Colloid systems and wetting agents; subcombinations thereof; pro – Continuous liquid or supercritical phase: colloid systems;... – Aqueous continuous liquid phase and discontinuous phase...
Reexamination Certificate
2000-04-13
2002-02-12
Lovering, Richard D. (Department: 1712)
Colloid systems and wetting agents; subcombinations thereof; pro
Continuous liquid or supercritical phase: colloid systems;...
Aqueous continuous liquid phase and discontinuous phase...
C424S070120, C514S941000, C516S906000, C528S015000, C556S460000
Reexamination Certificate
active
06346553
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to novel alkylmethylsiloxane-dimethylsiloxane-polyalkylene oxide copolymers and a method for their preparation. More specifically, the present invention relates to alkylmethylsiloxane-dimethylsiloxane-polyalkylene oxide copolymers which are substantially free of hydrocarbons, dimethylsiloxanes, and polyalkylene oxide polymers. The present invention further relates to preparation of these novel copolymers by multiple hydrosilylation reactions and an acid catalyzed cyclosiloxane ring opening polymerization reaction. These alkylmethylsiloxane-dimethylsiloxane-polyalkylene oxide copolymers have utility as non-ionic emulsifying agents in cosmetic, textile, construction and automotive applications.
BACKGROUND OF THE PRESENT INVENTION
There is considerable prior art relating to the synthesis of polydimethylsiloxane-polyalkylene oxide copolymers, alkylmethylsiloxane-polyalkylene oxide copolymers, and alkylmethylsiloxane-dimethylsiloxane-polyalkylene oxide copolymers.
Polydimethylsiloxane-polyalkylene oxide copolymers have been produced from silicon hydride containing siloxanes of the general structure
Me
3
SiO(Me
2
SiO)
x
(HMeSiO)
y
SiMe
3
wherein Me is Methyl, x is 0 to about 200, and y is 1 to about 100 and terminally unsaturated alkylene oxide polymers by a hydrosilylation coupling reaction utilizing a platinum catalyst. Examples of this type of coupling reaction and the resultant compositions were described in U.S. Pat. No. 2,868,824. The use of such compositions for preparing aqueous emulsions of cyclodimethylsiloxanes and other organic and silicone ingredients for personal care use is described in U.S. Pat. No. 4,311,695.
Alkylmethylsiloxane-polyalkylene oxide copolymers and alkylmethylsiloxane-dimethylsiloxane-polyalkylene oxide copolymers have been produced from silicone hydride containing siloxanes of the general structure
Me
3
SiO(Me
2
SiO)
x
(HMeSiO)
y
SiMe
3
wherein Me is Methyl, x is 0 to about 200, and y is 1 to about 100, and x+y is 2 or larger, alpha-olefins, and terminally unsaturated alkylene oxide polymers by hydrosilylation coupling reactions utilizing platinum catalysts. Such compositions are referenced in Chapter 7, FIG.11, page 195 of “Silicone Surfactants” (ISBN: 0-8247-0010-4) published by Marcel Decker, Inc., 1999.
In all of the above cases, stoichiometric excesses of unsaturated organic components are typically used during the hydrosilylation reactions of the silicone hydride containing siloxanes to ensure that no residual silicone hydride remains at the end of the coupling reaction. Complete consumption of silicone hydride ensures that gaseous hydrogen cannot form from the product either in storage or during subsequent use.
All of the above-described prior art surfactants, in addition to the problems associated with the excess silicone hydride, are also of limited use because they are only useful as either silicone-in-water or oil-in-water emulsifiers, but not both. Thus it would represent a notable advancement in the state of the art if a universal surfactant, i.e., one with utility as a surfactant for both silicone-in-water and oil-in-water systems could be developed.
SUMMARY OF THE INVENTION
The present invention provides near quantitative yields of novel alkylmethylsiloxane-dimethylsiloxane-polyalkylene oxide copolymers of the general formula
R(OCHR′CH
2
)
x
—O(CH
2
)
3
—Me
2
SiO(R″MeSiO)
y
(Me
2
SiO)
z
SiMe
2
(CH
2
)
3
—O—(CH
2
CHR′O)
x
R
wherein Me is Methyl, R is an alkyl group with 1 to about 4 carbon atoms, R′ is a hydrogen atom or an alkyl group with 1 to about 4 carbon atoms, R″ is a straight chain or branched alkyl group with from 4 to about 18 carbon atoms, x may range from about 10 to about 60, y may range from about 5 to about 100 and z may range from about 5 to about 200. In preferred embodiments, these novel copolymers are substantially free of residual silicone hydride functionality, dimethylsiloxanes, hydrocarbons and polyalkylene oxide polymers. By substantially free it is meant that the product copolymers are at least about 97% free of these residual components.
