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
1997-06-04
2001-02-20
Wilson, Donald R. (Department: 1713)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Mixing of two or more solid polymers; mixing of solid...
C525S071000, C525S074000, C525S093000, C525S261000, C525S286000, C524S321000, C524S433000
Reexamination Certificate
active
06191229
ABSTRACT:
FIELD OF THE INVENTION
The present invention generally relates to (meth)acryl syrup, a method of manufacturing the same, and a method of manufacturing molding materials including the same.
BACKGROUND OF THE INVENTION
Conventionally, molding materials including acryl syrup have been used in a variety of fields. For example, Japanese Examined Patent Application No. 11652/1989 (Tokukosho 64-11652) discloses crosslinkable acryl syrup including a polymer having a carboxyl group, and a crosslinkable monomer having a plurality of functional groups. Japanese Examined Patent Application No. 24357/1986 (Tokukosho 61-24357) discloses acryl syrup having a carboxyl group. Further, Japanese Examined Patent Application No. 2189/1978 (Tokukosho 53-2189) discloses syrup obtained by processing a thiol compound remaining in the syrup using maleic anhydride and a basic compound.
The thiol compound is typically used as a chain transfer agent for use in the polymerization reaction, and a stabilizer of the syrup. Therefore, the syrup obtained by a polymerization reaction in a presence of thiol compound contains unreacted thiol compound. Such residual thiol compound in the syrup may cause odor to be generated. The residual thiol compound also causes the viscosity to be gradually increased on storage, and may cause the syrup to be gelled. Furthermore, molded articles prepared from the molding materials including syrup are inferior in their solvent-resistance, water-resistance, and weathering resistance.
The described conventional acryl syrup is inferior in its storage stability (a so-called shelf life) as molding materials. Besides, a long time is required for curing such molding materials including acryl syrup, and the molded article prepared from the molding materials is inferior in its heat-resistance and solvent-resistance. On the other hand, when adopting the acryl syrup having no carboxyl group, a long time is required for manufacturing acryl syrup. The described deficiencies of the conventional acryl syrup have led to the need for development of a desirable (meth)acryl syrup and a manufacturing method of the same, and molding materials including the same.
Additionally, the method disclosed in Japanese Examined Patent Application No. 2189/1978 (Tokukosho 53-2189) is only applicable to the specific syrup. Thus, the method does not offer the solution of eliminating the described problems associated with the conventional (meth)acryl syrup.
The present invention is achieved in the hope of finding the solution to the above-mentioned problems. Accordingly, the first object of the present invention is to provide (meth)acryl syrup which shows an excellent storage stability as a molding material. The second object is to provide a manufacturing method of the (meth)acryl syrup which permits (meth)acryl syrup to be manufactured in a shorter time compared with the conventional method. The third object of the present invention is to provide molding materials which can be cured in shorter period of time compared with the conventional method, while having excellent properties in their heat-resistance, solvent-resistance, weathering resistance and water-resistance, etc.
DISCLOSURE OF THE INVENTION
Extensive studies have been made by the inventors of the present invention on (meth)acryl syrup, the manufacturing method of the same, and a molding material including the same. As a result, they have found that (meth)acryl syrup prepared, for example, by the following methods shows excellent storage stability (a so-called shelf life) as a molding material.
a) After polymerizing a monomer component including (meth)acrylic ester with a vinyl monomer having a carboxyl group in a presence of a thiol compound, the reaction mixture is processed with maleic anhydride and a basic compound; and
b) After polymerizing a monomer component including the (meth)acrylic ester in a presence of a thiol compound, the reaction mixture is processed with the maleic anhydride and a basic compound, and a vinyl monomer having a carboxyl group is added to the reaction mixture. They have also found that the molded article manufactured from the molding materials including (meth)acryl syrup prepared in the described methods shows excellent heat-resistance, solvent-resistance, weathering resistance and water-resistance to complete the present invention.
Namely, in order to solve the above problem, the method of manufacturing (meth)acryl syrup in accordance with the present invention is characterized by including the steps of:
(a) polymerizing a monomer component including (meth)acrylic ester with a vinyl monomer having a carboxyl group in a presence of a thiol compound; and
(b) processing a reaction mixture using maleic anhydride and a basic compound after the step (a).
In order to solve the above problem, another method of manufacturing (meth)acryl syrup in accordance with the present invention is characterized by including the steps of:
(a) polymerizing a monomer component including (meth)acrylic ester in a presence of a thiol compound; and
(b) processing a reaction mixture using maleic anhydride and a basic compound and adding a vinyl monomer having a carboxyl group to the reaction mixture after the step (a).
According to the described methods, by adopting the vinyl monomer having a carboxyl group and processing the reaction mixture with maleic anhydride and the basic compound, the (meth)acryl syrup which shows excellent storage stability as a molding material can be manufactured in a shorter period of time compared with the conventional method. The described method offers (meth)acryl syrup which shows excellent storage stability as a molding material can be achieved.
In order to solve the above problem, the molding material in accordance with the present invention is characterized by including (meth)acryl syrup prepared by any of the described methods of the present invention. In order to solve the described problem, a molding material in accordance with the present invention is characterized by including (meth)acryl syrup obtained by polymerizing a monomer component including (meth)acrylic ester in a presence of a thiol compound, and subsequently processing the resulting reaction mixture with maleic anhydride and the basic compound, and a vinyl monomer having a carboxyl group.
The described structure permits the molding material to be cured in a shorter period of time compared with the conventional (meth)acryl syrup, and offers the molding material which shows excellent properties in its heat-resistance, solvent-resistance, weathering resistance and water-resistance.
The present invention will now be described in further detail.
(i) A (meth)acryl syrup in accordance with the present invention is manufactured by polymerizing a monomer component including (meth)acrylic ester with a vinyl monomer having a carboxyl group in a presence of a thiol compound, and subsequently processing the reaction mixture with maleic anhydride and a basic compound;
(ii) Another (meth)acryl syrup in accordance with the present invention is manufactured by polymerizing a monomer component including (meth)acrylic ester in a presence of a thiol compound, and subsequently processing the reaction mixture with maleic anhydride and a basic compound and adding a vinyl monomer having a carboxyl group to the reaction mixture;
(iii) Still another (meth)acryl syrup in accordance with the present invention is manufactured by polymerizing a monomer component including (meth)acrylic ester in a presence of a thiol compound, and subsequently adding a vinyl ether compound and/or a vinyl thioether compound to the reaction mixture;
(iv) Still another (meth)acryl syrup in accordance with the present invention is manufactured by polymerizing a monomer component including (meth)acrylic ester with a vinyl monomer having a carboxyl group in a presence of a thiol compound, and subsequently adding a vinyl ether compound and/or a vinyl thioether compound to the reaction mixture;
(v) Still another (meth)acryl syrup in accordance with the present invention is manufactured by polymerizing a mono
Fukada Akihiko
Mizuta Keiichiro
Sasabe Masazumi
Kubovcik & Kubovcik
Nippon Shokubai Co. , Ltd.
Wilson Donald R.
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