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position containing an improved solvent for polysiloxanes
- 3,185,627 ‘ i ~‘ which is also compatible with a number of ingredients
SILICONE COMPOSITION which may be usedv with polysiloxanes. . ' ‘ _
‘Gus S. Kass, Chicago, Ill., assignor, by mesne assignments, Another object of the instant invention is to provide an
to Hazel Bishop Inc., Newark, N.J.,' a corporation of improved composition comprising a C1'—C3 alkyl C3-C14
New York . alkanoate and an organo-silicon polymer dissolved
No Drawing. Filed Sept. 3,‘ 1954,:Ser. No. 454,222
' 13 Claims. (Cl. 167-_—90) Y ‘ :therein. ' ' ‘
It is, therefore, an important object ‘of the instant in of different viscosities (centistokes at 25 ,°, C.), with iso- '
vention to provide a new and improved polysiloxane corn? ; t propyl'myristate (IPM) commercial grade.‘ " ‘
3,185,627
3 A
TABIJE 1 viscosity, since di?erent R groups attached to the silicon
Miscibility of isopropyl myristate and General Electric atoms in the molecule may also alter the viscosities. For
SF—96 Silicon Oils example, the viscosity range for dimethylpolysiloxane and
diphenylpolysiloxane having the same chain length will
be different. Commercial polysiloxanes which may be
Silicone Viscosity, ctsk. 10% Silicone, 45% Silicone, 96% Silicone, used in the practice of the invention to particular advan
90% IPM 75% IPM 10% IPM
tage include dimethylpolysiloxane (DC 200 ?uid and GE
Soluble_Q.___ SF-96 ?uid), diethylpolysiloxane (DC 400 ?uid), di—
phenylpolysiloxane (DC 500 ?uid), dimethylpolysilox
10 ane-diphenylpolysiloxane (DC 555 ?uid), lauryl methyl
polysiloxane (DC 1300 ?uid, and dilaurylpolysiloxane
(DC 1500 ?uid). In the usual cosmetic and dermato
logical preparation, silicone oils having viscosities within
60,000 the range of 100 to 100.0 centistokes are usually used, and
1m,nnn
15 such oils are readily dissolved by the instant alkyl alkano
ates. Further examples of ?uids which may be used in the
The mixture shown in Table 1 were all prepared at 7 practice of the instant invention are set forth in US.
room temperature (65—85° F.). When chilled to 45° F. Patents Nos. 2,384,384 and 2,377,689.
solutions of the high viscosity silicone in isopropyl my Polysiloxane resin forming material suitable for use
ristate separated into two distinct layers, but formed clear 20 in the practice of the instant invention are materials which
homogeneous solutions when they reached room’ tem ordinarily make use of heat to advance the polymer from
perature. The results shown in Table 1 were repeated an intermediate chain-like stage to a stage of advanced
with Dow Corning 200 Silicon Fluids (dimethylpolysilox- ' polymeric growth usually involving cross links between
ane). Comparable results will also be obtained using the chains. In cosmetic and dermatological preparations,
other C1-C3 alkyl C8—C14 alkanoates, such as ethyl ca 25 one of the more common uses for resin forming materials
prylate, ethyl pelargonate, isopropyl caprate, methyl un is in the treatment of hair, and the resin formers thus
decylate, methyl laurate, propyl laurate, methyl myris used may be described as resin forming materials which
tate, etc. The isopropyl caprate, laurate and myristate can be further polymerized at temperatures below about
esters appear to possess extremely good solvent proper 500° F. and preferably at temperatures in the range of
ties, and isopropyl laurate and myristate are particularly 30 300 to 450 °F. Materials of this‘type, and the prepara
suitable for use in formulations of cosmetic and derma tion thereof, are described in US. Patents Nos. 2,258,221,
tological preparations. The instant alkyl alkanoate esters 2,371,068, 2,389,477, 2,392,716, 2,371,050, 2,413,389,
are also of use in affording a mutual solvent for the sili 2,375,998 and 2,398,672. A typical example of a resin
cones and the fats, oils and waxes frequently used in such forming polysiloxane which is completely miscible with
cosmetic and dermatological preparations, and these alkyl 35 the instant alkyl alkanoates, such as isopropyl myristate,
alkanoates are non-toxic, non-irritating and non-sensitiz~ is a phenyl ethyl polysiloxane containing small amounts
ing. Particularly, the isopropyl myristate and laurate are of phenyl and ethyl polyisloxanes to effect curing at
free from odors. ' ' 350” F.
