Abstract
Four polyurethane/polyamide copolymer dispersions (PUCON-co-APAS) were prepared from castor oil-based polyol (CON). Castor oil (CO) was firstly transesterified with triethanolamine at 210 °C for different time intervals: 30, 60, 90 and 120 min, to produce CON30, CON60, CON90 and CON120 polyols, respectively. The hydroxyl and acid values, density, viscosity, chemical structure analysis of the CON polyols were determined. The polyols were used to prepare PUCON30-co-APAS, PUCON60-co-APAS, PUCON90-co-APAS, and PUCON120-co-APAS copolymer dispersions in five steps using prepolymer self-emulsification solvent process. The first step is the prepolymer preparation step, in which CON was reacted with dimethylolpropionic acid and excess toluene diisocyanate to produce PUCON NCO . The second step is the copolymerization step, in which PUCON NCO was reacted with amino-terminated aromatic polyamide sulfone. The following processes are neutralization, chain extension and dispersion steps. The prepared copolymer dispersions were characterized using FTIR, DLS, TGA, DSC and GPC. Additionally, the physical, chemical and mechanical properties of the prepared copolymers were studied. The results showed an increase in the hydroxyl number of CON with increasing transesterification time. Stronger H-bonds and smaller particle sizes are produced using CON with higher transesterification time in the preparation of the copolymer dispersions.
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Wang HH, Gen CT (2002) Synthesis of anionic water-borne polyurethane with the covalent bond of a reactive dye. J Appl Polym Sci 84:797–805
Devi DA, Raju KVSN, Aminabhavi TM (2007) Synthesis and characterization of moisture-cured polyurethane membranes and their applications in pervaporation separation of ethyl acetate/water azeotrope at 30 °C. J Appl Polym Sci 103:3405–3414
Witkiewicz W, Zieliński A (2006) Properties of the polyurethane (PU) light foams. Adv Mater Sci 6(2):35–51
Pan X, Webster DC (2012) New biobased high functionality polyols and their use in polyurethane coatings. ChemSusChem 5:419–429
Fu L, Yang L, Dai C, Zhao C, Ma L (2010) Thermal and mechanical properties of acrylated expoxidized-soybean oil-based thermosets. J Appl Polym Sci 117(4):2220–2225
Kim EH, Woo-Rom Lee WR, Myoung SW, Kim JP, Jung YG, Nam YS, Kyoung WS, Cho H (2010) Characterization of waterborne polyurethane for ecofriendly functional floor plate. Prog Org Coat 67(2):102–106
Jeon HT, Jang MK, Kim BK, Kim KH (2007) Synthesis and characterizations of waterborne polyurethane–silica hybrids using sol–gel process. Coll Surf A Physicochem Eng Asp 302(1–3):559–567
Hercule KM, Yan Z, Christophe MM (2011) Preparation and characterization of waterborne polyurethane crosslinked by urea bridges. Int J Chem 3(2):88–96
Orgiles-Calpena E, Aran-Ais F, Torro-Palau AM, Orgiles-Barcelo C (2012) Influence of the chain extender nature on adhesives properties of polyurethane dispersions. J Dispers Sci Technol 33:147–154
Mohamed HA, Badran BM, Rabie AM, Morsi SMM (2014) Synthesis and characterization of aqueous (polyurethane/aromatic polyamide sulfone) copolymer dispersions from castor oil. Prog Org Coat 77:965–974
Gao C, Xu X, Ni J, Lin W, Zheng Q (2009) Effects of castor oil, glycol semi-ester, and polymer concentration on the properties of waterborne polyurethane dispersions. Polym Eng Sci 49(1):162–167
Mequanint K, Sanderson R (2003) Nano-structure phosphorus-containing polyurethane dispersions: synthesis and crosslinking with melamine formaldehyde resin. Polymer 42(9):2631–2639
Athawale VD, Nimbalkar VR (2011) Waterborne coatings based on renewable oil resources: an overview. J Am Oil Chem Soc 88(2):159–185
Wu D, Qiu F, Xu H, Zhang J, Yang D (2011) Preparation, characterization, and properties of environmentally friendly waterborne poly(urethane acrylate)/silica hybrids. J Appl Polym Sci 119:1683–1695
Chen F, Hehl J, Su Y, Mattheis C, Greiner A, Agarwal S (2013) Smart secondary polyurethane dispersions. Polym Int 62:1750–1757
