Novel polymers and methods for their manufacture

Patent metadata

Field	Value
Publication number	US-2017355811-A1
Application number	US-201515527967-A
Country	US
Kind code	A1
Filing date	Nov 17, 2015
Priority date	Nov 18, 2014
Publication date	Dec 14, 2017
Grant date	—

Abstract

Embodiments of the invention relate to a novel class of polymers with superior mechanical properties and chemical stability, as compared to known polymers. These polymers are particularly well suited for use in anion exchange membranes (AEMs), including those employed in fuel cells. Novel methods for the manufacture of these polymers are also described.

First claim

What is claimed is:

1 . A method of forming a polyarylene, the method comprising:
reacting an aromatic compound and a trifluoroalkyl ketone in the presence of a strong acid to form a bromoalkylated precursor polymer; and reacting the bromoalkylated precursor polymer with a trialkylamine and sodium hydroxide to form a polyarylene having a main chain free of ether linkages.

2 . The method of claim 1 , wherein the trifluoroalkyl ketone includes at least one trifuloroalkyl ketone selected from a group consisting of: 7-bromo-1,1,1-trifluoroheptan-2-one and methyl trifluoromethyl ketone.

3 . The method of claim 1 , wherein the aromatic compound is selected from a group consisting of:

4 . The method of claim 3 , wherein the aromatic compound is

5 . The method of claim 1 , wherein the aromatic compound is selected from a group consisting of:

6 . A polymer of formula I prepared according to the method of claim 1

wherein Ar is an aromatic compound, r is from 100 to 1,000,000, R 2 is

R is an alkyl group, and n is from 1 to 20.

7 . The polymer of claim 6 , wherein Ar is

8 . The polymer of claim 7 having formula IA

wherein x+y=1.

9 . The polymer of claim 8 , wherein x is 1 and y is 0, or x is 0.65 and y is 0.35, or x is 0.44 and y is 0.56.

10 . A polymer of formula III prepared according to the method of claim 1

wherein Ar is an aromatic compound, R″ is

r is from 100 to 1,000,000, and m is from 0 to 20.

11 . A polymer according to formula I

wherein Ar is an aromatic compound, r is from 100 to 1,000,000, R 2 is

R is an alkyl group, and n is from 1 to 20.

12 . The polymer of claim 11 , wherein the aromatic compound is selected from a group consisting of:

13 . The polymer of claim 11 , prepared from a bromoalkylated precursor polymer of formula II according to the reaction:

wherein R 1 is

14 . The polymer of claim 11 , wherein the bromoalkylated precursor polymer of formula II is prepared according to the reaction:

15 . The polymer of claim 14 , wherein the strong acid is trifluoromethanesulfonic acid.

16 . The polymer of claim 11 having formula IA

wherein x+y=1.

17 . The polymer of claim 16 , wherein x is 1 and y is 0, or x is 0.65 and y is 0.35, or x is 0.44 and y is 0.56.

18 . A polymer according to formula III

wherein Ar is an aromatic compound, R″ is

r is from 100 to 1,000,000, and m is from 0 to 20.

19 . The polymer of claim 18 , wherein the aromatic compound is selected from a group consisting of:

20 . The polymer of claim 18 , prepared from a bromoalkylated precursor polymer of formula IV according to the reaction:

wherein R is

n is from 1 to 20, and R is an alkyl group.

Assignees

• Rensselaer Polytech Inst

Inventors

• Bae Chulsung
• Lee Woo-Hyung

Classifications

• C08G2261/312

  Non-condensed aromatic systems, e.g. benzene · CPC title

• C25B13/08

  based on organic materials · CPC title

• H01M8/1072

  by chemical reactions, e.g. in situ polymerisation or in situ crosslinking · CPC title

• H01M8/1039

  halogenated, e.g. sulfonated polyvinylidene fluorides · CPC title

• C09D5/14

  Paints containing biocides, e.g. fungicides, insecticides or pesticides (C09D5/16 takes precedence) · CPC title