Organic compounds -- part of the class 532-570 series – Organic compounds – Silicon containing
Reexamination Certificate
2000-11-03
2002-05-07
Shaver, Paul F. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Silicon containing
C106S287110
Reexamination Certificate
active
06384254
ABSTRACT:
This invention relates to a quaternary ammonium salt-containing polysiloxane which is useful in formulating a fiber or fabric treating agent composition having anti-microbial properties and imparting softness and home laundry durability to various fibers and fibrous materials, a method for preparing the same, and a fiber or fabric treating agent composition comprising the same.
BACKGROUND OF THE INVENTION
In the prior art, quaternary ammonium salt-containing silanes as typified by 3-(trimethoxysilyl)-propyldimethyloctadecylammonium chloride are widely used as a treating agent for imparting anti-microbial properties to various fibers and fibrous materials. They are less toxic, little stimulative or sensitive to the skin, and home laundry durable on natural fibers such as cotton, but less home laundry durable on synthetic fibers such as polyester and nylon. Since the quaternary ammonium salt-containing silanes are solid, they must be delivered in the form of an alcohol solution, typically methanol solution, which undesirably increases the transportation cost. Since methanol volatilizes upon application, the solution also has a problem of environmental pollution and lacks safety because of the potential risk of ignition.
To eliminate these drawbacks, JP-A 6-101174 proposes a polysiloxane having a quaternary ammonium salt on a side chain and JP-A 6-298775 proposes a compound having a quaternary ammonium salt at either end. These siloxanes are prepared from intermediates, which are expensive since a complex process, is required for their preparation. Additionally, the resulting siloxanes somewhat lack home laundry durability since their adsorption to fibers resorts to only the quaternary ammonium salt group.
SUMMARY OF THE INVENTION
An object of the invention is to provide a novel and improved quaternary ammonium salt-containing polysiloxane which has satisfactory anti-microbial properties and when blended as a main component in a fiber or fabric treating agent composition, imparts softness to various fibers and fibrous materials and maintains the softness even after washing. Another object is to provide a method for preparing the quaternary ammonium salt-containing polysiloxane at a low cost. A further object is to provide a fiber or fabric treating agent composition comprising the quaternary ammonium salt-containing polysiloxane as a main component.
We have found that a novel polysiloxane having a quaternary ammonium salt in the siloxane skeleton is prepared by effecting alcohol-elimination reaction between &agr;,&ohgr;-dihydroxydimethylpolysiloxane and a quaternary ammonium salt-containing trialkoxysilane. The starting reactants are relatively easy to prepare and hence, inexpensive. Because of inclusion of both the siloxane skeleton and the alkoxy group, the resulting polysiloxane is highly adsorptive to fibers and highly home laundry durable. Because of the lack of alcohol, the polysiloxane is safe. By using an aminosilane such as an aminopropylaminotrialkoxysilane or N-aminoethyl-3-aminopropyltrialkoxysilane in combination with the reactants, a polysiloxane containing both an amino group and a quaternary ammonium salt-containing group in the skeleton is obtained. The use of the compound has the advantage that softening and anti-microbial treatments can be accomplished at the same time.
It is noted that a siloxane having a quaternary ammonium salt in the siloxane skeleton is disclosed in JP-B49-11760. However, this polymer is used as a foam stabilizer, does not contain an alkoxy group necessary to impart home laundry durability, and does not utilize alcohol-elimination reaction for its synthesis. This polymer is different from the inventive polymer.
Accordingly, the present invention in a first aspect provides a quaternary ammonium salt-containing polysiloxane comprising at least one unit of the following general formula (1):
wherein R
1
is a substituted or unsubstituted monovalent organic group of 1 to 20 carbon atoms, R
2
is a monovalent organic group containing at least one quaternary ammonium salt, R
3
is an organoxy group represented by —OR
1
, and p is a positive number of 2 to 2,000.
In a second aspect, the invention provides a quaternary ammonium salt-containing polysiloxane comprising at least one terminal group of the following general formula (2):
Wherein R1, R2 and R3 are as defined above, and “a” is equal to 0 or 1.
