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Journal of Polymer Research

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01-03-2020 | ORIGINAL PAPER

Polypyrrole inter-layered low temperature curing benzoxazine matrices with enhanced thermal and dielectric properties

Authors: P. Prabunathan, A. Vasanthakumar, M. Manoj, A. Hariharan, M. Alagar

Published in: Journal of Polymer Research | Issue 3/2020

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Abstract

In the present work, curing reaction of benzoxazine was studied with the incorporation of different weight percentage of polypyrrole (PPy). Conventional benzoxazine derived from Bisphenol-F, aniline (BF-a) and bio-based benzoxazine derived from cardanol, furfurylamine (C-f) were synthesized and studied. Significant change in curing temperature (Tp) was observed with the addition of PPy to both C-f and BF-a monomers. With the incorporation of 5 wt% PPy, the Tp of C-f significantly reduced from 245 °C to 185 °C and similarly for BF-a monomer from 226 °C to 165 °C. The plausible mechanism of the benzoxazine ring opening reaction in presence of PPy is also discussed. Further, scanning electron microscopy (SEM) and X-ray diffraction studies suggest that the incorporation of PPy leads to the formation of fractal morphology. Consequently, the PPy inter-layered poly(C-f) and poly(BF-a) matrices contribute to the achievement of low value of dielectric constant (K = 3.39 and 3.83). In addition, PPy interlayer provokes enhanced thermal stability and higher LOI value. Thus, the present work demonstrates the catalytic role of PPy towards the curing reaction of benzoxazines and its contribution towards thermal and dielectric behaviour the of resulted matrices.

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Liao CS, Wang CF, Lin HC et al (2009) Fabrication of patterned superhydrophobic polybenzoxazine hybrid surfaces. Langmuir 25:3359–3362. https://doi.org/10.1021/la900176c CrossRefPubMed

Liu J, Lu X, Xin Z, Zhou C (2013) Synthesis and surface properties of low surface free energy silane-functional polybenzoxazine films. Langmuir 29:411–416. https://doi.org/10.1021/la303730m CrossRefPubMed

Qu L, Zhou C, Xin Z, Liu J (2012) Preparation and surface properties of fluorinated silane-functional polybenzoxazine films. Huagong Xuebao/CIESC J 63:1934–1942. https://doi.org/10.3969/j.issn.0438-1157.2012.06.041 CrossRef

Wen J, Wilkes GL (1996) Organic/inorganic hybrid network materials by the sol-gel approach. Chem Mater 8:1667–1681. https://doi.org/10.1021/cm9601143 CrossRef

Sawaryn C, Landfester K, Taden A (2011) Benzoxazine miniemulsions stabilized with multifunctional main-chain benzoxazine protective colloids. Macromolecules 44:5650–5658. https://doi.org/10.1021/ma200973g CrossRef

Alhwaige AA, Agag T, Ishida H, Qutubuddin S (2013) Biobased chitosan/polybenzoxazine cross-linked films: preparation in aqueous media and synergistic improvements in thermal and mechanical properties. Biomacromolecules 14:1806–1815. https://doi.org/10.1021/bm4002014 CrossRefPubMed

Wang MW, Lin CH, Juang TY (2013) Steric hindrance control synthesis of primary amine-containing benzoxazines and properties of the resulting poly(benzoxazine imide) thermosetting films. Macromolecules 46:8853–8863. https://doi.org/10.1021/ma401756d CrossRef

Pyun J, Matyjaszewski K (2001) [Chem.Mater 2001 Jeffry pyun] synthesis of Nanocomposite organic inorganic Hybrid.pdf. 3436–3448

Zhang K, Zhuang Q, Liu X et al (2013) A new benzoxazine containing benzoxazole-functionalized polyhedral oligomeric silsesquioxane and the corresponding polybenzoxazine nanocomposites. Macromolecules 46:2696–2704. https://doi.org/10.1021/ma400243t CrossRef

10.

