Nature-derived Ultrahigh-performance Aromatic Bioplastics
Author affiliations
DOI:
https://doi.org/10.15625/2525-2518/17116Keywords:
bioplastics, 3-amino-4-hydroxybenzoic acid, polybenzoxazole, polybenzimidazoleAbstract
Biomass, a renewable carbon source which can be processed using biorefinery system as an alternative of the conventional petroleum-based refineries. Aromatic precursor molecule synthesis involves chemical synthesis of fossil-fuel-based starting materials, such as benzene and xylene. These energy-intensive processes are usually producing many byproducts along with the desired molecule. If aromatic molecules can be extracted from natural resources involving minimum chemical conversions, that can be advantageous. Most of the reported approaches are expensive in nature and the outcomes with lower yield. Microbial fermentation of the lignocellulosic derivatives are ideal to establish sustainable society. In this chapter, we will focus on the aromatic building block preparations starting from nonedible feedstock such as kraft pulp. Aromatic aminobenzoic acid (3-amino-4-hydroxybenzoic acid) preparation from renewable resources and its use in various polymer preparations, such as polyaniline, polyester, and polybenzazole will be discussed here.
Downloads
References
Luo H., Abu-Omar M. M. - Chemicals From Lignin, In Encyclopedia of Sustainable Technologies, Abraham, M. A., Ed.; Elsevier: Oxford, 2017, pp. 573-585. https://doi.org/ 10.1016/B978-0-12-409548-9.10235-0.
DOI: https://doi.org/10.1016/B978-0-12-409548-9.10235-0
https://doi.org/ 10.1016/B978-0-12-409548-9.10235-0.">
High-Value Opportunities for Lignin - Unlocking Its Potential, Renewable Carbon News.Frost & Sullivan, 2012-11-07.
Helanto K., Matikainen L., Talja R., Rojas O. J. - Bio-Based Polymers for Sustainable Packaging and Biobarriers: A Critical Review, BioResources 14 (2) (2019) 4902-4951.
Iwata T. - Biodegradable and Bio-Based Polymers: Future Prospects of Eco-Friendly Plastics. Angewandte Chemie International Edition 54 (11) (2015) 3210-3215. https://doi.org/10.1002/anie.201410770.
DOI: https://doi.org/10.1002/anie.201410770
https://doi.org/10.1002/anie.201410770.">
Brodin M., Vallejos M., Opedal M. T., Area M. C. - Chinga-Carrasco, G. Lignocellulosics as Sustainable Resources for Production of Bioplastics - A Review, Journal of Cleaner Production 162 (2017) 646-664. https://doi.org/10.1016/j.jclepro.2017.05.209.
DOI: https://doi.org/10.1016/j.jclepro.2017.05.209
https://doi.org/10.1016/j.jclepro.2017.05.209.">
Yu J., Paterson N., Blamey J., Millan M. - Cellulose, Xylan and Lignin Interactions during Pyrolysis of Lignocellulosic Biomass, Fuel 191 (2017) 140-149. https://doi.org/ 10.1016/j.fuel.2016.11.057.
DOI: https://doi.org/10.1016/j.fuel.2016.11.057
https://doi.org/ 10.1016/j.fuel.2016.11.057.">
Yang J., Ching Y. C., Chuah C. H. - Applications of Lignocellulosic Fibers and Lignin in Bioplastics: A Review, Polymers 11 (5) (2019) 751. https://doi.org/10.3390/polym 11050751.
DOI: https://doi.org/10.3390/polym11050751
https://doi.org/10.3390/polym 11050751.">
Spiridon I., Leluk K., Resmerita A. M., Darie R. N. - Evaluation of PLA–Lignin Bioplastics Properties before and after Accelerated Weathering, Composites Part B: Engineering 69 (2015) 342-349. https://doi.org/10.1016/j.compositesb.2014.10.006.
DOI: https://doi.org/10.1016/j.compositesb.2014.10.006
https://doi.org/10.1016/j.compositesb.2014.10.006.">
Kawamoto H. - Lignin Pyrolysis Reactions, Journal of Wood Science 63 (2) (2017) 117-132. https://doi.org/10.1007/s10086-016-1606-z.
DOI: https://doi.org/10.1007/s10086-016-1606-z
https://doi.org/10.1007/s10086-016-1606-z.">
Saiz-Jimenez C., De Leeuw J. W. - Lignin Pyrolysis Products: Their Structures and Their Significance as Biomarkers, Organic Geochemistry 10 (4) (1986) 869-876. https://doi.org/ 10.1016/S0146-6380(86)80024-9.
