Poly(amidoamine) dendrimer-grafted carbon nanotubes as a hybrid multifunctional curing agent for epoxy-modified polyurethane
Source abstract
Abstract
Carbon nanotube (CNT) grafted with hyperbranched poly(amidoamine) (PAMAM) dendrimer (CNTD) were used as a multifunctional curing and composite agent of polyurethane (PU) terminated with epoxy units. Amino-functionalized CNT was used as the core for grafting the first generation of PAMAM dendrimer by sequential addition of methyl acrylate and ethylenediamine. Two different epoxy-terminated PUs (PUB and PU-PMDA) were prepared from the reaction of poly(ethylene glycol), excess amounts of hexamethylene diisocyanate, and different chain extenders (1,4-butanediol for PUB and pyromellitic dianhydride (PMDA) for PU-PMDA), and subsequent end group transformation of the isocyanate groups to epoxy functionalities using glycidol. Fourier transform infrared spectra and thermogravimetric analysis (TGA) results showed that CNTD was successfully prepared. TGA thermograms revealed that thermal decomposition of composites were carried out in two main steps related to the soft and hard segments. In addition, char content and thermal stability of the composites were increased with increasing the CNTD content. Most importantly, the PMDA chain extender resulted in high thermal stability of the epoxy-terminated PU composites. X-ray diffraction and scanning and transmission electron microscopies presented morphological and structural properties of nanotubes and hybrid composites.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Polymer composites and self-healing · Synthesis and properties of polymers · Epoxy Resin Curing Processes
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (67)
Show source-provided references
1. Gupta A, Kim BS (2019) Shape memory polyurethane biocomposites based on toughened polycaprolactone promoted by nano-chitosan. Nanomaterials 9:22510.3390/nano9020225 ↗
2. Kausar A (2019) Interpenetrating polymer network and nanocomposite IPN of polyurethane/epoxy: a review on fundamentals and advancements. Polym Technol Mater 58:691–706
3. Li Y, Duan L, Cheng L, Yang Y, Li Y, Cheng Y, Song D (2019) Thermal analysis and crystallization kinetics of polyurethane. J Therm Anal Calorim 135:2843–284810.1007/s10973-018-7594-z ↗
4. Yang W, Li R, Fang C, Hao W (2019) Surface modification of polyamide nanofiber membranes by polyurethane to simultaneously improve their mechanical strength and hydrophobicity for breathable and waterproof applications. Prog Org Coat 131:67–7210.1016/j.porgcoat.2019.02.012 ↗
5. Li M, Chen J, Shi M, Zhang H, Ma PX, Guo B (2019) Electroactive anti-oxidant polyurethane elastomers with shape memory property as non-adherent wound dressing to enhance wound healing. Chem Eng J 375:12199910.1016/j.cej.2019.121999 ↗
6. Xiao S, Laux KA, Wang H, Hu F, Sue HJ (2019) Physical correlation between abrasive wear performance and scratch resistance in model polyurethane elastomers. Wear 418–419:281–28910.1016/j.wear.2018.10.009 ↗
7. Wang C, Hong L, Tian C (2019) Preparation and properties of flame-retardant damping polyurethane and its application in floating deck. Polym Eng Sci 59:2136–214710.1002/pen.25216 ↗
8. Zhang S, Liu H, Yang S, Shi X, Zhang D, Shan C, Mi L, Liu C, Shen C, Guo Z (2019) Ultrasensitive and highly compressible piezoresistive sensor based on polyurethane sponge coated with a cracked cellulose nanofibril/silver nanowire layer. ACS Appl Mater Interfaces 11:10922–1093210.1021/acsami.9b00900 ↗