Hanbeyoglu B, Kiskan B, Yagci Y (2013) Hydroxyl functional polybenzoxazine precursor as a versatile platform for post-polymer modifications. Macromolecules 46:8434–8440. https://doi.org/10.1021/ma401888g CrossRef

11.

Lin RC, Mohamed MG, Kuo SW (2017) Benzoxazine/Triphenylamine-based Dendrimers prepared through facile one-pot Mannich condensations. Macromol Rapid Commun 38:1–7. https://doi.org/10.1002/marc.201700251 CrossRef

12.

Akkus B, Kiskan B, Yagci Y (2019) Counterion effect of amine salts on ring-opening polymerization of 1,3-Benzoxazines. Macromol Chem Phys 220:1–8. https://doi.org/10.1002/macp.201800268 CrossRef

13.

Liu J, Agag T, Ishida H (2010) Main-chain benzoxazine oligomers: a new approach for resin transfer moldable neat benzoxazines for high performance applications. Polymer (Guildf) 51:5688–5694. https://doi.org/10.1016/J.POLYMER.2010.08.059 CrossRef

14.

Liu J, Ishida H (2014) Anomalous isomeric effect on the properties of Bisphenol F-based Benzoxazines: toward the molecular Design for Higher Performance. Macromolecules 47:5682–5690. https://doi.org/10.1021/ma501294y CrossRef

15.

Ambrožič R, Šebenik U, Krajnc M (2015) Synthesis, curing kinetics, thermal and mechanical behavior of novel cardanol-based benzoxazines. Polymer (Guildf) 76:203–212. https://doi.org/10.1016/j.polymer.2015.08.065 CrossRef

16.

Li S, Yan S, Yu J, Yu B (2011) Synthesis and characterization of new benzoxazine-based phenolic resins from renewable resources and the properties of their polymers. J Appl Polym Sci 122:2843–2848. https://doi.org/10.1002/app.34342 CrossRef

17.

Wang J, Xu YZ, Fu YF, Liu XD (2016) Latent curing systems stabilized by reaction equilibrium in homogeneous mixtures of benzoxazine and amine. Sci Rep 6:1–7. https://doi.org/10.1038/srep38584 CrossRef

18.

Zhang K, Tan X, Wang Y, Ishida H (2019) Unique self-catalyzed cationic ring-opening polymerization of a high performance deoxybenzoin-based 1,3-benzoxazine monomer. Polymer (Guildf) 168:8–15. https://doi.org/10.1016/j.polymer.2019.01.089 CrossRef

19.

Liu C, Shen D, Sebastián RM et al (2013) Catalyst effects on the ring-opening polymerization of 1,3-benzoxazine and on the polymer structure. Polymer (Guildf) 54:2873–2878. https://doi.org/10.1016/j.polymer.2013.03.063 CrossRef

20.

Zhang L, Mao J, Wang S et al (2017) Meta-phenylenediamine formaldehyde oligomer: a new accelerator for benzoxazine resin. React Funct Polym 121:51–57. https://doi.org/10.1016/j.reactfunctpolym.2017.10.020 CrossRef

21.

Zong J, Ran Q (2019) Ring opening reaction of 3,4-Dihydro-2 H -1,3-Benzoxazine with amines at room temperature. ChemistrySelect 4:6687–6696. https://doi.org/10.1002/slct.201901447 CrossRef

22.

Agag T, Arza CR, Maurer FHJ, Ishida H (2010) Primary amine-functional benzoxazine monomers and their use for amide-containing monomeric benzoxazines. Macromolecules 43:2748–2758. https://doi.org/10.1021/ma902556k CrossRef

23.

Sun J, Wei W, Xu Y et al (2015) A curing system of benzoxazine with amine: reactivity, reaction mechanism and material properties. RSC Adv. https://doi.org/10.1039/c4ra16582a

24.

Li S, Zhao C, Gou H et al (2017) Synthesis and characterization of aniline-dimer-based electroactive benzoxazine and its polymer. RSC Adv 7:55796–55806. https://doi.org/10.1039/c7ra11349h CrossRef

25.

