US 12,146,051 B2
Epoxy resin compositions, prepreg, and fiber-reinforced composite materials
Swezin Than Tun, Tacoma, WA (US); Jonathan Hughes, Tacoma, WA (US); and Nobuyuki Arai, Tacoma, WA (US)
Assigned to Toray Industries, Inc., Tokyo (JP)
Appl. No. 17/276,659
Filed by Toray Industries, Inc., Tokyo (JP)
PCT Filed Sep. 20, 2019, PCT No. PCT/IB2019/001057
§ 371(c)(1), (2) Date Mar. 16, 2021,
PCT Pub. No. WO2020/058766, PCT Pub. Date Mar. 26, 2020.
Claims priority of provisional application 62/897,701, filed on Sep. 9, 2019.
Claims priority of provisional application 62/734,623, filed on Sep. 21, 2018.
Prior Publication US 2022/0033640 A1, Feb. 3, 2022
Int. Cl. C08L 63/00 (2006.01); C08G 59/24 (2006.01); C08G 59/32 (2006.01); C08G 59/50 (2006.01); C08J 5/04 (2006.01); C08J 5/24 (2006.01); C08L 81/06 (2006.01)
CPC C08L 63/00 (2013.01) [C08G 59/245 (2013.01); C08G 59/32 (2013.01); C08G 59/504 (2013.01); C08J 5/042 (2013.01); C08J 5/24 (2013.01); C08J 5/243 (2021.05); C08L 81/06 (2013.01); C08L 2201/08 (2013.01); C08L 2205/025 (2013.01); C08L 2205/035 (2013.01)] 23 Claims
 
1. An epoxy resin composition for a fiber-reinforced composite material comprising component (A), component (B), component (C), and component (D), and at least one thermoplastic resin, wherein the epoxy resin composition when cured has a weight loss of less than 1.0% when thermally soaked at 180° C. for 1000 hours, and wherein:
component (A) comprises at least one poly-naphthalene-based epoxy resin with an epoxy functionality of two as represented in Formula (I):

OG Complex Work Unit Chemistry
wherein R1 to R12 are each independently selected from the group consisting of hydrogen atoms, halogen atoms, C1 to C10 alkyl groups, C1 to C10 alkoxyl groups, C1 to C10 fluoroalkyl groups, cycloalkyl groups, aryl groups, aryloxyl groups, and glycidoxy groups, Y1 to Y3 are each independently selected from the group consisting of hydrogen atoms, halogen atoms, C1 to C10 alkyl groups, C1 to C10 alkoxyl groups, C1 to C10 fluoroalkyl groups, cycloalkyl groups, aryl groups, aryloxyl groups, and glycidoxy groups, wherein each benzene nucleus may be substituted with one or more Y groups, n is 0, k is 0 or an integer of 1, wherein the Y groups may be attached to either or both rings of each naphthalene nucleus; and each X is independently selected from the group consisting of a direct bond, —CH2—, —C(CH3)2—, —S—, —SO2—, —O—, —C(═O)O—, —C(═O)—, —C(═O)NH—, C1 to C6 alkylene groups, C1 to C6 alkoxylene groups, cycloalkylene groups, arylene groups and aryloxylene groups, wherein these groups are optionally employed individually or different groups are optionally employed in combination as X;
component (B) comprises at least one non-linear multi-phenyl epoxy resin in a total amount of from 10 to 35 PHR per 100 PHR of total epoxy resin;
component (C) comprises at least one epoxy resin having an epoxy functionality of at least three which is neither a poly-naphthalene-based epoxy resin nor a non-linear multi-phenyl epoxy resin that includes triglycidyl-p-aminophenol; and
component (D) comprises at least one amine curing agent.