Journal of Polymers and the Environment

, Volume 27, Issue 9, pp 1878–1896 | Cite as

Cardanol Functionalized Carboxylated Acrylonitrile Butadiene Rubber for Better Processability, Technical Properties and Biocompatibility

  • Satyajit Samantarai
  • Ahindra Nag
  • Nitesh Singh
  • Debabrata Dash
  • Amit Basak
  • Golok B. NandoEmail author
  • Narayan Ch. DasEmail author
Original paper


The present investigation deals with the latex stage functionalization of carboxylated acrylonitrile butadiene rubber (XNBR) by chemically grafting cardanol onto its backbone main chain to impart multifunctional characteristics to it. The grafting of cardanol onto XNBR in the latex stage has been accomplished successfully using benzoyl peroxide (BPO) as a free radical initiator. Cardanol grafted XNBR (C-g-XNBR) exhibited an increase in molecular weight (7.5%) with an increase in PDI (polydispersity index). The optimum grafting parameters were found to be of 1 phr BPO with 15 phr cardanol at a reaction temperature of 80 °C and a reaction time of 10 h using “Taguchi methodology”. The maximum percentage grafting (PG) and grafting efficiency (GE) were estimated to be 13.8 and 92.8%, respectively at the optimum combination of the reaction parameters. Differential scanning calorimetry and dynamic mechanical analysis results exhibited a decrease in Tg value for the functionalized elastomer. Thermogravimetric analysis displayed an increase in the thermal stability of C-g-XNBR. MTT [3-(4,5-dimethylthiazol-2yl)-2,5-diphenyltetrazolium bromide] assay and hemolysis studies proved that functionalized rubber as biocompatible. Moreover, functionalized XNBR exhibited a potential bactericidal effect against Staphylococcus aureus and Escherichia coli strains. Fire and flame retardancy study revealed an increased LOI (limiting oxygen index) for C-g-XNBR.


Functionalization XNBR Mooney viscosity MTT assay Limiting oxygen index 



One of the authors, Mr. S. Samantarai is grateful to the All India Council for Technical Education (AICTE), New Delhi, India, for providing a research fellowship to carry out this study. The authors thank Dr. Subhra Mohanty of Omnova Solutions Pvt. Ltd., Gujarat, India, for providing free latex samples. The authors would like to kindly acknowledge the cooperation received from Dr. Ragini Tilak, Department of Microbiology, IMS, BHU, Varanasi, U. P., India, for carrying out the antibacterial property evaluation study of the rubber samples.

Compliance with ethical standards

Conflict of interest

The authors declare no competing financial interest.


