In the present work, an attempt has been made to develop cow manure carbon-reinforced hybrid biophenol-based benzoxazine composites for antifouling coating applications. Bio-based benzoxazine with unsymmetrical molecular structure was synthesized using the mixture of a combination of cardanol and eugenol with diaminodiphenyl methane and paraformaldehyde, and the hybrid-benzoxazine obtained was characterized using different analytical techniques, viz., Fourier transform infrared, nuclear magnetic resonance and MALDI mass. Bio-based benzoxazine was further reinforced with varying weight percentages (1, 3 and 5 wt%) of biocarbon derived from cow manure to obtain hybrid composite coatings. The hybrid benzoxazine matrix and composites were studied for their thermal behaviour, contact angle (CA), morphology, corrosion-resistant behaviour and antifouling character to utilize them as coatings materials for different industrial applications. Results obtained from different studies inferred that the biocarbon-reinforced composites possess an enhanced value of glass transition temperature (249°C), high char yield (38.4%), improved CA (105.6°), higher efficiency of corrosion protection against mild steel surface (98%) and improved antimicrobial activity.
ArzaCRFroimowiczPIshidaH, Smart chemical design incorporating umbelliferone as natural renewable resource toward the preparation of thermally stable thermosets materials based on benzoxazine chemistry. RSC Adv2015; 5: 97855–97861.
2.
PuchotLVergePFouquetT, et al.Breaking the symmetry of dibenzoxazines: a paradigm to tailor the design of bio-based thermosets. Green Chem2016; 18: 3346–3353.
3.
HimejimaMKuboI. Antibacterial agents from the cashew Anacardium occidentale (Anacardiaceae) nut shell oil. J Agric Food Chem1991; 39: 418–421.
4.
RemaudGSMartinY-LMartinGG, et al.Detection of sophisticated adulterations of natural vanilla flavors and extracts: application of the SNIF-NMR method to vanillin and p-hydroxybenzaldehyde. J Agric Food Chem1997; 45: 859–866.
5.
RojoLVazquezBParraJ, et al.From natural products to polymeric derivatives of “eugenol”: a new approach for preparation of dental composites and orthopedic bone cements. Biomacromolecules2006; 7: 2751–2761.
6.
PillaiSPMenonSRMitscherLA, et al.Umbelliferone analogues and their potential to inhibit benzo(a)pyrene- and hydrogen peroxide-induced mutations. J Nat Prod1999; 62: 1358–1362.
7.
EkiertHKwiecienISzopaA, et al.Possibilities of arbutin production using plant biotechnology methods. Pol J Cosmetol2012; 15: 151–162.
8.
CraigJCWallerCWBilletsS, et al.New GLC analysis of urushiol congeners in different plant parts of poison ivy, toxicodendron radicans. J Pharm Sci1978; 67: 483–485.
9.
KaurCKapoorHC. Anti-oxidant activity and total phenolic content of some Asian vegetables. Int J Food Sci Technol2002; 37: 153–161.
10.
BonnaudLCholletBDumasL, et al.High-performance bio-based benzoxazines from enzymatic synthesis of diphenols. Macromol Chem Phys2019; 220: 1800312–1800322.
11.
MaH-XXuZ-BQiuJ-J, et al.Synthesis of artificial urushi via ring-opening reaction of benzoxazine with renewable cardanol. Polymer2017; 132: 41–50.
12.
ChengCZhangXChenX, et al.Self-healing polymers based on eugenol via combination of thiolene and thiol oxidation reactions. J Polym Res2016; 23: 1–12.
13.
BoronatTFombuenaVGarcia-SanogueraD, et al.Development of a biocomposite based on green polyethylene biopolymer and eggshell. Mater Des2015; 68: 177–185.
14.
NieSWuWPanY, et al.Studies on intumescent flame retardant polypropylene composites based on biodegradable wheat straw. Fire Mater2018; 42: 703–709.
15.
RamdaniNWangJHeX-Y, et al.Effect of crab shell particles on the thermomechanical and thermal properties of polybenzoxazine matrix. Mater Desig2014; 61: 1–7.
16.
DasRKarumbaiahKM. Biodegradable polyester-based blends and composites: manufacturing, properties, and applications. Biodegradable Polyesters2015; 13: 321–340.
17.
ZainiMAAOkayamaRMachidaM. Adsorption of aqueous metal ions on cattle-manure-compost based activated carbons. J Hazard Mater2009; 170: 1119–1124.
18.
BhattacharjyaDYuJ-S. Activated carbon made from cow dung as electrode material for electrochemical double layer capacitor. J Power Sources2014; 262: 224–231.
19.
SweetenJMAnnamalaiKThienB, et al.Co-firing of coal and cattle feedlot biomass (FB) fuels. Part I. Feedlot biomass (cattle manure) fuel quality and characteristics. Fuel2003; 82: 1167–1182.
20.
MegiattoJDOliveiraFBRosaDS, et al.Renewable resources as reinforcement of polymeric matrices: composites based on phenolic thermosets and chemically modified sisal fibers. Macromol Bio2007; 7: 1121–1131.
