Recent Progress of High Performance Thermosets Based on Norbornene Functional Benzoxazine Resins

Lu, Yin; Yu, Xinye; Han, Lu; Zhang, Kan

doi:10.3390/polym13091417

Title: Recent Progress of High Performance Thermosets Based on Norbornene Functional Benzoxazine Resins

Journal Article · Tue Apr 27 00:00:00 EDT 2021 · Polymers

DOI:https://doi.org/10.3390/polym13091417· OSTI ID:1815897

Lu, Yin ^[1]; Yu, Xinye ^[1]; Han, Lu ^[2];

^[1]

Jiangnan Univ., Wuxi, Jiangsu (China). School of Materials Science and Engineering. Research School of Polymeric Materials
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Chemical Sciences Division

With the growing demand for high performance polymeric materials in industry, several types of thermosets such as bismaleimides, advanced epoxy resins, cyanate esters, and phenolic resins have been widely investigated to improve the performance of thermosetting products. Among them, benzoxazine resins have received wide attention due to their extraordinarily rich molecular design flexibility, which can customize our needs and adapt increasing requirements. To further improve the properties of polybenzoxiazines, researchers have found that the introduction of a norbornene functional group into the benzoxazine moiety can effectively improve the comprehensive performance of polybenzoxazine thermosets. This article focused on reviewing the recent development of high-performance thermosets based on norbornene functional benzoxazine thermosetting resins.

View Accepted Manuscript (DOE)

Cite

Export

Save

Sponsoring Organization:: USDOE Office of Science (SC); National Natural Science Foundation of China (NSFC)

Grant/Contract Number:: AC05-00OR22725; 52073125; 51603093

OSTI ID:: 1815897

Journal Information:: Polymers, Vol. 13, Issue 9; ISSN 2073-4360

Publisher:: MDPICopyright Statement

Country of Publication:: United States

Language:: English

References (42)