DOI: https://doi.org/10.1016/S0146-6380(86)80024-9
https://doi.org/ 10.1016/S0146-6380(86)80024-9.">
Nag A., Matsumi N., Kaneko T. - Bio-Based Aromatics: Aminobenzoic Acid Derivatives for High-Performance Bioplastics, In Sustainability & Green Polymer Chemistry Volume 2: Biocatalysis and Biobased Polymers, ACS Symposium Series, American Chemical Society 1373 (2020) 99-121. https://doi.org/10.1021/bk-2020-1373.ch006.
DOI: https://doi.org/10.1021/bk-2020-1373.ch006
https://doi.org/10.1021/bk-2020-1373.ch006.">
Dwivedi S., Kaneko T. - Aromatic Bioplastics with Heterocycles, In Green Polymer Chemistry: New Products, Processes, and Applications; ACS Symposium Series, American Chemical Society 1310 (2018) 201-218. https://doi.org/10.1021/bk-2018-1310.ch014.
DOI: https://doi.org/10.1021/bk-2018-1310.ch014
https://doi.org/10.1021/bk-2018-1310.ch014.">
Nag A., Ali M. A., Kawaguchi H., Saito S., Kawasaki Y., Miyazaki S., Kawamoto H., Adi D. T. N., Yoshihara K., Masuo S., Katsuyama Y., Kondo A., Ogino C., Takaya N., Kaneko T., Ohnishi Y. - Ultrahigh Thermoresistant Lightweight Bioplastics Developed from Fermentation Products of Cellulosic Feedstock, Advanced Sustainable Systems 5 (1) (2021) 2000193. https://doi.org/10.1002/adsu.202000193.
DOI: https://doi.org/10.1002/adsu.202000193
https://doi.org/10.1002/adsu.202000193.">
Nag A., Ali M. A., Watanabe M., Singh M., Amornwachirabodee K., Kato S., Mitsumata T., Takada K., Kaneko T. - High-Performance Poly(Benzoxazole/Benzimidazole) Bio-Based Plastics with Ultra-Low Dielectric Constant from 3-Amino-4-Hydroxybenzoic Acid, Polymer Degradation and Stability 162 (2019) 29-35. https://doi.org/10.1016/ j.polymdegradstab.2019.01.036.
DOI: https://doi.org/10.1016/j.polymdegradstab.2019.01.036
https://doi.org/10.1016/ j.polymdegradstab.2019.01.036.">
Renewably Sourced Automotive Materials. https://www.dupont.com/knowledge/ renewably-sourced-interiors.html (accessed 2020-06-10).
https://www.dupont.com/knowledge/ renewably-sourced-interiors.html (accessed 2020-06-10).">
Holladay J. E., White J. F., Bozell J. J., Johnson D. - Top Value Added Chemicals from Biomass - Volume II, Results of Screening for Potential Candidates from Biorefinery Lignin, PNNL-16983, Pacific Northwest National Lab. (PNNL), Richland, WA (United States), National Renewable Energy Lab. (NREL), Golden, CO (United States), 2007.
DOI: https://doi.org/10.2172/921839
Bozell J. J., Petersen G. R. - Technology Development for the Production of Biobased Products from Biorefinery Carbohydrates—the US Department of Energy’s “Top 10” Revisited. Green Chemistry 12 (4) (2010), 539–554. https://doi.org/10.1039/B922014C.
DOI: https://doi.org/10.1039/b922014c
https://doi.org/10.1039/B922014C.">
Marshall A. L., Alaimo P. J. - Useful Products from Complex Starting Materials: Common Chemicals from Biomass Feedstocks, Chemistry – A European Journal 16 (17) (2010) 4970-4980. https://doi.org/10.1002/chem.200903028.
DOI: https://doi.org/10.1002/chem.200903028
https://doi.org/10.1002/chem.200903028.">
Gandini A., Belgacem M. N. - Chapter 1 - The State of the Art. In Monomers, Polymers and Composites from Renewable Resources, Belgacem, M. N., Gandini, A., Eds., Elsevier: Amsterdam, 2008, pp 1-16. https://doi.org/10.1016/B978-0-08-045316-3.000016.
