An Eco-Friendly Scheme for the Cross-Linked Polybutadiene Elastomer via Thiol–Ene and Diels–Alder Click Chemistry

We reported a novel method of producing the cross-linked polybutadiene elastomer which could be thermally recycled like the plastic materials without the sacrifice of functional utility. The commercial polybutadiene was first attached with furan via thiol–ene reaction, and the cross-linked network was then built via Diels–Alder click reaction between the bismaleimide and attached furan groups from polybutadiene. The obtained polymer had good solvent resistance from ambient temperature to 100 °C. The mechanical properties of modified polybutadiene could be tailored by the amount of attached furan and the ratio of furan to bismaleimide. Furthermore, the dynamic cross-linked polybutadiene had good thermally remolded and self-healing behaviors. By this method, the dynamic cross-linked polybutadiene could be recycled to use in a sustainable way. Concerning all the raw materials were available in large quantities without tedious and multistep synthetic routes, this work demonstrated the high performance recycli...

[1]  A. Sanyal.  Diels–Alder Cycloaddition‐Cycloreversion: A Powerful Combo in Materials Design , 2010 .

[2]  A. Lowe,et al.  Thiol-ene “click” reactions and recent applications in polymer and materials synthesis , 2010 .

[3]  Christopher N Bowman,et al.  Thiol-ene click chemistry. , 2010, Angewandte Chemie.

[4]  Stuart J Rowan,et al.  Dynamic covalent chemistry. , 2002, Angewandte Chemie.

[5]  Julia A. Kornfield,et al.  Facile, Efficient Routes to Diverse Protected Thiols and to Their Deprotection and Addition to Create Functional Polymers by Thiol-Ene Coupling , 2008 .

[6]  Fred Wudl,et al.  The world of smart healable materials , 2010 .

[7]  Amy M. Peterson,et al.  Room temperature self-healing thermoset based on the Diels-Alder reaction. , 2013, ACS applied materials & interfaces.

[8]  Youchun Zhang,et al.  Thermally Self-Healing Polymeric Materials : The Next Step to Recycling Thermoset Polymers? , 2009 .

[9]  Chia-Yun Hsieh,et al.  Crosslinked epoxy materials exhibiting thermal remendablility and removability from multifunctional maleimide and furan compounds , 2006 .

[10]  Qiang Wu,et al.  Bio‐Inspired High‐Performance and Recyclable Cross‐Linked Polymers , 2013, Advanced materials.

[11]  Ying‐Ling Liu,et al.  Self-healing polymers based on thermally reversible Diels–Alder chemistry , 2013 .

[12]  H. Sodano,et al.  Self‐Healing Polyurethanes with Shape Recovery , 2014 .

[13]  A. Gandini,et al.  Recycling Tires? Reversible Crosslinking of Poly(butadiene) , 2015, Advanced materials.

[14]  A. Gandini,et al.  Materials from renewable resources based on furan monomers and furan chemistry: work in progress , 2009 .

[15]  H. Schlaad,et al.  Thiol#Ene Modification of 1,2-Polybutadiene Using UV Light or Sunlight , 2008 .

[16]  S. Nutt,et al.  A Thermally Re-mendable Cross-Linked Polymeric Material , 2002, Science.

[17]  Tatiana Tambouratzis,et al.  A Methodological Study for Optimizing Material Selection in Sustainable Product Design , 2014 .

[18]  B. Adhikari,et al.  Reclamation and recycling of waste rubber , 2000 .

[19]  M. Taşdelen,et al.  Diels–Alder “click” reactions: recent applications in polymer and material science , 2011 .

[20]  Ying Wang,et al.  The status of recycling of waste rubber , 2001 .

[21]  Amy M. Peterson,et al.  Diffusion and Reaction Phenomena in Solution‐Based Healing of Polymer Coatings Using the Diels–Alder Reaction , 2012 .

[22]  C. Bowman,et al.  Thiol-click chemistry: a multifaceted toolbox for small molecule and polymer synthesis. , 2010, Chemical Society reviews.

[23]  Fred Wudl,et al.  Synthesis and Characterization of a Single-Component Thermally Remendable Polymer Network: Staudinger and Stille Revisited , 2008 .