9. Xi W, Qian L, Li L (2019) Flame retardant behavior of ternary synergistic systems in rigid polyurethane foams. Polymers (Basel) 11:20710.3390/polym11020207 ↗
10. Xie F, Zhang T, Bryant P, Kurusingal V, Colwell JM, Laycock B (2019) Degradation and stabilization of polyurethane elastomers. Prog Polym Sci 90:211–26810.1016/j.progpolymsci.2018.12.003 ↗
11. Golling FE, Pires R, Hecking A, Weikard J, Richter F, Danielmeier K, Dijkstra D (2019) Polyurethanes for coatings and adhesives—chemistry and applications. Polym Int 68:848–85510.1002/pi.5665 ↗
12. Hu J, Zhu Y, Huang H, Lu J (2012) Recent advances in shape—memory polymers : structure, mechanism, functionality, modeling and applications. Prog Polym Sci 37:1720–176310.1016/j.progpolymsci.2012.06.001 ↗
13. Hager MD, Bode S, Weber C, Schubert US (2015) Shape memory polymers: past, present and future developments. Prog Polym Sci 49–50:3–3310.1016/j.progpolymsci.2015.04.002 ↗
14. Masiulanis B, Zielin̂ski R (1985) Mechanical, thermal, and electric properties of polyurethaneimide elastomers. J Appl Polym Sci 30:2731–274110.1002/app.1985.070300702 ↗
15. Petrovic ZS, Zavargo Z, Flynn JH, Macknight WJ (1994) Thermal degradation of segmented polyurethanes. J Appl Polym Sci 51:1087–109510.1002/app.1994.070510615 ↗
16. Koberstein JT, Galembos AF, Leung LM (1992) Compression-molded polyurethane block copolymers. 1. Microdomain morphology and thermomechanical properties. Macromolecules 25:6195–620410.1021/ma00049a017 ↗
17. Chen TK, Chui JY, Shieh TS (1997) Glass transition behaviors of a polyurethane hard segment based on 4,4′-diisocyanatodiphenylmethane and 1,4-butanediol and the calculation of microdomain composition. Macromolecules 30:5068–507410.1021/ma9618639 ↗
18. Yeganeh H, Shamekhi MA (2004) Poly(urethane-imide-imide), a new generation of thermoplastic polyurethane elastomers with enhanced thermal stability. Polymer (Guildf) 45:359–36510.1016/j.polymer.2003.11.006 ↗
19. Liu J, Ma D, Li Z (2002) FTIR studies on the compatibility of hard—soft segments for polyurethane—imide copolymers with different soft segments. Eur Polym J 38:661–66510.1016/S0014-3057(01)00247-6 ↗
20. Patel NB, Mistry DB (2004) Synthesis and properties of polymers containing s-triazine rings in the main chain. Int J Polym Mater Polym Biomater 53:653–65810.1080/00914030490472854a ↗
21. Behnam R, Roghani-Mamaqani H, Salami-Kalajahi M, Mardani H (2020) Effect of aliphatic and aromatic chain extenders on thermal stability of graphene oxide/polyurethane hybrid composites prepared by sol–gel method. ChemistrySelect 5:962–96710.1002/slct.201903953 ↗
22. Tien YI, Wei KH (2001) Hydrogen bonding and mechanical properties in segmented montmorillonite/polyurethane nanocomposites of different hard segment ratios. Polymer (Guildf) 42:3213–322110.1016/S0032-3861(00)00729-1 ↗
23. Yazdi M, Haddadi Asl V, Pourmohammadi M, Roghani-Mamaqani H (2019) Mechanical properties, crystallinity, and self-nucleation of carbon nanotube-polyurethane nanocomposites. Polym Test 79:10601110.1016/j.polymertesting.2019.106011 ↗
24. Pourmohammadi-Mahunaki M, Haddadi-Asl V, Roghani-Mamaqani H, Koosha M, Yazdi M (2020) Halloysite-reinforced thermoplastic polyurethane nanocomposites: physico-mechanical, rheological, and thermal investigations. Polym Compos 41:3260–327010.1002/pc.25617 ↗
