Silicone modified phospholipid compositions

A silicone-containing phospholipid composition is provided having the general formula: ##STR1## wherein: A can be H, M or R--Y--; A, can be H, OH, OM or R--Y--O; A.sub.1 is selected from H, OH, OM or R--Y--O--; M is a cation; Y is alkylene or substantially alkylene; x is 0 or an integer from 1-5; and R is a quaternized organosilicone amidoamine reactant moiety of the formula: ##STR2## wherein: R.sub.10 is the silicone backbone chain to which at least one pyrrolidone containing amidoamine functional group is attached; R.sub.6 is hydrogen, alkyl, hydroxyalkyl, alkenyl cycloalkyl or polyoxyalkylene; R.sub.7 and R.sub.8 are selected from alkyl, hydroxyalkyl, carboxyalkyl and polyoxyalkylene; F is linear or branched alkylene; X.sup.- is an anion; n is 0 or 2; n.sup.1 is 0 or 1; n.sup.2 is 0 or 1; n.sup.3 is an integer from 2 to 12. B is --NR.sub.11 sulfur or oxygen, wherein R11 is hydrogen or lower alkyl; with the proviso that when n.sup.1 is 0 and n.sup.2 is 1, n.sup.1 is 1, when n is 2 and n.sup.2 is 1, n.sup.1 is 0 or 1 and when n is 2 and n.sup.2 is 0, n.sup.1 is 0; and; d is one or greater.

FIELD OF THE INVENTION 
The present invention relates to novel organosilicone compositions and, 
more particularly, to silicone compositions having a carboxyl functional 
group thereon and to derivatives thereof having at least one esterified 
phosphate group in the molecule. 
BACKGROUND OF THE INVENTION 
Phosphate esters, quaternary ammonium compounds, betaines and certain 
substituted betaines are known in the art and have been commercially used 
over the years for a variety of applications, including those requiring 
surfactant properties. More recently, various betaine derivatives having, 
in general, specific quaternary compounds linked to phosphate esters 
referred to as phosphobetaines, and more particularly "synthetic 
phospholipids," have been disclosed, for example, in U.S. Pat. Nos. 
4,215,064, 4,233,192 and 4,380,637 to Lindemann et al.; 4,209,449, 
4,336,385 and 4,503,002 to Mayhew et al.; 4,243,602, 4,283,542 and 
4,336,386 to O'Lenick et al; and 4,617,404 to Lukenbach et al. These 
synthetic phospholipids are disclosed as exhibiting outstanding foaming, 
viscosity building, wetting, cleansing, detergency, anti-static, 
conditioning and emulsifying properties, making them useful in industrial 
applications calling for high performance surface active agents. The 
synthetic phospholipids are also described as being highly stable 
compounds which are well tolerated by human tissue (i.e. they exhibit 
exceptionally low oral toxicity and ocular irritation) and, hence, are 
well suited for use in a variety of personal care applications including 
cosmetic formulations as well as in industrial processes. 
A variety of organosiloxane compositions including compositions which 
exhibit excellent properties as surface active agents, lubricants and the 
like are known and have been used commercially over the years, including 
for personal care and home care applications. In general, however, 
organosiloxane compositions are water insoluble, which has limited their 
use for many applications. Recently, particular types of betaine and 
phosphobetaine modified organosiloxanes having improved, although limited 
water solubility properties have been disclosed, for example, in U.S. Pat. 
Nos. 4,609,750 and 4,654,161 to Kollmeier et al. and U.S. Pat. No. 
5,091,493 to O'Lenick et al. Such compositions are suggested as exhibiting 
high foaming characteristics in water, substantivity to a variety of 
surfaces and reduced irritation to the eyes and skin. While, as indicated, 
certain organosilicone containing phosphobetaine compositions and methods 
for preparing the same heretofore have been suggested, there has been no 
disclosure or suggestion of the novel carboxyl functional silicone 
compositions and silicone-containing phospholipid compositions described 
in copending application Ser. No. 174,680 and Ser. No. 298,565 of which 
the present applications is a continuation in part, or of the novel 
silicone-containing phospholipid compositions and methods for preparing 
the same herein described, which compositions exhibit a wide range of 
properties including solubility in a variety of solvents, preferably 
water, and are useful for a variety of different applications. 
SUMMARY OF THE INVENTION 
It is accordingly an object of the present invention to provide novel 
silicone-containing compositions which exhibit improved solubility 
characteristics particularly improved aqueous solubility. 
It is another object of the present invention to provide novel 
silicone-containing phospholipid compositions which exhibit excellent 
surface-active properties including high foaming, are well tolerated by 
human tissue, are substantive to the surface of a variety of substrates 
such as fiber, and the like. 
It is a further object of the present invention to provide novel soluble, 
preferably water soluble silicone-containing phospholipid compositions 
having functional phophorous containing groups linked terminally, 
laterally, or combination(s) of terminal and lateral linkages to the 
polysiloxane, which compositions can be prepared with a variety of 
concentrations of silicone, as desired or required. 
It is still another object of the present invention to provide novel 
silicone-containing phospholipid compositions which exhibit improved 
aqueous solubility characteristics and can be prepared with varying 
concentrations of silicones as desired by reactions with halogen 
containing phosphate, phosphite or polyphosphate, ester reactants. 
