Top

Polymer Bulletin

Published in:

06-07-2020 | Original Paper

A novel synthesis of polybutadiene-based polyurethane binder and conductive graphene–polyurethane nanocomposites: a new approach to polybutadiene recycling

Authors: Zahra Rahmatpanah, Mir Mohammad Alavi Nikje

Published in: Polymer Bulletin | Issue 7/2021

Activate our intelligent search to find suitable subject content or patents.

search-config

AI-assisted search

Off

Abstract

Synthesis and characterization of a new class of polybutadiene polyol polyurethanes were investigated with three consecutive reactions, namely polybutadiene (PB) chain cleavage by a two-step oxidation reaction using meta-chloroperbenzoic acid (m-CPBA) and periodic acid (H₅IO₆) in order to prepare polybutadiene polyol precursor, continued by telechelic amine polyol synthesis by an amination reaction using diethanolamine (DEA) in the presence of sodium borohydride (NaBH₄) and finally telechelic polyurethane preparation by the reaction of synthesized polyol and toluene diisocyanate (TDI). Nanocomposites were prepared through an in situ polymerization reaction by incorporation of 1–3 wt% of graphene conductive nanosheets. Successful structural elucidation of the synthesized polymeric binder and nanocomposites was investigated by using well-known methods. TGA analysis revealed slower degradation and moderate thermal stability in higher weight percent nanocomposite. SEM images and XRD patterns resulted in fine nanoparticle distribution, lack of agglomeration and approximately constant nanoparticle size. Conductometry confirmed higher electrical conductivity data for nanocomposites by increasing graphene nanosheet contents.

Graphic abstract

previous article Swelling equilibria of novel propenamide/2-acrylamido-2-methyl-1-propanesulfonic acid/guar gum/clinoptilolite biohybrid hydrogels and application as a sorbent for BV1 removal

next article Synthesis and evaluation of the efficiency of antibacterial hydrogel beads based on the sodium alginate–ferula gum for delayed release of quercetin

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

über 102.000 Bücher
über 537 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Finance + Banking
Management + Führung
Marketing + Vertrieb
Maschinenbau + Werkstoffe
Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

inform now

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

über 67.000 Bücher
über 390 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Maschinenbau + Werkstoffe

Jetzt Wissensvorsprung sichern!

inform now

Available only for authorised users

Polgar LM, Van Duin M, Broekhuis A, Picchioni F (2015) Use of Diels–Alder chemistry for thermoreversible cross-linking of rubbers: the next step toward recycling of rubber products? Macromolecules 48:7096–7105. https://doi.org/10.1021/acs.macromol.5b01422CrossRef

Bai J, Li H, Shi Z, Yin J (2015) An eco-friendly scheme for the cross-linked polybutadiene elastomer via Thiol-Ene and Diels–Alder click chemistry. Macromolecules 48:3539–3546. https://doi.org/10.1021/acs.macromol.5b00389CrossRef

Bobade S, Wang Y, Mays J, Baskaran D (2014) Synthesis and characterization of ureidopyrimidone telechelics by CuAAC ‘click’ reaction: effect of Tg and polarity. Macromolecules 47:5040–5050. https://doi.org/10.1021/ma5007705CrossRef

Fainleib A, Pires RV, Lucas EF, Soares BG (2013) Degradation of non-vulcanized natural rubber—renewable resource for fine chemicals used in polymer synthesis. Polimeros 23:441–450. https://doi.org/10.4322/polimeros.2013.070CrossRef

Dong L, Zhou W, Sui X, Wang Z, Wu P, Zuo J, Cai H, Liu X (2016) Thermal, mechanical, and dielectric properties of epoxy resin modified using carboxyl-terminated polybutadiene liquid rubber. Elast Plast J 49:281–297. https://doi.org/10.1177/0095244316653261CrossRef

Morandi G, Kebir N, Campistron I, Gohier F, Laguerre A, Pilard JF (2007) Direct selective reductive amination of carbonyl telechelic oligoisoprenes: elaboration of promising tri- and tetrafunctionalized oligoisoprene intermediates. Tetrahedron Lett 48:7726–7730. https://doi.org/10.1016/j.tetlet.2007.07.089CrossRef

