Rapid curing thiol epoxy resin with improved compression strength performance

Patent metadata

Field	Value
Publication number	US-10570246-B2
Application number	US-201816047432-A
Country	US
Kind code	B2
Filing date	Jul 27, 2018
Priority date	Nov 3, 2015
Publication date	Feb 25, 2020
Grant date	Feb 25, 2020

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 NR1R2R3, wherein each of R1, R2, and R3 is independently linear or branched C1-20 alkyl or two or more of R1, R2, and R3 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 resin that is the reaction product of:
one or more polythiols, wherein at least one of the polythiols is 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;
one or more polyepoxides having from two to about ten epoxy moieties at a molar ratio of polyepoxides to polythiols of from about 0.85 to about 0.95;
one or more solid particulate fillers comprising from about 50% wt to about 55% wt of the resin; 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 a cycloalkyl.

2. The resin of claim 1 , wherein each of R 1 and R 2 is independently selected from C1-6 alkyl and R 3 is selected from a C7-20 alkyl.

3. The resin of claim 2 , wherein the one or more amine catalysts is between about 1% wt to about 3% wt of the resin.

4. The resin of claim 3 , wherein the one or more amine catalysts is N,N-dimethyltetradecylamine.

5. The resin of claim 3 , wherein 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.

6. A vehicle component comprising the resin of claim 2 disposed thereon.

7. The resin of claim 1 , wherein the molar ratio of polyepoxides to polythiols is about 0.9.

8. The resin of claim 1 , wherein 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.

9. The resin of claim 1 , wherein the one or more polythiols have about 20 equivalent molecular weight.

10. The resin of claim 9 , 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.

11. The resin of claim 1 , wherein at least one of the one or more polyepoxides has from four to about ten epoxy moieties.

12. A resin that is the reaction product of:
one or more polythiols, having from two to about ten thiol moieties,
one or more polyepoxides having from two to about ten epoxy moieties at a molar ratio of polyepoxides to polythiols of from about 0.85 to about 0.95;
one or more solid particulate fillers 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, 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 forma cycloalkyl.

13. The resin of claim 12 , wherein each instance of the solid particulate fillers is independently selected from the group consisting of crystalline silica, fumed silica, alumina, and mica.

14. A resin comprising:
1,3,5-tris(2-mercaptoethyl) cyclohexane;
N,N-dimethyltetradecylamine, 1,8-diazobicyclo[5.4.0]undec-7-ene, or salt thereof; and
one or more polyepoxides of the formula:

wherein a molar ratio of polyepoxides to 1,3,5-tris(2-mercaptoethyl) cyclohexane is from about 0.85 to about 0.95.

15. A method for forming a shim, comprising:
mixing one or more polythiols having from two to about ten thiol moieties with one or more polyepoxides having from two to about ten epoxy moieties and one or more solid particulate fillers to form a mixture, wherein a molar ratio of polyepoxides to polythiols of from about 0.85 to about 0.95; and
introducing an amine catalyst to the mixture to form a second mixture;
curing the second mixture; and
applying the second mixture to a vehicle component.

16. The method of claim 15 , wherein a molar ratio of polyepoxides to polythiols is about 0.9.

17. The method of claim 15 , wherein curing the second mixture is performed at a temperature of about 140° F. or less.

18. The method of claim 15 , further comprising applying the second mixture between two joined parts.

19. The method of claim 18 , wherein each of the two joined parts are vehicle components.

Assignees

• Boeing Co

Inventors

• Nowak Andrew Paul
• RODRIGUEZ April Rose
• Boundy Thomas Ian
• Pajel Carissa Ann
• Adjorlolo Alain A

Classifications

• C08G59/66

  Mercaptans · CPC title

• C08G59/10 Primary

  of polyamines with epihalohydrins or precursors thereof · CPC title

• C09J163/00

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

• C08G59/686

  containing nitrogen · CPC title

• C08J2363/00

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