One-Step Method for Direct Acrylation of Vegetable Oils: A Biobased Material for 3D Printing

The substitution of fossil resources by alternatives derived from biomass is a reality that is taking on a growing relevance in the chemical and energy industries. In this sense, fats, oils, and their derived products have become indispensable inputs due to their broad functional attributes, stable price and sustainable character. Acrylated vegetable oils are considered to be very versatile materials for very broad applications (such as in adhesives, coatings or inks) since, in the presence of photoinitiators, they can be polymerized by means of UV-initiated free radical polymerizations. The usual process for the synthesis of acrylate vegetable oils consists in reacting epoxidized oils derivatives with acrylic acid. Here, the influence of different catalysts on the activity and selectivity of the process of acrylation of epoxidized soybean oil is studied. In addition, a novel one-step method for direct acrylation of vegetable oils is also explored. This new approach advantageously uses the original vegetable resource and eliminates intermediate reactions, thus being more environmentally efficient. This study offers a simple and low-cost option for synthesizing a biomass-derived monomer and studies the potential for the 3D printing of complex structures via digital light processing (DLP) 3D printing of the thus-obtained novel sustainable formulations.

[1]  D. Kalita,et al.  Bio-based coating resins derived from cardanol using carbocationic polymerization and their evaluation as one-component alkyd-type coatings , 2023, Progress in Organic Coatings.

[2]  M. Ebrahimi,et al.  A facile method to synthesis of a highly acrylated epoxidized soybean oil with low viscosity: Combined experimental and computational approach , 2022, Polymer Testing.

[3]  S. Gaidukovs,et al.  Acrylation of biomass: a review of synthesis process – know how and future application directions , 2022, Current Opinion in Green and Sustainable Chemistry.

[4]  R. Sesana,et al.  DLP-printable fully biobased soybean oil composites , 2022, Polymer.

[5]  S. Lanceros‐Méndez,et al.  Bio‐based Piezo‐ and Thermo‐Resistive Photo‐Curable Sensing Materials from Acrylated Epoxidized Soybean Oil , 2022, Macromolecular Materials and Engineering.

[6]  P. Siwayanan,et al.  Acrylated Biopolymers Derived via Epoxidation and Subsequent Acrylation of Vegetable Oils , 2022, International Journal of Polymer Science.

[7]  M. Koç,et al.  Vat photopolymerization of polymers and polymer composites: Processes and applications , 2021, Additive Manufacturing.

[8]  M. Zanetti,et al.  Thermochromic photoluminescent 3D printed polymeric devices based on copper-iodide clusters , 2021, Additive Manufacturing.

[9]  A. Sousa,et al.  Plastics from renewable sources as green and sustainable alternative , 2021, Current Opinion in Green and Sustainable Chemistry.

[10]  Sharon Miller,et al.  Industry 4.0 and circular economy practices: A new era business strategies for environmental sustainability , 2021, Business Strategy and the Environment.

[11]  M. Baker,et al.  An efficient and easily adjustable heating stage for digital light processing set-ups , 2021 .

[12]  S. Gaidukovs,et al.  UV-Light Curing of 3D Printing Inks from Vegetable Oils for Stereolithography , 2021, Polymers.

[13]  M. Sangermano,et al.  New UV‐Curable Anticorrosion Coatings from Vegetable Oils , 2021, Macromolecular Materials and Engineering.

[14]  T. Palanisami,et al.  COVID pollution: impact of COVID-19 pandemic on global plastic waste footprint , 2021, Heliyon.

[15]  Zhanjun Wu,et al.  A Review of the Polymer for Cryogenic Application: Methods, Mechanisms and Perspectives , 2021, Polymers.

[16]  M. Hakkarainen,et al.  Cationic UV-Curing of Epoxidized Biobased Resins , 2020, Polymers.

[17]  P. Gruber,et al.  Polymer architecture as key to unprecedented high-resolution 3D-printing performance: The case of biodegradable hexa-functional telechelic urethane-based poly-ε-caprolactone , 2020, Materials Today.

[18]  Vincent S. D. Voet,et al.  Sustainable Photopolymers in 3D Printing: A Review on Biobased, Biodegradable, and Recyclable Alternatives. , 2020, Macromolecular rapid communications.