Zhou Q, Jie S, Li BG (2014) Preparation of hydroxyl-terminated polybutadiene with high cis-1,4 content. Ind Eng Chem Res 53:17884–17893. https://doi.org/10.1021/ie503652gCrossRef

Phinyocheep P, Phetphaisit CW, Derouet D, Campistron I, Brosse JC (2005) Chemical degradation of epoxidized natural rubber using periodic acid: preparation of epoxidized liquid natural rubber. Appl Polym Sci 95:6–15. https://doi.org/10.1002/app.20812CrossRef

Zhou Q, Jie S, Li BG (2015) Facile synthesis of novel HTPBs and EHTPBs with high cis-1,4 content and extremely low glass transition temperature. Polymer 67:208–215. https://doi.org/10.1016/j.polymer.2015.04.078CrossRef

10.

Morita A, Maughon BR, Bielawski CW, Grubbs RH (2000) A ring-opening metathesis polymerization (ROMP) approach to carboxyl- and amino-terminated telechelic poly(butadiene)s. Macromolecules 33:6621–6623. https://doi.org/10.1021/ma000013xCrossRef

11.

Kebir N, Morandi G, Campistron I, Laguerre A, Pilard JF (2005) Synthesis of well defined amino telechelic cis-1,4-oligoisoprenes from carbonyl telechelic oligomers; first studies of their potentialities as polyurethane or polyurea materials precursors. Polymer 46:6844–6854. https://doi.org/10.4322/polimeros.2013.070CrossRef

12.

Berto P, Grelier S, Peruch F (2017) Telechelic polybutadienes or polyisoprenes precursors for recyclable elastomeric networks. Macromolecules 38:2–7. https://doi.org/10.1002/marc.201700475CrossRef

13.

Rao BN, Yadav PJP, Malkappa K, Jana T, Sastry PU (2015) Triazine functionalized hydroxyl terminated polybutadiene polyurethane: influence of triazine structure. Polymer 77:323–333. https://doi.org/10.1016/polymer.2015.09.046CrossRef

14.

Mingjie H, Shuzhen T, Wei F, Le G, Xinghai L, Yunbai L, Chi H (2014) Vinyl-modified hyperbranched polyether cross-linked hydroxyl-terminated polybutadiene-based polyurethane membrane for pervaporation recovery of butanol. High Perform Polym 27:381–391. https://doi.org/10.1177/F0954008314553040CrossRef

15.

Trovatti E, Lacerda TM, Carvalho AJF, Gandini A (2015) Recycling tires? Reversible crosslinking of poly(butadiene). Adv Mater 27:1–4. https://doi.org/10.1002/adma.201405801CrossRef

16.

Nikje MMA, Hajifatheali H (2013) Performance of dimethyl dioxirane/nano-TiO₂ on epoxidation of polybutadiene and hydroxyl terminated polybutadiene. Elastomers Plast 45:457–469. https://doi.org/10.1177/F0095244312457800CrossRef

17.

Fang Y, Zhan M, Wang Y (2001) The status of recycling of waste rubber. Mater Des 22:123–127. https://doi.org/10.1016/S0261-3069(00)00052-2CrossRef

18.

Lotti L, Coiai S, Ciardelli F, Galimberti M, Passaglia E (2009) Thiol-Ene radical addition of L-cysteine derivatives to low molecular weight polybutadiene. Macromol Chem Phys 210:1471–1483. https://doi.org/10.1002/macp.200900164CrossRef

19.

Berto P, Pointet A, Coz CL, Grelier S, Peruch F (2017) Recyclable telechelic cross linked polybutadiene based on reversible Diels−Alder chemistry. Macromolecules 51:651–659. https://doi.org/10.1021/acs.macromol.7b02220CrossRef

20.

Kebir N, Campistron I, Laguerre A, Pilard JF, Bunel C (2011) New crosslinked polyurethane elastomers with various physical properties from natural rubber derivatives. Appl Polym Sci 122(3):1677–1687. https://doi.org/10.1002/app.34013CrossRef

21.

