New formulation methodology for distortional thermosets

Patent metadata

Field	Value
Publication number	US-2016194437-A1
Application number	US-201615013542-A
Country	US
Kind code	A1
Filing date	Feb 2, 2016
Priority date	Aug 9, 2013
Publication date	Jul 7, 2016
Grant date	—

Abstract

Methods and formulations for distortional thermosets are disclosed that display enhanced composite mechanical performances and robust sorption resistance. The composition includes an epoxy resin of formula (I):

and a diamine curing agent. The resultant distortional thermoset compositions possess superior out-life requirements and advantageous reaction kinetics for preparing prepreg compositions and materials.

First claim

What is claimed is:

1 . A composition, comprising one or more reaction products of an amount of:
an epoxy resin of formula (I):

and
a first diamine curing agent.

2 . The composition of claim 1 , wherein the composition has a von Mises strain of at least 0.300.

3 . The composition of claim 1 , wherein the diamine curing agent is selected from the group consisting of formulas (II)-(XXV):

and combinations thereof.

4 . The composition of claim 1 , wherein the epoxy resin of formula (I) is

5 . The composition of claim 1 , wherein the epoxy resin of formula (I) is

6 . The composition of claim 1 , wherein the epoxy resin of formula (I) is

7 . The composition of claim 1 , wherein the epoxy resin of formula (I) is

8 . The composition of claim 1 , wherein the epoxy resin of formula (I) is

9 . The composition of claim 1 , wherein the epoxy resin of formula (I) is

10 . The composition of claim 1 , wherein the epoxy resin of formula (I) is in stoichiometric excess relative to the diamine curing agent.

11 . The composition of claim 1 , wherein the diamine curing agent has a Fukui electrophilic index between about 0.04 and about 0.06.

12 . The composition of claim 1 , further comprising a second diamine curing agent.

13 . The composition of claim 12 , wherein the first diamine curing agent is 4,4′-sulfonyldianiline.

14 . The composition of claim 13 , wherein the second diamine curing agent has a curing reaction control value between about 1 and about 55 as relative reactivity compared to 4,4′-sulfonyldianiline by Mulliken-based correlations.

15 . The composition of claim 12 , wherein the second diamine curing agent has a curing reaction control value between about 1 and about 55 as relative reactivity compared to 4,4′-sulfonyldianiline by Mulliken-based correlations.

16 . The composition of claim 15 , wherein the second diamine curing agent has a curing reaction control value between about 1 and about 8 as relative reactivity compared to 4,4′-sulfonyldianiline by Mulliken-based correlations.

17 . The composition of claim 16 , wherein the first diamine curing agent has a curing reaction control value between about 24 and about 55 as relative reactivity compared to 4,4′-sulfonyldianiline by Mulliken-based correlations.

18 . The composition of claim 1 , wherein the first diamine curing agent comprises at least one electron-withdrawing moiety.

19 . The composition of claim 18 , wherein the at least one electron-withdrawing moiety is selected from the group consisting of: —SO 2 , —SO 3 H, —NO 2 , —CN, —CR 3 , —CHO, and —CO 2 H, wherein R is a halide.

20 . The composition of claim 12 , wherein the second diamine curing agent comprises at least one electron-withdrawing moiety.

21 . The composition of claim 20 , wherein the at least one electron-withdrawing moiety of the second diamine curing agent is selected from the group consisting of: —SO 2 , —SO 3 H, —NO 2 , —CN, —CR 3 , —CHO, and —CO 2 H, wherein R is a halide.

22 . The composition of claim 20 , wherein the first diamine curing agent comprises at least one electron-withdrawing moiety.

23 . The composition of claim 22 , wherein the at least one electron-withdrawing moiety is selected from the group consisting of: —SO 2 , —SO 3 H, —NO 2 , —CN, —CR 3 , —CHO, and —CO 2 H, wherein R is a halide.

24 . The composition of claim 12 , wherein a ratio of first diamine curing agent to second diamine curing agent is about 9:1 by weight.

25 . The composition of claim 1 , wherein the first diamine curing agent has three ring groups.

26 . The composition of claim 12 , wherein the first diamine curing agent is selected from the group consisting of 4,4′-sulfonyldianiline, 4,4′-thiodianiline, 3,3′-((sulfonylbis(4,1-phenylene))bis(oxy))dianiline, 4,4′-(1,4-phenylenedisulfonyl)dianiline, 4,4′-((sulfonylbis(4,1-phenylene))bis(oxy))dianiline, 4,4′-((propane-2,2-diylbis-(4,1-phenylene))bis(oxy))-dianiline, and 4,4′disulfanediyldianiline; and
wherein the second diamine curing agent is selected from the group consisting of 4,4′-methylenedianiline, 4,4′-oxydianiline, 3,3′-(1,3-phenylenebis(oxy))-dianiline, 4,4′-(1,3-phenylenebis(oxy))-dianiline, 4,4′-methylenebis(2-ethyl-aniline), 4,4′-methylenebis(2-ethyl-aniline), 3,3′-((2,2-dimethylpropane-1,3-diyl)bis(oxy))dianiline, 4,4′-(1,4-phenylenebis-(propane-2,2-diyl))dianiline, 3-(4-(4-aminobenzyl)-benzyl)aniline, 4,4′-(1,4-phenylenebis(propane-2,2-diyl))bis(2,6-dimethylaniline), 4,4′-(1,4-phenylenebis(oxy))-dianiline, 3,3′-((propane-2,2-diylbis-(4,1phenylene))bis(oxy))-dianiline, 3,3′-sulfonyldianiline, 4,4′-methylenebis(cyclo-hexan-1-amine), 4,4′-(pentane-1,5-diylbis-(oxy))dianiline, 4,4′-([1,1′-biphenyl]-4,4′-diylbis(oxy))dianiline, 4,4′-(1,3-phenylenebis-(propane-2,2-diyl))bis(2,6-diisopropylaniline), and 4,4′-(1,3-phenylenebis-(propane-2,2-diyl))dianiline.

27 . The composition of claim 26 , wherein a ratio of first diamine curing agent to second diamine curing agent is about 9:1 by weight.

28 . The composition of claim 1 , further comprising one or more fibers.

29 . The composition of claim 28 , wherein the one or more fibers is selected from the group consisting of graphite, fiberglass, nylon, aramids, aramid polymers, and spectra.

Assignees

• Boeing Co

Inventors

• Christensen Stephen
• Tucker Samuel J
• Wiggins Jeffrey S

Classifications

• C08J2377/06

  Polyamides derived from polyamines and polycarboxylic acids (C08J2377/10 takes precedence) · CPC title

• C08J2363/00

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

• C08G59/245 Primary

  aromatic · CPC title

• C08G59/5033 Primary

  aromatic · CPC title

• C08G59/504

  containing an atom other than nitrogen belonging to the amine group, carbon and hydrogen · CPC title