Modified cycloolefin addition polymer and curable resin...

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

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C525S332500, C525S210000, C525S211000, C525S286000, C526S281000, C526S282000

Reexamination Certificate

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06346581

ABSTRACT:

TECHNICAL FIELD
The present invention relates to modified cycloolefin addition polymers and curable (hardening) resin compositions containing such a polymer, and more particularly to modified cycloolefin addition polymers excellent in heat resistance, mechanical properties, solution viscosity characteristics, adhesion to metals, dielectric properties, low moisture absorption property, chemical resistance, etc., and curable resin compositions excellent in flexibility and thick film-forming property. The modified cycloolefin addition polymers and curable resin compositions containing such a polymer according to the present invention are particularly suitable for use in, for example, a field of electronic parts as interlayer insulating films, protective films, sealing materials, adhesives and the like.
BACKGROUND ART
Cycloolefin polymers such as norbornene polymers have attracted attention as insulating materials in an electrical and electronic field because they are excellent in dielectric properties and low water absorption property. Of the cycloolefin polymers, cycloolefin addition polymers typified by norbornene addition polymers generally have a high glass transition temperature and tend to be provided as polymers having a high degree of saturation and are hence suitable for use in field of which high heat resistance, chemical resistance (solvent resistance) and the like are required. It is also known that when a hardening (curing) agent is blended into a cycloolefin addition polymer to prepare a curable resin composition, the heat resistance and chemical resistance of the polymer are further improved.
For example, Japanese Patent Application Laid-Open No. 259784/1996 discloses a process in which a methyltetracyclododecene (MTD)/ethylene addition copolymer or MTD/ethylene/ethylidenenorbornene terpolymer is epoxy-modified, and a bisazide hardening agent or amine hardening agent is then blended into the resultant modified product to prepare a curable resin composition. This publication also discloses the fact that the use of such a curable resin composition permits the formation of an insulating film excellent in heat resistance and solvent resistance in addition to properties such as low water absorption property and dielectric properties. However, the film formed by using such a curable resin composition is insufficient in flexibility and hence difficult to form a thick film. In fact, these curable resin compositions have involved a problem that when a film having a thickness of at least 10 &mgr;m is actually formed to cure it, the resulting film tends to crack, and so its reliability as an insulating film is insufficient.
On the other hand, addition polymer of substituent-containing norbornenes or addition copolymers of such a substituent-containing norbornene with norbornene have been known as norbornene addition polymers containing a substituent group having a relatively great number of carbon atoms [Japanese Patent Application Laid-Open No. 198919/1996, U.S. Pat. No. 5,468,819, International Patent WO 95/14048, International Patent WO 96/37526, and Macromolecules, 29, 2755 (1996)]. Of these papers, Japanese Patent Application Laid-Open No. 198919/1996, U.S. Pat. No. 5,468,819 and International Patent WO 95/14048 disclose addition copolymers of a long chain linear alkyl-substituted norbornene with norbornene and describe the fact that when norbornene is copolymerized with the long chain alkyl-substituted norbornene, the glass transition temperature (Tg) of the resulting norbornene addition polymer is lowered. International Patent WO 96/37526, and Macromolecules, 29, 2755 (1996) describe addition polymers of norbornene having a long chain linear carboxylic ester as a substituent or addition copolymers of the ester group-containing norbornene with norbornene. However, these norbornene addition (co)polymers is insufficient in adhesion to metals and the like, and their use in application fields such as overcoating films, interlayer insulating films, passivation films, buffer coating films and sealing materials is limited to a great extent.
DISCLOSURE OF THE INVENTION
It is an object of the present invention to provide a modified cycloolefin addition polymer excellent in heat resistance, mechanical properties, solution viscosity characteristics, adhesion to metals, dielectric properties, low moisture absorption property, chemical resistance, etc.
Another object of the present invention is to provide a process for preparing a modified cycloolefin addition polymer having such excellent various properties.
A further object of the present invention is to provide a curable resin composition which is excellent in heat resistance, mechanical properties, solution viscosity characteristics, adhesion to metals, dielectric properties, low moisture absorption property, chemical resistance, etc., and also in flexibility and thick film-forming property and has a low coefficient of linear expansion.
The present inventors have carried out an extensive investigation with a view toward overcoming the above-described problems involved in the prior art. As a result, it has been found that a modified cycloolefin addition polymer obtained by introducing a functional group into a cycloolefin addition polymer containing a repeating unit (a) derived from a cycloolefin monomer having an organic group having at least 4 carbon atoms at its side chain is excellent in adhesion to metals and the like and also flexibility, so that no cracking occurs in a thick film even when the film is formed from the addition polymer to cure it. The modified cycloolefin addition polymer according to the present invention, and a curable resin composition comprising the polymer and a hardening agent are excellent in heat resistance, mechanical properties, solution viscosity characteristics, adhesion to metals, dielectric properties, low moisture absorption property, chemical resistance, etc. The present invention has been led to completion on the basis of these findings.
According to the present invention, there is thus provided a curable resin composition comprising a modified cycloolefin addition polymer (A) obtained by introducing a functional group into a cycloolefin addition polymer containing a repeating unit (a) derived from a cycloolefin monomer having an organic group having at least 4 carbon atoms at its side chain at a rate of introduction of the functional group of 0.1 to 50 mol % based on the whole repeating unit of the cycloolefin addition polymer, and a hardening agent (B).
According to the present invention, there is also provided a cured product obtained by curing the curable resin composition, particularly, a film.
According to the present invention, there is further provided a modified cycloolefin addition polymer (A) obtained by introducing a functional group into a cycloolefin addition polymer containing a repeating unit (a) derived from a cycloolefin monomer having an organic group having at least 4 carbon atoms at its side chain at a rate of introduction of the functional group of 0.1 to 50 mol % based on the whole repeating unit of the cycloolefin addition polymer, and having a weight average molecular weight (Mw) of 1,000 to 1,000,000.
According to the present invention, there is still further provided a process for preparing a modified cycloolefin addition polymer (A) having a weight average molecular weight (Mw) of 1,000 to 1,000,000, the process comprising graft-reacting an unsaturated compound having a functional group with a cycloolefin addition polymer containing a repeating unit (a) derived from a cycloolefin monomer having an organic group having at least 4 carbon atoms at its side chain, thereby introducing the functional group at a rate of introduction of the functional group of 0.1 to 50 mol % based on the whole repeating unit of the cycloolefin addition polymer.
According to the present invention, there is yet still further provided a process for preparing a modified cycloolefin addition polymer (A) having a weight average molecular weight (Mw) of 1,000 to 1,000,000, the proces

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