Chemical modification of nitrile rubber in the latex stage by functionalizing phosphorylated cardanol prepolymer: A bio-based plasticizer and a renewable resource
Restricted accessResearch articleFirst published online March, 2019
Chemical modification of nitrile rubber in the latex stage by functionalizing phosphorylated cardanol prepolymer: A bio-based plasticizer and a renewable resource
The present investigation deals with the functionalization of acrylonitrile butadiene rubber (NBR) by chemically grafting phosphorylated cardanol prepolymer (PCP) onto its backbone chain. The grafting of PCP onto NBR was accomplished in the latex stage successfully using benzoyl peroxide as the free radical initiator. The functionalized NBR (PCP-g-NBR) is characterized by ultraviolet–visible spectroscopy, Fourier transform infrared spectroscopy, nuclear magnetic resonance spectroscopy, and gel permeation chromatography. PCP-g-NBR exhibited an increase in molecular weight (4.4%) with an increase in the polydispersity. The grafting parameters have been optimized using “Taguchi L9 table” and the optimum conditions were found to be “3 phr of initiator concentration, 15 phr of the PCP concentration, reaction temperature of 70°C and reaction time of 6 h.” The percentage grafting and grafting efficiency were calculated to be 7.28 and 80.37%, respectively, under optimum processing conditions. The PCP-g-NBR exhibited a reduction in Wallace plasticity number as well as the Mooney viscosity and an enhanced plasticity retention index (PRI) as compared to neat NBR. The rheological measurements exhibited a higher flow behavior index for PCP-g-NBR than the NBR itself. Differential scanning calorimetry and dynamic mechanical analysis results exhibited a decrease in glass transition temperature on functionalization of NBR confirming enhanced plasticization. Thermogravimetric analysis results displayed an increase in thermal stability of the functionalized NBR than that of virgin NBR. The physico-mechanical properties of the PCP-g-NBR vulcanizates were at par with or even better than the neat NBR vulcanizates. 3-(4,5-Dimethylthiazol-2yl)-2,5-diphenyltetrazolium bromide assay and hemolysis studies indicated NBR and PCP-g-NBR are nontoxic and biocompatible.
TymanJHPBruceIE. Surfactant properties and biodegradation of polyethoxylates from phenolic lipids. J Surfact Deterg2004; 7: 169–173.
2.
VikramTNandoGB. Synthesis and characterization of cardanol-grafted natural rubber—the solution technique. J Appl Polym Sci2007; 105: 1280–1288.
3.
MenonARRPillaiCKSNandoGB. 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 Sci1999; 73: 813–818.
4.
MenonARRPillaiCKSNandoGB. Modification of natural rubber with phosphatic plasticizers: a comparison of cashew nut shell liquid prepolymer with 2-ethyl hexyl diphenyl phosphate. Eur Polym J1998; 34: 923–929.
5.
MenonARRPillaiCKSNandoGB. Chemical cross link density and network structure of natural rubber vulcanizates modified with phosphorylated cardanol prepolymer. J Appl Polym Sci1994; 51: 2157–2164.
6.
MenonARRVisconteLLY. Studies on blends of polychloropene and polybutadiene rubber containing phosphorylated cardanol prepolymer: melt rheology, cure characteristics, and mechanical properties. J Appl Polym Sci2006; 102: 3195–3200.
7.
GrecoABrunettiDRennaG. Plasticizer for poly(vinyl chloride) from cardanol as a renewable resource material. Polym Degrad Stab2010; 95: 2169–2174.
8.
CalòEGrecoAMaffezzoliA. Effects of diffusion of a naturally-derived plasticizer from soft PVC. Polym Degrad Stab2011; 96: 784–789.
9.
RahmanMBrazelCS. The plasticizer market: an assessment of traditional plasticizers and research trends to meet new challenges. Prog Polym Sci2004; 29(12): 1223–1248.
10.
BarnabéSBrarSKTyagiRD. Pre-treatment and bioconversion of wastewater sludge to value-added products—fate of endocrine disrupting compounds. Sci Tot Environ2009; 407: 1471–1488.
11.
BuiTTGiovanoulisGCousinsAP. Human exposure, hazard and risk of alternative plasticizers to phthalate esters. Sci Total Env2016; 541: 451–467.
12.
Diego LomonacoDMaiaFJNClementeCS. Thermal studies of new biodiesel antioxidants synthesized from a naturally occurring phenolic lipid. Fuel2012; 97: 552–559.
