Organic compounds -- part of the class 532-570 series – Organic compounds – Silicon containing
Reexamination Certificate
1994-12-16
2001-05-01
Shaver, Paul F. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Silicon containing
C554S039000, C554S077000, C546S014000, C548S110000, C549S214000
Reexamination Certificate
active
06225489
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to novel organosilicone compounds and, more particularly, to silicone containing derivatives having at least one esterified phosphate group in the molecule.
BACKGROUND OF THE INVENTION
Phosphate esters, quaternary amine 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, 4,380,637 and 4,382,036 to Lindemann et al.; U.S. Pat. Nos. 4,209,449, 4,336,385 and 4,503,002 to Mayhew et al.; U.S. Pat. Nos. 4,243,602, 4,283,542 and 4,336,386 to O'Lenick et al; and U.S. Pat. No. 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 compositions 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 well known and have been used commercially over the years, including for personal care and home care applications. In general, organosiloxane compositions are water-insoluble and the costs thereof are greater than many other commercial materials which has limited their use for many applications. Recently, particular types of betaine and phosphobetaine modified organosiloxanes 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 which have been suggested as exhibiting high foaming characteristics in water, substantivity to a variety of surfaces, reduced irritation to the eyes and skin and improved, although limited, water-solubility properties. While, as indicated, certain organosilicone compositions containing phosphobetaines and methods for preparing the same have been suggested, there has been no prior disclosure or suggestion of the novel silicone modified phospholipid compositions and preparation methods described in copending application Ser. No. 174,934, of which the present application is a continuation in part, or of the novel silicone modified phospholipid compositions and methods for preparing the same herein described which compositions exhibit a greater range of properties for different applications as well as providing means for closer control of the costs of the organosilicone products.
SUMMARY OF THE INVENTION
It is accordingly an object of the present invention to provide novel silicone-modified phospholipid compositions suitable for use in solvent and/or preferably aqueous based systems which exhibit excellent surface-active properties including high foaming, are well tolerated by human tissue, are substantive to the surface of natural and synthetic fiber, and the like.
It is another object of the present invention to provide novel water-soluble silicone-modified phospholipid compositions containing terminal, lateral (pendant) or combinations of terminal and lateral (pendant) silicone moieties and wherein the compositions can be prepared with a variety of concentrations of silicone as desired or required.
In accordance with the present invention, there has now been discovered novel phospholipid compositions that may be represented by the following general formula:
wherein:
A is selected from H, M, and R—Y—;
A
1
is selected from H, OH, OM, and R—Y—O—;
x is o or an interger from 1 to 5;
M is a cation, preferably an alkali metal;
Y is alkylene or substitued alkylene; and
R is selected from;
a) a quaternized organosilicone amidoamine moiety of the formula:
wherein:
R
1
is a silicone backbone chain as hereinafter described to which amidoamine and/or amine functional group(s) as herein described can be attached;
R
2
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
3
and R
4
, 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;
X
−
is an anion, preferably a halogen;
n is an integer from 2 to 12;
n
1
is zero or an integer from 1 to 12;
n
2
is 0 or 1;
n
3
is an integer from 1 to 5;
B is sulfur (S) or oxygen (O); with the proviso that when n
2
is 0, n
1
or n
3
is at least 1 and when n
2
is 1, n
1
and n
3
each is at least 1; and d is one or greater, preferably 2-10;
b) a quaternized organosilicone tertiary amine moiety of the formula:
wherein:
R
1
is a silicone backbone claim as hereinafter described to which amidoamine and/or amine functional groups can be attached;
R
6
is alkylene, hydroxyalkylene, arylene, alkarylene, aralkylene, heteroalkylene wherein the heteroatom can be N, S or O and there can be more than one of such hetero atoms in the chain;
X
−
is an anion, preferably a halogen;
d
1
is an integer of one or greater, preferably from 2 to 10; and
R
3
and R
4
are as hereinabove defined;
or a mixture of the quaternized organosilicone amidoamine moiety “a” and/or quaternized tertiary amine moiety “b” above and the moieties:
c) a quaternized organic amidoamine moiety of the formula:
wherein:
R
5
is alkyl, alkenyl, alkoxyalkyl or hydroxyalkyl of from 5 to 21 carbon atoms each, alkaryl or aryl of up to 20 carbon atoms;
R
2
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 of from 2 to 5 carbon atoms, within the oxyalkylene unit;
R
3
and R
4
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
3
and R
4
taken together with the nitrogen to which they are attached may represent an N-heterocycle;
X
−
is an anion, preferably a halogen;
g is 0 or 1;
n is integer from 2 to 12; and
n
4
is 1 or greater; and/or
d) an organic quaternized tertiary amine moiety of the formula:
wherein:
R
13
, R
14
and R
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
13
+R
14
+R
15
is between 10 and 24;
with the proviso that wherein R is a mixture of organosilicone amine and organic amine moieties, at least 5 equivalent weight percent to about 60 equivalent weight percent of the total equivalent weight of amine moieties of the phospholipid composition is a quaternized organosilicone amidoamine moiety, a quaternized organosilicone tertiary amine moiety or mixtures of the same.
The silicone backbone chain, R
1
, to which the amidoamine and/or amine functional groups as herein described are attached and which are shown herein as R
11
, corresponds to the general formula:
wherein:
R
7
and R
8
, which may be the same or different are selected from alkyl, aryl, capped or uncapped polyoxyalkylene, alkaryl, aralkylene and alkenyl (vinyl);
R
10
can be the same or different and can be selected from alkyl, aryl and olefinic (vinyl);
R
11
, which can be the same or different, can be selected from R
10
, —(CH
2
)
n1
—B
n2
—(CH
2
)
n3
—
Berger Abe
Fost Dennis L.
Lehrer Norman E.
Mona Industries, Inc.
Schoenberg Franklyn
Shaver Paul F.
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