Organic compounds -- part of the class 532-570 series – Organic compounds – Silicon containing
Reexamination Certificate
1999-03-17
2001-03-06
Vollano, Jean F. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Silicon containing
C556S457000, C556S467000, C556S488000
Reexamination Certificate
active
06197989
ABSTRACT:
This application is the national phase of PCT/JP97/02449, filed Jul. 15, 1997, now WO 98/03574.
TECHNICAL FIELD
The present invention relates to a novel fluorine-containing organic silicon compound and a method for its production. More particularly, it relates to a fluorine-containing organic silicon compound having, at both terminals of the molecule, hydroxyl groups bonded to Si groups via specific connecting groups. The compound of the present invention is useful for various industrial base materials which are required to have performances such as water and oil repellency, anti-fouling properties or release properties and as raw materials therefor.
BACKGROUND ART
A fluorine-containing organic silicon compound has been applied to various industrial fields by virtue of its nature such as its lubricating properties, water and oil repellency, oil resistance or chemical resistance. For example, it has been added to e.g. a resin to impart the above mentioned various properties to the resin.
As an example of such a fluorine-containing organic silicon compound, a fluorine-containing silicon oil represented by the following formula 15 may be mentioned.
Further, as a compound having a functional group incorporated to a fluorine-containing organic silicon compound, JP-A-8-109260 discloses a fluorine-containing organic silicon compound having a hydroxyl group which is directly bonded to a silicon atom at at least one terminal of the molecule.
The fluorine-containing organic silicon compound represented by the above formula 15 has had a problem that even if it is added to e.g. a resin for the purpose of imparting the above mentioned respective properties, the fluorine-containing organic silicon compound will ooze out on the resin surface as the time passes, whereby it has been difficult to impart the nature of the fluorine-containing organic silicon compound over a long period of time.
On the other hand, the fluorine-containing organic silicon compound disclosed in JP-A-8-109260 has a drawback such that the hydroxyl group directly bonded to the silicon atom is susceptible hydrolysis by a reaction with e.g. a hydroxyl group in air.
DISCLOSURE OF THE INVENTION
The present inventors have conducted a research strenuously to solve the above mentioned conventional problems and as a result, have found that a fluorine-containing organic silicon compound represented by the following formula 1 is capable of solving the above mentioned problems. The compound represented by the following formula 1 has, at both terminals of the molecule, hydroxyl groups bonded to Si groups via specific connecting groups, whereby when it is added to e.g. a resin, the hydroxyl group will have an inter action with the resin, and further, if the resin has a functional group reactive with a hydroxyl group, the two will react, so that it can stay in the resin over a long period of time, and it is capable of continuously imparting the nature of the fluorine-containing organic silicon compound over a long period of time. Further, the hydroxyl groups in the fluorine-containing organic silicon compound are bonded to Si groups via specific connecting groups, whereby the hydroxyl groups are not susceptible to hydrolysis, whereby there is a merit that the stability of the compound is high.
Namely, the present invention provides a fluorine-containing organic silicon compound represented by the following formula 1:
A
1
—X
1
— Formula 2
A
2
—X
2
—O—X
3
— Formual 3
A
3
—X
4
—O—X
5
— Formula 4
{In the formula 1, A
f
is at least one member selected from monovalent polyfluorohydrocarbon group-containing organic groups represented by the formulae 2, 3 and 4 provided that in the formulae 2 to 4, A
1
represents a 2 monovalent polyfluorohydrocarbon group; A
2
represents a monovalent polyfluorohydrocarbon group containing an etheric oxygen atom; A
3
represents a monovalent polyfluorohydrocarbon group; X
1
, X
2
, X
3
, X
4
and X
5
which are independent of one another, represent bivalent hydrocarbon groups; R
1
and R
2
which are independent of each other, represent bivalent organic groups; R
3
to R
9
which are independent of one another, represent monovalent organic groups; a is an integer of at least 1, and b is an integer of at least 0.}
Further, the present invention provides a method for producing a fluorine-containing organic silicon compound, which comprises adding at least one member selected from fluorine-containing unsaturated compounds represented by the following formulae 9, 10 and 11, to a H—Si group-containing organic silicon compound represented by the following formula 8:
A
1
—X
1
—(CH
2
)
r
CH
2
CH═CH
2
Formula 9
A
2
—X
2
—O—(CH
2
)
s
CH
2
CH═CH
2
Formula 10
A
3
—X
4
—O—(CH
2
)
t
CH
2
CH═CH
2
Formula 11
(In the formula 8, R
3
to R
9
which are independent of one another, represent monovalent organic groups; a is an integer of at least 1, and b is an integer of at least 0.)