  1. 1.
    Lithner D, Larsson Å, Dave G (2011) Environmental and health hazard ranking and assessment of plastic polymers based on chemical composition. Sci Tot Environ 409(18):3309–3324CrossRefGoogle Scholar
  2. 2.
    Van der Putte I, Groshart C, Okkerman PC (2000) European Commission DG ENV: Towards the establishment of a priority list of substances for further evaluation of their role in endocrine disruption. M0355008/1786Q710/11/00. BKH, Consulting Engineers and TNO, Nutrition and Food Research. Delft, The NetherlandsGoogle Scholar
  3. 3.
    Lithner D, Nordensvan I, Dave G (2012) Comparative acute toxicity of leachates from plastic products made of polypropylene, polyethylene, PVC, acrylonitrile-butadiene-styrene, and epoxy to Daphnia magna. Env Sci Pollut Res Int 19(5):1763–1772CrossRefGoogle Scholar
  4. 4.
    Pimentel MF, de Lima DP, Martins LR, Beatriz A, Santaella ST, Lotufo LV (2009) Ecotoxicological analysis of cashew nut industry effluents, specifically two of its major phenolic components, cardol and cardanol. Pan Am J Aquat Sci 4:363–368Google Scholar
  5. 5.
    Barnabé S, Brar SK, Tyagi RD, Beauchesne I, Surampalli RY (2009) Pre-treatment and bioconversion of sludge to value-added products—Fate of endocrine disrupting compounds. Sci Tot Environ 407:1471–1488CrossRefGoogle Scholar
  6. 6.
    Bui TT, Giovanoulis G, Cousins AP, Magnér J, Cousins IT, de Wit CA (2016) Human exposure, hazard and risk of alternative plasticizers to phthalate esters. Sci Total Environ 541:451–467CrossRefGoogle Scholar
  7. 7.
    Rahman M, Brazel CS (2004) The plasticizer market: an assessment of traditional plasticizers and research trends to meet new challenges. Prog Polym Sci 29:1223–1248CrossRefGoogle Scholar
  8. 8.
    Tyman JHP, Bruce IE (2004) Surfactant properties and biodegradation of polyethoxylates from phenolic lipids. J Surfactant Deterg 7:169–173CrossRefGoogle Scholar
  9. 9.
    Calò E, Greco A, Maffezzoli A (2011) Effects of diffusion of a naturally-derived plasticizer from soft PVC. Polym Degrad Stab 96:784–789CrossRefGoogle Scholar
  10. 10.
    Menon ARR, Visconte LLY (2006) Studies on blends of polychloroprene and polybutadiene rubber containing phosphorylated cardanol prepolymer: melt rheology, cure characteristics, and mechanical properties. J Appl Polym Sci 102(4):3195–3200CrossRefGoogle Scholar
  11. 11.
    Menon ARR, Pillai CKS, Nando GB (1994) Chemical cross link density and network structure of natural rubber vulcanizates modified with phosphorylated cardanol prepolymer. J Appl Polym Sci 51:2157–2164CrossRefGoogle Scholar
  12. 12.
    Vikram T, Nando GB (2007) Synthesis and characterization of cardanol-grafted natural rubber—The solution technique. J Appl Polym Sci 105(3):1280–1288CrossRefGoogle Scholar
  13. 13.
    Menon ARR, Pillai CKS, Nando GB (1998) Modification of natural rubber with phosphatic plasticizers: a comparison of phosphorylated cashew nut shell liquid prepolymer with 2-ethyl hexyl diphenyl phosphate. Eur Polym J 34:923–929CrossRefGoogle Scholar
  14. 14.
    Menon ARR, Pillai CKS, Nando GB (1999) Cure characteristics and physico-mechanical properties of natural rubber modified with phosphorylated cashew nut shell liquid prepolymer—A comparison with aromatic oil. J Appl Polym Sci 73:813–818CrossRefGoogle Scholar
  15. 15.
    Mohapatra S, Nando GB (2014) Cardanol: a green substitute for aromatic oil as a plasticizer in natural rubber. RSC Adv 4:15406–15418CrossRefGoogle Scholar
  16. 16.
    Mohapatra S, Nando GB (2013) Chemical modification of natural rubber in the latex stage by grafting cardanol, a waste from the cashew industry and a renewable resource. Ind Eng Chem Res 52:5951–5957CrossRefGoogle Scholar
