journal article·2014-07Open access

Fullerene-modified polyamide 6 by in situ anionic polymerization in the presence of PCBM

Nadya Dencheva, Hugo Gaspar, Sergej Filonovich, Olga Lavrova, Tito Busani, Gabriel Bernardo, Zlatan Denchev

Journal of Materials Science· Volume 49· Issue 14

Abstract

Activated anionic ring-opening polymerization of e-caprolactam (ECL) was carried out for the first time in the presence of [6,6]-phenyl-C61-butyric acid methyl ester (PCBM) to prepare polyamide 6 (PA6)-based composites comprising up to 3 wt% of this fullerene derivative. This in situ polymerization process produced high molecular weight composites containing 52–80 % of gel fraction at PCBM concentration ≥0.5 wt%. Spectral, thermo-mechanical, synchrotron X-ray, and scanning electron microscopy data were used to elucidate the structure and morphology of the PA6/PCBM composites. A mechanism of the chemical structure evolution was proposed starting with incipient complexation between ECL and PCBM, via subsequent chemical linking of ECL moieties on the C60 spheroid and final formation of star-burst and cross-linked morphologies. PCBM amounts of 0.1 wt% and more decreased the volume resistivity from 1012 Ω cm (neat PA6) to 109–107 Ω cm, thus opening the way for new applications of anionic PA6.
Source: openaire · Quality: candidate unverified · Source record ↗

Research context

OpenAlex topics: Conducting polymers and applications · Polymer Nanocomposites and Properties · Polymer Nanocomposite Synthesis and Irradiation

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (38)

