Enzymatically catalyzed polycondensation of p-xylylenediamine and diethyl sebacate resulted in oligo(p-xylylene sebacamide) with high melting temperatures (223-230 °C) and the enzymatic polycondensation of dimethyl terephthalate and 1,8-diaminooctane leads to oligo(octamethylene terephthalamide) with two melting temperatures at 186 and 218 °C. No oligoamides, but products 1 and 2, were formed from the enzymatic reaction of dimethyl terephthalate and p-xylylenediamine. All reactions were catalyzed by CAL-B, icutinase, or CLEA cutinase. All reactions catalyzed by CAL-B show higher conversion than reactions catalyzed by icutinase or CLEA cutinase. The highest DPmax of 15 was achieved in a one-step and two-step synthesis of oligo(p-xylylene sebacamide) catalyzed by CLEA cutinase.
Fusarium solani pisi cutinase-catalyzed synthesis of polyamides Stavila, E.; Arsyi, R. Z.; Petrovic, D. M.; Loos, K. a b s t r a c tPolyamides, or nylon, are widely used in fiber and engineering plastic materials, due to their good mechanical and thermal properties. Synthesis of oligomers from nylon-4,10, nylon-6,10, and nylon-8,10 were performed via polycondensation of diamines (1,4-butanediamine, 1,6-hexanediamine, and 1,8-diaminooctane) and diester (diethyl sebacate). These reactions were catalyzed by immobilized cutinase from Fusarium solani pisi on Lewatit beads, cutinase in the form of cross-linked enzyme aggregates (CLEA), or by immobilized Lipase B from Candida antarctica (N435). The highest maximal degree of polymerization (DP max ), up to 16, can be achieved in the synthesis of nylon-8,10 catalyzed by CLEA cutinase in diphenyl ether at 70°C. By performing a reaction at cutinase optimal temperature (70°C), CLEA cutinase in the synthesis of nylons shows good catalytic activity, like N435.
The enzymatic ring-opening copolymerization of ε-caprolactone (ε-CL) and β-lactam by using Candida antarctica lipase B (CAL-B) as catalyst was studied. Variation of the feed ratios of 25:75, 50:50, and 75:25 of ε-CL/β-lactam was performed. The products contain poly(ε-CL-co-β-lactam) and the homopolymers of poly(ε-CL) and poly(β-lactam). The structure of the copolymers was determined by MALDI-ToF MS. Poly(ε-CL-co-β-lactam) has an alternating and random structure consisting of alternating repeating units with oligo(ε-CL) or oligo(β-lactam). The highest fraction of the alternating copolymers resulted from the reaction with a feed ratio 50:50. The copolymer is a semicrystalline polymer with a T m at 124 °C and T g s at −15 and 50 °C. Interestingly, the copolymer also demonstrated cold crystallization at 29 and 74 °C, after quenching the sample from the melt in liquid nitrogen.
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