RAFT polymerisation of renewable terpene (meth)acrylates and the convergent synthesis of methacrylate–acrylate–methacrylate triblock copolymers

We now report the synthesis of well-defined terpene-based polymers and precise di- and multiblock copolymer architectures by use of RAFT, wide range of Tg and promising adhesive properties are observed.

[1]  S. Howdle,et al.  Synthesis of novel carvone (meth)acrylate monomers for the production of hydrophilic polymers with high terpene content , 2020 .

[2]  Martijn A. Droesbeke,et al.  Biosourced terpenoids for the development of sustainable acrylic pressure-sensitive adhesives via emulsion polymerisation , 2020, Green Chemistry.

[3]  Matthias Wendt,et al.  PhD thesis , 2020 .

[4]  L. Billon,et al.  Bioinspired Enzymatic Synthesis of Terpenoid-Based (Meth)acrylic Monomers: A Solvent-, Metal-, Amino-, and Halogen-Free Approach , 2020 .

[5]  S. Howdle,et al.  A ‘greener’ one-pot synthesis of monoterpene-functionalised lactide oligomers , 2020 .

[6]  L. Billon,et al.  On the nitroxide mediated polymerization of methacrylates derived from bio-sourced terpenes in miniemulsion, a step towards sustainable products , 2020 .

[7]  C.C.W.J. Clarijs,et al.  Strain hardening in glassy polymers: Influence of network density on elastic and viscous contributions , 2019, Journal of Polymer Science Part B: Polymer Physics.

[8]  J. Mays,et al.  Recent advances in thermoplastic elastomers from living polymerizations: Macromolecular architectures and supramolecular chemistry , 2019, Progress in Polymer Science.

[9]  Martijn A. Droesbeke,et al.  Sustainable Synthesis of Renewable Terpenoid-Based (Meth)acrylates Using the CHEM21 Green Metrics Toolkit , 2019, ACS Sustainable Chemistry & Engineering.

[10]  L. Billon,et al.  Renewable Terpene Derivative as a Biosourced Elastomeric Building Block in the Design of Functional Acrylic Copolymers. , 2019, Biomacromolecules.

[11]  S. Howdle,et al.  Polyacrylates Derived from Biobased Ethyl Lactate Solvent via SET-LRP. , 2019, Biomacromolecules.

[12]  J. Dubois,et al.  Catalysis for the synthesis of methacrylic acid and methyl methacrylate. , 2018, Chemical Society reviews.

[13]  Jinmei He,et al.  Fabrication of acrylic pressure-sensitive adhesives containing maleimide for heat-resistant adhesive applications , 2018, Polymer Bulletin.

[14]  Thomas H. Epps,et al.  From Tree to Tape: Direct Synthesis of Pressure Sensitive Adhesives from Depolymerized Raw Lignocellulosic Biomass , 2018, ACS central science.

[15]  V. Percec,et al.  SET-LRP of the Hydrophobic Biobased Menthyl Acrylate. , 2018, Biomacromolecules.

[16]  N. Bauer,et al.  Controlled Radical Polymerization of Myrcene in Bulk: Mapping the Effect of Conditions on the System , 2017 .

[17]  Sébastien Perrier,et al.  50th Anniversary Perspective: RAFT Polymerization—A User Guide , 2017 .

[18]  Jiahua Zhu,et al.  All acrylic-based thermoplastic elastomers with high upper service temperature and superior mechanical properties , 2017 .

[19]  S. Zwaag,et al.  Contributions of hard and soft blocks in the self-healing of metal-ligand-containing block copolymers , 2017 .

[20]  Seok-Ho Hwang,et al.  Preparation of biomass-based transparent pressure sensitive adhesives for optically clear adhesive and their adhesion performance , 2017 .

[21]  Andreas F. Thunemann,et al.  The modular small-angle X-ray scattering data correction sequence , 2017, Journal of applied crystallography.

[22]  Matthew D. Jones,et al.  Polymerisation of a terpene-derived lactone: a bio-based alternative to ε-caprolactone , 2017 .

[23]  U. Bornscheuer,et al.  From waste to value – direct utilization of limonene from orange peel in a biocatalytic cascade reaction towards chiral carvolactone , 2017 .

[24]  K. Baek,et al.  Control of hard block segments of methacrylate-based triblock copolymers for enhanced electromechanical performance , 2016 .

[25]  S. Howdle,et al.  Progress in the synthesis of sustainable polymers from terpenes and terpenoids , 2016 .

[26]  José A. Souto,et al.  A facile and green route to terpene derived acrylate and methacrylate monomers and simple free radical polymerisation to yield new renewable polymers and coatings , 2016 .

[27]  Andreas Greiner,et al.  Bio-based polycarbonate from limonene oxide and CO2 with high molecular weight, excellent thermal resistance, hardness and transparency , 2016 .

