Modified silicone compound, and thermosetting resin composition, prepreg, laminate plate and printed wiring board using same

Patent metadata

Field	Value
Publication number	US-11401381-B2
Application number	US-201213980385-A
Country	US
Kind code	B2
Filing date	Jan 17, 2012
Priority date	Jan 18, 2011
Publication date	Aug 2, 2022
Grant date	Aug 2, 2022

Abstract

There are provided a modified silicone compound prepared by reacting: (A) a siloxane diamine represented by the general formula (1); (B) a maleimide compound with at least two N-substituted maleimide groups in the molecular structure; and (C) an amine compound with an acidic substituent; and also provided a thermosetting resin composition, a prepreg, a laminated plate, and a printed wiring board that are formed by using this compound. The multi-layered printed wiring board produced by using the laminated plate formed by using the prepreg obtained from the modified silicone compound and the thermosetting resin composition of the present invention through laminate molding has an excellent glass transition temperature, coefficient of thermal expansion, copper foil adhesion, hygroscopicity, hygroscopic solder heat resistance, and copper-stuck solder heat resistance. Therefore, the multi-layered printed wiring board is useful as a highly integrated semiconductor package and a printed wiring board for an electronic device.

First claim

The invention claimed is:

1. A modified silicone compound prepared by reacting:
(A) a siloxane diamine component comprising a siloxane diamine represented by a general formula (1):

wherein a plurality of R 1 s each independently represent an alkyl group, a phenyl group, or a substituted phenyl group and may be the same as or different from each other, a plurality of R 2 s each independently represent an alkyl group, a phenyl group, or a substituted phenyl group and may be the same as or different from each other, R 3 and R 4 each independently represent an alkyl group, a phenyl group, or a substituted phenyl group, R 5 and R 6 represent C 3 H 6 , n represents an integer of 2-50, and at least one of the following conditions (i)-(iv) is met:
(i) at least one of the R 1 s represents a phenyl group or a substituted phenyl group,
(ii) at least one of the R 2 s represents a phenyl group or a substituted phenyl group,
(iii) R 3 represents a phenyl group or a substituted phenyl group, and
(iv) R 4 represents a phenyl group or a substituted phenyl group;

(B) a maleimide component comprising a maleimide compound with at least two N-substituted maleimide groups in a molecular structure, wherein an amount of the maleimide component (B) is 100-3000 parts by mass, based on 100 parts by mass of the siloxane diamine component (A);
(C) an amine component comprising an amine compound with an acidic substituent represented by a general formula (2):

wherein R 9 or a plurality of R 9 s each independently represent a hydroxyl, a carboxyl, or a sulfonic group that is an acidic substituent, R 10 or a plurality of R 10 s each independently represent a hydrogen atom, an aliphatic hydrocarbon group with 1-5 carbon atoms, or a halogen atom, x represents an integer of 1-5, y represents an integer of 0-4, and x+y=5, and
an amount of the amine compound represented by general formula (2) is 1-8.454 parts by mass, based on 100 parts by mass of the siloxane diamine represented by general formula (1); and
(D) an optional amine component comprising at least one selected from the group consisting of m-phenylenediamine, p-phenylenediamine, 1,4-bis(4-aminophenoxy)benzene, 4,4′-diaminodiphenylmethane, 3,3′-dimethyl-4,4′-diaminodiphenylmethane, 3,3′-diethyl-4,4′-diaminodiphenylmethane, 4,4′-diaminobenzophenone, 4,4′-diaminodiphenyl ether, 3,3′-diaminodiphenyl sulfone, 4,4′-diaminodiphenyl sulfone, benzidine, 4,4′-diaminodiphenyl sulfide, 4,4′-diamino-3,3′-biphenyldiol, and a guanamine.

2. A thermosetting resin composition comprising the modified silicone compound according to claim 1 .

3. The thermosetting resin composition according to claim 2 , further comprising an epoxy resin and/or a cyanate resin.

4. The thermosetting resin composition according to claim 2 , further comprising an inorganic filler.

5. A prepreg formed from the thermosetting resin composition according to claim 2 .

6. A laminated plate formed from the prepreg according to claim 5 through laminate molding.

7. A multi-layered printed wiring board produced from the laminated plate according to claim 6 .

8. The modified silicone compound according to claim 1 , wherein a ratio of C═C groups of the maleimide groups of the maleimide component (B) to total —NH 2 groups of the siloxane diamine component (A), the amine component (C) and the optional amine component (D) is 0.1≤C═C groups/total —NH 2 groups≤10.0.

