Cyclic olefin-based copolymer composition, varnish, and cross-linked product

Patent metadata

Field	Value
Publication number	US-12378377-B2
Application number	US-201917295072-A
Country	US
Kind code	B2
Filing date	Nov 22, 2019
Priority date	Nov 27, 2018
Publication date	Aug 5, 2025
Grant date	Aug 5, 2025

Abstract

A cyclic olefin-based copolymer resin composition includes a cyclic olefin-based copolymer (M); and a maleimide compound (L), in which the cyclic olefin-based copolymer (M) includes a cyclic olefin-based copolymer (m) including a repeating unit represented by a specific general formula, the maleimide compound (L) has a solubility parameter (SP value) obtained by Fedors method of 19 J 1/2 /cm 3/2 or more and 26 J 1/2 /cm 3/2 or less and includes a maleimide compound (l), which is a bismaleimide compound having at least two maleimide groups in a molecule, and when a total of the cyclic olefin-based copolymer (M) and the maleimide compound (L) is 100 parts by mass, a content of the maleimide compound (L) is 1 part by mass or more and 50 parts by mass or less.

First claim

The invention claimed is:

1. A cyclic olefin-based copolymer resin composition comprising:
a cyclic olefin-based copolymer (M); and
a maleimide compound (L)
wherein the cyclic olefin-based copolymer (M) includes a cyclic olefin-based copolymer (m) including
a repeating unit derived from one or more kinds of olefins represented by General Formula (I),
a repeating unit derived from one or more kinds of cyclic non-conjugated dienes represented by General Formula (III), and
a repeating unit derived from one or more kinds of cyclic olefins represented by General Formula (V),
the maleimide compound (L) has a solubility parameter (SP value) obtained by Fedors method of 19 J 1/2 /cm 3/2 or more and 26 J 1/2 /cm 3/2 or less and includes a maleimide compound which is a bismaleimide compound having at least two maleimide groups in a molecule, and
when a total of the cyclic olefin-based copolymer (M) and the maleimide compound (L) is 100 parts by mass, a content of the maleimide compound (L) is 1 part by mass or more and 50 parts by mass or less,

in General Formula (I), R 300 represents a hydrogen atom or a linear or branched hydrocarbon group having 1 to 29 carbon atoms,

in General Formula (III), u is 0 or 1, v is 0 or a positive integer, w is 0 or 1, R 61 to R 76 and R a1 and R b1 , which may be the same or different from each other, are a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a halogenated alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 15 carbon atoms, or an aromatic hydrocarbon group having 6 to 20 carbon atoms, R 104 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, t is a positive integer of 0 to 10, and R 75 and R 76 may bond with each other to form a monocyclic or polycyclic ring,

in General Formula (V), u is 0 or 1, v is 0 or a positive integer, w is 0 or 1, R 61 to R 78 and R a1 and R b1 , which may be the same or different from each other, are a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a halogenated alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 15 carbon atoms, or an aromatic hydrocarbon group having 6 to 20 carbon atoms, and R 75 to R 78 may bond with each other to form a monocyclic or polycyclic ring.

2. The cyclic olefin-based copolymer resin composition according to claim 1 ,
wherein, when a total number of moles of the repeating units in the cyclic olefin-based copolymer (m) is 100 mol %, a content of the repeating units derived from the cyclic non-conjugated dienes is in a range of 19 mol % or more and 40 mol % or less.

3. The cyclic olefin-based copolymer resin composition according to claim 1 ,
wherein, in the cyclic olefin-based copolymer (m), the cyclic non-conjugated diene forming the repeating unit derived from the cyclic non-conjugated dienes includes 5-vinyl-2-norbornene, and the cyclic olefin forming the repeating unit derived from the cyclic olefins includes tetracyclo[4.4.0.1 2,5 .1 7,10 ]-3-dodecene.

4. The cyclic olefin-based copolymer resin composition according to claim 1 ,
wherein a molecular weight of the maleimide compound (l) is 300 or more and 1000 or less.

5. The cyclic olefin-based copolymer resin composition according to claim 1 , further comprising:
a compatibility agent (C) for compatibilizing the cyclic olefin-based copolymer (M) and the maleimide compound (L).

6. The cyclic olefin-based copolymer resin composition according to claim 5 ,
wherein, when the total of the cyclic olefin-based copolymer (M) and the maleimide compound (L) is 100 parts by mass, a content of the compatibility agent (C) is 0.1 parts by mass or more and 10 parts by mass or less.

7. A varnish comprising:
the cyclic olefin-based copolymer resin composition according to claim 1 ; and a solvent.

8. The varnish according to claim 7 ,
wherein the solvent is formed of a mixed solvent including at least one non-polar solvent (X) and at least one polar solvent (Y).

9. The varnish according to claim 8 ,
wherein the non-polar solvent (X) includes at least one selected from the group consisting of toluene, xylene, cyclohexane, and decalin, and the polar solvent (Y) includes at least one selected from the group consisting of methyl isobutyl ketone, methyl ethyl ketone, diisobutyl ketone, methyl propyl ketone, and cyclohexanone, and
when a total amount of the non-polar solvent (X) and the polar solvent (Y) is 100% by mass,
a content of the non-polar solvent (X) is 70% by mass or more and 95% by mass or less, and
a content of the polar solvent (Y) is 5% by mass or more and 30% by mass or less.

10. A cross-linked product obtained by cross-linking the cyclic olefin-based copolymer resin composition according to claim 1 .

11. A film or sheet comprising:
the cross-linked product according to claim 10 .

12. A laminate comprising:
the cross-linked product according to claim 10 .

13. A circuit substrate comprising:
an electrically insulating layer including the cross-linked product according to claim 10 ; and
a conductor layer provided on the electrically insulating layer.

14. An electronic device comprising:
the circuit substrate according to claim 13 .

15. A prepreg comprising: the cyclic olefin-based copolymer resin composition according to claim 1 ; and
a sheet-like 1 fiber base material.

Assignees

• Mitsui Chemicals Inc

Inventors

• Murase Hirohiko
• Asahina Koutarou
• Takeuchi Fumito

Classifications

• H05K1/0353

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

• C08J5/24

  Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs · CPC title

• C08F287/00

  Macromolecular compounds obtained by polymerising monomers on to block polymers · CPC title

• C08J2365/00

  Characterised by the use of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C08J2307/00 - C08J2357/00, C08J2361/00 take precedence); Derivatives of such polymers · CPC title

• C08J5/18

  Manufacture of films or sheets · CPC title