Crystalline resin cured product, crystalline resin composite material, and method for producing the same
View Patent ↗Provided are a crystalline resin cured product which shows high thermal conductivity, low thermal expansion, high heat resistance, low moisture absorption, and good gas barrier properties and a crystalline resin composite material produced therefrom. Further provided is a method for producing the crystalline resin cured product and the crystalline resin composite material. The crystalline resin cured product is obtained by the reaction of an aromatic diglycidyl compound or a diglycidyl resin with an aromatic dihydroxy compound or with a dihydroxy resin and it shows a heat of melting of 10 J/g or more in differential thermal analysis while the endothermic peak corresponding to the melting appears in the range of 120 to 320° C. The crystalline resin composite material is obtained by combining the crystalline resin cured product with a filler or a base material. The crystalline resin cured product has a unit represented by -A-O—CH 2 —CH(OH)—CH 2 —O—B—, wherein A and B are divalent aromatic groups.
1. A crystalline resin cured product which is characterized in that the crystalline resin cured product contains a unit formed by the reaction of an aromatic diglycidyl compound with an aromatic dihydroxy compound and represented by the following general formula (2) in an amount of 50 wt % or more of the whole, and has a distinct melting point due to growth of the crystal domain, softens at a temperature above its melting point as the result of a loss of the crystal phase, and has a heat distortion temperature without clearly showing fluidity and, when analyzed by differential scanning calorimetry, the crystalline resin cured product absorbs a heat quantity of 10 J/g or more calculated on the basis of the resin components of the crystalline resin cured product as the crystals of the crystalline resin cured product melt and the endothermic peak appears in the range of 120 to 320° C., the reaction is performed at a temperature that is in the range of 60 to 250° C. and lower than the melting point of the crystalline resin cured product by 10 to 100° C.:
in general formula (2), A and B are divalent aromatic groups and they may be identical with or different from each other and wherein the aromatic diglycidyl compound and the aromatic dihydroxy compound are mixed in a ratio of 0.8 to 1.2 moles of the hydroxyl groups in the dihydroxy compound per 1 mole of the glycidyl groups in the aromatic diglycidyl compound;
and wherein the aromatic diglycidyl compound or the aromatic dihydroxy compound or both contain a unit represented by the following general formula (3):
in general formula (3), X is a linking group selected from a direct linkage and an ether linkage and n is an integer of 1 to 3.
2. A crystalline resin cured product as described in claim 1 wherein the main component of the crystalline resin cured product is obtained by the reaction of an aromatic diglycidyl compound with an aromatic dihydroxy compound.
3. A crystalline resin cured product as described in claim 2 wherein the aromatic diglycidyl compound or the aromatic dihydroxy compound have one kind or more of units selected from a 4,4′-diphenyl ether group, a 4,4′-diphenyl sulfide group, a 4,4′-diphenylmethane group, a 1,4-phenylene group, a 4,4′-biphenylene group, a 1,5-naphthylene group, a 2,6-naphthylene group, and a 9,10-anthracenylene group, the units being optionally substituted with a methyl group or a halogen atom or both.
4. A crystalline resin composite material comprising a filler or base material wherein the crystalline resin cured product described in claim 1 constitutes the matrix resin of the crystalline resin composite material.
5. A crystalline resin composite material as described in claim 4 wherein the filler or base material accounts for 10 to 90 wt % of the total weight.
6. A crystalline resin composite material as described in claim 4 wherein the heat distortion temperature falls in the range ±30° C. from the melting point of the crystalline resin cured product.
7. A crystalline resin cured product as described in claim 1 wherein the product has a structure formed by further using an epoxy resin curing agent other than the aromatic dihydroxy compound in the reaction with the aromatic diglycidyl compound.
8. A crystalline resin cured product as described in claim 7 wherein the aromatic diglycidyl compound and the aromatic dihydroxy compound are mixed in a ratio of 0.8 to 1.2 moles of the total hydroxyl groups in the dihydroxy compound and the epoxy curing agent per 1 mole of the glycidyl groups in the aromatic diglycidyl compound.
9. A crystalline resin cured product as described in claim 7 wherein the epoxy resin curing agent comprises an aromatic dihydroxy compound and an amine.
10. A crystalline resin cured product as described in claim 1 wherein the aromatic diglycidyl compound and the aromatic dihydroxy compound both contain a unit represented by formula (3).
11. A crystalline resin cured product as described in claim 1 wherein an epoxy resin curing catalyst is further used in the reaction of the aromatic diglycidyl compound and the dihydroxy compound.