US 11,879,033 B2
Polycyloolefinic polymers and anion exchange membranes derived therefrom
Paul A Kohl, Atlanta, GA (US); Mrinmay Mandal, Atlanta, GA (US); Matthew L Barchok, Akron, OH (US); Doug Skilskyj, Akron, OH (US); and Larry F Rhodes, Akron, OH (US)
Assigned to PROMERUS, LLC, Akron, OH (US); and GEORGIA TECH RESEARCH CORPORATION, Atlanta, GA (US)
Filed by PROMERUS, LLC, Akron, OH (US); and GEORGIA TECH RESEARCH CORPORATION, Atlanta, GA (US)
Filed on Jul. 30, 2021, as Appl. No. 17/389,593.
Claims priority of provisional application 63/058,738, filed on Jul. 30, 2020.
Prior Publication US 2022/0033571 A1, Feb. 3, 2022
Int. Cl. C08G 61/02 (2006.01); C08G 61/12 (2006.01); C08F 8/32 (2006.01); H01M 8/1004 (2016.01); H01M 50/414 (2021.01); B01J 41/13 (2017.01)
CPC C08G 61/02 (2013.01) [B01J 41/13 (2017.01); C08G 61/125 (2013.01); H01M 8/1004 (2013.01); H01M 50/414 (2021.01); C08G 2261/11 (2013.01); C08G 2261/12 (2013.01); C08G 2261/146 (2013.01); C08G 2261/148 (2013.01); C08G 2261/1412 (2013.01); C08G 2261/1644 (2013.01); C08G 2261/3242 (2013.01); C08G 2261/3324 (2013.01); C08G 2261/3325 (2013.01); C08G 2261/76 (2013.01)] 19 Claims
OG exemplary drawing
 
1. A polymer comprising:
a) one or more first repeating unit of formula (IA) derived from a monomer of formula (I):

OG Complex Work Unit Chemistry
wherein:
custom character represents a position at which the bonding takes place with another repeat unit;
Y and Y′ are the same or different and independently of each other selected from the group consisting of —CH2—, —CH2—CH2— and —O—;
m is an integer from 0 to 3;
at least one of R1, R2, R3 and R4 is a group of the formula R—X,
where R is selected from the group consisting of (C1-C10)alkylene, (C3-C8)cycloalkylene, (C1-C10)alkylene(C3-C8)cycloalkylene, (C1-C10)alkylene(C3-C8)cycloalkylene(C1-C10)alkylene, (C1-C10)alkylene(C6-C10)arylene and (C1-C10)alkylene(C6-C10)arylene(C1-C10)alkylene; and
X is a group of the formula N(R5)(R6)(R7)⊕OH⊖, where
at least one of R5, R6 and R7 is selected from the group consisting of: (C1-C10)alkyleneN(R5′)(R6′), (C3-C5)cycloalkyleneN(R5′)(R6′), (C1-C10)alkylene(C3-C8)cycloalkyleneN(R5′)(R6′), (C1-C10)alkylene(C3-C8)cycloalkylene(C1-C10)alkyleneN(R5′)(R6′), (C1-C10)alkylene(C6-C10)aryleneN(R5′)(R6′) and (C1-C10)alkylene(C6-C10)arylene(C1-C10)alkyleneN(R5′)(R6′); wherein
R5 and R6′ are the same or different and independently of each other selected from the group consisting of linear or branched (C1-C10)alkyl, (C3-C8)cycloalkyl, (C1-C10)alkyl(C3-C8)cycloalkyl and (C1-C10)alkyl(C6-C10)aryl;
the remaining R5, R6 and R7 are the same or different and independently of each other selected from the group consisting of linear or branched (C1-C10)alkyl, (C3-C8)cycloalkyl, (C1-C10)alkyl(C3-C8)cycloalkyl and (C1-C10)alkyl(C6-C10)aryl; and
the remaining R1, R2, R3 and R4 are independently of each other selected from the group consisting of hydrogen, linear or branched (C1-C10)alkyl, (C3-C8)cycloalkyl, (C1-C10)alkyl(C3-C8)cycloalkyl and (C1-C10)alkyl(C6-C10)aryl;
b) one or more second repeating unit of formula (IIA) derived from a monomer of formula (II):

OG Complex Work Unit Chemistry
wherein:
custom character represents a position at which the bonding takes place with another repeat unit;
Z and Z′ are the same or different and independently of each other selected from the group consisting of —CH2—, —CH2—CH2— and —O—;
n is an integer from 0 to 3; and
R8, R9, R10 and R11 are the same or different and independently of each other selected from the group consisting of hydrogen, linear or branched (C1-C10)alkyl, (C3-C8)cycloalkyl, (C1-C10)alkyl(C3-C8)cycloalkyl and (C1-C10)alkyl(C6-C10)aryl; and
wherein the polymer is a random polymer and wherein the first repeat unit is crosslinked with another first repeat unit on the same or different polymer chains such that the polymer has at least two percent of the available sites reacted between the repeat units and exhibits ion conductivity of at least 150 mS/cm at 80° C.