25. Caracciolo PC, Lores NJ, Abraham GA (2019) Polyurethane-based structures obtained by additive manufacturing technologies. Mater Biomed Eng 235–25810.1016/B978-0-12-816901-8.00008-0 ↗
26. Liu X, Guo J, Tang W, Li H, Gu X, Sun J, Zhang S (2019) Enhancing the flame retardancy of thermoplastic polyurethane by introducing montmorillonite nanosheets modified with phosphorylated chitosan. Compos Part A Appl Sci Manuf 119:291–29810.1016/j.compositesa.2019.02.009 ↗
27. Majka TM, Raftopoulos KN, Pielichowski K (2018) The influence of POSS nanoparticles on selected thermal properties of polyurethane-based hybrids. J Therm Anal Calorim 133:289–30110.1007/s10973-017-6942-8 ↗
28. Hezma AM, Elashmawi IS, Abdelrazek EM, Rajeh A, Kamal M (2017) Enhancement of the thermal and mechanical properties of polyurethane/polyvinyl chloride blend by loading single walled carbon nanotubes. Prog Nat Sci Mater Int 27:338–34310.1016/j.pnsc.2017.06.001 ↗
29. Xu S, Yu W, Jing M, Huang R, Zhang Q, Fu Q (2017) Largely enhanced stretching sensitivity of polyurethane/carbon nanotube nanocomposites via incorporation of cellulose nanofiber. J Phys Chem C 121:2108–211710.1021/acs.jpcc.6b11783 ↗
30. Szatkowski P, Pielichowska K, Blazewicz S (2017) Mechanical and thermal properties of carbon-nanotube-reinforced self-healing polyurethanes. J Mater Sci 52:12221–1223410.1007/s10853-017-1353-6 ↗
31. Abdollahi A, Roghani-Mamaqani H, Salami-Kalajahi M, Mousavi A, Razavi B, Shahi S (2018) Preparation of organic-inorganic hybrid nanocomposites from chemically modified epoxy and novolac resins and silica-attached carbon nanotubes by sol-gel process: investigation of thermal degradation and stability. Prog Org Coat 117:154–16510.1016/j.porgcoat.2018.01.001 ↗
32. Yeganeh H, Atai M, Talemi PH, Jamshidi S (2006) Synthesis, characterization and properties of novel poly(urethane-imide) networks as electrical insulators with improved thermal stability. Macromol Mater Eng 291:883–89410.1002/mame.200600120 ↗
33. Levchik SV, Weil ED (2004) Thermal decomposition, combustion and flame-retardancy of epoxy resins—a review of the recent literature. Polym Int 53:1901–192910.1002/pi.1473 ↗
34. Gholipour-mahmoudalilou M, Roghani-mamaqani H, Azimi R, Abdollahi A (2018) Synthesis of hyperbranched poly(amidoamine)-grafted graphene nanolayers as a composite and curing agent for epoxy resin. Appl Surf Sci 428:1061–106910.1016/j.apsusc.2017.09.237 ↗
35. Samadaei F, Salami-Kalajahi M, Roghani-Mamaqani H, Banaei M (2015) A structural study on ethylenediamine- and poly(amidoamine)-functionalized graphene oxide: simultaneous reduction, functionalization, and formation of 3D structure. RSC Adv 5:71835–7184310.1039/C5RA12086A ↗
36. Samadaei F, Salami-Kalajahi M, Roghani-Mamaqani H (2016) Grafting of poly(acrylic acid) onto poly(amidoamine)-functionalized graphene oxide via surface-mediated reversible addition-fragmentation chain transfer polymerization. Int J Polym Mater Polym Biomater 65:302–30910.1080/00914037.2015.1119686 ↗
37. Nonahal M, Rastin H, Saeb MR, Sari MG, Moghadam MH, Zarrintaj P, Ramezanzadeh B (2018) Epoxy/PAMAM dendrimer-modified graphene oxide nanocomposite coatings: nonisothermal cure kinetics study. Prog Org Coat 114:233–24310.1016/j.porgcoat.2017.10.023 ↗
38. Keramatinia M, Najafi F, Saeb MR (2017) Synthesis and viscoelastic properties of acrylated hyperbranched polyamidoamine UV-curable coatings with variable microstructures. Prog Org Coat 113:151–15910.1016/j.porgcoat.2017.09.005 ↗
