Silicon based quaternary ammonium functional compositions...

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

2001-10-24

2002-11-19

Shaver, Paul F. (Department: 1621)

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

Organic compounds

Silicon containing

C556S413000, C556S418000, C556S419000, C556S423000, C556S424000, C556S425000

Reexamination Certificate

active

06482969

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to silicon based quaternary ammonium functional compositions and to methods for making such compositions. More particularly, the invention relates to certain novel quaternary ammonium functional silicones and silanes, as well as methods to make quaternary ammonium functional silicones and silanes using cationizing agents.
BACKGROUND OF THE INVENTION
Quaternary ammonium functional organic materials are well known in the art. They can be made by methods such as the exhaustive alkylation of amines by alkyl halides. Because of their positive charge. quaternary ammonium functional organics are useful in treating materials/surfaces that are primarily negatively charged, such as in many textile and personal care applications. These materials have also been found to exhibit anti-microbial activity.
It has been found that cationic modification of polymers (including those making up fillers, fibers and surfaces, organic or silicon based) through addition or formation of quaternary ammonium functionality makes possible certain ionic interactions that are the basis of many useful properties (or their enhancement) and thus applications of such modified materials. These include increase in hydrophilic character, ability to act as a thickener and improved ability to pickup other materials such as dyes, coatings and conditioning agents.
Recently, such modification has been described for starch in PCT publication WO 99/62957 and for chitosan in the article by Loubaki et al. in 27
Eur. Polym. J
. 3:311-317 (1991). In the former, the cationizing agents, 2,3-epoxypropyltrimethylammonium chloride or equivalent chlorohydrin functional materials were used. Glycidyl trimethylammonium chloride was used in the work reported in the latter reference with reaction taking place at the amino groups of the chitosan.
Quaternary ammonium functional silicones and methods for making them have been known in the art for a number of years. 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, which 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.
A group of quaternary ammonium functional silanes covalently bonded to glass is disclosed by Tally et al. in U.S. Pat. No. 4,118,316. These materials are made by reacting amino silanes and glass beads to form silanized glass, followed by treatment with a halohydrin.
Considering the large number of applications possible, such as in personal care and textiles, there is a need for new quaternary ammonium functional silicones and silanes and methods for making them. The present invention is directed to filling these needs.
SUMMARY OF THE INVENTION
It is an object of this invention to provide novel, silicon based quaternary ammonium functional compositions. Thus, the invention relates to 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 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
−
.
It is a further object of this invention to provide methods to make silicon based quaternary ammonium functional compositions. Thus, this invention further relates to a method of making a silicon based quaternary ammonium functional composition, the method comprising:
reacting
(1) a quaternary ammonium compound having a substituent group, the substituent group having epoxide or halohydrin functionality, with
(2) a silicon based material having an organofunctional group, the silicon based material being an unsupported silicone or silane and the organofunctional group having carboxy or amino functionality.
DETAILED DESCRIPTION OF THE INVENTION
The compositions according to the present invention are silicon based quaternary ammonium functional compositions, including those that comprise 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 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
−
.
It should be understood that in this disclosure and the claims that follow that particular “R” and similarly designated groups may exhibit some variation, unless specifically stated otherwise. That is, variation allowed by the overall definition given. For example, if it is stated that R
99
in a certain chemical structure can be hydrogen, chlorine or a monovalent hydrocarbon, then the R
99
's in a particular sample of the corresponding material may actually vary among the stated possibilities of hydrogen, chlorine or various monovalent hydrocarbons (and still be covered by a corresponding claim). This variation can be between or within molecules as applicable.
As to optional “incorporated” functional groups, it should be understood that these may be “internal” as well as pendant groups. Such groups would not be included in any tally given for number of carbons, unless otherwise indicated.
It should be understood that in this

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