类玻璃高分子的再加工

doi:10.6023/A22020072

化学学报 ›› 2022, Vol. 80 ›› Issue (7): 1021-1041.DOI: 10.6023/A22020072 上一篇下一篇

综述

类玻璃高分子的再加工

何恩健^a, 姚艳锦^a, 张宇白^b, 危岩^a, 吉岩^a^,^*()

a 清华大学化学系生命有机磷化学及化学生物学教育部重点实验室北京 100084
b 中国石化石油化工科学研究院北京 100083

投稿日期:2022-02-15 发布日期:2022-04-05
通讯作者: 吉岩

作者简介:

何恩健, 男, 2021年本科毕业于中山大学化学学院, 现为清华大学化学系博士研究生, 导师吉岩副教授, 主要研究方向是含有动态共价键的液晶弹性体与高分子的开发与应用.

姚艳锦, 女, 2012年本科毕业于黔南民族师范学院化学化工学院, 2016年硕士毕业于华中师范大学化学学院, 现为清华大学化学系博士研究生, 导师为吉岩副教授, 主要研究方向是含有动态共价键的液晶弹性体材料的加工及应用研究.

张宇白, 女, 博士, 中级工程师, 2015年于吉林大学获得学士学位, 2016年于英国帝国理工学院获得硕士学位, 2020年于清华大学获得博士学位, 现为中国石化石油化工科学研究院职工.

危岩, 男, 1957年出生. 北京大学本科和硕士(1977~1981年)、纽约市立大学博士(1986年)、MIT博士后(1986~1987年), Drexel大学助理教授(1987年)、杜邦冠名副教授(1991年)、正教授(1995年)和瓦格納讲席教授(2004年). 曾获国家杰青基金(1998年)和教育部长江学者讲座教授(2005年)称号. 已发表学术论文1161篇(SCI引用45800余次, H指数108). 入选中组部千人计划, 于2009年底全职加盟清华大学, 主要研究方向为纳米高分子材料及其在生物医学、能源、水处理和3-D打印技术中的应用. 2014~2018年每年被爱思唯尔和汤姆森路透列为全球最高被引用的科学家之一. 2018年被聘为国家自然科学基金委基础科学中心“分子聚集发光”项目的骨干科学家.

吉岩, 女, 1977年出生, 现任清华大学化学系副教授. 本科及硕士毕业于天津大学; 2006年在北京大学获得博士学位; 2006~2011年在英国剑桥大学从事博士后研究, 2011年底加入清华大学. 2017年获国家自然科学基金优秀青年基金资助. 主要研究领域为含动态共价键的高分子、液晶弹性体、高分子纳米复合材料等.

基金资助:
国家自然科学基金(51722303); 国家自然科学基金(21674057)

Reprocessing of Vitrimer

Enjian He^a, Yanjin Yao^a, Yubai Zhang^b, Yen Wei^a, Yan Ji^a()

a The Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084
b Research Institute of Petroleum Processing, SINOPEC, Beijing 100083

Received:2022-02-15 Published:2022-04-05
Contact: Yan Ji
Supported by:
National Natural Science Foundation of China(51722303); National Natural Science Foundation of China(21674057)

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摘要/Abstract

类玻璃高分子(vitrimer)是一类含有动态共价键的共价交联聚合物网络, 结合了热固性聚合物和热塑性聚合物的优点. 在外界刺激作用下, 类玻璃高分子的动态共价键能够可逆断裂及形成, 而交联密度不会发生变化, 这种独特的性质使其能在保持三维交联网络结构的同时, 实现再加工、回收再利用、焊接和愈合等功能. 因此, 类玻璃高分子有望解决传统热固性聚合物无法进行再加工和回收再利用等问题, 推进资源的循环利用和社会可持续发展. 重点介绍了类玻璃高分子不同的再加工方式, 包括热加工、光热加工、电热加工和小分子辅助加工, 并对各个加工方式的原理、特点和应用进行总结. 最后, 对类玻璃高分子再加工的发展进行了展望.

