Organosilicone having a carboxyl functional group thereon

Details Organosilicone having a carboxyl functional group thereon Organosilicone having a carboxyl functional group thereon

2001-05-07

2003-05-20

Dawson, Robert (Department: 1712)

Drug, bio-affecting and body treating compositions

Live hair or scalp treating compositions

Polymer containing

C424S070122, C424S078030, C424S078020, C424S401000, C514S063000, C528S025000, C528S026000, C528S038000, C548S406000

Reexamination Certificate

active

06565837

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 directly preparing polysiloxanes containing functional carboxylic acid groups is known and indirect routes for their preparation have generally been used, such as 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 and diamino functional groups are well known and have been used in a variety of commercial applications, but none of such polysiloxanes also contain functional carboxyl groups or provide an amphoteric class of organosilicones. Accordingly, the development of a method for readily and more directly preparing polysiloxanes containing one or more functional carboxyl groups would be desirable and it would be particularly advantageous if such method employed readily available silicone materials such as amino or diamino functional polysiloxanes for preparing not only a variety of carboxyl functional polysiloxanes including an amphoteric class of capped or uncapped organosiloxanes and organosilicone derivatives thereof as well.
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 carboxyl functional silicone compositions or the method of preparing the same described in commonly assigned U.S. Pat. Nos. 5,596,061; 5,807,955 and 6,100,358, whose contents are incorporated by reference herein.
SUMMARY OF THE INVENTION
It is accordingly an object of the present invention to provide a method for directly and readily preparing organosilicone compositions having at least one pyrrolidone-containing carboxyl functional group thereon and particularly an amphoteric class of organosilicone compositions.
It is still a further object of the present invention to provide a method of using cosmetic and personal care preparations which include novel carboxyl functional polysiloxane compositions, including an amphoteric class of polysiloxane compositions.
In accordance with the present invention, there has now been discovered novel capped or uncapped polysiloxanes containing one or more carboxylic acid groups and/or the ester 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
, an amine or a diamine containing group of the formula —F
1
—B
n
2—F—NH
2
, an oxygen containing group of the formula —OR
11
, wherein R
11
is hydrogen or a lower alkyl (C
1-6
), and a pyrrolidone containing carboxyl functional group of the formula:
wherein at least one of R
1
is a pyrrolidone containing carboxyl or ester functional group or salt derivative thereof as shown; F
1
is linear or branched alkylene of 1-12 carbon atoms, preferably a linear or branched alkylene of 1-4 carbon atoms; F is linear or branched alkylene of 1-10 carbon atoms, preferably ethylene; R
2
is as defined below; R
5
can be hydrogen, lower alkyl (C
1-6
) or alkali metal; and B is —NR
9
, wherein R
9
is hydrogen or lower alkyl (C
1-6
) and further wherein n
2
is 0 or 1;
R
2
can be the same or different and can be selected from alkyl, aryl and olefinic (vinyl);
R
3
and R
4
, which may be the same or different, are selected from alkyl, aryl, capped or uncapped polyoxyalkylene, alkaryl, aralkylene and alkenyl (vinyl);
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 uncapped polysiloxanes containing one or more carboxylic acid groups and/or the ester derivatives thereof are provided. For such uncapped polysiloxane compositions at least one R
1
is an oxygen containing group of the formula —OR
1
, wherein R
11
is hydrogen or a lower alkyl (C
1-6
).
In a further 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 derivatives thereof, and particularly an amphoteric class of polysiloxane compositions, which comprises reacting an organosilicone fluid or composition having at least one diamine functional group which must contain at least one primary amine group with itaconic acid or an ester derivative 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 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 a still further aspect of the present invention there is provided a novel silicone-modified amidoamine composition having the formula:
wherein: R
10
is the silicone backbone chain as herein described to which at least one pyrrolidone containing amidoamine derivative of a pyrrolidone-containing carboxyl functional group can be attached as shown;
R
6
is hydrogen or alkyl, hydroxyalkyl or alkenyl of up to 6 carbon atoms each, cycloalkyl of up to 6 carbon atoms, or polyoxyalkylene of up to 10 carbon atoms within the oxyalkylene unit;
R
7
and R
8
, which may be the same or different, are selected from alkyl, hydroxyalkyl, carboxyalkyl of up to 6 carbon atoms in each alkyl; and polyoxyalkylene of up to 10 carbon atoms; in addition R
7
and R
9
taken together with the nitrogen to which they are attached may represent an N-heterocycle;
n
3
is an integer and is at least 1, preferably an integer from 2 to 12;
n
2
is 0 or 1 and B is —NR
9
, wherein R
9
is hydrogen or lower alkyl (C
1-6
);
F
1
is branched or linear alkylene of 1-12 carbon atoms;
F is branched or linear alkylene of 1-10 carbon atoms; and
d is at least one.
In a still further aspect of the present invention there is provided cosmetic and personal care preparations which contain at least 0.1%, preferably from 0.1% to 10%, of novel polysiloxanes containing one or more pyrrolidone-containing functional carboxyl groups and/or the ester or amidoamine derivatives thereof.
DETAILED DESCRIPTION OF THE INVENTION
In accordance with the present invention there are provided novel capped or uncapped polysiloxanes comprising a class of carboxyl functional polysiloxanes including an amphoteric class of such 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
, an amine or a diamine group of the formula —F
1
—B
n
2—F—NH
2
, an oxygen containing group of the formula OR
11
, wherein R
11
is hydrogen or lower alkyl (C
1-6
), and a pyrrolidone containing carboxyl functional group of the general formula:
wherein at least one R
1
is a pyrrolidone-containing carboxyl or ester functional group or salt derivative thereof as shown; F
1
is linear or branched alkylene of 1-12 carbon atoms, preferably a linear or branched alkylene of 1-4 carbon atoms including methylene, propylene and isobutylene ; F is linear or branched alkylene of 1-10 carbon atoms, preferably ethylene and isopropylene; R
2
is as defined below; R
5
is hydrogen, alkyl, preferably lower alkyl (C
1-6
), or an alkali metal; and B is —NR
9
, wherein R
9
is hydrogen or lower alkyl (C
1-6
) and further wherein n
2
is 0 or 1;
R
2
can be the same or different and can be selected from alkyl, aryl and olefinic (vinyl);
R
3
and R
4
, which may be the same or are selected from alkyl, aryl, capped or uncapped polyoxyalkylene, alkaryl, aralkylene and alkenyl (vinyl);
a can be an integer from 0 to 50,000; and
b can be an inte

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