Thermosetting Resins

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Xiaoqing Liu - One of the best experts on this subject based on the ideXlab platform.

  • Advances in sustainable Thermosetting Resins: From renewable feedstock to high performance and recyclability
    Progress in Polymer Science, 2021
    Co-Authors: Jingkai Liu, Jin Zhu, Shuaipeng Wang, Yunyan Peng, Weiwei Zhao, Xiaoqing Liu
    Abstract:

    Abstract In polymer science and industry, the important role of Thermosetting resin is well-recognized. However, most thermosets suffer from the overdependence on petroleum resource and in addition are linked to environmental concerns. The development of sustainable Thermosetting Resins thus has become an objective of contemporary research. Addressing this need generally requires renewable feedstocks, satisfied comprehensive properties, and long service life or recyclability. Herein, a systematic overview regarding recent advances in sustainable Thermosetting Resins is provided. Firstly, the origins and access of bio-based platform compounds successfully applied in the bio-based Thermosetting Resins are being discussed. Subsequently, the synthesis, structure-property relationships, and methodologies for the functionalization of three typical bio-based thermosets, including benzoxazine, epoxy resin and unsaturated polyester, are being reviewed. Finally, strategies for the recycling of bio-based thermoset waste products are being presented. The objective of this work is not only to summarize the recent progress on sustainable thermosets, but also help us understand them more deeply and widely in a short time, so as to promote their faster development.

  • Research progress on bio‐based Thermosetting Resins
    Polymer International, 2015
    Co-Authors: Xiaoqing Liu, Jin Zhu
    Abstract:

    Compared with the rapid progress on bio-based thermoplastics, research on bio-based Thermosetting Resins should have attracted much more attention, considering that they will have a bright future. In this paper, the current research progress on bio-based Thermosetting Resins is reviewed. We pay special attention to the synthesis and investigation of properties of epoxies and unsaturated polyesters derived from renewable plant oil, cardanol, rosin acid, lignin, glycerol, gallic acid, furan, isosorbide, itaconic acid, etc. This mini review gives an overall perspective for bio-based thermosets. (C) 2015 Society of Chemical Industry

  • synthesis and properties of full bio based Thermosetting Resins from rosin acid and soybean oil the role of rosin acid derivatives
    Green Chemistry, 2013
    Co-Authors: Xiaoqing Liu, Ruoyu Zhang, Ji Zhu, Yanhua Jiang
    Abstract:

    Two kinds of rosin acid derivatives were synthesized to serve as the rigid monomers to copolymerize with acrylated epoxidized soybean oil (AESO). Full bio-based Thermosetting Resins with satisfactory properties were then prepared. For comparison, petroleum-based divinylbenzene (DVB) was also used to copolymerize with the same AESO. The chemical structures of the synthesized rosin derivatives were confirmed by 1H NMR, 13C NMR and FT-IR before polymerization. The mechanical and thermal properties of the resulting thermosets were investigated by differential scanning calorimetry (DSC), dynamic mechanical analysis (DMA) and thermogravimetric analysis (TGA). Results demonstrated that the glass transition temperatures, tensile strength and modulus of the cured AESO were significantly improved after copolymerization with the rosin derivatives. The rosin acid derivatives showed great potential to replace petroleum-based rigid compounds for preparing soybean oil-based thermosets. The important information about how to design and synthesize more renewable thermosets with satisfactory properties was provided in this study.

Ying-ling Liu - One of the best experts on this subject based on the ideXlab platform.

  • the michael addition reaction of meldrum s acid ma an effective route for the preparation of reactive precursors for ma based Thermosetting Resins
    Polymer Chemistry, 2019
    Co-Authors: Chienho Huang, Ying-ling Liu
    Abstract:

    Meldrum's acid (MA) could be considered as a precursor of a highly reactive ketene group, and consequently is a suitable group for building up crosslinkable small molecular compounds and polymer chains. In this work, the Michael addition reaction of MA is applied for the preparation of multifunctional MA-containing compounds, exploring an effective route to synthesize multifunctional MA compounds, used as monomers for the corresponding MA-based Thermosetting Resins. Moreover, MA is utilized as a difunctional monomer to be polymerized with a bismaleimide (BMI) through the Michael addition reaction. A polymerization method directly using MA as a monomer for the synthesis of reactive and crosslinkable MA-containing polymers (poly(BMI-MA)) is demonstrated. The corresponding crosslinked CR-poly(BMI-MA) sample shows a high glass transition temperature (315 °C), high mechanical strength and a low dielectric constant of 3.15 at 1 MHz. A new type of MA reactive route and the corresponding high performance crosslinked Resins are demonstrated.

