Synthesis of alternating polyamide esters by melt and solution polycondensations of N,N′-Di(6-hydroxycaproyl) diamines and N-6-hydroxycaproyl aminoalcohol with terephthalic and adipic dimethyl esters and dichlorides

Abstract

SynopsisAlternating polyamide esters of structures A and B were obtained by melt polymerization of dimethyl adipate and terephthalate or by solution polymerization of adipoyl and terephthaloyl chlorides, with N,N'-di(6-hydroxycaproy1)diamines and an N-6-hydroxycaproyl aminoalcohol:where R1 is selected from dimethylene, hexamethylene, and p-phenylene radicals, and Rz is selected from tetramethylene or p-phenyl radical. Polyamide esters of structure A' were also prepared:Average values of melting points of the resulting polyamide esters were dependent on the starting diacid derivatives, amide diols, and methods of polymerizations as follows:where CPZ, CHD, CED, and CPPD are N,N'-di(6-hydroxycaproy1)-, each in this order: piperazine, hexamethylenediamine, ethylenediamine, and p-phenylenediamine. ECA is N-(2-hydroxyethyl)6-hydroxycaproamide. For a given polyamide ester obtained from the same starting materials and by the same method of polymerization, the melting points increased with inherent viscosities. Polyamide esters of high molecular weight were obtained from CHD with both adipic and terepbthalic derivatives both by melt and solution polymerizations. the other amide diols gave lower molecular weights. Solution polymerization gave colorless or light-colored polymers, while melt polymerization gave deeper-colored polymers.

Novel Biodegradable Copolymers with a Periodic Sequence Structure Derived from Succinate Butan‐1,4‐diol, and Butan‐1,4‐diamine

“…Many types of aliphatic polyester‐amides have been synthesized by various techniques 1–20. Copolymers with random, multi‐block, or alternative distributions of ester and amide groups were produced by bulk‐, melt‐, and solution polycondensation reactions, and the ester‐amide interchange reaction, and the structures, physical properties, and degradabilities of these polyester‐amides were characterized.…”

Concept and Synthesis of Poly(ester amide)s with One Isolated, Two or Three Consecutive Amide Bonds Randomly Distributed Along the Polyester Backbone

“…Regular PEAs with AAEE sequences can be synthesized by condensing preformed bisamide diols or bisester diamines with diacids or diacid chlorides in solution [37][38][39] or melt [37][38][39][40][41]. Other types of preformed monomers were condensed with activated esters in solution [37,[42][43][44][45][46][47][48] or with dicarboxylic acid dichlorides or activated esters by interfacial polymerisation [49][50][51][52][53][54][55][56][57].…”

“…Such preformed monomers can be condensed with dicarboxylic acids, acid chlorides or esters in solution or melt to yield PEAs. Bisamide diols can be synthesised by reacting diamines with lactones or hydroxy acids in melt or solution [38,39,[70][71][72][73][77][78][79]. In most cases this reaction is accompanied by successive oligomerization of the lactone via the formed hydroxyl groups even in the absence of a catalyst.…”

One‐pot synthesis of biodegradable and linear poly(ester amide)s based on renewable resources

“…Katayama et al . synthesized alternating polyamide esters by melt polymerization of dimethyl adipate and terephthalate or by solution polymerization of adipoyl and terephthaloyl chlorides . Katsarava et al .…”