In accordance with the present invention, there has now been discovered 
novel silicone containing phospholipid compositions that may be 
represented by the following general formula: 
##STR3## 
wherein: A is selected from H, M and R--Y--; 
A.sub.1 is selected from H, OH, OM and R--Y--O--; 
x is 0 or an integer from 1 to 5; 
M is a cation, preferably an alkali metal; 
Y is a alkylene or substituted alkylene; and 
R is a quaternized organosilicone amidoamine reactant moiety of the 
formula: 
##STR4## 
wherein: R.sub.10 is the silicone backbone chain to which a pyrrolidone 
containing carboxyl or ester functional group or amidoamine derivative 
thereof as herein described can be attached as shown; 
R.sub.6 is hydrogen or alkyl, hydroxyalkyl or alkenyl of up to 6 carbon 
atoms, cycloalkyl of up to 6 carbon atoms, or polyoxyalkylene of up to 10 
carbon atoms, preferably from 2 to 5 carbon atoms, within the oxyalkylene 
unit; 
R.sub.7 and R.sub.8, which may be the same or different, are selected from 
alkyl, hydroxyalkyl, carboxyalkyl of up to 6 carbon atoms in each alkyl 
moiety and polyoxyalkylene of up to 10 carbon atoms; in addition R.sub.7 
and R.sub.8 taken together with the nitrogen to which they are attached 
may represent an N-heterocycle; 
F, which can be the same or different, is linear or branched alkylene of 
1-12 carbon atoms; 
X.sup.- is an anion, preferably a halogen; 
n is 0 or 2; 
n.sup.1 is 0 or 1; 
n.sup.2 is 0 or 1; 
n.sup.3 is an integer from 2 to 12; 
B is --NR.sub.11, sulfur (S) or oxygen (O), wherein R.sub.11 is hydrogen or 
lower alkyl (C.sub.1-6) with the proviso that when n is 0 and n.sup.2 is 
1, n.sup.1 is 1, when n is 2 and n.sup.2 is 1, n.sup.3 is 0 or 1, and when 
n is 2 and n.sup.2 is 0, n.sup.1 is 0; and 
d is one or greater, preferably 2-10 
In a further aspect of the present inventions there is provided novel 
silicone-containing phospholipid compositions that may be represented by 
the following general formula: 
##STR5## 
wherein: A is selected from H, M and R--Y--; 
A.sub.1 is selected from H, OH, OM and R--Y--O--; 
M is a cation, preferably an alkali metal; 
x is 0 or an integer from 1 to 5; 
Y is alkylene or substituted alkylene; and 
R.sub.9 is a mixture of quaternized silicone-containing amidoamine, organic 
amidoamine and/or organic tertiary amine moieties selected from the group 
consisting of: 
a) a quaternized organosilicone amidoamine moiety of the formula: 
##STR6## 
wherein: R.sub.10 is a silicone backbone chain to which a pyrrolidone 
containing carboxyl or ester functional group or amido amine derivative 
thereof as hereinafter described can be attached; 
R.sub.6 is hydrogen or alkyl, hydroxyalkyl or alkenyl of up to 6 carbon 
atoms, cycloalkyl of up to 6 carbon atoms, or polyoxyalkylene of up to 10 
carbon atoms, preferably from 2 to 5 carbon atoms, within the oxyalkylene 
unit; 
R.sub.7 and R.sub.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.sub.7 and 
R.sub.8 taken together with the nitrogen to which they are attached may 
represent an N-hetercycle. 
F, which can be the same or different, is linear or branched alkylene of 
1-12 carbon atoms; 
X.sup.- is an anion, preferably a halogen; 
n is 0 or 2; 
n.sup.1 is 0 or 1; 
n.sup.2 is 0 or 1; 
n.sup.3 is an integer from 2 to 12; 
B is --NR.sub.11, sulfur (S) or oxygen (O) wherein R.sub.11 is hydrogen or 
lower alkyl (C.sub.1-6); with the proviso that when n is 0 and n.sup.2 is 
1, n.sup.1 is 1, when n is 2 and n.sup.2 is 1, n.sup.1 is 0 or 1 and when 
n is 2 and n.sup.2 is 0, n.sup.1 is 0; and 
d is one or greater, preferably 2-10; 
b) a quaternized organic amidoamine moiety of the formula: 
##STR7## 
wherein: R.sup.12 is alkyl, alkenyl, alkoxy or hydroxyalkyl of from 5 to 
21 carbon atoms each, alkaryl or aryl of up to 20 carbon atoms; 
R.sub.6 is hydrogen or alkyl, hydroxyalkyl or alkenyl of up to 6 carbon 
atoms, cycoalkyl of up to 6 carbon atoms, or polyoxyalkylene of up to 10 
carbon atoms, preferably of from 2 to 5 carbon atoms, within the 
oxyalkylene unit; 
R.sub.7 and R.sub.8 which may be the same or different, are selected from 
alkyl, hydroxyalkyl, carboxyalkyl of up to 6 carbon atoms in each alkyl 
moiety, and polyoxyalkylene of up to 10 carbon atoms; in addition R.sub.7 
and R.sub.8 taken together with the nitrogen to which they are attached 
may represent an N-heterocycle; 
X.sup.- is an anion, preferably a halogen; 
g is 0 or 1; 
n.sup.3 is integer from 2 to 12; and 
n.sup.4 is 1 or greater; and 
c) an organic quaternized tertiary amine moiety of the formula: 
##STR8## 
wherein: R.sub.13, R.sub.14 and R.sub.15 are the same or different and are 
alkyl, substituted alkyl, alkyl aryl or alkenyl groups of up to 16 carbon 
atoms with the proviso that the total carbon atoms in R.sub.13 +R.sub.14 
+R.sub.15 is between 10 and 24; 
with the proviso that at least 5 equivalent weight percent to about 70 
equivalent weight percent of the total equivalent weight of amine moieties 
of the phospholipid composition is a quaternized organosilicone amidoamine 
moiety. 
It is evident from the general phospholipid formulae above that the 
functional phosphorus containing group(s) can be linked terminally, 
laterally or both terminally and laterally to the polysiloxane chain 
through the amidoamine and/or tertiary amine functional group. 
In a still further aspect of the present invention there is provided a 
method of preparing novel phospholipid compositions that may be 
represented by the general formula: 
##STR9## 
wherein: A is selected from H, M and R--Y--; 
A.sub.1 is selected from H, OH, OM and R--Y--O--; 
Y is alkylene or substituted alkylene; 
M is a cation, preferably an alkali metal; 
x is 0 or an integer from 1 to 5; and 
R.sub.9 is a mixture of quaternized amidoamine and/or tertiary amine 
moieties as hereinabove defined; 
which comprises reacting the combination of an organic amidoamine and/or 
organic tertiary amine reactant and a silicone-containing amidoamine 
reactant with a polyphosphate, phosphite or phosphate ester halide 
reactant in the equivalent weight ratios of from about 0.7 to 3.3 of total 
amidoamine and/or tertiary amine reactants to 1 of polyphosphate, 
phosphite or phosphate ester halide reactant until the amine reactant is 
completely reacted, with the proviso that at least 5 equivalent weight 
percent to about 70 equivalent weight percent of the total equivalent 
weight of amine reactants will be silicone containing, said polyphosphate, 
phosphite or phosphate ester halide reactant being of the general formula: 
##STR10## 
wherein: A.sub.2 is selected from H, M and X--Y--; 
A.sub.3 is selected from H, OH, OM and R--Y--O--; 
x is 0 or an integer from 1 to 5; 
M is a cation, preferably alkali metal; 
Y is alkylene or substituted alkylene; and 
X is halogen.

