苯并噁嗪树脂的合成及在形状记忆聚合物中的应用研究进展

doi:10.3969/j.issn.1673-5854.2020.06.014

Abstract

Abstract:

Benzoxazine resins, a new type of thermosetting resin, are featured by strong molecular design ability, flame retardancy, high corrosion resistance, independence on strong acids during thermosetting, and no release of small molecules and thus they are widely used in aviation, architecture, electronics and other fields. In this study, the methods of benzoxazine monomer(solvent method, solvent-free method and suspension method), the synthesis methods to reduce the ring opening polymerization temperature of benzoxazine(synthesis of benzoxazines with special groups and addition of catalysts), and the application of benzoxazine resins into shape memory polymers were introduced(mixed with other polymers and chemical modification of benzoxazine). Moreover, the existing problems concerning benzoxazine shape memory polymers were summarized. Finally, the prospects about the development of benzoxazine resins in shape memory polymers were proposed.

Key words: benzoxazine resins, synthesis, ring-opening polymerization, shape memory

CLC Number:

TQ35

Zheng PAN, Caiying BO, Lihong HU, Meng ZHANG, Xiaoli REN. Synthesis of Benzoxazine Resin and Its Application in Shape Memory Polymers[J]. Biomass Chemical Engineering, 2020, 54(6): 91-102.

