Abstract
A series of novel hydroxyl-terminated hyperbranched polyurethanes (HBPUs) were synthesized via stepwise polymerization by diethanolamine (DEOA), isophorone diisocyanate (IPDI) and trimethylolpropane (TMP). It is interesting to note that the HBPUs can be purified by water. The HBPUs were characterized with 1H nuclear magnetic resonance (NMR), 13C NMR, Fourier transform infrared spectroscopy (FT-IR) and elemental analysis. The average degree of branching (DB) of HBPUs was calculated from the first generation to the fourth generation to be 1.00, 0.74, 0.59 and 0.57 by quantitative 13C NMR, respectively. The branching model and molecular structure of HBPUs were deduced by the 13C NMR and the value of DB. To investigate the changes of hydrogen bonding interaction in HBPUs with a variation in structure of different generations, the deconvolution of FT-IR spectra was carried out using Origin 7.0 software through the Gaussian curve-fitting method. The ratio of hydrogen-bonded -NH and -OH groups of HBPUs was calculated to be 80.8%, 85.1%, 84.8% and 85.4% from the first generation to the fourth generation by deconvoluted -NH and -OH zone, respectively. The interaction of hydrogen bonding and glass transition temperature (Tg) of HBPUs increased with the increase of generation. The trend of thermal stability and Tg coincide with the change of hydrogen-bonded interactions.
References
[1] Ji SH, Bruchmann B, Wurm F, Klok HA. J. Polym. Sci., Part A: Polym. Chem. 2012, 50, 25–34.Search in Google Scholar
[2] Satpathi H, Ghosh A, Komber H, Banerjee S, Voit B. Eur. Polym. J. 2011, 47, 196–207.Search in Google Scholar
[3] Mishra AK, Narayan R, Raju KVSN. Prog. Org. Coat. 2010, 74, 491–501.Search in Google Scholar
[4] Maminski ML, Parzuchowski PG, Trojanowska A, Dziewulski S. Biomass Bioenergy 2011, 35, 4461–4468.10.1016/j.biombioe.2011.09.012Search in Google Scholar
[5] Zill AT, Licha K, Haag R, Zimmerman SC. New J. Chem. 2012, 36, 419–427.Search in Google Scholar
[6] Yang W, Pan CY, Liu XQ, Wang J. Biomacromolecules 2011, 12, 1523–1531.10.1021/bm1014816Search in Google Scholar PubMed
[7] Pang Y, Liu JY, Su Y, Wu JL, Zhu LJ, Zhu XY, Yan DY, Zhu BS. Polym. Chem. 2011, 2, 1661–1670.Search in Google Scholar
[8] Kumar A, Ramakrishnan S. J. Chem. Soc., Chem. Commun. 1993, 18, 1453–1454.Search in Google Scholar
[9] Spindler R, Frechet JMJ. Macromolecules 1993, 26, 4809–4813.10.1021/ma00070a013Search in Google Scholar
[10] Žagar E, Žigon M. Prog. Polym. Sci. 2011, 36, 53–88.Search in Google Scholar
[11] Lin KR, Chien YHC, Chang CC, Hsieh KH, Leung MK. Macromolecules 2008, 41, 4158–4164.10.1021/ma800127vSearch in Google Scholar
[12] Nasar AS, Jikei M, Kakimoto M-A. Eur. Polym. J. 2003, 39, 1201–1208.Search in Google Scholar
[13] Komber H, Georgi U, Voit B. Macromolecules 2009, 42, 8307–8315.10.1021/ma901614rSearch in Google Scholar
[14] Ye L, Letchford K, Heller M, Liggins R, Guan D, Kizhakkedathu JN, Brooks DE, Jackson JK, Burt HM. Biomacromolecules 2011, 12, 145–155.10.1021/bm101080pSearch in Google Scholar PubMed
[15] Zhong L, He XH, Zhou YF, Yan DY, Pan CY. Acta Polymerica Sinica 2007, 10, 986–992.Search in Google Scholar
[16] Jena KK, Raju KVSN, Prathab B, Aminabhavi TM. J. Phys. Chem. B 2007, 111, 8801–8811.10.1021/jp070513tSearch in Google Scholar PubMed
[17] Mishra AK, Narayan R, Raju KVSN, Aminabhavi TM. Prog. Org. Coat. 2012, 74, 134–141.Search in Google Scholar
[18] Mishra AK, Narayan R, Aminabhavi TM, Pradhan SK, Raju KVSN. J. Appl. Polym. Sci. 2012, 125, E67–E75.Search in Google Scholar
[19] Mishra AK, Allauddin S, Narayan R, Aminabhavi TM, Raju KVSN. Ceram. Int. 2012, 38, 929–934.Search in Google Scholar
[20] Jena KK, Sahoo S, Narayan R, Aminabhavi TM, Raju KVSN. Polym. Int. 2011, 60, 1504–1513.Search in Google Scholar
[21] Narayan R, Chattopadhyay DK, Raju KVSN, Mallikarjuna NN, Jawalkar SS, Aminabhavi TM. J. Appl. Polym. Sci. 2006, 100, 2422–2435.Search in Google Scholar
[22] Wang MC, Lin JJ, Tseng HJ, Hsu SH. ACS Appl. Mater. Interfaces 2012, 4, 338–350.10.1021/am2014103Search in Google Scholar PubMed
[23] Thomasson D, Boisson F, Girard-Reydet E, Mechin F. React. Funct. Polym. 2006, 66, 1462–1481.Search in Google Scholar
[24] Oh ST, Kim WR, Kim SH, Chung YC, Park JS. Fibers Polym 2011, 12, 159–165.10.1007/s12221-011-0159-4Search in Google Scholar