21.
ShenXDaiJLiuY, et al.Synthesis of high performance polybenzoxazine networks from bio-based furfurylamine: furan vs benzene ring. Polymer2017; 122: 258–269.
22.
ZhangZLiHYangY, et al.Cow dung-derived nitrogen-doped carbon as a cost effective, high activity, oxygen reduction electrocatalyst. RSC Adv2015; 5: 27112–27119.
23.
WeiJLinZHeZ, et al.Bagasse activated carbon with TETA/TEPA modification and adsorption properties of CO2. Water Air Soil Pollution2017; 228.DOI. org/10.1007/s11270-017-3317-5.
24.
GhasemiMMashhadiSAsifM, et al.Microwave-assisted synthesis of tetraethylenepentamine functionalized activated carbon with high adsorption capacity for Malachite green dye. J Mol Liq2016; 213: 317–325.
25.
SelvarajVJayanthiKPLakshmikandhanT, et al.Development of polybenzoxazine/TSBA-15 composite from renewable resource cardanol for low k applications. RSC Adv2015; 5: 48898–48907.
26.
ShuaiZQichaoRQiangF, et al.Thermal responsiveness of hydrogen bonding and dielectric property of polybenzoxazines with different Mannich bridge structures. Polymer2019; 175: 302–309.
27.
KimH-DHatsuoI. A study on hydrogen-bonded network structure of polybenzoxazines. J Phys Chem A2002; 106: 3271–3280.
28.
HanLZhangKIshidaH, et al.Study of the effects of intramolecular and intermolecular hydrogen-bonding systems on the polymerization of amide-containing benzoxazines. Macromol Chem Phys2017; 218: 1600562–1600571.
29.
ShamilSLeïlaBCamiloZ, et al.Positive effect of functional side groups on the structure and properties of benzoxazine networks and nanocomposites. Polym Chem2019; 10: 5251–5264.
30.
AhmadJALewisSClarkR, et al.Vapor phase GC-IR identification of regioisomeric N-methoxybenzyl-4- substituted-2,5-dimethoxyphenethylamines (NBOMe). Forens Chem2019; 16: 100181–100186.
31.
ThirukumaranPParveenSASarojadeviM. Synthesis and copolymerization of fully biobased benzoxazines from renewable resources. ACS Sustainab Chem Eng2014; 2: 2790–2801.
32.
SelvarajVJayanthiKPAlagarM, Synthesis and characterization of cardanol based fluorescent composite for optoelectronic and antimicrobial applications. Polymers2017; 108: 449–461.
33.
KiskanBKozBYagciY. Synthesis and characterization of fluid 1,3-benzoxazine monomers and their thermally activated curing. J Polym Sci Part A: Polym Chem2009; 47: 6955–6961.
34.
AgagTAnSYIshidaH. 1,3-Bis(benzoxazine) from cashew nut shell oil and diaminodiphenyl methane and its composites with wood flour. J Appl Polym Sci2012; 127: 2710–2714.
35.
AbarroGJPodschunJDiazLJ, et al.Benzoxazines with enhanced thermal stability from phenolated organosolv lignin. RSC Adv2016; 6: 107689–107698.
36.
TakeichiTThongpradithSKawauchiT. Copolymers of vinyl-containing benzoxazine with vinyl monomers as precursors for high performance thermosets. Molecules2015; 20: 6488–6503.
37.
RimdusitSIshidaH. Synergism and multiple mechanical relaxations observed in ternary systems based on benzoxazine, epoxy, and phenolic resins. J Polym Sci Part B: Polym Phys2000; 38: 1687–1698.
38.
BuketABarisKYusufY. Cyanuric chloride as a potent catalyst for the reduction of curing temperature of benzoxazines. Polym Chem2020; 11: 1025–1032.
39.
WangXGaoYWangW, et al.Different amine-functionalized poly(diphenyl substituted acetylenes) from the same precursor. Polym Chem2016; 7: 5312–5321.
40.
GhaniNAYusufNYMIsahakWNRW, et al.Modification of activated carbon from biomass nypa and amine functional groups as carbon dioxide adsorbent. J Phys Sci2017; 28: 227–240.
41.
GoscianskaJFathyNAAboeleninRMM. Adsorption of solophenyl red 3BL polyazo dye onto amine-functionalized mesoporous carbons. J Col Interf Sci2017; 505: 593–604.
42.
ZeidAOthmanALYilmazE, et al.Triethylenetetramine modified multiwalled carbon nanotubes for the efficient preconcentration of Pb(ii), Cu(ii), Ni(ii) and Cd(ii) before FAAS detection. RSC Adv2015; 5: 106905–106911.
43.
ShuJChengSXiaH, et al.Copper loaded on activated carbon as an efficient adsorbent for removal of methylene blue. RSC Adv2017; 7: 14395–14405.
44.
Qi-chaoRQiaoTCaoL, et al.Investigation of processing, thermal, and mechanical properties of a new composite matrix-benzoxazine containing aldehyde group. Polym Adv Technol2010; 21: 170–176.