DESCRIPTION OF THE PREFERRED EMBODIMENTS 
In accordance with the present invention, there are provided novel 
phospholipid compositions which comprise a class of silicone-containing 
phospholipid compositions represented by the general formula: 
##STR11## 
wherein: A is selected from H, M and R--Y--; 
A.sub.1 is selected from H, OH, OM and R--Y--O--; 
x is 0 or an integer from 1 to 5; 
M is a cation, preferably an alkali metal; 
Y may be alkylene, optionally interrupted by up to 3 oxygen atoms, of up to 
12 carbon atoms, which alkylene chain may optionally be substituted with 
lower alkyl, alkoxyalkyl or hydroxyalkyl, e.g. not more than 10 carbon 
atoms each; and 
R is a novel quaternized organosilicone amidoamine reactant moiety of the 
formula: 
##STR12## 
wherein: R.sub.10 is the silicone backbone chain to which at least one 
pyrrolidone containing carboxyl or ester functional group or amidoamine 
derivative thereof is attached as herein described; 
R.sub.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, preferably from 2 to 5 carbon atoms, within the 
oxyalkylene unit; 
R.sub.7 and R.sub.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.sub.7 and 
R.sub.8 taken together with the N to which they are attached may represent 
an N-hetercycle. 
F, which can be the same or different, is a linear or branched alkylene of 
1-12 carbon atoms; 
X.sup.- is an anion, preferably a halogen; 
n is 0 or 2; 
n.sup.1 is 0 or 1; 
n.sup.2 is 0 or 1; 
n.sup.3 is an integer from 2 to 12; 
B is, --NR.sub.11, sulfur (S) or oxygen (O), wherein 
R.sub.11 is H or a lower alkyl (C.sub.1-6); with the proviso that when n is 
0 and n.sup.2 is 1, n.sup.1 is 1, when n is 2 and n.sup.2 is 0, n.sup.1 is 
0 or 1 and when n is 2 and n.sup.2 is 0, n.sup.1 is 0; and 
d is one or greater, preferably 2-10. 
In an alternate embodiment of the present invention, there are also 
provided novel phospholipid compositions including high molecular weight 
polysiloxanes which comprise a class of silicone-containing phospholipid 
compositions which exhibit a surprising and unexpected solubility in 
aqueous systems and/or aqueous/co-solvent systems. Such novel 
silicone-containing phospholipid compositions may be represented by the 
general formula: 
##STR13## 
wherein: A is selected from H, M and R--Y--; 
A.sub.1 is selected from H, OH, OM and R--Y--O--; 
M is a cation, preferably an alkali metal; 
x is 0 or an integer from 1 to 5; 
Y may be alkylene optionally interrupted by up to 3 oxygen atoms, of up to 
12 carbon atoms which alkylene chain may optionally be substituted with 
lower alkyl, alkoxyalkyl or hydroxyalkyl, e.g. not more than 10 carbon 
atoms each; and 
R.sub.9 is a mixture of quaternized amidoamine and/or tertiary amine 
moieties selected from the group consisting of: 
a) a quaternized organosilicone amidoamine moiety of the formula: 
##STR14## 
wherein: R.sub.10 is a silicone backbone chain to which at least one 
pyrrolidone containing carboxyl or ester functional group or amidoamine 
derivative thereof as herein described can be attached; 
R.sub.6 is hydrogen or alkyl, hydroxyalkyl or alkenyl of up to 6 carbon 
atoms each, or cycloalkyl of up to 6 carbon atoms, or polyoxyalkylene of 
up to 10 carbon atoms, preferably from 2 to 5 carbon atoms, within the 
oxyalkylene unit; 
R.sub.7 and R.sub.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.sub.7 and 
R.sub.8 taken together with the N to which they are attached may represent 
an N-hetercycle; 
X.sup.- is an anion, preferably a halogen; 
n is 0 or 2; 
n.sup.1 is 0 or 1; 
n.sup.2 is 0 or 1; 
n.sup.3 is an integer from 2 to 12; 
B is --NR.sub.11, sulfur (S) or oxygen (O), wherein R.sub.11 is hydrogen or 
lower alkyl; with the proviso that when n is 0 and n.sup.2 is 1, n.sup.1 
is 1, when n is 2 and n.sup.2 is 1, n.sup.2 is 0 or 1 and when n is 2 and 
n.sup.1 is 0, n.sup.1 is 0; and 
d is one or greater, preferably 2-10; 
b) a quaternized organic amidoamine moiety of the formula: 
##STR15## 
wherein: R.sub.12 is alkyl, alkenyl, alkoxy or hydroxyalkyl of from 5 to 
21 carbon atoms each, alkaryl or aryl of up to 20 carbon atoms; 
R.sub.6 is hydrogen or alkyl, hydroxyalkyl or alkenyl of up to 6 carbon 
atoms each, cycoalkyl of up to 6 carbon atoms, or polyoxyalkylene of up to 
10 carbon atoms, preferably of from 2 to 5 carbon atoms, within the 
oxyalkylene unit; 
R.sub.7 and R.sub.8 which may be the same or different, are selected from 
alkyl, hydroxyalkyl, carboxyalkyl of up to 6 carbon atoms in each alkyl 
moiety, and polyoxyalkylene of up to 10 carbon atoms; in addition R.sub.7 
and R.sub.8 taken together with the nitrogen to which they are attached 
may represent an N-heterocycle; 
X.sup.- is an anion, preferably a halogen; 
g is 0 or 1; 
n.sup.3 is integer from 2 to 12; and 
n.sup.4 is 1 or greater; and 
c) an organic quaternized tertiary amine moiety of the formula: 
##STR16## 
wherein: R.sub.13, R.sub.14 and R.sub.15 are the same or different and are 
alkyl, substituted alkyl, alkyl aryl or alkenyl groups of up to 16 carbon 
atoms with the proviso that the total carbon atoms in R.sub.13 +R.sub.14 
+R.sub.15 is between 10 and 24; 
X.sup.- is an anion, preferably a halogen; 
with the proviso that at least 5 equivalent weight percent to about 70 
equivalent weight percent of the total equivalent weight of amine moieties 
of the phospholipid composition is a quaternized organosilicone amidoamine 
moiety. 
