Abstract
The new unsaturated poly(ester-urethane) was synthesized by the reaction of 4,4′-methylenediphenyldiisocyanate with 4,4′-di(2,3-butenhydroxyl) terephthalate in the ratio of 1:1. 4,4′-di(2,3-butenhydroxyl) terephthalate was first prepared by reacting 2 mol of cis-2-butene-1, 4-diol with 1 mol of terephthalic acid. The terephthalic acid used was derived from the recycling of PET bottles via subjection to saponification process. The synthesized compounds were characterized by CHN analysis, FT-IR, 1H NMR and UV–Vis spectroscopy, with consistency of results showing the presence of the new unsaturated poly(ester-urethane) II. Thermal properties of the new polymer was verified by differential scanning calorimetry and thermogravimetric analysis, whereas the mechanical properties were characterized by tensile, elongation, hardness, adhesion and impact testing. The electrical conductivity and the electrical resistance of the compound were observed with increasing applied voltage.
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References
Scheirs J, Long TE (2003) Modern polyesters: chemistry and technology of polyesters and copolyesters. John Wiley & Sons, Hoboken, p 37
David EN, Medhat SF (2005) New motivation for the depolymerization products derived from poly (Ethylene Terephthalate) (PET) waste: a review. Macromol Mater Eng 290:13–30
Sinha V, Patel MR, Patel JV (2010) PET waste management by chemical recycling: a review. J Polym Environ 18:8–25
Recovery Process for Ethylene Glycol and Dimethylterephthalate (1991) U.S. Patent 5,051,528
Vaidya UR, Nadkarni VM (2003) Unsaturated polyester from PET waste: kinetics of polycondensation. J Appl Polym Sci 34:235–245
Baliga S, Wong TW (2003) Depolymerisation of poly (ethylene terephthalate) from post-consumer soft-drink bottles. J Polym Sci Part A: Polym Chem 27:2071–2082
Campanelli JR, Kamal MR, Cooper DG (1993) A kinetic study of the hydrolytic degradation of poly (ethylene terephthalate) at high temperature. J Appl Polym Sci 48:443–451
Yoshioka T, Sato T, Okuwa A (1994) A Hydrolysis of PET waste by sulfuric acid at 150 °C for a chemical recycling. J Appl Polym Sci 52:1353–1355
Oku A, Hu LC, Yamada E (1997) Alkali decomposition of poly (ethylene terephthalate) with sodium hydroxide in non-aqueous ethylene glycol. J Appl Polym Sci 63:595–601
Firas A, Dumitru P (2005) Recycling of PET. Eur Polym J 41:1453–1477
Cesare L, Piero M, Corrado B, Giancarlo B (2006) Chemical recovery of useful chemicals from polyester (PET) waste for resource conservation: a survey of state of the art. J Polym Environ 14:89–101
Vaidya UR, Nadkarni VM (1987) Unsaturated polyester resins from poly (ethylene terephthalate) waste—synthesis and characterization. Ind Eng Chem Res 26:194–198
Aslan S, Immirzi B, Laurienzo P (1997) Unsaturated polyester resin from glycolyzed polyethyleneterephthalate: synthesis and comparison of properties and performance with virgin resin. J Mater Sci 32:2329–2336
Vaidya UR, Nadkarni VM (1988) Polyester polyols for polyurethanes from PET waste: kinetics of polycondensation. J Appl Polym Sci 35:775–785
Atta AM, El-Kafrawy AF, Aly MH, Abdel-Azim AA (2007) A New epoxy resins based on recycled poly (ethylene terephthalate) as organic coatings. Prog Org Coat 58:13–22
Karayannidis GP, Achilias DS, Sideridou ID, Bikiaris DN (2005) Alkyd resins derived from glycolized waste poly (ethylene terephthalate). Eur Polym J 41:201–210
Atta AM, Elnagdy SI, Abdel-Raouf ME, Elsaeed SM, Abdel-Azim AA (2005) Compressive properties and curing behaviour of unsaturated polyester resins in the presence of vinyl ester resins derived from recycled poly (ethylene terephthalate). J Polym Res 12:373–383
Lamda NMK, Woodhouse KA, Cooper SL (1998) Polyurethanes in biomedical applications. CRC Press, Boca Raton FL
Moehle RT, Farnworth CL, Hibdon D, Patterson RC (2006) U.S. Patent 20060200111
Sridharan S (2004) U.S. Patent 2004197501
Lakshmi SN, Cato TL (2007) Biodegradable polymers as biomaterials. Prog Polym Sci 32:762–798
Umare SS, Chandure AS (2008) Synthesis, characterization and biodegradation studies of poly(ester urethane)s. Chem Eng J 142(1):65–77
Claes GG (2007) Transparent conductors as solar energy materials: a panoramic review. Sol Energ Mat Sol C 91:1529–1598
ASTM D 412: 06ae2 (2006) Standard test methods for vulcanized rubber and thermoplastic elastomers—tension
Issam AM, Ismail J (2006) New aromatic poly(azomethine urethane)s containing o-tolidine moiety in the polymer backbone. Des Monomers Polym 9(3):237–246
Schoonover JR, Darla GT, Osborn JC, Orler EB, Wrobleski DA, Marsh AL, Wang H, Palmer RA (2001) Infrared linear dichroism study of a hydrolytically degraded poly (ester urethane). Polym Degrad Stabil 74:87–96
Schoonover JR, Dattelbaum DM, Osborn JC, Bridgewater JS, Kenney JW III (2003) Pressure-dependent Fourier transform infrared spectroscopy of a poly (ester urethane). Spectrochim Acta A 59:309–319
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The authors would like to acknowledge University Sains Malaysia for short term grant No. 304/PTEKIND/6311031. The authors would like to thank Dr. Shahrom Mahmud for his assistance in measuring the conductivity.
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Issam, A.M., Hena, S. & Nurul Khizrien, A.K. A New Unsaturated Poly(ester-urethane) Based on Terephthalic Acid Derived from Polyethylene Terephthalate (PET) of Waste Bottles. J Polym Environ 20, 469–476 (2012). https://doi.org/10.1007/s10924-011-0407-0
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DOI: https://doi.org/10.1007/s10924-011-0407-0