Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2000-07-24
2001-10-02
Lambkin, Deborah C. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
active
06297383
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to organosilane and organosilicone compounds and, more particularly, to novel organosilane compounds and organosiloxane compounds and oligomers containing a functional carboxyl group and to a method of making the same.
BACKGROUND OF THE INVENTION
Various organosilane and organosiloxane monomers or compounds including organosiloxane oligomers containing one or more organofunctional groups such as amines, vinyls, mercaptans, epoxies, halogens, and the like are widely known. These compounds have been used in a variety of ways such as coupling agents and adhesion promoters for inorganic materials, as reactants for modifying the properties of organic polymers, as cross-linking agents for curable organic polymer systems, as additives for a variety of home care and personal care compositions, as well as monomers for the preparation of silicon containing polymers.
While silane and siloxane monomers containing a variety of organofunctional groups are well known and can be readily prepared, organosilane and organosiloxane monomers containing functional carboxyl groups are generally not available commercially. Heretofore, no convenient method for preparing such monomers with carboxyl functional groups has been known and indirect procedures would generally have to be used for their preparation. Accordingly, the development of organosilane and organosiloxane monomers or compounds containing one or more organofunctional carboxyl groups and methods for readily preparing these compounds would be desirable. It would be particularly advantageous if methods for preparing such compounds not only employed readily available materials, but carboxyl-functional organosilicone monomers and oligomers could be prepared containing other functional groups as well, such as halogen groups, which makes possible the preparation of a variety of organosilicone derivatives including oligomers thereof.
While, as indicated, organosilane and organosiloxane compounds containing a variety of functional groups and methods for preparing the same, heretofore, have been known and used, there is no known disclosure or suggestion of the novel carboxyl-functional organosilane and organosiloxane compounds and oligomers of the present invention or of the method for making the same herein described.
SUMMARY OF THE INVENTION
It is accordingly an object of the present invention to provide a novel class of organosilane and organosiloxane compounds having at least one functional carboxylic ester group thereon and which may also include a variety of other functional groups as well.
It is another object of the present invention to provide a novel class of organosilane and organosiloxane compounds having at least one pyrrolidone-containing carboxylic ester and/or acid functional groups thereon including an amphoteric class of organosilane and organosiloxane compounds which may also include other functional groups as well.
It is yet another object of the present invention to provide a novel class of organosiloxane compounds and oligomers having at least one functional carboxylic ester and/or acid group thereon.
It is a further object of the present invention to provide a process for readily producing organosilane and organosiloxane compounds containing at least one carboxylic ester functional group.
These and other objects will become apparent from the dscription to follow.
In accordance with the present invention, there has now been discovered novel organosilane and organosiloxane compounds containing one or more functional carboxylic ester group(s) that may be represented by the following general formula:
wherein:
R, which can be the same or different, are hydrolyzable groups such as but not limited to halogen, acyloxy, N,N-dialkylaminoxy, N-alkylamido, monoalkylamino, dialkylamino, isocyanato, alkylthio, cyano or alkoxy;
R
1
which can be the same or different, are substituted or unsubstituted alkyl, cycloalkyl, substituted or unsubstituted aryl, aralkyl, alkenyl, alkynyl or —O—Si—(R
1
)
3
;
x can be zero to 3;
R
2
is linear or branched alkylene of 1-12 carbon atoms, preferably methylene;
R
5
is hydrogen or alkyl (C
1-10
);
B is —NR
10
, wherein R
10
is a dicarboxylic ester group of the formula —CH
2
—CH(COOR
6
)—CH
2
COOR
6
;
R
6
is alkyl (C
1-20
)or trialkylsilyl;
F is linear or branched alkylene of 1-10 carbon atoms, preferably ethylene;
In another aspect of the present invention there are provided novel organosiloxane compounds and oligomers containing one or more functional carboxylic ester groups that may be represented by the formula:
wherein:
R which can be the same or different, are hydrolyzable groups such as but not limited to halogen, hydroxy, alkoxy, alkoxyalkoxy, acyloxy, N,N-dialkylaminoxy, N-alkylamido, monoalkylamino, dialkylamino, isocyanato, alkylthio or cyano;
R
1
are as hereinabove defined;
R
7
and R
8
, which may be the same or different, are selected from alkyl, aryl, capped or uncapped polyoxyalkylene, alkaryl, aralkylene, alkenyl or alkynyl;
M can be the same or different and is selected from hydrogen, R, R
1
and —CH
2
—CHR
5
—R
2
—B—F—R
3
, with the proviso that at least one M is —CH
2
—CHR
5
—R
2
—B—F—R
3
;
y can be zero to 2;
a is from zero to 10;
b is from zero to 10;
R
2
, R
3
, R
5
, R
6
, B and F are as defined hereinabove.
