Synthesis of benzoxazine from eugenol and its co-polymerization with a gallic acid-based epoxy resin for flame retardant application

被引:8
作者
Patil, Dhananjay A. [1 ]
Naiker, Vidhukrishnan E. [1 ]
Phalak, Ganesh A. [1 ]
More, Aarti P. [1 ]
Mhaske, S. T. [1 ]
机构
[1] Inst Chem Technol, Dept Polymer & Surface Engn, Mumbai 400019, Maharashtra, India
关键词
Bio-based; Epoxy; Gallic acid; Eugenol; Benzoxazine; Flame retardant; FULLY BIOBASED BENZOXAZINES; BIO-BASED POLYBENZOXAZINE; RENEWABLE RESOURCE; CARDANOL; VANILLIN; MONOMER; COPOLYMERIZATION; FURFURYLAMINE; PHOSPHORUS; COMPOSITE;
D O I
10.1007/s00289-023-05055-2
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Polybenzoxazines (PBz) are a new type of resin belonging to the category of phenolic resins. As polybenzoxazines are addition-curable polymers, this obviates many of the shortcomings associated with conventional phenolic resins while endowing them with excellent thermal, physical, and thermo-physical properties and surpass the features of many conventional and state-of-the-art polymers. They even possess excellent design flexibility. In this study, a benzoxazine monomer was successfully synthesized from eugenol (Eu), ethylenediamine, and paraformaldehyde utilizing a solventless approach. The synthesized benzoxazine resin was characterized for its structural elucidation via FTIR, 1H, and 13C NMR spectroscopy and was used for crosslinking a petroleum-based epoxy and a gallic acid-based epoxy. The effects of the presence of benzoxazine on the thermal and flame retardant properties of the films were evaluated using TGA and DSC analysis and the LOI and UL 94 tests, respectively. It was found that the benzoxazine in the epoxy systems led to an increase in thermal stability and flame retardancy. The gallic acid-based epoxy system showed better thermal and flame retardant properties compared to the petroleum-based epoxy system, thus showing potential to replace the petroleum-based epoxy for high-performance applications.
引用
收藏
页码:7441 / 7465
页数:25
相关论文
共 56 条
[1]   1,3-Bis(benzoxazine) from Cashew Nut Shell Oil and Diaminodiphenyl Methane and Its Composites with Wood Flour [J].
Agag, Tarek ;
An, Si Young ;
Ishida, Hatsuo .
JOURNAL OF APPLIED POLYMER SCIENCE, 2013, 127 (04) :2710-2714
[2]   A new synthetic approach for difficult benzoxazines: Preparation and polymerization of 4,4′-diaminodiphenyl sulfone-based benzoxazine monomer [J].
Agag, Tarek ;
Jin, Lin ;
Ishida, Hatsuo .
POLYMER, 2009, 50 (25) :5940-5944
[3]   Synthesis, curing kinetics, thermal and mechanical behavior of novel cardanol-based benzoxazines [J].
Ambrozic, Rok ;
Sebenik, Urska ;
Krajnc, Matjaz .
POLYMER, 2015, 76 :203-212
[4]   Multi-functionalization of gallic acid. Synthesis of a novel bio-based epoxy resin [J].
Aouf, Chahinez ;
Nouailhas, Helene ;
Fache, Maxence ;
Caillol, Sylvain ;
Boutevin, Bernard ;
Fulcrand, Helene .
EUROPEAN POLYMER JOURNAL, 2013, 49 (06) :1185-1195
[5]   Electrochemical manipulation of adhesion strength of polybenzoxazines on metal surfaces: from strong adhesion to dismantling [J].
Aydogan, C. ;
Kiskan, B. ;
Hacioglu, S. O. ;
Toppare, L. ;
Yagci, Y. .
RSC ADVANCES, 2014, 4 (52) :27545-27551
[6]   Renewable Benzoxazine Monomers from "Lignin-like" Naturally Occurring Phenolic Derivatives [J].
Comi, Marc ;
Lligadas, Gerard ;
Ronda, Juan C. ;
Galia, Marina ;
Cadiz, Virginia .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2013, 51 (22) :4894-4903
[7]   Biobased Benzoxazine Derived from Daidzein and Furfurylamine: Microwave-Assisted Synthesis and Thermal Properties Investigation [J].
Dai, Jinyue ;
Teng, Na ;
Peng, Yunyan ;
Liu, Yuan ;
Cao, Lijun ;
Zhu, Jin ;
Liu, Xiaoqing .
CHEMSUSCHEM, 2018, 11 (18) :3175-3183
[8]   Chavicol benzoxazine: Ultrahigh Tg biobased thermoset with tunable extended network [J].
Dumas, Ludovic ;
Bonnaud, Leila ;
Olivier, Marjorie ;
Poorteman, Marc ;
Dubois, Philippe .
EUROPEAN POLYMER JOURNAL, 2016, 81 :337-346
[9]   High performance bio-based benzoxazine networks from resorcinol and hydroquinone [J].
Dumas, Ludovic ;
Bonnaud, Leila ;
Olivier, Marjorie ;
Poorteman, Marc ;
Dubois, Philippe .
EUROPEAN POLYMER JOURNAL, 2016, 75 :486-494
[10]   Eugenol-based benzoxazine: from straight synthesis to taming of the network properties [J].
Dumas, Ludovic ;
Bonnaud, Leila ;
Olivier, Marjorie ;
Poorteman, Marc ;
Dubois, Philippe .
JOURNAL OF MATERIALS CHEMISTRY A, 2015, 3 (11) :6012-6018