[28]  D. Irvine,et al.  Molecular Design of Squalene/Squalane Countertypes via the Controlled Oligomerization of Isoprene and Evaluation of Vaccine Adjuvant Applications. , 2016, Biomacromolecules.

[29]  Gergely Kali,et al.  Bio-based polymyrcene with highly ordered structure via solvent free controlled radical polymerization , 2015 .

[30]  R. Vendamme,et al.  Recent synthetic approaches and emerging bio-inspired strategies for the development of sustainable pressure-sensitive adhesives derived from renewable building blocks , 2014 .

[31]  M. Jonsson,et al.  Bringing D-limonene to the scene of bio-based thermoset coatings via free-radical thiol–ene chemistry: macromonomer synthesis, UV-curing and thermo-mechanical characterization , 2014 .

[32]  R. Sheldon.  Green and sustainable manufacture of chemicals from biomass: state of the art , 2014 .

[33]  Daniel J. Keddie,et al.  A guide to the synthesis of block copolymers using reversible-addition fragmentation chain transfer (RAFT) polymerization. , 2014, Chemical Society reviews.

[34]  S. Perrier,et al.  Exploitation of the Degenerative Transfer Mechanism in RAFT Polymerization for Synthesis of Polymer of High Livingness at Full Monomer Conversion , 2014 .

[35]  Thomas Maschmeyer,et al.  Rapid and quantitative one-pot synthesis of sequence-controlled polymers by radical polymerization , 2013, Nature Communications.

[36]  M. Kamigaito,et al.  1:2‐sequence‐regulated radical copolymerization of naturally occurring terpenes with maleimide derivatives in fluorinated alcohol , 2013 .

[37]  M. Meier,et al.  Renewable polyamides and polyurethanes derived from limonene , 2013 .

[38]  Graeme Moad,et al.  RAFT Agent Design and Synthesis , 2012 .

[39]  S. Howdle,et al.  Controlled oligomerisation of isoprene-towards the synthesis of squalene analogues , 2012 .

[40]  M. Meier,et al.  Terpene-Based Renewable Monomers and Polymers via Thiol–Ene Additions , 2011 .

[41]  M. Hillmyer,et al.  Functional biorenewable polyesters from carvone-derived lactones , 2011 .

[42]  Jane E. Wissinger,et al.  Pressure-Sensitive Adhesives from Renewable Triblock Copolymers , 2011 .

[43]  Shiping Zhu,et al.  Polystyrene-block-poly(n-butyl acrylate)-block-polystyrene Triblock Copolymer Thermoplastic Elastomer Synthesized via RAFT Emulsion Polymerization , 2010 .

[44]  A. M. D. Ilarduya,et al.  Poly(ethylene‐co‐1,4‐cyclohexylenedimethylene terephthalate) copolyesters obtained by ring opening polymerization , 2009 .

[45]  Hui Liang,et al.  Controlled radical copolymerization of β-pinene and n-butyl acrylate , 2007 .

[46]  Yi Wang,et al.  Reversible addition-fragmentation chain transfer radical copolymerization of β-pinene and methyl acrylate , 2006 .

[47]  Jennifer Markarian,et al.  Advances in PVC heat and light stabilization , 2004 .

[48]  Yong-Chan Chung,et al.  Comparison of thermal/mechanical properties and shape memory effect of polyurethane block-copolymers with planar or bent shape of hard segment , 2003 .

[49]  Graeme Moad,et al.  Living free radical polymerization with reversible addition-fragmentation chain transfer (RAFT polymerization): Approaches to star polymers , 2003 .

[50]  J. Lai,et al.  Functional Polymers from Novel Carboxyl-Terminated Trithiocarbonates as Highly Efficient RAFT Agents , 2002 .

[51]  Richard J. Spontak,et al.  Thermoplastic elastomers: fundamentals and applications , 2000 .

[52]  L. Daroczi,et al.  Starpolymers by soft-hard-soft block copolymers , 1997 .

[53]  A. Gent.  A New Constitutive Relation for Rubber , 1996 .

[54]  B. Boyes,et al.  Size Exclusion Chromatography , 1988 .

[55]  S. Bahadur.  Strain hardening equation and the prediction of tensile strength of rolled polymers , 1973 .

[56]  Jacqueline I. Kroschwitz,et al.  Encyclopedia of Polymer Science and Technology , 1970 .

[57]  V. Garcia,et al.  Gelatin and pregelatinized starch orally disintegrating films: Properties and stability of vitamin C , 2017 .

[58]  Jianying Ma,et al.  Kinetic investigations of RAFT polymerization: Difunctional RAFT agent mediated polymerization of methyl methacrylate and styrene , 2014, Macromolecular Research.

[59]  L. Leibler,et al.  Block copolymers in tomorrow's plastics , 2005, Nature materials.

[60]  P. Cutler.  Size-exclusion chromatography. , 2004, Methods in molecular biology.

[61]  T. Fox.  Influence of Diluent and of Copolymer Composition on the Glass Temperature of a Poly-mer System , 1956 .