IP Library Granted Patent US 12,460,077
Granted Patent B2
US 12,460,077 · App. 17/783,368 · Granted Nov 4, 2025

Curable resin compositions containing an aliphatic polyketone toughener and composites made therefrom

Inventors: Kevin Wacker (The Woodlands, TX); Dong Le (The Woodlands, TX); Derek Kincaid (The Woodlands, TX)
Assignee: HUNTSMAN ADVANCED MATERIALS AMERICAS LLC
C08L63/00C08G59/22C08G59/32C08G59/4064C08G67/02C08G75/23C08J5/243C08L73/00C08J2363/00C08J2473/00C08J2481/06C08L2203/30C08L2205/02C08L2205/035
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Quick Facts
Patent No.
US 12,460,077
App. No.
17/783,368
Granted
Nov 4, 2025
Kind
B2
Abstract

The present disclosure provides a curable resin composition including a thermoset resin, an aliphatic polyketone as a toughener and a hardener. The curable resin composition may be combined with reinforcing fibers and then cured to form a fiber-reinforced composite article having a high glass transition temperature, excellent mechanical properties and low moisture absorption. The fiber-reinforced composite article may be used in various applications, such as in transport applications including aerospace, aeronautical, nautical and land vehicles.

Claims (15)

1 . A curable resin composition comprising (a) from wt. % to wt. %, based on the total weight of the curable resin composition, of a thermoset resin, (b) from 2 wt. % to 12.5 wt. %, based on the total weight of the curable resin composition, of an aliphatic polyketone toughener, and (c) from 15 wt. % to 25 wt. %, based on the total weight of the curable resin composition, of a hardener, and from 15 wt. % to 25 wt. %, based on the total weight of the curable resin composition, of an additional toughener, wherein the curable resin has a glass transition of at least 190° C. after curing.

2 . The curable resin composition of claim 1 , wherein the thermoset resin is an epoxy resin.

3 . The curable resin composition of claim 2 , wherein epoxy resin is selected from a difunctional epoxy resin, a trifunctional epoxy resin, a tetrafunctional epoxy resin and a mixture thereof.

4 . The curable resin composition of claim 2 , wherein the aliphatic polyketone is a linear alternating polymer of carbon monoxide and ethylene.

5 . The curable resin composition of claim 2 , wherein the aliphatic polyketone is a terpolymer of carbon monoxide, ethylene and one of propylene, n-butene, n-octene or n-dodecene.

6 . The curable resin composition of claim 1 , wherein the additional toughener comprise polyether sulphone, polyether ethersulphone, polyphenyl sulphone, polysulphone, polyimide, polyetherimide, aramid, polyamide, polyester, polyetheretherketone, polyurethane, polyurea, polyarylether, polyarylsulphides, polycarbonates, polyphenylene oxide, modified polyphenylene oxide or a mixture thereof.

7 . A fiber-reinforced resin composition comprising reinforcing fibers and the curable resin composition of claim 1 .

8 . The fiber-reinforced resin composition of claim 7 , wherein the reinforcing fibers are selected from graphite fibers, glass fibers, fibers formed of silicon carbide, fibers formed of alumina, fibers formed of boron, fibers formed of quartz, fibers formed from an organic polymer and a mixture thereof.

9 . The fiber-reinforced resin composition of claim 7 , wherein the reinforcing fibers are present in an amount of about 50 wt. % to about 90 wt. % by weight, based on the total weight of the fiber-reinforced resin composition.

10 . A method of producing a fiber-reinforced composite article including the steps of: (i) contacting reinforcing fibers with the curable resin composition of claim 1 in a mold to coat and/or impregnate the reinforcing fibers; and (ii) curing the coated and/or impregnated reinforcing fibers at a temperature of at least about 60° C.

11 . A fiber-reinforced composite article produced according to the method of claim 10 .

12 . The fiber-reinforced composite article of claim 11 , wherein the composite article is a primary or secondary aerospace structural material.

13 . A method of producing a fiber-reinforced composite article including the step of: contacting reinforcing fibers with the curable resin composition of claim 1 to coat and/or impregnate the reinforcing fibers and curing the coated and/or impregnated reinforcing fibers.

14 . A method of producing a fiber-reinforced composite article in a RIM system including the steps of: a) introducing a fiber preform comprising reinforcing fibers into a mold; b) injecting the curable resin composition of claim 1 into the mold; c) allowing the curable resin composition to impregnate the fiber preform; d) heating the impregnated fiber preform at a temperature of least about 60° C. for a period of time to produce an at least partially cured fiber-reinforced composite article; and e) optionally subjecting the partially cured fiber-reinforced composite article to post curing operations at a temperature of from about 100° C. up to about 350° C.

15 . A method of producing a fiber-reinforced composite article in a VaRTM system including the steps of: a) introducing a fiber preform comprising reinforcing fibers into a mold; b) injecting the curable resin composition of claim 1 into the mold; c) reducing the pressure within the mold; d) maintaining the mold at about the reduced pressure; e) allowing the curable resin composition to impregnate the fiber preform; f) heating the impregnated fiber preform at a temperature of at least about 60° C. for a period of time to produce an at least partially cured fiber-reinforced composite article; and optionally subjecting the at least partially cured fiber-reinforced composite article to post curing operations at a temperature of from about 100° C. to about 350° C.

Assignments (3)
SECURITY INTEREST Recorded May 4, 2026
From: HUNTSMAN INTERNATIONAL LLC; HUNTSMAN ADVANCED MATERIALS AMERICAS LLC; HUNTSMAN NANOCOMP LLC; HUNTSMAN PETROCHEMICAL LLC
To: CITIBANK N.A.
Reel/Frame 075498/0663 →
PATENT SECURITY AGREEMENT Recorded Mar 10, 2026
From: HUNTSMAN INTERNATIONAL LLC; HUNTSMAN ADVANCED MATERIALS AMERICAS LLC; HUNTSMAN NANOCAMP LLC; HUNTSMAN PETROCHEMICAL LLC
To: CITIBANK, N.A.
Reel/Frame 075106/0238 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 19, 2023
From: WACKER, KEVIN; LE, DONG; KINCAID, DEREK
To: HUNTSMAN ADVANCED MATERIALS AMERICAS LLC
Reel/Frame 063378/0061 →
Continuity (2)
Provisional Application 62946085 · Dec 10, 2019
Related Publication 20230016920A1 · Jan 19, 2023
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