生物基席夫碱自修复聚氨酯的制备与性能研究

doi:10.3969/j.issn.0253-2417.2024.02.010

Abstract

Abstract:

Dynamic covalent bonds were a type of chemical bond that can be broken and restored under specific conditions. Among them, Schiff base was a dynamic covalent bond formed by the condensation of aldehydes and amine compounds. A bio-based Schiff base compound(MV/S) was synthesized by the reaction between the amine group of 1, 8-p-menthanediamine(MD) with the aldehyde group of vanillin. A Schiff base compound(EV/S) without aliphatic ring was synthesized by replacing MD with ethylenediamine. Using MV/S and EV/S as chain extenders, the self-healing Schiff base polyurethane films(PU/SM and PU/SE) were prepared, At the sametime, the polyurethane without Schiff base(PU/BDO) prepared without MV/S and EV/S was used as a blank control to determine the effect of MD on the properties of self-healing polyurethane. Various analytical and testing methods were employed to study the structure, mechanical properties, and self-healing performance of the polyurethanes. The results showed that the tensile strength of PU/SM was 30.7 MPa, which was 20.1 MPa higher than that of PU/BDO. TG/DTG analysis revealed that the introduction of MD significantly improved the heat resistance of PU/SM. Comparison at the same temperature showed a significant reduction in relaxation time of PU/SM compared to that of PU/SE, indicating that the introduction of MD promoted the exchange rate of dynamic covalent bonds. Compared with PU/SE, PU/SM exhibited a faster relaxation rate, and the activation energy was reduced by 35. 84 kJ/mol. The results of self-healing performance tests demonstrated that PU/SM had superior self-healing properties compared to PU/BDO and PU/SE, with a self-healing rate of 77% for the sheared PU/SM film after 24 h of heating at 80 ℃.

Key words: 1, 8-mentane-p-diamine, relaxation time, self-repairing, environmentally friendly

CLC Number:

TQ35

Xu FAN, Fuhao DONG, He LIU, Jianxin JIANG, Zhanqian SONG. Preparation and Properties of Bio-based Schiff Base Self-repairing Polyurethane[J]. Chemistry and Industry of Forest Products, 2024, 44(2): 71-78.

