Organic compounds -- part of the class 532-570 series – Organic compounds – Silicon containing
Reexamination Certificate
2000-02-28
2001-01-16
Shaver, Paul F. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Silicon containing
C528S025000
Reexamination Certificate
active
06175028
ABSTRACT:
BACKGROUND OF THE INVENTION
(1) Field of Invention
The present invention relates to a (a) novel silicone phosphate ester, (b) a method for preparation of said phosphate ester and (c) application of said phosphate ester in industrial and personal care applications.
The compounds of the present invention are made by reacting certain epoxy containing silicone compounds and a salt of an alkyl phosphate ester under aqueous conditions. The resulting compound is quite stable and offers excellent emulsification properties. In addition, compounds of the present invention may also contain a pendant hydroxyl group which alters the water solubility and emulsification properties of the compound. In a preferred embodiment the hydroxy containing group may also contain a polyoxyethylene group and a polyoxypropylene group. The ability to regulate the type of polyoxylakylene group and amount present in the silicone polymer results in a series of products ranging widely in water/oil solubility. The technology used to produce the compounds of the present invention is very flexible and allows us to prepare performance tailored molecules for specific applications.
(2) Object of the Invention
It is the object of the present invention to provide novel a process for the preparation of stable emulsions and microemulsions of oils in water using as an emulsifier a series of novel phosphated silicone polymers.
(3) Description of the Arts and Practices
U.S. Pat. No. 5,070,171, incorporated herein by reference, to O'Lenick, Jr. discloses the preparation dimethicone copolyol phosphates. The compounds of this technology are prepared by reacting a hydroxy containing silicone with a phosphating reagent. While the products are interesting there are several drawbacks. Firstly, there is no way to provide for an alkyl group on the phosphate. Secondly, we have discovered that there is functional improvement to be had by having a free hydroxyl group present in the molecule. This group improves wetting and emulsification. '171 provides for phosphation of all hydroxyl groups. If one were to try to phosphate only some of the hydroxyl groups, there is no way to predict which will phosphate and which will not. This is because all of the hydroxyl groups have identical reactivity.
The Invention
SUMMARY OF THE INVENTION
The compounds of the present invention are made by reacting certain epoxy containing silicone compounds and a salt of an alkyl phosphate ester under aqueous conditions. The resulting compound is quite stable and offers excellent emulsification properties. In addition, compounds of the present invention may also contain a pendant hydroxyl group which alters the water solubility and emulsification properties of the compound. In a preferred embodiment the hydroxy containing group may also contain a polyoxyethylene group and a polyoxypropylene group. The ability to regulate the type of polyoxylakylene group and amount present in the silicone polymer results in a series of products ranging widely in water/oil solubility. The technology used to produce the compounds of the present invention is very flexible and allows us to prepare performance tailored molecules for specific applications.
DETAILED DESCRIPTION OF THE INVENTION
The compounds of the present invention have several key portions in the molecule. Those groups include (a) an alkyl phosphate group, (b) a hydroxy propyl linkage group to silicone polymer, and (c) a silicone polymer that contains water soluble polyoxyalkylene groups. These groups and their positioning in the molecule result in unique properties for the molecule. These include emulsification properties, wetting properties, particularly for hydrophobic pigments, and a lubricious skin feel. This combination of properties has heretofore been unattainable in one molecule.
Compounds of the invention conform to the following structure:
wherein;
R
1
is: CH
3
(CH
2
)
s
—O—(CH
2
CH
2
—O)
z
—(CH
2
CH(CH
3
)O)
y—(CH2CH2-O)x-;
s is an integer ranging from 3 to 21;
R
2
is:
Me is methyl;
a is an integer from 0 to 200;
b is an integer from 0 to 200;
c is an integer from 1 to 200;
R
3
is —(CH
2
)
3
—(OCH
2
CH
2
)
i
—(OCH
2
CH(CH
3
))
j
—(OCH
2
CH
2
)
k
—OH;
x, y and z are integers and are independently ranging from 0 to 20;
i, j and k are integers and are independently ranging from 0 to 20;
g ranges from 1 to 3;
e and f range from 0 to 2 with the proviso that e+f+g=3;
M is selected from the group consisting of H, Na, K, Li, and NH
4
.
Illustrative of the sequence for the preparation of the compounds of the present is as follows;
In a 30% aqueous solution the disodium salt of a phosphate ester (pH 10.4) is reacted with an epoxy dimethicone copolyol to produce the phosphate ester of the present invention:
The compounds of the present invention are very good ingredients in a variety of applications that require the presence of both the phosphate and hydroxy group. These applications include:
(a) emulsion polymerization;
(b) urethane foams as modifiers of bubble structure;
(c) pigment dispersion agents for hydrophobic pigments;
(d) personal care applications for excellent skin feel.
Preferred Embodiments
In a preferred embodiment s is 11.
In a preferred embodiment s is 13.
In a preferred embodiments is 16.
In a preferred embodiment x, y, and z are each zero.
In a preferred embodiment x ranges from 3 to 10.
In a preferred embodiment y ranges from 1 to 10.
In a preferred embodiment i, j and k are each zero.
In a preferred embodiment i ranges from 3 to 10.
In a preferred embodiment s is 11 and x ranges from 3 to 10.
In a preferred embodiment s is 13 and x ranges from 3 to 10.
In a preferred embodiment s is 15 and x ranges from 3 to 10.
In a preferred embodiment s is 11 and i ranges from 3 to 10.
In a preferred embodiment s is 13 and i ranges from 3 to 10.
In a preferred embodiment s is 15 and i ranges from 3 to 10.
REFERENCES:
patent: 3849462 (1974-11-01), Lengnick
patent: 5070171 (1991-12-01), O'Lenick
patent: 5099051 (1992-03-01), Beck et al.
patent: 5481015 (1996-01-01), Nomura
patent: 5627296 (1997-05-01), Dauth et al.
patent: 5872272 (1999-02-01), Yano et al.
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