In a third aspect, the invention provides a method for preparing the quaternary ammonium salt-containing polysiloxane defined above, comprising effecting alcohol-elimination reaction between (A) an organopolysiloxane of the following general formula (5):
wherein R
1
and p are as defined above and (B) an organosilane of the following general formula (6):
wherein R
1
, R
2
, and R
3
are as defined above and “a” is 0 or 1.
Also contemplated herein is a fiber or fabric treating agent composition comprising the quaternary ammonium salt-containing polysiloxane defined above as a main component.
DESCRIPTION OF THE PREFERRED EMBODIMENT
In the present invention, the quaternary ammonium salt-containing polysiloxane is defined as comprising at least one unit of the general formula (1) and/or the general formula (2):
wherein R
1
is a substituted or unsubstituted monovalent organic group of 1 to 20 carbon atoms, R
2
is a monovalent organic group containing at least one quaternary ammonium salt, R
3
is an organoxy group represented by —OR
1
, and p is a positive number of 2 to 2,000.
wherein R
1
, R
2
, and R
3
are as defined above, and “a” is equal to 0 or 1.
The organic groups represented by R
1
are substituted or unsubstituted monovalent organic groups of 1 to 20 carbon atoms, especially 1 to 3 carbon atoms. Illustrative examples of R
1
in the organopolysiloxane include alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, octyl, decyl, dodecyl, tetradecyl, octadecyl and eicosyl; alkenyl groups such as vinyl, allyl, propenyl, butenyl and hexenyl; aryl groups such as phenyl and tolyl; aralkyl groups such as benzyl, phenylethyl, and phenylpropyl; cycloalkyl groups such as cyclopentyl and cyclohexyl; and substituted ones of the foregoing groups in which some or all of the hydrogen atoms attached to carbon atoms are replaced by halogen atoms, for example, halogenated alkyl groups such as chloromethyl, trifluoropropyl and chlorophenyl, and halogenated aryl groups such as halogenated phenyl. Of these, it is preferred that methyl, phenyl and/or trifluoropropyl account for at least 90 mol % of the R
1
groups.
Moreover, in the monovalent hydrocarbon groups (typically alkyl) represented by R
1
, some of the hydrogen atoms may be replaced by monovalent nitrogenous organic groups such as amino and alkylamino groups. Alternatively, the monovalent hydrocarbon groups represented by R
1
may be separated by dibalent nitrogenous organic groups such as NH, NCH
3
and NC
2
H
5
groups.
In formula (1), R
2
is a monovalent organic group containing at least one quaternary ammonium salt, preferably a monovalent organic group of the following general formula (3):
—CH
2
CH
2
CH
2
N
+
R
4
R
5
R
6
Cl
−
(3)
wherein R
4
and R
5
, which may be the same or different, are each a monovalent hydrocarbon group of 1 to 3 carbon atoms, and R
6
is a monovalent hydrocarbon group of 1 to 30 carbon atoms. More preferably, R
2
is a monovalent organic group of the following general formula (4):
—CH
2
CH
2
CH
2
N
+
(CH
3
)
2
C
n
H
2n+1
Cl
−
(4)
wherein n is a positive number of 12 to 24. Examples of the monovalent hydrocarbon groups represented by R
4
, R
5
and R
6
are as exemplified above for R
1
, examples of R
4
and R
5
being of 1 to 3 carbon atoms and examples of R
6
being of 1 to 30 carbon atoms. Most preferably, R
2
is
—CH
2
CH
2
CH
2
N
+
(CH
3
)
2
C
18
H
37
Cl
−
or —CH
2
CH
2
CH
2
N
+
(CH
3
)
2
CH
2
CH
6
H
5
Cl
−
.
R
3
is an organoxy group represented by —OR
1
, preferably an alkoxy group of 1 to 6 carbon atoms. Illustrative examples of R
3
are methoxy, ethoxy, and propoxy groups, with
Shaver Paul F.
Shin-Etsu Chemical Co. , Ltd.
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