Rapid cure polymeric resins

Patent metadata

Field	Value
Publication number	US-10189925-B2
Application number	US-201715664230-A
Country	US
Kind code	B2
Filing date	Jul 31, 2017
Priority date	Dec 22, 2014
Publication date	Jan 29, 2019
Grant date	Jan 29, 2019

Abstract

A polysulfide material having reactive vinyl end groups and a method of making a vinyl end-capped polysulfide material are described. The vinyl end-capped polysulfide material has potential applications as a sealant, an adhesive, a coating, a caulking, or the like. In a specific example, the polysulfide material may be used as a precursor material for a sealant resin in the manufacturing of an integral fuel tank of an aircraft. An example method for making polysulfide materials includes contacting a vinyl-functionalized aryl halide and/or a vinyl-functionalized heteroaryl halide with dithiols and/or trithiols in the presence of an organic solvent.

First claim

What is claimed is:

1. A polymer of formula (I):

wherein:
each instance of R 1 is —C 1-5 —O—C 1-5 —O—C 1-5 —;
each instance of R 2 is the same or different and is selected from

 each instance of R 24 is independently selected from hydrogen, alkyl, or alkoxy;
“Linker” is of formula (II):

c is less than 1.0;
d is 0 when c is 0; and
a+b+d is from about 7 to about 38.

2. The polymer of claim 1 , wherein each instance of R 24 is hydrogen.

3. The polymer of claim 2 , wherein each instance of R 2 is the same or different and is selected from -aryl-alkyl- or -aryl-.

4. The polymer of claim 3 , wherein each instance of R 2 is the same or different and is selected from -benzyl- or -phenyl-.

5. The polymer of claim 1 , wherein each instance of R 24 is alkyl.

6. The polymer of claim 5 , wherein each instance of R 2 is the same or different and is selected from -aryl-alkyl- or -aryl-.

7. The polymer of claim 6 , wherein each instance of R 2 is the same or different and is selected from -benzyl- or -phenyl-.

8. The polymer of claim 1 , wherein each instance of R 24 is alkoxy.

9. The polymer of claim 8 , wherein each instance of R 2 is the same or different and is selected from -aryl-alkyl- or -aryl-.

10. The polymer of claim 9 , wherein each instance of R 2 is the same or different and is selected from -benzyl- or -phenyl-.

11. The polymer of claim 1 , wherein the carbon to sulfur ratio of the polymer is from about 2:1 to about 3:1.

12. A component comprising the polymer of claim 1 disposed thereon.

13. The component of claim 12 , wherein the component is a wing assembly, a fuselage, a fuel tank, a pane of glass, or a hull.

14. The component of claim 12 , wherein the component comprises at least one of aluminum, steel, carbon fiber, glass, stone, or concrete.

15. A resin comprising the reaction product of the polymer of claim 1 and an initiator.

16. The resin of claim 15 , further comprising a filler material.

17. The resin of claim 16 , wherein the filler material is a carbon particle, carbon fiber, clay, nylon fiber, nylon particle, fullerene, fused silica particle, fused silica fiber, or a metal.

18. The resin of claim 17 , wherein the filler material is at least one of titanium dioxide or carbon black particles.

19. A polymer blend comprising:
a first polymer of formula (I):

wherein:
each instance of R 1 is —C 1-5 —O—C 1-5 —O—C 1-5 —;
each instance of R 2 is the same or different and is selected from

 each instance of R 24 is the same or different and is selected from hydrogen, alkyl, or alkoxy;
“Linker” is of formula (II):

c is less than 1.0;
d is 0 when c is 0; and
a+b+d is from about 7 to about 38; and

a second polymer of formula (I):

wherein:
each instance of R 1 is —C 1-5 —O—C 1-5 —O—C 1-5 —,
each instance of R 2 is the same or different and is selected from

 each instance of R 24 is the same or different and is selected from hydrogen (H), alkyl, or alkoxy;
“Linker” is of formula (II):

c=0, d=0, and
a+b is from about 7 to about 38.

20. A resin comprising the reaction product of the polymer blend of claim 19 and an initiator.

Assignees

• Boeing Co

Inventors

• Zweig Andrew M

Classifications

• C08F12/34

  Monomers containing two or more unsaturated aliphatic radicals · CPC title

• C08F12/30

  Sulfur · CPC title

• C08F12/22

  Oxygen · CPC title

• C07C323/12 Primary

  the carbon skeleton being acyclic and saturated · CPC title

• C08F212/34 Primary

  Monomers containing two or more unsaturated aliphatic radicals · CPC title