Thermoresponsive behavior of non-isocyanate poly(hydroxyl)urethane for biomedical composite materials
Source abstract
Abstract
In this work, non-isocyanate poly(hydroxyl)urethane (NIPHU) was prepared. The chemical structures of the cyclic carbonated polypropylene glycol diglycidyl ether and NIPHU were confirmed. The thermoresponsive behavior of NIPHU was researched by Rayleigh light scattering, dynamic light scattering, and scanning electron microscopy upon heating and cooling. A reversible thermoresponsive behavior from micelles to aggregated structures was discovered above the critical micelle concentration (CMC). Thermoresponsive behavior processes, including a micelle stage, aggregation upon heating, disaggregation, a fusion stage, further disaggregate stage, and an additional micelle stage upon cooling, were revealed when the concentration was equal to or below the CMC. Furthermore, the hemocompatibility and biocompatibility of NIPHU were good, as confirmed by a low toxicity by hemolysis, a low cytotoxicity toward L929 cells, and the observed confocal laser scanning microscopy images of the live/dead-stained cells. The potential application of NIPHU should therefore be explored as the component of biomedical composite materials. Reversible thermoresponsive behavior of non-isocyanate poly(hydroxyl)urethane were investigated
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Polymer composites and self-healing · Advanced Polymer Synthesis and Characterization · biodegradable polymer synthesis and properties
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (42)
Show source-provided references
1. Beniah G, Chen X, Uno B, Liu K, Leitsch E, Jeon J, Heath W, Scheidt K, Torkelson JM (2017) Combined effects of carbonate and soft-segment molecular structures on the nanophase separation and properties of segmented polyhydroxyurethane. Macromolecules 50(8):3193–320310.1021/acs.macromol.6b02513 ↗
2. Zou W, Huang J, Zeng W, Lu X (2020) Effect of ethylene–butylacrylate–glycidyl methacrylate on compatibility properties of poly (butylene terephthalate)/ thermoplastic polyurethane blends. ES Energy & Environment 9:67–73
3. Bossion A, Aguirresarobe R, Irusta L, Taton D, Cramail H, Grau E, Mecerreyes D, Su C, Liu G, Muller A (2018) Unexpected synthesis of segmented poly(hydroxyurea–urethane)s from dicyclic carbonates and diamines by organocatalysis. Macromolecules 51(15):5556–556610.1021/acs.macromol.8b00731 ↗
4. Ma Z, Li C, Fan H, Wan J, Luo Y, Li B (2017) Polyhydroxyurethanes (PHUs) derived from diphenolic acid and carbon dioxide and their application in solvent- and water-borne PHU coatings. Ind Eng Chem Res 56(47):14089–1410010.1021/acs.iecr.7b04029 ↗
5. Janvier M, Ducrot P, Allais F (2017) Isocyanate-free synthesis and characterization of renewable poly(hydroxy)urethanes from syringaresinol. ACS Sustain Chem Eng 5(10):8648–865610.1021/acssuschemeng.7b01271 ↗
6. Deepa P, Jayakannan M (2007) Solvent-induced self-organization approach for polymeric architectures of micropores, hexagons and spheres based on polyurethanes prepared via novel melt transurethane methodology. J Polym Sci A 45(12):2351–236610.1002/pola.22058 ↗
7. Deepa P, Jayakannan M (2008) Polyurethane–oligo(phenylenevinylene) random copolymers: π-Conjugated pores, vesicles, and nanospheres via solvent-induced self-organization. J Polym Sci A 46(17):5897–591510.1002/pola.22907 ↗
8. Sharma B, Hocker LT, Benthem R (2005) Synthesis and characterization of alternating poly(amide urethane)s from ε-caprolactone, diamines and diphenyl carbonate. Polymer London 46:1775–178310.1016/j.polymer.2004.11.024 ↗
9. Maisonneuve L, Lamarzelle O, Rix E, Grau E, Cramail H (2015) Isocyanate-free routes to polyurethanes and poly(hydroxy Urethane)s. Chem Rev 115:12407–1243910.1021/acs.chemrev.5b00355 ↗