Ge Z, Luo Y (2013) Synthesis and characterization of siloxane-modified two-component waterborne polyurethane. Prog Org Coat 76:1522–1526
Choi SH, Kim DH, Raghu AV, Reddy KR, Lee H, Yoon KS, Jeong HM, Kim BK (2012) Properties of graphene/waterborne polyurethane nanocomposites cast from colloidal dispersion mixtures. J Macromol Sci Part B Phys 51:197–207
Xia Y, Larock RC (2011) Preparation and properties of aqueous castor oil-based polyurethane–silica nanocomposite dispersions through a sol–gel process. Macromol Rapid Commun 32:1331–1337
Costa APO, Silva RB, Gerbase AE, Petzhold CL (2012) Synthesis and characterization of soybean-oil-based polyurethane composites containing industrial and agricultural residual wastes as fillers. J Appl Polym Sci 123:1370–1376
John J, Bhattacharya M, Turner RB (2002) Characterization of polyurethane foams from soybean oil. J Appl Polym Sci 86:3097–3107
Williams CK, Hillmyer MA (2008) Polymers from renewable resources: a perspective for a special issue of polymer reviews. Polym Rev 48:1–10
Wang C, Chen X, Chen J, Liu C, Xie H, Cheng R (2011) Synthesis and characterization of novel polyurethane acrylates based on soy polyols. J Appl Polym Sci 122:2449–2455
Lu Y, Larock RC (2011) Synthesis and properties of grafted latices from a soybean oil-based waterborne polyurethane and acrylics. J Appl Polym Sci 119:3305–3314
Javni I, Petrovic ZS, Guo A, Fuller R (2000) Thermal stability of polyurethanes based on vegetable oils. J Appl Polym Sci 77(8):1723–1734
Saxena PK, Srinivasan SR, Hrouz J, Ilavsky M (1992) The effect of castor oil on the structure and properties of polyurethane elastomers. J Appl Polym Sci 44(8):1343–1347
Liu TM, Bui VT (1995) Instrumented impact testing of castor-oil-based polyurethanes. J Appl Polym Sci 56(3):345–354
Mileo PC, Mulinari DR, Baptista CARP, Rocha GJM, Gonçalves AR (2011) Mechanical behaviour of polyurethane from castor oil reinforced sugarcane straw cellulose composites. Proced Eng 10:2068–2073
Suthar B, Dave M, Jadav K (1993) Sequential-interpenetrating polymer networks from castor oil-based polyesters. J Appl Polym Sci 50(12):2143–2147
Rodrigues JME, Pereira MR, De Souza AG, Carvalho ML, Neto AAD, Dantas TNC, Fonseca JLC (2005) DSC monitoring of the cure kinetics of a castor oil-based polyurethane. Thermochim Acta 427(1–2):31–36
Valero MF, Pulido JE, Ramırez A, Cheng Z (2008) Polyurethanes sintetized of polyols obtained from castor oil modified by transesterification with pentaerythritol. Quim Nova 31(8):2076–2082
Kaushik A, Singh P (2005) Synthesis and characterization of castor oil/trimethylol propane polyol as raw materials for polyurethanes using time-of-flight mass spectroscopy. Int J Polym Anal Char 10(5–6):373
Kaushik A, Singh P (2012) Castor oil/trimethylol propane-based polyurethane reactions: modeling in a batch reactor. J Appl Polym Sci 125:E51–E60
Reddy KR, Raghu AV, Jeong HM, Siddaramaiah (2009) Synthesis and characterization of pyridine-based polyurethanes. Des Monomers Polym 12:109–118
Reddy KR, Raghu AV, Jeong HM (2008) Synthesis and characterization of novel polyurethanes based on 4,4′-{1,4-phenylenebis [methylylidenenitrilo]} diphenol. Polym Bull 60:609–616
Bellomo MR, Di Pasquale G, La Rosa A, Pollicino A, Siracusa G (1996) New aromatic polyamide materials containing sulfone, ether and ketone linkages. Polymer 37(13):2877–2881
Imai Y (1996) Recent advances in synthesis of high-temperature aromatic polymers. React Funct Polym 30:3–15
Liu YJ, Pei XL, Sheng SR, Yang F, Liu XL, Song CS (2012) Synthesis and characterization of novel aromatic poly(ester amide)s containing pendant trifluoromethylphenoxy groups. J Appl Polym Sci 125:3904–3912
Zhang G, Li D, Huang G, Wang X, Long S, Yang J (2011) Synthesis and properties of polyamides containing high contents of thioether units. React Funct Polym 71:775–781
Pal RR, Patil PS, Salunkhe MM, Maldar NN, Wadgaonkar PP (2009) Synthesis, characterization and constitutional isomerism study of new aromatic polyamides containing pendant groups based on asymmetrically substituted meta-phenylene diamines. Eur Polymer J 45:953–959
