Carboxy amphoteric surfactant complexes

Details Carboxy amphoteric surfactant complexes Carboxy amphoteric surfactant complexes

2000-01-18

2001-06-26

Nazario-Gonzalez, Porfirio (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Compounds having the group -c

C562S433000

Reexamination Certificate

active

06252107

ABSTRACT:

FIELD OF THE INVENTION
The present invention is directed to a class of compounds that are made by neutralizing the amino group in an amphoteric surfactant with the carboxylic acid group in an alkoxylated fatty alcohol compound. The complex has (a) lower irritation, (b) better foaming properties and (c) improved substantivity to a variety of substrates.
BACKGROUND OF THE INVENTION
The present invention relates to specific salts of amphoteric surfactants and carboxy fatty compounds. The compounds have unique properties including high foam, detergency and most importantly low irritation to the eye and skin. This makes the compounds of the present invention particularly well suited for personal care applications. Additionally, the compounds of the present invention are useful in industrial applications where detergency and substantivity are required. One particular application is in metal cleaning and corrosion inhibition. The compounds of the present invention provide both detergency and corrosion inhibition when applied to metal surfaces.
Amphoteric surfactants have been known for many years. The amphoteric compounds useful in the preparation of the compounds of the present invention are amino propronates. U.S. Pat. No. 3,417,136 to Hovoden describes the basic technology used to make amphoteric surfactants of the class which is useful for the preparation of the complexes of the present invention.
Silicone carboxy complexes are disclosed in U.S. Pat. No. 5,739,371 issued April 1998 to O'Lenick, incorporated herein by reference. That specific patent disclosed that silicone polymers were needed to observe the beneficial effects observed. We have now surprisingly observed that the same effect is obtained using fatty alcohol carboxylates in place of silicone carboxylates. This has very far reaching impact upon cost and formulation latitude in personal care products.
SUMMARY OF THE INVENTION
The compounds of the present invention are salts of an amphoteric and an alkoxylated alkyl carboxylate. The preparation of the specific salt compounds of the present invention results in properties heretofore unattainable. Specifically, the fatty amphoteric compounds of the present invention are good detergents, but are somewhat irritating to the skin and eyes. This irritation results in a defatting of the skin and an unacceptable feel on the skin. The alkoxylated alkyl carboxylate per se is neither a good detergent nor very mild to the skin. Surprisingly, both together in a salt of the present invention, the compounds of the present invention are very mild to skin and eye, and possess outstanding detergency. This combination of properties make compounds of the present invention applicable many personal care applications, where the cost of silicone is prohibitive.
Another very useful application for the salts of the present invention is in two in one shampoos. If one makes a complex of a standard fatty quaternary compound and a standard fatty anionic surfactant, the resulting salt is water insoluble and of very little usefulness in either cleaning or conditioning hair. The salts of the present invention are water soluble and unexpectedly provide both detergency and conditioning to the hair in a single application.
OBJECT OF THE INVENTION
It is the object of the present invention to provide a series of amphoteric/carboxy salts. These compounds have an outstanding combination of properties making them useful in personal care, and industrial applications. Another aspect of the present invention is a process for using the compounds of the present invention in cleaning and conditioning hair with the application of a single compound.
DETAILED DESCRIPTION OF THE INVENTION
The amphoteric surfactants from which the compounds of the present invention are based have the following structure:
R
3
—N—(CH
2
CH
2
C(O)—O
−
M
+
)
2
R
3
is selected from the group selected from CH
3
—(CH
2
)d— and CH
3
—(CH
2
)
e
—O—;
d is an integer ranging from 7 to 19;
e is an integer ranging from 7 to 19;
M is selected from Na, K, and Li.
The nitrogen group in the molecule is a tertiary amine and can be neutralized with a carboxylic acid. Such an acid is the alkoxylated acid useful in the preparation of the compounds of the current invention. The reaction is a neutralization reaction and can be explained by the following reaction sequence:
R
3
—N—(CH
2
CH
2
C(O)—O
−
M
+
)
2
+RC(O)OH An organic Base An Organic Acid R
3
-N+(H)-(CH
2
CH
2
C(O)-O- M+)
2
RC(O)O An organic salt
The compounds of the present invention are salts which conform to the following structure:
 A
−
B
+
wherein
A is R
1
—O—C(O)—R
2
—C(O)O
R
1
is CH
3
—(CH
2
)
n
—O—(CH
2
CH
2
O)
a
—(CH
2
CH(CH
3
)O)
b
—(CH
2
CH
2
O)
c
—;
n is an integers ranging from 7 to 21;
a and c are integers independently ranging from 0 to 20, with the proviso that a+b be greater than 5;
b is an integer ranging from 0 to 20;
R
2
is selected from the group consisting of
—CH
2
—CH
2
—,
—CH═CH—,
and
and B is
R3—N
+
(H)—(CH
2
CH
2
C(O)O
−
M
+
)
2
R
3
is selected from the group selected from CH
3
—(CH
2
)
d
— and CH
3
—(CH
2
)
e
—O—;
d is an integer ranging from 7 to 19;
e is an integer ranging from 7 to 19:
M is selected from Na, K, and Li.
Preferred Embodiments
In a preferred embodiment R3 is CH
3
—(CH
2
)
d
—.
In another preferred embodiment R3 is CH
3
—(CH
2
)
e
—O—.
In a preferred embodiment d is 7.
In a preferred embodiment d is 9.
In a preferred embodiment d is 11.
In a preferred embodiment d is 13.
In a preferred embodiment d is 15.
In a preferred embodiment d is 17.
In a preferred embodiment d is 19.
In a preferred embodiment e is 7.
In a preferred embodiment e is 9.
In a preferred embodiment e is 11.
In a preferred embodiment e is 13.
In a preferred embodiment e is 15.
In a preferred embodiment e is 17.
In a preferred embodiment e is 19.


REFERENCES:
patent: 3417136 (1968-12-01), Hovden
patent: 5739371 (1998-04-01), O'Lenick, Jr.

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