Kocaarslan A, Kiskan B, Yagci Y (2017) Ammonium salt catalyzed ring-opening polymerization of 1,3-benzoxazines. Polymer (Guildf) 122:340–346. https://doi.org/10.1016/j.polymer.2017.06.077 CrossRef

26.

Agag T, Geiger S, Alhassan SM et al (2010) Low-viscosity polyether-based main-chain benzoxazine polymers: precursors for flexible thermosetting polymers. Macromolecules 43:7122–7127. https://doi.org/10.1021/ma1014337 CrossRef

27.

Zhang K, Han L, Froimowicz P, Ishida H (2017) A smart latent catalyst containing o-Trifluoroacetamide functional Benzoxazine: precursor for low temperature formation of very high performance Polybenzoxazole with low dielectric constant and high thermal stability. Macromolecules 50:6552–6560. https://doi.org/10.1021/acs.macromol.7b00887 CrossRef

28.

Liu Y-C, Chuang TC (2003) Synthesis and characterization of gold/Polypyrrole Core−Shell Nanocomposites and elemental gold nanoparticles based on the gold-containing Nanocomplexes prepared by electrochemical methods in aqueous solutions. J Phys Chem B 107:12383–12386. https://doi.org/10.1021/jp035680h CrossRef

29.

Barrau S, Demont P, Maraval C et al (2005) Glass transition temperature depression at the percolation threshold in carbon nanotube-epoxy resin and polypyrrole-epoxy resin composites. Macromol Rapid Commun 26:390–394. https://doi.org/10.1002/marc.200400515 CrossRef

30.

Navale ST, Mane AT, Chougule MA et al (2014) Highly selective and sensitive room temperature NO2 gas sensor based on polypyrrole thin films. Synth Met 189:94–99. https://doi.org/10.1016/J.SYNTHMET.2014.01.002 CrossRef

31.

Mane AT, Navale ST, Sen S et al (2015) Nitrogen dioxide (NO2) sensing performance of p-polypyrrole/n-tungsten oxide hybrid nanocomposites at room temperature. Org Electron 16:195–204. https://doi.org/10.1016/j.orgel.2014.10.045 CrossRef

32.

Li SF, Huang WD (2011) Synthesis of new Benzoxazine from Cardanol-furfural resin and the properties of the corresponding polymer. Adv Mater Res 236–238:317–320. https://doi.org/10.4028/www.scientific.net/AMR.236-238.317 CrossRef

33.

Hariharan A, Srinivasan K, Murthy C, Alagar M (2018) Synthesis and characterization of a novel class of low temperature cure Benzoxazines. J Polym Res 25:20–13. https://doi.org/10.1007/s10965-017-1423-0 CrossRef

34.

Bonnaud L, Chollet B, Dumas L et al (2019) High-performance bio-based Benzoxazines from enzymatic synthesis of Diphenols. Macromol Chem Phys 220:1800312. https://doi.org/10.1002/macp.201800312 CrossRef

35.

Wang MW, Jeng RJ, Lin CH (2015) Study on the ring-opening polymerization of Benzoxazine through multisubstituted Polybenzoxazine precursors. Macromolecules 48:530–535. https://doi.org/10.1021/ma502336j CrossRef

36.

Viet CX, Lan DNU, Hung TK (2018) Thermal curing of Benzoxazine blends from Cardanol- Furfurylamine and Diphenolic acid-aniline. IOP Conf Ser Mater Sci Eng 429:012068. https://doi.org/10.1088/1757-899X/429/1/012068 CrossRef

37.

Devaraju S, Krishnadevi K, Sriharshitha S, Alagar M (2019) Design and development of environmentally friendly Polybenzoxazine–silica hybrid from renewable bio-resource. J Polym Environ 27:141–147. https://doi.org/10.1007/s10924-018-1327-z CrossRef

38.

