Wood pulp industry by-product valorization for acrylate synthesis and bio-based polymer development via Michael addition reaction
Source abstract
Abstract
It is crucial to adapt the processing of forest bio-resources into biochemicals and bio-based advanced materials in order to transform the current economic climate into a greener economy. Tall oil, as a by-product of the Kraft process of wood pulp manufacture, is a promising resource for the extraction of various value-added products. Tall oil fatty acids-based multifunctional Michael acceptor acrylates were developed. The suitability of developed acrylates for polymerization with tall oil fatty acids-based Michael donor acetoacetates to form a highly cross-linked polymer material via the Michael addition was investigated. With this novel strategy, valuable chemicals and innovative polymer materials can be produced from tall oil in an entirely new way, making a significant contribution to the development of a forest-based bioeconomy. Two different tall oil-based acrylates were successfully synthesized and characterized. Synthesized acrylates were successfully used in the synthesis of bio-based thermoset polymers. Obtained polymers had a wide variety of mechanical and thermal properties (glass transition temperature from –12.1 to 29.6 °C by dynamic mechanical analysis, Young's modulus from 15 to 1 760 MPa, and stress at break from 0.9 to 16.1 MPa). Gel permeation chromatography, Fourier-transform infrared (FT-IR) spectroscopy, matrix-assisted laser desorption/ionization-time of flight mass spectrometry, and nuclear magnetic resonance were used to analyse the chemical structure of synthesized acrylates. In addition, various titration methods and rheology tests were applied to characterize acrylates. The chemical composition and thermal and mechanical properties of the developed polymers were studied by using FT-IR, solid-state nuclear magnetic resonance, thermal gravimetric analysis, differential scanning calorimetry, dynamic mechanical analysis, and universal strength testing apparatus.
Source: openalex_inverted_index · Quality: baseline
Research context
OpenAlex topics: biodegradable polymer synthesis and properties · Lignin and Wood Chemistry · Polymer composites and self-healing
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (64)
Show source-provided references
1. Impact of different epoxidation approaches of tall oil fatty acids on rigid polyurethane foam thermal insulation10.3390/ma14040894 ↗
2. The crude tall oil value chain: global availability and the influence of regional energy policies10.1016/j.jclepro.2020.124616 ↗
3. A facile method to synthesis of a highly acrylated epoxidized soybean oil with low viscosity: combined experimental and computational approach10.1016/j.polymertesting.2022.107727 ↗
4. DMA analysis of the structure of crosslinked poly(methyl methacrylate)s
5. Partially acrylated linseed oil UV-cured coating containing a dihemiacetal ester for the corrosion protection of an aluminium alloy
6. State-of-the-art UV-assisted 3D printing via a rapid syringe-extrusion approach for photoactive vegetable oil acrylates produced in one-step synthesis10.1039/D2ME00085G ↗
7. Bio-based coating materials derived from acetoacetylated soybean oil and aromatic dicarboxaldehydes10.3390/polym11111809 ↗
8. Characterisation of epoxidised trimethylolpropane trioleate: NMR and thermogravimetric analysis
9. Claux · 2023
10. Fully bio-derived CO2 polymers for non-isocyanate based polyurethane synthesis10.1039/C9GC03488A ↗
11. European Commission, 2019. The European Green Deal. Available at: https://www.europarl.europa.eu/RegData/etudes/ATAG/2019/644205/EPRS_ATA(2019)644205_EN.pdf#:∼:text=The%20European%20Green%20Deal%20is%20a%20programme%20outlined,an%20extraordinary%20plenary%20session%20on%2011%20December%202019.
12. Photo-cured materials from vegetable oils
13. The application of timoho fiber coating to improve the composite performance10.1016/j.rineng.2022.100499 ↗
14. Developing acrylated epoxidized soybean oil coating for improving moisture sensitivity and permeability of starch-based film10.1016/j.ijbiomac.2018.11.239 ↗
15. An exploration of the Knoevenagel condensation to create ambient curable coating materials based on acetoacetylated castor oil10.1016/j.porgcoat.2018.12.015 ↗
16. A coating from nature10.1126/sciadv.abe0026 ↗
17. Calculation of crosslink density in short chain networks10.1016/S0300-9440(97)00081-7 ↗
18. Synthesis and application of UV-curable phosphorous-containing acrylated epoxidized soybean oil-based resins10.1016/j.biortech.2019.02.012 ↗
19. Synthesis and characterization of hyperbranched polyurethane hybrids using tetraethoxysilane (TEOS) as cross-linker10.1021/ie800884y ↗
20. Isocyanate free polyurethanes from new CNSL based bis-cyclic carbonate and its application in coatings10.1016/j.eurpolymj.2014.05.008 ↗
21. Non-isocyanate polyurethanes: from chemistry to applications10.1039/c2ra21938g ↗
22. Synthesis and characterization of a polyurethane phase separated to nano size in an epoxy polymer10.3390/coatings9050319 ↗
23. Rapeseed oil as feedstock for high functionality polyol synthesis10.7569/JRM.2017.634116 ↗
