Phosphate polymers

Details Phosphate polymers Phosphate polymers

2002-03-22

2003-05-20

Pezzuto, Helen L. (Department: 1713)

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

Synthetic resins

Polymers from only ethylenic monomers or processes of...

C526S264000, C526S274000, C526S287000, C526S288000, C526S303100, C526S317100

Reexamination Certificate

active

06566474

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention deals with the composition, and application of novel phosphate polymers. The compounds are useful as in personal care applications due to their outstanding emulsification properties, and because they are polymeric do not penetrate skin, making them non-irritating. The properties of these novel compounds that makes them well suited for these applications is the fact that they are substantive to fibers, hair and skin and also very mild to the skin and eyes and provide protection from environmental factors like acid rain and other pollutions which come in contact with hair and skin. The use of the compounds results in several additional desirable properties heretofore unattainable. This includes overcoming the problem of eye and skin irritation using traditional cationic conditioning agents.
2. Arts and Practices
The prior practices for providing softening, anti-tangle, and conditioning properties for use in personal care, textile and related applications has been incorporation of quaternary compounds. These materials have been used for many years despite some significant drawbacks including irritation, negative impact on the aquatic environment, build up and yellowing of the substrate upon which they are applied.
U.S. Pat. No. 5,162,472 to O'Lenick discloses free radical polymers which incorporate silicone into the backbone. While these materials have desirable properties, they do not have an ionizable phosphate group in the molecule.
The references cited herein are incorporated by reference to the extent applicable. Ratios and percentages are by weight and temperatures are Celsius unless otherwise stated.
THE INVENTION
Object of the Invention
It is the object of the current invention to provide a novel series of anionic free radical polymers. The polymers are made by homo-polymerization of the novel phosphate monomer or by polymerization with a variety of other vinyl containing free radical reactive monomers. The formation of a high molecular weight polymer results in less penetration of the skin by the compounds of the present invention and a very effective conditioner that remains on the surfact of the hair or skin where the conditioning agent is most effective.
It is another object of the current invention to provide a novel allyl alkoxy phosphates used as an intermediate in the preparation of the compounds of the present invention.
Still another objective of the current invention to provide personal care compositions which contain an effective conditioning amount of the compounds of the current invention. That effective conditioning concentration will vary from 0.1 to 20% of the composition. The compounds of the present invention have outstanding conditioning properties when applied to hair and skin.
SUMMARY OF THE INVENTION
The present invention is directed to free radical polymers which contain a phosphate group as one of the functional groups polymerized. The compounds of the invention are prepared by the free radical polymerization of a novel allyl phosphate monomer.
The phosphate functional allyl monomer is polymerized and subsequently used as the emulsification and conditioning agents for hair and skin.
The allyl alkoxy phosphate used to make the compounds of the present invention conform to the following structure:
(R)
x
—P(O)—(OH)
y
wherein;
R is CH
2
═CH—CH
2
—O—(CH
2
CH
2
O)
s
—(CH
2
CH(CH
3
)O)
t
—(CH
2
CH
2
O)
u
;
s, t and u are integers each independently ranging from 0 to 20;
x and y are each independently 1 or 2, with the proviso that x+y=3.