> Also, various other organo-silicon polymers may be Speci?c examples of compositions embodying the in
used in the practice of the instant invention. The poly 4,0 stant invention include the following:
siloxane oils are used most predominantly in cosmetic
and dermatological preparations, but in certain cases the EXAMPLE 1
1 Parts
polysiloxane resin formers are also used and (prior to
their heat treatment to impart resinous properties thereto) General Electric SF-96 Silicone-dimethylpolysiloxane
such polysiloxane resin formers may also be used. As 45 (500 ctsk.) ______________________________ __ 1.0
Isopropyl myristate _________________________ __ 9.0
will be appreciated, the molecular structure of the resin
Mineral oil (80/90 Saybolt viscosity) __________ __ 3.0
formers is substantially the same as that of the oils, with
the exception that a relatively small amount of hydrolyza The silicone was ?rst dissolved in isopropyl myristate
ble groups are present in the molecule. and then the mineral oil stirred in. A clear solution re
In general, the molecular structure (at least for pur 50 sulted.
poses of solvent analysis) of the polysiloxane oils and EXAMPLE 2 ,
structural formula hereinbefore and the difference is that General Electric Silicone SF-96 dimethylpolysilox
a slight number of the R groups in the resin former are ane (500‘ ctsk.) __________________________ __ 1.0
hydrolyzable to permit cross linking. Prior to such cross 55 Isopropyl myristate _________________________ __ 9.0
linking, however, the number and character of such hy Petrolatum ________________________________ __ 1.0
drolyzable groups is such that the overall solvent prop _ The petrolatum was stirred into a warm solution of the
erties of the polysiloxanes are quite similar. Depending sillcone oil in isopropyl myristate, and then cooled. A
upon the molecular Weight, as de?ned by the number of clear, stable solution resulted.
building units de?ned as n in the formula, the polysilox 60
'anes may range from a ?uid of low viscosity, representing EXAMPLE 3 ‘
, Parts
a chain with a few Si-——O—Si linkages, to a viscous sub
stantially solid material having wax-like proper-ties, rep Dow Corning 200 Fluid-dimethylpolysiloxane (350
ctsk.) '___________________________________ __ 1.0
resenting a chain with thousands of such building units
‘therein. Each such polysiloxane molecule is terminated Isopropy myristate __________________________ __ 9.0
with what is referred to as a blocking unit which corre Mineral oil ‘(80/90 Saybolt viscosity) ___________ __ 5.0
sponds to one of the R groups on the terminal silicon atom Formed a clear liquid. ' '
in the formula and, when properly blocked, the molecule
becomes stable to heat and moisture (if no hydrolyzable EXAMPLE 4
groups have been incorporated in the molecule at other 70 Parts
General Electric Viscasil - dimethylpolysiloxane
locations). The various polysiloxane ?uids or lubricants
are de?ned primarily ‘on the basis of their viscosities meas (‘100,00 ctsk.) __________________________ __ 1.0
ured at a temperature of about 25° C. Such viscosities Isopropyl myristate ________________________ __ 22.0
may range from 1 centistoke to as much as 100,000 centi Mineral oil (65/75 Saybolt viscosity) _________ __ 2.0
stokes. The chain length alone does not control the 75 A clearv stable solution resulted.
8,185,627
'5 I. g _ 6
EXAMPLE 5' alkanoate esters here used are particularly suitable for
(A) Dow ,Corning 200 Elnid-dimethylpolysiloxane ‘
. ' a -, Parts
dissolving dimethylpolysiloxanes having viscos-ities in the
range of about 1 to about 100,000 centistokes.’