Preferred silicone-containing phospholipid compositions of the invention 
wherein Y is 2-hydroxypropylene comprise a class of compositions which may 
be represented by the general formule; 
##STR17## 
wherein A, R and R.sub.9 are as defined above. 
The silicone backbone chain R.sub.10 to which the pyrrolidone containing 
amidoamine functional group hereinabove shown (represented below as 
R.sub.1) are attached corresponds to the general formula: 
##STR18## 
wherein: R.sub.1, which can be the same or different, can be selected from 
R.sub.2, a primary amine and a pyrrolidone containing group of the 
formula: 
##STR19## 
wherein at least one of R.sub.1 is a pyrrolidone containing amidoamine 
functional group as shown; F, which can be the same or different is a 
linear or branched alkylene of 1-12 carbon atoms; R.sub.2 is as defined 
below; R.sub.7 and R.sub.8 which may be the same or different are selected 
from alkyl, hydroxyalkyl, carboxyalkyl of up to 10 carbon atoms; in 
addition R.sub.7 and R.sub.8 taken together with the nitrogen to which 
they are attached may represent N-heterocycle; n is 0 or 2; n.sup.1 is 0 
or 1; n.sup.2 is 0 or 1; n.sup.3 is an integer from 2 to 12; and B is 
--NR.sub.11, sulfur (S) or oxygen (O), wherein R.sub.11 is hydrogen or 
lower alkyl (C.sub.1-6); with the proviso that when n is 0 and n.sup.2 is 
1, n.sup.1 is 1, when n is 2 and n.sup.2 is 1, n.sup.1 is 0 or 1, and when 
n is 2 and n.sup.2 is 0, n.sup.1 is 0; 
R.sub.2 can be the same or different and can be selected from alkyl, aryl 
and olefinic (vinyl); 
R.sub.3 and R.sub.4, which may be the same or different, are selected from 
alkyl, aryl, capped or uncapped polyoxyalkylene, alkaryl, aralkylene and 
alkenyl (vinyl); 
e can be an integer from 0 to 50,000; and 
f can be an integer from 0 to 100. 
It is evident from the general formulae of the novel phospholipid 
compositions of the invention that the functional phosphorus containing 
group(s) can be linked terminally, laterally or both terminally and 
laterally to the siloxane chain through the amidoamine functional 
containing alkylene and/or alkylene containing heteroatom group. 
In accordance with the invention, the phospholipid compositions of the 
invention can be prepared by reacting corresponding silicone containing 
amidoamine reactants or alternatively, combinations of silicone containing 
amidoamine and organic amidoamine and/or tertiary amine reactants with 
phosphate, polyphosphate or phosphite ester halide reactants in 
appropriate stoichiometric quantities as will be described in detail 
hereinafter to obtain the desired products of the formulae: 
##STR20## 
and preferably 
##STR21## 
wherein: A is as defined hereinabove; 
A.sub.1 is as defined hereinabove; 
Y is as defined hereinabove; 
x is as defined hereinabove; 
M is as defined hereinabove; and 
R is a quaternized organosilicone amidoamine moiety as defined hereinabove 
or, alternatively, 
R.sub.9 is a mixture of moieties selected from the group consisting of a 
quaternized organosilicone amidoamine moiety, quaternized organic 
amidoamine and/or organic quaternized tertiary amine moiety as defined 
hereinabove; 
with the proviso that at least 5 equivalent weight percent to about 70 
equivalent weight percent of the total equivalent weight of amine moieties 
of the phospholipid composition is a quaternized organosilicone amidoamine 
moiety. 
The intermediate reactants required in the processes for preparing the 
silicone-modified phospholipid compounds of the invention can be prepared 
as described hereinafter. 
Phosphate, polyphosphate and/or phosphite ester intermediate reactants 
suitable for use can be prepared by known procedures illustrated as 
follows: 
##STR22## 
wherein: A.sub.2 is selected from H, M and X--Y--; 
A.sub.3 is selected from H, OH, OM and X--Y--O--; 
A.sub.4 is H, OM or OH; 
A.sub.5 is H or M; 
a is from 0.5 to 3.5. preferably 1 to 3; 
b is from 1 to 3; preferably 1 to 2; 
M is a cation, preferably an alkali metal; 
x is 0 or an integer from 1 to 5; 
X is halogen; and 
Y is 2-hydroxypropylene. 
The above coupling reaction (I) is carried out in all aqueous media, 
preferably in the range of 30-50% concentration, having a pH range of 
5.0-8.0. 
##STR23## 
wherein: A.sub.6 is selected from H or OH; 
A.sub.7 is selected from H, OH or X--Y--O--; 
A.sub.8 is H or --Y--X; 
a is from 0.5 to 7, preferably from about 1 to 3; 
x is 0 or an integer from 1 to 5; 
X is halogen; and 
Y is 2-hydroxypropylene. 
The above reaction (II) is preferably carried out in the absence of water. 
Phosphate, phosphite and polyphosphate ester halide intermediate reactants 
for preparing phosphobetaine, pyrophospobetaine and the like compositions 
of the invention can also be prepared by known procedures such as 
disclosed, for example, in U.S. Pat. No. 4,617,414. 
Also suitable as phosphate and phosphite intermediate halide reactants are 
such reactants prepared by known procedures illustrated as follows: 
##STR24## 
wherein: a is 0 or an integer from 1 to 2; 
X is halogen; preferably bromine; and 
R.sub.16 is alkylene. 
##STR25## 
wherein: X is a halogen; preferably bromine; and 
R.sub.16 is alkylene. 
Carrying out reactions III(a) and IV(b) in the presence of a teritary amine 
HC1 acceptor is preferred to prevent any secondary reaction with the 
generated HCl gas. 
Silicone-containing amidoamines suitable for use as intermediate reactants 
in preparing the phospholipid compositions of the invention can be 
prepared as follows: 
##STR26## 
wherein: R.sub.10 is a silicone backbone chain to which at least one 
pyrrolidone containing carboxyl or ester functional group or amidoamine 
derivative thereof is attached as hereinabove shown; 
R.sub.5 is hydrogen, lower alkyl (C.sub.1-6) or alkali metal; 
R.sub.6 is hydrogen or alkyl, hydroxyalkyl or alkenyl up to 6 carbon atoms 
each, cycloalkyl of up to 6 carbon atoms or polyoxyalkylene of up to 10 
carbon atoms, preferably from 2 to 5 carbon atoms, within the oxyalkylene 
unit and at least one R.sub.6 is hydrogen; 
F, which can be the same or different is linear or branched alkylene of 
1-12 carbon atoms; 
R.sub.7 and R.sub.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.sub.7 and 
R.sub.8 taken together with the nitrogen to which they are attached may 
represent an N-hetercycle. 
