High heat and high toughness epoxy compositions, articles, and uses thereof

Patent metadata

Field	Value
Publication number	US-2020181391-A1
Application number	US-201716333457-A
Country	US
Kind code	A1
Filing date	Sep 26, 2017
Priority date	Sep 26, 2016
Publication date	Jun 11, 2020
Grant date	—

Abstract

A high heat epoxy composition comprising: a high heat epoxy compound; a thermoplastic polymer; and a hardener; wherein a cured sample of the high heat epoxy composition has a glass transition temperature greater than or equal to 200° C., preferably greater than 220° C., or preferably greater than 240° C., measured as per ASTM D3418; or wherein a cured sample of the composition has a fracture toughness greater than 150 J/m 2 , preferably greater than 170 J/m 2 , preferably greater than 190 J/m 2 , measured as per ASTM D5045 is provided.

First claim

1 . A high heat epoxy composition comprising:
a thermoplastic polymer; an epoxy hardener; and a high heat epoxy compound of formula:

wherein
R 1 and R 2 at each occurrence are each independently an epoxide-containing functional group;
R a and R b at each occurrence are each independently halogen, C 1 -C 12 alkyl, C 2 -C 12 alkenyl, C 3 -C 8 cycloalkyl, or C 1 -C 12 alkoxy;
p and q at each occurrence are each independently 0 to 4;
R 13 at each occurrence is independently a halogen or a C 1 -C 6 alkyl group;
c at each occurrence is independently 0 to 4;
R 14 at each occurrence is independently a C 1 -C 6 alkyl, phenyl, or phenyl substituted with up to five halogens or C 1 -C 6 alkyl groups;
R g at each occurrence is independently C 1 -C 12 alkyl or halogen, or two R g groups together with the carbon atoms to which they are attached form a four-, five, or six-membered cycloalkyl group; and
t is 0 to 10; and

wherein a cured sample of the high heat epoxy composition has a glass transition temperature of greater than or equal to 200° C. measured as per ASTM D3418.

2 . The composition of claim 1 , wherein the cured sample of the high heat epoxy composition has a glass transition temperature of 200° C. to 270° C., as measured as per ASTM D3418.

3 . The composition of claim 1 , wherein the cured sample of the high heat epoxy composition has a fracture toughness of greater than 150 J/m 2 , measured as per ASTM D5045.

4 . The composition of claim 1 , wherein the cured sample of the high heat epoxy composition has a fracture toughness that is at least 10% greater than a fracture toughness of a cured sample of a comparable high heat epoxy composition without the thermoplastic polymer, wherein the fracture toughness is measured as per ASTM D5045.

5 . The composition of claim 1 , wherein the thermoplastic polymer is selected from a polyetherimide, amine terminate polyetherimide, polyethersulfone, polyphenylene sulfone, polysulfone, polyarylsulfone, polyaryl ether, polyphenylene ether, polyetheretherketone, polyetherketone, polyetherketoneketone, polyketone sulfide, polyaryletherketone, aromatic polyamide, polyamideimide, polysiloxane, polyimide siloxane, polyimide, or a combination thereof.

6 . The composition of claim 1 , wherein the composition comprises greater than 0 to 25 wt % of the thermoplastic polymer.

7 . The composition of claim 1 , wherein the epoxy hardener is an aromatic diamine compound.

8 . The composition of claim 1 , wherein R 1 and R 2 at each occurrence are each independently:

wherein R 3a and R 3b are each independently hydrogen or C 1 -C 12 alkyl.

9 . The composition of claim 1 , wherein the high heat epoxy compound has the formula (1-a), (2-a), or (4-b),

10 . The composition of claim 1 , wherein 10 to 40 wt % of a solvent is used to prepare the high heat epoxy composition.

11 . The composition of claim 10 , wherein the solvent is selected from dioxane, methylene chloride, chloroform, or a combination thereof.

12 . The composition of claim 1 , comprising 50 to 95 wt %, of a high heat epoxy compound having formula (1-a)

and 1 to 20 wt % of a polyethersulfone or a polyetherimide.

13 . A cured composition comprising a product obtained by curing the composition of claim 1 .

14 . The cured composition of claim 13 , wherein the cured composition has a fracture toughness of 150 J/m 2 or greater, as measured per ASTM D5045.

15 . An article comprising the cured composition of claim 13 .

16 . The article of claim 15 , wherein the article is a coating, encapsulant, adhesive, or matrix polymer for composites.

17 . The composition of claim 7 , wherein the aromatic diamine compound is selected from 4-aminophenyl sulfone, 3-aminophenyl sulfone, 4,4′-methylenedianiline, 4,4′-methylenebis(2,6-diethylaniline), m-phenylenediamine, p-phenylenediamine, 2,4-bis(p-aminobenzyl)aniline, 3,5-diethyltoluene-2,4-diamine, 3,5-diethyltoluene-2,6-diamine, m-xylylenediamine, p-xylylenediamine, or a combination thereof.

18 . The composition of claim 1 , wherein the composition does not comprise a solvent.

19 . The composition of claim 1 , comprising 50 to 95 wt % of a high heat epoxy compound having formula (1-a)

and 1 to 20 wt % of a polyetherimide.

20 . The composition of claim 1 , comprising 3 to 15 wt % of the thermoplastic polymer selected from a polyethersulfone, a polyetherimide, or a combination thereof;
15 to 25 wt % of the epoxy hardener; and 65 to 85 wt % of the high heat epoxy compound of formula (I), (II), or (IV), wherein the cured sample of the high heat epoxy composition has
a glass transition temperature of greater than or equal to 240° C., as measured per ASTM D3418, and
a fracture toughness of greater than 170 J/m 2 , as measured per ASTM D5045.

Assignees

• Sabic Global Technologies Bv

Inventors

• Sista Prakash
• Bajaj Devendra
• Peters Edward Norman

Classifications

• C08L63/00 Primary

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

• C08G59/5033

  aromatic · CPC title

• C08G59/26

  heterocyclic · CPC title

• C08G59/245

  aromatic · CPC title

• C08L81/06

  Polysulfones; Polyethersulfones · CPC title