Thermosetting resin composition and use thereof

Details Thermosetting resin composition and use thereof Thermosetting resin composition and use thereof

2002-01-30

2003-12-23

Dawson, Robert (Department: 1712)

Stock material or miscellaneous articles

Composite

Of addition polymer from unsaturated monomers

C523S466000, C525S333300, C525S328200, C525S327400

Reexamination Certificate

active

06667107

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a thermosetting resin composition, and a prepreg and a laminated sheet for electrically insulating material using the thermosetting resin composition.
2. Prior Art
As printed wiring boards for electronic appliance, laminated sheets mainly using an epoxy resin have been widely used. However, in accordance with tendencies that a pattern becomes finer due to the increase in the mounting density in electronic appliance, the surface mount system is generally employed, the signal propagation velocity becomes higher, and the frequency of the signal used becomes higher, a development of printed wiring board materials having a low dielectric loss and an improved heat resistance are strongly desired.
As a prior art of a resin composition or laminated sheet using an epoxy resin as a curing agent and using a copolymer resin comprising styrene and maleic anhydride, for example, Japanese Unexamined Patent Publication No. 109476/1974 has a description about a flexible printed wiring board from a flexible epoxy resin and a copolymer resin which comprises styrene and maleic anhydride, wherein a reactive epoxy diluent and an acrylonitrile-butadiene copolymer are necessary for imparting flexibility to the printed wiring board. In addition, Japanese Unexamined Patent Publication No. 221413/1989 has descriptions about a copolymer resin having an acid value of 280 or more, which is obtained from an epoxy resin, an aromatic vinyl compound, and maleic anhydride, and about an epoxy resin compound containing dicyanamide. Further, Japanese Unexamined Patent Publication No. 25349/1997 has descriptions about a prepreg and a laminated sheet material for electrical appliance, comprising a brominated epoxy resin, a copolymer resin comprising styrene and maleic anhydride (epoxy resin curing agent), a styrene compound, and a solvent. Japanese Unexamined Patent Publications No. 17685/1998 and No. 17686/1998 have descriptions about a prepreg and a laminated sheet material for electrical appliance, comprising an epoxy resin, a copolymer resin of an aromatic vinyl compound and maleic anhydride, and a phenolic compound. Japanese Unexamined national Patent Publication (kohyo) No. 505376/1998 has descriptions about a resin composition, a laminated sheet, and a printed wiring board, comprising an epoxy resin, a cross-linking agent for carboxylic anhydride-type epoxy resin, and an allyl network-forming compound. However, these prior art materials do not have performance required for the tendency that the pattern becomes finer and the frequency of the signal becomes higher, that is, they do not have low dielectric loss, excellent heat resistance, excellent moisture resistance, and excellent adhesion to a copper foil.
SUMMARY OF THE INVENTION
It is an object of the present invention to provide a thermosetting rein composition free of the above-stated problems, which composition is excellent in all, low dielectric loss, heat resistance, moisture resistance, and adhesion to a copper foil, and the use thereof, for example, a prepreg and a laminated sheet.
In one aspect, the present invention is directed to a thermosetting resin composition comprising:
(1) a copolymer resin comprising (a) a monomer unit represented by the following general formula (I):
wherein R
1
represents a hydrogen atom, a halogen atom, or a hydrocarbon group having 1 to 5 carbon atoms; R
2
or each of R
2
's independently represents a halogen atom, an aliphatic hydrocarbon group having 1 to 5 carbon atoms, or an aromatic hydrocarbon group; x is an integer of 0 to 3, preferably 0; and m is a natural number, and
(b) a monomer unit represented by the following general formula (II):
wherein n is a natural number; and
(2) a thermosetting resin which is cured together with said component (1),
wherein a cured product of said composition has a dielectric constant of 3.0 or less at a frequency of 1 GHz or more and has a glass transition temperature of 170° C. or more, and the composition is not constituted only by said (1).
In one aspect of the present invention, it is preferred to use a thermosetting resin composition wherein the said component (1) is replaced by (1)′ a copolymer resin comprising the said monomer unit (a) and (b), and further comprises, as a monomer unit (c), N-phenylmaleimide represented by the following general formula (III):
wherein R
3
represents a halogen atom, an aliphatic hydrocarbon group having 1 to 5 carbon atoms, an aromatic hydrocarbon group, a hydroxyl group, a thiol group, or a carboxyl group; y is an integer of 0 to 3, preferably 0; and r is a natural number,
and/or a derivative thereof. In addition, it is also preferred that the component (2) a thermosetting resin is (2)′ a cyanate resin having at least two cyanate groups per molecule.
In another aspect, the present invention is directed to a thermosetting resin composition comprising:
(1) a copolymer resin comprising
(a) a monomer unit represented by the following general formula (I):
wherein R
1
represents a hydrogen atom, a halogen atom, or a hydrocarbon group having 1 to 5 carbon atoms; R
2
or each of R
2
's independently represents a halogen atom, an aliphatic hydrocarbon group having 1 to 5 carbon atoms, an aromatic hydrocarbon group, or a hydroxyl group; x is an integer of 0 to 3, preferably 0; and m is a natural number, and
(b) a monomer unit represented by the following general formula (II):
wherein n is a natural number; and
(2)′ a cyanate resin having at least two cyanate groups per molecule.
In another aspect of the present invention, it is preferred to use a thermosetting resin composition wherein the said component (1) is replaced by (1)′ a copolymer resin comprising the said monomer unit (a) and (b), and further comprises, as a monomer unit (c), N-phenylmaleimide represented by the following general formula (III):
wherein R
3
represents a halogen atom, an aliphatic hydrocarbon group having 1 to 5 carbon atoms, an aromatic hydrocarbon group, a hydroxyl group, a thiol group, or a carboxyl group; y is an integer of 0 to 3, preferably 0; and r is a natural number and/or a derivative thereof.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
Hereinafter, the present invention will be described in more detail.
In the present invention, component (1) or (1)′ is a copolymer resin comprising styrene and maleic anhydride. In the present invention, the monomer unit (a) is obtained from a compound, such as styrene, 1-methylstyrene, vinyltoluene, dimethylstyrene, chlorostyrene, or bromostyrene, and these compounds can be used individually or in combination. Further, various polymerizable components other than the above-stated monomer units may be copolymerized, and examples of these polymerizable components include vinyl compounds, such as ethylene, propylene, butadiene, isobutylene, acrylonitrile, vinyl chloride, and fluoroethylene, and compounds having a methacryloyl group or an acryloyl group, such as methacrylate such as methyl methacrylate, and acrylate such as methyl acrylate. A substituent, such as an allyl group, a methacryloyl group, an acryloyl group, or a hydroxyl group, can be optionally introduced into the component (a) through a Friedel-Crafts reaction or a reaction using a metal catalyst, such as lithium.
In the present invention, various hydroxyl group-containing compounds, amino group-containing compounds, cyanate group-containing compounds, and epoxy group-containing compounds can be introduced into the monomer unit (b).
In the present invention, as the monomer units (c), preferred are N-phenylmaleimide and derivatives of N-phenylmaleimide, which have a phenolic hydroxyl group, from the viewpoint of obtaining excellent dielectric property and an appropriate glass transition temperature, and especially preferred is N-phenylmaleimide from the viewpoint of obtaining excellent heat resistance and excellent moisture resistance. Examples of derivatives of N-phenylmaleimide include compounds represented by general formulae (IV) to (IX):

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