Abstract
A series of chitosan derivatives, namely polydiethylamino-ethylmethacrylate-chitosan-graft-copolymer (chitosan-g-DEAEMA), polycarboxy-chitosan-graft copolymer (chitosan-g-COOH), polyvinyl alcohol chitosan-graft-copolymer (chitosan-g-VOH), and carboxymethyl-chitosan (CM-chitosan), were synthesized and investigated as antioxidants for natural rubber (NR) and acrylonitrile butadiene rubber (NBR) mixes and vulcanizates to increase their durability. The rheometric characteristics of the rubber mixes were determined using an oscillating disc rheometer. The physico-mechanical properties of the rubber vulcanized were measured before and after exposure to thermal oxidative aging. It was found that the CM-chitosan had an accelerating effect on the curing process of NR and NBR. Also, the investigated polymers enhanced the properties of rubbers (NR and NBR) especially after ageing up to 7 days compared with commercial antioxidants, such as phenyl ß-naphthylamine (PßN) and N-isopropel-Nphenyl-p-phenylene diamine (IPPD) which are used in the rubber industry. After ageing, the retained values of tensile strength, modulus at 100 % strain, and elongation at break were improved. The optimum concentration of the investigated compounds used to give good properties was found to be 1–2 parts per 100 of rubber (phr). In addition, these prepared polymers showed a decrease in the equilibrium swelling of rubber in toluene which is the proper solvent and consequently increases the crosslink density for rubbers.
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References
S. Al-Malaika, Mechanisms of antioxidant action and stabilization technology—the aston experience. Polym. Degrad. Stab. 34(1), 1–36 (1991)
D. Barnard, P.M. Lewis, In Natural Rubber Science and Technology, ed by A.D. Roberts. Oxidative Ageing (Oxford University Press, Oxford, 1988) pp. 621–675
L.V. Abad, L.S. Relleve, C.T. Aranilla, A.K. Aliganga, C.M. San Diego, A.M. dela Rosa, Natural antioxidants for radiation vulcanization of natural rubber latex. Polym. Degrad. Stab. 76, 275–279 (2002)
J. Pospisil, Chain-breaking stabilizers in polymers: the current status. Polym. Degrad. Stab. 49, 99–110 (1995)
J.Q. Pan, N.C. Liu, W.W.Y. Lau, Synthesis and properties of new polymerizable antioxidants. Polym. Degrad. Stab. 62, 315–322 (1998)
A.A. Wazzan, M.N. Ismail, M.A. Abd El-Ghaffar, Evaluation of some polyaromatic amines as antirads and antifatigue agents in SBR vulcanizates. Int. J. Polym. Anal. Charact. 10(1), 57–69 (2005)
E.A.M. Youssef, D. El-Nashaar, M.A. Abd El-Ghaffar, Evaluation of itaconic acid aromatic diamine adducts as novel antioxidants polymers. Part 1: evaluation as antioxidants for natural rubber vulcanizates. Pigm. Resin Technol. 32, 219–234 (2003)
R.N. Datta, N.M. Huntink, S. Datta, A.G. Talma, Rubber vulcanizates degradation and stabilization. Rubber Chem. Technol. 80, 436–480 (2007)
N.M. Huntink, R.N. Datta, J.W.M. Nordermeer, Addressing durability of rubber compounds. Rubber Chem. Technol. 77, 476–511 (2004)
G.A.M. Nawwar, E.M.A. Yakout, M.S.A. El-Sadiek, S.H. Salwa, El-Sabbagh, Synthesis and evaluation of new antioxidants for styrene butadiene rubber. Pigm. Resin Technol. 40(6), 399–409 (2011)
E.M.A. Yakout, S.H. El-Sabbagh, New uracil derivatives as antioxidants for natural rubber. Pigm. Resin Technol. 36(4), 224–234 (2007)
G.A.M.Nawwar, S.H. El-Sabbagh and M. Email, Method for improvement Rheological and physico-mechanical properties of rubber utilizing lignin (from rice straw), (2009), Egyptian Patent No. 258
N.A. Abdelwahab, D.E. El-Nashar, M.A. Abd El-Ghaffar, Polyfuran, polythiophene and their blend as novel antioxidants for styrene-butadiene rubber vulcanizates. Mater. Des. 32, 238–245 (2011)
G.A.F. Roberts, Chitin Chemistry (The Macmillan Press, Basingstoke, 1992)
P.M. Visakh, M. Monti, D. Puglia, M. Rallini, C. Santulli, F. Sarasini, S. Thomas, J.M. Kenny, Mechanical and thermal properties of crab chitin reinforced carboxylated SBR composites. Express Polym. Lett. 6(5), 396–409 (2012)
S.M. El-Sawy, Y.M. Abu-Ayana, F.A. Abdel-Mohdy, Some chitin/chitosan derivatives for corrosion protection and waste water treatments. Anti-Corros. Methods Mater 48, 227–235 (2001)
A.L. Vogel, Elementary Practical Organic Chemistry. Part (3). Quantitative Organic Chemistry (2nd ed) (Longman Group Ltd., London, 1995), p. 652
A.L. Vogel, Elementary Practical Organic Chemistry. Part (3). Quantitative Organic Chemistry (2nd ed) (Longman Group Ltd., London, 1995), pp. 824–827
P.P. Flory, Principles of Polymer Chemistry (Cornell University, Ithaca, 1953)
M.N. Ismail, A.I. Khalaf, Styrene–butadiene rubber/graphite powder composites: rheometrical Physicomechanical, and morphological properties. J. Appl. Polym. Sci. 120, 298–304 (2011)
M.A. Abd El-Ghaffar, D.E. El-Nashar, E.A.M. Youssef, Maleic acid/phenylene diamine adducts as new antioxidant amide polymers for rubber (NR and SBR) vulcanizates. Polym. Degrad. Stab. 82(1), 47–57 (2003)
F.M. Helaly, W.M. Darwish, M.A. Abd El-Ghaffar, Effect of some polyaromatic amines on the properties of NR and SBR vulcanizates. Polym. Degrad. Stab. 64, 251–257 (1998)
A. Gregorova, B. Kosikova, R. Moravcik, Stabilization effect of lignin in natural rubber. Polym. Degrad. Stab. 91, 229–233 (2006)
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Khalaf, A.I., Helaly, F.M. & El-Sawy, S.M. Effect of chitosan derivatives as rubber antioxidants for increasing durability. Res Chem Intermed 40, 1383–1401 (2014). https://doi.org/10.1007/s11164-013-1046-y
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DOI: https://doi.org/10.1007/s11164-013-1046-y