应用化学 ›› 2024, Vol. 41 ›› Issue (8): 1073-1084.DOI: 10.19894/j.issn.1000-0518.240032
• 综合评述 •
吕小军1, 赵卿波1, 赵洪福1, 刘三荣2(), 毕吉福2, 唐博阳3
收稿日期:
2024-01-30
接受日期:
2024-06-18
出版日期:
2024-08-01
发布日期:
2024-08-27
通讯作者:
刘三荣
基金资助:
Xiao-Jun LYU1, Qing-Bo ZHAO1, Hong-Fu ZHAO1, San-Rong LIU2(), Ji-Fu BI2, Bo-Yang TANG3
Received:
2024-01-30
Accepted:
2024-06-18
Published:
2024-08-01
Online:
2024-08-27
Contact:
San-Rong LIU
About author:
liusanrong@ciac.ac.cnSupported by:
摘要:
端羟基液体丁二烯橡胶(HTPB)的活性端羟基在适当条件下可制备成大分子引发剂,将具有特定功能的聚合物通过嵌段共聚改性的方法连接在HTPB的两端,形成结构多样、功能丰富的嵌段聚合物。 本文综述了近年来利用HTPB制备的嵌段聚合物在火箭推进剂性能改进、刺激响应性聚合物、可拉伸半导体材料和两亲性聚合物等方面的研究进展,并对利用HTPB制备新型嵌段聚合物的未来进行了展望。
中图分类号:
吕小军, 赵卿波, 赵洪福, 刘三荣, 毕吉福, 唐博阳. 基于端羟基聚丁二烯液体橡胶制备功能性嵌段聚合物的研究进展[J]. 应用化学, 2024, 41(8): 1073-1084.
Xiao-Jun LYU, Qing-Bo ZHAO, Hong-Fu ZHAO, San-Rong LIU, Ji-Fu BI, Bo-Yang TANG. Research Progress in the Preparation of Functional Block Polymers Based on Hydroxy-Terminated Polybutadiene Liquid Rubber[J]. Chinese Journal of Applied Chemistry, 2024, 41(8): 1073-1084.
图2 五嵌段共聚物生物杂化物PCysMAM-b-PDMAEMA-b-PB-b-PDMAEMA-b-PCysMAM的合成[32]
Fig.2 Synthesis of PCysMAM-b-PDMAEMA-b-PB-b-PDMAEMA-b-PCysMAM pentablock copolymer biohybrids[32]
图5 端羟基聚丁二烯-聚(环氧化物)离子液体-聚(聚氨酯脲)(HTPB-PEIL-PU)膜的制备及性能[39]
Fig.5 Preparation and properties of hydroxy-terminated polybutadiene poly(epoxide) ionic liquid poly(urethane urea) (HTPB-PEIL-PU) film[39]
1 | 韩孝族. 端羟基液体聚丁二烯橡胶[J]. 特种橡胶制品, 1984(2): 12-24. |
HAN X Z. Hydroxy-terminated liquid polybutadiene rubber[J]. Spec Purp Rubber Prod, 1984(2): 12-24. | |
2 | 刘晟男, 艾纯金, 张定军, 等. 端羟基聚丁二烯液体橡胶制备技术的研究进展[J]. 合成橡胶工业, 2023, 46(2): 158-162. |
LIU S N, AI C J, ZHANG D J, et al. Research progress in preparation technology of hydroxyl-terminated butadiene liquid rubber[J].China Synth Rubber Ind, 2023, 46(2): 158-162. | |
3 | 肖春, 刘慧慧, 郑保辉, 等. 新型含能增塑剂A16对HTPB的增塑性能[J]. 含能材料, 2020, 28(6): 552-556. |
XIAO C, LIU H H, ZHENG B H, et al. Plasticization of A16 energetic plasticizer to HTPB[J]. Chin J Energy Mater, 2020, 28(6): 552-556. | |
4 | WU B Y, ZHE Y, DO H K, et al. Waterproof, highly tough, and fast self-healing polyurethane for durable electronic skin[J]. ACS Appl Mater Interfaces, 2020, 12:11072-11083. |
5 | 刘建新, 汪存东, 潘洪波, 等. 含能叠氮高分子粘合剂的研究进展[J]. 高分子通报, 2014(9): 10-18. |
LIU J X, WANG C D, PAN H B, et al. Process in the research into energetica azide polymer binders[J].Chin Polym Bull, 2014(9): 10-18. | |
6 | 闫镒腾, 白森虎, 薛金强, 等. GAP的合成与化学改性研究进展[J]. 含能材料, 2023, 31(2): 190-200. |
YAN Y T, BAI S H, XUE J Q, et al. Progress in the synthesis and chemical modification of glycidyl azide polymer[J]. Chin J Energy Mater, 2023, 31(2): 190-200. | |
7 | 丁海琴, 肖乐勤, 菅晓霞, 等. 聚叠氮缩水甘油醚聚氨酯弹性体的低温粘弹特性[J]. 高分子材料科学与工程, 2012, 28(9): 80-83. |
DING H Q, XIAO L Q, JIAN X X, et al. Cryogenic viscoelasticities of GAP-based polyurethane elastomer[J]. Polym Mater Sci Eng, 2012, 28(9): 80-83. | |
8 | VASUDEVAN V, SUNDARARAJAN G. Synthesis of GAP-PB-GAP triblock copolymer and application as modifier in AP/HTPB composite propellant[J]. Propell Explos Pyrot, 1999, 24: 295-300. |
