Polyamides, and methods of producing thereof

A method of producing a polymer comprising:

• a) combining a compound of formula (1) with a nitrogen-containing compound of formula (2) under aqueous conditions to produce a compound of formula (3-a), wherein:
• the compound of formula (1) is
• wherein each R1a, R1b, R1c and R1d is independently H or alkyl,
• the nitrogen-containing compound of formula (2) is R2—NH2, wherein R2 is H or alkyl, and
• the compound of formula (3-a) is
• wherein R1a, R1b, R1c and R1d are as defined above for formula (1), and R2 is as defined above for formula (2);
• and
• b) combining the compound of formula (3-a) with a weak base to produce the polymer,
• wherein the polymer comprises repeating units of formula
• or a salt thereof, wherein R1a, R1b, R1c, R1d and R2 are as defined above for formula (3-a).

A method of producing a polymer, comprising:

• a) combining a compound of formula (3-b) with an alcohol of formula (4) and a halogenating agent to produce a compound of formula (5), wherein:
• the compound of formula (3-b) is
• wherein each R1a, R1b, R1c, R1d and R2 is independently H or alkyl,
• the alcohol of formula (4) is R3OH, wherein R3 is alkyl, and
• the compound of formula (5) is
• wherein R1a, R1b, R1c, R1d and R2 are as defined above for formula (3-b), and R3 is as defined above for formula (4);
• and
• b) condensing the compound of formula (5) to produce the polymer,
• wherein the polymer comprises repeating units of formula
• wherein R1a, R1b, R1c, R1d and R2 are as defined above for formula (3-b).

A method of producing a polymer comprising:

• a) combining a compound of formula (1) with a nitrogen-containing compound of formula (2) and an organic solvent, or combining a compound of formula (1) with a nitrogen-containing compound of formula (2) under non-aqueous conditions, to produce a compound of formula (3-b), wherein:
• the compound of formula (1) is
• wherein each R1a, R1b, R1c and R1d is independently H or alkyl,
• the nitrogen-containing compound of formula (2) is R2—NH2, wherein R2 is H or alkyl;
• and
• the compound of formula (3-b) is
• wherein R1a, R1b, R1c and R1d are as defined above for formula (1), and R2 is as defined above for formula (2);
• b) combining the compound of formula (3-b) with an alcohol of formula (4) and a halogenating agent to produce a compound of formula (5), wherein:
• the alcohol of formula (4) is R3OH, wherein R3 is alkyl;
• and
• the compound of formula (5) is
• wherein R1a, R1b, R1c, R1d and R2 are as defined above for formula (3-b), and R3 is as defined above for formula (4);
• and
• c) condensing the compound of formula (5) to produce the polymer,
• wherein the polymer comprises repeating units of formula
• wherein R1a, R1b, R1c, R1d and R2 are as defined above for formula (3-b).