[25] Fong N, Simmons A, Poole-Warren LA. Acta Biomater. 2010, 6, 2554–2561.Search in Google Scholar
[26] Rannard SP, Davis NJ, Herbert I. Macromolecules 2004, 37, 9418–9430.10.1021/ma0489218Search in Google Scholar
[27] Yin S, Sun N, Feng CY, Wu ZM, Xu ZH, Jiang SH. Adv. Mater. Res. 2012, 554–556, 126–129.Search in Google Scholar
[28] Mishra AK, Allauddin S, Radhika KR, Narayan R, Raju KVSN. Polym. Adv. Technol. 2011, 22, 882–890.Search in Google Scholar
[29] Jena KK, Raju KVSN. Ind. Eng. Chem. Res. 2007, 46, 6408–6416.Search in Google Scholar
[30] Hatada K, Ute K, Oka KI, Pappas SP. J. Polym. Sci., Part A: Polym. Chem. 1990, 28, 3019–3027.Search in Google Scholar
[31] Bialas N, Höcker H, Marschner M, Ritter W. Die Makromolekulare Chemie 1990, 191, 1843–1852.10.1002/macp.1990.021910810Search in Google Scholar
[32] Hawker CJ, Lee R, Frechet JMJ. J. Am. Chem. Soc. 1991, 113, 4583–4588.Search in Google Scholar
[33] Mishra AK, Chattopadhyay DK, Sreedhar B, Raju KVSN. Prog. Org. Coat. 2006, 55, 231–243.Search in Google Scholar
[34] Kumari S, Mishra AK, Krishna AVR, Raju KVSN. Prog. Org. Coat. 2007, 60, 54–62.Search in Google Scholar
[35] Mishra RS, Khanna AS. Prog. Org. Coat. 2011, 72, 769–777.Search in Google Scholar
[36] Chattopadhyay DK, Mishra AK, Sreedhar B, Raju KVSN. Polym. Degrad. Stab. 2006, 91, 1837–1849.Search in Google Scholar
[37] Grassie N, Zulfiqar M. J. Polym. Sci., Polym. Chem. Ed. 1978, 16, 1563–1574.Search in Google Scholar
[38] Priyanka KG, Mishra AK, Kantheti S, Narayan R, Raju KVSN. J. Appl. Polym. Sci. 2012, 126, 2024–2034.Search in Google Scholar
Supplemental Material
The online version of this article (DOI: 10.1515/polyeng-2013-0313) offers supplementary material, available to authorized users.
©2014 by De Gruyter
Articles in the same Issue
- Frontmatter
- Original articles
- Kinetic degradation and storage stability of β-carotene encapsulated by spray drying using almond gum and gum arabic as wall materials
- Photo-polymerization of methacrylate based polymer electrolyte for dye-sensitized solar cell
- Synthesis and characterization of novel hydroxyl-terminated hyperbranched polyurethanes
- Electron beam modified nylon 6-clay nanocomposites: morphology and water absorption behavior
- The effect of ultraviolet irradiation and temperature on the resilience of high density polyethylene
- Polyaminoamide dendrimers surface-modified with anionic terminal groups for use as calcium carbonate scale inhibitors
- Technical feasibility of a new approach to electromagnetic interference (EMI) shielding of injection molded parts using in-mold coated (IMC) nanopaper
- Study on crystallization performance of polyethylene terephthalate/polybutylene terephthalate alloys
- Numerical study of polymer melt flow in a three-dimensional sudden expansion: viscous dissipation effects
- Enhancement of mechanical properties of polypropylene by blending with styrene-(ethylene-butylene)-styrene tri-block copolymer
- Development and fabrication of cement reinforced polypropylene composite material spur gear
Articles in the same Issue
- Frontmatter
- Original articles
- Kinetic degradation and storage stability of β-carotene encapsulated by spray drying using almond gum and gum arabic as wall materials
- Photo-polymerization of methacrylate based polymer electrolyte for dye-sensitized solar cell
- Synthesis and characterization of novel hydroxyl-terminated hyperbranched polyurethanes
- Electron beam modified nylon 6-clay nanocomposites: morphology and water absorption behavior
- The effect of ultraviolet irradiation and temperature on the resilience of high density polyethylene
- Polyaminoamide dendrimers surface-modified with anionic terminal groups for use as calcium carbonate scale inhibitors
- Technical feasibility of a new approach to electromagnetic interference (EMI) shielding of injection molded parts using in-mold coated (IMC) nanopaper
- Study on crystallization performance of polyethylene terephthalate/polybutylene terephthalate alloys
- Numerical study of polymer melt flow in a three-dimensional sudden expansion: viscous dissipation effects
- Enhancement of mechanical properties of polypropylene by blending with styrene-(ethylene-butylene)-styrene tri-block copolymer
- Development and fabrication of cement reinforced polypropylene composite material spur gear