13.
Castro DantasTNDantasMSGDantas NetoAA. Novel antioxidants from cashew nut shell liquid applied to gasoline stabilization. Fuel2003; 82(12): 1465–1469.
14.
FaçanhaMARMazzettoSECariocaJOB. Evaluation of antioxidant properties of a phosphorated cardanol compound on mineral oils (NH10 and NH20). Fuel2007; 86(15): 2416–2421.
15.
BalachandranVSJadhavSRPradhanP. Adhesive vesicles through adaptive response of a biobased surfactant. Angew Chem Int Ed Engl2010; 49(3): 9509–9512.
16.
ChoiYSKimKHKimDG. Synthesis and characterization of self-cross-linkable and bactericidal methacrylate polymers having renewable cardanol moieties for surface coating applications. RSC Adv2014; 4: 41195–41203.
17.
KimDGKangHChoiYS. 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 Chem2013; 4: 5065–5073.
18.
PuangmaleeSPetsomAThamyongkitP. A porphyrin derivative from cardanol as a diesel fluorescent marker. Dyes and Pigm2009; 82(1): 26–30.
19.
PizziA. Recent developments in eco-efficient bio-based adhesives for wood bonding: opportunities and issues. Adhesion Sci Technol2006; 20: 829–846.
20.
AggarwalLKThapliyalPCKaradeSR. Anticorrosive properties of the epoxy-cardanol resin based paints. Prog Org Coat2007; 59: 76–80.
21.
SureshKI. Rigid polyurethane foams from cardanol: synthesis, structural characterization, and evaluation of polyol and foam properties. ACS Sustainable Chem Eng2013; 1: 232–242.
22.
MenonARR. Flame retardant characteristics of natural rubber modified with a bromo derivative of phosphorylated cashew nut shell liquid. J Fire Flam1997; 15(1): 3–13.
23.
CalòEMaffezzoliAMeleG. Synthesis of a novel cardanol-based benzoxazine monomer and environmentally sustainable production of polymers and biocomposites. Green Chem2007; 9: 754–759.
24.
IllyNFacheMMénardR. Phosphorylation of bio-based compounds: the state of the art. Polym Chem2015; 6: 6257–6291.
25.
MohapatraSNandoGB. Cardanol: a green substitute for aromatic oil as a plasticizer in natural rubber. RSC Adv2014; 4: 15406–15418.
26.
MohapatraSNandoGB. 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 Res2013; 52: 5951–5957.
27.
SamantaraiSMahataDNagA. Functionalization of acrylonitrile butadiene rubber with meta-pentadecenyl phenol, a multifunctional additive and a renewable resource. Rubber Chem Technol2017; 90(4): 683–698.
28.
BhuniaHPJanaRNBasakA. Synthesis of polyurethane from cashew nut shell liquid (CNSL), a renewable resource. J Polym Sci A Polym Chem1998; 36: 391–400.
29.
BhuniaHPNandoGBChakiTK. Synthesis and characterization of polymers from cashew nut shell liquid (CNSL), a renewable resource II. Synthesis of polyurethanes. Eur Polym J1999; 35(8): 1381–1391.
30.
BhuniaHPNandoGBBasakA. Synthesis and characterization of polymers from cashew nut shell liquid (CNSL), a renewable resource III. Synthesis of a polyether. Eur Polym J1999; 35(9): 1713–1722.
31.
BhuniaHPBasakAChakiTK. Synthesis and characterization of polymers from cashew nut shell liquid (CNSL), a renewable resource V. Synthesis of copolyester. Eur Polym J2000; 36(6): 1157–1165.
32.
VoirinCCaillolSSadavarteNV. Functionalization of cardanol: towards biobased polymers and additives. Polym Chem2014; 5: 3142–3162.
33.
RiosMAdSMazzettoSE. Effect of organophosphate antioxidant on the thermo-oxidative degradation of a mineral oil. J Therm Anal Calorim2013; 111(11): 553–559.
34.
RiosMAdSMazzettoSE. Thermal behavior of phosphorous derivatives of hydrogenated cardanol. Fuel Process Technol2012; 96: 1–8.
35.
RiosMADSNascimentoTLSantiagoSN. Cashew nut shell liquid: a versatile raw material utilized for synthesis of phosphorous compounds. Energy Fuels2009; 23(11): 5432–5437.
