Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – At least one aryl ring which is part of a fused or bridged...
Reexamination Certificate
2001-05-16
2003-03-25
Moore, Margaret G. (Department: 1712)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
At least one aryl ring which is part of a fused or bridged...
C424S401000, C524S379000, C524S386000, C528S027000, C528S031000, C528S403000
Reexamination Certificate
active
06538061
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to silicone compositions, more particularly to compositions comprising a silicone polymer network comprising cross-links derived from epoxide or oxirane moieites.
BACKGROUND OF THE INVENTION
The personal care industry thrives on being able to deliver multiple performance products based on mixtures of several components, with each having performance characteristics important to or desirable in the final formulation. One desirable characteristic is the ability to provide a silky initial feel derived from low molecular weight silicones, such as for example, octamethylcyclotetrasilioxane or decamethylcyclopentasiloxane, in the formulation while maintaining a high, but shear-thinnable viscosity. While these low molecular weight silicones provide the desired feel characteristics, they are also low viscosity, highly flowable liquids. Thus they are not easily held in a formulation, preferring rather to separate and flow out of a given container or flow uncontrollably across the skin when used in a specific application. Further, it desirable to achieve an initial silky feel while providing a smooth, low-residue feel upon dry-down. Polymeric silicone gels prepared in volatile silicone have been found to deliver desirable initial feel of volatile, low viscosity silicones to formulations while at the same time provide high viscosity and a smooth silky feel on dry-down, see for example, U.S. Pat. Nos.5,760,116, 5,493,041 and 4,987,169.
Such polymeric silicone gels have typically been made by the hydrosilylation reaction, which requires the use of both SiH functional groups and terminal olefinic groups to form crosslinked siloxane polymers. Thus only siloxane structures that can incorporate silylhydride groups and optionally, vinyl functional siloxane groups, can be utilized in making these materials. Further this method of generating crosslinked siloxane polymers limits the range of desirable organofunctional groups that may be incorporated into the polymeric structure to create additional performance advantages in complex formulations. Thus attempts to include organofunctional groups into the crosslinked siloxane polymer include unsaturated organic groups compatible with the hydrosilylaton reaction.
SUMMARY OF THE INVENTION
A cosmetic composition comprising the reaction products of
M
a
M
H
b
M
E
c
D
d
D
H
e
D
E
f
T
g
T
H
h
T
E
i
Q
j
where
M=R
1
R
2
R
3
SiO
1/2
;
M
H
=R
4
R
5
HSiO
1/2
;
M
E
=R
6
R
7
R
E
SiO
1/2
;
D=R
8
R
9
SiO
2/2
;
D
H
=R
10
HSiO
2/2
;
D
E
=R
11
R
E
SiO
2/2
;
T=R
12
SiO
3/2
;
T
H
=HSiO
3/2
;
T
E
=R
E
SiO
3/2
; and
Q=SiO
4/2
;
where R
1
, R
2
, R
3
, R
8
, R
9
and R
12
are independently monovalent hydrocarbon radicals having from one to sixty carbon atoms; R
4
, R
5
and R
10
are independently monovalent hydrocarbon radicals having from one to sixty carbon atoms or hydrogen; R
6
, R
7
, R
11
are independently monovalent hydrocarbon radicals having from one to sixty carbon atoms or R
E
; each R
E
is independently a monovalent hydrocarbon radical containing one or more oxirane moieties having from one to sixty carbon atoms; the stoichiometric subscripts a, b, c, d, e, f, g, h, i, and j are either zero or positive subject to the following limitations: a+b+c>1; b+e+h>1; c+f+i>1; b+e+h>c+f+i; and when d+e+f+g+h+i+j=0, a+b+c=2. In a preferred embodiment the reaction product of the present invention is a polyether siloxane copolymer network. In another preferred embodiment the reaction product of the present invention is a polyether siloxane copolymer network swollen with a volatile low molecular weight silicon containing compound. These compositions are useful for a variety of personal care compositions.