B is --NR.sub.11, sulfur or oxygen wherein R.sub.11 is hydrogen or lower 
alkyl (C.sub.1-6); with the proviso that when n is 0 and n.sup.2 is 1, 
n.sup.1 is 1, when n is 2 and n.sup.2 is 1, n.sup.1 is 0 or 1 and when n 
is 2 and n.sup.2 is 0, n.sup.1 is 0; 
n is 0 or 2; 
n.sup.1 is 0 or 1; 
n.sup.2 is 0 or 1; 
n.sup.3 is an integer from 2 to 12; 
d and D is an integer from 1 or greater, generally from 1-50 and preferably 
2-10. The reactant ratio of the amine reactant to the carboxyl reactant on 
the silicon is preferably 1:1 but can be varied in ratio from 1:0.8 to 
1:1.2. 
Silicone-containing amidoamines suitable for use as intermediate reactants 
are, thus, readily prepared by the above coupling reaction (V) from the 
novel polysiloxane compositions having one or more pyrrolidone containing 
functional carboxyl or ester group(s) as herein described. 
The above coupling reaction (V) for preparing the silicone-containing 
amidoamine intermediate can be carried out neat or can be carried out in 
an inert solvent such as xylene, toluene, chlorobenzene or the like. While 
the equivalent weight of suitable silicone-modified intermediate 
amidoamine reactants is not critical, preferably the equivalent weight of 
such reactants is from about 500 to 1500. 
The novel carboxyl functional polysiloxanes or derivatives thereof 
(terminal, lateral or combinations of terminal and lateral) applicable for 
use in preparing the silicone-containing amidoamine intermediate reactants 
of the invention as set forth in the reaction sequence (V) illustrated 
above can be prepared by procedures such as disclosed in parent 
application Ser. No. 298,565, filed Aug. 31, 1994 and in the application 
Ser. No. 420,746 filed concurrently herewith. Such procedures include the 
reaction of corresponding silicone compositions or fluids having one or 
more functional primary amine groups with up to about one equivalent, 
preferably about stoichiometric quantities, of itaconic acid or its ester 
per functional amine group at an elevated temperature for the time 
sufficient for substantially all of the itaconic acid or its ester to 
react with the functional primary amine group(s). Preferably, from about 
0.9 to about 1.1 equivalents of itaconic acid or its ester per functional 
primary amine group is reacted with the silicone fluid wherein 
substantially all itaconic acid is reacted with the functional primary 
amine group(s) and polysiloxane compositions with at least one pyrrolidone 
containing functional carboxyl group(s) and/or its ester are formed. 
The reaction can be carried out neat or in an inert solvent such as 
alcohol, hydrocarbon solvent, chlorinated hydrocarbon and the like, in 
general, at elevated temperature, preferably from about 90.degree. C. to 
about 130.degree. C. The reaction proceeds readily and generally complete 
reaction of the itaconic acid or its ester with the available functional 
primary amine groups will occur in from about 1 to 5 hours, with routine 
analytical techniques for amine and acid values as well as monitoring 
water and/or alcohol evolution being used to determine completion of the 
reaction. 
Primary amine functional silicone fluids suitable for use having one or 
more primary amine functional group(s) linked terminally, laterally or 
both terminally and laterally, are well known and are available 
commercially, for example, from Dow Corning, Th. Goldschmidt AG and 
Shin-Etsu. While the equivalent weight of the silicone fluids or 
compositions which may be employed in the preparation of the pyrrolidone 
containing carboxyl functional polysiloxanes is not critical, and suitable 
compositions may have equivalent weights of 5,000 or even higher, silicone 
fluids having equivalent weights from about 500 to about 1500 are in 
general preferred. 
As indicated, the polysiloxanes compositions are readily prepared by 
reaction of primary amine functional silicone fluids with itaconic acid or 
its ester. Itaconic acid (methylene succinic acid) is a compound of the 
formula: 
EQU CH.sub.2 =C(COOR.sub.11)CH.sub.2 COOR.sub.11 
wherein: 
R.sub.11, which can be the same or different is hydrogen or lower alkyl 
(C.sub.1-6). 
The compound is available commercially from Pfizer Chemicals Division and 
from Norflex, Inc., Greensboro, N.C. and is produced by known fermentation 
techniques although chemical synthesis methods are also known. 
As noted above, silicone-containing phospholipid compositions of the 
invention can be prepared by reacting the desired silicone-containing 
amidoamine and phosphate, phosphite and/or polyphosphate ester halide 
reactants in appropriate desired stoichiometric proportions, in general, 
in molar equivalents of from about 0.7 to 3.3 of the amidoamine functional 
silicone reactant to 1 of the phosphate ester halide reactant. Such 
reaction can be carried out in a water solution or in conjunction with a 
co-solvent such as isopropyl alcohol, ethylene glycol, propylene glycol, 
ethyl cellosolve or the like. The reaction is carried out generally at 
elevated temperatures up to about 100.degree. C., preferably from about 
75.degree. to 95.degree. C., for a time ranging from about 1 to 5 hours, 
and generally until the amidoamine is substantially completely reacted. 
The course of the reaction can be determined by alkali number titration, 
ionic chloride determination, etc. 
The reaction of the silicone-containing amidoamine and phosphate, phosphite 
and/or polyphosphate ester halide reactants can be readily carried out in 
an aqueous or an aqueous/organic co-solvent reaction system wherein the 
amine equivalent weight of silicone fluid reactant is in the range up to 
about 2,000. Reactions will go to completion as demonstrated by 
homogeneity of the reaction mixture. When the amine equivalent weight of 
the silicone reactant is greater than about 1,200 to 2,000, the reactants 
are partially or completely insoluble in the reaction system and an 
incomplete reaction will result unless a co-solvent is used as referenced 
above. With silicone-containing amidoamine reactants having amine 
equivalent weights above about 2,000 to about 6,000, the addition of a 
co-solvent to an aqueous reaction system will not increase the solubility 
of the reactants as evidenced by phase separation and/or other signs of 
incomplete reaction. 