  17. 17.
    Bhunia HP, Jana RN, Basak A, Lenka S, Nando GB (1998) Synthesis of polyurethane from cashew nut shell liquid (CNSL), a renewable resource. J Polym Sci Part A 36:391–400CrossRefGoogle Scholar
  18. 18.
    Balachandran VS, Jadhav SR, Pradhan P, Carlo SD, John G (2010) Adhesive vesicles through adaptive response of a biobased surfactant. Angew Chem Int Ed Engl 49(3):9509–9512CrossRefGoogle Scholar
  19. 19.
    Greco A, Brunetti D, Renna G, Mele G, Maffezzoli A (2010) Plasticizer for poly(vinyl chloride) from cardanol as a renewable resource material. Polym Degrad Stab 95:2169–2174CrossRefGoogle Scholar
  20. 20.
    Kim DG, Kang H, Choi YS, Han S, Lee JC (2013) Photo-cross-linkable star-shaped polymers with poly (ethylene glycol) and renewable cardanol side groups: synthesis, characterization and application to antifouling coatings for filtration membranes. Polym Chem 4:5065–5073CrossRefGoogle Scholar
  21. 21.
    Puangmalee S, Petsom A, Thamyongkit P (2009) A porphyrin derivative from cardanol as a diesel fluorescent marker. Dyes Pigment 82(1):26–30CrossRefGoogle Scholar
  22. 22.
    Pizzi A (2006) Recent developments in eco-efficient bio-based adhesives for wood bonding: opportunities and issues. Adhes Sci Technol 20:829–846CrossRefGoogle Scholar
  23. 23.
    Aggarwal LK, Thapliyal PC, Karade SR (2007) Anticorrosive properties of the epoxy-cardanol resin based paints. Prog Org Coat 59:76–80CrossRefGoogle Scholar
  24. 24.
    Suresh KI (2013) Rigid polyurethane foams from cardanol: synthesis, structural characterization, and evaluation of polyol and foam properties. ACS Sustain Chem Eng 1:232–242CrossRefGoogle Scholar
  25. 25.
    Calò E, Maffezzoli A, Mele G, Martina F, Mazzetto SE, Tarzia A, Stifani C (2007) Synthesis of a novel cardanol-based benzoxazine monomer and environmentally sustainable production of polymers and biocomposites. Green Chem 9:754–759CrossRefGoogle Scholar
  26. 26.
    Samantarai S, Mahata D, Nag A, Nando GB, Das NC (2017) Functionalization of acrylonitrile butadiene rubber with meta-pentadecenyl phenol, a multifunctional additive and a renewable resource. Rubber Chem Technol 90(4):683–698CrossRefGoogle Scholar
  27. 27.
    Samantarai S, Nag A, Singh N, Dash D, Nando GB, Das NC (2019) Physico-mechanical and dynamic mechanical properties of meta-pentadecenyl phenol functionalized acrylonitrile–butadiene rubber nanoclay composites. Rubber Chem Technol. Google Scholar
  28. 28.
    Bhunia HP, Nando GB, Chaki TK, Basak A, Lenka S, Nayak PL (1999) Synthesis and characterization of polymers from cashew nut shell liquid (CNSL), a renewable resource II. Synthesis of polyurethanes. Eur Polym J 35(8):1381–1391CrossRefGoogle Scholar
  29. 29.
    Bhunia HP, Nando GB, Basak A, Lenka S, Nayak PL (1999) Synthesis and characterization of polymers from cashew nut shell liquid (CNSL), a renewable resource III. Synthesis of a polyether. Eur Polym J 35(9):1713–1722CrossRefGoogle Scholar
  30. 30.
    Bhunia HP, Basak A, Chaki TK, Nando GB (2000) Synthesis and characterization of polymers from cashew nut shell liquid (CNSL), a renewable resource V. Synthesis of copolyester. Eur Polym J 36(6):1157–1165CrossRefGoogle Scholar
  31. 31.
    Voirin C, Caillol S, Sadavarte NV, Tawade BV, Boutevin B, Wadgaonkar PP (2014) Functionalization of cardanol: towards biobased polymers and additives. Polym Chem 5:3142–3162CrossRefGoogle Scholar
  32. 32.
    Menon ARR (1997) Flame retardant characteristics of natural rubber modified with a bromo derivative of phosphorylated cashew nut shell liquid. J Fire Flam 15(1):3–13Google Scholar
  33. 33.