39. Azimi R, Roghani-mamaqani H, Gholipour-mahmoudalilou M (2017) Grafting poly(amidoamine) dendrimer-modified silica nanoparticles to graphene oxide for preparation of a composite and curing agent for epoxy resin Reza. Polymer (Guildf) 126:152–16110.1016/j.polymer.2017.08.037 ↗
40. Wan J, Fan H, Li BG, Xu CJ, Bu ZY (2011) Synthesis and nonisothermal reaction of a novel acrylonitrile-capped poly(propyleneimine) dendrimer with epoxy resin. J Therm Anal Calorim 103:685–69210.1007/s10973-010-1006-3 ↗
41. Cheng Y, Chen D, Fu R, He P (2005) Behavior of polyamidoamine dendrimers as curing agents in bis-phenol A epoxy resin systems. Polym Int 54:495–49910.1002/pi.1748 ↗
42. Pourhosseini-Pakdel Z, Roghani-Mamaqani H, Azimi R, Gholipour-Mahmoudalilou M (2018) Multifunctional curing component for epoxidized novolac resin by grafting poly(amidoamine) on carbon nanotubes using a divergent method. Polym Adv Technol 29:2216–222310.1002/pat.4329 ↗
43. Peterson J, Allikmaa V, Subbi J, Pehk T, Lopp M (2003) Structural deviations in poly(amidoamine) dendrimers: a MALDI-TOF MS analysis. Eur Polym J 39:33–4210.1016/S0014-3057(02)00188-X ↗
44. Yiyun C, Tongwen X (2005) Solubility of nicotinic acid in polyamidoamine dendrimer solutions. Eur J Med Chem 40:1384–138910.1016/j.ejmech.2005.08.001 ↗
45. Yeganeh H, Lakouraj MM, Jamshidi S (2005) Synthesis and properties of biodegradable elastomeric epoxy modified polyurethanes based on poly(ε-caprolactone) and poly(ethylene glycol). Eur Polym J 41:2370–237910.1016/j.eurpolymj.2005.05.004 ↗
46. Song J, Wu G, Shi J, Ding Y, Chen G, Li Q (2010) Properties and morphology of interpenetrating polymer networks based on poly(urethane-imide) and epoxy resin. Macromol Res 18:944–95010.1007/s13233-010-1009-8 ↗
47. Lin M, Shu Y, Tsen W, Chuang F (1999) Synthesis of polyurethane–imide (PU–imide) copolymers with different dianhydrides and their properties. Polym Int 48:433–44510.1002/(SICI)1097-0126(199906)48:6<433::AID-PI161>3.0.CO;2-1 ↗
48. Ebrahimi H, Roghani-Mamaqani H, Salami-Kalajahi M (2018) Preparation of carbon nanotube-containing hybrid composites from epoxy, novolac, and epoxidized novolac resins using sol–gel method. J Therm Anal Calorim 132:513–52410.1007/s10973-018-6992-6 ↗
49. Yang L, Chen J, Wei X, Liu B, Kuang Y (2007) Ethylene diamine-grafted carbon nanotubes: A promising catalyst support for methanol electro-oxidation. Electrochim Acta 53:777–78410.1016/j.electacta.2007.07.052 ↗
50. Zang Z, Hu Z, Li Z, He Q, Chang X (2009) Synthesis, characterization and application of ethylenediamine-modified multiwalled carbon nanotubes for selective solid-phase extraction and preconcentration of metal ions. J Hazard Mater 172:958–96310.1016/j.jhazmat.2009.07.078 ↗
51. Behnam R, Roghani-Mamaqani H, Salami-Kalajahi M (2019) Preparation of carbon nanotube and polyurethane-imide hybrid composites by sol–gel reaction. Polym Compos 40:E1903–E190910.1002/pc.25193 ↗
52. Gnanarajan TP, Nasar AS, Iyer NP, Radhakrishnan G (2000) Synthesis of poly(urethane-imide) using aromatic secondary amine-blocked polyurethane prepolymer. J Polym Sci Part A Polym Chem 38:4032–403710.1002/1099-0518(20001115)38:22<4032::AID-POLA30>3.0.CO;2-R ↗