DOI: https://doi.org/10.1016/B978-0-08-045316-3.00001-6
https://doi.org/10.1016/B978-0-08-045316-3.000016.">
Gandini A. - The Irruption of Polymers from Renewable Resources on the Scene of Macromolecular Science and Technology, Green Chemistry 13 (5) (2011) 1061-1083. https://doi.org/10.1039/C0GC00789G.
DOI: https://doi.org/10.1039/c0gc00789g
https://doi.org/10.1039/C0GC00789G.">
Gandini A. - Furans as Offspring of Sugars and Polysaccharides and Progenitors of a Family of Remarkable Polymers: A Review of Recent Progress, Polymer Chemistry 1 (3) (2010) 245-251. https://doi.org/10.1039/B9PY00233B.
DOI: https://doi.org/10.1039/B9PY00233B
https://doi.org/10.1039/B9PY00233B.">
Gandini A., Silvestre A. J. D., Neto C. P., Sousa A. F., Gomes M. - The Furan Counterpart of Poly(Ethylene Terephthalate): An Alternative Material Based on Renewable Resources, Journal of Polymer Science Part A: Polymer Chemistry 47 (1) (2009) 295-298. https://doi.org/10.1002/pola.23130.
DOI: https://doi.org/10.1002/pola.23130
https://doi.org/10.1002/pola.23130.">
Mialon L., Vanderhenst R., Pemba A. G., Miller S. A. - Polyalkylenehydroxybenzoates (PAHBs): Biorenewable Aromatic/Aliphatic Polyesters from Lignin, Macromolecular Rapid Communications 32 (17) (2011) 1386-1392. https://doi.org/10.1002/ marc.201100242.
DOI: https://doi.org/10.1002/marc.201100242
https://doi.org/10.1002/ marc.201100242.">
Kumar N., Pruthi V. - Potential Applications of Ferulic Acid from Natural Sources, Biotechnol Rep (Amst) 4 (2014) 86-93. https://doi.org/10.1016/j.btre.2014.09.002.
DOI: https://doi.org/10.1016/j.btre.2014.09.002
https://doi.org/10.1016/j.btre.2014.09.002.">
Hatakeyama H., Hatakeyama T. - Lignin Structure, Properties, and Applications, In: Biopolymers: Lignin, Proteins, Bioactive Nanocomposites, Abe A., Dusek K., Kobayashi, S. (Eds.), Advances in Polymer Science, Springer: Berlin, Heidelberg, 2010, pp. 1-63. https://doi.org/10.1007/12_2009_12.
DOI: https://doi.org/10.1007/12_2009_12
https://doi.org/10.1007/12_2009_12.">
Mialon L., G. Pemba A., Miller S. - Biorenewable Polyethylene Terephthalate Mimics Derived from Lignin and Acetic Acid, Green Chemistry 12 (10) (2010) 1704-1706. https://doi.org/10.1039/C0GC00150C.
DOI: https://doi.org/10.1039/c0gc00150c
https://doi.org/10.1039/C0GC00150C.">
Kaneko T., Thi T. H., Shi D. J., Akashi M. - Environmentally Degradable, High-Performance Thermoplastics from Phenolic Phytomonomers, Nature Materials 5 (12) (2006) 966-970. https://doi.org/10.1038/nmat1778.
DOI: https://doi.org/10.1038/nmat1778
https://doi.org/10.1038/nmat1778.">
Takeshima H., Satoh K., Kamigaito M. - Bio-Based Functional Styrene Monomers Derived from Naturally Occurring Ferulic Acid for Poly(Vinylcatechol) and Poly(Vinylguaiacol) via Controlled Radical Polymerization. Macromolecules 50 (11) (2017) 4206-4216. https://doi.org/10.1021/acs.macromol.7b00970.
DOI: https://doi.org/10.1021/acs.macromol.7b00970
https://doi.org/10.1021/acs.macromol.7b00970.">
Miyaji H., Satoh K., Kamigaito M. - Bio-Based Polyketones by Selective Ring-Opening Radical Polymerization of α-Pinene-Derived Pinocarvone, Angewandte Chemie International Edition 55 (4) (2016) 1372-1376. https://doi.org/10.1002/anie.201509379.
DOI: https://doi.org/10.1002/anie.201509379
https://doi.org/10.1002/anie.201509379.">
Tabata Y., Abe H. - Synthesis and Properties of Alternating Copolymers of 3-Hydroxybutyrate and Lactate Units with Different Stereocompositions, Macromolecules 47 (21) (2014) 7354-7361. https://doi.org/10.1021/ma501783f.