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References 27

1	周永红, 潘政, 张猛. 生物基聚氨酯材料的研究进展[J]. 生物质化学工程, 2023, 57 (1): 1- 12.
	ZHOU Y H , PAN Z , ZHANG M . Recent progress in synthesis and application of bio-based polyurethanes[J]. Biomass Chemical Engineering, 2023, 57 (1): 1- 12.
2	CORTEN C C , URBAN M W . Repairing polymers using oscillating magnetic field[J]. Advanced Materials, 2009, 21 (48): 5011- 5015. doi: 10.1002/adma.200901940
3	YANG L , LU X L , WANG Z H , et al. Diels-Alder dynamic crosslinked polyurethane/polydopamine composites with NIR triggered self-healing function[J]. Polymer Chemistry, 2018, 9 (16): 2166- 2172. doi: 10.1039/C8PY00162F
4	LIN C H , SHENG D K , LIU X D , et al. NIR induced self-healing electrical conductivity polyurethane/graphene nanocomposites based on Diels-Alder reaction[J]. Polymer, 2018, 140, 150- 157. doi: 10.1016/j.polymer.2018.02.036
5	AKINDAYO J O , BEG M D H , GHAZALI S , et al. Polyurethane types, synthesis and applications: A review[J]. RSC Advances, 2016, 6 (115): 114453- 114482. doi: 10.1039/C6RA14525F
6	KIM H D , LEE T J , HUH J H , et al. Preparation and properties of segmented thermoplastic polyurethane elastomers with two different soft segments[J]. Journal of Applied Polymer Science, 1999, 73 (3): 345- 352. doi: 10.1002/(SICI)1097-4628(19990718)73:3<345::AID-APP5>3.0.CO;2-T
7	WEI Y Y , MA X Y . The self-healing cross-linked polyurethane by Diels-Alder polymerization[J]. Advances in Polymer Technology, 2018, 37 (6): 1987- 1993. doi: 10.1002/adv.21857
8	ZHENG K W, TIAN Y Z, FAN M J, et al. Recyclable, shape-memory, and self-healing soy oil-based polyurethane crosslinked by a thermoreversible Diels-Alder reaction[J/OL]. Journal of Applied Polymer Science, 2018, 135(13): 46049[2023-01-10]. https://doi.org/10.1002/app.46049.
9	LI T , XIE Z N , WENG Y X , et al. Design of a self-healing cross-linked polyurea with dynamic cross-links based on disulfide bonds and hydrogen bonding[J]. European Polymer Journal, 2018, 107, 249- 257. doi: 10.1016/j.eurpolymj.2018.08.005
10	GAO W T , BIE M Y , QUAN Y W , et al. Self-healing, reprocessing and sealing abilities of polysulfide-based polyurethane[J]. Polymer, 2018, 151, 27- 33. doi: 10.1016/j.polymer.2018.07.047
11	DENG X Y , XIE H , DU L , et al. Polyurethane networks based on disulfide bonds: From tunable multi-shape memory effects to simultaneous self-healing[J]. Science China Materials, 2018, 62 (3): 437- 447.
12	YUAN C E , RONG M Z , ZHANG M Q . Self-healing polyurethane elastomer with thermally reversible alkoxyamines as crosslinkages[J]. Polymer, 2014, 55 (7): 1782- 1791. doi: 10.1016/j.polymer.2014.02.033
13	ERICE A , DE LUZURIAGA A R , MATXAIN J M , et al. Reprocessable and recyclable crosslinked poly(urea-urethane)s based on dynamic amine/urea exchange[J]. Polymer, 2018, 145, 127- 136. doi: 10.1016/j.polymer.2018.04.076
14	YAN P Y , ZHAO W , FU X W , et al. Multifunctional polyurethane-vitrimers completely based on transcarbamoylation of carbamates: Thermally-induced dual-shape memory effect and self-welding[J]. RSC Advances, 2017, 7 (43): 26858- 26866. doi: 10.1039/C7RA01711A
15	CHEN X , LI L Q , JIN K L , et al. Reprocessable polyhydroxyurethane networks exhibiting full property recovery and concurrent associative and dissociative dynamic chemistry via transcarbamoylation and reversible cyclic carbonate aminolysis[J]. Polymer Chemistry, 2017, 8 (41): 6349- 6355. doi: 10.1039/C7PY01160A
16	FORTMAN D J, BRUTMAN J P, HILLMYER M A, et al. Structural effects on the reprocessability and stress relaxation of crosslinked polyhydroxyurethanes[J/OL]. Journal of Applied Polymer Science, 2017, 134(45): 44984[2023-01-10]. https://doi.org/10.1002/app.44984.
17	MATSUKIZONO H , ENDO T . Reworkable polyhydroxyurethane films with reversible acetal networks obtained from multifunctional six-membered cyclic carbonates[J]. Journal of the American Chemical Society, 2018, 140 (3): 884- 887. doi: 10.1021/jacs.7b11824
18	DU W N , JIN Y , LAI S Q , et al. Near-infrared light triggered shape memory and self-healable polyurethane/functionalized graphene oxide composites containing diselenide bonds[J]. Polymer, 2018, 158, 120- 129. doi: 10.1016/j.polymer.2018.10.059
19	ZHANG Z P , RONG M Z , ZHANG M Q . Polymer engineering based on reversible covalent chemistry: A promising innovative pathway towards new materials and new functionalities[J]. Progress in Polymer Science, 2018, 80, 39- 93. doi: 10.1016/j.progpolymsci.2018.03.002
20	AL ZOUBI W , AL-HAMDANI A A S , KASEEM M . Synthesis and antioxidant activities of Schiff bases and their complexes: A review[J]. Applied Organometallic Chemistry, 2016, 30 (10): 810- 817. doi: 10.1002/aoc.3506
21	LEI Z Q , XIE P , RONG M Z , et al. Catalyst-free dynamic exchange of aromatic Schiff base bonds and its application to self-healing and remolding of crosslinked polymers[J]. Journal of Materials Chemistry A, 2015, 3 (39): 19662- 19668. doi: 10.1039/C5TA05788D
22	JIA P Y, SHI Y X, SONG F, et al. Bio-based and degradable vitrimer-graphene/graphene oxide composites with self-healing ability stimulated by heat, electricity and microwave as temperature and fire warning sensors[J/OL]. Composites Science and Technology, 2022, 227: 109573[2023-01-10]. https://doi.org/10.1016/j.compscitech.2022.109573.
23	FAN X, YANG X X, WANG S B, et al. Modified cellulose nanocrystals are used to enhance the performance of self-healing siloxane elastomers[J/OL]. Carbohydrate Polymers, 2021, 273: 118529[2023-01-10]. https://doi.org/10.1016/j.carbpol.2021.118529.
24	ZYCH A , TELLERS J , BERTOLACCI L , et al. Biobased, biodegradable, self-healing boronic ester vitrimers from epoxidized soybean oil acrylate[J]. ACS Applied Polymer Materials, 2020, 3 (2): 1135- 1144.
25	DONG F H , YANG X X , GUO L Z , et al. Self-healing polyurethane with high strength and toughness based on a dynamic chemical strategy[J]. Journal of Materials Chemistry A, 2022, 10 (18): 10139- 10149. doi: 10.1039/D2TA00802E
26	董阜豪, 钱约翰, 王玉琪, 等. 光固化甲基丙烯酸异冰片酯-水性聚氨酯的制备及性能研究[J]. 林产化学与工业, 2021, 41 (3): 71- 76.
	DONG F H , QIAN Y H , WANG Y Q , et al. Preparation and performance of UV-curable isobornyl methacrylate-waterborne polyurethane[J]. Chemistry and Industry of Forest Products, 2021, 41 (3): 71- 76.
27	陈兴幸, 钟倩云, 王淑娟, 等. 动态共价键高分子材料的研究进展[J]. 高分子学报, 2019, 50 (5): 469- 484.
	CHEN X X , ZHONG Q Y , WANG S J , et al. Progress in dynamic covalent polymers[J]. Acta Polymerica Sinica, 2019, 50 (5): 469- 484.

Preparation and Properties of Bio-based Schiff Base Self-repairing Polyurethane

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样品sample	PTMEG	HMDI	MV/S	EV/S	BDO
PU/BDO	1	2	0	0	1
PU/SM	1	3	1	0	1
PU/SE	1	3	0	1	1