    Ravichandran S, Bouldin RM, Kumar J, Nagarajan RA (2011) A renewable waste material for the synthesis of a novel non-halogenated flame retardant polymer. J Clean Prod 19(5):454–458CrossRefGoogle Scholar
  34. 34.
    Choi YS, Kim KH, Kim DG, Kim HJ, Cha SH, Lee JC (2014) Synthesis and characterization of self-cross-linkable and bactericidal methacrylate polymers having renewable cardanol moieties for surface coating applications. RSC Adv 4:41195–41203CrossRefGoogle Scholar
  35. 35.
    Sharma P, Shukla S, Lochab B, Kumar D, Kumar Roy P (2014) Microencapsulated cardanol derived benzoxazines for self-healing applications. Mater Lett 133:266–268CrossRefGoogle Scholar
  36. 36.
    Wang X, Kalali EN, Wang DY (2015) Renewable cardanol-based surfactant modified layered double hydroxide as a flame retardant for epoxy resin. ACS Sustain Chem Eng 3(12):3281–3290CrossRefGoogle Scholar
  37. 37.
    Mehat NM, Kamaruddin S (2012) Quality control and design optimization of plastic product using Taguchi method: a comprehensive review. Int J Plast Technol 16:194–209CrossRefGoogle Scholar
  38. 38.
    Samantarai S, Nag A, Singh N, Dash D, Basak A, Nando GB, Das NC (2018) Chemical modification of nitrile rubber in the latex stage by functionalizing phosphorylated cardanol prepolymer: a bio-based plasticizer and a renewable resource. J Elast Plast. Google Scholar
  39. 39.
    Mallick RL, Kumari S, Singh N, Sonkar VK, Dash D (2015) Prion protein fragment (106–126) induces prothrombotic state by raising platelet intracellular calcium and microparticle release. Cell Calcium 57(4):300–315CrossRefGoogle Scholar
  40. 40.
    Mahanta AK, Mittal V, Singh N, Dash D, Malik S, Kumar M, Maiti P (2015) Polyurethane-grafted Chitosan as new biomaterials for controlled drug delivery. Macromolecules 48:2654–2666CrossRefGoogle Scholar
  41. 41.
    Singh SK, Singh MK, Nayak MK, Kumari S, Shrivastava S, Gracio JA (2011) Thrombus inducing property of atomically thin graphene oxide sheets. ACS Nano 5:4987–4996CrossRefGoogle Scholar
  42. 42.
    Radomski A, Jurasz P, Alonso-Escolano D, Drews M, Morandi M, Malinski T (2005) Nanoparticle-induced platelet aggregation and vascular thrombosis. Br J Pharmacol 146:882–893CrossRefGoogle Scholar
  43. 43.
    Bihari P, Holzer M, Praetner M, Fent V, Lerchenberger M, Reichel CA, Rehberg M, Lakatos S, Krombach F (2010) Single-walled carbon nanotubes activate platelets and accelerate thrombus formation in the microcirculation. Toxicology 269:148–154CrossRefGoogle Scholar
  44. 44.
    Semberova J, Lacerda SHDP, Simakova O, Holada K, Gelderman MP, Simak J (2009) Carbon nanotubes activate blood platelets by inducing extracellular Ca2+ influx sensitive to calcium entry inhibitors. Nano Lett 9:3312–3317CrossRefGoogle Scholar
  45. 45.
    Devasagayam TPA, Tilak JC, Boloor KK, Sane KS, Ghaskabdi SS, Lele RD (2004) Free radicals and antioxidants in human health: current status and future prospects. J Assoc Physicians India 52:794–804Google Scholar
  46. 46.
    Krötz F, Sohn HY, Pohl U (2004) Reactive oxygen species: players in the platelet game. Arterioscler Thromb Vasc Biol 24:1988–1996CrossRefGoogle Scholar
  47. 47.
    Jackson SP (2011) Arterial thrombosis—Insidious, unpredictable and deadly. Nat Med 17:1423–1436CrossRefGoogle Scholar

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© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Rubber Technology CentreIndian Institute of Technology, KharagpurKharagpurIndia
  2. 2.Department of ChemistryIndian Institute of Technology, KharagpurKharagpurIndia
  3. 3.Department of BiochemistryIMS, Banaras Hindu UniversityVaranasiIndia

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