Aradhana R, Mohanty S, Nayak SK (2019) Synergistic effect of polypyrrole and reduced graphene oxide on mechanical, electrical and thermal properties of epoxy adhesives. Polymer (Guildf) 166:215–228. https://doi.org/10.1016/j.polymer.2019.02.006 CrossRef

39.

Zhang K, Yu X, Kuo SW (2019) Outstanding dielectric and thermal properties of main chain-type poly(benzoxazine-: co -imide- co -siloxane)-based cross-linked networks. Polym Chem 10:2387–2396. https://doi.org/10.1039/c9py00464e CrossRef

40.

Rajesh Kumar S, Dhanasekaran J, Krishna Mohan S (2015) Epoxy benzoxazine based ternary systems of improved thermo-mechanical behavior for structural composite applications. RSC Adv 5:3709–3719. https://doi.org/10.1039/c4ra10901e CrossRef

41.

Kumaresan I, Pichaimani P, Ellappan S, Paramasivam M (2018) Ceria doped mullite reinforced polybenzoxazine nanocomposites with improved UV-shielding and thermo-mechanical properties. Polym Compos 39:2073–2080. https://doi.org/10.1002/pc.24169 CrossRef

42.

Pattanayak P, Pramanik N, Kumar P, Kundu PP (2018) Fabrication of cost-effective non-noble metal supported on conducting polymer composite such as copper/polypyrrole graphene oxide (Cu2O/PPy–GO) as an anode catalyst for methanol oxidation in DMFC. Int J Hydrog Energy 43:11505–11519. https://doi.org/10.1016/J.IJHYDENE.2017.04.300 CrossRef

43.

Liu A, Li C, Bai H, Shi G (2010) Electrochemical deposition of polypyrrole/sulfonated graphene composite films. J Phys Chem C 114:22783–22789. https://doi.org/10.1021/jp108826e CrossRef

44.

Chen F, Xing Y, Wang Z et al (2016) Nanoscale Polydopamine (PDA) meets π–π interactions: an Interface-directed Coassembly approach for Mesoporous nanoparticles. Langmuir 32:12119–12128. https://doi.org/10.1021/acs.langmuir.6b03294 CrossRefPubMed

45.

Sasi kumar R, Padmanathan N, Alagar M (2015) Design of hydrophobic polydimethylsiloxane and polybenzoxazine hybrids for interlayer low k dielectrics. New J Chem 39:3995–4008. https://doi.org/10.1039/C4NJ02188F CrossRef

46.

Kim SH, Jang SH, Byun SW et al (2003) Electrical properties and EMI shielding characteristics of polypyrrole-nylon 6 composite fabrics. J Appl Polym Sci 87:1969–1974. https://doi.org/10.1002/app.11566 CrossRef

47.

Omastová M, Kosina S, Pionteck J et al (1996) Electrical properties and stability of polypyrrole containing conducting polymer composites. Synth Met 81:49–57. https://doi.org/10.1016/0379-6779(96)80228-1 CrossRef

48.

Zhang T, Wang J, Feng T et al (2015) A novel high performance oxazine derivative: design of tetrafunctional monomer, step-wise ring-opening polymerization, improved thermal property and broadened processing window. Polym Chem. https://doi.org/10.1039/x0xx00000x

49.

Lin RC, Kuo SW (2018) Well-defined benzoxazine/triphenylamine-based hyperbranched polymers with controlled degree of branching. RSC Adv 8:13592–13611. https://doi.org/10.1039/c8ra00506k CrossRef

50.

Mohamed MG, Hsiao CH, Luo F et al (2015) Multifunctional polybenzoxazine nanocomposites containing photoresponsive azobenzene units, catalytic carboxylic acid groups, and pyrene units capable of dispersing carbon nanotubes. RSC Adv 5:45201–45212. https://doi.org/10.1039/c5ra07983g CrossRef

51.

Zhang X, Yan X, Guo J et al (2015) Polypyrrole doped epoxy resin nanocomposites with enhanced mechanical properties and reduced flammability. J Mater Chem C 3:162–176. https://doi.org/10.1039/c4tc01978d CrossRef

52.

