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Study on ester-amide exchange reactions between Nylon 1010 and Ethylene-vinyl acetate rubber with different metal derivatives

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Abstract

Ester-exchange reaction was a useful method to improve the compatibility of polymer blends. In this article, ester-amide exchange reaction between Nylon 1010 and Ethylene-vinyl acetate rubber (EVM) was studied in the presence of different Ti and Zn derivatives as catalysts. The chemical reactions were studied by 1H NMR. Catalytic activities of Ti(OBu)4, TiO(OOCCH3)2, ZnO and Zn(OOCCH3)2 were compared and Ti(OBu)4 showed the highest catalytic reactivity. Melt flow index (MFI) of Nylon 1010/EVM blends indicated that crosslinking and degradation took place in the reactive blends. Gel permeation chromatography (GPC) provided the evidence for the degradation behavior during melt blending. SEM images showed that the compatibility of the blends was improved at the presence of catalyst. SAXS results showed that the long period of Nylon 1010/EVM decreased after adding Ti(OBu)4, implying the formation of imperfect crystallites in Nylon 1010/EVM/Ti(OBu)4 blend.

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References

  1. Soccio M, Lotti N, Finelli L, Gazzano M, Munari A (2009) Miscibility of biodegradable poly(propylene succinate)/poly(propylene adipate) blends: Effect of the transesterification reactions. Eur Polym J 45(11):3236–3248

    Article  CAS  Google Scholar 

  2. Jafari SH, Khonakdar HA, Asadinezhad A, Häubler L, Böhme F, Komber H (2009) On the interrelationship of transreactions with thermal properties and dynamic mechanical analysis of PTT/PEN blends. Macromol Chem Phys 210(16):1291–1302

    Article  CAS  Google Scholar 

  3. Aravind I, Eichhorn KJ, Komber H, Jehnichen D, Zafeiropoulos NE, Ahn KH, Grohens Y, Stamm M, Thomas S (2009) A study on reaction-induced miscibility of poly(trimethylene terephthalate)/polycarbonate blends. J Phys Chem B 113(6):1569–1578

    Article  CAS  Google Scholar 

  4. Zhang C, Huang Y, Luo C, Jiang L, Dan Y (2013) Enhanced ductility of polylactide materials: Reactive blending with pre-hot sheared natural rubber. J Polym Res 20(4):121–129

    Article  Google Scholar 

  5. Borah JS, Chaki TK (2011) Dynamic rheological, morphology and mechanical properties of compatibilized LLDPE/EMA blends. J Polym Res 18(5):907–916

    Article  CAS  Google Scholar 

  6. Chang HH, Wu JS, Chang FC (1994) Reactive compatibilization of ABS/Nylon 6,6 blends: Effects of reactive group concentration and blending sequence. J Polym Res 1(3):235–245

    Article  CAS  Google Scholar 

  7. Hemmati M, Narimani A, Shariatpanahi H, Fereidoon A, Ahangari MG (2011) Study on Morphology, Rheology and Mechanical Properties of Thermoplastic Elastomer Polyolefin (TPO)/Carbon Nanotube Nanocomposites with Reference to the Effect of Polypropylene-grafted-Maleic Anhydride (PP-g-MA) as a Compatibilizer. Int J Polym Mater 60(6):384–397

    Article  CAS  Google Scholar 

  8. Lusinchi JM, Boutevin B, Torres N, Robin JJ (2001) In situ compatibilization of HDPE/PET blends. J Appl Polym Sci 79(5):874–880

    Article  CAS  Google Scholar 

  9. Yang ZG, Mai KC (2010) Crystallization and melting behavior of beta-nucleated isotactic polypropylene/polyamide 6 blends with maleic anhydride grafted polyethylene-vinyl acetate as a compatibilizer. Thermo Acta 511(1–2):152–158

    Article  CAS  Google Scholar 

  10. Wang YL, Hu XA, Li H, Ji X, Li ZM (2010) Polyamide-6/Poly(lactic acid) Blends Compatibilized by the Maleic Anhydride Grafted Polyethylene-Octene Elastomer. Polym-Plast Technol Eng 49(12):1241–1246

    Article  CAS  Google Scholar 

  11. Chiu FC, Lai SM, Li HC, Chen CC (2011) Characterization of nylon 6/ABS blends with and without a maleated polybutadiene as compatibilizer. J Polym Res 18(4):627–635

