Reprocessing of Vitrimer

doi:10.6023/A22020072

Acta Chimica Sinica ›› 2022, Vol. 80 ›› Issue (7): 1021-1041.DOI: 10.6023/A22020072 Previous Articles Next Articles

Review

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)

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

Cite this article

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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Fig. & Tab. 21

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]

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

Figure 2. The viscoelastic behavior of vitrimer[8]

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]

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]

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]

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]

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

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

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]

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

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

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]

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

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

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]

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]

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

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]

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]

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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