(350 ,ctsk.) _________________ __»___’__a-__ 1.0, In general, in the preparation of cosmetic and def-l '
- (B) Lanolin
Isopropyl__________________
myristate ____..>_"_ ______________
__' ___________ _'_
__ 9.0
1‘.0_ Cu matological formulations embodying the instant inven
tion, the alkyl alkanoate ester component (which will‘ be I
Isopropyl myristate _' _________ _;_a _______ __ 9.0
‘used in forming a single phase or solution of the poly
Prepared solutions and B separately, then mixed the siloxane plus an additional cosmetic ingredient) should
> two solutions together. 'A ‘clear stable solution resulted. comprise, at ‘least ‘about 60 Weight percent of the single
EXAMPLE 6 '
10 phase, and preferably about 80%. In order to have an
. v . ‘ Parts
appreciable amount of the polysiloxane, at least about
.Dimethylpolysilo'xane Oil, 500 ctsk; (_GESF-96) ‘__ 10.0 1% should be used and preferably the maximum is not
‘Isopropyl myristate ___, _______ __' ________ __V_____ 85.0‘ greater than about 10 to 20%. In order to have an
Undecylenic acid __a ____ -1 ________ -1 ____ __'___ 5.0 appreciable amount of any of the other individual cos
15 metic ingredients at least about 1% should be used and
A>'clear,;stable liquid resulted. preferably not more than about 10 to 20% is used in the
' ‘ EXAMPLE 7 case‘ of such cosmetic ingredients as petrolatum, lanolin,
, ' ' ‘ ‘ ' I - . Parts
C8—C2O fatty acids and C8-C20 fatty alcohols. In the case
,rlsopropyhmyristate _____________ __‘ ______ __'_1_ 88.0
of mineral oil, however, it appears that larger amounts’
Sun screening compound _______________ __‘_____ 1.5 up to about 50% may be used.
‘General. Electric. Viscasil - dimethylpolysiloxane Another aspect of the instant invention resides in the
‘(100,00 ctsk. silicone) ___._‘___~_-_____‘.._._; ____ _f 3.0 use of the various C8—-C20 fatty acids, such as undecylenic
,Mineral oil (65/75 Saybolt viscosity) ________ __ 7.5 and stearic acids, the C8-C20 fatty alcohols‘ such as lauryl
JV‘ This formed a clear stable liquid useful as a water and stearyl alcohols and/ or certain natural oils which are
resistant sun tan oil. ' > _ ' glycerides of the 084320 fatty acids, as for example,
EXAMPLE 8 ' > .
sesame oil, all of which ingredients are used as soothing
, Parts agents and the like in cosmetic and dermatological prepa
~Dimethylpolysiloxane oil, 30,00 ctsk. (on SF-96) _I_ 10.0 rations. Such ingredients'may be used in amounts rang
.Isopropyl myristate __g _____________________ __ 90.0 ing from about 1% to about 10 to 20% as above indicated.
3O Still another aspect of the instant invention resides in
‘ Formed a clear, ‘stable
EXAMPLEQ
solution. ' t the preparation of unique dispersions of the instant .poly
- siloxanes in water. These unusual compositions may be
. '2 ' a - ‘ " . . Parts
1 ‘formed initially using’ small amounts of water so as to
.Dimethylpolysiloxa'ne oil, 300 ctsk. __;___~_;____‘ 1.0_ obtain a clear viscous gel wherein the particle sizes of the
"Isopropyl myristate ______________________ __.__ 18.0 dispersed (polysiloxane) phase may be so small that clear,
'fStearyl alcohol _____________ __‘_'_____‘_‘ ______ ___r 1.0 bright colloidal dispersions result. Such gels are dilutable
A’ clear, stable solution resulted. in?nitely in Water. In the preparation of these unusual
EXAMPLE 1o .
dispersions, the alkyl alkanoate and the polysiloxane still
comprise a single phase system, although this is the dis
‘
40 ‘persed phase. It has been found that using the usual
‘ ~ ' > g \ Parts