Accelerated peroxide-cured resin compositions having extended open times

Patent metadata

Field	Value
Publication number	US-12486381-B2
Application number	US-202318527509-A
Country	US
Kind code	B2
Filing date	Dec 4, 2023
Priority date	Feb 19, 2018
Publication date	Dec 2, 2025
Grant date	Dec 2, 2025

Abstract

Curable resin compositions having extended open times at ambient temperatures and short cure times at elevated temperatures are prepared using a curable resin, a combination of room-temperature-stable liquid peroxides (including at least one perketal), a promoter salt, a thiol-functionalized organic accelerator and a free radical trap. The curable resin compositions are useful in pultrusion, cure-in-place pipe and resin transfer molding applications, among others.

First claim

What is claimed is:

1 . A system for curing a curable resin, wherein the system comprises a first component and a second component and wherein the first component comprises at least one room-temperature-stable organic peroxide, other than a perketal, which is liquid at 25° C.; and at least one room-temperature-stable perketal which is liquid at 25° C. and the second component comprises at least one salt of at least one metal selected from the group consisting of Li, Al, Mg, Co, Ni, Cr, Sn, Au, Pd and Pt and at least one thiol-functionalized organic compound, wherein at least one free radical trap is present in at least one of the first component or the second component.

2 . The system of claim 1 , wherein the at least one thiol-functionalized organic compound includes at least one thiol-functionalized organic compound comprised of two or more thiol functional groups.

3 . The system of claim 1 , wherein the at least one thiol-functionalized organic compound includes at least one α-mercaptoacetate or β-mercaptopropionate ester of an alcohol.

4 . The system of claim 1 , wherein the at least one thiol-functionalized organic compound includes at least one thiol-functionalized organic compound selected from the group consisting of dipentene-dimercaptan; ethylcyclohexyldimercaptan; ethylene-1,2-bis-3-mercaptoacetate; ethylene-1,2-bis-3-mercaptopropionate; 1,2,3-propanetrithiol; 1,2,6-hexanetrithiol; pentaerythritolthiol; pentaerythritol tetramercaptoacetate; pentaerythritol tetramercaptopropionate; trimethylol propane tris(3-mercaptopropionate); 1,1,1-propanetriyl tris(mercaptoacetate) and thiolic derivatives of the formula: R—(R′—CH(OH)—CH 2 —SH) n wherein R is a linear alkyl group having 3-30 carbon atoms, R′ is a linear alkylene group having 3-30 carbon atoms and n is an integer of 2-6.

5 . The system of claim 1 wherein the at least one free radical trap includes at least one nitroxide radical.

6 . The system of claim 5 , wherein the at least one nitroxide radical is selected from the group consisting of SG-1 free radicals and TEMPO free radicals.

7 . The system of claim 1 , wherein the at least one room-temperature-stable organic peroxide other than a perketal, includes at least one room-temperature-stable perester or percarbonate which is liquid at 25° C. and is selected from the group consisting of t-butyl peroxybenzoate, t-amyl peroxybenzoate, t-butyl peroxyacetate, t-amyl peroxyacetate, t-butyl peroxy-3,5,5-trimethylhexanoate, OO-(t-butyl) O-isopropyl monoperoxycarbonate, OO-(t-butyl) O-(2-ethylhexyl) monoperoxycarbonate, OO-(t-amyl) O-(2-ethylhexyl) monoperoxycarbonate, and polyether poly-t-butylperoxy carbonate.

8 . The system of claim 1 , wherein the at least room-temperature-stable perketal includes at least one room-temperature-stable perketal selected from the group consisting of 1,1-di(t-amylperoxy)-cyclohexane, 1,1-di(t-butylperoxy)-cyclohexane, 1,1-di(t-butylperoxy)-3,3,5-trimethylcyclohexane, ethyl 3,3-di(t-amylperoxy)butyrate and n-butyl 4,4-di(t-butylperoxy)valerate.

9 . The system of claim 1 , wherein the at least one salt includes at least one transition metal halide.

10 . A cured resin produced using the system of claim 1 .

11 . A composite comprised of the cured resin of claim 10 and, optionally, at least one reinforcing filler.