Mosiewicki MA, Dell’Arciprete GA, Aranguren MI, Marcovich NE (2009) Polyurethane foams obtained from castor oil-based polyol and filled with wood flour. J Compos Mater 43(25):3057–3072
Dave VJ, Patel HS (2013) Synthesis and characterization of interpenetrating polymer networks from transesterified castor oil based polyurethane and polystyrene. J Saudi Chem Soc. doi:10.1016/j.jscs.2013.08.001
Veronese VB, Menger RK, de C, Forte MM, Petzhold CL (2011) Rigid polyurethane foam based on modified vegetable oil. J Appl Polym Sci 120:530–537
Ristic IV, Budinski-Simendic J, Krakovsky I, Valentova H, Radicevic R, Cakic S, Nikolic N (2012) The properties of polyurethane hybrid materials based on castor oil. Mater Chem Phys 132(1):74–81
Guclu G (2010) Alkyd resins based on waste PET for water-reducible coating applications. Polym Bull 64:739–748
Garcia-Pacios V, Costa V, Colera M, Martin-Martınez JM (2010) Affect of polydispersity on the properties of waterborne polyurethane dispersions based on polycarbonate polyol. Int J Adhes Adhes 30:456–465
Garcia-Pacios V, Iwata Y, Colera M, Martin-Martınez JM (2011) Influence of the solids content on the properties of waterborne polyurethane dispersions obtained with polycarbonate of hexanediol. Int J Adhes Adhes 31:787–794
Perez-Liminana MA, Aran-Ais F, Torro-Palau AM, Orgiles-Barcel C, Martin-Martinez JM (2007) Influence of the hard-to-soft segment ratio on the adhesion of water-borne polyurethane adhesive. J Adhes Sci Technol 21(8):755–773
Gao Z, Peng J, Zhong T, Sun J, Wang X, Yue C (2012) Biocompatible elastomer of waterborne polyurethane based on castor oil and polyethylene glycol with cellulose nanocrystals. Carbohydr Polym 87:2068–2075
Cakic SM, Spirkova M, Ristic IS, B-Simendic JK, M-Cincovic M, Poreba R (2013) The waterborne polyurethane dispersions based on polycarbonate diol: effect of ionic content. Mater Chem Phys 138:277–285
Mishra AK, Narayan R, Aminabhavi TM, Pradhan SK, Raju KVSN (2012) Hyperbranched polyurethane-urea-imide/o-clay-silica hybrids: synthesis and characterization. J Appl Polym Sci 125:E67–E75
Sebenik U, Krajnc M (2004) Seeded semibatch emulsion copolymerization of methyl methacrylate and butyl acrylate using polyurethane dispersion: effect of soft segment length on kinetics. Coll Surf A Physicochem Eng Asp 233:51–62
Choi HS, Noh ST, Choi KB (1999) Effects of anionic center on properties of polyurethane anionomer dispersion. J Ind Eng Chem 5(1):52–58
Garcia-Pacios V, Colera M, Iwata Y, Martin-Martınez JM (2013) Incidence of the polyol nature in waterborne polyurethane dispersions on their performance as coatings on stainless steel. Prog Org Coat 76:1726–1729
David G, Simionescu BC, Ibanescu S, Vearba F (2011) Effect of montmorillonite content in nanocomposites of segmented polyurethanes with poly(2-alkyl-2-oxazoline) sequences. High Perform Polym 23(1):74–84
Chen Y, Chen YL (1992) Aqueous dispersions of polyurethane anionomers: effects of countercation. J Appl Polym Sci 46:435–443
Kumar MNS, Siddaramaiah (2007) Thermogravimetric analysis and morphological behavior of castor oil based polyurethane-polyester nonwoven fabric composites. J Appl Polym Sci 106:3521–3528
Patel MR, Shukla JM, Patel NK, Patel KH (2009) Biomaterial based novel polyurethane adhesives for wood to wood and metal to metal bonding. Mater Res 12(4):385–393
Hourston DJ, Williams GD, Satguru R, Padget JC, Pears D (1999) The influence of the degree of neutralization, the ionic moiety, and the counterion on water-dispersible polyurethanes. J Appl Polym Sci 74:556–566
Nanda AK, Wicks DA, Madbouly SA, Otaigbe JU (2005) Effect of ionic content, solid content, degree of neutralization, and chain extension on aqueous polyurethane dispersions prepared by prepolymer method. J Appl Polym Sci 98:2514–2520
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Mohamed, H.A., Morsi, S.M.M., Badran, B.M. et al. Polyurethane/aromatic polyamide sulfone copolymer dispersions from transesterified castor oil. Polym. Bull. 74, 531–554 (2017). https://doi.org/10.1007/s00289-016-1728-x
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DOI: https://doi.org/10.1007/s00289-016-1728-x