Silicon based quaternary ammonium functional compositions...

Details Silicon based quaternary ammonium functional compositions... Silicon based quaternary ammonium functional compositions...

2001-10-24

2003-08-19

Venkat, Jyothsan (Department: 1615)

Drug, bio-affecting and body treating compositions

Live hair or scalp treating compositions

Polymer containing

C424S070100, C424S070190, C424S070270, C424S070200, C424S401000, C514S937000

Reexamination Certificate

active

06607717

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to silicon based quaternary ammonium functional compositions and to their applications. More particularly, the invention relates to novel emulsions and other formulations containing quaternary ammonium functional silicones, methods of making these emulsions and other formulations, and their uses.
BACKGROUND OF THE INVENTION
Because of their positive charge, quaternary ammonium functional silicones are useful in treating materials and surfaces that are primarily negatively charged, such as in many textile and personal care applications. The quaternary ammonium functionality makes possible certain ionic interactions that are the basis of many useful properties. These include increased hydrophilic character, ability to act as a thickener, and improved ability to aid in the deposition of other materials such as coatings and conditioning agents.
Some quaternary ammonium functional silicones and methods for making them are known in the art. For example, Reid in U.S. Pat. No. 3,389,160 discloses a group of these materials and a two step method for making them. In the first step, an epoxy functional silicone is reacted with a secondary amine to form a tertiary amine functional silicone. The product is reacted with an alkyl halide to yield a quaternary ammonium functional silicone in the second step.
Margida in U.S. Pat. No. 4,895,964 discloses certain pendant quaternary ammonium functional silicones and a one step method for making them. Here, a tertiary amine salt is reacted with a pendant epoxy functional silicone. A group of terminal quaternary ammonium functional silicones is disclosed by Schaefer et al. in U.S. Pat. No. 4,891,166, as well as a method for making them. This method is similar to the method in Margida, except that a terminal epoxy functional silicone is used.
McCarthy et al. in U.S. Pat. No. 5,164,522 discloses a class of quaternary ammonium functional silicones and a method for making them; the method involves treating diamine functional silicones with ethylene oxide followed by reaction with dimethyl sulfate. In U.S. Pat. No. 5,098,979 to O'Lenick, another group of quaternary ammonium functional silicones is disclosed along with a two step method for making them. This method involves reacting a silicone polyether having a terminal —OH group with epichlorohydrin (an epoxide), and the resulting product is reacted with a tertiary amine.
Most recently, new quaternary ammonium functional silicones and methods for making them are disclosed in a companion U.S. patent application to the present case, filed the same day, invented by Helmrick and Kennan, and entitled, “Silicon Based Quaternary Ammonium Functional Compositions and Methods For Making Them”, which is hereby incorporated by reference. Some of these silicones have been found to perform especially well in a number of personal care applications and are described below. The present invention concerns emulsions and other formulations of these silicones, methods of making these materials and their uses.
SUMMARY OF THE INVENTION
It is an object of this invention to provide novel quaternary ammonium functional silicon based compositions. Thus, this invention relates to a quaternary ammonium functional silicone (“silicone quat”) based composition comprising:
(A) a Kennan silicone quat (as defined herein below);
(B) a surface active agent; and
(C) water.
A further object of this invention is to provide methods to make silicone based quaternary ammonium functional compositions and more particularly emulsions. Thus, this invention relates to a method for making a quaternary ammonium functional silicone based composition, the method comprising:
combining at least one member of the group consisting of
Kennan silicone quat based emulsions;
