeno silane with an .alpha.-olefin. 
The resulting dimethyl alkyl halogeno silane is converted to dimethyl 
alkyl silanol by the action of an alkaline base as NaOH. The resulting 
silanol is dehydrated, for example, in the presence of phosphoric acid to 
obtain finally a dialkyl tetra methyl di-siloxane. 
The organo-silicon compounds of formula (I) wherein m=1 and n=1 can be 
prepared by reacting a dimethyl halogeno silane with a dimethyl alkyl 
silanol. The resulting alkyl tetramethyl disiloxane is reacted with a 
diallylic derivative in the presence of a catalyst such as chloroplatinic 
acid. 
Representative organo-silicon compounds of formula (I) usefully employed in 
the present invention include those appearing in Table A below, and 
preferably, compounds Nos. A.sub.4, A.sub.5, A.sub.7, A.sub.8, A.sub.9 and 
A.sub.10 of this table. 
Representative particularly appropriate emulsifying agents usefully 
employed with the organo-silicon compounds of formula (I) indicated above 
include polyglycerol ethers and principally polyglycerol ethers E.sub.1, 
E.sub.2 and E.sub.3 whose characteristics are also indicated at the end of 
Table A below. Polyglycerol esters and oxyethylenated sorbitan esters can 
also be employed. 
These polyglycerolated emulsifying agents are perfectly compatible with the 
organo-silicon compounds and certain binary mixtures are particularly 
effective. Where emulsions are provided in the form of creams, a 50:50 
weight mixture of E.sub.1 :E.sub.2 emulsifying agent is particularly 
effective. Where the emulsion is provided in the form of a milk, a 70:30 
weight mixture of E.sub.3 :E.sub.2 emulsifying agents is highly desirable. 
TABLE A 
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No. Organo-silicon compounds useful in the invention 
______________________________________ 
A.sub.1 
(CH.sub.3).sub.2 Si(C.sub.10 H.sub.21).sub.2 
A.sub.3 
[(CH.sub.3).sub.2 Si(C.sub.8 H.sub.17)].sub.2 O 
A.sub.4 
[R(CH.sub.3).sub.2 Si].sub.2 O wherein R = a mixture of C.sub.12 
H.sub.25 
and C.sub.14 H.sub.29 
A.sub.5 
[C.sub.14 H.sub.29 (CH.sub.3).sub.2 Si].sub.2 O 
A.sub.7 
[C.sub.14 H.sub.29 (CH.sub.3).sub.2 Si(CH.sub.2).sub.3 ].sub.2 Si(C 
H.sub.3).sub.2 
A.sub.8 
[C.sub.14 H.sub.29 (CH.sub.3).sub.2 Si(CH.sub.2).sub.3 ].sub.2O 
A.sub.9 
[C.sub.14 H.sub.29 (CH.sub.3).sub.2 SiOSi(CH.sub.3).sub.2 (CH.sub.2 
).sub.3 ]Si(CH.sub.3).sub.2 
.sub. A.sub.10 
[C.sub.16 H.sub.33 (CH.sub.3).sub.2 Si].sub.2 O 
______________________________________ 
Emulsifying agents useful in the invention 
polyglycerol esters 
oxyethylenated sorbitan esters 
polyglycerol ethers of the formula RO--C.sub.2 H.sub.3 O(CH.sub.2 
OH)].sub.n' H wherein R is a mixture of --C.sub.16 H.sub.33 and C.sub.18 
H.sub.37, n' being a whole or decimal number having a statistical value of 
2 to 6, principally polyglycerol ethers E.sub.1 for which n'=6; E.sub.2 
for which n'=2 and E.sub.3 for which n'=4. 
The below non-limiting examples are given to provide a better understanding 
of the present invention. Unless otherwise stated, all parts and 
percentages are by weight. 
Tables I, II, III and IV below, describe respectively the compositions in 
the form of creams, milks, oils and oil-alcohol lotions which are useful 
in the cosmetic industry. 
Columns (1) to (10) have the following meanings: 
(1) No. of the Example of the composition; 
(2) Product of formula (I), designated by reference to Table A; 
(3) Other fatty products or materials (FP) compatible with the products of 
(2); 
(4) Emulsifying agents (EA) defined with reference to Table A; 
(5) Sterile demineralized water; 
(6) Ethyl alcohol; 
(7) Various components other than those of columns (2) to (6) and present 
in the composition as an active component; 
(8) Percent of (2) in the total fatty phase; 
(9) Ratio [(2)+(3)]:(4), indicated such as it appears below in columns (2) 
(3) and (4) and/or converted to 100 parts by weight; 
(10) Types of products corresponding to the composition prepared. 
Tables I and II correspond respectively to the cream and milk type 
compositions. In each of Examples C.sub.1 to C.sub.8, as well as Examples 
L.sub.1 to L.sub.4, the fatty phase can contain from 0 to 70 weight 
percent of a fatty material, other than the organo-silicon compound of 
formula (I), including, for instance, mineral oils such as paraffin oil; 
treated animal oil such as cosbiol; synthetic oils such as Purcellin oil; 
or other esters such as isopropyl palmitate or myristate; lanolin 
derivatives; vegetable oils such as sweet almond oil; olive oil, avocado 
oil; or also synthetic triglycerides. 
The previously mentioned emulsifying agents and principally the 
polyglycerol ethers, E.sub.1, E.sub.2 and E.sub.3 can be replaced by the 
following emulsifying agents: oxyethylenated fatty alcohols, known under 
the trade name BR1J type 56 ATLAS; oxyethylenated fatty acids, known under 
the trade name M1RJ type 49; oxyethylenated sorbitan esters, known under 
the trade name TWEEN 60; and soaps such as triethanolamine fatty acids 
salts like triethanolamine stearate. 
Where the composition of the present invention consists essentially of an 
oil product and oil-alcohol lotion, the oily phase can comprise up to 75 
weight percent of a fatty material other than the organo-silicon compounds 
of formula (I), said other fatty material being those mentioned above. 
The various components in column (7) can be either products having 
pharmacologic activity or components used for cosmetic purposes or 
components for modifying the appearance or preservation characteristics of 
the composition.