9 | REDDY T S, NAIR J K, SATPUTE R S. Bis(azidomethyl) oxetane/hydroxyl-terminated polybutadiene/bis(azidomethyl) oxetane triblock copolymer: synthesis and characterization[J]. J Appl Polym Sci, 2007, 106(3): 1885-1888. |
10 | MOHAN Y M, RAJU K M. Synthesis and characterization of HTPB-GAP cross-linked co-polymers[J].Des Monomers Polym, 2005, 8(2): 159-175. |
11 | CAPPELLO M, LAMIA P, MURA C. Azidated ether-butadiene-ether block copolymers as binders for solid propellants[J]. J Energy Mater, 2016, 34(3): 318-341. |
12 | FILIPPI S, MORI L, CAPPELLO M. Glycidyl azide-butadiene block copolymers: synthesis from the homopolymers and a chain extender[J]. Propellants Explos Pyrotech, 2017, 42(7): 826-835. |
13 | CAPPELLO M, FILIPPI S, MORI L. Glycidyl azide-butadiene block copolymers: 2 synthesis from a mesylated precursor[J]. Propellants Explos Pyrotech, 2017, 42(8): 974-981. |
14 | 王晓川, 莫洪昌, 舒远杰, 等. 一种三嵌段含能硝酸酯粘合剂及其合成方法: 中国, 107868596A[P]. 2018-04-03. |
WANG X C, MO H C, SHU Y J, et al. The invention relates to a three-block energetic nitrate ester adhesive and a synthesis method thereof: CN, 107868596A[P]. 2018-04-03. | |
15 | 柴春鹏, 罗运军, 郭素芳, 等. 端羟基聚丁二烯与ε-己内酯新型嵌段共聚物的合成与表征[J]. 含能材料, 2008(3): 301-304. |
CHAI C P, LUO Y J, GUO S F, et al. Synthesis and characteriza tion of novelpoly(ECL) block HTPB block poly(ECL) trblock copolymer[J]. Chin J Energ Mater, 2008(3): 301-304. | |
16 | MENG F L, ZHENG S X, ZHANG W A, et al. Nanostructured thermosetting blends of epoxy resin and amphiphilic poly(ε-caprolactone)-block-polybutadiene-block-poly(ε-caprolactone)triblock copolymer[J]. Macromolecules, 2006, 39: 711-719. |
17 | LEMOINE M, BRACHAIS C H, BONI G, et al. Characterizations of thermoplastic block elastomers based on polybutadiene and ε-caprolactone[J]. J Macromol Sci A, 2010, 47(8): 794-803. |
18 | PITET L M, HILLMYER M A. Combining ring-opening metathesis polymerization and cyclic ester ring-opening polymerization to form ABA triblock copolymersfrom 1,5-cyclooctadiene and D,L-lactide[J]. Macromolecules, 2009, 42: 3674-3680. |
19 | KIM N Y, YUN Y S, LEE J Y, et al. Enhanced impact properties of polylactide by poly(lactide-b-butadiene-b-lactide) triblock copolymer[J]. Macromol Res, 2011, 19( 9): 943-947. |
20 | LEE I, PANTHANI T R, BATES F S. Sustainable poly(lactide-b-butadiene) multiblock copolymers with enhanced mechanical properties[J]. Macromolecules, 2013, 46(18): 7387-7398. |
21 | DELGADO P A, HILLMYER M A. Combining block copolymers and hydrogen bonding for poly(lactide) toughening[J]. RSC Adv, 2014, 4(26): 13266-13273. |
22 | 张万斌, 范晓东, 范伟伟, 等. 聚丁二烯-聚四氢呋喃三嵌段共聚物的合成与热性能[J]. 高分子材料科学与工程, 2014, 30(5): 34-38. |
ZHANG W B, FAN X D, FAN W W,et al. Synthesis of triblock mPEO-b-PLLA-b-mPEO tthermosensitive hydrogel[J]. Polym Mater Sci Eng, 2014, 30(5): 34-38. | |
23 | 张万斌, 范晓东, 朱秀忠, 等. 聚四氢呋喃-聚丁二烯-聚四氢呋喃三嵌段共聚物的合成与力学性能[J]. 固体火箭技术, 2015, 38(2): 251-255. |