Figures/Tables 10

Fig.1

Fig.2

Fig.3

Fig.4

Fig.5

Fig.6

Fig.7

Fig.8

Fig.9

Fig.10

References 55

1	HAN L , SALUM M L , ZHANG K , et al. Intrinsic self-initiating thermal ring-opening polymerization of 1, 3-benzoxazines without the influence of impurities using very high purity crystals[J]. Journal of Polymer Science Part A:Polymer Chemistry, 2017, 55 (20): 3434- 3445. doi: 10.1002/pola.28723
2	ZHANG K , LIU J , ISHIDA H . An ultrahigh performance cross-linked polybenzoxazole via thermal conversion from poly (benzoxazine amic acid) based on smart o-benzoxazine chemistry[J]. Macromolecules, 2014, 47 (24): 8674- 8681. doi: 10.1021/ma502297m
3	WU J B , XI Y , MCCANDLESS G T , et al. Synthesis and characterization of partially fluorinated polybenzoxazine resins utilizing octafluorocyclopentene as a versatile building block[J]. Macromolecules, 2015, 48 (17): 6087- 6095. doi: 10.1021/acs.macromol.5b01014
4	顾宜. 苯并噁嗪树脂——一类新型热固性工程塑料[J]. 热固性树脂, 2002, 17 (2): 31- 34, 39.
5	王旭, 徐日炜, 余鼎声, 等. 溶液法合成烯丙基苯并噁嗪中间体与其固化性能的研究[J]. 北京化工大学学报(自然科学版), 2003, 30 (4): 33- 36.
6	张芮, 楼畅, 陆馨, 等. 硅烷改性主链型聚苯并噁嗪防腐蚀涂层的制备与性能[J]. 华东理工大学学报(自然科学版), 2019, 45 (1): 9- 14.
7	SALUM M L , IGUCHI D , ARZA C R , et al. Making benzoxazines greener:Design, synthesis, and polymerization of a biobased benzoxazine fulfilling two principles of green chemistry[J]. ACS Sustainable Chemistry & Engineering, 2018, 6 (10): 13096- 13106.
8	KAYA G , KISKAN B , YAGCI Y . Phenolic naphthoxazines as curing promoters for benzoxazines[J]. Macromolecules, 2018, 51 (5): 1688- 1695. doi: 10.1021/acs.macromol.8b00218
9	KISKAN B , AYDOGAN B , YAGCI Y . Synthesis, characterization, and thermally activated curing of oligosiloxanes containing benzoxazine moieties in the main chain[J]. Journal of Polymer Science Part A:Polymer Chemistry, 2009, 47 (3): 804- 811. doi: 10.1002/pola.23197
10	ZHANG K , LIU Y Q , ISHIDA H . Polymerization of an AB-type benzoxazine monomer toward different polybenzoxazine networks:When Diels-Alder reaction meets benzoxazine chemistry in a single-component resin[J]. Macromolecules, 2019, 52 (19): 7386- 7395. doi: 10.1021/acs.macromol.9b01581
11	ISHIDA H , RODRIGUEZ Y . Curing kinetics of a new benzoxazine-based phenolic resin by differential scanning calorimetry[J]. Polymer, 1995, 36 (16): 3151- 3158. doi: 10.1016/0032-3861(95)97878-J
12	王琦玲, 赵勃. 新型酚醛树脂——苯并噁嗪的研究进展[J]. 化工中间体, 2011, (6): 6- 8, 15.
13	邹志量, 王洛礼, 胡伟, 等. 苯并恶嗪的无溶剂法合成及表征[J]. 辽宁化工, 2006, 35 (9): 510- 513.
14	曹宏伟, 徐日炜, 张炳伟, 等. 一种不含β-氢的苯并噁嗪的表征分析及催化固化研究[J]. 高等学校化学学报, 2005, 26 (7): 1298- 1303.
15	张炳伟, 徐日炜, 丁雪佳, 等. 一种新型苯并噁嗪的合成与表征及其热性能的研究[J]. 热固性树脂, 2004, 19 (2): 1- 4, 8.
16	OLIVEIRA J R , KOTZEBUE L R V , RIBEIRO F W M , et al. Microwave-assisted solvent-free synthesis of novel benzoxazines:A faster and environmentally friendly route to the development of bio-based thermosetting resins[J]. Journal of Polymer Science Part A:Polymer Chemistry, 2017, 55 (21): 3534- 3544. doi: 10.1002/pola.28755
17	ORAZIO A A , MOHAMED S B , GIANFRANCO F , et al. Solvent free synthesis of novel mono-and bis-benzoxazines from cashew nut shell liquid components[J]. Current Organic Chemistry, 2012, 16 (21): 2613- 2621. doi: 10.2174/138527212804004616
18	LIU Y Q, YIN R, YU X Y, et al.Modification of solventless-synthesized benzoxazine resin by phthalonitrile group: An effective approach for enhancing thermal stability of polybenzoxazines[J/OL]. Macromolecular Chemistry and Physics, 2019, 220(1): 1800291[2020-04-28].https://doi.org/10.1002/macp.201800291.
19	裴顶峰, 顾宜, 蔡兴贤. 二烯丙基二苯并噁嗪中间体的结构与固化行为[J]. 高分子学报, 1998, (5): 595- 598.
20	王乐萌.几种催化剂对苯并噁嗪开环聚合及热性能的影响[D].南宁:南宁师范大学, 2019.