Show source-provided references
1. Vanlaeke P, Swinnen A, Haeldermans I, Vanhoyland G, Aernouts T, Cheyns T, Deibel C et al (2006) P3HT/PCBM bulk heterojunction solar cells: relation between morphology and electro-optical characteristics. Sol Energy Mater Sol Cells 90:2150–215810.1016/j.solmat.2006.02.010 ↗
2. Xu H, Li J, Leung BHK, Poon CCY, Ong BS, Zhang Y, Zhao N (2013) A high-sensitivity near-infrared phototransistor based on an organic bulk heterojunction. Nanoscale 5:11850–1185510.1039/c3nr03989g ↗
3. Benjamin SC, Arzhang A, Briggs AD, Britz DA, Gunlycke D, Jefferson J et al (2006) Towards a fullerene-based quantum computer. J Phys Condens Matter 18:S867–S88310.1088/0953-8984/18/21/S12 ↗
4. Wang C, Guo ZX, Fu S, Wu W, Zhu D (2004) Polymers containing fullerene or carbon nanotube structures. Prog Polym Sci 29:1079–114110.1016/j.progpolymsci.2004.08.001 ↗
5. Jin X, Hu JY, Tint ML, Ong SL, Biryulin Y, Polotskaya G (2007) Estrogenic compounds removal by fullerene-containing membranes. Desalination 214:83–9010.1016/j.desal.2006.10.019 ↗
6. Dyakonov V, Zoriniants G, Scharber M, Brabec JC, Janssen RAJ, Hummelen JC, Sariciftci NS (1999) Photoinduced charge carriers in conjugated polymer–fullerene composites studied with light-induced electron-spin resonance. Phys Rev B 59:8019–802510.1103/PhysRevB.59.8019 ↗
7. Brabec CJ, Johansson H, Cravino A, Sariciftci NS, Comoretto D, Dellepiane G, Moggio I (1999) The spin signature of charged photoexcitations in carbazolyl substituted polydiacetylene. J Chem Phys 111:10354–1036110.1063/1.480384 ↗
8. Lu Z, He C, Chung TC (2001) Composites of multifunctional benzylaminofullerene with low density polyethylene. Polymer 42:5233–523710.1016/S0032-3861(00)00806-5 ↗
9. Baltá-Calleja FJ, Giri L, Asano T, Mieno T, Sakurai A, Ohnuma M, Sawatari C (1996) Structure and mechanical properties of polyethylene–fullerene composites. J Mater Sci 31(19):5153–5157. doi: 10.1007/BF0035591810.1007/BF00355918 ↗
10. Weng D, Lee HK, Levon K, Mao J, Scrivens WA, Stephens EB, Tour JM (1999) The influence of Buckminster fullerenes and their derivatives on polymer properties. Eur Polym J 35:867–87810.1016/S0014-3057(98)00055-X ↗
11. Brabec CJ, Dyakonov V, Sariciftci NS, Graupner W, Leising G, Hummelen JC (1998) Investigation of photoexcitations of conjugated polymer/fullerene composites embedded in conventional polymers. J Chem Phys 109:1185–119510.1063/1.476664 ↗
12. Campbell K, Gurun B, Sumpter BG, Thio YS, Bucknall DG (2011) Role of conformation in π–π interactions and polymer/fullerene miscibility. Phys Chem B 115:8989–899510.1021/jp203153m ↗
13. Bucknall DG, Bernardo G, Shofner ML, Nabankur D, Raghavan D, Sumpter BG, Sides S et al (2012) Phase-morphology and molecular structure correlations in model fullerene–polymer nanocomposites. Mater Sci Forum 714:63–6610.4028/www.scientific.net/MSF.714.63 ↗
14. Dencheva N, Denchev Z (2013) Clay distribution and crystalline structure evolution in polyamide 6/montmorillonite composites prepared by activated anionic polymerization. J Appl Polym Sci 130:1228–123810.1002/app.39274 ↗
15. Kelar K (2006) Polyamide 6 modified with fullerenes prepared via anionic polymerization of ε-caprolactam. Polimery 51:415–424 (in Polish)10.14314/polimery.2006.415 ↗
16. Zuev VV, Ivanova IG (2012) Mechanical and electrical properties of polyamide-6-based nanocomposites reinforced by fulleroid fillers. Polym Eng Sci 52:1206–121110.1002/pen.22188 ↗
17. Zuev VV, Shlikov AV (2012) Polyamide 12/fullerene C60 composites: investigation on their mechanical and dielectric properties. J Polym Res 19:9925–993010.1007/s10965-012-9925-2 ↗
18. Zuev VV, Kostromin SV, Shlikov AV (2012) Mechanics of polymer nanocomposites modified with fulleroid nanofillers. Vysokomol Soedin Ser A 52:815–819
19. Ivanova L, Kulichikhin SG, Alkaeva OF, Akimushkina NM, Vyrsky UP, Malkin AY (1978) Determining of molecular characteristics of polycaproamide. Vysokomol Soedin Ser A 20(12):2813–2816
20. POLAR, version 2.7.3; Copyright® 1997–2008 by Stonybrook Technology and Applied research, Inc, USA
21. Roda J (2009) Polyamides. In: Dubois P, Coulembier O, Raquez J-M (eds) Handbook of ring-opening polymerization. Wiley-VCH, Weinheim, p 177
22. Dan F, Vasiliu-Oprea C (1998) Anionic polymerization of caprolactam in organic media: morphological aspects. Colloid Polym Sci 276:483–49510.1007/s003960050270 ↗
23. Wudl F, Hirsch A, Khemani KC, Suzuki T, Allemand PM, Kosch A et al (1992) Survey of chemical reactivity of C60, electrophile and dieno-polarophile par excellence. ACS Symp Ser 481:161–17510.1021/bk-1992-0481.ch011 ↗
24. Hirsch A, Brettreich M (2005) Fullerenes: chemistry and reactions. Wiley-VCH, Weinheim, p 87
25. Prato M (1999) Fullerene materials. In: Hirsch A (ed) Topics in current chemistry. Fullerenes and related structures, vol 199. Springer, Berlin, pp 173–18710.1007/3-540-68117-5_5 ↗
26. Dencheva N, Nunes T, Oliveira JM, Denchev Z (2005) Microfibrillar composites based on polyamide/polyethylene blends. 1. Structure investigations in oriented and isotropic polyamide 6. Polymer 46:887–90110.1016/j.polymer.2004.11.105 ↗
27. Krusic PJ, Wasserman E, Parkinson BA, Malone B, Holler ER Jr, Keizer PN et al (1991) Electron spin resonance study of the radical reactivity of C60. J Am Chem Soc 113:6274–627510.1021/ja00016a056 ↗
28. Morton JR, Preston KF, Krusic PJ, Hill SA, Wasserman E (1992) The dimerization of fullerene RC60 radicals [R = alkyl]. J Am Chem Soc 114:5454–545510.1021/ja00039a083 ↗
29. Troitskii BB, Troitskaya LS, Anikina LI, Denisova VN, Novikova MA, Khokhlova LV (2001) Inhibiting effect of fullerenes C60 and C70 on high-temperature oxidative degradation of copolymers of methyl methacrylate with methacrylic acid and methacrylamide. J Polym Mater 48:251–26510.1080/00914030108050785 ↗
30. Pearce EM, Shalaby SW, Barker RH (1975) Retardation of combustion of polyamides. In: Lewin M, Atlas SM, Pearce EM (eds) Flame retardant polymeric materials. Plenum, New York, pp 239–27510.1007/978-1-4684-2148-4_6 ↗
31. Troitskii BB, Troitskaya LS, Dmitriev AA, Yakhnov AS (2000) Inhibition of thermo-oxidative degradation of poly(methyl methacrylate) and polystyrene by C60. Eur Polym J 36:1073–108410.1016/S0014-3057(99)00156-1 ↗
32. Kelar K, Jurkowski B (2007) Properties of anionically polymerized ε-caprolactam in the presence of carbon nanotubes. J Appl Polym Sci 104:3010–301710.1002/app.24568 ↗
33. Wilkinson AN, Man Z, Stanford JL, Matikainen P, Clemens ML, Lees GC et al (2006) Structure and dynamic mechanical properties of melt intercalated polyamide 6/montmorillonite nanocomposites. Macromol Mater Eng 291:917–92810.1002/mame.200600150 ↗
34. Jha A, Bhowmick AK (1998) Thermal degradation and ageing behavior of novel thermoplastic elastomeric nylon-6/acrylate rubber reactive blends. Polym Degrad Stab 62:575–58610.1016/S0141-3910(98)00044-5 ↗
35. Shen L, Du Q, Wang H, Zhong W, Yang Y (2004) In situ polymerization and characterization of polyamide-6/silica nanocomposites derived from water glass. Polym Int 53:1153–116010.1002/pi.1520 ↗
36. ANSI/ESD S541-2008: packaging material standards for ESD sensitive items (2008)
37. Busani T, Devine RAB (2005) The importance of network structure in high-k dielectrics: LaAlO3, Pr2O3, and Ta2O5. J Appl Phys 98:4410210.1063/1.2012513 ↗
38. Odian G (2004) Principles of polymerization, 4th edn. Wiley, Hoboken, pp 575–57710.1002/047147875X ↗