Epoxy resin composition, prepreg, resin-coated metal foil, resin sheet, laminate and multilayer board
View Patent ↗An epoxy resin composition contains a polyfunctional epoxy resin (A), a polyphenylene ether compound (B) and a phosphorus-modified curing agent (C). A polyphenylene ether (B1) having a number-average molecular weight of 500 to 3000 and an average of 1.0 to 3.0 hydroxyl groups per molecule, and an epoxy resin (B2) obtained by reacting this polyphenylene ether (B1) with an epoxy resin (D) having an average of 2.3 or fewer epoxy groups per molecule and the like, are included as the polyphenylene ether compound (B). A phosphorus-modified epoxy resin (P) is included in at least one selected from the polyfunctional epoxy resin (A), the epoxy resin (D) and a component other than the (A), (B) and (C) above. The phosphorus content is 1.5 to 4.5 mass % as a percentage of the resin solids in the epoxy resin composition.
1. An epoxy resin composition containing:
a polyfunctional epoxy resin (A);
a polyphenylene ether compound (B);
a phosphorus-modified curing agent (C); and
a component other than (A), (B) and (C), wherein:
the polyfunctional epoxy resin (A) includes an average of 3 or more epoxy groups per molecule,
the polyphenylene ether compound (B) includes an epoxy resin (B2) obtained by reacting a polyphenylene ether (B1) with an epoxy resin (D), the epoxy resin (D) having an average of 2.3 or fewer epoxy groups per molecule, and the polyphenylene ether (B1) having a number-average molecular weight of 500 to 2000 and an average of 1.0 to 3.0 hydroxyl group per molecule,
at least one selected the group consisting of the polyfunctional epoxy resin (A), the epoxy resin (D), and the component other than the (A), (B) and (C) includes a phosphorus-modified epoxy resin (P),
the phosphorus content is 1.5 to 4.5 mass % as a percentage of resin solids in the epoxy resin composition,
the phosphorus-modified curing agent (C) is a resultant in a reaction between a first compound and an organic phosphorus second compound of the following Formula (I);
the first compound is a resultant in an etherification between at least one monomer alcohol and a condensation product,
the condensation product is a resultant in a condensation between formaldehyde and a phenol compound,
wherein each R independently represents hydrogen or a C 1-6 hydrocarbon group, and n is an integer from 0 to 4,
a solids content of the phosphorus-modified curing agent (C) falls within a range of 3.9 to 43 mass % with respect to solids mass of the polyfunctional epoxy resin (A) and the polyphenylene ether compound (B), and
the polyfunctional epoxy resin (A), the polyphenylene ether compound (B) and the phosphorus-modified epoxy resin (P) are miscible.
2. The epoxy resin composition according to claim 1 , wherein the polyphenylene ether (B1) has an average of 1.5 to 2.5 hydroxyl groups per molecule.
3. The epoxy resin composition according to claim 2 , wherein the phosphorus-modified epoxy resin (P) is obtained by reacting an epoxy resin including a novolac epoxy resin or a bifunctional epoxy resin with a reaction product of a quinone compound and an organic phosphorus compound represented by Formula (I) below:
wherein each R independently represents hydrogen or a C 1-6 hydrocarbon group, and n is an integer from 0 to 4.
4. The epoxy resin composition according to claim 2 , wherein the polyfunctional epoxy resin (A) includes at least one of a cresol novolac epoxy resin and a phenol novolac epoxy resin.
5. The epoxy resin composition according to claim 2 , wherein the component other than (A), (B) and (C) includes the epoxy resin (D) having an average of 2.3 or fewer epoxy groups per molecule, and
the solids content of the phosphorus-modified curing agent (C) is 11.05 mass % with respect to solids mass of the polyfunctional epoxy resin (A) and the polyphenylene ether compound (B).
6. The epoxy resin composition according to claim 2 , further including a curing agent (E) containing no phosphorus atoms.
7. The epoxy resin composition according to claim 2 , further including an inorganic filler in an amount of 35 to 350 mass % of the resin solids in the epoxy resin composition.
8. The epoxy resin composition according to claim 1 , wherein the phosphorus-modified epoxy resin (P) is obtained by reacting an epoxy resin including a novolac epoxy resin or a bifunctional epoxy resin with a reaction product of a quinone compound and an organic phosphorus compound represented by Formula (1) below:
wherein each R independently represents hydrogen or a C 1-6 hydrocarbon group, and n is an integer from 0 to 4.
9. The epoxy resin composition according to claim 8 , wherein the polyfunctional epoxy resin (A) includes at least one of a cresol novolac epoxy resin and a phenol novolac epoxy resin.