21	ZHANG K , YU X Y . Catalyst-free and low-temperature terpolymerization in a single-component benzoxazine resin containing both norbornene and acetylene functionalities[J]. Macromolecules, 2018, 51 (16): 6524- 6533. doi: 10.1021/acs.macromol.8b01558
22	顾奕, 郭颖, 袁荞龙, 等. 增韧双马来酰亚胺与烯丙基苯并噁嗪共混物的性能[J]. 宇航材料工艺, 2012, 42 (5): 45- 50.
23	AGAG T , TAKEICHI T . Synthesis and characterization of novel benzoxazine monomers containing allyl groups and their high performance thermosets[J]. Macromolecules, 2003, 36 (16): 6010- 6017. doi: 10.1021/ma021775q
24	OHASHI S , KILBANE J , HEYL T , et al. Synthesis and characterization of cyanate ester functional benzoxazine and its polymer[J]. Macromolecules, 2015, 48 (23): 8412- 8417. doi: 10.1021/acs.macromol.5b02285
25	GILBERT E, MORALES G, SPONTÓN M, et al.Design of thermosetting polymeric systems based on benzoxazines modified with maleic anhydride[J/OL]. Journal of Applied Polymer Science, 2018, 135(17): 46183[2020-04-28].https://doi.org/10.1002/app.46183.
26	KISKAN B , KOZ B , YAGCI Y . Synthesis and characterization of fluid 1, 3-benzoxazine monomers and their thermally activated curing[J]. Journal of Polymer Science Part A:Polymer Chemistry, 2009, 47 (24): 6955- 6961. doi: 10.1002/pola.23735
27	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 (3): 1185- 1187. doi: 10.1021/ma902416h
28	ZHANG K , FROIMOWICZ P , HAN L , et al. Hydrogen-bonding characteristics and unique ring-opening polymerization behavior of ortho-methylol functional benzoxazine[J]. Journal of Polymer Science Part A:Polymer Chemistry, 2016, 54 (22): 3635- 3642. doi: 10.1002/pola.28253
29	WANG Y X , ISHIDA H . Cationic ring-opening polymerization of benzoxazines[J]. Polymer, 1999, 40 (16): 4563- 4570. doi: 10.1016/S0032-3861(99)00074-9
30	WANG Y X , ISHIDA H . Synthesis and properties of new thermoplastic polymers from substituted 3, 4-dihydro-2H-1, 3-benzoxazines[J]. Macromolecules, 2000, 33 (8): 2839- 2847. doi: 10.1021/ma9909096
31	ZHANG S , RAN Q C , FU Q , et al. Controlled polymerization of 3, 4-dihydro-2H-1, 3-benzoxazine and its properties tailored by Lewis acids[J]. Reactive & Functional Polymers, 2019, 139, 75- 84.
32	LIU C , SHEN D M , SEBASTIÁN R M , et al. Mechanistic studies on ring-opening polymerization of benzoxazines:A mechanistically based catalyst design[J]. Macromolecules, 2011, 44 (12): 4616- 4622. doi: 10.1021/ma2007893
33	ARSLAN M, KISKAN B, YAGCI Y.Ring-opening polymerization of 1, 3-benzoxazines via borane catalyst[J/OL]. Polymers, 2018, 10(3): 239[2020-04-28].https://doi.org/10.3390/polym10030239.
34	SUDO A , HIRAYAMA S , ENDO T . Highly efficient catalysts-acetylacetonato complexes of transition metals in the 4th period for ring-opening polymerization of 1, 3-benzoxazine[J]. Journal of Polymer Science Part A:Polymer Chemistry, 2010, 48 (2): 479- 484. doi: 10.1002/pola.23810
35	SUDO A , YAMASHITA H , ENDO T . Ring-opening polymerization of 1, 3-benzoxazines by p-toluenesulfonates as thermally latent initiators[J]. Journal of Polymer Science Part A:Polymer Chemistry, 2011, 49 (16): 3631- 3636. doi: 10.1002/pola.24801
36	AKKUS B, KISKAN B, YAGCI Y.Counterion effect of amine salts on ring-opening polymerization of 1, 3-benzoxazines[J/OL]. Macromolecular Chemistry and Physics, 2019, 220(1): 1800268[2020-04-28].https://doi.org/10.1002/macp.201800268.
37	SUN J Q , WEI W , XU Y Z , et al. A curing system of benzoxazine with amine:Reactivity, reaction mechanism and material properties[J]. RSC Advances, 2015, 5 (25): 19048- 19057. doi: 10.1039/C4RA16582A
38	BEYAZKILIC Z , KAHVECI M U , AYDOGAN B , et al. Synthesis of polybenzoxazine precursors using thiols:Simultaneous thiol-ene and ring-opening reactions[J]. Journal of Polymer Science Part A:Polymer Chemistry, 2012, 50 (19): 4029- 4036. doi: 10.1002/pola.26202
