Organic compounds -- part of the class 532-570 series – Organic compounds – Silicon containing
Reexamination Certificate
2001-12-05
2002-09-10
Shaver, Paul F. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Silicon containing
C556S445000, C556S447000, C556S463000, C106S012000, C106S013000, C106S287120
Reexamination Certificate
active
06448428
ABSTRACT:
BACKGROUND OF THE INVENTION
Field of the Invention
The present invention relates to a novel fluorine-containing organic silicon compound and a method for its production. Particularly, it relates to a fluorine-containing organic silicon compound having a hydroxyl group directly bonded to a silicon atom, and a method for its production.
DESCRIPTION OF THE BACKGROUND
An organic silicon compound having fluorine atoms is excellent in e.g. lubricating properties, water and oil repellency and oil and chemical resistance and thus is applied to various industrial fields. For example, when it is used as an additive to a surface treating agent or a resin, it is possible to impart the above-mentioned properties to the surface of a substrate or a molded product of the resin. As a specific example of such a fluorine-containing organic silicon compound, a fluorine-containing silane coupling agent made of a compound represented by the following formula (11) may be mentioned.
ASiY
3
(11)
(In the formula (11), A represents R(CH
2
)
2
— (R is a perfluoroalkyl group), Y represents a hydrolysable group such as a halogen atom or an alkoxy group.)
Further, in a method of hydrolyzing a non-fluorine type silicon compound having a Si—Y moiety to produce a corresponding compound having a Si—OH moiety, a method of reacting while dropwise adding ammonia to the reaction system, is known.
However, in a case where the surface of a substrate was treated with a fluorine-containing silane coupling agent made of a compound represented by the formula (11), there was a problem that attached water remained on the surface, although the surface showed water and oil repellency and oil and chemical resistance.
Further, in the method of reacting while dropwise adding ammonia, the reaction operation was cumbersome, and it was necessary to control the flow rate in order to maintain the pH in the reaction system within a predetermined range. Further, use of ammonia brought about a problem from the viewpoint of working environment or a problem of odor.
SUMMARY OF THE INVENTION
The present invention has an object to provide a novel fluorine-containing organic silicon compound excellent in e.g. lubricating properties, water and oil repellency, and oil and chemical resistance. Namely, it has an object to provide a fluorine-containing organic silicon compound useful as an additive to be added to a surface treating agent and various resin compositions. A surface treating agent containing the compound as an essential component, is capable of imparting to the surface of a substrate a nature of readily removing water attached to the surface of the substrate.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
The present invention provides a fluorine-containing organic silicon compound represented by the following formula (1):
provided that the symbols in the formula (1) have the following meanings:
R
1
and R
2
: respectively independently monovalent hydrocarbon groups;
A
f
: a group represented by the following formula (2), (3), (4) or (5):
A
1
—X
1
— (2)
A
2
—X
2
—O—X
1
— (3)
A
1
—X
2
—O—X
1
— (4)
A
2
—X
1
— (5)
provided that the symbols in the formulae (2), (3), (4) and (5) have the following meanings:
A
1
: a monovalent polyfluorohydrocarbon group;
A
2
: a monovalent polyfluorohydrocarbon group containing an etheric oxygen atom;
X
1
: —(CH
2
)
a
— (a is an integer of at least 3);
X
2
: a bivalent hydrocarbon group. Further, the present invention provides a method for producing a fluorine-containing silicon compound represented by the above formula (1), which comprises hydrolyzing a fluorine-containing silicon compound represented by the following formula (10). Namely, it provides a method for producing a fluorine-containing organic silicon compound, wherein the hydrolysis is carried out while neutralizing hydrogen halide formed during the hydrolysis with a base.
provided that the symbols in the formula (10) have the following meanings:
X: a halogen atom;
R
1
, R
2
and A
f
: the same meanings as the meanings in the formula (1).
The fluorine-containing organic silicon compound of the present invention is represented by the following formula (1):
In the following, the meanings of the symbols in the formula (1) will be explained.