10. Gabriel R, Paweł G, Parzuchowski M, Mazurek (2015) Non-isocyanate polyurethanes: synthesis, properties, and applications. Polym Adv Technol 26:707–76110.1002/pat.3522 ↗
11. Nohra B, Candy L, Blanco J, Guerin C, Raoul Y, Mouloungui Z (2013) From petrochemical polyurethanes to biobased polyhydroxyurethanes. Macromolecules 46(10):3771–379210.1021/ma400197c ↗
12. Zhang K, Nelson A, Talley S, Chen M, Margaretta E, Hudson A, Moore R, Long T (2016) Non-isocyanate poly(amide-hydroxyurethane)s from sustainable resources. Green Chem 18(17):4667–468110.1039/C6GC01096B ↗
13. Schimpf V, Ritter B, Weis P, Parison K, Mulhaupt R (2017) High purity limonene dicarbonate as versatile building block for sustainable non-isocyanate polyhydroxyurethane thermosets and thermoplastics. Macromolecules 50(3):944–95510.1021/acs.macromol.6b02460 ↗
14. Guelcher S, Srinivasan A, Dumas J, Didier J, Mcbride S, Hollinger J (2008) Synthesis, mechanical properties, biocompatibility, and biodegradation of polyurethane networks from lysine polyisocyanates. Biomaterials 29(12):1762–177510.1016/j.biomaterials.2007.12.046 ↗
15. Guelcher S (2008) Biodegradable polyurethanes: synthesis and applications in regenerative medicine. Tissue Eng Part B Rev 14(1):3–1710.1089/teb.2007.0133 ↗
16. Storey J, Wiggins A, Puckett (1994) Hydrolyzable poly(ester-urethane) networks from L-lysine diisocyanate and D, L-lactide/ϵ-caprolactone homo- and copolyester triols. J Polym Sci, Part A: Polym Chem 32:2345–236310.1002/pola.1994.080321216 ↗
17. Bello D, Herrick C, Smith T, Woskie S, Streicher R, Cullen M, Liu Y, Redlich C (2006) Skin exposure to isocyanates: reasons for concern. Environ Health Perspect 115(3):328–33510.1289/ehp.9557 ↗
18. Schmidt S, Gatti F, Luitz M, Ritter B, Bruchmann B, Mulhaupt R (2017) Erythritol dicarbonate as intermediate for solvent- and isocyanate-free tailoring of bio-based polyhydroxyurethane thermoplastics and thermoplastic elastomers. Macromolecules 50(6):2296–230310.1021/acs.macromol.6b02787 ↗
19. Panchireddy S, Grignard B, Thomassin J, Jerome C, Detrembleur C (2018) Catechol containing polyhydroxyurethanes as high-Performance coatings and adhesives. ACS Sustain Chem Eng 6(11):14936–1494410.1021/acssuschemeng.8b03429 ↗
20. Liu C, Yin Q, Li X, Hao L, Zhang W, Bao Y, Ma J (2021) A waterborne polyurethane–based leather finishing agent with excellent room temperature self-healing properties and wear-resistance. Adv Compos Hybrid Mater 4:274–28510.1007/s42114-021-00221-4 ↗
21. Gao Q, Pan Y, Zheng G, Ci L, Shen C, Liu X (2021) Flexible multilayered MXene/thermoplastic polyurethane films with excellent electromagnetic interference shielding, thermal conductivity, and management performances. Adv Compos Hybrid Mater 4:138–14910.1007/s42114-021-00206-3 ↗
22. Schmidt S, Ritter B, Kratzert D, Bruchmann B, Mülhaupt R (2016) Isocyanate-free route to poly(carbohydrate–urethane) thermosets and 100% bio-based coatings derived from glycerol feedstock. Macromolecules 49:7268–727610.1021/acs.macromol.6b01485 ↗
23. Schimpf V, Max J, Stolz B, Heck B, Mulhaupt R (2019) Semicrystalline non-isocyanate polyhydroxyurethanes as thermoplastics and thermoplastic elastomers and their Use in 3D printing by fused filament fabrication. Macromolecules 52(1):320–33110.1021/acs.macromol.8b01908 ↗
24. Schimpf V, Asmacher A, Fuchs A, Bruchmann B, Mulhaupt R (2019) Polyfunctional acrylic non-isocyanate hydroxyurethanes as photocurable thermosets for 3D printing. Macromolecules 52(9):3288–329710.1021/acs.macromol.9b00330 ↗
25. Grignard B, Thomassin J, Gennen S, Poussard L, Bonnaud L, Raquez J, Dubois P, Tran M, Park CB, Jerome C (2016) CO2-blown microcellular non-isocyanate polyurethane (NIPU) foams: from bio- and CO2-sourced monomers to potentially thermal insulating materials. Green Chem 18(7):2206–221510.1039/C5GC02723C ↗