关键词: 类玻璃高分子, 热固性聚合物, 动态共价键, 再加工

Vitrimers are a kind of covalently cross-linked polymer networks containing dynamic covalent bonds, which combine the advantages of both thermosets and thermoplastics. Under external stimuli, the dynamic covalent bonds in the networks break and reform reversibly, while the cross-link density keeps unchanged. This unique property enables this kind of materials to maintain the three-dimensional cross-linked networks and exhibit various fascinating features such as reprocessing, recycling, welding, healing, etc. Thus, vitrimers are expected to solve the problems that traditional thermosets cannot be reprocessed and recycled, making it possible to promote resource recycling towards a green and sustainable society. This review mainly focuses on the reprocessing methods of vitrimers, including thermal processing, photothermal processing, electrothermal processing and small-molecule assisted processing. Then, the principles, characteristics and applications of each reprocessing method are summarized. Furthermore, the development prospects of vitrimer reprocessing are discussed.

Key words: vitrimer, thermoset, dynamic covalent bonds, reprocessing

引用此文

何恩健, 姚艳锦, 张宇白, 危岩, 吉岩. 类玻璃高分子的再加工[J]. 化学学报, 2022, 80(7): 1021-1041.

Enjian He, Yanjin Yao, Yubai Zhang, Yen Wei, Yan Ji. Reprocessing of Vitrimer[J]. Acta Chimica Sinica, 2022, 80(7): 1021-1041.

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图/表 21

图1. AIE 分子测定Tv的机理[55]

Figure 1. The mechanism of Tv determination by AIE molecules[55]

体系	材料	催化剂	T_g/℃	T_v/℃	加工方法	加工温度及条件	文献
酯交换	环氧与脂肪酸	乙酸锌	24	57**	注射	250 ℃; 1.6 MPa压力注射30 s	[5]
	环氧与酸酐	乙酰丙酮锌	96	165*	热压	240 ℃; 热压2 min	[5]
	环氧与己二酸	双环胍	45	160*	焊接	230 ℃; 焊接3 min	[13]
	环氧液晶与癸二酸	双环胍	55	160*	重塑形	160 ℃; 塑形30 s	[14]
	环氧橡胶与十二烷二酸	乙酸锌	–12.7	185*	修复	200 ℃; 热台加热修复30 min	[15]
氨基交换	间乙烯胺酯	—	87	29**	热压	150 ℃; 热压30 min	[16]
	间乙烯胺酯	—	5	–17**	挤出	150 ℃; 1~4 r/min剪切速率挤出	[18]
	聚硅氧烷基聚脲	—	–114	70***	3D打印	70 ℃; 8/10 mm•s^–1 3D打印	[19]
烷基交换	三唑鎓离子盐	—	–11	98**	热压	160 ℃; 20 MPa压力热压60 min	[20]
	三唑鎓离子盐	—	–11	98**	重塑形	170 ℃; 1.5%•min^–1变形速率塑形	[20]
	三烷基锍盐	—	–20	65**	热压	16 ℃; 100 kPa压力热压45 min	[22]
亚胺交换	生物基聚亚胺	—	–10	–58.3**	热压	120 ℃; 热压10 min	[27]
亚胺交换	聚亚胺	—	102	56.5**	焊接	110 ℃; 200 g负载下焊接30 min	[28]
氨基甲酸酯交换	含自由羟基的聚氨酯	—	54	111**	热压	160 ℃; 4 MPa压力热压8 h	[29]
氨基甲酸酯交换	含自由羟基的聚氨酯	—	42	95**	热压	160 ℃; 4 MPa压力热压3σ*时间	[30]

表1. 类玻璃高分子的组成、特征温度、加工方法与条件

Table 1. Composition, characteristic temperature, processing methods and conditions of vitrimers

图2. 类玻璃高分子的黏弹性行为[8]

Figure 2. The viscoelastic behavior of vitrimer[8]

图3. (a)间乙烯胺酯类玻璃高分子的合成配方[37]; (b, c) PTHF与PPG类玻璃高分子的阿伦尼乌斯曲线[37]; (d, e)聚醚与非聚醚基类玻璃高分子的阿伦尼乌斯曲线[37]; (f, g)不同催化剂含量与种类的类玻璃高分子的阿伦尼乌斯曲线[12]

Figure 3. (a) Synthetic formula of vinylogous urethane vitrimers[37]; (b, c) Arrhenius plots of PTHF and PPG vitrimers[37]; (d, e) Arrhenius plots of polyethers and non-polyether matrices vitrimers[37]; (f, g) Arrhenius plots of vitrimers with different content and nature of catalyst[12]