ZHANG W B, FAN X D, ZHU X Z, et al. Synthesis and mechanical properties of poly-(tetrahydrofuran)-poly-(butadiene)-poly-(tetrahydrofuran) triblock copolymer[J]. J Solid Rocket Technol, 2015, 38(2): 251-255. | |
24 | SINGH H, SINGH D, CHIMURKAR D, et al. High volumetric specific impulse composite propellant based on terminally functionalized block copolymers of polybutadiene and ε-caprolactone[J]. Propellants Explos Pyrotech, 2020, 45(4): 647-656. |
25 | KIM N Y, YUN Y S, LEE J Y,et al. Enhanced impact properties of polylactide by poly(lactide-b-butadiene-b-lactide) triblock copolymer[J]. Macromol Res, 2011, 19(9): 943-947. |
26 | ZHANG W B, FAN X D, TIAN W, et al. Preparation of a P(THF-co-PO)-b-PB-b-P(THF-co-PO) triblock copolymer via cationic ring-opening polymerization and its use as a thermoset polymer[J]. RSC Adv, 2015, 5(81): 66073-66081. |
27 | 范晓东, 张万斌, 范伟伟. 端羟基聚丁二烯-聚四氢呋喃三嵌段共聚物及其制备方法: 中国, 102604071B[P]. 2013-12-04. |
FAN X D, ZHANG W B, FAN W W. Preparation method of hydroxy-terminated polybutadiene-polytetrahydrofuran triblock copolymer: CN, 102604071B[P]. 2013-12-04. | |
28 | 李娜, 甘孝贤, 莫洪昌, 等. 端环氧基聚丁二烯的合成研究[J]. 含能材料, 2011, 19(5): 505-508. |
LI N, GAN X X, MO H C, et al. Synthesis of epoxy terminated polybutadiene[J]. Chin J Energy Mater, 2011, 19(5): 505-508. | |
29 | ZHANG W S, ZHANG T, LIU H H, et al. Synthesis and characterization of a novel hydroxy telechelic polyfluoroether to enhance the properties of HTPB solid propellant binders[J]. J Colloids Surf A: Physicochem Eng Aspects, 2022, 648(5): 129199. |
30 | LIANG J H, NIE J X, ZHANG H J, et al. Interaction mechanism of composite propellant components under heating conditions[J]. Polymers, 2023, 15: 2485. |
31 | 张志斌, 唐昌伟, 邱凯, 等. 生物医用智能高分子材料刺激响应性研究[J]. 生物医学工程学杂志, 2004(5): 852-855. |
ZHANG Z B, TANG C W, QIU K, et al. The advance in researches for biomedical intelligent polymer materials[J]. J Biomed Eng, 2004(5): 852-855. | |
32 | KUMAR D, MOHAMMAD S A, KUMAR A, et al. An amino acid-derived ABCBA-type antifouling biohybrid with multi-stimuli responsivity and contaminant removal capability[J]. Polym Chem, 2022, 13: 1960-1969. |
33 | MOHAMMAD S A, DOLUI S, KUMAR D, et al. L-histidine-derived smart antifouling biohybrid with multistimuli responsivity[J]. Biomacromolecules, 2021, 22: 3941-3949. |
34 | 曾海兵. 支化结构聚氨酯-脲弹性体的制备及其微相分离结构与机电性能关系研究[B]. 北京: 北京化工大学, 2023. |
ZENG H B. Preparation of branched polyurethane-urea elastomer and relation microphase separation with electromechanical properties[B]. Beijing: Beijing University of Chemical Technology, 2023. | |
35 | AN C B, DONG W J, PEI D D, et al. Elastic semiconductor blends with high strain cycling durability using an oligothiophene-based multiblock polyurethane matrix[J]. Macromolecules, 2023, 56: 5314-5325. |
36 | PEI D D, AN C B, ZHAO B, et al. Polyurethane-based stretchable semiconductor nanofilms with high intrinsic recovery similar to conventional elastomers[J]. ACS Appl Mater Interfaces, 2022, 14: 33806-33816. |
37 | 赵瑾朝. 聚氨酯/表面修饰碳纳米管复合材料的制备与导热、电绝缘行为[D]. 武汉: 华中科技大学, 2011. |
