Functionalization of trans-3-hexenedioic acid for the production of hydrophobic polyamides and chemical resistance thereof

A process for preparation of a polymer having the structure of formula (I):

• wherein
• X is NH or O;
• R is independently selected from the group consisting of H and C1-20 alkyl;
• R1 and R2 are independently selected from the group consisting of H, C1-100 alkyl, and —S—R3—R4;
• R3 is C1-100 alkylene;
• R4 is selected from the group consisting of —PO3−, —SO3−, —NH3+, —S−, —PO3H, —SO3H, —NH2, —SH, and —H;
• i is 1 to 1,000,000;
• j is 1 to 1,000,000;
• m is 1 to 30;
• n is 1 to 30;
• o is 1 to 30;
• s is 1 to 50;
• and
• is a terminal group of the polymer;
• or a salt thereof,
• said process comprising:
• providing a compound having the structure of formula (II):
• providing a compound having the structure of formula (III):
• providing a compound having the structure of formula (IV):
• and
• reacting the compound of formula (II), the compound of formula (III), and the compound of formula (IV) under conditions effective to produce the polymer of formula (I).