The present invention also provides a method of rapidly producing the novel alkylmethylsiloxane-dimethylsiloxane-polyalkylene oxide copolymers of the present invention having the general formula
R(OCHR′CH
2
)
x
—O(CH
2
)
3
—Me
2
SiO(R″MeSiO)
y
(Me
2
SiO)
z
SiMe
2
(CH
2
)
3
—O—(CH
2
CHR′O)
x
R
wherein Me is Methyl, R is an alkyl group with 1 to about 4 carbon atoms, R′ is a hydrogen atom or an alkyl group with 1 to about 4 carbon atoms, R″ is a straight chain or branched alkyl group with from 4 to about 18 carbon atoms, x may range from about 10 to about 60, y may range from about 5 to about 100 and z may range from about 5 to about 200, which are preferably substantially free of residual silicone hydride functionality, dimethylsiloxanes, hydrocarbons and polyalkylene oxide polymers, the method comprising the steps of:
(a) hydrosilylation of a straight chain or branched alphaolefin with from about 4 to about 18 carbons with a silicone hydride containing cyclosiloxane of the general formula:
(HMeSiO)
a
(Me
2
SiO)
b
wherein Me is Methyl, a ranges from 1 to 2, b ranges from 2 to about 6, and a+b ranges from 4 to about 7 using a platinum hydrosilylation catalyst, followed by distillation of the alkylated cyclosiloxane products of the general formula:
(R″MeSiO)
a
(Me
2
SiO)
b
wherein Me is Methyl, R″ is a straight chain or branched alkyl group containing from 4 to about 18 carbon atoms, a ranges from 1 to 2, b ranges from 2 to about 6, and a+b ranges from 4 to about 7,
(b) acid catalyzed polymerization of a mixture of tetramethyldisiloxane and the alkylated cyclosiloxanes of the general formula:
(R″MeSiO)
a
(Me
2
SiO)
b
and optionally a cyclosiloxane of the general formula:
(Me
2
SiO)
c
wherein Me is Methyl, R″ is a straight chain or branched alkyl group with from about 4 to about 18 carbon atoms, a may range from 1 to 2, b may range from 1 to about 6, a+b may range from 3 to about 7, and c may range from 4 to about 7 to form a silicone hydride containing polymer of the general formula:
HMe
2
SiO(R″MeSiO)
y
(Me
2
SiO)
z
SiMe
2
H
wherein Me is Methyl, R″ is a straight chain or branched alkyl group with from 4 to about 18 carbon atoms, y can range from 5 to about 100 and z may range from 5 to about 200, and
(c) hydrosilylation of a terminally unsaturated alkylene oxide polymer of the general formula
H
2
C═CH—CH
2
—O(CH
2
CR′O)
x
R
wherein R is an alkyl group with 1 to about 4 carbon atoms, R′ is a hydrogen atom or an alkyl group with 1 to about 4 carbon atoms and x can range from about 10 to about 40 by the silicone hydride containing polymer of the general formula:
HMe
2
SiO(R″MeSiO)
y
(Me
2
SiO)
z
SiMe
2
H
wherein Me is Methyl, R″ is a straight chain or branched alkyl group with from 4 to about 18 carbon atoms, y can range from 5 to about 100 and z may range from 5 to about 200, in the presence of a co-solvent comprising a linear or branched aliphatic alcohol with from 1 to about 4 carbon atoms and catalyzed by a platinum hydrosilylation catalyst to form a solution of an alkylmethylsiloxane-dimethylsiloxane-polyalkylene oxide copolymer of the general formula:
R(OCHR′CH
2
)
x
—O(CH
2
)
3
—Me
2
SiO(R″MeSiO)
y
(Me
2
SiO)
z
SiMe
2
(CH
2
)
3
—O—(CH
2
CHR′O)
x
R
wherein Me is Methyl, R is an alkyl group with 1 to about 4 carbon atoms, R′ is a hydrogen atom or an alkyl group with 1 to about 4 carbon atoms, R″ is a straight chain or branched alkyl group with from 4 to about 18 carbon atoms, x may range from about 10 to about 60, y may range from about 5 to about 100 and z may range from about 5 to about 200, and optionally,
d) devolatilization of the alkylmethylsiloxane-dimethylsiloxane-polyalkylene oxide copolymer solution in the cosolvent to provide the alkylmethylsiloxane-dimethylsiloxane-polyalkylene oxide poly
Buese Mark A.
LeGrow Gary E.
Archimica ( Florida), Inc.
Hedman & Costigan ,P.C.
Lovering Richard D.
LandOfFree
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