  • Thermosetting Resins based on a self crosslinkable monomer polymer possessing meldrum s acid groups
    Macromolecular Chemistry and Physics, 2017
    Co-Authors: Yu-kai Chou, Yi Chen, Liang-kai Lin, Ying-ling Liu
    Abstract:

    Thermosetting Resins based on Meldrum's acid (MA) derivatives as monomers show high thermal stability and inherent low-dielectric constants. In this work, a multifunctional MA derivative (MA-bisF) possessing two MA and two furan groups is newly prepared. Characterization of MA-bisF has been carried out with Fourier transform infrared, 1H NMR, mass spectroscopy, and elemental analysis. Self-crosslinking MA-bisF results in the corresponding Thermosetting resin mediating the addition reaction between ketene/ketene and ketene/furan groups. MA-bisF is also utilized as a modifier for bismaleimide (BMI) Resins through polymerizing MA-bisF and BMI through Diels–Alder reaction. The corresponding crosslinked MA-bisF/BMI resin possesses a high content of fused-ring structure and a high crosslinking density, so as to exhibit high thermal stability (392 °C), high glass transition temperature (262 °C), high char yield (48 wt%), and a low-dielectric constant of 2.78 at 1 MHz. A new type of reactive polymers and the corresponding high-performance crosslinked Resins has been demonstrated.

  • Thermosetting Resins Based on a Self‐Crosslinkable Monomer/Polymer Possessing Meldrum's Acid Groups
    Macromolecular Chemistry and Physics, 2017
    Co-Authors: Yu-kai Chou, Yi Chen, Liang-kai Lin, Ying-ling Liu
    Abstract:

    Thermosetting Resins based on Meldrum's acid (MA) derivatives as monomers show high thermal stability and inherent low-dielectric constants. In this work, a multifunctional MA derivative (MA-bisF) possessing two MA and two furan groups is newly prepared. Characterization of MA-bisF has been carried out with Fourier transform infrared, 1H NMR, mass spectroscopy, and elemental analysis. Self-crosslinking MA-bisF results in the corresponding Thermosetting resin mediating the addition reaction between ketene/ketene and ketene/furan groups. MA-bisF is also utilized as a modifier for bismaleimide (BMI) Resins through polymerizing MA-bisF and BMI through Diels–Alder reaction. The corresponding crosslinked MA-bisF/BMI resin possesses a high content of fused-ring structure and a high crosslinking density, so as to exhibit high thermal stability (392 °C), high glass transition temperature (262 °C), high char yield (48 wt%), and a low-dielectric constant of 2.78 at 1 MHz. A new type of reactive polymers and the corresponding high-performance crosslinked Resins has been demonstrated.

  • a cocatalytic effect between meldrum s acid and benzoxazine compounds in preparation of high performance Thermosetting Resins
    Macromolecular Rapid Communications, 2017
    Co-Authors: Yi Chen, Liang-kai Lin, Shujen Chiang, Ying-ling Liu
    Abstract:

    In this work, a cocatalytic effect between Meldrum's acid (MA) and benzoxazine (Bz) compounds has been explored to build up a self-promoting curing system. Consequently, the MA/Bz reactive blend exhibits a relatively low reaction temperature compared to the required temperatures for the cross-linking reactions of the pure MA and Bz components. This feature is attractive for energy-saving processing issues. Moreover, the Thermosetting Resins based on the MA/Bz reactive blends have been prepared. The MA component can generate additional free volume in the resulting Resins, so as to trap air in the resin matrix and consequently to bring low dielectric constants to the Resins. The MA-containing agent is an effective modifier for benzoxazine Resins to reduce their dielectric constants.

  • Novel Thermosetting Resins based on 4-(N-maleimido)phenylglycidylether III. Studies on the thermal degradation kinetics and mechanisms of the cured Resins
    Polymer Degradation and Stability, 2004
    Co-Authors: Ying-ling Liu, Wen-lung Wei, Yu-jane Chen, Mei-hui Tsai
    Abstract:

    The thermal degradation kinetics and mechanisms of Thermosetting Resins based on 4-(N-maleimido)phenylglycidylether (MPGE) were investigated with TGA, GC/MS, and FTIR. Two samples from MPGE cured with 4,4#-diaminodiphenylmethane (DDM) and diethylphosphite (DEP), respectively, were studied. The MPGE based Resins showed good thermal stability over conventional epoxy Resins. The degradation of MPGEeDEP was found to be initially triggered at the phosphonic ester linkage, while MPGEeDDM reacted at the epoxy linkage. Introducing phosphorus therefore significantly altered the patterns, activation energies, and mechanisms of the degradation reactions of the MPGE Resins. This change caused the MPGEeDEP resin to show good thermal stability, high activation energies of degradation, and enriched char formation. 2004 Elsevier Ltd. All rights reserved.