24. Influence of different synthesis conditions on the chemo-enzymatic epoxidation of tall oil fatty acids10.1016/j.procbio.2022.08.024 ↗
25. Catalyst-free lignin valorization by acetoacetylation. Structural elucidation by comparison with model compounds10.1039/C8GC01071D ↗
26. The effect of fatty acid composition on the acrylation kinetics of epoxidized triacylglycerols10.1007/s11746-002-0435-4 ↗
27. Synthesis and characterization of acrylic polyols and polymers from soybean oils for pressure-sensitive adhesives10.1039/C5RA04399A ↗
28. Synthesis and characterization of novel renewable tung oil-based UV-curable active monomers and bio-based copolymers10.1016/j.porgcoat.2019.01.007 ↗
29. TRPA1 and issues relating to animal model selection for extrapolating toxicity data to humans10.1177/0960327119877460 ↗
30. Highly functional bio-based acrylates with a hard core and soft arms: from synthesis to enhancement of an acrylated epoxidized soybean oil-based UV-curable coating10.1016/j.porgcoat.2019.05.025 ↗
31. Fatty acid-based radically polymerizable monomers: from novel poly(meth)acrylates to cutting-edge properties10.1021/acs.biomac.8b01156 ↗
32. Thiol-ene” photo-cured hybrid materials based on POSS and renewable vegetable oil10.1039/c1jm11425e ↗
33. Menard · 1999
34. Synthesis and radiation curing of acrylated castor oil glycerides10.1007/s11998-014-9596-5 ↗
35. Synthesis of gels by means of Michael addition reaction of multi-functional acetoacetate and diacrylate compounds and their application to ionic conductive gels10.1002/pol.20210388 ↗
36. Synthesis of porous polymers by means of Michael addition reaction of multifunctional acetoacetate and poly(ethylene glycol) diacrylate10.1016/j.eurpolymj.2021.110901 ↗
37. Michael addition curable coatings from renewable resources with enhanced adhesion performance10.1007/s11998-020-00351-2 ↗
38. Thinking green: sustainable polymers from renewable resources10.3390/polym10090952 ↗
39. The exploration of Michael-addition reaction chemistry to create high performance, ambient cure thermoset coatings based on soybean oil10.1016/j.porgcoat.2017.04.004 ↗
40. Renewable polymers and plastics: performance beyond the green10.1016/j.nbt.2020.10.003 ↗
41. Bioprocess development for biolubricant production using non-edible oils, agro-industrial byproducts and wastes10.1016/j.jclepro.2022.131956 ↗
42. Epoxidation of tall oil fatty acids and tall oil fatty acids methyl esters using the SpinChem® rotating bed reactor10.1007/s10924-022-02556-5 ↗
43. The synthesis of bio-based Michael donors from tall oil fatty acids for polymer development10.3390/polym14194107 ↗
44. Bio-based polymer developments from tall oil fatty acids by exploiting Michael addition10.3390/polym14194068 ↗
45. Effect of cross-linking on dynamic mechanical and fracture behavior of epoxy variants10.1016/j.compositesb.2015.09.017 ↗
46. UV-curable PUDs based on sustainable acrylated polyol: study of their hydrophobic and oleophobic properties10.1016/j.porgcoat.2013.11.029 ↗
47. Bioplastics for a circular economy10.1038/s41578-021-00407-8 ↗
48. Synthesis of radiation curable palm oil-based epoxy acrylate: NMR and FTIR spectroscopic investigations10.3390/molecules200814191 ↗
49. Byproducts from the vegetable oil industry: the challenges of safety and sustainability10.3390/su14042039 ↗
50. From rigid and flexible foams to elastomers via Michael addition chemistry10.1016/j.polymer.2016.10.054 ↗
51. Materials for the biorefinery: high bio-content, shape memory Kraft lignin-derived non-isocyanate polyurethane foams using a non-toxic protocol10.1039/D0GC01659D ↗
52. One-step synthesis of novel renewable vegetable oil-based acrylate prepolymers and their application in UV-curable coatings10.3390/polym12051165 ↗
53. Cardanol modified fatty acids from camelina oils for flexible bio-based acrylates coatings10.1016/j.porgcoat.2018.02.008 ↗
54. Preparation and properties of plant-oil-based epoxy acrylate-like resins for UV-curable coatings10.3390/polym12092165 ↗
55. Acetoacetylated castor oil in coatings applications10.1016/S0300-9440(01)00223-5 ↗
56. A review of wood biomass-based fatty acids and rosin acids use in polymeric materials10.3390/polym12112706 ↗
57. An ambient curable coating material based on the Michael addition reaction of acetoacetylated castor oil and multifunctional acrylate10.3390/coatings9010037 ↗
58. Transacetoacetylation with tert-butyl acetoacetate: synthetic applications10.1021/jo00005a013 ↗
59. Photocrosslinking of an acrylated epoxidized linseed oil: kinetics and its application for optimized wood coatings10.1007/s10924-012-0511-9 ↗
60. Vegetable oil-based polymeric materials: synthesis, properties, and applications10.1039/c0gc00264j ↗
61. An ambient-cured coating film obtained via a Knoevenagel and Michael addition reactions based on modified acetoacetylated castor oil prepared by a thiol-ene coupling reaction10.1016/j.porgcoat.2019.06.026 ↗
62. Biobased polyurethanes prepared from different vegetable oils10.1021/am5071333 ↗
63. Effects of catalyst type and reaction parameters on one-step acrylation of soybean oil10.1021/sc400206t ↗
64. One-step acrylation of soybean oil (SO) for the preparation of SO-based macromonomers10.1039/c3gc36961g ↗