AqilahHamuzan H, Badri KH (2016) The role of isocyanates in determining the viscoelastic properties of polyurethane, vol 1784. American Institute of Physics, pp 1–6. https://doi.org/10.1063/1.4966757

22.

Prociak A, Malewska E, Bak S (2016) Influence of isocyanate index on selected properties of flexible polyurethane foams modified with various bio-components. Renew Mater 4:78–85. https://doi.org/10.1007/s10924-019-01527-7CrossRef

23.

Gama NW, Ferreira A, Timmons AB (2018) Polyurethane foams: past, present, and future. Materials 11:1841–1876. https://doi.org/10.3390/ma11101841CrossRefPubMedCentral

24.

Krebs M, Hubel R (2016) The adjustment of physical properties of viscoelastic foam—the role of different raw materials. American Chemistry Council. https://www.pu-additives.com

25.

Li Z, Dong S, Yu G, Li Z, Liu Y, Ye C, Oin J (2007) Novel second-order nonlinear optical main-chain polyurethanes: adjustable subtle structure. improved thermal stability and enhanced nonlinear optical property. Polymer 48:5520–5529. https://doi.org/10.1016/j.polymer.2007.07.052CrossRef

26.

Bakar M, Duk R, Przybylek M, Kostrzewa M (2008) Mechanical and thermal properties of epoxy resin modified with polyurethane. Reinf Plast Compos 28:5520–5529. https://doi.org/10.1177/0731684408091703CrossRef

27.

Han NR, Cho JW (2016) Click coupled stitched graphene sheets and their polymer nanocomposites with enhanced photothermal and mechanical properties. Compos part C 87:78–85. https://doi.org/10.1016/j.compositesa.2016.04.015CrossRef

28.

Pielichowska K, Bieda J, Szatkowski P (2016) Polyurethane/graphite nano-platelet composites for thermal energy storage. Renew Energy 91:456–465. https://doi.org/10.1016/j.renene.2016.01.076CrossRef

29.

Zhang YF, Zhao YH, Bai SL, Yuan X (2016) Numerical simulation of thermal conductivity of graphene filled polymer composites. Compos B 106:324–331. https://doi.org/10.1016/j.compositesb.2016.09.052CrossRef

30.

Seyedin S, Razal JM, Innis PC, Jalili R, Wallace GG (2016) Compositional effects of large graphene oxide sheets on the spinnability and properties of polyurethane composite fibers. Adv Mater 3:1–10. https://doi.org/10.1002/admi.201500672CrossRef

31.

Chen T, Zhao Y, Pen L, Lin M (2015) Insight into effect of hydrothermal preparation process of nanofillers on dielectric, creep and electromechanical performance of polyurethane dielectric elastomer/reduced graphene oxide composites. Mater Sci 26:10164–10171. https://doi.org/10.1007/s10854-015-3703-yCrossRef

32.

Fallahi H, Azizi H, Ghasemi I, Karrabi M (2017) Preparation and properties of electrically conductive, flexible and transparent silver nanowire/poly (lactic acid) nanocomposites. Org Electron 44:74–84. https://doi.org/10.1016/j.orgel.2017.01.043CrossRef

33.

Jasmi F, Azeman NH, Bakar AAA, Zan MSD, Badri KH, Suait MS (2018) Ionic conductive polyurethane-graphene nanocomposite for performance enhancement of optical fiber Bragg grating temperature sensor. IEEE Access 6:47355–47363. https://doi.org/10.1109/ACCESS.2018.2867220CrossRef

34.

Liu BT, Kuo HL (2013) Graphene/silver nanowire sandwich structures for transparent conductive films. Carbon 63:390–396. https://doi.org/10.1016/j.carbon.2013.06.094CrossRef

35.

Yaghoubi A, Nikje MMA (2018) Silanization of multi-walled carbon nanotubes and the study of its effects on the properties of polyurethane rigid foam nanocomposites. Compos A 109:338–344. https://doi.org/10.1016/j.compositesa.2018.03.028CrossRef

36.

