Bio-Based Epoxy Resins Derived From Eugenol With Low Dielectric Constant

In this paper, a series of bio-based epoxy resins containing organic silicone were prepared from eugenol through a mild synthetic route. Then, 4,4'-diaminophenyl methane (DDM) was applied to cure these epoxy resins, and bisphenol A epoxy resin (DGEBA) was used as a control. The chemical structures of the synthesized resins were characterized by nuclear magnetic resonance (H-1-NMR). Properties of the cured epoxy resins were investigated by dielectric test, differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), dynamic mechanical analysis (DMA), and scanning electron microscopy (SEM). Compared with DGEBA, the bio-based epoxy resin containing cyclic organic silicon structure exhibited a dramatically lower dielectric constant at both low and high frequencies (3.46, 1 kHz, room temperature). Moreover, the silicone-modified bio-based epoxy resins demonstrated no weight loss below 325 degrees C and higher residues at 800 degrees C than that of DGEBA.

[1]  Xiaoqing Liu,et al.  UV-thermal dual cured anti-bacterial thiol-ene networks with superior performance from renewable resources , 2017 .

[2]  X. Sui,et al.  Dielectric spectroscopy characterization of relaxation process in Ni/epoxy composites , 2016 .

[3]  C. Li,et al.  Green Synthesis of a Bio-Based Epoxy Curing Agent from Isosorbide in Aqueous Condition and Shape Memory Properties Investigation of the Cured Resin , 2016 .

[4]  Lingqian Kong,et al.  Low k epoxy resin containing cycloaliphatic hydrocarbon with high crosslinking density , 2016 .

[5]  M. Al-Maadeed,et al.  Improved flexible, controlled dielectric constant material from recycled LDPE polymer composites , 2016, Journal of Materials Science: Materials in Electronics.

[6]  R. Sun,et al.  Fibrous Epoxy Substrate with High Thermal Conductivity and Low Dielectric Property for Flexible Electronics , 2016 .

[7]  Lei Li,et al.  Enhancement of dielectric constants of epoxy thermosets via a fine dispersion of barium titanate nanoparticles , 2016 .

[8]  B. Bae,et al.  Thermally Stable Siloxane Hybrid Matrix with Low Dielectric Loss for Copper-Clad Laminates for High-Frequency Applications. , 2016, ACS applied materials & interfaces.

[9]  E. Vigueras-Santiago,et al.  Sweet polymers: Synthesis and characterization of xylitol-based epoxidized linseed oil resins , 2016 .

[10]  Tomonori Saito,et al.  Lignin-Derived Advanced Carbon Materials. , 2015, ChemSusChem.

[11]  Soo-Jin Park,et al.  Synthesis and application of epoxy resins: A review , 2015 .

[12]  R. Sun,et al.  Thermally reversible and self‐healing novolac epoxy resins based on Diels–Alder chemistry , 2015 .

[13]  W. Law,et al.  Enhancing the Heat Transfer Efficiency in Graphene-Epoxy Nanocomposites Using a Magnesium Oxide-Graphene Hybrid Structure. , 2015, ACS applied materials & interfaces.

[14]  M. Mariatti,et al.  Dielectric properties and thermal properties of calcium copper titanate and barium titanate hybrid fillers filled epoxy thin film composites for electronic packaging applications , 2015, Journal of Materials Science: Materials in Electronics.

[15]  S. Amico,et al.  Avaliação das características da resina epóxi com diferentes aditivos desaerantes , 2015 .

[16]  A. Satapathy,et al.  Epoxy Composites Filled with Micro-Sized AlN Particles for Microelectronic Applications , 2015 .

[17]  Y. Mai,et al.  High-performance epoxy/silica coated silver nanowire composites as underfill material for electronic packaging , 2014 .

[18]  A. Duval,et al.  A review on lignin-based polymeric, micro- and nano-structured materials , 2014 .

[19]  A. Satapathy,et al.  Thermal and dielectric behavior of epoxy composites filled with ceramic micro particulates , 2014 .