The compounds are made by the reaction of allyl alcohol alkoxylates, which-are commercially available with a phosphating agent selected from polyphosphoric acid or P
2
0
5
.
When polyhosphohric acid is used the products are primarily compounds in which x is 1 and y is 2.
CH
2
═CH—CH
2
—O—(CH
2
CH
2
O)
s
—(CH
2
CH(CH
3
)O)
t
—(CH
2
CH
2
O)
u
—H allyl alcohol alkoxylate+Polyphosphoric Acid→CH
2
═CH—CH
2
—O—(CH
2
CH
2
O)
s
—(CH
2
CH(CH
3
)O)
t
—(CH
2
CH
2
O)
u
P(O)—(OH)
2
When P
2
O
5
is used the products are primarily compounds in which x is 2 and y is 1.
CH
2
═CH—CH
2
—O—(CH
2
CH
2
O)
s
—(CH
2
CH(CH
3
)O)
t
—(CH
2
CH
2
O)
cu
—H allyl alcohol alkoxylate+P
2
O
5
→(CH
2
═CHCH
2
—O(CH
2
CH
2
O)
s
—(CH
2
CH(CH
3
)O)
t
—(CH
2
CH
2
O)
u
)
2
P(O)—(OH)
These allyl alkoxy phosphates are key materials to synthesis the polymers of the present invention. The polymers conform to the following structure;
wherein;
R′ is —CH
2
—O—(CH
2
CH
2
O)
s
—(CH
2
CH(CH
3
)O)
t
—(CH
2
CH
2
O)
u
—P(O)—(OH)
2
s, t and u are integers each independently ranging from 0 to 20;
1 is an integer from 10 to 2,000.
The compounds of the current invention are prepared by the free radical reaction of the allyl alkoxy phosphate containing monomer.
The compounds of the current invention conform to the following generic structure;
wherein;
R′ is selected from the group consisting of CH3 and H;
a is an integer from 1 to 100;
b, c, d, e, and f are integers ranging from 0 to 100;
R
1
is —CH
2
—O—(CH
2
CH
2
O)
s
—(CH
2
CH(CH
3
)O)
t
—(CH
2
CH
2
O)
u
P(O)—(OH)
2
s, t and u are independently integers ranging from 0 to 20;
R
2
is —C(O)—{overscore (M)}
+
M is selected from H, Na, K, Li, and NH 4;
R
3
is
R
4
is
R
10
, R
11
and R
12
are selected from H, methyl and ethyl;
R
5
is —C(O)—NH
2
R
6
is —C(0)—N(H)—(CH
2
)
q
—SO
3
−
M
+
q is an integer ranging from 1 to 5.
The compounds of the current invention are prepared by the free radical reaction of a meadowfoam ester containing monomer and other monomers selected from the following;
R
1
is derived from the monomer conforming to the following structure;
CH
2
═CH—CH
2
—O—(CH
2
CH
2
O)
s
—(CH
2
CH(CH
3
)O)
t
—(CH
2
CH
2
O)
u
P(O)—(OH)
2
s, t and u are independently integers ranging from 0 to 20;
R
2
is derived from the following monomer CH
2
═CH—C(O)—O
−
M
+
Acrylic acid and methacrylic acid is available from Dow.
R
3
is derived from the following monomer;
Vinyl pyrrolidone is available commercially from BASF.
R
4
is derived from the following monomer;
R
10
, R
11
and R
12
are selected from H, methyl and ethyl;
These monomers are available from CPS Corporation.
R
5
is derived from the following monomer CH
2
═CH—C(O)—NH
2
Acrylamide is available from Dow Chemical.
R
6
is derived from the following monomer;
CH
2
═CH—C(O)—N(H)—(CH
2
)
q
—SO
3
−
M
+
These materials are available from Lubrizol Inc.
These materials are reacted in a solvent, typically water under the influence of a free radical catalyst. Free radical polymerization is well known to those skilled in the art.
Preferred Embodiments
In a preferred embodiment b, c, d, e, and f are all zero and a and b are independently integers ranging from 1 to 100.
In a preferred embodiment b, d, e and f are all zero and a and c are independently integers ranging from 1 to 100.
In a preferred embodiment b, c, e and f are all zero and a and d are independently integers ranging from 1 to 100.
In a preferred embodiment b, c, d and f are all zero and a and e are independently integers ranging from 1 to 100.
In a preferred embodiment b, c, d and e are all zero and a and f are independently integers ranging from 1 to 100.
In a preferred embodiment x and y are 0.


REFERENCES:
patent: 4479893 (1984-10-01), Hirota et al.
patent: 5162472 (1992-11-01), O'Lenick
patent: 6117915 (2000-09-01), Pereira et al.
patent: 0 985 401 (2000-03-01), None
patent: 96/14145 (1996-05-01), None

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