Stock material or miscellaneous articles – Composite – Of polyamidoester
Reexamination Certificate
1998-12-17
2001-07-17
Acquah, Samuel A. (Department: 1711)
Stock material or miscellaneous articles
Composite
Of polyamidoester
C524S591000, C524S589000, C524S590000, C524S462000, C528S049000, C528S070000, C428S423100, C428S423400, C428S423500, C428S423900
Reexamination Certificate
active
06261695
ABSTRACT:
The present invention relates to a coating composition, a treating method employing the composition and a substrate treated by the treating method. More particularly, the present invention relates to a coating composition which is capable of forming a coating film excellent in water and oil repellency, antifouling properties and solvent resistance, on a substrate surface, and a substrate treated with such a composition.
It is common to treat a substrate surface with a composition containing a compound having water and oil repellency in order to impart oil and water repellency to the substrate surface. As such a composition, a composition is known wherein a polymer obtained by addition polymerization of an acrylic acid ester containing a fluoroalkyl group, or a compound obtained by an addition reaction of a polyisocyanate to a hydroxy compound containing a fluoroalkyl group, is made in the form of an aqueous dispersion or an organic solvent solution.
Further, an alkoxypolyalkylene fluorocarbamate is also known which is obtained by reacting a polyisocyanate, a fluorine compound, a hydrophilic reactant and water (JP-A-7-505190).
With conventional compositions, a crosslinking agent such as a melamine compound, a urea compound or a polyisocyanate may sometimes be added at the time of processing, but they have had drawbacks that even if such a crosslinking agent is added, it is difficult to attain firm bonding to the substrate, high density crosslinking can hardly be obtained, and the solvent resistance is inadequate.
Especially when they are used for treating a substrate having a flat surface made of e.g. a synthetic resin, an elastomer, a metal, a plant structural material, a ceramics or a stone material, or a base material with the surface flattened as coated by e.g. a synthetic resin or an elastomer, there has been a problem that the coating film formed on the substrate surface can not be maintained in a stable state after the treatment. For example, there has been a problem that the coating film is easily peeled or removed by wiping with an organic solvent, or the coating surface is easily soiled or modified by a substance having a substantial dissolving power such as cigarette nicotine or an adhesive agent of an adhesive tape.
It is an object of the present invention to provide a coating composition capable of forming a coating film which firmly bonds to a substrate surface and will not be peeled or removed even by an organic solvent, a treating method employing such a composition, and a treated substrate.
Namely, the present invention provides a coating composition comprising a fluorine-containing compound of the following formula 1, at least one polyisocyanate, water and at least one organic solvent:
R
f
—Q—A 1
wherein R
f
is a monovalent fluorine-containing organic group having from 2 to 20 carbon atoms, Q is a single bond or a bivalent linking group, and A is a group having a hydrogen atom reactive with an isocyanate group, a treating method employing such a composition, and a treated substrate.
Now, the present invention will be described in detail with reference to the preferred embodiments.
In the fluorine-containing compound of the formula 1 (hereinafter referred to as the fluorine-containing compound (1)) contained in the coating composition of the present invention, R
f
is a monovalent fluorine-containing organic group having from 2 to 20 carbon atoms.
In this specification, “a monovalent fluorine-containing organic group” means a monovalent organic group containing at least one fluorine atom. The monovalent fluorine-containing organic group is preferably “a monovalent fluorine-containing hydrocarbon group” which is a group having at least one hydrogen atom of a hydrocarbon group substituted by a fluorine atom.
Further, the monovalent fluorine-containing hydrocarbon group may be “a monovalent fluorine-containing aromatic hydrocarbon group” having at least one hydrogen atom of a monovalent aromatic hydrocarbon group substituted by a fluorine atom, or “a monovalent fluorine-containing aliphatic hydrocarbon group” having at least one hydrogen atom of a monovalent aliphatic hydrocarbon group substituted by a fluorine atom. Preferred is a monovalent fluorine-containing aliphatic hydrocarbon group. Further, the monovalent fluorine-containing hydrocarbon group may have at least one etheric oxygen atom or thioetheric sulfur atom inserted between the carbon-carbon bond.
The carbon number of the monovalent fluorine-containing hydrocarbon group is preferably from 2 to 18, particularly preferably from 4 to 12. Further, the carbon number of the monovalent fluorine-containing aromatic hydrocarbon group is preferably from 6 to 12, particularly preferably from 6 to 8.
When R
f
is a monovalent fluorine-containing aliphatic hydrocarbon group, it is preferably “a fluorine-containing alkyl group” having at least one hydrogen atom of an alkyl group substituted by a fluorine atom, particularly preferably “a polyfluoroalkyl group” having at least two hydrogen atoms of an alkyl group substituted by fluorine atoms. In the case of a polyfluoroalkyl group, it is preferred that a fluorine atom is bonded to the carbon atom of R
f
which is bonded to Q. It is preferred that 1 to 3 fluorine atoms are bonded to a carbon atom present at a terminal of R
f
.
When R
f
is a polyfluoroalkyl group, the carbon number is preferably from 2 to 20, particularly preferably from 2 to 18, most preferably from 4 to 12. Further, such a polyfluoroalkyl group may have at least one etheric oxygen atom or thioetheric sulfur atom inserted between the carbon-carbon bond of the alkyl group.
When R
f
is a polyfluoroalkyl group, the fluorinated ratio of the polyfluoroalkyl group, i.e. the proportion of fluorine atoms in the polyfluoroalkyl group, is preferably at least 60%, particularly preferably at least 80%, when represented by [(number of fluorine atoms in the polyfluoroalkyl group)/(number of hydrogen atoms in the alkyl group having the same carbon number corresponding to the fluoroalkyl group)]×100%. Further, the polyfluoroalkyl group is preferably a perfluoroalkyl group, whereby said fluorinated ratio is substantially 100%.
Further, the polyfluoroalkyl group may have a linear structure or a branched structure, preferably a linear structure. In the case of a branched structure, the branched portion preferably has a short chain having from 1 to 3 carbon atoms. The perfluoroalkyl group may have a linear structure or a branched structure, preferably a linear chain group of the formula CF
3
(CF
2
)
n
—, wherein n is preferably an integer of from 3 to 15, particularly preferably an integer of from 5 to 11. Further, R
f
may be a mixture of two or more types having different carbon numbers.
Further, when R
f
is a monovalent fluorine-containing aromatic hydrocarbon group, it is preferably a group having at least one hydrogen atom in a monovalent aromatic hydrocarbon group containing a phenyl group substituted by a fluorine atom. The monovalent aromatic hydrocarbon group containing a phenyl group is preferably an aryl group, an aralkyl group such as a benzyl group, or a group having a lower alkyl group substituted on such a group.
The following structures may be mentioned as specific examples for R
f
in the fluorine-containing compound (1). The following examples include “structural isomeric groups” which are structurally different groups having the same molecular formula.
C
2
F
5
—, C
3
F
7
— [including both CF
3
(CF
2
)
2
— and (CF
3
)
2
CF—], C
4
F
9
— [including 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
CF(CF
3
)CF
2
—], 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
15
F
31
—, H(CF
2
)
t
— wherein t is an integer of from 2 to 18, and (CF)
2
CFC
s
F
2s
— wherein s is an integer of from 1 to 15.
CF
3
(CF
Acquah Samuel A.
Asahi Glass Company Ltd.
Oblon & Spivak, McClelland, Maier & Neustadt P.C.
Rajguru U. K.
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