Enzymatic Synthesis and Chemical Recycling of Polythiocaprolactone

Shimokawa, Keisuke; Katô, Makoto; Matsumura, Shuichi

doi:10.1002/macp.201000488

Cited by 19 publications

(13 citation statements)

References 36 publications

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“…Crude material was carried forward without purification; characterization matched the literature. 26 1 H NMR (CDCl 3 ): δ = 2.57–2.49 (q, 2H; –CH 2 SH), 2.39–2.34 (t, 2H; –CH 2 COOH), 1.70–1.59 (m, 2H; –CH 2 CH 2 SH), 1.50–1.42 (m, 2H; CH 2 CH 2 COOH), 1.37–1.31 (m, 2H; –CH 2 (CH 2 )2SH).…”

Section: Methodsmentioning

confidence: 99%

Poly(thioester) by Organocatalytic Ring-Opening Polymerization

Bannin

Kiesewetter

2015

Macromolecules

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Organocatalysts typically used for the ring-opening polymerization (ROP) of cyclic ester monomers are applied to a thiolactone, ε-thiocaprolactone (tCL). In the absence of an H-bond donor, a nucleophilic polymerization mechanism is proposed. Despite the decreased ability of thioesters and thiols (versus esters and alcohols) to H-bond, H-bonding organocatalysts—a thiourea in combination with an H-bond accepting base—are also effective for the ROP of tCL. The increased nucleophilicity of thiols (versus alcohols) is implicated in the increased Mw/Mn of the poly(thiocaprolactone) versus poly(caprolactone), but deleterious transesterification is suppressed in the presence of a thiourea. The thioester monomer, tCL, is shown to be thermodynamically similar to ε-caprolactam but kinetically similar to ε-caprolactone.

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Section: Methodsmentioning

confidence: 99%

Poly(thioester) by Organocatalytic Ring-Opening Polymerization

Bannin

Kiesewetter

2015

Macromolecules

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“…In addition, using a lipase as the catalyst in anhydrous dilute solution, polyesters can be easily depolymerized into repolymerizable cyclic oligomers. In such a way, lipases may also contribute to the establishment of sustainable polymer production and chemical recycling systems [10][11][12].…”

Section: Open Accessmentioning

confidence: 99%

Enzymatic Synthesis and Chemical Recycling of Novel Polyester-Type Thermoplastic Elastomers

Yagihara

Matsumura

2012

Polymers

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Novel polyester-type thermoplastic elastomers based on poly(alkylene succinate)s were synthesized by the lipase-catalyzed copolymerization of cyclic diol/succinate oligomer and cyclic diol/alkylthiosuccinate oligomer. These copolymers exhibited biodegradabilities by activated sludge and a wide range of thermal and mechanical properties that were dependent on the molecular structure and the content of side alkylthio groups. The degree of crystallinity of the copolymer decreased with increasing content of alkylthio groups, which were introduced into the polymer chain as a soft segment. Furthermore, lipase-catalyzed depolymerization of these copolymers into cyclic oligomers and repolymerization of the oligomers was carried out. A repolymerized copolymer having the same M w and monomer composition as the initial copolymer was obtained, indicating the chemical recyclability of the copolymer.

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“…6-mercaptohexanoic acid synthesis protocol was adapted from Shimokawa et al [30]. The reaction is shown in Scheme 1.…”

Section: Methodsmentioning

confidence: 99%

Original Macromolecular Architectures Based on poly(ε-caprolactone) and poly(ε-thiocaprolactone) Grafted onto Chitosan Backbone

Unlu

Pollet

Avérous

2018

IJMS

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Polyester and/or polythioester grafted chitosan copolymers were synthesized. For that, poly(ε-caprolactone) (PCL), poly(ε-thiocaprolactone) (PTCL), and their copolymers were first synthesized by ring opening polymerization. Copolymers with caprolactone:thiocaprolactone (CL:TCL) molar ratios of 2:1, 1:1, 1:2 were synthesized. All of the synthesized macromolecular architectures were characterized using different spectral (Fourier transform infrared (FTIR), proton nuclear magnetic resonance (1H-NMR), X-Ray diffraction (XRD)) and thermal (Differential scanning calorimetry (DSC), Thermogravimetric analysis (TGA)) methods. Grafting was then performed according two distinct routes: (i) using a blend of both homopolymers (PCL and PTCL) or (ii) using pre-synthesized copolymers with controlled CL:TCL ratios. Hexamethylene diisocyanate was used as a grafting/coupling agent through urethane bonds with high yield. Grafting preferentially occurred at sulfur sites. The results indicated that PTCL is more reactive and favorable than PCL for grafting onto chitosan. With the homopolymers blend grafting route, the corresponding materials mostly had a higher PTCL portion than expected. To obtain polyester grafted chitosan with a determined CL:TCL ratio, the copolymer grafting route would yield better results.

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Enzymatic Synthesis and Chemical Recycling of Polythiocaprolactone

Cited by 19 publications

References 36 publications

Poly(thioester) by Organocatalytic Ring-Opening Polymerization

Poly(thioester) by Organocatalytic Ring-Opening Polymerization

Enzymatic Synthesis and Chemical Recycling of Novel Polyester-Type Thermoplastic Elastomers

Original Macromolecular Architectures Based on poly(ε-caprolactone) and poly(ε-thiocaprolactone) Grafted onto Chitosan Backbone

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