(In the formulae 9 to 11, A
1
represents a monovalent 2 polyfluorohydrocarbon group; A
2
represents a monovalent polyfluorohydrocarbon group containing an etheric oxygen atom; A
3
represents a monovalent polyfluorohydrocarbon group; X
1
, X
2
and X
4
which are independent of one another, represent bivalent hydrocarbon groups; and r, s and t which are independent of one another, represent integers of from 0 to 7.)
Still further, the present invention provides a method for producing a fluorine-containing organic silicon organic compound represented by the formula 1, which comprises subjecting a fluorine-containing cyclic compound represented by the following formula 13 to ring-opening polymerization in the presence of a compound represented by the following formula 12, if necessary together with a hydrocarbon type cyclic compound represented by the following formula 14:
BEST MODE FOR CARRYING OUT THE INVENTION
Now, the fluorine-containing organic compound of the present invention and the method for its production will be described in detail.
The fluorine-containing organic silicon compound of the present invention is represented by the following formula 1:
In the above formula 1, R
1
and R
2
which are independent of each other, represent bivalent organic groups, and R
3
to R
9
which are independent of one another, represent monovalent organic groups. Here, “organic groups” are groups containing carbon, preferably hydrocarbon groups. In this specification, “hydrocarbon groups” mean groups comprising carbon atoms and hydrogen atoms, unless otherwise specified. The hydrocarbon groups may be aromatic hydrocarbon groups or aliphatic hydrocarbon groups, but they are preferably aliphatic hydrocarbon groups, particularly preferably alkyl groups.
R
3
to R
9
are preferably monovalent hydrocarbon groups, particularly preferably alkyl groups. Further, R
1
and R
2
are preferably bivalent hydrocarbon groups, particularly preferably alkylene groups. The number of carbon atoms of these alkyl groups and alkylene groups is preferably from about 1 to 10, particularly preferably from 1 to 4. The alkyl groups and the alkylene groups are, respectively, preferably of straight chain structures.
In the above formula 1, A
f
represents at least one member selected from monovalent polyfluorocarbon group-containing organic groups represented by the following formulae 2, 3 and 4, preferably one member:
A
1
—X
1
— Formula 2
A
2
—X
2
—O—X
3
— Formula 3
A
3
—X
4
—O—X
5
— Formula 4
In the formulae 2 to 4, A
1
and A
3
which are independent of each other, represent monovalent polyfluorohydrocarbon groups, and A
2
represents a monovalent polyfluorohydrocarbon group containing an etheric oxygen atom.
“A polyfluorohydrocarbon group” is a group having at least two hydrogen atoms of a hydrocarbon group substituted by fluorine atoms and is preferably a polyfluoroalkyl group. Further, “a polyfluorohydrocarbon group containing an etheric oxygen atom” is a group having an etheric oxygen atom inserted between a carbon—carbon bond of
Furukawa Yutaka
Kotera Mami
Kumai Seisaku
Murphy Gerald J.
Ruckle, Jr. Robert E.
Asahi Glass Company Ltd.
Oblon & Spivak, McClelland, Maier & Neustadt P.C.
Vollano Jean F.
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