Dimethicone copolyol amido quats

Details Dimethicone copolyol amido quats Dimethicone copolyol amido quats

2000-12-06

2001-11-06

Moore, Margaret G. (Department: 1712)

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

Synthetic resins

From silicon reactant having at least one...

C528S031000, C528S026000, C528S041000, C556S419000

Reexamination Certificate

active

06313256

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Technical Field of the Invention
The present invention relates to novel dimethicone copolyol amido quaternary compounds bearing a cationic group and an amido group. This invention also relates a series of such products having differing amounts of water-soluble groups, silicone soluble groups and fatty 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 silicone containing surfactants prepared over the years for specific applications. For example, U.S. Pat. No. 5,153,294 issued in March 1994 discloses silicone alkoxylated quats. These ester containing carboxylates are prepared by the reaction of chloroacetic acid and a dimethicopne copolyol to male a chloro intermediate. The resulting product contains a silicone soluble group, a water-soluble group (polyoxyalkylene glycol) on a silicone backbone. The product however containing the ester group is sensitive to a process called hydrolysis. If placed in aqueous solution at a pH of 5 or below or a pH of 10 of above, the ester cleaves giving the starting dimethicone copolyol and succinic acid or it's salt. This hydrolytic instability limits the usefulness of this type of product since many processes are not run within this range. Another shortcoming of these compounds is the fact that in forming the ester linkage, the hydroxyl group on the molecule is reacted out. There are many instances in which a reactive hydroxyl group is desirable. For example, in the preparation of urethanes, this hydroxyl group is needed to react with isocynate to make flexible urethane. Another example is in making release coatings for paper. The presence of both a carboxyl and hydroxyl group offers the ability to make heretofore unavailable crosslinked systems.
It was not until the compounds of the present invention that molecules having a water-soluble group, silicone soluble group, fatty soluble groups as well as a cationic group were available.
3. Summary of the Invention
The present invention is directed toward the provision of a series of novel silicone compounds that have cationic groups and hydroxyl groups (water-soluble) and an amido group that provides outstanding foaming and conditioning properties. This allows for the preparation of very mild conditioning useful in the formulation of personal care products. 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:
R
2
is selected from the group consisting of —CH
3
, CH
2
—C
6
H
5
— —CH
2
C(O)—O
−
, and CH
2
CH(OH)CH
2
OH.
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 silicone compounds that have cationic groups and hydroxyl groups. The carboxylic linkage has 10 carbon atoms and consequently has fatty soluble properties. The products of the present invention have amido groups linked to the cationic group through a amidopropyl dimethyl group.
Another objective of the present invention is the preparation of an intermediate useful in the preparation of the compounds of the present invention.
Other objectives will become clear from reading the specifications and claims of the present patent.
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
R
2
is selected from the group consisting of —CH
3
, —CH
2
—CH
6
H
5
, —CH
2C(O)—O
−
, and —CH
2
CH(OH)CH
2
OH.
The products are made by reacting the following compounds with dimethylaminopropyl amine, followed by reaction with benzyl chloride, methyl chloride and/ or monochloro glycerin 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.
To produce an intermediate conforming to the following structure:
The silicone amido amine is then reacted with benzyl chloride, sodium monochloro acetate, monochloro glycerin or methyl chloride to produce a compound on which there is a (+) charge on the nitrogen bearing the two methyl groups.
In order to make the amido amine intermediate useful in making the products of the present invention, of the a intermediate methyl ester conforming to the following structure is first prepared:
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 methyl ester is prepared by the hydrosilylation reaction of a silicone polymer and specific alpha vinyl compounds.
+b CH
2
═CH—(CH
2
)
8
C(O)OCH
3
+c CH
2
═CH—CH
2
—O—(CH
2
CH
2
—O)
x
—(CH
2
CH(CH
3
)O)
y
—(CH
2
CH
2
—O)
z
H
 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 preparation of the intermediate is critical to the synthesis of the compounds of the present invention. If one tries to hydrosilylate a carboxylic acid directly, the reaction fails. The carboxylic acid group reacts with the Si-H and the desired product is not achieved. The hydrosilylation using the methyl ester however is essentially quantitative and proceeds to give the desired product.
Preferred Embodiments
In a set of preferred embodiments the compound of the present invention is the amido amine compound conforming to the following structure:
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.
In a preferred embodiment of the amido amine d is 0.
In a preferred embodiment of the amido amine d is an integer ranging from 1 to 20.
In a preferred embodiment of the amido amine b in an integer ranging from 1 to 5.
In a preferred embodiment of the amido amine b is an integer ranging from 6 to 20.
In a preferred embodiment of the amido amine c is an integer ranging from 1 to 5.
In a preferred embodiment of the amido amine c in an integer ranging from 6 to 20.
In a preferred embodiment of the amido amine a is an integer ranging from 1 to 5.
In a preferred embodiment of the amido amine a in an integer ranging from 6 to 20.
In another set of preferred embodiments of the present invention is the silicone polymer conforming to the following structure:
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
R
2
is selected from the group consisting of —CH
3
, —CH
2
—C
6
H
5
, —CH
2
C(O)—O
−
, and —CH
2
CH(OH)CH
2
OH.
In a preferred embodiment of the silicone polymer set d is 0.
In a preferred em

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