In yet another aspect of the present invention there is provided a method for preparing organosilane or organosiloxane monomers containing one or more pyrrolidone-containing functional carboxyl ester groups which comprises reacting a N-alkenyl pyrrolidone containing a carboalkoxyl group of the formula
CH
2
═CR
5
—R—B—F—R
3
wherein:
R
2
, R
3
, R
5
, R
6
, F and B are as hereinabove defined.
with an organosilane hydride having one or more hydride groups of the formula
wherein:
R, which can be the same or different, are hydrolyzable groups such as but not limited to halogen, alkoxy, alkoxyalkoxy, acyloxy, N,N-Dialkylaminoxy, N-alkylamido, monoalkylamino, dialkylamino, isocyanato, alkylthio or cyano;
R
1
and x are as hereinabove defined;
at an elevated temperature (preferably between 65° C. and 130° C.) in the presence of a noble metal catalyst for a time sufficient to react the hydride group(s) on the silicon atom with the olefinic group on the pyrrolidone.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
In accordance with the present invention there are provided novel organosilane and organosiloxane monomers or compounds containing a carboxylic ester functional group which may be represented by the general formula:
wherein:
R which can be the same or different, are hydrolyzable groups such as but not limited to halogen, acyloxy, N,N-Dialkylaminoxy, N-alkylamido, monoalkylamino, dialkylamino, isocyanato, alkylthio, cyano or alkoxy;
R
1
which can be the same or different, are substituted or unsubstituted alkyl, preferably lower alkyl (C
1
-C
6
);cycloalkyl, e.g. cycloheptyl; aralkyl, e.g. benzyl, phenylethyl etc.; substituted or unsubstituted aryl; alkenyl; alkynyl or —OSi(R
1
)
3
;
x can be zero to 3;
R
2
is linear or branched alkylene of 1-12 carbon atoms, preferably methylene;
R
5
is hydrogen or alkyl C
1-10
) preferably methyl;
B is —NR
10
, wherein R
10
is hydrogen or a dicarboxylic ester group of the formula —CH
2
—CH(COOR
6
)—CH
2
COOR
6
;
R
6
is alkyl (C
1-20
) or trialkylsilyl;
F is linear or branched alkylene of 1-10 carbon atoms, preferably ethylene;
In accordance with the present invention there are also provided organosiloxane compounds and oligomers containing one or more functional carboxyl groups that may be represented by the formula:
wherein:
R, which can be the same or different, are hydrolyzable groups such as but not limited to halogen, hydroxy, alkoxy, alkoxyalkoxy, acyloxy, N,N-dialkylaminoxy, N-alkylamido, monoalkylamino, dialkylamino, isocyanato, alkylthio or cyano;
R
1
which can be the same or different, are substituted or unsubstituted alkyl, cycloalkyl, substituted or unsubstituted aryl, aralkyl, alkenyl, alkynyl or —O—Si—(R
1
)
3
;
R
7
and R
8
, which may be the same or different, ar
Berger Abe
Fost Dennis L.
Lambkin Deborah C.
Mona Industries, Inc.
Ramstad Polly E.
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