Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From silicon reactant having at least one...
Reexamination Certificate
1998-10-06
2001-05-08
Dawson, Robert (Department: 1712)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From silicon reactant having at least one...
C528S025000, C528S038000, C548S406000
Reexamination Certificate
active
06228967
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to novel organosilicone compositions and, more particularly, to silicone compositions having a carboxyl functional group thereon.
BACKGROUND OF THE INVENTION
While some carboxyl functional organosilicones are known, they are generally difficult and expensive to prepare and the commercial use thereof has therefore been limited. Heretofore, no convenient method for preparing polysiloxanes containing functional carboxylic acid groups is known and generally complex routes for their preparation have generally been used, including hydrosilylation of an unsaturated ester followed by hydrolysis, or alternatively, by hydrolysis of nitrile-containing silicone fluids. However, polysiloxanes containing one or more functional groups such as amino groups are well known and have been used in a variety of commercial applications but none of such polysiloxanes also contain functional carboxyl groups. Accordingly, the development of a method for readily preparing polysiloxanes containing one or more functional carboxyl groups would be desirable and it would be particularly advantageous if such method employed more readily available materials such as amino functional polysiloxanes for not only preparing carboxyl functional polysiloxanes but a variety of organosilicone derivatives thereof as well, including ester, amide and the like derivatives of silicone-containing compositions.
While, as indicated, certain polysiloxanes containing functional carboxylic acid groups and methods for preparing the same have heretofore been suggested, there is no disclosure or suggestion of the novel pyrrolidone-containing carboxyl functional silicone compositions described in copending application Ser. No. 08/651,730, now U.S. Pat. No. 5,817,730 of which the present application is a continuation in part, or of the novel ester and amide derivatives of pyrrolidone-containing carboxyl functional silicone compositions of the present invention.
SUMMARY OF THE INVENTION
It is accordingly an object of the present invention to provide novel organosilicone compositions having at least one pyrrolidone-containing carboxyl functional group thereon and ester and/or amide derivatives thereof.
It is another object of the present invention to provide a method for readily preparing organosilicone compositions having at least one pyrrolidone-containing carboxyl functional group thereon.
It is a further object of the present invention to provide improved cosmetic and personal care preparations which include novel carboxyl-functional silicone-containing compositions and/or ester or amide derivatives thereof.
In accordance with the present invention, there has now been discovered novel polysiloxanes containing one or more carboxylic acid groups and the ester and/or amide derivatives thereof that may be represented by the following general formula:
wherein:
R
1
, which can be the same or different, can be selected from R
2
, a primary amine containing group, and a pyrrolidone containing ester or amide functional group of the formula:
wherein at least one of R
1
is a pyrrolidone containing ester or amide functional group as shown; F, which can be the same or different, is linear or branched alkylene of 1-12 carbon atoms; R
2
is as defined below; D can be nitrogen or oxygen; R
5
can be hydrogen, alkyl or capped or uncapped polyoxyalylene; x is 1 or 2, with the proviso that if D is oxygen, x is 1, and when x is 2 R
5
can be the same or different; n is zero or 2; n
1
is zero or 1; n
2
is zero or 1; and B is —NR
9
, sulfur (S) or oxygen (O), wherein R
9
is hydrogen or lower alkyl (C
1-6
), with the proviso that when n is 0 and n
2
is 1, n
1
, is 1, when n is 2 and n
2
is 1, n
1
is 0 or 1 and when n is 2 and n
2
is 0, n
1
is 0;
R
2
can be the same or different and can be selected from alkyl, aryl, alkenyl, or alkynyl;
R
3
and R
4
, which may be the same or different, are selected from alkyl, aryl, capped or uncapped polyoxyalkylene, alkaryl, aralkylene, alkenyl or alkynyl;
a can be an integer from 0 to 50,000; and
b can be an integer from 0 to 100.
In another aspect of the present invention there is provided a method for preparing polysiloxanes containing one or more pyrrolidone-containing functional carboxylic acid groups and/or the ester and amide thereof, which comprises first reacting an organosilicone fluid or composition having at least one primary amine functional group with itaconic acid or an ester thereof at an elevated temperature (preferably from about 90° C. to about 130° C.) for a time sufficient to react, preferably substantially completely react (generally ranging from about 1-5 hours), the itaconic acid or ester derivative thereof with the functional primary amine group(s) on the silicone fluid or composition to form an organosilicone composition having at least one pyrrolidone-containing carboxyl functional group.
In yet another aspect of the present invention there is provided an alternate method for preparing polysiloxanes containing one or more ester derivatives of carboxylic acid pyrrolidone groups which comprises reacting an organosilicone fluid or composition having one or more hydride groups (terminal or lateral) on the polysiloxane chain with an N-alkenyl carboalkoxyl group containing a pyrrolidone nucleus portion in the presence of a noble metal catalyst, preferably soluble platinum catalyst, at an elevated temperature (preferably between about 65° C. and 130° C.) for the time sufficient to react, preferably substantially completely react, the hydride groups on the silicone fluid or composition with the pyrrolidone group.
In a still further aspect of the present invention there are provided cosmetic and personal care compositions comprising from about 0.1% to about 10%, preferably from about 1% by weight of pyrrolidone-containing carboxyl functional organosilicone compositions and ester and amide derivatives thereof.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
In accordance with the present invention there are provided novel polysiloxanes comprising a class of functional polysiloxanes which may be represented by the general formula:
wherein:
R
1
, which can be the same or different, can be selected from R
2
, a primary amine containing group, preferably of the formula —(CH
2
)
n
—F
n1
—B
n2
—F—NH
2
, and a pyrrolidone containing. ester or amide functional group of the general formula:
wherein at least one R
1
is a pyrrolidone-containing ester or amide functional group as shown; F, which can be the same or different, is linear or branched alkylene of 1-12 carbon atoms, preferably ethylene, propylene or isobutylene; R
2
is as defined below; D is nitrogen or oxygen; R
5
is hydrogen, saturated or unsaturated, branched or straight chain, substituted or unsubstituted alkyl of 6 to 22 carbon atoms or capped or uncapped polyoxyalkylene, preferably derived from ethylene oxide, propylene oxide or mixtures of the same of 6 to 22 carbon atoms; x is 1 or 2 with the proviso that if D is oxygen, x is 1, and when x is 2, R
5
can be the same or different; n is 0 or 2; n
1
is 0 or 1; n
2
is 0 or 1; and B is —NR
9
, sulfur (S) or oxygen (O), wherein R
9
is hydrogen or lower alkyl (C
1-6
); with the proviso when n is 0 and n
2
is 1, n
1
is 1, when n is 2 an n
2
is 1, n
1
is 0 or 1 and when n is 2 and n
2
is 0, n
1
is 0;
R
2
can be the same or different and can be selected from alkyl, aryl, alkenyl and alkynyl;
R
3
and R
4
, which may be the same or are selected from alkyl, aryl, capped or uncapped polyoxyalkylene, alkaryl, aralkylene, alkenyl or alkynyl;
a can be an integer from 0 to 50,000;
b can be an integer from 0 to 100; with the proviso that when a is zero, all R
1
can be the same or different pyrrolidone-containing ester or amide functional groups or only the terminal R
1
groups are R
2
groups, and R
3
can be the same or different than the R
2
groups.
It is evident from the general formula above that the polysiloxane compositions of the present invention have one or more pyrrolidone-containing functional ester or amide group(s) linked termi
Berger Abe
Fost Dennis L.
Dawson Robert
Mona Industries, Inc.
Ramstad Polly E.
Robertson Jeffrey B.
Schoenberg Franklyn
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