Bio-based alternative to the diglycidyl ether of bisphenol A with controlled materials properties.
Bio-based alternative to the diglycidyl ether of bisphenol A with controlled materials properties.
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DOI：
10.1021/acs.biomac.5b00014
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发表时间：
2015-02
影响因子：
6.2
通讯作者：
A. Maiorana;Stephen Spinella;R. Gross
中科院分区：
文献类型：
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作者：
A. Maiorana;Stephen Spinella;R. Gross
以双酚酸（DPA）为原料，通过将游离酸转化为正烷基酯，酚羟基转化为二缩水甘油醚，合成了一系列生物基环氧单体。NMR实验证实，具有甲酯和乙酯的二苯酚酯的二缩水甘油醚（DGEDP）具有6摩尔%和3摩尔%的缩水甘油酯。将DGEDP正烷基酯的链长从甲基增加到正戊基导致环氧树脂粘度大幅降低（700-11 Pa·s）。用异佛尔酮二胺固化的DPA环氧树脂的储能模量也随正烷基酯链长（例如，3300和2100 MPa）。固化材料的α转变温度显示随着酯长度增加从158 °C线性降低至86 °C。杨氏模量和拉伸强度分别为约1150和40 MPa，对于所有测试的固化树脂（包括DGEBA）和变化不大的酯长度的函数。不同的环氧树脂，由FTIR和DSC测定的固化度，接近理论最大值。这项工作的结果表明，二缩水甘油醚的n-烷基二酚酯代表一个新的家庭的生物基液体环氧树脂，固化时，具有类似的性能，从DGEBA。
A series of biobased epoxy monomers were prepared from diphenolic acid (DPA) by transforming the free acid into n-alkyl esters and the phenolic hydroxyl groups into diglycidyl ethers. NMR experiments confirmed that the diglycidyl ethers of diphenolates (DGEDP) with methyl and ethyl esters have 6 and 3 mol % of glycidyl ester. Increasing the chain length of DGEDP n-alkyl esters from methyl to n-pentyl resulted in large decreases in epoxy resin viscosity (700-to-11 Pa·s). Storage modulus of DPA epoxy resins, cured with isophorone diamine, also varied with n-alkyl ester chain length (e.g., 3300 and 2100 MPa for the methyl and n-pentyl esters). The alpha transition temperature of the cured materials showed a linear decrease from 158 to 86 °C as the ester length increases. The Young's modulus and tensile strengths were about 1150 and 40 MPa, respectively, for all the cured resins tested (including DGEBA) and varied little as a function of ester length. Degree of cure for the different epoxy resins, determined by FTIR and DSC, closely approached the theoretical maximum. The result of this work demonstrates that diglycidyl ethers of n-alkyl diphenolates represent a new family of biobased liquid epoxy resins that, when cured, have similar properties to those from DGEBA.