Surprisingly and unexpectedly, it has been found that alternate embodiments 
of the phospholipid compositions of the invention can be prepared in 
substantially completely soluble reaction systems using amidoamine 
functional silicone reactants as herein described having amine equivalent 
weights in excess of about 2,500 to about 6,000, or even greater, by also 
incorporating in the reaction system organic tertiary amine and/or 
preferably organic amidoamine reactants as herein described, in 
conjunction with the functional amidoamine silicone reactants. Suitable 
organic tertiary amino and/or amidoamine-containing reactants are added to 
the reaction system as a partial replacement of a substantially molar 
equivalent amount of the functional amidoamine silicone reactant, thus 
substantially maintaining the above noted molar equivalent ratios of amine 
reactants to phosphate ester halide reactants in the reaction mixture. 
Organic amidoamine intermediate reactants suitable for use in preparing the 
phospholipid compositions of the invention can be prepared as follows: 
##STR27## 
wherein: R.sub.12 is alkyl, alkenyl, alkoxy or hydroxyalkyl of from 5 to 
21 carbon atoms each alkaryl or aryl up to 20 carbon atoms; 
R.sub.6 is hydrogen or alkyl, hydroxyalkyl or alkenyl of up to 6 carbon 
atoms, cycoalkyl of up to 6 carbon atoms, or polyoxalkylene of up to 10 
carbon atoms, preferably of from 2 to 5 carbon atoms, within the 
oxyalkylene unit; 
R.sub.7 and R.sub.8 is as hereinabove defined; 
R.sub.5 is hydrogen or alkyl; 
g is 0 or 1; 
n.sup.3 is an integer from 2 to 12; and 
n.sup.4 is 1 or greater. 
The organic amidoamines suitable for use as intermediate reactants in 
preparing the phospholipid compositions are known or are generally 
prepared in accordance with conventional techniques such as shown in the 
above coupling reaction (VI). A variety of commercially available tertiary 
amino alkyl amines are suitable for use in reaction with an acid or acid 
derivative to prepare suitable amidoamines, as are the amidoamines 
themselves. Suitable tertiary amino alkyl amines can be primary or 
secondary amines with the proviso that the total number of carbons in the 
acid portion of the molecule be greater than 6, i.e. to give a hydrophobic 
moiety necessary for surface activity properties. Suitable amidoamines may 
be derived from acyl derivatives of aminoacid products such as glycine and 
sarcosine (N-methylglycine) including for example, products available 
under the Tradename HAMPOSYL from the Hampshire Chemical Co. 
Organic tertiary amine reactants also suitable for use in preparing the 
phospholipid compositions of the invention can be prepared using 
procedures well known in the art and many suitable compositions are 
available. 
Exemplary tertiary amines include: 
tributylamine 
bis(hydroxyethyl)hexylamine 
bis(2-hydroxyethyl)cocoamine 
N,N-dimethyl-dodecylamine 
N,N-dimethyl-tetradecylamine 
N,N-dimethyl-hexadecylamine 
N,N-dimethyl-cocoamine 
N,N-dimethyl-cetylamine 
dimethyl (C.sub.8-16) alkyl amine. 
N,N-dimethyl-octadecylamine 
The reaction of a combination of organic tertiary amine and/or preferably 
organic amidoamine reactant(s) and silicone-containing amidoamine 
reactants with phosphate, phosphite and/or polyphosphate ester halide 
reactants will proceed to completion at an elevated temperature, 
preferably a temperature ranging from about 75.degree. C. to 95.degree. 
C., with the formation of the silicone-containing phospholipid 
compositions of the invention. In a particularly preferred embodiment, 
when using a silicone-containing amidoamine reactant having an amine 
equivalent weight in excess of about 4,000, preferably, the organic 
amidoamine reactant to be used is an N-acylated amidoamine reactant 
derived from an amino acid or a mixture of such N-acylated amidoamine and 
an organic amidoamine reactant wherein the amount of N-acylated amidoamine 
used should be in excess of the stoichiometric amount of total amine 
reactants required. In general, the amount of said N-acylated amidoamine 
reactant to be used should be in a range of from about 25 to about 200, 
preferably 50 to 150, mole percent excess of the total stoichiometric 
amine reactant used in the coupling reaction. The order of addition of the 
reactants is not critical although it may be advantageous to add the 
excess amount of N-acylated amidoamine reactant derived from an amino acid 
after all the other ingredients have been added. While a heterogeneous 
mixture may result when all reactants are admixed, the reaction system 
becomes homogenous as the reaction proceeds. The reaction may start slowly 
while the mixture is heterogeneous but the reaction mixture will become 
substantially clear as the reaction proceeds. In accordance with the 
process of the invention, silicone-containing phospholipid compositions 
which contain at least weight percent to about 70 weight percent of the 
silicone composition portion of the total solids of the reaction product 
can be prepared, which silicone-containing phospholipid compositions will 
be completely soluble in aqueous/solvent or, preferably, aqueous systems 
while exhibiting surface active properties including low surface tension, 
high foaming and substantivity characteristics, low ocular and skin 
irritation and the like. Thus, it is possible by choice of particular 
amidoamine functional silicone, organic amidoamine and/or tertiary amine 
and phosphate ester halide reactants to obtain soluble and, preferably, 
aqueous soluble silicone-containing phospholipid composition with a wide 
range of surface active agent properties suitable for use in a variety of 
applications. 
The novel silicone-containing phospholipid compositions of the invention 
are good surfactants and exhibit good foam volume with excellent foam 
stability. Moreover, the novel phospholipid compositions are 
non-irritating to the eyes and skin, are highly substantive to fiber as 
well as a variety of other characteristics making them well suited for 
personal care and home care applications. 
The preparation of specific compositions of the invention is illustrated by 
the following specific examples which are provided herein for purposes of 
illustration only and are not intended to limit the scope therein. 
EXAMPLE 1 
An alpha-omega bis primary amino alkyl diamino functional polysiloxane 
fluid obtained commercially under the designation Tegomer A-Si2120 from 
Goldschmidt Company is used in this example. The amine content of the 
fluid is 3.5% which corresponds to a molecular weight of 914. 
