Rapid cure polymeric resins

Patent metadata

Field	Value
Publication number	US-9751966-B2
Application number	US-201514924079-A
Country	US
Kind code	B2
Filing date	Oct 27, 2015
Priority date	Dec 22, 2014
Publication date	Sep 5, 2017
Grant date	Sep 5, 2017

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 -alkyl-O-alkyl-O-alkyl-;
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 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 2 is the same or different and is selected from -aryl-alkyl- or -aryl-.

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

4. The polymer of claim 3 , wherein each instance of R 1 is -ethyl-O-methyl-O-ethyl-.

5. The polymer of claim 1 , wherein each instance of R 2 is -heteroaryl-.

6. The polymer of claim 1 , wherein each instance of R 2 is -heteroaryl-alkyl-.

7. The polymer of claim 1 , wherein each instance of -alkyl- of R 1 is selected from the group consisting of -methyl-, -ethyl-, and -propyl-.

8. The polymer of claim 1 , wherein c is greater than 0 and the Linker of formula (I) is:

9. The polymer of claim 8 , wherein each instance of R 1 is -ethyl-O-methyl-O-ethyl- and each instance of R 2 is -benzyl-.

10. The polymer of claim 8 , wherein each instance of -alkyl- of R 1 is selected from the group consisting of -methyl-, -ethyl-, and -propyl-.

11. The polymer of claim 1 , wherein c=0, and the polymer of formula (I) is selected from the group consisting of:

Ex.
R 2
R 1

 1a

—ethyl—O—methyl—O—ethyl—

 2a

—ethyl—O—methyl—O—ethyl—

 3a

—ethyl—O—methyl—O—ethyl—

 4a

—ethyl—O—methyl—O—ethyl—

 5a

—ethyl—O—methyl—O—ethyl—

 6a

—ethyl—O—methyl—O—ethyl—

 7a

—ethyl—O—methyl—O—ethyl—

 8a

—ethyl—O—methyl—O—ethyl—

 9a

—ethyl—O—methyl—O—ethyl—

10a

—ethyl—O—methyl—O—ethyl—

11a

—ethyl—O—methyl—O—ethyl—

12a

—ethyl—O—methyl—O—ethyl—

13a

—ethyl—O—methyl—O—ethyl—

14a

—ethyl—O—methyl—O—ethyl—

15a

—ethyl—O—methyl—O—ethyl—

16a

—ethyl—O—methyl—O—ethyl—

17a

Assignees

• Boeing Co

Inventors

• Zweig Andrew M

Classifications

• C07C323/12 Primary

  the carbon skeleton being acyclic and saturated · CPC title

• C08F12/22

  Oxygen · CPC title

• C08F212/34 Primary

  Monomers containing two or more unsaturated aliphatic radicals · CPC title

• C08F12/30

  Sulfur · CPC title

• C08F12/34

  Monomers containing two or more unsaturated aliphatic radicals · CPC title