Ramdani N, Derradji M, Feng T et al (2015) Preparation and characterization of thermally-conductive silane-treated silicon nitride filled polybenzoxazine nanocomposites. Mater Lett 155:34–37. https://doi.org/10.1016/J.MATLET.2015.04.097 CrossRef

53.

Hamerton I, Howlin BJ, Mitchell AL et al (2012) Systematic examination of thermal, mechanical and dielectrical properties of aromatic polybenzoxazines. React Funct Polym 72:736–744. https://doi.org/10.1016/J.REACTFUNCTPOLYM.2012.07.001 CrossRef

54.

Chen S-HSW-A (2002) Microelectronic or optoelectronic package having a polybenzoxazine-based film as an underfill material. US20070117263A1

55.

Zhang K, Yu X (2018) Catalyst-free and low-temperature Terpolymerization in a single-component Benzoxazine resin containing both Norbornene and acetylene functionalities. Macromolecules 51:6524–6533. https://doi.org/10.1021/acs.macromol.8b01558 CrossRef

56.

Das-Gupta DK, Doughty K (1988) Polymer-ceramic composite materials with high dielectric constants. Thin Solid Films 158:93–105. https://doi.org/10.1016/0040-6090(88)90306-9 CrossRef

57.

Cherney EA (2005) Silicone rubber dielectrics modified by inorganic fillers for outdoor high voltage insulation applications. IEEE Trans Dielectr Electr Insul 1108–1115. https://doi.org/10.1109/TDEI.2005.1561790

58.

Armelin E, Pla R, Liesa F et al (2008) Corrosion protection with polyaniline and polypyrrole as anticorrosive additives for epoxy paint. Corros Sci 50:721–728. https://doi.org/10.1016/j.corsci.2007.10.006 CrossRef

59.

Kim BG, Kim YS, Kim YH et al (2016) Nano-scale insulation effect of polypyrrole/polyimide core-shell nanoparticles for dielectric composites. Compos Sci Technol 129:153–159. https://doi.org/10.1016/j.compscitech.2016.04.028 CrossRef

60.

Martens HCF, Brom HB, Reedijk JA et al (1999) Dielectric study of polypyrrole/epoxy composites. Synth Met 102:1236–1237. https://doi.org/10.1016/S0379-6779(98)01434-9 CrossRef

61.

Prabunathan P, Thennarasu P, Song JK, Alagar M (2017) Achieving low dielectric, surface free energy and UV shielding green nanocomposites: via reinforcing bio-silica aerogel with polybenzoxazine. New J Chem 41:5313–5321. https://doi.org/10.1039/c7nj00138j CrossRef

62.

Le TH, Kim Y, Yoon H (2017) Electrical and electrochemical properties of conducting polymers. Polymers (Basel) 9:150CrossRef

63.

Shih HK, Hsieh CC, Mohamed MG, Zhu CY, Kuo SW (2016) Ternary polybenzoxazine/POSS/SWCNT hybrid nanocomposites stabilized through supramolecular interactions. Soft Matter 12:1847–1858. https://doi.org/10.1039/c5sm02569a CrossRefPubMed

64.

Mohamed MG, Kuo SW (2019) Functional silica and carbon nanocomposites based on polybenzoxazines. Macromol Chem Phys 220:1–13. https://doi.org/10.1002/macp.201800306 CrossRef

Title: Polypyrrole inter-layered low temperature curing benzoxazine matrices with enhanced thermal and dielectric properties
Authors: P. Prabunathan
A. Vasanthakumar
M. Manoj
A. Hariharan
M. Alagar
Publication date: 01-03-2020
Publisher: Springer Netherlands
Published in: Journal of Polymer Research / Issue 3/2020
Print ISSN: 1022-9760
Electronic ISSN: 1572-8935
DOI: https://doi.org/10.1007/s10965-020-2022-z

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