Polyimide resin composition, and (polyimide resin)-fiber composite material

Patent metadata

Field	Value
Publication number	US-10093789-B2
Application number	US-201414909335-A
Country	US
Kind code	B2
Filing date	Aug 4, 2014
Priority date	Aug 6, 2013
Publication date	Oct 9, 2018
Grant date	Oct 9, 2018

Abstract

[1] A polyimide resin composition containing a polyimide resin (A) and an additive (B), the polyimide resin (A) containing a repeating structural unit represented by the following formula (1) and a repeating structural unit represented by the following formula (2), a content ratio of the repeating structural unit of formula (1) with respect to the total of the repeating structural unit of formula (1) and the repeating structural unit of formula (2) being from 40 to 70 mol %; and [2] a composite material containing a fiber material (C) impregnated with a polyimide resin (A) containing a repeating structural unit represented by the following formula (1) and a repeating structural unit represented by the following formula (2), a content ratio of the repeating structural unit of formula (1) with respect to the total of the repeating structural unit of formula (1) and the repeating structural unit of formula (2) being from 40 to 70 mol %:

wherein R 1 represents a divalent group having from 6 to 22 carbon atoms containing at least one alicyclic hydrocarbon structure; R 2 represents a divalent chain aliphatic group having from 5 to 20 carbon atoms; and X 1 and X 2 each independently represent a tetravalent group having from 6 to 22 carbon atoms containing at least one aromatic ring.

First claim

The invention claimed is:

1. A polyimide resin composition, comprising:
a polyimide resin, and
an additive,
wherein the polyimide resin comprises a repeating structural unit represented by formula (1) and a repeating structural unit represented by formula (2),
a content ratio of the repeating structural unit of formula (1) with respect to a total of the repeating structural unit of formula (1) and the repeating structural unit of formula (2) is from 40 to 70 mol %:

wherein
R 1 represents a divalent group comprising 6 to 22 carbon atoms comprising an alicyclic hydrocarbon structure;
R 2 represents a divalent chain aliphatic group comprising 5 to 12 carbon atoms; and
X 1 and X 2 each independently represents a tetravalent group comprising 6 to 22 carbon atoms comprising an aromatic ring;
the additive is at least one selected from the group consisting of a filler, a flame retardant, a colorant, a slidability-improving agent, and an antioxidant; and
the polyimide resin has a melting point of 360° C. or less and a glass transition temperature of 200° C. or more.

2. The polyimide resin composition according to claim 1 , wherein R 1 represents a divalent group represented by formula (R1-1) or formula (R1-2):

wherein
m 11 and m 12 each independently represents an integer of from 0-2; and
m 13 to m 15 each independently represents an integer of from 0-2.

3. The polyimide resin composition according to claim 1 , wherein R 1 represents a divalent group represented by formula (R1-3):

4. The polyimide resin composition according to claim 1 , wherein R 2 represents an alkylene group comprising 5 to 12 carbon atoms.

5. The polyimide resin composition according to claim 1 , wherein X 1 and X 2 each independently represents a tetravalent group represented by one of formula (X-1), formula (X-2), formula (X-3) or formula (X-4):

wherein
R 11 to R 18 each independently represents an alkyl group comprising 1 to 4 carbon atoms;
p 11 to p 13 each independently represents an integer of from 0-2;
p 14 , p 15 , p 16 and p 18 each independently represents an integer of from 0-3;
p 17 represents an integer of from 0-4; and
L 11 to L 13 each independently represents a single bond, an ether group, a carbonyl group or an alkylene group comprising 1 to 4 carbon atoms.

6. The polyimide resin composition according to claim 1 , wherein the polyimide resin further comprises a repeating structural unit represented by formula (3), and
a content ratio of the repeating structural unit of formula (3) with respect to the total of the repeating structural unit of formula (1) and the repeating structural unit of formula (2) being 25 mol % or less:

wherein
R 3 represents a divalent group comprising 6 to 22 carbon atoms comprising an aromatic ring; and
X 3 represents a tetravalent group comprising 6 to 22 carbon atoms comprising an aromatic ring.

7. The polyimide resin composition according to claim 1 , wherein the filler is at least one selected from the group consisting of silica, alumina, kaolinite, wollastonite, mica, talc, clay, sericite, magnesium carbonate, magnesium sulfate, glass beads, glass fiber, carbon fiber, alumina fiber, potassium titanate whisker, aluminum borate whisker, magnesium-based whisker, silicon-based whisker, acrylic fiber, poly(benzimidazole) fiber, and wholly aromatic polyimide fiber.

8. The polyimide resin composition according to claim 1 , wherein the flame retardant is at least one selected from the group consisting of a halogen-based flame retardant, a phosphorus-based flame retardant, and a metal oxide-based flame retardant.

9. The polyimide resin composition according to claim 1 , wherein the colorant is at least one selected from the group consisting of a blue dye, a green dye, graphite, carbon black, titanium dioxide, calcium sulfate, and calcium carbonate.

10. The polyimide resin composition according to claim 1 , wherein the slidability-improving agent is at least one selected from the group consisting of molybdenum disulfide, a metallic soap, a mineral oil, a synthetic oil, a wax, a fluorine-based resin, a polyolefin, and a spherical phenol.

11. The polyimide resin composition according to claim 1 , wherein the antioxidant is at least one selected from the group consisting of a phenol-based antioxidant, a sulfur-based antioxidant, a phosphorus-based antioxidant, and an amine-based antioxidant.

12. A molded article, comprising the polyimide resin composition according to claim 1 .

13. A method for producing a molded article, comprising heat-molding the polyimide resin composition according to claim 1 at a temperature of from 300 to 400° C.

14. A film, comprising the polyimide resin composition according to claim 1 .

15. A fiber, comprising the polyimide resin composition according to claim 1 .

16. A heat-resistant adhesive, comprising the polyimide resin composition according to claim 1 .

17. A color filter, comprising the polyimide resin composition according to claim 1 .

18. A solar cell substrate, comprising the polyimide resin composition according to claim 1 .

19. A bearing for automobiles, comprising the polyimide resin composition according to claim 1 .

20. A bearing for copiers, comprising the polyimide resin composition according to claim 1 .

21. A fixing belt or an intermediate transfer belt, comprising the polyimide resin composition according to claim 1 .

22. A composite material, comprising:
a fiber material impregnated with a polyimide resin comprising a repeating structural unit represented by formula (1) and a repeating structural unit represented by formula (2),
a content ratio of the repeating structural unit of formula (1) with respect to a total of the repeating structural unit of formula (1) and the repeating structural unit of formula (2) is from 40 to 70 mol %:
wherein

R 1 represents a divalent group comprising 6 to 22 carbon atoms comprising an alicyclic hydrocarbon structure;
R 2 represents a divalent chain aliphatic group comprising 5 to 20 carbon atoms; and
X 1 and X 2 each independently represents a tetravalent group comprising 6 to 22 carbon atoms comprising an aromatic ring.

23. A molded article, comprising the composite material according to claim 22 .

24. A method for producing a molded article, comprising heat-molding the composite material according to claim 22 at a temperature of from 300 to 400° C.

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Sato Yuuki
• Mitadera Jun

Classifications

• D01F6/74

  from polycondensates of cyclic compounds, e.g. polyimides, polybenzimidazoles · CPC title

• C08K5/18

  with aromatically bound amino groups · CPC title

• C08G73/105

  with oxygen only in the diamino moiety · CPC title

• C08K5/0008

  Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59 · CPC title

• C08J5/18

  Manufacture of films or sheets · CPC title