Jin Zhu - One of the best experts on this subject based on the ideXlab platform.

  • Advances in sustainable Thermosetting Resins: From renewable feedstock to high performance and recyclability
    Progress in Polymer Science, 2021
    Co-Authors: Jingkai Liu, Jin Zhu, Shuaipeng Wang, Yunyan Peng, Weiwei Zhao, Xiaoqing Liu
    Abstract:

    Abstract In polymer science and industry, the important role of Thermosetting resin is well-recognized. However, most thermosets suffer from the overdependence on petroleum resource and in addition are linked to environmental concerns. The development of sustainable Thermosetting Resins thus has become an objective of contemporary research. Addressing this need generally requires renewable feedstocks, satisfied comprehensive properties, and long service life or recyclability. Herein, a systematic overview regarding recent advances in sustainable Thermosetting Resins is provided. Firstly, the origins and access of bio-based platform compounds successfully applied in the bio-based Thermosetting Resins are being discussed. Subsequently, the synthesis, structure-property relationships, and methodologies for the functionalization of three typical bio-based thermosets, including benzoxazine, epoxy resin and unsaturated polyester, are being reviewed. Finally, strategies for the recycling of bio-based thermoset waste products are being presented. The objective of this work is not only to summarize the recent progress on sustainable thermosets, but also help us understand them more deeply and widely in a short time, so as to promote their faster development.

  • Research progress on bio‐based Thermosetting Resins
    Polymer International, 2015
    Co-Authors: Xiaoqing Liu, Jin Zhu
    Abstract:

    Compared with the rapid progress on bio-based thermoplastics, research on bio-based Thermosetting Resins should have attracted much more attention, considering that they will have a bright future. In this paper, the current research progress on bio-based Thermosetting Resins is reviewed. We pay special attention to the synthesis and investigation of properties of epoxies and unsaturated polyesters derived from renewable plant oil, cardanol, rosin acid, lignin, glycerol, gallic acid, furan, isosorbide, itaconic acid, etc. This mini review gives an overall perspective for bio-based thermosets. (C) 2015 Society of Chemical Industry

Thomas J Groshens - One of the best experts on this subject based on the ideXlab platform.

  • sustainable hydrophobic Thermosetting Resins and polycarbonates from turpentine
    Green Chemistry, 2016
    Co-Authors: Benjamin G Harvey, Andrew J Guenthner, Josiah T Reams, Thomas A Koontz, Perrin J Storch, Thomas J Groshens
    Abstract:

    Carvacrol is a renewable phenol that can be derived from abundant components of pine resin. To demonstrate the utility of carvacrol for polymer applications, a bisphenol was synthesized from carvacrol and converted to both a cyanate ester resin (CarvCy) and polycarbonate. A cured resin disk prepared from CarvCy exhibited a Tg of 224 °C and a water uptake of only 0.7% after being immersed in 85 °C water for four days. The wet Tg of the material was only 3 °C lower than the dry Tg showing that the cured resin was virtually unaffected by exposure to hot water. Despite the presence of aliphatic groups on the aromatic rings, the cured resin exhibited good thermal stability with only 5% weight loss at 390 °C. The polycarbonate prepared from carvacrol had Mn = 10 200, Mw/Mn = 1.60, Tg = 119 °C, and even better thermal stability than the cyanate ester with 5% weight loss observed at 421 °C. The results provide compelling evidence that the sustainable phenol carvacrol can be used as a platform molecule for the generation of high performance polymers with exceptional properties.

  • renewable Thermosetting Resins and thermoplastics from vanillin
    Green Chemistry, 2015
    Co-Authors: Benjamin G Harvey, Andrew J Guenthner, Heather A Meylemans, Shannon R L Haines, Kevin R Lamison, Thomas J Groshens, Lee R Cambrea, Matthew C Davis, William W Lai
    Abstract:

    Two cyanate ester Resins and a polycarbonate thermoplastic have been synthesized from vanillin. The bisphenol precursors were prepared by both an electrochemical route as well as by a McMurry coupling reaction. 1,2-Bis(4-cyanato-3-methoxyphenyl)ethene (6) had a high melting point of 237 °C and did not cure completely under a standard cure protocol. In contrast, the reduced version, 1,2-bis(4-cyanato-3-methoxyphenyl)ethane (7) melted at 190 °C and underwent complete cure to form a thermoset material with Tg = 202 °C. 7 showed thermal stability up to 335 °C and decomposed via formation of phenolics and isocyanic acid. A polycarbonate was then synthesized from the reduced bisphenol by a transesterification reaction with diphenylcarbonate. The polymer had Mn = 3588, Mw/Mn = 1.9, and a Tg of 86 °C. TGA/FTIR data suggested that the polycarbonate decomposed via formation of benzodioxolones with concomitant elimination of methane. The results show that vanillin is a useful precursor to both Thermosetting Resins and thermoplastics without significant modification.