图4. (a)压力对材料实际接触面积的影响; (b)压力对再加工样品断裂强度的影响[70]; (c)压力对再加工样品弹性模量的影响[70]

Figure 4. (a) Influence of pressure on real contact area of materials; (b) influence of pressure on fracture strength of reprocessed samples[70]; (c) influence of pressure on elastic modulus of reprocessed samples[70]

图5. 类玻璃高分子的注射成型再加工: (a)破碎的类玻璃高分子经挤出机再加工形成完整的样条[5]; (b)破碎的类玻璃高分子被再加工成矩形的样品[71]; (c)通过挤出加工和热压加工得到的类玻璃高分子样品[33]; (d) HDPE、HDPE类玻璃高分子和再加工HDPE类玻璃高分子的拉伸性能[33]

Figure 5. The reprocessing of vitrimers by injection molding: (a) the broken vitrimers are reprocessed by extrusion machine to form a complete sample[5]; (b) small pieces of vitrimer are reprocessed into a rectangular shaped sample[71]; (c) vitrimer samples were obtained by extrusion and hot-pressing[33]; (d) tensile properties of HDPE, HDPE vitrimer, and reprocessed HDPE vitrimer[33]

图6. 类玻璃高分子的热压再加工: (a)合成的和热压再加工得到的类玻璃高分子样品的拉伸试验[5]; (b)聚羟基氨酯类玻璃高分子研磨样品经热压再加工成拉伸样条的照片及机理[29]; (c)固化的碳纤维增强的类玻璃高分子复合材料层压板的热压再加工[60]

Figure 6. The reprocessing of vitrimers by hot-pressing: (a) tensile test for vitrimer samples as synthesized and as reprocessed by hot-pressing[5]; (b) the photographs and mechanism of a ground sample of polyhydroxyurethane vitrimer reprocessed into tensile bars by hot-pressing[29]; (c) the reprocessing of cured carbon fiber reinforced vitrimer composite laminate by hot-pressing[60]

图7. 不同加工条件下得到的再加工样品图像[68]: (a)不同的粒径大小和温度; (b)不同的时间和温度; (c)不同的粒径大小和压力

Figure 7. Images of reprocessed samples obtained under different processing conditions[68]: (a) different particle size and temperature; (b) different time and temperature; (c) different particle size and pressure

图8. 自增强类玻璃高分子[90]: (a)合成配方与自增强机理; (b)储能模量与交联密度随加工次数的变化; (c)机械性能随加工次数的变化

Figure 8. Self-strengthening vitrimers[90]: (a) synthetic formula and self-strengthening mechanism; (b) storage modulus and crosslinking density vary with reprocessing times; (c) mechanical properties vary with reprocessing times

图9. 类玻璃高分子的工具辅助再加工: (a)环氧液晶弹性体的微图案的擦除与恢复[14]; (b) BA与BP焊接物微图案随温度的变化[91]; (c)在高温条件下利用销形模具诱导液晶基元排列制备得到xLCE驱动器[14]; (d) xLCE在升降温过程中的可逆变形驱动[14]; (e)液晶弹性体微阵列的加工过程[94]

Figure 9. Tool-assisted reprocessing of vitrimers: (a) erasing and regaining of micropattern of epoxy liquid-crystal elastomer[14]; (b) the micropattern varies with temperature of the joint BA and BP[91]; (c) a xLCE actuator was prepared by inducing the alignment of liquid-crystal mesogens with a pin-shaped mold at high temperature[14]; (d) reversible actuation of xLCE during heating and cooling [14]; (e) fabrication of liquid-crystal elastomer micro array[94]

图10. 类玻璃高分子的焊接再加工[11]: (a)焊接样条的拉伸试验示意图; (b)不同催化剂含量的焊接样条的拉伸试验(150 ℃下焊接1 h); (c)不同焊接条件下催化剂摩尔分数为5%的焊接样条的拉伸试验; (d)不同环氧与酸酐化学计量比的焊接样条的断裂应力; (e)多次焊接样条的断裂应力

Figure 10. Vitrimers reprocessed by welding[11]: (a) the photograph of welded sample during tensile test; (b) tensile test of welded samples loaded with different catalyst contents (welded at 150 ℃ for 1 h); (c) tensile test of welded samples with x=5% catalyst under different welding conditions; (d) force at break of welded samples with different stoichiometry between epoxy and anhydride; (e) force at break of welded samples with multiple times of welding

