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
2000-01-27
2001-08-21
Acquah, Samuel A. (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Mixing of two or more solid polymers; mixing of solid...
C528S295500, C528S302000, C528S306000, C528S308000, C525S437000, C525S444000, C522S006000
Reexamination Certificate
active
06277929
ABSTRACT:
The present invention relates to a polymerizable unsaturated compound exhibiting, after being cured, excellent adhesive property, heat resistance, water resistance and flexibility, and to a method for production thereof.
The invention further relates to a curable resin composition comprising said polymerizable unsaturated compound and a diluent, and a molded article obtained by curing said curable resin composition.
Curable resin compositions such as UV-curable resin composition and the like are characterized in that they have a high drying velocity and do not pollute the working environment. Thus, the curable resin compositions are used in many fields including coating materials, inks, adhesives, etc. Recently, the demand of (meth)acrylate type curable resin compositions is increasing as casting type gasket, sealing material and coating material, and the requirement for their quality is becoming more and more severe. In cases of gasket and sealing material, flexibility and adhesiveness are required from the viewpoint of tightness of bonding to substrate and, in addition, high durabilities such as water resistance and heat resistance are severely demanded under high-temperature, high-humidity conditions.
As prior acrylate type curable resin composition, for instance, a curable resin composition comprising a polymerizable unsaturated polybutadiene obtainable by reacting a polybutadiene-polyol/polyisocyanate/hydroxyalkyl acrylate system is disclosed in JP-A-Sho 58(1983)-76414 and JP-A-Sho 61(1986)-21120. Although the cured articles obtained from such a composition containing polymerizable unsaturated polybutadiene are excellent in flexibility and water resistance, they are inferior in adhesiveness and heat resistance. In “UV, EB-Curable Materials” (published by CMC Corp.), p.74, (1992), there is disclosed a curable resin composition comprising a polymerizable unsaturated polyurethane prepared by subjecting a dicarboxylic acid such as adipic acid, succinic acid, terephthalic acid, isophthalic acid or the like to a polycondensation with a glycol such as ethylene glycol, diethylene glycol, neopentyl glycol, 1,4-butanediol or the like to form a polyester-polyol and then reacting the polyester-polyol with a polyisocyanate and a hydroxyalkyl acrylate. Although cured articles of this composition comprising a polymerizable unsaturated polyurethane have a high heat resistance, they are inferior in flexibility, adhesiveness and water resistance. Further, in JP-A-Hei 2(1990)-248414, there is disclosed a curable resin composition comprising a polymerizable unsaturated polyester prepared by subjecting adipic acid to a polycondensation with 2-butyl-2-ethyl-1,3-propanediol to obtain a polyester-polyol and then esterifying the polyester-polyol with acrylic acid. Although cured article of this composition comprising the polymerizable unsaturated polyester is improved in heat resistance, it is inferior in adhesiveness, water resistance and flexibility.
It is an object of the present invention to provide a polymerizable unsaturated compound giving, after cure, a material superior in adhesion to substrate and excellent in heat resistance, water resistance and flexibility.
It is another object of the present invention to provide a curable resin composition comprising a polymerizable unsaturated compound and a diluent and excellent in adhesiveness, water resistance, heat resistance and flexibility.
It is a yet another object of the present invention to provide a molded article excellent in air-tightness and durability under high-temperature and high-humidity conditions which can be obtained by curing a curable resin composition.
The present inventors conducted extensive studies with the aim of overcoming the problems of prior art. As a result, it was found that a curable resin composition superior in adhesiveness to substrate and excellent in flexibility, heat resistance and water resistance can be obtained by using, as a polymerizable unsaturated ingredient, (1) a polymerizable unsaturated polyester obtained by subjecting polymerized fatty acid-containing polybasic carboxylic acid to a polycondensation with a polyhydric alcohol to prepare a polyester-polyol and then esterifying the polyester-polyol with an unsaturated carboxylic acid and/or (2) an unsaturated (poly)urethane obtained by reacting said polymerized fatty acid-containing polyester-polyol with a polyisocyanate and an active hydrogen-containing polymerizable unsaturated compound. Further, it was also found that molded articles such as gasket and the like obtained by curing said curable resin composition are quite superior in air tightness and durability under high-temperature and high-humidity conditions. Based on these findings, the present invention was accomplished.
According to the present invention, there is provided an unsaturated polyester (i) having a weight-average molecular weight of 1,000-100,000 and at least two polymerizable carbon-carbon unsaturated bonds in the molecule thereof, said unsaturated polyester (i) being obtained by subjecting a polybasic carboxylic acid component containing at least one member selected from the group consisting of polymerized fatty acid and polymerized fatty acid ester to a polycondensation reaction with a polyhydric alcohol to prepare a polyester-polyol (a), followed by esterifying (a) with an unsaturated carboxylic acid (b) having a polymerizable carbon-carbon unsaturated bond in the molecule thereof.
Further, according to the present invention, there is provided a method for producing said unsaturated polyester (i) characterized by subjecting a polybasic carboxylic acid component containing at least one member selected from the group consisting of polymerized fatty acid and polymerized fatty acid ester to a polycondensation reaction with a polyhydric alcohol to prepare a polyester-polyol (a), followed by reacting (a) with an unsaturated carboxylic acid (b) having a polymerizable carbon-carbon unsaturated bond in the molecule thereof.
Further, according to the present invention, there is provided an unsaturated (poly)urethane (ii) having a weight-average molecular weight (Mw) of 1,000-100,000 and at least two polymerizable carbon-carbon unsaturated bonds in the molecule thereof, said unsaturated (poly)urethane (ii) being obtained by subjecting a polybasic carboxylic acid component containing at least one member selected from the group consisting of polymerized fatty acid and polymerized fatty acid ester to a polycondensation reaction with a polyhydric alcohol to prepare a polyester-polyol (c), followed by reacting (c) with a polyisocyanate (d) and at least one active hydrogen-containing polymerizable unsaturated compound (e) selected from the group consisting of acrylic acid, methacrylic acid, acrylamide, methacrylamide, active hydrogen-containing acrylic esters, active hydrogen-containing methacrylic esters and active hydrogen-containing styrenes represented by the following general formula (8):
CH
2
═CR
10
—B—X (8)
wherein R
10
is hydrogen atom or alkyl group, B is phenylene group and X is hydroxyl group, amino group or carboxyl group.
Further, according to the present invention, there is provided a method for producing the unsaturated (poly)urethane (ii) characterized by subjecting a polybasic carboxylic acid component containing at least one member selected from the group consisting of polymerized fatty acid and polymerized fatty acid ester to a polycondensation reaction with a polyhydric alcohol to prepare a polyester-polyol (c), followed by reacting the polyester-polyol (c) with a polyisocyanate (d) and the above-mentioned active hydrogen-containing polymerizable unsaturated compound
Further, according to the present invention, there is provided a method for producing the unsaturated (poly)urethane (ii) characterized by subjecting a polybasic carboxylic acid component containing at least one member selected from the group consisting of polymerized fatty acid and polymerized fatty acid ester to a polycondensation reaction with a polyhydric alcohol to prepare a polyester-p
Hayashi Hiroshi
Kawabuchi Ichiro
Kitahara Shizuo
Acquah Samuel A.
Lyon & Lyon LLP
Neuman Kristin H.
Shalek James H.
Vantico Inc.
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