39	KAWAGUCHI A W , SUDO A , ENDO T . Promoting effect of thiophenols on the ring-opening polymerization of 1, 3-benzoxazine[J]. Journal of Polymer Science Part A:Polymer Chemistry, 2014, 52 (17): 2523- 2527. doi: 10.1002/pola.27266
40	ARSLAN M , KISKAN B , YAGCI Y . Combining elemental sulfur with polybenzoxazines via inverse vulcanization[J]. Macromolecules, 2016, 49 (3): 767- 773. doi: 10.1021/acs.macromol.5b02791
41	KAWAGUCHI A W , SUDO A , ENDO T . Synthesis of highly polymerizable 1, 3-benzoxazine assisted by phenyl thio ether and hydroxyl moieties[J]. Journal of Polymer Science Part A:Polymer Chemistry, 2012, 50 (8): 1457- 1461. doi: 10.1002/pola.25923
42	张帝.双酚A型苯并噁嗪/碘鎓盐的热催化固化[D].成都:西南石油大学, 2016: 24-26.
43	WANG X J, GUO X G, YE J L, et al.Freestanding 3D mesostructures, functional devices, and shape-programmable systems based on mechanically induced assembly with shape memory polymers[J/OL]. Advanced Materials, 2019, 31(2): 1805615[2020-04-28].https://doi.org/10.1002/adma.201805615.
44	ZHANG Y C, LI Y, HU Y L, et al.Localized self-growth of reconfigurable architectures induced by a femtosecond laser on a shape-memory polymer[J/OL]. Advanced Materials, 2018, 30(49): 1803072[2020-04-28].https://doi.org/10.1002/adma.201803072.
45	ERDEN N , JANA S C . Synthesis and characterization of shape-memory polyurethane-polybenzoxazine compounds[J]. Macromolecular Chemistry and Physics, 2013, 214 (11): 1225- 1237. doi: 10.1002/macp.201200315
46	GU S , JANA S . Effects of polybenzoxazine on shape memory properties of polyurethanes with amorphous and crystalline soft segments[J]. Polymers, 2014, 6 (4): 1008- 1025. doi: 10.3390/polym6041008
47	RIMDUSIT S, LOHWERATHAMA M, HEMVICHIAN K, et al.Shape memory polymers from benzoxazine-modified epoxy[J/OL]. Smart Materials and Structures, 2013, 22(7): 075033[2020-04-28].https://iopscience.iop.org/article/10.1088/0964-1726/22/7/075033.
48	TANPITAKSIT T , JUBSILP C , RIMDUSIT S . Effects of benzoxazine resin on property enhancement of shape memory epoxy:A dual function of benzoxazine resin as a curing agent and a stable network segment[J]. Express Polymer Letters, 2015, 9 (9): 824- 837. doi: 10.3144/expresspolymlett.2015.77
49	郑剑.形状记忆苯并噁嗪及其环氧树脂聚合物的制备和性能研究[D].北京:中国科学院大学, 2015: 60.
50	SCHÄFER H , HARTWIG A , KOSCHEK K . The nature of bonding matters:Benzoxazine based shape memory polymers[J]. Polymer, 2018, 135, 285- 294. doi: 10.1016/j.polymer.2017.12.029
51	ZHANG S N , PENG Y Q , XUE W H , et al. Synthesis, dynamic mechanical properties, and shape memory effect of polybenzoxazines based on monofluorophenol isomers and polyetheramines[J]. Polymer, 2019, 166, 169- 177. doi: 10.1016/j.polymer.2019.01.048
52	LIU Y F , HUANG J B , SU X H , et al. Shape memory polybenzoxazines based on polyetheramine[J]. Reactive and Functional Polymers, 2016, 102, 62- 69. doi: 10.1016/j.reactfunctpolym.2016.03.010
53	LIU Y F, SONG S N, SU X H, et al.Effect of methyl position on the dynamic mechanical and shape-memory properties of cresol-based polybenzoxazines[J/OL]. Journal of Applied Polymer Science, 2017, 134(42): 45443[2020-04-28].https://doi.org/10.1002/app.45443.
54	ZHANG S , RAN Q C , FU Q , et al. Preparation of transparent and flexible shape memory polybenzoxazine film through chemical structure manipulation and hydrogen bonding control[J]. Macromolecules, 2018, 51 (17): 6561- 6570. doi: 10.1021/acs.macromol.8b01671
55	ARSLAN M , KISKAN B , YAGCI Y , et al. Benzoxazine-based thermoset with autonomous self-healing and shape recovery[J]. Macromolecules, 2018, 51 (24): 10095- 10103. doi: 10.1021/acs.macromol.8b02137