    Article  CAS  Google Scholar 

  12. Singh H, Gupta NK (2011) Evolution of properties in ABS/PA6 blends compatibilized by fixed weight ratio SAGMA copolymer. J Polym Res 18(6):1365–1377

    Article  CAS  Google Scholar 

  13. Harada M, Ohya T, Iida K, Hayashi H, Hirano K, Fukuda H (2007) Increased impact strength of biodegradable poly(lactic acid)/poly(butylene succinate) blend composites by using isocyanate as a reactive processing agent. J Appl Polym Sci 106(3):1813–1820

    Article  CAS  Google Scholar 

  14. Jun JB, Park JG, Kim DH, Suh KD (2001) Blends of polybutyleneterephthalate with ethylene-propylene elastomer containing isocyanate functional group. Eur Polym J 37(3):597–602

    Article  CAS  Google Scholar 

  15. Bae TY, Park KY, Kim DH, Suh KD (2001) Poly(ethylene terephthalate)/polypropylene reactive blends through isocyanate functional group. J Appl Polym Sci 81(5):1056–1062

    Article  CAS  Google Scholar 

  16. Kim DH, Park KY, Kim JY, Sum KDO (2000) Improved compatibility of high-density polyethylene/poly(ethylene terephthalate) blend by the use of blocked isocyanate group. J Appl Polym Sci 78(5):1017–1024

    Article  CAS  Google Scholar 

  17. Park SH, Park KY, Suh KD (1998) Compatibilizing effect of isocyanate functional group on polyethylene terephthalate/low density polyethylene blends. J Polym Sci Part B: Polym Phys 36(3):447–453

    Article  CAS  Google Scholar 

  18. Jeziórska R, Szadkowska A, Studziński M (2007) Compatibilization of polyolefins waste based blends by reactive modifiers with anhydride or oxazoline functional groups. Polim 52(5):371–374

    Google Scholar 

  19. Sangaj N, Mohite A, Sadasivam G, Franklin S, Guo H (2010) Oxazoline functionalized polystyrene as a compatibilizer for dispersion of organoclay in polyphenylene ether blends. J Appl Polym Sci 117(3):1718–1730

    CAS  Google Scholar 

  20. Oliveira MG, Gomes ACO, Almeida MSM, Soares BG (2004) Reactive compatibilization of NBR/EPDM blends by the combination of mercapto and oxazoline groups. Macromol Chem Phys 205(4):465–475

    Article  CAS  Google Scholar 

  21. Soares BG, Almeida MSM, Guimarães PIC (2004) The reactive compatibilization of NBR/EVA blends with oxazoline-modified nitrile rubber. Eur Polym J 40(9):2185–2194

    Article  CAS  Google Scholar 

  22. Jeziórska R (2005) Studies on reactive compatibilisation of polyamide 6/poly(butylene terephthalate) blends by low molecular weight bis-oxazoline. Polym Degrad Stab 90(2):224–233

    Article  Google Scholar 

  23. Narathichat M, Kummerlöwe C, Vennemann N, Sahakaro K, Nakason C (2012) Influence of epoxide level and reactive blending on properties of epoxidized natural rubber and nylon-12 blends. Adv Polym Technol 31(2):118–129

    Article  CAS  Google Scholar 

  24. Martin P, Maquet C, Legras R, Bailly C, Leemans L, Van Gurp M, Van Duin M (2004) Particle-in-particle morphology in reactively compatibilized poly(butylene terephthalate)/epoxide-containing rubber blends. Polymer 45(10):3277–3284

    Article  CAS  Google Scholar 

  25. Mo J, Xia L, Pan P, Shentu B, Weng Z (2013) Reactive blend of epoxy-novolac resin and epoxide-terminated low-molecular-weight poly(phenylene oxide). J Appl Polym Sci 127(6):4879–4888

    Article  CAS  Google Scholar 

  26. Yao Z, Sun JM, Wang Q, Cao K (2012) Study on Ester-Amide Exchange Reaction between PBS and PA6IcoT. Ind Eng Chem Res 51(2):751–757

    Article  Google Scholar 

  27. Zahedi P, Arefazar A (2008) Blends of polyethylene terephthalate/polycarbonate by the use of lanthanum acetyl acetonate catalyst. J Appl Polym Sci 107(5):2917–2922

