# US 12,180,338 B2 · Bioadvantaged nylon: polycondensation of 3-hexenedioic acid with hexamethylenediamine

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- Number: US 12,180,338 B2
- Document ID: US12180338B2
- Status: Granted
- Kind: B2
- Application number: 18/623,237
- Filed: 2024-04-01
- Published: 2024-09-05
- Granted: 2024-12-31
- Earliest claimed: 2015-11-10
- Assignees: Iowa State University Research Foundation, Inc.
- Applicants: Iowa State University Research Foundaton, Inc.
- Inventors: Nacu Hernandez; Mengguo Yan; Eric William Cochran; John Edward Matthiesen; Jean-Philippe Tessonnier
- Web page: https://patentgrep.com/patent/US12180338B2

## CPC

- C08G 69/265: {from at least two different diamines or at least two different dicarboxylic acids}
- C08G 69/26: derived from polyamines and polycarboxylic acids
- C08G 69/28: Preparatory processes
- C08G 69/48: Polymers modified by chemical after-treatment
- C08G 77/455: containing polyamide, polyesteramide or polyimide sequences
- C08G 81/028: {containing polyamide sequences}
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

The present invention relates to a polymer comprising a repeating group having the structure of formula (I) wherein R, R1, R2, R3, R4, X, and s are as described herein and salt thereof. Also disclosed is a process of synthesizing such polymers.

## Claims

### Claim 1

A polymer comprising a repeating group having the structure of formula (I):
wherein
X is NH;
R is independently selected from the group consisting of H and C1-20 alkyl;
R1, R2, R3, and R4 are independently selected from the group consisting of H and —U—C1-1002 alkyl substituted 1-2 times with a substituent independently selected at each occurrence thereof from the group consisting of —OH, —SO3R5, —P(O)(OR5)2, —N(R5)2, —N(R5)3+Hal−, and
with the proviso that at least one of R1, R2, R3, or R4 is not hydrogen;
A and I are independently selected from a point of attachment to formula (I) or R1, R2 R3, or R4; or —Si(R6)3;
B, C, D, E, F, G, and H are independently selected from the group consisting of a bond, O, or Si;
R5 is independently selected at each occurrence thereof from the group consisting of H, C1-6 alkyl, and halogen;
R6 is optional, and if present, is independently selected at each occurrence thereof from the group consisting of H, OH, halogen, C1-6 alkyl, —CN, and phenyl, wherein each phenyl and C1-6 alkyl can be optionally substituted 1-4 times with a substituent independently selected at each occurrence thereof from the group consisting of H, —OH, halogen, —CN, —N(R7)2, —C(O)R7, and —C(O)—X—CH2—(CH2)s—XR7;
R7 is independently selected at each occurrence thereof from the group consisting of H, C1-6 alkyl, and
U is optional and, if present, is —(S)p—;
is a terminal group of the polymer;
d is 1-1,000,000;
e is 1-1,000,000;
m is 0 to 1,000,000;
n is 0 to 10;
p is 1 to 8; and
s is 1 to 50;
or a salt thereof.

### Claim 2 (depends on 1)

The polymer of claim 1, wherein the polymer has 2-10,000,000 repeating groups with the structure of formula (I).

### Claim 3 (depends on 1)

The polymer of claim 1, wherein R1, R2, R3, and R4 are independently selected from the group consisting of H and —U—C1-1002 alkyl substituted 1-2 times with a substituent independently selected at each occurrence thereof from the group consisting of —OH, —SO3R5, —P(O)(OR5)2, —N(R5)2, and —N(R5)3+Hal−.

### Claim 4 (depends on 1)

The polymer of claim 1, wherein the repeating group has the structure of formula (Ib):

### Claim 5 (depends on 1)

The polymer of claim 1, wherein the repeating group has the structure of formula (Ib′):

### Claim 6 (depends on 1)

The polymer of claim 1, wherein the repeating group has the structure of formula (Ic):

### Claim 7 (depends on 1)

The polymer of claim 1, wherein the repeating group has the structure of formula (Ic′):

### Claim 8 (depends on 1)

The polymer of claim 1, wherein the repeating group has the structure of formula (Id):

### Claim 9 (depends on 1)

The polymer of claim 1, wherein the repeating group has the structure of formula (Id′):

### Claim 10 (depends on 1)

The polymer of claim 1, wherein the repeating group has the structure of formula (Ie):

### Claim 11 (depends on 1)

The polymer of claim 1, wherein the repeating group has the structure of formula (Ie′):