含DOPO的双酚A-单苯并(口恶)嗪合成、表征及其固化特性

doi:10.3969/j.issn.0438-1157.2014.09.055

化工学报 ›› 2014, Vol. 65 ›› Issue (9): 3705-3711.DOI: 10.3969/j.issn.0438-1157.2014.09.055

• 材料化学工程与纳米技术 • 上一篇下一篇

含DOPO的双酚A-单苯并(口恶)嗪合成、表征及其固化特性

刘建华¹, 史铁钧¹, 徐国梅^1,2, 王权¹, 王启东¹

1 合肥工业大学化工学院, 安徽合肥 230009;
2 皖西学院材料与化工学院, 安徽六安 237012

收稿日期:2013-12-30 修回日期:2014-03-14 出版日期:2014-09-05 发布日期:2014-09-05
通讯作者: 史铁钧
基金资助:
国家自然科学基金项目（51273054）。

Synthesis, characterization and curing characteristics of single benzoxazine containing DOPO based on bisphenol A

LIU Jianhua¹, SHI Tiejun¹, XU Guomei^1,2, WANG Quan¹, WANG Qidong¹

1 School of Chemical Engineering, Hefei University of Technology, Hefei 230009, Anhui, China;
2 Department of Materials and Chemical Engineering, West Anhui University, Lu'an 237012, Anhui, China

Received:2013-12-30 Revised:2014-03-14 Online:2014-09-05 Published:2014-09-05
Supported by:
supported by the National Natural Science Foundation of China (51273054).

摘要/Abstract

摘要： 以双酚A、苯胺、多聚甲醛为原料，合成了双酚A-双苯并(口恶)嗪（DBOZ），再用其与DOPO（9，10-二氢-9-氧杂-10-磷杂菲-10-氧化物）反应，合成了含DOPO的双酚A-单苯并(口恶)嗪（DBDO）。采用红外、核磁共振（氢谱核磁共振和碳谱核磁共振）等分析手段对DBOZ和DBDO的化学结构进行了表征；采用差示扫描量热仪对DBOZ和DBDO的固化特性进行研究，使用热重分析分析了所得聚苯并(口恶)嗪的热稳定性。结果表明：在N₂气氛中，DBOZ在205℃左右开环聚合，热分解温度为312℃，在373℃分解速度达到最快，在800℃时的残碳率为37.19%；在N₂气氛中，DBDO的热分解温度为353℃，在443℃分解速度达到最快，在800℃时的残碳率为39.60%。

关键词: 合成, 聚合, 热稳定性, 核磁共振, 双酚A-双苯并(口恶)嗪, 含DOPO的双酚A-单苯并(口恶)嗪

Abstract: Double benzoxazine based on bisphenol A（DBOZ）was synthesized from bisphenol A, aniline and paraformaldehyde, and the single benzoxazine containing DOPO based on bisphenol A（DBDO）was synthesized from DBOZ and DOPO. FT-IR, NMR (¹H NMR and ¹³CNMR) were used to characterize the chemical structure of DBOZ and DBDO. Curing characteristics were studied with DSC and thermostability was studied with TG. In N₂ atmosphere, the ring opening polymerization of DBOZ took place at about 205℃, and initial decomposition temperature was 312℃. At 373℃, the fastest decomposition was achieved. At 800℃, carbon residue was 37.19%. In N₂ atmosphere, initial decomposition temperature of DBDO was 353℃. At 443℃, the fastest decomposition was achieved. At 800℃, carbon residue was 39.60%.

Key words: synthesis, polymerization, thermostability, NMR, double benzoxazine based on bisphenol A, single benzoxazine containing DOPO based on bisphenol A

中图分类号:

O631

刘建华, 史铁钧, 徐国梅, 王权, 王启东. 含DOPO的双酚A-单苯并(口恶)嗪合成、表征及其固化特性[J]. 化工学报, 2014, 65(9): 3705-3711.

LIU Jianhua, SHI Tiejun, XU Guomei, WANG Quan, WANG Qidong. Synthesis, characterization and curing characteristics of single benzoxazine containing DOPO based on bisphenol A[J]. CIESC Journal, 2014, 65(9): 3705-3711.

