# US 11,111,333 B2 · Resin compositions and resin infusion process

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- Number: US 11,111,333 B2
- Document ID: US11111333B2
- Status: Granted
- Kind: B2
- Application number: 16/169,062
- Filed: 2018-10-24
- Published: 2019-05-02
- Granted: 2021-09-07
- Earliest claimed: 2017-10-26
- Assignees: Cytec Industries Inc.
- Applicants: Cytec Industries Inc.
- Inventors: Jonathan E. Meegan; Marco Aurilia
- Web page: https://patentgrep.com/patent/US11111333B2

## CPC

- C08G 59/38: together with di-epoxy compounds
- B29C 70/48: and impregnating the reinforcements in the closed mould, e.g. resin transfer moulding [RTM] {, e.g. by vacuum}
- C08G 59/188: {using encapsulated compounds}
- C08G 59/226: {Mixtures of di-epoxy compounds}
- C08G 59/26: heterocyclic
- C08G 59/3218: {Carbocyclic compounds}
- C08G 59/5033: {aromatic}
- C08L 63/00: Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- C08L 63/04: Epoxynovolacs
- C08G 2120/00: Compositions for reaction injection moulding processes
- C08L 9/06: Copolymers with styrene
- C08L 2207/53: Core-shell polymer
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- B29C: SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING (making preforms B29B11/00; making laminated products by combining previously unconnected layers which become one product whose layers will remain together B32B37/00 - B32B41/00)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

Curable epoxy resin compositions suitable for liquid resin infusion processes. In one embodiment, the resin composition contains (a) at least two polyepoxides, one of which is triglycidyl ether of tris(hydroxyphenyl)methane, (b) an aromatic amine curing agent, and (c) core-shell rubber particles. In another embodiment, the resin composition (a) at least two polyepoxides, one of which is diglycidyl ether of bis(hydroxyphenyl)fluorene, (b) an aromatic amine curing agent, and (c) core-shell rubber particles.

## Claims

### Claim 1

A curable epoxy resin composition suitable for liquid resin infusion, comprising:
(A) a combination of polyepoxides consisting of: (i) triglycidyl ether of tris(hydroxyphenyl)-methane represented by Formula I:
(ii) diglycidyl ether of Bisphenol F or Bisphenol A;
(iii) a difunctional epoxide represented by the following Formula II:
and
(iv) an epoxy novolac resin represented by the following Formula III:
where n=1 to 5, and R=H
(B) 9,9-bis(4-amino-3-chlorophenyl)fluorene and/or 9,9-bis(4-aminophenyl)fluorene; and
(C) core-shell rubber particles,
wherein the weight percentages of the polyepoxides, based on the total weight of the epoxy resin composition, are as follows: 2% to 10% polyepoxide (i); 24% to 38% polyepoxides (ii) and (iii) combined; and 1% to 7% polyepoxide (iv),
wherein the molar ratio of component (B) to component (A) is 1:1 to 2:1,
wherein the amount of core-shell rubber particles is in the range of 0.3% to 10% by weight, based on the total weight of the epoxy resin composition, and
wherein the curable epoxy resin composition is void of any thermoplastic polymer.

### Claim 2 (depends on 1)

The curable epoxy resin composition of claim 1, wherein the epoxy novolac resin is represented by the following formula:

### Claim 3 (depends on 1)

The curable epoxy resin composition of claim 1, wherein the curable epoxy resin composition has viscosity of less than 10 Poise at a temperature within the range of 90° C. to 160° C.

### Claim 4 (depends on 1)

A liquid resin infusion (LRI) manufacturing method for producing a molded article, comprising the steps of providing a fibrous preform configured to receive liquid resin, infusing the fibrous preform with the curable epoxy resin composition of claim 1, and curing the resin-infused preform at a curing temperature (Tc).

### Claim 5 (depends on 4)

The method of claim 4, further comprising:
a. placing the fibrous preform in a closed mold;
b. heating the mold to an initial temperature;
c. injecting the curable epoxy resin composition into the mold so as to infuse the fibrous preform with the epoxy resin composition; and
d. curing the resin-infused preform at the curing temperature (Tc), which is higher than the initial temperature, for a time period sufficient to form a hardened article.