Hoseini Z, Nikje MMA (2018) Synthesis and characterization of a novel thermally stable water dispersible polyurethane and its magnetic nanocomposites. Iran Polym J 27:733–743. https://doi.org/10.1007/s13726-018-0650-5CrossRef

37.

Wu G, Xu X, He X, Yan Y (2018) Preparation and characterization of graphene oxide-modified Sapium sebiferum oil-based polyurethane composites with improved thermal and mechanical properties. Polymers 10:1–13. https://doi.org/10.3390/polym10020133CrossRef

38.

Kaur G, Adhikari R, Cass P, Bown M, Evans MDM, Vashi AV, Gunatillakea P (2015) Graphene/polyurethane composites: fabrication and evaluation of electrical conductivity, mechanical properties and cell viability. RCS Adv 5:98762–98772. https://doi.org/10.1039/C5RA20124KCrossRef

39.

Ding JN, Fan Y, Zao CX, Liu YB, Yu CT, Yuan NY (2011) Electrical conductivity of waterborne polyurethane/graphene composites prepared by solution mixing. Compos Mater 46:747–752. https://doi.org/10.1177/0021998311413835CrossRef

40.

Nikje MMA, Moghaddam ST, Noruzian M, Farahmand-Nejad MA, Shabani K, Haghshenas M, Shakhesi S (2013) Preparation and characterization of flexible polyurethane foam nanocomposites reinforced by magnetic core-shell Fe₃O₄@APTS nanoparticles. Colloid Polym Sci 292:627–633. https://doi.org/10.1007/s00396-013-3099-2CrossRef

41.

Talapatra A, Datta D (2019) Graphene-reinforced thermoplastic polyurethane nanocomposites: a simulation and experimental study. Thermoplast Compos Mater. https://doi.org/10.1177/0892705719839459(2019)1-19CrossRef

42.

Lin SC, Ma CCM, Liao WH, Wang JA, Zeng SJ, Hsu SY, Chen YH, Hsiao ST, Cheng TY, Lin CW, Hsiao PY (2016) Preparation of a graphene–silver nanowire hybrid/silicone rubber composite for thermal interface materials. Taiwan Inst Chem Eng 68:396–406. https://doi.org/10.1016/j.jtice.2016.08.009CrossRef

43.

Fernández SG, Ugarte L, Rodriguez CP, Zubitur M, Corcuera MA, Eceiza A (2016) Flexible polyurethane foam nanocomposites with modified layered double hydroxides. Appl Clay Sci Part C 123:109–120. https://doi.org/10.1016/j.clay.2016.01.015CrossRef

44.

Dai L, Mau AWH, Hans JG, Winkler D, Spurling TH, Hong X, Yanga Y, Whiteb JW (1995) “I₂-Doping” of 1,4-polydienes. Synth Metals 69:563–566. https://doi.org/10.1016/0379-6779(94)02570-OCrossRef

Title: A novel synthesis of polybutadiene-based polyurethane binder and conductive graphene–polyurethane nanocomposites: a new approach to polybutadiene recycling
Authors: Zahra Rahmatpanah
Mir Mohammad Alavi Nikje
Publication date: 06-07-2020
Publisher: Springer Berlin Heidelberg
Published in: Polymer Bulletin / Issue 7/2021
Print ISSN: 0170-0839
Electronic ISSN: 1436-2449
DOI: https://doi.org/10.1007/s00289-020-03288-z

Springer Professional

Abstract

Graphic abstract

Please log in to get access to your license.

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Springer Professional "Technik"

Other articles of this Issue 7/2021

Mechanical behavior of ABS plastic-matrix nanocomposites with three different carbon-based nanofillers

Synthesis and evaluation of the efficiency of antibacterial hydrogel beads based on the sodium alginate–ferula gum for delayed release of quercetin

Comparative studies of thermal and mechanical properties of macrocyclic versus linear polylactide

Preparation of anion exchange membrane by incorporating IRMOF-3 in quaternized chitosan

Effect of vulcanization systems on the properties of natural rubber latex films

Biocomposites based on plasticized starch: thermal, mechanical and morphological characterization

Premium Partners