腰果酚含羟基苯并恶嗪的制备及固化反应研究
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摘要
以天然资源腰果酚合成了1种含有羟基的苯并恶嗪(CBozH),并利用红外光谱(FT-IR)及核磁共振光谱(1H-NMR和13C-NMR)表征了其化学结构。采用非等温示差扫描量热(DSC)法研究了CBozH的热固化反应过程,通过Kissinger方程、Crane方程和T-β外推法得到了该体系的固化反应温度及动力学参数。研究表明,CBozH的热固化反应表观活化能为85.47 kJ/mol,反应级数为0.909 4,凝胶温度为181℃,固化温度为217℃,后固化温度252℃。热重分析表明,CBozH开环聚合物(PCBozH)具有较好的热稳定性。
The benzoxazine monomer containing hydroxyl group(CBozH) was synthesized from cardanol,and characterized by Fourier transform infrared spectroscopy(FT-IR) and nuclear magnetic resonance spectroscopy(1 H-NMR and 13 C-NMR).The curing process of the CBozH was investigated by the differential scanning calorimetry(DSC). The kinetic parameters and curing temperature for CBozH were caculated and established by the Kissinger equation,Crane equation and T-βextrapolation method. The results showed that the apparent activation energy of ring-opening polymerization of CBozH was85. 47 k J/mol and the reaction order was 0. 909 4. The theoretical gel temperature,curing temperature and post curing temperature was 181 ℃,217 ℃ and 252 ℃,respectively. The thermogravimetric analysis showed that CBozH ring open polymer(PCBozH) had good thermal stability.
The benzoxazine monomer containing hydroxyl group(CBozH) was synthesized from cardanol,and characterized by Fourier transform infrared spectroscopy(FT-IR) and nuclear magnetic resonance spectroscopy(1 H-NMR and 13 C-NMR).The curing process of the CBozH was investigated by the differential scanning calorimetry(DSC). The kinetic parameters and curing temperature for CBozH were caculated and established by the Kissinger equation,Crane equation and T-βextrapolation method. The results showed that the apparent activation energy of ring-opening polymerization of CBozH was85. 47 k J/mol and the reaction order was 0. 909 4. The theoretical gel temperature,curing temperature and post curing temperature was 181 ℃,217 ℃ and 252 ℃,respectively. The thermogravimetric analysis showed that CBozH ring open polymer(PCBozH) had good thermal stability.
引文
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[3]Arslan M,Kiskan B,Yagci Y. Benzoxazine-based thermoset with autonomous self-healing and shape recovery[J]. Macromolecules,2018,51(24):10095-10103.
[4]Pratibha S,Bimlesh L,Devendra K,et al. Sustainable bisbenzoxazines from cardanol and PET-derived terephthalamides[J].ACS Sustainable Chemistry&Engineering,2016,4(3):1085-1093.
[5]Sharma P,Lochab B,Kumar D,et al. Interfacial encapsulation of bio-based benzoxazines in epoxy shells for temperature triggered healing[J]. Journal of Applied Polymer Science,2015,132(47):132-138.
[6]Kudoh R, Sudo A, Endo T. A highly reactive benzoxazine monomer,1-(2-Hydroxyethyl)-1,3-benzoxazine:activation of benzoxazine by neighboring group participation of hydroxyl group[J]. Macromolecules 2010,43(3):1185–1187.
[7]Oie H,Mori A,Sudo A,et al. Synthesis of networked polymer based on ring-opening addition reaction of 1,3-benzoxazine with resorcinol[J]. Journal of Polymer Science Part A:Polymer Chemistry,2012,50(22):4756–4761.
[8]Oie H,Sudo A,Endo T. Acceleration effect of N-allyl group on thermally induced ring-opening polymerization of 1,3-benzoxazine[J]. Journal of Polymer Science Part A:Polymer Chemistry,2010,48(23):5357-5363.
[9]Delage B,Briou B,Brossier T,et al. Polyoxazoline associated with cardanol for bio-based linear alkyl benzene sarfactants[J].Polymer International,2019,68(4):755-763.
[10]Huo S P,Wu G M,Chen J,et al. Constructing polyurethane foams of strong mechanical property and thermostability by two novel environment friendly bio-based polyols[J]. Korean Journal Chemistry Engineering,2015,33(3):1-7.
[11]Coline V, Sylvain C, Nilakshi V S, et al. Functionalization of cardanol:towards biobased polymers and additives[J]. Polymer Chemistry,2014,5(9):3142-3162.
[12]Kathalewar M,Sabnis A. Epoxy resin from cardanol as partial replacement of bisphenol-A-based epoxy for coating application[J].Journal of Coatings Technology and Research,2014,11(4):601-618.
[13]Vincent F,Claire N,Sylvain C,et al. Biobased amines:from synthesis to polymers;present and future[J]. Chemistry Reviews,2016,116(12),14181-14224.
[14]Huo S,Jin C,Liu G,et al. Preparation and properties of biobased autocatalytic polyols and their polyurethane foams[J]. Polymer Degradation and Stability,2019,159:62-69.
[15]Andrade T,Araújo B Q,CitóA,et al. Antioxidant properties and chemical composition of technical cashew nut shell liquid(CNSL)[J]. Food Chemistry,2011,126(3):1044-1048.
[16]Dendena B,Corsi S. Cashew,from seed to market:a review[J].Agronomy for Sustainable Development,2014,34(4):753-772.
[17]Hedaoo R K,Gite V V. Renewable resource-based polymeric microencapsulation of natural pesticide and its release study:an alternative green approach[J]. RSC Advance,2014,4(36):18637-18644.
[18]张程夕,凌鸿,顾宜.腰果酚型苯并噁嗪的固化特性[J].高分子材料科学与工程,2011,27(5):92-95.
[19]CalòE,Maffezzoli A,Mele G,et al. Synthesis of a novel cardanolbased benzoxazine monomer and environmentally sustainable production of polymers and bio-composites[J]. Green Chemistry,2007,9(7):754-759.
[20]Maria L S,Daniela I,Carlos R A,et al. Making benzoxazines greener:design,dynthesis,and polymerization of a bio-based benzoxazine fulfilling two principles of green chemistry[J]. ACS Sustainable Chemistry&Engineering,2018,6(10):13096-13106.
[21]Matusita K,Komatsu T,Yokota R. Kinetics of non-isothermal crystallization process and activation-energy for crystal-growth in amorphous materials[J]. Journal of Materials Science,1984,19(1):291-296.
[22]Han C H,Wang L,Zhao D Y. Curing process of epoxy resin using low molecular polyamide 651 as curing agent[J]. Advanced Materials Research,2014,936:63-66.
[23]Kaelble D H,Smith T. Analysis of curing kinetics in polymer composites[J]. Journal of Polymer Science Part A:Polymer Chemistry,2010,11(8):247-254.
[24]Low H Y,Ishida H. Structural effects of phenols on the thermal and thermo-oxidative degradation of polybenzox-azines[J]. Polymer,1999,40(15):4365-4376.