Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Mixing of two or more solid polymers; mixing of solid...
Reexamination Certificate
1999-04-28
2001-01-16
Dawson, Robert (Department: 1712)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Mixing of two or more solid polymers; mixing of solid...
C525S418000, C556S482000, C528S196000, C528S219000, C528S272000
Reexamination Certificate
active
06174966
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a coating agent composition, and more particularly to a coating agent composition containing a polymer having alkoxysilyl groups and a principal chain comprising a polycarbonate or a polyarylate. The present invention is also directed to a method of preparing the coating agent composition and to a coating material prepared therefrom.
BACKGROUND OF THE INVENTION
Numerous compositions have been proposed as organopolysiloxane compositions which form cured coating films at room temperature. For example, a composition consisting of a hydroxy group-containing organopolysiloxane resin, organoalkoxysilanes and an organic solvent has been proposed in Japanese Patent Application Kokai No. 51-148749. However, cured coating films produced from a composition consisting chiefly of this type of organopolysiloxane resin are inferior in terms of wear resistance, and are unsuitable for some applications.
Furthermore, polycarbonates and polyarylates are known as coating agents, and are widely used in optical applications, etc. For example, a medical material containing a polycarbonate with cross-linkable silyl groups as an active ingredient has been proposed (see Japanese Patent Application Kokai No. 58-109062). However, cured coating films produced from compositions containing a polycarbonate with cross-linkable silyl groups have inferior water-repellent properties, and, therefore, cannot be used in some applications.
SUMMARY OF THE INVENTION
The present invention is directed to a coating agent composition comprising:
(A) 100 parts by weight of a polymer having at least two alkoxysilyl groups, wherein the polymer has a number average molecular weight of 500 to 500,000, the polymer has a principal chain comprising a polycarbonate or a polyarylate, and the alkoxysilyl groups in the polymer have the formula:
—SiR
3−a
(OR′)
a
wherein R is a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, R′ is a substituted or unsubstituted monovalent hydrocarbon group having 1 to 8 carbon atoms, and a is from 1 to 3;
(B) 50 to 2,000 parts by weight of an organic solvent;
(C) 1 to 90 parts by weight of an organosilane, wherein the organosilane is a compound having the formula R″
e
SiY
4−e
or a partially hydrolyzed condensate thereof, wherein R″ is a substituted or unsubstituted monovalent hydrocarbon group or a hydrogen atom, Y is a hydrolyzable group, and e is from 0 to 2; and
(D) a cure catalyst in an amount sufficient to cure the composition.
The present invention is also directed to a method of preparing a coating agent composition, comprising mixing Components (A) to (D) above.
The present invention is further directed to a coating material prepared by curing the aforementioned coating agent composition.
DETAILED DESCRIPTION OF THE INVENTION
Component (A) of the present invention is a polymer having at least two alkoxysilyl groups. The alkoxysilyl groups may be located at pendant and/or terminal positions in the polymer. The polymer also has a number average molecular weight of 500 to 500,000 and has a principal chain comprising a polycarbonate or a polyarylate. The alkoxysilyl groups in component (A) have the formula:
—SiR
3−a
(OR′)
a
wherein R is a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, R′ is a substituted or unsubstituted monovalent hydrocarbon group having 1 to 8 carbon atoms, and a is from 1 to 3. Such alkoxysilyl groups are ordinarily bonded to carbon atoms in component (A). Alternatively, the alkoxysilyl groups may be bonded to silicon atoms in component (A) through siloxane bonds. In other words, the alkoxysilyl groups may be bonded to the principal chains in the polymer via siloxane bonds.
As stated above, the principal chain of component (A) can comprise a polycarbonate. The constituent units of the polycarbonates include constituent units having the formula:
wherein R
2
is selected from the group consisting of hydrogen atoms, halogen atoms, monovalent hydrocarbon groups having 1 to 4 carbon atoms, and monovalent hydrocarbon groups having 1 to 4 carbon atoms and containing at least one alkoxysilyl group; and D is selected from the group consisting of divalent hydrocarbon groups having 1 to 20 carbon atoms, —O—, —S—, —CO—, —SO
2
—, and divalent hydrocarbon groups having 1 to 20 carbon atoms and containing at least one alkoxysilyl group.
