Phosphorus-containing active esters modified dicyclopentadiene epoxy resins with simultaneously improved flame retardancy, thermal stability, and dielectric properties

被引:32
作者
Fu, Zhenye [1 ]
Ma, Zirui [1 ]
Liu, Jiuhong [1 ]
Li, Chunhui [1 ]
Liu, Chuanmei [1 ]
Wang, Qidong [1 ]
Song, Liang [1 ]
Yu, Qing [1 ]
Cheng, Guiqing [1 ]
Han, Yuxi [1 ]
Liu, Hailong [2 ]
Wang, Zhongwei [1 ,2 ]
机构
[1] Shandong Univ Sci & Technol, Coll Mat Sci & Engn, Qingdao 266590, Peoples R China
[2] Shandong Key Lab Adv Organosilicon Mat & Technol, Zibo 256401, Peoples R China
关键词
Active ester; Epoxy resin; Flame retardant; Dielectric constant; Dielectric loss; CURING KINETICS; HYBRID; BENZOYLATION; MECHANISM; BENZOATE; NITROGEN; OXIDE;
D O I
10.1016/j.cej.2024.148998
中图分类号
X [环境科学、安全科学];
学科分类号
08 ; 0830 ;
摘要
In the pursuit of epoxy thermosets with low dielectric properties and excellent flame retardancy, the 2(diphenylphosphino)-1,4-benzenediol active ester (DPO-HQ-AE). and 10-(2,5-dihydroxyphenyl)-9,10-dihydro-9oxa-10-phosphaphenanthrene-10-oxide active ester (DOPO-HQ-AE) were synthesized as bifunctional phosphorus-containing active ester flame retardants. The molecular structures of DPO-HQ-AE and DOPO-HQ-AE were characterized by MS, 1H NMR, 13C NMR, 31P NMR and FTIR. The flame retardancy, thermal stability, crosslink density, water absorption and dielectric properties of active ester cured dicyclopentadiene (DCPD) epoxy resins were investigated. DCPD/DPO-HQ-AE with a phosphorus content of 0.9 wt% passed the UL-94 V0 test. Meanwhile, DCPD/DOPO-HQ-AE containing 1.2 wt% phosphorus achieved a V-0 rating. DPO-HQ-AE and DOPO-HQ-AE showed noticeable gas-phase flame-retardant mechanism with active phosphorus species in the gas phase of pyrolysis. At the frequency of 1 GHz, the dielectric constant and dielectric loss of DCPD/DPO-HQ-AE-0.9 were 2.67 and 0.0042, respectively. Compared with the unmodified epoxy resin, the dielectric loss was reduced by approximately 5.5 times. The as-prepared epoxy thermosets with high thermal stability, excellent flame retardancy, low dielectric properties and low water absorption satisfied the requirements of high-speed and highfrequency encapsulation materials.
引用
收藏
页数:11
相关论文
共 71 条
[1]   The epoxy resin system: function and role of curing agents [J].
Aziz, Tariq ;
Haq, Fazal ;
Farid, Arshad ;
Cheng, Li ;
Chuah, Lai Fatt ;
Bokhari, Awais ;
Mubashir, Muhammad ;
Tang, Doris Ying Ying ;
Show, Pau Loke .
CARBON LETTERS, 2024, 34 (01) :477-494
[2]   Recent advances in bio-based epoxy resins and bio-based epoxy curing agents [J].
Baroncini, Elyse A. ;
Yadav, Santosh Kumar ;
Palmese, Giuseppe R. ;
Stanzione, Joseph F., III .
JOURNAL OF APPLIED POLYMER SCIENCE, 2016, 133 (45)
[3]   Allylamino diphenylphosphine oxide and poss containing flame retardant photocured hybrid coatings [J].
Cakmakci, Emrah .
PROGRESS IN ORGANIC COATINGS, 2017, 105 :37-47
[4]   Flame retardancy, dielectric performance, pyrolysis behavior of epoxy resin and cyanate ester composites containing a multifunctional flame retardant [J].
Cen, Xinhao ;
Cao, Zhilin ;
Wang, Zhengzhou .
JOURNAL OF VINYL & ADDITIVE TECHNOLOGY, 2024, 30 (02) :423-438
[5]   Solid-Phase Benzoylation of Phenols and Alcohols in Microwave Reactor: An Ecofriendly Protocol [J].
Chakraborty, Suchandra ;
Saha, Ahana ;
Basu, Kaushik ;
Saha, Chandan .
SYNTHETIC COMMUNICATIONS, 2015, 45 (20) :2331-2343
[6]   The reaction of activated esters with epoxides for self-curable, highly flexible, A2B2- and A3B3-type epoxy compounds [J].
Chen, Chien-Han ;
Lin, Chia-Min ;
Juang, Tzong-Yuan ;
Abu-Omar, Mandi M. ;
Lin, Ching-Hsuan .
POLYMER CHEMISTRY, 2019, 10 (29) :3983-3995
[7]   Phosphinated Poly(aryl ether) s with Acetic/Phenyl Methacrylic/Vinylbenzyl Ether Moieties for High-Tg and Low-Dielectric Thermosets [J].
Chen, Chien-Han ;
Liu, Chan-Hua ;
Ariraman, Mathivathanan ;
Lin, Ching-Hsuan ;
Juang, Tzong-Yuan .
ACS OMEGA, 2018, 3 (06) :6031-6038
[8]   A DOPO-based phosphorus-nitrogen flame retardant bio-based epoxy resin from diphenolic acid: Synthesis, flame-retardant behavior and mechanism [J].
Chi, Zhiyuan ;
Guo, Zongwei ;
Xu, Zice ;
Zhang, Mengjie ;
Li, Ming ;
Shang, Lei ;
Ao, Yuhui .
POLYMER DEGRADATION AND STABILITY, 2020, 176
[9]   Preparation of fluorinated epoxy-phthalonitrile resins with excellent thermal stability and low dielectric constant [J].
Dong, Jinghui ;
Sang, Xiaoming ;
Yin, Weihao ;
Chen, Xinggang .
JOURNAL OF APPLIED POLYMER SCIENCE, 2023, 140 (12)
[10]   Fluid uptake behavior of multifunctional epoxy blends [J].
Frank, Katherine ;
Childers, Christopher ;
Dutta, Dhanadeep ;
Gidley, David ;
Jackson, Matthew ;
Ward, Steve ;
Maskell, Rob ;
Wiggins, Jeffrey .
POLYMER, 2013, 54 (01) :403-410