  • high tg Thermosetting Resins from resveratrol
    Polymer Chemistry, 2013
    Co-Authors: Jessica J Cash, Benjamin G Harvey, Andrew J Guenthner, Heather A Meylemans, Kevin R Lamison, Thomas J Groshens, Matthew C Davis, Michael D Ford, Joseph M Mabry, Josiah T Reams
    Abstract:

    The tricyanate esters of the natural product resveratrol (1) and dihydroresveratrol (2) were synthesized and subjected to thermal curing which gave polycyanurate network polymers which exhibited glass transition temperatures of >340 °C and 334 °C, respectively. Thermal decomposition temperatures of 412 °C and 403 °C for polycyanurates of 1 and 2, respectively, were typical of this class. However, char yields (600 °C) of 71% and 66% for 1 and 2, respectively, were more than double that from the polycyanurate of bisphenol A dicyanate (25%).

Benjamin G Harvey - One of the best experts on this subject based on the ideXlab platform.

  • sustainable hydrophobic Thermosetting Resins and polycarbonates from turpentine
    Green Chemistry, 2016
    Co-Authors: Benjamin G Harvey, Andrew J Guenthner, Josiah T Reams, Thomas A Koontz, Perrin J Storch, Thomas J Groshens
    Abstract:

    Carvacrol is a renewable phenol that can be derived from abundant components of pine resin. To demonstrate the utility of carvacrol for polymer applications, a bisphenol was synthesized from carvacrol and converted to both a cyanate ester resin (CarvCy) and polycarbonate. A cured resin disk prepared from CarvCy exhibited a Tg of 224 °C and a water uptake of only 0.7% after being immersed in 85 °C water for four days. The wet Tg of the material was only 3 °C lower than the dry Tg showing that the cured resin was virtually unaffected by exposure to hot water. Despite the presence of aliphatic groups on the aromatic rings, the cured resin exhibited good thermal stability with only 5% weight loss at 390 °C. The polycarbonate prepared from carvacrol had Mn = 10 200, Mw/Mn = 1.60, Tg = 119 °C, and even better thermal stability than the cyanate ester with 5% weight loss observed at 421 °C. The results provide compelling evidence that the sustainable phenol carvacrol can be used as a platform molecule for the generation of high performance polymers with exceptional properties.

  • renewable Thermosetting Resins and thermoplastics from vanillin
    Green Chemistry, 2015
    Co-Authors: Benjamin G Harvey, Andrew J Guenthner, Heather A Meylemans, Shannon R L Haines, Kevin R Lamison, Thomas J Groshens, Lee R Cambrea, Matthew C Davis, William W Lai
    Abstract:

    Two cyanate ester Resins and a polycarbonate thermoplastic have been synthesized from vanillin. The bisphenol precursors were prepared by both an electrochemical route as well as by a McMurry coupling reaction. 1,2-Bis(4-cyanato-3-methoxyphenyl)ethene (6) had a high melting point of 237 °C and did not cure completely under a standard cure protocol. In contrast, the reduced version, 1,2-bis(4-cyanato-3-methoxyphenyl)ethane (7) melted at 190 °C and underwent complete cure to form a thermoset material with Tg = 202 °C. 7 showed thermal stability up to 335 °C and decomposed via formation of phenolics and isocyanic acid. A polycarbonate was then synthesized from the reduced bisphenol by a transesterification reaction with diphenylcarbonate. The polymer had Mn = 3588, Mw/Mn = 1.9, and a Tg of 86 °C. TGA/FTIR data suggested that the polycarbonate decomposed via formation of benzodioxolones with concomitant elimination of methane. The results show that vanillin is a useful precursor to both Thermosetting Resins and thermoplastics without significant modification.

  • high tg Thermosetting Resins from resveratrol
    Polymer Chemistry, 2013
    Co-Authors: Jessica J Cash, Benjamin G Harvey, Andrew J Guenthner, Heather A Meylemans, Kevin R Lamison, Thomas J Groshens, Matthew C Davis, Michael D Ford, Joseph M Mabry, Josiah T Reams
    Abstract:

    The tricyanate esters of the natural product resveratrol (1) and dihydroresveratrol (2) were synthesized and subjected to thermal curing which gave polycyanurate network polymers which exhibited glass transition temperatures of >340 °C and 334 °C, respectively. Thermal decomposition temperatures of 412 °C and 403 °C for polycyanurates of 1 and 2, respectively, were typical of this class. However, char yields (600 °C) of 71% and 66% for 1 and 2, respectively, were more than double that from the polycyanurate of bisphenol A dicyanate (25%).