[1]	Anxiang ZHU,Tingfei DENG,Xiong PAN,Yan TIAN,Xiaosheng YANG. Preparation and Properties of Herba Epimedii Dregs Fungus Chaff Composite Super Absorbent Resin [J]. Biomass Chemical Engineering, 2020, 54(4): 16-22.
[2]	Ronghui XU,Guosheng WANG. Research Progress in Synthesis and Application of δ-Valerolactone Base on Furfural [J]. Biomass Chemical Engineering, 2020, 54(1): 60-66.
[3]	Haibo ZHANG,Jianxin JIANG,Shibin SHANG,Zhanqian SONG. Preparation and Self-polymerization Kinetics of N-methyl-N, N-divinyl-3-dehydroabietoyloxypropan-1-ammonium Bromide [J]. Biomass Chemical Engineering, 2019, 53(1): 1-7.
[4]	LI Baowei, DAO Jianhua. Preparation and Properties of Silicone Rubber Modified by Dehydroabietic Amine [J]. bce, 2018, 52(6): 38-44.
[5]	XIE Zhipeng, HUANG Daozhan, HUANG Yanpei, HUANG Yanni. One-step Catalytic Synthesis and Herbicidal Activity of (1S,4R)-4,7,7-Trimethyl-6-oxabicyclo[3.2.1] octane-1,4-diol [J]. bce, 2018, 52(3): 23-28.
[6]	ZHAO Xinkun, LI Helong, SHE Diao, SUN Runcang. Status and Prospect of Lignin Model Compounds Synthesis [J]. bce, 2018, 52(1): 41-52.
[7]	HU Yajie, FU Genque, YUE Panpan, LI Nan, PENG Feng, SUN Runcang. Research Progress on Preparation and Application of Amino Cellulose [J]. bce, 2017, 51(6): 48-54.
[8]	JIN Can, ZHANG Xue-yan, XIONG Kai, WU Guo-min, LIU Gui-feng, CHEN Jian, KONG Zhen-wu. Progress in Preparation and Utilization of Gallic Acid Derivatives [J]. bce, 2015, 49(4): 49-56.
[9]	XIAO Feng-long, WEI Min, ZHAO Jian. Advance in Research of Polyaspartic Acid [J]. bce, 2014, 48(6): 50-55.
[10]	JIANG Ping, HU Hai-ke, DU Qing-lin. Optimization of Synthesis of 2,3,4-Trihydroxybenzoic Acid with Water by Response Surface Method [J]. bce, 2014, 48(3): 36-39.
[11]	BEI Ying;AI Qing;REN Shi-xue;FANG Gui-zhen. The Synthesis of Spherical Diethanolamine Based Lignin and Its Adsorption Character of Cu²⁺ [J]. , 2012, 46(4): 27-31.
[12]	LU Ze-xiang;FAN Li-wei;GUO Wen-zhen;CHEN Cui-xia;HUANG Biao. Ultrasonic-assisted Synthesis of 1-Methyl-3-benzylimidazliu Chloride Ionic Liquid and Its Solubility for Wood [J]. , 2010, 44(5): 21-24.
[13]	SUI Guan-hua;ZHAO Zhen-dong;BI Liang-wu;LI Dong-mei;WANG Jing. Research Progress on Synthesis and Application of Nopadiene [J]. , 2009, 43(6): 55-59.
[14]	BO Cai-ying;BI Liang-wu;ZHAO Zhen-dong;LI Dong-mei;GU Yan;WANG Jing;ZHANG Qiu-ge;WANG Yu-min;ZHOU Yong-hong. Study on Synthesis and Structure Identification of Terpenyl Gallates [J]. , 2009, 43(2): 1-5.
[15]	WEI Rui-song;DUAN Wen-gui;CEN Bo;LIANG Jian-lin. Microwave Assisted Synthesis of Hydrogenated Rosin-polyethylene Glycol-citric Acid Ester [J]. , 2007, 41(4): 17-21.

Synthesis of Benzoxazine Resin and Its Application in Shape Memory Polymers

RichHTML

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 10

References 55

Related Articles 15

Recommended Articles

Metrics

Comments