Crystallizable and Tough Aliphatic Thermoplastic Polyureas Synthesized through a Nonisocyanate Route

Li, Suqing; Sang, Zhihui; Zhao, Ji; Zhang, Zhiyuan; Zhang, Junying; Yang, Wantai

doi:10.1021/acs.iecr.5b04083

Cited by 39 publications

(27 citation statements)

References 48 publications

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“…This indicates that during the chain extension, some of the secondary –OH groups reacted with the N=C=O group of the PU prepolymer. On the other hand, the H-PU spectrum (with no free –OHs) exhibits only the –NH stretching of the urethane unit (3310 cm −1 ) and the –C–O–C– stretching of polyol (1107 cm −1 ) ( Supplementary Material, Figure S1 ) [ 49 , 50 , 51 , 52 ]. The molecular weights (M n and M w ) and PDIs measured with GPC for S-PU and H-PU are summarized in Table 1 (Raw data of GPC in Supplementary Material, Figure S2 ).…”

Section: Resultsmentioning

confidence: 99%

Sorbitol as a Chain Extender of Polyurethane Prepolymers to Prepare Self-Healable and Robust Polyhydroxyurethane Elastomers

2018

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A self-healable polyhydroxyurethane (S-PU) was synthesized from sorbitol, a biomass of polyhydric alcohol, by a simple process that is suitable for practical applications. In the synthesis, only two primary hydroxyl groups of sorbitol were considered for the chain extension of the polyurethane (PU) prepolymers to introduce free hydroxyl groups in PU. As a control, conventional PU was synthesized by hexane diol mediated chain extension. Relative to the control, S-PU showed excellent intrinsic self-healing property via exchange reaction, which was facilitated by the nucleophilic addition of the secondary hydroxyl groups without any catalytic assistance and improved tensile strength due to the enhanced hydrogen bonding. We also investigated the effect of the exchange reaction on the topological, mechanical, and rheological properties of S-PU. The suggested synthetic framework for S-PU is a promising alternative to the conventional poly hydroxyurethane, in which cyclic carbonates are frequently reacted with amines. As such, it is a facile and environmentally friendly material for use in coatings, adhesives, and elastomers.

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Section: Resultsmentioning

confidence: 99%

Sorbitol as a Chain Extender of Polyurethane Prepolymers to Prepare Self-Healable and Robust Polyhydroxyurethane Elastomers

2018

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“…Mechanical analysis was conducted at a crosshead speed of 100 mm min À1 at 25 C. The resilience of elastomers was detected as described in the literature. 30…”

Section: Characterizationmentioning

confidence: 99%

“…[22][23][24] Zhao et al synthesized a series of aliphatic segmented poly(amide urethane)s containing short nylon-6 segments 25 , poly(ether amide urethane)s containing poly(ethylene glycol) (PEG) sequences and short nylon-6 segments, 26 poly(ether urethane)s (PEIUs) with short or long PEG segments, 27,28 and aliphatic polyureas. 29,30 They are all crystallizable thermoplastics with good thermal and mechanical properties.…”

Section: Introductionmentioning

confidence: 99%

Influence of crystallizable units on the properties of aliphatic thermoplastic poly(ether urethane)s synthesized through a non-isocyanate route

Zhao

Zhang

et al. 2017

Journal of Elastomers & Plastics

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A simple non-isocyanate route synthesizing crystallizable aliphatic segmented thermoplastic poly(ether urethane)s (PEIUs) and elastomers with high melting temperature ( Tm) and good mechanical properties is described. Three poly(ethylene hexanediurethane) prepolymers (PrePEHDUs) were prepared through the self-transurethane polycondensation of bis(hydroxyethyl) hexanediurethane. Melt polycondensation of PrePEHDUs, poly(ethylene glycol)1500, and bis(hydroxyethyl) isophoronediurethane was conducted at 170°C under a reduced pressure of 399 Pa, and a series of segmented PEIUs containing irregular units were synthesized. The PEIUs were characterized by gel permeation chromatography, Fourier transform infrared spectroscopy, 1proton nuclear magnetic resonance, 13carbon nuclear magnetic resonance (C-NMR), 2D 13C–1H heteronuclear single quantum coherence (HSQC) NMR, distortionless enhancement by polarization transfer (DEPT)-135 13C-NMR, differential scanning calorimetry, thermogravimetric analysis, wide-angle X-ray diffraction, atomic force microscopy, and tensile tests. The PEIUs exhibited a number-average molecular weight up to 20700 g/mol, Tm up to 141.1°C, initial decomposition temperature at over 243.1°C, and tensile strength up to 49.44 MPa. By tuning the length and amount of crystallizable segments, crystallizable PEIU thermoplastic elastomers were prepared. They exhibited tensile strength up to 20.85 MPa, elongation at break above 125.43%, and resilience above 65.69%.

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“…Researchers reported aliphatic NI-TPUs synthesized through transurethane polycondensation, including amorphous 14,15 and crystallizable 16,17 polyurethanes, poly(amide urethane)s, [18][19][20] poly(ether amide urethane)s, 21 poly(ether urethane)s, 22,23 and polyureas. [24][25][26] These NI-TPUs are thermoplastics other than NI-TPUEs because they lack resilience. In our previous work, we synthesized several amorphous NI-TPUEs containing irregular polyurethane HSs and poly(ethylene glycol) SSs, 27 and several crystallized NI-TPUEs containing crystallizable polyurethane HSs and poly(tetramethylene ether) (PTME), 28 poly(butylene adipate) (PBA), 29 or polycaprolactone (PCL) SSs.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and thermal and mechanical properties of nonisocyanate poly(ether urethane) thermoplastic elastomers containing dibutylene terephthalate and poly(tetramethylene ether) segments

Wang

Zhao

et al. 2020

Journal of Elastomers & Plastics

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Several novel semiaromatic poly(ether urethane) thermoplastic elastomers were synthesized through a nonisocyanate route. The nonisocyanate thermoplastic polyurethane elastomers (NI-TPUEs) were prepared via a transurethane polycondensation of bis(hydroxyethyl) hexanediurethane with bis(4-hydroxybutyl) terephthalate and poly(tetramethylene glycol)s under a reduced pressure of 3 mmHg at 170°C. The NI-TPUEs were fully characterized. The influence of hard segment (HS) contents on thermal and mechanical properties was studied. Gel permeation chromatography characterization demonstrated that high molecular weight of NI-TPUEs was obtained. Wide-angle X-ray scattering and thermal characterization verified that NI-TPUEs were crystallizable and had a relatively high melting point. Atomic force microscopy exhibited microphase separation between the crystallized HSs and amorphous phases. High content of HSs and flexible poly(tetramethylene ether) soft segments leads to good crystallization, excellent mechanical property, and good resilience of NI-TPUEs.

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Crystallizable and Tough Aliphatic Thermoplastic Polyureas Synthesized through a Nonisocyanate Route

Cited by 39 publications

References 48 publications

Sorbitol as a Chain Extender of Polyurethane Prepolymers to Prepare Self-Healable and Robust Polyhydroxyurethane Elastomers

Sorbitol as a Chain Extender of Polyurethane Prepolymers to Prepare Self-Healable and Robust Polyhydroxyurethane Elastomers

Influence of crystallizable units on the properties of aliphatic thermoplastic poly(ether urethane)s synthesized through a non-isocyanate route

Synthesis and thermal and mechanical properties of nonisocyanate poly(ether urethane) thermoplastic elastomers containing dibutylene terephthalate and poly(tetramethylene ether) segments

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