Bioadvantaged nylon: polycondensation of 3-hexenedioic acid with hexamethylenediamine

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 C 1-20 alkyl;

R 1 , R 2 , R 3 , and R 4 are independently selected from the group consisting of H and —U—C 1-1002 alkyl substituted 1-2 times with a substituent independently selected at each occurrence thereof from the group consisting of —OH, —SO 3 R 5 , —P(O)(OR 5 ) 2 , —N(R 5 ) 2 , —N(R 5 ) 3 + Hal − , and

with the proviso that at least one of R 1 , R 2 , R 3 , or R 4 is not hydrogen;

A and I are independently selected from a point of attachment to formula (I) or R 1 , R 2 R 3 , or R 4 ; or —Si(R 6 ) 3 ;

B, C, D, E, F, G, and H are independently selected from the group consisting of a bond, O, or Si;

R 5 is independently selected at each occurrence thereof from the group consisting of H, C 1-6 alkyl, and halogen;

R 6 is optional, and if present, is independently selected at each occurrence thereof from the group consisting of H, OH, halogen, C 1-6 alkyl, —CN, and phenyl, wherein each phenyl and C 1-6 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(R 7 ) 2 , —C(O)R 7 , and —C(O)—X—CH 2 —(CH 2 ) s —XR 7 ;

R 7 is independently selected at each occurrence thereof from the group consisting of H, C 1-6 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.

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

3. The polymer of claim 1 , wherein R 1 , R 2 , R 3 , and R 4 are independently selected from the group consisting of H and —U—C 1-1002 alkyl substituted 1-2 times with a substituent independently selected at each occurrence thereof from the group consisting of —OH, —SO 3 R 5 , —P(O)(OR 5 ) 2 , —N(R 5 ) 2 , and —N(R 5 ) 3 + Hal − .

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

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

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

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

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

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

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

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