In the present invention, “a hydrocarbon group” means a group comprising carbon atoms and hydrogen atoms unless otherwise specified. The hydrocarbon group may be an aromatic hydrocarbon group or an aliphatic hydrocarbon group, but it is preferably an aliphatic hydrocarbon group. As a monovalent aliphatic hydrocarbon group, an alkyl group is preferred. As a bivalent aliphatic hydrocarbon group, an alkylene group is preferred, and a polymethylene group is more preferred. The number of carbon atoms in an alkyl group and in an alkylene group is preferably from about 1 to 10, particularly preferably from 1 to 4. Further, the alkyl group and the alkylene group are preferably of a straight chain structure.
R
1
and R
2
respectively independently represent monovalent hydrocarbon groups, preferably methyl groups.
A
f
is a group represented by the following formula (2), (3), (4) or (5):
A
1
—X
1
— (2)
A
2
—X
2
—O—X
1
— (3)
A
1
—X
2
—O—X
1
— (4)
A
2
—X
1
— (5)
Here, A
1
represents a monovalent polyfluorohydrocarbon group. The “monovalent polyfluorohydrocarbon group” means a group having at least two hydrogen atoms of a monovalent hydrocarbon group substituted by fluorine atoms. As such a group, a polyfluoroalkyl group is preferred.
The number of fluorine atoms in the polyfluorohydrocarbon group is preferably at least 60%, more preferably at least 80%, when it is represented by (the number of fluorine atoms in the polyfluorohydrocarbon group)/(the number of hydrogen atoms in a hydrocarbon group having the same number of carbon atoms corresponding to the polyfluorohydrocarbon group)×100(%). Particularly preferred is a perfluorohydrocarbon group wherein it is substantially 100% (a group having substantially all of hydrogen atoms of a hydrocarbon group substituted by fluorine atoms).
The structure of the monovalent polyfluorohydrocarbon group may be a straight chain or branched structure, but a straight chain structure is preferred. In the case of a branched structure, the branched moiety is preferably a short chain having from about 1 to 3 carbon atoms, and it is preferably a structure wherein the branched moiety is present at a terminal portion of A
1
.
A
1
is particularly preferably a perfluoroalkyl group.
The following examples may be mentioned as specific examples of A
1
. Further, structurally isomeric groups other than the following are included in A
1
.
C
4
F
9
— (including structural isomeric groups such as CF
3
(CF
2
)
3
—, (CF
3
)
2
CFCF
2
—, (CF
3
)
3
C— and CF
3
CF
2
CF(CF
3
)—), C
5
F
11
— (including structural isomeric groups such as CF
3
(CF
2
)
4
—, (CF
3
)
2
CF(CF
2
)
2
—, (CF
3
)
3
CCF
2
— and CF
3
(CF
2
)
2
CF (CF
3
) —), C
6
F
13
— (including structural isomeric groups such as CF
3
(CF
2
)
2
C(CF
3
)
2
—), C
8
F
17
—, C
10
F
21
—, C
12
F
25
—, C
14
F
29
—, C
16
F
33
—, C
18
F
37
—, C
20
F
41
— and (CF
3
)
2
CF(CF
2
)
s
— (s is an integer of 0 or at least 1).
A
2
represents a monovalent polyfluorohydrocarbon group containing an etheric oxygen atom. The “polyfluorohydrocarbon group containing an etheric oxygen atom” means a group having one or at least two etheric oxygen atoms inserted between a carbon-carbon bond of the above-mentioned polyfluorohydrocarbon group. As such a group, a group containing a polyfluorooxyalkylene moiety is preferred.
A
2
is particularly preferably a group containing perfluorooxyalkylene, more preferably a group containing perfluorooxyalkylene and having a perfluoroalkyl group at the terminal. As such a perfluorooxyalkylene, perfluorooxymethylene, perfluorooxyethylene, perfluorooxypropylene or perfluorooxybutylene may, for example, be mentioned.
Specific examples of A
2
may be CF
3
(CF
2
)
4
OCF(CF
3
)—, F[CF(CF
3
)CF
2
O]
u
CF(CF
3
)CF
2
CF
2
— (u is
Furukawa Yutaka
Yoneda Takashige
Asahi Glass Company Limited
Shaver Paul F.
LandOfFree
Fluorine-containing organic silicon compound and method for... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Fluorine-containing organic silicon compound and method for..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Fluorine-containing organic silicon compound and method for... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2850494