图11. 多组分类玻璃高分子的焊接[91]: (a)三组分类玻璃高分子按不同的顺序焊接成条带结构实现多重形状记忆; (b)多组分类玻璃高分子焊接形成具有四重形状记忆效应的立方体1; (c)多组分类玻璃高分子焊接形成具有四重形状记忆效应的立方体2

Figure 11. Welding of multicomponent vitrimers[91]: (a) three components of vitrimers were welded into strips in different order to achieve multiple shape memory; (b) multicomponent vitrimers were welded to form cube1 with quadruple shape memory effect; (c) multicomponent vitrimers were welded to form cube2 with quadruple shape memory effect

图12. 类玻璃高分子的热修复: (a) (i~iv)在220 ℃对流烘箱中进行热修复; (v)热压机微压力作用下的热修复[105]; (b) (i)将类玻璃高分子样品切成两半; (ii)两半样条在200 ℃加热后完全愈合成一个整体; (iii)类玻璃高分子样品愈合前后的拉伸试验[15]

Figure 12. Thermal repairing of vitrimers: (a) (i~iv) thermal repairing in a convection oven at 220 ℃; (v) thermal repairing by hot-pressing with a slight pressure[105]; (b) (i) vitrimer sample was cut into two halves; (ii) the two halves of sample were healed completely into a whole after heating at 200 ℃; (iii) tensile test of vitrimer sample before and after healing[15]

图13. 类玻璃高分子的3D打印再加工[19]: (a)类玻璃高分子再回收过程; (b)多次回收的类玻璃高分子的机械性能; (c)多次回收的类玻璃高分子的傅立叶变换红外谱图

Figure 13. The reprocessing of vitrimers by 3D printing[19]: (a) recycle process of the vitrimer; (b) mechanical properties of vitrimer with multiple recycle times; (c) FT-IR spectra of vitrimer with multiple recycle times

图14. 类玻璃高分子的挤出成型再加工: (a)类玻璃高分子的挤出和回收[18]: (i)类玻璃高分子、双螺杆挤出机装置和从挤出机挤出的类玻璃高分子; (ii)类玻璃高分子挤出样品; (b)类玻璃高分子复合材料的形成[71]: (i)挤出成型示意图; (ii)聚氨酯类玻璃高分子与10%(质量分数)碳纳米结构通过挤出成型进行再加工; (iii)未填充和纳米填充的聚氨酯类玻璃高分子的拉伸试验

Figure 14. The reprocessing of vitrimers by extrusion: (a) extrusion and recycle of vitrimer[18]: (i) vitrimer pieces, double-twinscrew extruder setup and vitrimer extruded from extruder; (ii) vitrimer extrudate; (b) formation of vitrimer composite materials[71]: (i) illustration of extrusion molding; (ii) PU vitrimer with w=10% carbon nanostructures reprocessed by extrusion molding; (iii) tensile test of neat and nanofilled PU vitrimer

图15. 类玻璃高分子的热局部加工: (a) (i)利用紫外光对正在进行流变实验的样条进行照射实现应力松弛加速; (ii)通过局部紫外光照射激活酯交换反应以实现试样局部加工的示意图; (iii)局部再加工过程的照片[113]; (b)矩形样品(i、ii)和花瓣状样品(iii、iv)的双波长数字光处理3D打印及热局部加工[114]

Figure 15. The local reprocessing of vitrimers by heat: (a) (i) stress relaxation is accelerated by irradiating the sample under rheological experiment by UV irradiation; (ii) schematic diagram of transesterification reaction activated by local UV irradiation to realize local processing of sample; (iii) photographs of the local reprocessing process[113]; (b) dual-wavelength digital light processing 3D-printing process and local reprocessing process through heat of rectangular sample (i and ii) and petal-shaped sample (iii and iv)[114]

