Polyfunctional phenylene ether oligomer, derivative thereof, resin composition containing the same, and use thereof

Abstract

A polyfunctional phenylene ether oligomer (B) having 3 to less than 9 phenolic hydroxyl groups, obtained by reacting a polyfunctional phenol (A) having 3 to less than 9 phenolic hydroxyl groups per molecule and having alkyl groups and/or alkylene groups at 2- and 6-positions of at least one of the phenolic hydroxyl groups with a monohydric phenol compound of the formula (1), derivatives thereof, resin compositions containing the derivatives, curable films obtained therefrom and cured films thereof,

Description

BRIEF DESCRIPTION OF DRAWINGS

In each of the following figures, a vertical axis shows the intensity of absorption and a horizontal axis shows ppm.

FIG. 1 shows ¹H-NMR spectrum of a polyfunctional phenylene ether oligomer (a) obtained in Example 1.

FIG. 2 shows ¹H-NMR spectrum of a polyfunctional phenylene ether oligomer (c) obtained in Example 3.

FIG. 3 shows ¹H-NMR spectrum of a polyfunctional phenylene ether oligomer (d) obtained in Example 4.

FIG. 4 shows ¹H-NMR spectrum of a polyfunctional phenylene ether oligomer (e) obtained in Example 5.

FIG. 5 shows ¹H-NMR spectrum of a polyfunctional phenylene ether oligomer (f) obtained in Example 6.

FIG. 6 shows ¹H-NMR spectrum of a polyvinyl benzyl ether compound (h) obtained in Example 7.

FIG. 7 shows ¹H-NMR spectrum of a polyvinyl benzyl ether compound (j) obtained in Example 9.

FIG. 8 shows ¹H-NMR spectrum of a polyvinyl benzyl ether compound (k) obtained in Example 10.

FIG. 9 shows ¹H-NMR spectrum of a polyvinyl benzyl ether compound (1) obtained in Example 11.

FIG. 10 shows ¹H-NMR spectrum of a polyvinyl benzyl ether compound (m) obtained in Example 12.

FIG. 11 shows ¹H-NMR spectrum of a polyfunctional epoxy resin (p) obtained in Example 35.

FIG. 12 shows ¹H-NMR spectrum of a polyfunctional epoxy resin (r) obtained in Example 37.

FIG. 13 shows ¹H-NMR spectrum of a polyfunctional epoxy resin (s) obtained in Example 38.

FIG. 14 shows ¹H-NMR spectrum of a polyfunctional epoxy resin (t) obtained in Example 39.

FIG. 15 shows ¹H-NMR spectrum of a polyfunctional epoxy resin (u) obtained in Example 40.

Claims

1. A polyvinyl benzyl ether compound (C) obtained by vinyl-benzylating a phenolic hydroxyl group of a polyfunctional phenylene ether oligomer (B) having 3 to less than 9 phenolic hydroxyl groups, the polyfunctional phenylene ether oligomer (B) being obtained by reacting a polyfunctional phenol (A) having 3 to less than 9 phenolic hydroxyl groups per molecule and having two groups which are the same or different and are selected from the group consisting of an alkyl group and an alkylene group at 2- and 6-positions of at least one of the 3 to less than 9 phenolic hydroxyl groups with a monohydric phenol compound represented by the formula (1),

2. The polyvinyl benzyl ether compound (C) according to claim 1, wherein the polyfunctional phenylene ether oligomer (B) has a number average molecular weight of 700 to 3,000 as polystyrene.

3. The polyvinyl benzyl ether compound (C) according to claim 1, wherein the monohydric phenol compound represented by the formula (1) is a compound of the formula (2), a compound of the formula (3) or a mixture of compounds of the formula (2) and the formula (3).

4. The polyvinyl benzyl ether compound (C) according to claim 1, wherein the polyfunctional phenol (A) is at least one compound selected from the group consisting of a compound represented by the formula (4), a compound represented by the formula (5), a compound represented by the formula (6) and a compound represented by the formula (7),

5. An aromatic vinylic curable resin composition containing the polyvinyl benzyl ether compound (C) as defined in claim 1.