53. Noparvar-Qarebagh A, Roghani-Mamaqani H, Salami-Kalajahi M (2015) Functionalization of carbon nanotubes by furfuryl alcohol moieties for preparation of novolac phenolic resin composites with high carbon yield values. Colloid Polym Sci 293:3623–363110.1007/s00396-015-3741-2 ↗
54. Deng XY, Xie H, Du L, Fan CJ, Cheng CY, Yang KK, Wang YZ (2019) Polyurethane networks based on disulfide bonds: from tunable multi-shape memory effects to simultaneous self-healing. Sci China Mater 62:437–44710.1007/s40843-018-9318-7 ↗
55. Sahoo NG, Jung YC, Yoo HJ, Cho JW (2006) Effect of functionalized carbon nanotubes on molecular interaction and properties of polyurethane composites. Macromol Chem Phys 207:1773–178010.1002/macp.200600266 ↗
56. Roghani-mamaqani H, Haddadi-asl V (2014) Reverse atom transfer radical polymerization of methyl methacrylate in the presence of Azo-functionalized carbon nanotubes: a grafting from approach. Colloid Polym Sci 292:2971–298110.1007/s00396-014-3349-y ↗
57. Irani M, Mir Mohamad Sadeghi G, Haririan I (2018) Electrospun biocompatible poly(ε-caprolactonediol)-based polyurethane core/shell nanofibrous scaffold for controlled release of temozolomide. Int J Polym Mater Polym Biomater 67:361–36610.1080/00914037.2017.1331350 ↗
58. Chen S, Ma C, Zhang G (2017) Biodegradable polymer as controlled release system of organic antifoulant to prevent marine biofouling. Prog Org Coat 104:58–6310.1016/j.porgcoat.2016.12.011 ↗
59. Nemati H, Roghani-Mamaqani H, Salami-Kalajahi M (2019) Preparation of polyurethane-acrylate and silica nanoparticle hybrid composites by a free radical network formation method. Bull Mater Sci 42:21910.1007/s12034-019-1917-y ↗
60. Behnam R, Roghani-Mamaqani H, Salami-Kalajahi M (2019) Incorporation of silica nanoparticles and polyurethane into hybrid composites for increase of char residue. J Therm Anal Calorim 135:3311–331910.1007/s10973-018-7581-4 ↗
61. Wu T, Liu Y, Li N, Huang GW, Qu CB, Xiao HM (2019) Cryogenic mechanical properties of epoxy resin toughened by hydroxyl-terminated polyurethane. Polym Test 74:45–5610.1016/j.polymertesting.2018.11.048 ↗
62. He X, Liu G, Yan B, Suo H, Zhao C (2016) Significant enhancement of electrochemical behaviour by incorporation of carboxyl group functionalized carbon nanotubes into polyaniline based supercapacitor. Eur Polym J 83:53–5910.1016/j.eurpolymj.2016.08.001 ↗
63. Najafi-Shoa S, Roghani-Mamaqani H, Salami-Kalajahi M, Azimi R, Gholipour-Mahmoudalilou M (2016) Incorporation of epoxy resin and carbon nanotube into silica/siloxane network for improving thermal properties. J Mater Sci 51:9057–907310.1007/s10853-016-0158-3 ↗
64. Roghani-Mamaqani H, Haddadi-Asl V, Mortezaei M, Khezri K (2014) Furfuryl alcohol functionalized graphene nanosheets for synthesis of high carbon yield novolak composites. J Appl Polym Sci 131:1–810.1002/app.40273 ↗
65. Risoluti R, Gullifa G, Carcassi E, Masotti A (2020) TGA/chemometrics addressing innovative preparation strategies for functionalized carbon nanotubes. J Pharm Anal 10:351–35510.1016/j.jpha.2020.02.009 ↗
66. Lee RS, Chen WH, Lin JH (2011) Polymer-grafted multi-walled carbon nanotubes through surface-initiated ring-opening polymerization and click reaction. Polymer (Guildf) 52:2180–218810.1016/j.polymer.2011.03.020 ↗
67. Mardani H, Roghani H, Khezri K, Salami M (2020) Polystyrene-attached graphene oxide with different graft densities via reversible addition-fragmentation chain transfer polymerization and grafting through approach. Appl Phys A 126:1–1110.1007/s00339-020-3428-5 ↗