Examples of monovalent hydrocarbon groups represented by R
2
include, but are not limited to, alkyl groups, such as methyl, ethyl, propyl, and butyl; and alkenyl groups, such as vinyl and allyl. Preferably, at least 50% of the groups denoted by R
2
are hydrogen atoms.
Concrete examples of divalent hydrocarbon groups represented by D include alkylidene, aryl-substituted alkylidene, alkylene, cycloalkylene, arylene, and groups formed by bonding between any of the preceding groups. The structure of the alkylidene groups may be linear, branched or cyclic.
Polycarbonates having the aforementioned structure can be prepared by reacting phosgene, a carbonic acid diester or a polycarbonate oligomer with a dihydric phenol compound having the formula:
wherein R
2
and D are as defined above.
Examples of such dihydric phenol compounds include bis(4-hydroxyphenyl)methane, bis(4-hydroxyphenyl)ether, bis(4-hydroxyphenyl)sulfone, bis(4-hydroxyphenyl) sulfoxide, bis(4-hydroxyphenyl)sulfide, bis(4-hydroxyphenyl)ketone, 1,1-bis(4-hydroxyphenyl)ethane, 2,2-bis(4-hydroxyphenyl)propane, 2,2-bis(4-hydroxyphenyl)hexafluoropropane, 2,2-bis(4-hydroxyphenyl)butane, 1,1-bis(4-hydroxyphenyl)cyclohexane, 2,2-bis(4-hydroxy-3,5-dibromophenyl)propane, 2,2-bis(4-hydroxy-3,5-dichlorophenyl)propane, 2,2-bis(4-hydroxy-3-bromophenyl)propane, 2,2-bis(4-hydroxy-3-chlorophenyl)propane, 2,2-bis(4-hydroxy-3,5-diemthylphenyl)propane, 1,1-bis(4-hydroxyphenyl)-1-phenylethane and bis(4-hydroxyphenyl)diphenylmethane. Among these, 2,2-bis(4-hydroxyphenyl)propane and 1,1-bis(4-hydroxyphenyl)cyclohexane are especially desirable.
Also, as stated above, the principal chains of component (A) can comprise a polyarylate. The constituent units of the polyarylate include consituent units having the formula:
wherein R
2
and D are as defined above, and E is a substituted or unsubstituted divalent hydrocarbon group having 1 to 20 carbon atoms or a divalent hydrocarbon group having 1 to 20 carbon atoms and containing at least one alkoxysily group, provided at least 50 mole % of the groups denoted by E are aromatic hydrocarbon groups.
Examples of aromatic hydrocarbon groups represented by E include ortho-phenylene, meta-phenylene, para-phenylene, naphthylene, and diphenylenealkane. Examples of divalent hydrocarbon groups other than aromatic groups include alkylene groups, cycloalkylene groups and halogen-substituted alkylene or cycloalkylene groups. Polyarylate having the aforementioned structure can be prepared, for example, by reacting the aforementioned dihydric phenol compounds with aromatic dicarboxylic acids. Reaction methods which can be used include ordinary melt polymerization methods, interfacial polymerization methods, solution polymerization methods, and other common polymerization methods.
Component (A) of the present invention can be prepared by reacting an alkoxysilane containing silicon-bonded hydrogen atoms, having the formula:
HSiR
(3−a)
(OR′)
a
wherein R and R′ are as defined above and a is from 1 to 3, with a polycarbonate or a polyarylate having unsaturated groups selected from the group consisting of alkenyl, alkenyloxy, alkynyl, and alkynyloxy. The unsaturated groups can be located at pendant and/or terminal positions in the polycarbonate or polyarylate.
Examples of alkenyl groups include vinyl, allyl, and 5-hexenyl. Examples of alkynyl groups include ethynyl. Examples of alkenyloxy groups include vinyloxy, allyloxy, 5-hexenyloxy. Examples of alkynyloxy groups include ethynyloxy.
Examples of alkenyl group-containing polymers suitable for use as component (A) in the present composition inc
Kobayashi Hideki
Masatomi Toru
Dawson Robert
Dow Corning Toray Silicone Co. Ltd.
Milco Larry A.
Peng Kuo-Liang
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