Thermoplastic Polyurethanes Stemming from Castor Oil: Green Synthesis and Their Application in Wood Bonding
Source abstract
Abstract
We report an efficient and green approach to synthesize a linear castor oil-based polyurethane (CPU) without using any solvent or catalyst. Diol monomers were first synthesized by the aminolysis reaction between castor oil and diamines; this was accomplished within 6 h at 130 °C. Polymerization of the diols and isocyanate was further confirmed by Fourier transform infrared (FTIR), 1H-nuclear magnetic resonance (1H-NMR), and gel permeation chromatography analyses. The resultant CPUs showed a good thermal stability with an initial degradation temperature higher than 300 °C, and their mechanical and wood bonding property can be modulated by the structures of diamine. In addition, the CPUs possessed a satisfying water resistance property with the water absorption amount lower than 2%. The green conversion of castor oil to thermoplastic polyurethane affords new opportunities in bio-based industries.
Source: crossref · Quality: baseline
Research context
OpenAlex topics: Polymer composites and self-healing · Lignin and Wood Chemistry · Carbon dioxide utilization in catalysis
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
Affiliations
Aviation Engineering Institute, Civil Aviation Flight University of China, Guanghan 618307, China
Funding
National Natural Science Foundation of China · Science Research Foundation of Civil Aviation Flight University of China
References (51)
Show source-provided references
1. From vegetable oils to polyurethanes: Synthetic routes to polyols and main industrial products10.1080/15583724.2011.640443 ↗
2. The selective reaction of primary amines with carbonyl imidazole containing compounds: Selective amide and carbamate synthesis10.1021/ol006020n ↗
3. Achieving functional group diversity in parallel synthesis: Solution-phase synthesis of a library of ureas, carbamates, thiocarbamates, and amides using carbamoylimidazolium salts10.1016/j.tetlet.2008.06.096 ↗
4. Convenient method for the preparation of carbamates, carbonates, and thiocarbonates10.1021/ol7024108 ↗
5. Cheminform abstract: Perspectives on the synthesis of organic carbamates
6. Sustainable routes to polyurethane precursors10.1039/c3gc40440d ↗
7. Recent advances in vegetable oil-based polyurethanes10.1002/cssc.201000378 ↗
8. Soy-castor oil based polyols prepared using a solvent-free and catalyst-free method and polyurethanes therefrom10.1039/c3gc40531a ↗
9. Vegetable oil-based polymeric materials: Synthesis, properties, and applications10.1039/c0gc00264j ↗
10. Thermally stable, transparent, pressure-sensitive adhesives from epoxidized and dihydroxyl soybean oil10.1021/bm200188u ↗
11. Self-healable polymer networks based on the cross-linking of epoxidised soybean oil by an aqueous citric acid solution10.1039/c3gc41384e ↗
12. Renewable resource-based epoxy resins derived from multifunctional poly(4-hydroxybenzoates)10.1039/c3gc37088g ↗
13. Full biobased polymeric material from plant oil and poly(lactic acid) with a shape memory property10.1021/sc500310s ↗
14. Production of poly(3-hydroxybutyrate-co-3-hydroxyhexanoate) from plant oil by engineered Ralstonia eutropha strains10.1128/AEM.02429-10 ↗
15. Biosynthesis and biocompatibility of poly(3-hydroxybutyrate-co-4-hydroxybutyrate) produced by cupriavidus necator from spent palm oil10.1016/j.bej.2009.11.005 ↗
16. Production of poly(3-hydroxybutyrate-co-3-hydroxyvalerate) by cupriavidus necator from waste rapeseed oil using propanol as a precursor of 3-hydroxyvalerate10.1007/s10529-010-0376-8 ↗
17. Biodiesel production: A review10.1016/S0960-8524(99)00025-5 ↗
18. Sulfur-containing fatty acid-based plasticizers via thiol-ene addition and oxidation: Synthesis and evaluation in PVC formulations10.1039/C3GC42172D ↗