图16. 类玻璃高分子的光热加工: (a)通过遮光板实现选择性焊接[13]; (b)照射焊接[13]: (i)不含碳纳米管的类玻璃高分子与含有碳纳米管的类玻璃高分子的焊接; (ii)使用含有碳纳米管的类玻璃高分子作为粘合剂连接两个不含碳纳米管的类玻璃高分子; (iii)将普通环氧树脂与含有碳纳米管的类玻璃高分子连接; (iv)将热塑性聚乙烯与含有碳纳米管的类玻璃高分子连接; (c)金/类玻璃高分子复合材料的塑性变形[127]; (d) PDA-xLCE样品制备过程示意图[95]; (e) (i)利用不同强度的光对PDA-xLCE样品进行重塑形; (ii)利用辐照实现含有针孔的PDA-xLCE样品的愈合; (iii)利用辐照实现含有切口的PDA-xLCE样品的愈合[95]; (f) (i)含划痕(上)和针孔(下)的ACAT类玻璃高分子的光致愈合; (ii)含划痕(上)和针孔(下)的ACAT类玻璃高分子的热致愈合; (iii)热致愈合与光致愈合的对照实验[45]

Figure 16. Photothermal processing of vitrimers: (a) selective welding is achieved by mask[13]; (b) irradiation welding[13]: (i) welding non-CNT vitrimer with CNT vitrimer; (ii) using CNT vitrimer as adhesive to weld two pieces of non-CNT vitrimer; (iii) welding normal epoxy with CNT vitrimer, (iv) welding thermoplastic PE with CNT vitrimer; (c) the plastic deformation of Au/vitrimer composites[127]; (d) schematic diagram of preparation process of PDA-xLCE sample[95]; (e) (i) reshaping of the PDA-xLCE sample by different intensitiy of light; (ii) healing of a PDA-xLCE sample containing a needle pierced hole by irradiation; (iii) healing of a PDA-xLCE sample containing a cut by irradiation[95]; (f) (i) light-triggered healing of ACAT-vitrimer containing a cut (top) and needle pierced hole (bottom); (ii) heat-triggered healing of ACAT-vitrimer containing a cut (top) and needle pierced hole (bottom); (iii) control experiment of thermal-triggered healing and photo-triggered healing[45]

图17. 类玻璃高分子薄膜的电愈合[124]: (a, b)用针在薄膜ACNTS一侧穿孔后然后施加13 V电压对薄膜进行愈合; (c, d)用刀片在薄膜CNT-xLCEs一侧划伤后然后施加13 V电压对薄膜进行愈合; (e)初始薄膜、愈合薄膜和切割后薄膜的拉伸试验; (f)类玻璃高分子薄膜在破裂/愈合过程中电阻的变化

Figure 17. Healing of the vitrimer films by electricity[124]: (a, b) the ACNTS side of the film was perforated with a needle and the film was healed with an applied voltage of 13 V; (c, d) the CNT-xLCE side of the film was scratched with a blade and the film was healed with an applied voltage of 13 V; (e) tensile test of the pristine film, healed film, and film after cutting; (f) changes in electrical resistance of vitrimer film during breaking/healing cycles

图18. (a)环氧类玻璃高分子墨水的3D打印化学降解再聚合循环示意图[108]; (b)生物基环氧类玻璃高分子的回收工艺[138]; (c)类玻璃高分子复合材料的闭环回收[131]

Figure 18. (a) Illustration of the chemical degradation and repolymerization cycle of 3D printing of epoxy vitrimer ink[108]; (b) recycling process of the bio-based epoxy vitrimer[138]; (c) the closed-loop recycling of vitrimer composites[131]

图19. (a)类玻璃高分子复合材料表面损伤修复[131]; (b)溶剂辅助环氧类玻璃高分子焊接[137]; (c)环氧类玻璃高分子的水驱动可塑性[102]; (d)硅氧烷类玻璃高分子的水驱动可塑性[82]

Figure 19. (a) Repairing vitrimer composite with surface damage[131]; (b) solvent-assisted welding of epoxy vitrimer[137]; (c) water-driven malleability of epoxy vitrimer[102]; (d) water-driven malleability of PDMS vitrimer[82]

图20. (a)溶剂辅助预拉伸薄膜形状编程; (b)溶剂辅助环氧类玻璃高分子再编程、擦除和再配置; (c)溶剂辅助环氧类玻璃高分子愈合; (d)溶剂辅助环氧类玻璃高分子焊接[54]

Figure 20. (a) Solvent-assisted shape programming of pre-strained films; (b) solvent-assisted reprogramming, erasing and reconfiguring of epoxy vitrimer; (c) solvent-assisted healing of epoxy vitrimer; (d) solvent-assisted welding of epoxy vitrimer[54]

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类玻璃高分子的再加工

Reprocessing of Vitrimer

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