Bioadvantaged nylon: polycondensation of 3-hexenedioic acid with hexamethylenediamine

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;
• a is 1-1,000,000;
• b is 1-1,000,000;
• c is 1-1,000,000;
• 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.