Cyanate ester/aryl ethynyl polyimide resins for composite materials

Patent metadata

Field	Value
Publication number	US-10040906-B2
Application number	US-201615200155-A
Country	US
Kind code	B2
Filing date	Jul 1, 2016
Priority date	Jul 3, 2015
Publication date	Aug 7, 2018
Grant date	Aug 7, 2018

Abstract

A polymerizable thermoset composition including a polymerizable organic cyanate ester resin and a polymerizable aryl ethynyl-terminated polyimide, a polymerized thermoset, a process for the production of the polymerized thermoset as well as the use of the polymerizable thermoset composition for the production of lightweight construction components, preferably carbon fiber composite materials (CFC), and a lightweight construction component, preferably carbon fiber composite material (CFC), containing the polymerized thermoset are described.

First claim

The invention claimed is:

1. A polymerizable thermoset composition comprising:
a) a cross-linkable organic cyanate ester resin;
b) a cross-linkable aryl ethynyl-terminated polyimide, and
c) at least one allyl compatibilizer comprising at least two functional groups, wherein the functional groups are each independently selected from the group consisting of hydroxides, primary amines, secondary amines, anhydrides, cyanate esters, and epoxides.

2. The polymerizable thermoset composition as claimed in claim 1 , wherein the cross-linkable organic cyanate ester resin is a compound of the formula (I):

wherein R represents an alkyl, alkenyl or aryl group.

3. The polymerizable thermoset composition as claimed in claim 1 , wherein the cross-linkable organic cyanate ester resin is a compound of the formula (II):

wherein R 1 , R 2 and R 3 , independently of each other, represent hydrogen or C 1 -C 10 alkyl and n represents an integer from 0 to 20.

4. The polymerizable thermoset composition as claimed in claim 1 , wherein the cross-linkable aryl ethynyl-terminated polyimide is a compound of the formula (III):

wherein Ar represents an intermediate segment which is selected from the group consisting of

R 4 represents a group selected from the group consisting of

R 5 represents a group selected from the group consisting of

wherein X represents a group selected from the group consisting of —O—, —S—, —S(O 2 )—, —C(O)—, —C(CH 3 ) 2 —, —C(CF 3 ) 2 —, —CH 2 —, 3-oxyphenoxy, 4-oxyphenoxy, 4′-oxy-4-biphenoxy and 4-[1-(4-oxyphenyl)-1-methylethyl]-phenoxy, and m represents an integer from 1 to 40.

5. The polymerizable thermoset composition as claimed in claim 1 , wherein the polymerizable thermoset composition contains the cross-linkable organic cyanate ester resin and the cross-linkable aryl ethynyl-terminated polyimide in a ratio by weight (wt/wt) of 200:10 to 20:10.

6. The polymerizable thermoset composition as claimed in claim 1 , wherein the at least one allyl compatibilizer is a compound of the formula (IV):

wherein R 6 represents a group selected from the group consisting of —O—, —S—, —S(O) 2 —, —C(O)—, —C(CH 3 ) 2 —, —C(CF 3 ) 2 —, —CH 2 —, 3-oxyphenoxy, 4-oxyphenoxy, 4′-oxy-4-biphenoxy and 4-[1-(4-oxyphenyl)-1-methylethyl]-phenoxy; and Y each independently represents a functional group selected from the group consisting of hydroxides, primary amines, secondary amines, anhydrides, cyanate esters, and epoxides.

7. The polymerizable thermoset composition as claimed in claim 1 , wherein the cross-linkable organic cyanate ester resin and the cross-linkable aryl ethynyl-terminated polyimide react through the at least one allyl compatibilizer with the formation of a covalently bonded interpenetrating polymeric system.

8. The polymerizable thermoset composition as claimed in claim 1 , wherein the polymerizable thermoset composition contains the cross-linkable organic cyanate ester resin and the cross-linkable aryl ethynyl-terminated polyimide and the at least one allyl compatibilizer in a ratio by weight (wt/wt/wt) of 150:6:1 to 5:2:1.

9. A polymerized thermoset which is a reaction product of the polymerizable thermoset composition as claimed in claim 1 .

10. A process for the production of a polymerized thermoset, comprising the following steps:
i) providing the polymerizable thermoset composition as described in claim 1 ; and
ii) polymerizing the polymerizable thermoset composition from step i) at a temperature in the range 100° C. to 330° C.

Assignees

• Airbus Defence & Space Gmbh

Inventors

• Meier Christoph
• Parlevliet Patricia
• Doering Manfred

Classifications

• C08G73/0655

  from polycyanurates · CPC title

• C08L63/00

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

• C08L79/06

  Polyhydrazides; Polytriazoles; Polyamino-triazoles; Polyoxadiazoles · CPC title

• C08G73/16 Primary

  Polyester-imides · CPC title

• C08G73/0644 Primary

  Poly(1,3,5)triazines · CPC title