[20]  J. Puiggalí,et al.  Synthesis, Properties and Applications of Biodegradable Polymers Derived from Diols and Dicarboxylic Acids: From Polyesters to Poly(ester amide)s , 2014, International journal of molecular sciences.

[21]  Bernard Boutevin,et al.  Biobased thermosetting epoxy: present and future. , 2014, Chemical reviews.

[22]  Bo-geng Li,et al.  Novel silicon-modified phenolic novolacs and their biofiber-reinforced composites: Preparation, characterization and performance , 2013 .

[23]  H. Takagi,et al.  Evaluation of epoxy resins synthesized from steam-exploded bamboo lignin , 2013 .

[24]  Wanshuang Liu,et al.  Thermo-initiated cationic polymerization of phosphorus-containing cycloaliphatic epoxides with tunable degradable temperature , 2012 .

[25]  Wanshuang Liu,et al.  Synthesis and properties of two novel silicon‐containing cycloaliphatic epoxy resins for electronic packaging application , 2012 .

[26]  S. Caillol,et al.  From Vegetable Oils to Polyurethanes: Synthetic Routes to Polyols and Main Industrial Products , 2012 .

[27]  B. Ashrafi,et al.  Enhancement of mechanical performance of epoxy/carbon fiber laminate composites using single-walled carbon nanotubes , 2011 .

[28]  E. Bekyarova,et al.  Oxidized Graphite Nanoplatelets as an Improved Filler for Thermally Conducting Epoxy-Matrix Composites , 2011 .

[29]  Erol Sancaktar.  Electrically Conductive Epoxy Adhesives , 2011 .

[30]  Wanshuang Liu,et al.  Phosphorus-containing liquid cycloaliphatic epoxy resins for reworkable environment-friendly electronic packaging materials , 2010 .

[31]  Guangfu Zeng,et al.  Study on preparation and properties of epoxy resin modified by amine-terminated polyimide as electronic packaging materials , 2010, 2010 11th International Conference on Electronic Packaging Technology & High Density Packaging.

[32]  M. J. Thomas,et al.  Dielectric Properties of Epoxy-${\rm Al}_{2}{\rm O}_{3}$ Nanocomposite System for Packaging Applications , 2010, IEEE Transactions on Components and Packaging Technologies.

[33]  S. Hiziroglu,et al.  Effect of resin compositions on microwave processing and thermophysical properties of benzoxazine‐epoxy‐phenolic ternary systems filled with silicon carbide (SiC) whisker , 2009 .

[34]  Jian He,et al.  Simultaneously improved toughness and dielectric properties of epoxy/core‐shell particle blends , 2008 .

[35]  K. Hu,et al.  Comparative study on the curing kinetics and mechanism of a lignin-based-epoxy/anhydride resin system , 2007 .

[36]  M. Sham,et al.  Curing behavior and residual stresses in polymeric resins used for encapsulanting electronic packages , 2005 .

[37]  Wen‐Chang Chen,et al.  Organic–inorganic hybrid materials from a new octa(2,3-epoxypropyl)silsesquioxane with diamines , 2005 .

[38]  Wolfgang G. Glasser,et al.  Recent Industrial Applications of Lignin: A Sustainable Alternative to Nonrenewable Materials , 2002 .

[39]  P. Gonon,et al.  Dielectric properties of epoxy/silica composites used for microlectronic packaging, and their dependence on post-curing , 2001 .

[40]  Chun-Shan Wang,et al.  Modification of epoxy resin with siloxane containing phenol aralkyl epoxy resin for electronic encapsulation application , 2001 .

[41]  D. Ratna,et al.  Toughened epoxy adhesive modified with acrylate based liquid rubber , 2000 .

[42]  D. Ratna,et al.  Epoxidized soybean oil toughened epoxy adhesive , 2000 .

[43]  Ching-Ping Wong,et al.  Syntheses and characterizations of thermally reworkable epoxy resins II , 1999 .

[44]  D.D.L. Chung,et al.  Short carbon fiber reinforced epoxy coating as a piezoresistive strain sensor for cement mortar , 1998 .

[45]  Chee Choong Kooi,et al.  Preparation and properties of POSS/epoxy composites for electronic packaging applications , 2009 .