12 . The composite of claim 11 , wherein the composite is in the form of a pultruded article or a cured-in-place pipe.

13 . A system for curing a curable resin, wherein the system comprises a first component and a second component and wherein the first component comprises at least one room-temperature-stable organic peroxide, other than a perketal, which is liquid at 25° C.; and at least one room-temperature-stable perketal which is liquid at 25° C. and the second component comprises at least one zinc halide and at least one thiol-functionalized organic compound, wherein at least one free radical trap is present in at least one of the first component or the second component.

14 . The system of claim 13 , wherein the at least one thiol-functionalized organic compound includes at least one thiol-functionalized organic compound comprised of two or more thiol functional groups.

15 . The system of claim 13 , wherein the at least one thiol-functionalized organic compound includes at least one α-mercaptoacetate or β-mercaptopropionate ester of an alcohol.

16 . The system of claim 13 , wherein the at least one thiol-functionalized organic compound includes at least one thiol-functionalized organic compound selected from the group consisting of dipentene-dimercaptan; ethylcyclohexyldimercaptan; ethylene-1,2-bis-3-mercaptoacetate; ethylene-1,2-bis-3-mercaptopropionate; 1,2,3-propanetrithiol; 1,2,6-hexanetrithiol; pentaerythritolthiol; pentaerythritol tetramercaptoacetate; pentaerythritol tetramercaptopropionate; trimethylol propane tris(3-mercaptopropionate); 1,1,1-propanetriyl tris(mercaptoacetate) and thiolic derivatives of the formula: R—(R′—CH(OH)—CH 2 —SH) n wherein R is a linear alkyl group having 3-30 carbon atoms, R′ is a linear alkylene group having 3-30 carbon atoms and n is an integer of 2-6.

17 . The system of claim 13 , wherein the at least one free radical trap includes at least one nitroxide radical.

18 . The system of claim 17 , wherein the at least one nitroxide radical is selected from the group consisting of SG-1 free radicals and TEMPO free radicals.

19 . The system of claim 13 , wherein the at least one room-temperature-stable organic peroxide other than a perketal, includes at least one room-temperature-stable perester or percarbonate which is liquid at 25° C.

20 . The system of claim 19 , wherein the at least one room-temperature-stable perester or percarbonate which is liquid at 25° C. is selected from the group consisting of t-butyl peroxybenzoate, t-amyl peroxybenzoate, t-butyl peroxyacetate, t-amyl peroxyacetate, t-butyl peroxy-3,5,5-trimethylhexanoate, OO-(t-butyl) O-isopropyl monoperoxycarbonate, OO-(t-butyl) O-(2-ethylhexyl) monoperoxycarbonate, OO-(t-amyl) O-(2-ethylhexyl) monoperoxycarbonate, and polyether poly-t-butylperoxy carbonate.

21 . The system of claim 13 , wherein the at least room-temperature-stable perketal includes at least one room-temperature-stable perketal selected from the group consisting of 1,1-di(t-amylperoxy)-cyclohexane, 1,1-di(t-butylperoxy)-cyclohexane, 1,1-di(t-butylperoxy)-3,3,5-trimethylcyclohexane, ethyl 3,3-di(t-amylperoxy)butyrate and n-butyl 4,4-di(t-butylperoxy)valerate.

22 . A cured resin produced using the system of claim 13 .

23 . A composite comprised of the cured resin of claim 22 and, optionally, at least one reinforcing filler.

24 . The composite of claim 23 , wherein the composite is in the form of a pultruded article or a cured-in-place pipe.

Assignees

• Arkema Inc

Inventors

• Crocker Evan

Classifications

• B29K2309/08

  Glass · CPC title

• B29K2071/00

  Use of polyethers {, e.g. PEEK, i.e. polyether-etherketone or PEK, i.e. polyetherketone or derivatives thereof}, as moulding material · CPC title

• B29K2067/00

  Use of polyesters {or derivatives thereof}, as moulding material · CPC title

• B29C70/521

  and impregnating the reinforcement before the die · CPC title

• C08L2203/18

  used for pipes · CPC title