基于愈创木酚的生物基固化剂对环氧树脂的固化性质
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摘要
将生物基化合物丁二酸酐和具有芳环刚性结构的愈创木酚通过傅克反应制备得到同时具有酚羟基和羧酸基团的化合物3-(4-羟基-3-甲氧基苯甲酰)丙酸(GSA)。结果发现:GSA可以作为环氧树脂的固化剂,与常用的石油基固化剂4,4-二氨基二苯砜(DDS)相比,GSA的固化体系具有更高的固化反应速率常数。在相同的固化条件下,用GSA固化得到的双酚A型环氧树脂的玻璃化转变温度比DDS固化得到的高了40℃,5%热失重温度提高了107.8℃,显示出了更为优异的热稳定性。本研究对构筑高性能生物基高分子材料提供了借鉴思路。
Bio-based compound 3-(4-hydroxy-3-methoxybenzoyl) propionic acid(GSA) containing both phenolic hydroxyl and carboxylic acid group was synthesized by Friedel-Crafts reaction of succinic anhydride and guaiacol with rigid structure of aromatic ring. GSA could be used as curing agent for epoxy resin.Compared with the commonly used petroleum-based curing agent 4,4-diaminodiphenyl sulfone(DDS),the curing system of GSA had higher curing reaction rate constant.Under the identical curing conditions,the glass transition temperature and the 5% weight loss temperature of bisphenol A epoxy resin cured with GSA were 40 ℃ and 107.8 ℃ higher than that of DDS,respectively,showing better thermal stability of GSA curing system.This study provides a path for the construction of high-performance bio-based polymer materials.
Bio-based compound 3-(4-hydroxy-3-methoxybenzoyl) propionic acid(GSA) containing both phenolic hydroxyl and carboxylic acid group was synthesized by Friedel-Crafts reaction of succinic anhydride and guaiacol with rigid structure of aromatic ring. GSA could be used as curing agent for epoxy resin.Compared with the commonly used petroleum-based curing agent 4,4-diaminodiphenyl sulfone(DDS),the curing system of GSA had higher curing reaction rate constant.Under the identical curing conditions,the glass transition temperature and the 5% weight loss temperature of bisphenol A epoxy resin cured with GSA were 40 ℃ and 107.8 ℃ higher than that of DDS,respectively,showing better thermal stability of GSA curing system.This study provides a path for the construction of high-performance bio-based polymer materials.
引文
[1] ISIKGOR F H,BECER C R.Lignocellulosic biomass:a sustainable platform for the production of bio-based chemicals and polymers[J].Polym Chem,2015,6:4497-4559.
[2] SCHNEIDERMAN D K,HILLMYER M A.50th Anniversary perspective:there is a great future in sustainable polymers[J].Macromolecules,2017,50:3733-3749.
[3] XIE F W,HALLEY P J,AVEROUS L.Rheology to understand and optimize processibility,structures and properties of starch polymeric materials[J].Prog Polym Sci,2012,37:595-623.
[4] SIONKOWSKA A.Current research on the blends of natural and synthetic polymers as new biomaterials:review[J].Prog Polym Sci,2011,36:1254-1276.
[5] CHEN G Q,PATEL M K.Plastics derived from biological sources—present and future:a technical and environmental review[J].Chem Rev,2012,112:2082-2099.
[6] MA S Q,LI T T,LIU X Q,et al.Research progress on bio-based thermosetting resins[J].Polym Int,2016,65:164-173.
[7] AUVERGNE R,CAILLOL S,DAVID G,et al.Biobased thermosetting epoxy:present and future[J].Chem Rev,2014,114:1082-1115.
[8] HONG J,RADOJCIC D,IONESCU M,et al.Advanced materials from corn:isosorbide-based epoxy resin[J].Polym Chem,2014,5:5360-5368.
[9] MA S Q,WEBSTER D C,JABEEN F.Hard and flexible,degradable thermosets from renewable bioresources with the assistance of water and ethanol[J].Macromolecules,2016,49:3780-3788.
[10] ZHAO S,ABU-OMAR M M.Renewable thermoplastics based on lignin-derived polyphenols[J].Macromolecules,2017,50:3573-3581.
[11] ROUDSARI G M,MOHANTY A K,MISRA M.Study of the curing kinetics of epoxy resins with biobased hardener and epoxidized soybean oil[J].ACS Sustainable Chem Eng,2014,2:2111-2116.
[12] MAHMOUD E,WATSON D A,LOBO R F.Renewable production of phthalic anhydride from biomass-derived furan and maleic anhydride[J].Green Chem,2014,16(1):167-175.
