Rapid curing thiol epoxy resin with improved compression strength performance

Patent metadata

Field	Value
Publication number	US-9611375-B1
Application number	US-201514931518-A
Country	US
Kind code	B1
Filing date	Nov 3, 2015
Priority date	Nov 3, 2015
Publication date	Apr 4, 2017
Grant date	Apr 4, 2017

Abstract

Aspects described herein generally describe epoxy resins and methods of epoxy resin formation. In some embodiments, a resin includes the reaction product of one or more polythiols, one or more polyepoxides, one or more fillers and one or more amine catalysts. Polythiols have between two and about ten thiol moieties. Polyepoxides have between two and about ten epoxy moieties. One or more amine catalysts of the formula NR 1 R 2 R 3 , wherein each of R 1 , R 2 , and R 3 is independently linear or branched C1-20 alkyl or two or more of R 1 , R 2 , and R 3 combine to form cycloalkyl. The resin has a compressive strength of at least 14 ksi at 2% offset at 70° F. and at least 8 ksi at 2% offset at 190° F.

First claim

What is claimed is:

1. A vehicle component comprising a resin that is the reaction product of:
one or more polythiols having between two and about ten thiol moieties;
one or more polyepoxides having between two and about ten epoxy moieties;
one or more solid particulate fillers; and
one or more amine catalysts of the formula NR 1 R 2 R 3 , wherein each of R 1 , R 2 , and R 3 is independently linear or branched C1-20 alkyl or two or more of R 1 , R 2 , and R 3 combine to form cycloalkyl, and
wherein the molar ratio of polyepoxides to polythiols is about 0.9 and the resin has a compressive strength of at least 14 ksi at 2% offset at 70° F. and at least 8 ksi at 2% offset at 190° F.

2. The vehicle component of claim 1 , wherein the one or more polythiols has an equivalent molecular weight of between about 20 to about 115.

3. The vehicle component of claim 1 , wherein at least one of the one or more polythiols is of the formula SH—R—SH, wherein R is selected from the group consisting of alkyl, cycloalkyl, thiol-substituted alkyl, and thiol-substituted cycloalkyl.

4. The vehicle component of claim 1 , wherein each instance of the polythiol is independently selected from the group consisting of 1,2,3-propanetrithiol, 1,2,4-tris(2-mercaptoethyl) cyclohexane, and 1,3,5-tris(2-mercaptoethyl)cyclohexane.

5. The vehicle component of claim 1 , wherein each instance of the solid particulate fillers is independently selected from the group consisting of crystalline silica, fumed silica, methylated fumed silica, alumina, mica, silicate, talc, aluminosilicate, barium sulfate, diatomite, calcium carbonate, calcium sulfate, carbon, and wollastonite.

6. The vehicle component of claim 1 , wherein each instance of the one or more amine catalysts is independently selected from the group consisting of diisopropylethylamine, N-alkyl-piperidine, N-alkyl-piperazine, 1,4-diazabicyclo[2.2.2]octane, 1,8-diazabicyclo[5.4.0]undec-7-ene, trimethylamine, triethylamine, tripropylamine, N,N-dimethylethylamine, N,N-dimethylpropylamine, N,N-dimethylbutylamine, N,N-dimethylpentylamine, N,N-dimethylhexylamine, N,N-dimethylheptylamine, N,N-dimethyloctylamine, N,N-dimethylnonylamine, N,N-dimethyldecylamine, N,N-dimethylundecylamine, N,N-dimethyldodecylamine, N,N-dimethyltridecylamine, N,N-dimethyltetradecylamine, N,N-dimethylpentadecylamine, N,N-dimethylhexadecylamine, N,N-dimethylheptadecylamine, N,N-dimethyloctadecylamine, N,N-dimethylnonadecylamine, N,N-dimethyleicosylamine, N,N-diethylpropylamine, N,N-diethylbutylamine, N,N-diethylpentylamine, N,N-diethylhexylamine, N,N-diethylheptylamine, N,N-diethyloctylamine, N,N-diethylnonylamine, N,N-diethyldecylamine, N,N-diethylundecylamine, N,N-diethyldodecylamine, N,N-diethyltridecylamine, N,N-diethyltetradecylamine, N,N-diethylpentadecylamine, N,N-diethylhexadecylamine, N,N-diethylheptadecylamine, N,N-diethyloctadecylamine, N,N-diethylnonadecylamine, N,N-diethyleicosylamine, N,N-dipropylbutylamine, N,N-dipropylpentylamine, N,N-dipropylhexylamine, N,N-dipropylheptylamine, N,N-dipropyloctylamine, N,N-dipropylnonylamine, N,N-dipropyldecylamine, N,N-dipropylundecylamine, N,N-dipropyldodecylamine, N,N-dipropyltridecylamine, N,N-dipropyltetradecylamine, N,N-dipropylpentadecylamine, N,N-dipropylhexadecylamine, N,N-dipropylheptadecylamine, N,N-dipropyloctadecylamine, N,N-dipropylnonadecylamine, and N,N-dipropyleicosylamine.

7. The vehicle component of claim 6 , wherein the one or more amine catalysts is N,N-dimethyltetradecylamine.

8. The vehicle component of claim 1 , wherein the one or more amine catalysts is a salt.

9. The vehicle component of claim 1 , wherein the one or more amine catalysts is between about 0.1% wt to about 10% wt of the resin.

10. The vehicle component of claim 1 , wherein the one or more amine catalysts is between about 1% wt to about 3% wt of the resin.

11. The vehicle component of claim 1 , wherein at least one of the one or more polyepoxides has between four and about ten epoxy moieties.

12. The vehicle component of claim 1 , wherein each instance of the one or more polyepoxides is independently selected from the group consisting of N,N,N′,N′-tetraglycidyl-4,4′-diaminodiphenylmethane, poly[(phenyl glycidyl ether)-codicyclopentadiene], tetraphenylolethane glycidyl ether, and tris(4-hydroxyphenyl)methane triglycidyl ether.

13. The vehicle component of claim 12 , wherein at least one of the one or more polyepoxides is tetraphenylolethane glycidyl ether or tris(4-hydroxyphenyl)methane triglycidyl ether.

14. The vehicle component of claim 12 , wherein the one or more amine catalysts is N,N-dimethyltetradecylamine.

15. The vehicle component of claim 1 , wherein the one or more solid particulate fillers is between about 10% wt to about 75% wt of the resin.

16. The vehicle component of claim 15 , wherein the one or more solid particulate fillers is between about 50% wt to about 55% wt of the resin.

17. The vehicle component of claim 1 , wherein the vehicle component is a panel, a coated lap joint between two or more panels, a wing-to-fuselage assembly, structural aircraft composite, fuselage body-joint or wing rib-to-skin joint.

Assignees

• Boeing Co

Inventors

• Nowak Andrew P
• Rodriguez April R
• Boundy Thomas
• Pajel Carissa A
• Adjorlolo Alain A

Classifications

• C08G59/66

  Mercaptans · CPC title

• C08J2363/00

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

• C09J163/00

  Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins · CPC title

• C08G59/10 Primary

  of polyamines with epihalohydrins or precursors thereof · CPC title

• C08K9/06

  with silicon-containing compounds · CPC title