Resin composition, prepreg, and laminate

Patent metadata

Field	Value
Publication number	US-9512329-B2
Application number	US-201214119342-A
Country	US
Kind code	B2
Filing date	May 23, 2012
Priority date	May 27, 2011
Publication date	Dec 6, 2016
Grant date	Dec 6, 2016

Abstract

A resin composition contains a cyanate ester compound, a maleimide compound, an epoxy resin, a silicone rubber powder, and an inorganic filler. The cyanate ester compound contains a compound represented by the following formula. The silicone rubber powder is contained in an amount of 40 to 150 parts by mass based on 100 parts by mass in total of the cyanate ester compound, the maleimide compound, and the epoxy resin. The inorganic filler is contained in an amount of 100 to 340 parts by mass based on 100 parts by mass in total of the cyanate ester compound, the maleimide compound, and the epoxy resin. A total content of the silicone rubber powder and the inorganic filler is 140 to 380 parts by mass based on 100 parts by mass in total of the cyanate ester compound, the maleimide compound, and the epoxy resin.

First claim

The invention claimed is:

1. A resin composition comprising a cyanate ester compound (A), a maleimide compound (B), an epoxy resin (C), a silicone rubber powder (D), and an inorganic filler (E),
wherein the cyanate ester compound (A) comprises a compound represented by the following formula (I):

wherein R represents a hydrogen atom or a methyl group, and n represents an integer of 1 or more;
the silicone rubber powder (D) is contained in an amount of 40 to 150 parts by mass based on 100 parts by mass in total of the cyanate ester compound (A), the maleimide compound (B), and the epoxy resin (C);
the inorganic filler (E) is contained in an amount of 100 to 340 parts by mass based on 100 parts by mass in total of the cyanate ester compound (A), the maleimide compound (B), and the epoxy resin (C); and
a total content of the silicone rubber powder (D) and the inorganic filler (E) is 140 to 380 parts by mass based on 100 parts by mass in total of the cyanate ester compound (A), the maleimide compound (B), and the epoxy resin (C).

2. The resin composition according to claim 1 , wherein the inorganic filler (E) is at least one selected from the group consisting of silicas, a metal hydrate, zinc borate, aluminum oxide, boron nitride, magnesium oxide, aluminum nitride, silicon nitride, and magnesium carbonate.

3. The resin composition according to claim 2 , wherein the inorganic filler (E) comprises the silicas.

4. The resin composition according to claim 1 , wherein the epoxy resin (C) comprises a polyoxynaphthylene-based epoxy resin represented by the following formula (II):

wherein each of Ar independently represents a naphthylene or phenylene group, provided that at least one hydrogen atom in both the naphthylene and phenylene groups may be substituted by an alkyl group having 1 to 4 carbon atoms or a phenylene group;
R 1 represents a hydrogen atom or a methyl group;
each of R 2 independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aralkyl group represented by the following formula (III):

wherein R 4 and R 5 each independently represent a hydrogen atom or a methyl group; Ar represents a phenylene or naphthylene group, provided that 1 to 3 hydrogen atoms in the phenylene or naphthylene group may be nuclearly substituted by an alkyl group having 1 to 4 carbon atoms; and o is a real number of 0.1 to 4 on average; and
R 3 represents a hydrogen atom, an aralkyl group represented by the formula (III), or an epoxy group-containing aromatic hydrocarbon group represented by the following formula (IV):

wherein R 6 represents a hydrogen atom or a methyl group; Ar represents a naphthylene group, provided that at least one hydrogen atom in the naphthylene group may be substituted by an alkyl group having 1 to 4 carbon atoms, an aralkyl group, or a phenylene group; and p is an integer of 1 or 2;
m and n each are an integer of 0 to 4, provided that m and n are not simultaneously 0; and
the position of binding to the naphthalene structure site may be any of the 1- to 8-positions.

5. The resin composition according to claim 4 , wherein Ar in the formula (II) is a naphthylene group, provided that at least one hydrogen atom in the naphthylene group may be substituted by an alkyl group having 1 to 4 carbon atoms or a phenylene group.

6. The resin composition according to claim 4 , wherein m and n in the formula (II) are an integer of 0 to 2, provided that m and n are not simultaneously 0.

7. The resin composition according to claim 4 , wherein the epoxy resin (C) comprises at least one or more selected from the group consisting of compounds represented by the following formula (V) and the following formula (VI):

wherein R 7 represents a hydrogen atom or a methyl group; and each of R 8 independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aralkyl group represented by the formula (III);

wherein R 9 represents a hydrogen atom or a methyl group; and each of R 10 independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aralkyl group represented by the formula (III).

8. The resin composition according to claim 4 , wherein the epoxy resin (C) comprises a polyoxynaphthylene-based epoxy resin represented by the formula (II) and an anthracene-based epoxy resin.

9. The resin composition according to claim 8 , wherein the anthracene-based epoxy resin comprises a dihydroanthracene-based epoxy resin represented by the following formula (VII):

wherein R 11 to R 20 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; and n represents an integer of 0 or more.

10. The resin composition according to claim 1 , wherein the cyanate ester compound (A) is contained in an amount meeting a ratio (CN/Ep) in a range of 0.65 to 2.5 wherein CN represents the number of cyanate groups in the cyanate ester compound (A); and Ep represents the number of epoxy groups in the epoxy resin (C).

11. The resin composition according to claim 1 , wherein the maleimide compound (B) is contained in an amount of 3 to 50 parts by mass based on 100 parts by mass in total of the cyanate ester compound (A), the maleimide compound (B), and the epoxy resin (C).

12. A prepreg comprising: a substrate; and the resin composition according to claim 1 impregnated into or coated on the substrate.

13. The prepreg according to claim 12 , wherein the substrate is a glass cloth made of S-glass or T-glass.

14. The prepreg according to claim 13 , wherein provided that warp threads and weft threads of the glass cloth are made of monofilaments with an average diameter of 5 μm or more; the number of the driven warp threads is defined as X (thread/inch); and the number of the driven weft threads is defined as Y (thread/inch), the total of X and Y is 110 to 200.

15. The prepreg according to claim 13 , wherein provided that warp threads and weft threads of the glass cloth are made of monofilaments with an average diameter of 4.5 μm or less; the number of the driven warp threads is defined as X (thread/inch); and the number of the driven weft threads is defined as Y (thread/inch), the total of X and Y is 130 to 240.

16. A laminate obtained by curing the prepreg according to claim 12 .

17. A metal foil-clad laminate obtained by stacking and curing the prepreg according to claim 12 and a metal foil.

Assignees

• Nobukuni Takeshi
• Kato Yoshihiro
• ITO Meguru
• HAMAJIMA Tomoki
• Mitsubishi Gas Chemical Co

Inventors

• Nobukuni Takeshi
• Kato Yoshihiro
• ITO Meguru
• HAMAJIMA Tomoki

Classifications

• C08J2363/00

  Characterised by the use of epoxy resins; Derivatives of epoxy resins · CPC title

• H05K2201/0212

  Resin particles · CPC title

• C08L79/04

  Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors · CPC title

• H05K1/0353

  consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement · CPC title

• C09D163/00 Primary

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