9. The modified silicone compound according to claim 1 , wherein an amine equivalent of the siloxane diamine component (A) is 430-2,200.

10. The thermosetting resin composition according to claim 3 , wherein the epoxy resin includes at least one selected from the group consisting of a biphenyl aralkyl epoxy resin and a naphthalene epoxy resin, and the cyanate resin includes at least one selected from the group consisting of a novolac cyanate resin and bisphenol cyanate resin.

11. The thermosetting resin composition according to claim 10 , further comprising an imidazole curing accelerator.

12. The thermosetting resin composition according to claim 11 , further comprising at least one inorganic filler selected from the group consisting of silica and boehmite.

13. The modified silicone compound according to claim 1 , wherein
the maleimide component (B) comprises one or more of bis(4-maleimide phenyl)methane and polyphenylmethane maleimide,
the amine component (C) comprises aminophenol, and
the optional amine component (D) comprises one or more of 3,3′-diethyl-4,4′-diaminodiphenylmethane and 3,3′-diaminodiphenylsulfone.

14. A prepreg comprising a semi-cured form of the thermosetting resin composition according to claim 2 .

15. A laminated plate comprising a cured form of the prepreg according to claim 14 .

16. A multi-layered printed wiring board comprising the laminated plate according to claim 15 .

17. A modified silicone compound prepared by reacting reactants comprising:
(A) a siloxane diamine component comprising a siloxane diamine represented by a general formula (1):

wherein a plurality of R 1 s each independently represent an alkyl group, a phenyl group, or a substituted phenyl group and may be the same as or different from each other, a plurality of R 2 s each independently represent an alkyl group, a phenyl group, or a substituted phenyl group and may be the same as or different from each other, R 3 and R 4 each independently represent an alkyl group, a phenyl group, or a substituted phenyl group, R 5 and R 6 represent C 3 H 6 , n represents an integer of 2-50, and at least one of the following conditions (i)-(iv) is met:
(i) at least one of the R 1 s represents a phenyl group or a substituted phenyl group,
(ii) at least one of the R 2 s represents a phenyl group or a substituted phenyl group,
(iii) R 3 represents a phenyl group or a substituted phenyl group, and
(iv) R 4 represents a phenyl group or a substituted phenyl group;

(B) a maleimide component comprising a maleimide compound with at least two N-substituted maleimide groups in a molecular structure, wherein an amount of the maleimide component (B) is 100-3000 parts by mass, based on 100 parts by mass of the siloxane diamine component (A);
(C) an amine component comprising an amine compound with an acidic substituent represented by a general formula (2):

wherein R 9 or a plurality of R 9 s each independently represent a hydroxyl, a carboxyl, or a sulfonic group that is an acidic substituent, R 10 or a plurality of R 10 s each independently represent a hydrogen atom, an aliphatic hydrocarbon group with 1-5 carbon atoms, or a halogen atom, x represents an integer of 1-5, y represents an integer of 0-4, and x+y=5, and
an amount of the amine compound represented by general formula (2) is 1-8.454 parts by mass, based on 100 parts by mass of the siloxane diamine represented by general formula (1); and
(D) an optional amine component comprising an amine compound including at least two primary amino groups per molecule.

Assignees

• Kotake Tomohiko
• Miyatake Masato
• Nagai Shunsuke
• Hashimoto Shintaro
• Inoue Yasuo
• Takanezawa Shin
• Murai Hikari
• Showa Denko Materials Co Ltd

Inventors

• Kotake Tomohiko
• Miyatake Masato
• Nagai Shunsuke
• Hashimoto Shintaro
• Inoue Yasuo
• Takanezawa Shin
• Murai Hikari

Classifications

• C09D163/00

  Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins · CPC title

• C08L63/00

  Compositions of epoxy resins; Compositions of derivatives of epoxy resins · CPC title

• C08J2379/08

  Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors · CPC title

• C08G73/125

  the unsaturated precursors containing atoms other than carbon, hydrogen, oxygen or nitrogen in the main chain · CPC title

• H05K1/0346

  containing N · CPC title