45.
LiuY-LYuJ-MChouC-I. Preparation and properties of novel benzoxazine and polybenzoxazine with maleimide groups. J Polym Sci Part A: Polym Chem2004; 42: 5954–5963.
46.
KimH-DIshidaH. A study on hydrogen-bonded network structure of polybenzoxazines. J Phys Chem A2002; 106: 3271–3280.
47.
MengFIshidaHLiuX. Introduction of benzoxazine onto the graphene oxide surface by click chemistry and the properties of graphene oxide reinforced polybenzoxazine nanohybrids. RSC Adv2014; 4: 9471–9475.
48.
LorjaiPWongkasemjitSChaisuwanT. Preparation of polybenzoxazine foam and its transformation to carbon foam. Mater Sci Eng A2009; 527: 77–84.
49.
HongliXWenliZZaijunL, et al.Hybrid polybenzoxazine with tunable properties. RSC Adv2013; 3: 3677–3682.
50.
LlorensEArmelinEPerez-MadrigalMDM, et al.Nanomembranes and nanofibers from biodegradable conducting polymers. Polymer2013; 5: 1115–1157.
51.
AleshinA. Quasi-one-dimensional transport in conducting polymer nanowires. Phys Solid State2007; 49: 2015–2033.
52.
ThirukumaranPShakilaAMuthusamyS, et al.Synthesis and characterization of novel bio-based benzoxazines from eugenol. RSC Adv2014; 4: 7959–7986.
53.
SharmaPKumarDPrasunK, et al.Poly(benzoxazine-co-urea): a solventless approach towards the introduction of alternating urea linkages in polybenzoxazine. Chem Select2017; 2: 5372–5377.
54.
LekesizTOHacalogluJ, Effects of curing on structure and thermal characteristics of polybenzoxazine based on p-nitroaniline. Polym Degrad Stabil2016; 129: 363–373.
55.
LinCChangSLShenTY, et al.Flexible polybenzoxazine thermosets with high glass transition temperatures and low surface free energies. Polym Chem2012; 3: 935–945.
56.
SasikumarRPadmanathanNAlagarM. Design of hydrophobic polydimethylsiloxane and polybenzoxazine hybrids for interlayer low k dielectrics. New J Chem2015; 39: 3995–4008.
57.
Chi-HaoCTsao-ChengHChih-WeiP, et al.Novel anticorrosion coatings prepared from polyaniline/graphene composites. Carbon2012; 50: 5044–5051.
58.
ZhouCLinJLuX, et al.Enhanced corrosion resistance of polybenzoxazine coatings by epoxy incorporation. RSC Adv2016; 6: 28428–28434.
59.
KrishnadeviKSelvarajVPrasannaD. Thermal, mechanical and antibacterial properties of cyclophosphazene incorporated benzoxazine blended bismaleimide composites. RSC Adv2015; 5: 913–921.
60.
ChengHMaoLWangL, et al.Bidirectional regulation of zinc embedded titania nanorods: antibiosis and osteoblastic cell growth. RSC Adv2015; 5: 14470–14481.
61.
WangJChenYChenY, et al.Fabrication and characterization of superhydrophilic and antibacterial surfaces by silver nanoparticle self-assembly. Col Polym Sci2017; 295: 2191–2196.
62.
LoskillPHählHThewesN, et al.Influence of the subsurface composition of a material on the adhesion of Staphylococci. Langmuir2012; 28: 7242–7248.
63.
ChenYHarapanahalliAKBusscherHJ, et al.Nanoscale cell wall deformation impacts long-range bacterial adhesion forces on surfaces. Appl Environ Microbiol2013; 80: 637–643.
64.
LiangXOuXZhengF, et al.Surface modification of Na3V2(PO4)3 by nitrogen and sulfur dual-doped carbon layer with advanced sodium storage property. ACS Appl Mater Interf2017; 9: 13151–13162.
65.
NordinNIMSaidSMRamliR, et al.Impact of aluminium addition on the corrosion behaviour of Sn–1.0Ag–0.5Cu lead-free solder. RSC Adv2015; 5: 99058–99064.
66.
ZachariahSChuoT-WLiuY-L. Crosslinked polybenzoxazine coatings with hierarchical surface structures from a biomimicking process exhibiting high robustness and anticorrosion performance. Polymer2018; 155: 168–176.
67.
ChangluZXinLZhongX, et al.Polybenzoxazine/SiO2 nanocomposite coatings for corrosion protection of mild steel. Corros Sci2014; 80: 269–275.
68.
EugeneBCChristopher AlCDLPatrickGT, et al.Superhydrophobic rubber-modified polybenzoxazine/SiO2 nanocomposite coating with anticorrosion, anti-ice, and superoleophilicity properties. Ind Eng Chem Res2017; 56(6): 1485–1497.
69.
LinS-CWuC-SYehJ-M, et al.Reaction mechanism and synergistic anticorrosion property of reactive blends of maleimide-containing benzoxazine and amine-capped aniline trimer. Polym Chem2014; 5: 4235–4244.