Kennan silicone quats diluted in
hydrocarbons, alcohols, silicones other than quaternary ammonium functional silicones or mixtures thereof;
Kennan silicone quats; and
mixtures thereof
with at least one member of the group consisting of a Kennan silicone quat, a surface active agent and water.
The invention also relates to a method for making a quaternary ammonium functional silicone based emulsion, the method comprising:
(1) mixing a Kennan silicone quat and at least one surface active agent optionally diluted with water; and
(2) combining water and at least a portion of the mixture from (1) if water is not already present therein.
In addition, the invention further relates to silicone quaternary ammonium functional compositions expressed in terms of the methods used to make them:
the composition produced by the method comprising combining at least a Kennan silicone quat, a surface active agent and water; and
the composition produced by the method comprising emulsifying a Kennan silicone quat with at least a surface active agent and water.
DETAILED DESCRIPTION OF THE INVENTION
The compositions according to the present invention are based on members of a class of silicon based quaternary ammonium functional materials first disclosed in the companion to this case identified previously. This class can be described as follows.
A silicon based quaternary ammonium functional composition comprising the group, —R
1
—Z—Q
3
,
where, —R
1
— is either a divalent hydrocarbon group, which may optionally incorporate ether or ester functionality, or —R
17
N(Q
1
)R
18
—, and is covalently bonded to Si in an unsupported (free, not covalently bonded to a support such as a glass bead) silicone or silane;
—Z— is —C(O)O— or —N(Q
2
)—;
—Q
3
is —CH(R
3
)CH(OH)YN
+
(R
4
)(R
5
)(R
6
) X
−
, hydrogen or a monovalent hydrocarbon group that may optionally incorporate hydroxy, diol, amide, ether or ester functionality;
—R
17
— and —R
18
— are independently divalent hydrocarbon groups that may optionally incorporate ether or ester functionality;
—Q
1
and —Q
2
are independently
—CH(R
3
)CH(OH)YN
+
(R
4
)(R
5
)(R
6
)X
−
, hydrogen or a monovalent hydrocarbon group that may optionally incorporate hydroxy, diol, amide, ether or ester functionality;
Y is a divalent hydrocarbon group;
R
3
is a monovalent hydrocarbon group or hydrogen;
R
4
, R
5
and R
6
are independently monovalent hydrocarbon groups; and
X
−
is a counter ion,
with the proviso that at least one of —Q
1
, —Q
2
and —Q
3
is —CH(R
3
)CH(OH)YN
+
(R
4
)(R
5
)(R
6
) X
−
.
Members of this class of silicon based materials that are of special interest in relation to the present invention are those comprising an —R
1
— covalently bonded to Si in an unsupported silicone. In this disclosure and the claims that follow, this group of materials of special interest will be designated as “Kennan silicone quats”.
In this disclosure and the claims that follow, a subset of the Kennan silicone quats, to be designated as “type I Kennan silicone quats” (the type I embodiment in the companion case previously identified), is defined as follows.
A silicone composition having an average formula (based on the silicone molecules and their number present in a given sample):
where R
21
, R
22
, R
23
, R
30
and R
31
are independently hydroxy, phenoxy, alkoxy or monovalent hydrocarbon groups;
R
24
, R
25
and R
27
are independently monovalent hydrocarbon groups;
R
28
is a monovalent hydrocarbon group, or contains nitrogen and may at least in part represent a group or groups of the form —R
1
—Z—Q
3
;
R
26
and R
29
contain nitrogen and where present represent, at least in part, a group or groups of the form —R
1
—Z—Q
3
;
—R
1
— is either a divalent hydrocarbon group, that may optionally incorporate ether or ester functionality, or —R
17
N(Q
1
)R
18
—;
—R
17
— and —R
18
— are independently divalent hydrocarbon groups that may optionally incorporate ether or ester functionality;
—Q
1
is —CH
2
CH(OH)CH
2
N
+
(R
4
)(R
5
)(R
6
) X
−
, hydrogen or a monovalent hydrocarbon group that may optionally incorporate hydroxy, diol, amide, ether or ester functionality;
R
4
, R
5
and R
6
are independently monovalent hydrocarbon groups;
X
−
is a counter ion;
—Z— is —N(Q
2
)—;
—Q
3
and —Q

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