Studies on the isomeric effect of nitrile functionality on the polymerization and thermal properties of ortho-norbornene-based benzoxazine resins Yu, Xinye; Zhang, Kan Journal of Polymer Research, Vol. 27, Issue 5 https://doi.org/10.1007/s10965-020-02087-4	journal	May 2020
High-performance maleimide and nitrile-functionalized benzoxazines with good processibility for advanced composites applications Chaisuwan, Thanyalak; Ishida, Hatsuo Journal of Applied Polymer Science, Vol. 101, Issue 1 https://doi.org/10.1002/app.23509	journal	January 2006
Processing and characterization of carbon fibre-reinforced polynaphthoxazine composite Shen, S. B.; Ishida, H. Journal of Materials Science, Vol. 31, Issue 22 https://doi.org/10.1007/BF01152144	journal	November 1996
Alkynyl-functionalized benzoxazine containing phthalide side group: Synthesis, characterization and curing mechanism Xiong, Xuhai; Zhang, zhaopeng; Ren, Rong Polymer Testing, Vol. 72 https://doi.org/10.1016/j.polymertesting.2018.10.019	journal	December 2018
A Smart Latent Catalyst Containing o -Trifluoroacetamide Functional Benzoxazine: Precursor for Low Temperature Formation of Very High Performance Polybenzoxazole with Low Dielectric Constant and High Thermal Stability Zhang, Kan; Han, Lu; Froimowicz, Pablo Macromolecules, Vol. 50, Issue 17 https://doi.org/10.1021/acs.macromol.7b00887	journal	August 2017
Resveratrol-based tri-functional benzoxazines: Synthesis, characterization, polymerization, and thermal and flame retardant properties Zhang, Kan; Han, Mengchao; Han, Lu European Polymer Journal, Vol. 116 https://doi.org/10.1016/j.eurpolymj.2019.04.036	journal	July 2019
Adapting benzoxazine chemistry for unconventional applications Kiskan, Baris Reactive and Functional Polymers, Vol. 129 https://doi.org/10.1016/j.reactfunctpolym.2017.06.009	journal	August 2018
Anomalous Isomeric Effect on the Properties of Bisphenol F-based Benzoxazines: Toward the Molecular Design for Higher Performance Liu, Jia; Ishida, Hatsuo Macromolecules, Vol. 47, Issue 16 https://doi.org/10.1021/ma501294y	journal	August 2014
Thermally Activated Structural Changes of a Norbornene–Benzoxazine–Phthalonitrile Thermosetting System: Simple Synthesis, Self-Catalyzed Polymerization, and Outstanding Flame Retardancy Zhang, Kan; Yu, Xinye; Wang, Yuting ACS Applied Polymer Materials, Vol. 1, Issue 10 https://doi.org/10.1021/acsapm.9b00668	journal	August 2019
Bis(benzoxazine-maleimide)s as a novel class of high performance resin: Synthesis and properties Jin, Lin; Agag, Tarek; Ishida, Hatsuo European Polymer Journal, Vol. 46, Issue 2 https://doi.org/10.1016/j.eurpolymj.2009.09.013	journal	February 2010
Condensation Products of Aldehydes and Ketones with o-Aminobenzyl Alcohol and o-Hydroxybenzylamine Holly, Frederick W.; Cope, Arthur C. Journal of the American Chemical Society, Vol. 66, Issue 11 https://doi.org/10.1021/ja01239a022	journal	November 1944
Synthesis and characterization of a novel siloxane-imide-containing polybenzoxazine: Novel siloxane-imide-containing polybenzoxazine Chen, Kai-Chi; Li, Hsun-Tien; Chen, Wen-Bin Polymer International, Vol. 60, Issue 3 https://doi.org/10.1002/pi.2966	journal	November 2010
Benzoxazole Resin: A Novel Class of Thermoset Polymer via Smart Benzoxazine Resin Agag, Tarek; Liu, Jia; Graf, Robert Macromolecules, Vol. 45, Issue 22 https://doi.org/10.1021/ma300924s	journal	November 2012
Polyimides containing aliphatic/alicyclic segments in the main chains Zhuang, Yongbing; Seong, Jong Geun; Lee, Young Moo Progress in Polymer Science, Vol. 92 https://doi.org/10.1016/j.progpolymsci.2019.01.004	journal	May 2019
Thermally curable main-chain benzoxazine prepolymers via polycondensation route Demir, Kubra Dogan; Kiskan, Baris; Aydogan, Binnur Reactive and Functional Polymers, Vol. 73, Issue 2 https://doi.org/10.1016/j.reactfunctpolym.2012.04.016	journal	February 2013