91.4 grams of the above polysiloxane fluid (0.1 moles) is admixed with 26 
grams (0.2 moles) of Itaconic Acid in a reaction vessel. Upon combination 
of the reactants, a heterogeneous mixture is formed. External heat is 
applied to the reaction vessel bringing the reaction mixture to a 
temperature of about 110.degree. C., whereupon the reaction mixture 
becomes completely homogeneous while the temperature rises to 140.degree. 
C. 
After a heating period of 4 hours, a total of 7 1/2 ml. of volatiles are 
collected. The acid value of the reaction mixture is 81.6 (theoretical 
95.5) while the alkali number is nil, thus confirming that there is the 
presence of carboxyl groups on the product. 
EXAMPLE 2 
An alpha, omega-Bis primary amino alkyl dimethyl polysiloxane fluid with an 
average molecular weight about 1579.5 and having the general formula: 
##STR28## 
obtained commercially from Shin-Etsu under the designation X-22161A is 
used in this example. 
A mixture of 994.5 grams of the above polysiloxane fluid (0.6296 moles) and 
163.7 grams (1.25 moles) of Itaconic Acid is formed in a reaction vessel 
and heated (slowly to about 90.degree. C. at which point an exotherm 
occurs raising the reaction vessel temperature to 130.degree. C. and water 
starts to evolve. 
The reaction mixture is heated to and maintained at a temperature of 
140.degree. C. to 150.degree. C. for a period of 3 hours during which time 
about 20 ml. of water and other volatiles are collected. A clear, yellow 
viscous liquid is formed having an alkali number of 0. 
The mixture is then cooled to 90.degree. C. and 192.6 grams (an excess) of 
dimethylamino propylamine is admixed therewith. The temperature in the 
reaction vessel is increased to 170.degree. C. to 185.degree. C. and 
maintained at that temperature for an 4 additional hours during which time 
a total of 92 ml. of volatiles is collected. 
The reaction mixture is then cooled to about 50.degree. C. and subjected to 
a vacuum of 30 mm. While the vacuum is slowly drawn to 3 mm, the reaction 
vessel temperature is increased from 75.degree. C. to 150.degree. C. The 
product residue is then collected from the reaction vessel a 92% yield 
with an alkali number of 67 (theoretical alkali number is 57). 
200.88 grams of the reaction product above (0.12 moles) is then admixed 
with 75.4 grams of 40% active phosphate ester halide reactant and a 2:1 
mixture of propylene glycol and water to obtain a solution having 30% 
solids. The phosphate ester halide reactant used is prepared by the 
reaction of 3 moles of epichlorohydrin and one mole of sodium dihydrogen 
phosphate. 
The reaction admixture is heated for 4 hours at a temperature range of 
75.degree. C. to 85.degree. C. whereupon a homogeneous, clear liquid 
solution is obtained having a NaC1 content of 1.8% (theoretical NaC1 is 
1.86%). 
The product formed when mixed with water produced a great deal of stable 
foam whereas the polysiloxane functional amino fluid used as a starting 
material in the example provided no foam when mixed with water. 
EXAMPLE 3 
Another sample of a diamino polysiloxane fluid such as used in example 2 is 
used in this example. The average molecular weight of the sample is 1729 
which corresponds to a percent amine of 1.85%. 
To 43.2 grams (0.025 moles) of the above siloxane fluid in a reaction 
vessel is added with mixing 6.5 grams (0.05 moles) of Itaconic acid. The 
mixture is heated to 90.degree. C. whereupon an exotherm occurs raising 
the temperature to 130.degree. C. and resulting in a liquified viscous 
yellow mass. The reaction mixture is heated to and maintained at a 
temperature of 135.degree.-140.degree. C. for 3 hours while some volatiles 
are collected and at which point the alkali number is zero. 
There is then added to the reaction mixture 7.7 grams (0.075 moles, 50% 
excess) of dimethylamino propylamine (DMAPA) and the temperature is raised 
to 165.degree. C. where it is held for four additional hours. The reaction 
mixture is subjected to vacuum stripping to remove excess DMAPA at a 
reaction vessel temperature of 125.degree. C. and a vacuum of 10 mm. The 
alkali number of the reaction product residue is 54 (theoretical 52.9). 
A combination of 21.2 grams (0.01 moles) of the reaction product above, 
6.25 grams (0.0061 mole) of 40% active phosphate ester halide reactant 
prepared as in example 2, 16 grams of isopropanol and 16 grams of water 
having a solid content of 40% is prepared in a reaction vessel. The 
combined reactants are heated to a temperature of 95.degree. C. for 
four-five hours at which time a clear yellow solution is obtained having a 
NaC1 content of 2.4% (theoretical 1.9%). 
The product formed when added to water produces a great deal of stable 
foam. 
EXAMPLE 4 
A pendant (lateral) amino functional silicone fluid having an average 
molecular weight of 4400 obtained from Shin-Etsu under the product 
designation KF865 is used in this example. 
88 grams (0.02 moles) of the silicone fluid is admixed with 2.6 grams of 
Itaconic acid (0.02 moles) and heated to a temperature of 
130.degree.-140.degree. C. whereupon a clear melt is obtained and then 
continued heating for an additional two hours. 
After heating for two hours, the reaction mixture is cooled to 70.degree. 
C. and 4.08 grams (an excess) of dimethylamino propyl amine (DMAPA) is 
admixed therewith. The reaction mixture is then heated to a temperature of 
165.degree. C. for four hours, cooled to 70.degree. C. and vacuum stripped 
at 30-10 mm for three hours while slowly raising the temperature to 
110.degree. C. 
The reaction product residue is a clear liquid having an alkali number of 
12.3 (theoretical 12.2) and an acid number of 0. I.R. analysis confirms 
the presence of an amide linkage. 
EXAMPLE 5 
A pendant (lateral) aminofunctional silicone fluid obtained from Shin-Etsu 
under the product designation KF 865 is used in this example. The silicone 
fluid has an amine value of 0.2219 percent which corresponds to an amine 
equivalent weight of 5675. 
665.9 grams (0.1173 equiv. wt.) of the silicone fluid and 15.25 grams of 
Itaconic acid (0.1173 mole) are combined with 150 ml of xylene in a 
reaction vessel and heated to a temperature of 130.degree.-140.degree. C. 
under reflux. After heating for 4 to 5 hours under reflux, 2.3 ml of water 
is removed (theory 2.1). 