26. Sang G, Xu P, Yan T, Murugadoss V, Naik N, Ding Y, Guo Z (2021) Interface engineered microcellular magnetic conductive polyurethane nanocomposite foams for electromagnetic interference shielding. Nanomicro Lett 13(1):153
27. Figovsky O, Shapovalov L, Leykin A, Birukova O, Potashnikova R (2013) Progress in elaboration of nonisocyanate polyurethanes based on cyclic carbonates. International Letters of Chemistry, Physics and Astronomy 30(2):52–6610.18052/www.scipress.com/ILCPA.3.52 ↗
28. Figovsky O, Shapovalov L, Axenov O (2004) Advanced coatings based upon non-isocyanate polyurethanes for industrial applications. Surface Coatings International Part B-coatings Transactions 87(2):83–9010.1007/BF02699601 ↗
29. Gennen S, Grignard B, Thomassin J, Gilbert B, Vertruyen B, Jerome C, Detrembleur C (2016) Polyhydroxyurethane hydrogels: synthesis and characterizations. Eur Polymer J 84:849–86210.1016/j.eurpolymj.2016.07.013 ↗
30. Zhang Y, Xie S, Zhang D, Ren B, Liu Y, Tang L, Chen Q, Yang J, Wu J, Tang J, Zheng J (2019) Thermo-Responsive and Shape-Adaptive Hydrogel Actuators from Fundamentals to Applications. Engineered Science 6:1–11
31. Wei H, Li A, Kong D, Li Z, Cui D, Li T, Dong B, Guo Z (2021) Polypyrrole/reduced graphene aerogel film for wearable piezoresisitic sensors with high sensing performances. Adv Compos Hybrid Mater 4:86–9510.1007/s42114-020-00201-0 ↗
32. Zhao Y, Niu M, Yang F, Jia Y, Cheng Y (2019) Ultrafast Electro-Thermal Responsive Heating Film Fabricated from Graphene Modified Conductive Materials. Engineered Science 3:33–38
33. Huang H, Han L, Wang Y, Yang Z, Zhu F, Xu M (2020) Tunable thermal-response shape memory bio-polymer hydrogels as body motion sensors. Engineered Science 9:60–67
34. Blackman L, Gibson M, Oreilly R (2017) Probing the causes of thermal hysteresis using tunable Nagg micelles with linear and brush-like thermoresponsive coronas. Polym Chem 8(1):233–24410.1039/C6PY01191H ↗
35. Tao Z, Peng K, Fan Y, Liu Y, Yang H (2016) Multi-stimuli responsive supramolecular hydrogels based on Fe3+ and diblock copolymer micelle complexation. Polym Chem 7(7):1405–141210.1039/C5PY01742D ↗
36. Wang T, Zhang X, Li X, Gao X, Song L (2016) Crystallization and morphology transition of P2VP-b-PEO block copolymer micelles composed of an amorphous core and a crystallizable corona. Polym Bull 73(3):773–78910.1007/s00289-015-1519-9 ↗
37. Petzetakis N, Walker D, Dove A, Oreilly R (2012) Crystallization-driven sphere-to-rod transition of poly(lactide)-b-poly(acrylic acid) diblock copolymers: mechanism and kinetics. Soft Matter 8(28):7408–741410.1039/c2sm25247c ↗
38. Zhang J, Han F, Wei X, Shui L, Gong H, Zhang P (2010) Spectral studies of hydrogen bonding and interaction in the absorption processes of sulfur dioxide in poly(ethylene glycol) 400 + water binary system. Ind Eng Chem Res 49:2025–203010.1021/ie9014759 ↗
39. Wang Z, Gan Y, Yan C, Huang Y, Jiang W (2016) Mechanism study of reversible transition between self-assembly and disassembly of ABC triblock copolymer micelles. Polymer 90:276–28110.1016/j.polymer.2016.03.036 ↗
40. Bhargava P, Tu Y, Zheng J, Xiong H, Quirk R, Cheng S (2007) Temperature-induced reversible morphological changes of polystyrene -block -poly (ethylene oxide) micelles in solution. J Am Chem Soc 129(5):1113–112110.1021/ja0653019 ↗
41. Polik W, Burchard W (1983) Static light scattering from aqueous poly(ethylene oxide) solutions in the temperature range 20–90°C. Macromolecules 16(6):978–98210.1021/ma00240a030 ↗
42. Cheng H, Shen L, Wu C (2006) LLS and FTIR studies on the hysteresis in association and dissociation of poly(N-isopropylacrylamide) chains in water. Macromolecules 39(6):2325–232910.1021/ma052561m ↗