ZHAO J C. Preparation,thermal conductivity and electrical resistivity properties of polyurethane/functionalized multi-walled carbon nanotubes composites[D]. WuHan: Huazhong University of Science and Technology, 2011. | |
38 | LUO Y L, MIAO Y, XU F, et al. Synthesis, phase behavior, and simulated in vitro degradation of novel HTPB-b-PEG polyurethane copolymers[J]. Macromol Res, 2011, 19(12): 1233-1241. |
39 | TANG T Y, LING T, XU M F,et al. Selective recovery of n-butanol from aqueous solutions with functionalized poly(epoxide ionic liquid)-based polyurethane membranes by pervaporation[J]. ACS Omega, 2018, 3: 16175-16183. |
40 | WU D L, MA Q H, ZHANG B Y, et al. Mechanically ductile, self-healable, low-temperature, and water tolerant polyurethane for high-performance strain sensor[J]. ACS Appl Polym Mater, 2023, 5: 9997-10009. |
41 | 张新建, 牛莉, 孙燕, 等. 温度敏感性(PNIPAM)2-b-HTPB-b-(PNIPAM)2嵌段共聚物药物包覆与释放性能研究[J]. 新余学院学报, 2022,27(4): 17-23. |
ZHANG X J, NIUA L, SUN Y, et al. Study on drug coating and release properties of temperature sensitive (PNIPAM)2-b-HTPB-b-(PNIPAM)2 block copolymer[J]. J Xinyu Univ, 2022, 27(4):17-23. | |
42 | 张万斌, 罗杰, 张光华, 等. 聚乙二醇-聚丁二烯-聚乙二醇三嵌段共聚物的制备及性能[J]. 高分子材料科学与工程, 2020, 36(10): 155-159, 169. |
ZHANG W B, LUO J, ZHANG G H, et al. Synthesis and properties of PEG-b PB-b-PEG triblck copolymer[J]. Polym Mater Sci Eng, 2020, 36(10): 155-159, 169. | |
43 | 张万斌, 罗杰, 张光华, 等. 基于迈克尔加成构筑聚丁二烯三嵌段共聚物[J]. 陕西科技大学学报, 2020, 38(4) :70-73, 92. |
ZHANG W B, LUO J, ZHANG G H, et al. Synthesis of polybutadiene based triblock copolymervia Michael addition reaction[J]. J Shanxi Univ (Sci Technol), 2020, 38(4): 70-73, 92. | |
44 | 赵亚静, 胡激江, 介素云, 等. HTPB引入方式对不饱和树脂改性效果的影响[J]. 化工学报, 2023, 74(2): 883-892. |
ZHAO Y J, HU J J, JIE S Y, et al. Modification of unsaturated polyester resin by HTPB: effect of introducing method of the rubber[J]. 2023, 74(2): 883-892. | |
45 | HUO L X, GUO J S, YANG F H, Esterification of hydrogenated hydroxyl-herminated polybutadiene as a high-performance lubricating oil[J]. Ind Eng Chem Res, 2022, 61: 2685-2692. |
46 | MA R, ZHAO T B, PU H R, et al. Synthesis of interpenetrating polymer networks based on triisocyanate-terminated and modified poly(urethane-imide) with superior mechanical properties[J]. ACS Omega, 2020, 5: 6911-6918. |
[1] | 程金华, 姜鸿基. 末端四苯乙烯荧光团标记法研究双亲性嵌段聚合物的自组装行为[J]. 应用化学, 2019, 36(4): 440-450. |
[2] | 张帆, 王璐璐, 王吉林, 封瑞江, 张扬. 原位聚合Gemini型阳离子分子-苯乙烯嵌段聚合物构筑阴离子导电膜[J]. 应用化学, 2016, 33(6): 693-700. |
[3] | 贾若琨, 李婷婷, 周诗宇. 聚苯乙烯-嵌段-聚丁二烯有序多孔膜在可收缩膜上的形变研究和光学性质[J]. 应用化学, 2014, 31(05): 560-565. |
[4] | 程林, 王凤洋. 两亲性杂壳聚合物粒子的高效制备及以其作为模板合成金纳米簇合物[J]. 应用化学, 2011, 28(02): 149-153. |
[5] | 张健, 韩孝族. 液体橡胶增韧环氧树脂/咪唑体系的形态与力学性能[J]. 应用化学, 2005, 22(12): 1333-1337. |
[6] | 朱路, 马晓梅, 郑震, 唐小真. 含有离子传输单元的聚对苯亚乙烯聚氧化乙烯多嵌段聚合物致发光材料的合成[J]. 应用化学, 2004, 21(11): 1155-1159. |
[7] | 方天如, 徐正炎, 徐素贤. 水溶性聚合物和两亲聚合物 16.聚苯乙烯/聚丙烯酰胺嵌段聚合物的合成和表征[J]. 应用化学, 1993, 0(1): 16-20. |
[8] | 刘元社, 安立华, 单复, 骆韫珠. 端羟基聚丁二烯预聚物的表征[J]. 应用化学, 1989, 0(5): 35-38. |
阅读次数 | ||||||
全文 |
|
|||||
摘要 |
|
|||||