6. An aromatic vinylic cured product obtained by curing the curable resin composition as defined in claim 5.

7. The aromatic vinylic curable resin composition according to claim 5, which further contains a styrenic thermoplastic elastomer (D).

8. The aromatic vinylic curable resin composition according to claim 7, wherein the styrenic thermoplastic elastomer (D) has a weight average molecular weight of 30,000 to 300,000 as polystyrene.

9. The aromatic vinylic curable resin composition according to claim 7, wherein the styrenic thermoplastic elastomer (D) has a styrene content of 20 to 49% by weight.

10. A curable film obtained by processing the aromatic vinylic curable resin composition as defined in claim 7 into a film form.

11. A cured film obtained by curing the curable film as defined in claim 10.

12. A conductor-layer-formed curable film obtained by forming a conductor layer on at least one surface of the curable film as defined in claim 10.

13. A conductor-layer-formed cured film obtained by curing the conductor-layer-formed curable film as defined in claim 12.

14. A polyfunctional epoxy resin (E) obtained by glycidylating a phenolic hydroxyl group of a polyfunctional phenylene ether oligomer (B) having 3 to less than 9 phenolic hydroxyl groups, the polyfunctional phenylene ether oligomer (B) being obtained by reacting a polyfunctional phenol (A) having 3 to less than 9 phenolic hydroxyl groups per molecule and having two groups which are the same or different and are selected from the group consisting of an alkyl group and an alkylene group at 2- and 6-positions of at least one of the 3 to less than 9 phenolic hydroxyl groups with a monohydric phenol compound represented by the formula (1).

15. The polyfunctional epoxy resin (E) according to claim 14, wherein the polyfunctional phenylene ether oligomer (B) has a number average molecular weight of 700 to 3,000 as polystyrene.

16. The polyfunctional epoxy resin (E) according to claim 14, wherein the monohydric phenol compound represented by the formula (1) is a compound of the formula (2), a compound of the formula (3) or a mixture of compounds of the formula (2) and the formula (3).

17. The polyfunctional epoxy resin (E) according to claim 14, wherein the polyfunctional phenol (A) is at least one compound selected from the group consisting of a compound represented by the formula (4), a compound represented by the formula (5), a compound represented by the formula (6) and a compound represented by the formula (7).

18. An epoxy resin composition containing the polyfunctional epoxy resin (E) as defined in claim 14.

19. An epoxy curable resin composition containing the polyfunctional epoxy resin (E) as defined in claim 14 and a curing agent.

20. An epoxy cured product obtained by curing the epoxy curable resin composition as defined in claim 19.

21. A polyfunctional phenylene ether oligomer (B) having 3 to less than 9 phenolic hydroxyl groups, which oligomer (B) is obtained by reacting a polyfunctional phenol (A) having 3 to less than 9 phenolic hydroxyl groups per molecule and having two groups which are the same or different and are selected from the group consisting of an alkyl group and an alkylene group at 2- and 6-positions of at least one of the 3 to less than 9 phenolic hydroxyl groups with a monohydric phenol compound represented by the formula (1).

22. The polyfunctional phenylene ether oligomer (B) according to claim 21, wherein the polyfunctional phenylene ether oligomer (B) has a number average molecular weight of 700 to 3,000 as polystyrene.

23. The polyfunctional phenylene ether oligomer (B) according to claim 21, wherein the monohydric phenol compound represented by the formula (1) is a compound of the formula (2), a compound of the formula (3) or a mixture of compounds of the formula (2) and the formula (3).

24. The polyfunctional phenylene ether oligomer (B) according to claim 21, wherein the polyfunctional phenol (A) is at least one compound selected from the group consisting of a compound represented by the formula (4), a compound represented by the formula (5), a compound represented by the formula (6) and a compound represented by the formula (7).