Cationic complexes of polyoxyalkylene glycol dicarboxylates

Details Cationic complexes of polyoxyalkylene glycol dicarboxylates Cationic complexes of polyoxyalkylene glycol dicarboxylates

2000-07-07

2002-06-25

Truong, Duc (Department: 1711)

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

Synthetic resins

From carboxylic acid or derivative thereof

C528S308000, C528S486000, C528S492000

Reexamination Certificate

active

06410679

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention deals with the composition, and application of novel carboxylated polymers, and complexes thereof. The complexes useful as softening, anti-tangle, and conditioning agents for use in personal care applications due to their outstanding mildness. 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 complex 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 form monolayers on the hair nor do they provide the protection to the hair offered by the present invention.
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 cationic complexes using traditional cationic compounds and polyoxyalkylene dicarboxylates. The formation of a high molecular weight complexes 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 polyoxyalkylene dicarboxylate used as an intermediate in the preparation of the compounds of the present invention.
It is 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 complexes made by the formation of salts using a cationic surfactant and a dicarboxylic polyoxyalkylene compound. These complexes have outstanding conditioning on hair, exceptional feel on skin and are well tolerated by skin and eyes. The compounds can be formulated with dimethicone copolyols to provide a multipurpose cosmetic conditioner.
The polyoxyalkylene dicarboxy is complexed with a variety of quaternary compounds to form the conditioning quats of the present invention.
The polyoxyalkylene dicarboxylate used to make the compounds of the present invention conform to the following structure:
R
1
—O—(CH
2
CH
2
O)
a
—(CH
2
CH(CH
3
)O)
b
—(CH
2
CH
2
O)
c
—R
1
wherein:
a, b and c are integers each independently ranging from 0 to 20;
R
1
is selected from the group consisting of
—C(O)—CH
2
—CH
2
—C(O)—OH;
—C(O)—CH═CH—C(O)—OH; and
The compounds are made by the reaction of polyoxyalkylene glycols (PEGS and PPGS), which are commercially available with succinic anhydride, maleic anhydride and phthalic anhydride.
H—O—(CH
2
CH
2
O)
a
—(CH
2
CH(CH
3
)O)
b
—(CH
2
CH
2
O)
c
—H+2 moles of
succinic anhydride
R
1
—O—(CH
2
CH
2
O)
a
—(CH
2
CH(CH
3
)O)
b
—(CH
2
CH
2
O)
c
—R
1
wherein R
1
is —C(O)—CH
2
—CH
2
—C(O)—OH.
The same reaction is conducted with maleic anhydride and phthalic anhydride to give the other compounds.
HO—(CH
2
CH
2
O)
a
—(CH
2
CH(CH
3
)O)
b
—(CH
2
CH
2
O)
c
—H+2 moles of
maleic anhydride
R
1
—O—(CH
2
CH
2
O)
a
—(CH
2
CH(CH
3
)O)
b
—(CH
2
CH
2
O)
c
—R
1
wherein R
1
is —C(O)—CH
2
═CH
2
—C(O)—OH.
—H—O—(CH
2
CH
2
O)
a
—(CH
2
CH(CH
3
)O)
b
—(CH
2
CH
2
O)
c
—H+2 moles of
Phthalic anhydride
 R
1
—O—(CH
2
CH
2
O)
a
—(CH
2
CH(CH
3
)O)
b
—(CH
2
CH
2
O)
c
—R
1
wherein R
1
is
These polyoxyalkylene dicarboxylates are key materials to synthesis the carboxy complex.
Complex
The complex compound of the present invention conform to the following structure;
R
2
—O—(CH
2
CH
2
O)
a
—(CH
2
CH(CH
3
)O)
b
—(CH
2
CH
2
O)
c
—R
2
wherein;
R
2
is selected from the group consisting of;
—C(O)—CH
2
—CH
2
—C(O)—O
−
;
—C(O)—CH═CH—C(O)—O
−
; and
R
4
is CH
3
or
Preferred Embodiments
Polyoxyalkylene Dicarboxylates
In a preferred embodiment
R
1
is —C(O)—CH
2
—CH
2
—C(O)—OH;
In another preferred embodiment
R
1
is —C(O)—CH═CH—C(O)—OH;
In another preferred embodiment R
1
is
Complex
In a preferred embodiment
R
2
is —C(O)—CH
2
—CH
2
—C(O)—O
−
.
In a preferred embodiment
R
2
is —C(O)—CH═CH—C(O)—O
−
.
In a preferred embodiment R
2
is


REFERENCES:
patent: 3856830 (1974-12-01), Kuehn et al.
patent: 5162472 (1992-11-01), O'Lenick, Jr.
patent: 5873908 (1999-02-01), Dahmen et al.
patent: 59021780 (1984-02-01), None
patent: 07185289 (1995-07-01), None
patent: WO-9711130 (1997-03-01), None
patent: 09286851 (1997-11-01), None
patent: 10067549 (1998-03-01), None
patent: 102591887 (1998-09-01), None
Oliver et al , Nanoparticles Built of Cross-linked Heterotelechelic,,,Macromolecules, 2000, 33, 4780-4790.

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