Phosphated fluoro alkyl dimethicone copolyol esters

Details Phosphated fluoro alkyl dimethicone copolyol esters Phosphated fluoro alkyl dimethicone copolyol esters

2002-11-19

2004-06-08

Robertson, Jeffrey B. (Department: 1712)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

From silicon reactant having at least one...

C528S026000, C528S029000, C528S031000, C528S032000, C528S041000, C528S042000, C525S474000, C556S404000, C556S445000, C556S473000

Reexamination Certificate

active

06747116

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Technical Field of the Invention
The present invention relates to novel phosphated fluoro dimethicone copolyol ester compounds in which the fluoro group is attached to the silicon atom through a fatty group, and the water-soluble group is connected to silicon through a different silicon atom. This invention also relates a series of such products having differing amounts of water-soluble groups, silicone soluble groups, fatty soluble groups and fluoro-soluble groups. By careful selection of the compounds so constructed, very efficient mild conditioning agents may be achieved.
2. Description of the Arts
There have been several fluoro silicone compounds disclosed in the art. They include U.S. Pat. No. 5,446,114 to O'Lenick issued August 1995. This patent teaches that “the compounds of the invention arc prepared by reacting a silanic hydrogen containing silicone polymer with a vinyl containing fluoro compound and an allyl alcohol alkoxylate.” This results in a molecule with two functional groups water soluble groups and fluoro groups, both independently linked to a different silicon atom.
U.S. Pat. No. 5,473,038 to O'Lenick issued December 1995 teaches that “compounds of the invention are prepared by reacting a silanic hydrogen containing silicone polymer with a vinyl containing fluoro compound alpha olefin”. This results in a molecule with two functional groups alkyl groups and fluoro groups, both independently linked to a different silicon atom.
U.S. Pat. No. 6,087,517 to O'Lenick issued July 2000, teaches “the invention relates to a series of novel silicone fluorinated dimethicone copolyol phosphates. The compounds of the invention are prepared by reacting a fluoro dimethicone copolyol disclosed in U.S. Pat. No. 5,446,144 with a suitable phosphating agent.” This invention introduces a phosphate group onto the hydroxyl functional group of the compounds of U.S. Pat. No. 5,446,144. This results in a molecule with two functional groups alkyl groups and fluoro groups, both independently linked to a different silicon atom.
U.S. Pat. No. 6,008,397 to O'Lenick, issued December 28, 1999, “discloses novel fluoro esters made by reacting (a) a carboxy silicone, and (b) the hydroxyl group of fluoro alcohol.” The compounds of the '397 invention contain short linking groups derived from anhydrides and link the fluoro group through the water soluble group to one silicon atom.
We have surprisingly found that products made by the reaction of silicone methyl ester having 11 carbon atoms directly with the fluoro group, having a phosphated water soluble group containing polyoxyalkylene groups on another silicon atom results in an anionic fluoro-fatty silicone dimethicone copolyol phosphate. The compounds give unique emulsification properties with fluoro and fatty compounds or both, and have an outstanding gloss when applied lo the skin.
We have also surprisingly found that by having a bulky alkyl group linked to silicone, unique skin feel and conditioning properties result. The compounds of the prior art have the ester moiety linked through a water-soluble phosphated polyoxyalkylene group, resulting in a surface-active agent with different properties than the compounds of the present invention. The compounds linked through the polyoxyalkylene group are less efficient emulsifiers and do not provide the same degree of conditioning to the skin. The addition of the phosphate group results in unique emulsification and pigment dispersion properties.
SUMMARY OF THE INVENTION
The present invention is directed toward the provision of a series of novel silicone phosphate compounds that have a C-11 alkyl group linked to both a fluoro alcohol group and a silicon atom on opposite ends of the molecule. On one side the C-11 is linked through a carbon silicon bond and on the end of the C-11 group there is a fluoro alcohol linked through an ester group and to a silicon atom and ester groups linked through a hydrophobic group to silicon.
The water-soluble hydroxyl groups are likewise linked directly to another silicon group The compounds of the
present invention have the formula:
wherein;
a is an integer ranging from 0 to 2000;
b is an integer ranging from 1 to 20;
c is an integer ranging from 1 to 20;
d is an integer ranging from 0 to 20;
n is an integer ranging from 10 to 20;
x is an integer ranging 0 to 20;
y is an integer ranging 0 to 20;
z is an integer ranging 0 to 20;
R
1
is
CF
3
—(CF
2
)
m
—CH
2
CH
2
—O—;
m is an integer ranging from 3 to 18.
DETAILED DESCRIPTION OF THE INVENTION
Objective of the Invention
It is the object of the present invention is the provision of a series of novel phosphated silicone compounds that have specific hydrophilic fluoro ester groups linked through an 11-carbon linkage directly to silicon.
Detailed Description of the Invention
The compounds of the present invention conform to the formula;
wherein;
a is an integer ranging from 0 to 2000;
b is an integer ranging from 1 to 20;
c is an integer ranging from 1 to 20;
d is an integer ranging from 0 to 20;
n is an integer ranging from 10 to 20;
x is an integer ranging 0 to 20;
y is an integer ranging 0 to 20;
z is an integer ranging 0 to 20;
R
1
is
CF
3
—(CF
2
)
m
—CH
2
CH
2
—O—;
m is an integer ranging from 3 to 18.
The products are made by rearing fluoro duthicone copolyols with polyphosphoric acid to give the compounds of the present invention.
wherein:
a is an integer ranging from 0 to 2000;
b is an integer ranging from 1 to 20;
c is an integer ranging from 1 to 20;
d is an integer ranging from 0 to 20;
n is an integer ranging from 10 to 20;
x is an integer ranging 0 to 20;
y is an integer ranging 0 to 20;
z is an integer ranging 0 to 20:
R
1 is
CF
3
—(CF
2
)—CH
2
CH
2
—O—;
m is an integer ranging from 3 to 18.
An intermediate compound is prepared by the hydrosilyation reaction of a silicone polymer and specific alpha vinyl
wherein:
a is an integer ranging from 0 to 2000;
b is an integer ranging from 1 to 20;
c is an integer ranging from 1 to 20;
d is an integer ranging from 0 to 20;
n is an integer ranging from 10 to 20;
x is an integer ranging 0 to 20;
y is an integer ranging 0 to 20;
z is an integer ranging 0 to 20.
The subsequent reaction is as follows;
R
1
is
CF
3
—(CF
2
)
m
—CH
2
—O—;
m is an integer ranging from 3 to 18.
Preferred Embodiments
In a preferred embodiment of the silicone polymer set d is 0.
In a preferred embodiment of the silicone polymer set d is an integer ranging from 1 to 20.
In a preferred embodiment of the silicone polymer set b in an integer ranging from 1 to 5.
In a preferred embodiment of the silicone polymer set b is an integer ranging from 6 to 20.
In a preferred embodiment of the silicone polymer set c is an integer ranging from 1 to 5.
In a preferred embodiment of the silicone polymer set c in an integer ranging from 6 to 20.
In a preferred embodiment of the silicone polymer set a is an integer ranging from 1 to 5.
In a preferred embodiment of the silicone polymer set a in an integer ranging from 6 to 20.


REFERENCES:
patent: 5446114 (1995-08-01), O'Lenick, Jr.
patent: 5481015 (1996-01-01), Nomura
patent: 6087517 (2000-07-01), O'Lenick, Jr.
patent: 6175028 (2001-01-01), O'Lenick, Jr.
patent: 6245924 (2001-06-01), Imperante
patent: 6485731 (2002-11-01), Calello et al.

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