DETAILED DESCRIPTION OF THE INVENTION
The compositions of the present invention comprise the reaction products of an epoxy functional hydrido siloxane molecule having the following formula:
M
a
M
H
b
M
E
c
D
d
D
H
e
D
E
f
T
g
T
H
h
T
E
i
Q
j
where
M=R
1
R
2
R
3
SiO
1/2
;
M
H
=R
4
R
5
HSiO
1/2
;
M
E
=R
6
R
7
R
E
SiO
1/2
;
D=R
8
R
9
SiO
2/2
;
D
H
=R
10
HSiO
2/2
;
D
E
=R
11
R
E
SiO
2/2
;
T=R
12
SiO
3/2
;
T
H
=HSiO
3/2
;
T
E
=R
E
SiO
3/2
; and
Q=SiO
4/2
;
where R
1
, R
2
, R
3
, R
8
, R
9
and R
12
are independently monovalent hydrocarbon radicals having from one to sixty carbon atoms; R
4
, R
5
and R
10
are independently monovalent hydrocarbon radicals having from one to sixty carbon atoms or hydrogen; R
6
, R
7
, R
11
are independently monovalent hydrocarbon radicals having from one to sixty carbon atoms or R
E
; each R
E
is independently a monovalent hydrocarbon radical containing one or more oxirane moieties having from one to sixty carbon atoms; the stoichiometric subscripts a, b, c, d, e, f, g, h, i, and j are either zero or positive subject to the following limitations: a+b+c>1; b+e+h>1; c+f+i>1; b+e+h>c+f+i; and when d+e+f+g+h+i+j=0, a+b+c=2.
One method of producing the composition of the present invention is to react a molecule having the following formula:
M
a
M
H
b′
D
d
D
H
e′
T
g
T
H
h′
Q
j
wherein the definitions and relationships are as later defined (and also consistent with those defined above) under hydrosilylation conditions with an olefinically unsaturated molecule containing one or more oxirane moieties under conditions of stoichiometry where the molar quantity of oxirane is less than the molar quantity of silyl hydride. As used herein the phrase “an olefinically unsaturated molecule containing one or more oxirane moieties” means a molecule possessing one or more interior, pendant or terminal carbon carbon double bonds simultaneously with one or more interior, pendant or terminal three membered oxygen containing heterocyclic rings (chemically the phrase “three membered oxygen containing heterocyclic ring” is used herein interchangeably with the oxirane or epoxide structures). The simplest chemical structure exemplified by such a definition is:
but also includes alicyclic structures exemplified by:
Where the subscript k may be zero or a positive integer, more preferably a positive integer ranging generally from 0 to about 10. It should be noted that both exemplified structures are terminal in both the olefinic moiety and the oxirane (epoxide) moiety. A more general chemical structure is:
where R
13
, R
14
, R
15
, R
16
, R
17
and R
18
are each independently selected from the group of hydrogen and monovalent hydrocarbon radicals having from one to sixty carbon atoms, Q
m
is a di- or trivalent hydrocarbon radical having from one to sixty carbon atoms, Q
n
is a divalent hydrocarbon radical having from one to sixty carbon atoms with the subscripts m and n independently zero or one subject to the limitation that when Qm is trivalent R
14
is absent and Q
m
forms a bond with the carbon bearing R
13
and where R
16
and R
18
may be either cis- or trans- to each other. Thus one possible synthetic pathway to prepare the reaction products of the present invention is as follows:
reacting under hydrosilylation conditions to yield M
a
M
H
b
M
E
c
D
d
D
H
e
D
E
f
T
g
T
H
h
T
E
i
Q
j
where the stoichiometric coefficient, &agr;, is less than the sum of b′+e′+h′. It should be noted that the stoichiometric coefficients b, e, and h define the quantity of hydride bearing species M
H
, D
H
and T
H
in both reactant and product and are related one to other in that fashion but because some of the hydride bearing functions have reacted with an olefinically unsaturated molecule containing one or more oxirane moieties the following relationships must necessarily obtain: b′+e′+h′>b+e+h and b+c+e+f+h+i=b′+e′+h&
Chaiyawat Atchara
O'Brien Michael J.
General Electric Company
Moore Margaret G.
Wheelock Kenneth S.
Zimmer Marc S
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