参考文献 17

[1]	Holly F W, Cope A C. Condensation products of aldehydes and ketones with o-aminobenzyl alcohol and o-hydroxybenzylamine [J]. J. Am. Chem. Soc., 1944, 66: 1875-1879
[2]	Ning X, Ishida H. Phenolic materials via ring-opening polymerization: phenolic materials via ring-opening polymerization: synthesis and characterization of bisphenol-A based benzoxazines and their polymers [J]. J. Polym. Sci., Part A: PolymChem, 1994, 32: 1121-1129
[3]	Herrera P V, Doyama K, Abe H, Ishida H. Sythesis and characterization of highly fluorinated polymer with the benzoxazine moiety in the main chain [J]. Macromalecules, 2008, 41: 9704-9714
[4]	Ishida H, Rodriguez Y. Catalyzing the curing reaction of a new benzoxazine-based phenolic resin [J]. Appl. Polym. Sci., 1995, 58: 1751-1761
[5]	Ning X, Ishida H. Phenolic materials via ring-opening polymerization of benzoxazines: effect of molecular structure on mechanical and dynamic mechanical properties [J]. J. Polym. Sci. Part B: PolymPhysics, 1994, 32: 921-927
[6]	Ghosh N N, Kiskan B, Yagci Y. Polybenzoxazines-new high performance thermosetting resins:synthesis and properties [J]. Prog. Polym. Sci., 2007, 32: 1344-1391
[7]	Ishida H, Low H Y. A study on the volumetric expansion of benzoxazine-based phenolic resin [J]. Macromalecules, 1997, 30: 1099-1106
[8]	Lin Jin, Tarek A, Hatsuo I. Bis(benzoxazine-maleimide)s as a novel class of high performance resin:synthesis and properties [J]. Eur. Polym. J., 2010, 46: 354-363
[9]	Su Haixiao (苏海晓), Zhong Liu (钟柳), Chen Baoshu (陈宝书), Liu Jiping (刘吉平), Li Jiang (李姜), Liu Zhiguo (刘治国). Synthsis and characterization of DOPO-containing 1,3-benzoxazine derivatives// The Momograph of China Academic Annual Conference on Flame Retarding in 2013 [C]. Beijing, 2013: 260-268
[10]	Yusuf Y, Baris K, Narendra N G. Recent advancement on polybenzoxazine-a newly developed high performance thermoset [J]. J. Polym. Sci. Part A: Polym. Chem., 2009, 47: 5565-5576
[11]	Sun Jianxin (孙建新), Shi Tiejun (史铁钧), Xu Hui (徐慧), Wu Xinglin (吴星林). Synthesis, structure and thermal properties of bisphenol fluorene diamine benzoxazine [J].Chemical Journal of Chinese Universities Universities (高等学校化学学报), 2011, 32: 1216-1220
[12]	Wen Tinglei (文听雷), Shi Tiejun (史铁钧), Zhang Ming (张明), Chen Sufeng (陈苏峰), Wang Xiaoyan (王小艳). Synthesis, characterization and non-isothermal curing kinetics of PT-eda benzoxazine [J]. Journal of Solid Rocket Technology (固体火箭技术), 2013, 36: 408-412
[13]	Wang Qidong (王启东), Shi Tiejun (史铁钧), Xu Guomei (徐国梅). Synthesis, characterization of PT-ala and thermal degradation kinetics of its polymer [J]. CIESC Journal (化工学报), 2013, 64: 3851-3857
[14]	Hou Chien Chang, Hung Tse Lin, Ching Hsuan Lin. Benzoxazine-based phosphinated bisphenols and their application in preparing flame- retardant, low dielectric cyanate ester thermosets [J]. Polym. Chem., 2012, 3: 970-978
[15]	Dunkers J, Ishida H. Reaction of benzoxazine-based phenolic resins with strong and weak carboxylic acids and phenols as catalysts [J]. Polym. Sci. Part A: Polym. Chem., 1999, 37: 1913-1921
[16]	Chaisuwan T, Ishida H. Highly processible maleimide and nitrile functionalized benzoxazines for advanced composites applications [J]. Appl. Polym. Sci., 2010, 117: 2559-2565
[17]	Kudoh R, Sudo A, Endo T. A highly reactive benzoxazine monomer, 1-(2-hydroxyethyl)-1,3-benzoxazine: activation of benzoxazine by neighboring group participation of hydroxyl group [J]. Macromolecules, 2010, 43: 1185-1187

含DOPO的双酚A-单苯并(口恶)嗪合成、表征及其固化特性

Synthesis, characterization and curing characteristics of single benzoxazine containing DOPO based on bisphenol A

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