Outstanding dielectric and thermal properties of main chain-type poly(benzoxazine- co -imide- co -siloxane)-based cross-linked networks Zhang, Kan; Yu, Xinye; Kuo, Shiao-Wei Polymer Chemistry, Vol. 10, Issue 19 https://doi.org/10.1039/C9PY00464E	journal	January 2019
Synthesis, characterization and structural thermally rearrangement of ortho-amide functional benzoxazine containing acetylene group Sun, Lin; Zhang, Kan; Min, Chunying Thermochimica Acta, Vol. 668 https://doi.org/10.1016/j.tca.2018.08.003	journal	October 2018
PMR-15 processing, properties and problems—a review Wilson, Douglas British Polymer Journal, Vol. 20, Issue 5 https://doi.org/10.1002/pi.4980200505	journal	January 1988
Synthesis, curing behavior and thermal properties of fluorene-containing benzoxazines based on linear and branched butylamines Wang, Jun; Ren, Tian-tian; Wang, Yu-dan Reactive and Functional Polymers, Vol. 74 https://doi.org/10.1016/j.reactfunctpolym.2013.10.008	journal	January 2014
Synthesis and characterization of maleimide and norbornene functionalized benzoxazines Ishida, Hatsuo; Ohba, Sharon Polymer, Vol. 46, Issue 15 https://doi.org/10.1016/j.polymer.2005.04.080	journal	July 2005
Low-Surface-Free-Energy Materials Based on Polybenzoxazines Wang, Chih-Feng; Su, Yi-Che; Kuo, Shiao-Wie Angewandte Chemie, Vol. 118, Issue 14 https://doi.org/10.1002/ange.200503957	journal	March 2006
Remarkable improvement of thermal stability of main-chain benzoxazine oligomer by incorporating o -norbornene as terminal functionality Zhang, Kan; Qiu, Jiaming; Li, Songjun Journal of Applied Polymer Science, Vol. 134, Issue 41 https://doi.org/10.1002/app.45408	journal	June 2017
Catalyst-Free and Low-Temperature Terpolymerization in a Single-Component Benzoxazine Resin Containing Both Norbornene and Acetylene Functionalities Zhang, Kan; Yu, Xinye Macromolecules, Vol. 51, Issue 16 https://doi.org/10.1021/acs.macromol.8b01558	journal	August 2018
Synthesis, curing and physical behaviour of maleimide-terminated poly(ether ketones) Lyle, G. D.; Senger, J. S.; Chen, D. H. Polymer, Vol. 30, Issue 6 https://doi.org/10.1016/0032-3861(89)90067-0	journal	June 1989
Thermally stable polybenzoxazines via ortho-norbornene functional benzoxazine monomers: Unique advantages in monomer synthesis, processing and polymer properties Zhang, Kan; Ishida, Hatsuo Polymer, Vol. 66 https://doi.org/10.1016/j.polymer.2015.04.044	journal	June 2015
Synthesis and performance enhancement of novel polybenzoxazines with low surface free energy: Low-surface-free-energy novel polybenzoxazines Chen, Kai-Chi; Li, Hsun-Tien; Huang, Shu-Chen Polymer International, Vol. 60, Issue 7 https://doi.org/10.1002/pi.3046	journal	March 2011
A Study on the Volumetric Expansion of Benzoxazine-Based Phenolic Resin Ishida, Hatsuo; Low, Hong Yee Macromolecules, Vol. 30, Issue 4 https://doi.org/10.1021/ma960539a	journal	February 1997
Thermally Curable Polyoxanorbornene by Ring Opening Metathesis Polymerization: Thermally Curable Polyoxanorbornene by ROMP Tasdelen, Mehmet Atilla; Durmaz, Hakan Macromolecular Chemistry and Physics, Vol. 212, Issue 19 https://doi.org/10.1002/macp.201100258	journal	August 2011
Direct synthesis of poly(benzoxazine imide) from an ortho -benzoxazine: its thermal conversion to highly cross-linked polybenzoxazole and blending with poly(4-vinylphenol) El-Mahdy, Ahmed F. M.; Kuo, Shiao-Wei Polymer Chemistry, Vol. 9, Issue 14 https://doi.org/10.1039/C8PY00087E	journal	January 2018
An Investigation of Stable Free Radicals in Polyimides Using EPR Spectroscopy Ahn, Myong K.; Stringfellow, Thomas C.; Lei, Jianming MRS Proceedings, Vol. 305 https://doi.org/10.1557/PROC-305-217	journal	January 1993
