Thermoplastic polyurethane elastomers from bio-based poly(δ-decalactone) diols

Tang, Donglin; Macosko, Christopher W.; Hillmyer, Marc A.

doi:10.1039/c3py01120h

Cited by 51 publications

(48 citation statements)

References 18 publications

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“…33 Organocatalytic ROP of renewable 5-alkyl δlactones has also been studied, 41,43,45 however, significantly less than the non-substituted ones. 33 Organocatalytic ROP of renewable 5-alkyl δlactones has also been studied, 41,43,45 however, significantly less than the non-substituted ones.…”

Section: Resultsmentioning

confidence: 99%

“…Therefore, the preparation of polyether-polyester block copolymers is generally tedious as multiple steps of synthesis, isolation and purification are required. [41][42][43][44][45][46] The effectiveness of the organic acid catalyst (diphenyl phosphate) for the ROP of the substituted lactones was first investigated aiming at conditions to reach high monomer conversions and controlled molecular weights. Similarly to their metallic counterparts, organic catalysts also need to be appropriately chosen for each specific monomer type to achieve the best compromise between polymerization rate and control.…”

Section: Introductionmentioning

confidence: 99%

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Polymerization of 5-alkyl δ-lactones catalyzed by diphenyl phosphate and their sequential organocatalytic polymerization with monosubstituted epoxides

Zhao

Hadjichristidis

2015

Polym. Chem.

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ARTICLE This journal isOrganocatalytic ring-opening polymerization (ROP) of three renewable 5-alkyl δ-lactones, namely, δ-hexalactone (HL), δ-nonalactone (NL) and δ-decalactone (DL), using diphenyl phosphate (DPP) was investigated. Room temperature together with a relatively high monomer concentration (≥ 3 M) was demonstrated to be suited for the achievement of a living manner of the ROP, a high conversion of the lactone, a controlled molecular weight and a low dispersity of the polyester. HL, carrying a 5-methyl substituent, showed a much higher reactivity (polymerization rate) and a slightly higher equilibrium conversion than the ones with longer alkyl substituents (NL and DL). The effectiveness of DPP-catalyzed ROP of 5-alkyl δ-lactones facilitated the one-pot performance following the t-BuP 4 -promoted ROP of monosubstituted epoxides. It has been shown in an earlier study that substituted polyethers acted as "slow initiators" for non-substituted lactones. However, efficient initiations were observed in the present study as substituted lactones were polymerized from the substituted polyethers, which therefore has reinforced the previously developed "catalyst switch" strategy making it a more versatile tool for the synthesis of well-defined polyether-polyester block copolymers involving a large variety of epoxide and lactone monomers. ARTICLEThis journal is ARTICLE This journal is ARTICLE This journal is ARTICLE This journal is ARTICLEThis journal is Scheme 2. Reaction scheme toward the synthesis of polyether-polyester diblock copolymer via sequential organocatalytic ROP of a monosubstituted epoxide and a 5alkyl δ-lactone using the base→acid "catalyst switch" strategy. ARTICLE This journal is ARTICLE This journal is ARTICLEThis journal is

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Polymerization of 5-alkyl δ-lactones catalyzed by diphenyl phosphate and their sequential organocatalytic polymerization with monosubstituted epoxides

Zhao

Hadjichristidis

2015

Polym. Chem.

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“…In short, this simple way of preparing α,ω-hydroxyl-terminated poly(lactone) shows significant advances over previously reported synthetic methods. 43,44 Synthesis of Carboxy-Telechelic Poly(carvomenthide). The secondary hydroxyl terminal groups of the PCM samples were (Figure 1d).…”

Section: Synthesis Of Prepolymers Synthesis Of Carvomenthidementioning

confidence: 99%

Thermoset Elastomers Derived from Carvomenthide

Yang

Lee

Choi³

et al. 2014

Biomacromolecules

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Renewable thermoset elastomers were prepared using the plant-based monomer carvomenthide. Controlled ring-opening transesterification polymerization of carvomenthide using diethylene glycol as an initiator gave α,ω-dihydroxyl poly(carvomenthide) (HO-PCM-OH), which was subsequently converted to carboxy-telechelic poly(carvomenthide) (HOOC-PCM-COOH) by esterification with excess succinic anhydride through a one-pot, two-step process, leading to no crystallinity, high viscosity, strong thermal resistance, and low glass transition temperature of the resulting functionalized polyester. Thermal curing processes of the resulting 3, 6, and 12 kg mol(-1) prepolymers were achieved with trifunctional aziridine to give cross-linked PCM elastomers. The thermal properties, mechanical behavior, and biocompatibility of the rubbery thermoset products were investigated by differential scanning calorimetry, thermal gravimetric analysis, dynamic mechanical analysis, tensile tests under static and cyclic loads, and cell adherence. These new materials are useful candidates to satisfy the design objective for the engineering of a variety of soft tissues.

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“…Naturally occurring polymers such as cellulose, protein, and natural rubber have been widely utilized to design polymeric products . On the contrary, production of synthetic polymer from biomass, such as vegetable oils, terpenes, sugar, furfural, lignin, and lactic acid, is a fast‐growing research area . Among the large and diverse class of renewable biomass, terpenes, primary constituents of essential oil and plants are major biosynthetic building blocks in the area of sustainable polymers.…”

Section: Introductionmentioning

confidence: 99%

Sustainable self‐healing elastomers with thermoreversible network derived from biomass via emulsion polymerization

Sahu

Bhowmick

2019

J. Polym. Sci. Part A: Polym. Chem.

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Motivated by the growing demand for greener and sustainable polymer systems, self‐healing elastomers were prepared by emulsion polymerization of terpene and furfural‐based monomers. Both the method and the monomers were green and sustainable. The synthesized copolymers showed molecular weights between 59,080 and 84,210 Da and glass‐transition temperature (Tg) between −25 and −40 °C, implying rubbery properties. A set of one‐dimensional (1D) and two‐dimensional (2D) NMR spectroscopy supported the formation of the copolymer and nuclear spin–spin coupling in the copolymer. Reactivity ratios were determined by conventional linear method. A thermoreversible network was achieved for the first time by reacting the furan‐based polymer with bismaleimide (BM) as a crosslinker, via a Diels−Alder (DA) coupling reaction. The reversible nature of the polymer network was evidenced from infrared and NMR spectroscopy. The thermoreversible character of the DA crosslinked adduct was confirmed by applying retro‐DA reaction (observed in differential scanning calorimeter [DSC] analysis) and mechanical recovery was verified by repeated heating and cooling cycles. The network polymers displayed excellent self‐healing ability, triggered by heating at 130 °C for 4–12 h, when their scratched surface was screened by microscopic visualization. The healing efficiency of the crosslinked DA‐adduct was calculated as 78%, using atomic force microscopy. This work provides a green and efficient approach to prepare new green and functional materials. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 738–751

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Thermoplastic polyurethane elastomers from bio-based poly(δ-decalactone) diols

Cited by 51 publications

References 18 publications

Polymerization of 5-alkyl δ-lactones catalyzed by diphenyl phosphate and their sequential organocatalytic polymerization with monosubstituted epoxides

Polymerization of 5-alkyl δ-lactones catalyzed by diphenyl phosphate and their sequential organocatalytic polymerization with monosubstituted epoxides

Thermoset Elastomers Derived from Carvomenthide

Sustainable self‐healing elastomers with thermoreversible network derived from biomass via emulsion polymerization

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