生物质化学工程 ›› 2020, Vol. 54 ›› Issue (6): 91-102.doi: 10.3969/j.issn.1673-5854.2020.06.014
潘政1, 薄采颖1,*(), 胡立红1,2, 张猛1, 任晓丽1
收稿日期:
2020-06-30
出版日期:
2020-11-30
发布日期:
2020-12-01
通讯作者:
薄采颖
E-mail:newstar2002@163.com
作者简介:
薄采颖,助理研究员,博士,主要从事生物质资源转化与利用研究; E-mail:newstar2002@163.com基金资助:
Zheng PAN1, Caiying BO1,*(), Lihong HU1,2, Meng ZHANG1, Xiaoli REN1
Received:
2020-06-30
Online:
2020-11-30
Published:
2020-12-01
Contact:
Caiying BO
E-mail:newstar2002@163.com
摘要:
苯并噁嗪树脂作为一类新型的热固性树脂,具有分子设计性强、阻燃性能和耐腐蚀性能优异、固化时不需要强酸、无小分子放出等优点,在航空、建筑、电子等领域获得了广泛应用。本文主要介绍了苯并噁嗪单体的合成方法(溶剂法、无溶剂法和悬浮法)、降低苯并噁嗪开环聚合温度的方法(合成具有特殊基团的苯并噁嗪单体、添加催化剂)及苯并噁嗪树脂在形状记忆聚合物中的应用(与其他聚合物混合,纯苯并噁嗪化学改性),对苯并噁嗪形状记忆聚合物目前存在的问题进行了概述并对苯并噁嗪形状记忆聚合物的发展前景做出了展望。
中图分类号:
潘政, 薄采颖, 胡立红, 张猛, 任晓丽. 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[J]. 生物质化学工程, 2020, 54(6): 91-102.
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.
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 |
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