    Article  CAS  Google Scholar 

  28. Soccio M, Lotti N, Finelli L, Gazzano M, Munari A (2008) Influence of transesterification reactions on the miscibility and thermal properties of poly(butylene/diethylene succinate) copolymers. Eur Polym J 44(6):1722–1732

    Article  CAS  Google Scholar 

  29. Moura I, Nogueirab R, Bounor-Legarec V, Machadoa AV (2012) Synthesis of EVA-g-PLA copolymers using transesterification reactions. Mater Chem Phys 134(1):103–110

    Article  CAS  Google Scholar 

  30. Coltelli M-B, Bianchi S, Savi S, Liuzzo V, Aglietto M (2003) Metal catalysis to improve compatibility at PO/PET blends interfaces. Macromol Symp 204(1):227–236

    Article  CAS  Google Scholar 

  31. Coltelli MB, Bianchi S, Aglietto M (2007) Poly(ethylene terephthalate) (PET) degradation during the Zn catalysed transesterification with dibutyl maleate functionalized polyolefins. Polymer 48(5):1276–1286

    Article  CAS  Google Scholar 

  32. Pillon LZ, Utracki LA, Pillon DW (1987) Spectroscopic study of poly(ethylene terephthalate)/poly(amide-6,6) blends. Polym Eng Sci 27(8):562–567

    Article  CAS  Google Scholar 

  33. Tang M, Hou J, Lei L, Liu X, Guo S, Wang Z, Chen K (2010) Preparation, characterization and properties of partially hydrolyzed ethylene vinyl acetate copolymer films for controlled drug release. Int J Pharm 400(1–2):66–73

    Article  CAS  Google Scholar 

  34. Singh AK, Prakash R, Pandey D (2011) Reactive Compatibilization of Polycarbonate and Poly(methyl methacrylate) in the Presence of a Novel Transesterification Catalyst SnCl2 · 2H2O. J Phy Chem B 115(7):1601–1607

    Article  CAS  Google Scholar 

  35. Wang XL, Zhang J, Xu JY (2006) Preparation of titanates catalysts and their catalytic behaviors to transesterification (I): Ester exchange reaction of ethyl benzoate with isoamylol. J Xi’an Shiyou Uni Nat Sci Ed 21(3):67–69

    CAS  Google Scholar 

  36. Sun D, Xie S, Deng J, Chao Z (2010) Methoxycarbonylation of 1, 6-hexanediamine with dimethyl carbonate to dimethylhexane-1,6-dicarbamate catalyzed by Zn(OAc)2. Spec Pet 27(6):9–13

    CAS  Google Scholar 

  37. Coltelli MB, Aglietto M, Ciardelli F (2008) Influence of the transesterification catalyst structure on the reactive compatibilization and properties of poly(ethylene terephthalate) (PET)/dibutyl succinate functionalized poly(ethylene) blends. Eur Polym J 44(5):1512–1524

    Article  CAS  Google Scholar 

  38. Costache MC, Jiang DD, Wilkie CA (2005) Thermal degradation of ethylene–vinyl acetate coplymer nanocomposites. Polymer 46(18):6947–6958

    Article  CAS  Google Scholar 

  39. Sailer C, Handge UA (2007) Melt viscosity, elasticity, and morphology of reactively compatibilized polyamide 6/styrene-aerylonitrile blends in shear and elongation. Macromolecules 40(6):2019–2028

    Article  CAS  Google Scholar 

  40. Bose S, Bhattacharyya AR, Kodgire PV, Misra A (2007) Fractionated crystallization in PA6/ABS blends: Influence of a reactive compatibilizer and multiwall carbon nanotubes. Polymer 48(1):356–362

    Article  CAS  Google Scholar 

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Acknowledgments

This work was supported by research grants from the National Natural Science Foundation of China (51073092).

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Correspondence to Yong Zhang.

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Lu, X., Zhang, H. & Zhang, Y. Study on ester-amide exchange reactions between Nylon 1010 and Ethylene-vinyl acetate rubber with different metal derivatives. J Polym Res 21, 539 (2014). https://doi.org/10.1007/s10965-014-0539-8

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  • DOI: https://doi.org/10.1007/s10965-014-0539-8

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