17.9 grams of dimethylpropyl amine (DMAPA) is then admixed with the 
reaction mixture and heated under reflux at a temperature of 
160.degree.-170.degree. C. for a period of about 4 hours during which time 
an additional 2.1 grams of water is removed. The reaction mixture is 
cooled to about 70.degree. C. and vacuum stripped at 30-40 mm to remove 
low boiling volatiles. A vacuum of 5-10 mm is then applied to the reaction 
mixture and the reaction vessel is heated for three hours at 140.degree. 
C. The reaction product is a clear liquid having an alkali number of 9 
(theoretical 9.55) which corresponds to an amine equivalent weight of 
6233. 
264 grams (0.9428 moles) of cocoyl sarcosine obtained as HAMPOSYL C from 
Hampshire Chemical Corp. is reacted in another reaction vessel with 144 
grams (an excess) of dimethylaminopropyl amine in 150 ml of refluxing 
xylene under a nitrogen atmosphere, with water being removed as it is 
formed. After 4 hours, water no longer evolves and the xylene and any 
volatiles are removed by heating the reaction mixture to 130.degree. C. at 
10 mm vacuum for 3 hours. 348 grams of a product having an alkali number 
of 185 is obtained. 
12.4 grams (0.002 equiv. wt.) of the above silicone/DMAPA product are 
combined with 2.4 grams (0.008 moles) of the above sarcosine/DMAPA 
product; 3.12 grams (0.0033 moles) of a 40% concentration of a phosphate 
ester halide reactant prepared by the reaction of 3 moles of 
epichlorohydrin with one mole of 85% phosphoric acid in the presence of 
one mole sodium hydroxide and 36 ml water in a reaction vessel. The 
reactant mixture is heated for 4 hours at a temperature of 
85.degree.-90.degree. C. The reaction mixture is hazy and non-homogeneous. 
Upon the addition of 2.67 grams (0.009 mole) additional grams of the 
sarcosine/DMAPA, the reaction mixture immediately becomes clear and 
homogeneous. The silicone content of the reaction product based on the 
total solids is 64%. The product when added to water produces a great deal 
of stable foam. 
EXAMPLE 6 
A mixture of the silicone/DMAPA and the 40% active solution of 
chlorohydroxy propyl phosphate reactants of example 5 when charged to a 
reaction vessel forms a completely non-homogeneous mixture even when 
heated at 100.degree. C. for several hours with only oily phases coating 
the reaction vessel. 
EXAMPLE 7 
The silicone/DMAPA, cocoyl sarcosine DMAPA and phosphate ester reactants of 
example 5 are used in this example. 
A combination of 18.7 grams (0.003 equiv.) of silicone/DMAPA; 2.12 grams 
(0.007 equiv.) of sarcosine/DMAPA; 3.12 grams of phosphate ester halide 
and 50 grams of water is formed in a reaction vessel and heated to 
85.degree.-90.degree. C. for 3 hours. The reaction mixture becomes thick 
and difficult to agitate with only a small liquid phase. There is now 
added to the reaction mixture 20 grams of water and 5 grams (0.016 equiv.) 
of the cocoylsarcosine/DMAPA and the reaction mixture is heated for two 
additional hours. A homogenous, clear solution results having a silicone 
solid content of 69%. 
EXAMPLE 8 
DiSodium 1, 3 Bis 3 chloro-2 hydroxy propyl pyrophosphate is prepared by 
charging 446 parts of Na.sub.4 P.sub.2 O.sub.7 10H.sub.2 O (1 mole) and 
178 parts H.sub.4 P.sub.2 O.sub.7 (1 mole) with 1000 parts deionized water 
to a reaction vessel and reacting the same with 320 parts epichlorohydrin 
at 60.degree.-80.degree. C. for 3-4 hours. 81.4 parts (0.2 equivalents) of 
the above reaction product is combined with a mixture of a pendant 
trimethylsilyl silicone pyrrolidone containing amidoamine having an 
equivalent weight of 1845 (0.05 equivalent) and 57.6 parts of 
N-Dimethylaminopropyl linoleamide (0.15 equivalents) and then diluted with 
480 grams of water to a 30% concentration. After the solution is adjusted 
to a pH of 8, the reaction mixture is heated to 90.degree.-95.degree. for 
a period of 4-5 hours at which time a clear solution forms. The reaction 
is monitored via argentometric estimation for covalent chloride to ionic 
chloride and the reaction is completed in 5 hours. 
The reaction product foams well in water. 
EXAMPLE 9 
A 3-chloro-2 hydroxypropylester salt of phosphorous acid is prepared by 
charging 41 grams (0.5 mole) of phosphorus, 409 grams of water and 50 
grams of 50% NaOH solution (0.6 mole) to a reaction vessel and warmed to 
75.degree. C. 46.25 grams (0.5 mole) of epichlorohydrin is then added and 
the reaction mixture is heated to 75.degree. C. for 11/2 hours with 
stirring. 
196 parts of the combined epichlorohydrinphosphite reaction mixture is 
admixed with 50% sodium hydroxide solution to achieve a pH of 8 followed 
by adding the combination of a pendant trimethylsilyl capped pyrrolidone 
containing silicone amidoamine having an equivalent weight of 3500 and 
27.3 parts of cocoyl safcosine amidoamine (0.09 equivalents). The reaction 
mixture is diluted with water to achieve 25% solids. 
The reaction mixture is heated to 90.degree. C. for 2 hours whereupon a 
clear aqueous solution is formed. 
EXAMPLE 10 
3-Bromopropyl diacid phosphate (BrCH.sub.2 CH.sub.2 CH.sub.2 OPO(OH).sub.2) 
is prepared by reacting 3-Bromopropyl with POCl.sub.3 while utilizing one 
equivalnet of triethyamine in the methylene chloride solvent. The 
Dichloride is isolated and hydroyzed to the diacid with water. The pH of 
the product in water is adjusted to 8 followed by the addition of an 
equivalent amount of 50:50 combination of a trimethylsilyl capped 
pyrrolidone containing silicone amidoamine having an equivalent weight of 
1845 and N-Dimethyl aminopropyl derivative of linoleamide. The reaction 
mixture is adjusted with water to 30% of total solids. 
The reaction mixture is heated for 4 hours at 90.degree. C. A clear 
solution is formed. 
Although some preferred embodiments have been described, many modifications 
and variations may be made thereto in light of the above teachings. It is 
therefore to be understood that within the scope of the appended claims, 
the invention may be practiced otherwise than as specifically described 
and illustrated.