The present work reports on the synthesis of an easily processable phthalonitrile monomer (BBPN) with isobutyl segment. The effect of various curing agents on curing behaviors, thermal and adhesive properties of BBPN has been evaluated. The novel phthalonitrile monomer was synthesized through nucleophilic substitution of 2,2-bis(4-hydroxyphenyl)butane (BPB) and 4-nitrophthalonitrile, and its chemical structure was characterized with FTIR, ¹H NMR and ¹³C NMR analyses. Four different aromatic diamines derived from different catalytic activities such as p-phenylenediamine (p-PD), m-tolidine (m-TB), o-tolidine (o-TB), and 2,2′-bis(trifluoromethyl)benzidine (TFMB) were used as curing agents. The curing kinetics of BBPN/aromatic diamine samples were investigated by non-isothermal differential scanning calorimetry (DSC) at different heating rates. The average activation energy was calculated based on Kissinger’s and Ozawa’s methods varied in the range of 66.61–79.00 kJ mol⁻¹. The thermal properties of the obtained polymers were investigated by dynamic mechanical thermal analysis (DMA) and thermogravimetric analysis (TGA). Compared to other three systems, the cured BBPN/p-PD exhibited better thermal stability and higher glass-transition temperature (T_g), suggesting its higher degree of cross-linking. Moreover, the BBPN/diamine systems were used to bond aluminum sheet, and the average values of lap shear strengths were in the range of 13.8–19.6 MPa at room temperature and 9.2–11.5 MPa at 300 °C, respectively.

中文翻译：

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邻苯二甲腈/芳族二胺体系的固化动力学，热学和粘合性能

本工作报道了具有异丁基链段的易于加工的邻苯二甲腈单体（BBPN）的合成。已经评估了各种固化剂对BBPN的固化行为，热和粘合性能的影响。通过2,2-双（4-羟苯基）丁烷（BPB）和4-硝基邻苯二甲腈的亲核取代反应合成了新型的邻苯二甲腈单体，并通过FTIR，¹ H NMR和¹³ C NMR分析对其化学结构进行了表征。从不同的催化活性衍生四种不同的芳族二胺如p苯二胺（p -PD），米-tolidine（米-TB），Ô -tolidine（ø-TB）和2,2'-双（三氟甲基）联苯胺（TFMB）作为固化剂。通过非等温差示扫描量热法（DSC）在不同的加热速率下研究了BBPN /芳族二胺样品的固化动力学。根据基辛格和小泽的方法计算出平均活化能，其范围在66.61–79.00 kJ mol ^-1之间。通过动态机械热分析（DMA）和热重分析（TGA）研究了获得的聚合物的热性能。与其他三种体系相比，固化的BBPN / p -PD表现出更好的热稳定性和更高的玻璃化转变温度（T _g），表明其具有较高的交联度。此外，BBPN /二胺体系用于粘合铝板，室温下的搭接剪切强度平均值分别在13.8-19.6 MPa和300°C的9.2-11.5 MPa范围内。