[19]  M. Sangermano,et al.  Sustainable access to fully biobased epoxidized vegetable oil thermoset materials prepared by thermal or UV-cationic processes , 2020, RSC advances.

[20]  J. Ostrauskaite,et al.  High biorenewable content acrylate photocurable resins for DLP 3D printing , 2020 .

[21]  C. Pirri,et al.  Multiacrylated Cyclodextrin: A Bio‐Derived Photocurable Macromer for VAT 3D Printing , 2020 .

[22]  Zhuohong Yang,et al.  One-Step Synthesis of Novel Renewable Vegetable Oil-Based Acrylate Prepolymers and Their Application in UV-Curable Coatings , 2020, Polymers.

[23]  M. Ghobakhloo.  Industry 4.0, digitization, and opportunities for sustainability , 2020 .

[24]  Xiaoya Liu,et al.  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 coating , 2019, Progress in Organic Coatings.

[25]  Chengbo Liu,et al.  Preparation of high solid loading and low viscosity ceramic slurries for photopolymerization-based 3D printing , 2019, Ceramics International.

[26]  S. Sahoo,et al.  Synthesis and characterization of low viscous and highly acrylated epoxidized methyl ester based green adhesives derived from linseed oil , 2019, International Journal of Adhesion and Adhesives.

[27]  S. Lanceros‐Méndez,et al.  State‐of‐the‐Art and Future Challenges of UV Curable Polymer‐Based Smart Materials for Printing Technologies , 2019, Advanced Materials Technologies.

[28]  O. Kazantsev,et al.  Recent advances in the field of selective epoxidation of vegetable oils and their derivatives: a review and perspective , 2017 .

[29]  Thomas F. Garrison,et al.  Recent advances in vegetable oil-based polymers and their composites , 2017 .

[30]  A. Bandyopadhyay,et al.  Additive manufacturing: scientific and technological challenges, market uptake and opportunities , 2017 .

[31]  Lixin Wu,et al.  Structure-property relationship of nano enhanced stereolithography resin for desktop SLA 3D printer , 2016 .

[32]  D. Bieliński,et al.  Influence of Network Structure on Glass Transition Temperature of Elastomers , 2016, Materials.

[33]  S. Mohanty,et al.  Study of thermal stability and thermo-mechanical behavior of functionalized soybean oil modified toughened epoxy/organo clay nanocomposite , 2015 .

[34]  X. Sun,et al.  Synthesis and characterization of acrylic polyols and polymers from soybean oils for pressure-sensitive adhesives , 2015 .

[35]  Jinwen Zhang,et al.  Effects of Catalyst Type and Reaction Parameters on One-Step Acrylation of Soybean Oil , 2014 .

[36]  Vincent Lapinte,et al.  The use of renewable feedstock in UV-curable materials - A new age for polymers and green chemistry , 2013 .

[37]  Jinwen Zhang,et al.  One-step acrylation of soybean oil (SO) for the preparation of SO-based macromonomers , 2013 .

[38]  Li-Yu Fu,et al.  Thermal and mechanical properties of acrylated expoxidized‐soybean oil‐based thermosets , 2010 .

[39]  A. Bukowska,et al.  Reactivity of Some Carboxylic Acids in Reactions with Some Epoxides in the Presence Chromium (III) Ethanoate , 2002 .

[40]  Richard P. Wool,et al.  Development and application of triglyceride‐based polymers and composites , 2001 .

[41]  Kristi S. Anseth,et al.  Reaction behaviour and kinetic constants for photopolymerizations of multi(meth)acrylate monomers , 1994 .

[42]  R. Landel,et al.  Mechanical Properties of Polymers and Composites , 1993 .

[43]  J. McCutcheon.  Wijs Iodine Method , 1940 .

[44]  S. Gaidukovs,et al.  State-of-the-art UV-assisted 3D printing via a rapid syringe-extrusion approach for photoactive vegetable oil acrylates produced in one-step synthesis , 2022, Molecular Systems Design & Engineering.

[45]  Zhuohong Yang,et al.  UV/thermal dual curing of tung oil-based polymers induced by cationic photoinitiator , 2019, Progress in Organic Coatings.

[46]  V. Mannari,et al.  Development of soy-based UV-curable acrylate oligomers and study of their film properties , 2013 .