IP Library Granted Patent US 12,168,709
Granted Patent B2
US 12,168,709 · App. 18/260,382 · Granted Dec 17, 2024

Thermosetting resin composition, prepreg, laminate, metal-clad laminate, printed wiring board, and high-speed communication compatible module

Inventors: Koji Morita (Tokyo, JP); Ryo Shimokawa (Tokyo, JP); Shinji Tsuchikawa (Tokyo, JP); Keiichi Kasuga (Tokyo, JP); Chihiro Hayashi (Tokyo, JP); Tomio Iwasaki (Tokyo, JP)
Assignee: RESONAC CORPORATION
C08F283/04
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Quick Facts
Patent No.
US 12,168,709
App. No.
18/260,382
Granted
Dec 17, 2024
Kind
B2
Abstract

A thermosetting resin composition containing a maleimide compound (a) having at least one N-substituted maleimide group, and a compound (b) represented by the following general formula (1) exhibiting no reactivity with the maleimide group of the component (a) (X b1 represents a single bond or a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 5 carbon atoms; R b1 and R b2 each independently represent a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 ring carbon atoms, a substituted or unsubstituted heterocyclic aromatic hydrocarbon group having 5 to 20 ring atoms, an oxygen atom-containing group, or a group containing a combination of these groups; and m and n each independently represent an integer of 0 to 5).

Claims (32)

1. A thermosetting resin composition comprising:

a maleimide compound (a) having at least one N-substituted maleimide group, and

a compound (b) represented by the following general formula (1) exhibiting no reactivity with the maleimide group of the component (a):

wherein in the general formula (1), X b1 represents a single bond or a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 5 carbon atoms; R b1 and R b2 each independently represent a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 ring carbon atoms, a substituted or unsubstituted heterocyclic aromatic hydrocarbon group having 5 to 20 ring atoms, an oxygen atom-containing group, or a group containing a combination of these groups; and m and n each independently represent an integer of 0 to 5,

wherein substituents that the groups in the general formula (1) can have are substituents exhibiting no reactivity with the maleimide group of the component (a) at 200° C. or less.

2. The thermosetting resin composition according to claim 1 , wherein the component (a) contains a maleimide compound (a1) having at least two N-substituted maleimide groups.

3. The thermosetting resin composition according to claim 1 , wherein the component (a) contains a reaction product of a maleimide compound (a1) having at least two N-substituted maleimide groups, and at least one kind selected from the group consisting of a monoamine compound (a2) and an amine compound (a3) having at least two amino groups.

4. The thermosetting resin composition according to claim 2 , wherein the component (a1) is a maleimide compound having an aliphatic hydrocarbon group between nitrogen atoms of optional two N-substituted maleimide groups among the multiple N-substituted maleimide groups (provided that no aromatic hydrocarbon group exists), or a maleimide compound having an aromatic hydrocarbon group between nitrogen atoms of optional two N-substituted maleimide groups among the multiple N-substituted maleimide groups.

5. A thermosetting resin composition comprising:

a maleimide compound (a) having at least one N-substituted maleimide group, wherein the component (a) contains a reaction product of a maleimide compound (a1) having at least two N-substituted maleimide groups and a silicone compound (a3′) having at least two amino groups, and

a compound (b) represented by the following general formula (1) exhibiting no reactivity with the maleimide group of the component (a):

wherein in the general formula (1), X b1 represents a single bond or a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 5 carbon atoms; R b1 and R b2 each independently represent a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 ring carbon atoms, a substituted or unsubstituted heterocyclic aromatic hydrocarbon group having 5 to 20 ring atoms, an oxygen atom-containing group, or a group containing a combination of these groups; and m and n each independently represent an integer of 0 to 5.

6. The thermosetting resin composition according to claim 5 , wherein the component (a) is a reaction product of the component (a1), the component (a3′), and an amine compound (a3) having at least two amino groups (provided that the component (a3′) is excluded).

7. The thermosetting resin composition according to claim 1 , wherein the component (b) is represented by the following general formula (1′):

wherein in the general formula (1′), R b1 , R b2 , m, and n have the same meanings as in the general formula (1).

8. The thermosetting resin composition according to claim 1 , wherein the component (b) has a boiling point of 260° C. or more under one atmosphere (101.325 kPa).

9. The thermosetting resin composition according to claim 1 , wherein the component (b) is at least one kind selected from the group consisting of diethylbiphenyl and benzylbiphenyl.

10. The thermosetting resin composition according to claim 1 , wherein in the general formula (1), R b1 and R b2 represent oxygen atom-containing groups.

11. The thermosetting resin composition comprising:

a maleimide compound (a) having at least one N-substituted maleimide group, and

a compound (b) represented by the following general formula (1) exhibiting no reactivity with the maleimide group of the component (a);

wherein in the general formula (1), X b1 represents a single bond or a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 5 carbon atoms; R b1 and R b2 each independently represent a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 ring carbon atoms, a substituted or unsubstituted heterocyclic aromatic hydrocarbon group having 5 to 20 ring atoms, an oxygen atom-containing group, or a group containing a combination of these groups; and m and n each independently represent an integer of 0 to 5,

wherein the thermosetting resin composition has a content of the component (b) of 0.001 to 1.0 mol per 1 mol of the component (a).

12. The thermosetting resin composition according to claim 1 , wherein the thermosetting resin composition further comprises an inorganic filler (c).

13. The thermosetting resin composition according to claim 1 , wherein the thermosetting resin composition further comprises a thermosetting resin (d).

14. The thermosetting resin composition according to claim 1 , wherein the thermosetting resin composition further comprises a curing accelerator (e).

15. The thermosetting resin composition according to claim 1 , wherein the thermosetting resin composition further comprises a monoamine compound (f).

16. The thermosetting resin composition according to claim 1 , wherein the thermosetting resin composition further comprises an amine compound (g) having at least two amino groups.

17. A prepreg comprising a semi-cured material of the thermosetting resin composition according to claim 1 .

18. A laminate comprising a cured material of the prepreg according to claim 17 .

19. A printed wiring board comprising the laminate according to claim 18 , and a circuit formed thereon.

20. A high-speed communication compatible module comprising the printed wiring board according to claim 19 .

Assignments (2)
CHANGE OF ADDRESS Recorded Feb 9, 2024
From: RESONAC CORPORATION
To: RESONAC CORPORATION
Reel/Frame 066547/0677 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 11, 2023
From: MORITA, KOJI; SHIMOKAWA, RYO; TSUCHIKAWA, SHINJI; KASUGA, KEIICHI; HAYASHI, CHIHIRO; IWASAKI, TOMIO
To: RESONAC CORPORATION
Reel/Frame 064213/0355 →