19. Biodegradable and biocompatible epoxidized vegetable oil modified thermostable poly(vinyl chloride): Thermal and performance characteristics post biodegradation with Pseudomonas aeruginosa and Achromobacter sp.10.1016/j.jhazmat.2012.01.043 ↗
20. Fatty acid derived renewable polyamides via thiol-ene additions10.1039/c2gc35982k ↗
21. Thermosetting allyl resins derived from soybean oil
22. Thermo-mechanical and antibacterial properties of soybean oil-based cationic polyurethane coatings: Effects of amine ratio and degree of crosslinking10.1002/mame.201300423 ↗
23. Synthesis and properties of alkoxysilane castor oil and their polyurethane/urea-silica hybrid coating films10.1021/sc3001756 ↗
24. Aqueous cationic polyurethane dispersions from vegetable oils10.1002/cssc.200900251 ↗
25. Soybean oil-isosorbide-based waterborne polyurethane-urea dispersions10.1002/cssc.201000411 ↗
26. Reduction of epoxidized vegetable oils: A novel method to prepare bio-based polyols for polyurethanes10.1002/marc.201400039 ↗
27. New biobased high functionality polyols and their use in polyurethane coatings10.1002/cssc.201100415 ↗
28. Effects of unsaturation and different ring-opening methods on the properties of vegetable oil-based polyurethane coatings10.1016/j.polymer.2014.01.014 ↗
29. Copolymers of tetrahydrofuran and epoxidized vegetable oils: Application to elastomeric polyurethanes10.1039/C3PY01527K ↗
30. Castor oil-based hyperbranched polyurethanes as advanced surface coating materials10.1016/j.porgcoat.2012.09.001 ↗
31. Sustainable waterborne polyurethane ionomer reinforced poly(vinyl alcohol) composite films10.1016/j.compscitech.2014.03.018 ↗
32. Rheological behavior of environmentally friendly castor oil-based waterborne polyurethane dispersions10.1021/ma400200y ↗
33. Biodegradable foam plastics based on castor oil10.1021/bm7009152 ↗
34. Cathodically electrodepositable novel coating system from castor oil10.1002/app.1992.070441101 ↗
35. Two-package polyurethane coatings based on castor oil-modified polyesteramides for industrial maintenance coatings
36. Poly (urethane fatty amide) resin from linseed oil—A renewable resource10.1016/j.porgcoat.2008.07.006 ↗
37. Rapid approach to biobased telechelics through two one-pot thiol-ene click reactions10.1021/bm100290n ↗
38. Thermoplastic polyurethanes from undecylenic acid-based soft segments: Structural features and release properties10.1002/mabi.201200433 ↗
39. Plant oils as platform chemicals for polyurethane synthesis: Current state-of-the-art10.1021/bm100839x ↗
40. Morphology and properties of thermoplastic polyurethanes with dangling chains in ricinoleate-based soft segments10.1016/j.polymer.2008.07.027 ↗
41. Polyester polyols and polyurethanes from ricinoleic acid10.1002/app.27783 ↗
42. (2003). GB/T 7124-2008 ISO 4587:2003 Adhesive Test of Tensile Shear Strength.
43. Expedient Synthesis of N-Acyl Anthranilamides and β-Enamine Amides by the Rh(III)-Catalyzed Amidation of Aryl and Vinyl C–H Bonds with Isocyanates10.1021/ja203495c ↗
44. The reactions of isocyanates and isocyanate derivatives at elevated temperatures10.5254/1.3542399 ↗
45. Effect of block ratio and strain amplitude on thermal, structural, and shape memory properties of segmented polycaprolactone-based polyurethanes10.1007/s10853-014-8466-y ↗
46. Thermal decomposition of energetic thermoplastic elastomers of poly(glycidyl nitrate)10.1002/app.40965 ↗
47. Anticorrosive conductive polyurethane multiwalled carbon nanotube nanocomposites10.1039/c3ta11966a ↗
48. Strain sensitive polyurethane nanocomposites reinforced with multiwalled carbon nanotubes10.1166/eef.2014.1093 ↗
49. Polyurethane wood adhesive from palm oil-based polyester polyol10.1080/01694243.2014.883772 ↗
50. A solventless castor oil-based pu adhesive for wood and foam substrates10.1016/j.ijadhadh.2010.07.001 ↗
51. Biomaterial based novel polyurethane adhesives for wood to wood and metal to metal bonding10.1590/S1516-14392009000400003 ↗