Abstract
In this study, 4,4′-diphenylmethane diisocyanate and polytetramethylene glycol were used to prepare a prepolymer, and 2,6-pyridinedimethanol (2,6-PDM) was then used as a chain extender to prepare a novel polyurethane (PDM/PUs). Gel permeation chromatography analysis shows that the molecular weight of PDM/PUs increases as the 2,6-PDM content increases. Fourier transform infrared spectroscopy analyses demonstrate that by increasing the 2,6-PDM content, PDM/PUs will form strong hydrogen bonds. The thermal analysis of PDM/PUs indicates that the initial decomposition temperature of PDM/PUs-03 is approximately 10 °C higher than that of PDM/PUs-01. Differential Scanning Calorimetry and Dynamic Mechanical Analysis analyses indicate that increases in the 2,6-PDM content produce significant enhancements in the glass transition temperature (T g) and the dynamic T g of PDM/PUs. Stress–strain tests indicate that 2,6-PDM can increase the maximum stress and Young’s modulus of PDM/PUs while reducing the elongation rate at break. The results of moisture absorption rate test indicate that when the 2,6-PDM content and ambient humidity increase, the water absorption rate of PDM/PUs increases. Moreover, PDM/PUs exhibits good shape recovery (>90 %).
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References
Comstock MJ (1981) Urethane Chemistry and Applications. ACS Chapter 1
Datta J (2010) Synthesis and investigation of glycolysates and obtained polyurethane elastomers. J Elastom Plast 42:117–127
Datta J, Laski M, Kucinska-Lipka J (2007) The properties of polyurethane elastomers to he used as polymer cores in sandwich plate systems (SPS). Przemysł Chemiczny 86:63–67
Datta J, Rohn M (2008) Structure, thermal stability and mechanical properties of polyurethanes, based on glycolysate from polyurethane foam waste, prepared with use of 1,6-hexanediol as a glycol. Polimery 53:871–875
Datta J, Rohn M (2007) Glycolysis of polyurethane wastes. Part II. Purification and use of glycolysis products. Polimery 52:627–633
Datta J, Pasternak S (2005) Oligourethane glycols obtained in glycolysis of polyurethane foam as semi-finished products for cast urethane elastomers preparation. Polimery 50:352–357
Cho JW, So JH (2006) Polyurethane-silver fibers prepared by infiltrationand reduction of silver nitrate. Mater Lett 60:2653–2656
Schollenberger CS (1990) Polyurethane and isocyanate based adhesives. Handbook of adhesives New York: Van Nostrand Reinhold Chapter 20
Lee BS, Chun BC, Chung YC, Sul KI, Cho JW (2001) Structure and thermomechanical properties of polyurethane block copolymers with shape memory effect. Macromolecules 34:6431–6437
Plominskamichalak B, Lisowska R, Balas A (1994) Properties of poly(ester-ether) microcellular urethane elastomer systeme. J Elastom Plast 26:327–334
Galan RJ, Narayan T, Markovs RA (1990) Novel Polyurethane Shoe Sole Systems Having Superior Low Temperature Flex Properties. J Elastom Plast 22:22–31
Tsou CH, Lee HT, Tsai HA, Cheng HJ, Suen MC (2013) Synthesis and properties of biodegradable polycaprolactone/polyurethanes by using 2,6-pyridinedimethanol as a chain extender. Polym Degrad Stab 98:643–650
Chen SJ, Hu JL, Chen SG, Zhang CL (2011) Study on the structure and morphology of supramolecular shape memory polyurethane containing pyridine moieties. Smart Mater Struct 20:065003–065009
Connell EMO, Yang CZ, Root TW, Cooper SL (1996) Spectroscopic studies of pyridine-containing polyurethanes blended with metal acetates. Macromolecules 29:6002–6010
Ratna D, Karger-Kocsis J (2008) Recent advances in shape memory polymers and composites: a review. J Mater Sci 43:254–269
Behl M, Lendlein A (2007) Actively moving polymers. Soft Matter 3:58–67
Huang WM, Yang B, Zhao Y, Ding Z (2010) Thermo-moisture responsive polyurethane shape-memory polymer and composites: a review. J Mater Chem 20:3367–3381
Hu JL, Chen SJ (2010) A review of actively moving polymers in textile applications. J Mater Chem 20:3346–3355
Chen S, Hu J, Zhuo H, Yuen C, Chan L (2010) Study on the thermal-induced shape memory effect of pyridine containing supra- molecular polyurethane. Polymer 51:240–248
Cho JW, Kim JW, Jung YC, Goo NS (2005) Electroactive shape-memory polyurethane composites incorporating carbon nanotubes. Macromol Rapid Commun 26:412–416
Lendlein A, Jiang HY, Junger O, Langer R (2005) Light-induced shape-memory polymers. Nature 434:879–882
Yuan Z, Ji B, Wu LB (2009) Synthesis and thermal induced shape memory properties of biodegradable segmented poly(ester-urethane)s. Acta Polym Sin 41:153–158
Hollander SD, Assche GV, Mele BV, Prez FD (2009) Studies of the moisture-sensitive shape memory effect of pyridine-containing polyurethanes. Polymer 50:4447–4454
Chen S, Hu J, Yuen CW, Chan L (2009) Supramolecular polyurethane networks containing pyridine moieties for shape memory materials. Mater Lett 63:1462–1464
Zhu Y, Hu JL, Liu YJ (2009) Shape memory effect of thermoplastic segmented polyurethanes with self-complementary quadruple hydrogen bonding in soft segments. Eur Phys J E 28:3–10
Vogt BD, Soles CL, Lee HJ, Lin EK, Wu W (2005) Moisture absorption into ultrathin hydrophilic polymer films on different substrate surfaces. Polymer 46:1635–1642
Chen S, Hu J, Chen S (2012) Studies of the moisture-sensitive shape memory effect of pyridine-containing polyurethanes. Polym Int 61:314–320
Brunette CM, Hsu SL, Macknight WJ (1982) Hydrogen-bonding properties of hard-segment model compounds in polyurethane block copolymers. Macromolecules 15:71–77
Arun Prasath R, Nanjundan S, Pakula T, Klapper M (2004) Thermal and dynamic mechanical behaviour of calcium containing co-polyurethanes. Polym Degrad Stab 85:911–923
Rueda-Larraz L, Fernandez d’Arlas B, Tercjak A, Ribes A, Mondragon I, Eceiza A (2009) Synthesis and microstructureemechanical property relationships of segmented polyurethanes based on a PCL-PTHF-PCL block copolymer as soft segment. Eur Polym J 45:2096–2109
Papai I, Jancso G (2000) Hydrogen bonding in methyl-substituted pyridine-water complexes. J Phys Chem A 104:2132–2137
Chen Shaojun Hu, Jinlian Yuen Chun-wah, Laikuen Chan (2009) Novel moisture-sensitive shape memory polyurethanes containing pyridine moieties. Polymer 50:4424–4428
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Chiu, SH., Wu, CL., Tsou, CY. et al. Study of the synthesis and properties of polyurethane containing pyridyl units for shape memory. Polym. Bull. 73, 1303–1320 (2016). https://doi.org/10.1007/s00289-015-1548-4
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DOI: https://doi.org/10.1007/s00289-015-1548-4