10. The epoxy resin composition according to claim 1 , wherein the polyfunctional epoxy resin (A) includes at least one of a cresol novolac epoxy resin and a phenol novolac epoxy resin.
11. The epoxy resin composition according to claim 1 , wherein the component other than (A), (B) and (C) includes the epoxy resin (D having an average of 2.3 or fewer epoxy groups per molecule, and
the solids content of the phosphorus-modified curing agent (C) is 11.05 mass % with respect to solids mass of the polyfunctional epoxy resin (A) and the polyphenylene ether compound (B).
12. The epoxy resin composition according to claim 11 , further including a curing agent (E) containing no phosphorus atoms.
13. The epoxy resin composition according to claim 12 , further including an inorganic filler in an amount of 35 to 350 mass % of the resin solids in the epoxy resin composition.
14. The epoxy resin composition according to claim 11 , further including an inorganic filler in an amount of 35 to 350 mass % of the resin solids in the epoxy resin composition.
15. The epoxy resin composition according to claim 1 , further including a curing agent (E) containing no phosphorus atoms.
16. The epoxy resin composition according to claim 15 , further including an inorganic filler in an amount of 35 to 350 mass % of the resin solids in the epoxy resin composition.
17. The epoxy resin composition according to claim 1 , further including an inorganic filler in an amount of 35 to 350 mass % of the resin solids in the epoxy resin composition.
18. A prepreg, obtained by drying a base material that has been impregnated with the epoxy resin composition according to claim 1 .
19. A resin-coated metal foil, obtained by drying a metal foil that has been coated with the epoxy resin composition according to claim 1 .
20. A resin sheet, obtained by drying an organic film that has been coated with the epoxy resin composition according to claim 1 .
21. A laminate, comprising a desired number of at least one selected from a prepreg obtained by drying a base material that has been impregnated with the epoxy resin composition according to claim 1 , a resin-coated metal foil obtained by drying a metal foil that has been coated with the epoxy resin composition according to claim 1 and a resin sheet obtained by drying an organic film that has been coated with the epoxy resin composition according to claim 1 , which have been stacked, heated, pressed and laminate molded.
22. A multilayer board, comprising at least one selected from a prepreg obtained by drying a base material that has been impregnated with the epoxy resin composition according to claim 1 , a resin-coated metal foil obtained by drying a metal foil that has been coated with the epoxy resin composition according to claim 1 and a resin sheet obtained by drying an organic film that has been coated with the epoxy resin composition according to claim 1 , which have been laid over an inner-layer circuit board, and heated, pressed and laminate molded.
23. The epoxy resin composition according to claim 1 , wherein an epoxy equivalent of the phosphorus-modified epoxy resin (P) is 200 g/eq to 600 g/eq.
24. The epoxy resin composition according to claim 1 , wherein the epoxy resin (B2) has an average of 2.3 or fewer epoxy groups per molecule.
25. The epoxy resin composition according to claim 1 , wherein the polyfunctional epoxy resin (A) includes the phosphorus-modified epoxy resin (P).
26. The epoxy resin composition according to claim 1 , wherein:
the polyfunctional epoxy resin (A) includes the phosphorus-modified epoxy resin (P), and
the phosphorus-modified epoxy resin (P) is obtained by reacting an epoxy resin including a novolac epoxy resin or a bifunctional epoxy resin with a reaction product of a quinone compound and an organic phosphorus compound represented by Formula (1) below:
wherein each R independently represents hydrogen or a C 1-6 hydrocarbon group, and n is an integer from 0 to 4.
27. The epoxy resin composition according to claim 1 , wherein:
the polyfunctional epoxy resin (A) includes the phosphorus-modified epoxy resin (P) and an epoxy resin including no phosphorous atoms, and
the epoxy resin including no phosphorous atoms includes a cresol novolac epoxy resin.
28. The epoxy resin composition according to claim 1 , wherein:
the epoxy resin (D) includes the phosphorus-modified epoxy resin (P), and
the phosphorus-modified epoxy resin (P) includes a bifunctional phosphorous-modified epoxy resin.
29. The epoxy resin composition according to claim 1 , wherein:
the component other than the (A), (B) and (C) includes the phosphorus-modified epoxy resin (P), and
the phosphorus-modified epoxy resin (P) includes a bifunctional phosphorous-modified epoxy resin.
30. The epoxy resin composition according to claim 1 , further containing:
a curing agent (E) including no phosphorus atoms; and
a solvent, wherein
the solvent includes N, N-dimethylformamide.