36.
RavichandranSBouldinRMKumarJ. A renewable waste material for the synthesis of a novel non-halogenated flame retardant polymer. J Clean Prod2011; 19(5): 454–458.
37.
PillaiCKSPrasadVSSudhaJD. Polymeric resins from renewable resources II. Synthesis and characterization of flame-retardant prepolymers from cardanol. J Appl Polym Sci1990; 41(9–10): 2487–2501.
38.
AntonyR. Synthesis, characterization and thermal studies of cardanol based polyphosphate esters. J Polym Sci A Polym Chem1993; 31(13): 3187–3191.
39.
HugoW. Inhibition and Destruction of the Microbial Cell. London, New York: Academic Press, 1971, p. xiii.
40.
LalithaKNagarajanS. Strongly fluorescent organogels and self-assembled nanostructures from pyrene coupled coumarin derivatives: application in cell imaging. J Mater Chem B2015; 3: 5690–5701.
41.
BalachandranVSJadhavSRVemulaPK. Recent advances in cardanol chemistry in a nutshell: from a nut to nanomaterials. Chem Soc Rev2013; 42: 427–438.
42.
VemulaPKJohnG. Crops: a green approach toward self-assembled soft materials. Acc Chem Res2008; 41: 769–782.
43.
JohnGMasudaMOkadaY. Nanotube formation from renewable resources via coiled nanofibers. Adv Mater2001; 13: 715–718.
44.
TymanJHPKozubekA. Resorcinolic lipids, the natural non-isoprenoid phenolic amphiphiles and their biological activity. Chem Rev1999; 99(1): 1–26.
45.
ChoiYSKangHKimDG. Mussel inspired dopamine and plant-based cardanol-containing polymer coatings for multifunctional filtration membranes. ACS Appl Mater Interfaces2014; 6(23): 21297–21307.
46.
KumarAVemulaPKAjayanPM. Silver nano-particle-embedded antimicrobial paints based on vegetable oil. Nat Mater2008; 7: 236–241.
47.
LomonacoDSantiagoGMPFerreiraYS. Study of technical CNSL and its main components as new green larvicides. Green Chem2009; 11: 31–33.
48.
SchneiderBUCMezaABeatrizA. Cardanol: toxicogenetic assessment and its effects when combined with cyclophosphamide. Genet Mol Biol2016; 39(2): 279–289.
49.
MehatNMKamaruddinS. Quality control and design optimization of plastic product using Taguchi method: a comprehensive review. Int J Plast Technol2012; 16: 194–209.
50.
MallickRLKumariSSinghN. Prion protein fragment (106–126) induces prothrombotic state by raising platelet intracellular calcium and microparticle release. Cell Calcium2015; 57(4): 300–315.
51.
MahantaAKMittalVSinghN. Polyurethane-grafted Chitosan as new biomaterials for controlled drug delivery. Macromolecules2015; 48: 2654–2666.
52.
SantraRNSamantarayBKBhowmickAK. In situ compatibilization of low-density polyethylene and polydimethylsiloxane rubber blends using ethylene-methyl acrylate copolymer as a compatibilzer. J Appl Polym Sci1993; 49: 1145–1158.
53.
SantraRNRoySTikkuVK. In-situ compatibilization of thermoplastic polyurethane and polydimethylsiloxane rubber by using ethylene methyl acrylate copolymer as a reactive polymeric compatibilizer. Adv Polym Technol1995; 14(1): 59–66.
BihariPHolzerMPraetnerM. Single-walled carbon nanotubes activate platelets and accelerate thrombus formation in the microcirculation. Toxicology2010; 269: 148–154.
57.
SemberovaJLacerdaSHDPSimakovaO. Carbon nanotubes activate blood platelets by inducing extracellular Ca2+ influx sensitive to calcium entry inhibitors. Nano Lett2009; 9: 3312–3317.
58.
DevasagayamTPATilakJCBoloorKK. Free radicals and antioxidants in human health: current status and future prospects. J Assoc Physicians India2004; 52: 794–804.
59.
KrötzFSohnHYPohlU. Reactive oxygen species: players in the platelet game. Arterioscler Thromb Vasc Biol2004; 24: 1988–1996.
60.
JacksonSP. Arterial thrombosis—insidious, unpredictable and deadly. Nat Med2011; 17: 1423–1436.
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