[13] STEMMELEN M,LAPINTE V,HABAS J P,et al.Plant oil-based epoxy resins from fatty diamines and epoxidized vegetable oil[J].Eur Polym J,2015,68:536-545.
[14] JAILLET F,DESROCHES M,AUVERGNE R,et al.New biobased carboxylic acid hardeners for epoxy resins[J].Eur Lipid Sci Technol,2013,115:698-708.
[15] HU F S,YADAV S K,LA SCALA J J,et al.Preparation and characterization of furan-based renewable thermosetting epoxy-amine system[J].Macromol Chem Phys,2015,216:1441-1446.
[16] DING C,MATHARU A S.Recent developments on biobased curing agents:a review of their preparation and use[J].ACS Sustainable Chem Eng,2014,2:2217-2236.
[17] SONG Y Y,ZONG L S,BAO F,et al.Reduced curing kinetic energy and enhanced thermal resistance of phthalonitrile resins modified with inorganic particles[J].Polym Adv Technol,2018,29:1922-1929.
[18] QI Y,WENG Z H,WANG J Y,et al.A novel bio-based phthalonitrile resin derived from catechin:synthesis and comparison of curing behavior with petroleum-based counterpart[J].Polym Int,2018,67:322-329.
[2] SCHNEIDERMAN D K,HILLMYER M A.50th Anniversary perspective:there is a great future in sustainable polymers[J].Macromolecules,2017,50:3733-3749.
[3] XIE F W,HALLEY P J,AVEROUS L.Rheology to understand and optimize processibility,structures and properties of starch polymeric materials[J].Prog Polym Sci,2012,37:595-623.
[4] SIONKOWSKA A.Current research on the blends of natural and synthetic polymers as new biomaterials:review[J].Prog Polym Sci,2011,36:1254-1276.
[5] CHEN G Q,PATEL M K.Plastics derived from biological sources—present and future:a technical and environmental review[J].Chem Rev,2012,112:2082-2099.
[6] MA S Q,LI T T,LIU X Q,et al.Research progress on bio-based thermosetting resins[J].Polym Int,2016,65:164-173.
[7] AUVERGNE R,CAILLOL S,DAVID G,et al.Biobased thermosetting epoxy:present and future[J].Chem Rev,2014,114:1082-1115.
[8] HONG J,RADOJCIC D,IONESCU M,et al.Advanced materials from corn:isosorbide-based epoxy resin[J].Polym Chem,2014,5:5360-5368.
[9] MA S Q,WEBSTER D C,JABEEN F.Hard and flexible,degradable thermosets from renewable bioresources with the assistance of water and ethanol[J].Macromolecules,2016,49:3780-3788.
[10] ZHAO S,ABU-OMAR M M.Renewable thermoplastics based on lignin-derived polyphenols[J].Macromolecules,2017,50:3573-3581.
[11] ROUDSARI G M,MOHANTY A K,MISRA M.Study of the curing kinetics of epoxy resins with biobased hardener and epoxidized soybean oil[J].ACS Sustainable Chem Eng,2014,2:2111-2116.
[12] MAHMOUD E,WATSON D A,LOBO R F.Renewable production of phthalic anhydride from biomass-derived furan and maleic anhydride[J].Green Chem,2014,16(1):167-175.
[13] STEMMELEN M,LAPINTE V,HABAS J P,et al.Plant oil-based epoxy resins from fatty diamines and epoxidized vegetable oil[J].Eur Polym J,2015,68:536-545.
[14] JAILLET F,DESROCHES M,AUVERGNE R,et al.New biobased carboxylic acid hardeners for epoxy resins[J].Eur Lipid Sci Technol,2013,115:698-708.
[15] HU F S,YADAV S K,LA SCALA J J,et al.Preparation and characterization of furan-based renewable thermosetting epoxy-amine system[J].Macromol Chem Phys,2015,216:1441-1446.
[16] DING C,MATHARU A S.Recent developments on biobased curing agents:a review of their preparation and use[J].ACS Sustainable Chem Eng,2014,2:2217-2236.
[17] SONG Y Y,ZONG L S,BAO F,et al.Reduced curing kinetic energy and enhanced thermal resistance of phthalonitrile resins modified with inorganic particles[J].Polym Adv Technol,2018,29:1922-1929.
[18] QI Y,WENG Z H,WANG J Y,et al.A novel bio-based phthalonitrile resin derived from catechin:synthesis and comparison of curing behavior with petroleum-based counterpart[J].Polym Int,2018,67:322-329.