Combining benzoxazine and ketene chemistries for self-healing of high performance thermoset surfaces Arslan, Mustafa; Motallebzadeh, Amir; Kiskan, Baris Polymer Chemistry, Vol. 9, Issue 15 https://doi.org/10.1039/C8PY00293B	journal	January 2018
Novel thermosetting resins based on 4-(N-maleimidophenyl)glycidylether: II. Bismaleimides and polybismaleimides Liu, Ying-Ling; Chen, Yu-Jane Polymer, Vol. 45, Issue 6 https://doi.org/10.1016/j.polymer.2004.01.001	journal	March 2004
Mechanistic Pathways for the Polymerization of Methylol-Functional Benzoxazine Monomers Baqar, Mohamed; Agag, Tarek; Huang, Rongzhi Macromolecules, Vol. 45, Issue 20 https://doi.org/10.1021/ma301963d	journal	October 2012
Thermally Curable Acetylene-Containing Main-Chain Benzoxazine Polymers via Sonogashira Coupling Reaction Dogan Demir, Kubra; Kiskan, Baris; Yagci, Yusuf Macromolecules, Vol. 44, Issue 7 https://doi.org/10.1021/ma1029746	journal	March 2011
Synthesis and Characterization of Partially Fluorinated Polybenzoxazine Resins Utilizing Octafluorocyclopentene as a Versatile Building Block Wu, Jingbo; Xi, Yang; McCandless, Gregory T. Macromolecules, Vol. 48, Issue 17 https://doi.org/10.1021/acs.macromol.5b01014	journal	August 2015
Intrinsic self-initiating thermal ring-opening polymerization of 1,3-benzoxazines without the influence of impurities using very high purity crystals Han, Lu; Salum, María Laura; Zhang, Kan Journal of Polymer Science Part A: Polymer Chemistry, Vol. 55, Issue 20 https://doi.org/10.1002/pola.28723	journal	July 2017
A high performance polybenzoxazine via smart ortho -norbornene functional benzoxazine monomer based on ring-opening metathesis polymerization Zhang, Kan; Liu, Yuqi; Wang, Yuting High Performance Polymers, Vol. 31, Issue 5 https://doi.org/10.1177/0954008318780995	journal	June 2018
Phenolic materials via ring-opening polymerization: Synthesis and characterization of bisphenol-A based benzoxazines and their polymers Ning, Xin; Ishida, Hatsuo Journal of Polymer Science Part A: Polymer Chemistry, Vol. 32, Issue 6 https://doi.org/10.1002/pola.1994.080320614	journal	April 1994
Unique self-catalyzed cationic ring-opening polymerization of a high performance deoxybenzoin-based 1,3-benzoxazine monomer Zhang, Kan; Tan, Xiaoxiao; Wang, Yuting Polymer, Vol. 168 https://doi.org/10.1016/j.polymer.2019.01.089	journal	April 2019
Performance enhancement of polybenzoxazine by hybridization with polysiloxane Ardhyananta, Hosta; Wahid, Mohd. Haniff; Sasaki, Masahiro Polymer, Vol. 49, Issue 21 https://doi.org/10.1016/j.polymer.2008.08.030	journal	October 2008
Ortho -Imide and Allyl Groups Effect on Highly Thermally Stable Polybenzoxazine/Double-Decker-Shaped Polyhedral Silsesquioxane Hybrids Chen, Wei-Cheng; Kuo, Shiao-Wei Macromolecules, Vol. 51, Issue 23 https://doi.org/10.1021/acs.macromol.8b02207	journal	November 2018
A soluble nadimide end-capped fluorinated resin Pascal, Thierry; Audigier, Dominique; Mercier, Régis Polymer, Vol. 32, Issue 6 https://doi.org/10.1016/0032-3861(91)90601-e	journal	January 1991

Similar Records

Bioinspired Design Provides High-Strength Benzoxazine Structural Adhesives

Journal Article · Wed Jul 24 00:00:00 EDT 2019 · Angewandte Chemie (International Edition) · OSTI ID:1815897

Higginson, Cody J.; Malollari, Katerina G.; Xu, Yunqi; +3 more

New hybrid thermosets based on epoxy resins and benzocylobutenes

Conference · Sun Dec 31 00:00:00 EST 1995 · OSTI ID:1815897

Brennan, D J; White, J E; Burks, B T

Cyclic imino ethers in practical step-growth polymerizations

Conference · Fri Dec 31 00:00:00 EST 1993 · OSTI ID:1815897

Culbertson, B M

Related Subjects

36 MATERIALS SCIENCE
42 ENGINEERING
benzoxazine
norbornene
polybenzoxazine
high performance

Title: Recent Progress of High Performance Thermosets Based on Norbornene Functional Benzoxazine Resins

Citation Formats

References (42)

Similar Records

Related Subjects