DOI: https://doi.org/10.1021/ma501783f
https://doi.org/10.1021/ma501783f.">
Fujita T., Nguyen H. D., Ito T., Zhou S., Osada L., Tateyama S., Kaneko T., Takaya N. - Microbial Monomers Custom-Synthesized to Build True Bio-Derived Aromatic Polymers, Appl. Microbiol Biotechnol 97 (20) (2013) 8887-8894. https://doi.org/10.1007/s00253-013-5078-4.
DOI: https://doi.org/10.1007/s00253-013-5078-4
https://doi.org/10.1007/s00253-013-5078-4.">
Mu W., Liu F., Jia J., Chen C., Zhang T., Jiang B. - 3-Phenyllactic Acid Production by Substrate Feeding and PH-Control in Fed-Batch Fermentation of Lactobacillus Sp. SK007. Bioresource Technology 100 (21) (2009) 5226-5229. https://doi.org/10.1016/j.biortech. 2009.05.024.
DOI: https://doi.org/10.1016/j.biortech.2009.05.024
https://doi.org/10.1016/j.biortech. 2009.05.024.">
Niggeweg R., Michael A. J., Martin C. - Engineering Plants with Increased Levels of the Antioxidant Chlorogenic Acid. Nature Biotechnology 22 (6) (2004) 746-754. https://doi. org/10.1038/nbt966.
DOI: https://doi.org/10.1038/nbt966
Kyndt J. A., Hurley J. K., Devreese B., Meyer T. E., Cusanovich M. A., Tollin G., Van Beeumen J. J. and Rhodobacter Capsulatus Photoactive Yellow Protein: Genetic Context, Spectral and Kinetics Characterization, and Mutagenesis, Biochemistry 43 (7) (2004) 1809-1820. https://doi.org/10.1021/bi035789f.
DOI: https://doi.org/10.1021/bi035789f
https://doi.org/10.1021/bi035789f.">
Kort R., Phillips-Jones M. K., van Aalten D. M. F., Haker A., Hoffer S. M., Hellingwerf K. J., Crielaard W. - Sequence, Chromophore Extraction and 3-D Model of the Photoactive Yellow Protein from Rhodobacter Sphaeroides1The Nucleotide Sequences Reported in This Paper Have Been Submitted to the EMBL Nucleotide Sequence Database under Accession Numbers AJ002398 and X98889.1. Biochim, Biophys. Acta BBA - Protein Struct. Mol. Enzymol. 1385 (1998) 1-6. https://doi.org/10.1016/S0167-4838(98)00050-8.
DOI: https://doi.org/10.1016/S0167-4838(98)00050-8
https://doi.org/10.1016/S0167-4838(98)00050-8.">
Weng W., Markel E. J., Dekmezian A. H. - Synthesis of Long-Chain Branched Propylene Polymers via Macromonomer Incorporation, Macromolecular Rapid Communications 22 (18) (2001) 1488-1492. https://doi.org/10.1002/1521-3927(20011201)22:18<1488::AID-MARC1488>3.0.CO,2-I.
DOI: https://doi.org/10.1002/1521-3927(20011201)22:18<1488::AID-MARC1488>3.0.CO;2-I
https://doi.org/10.1002/1521-3927(20011201)22:18<1488::AID-MARC1488>3.0.CO,2-I.">
Johnson O. H., Green D. E., Pauli R. - The antibacterial action of derivatives and analogues of p-aminobenzoic acid, Journal of Biological Chemistry 153 (1) (1944) 37-47.
DOI: https://doi.org/10.1016/S0021-9258(18)51210-2
Kaneko T., Tateyam S., Okajima M., Hojoon S., Takaya N. - Ultrahigh Heat-Resistant, Transparent Bioplastics from Exotic Amino Acid, Materials Today: Proceedings 3 (2016) S21-S29. https://doi.org/10.1016/j.matpr.2016.01.004.
DOI: https://doi.org/10.1016/j.matpr.2016.01.004
https://doi.org/10.1016/j.matpr.2016.01.004.">
Matsushita Y., Nakamura A., Aoki D., Yagami S., Fukushima K. - Bio-Based Polymer from Ferulic Acid by Electropolymerization, BioResources 11 (4) (2016) 9789-9802.
DOI: https://doi.org/10.15376/biores.11.4.9789-9802
Tateyama S., Masuo S., Suvannasara P., Oka Y., Miyazato A., Yasaki K., Teerawatananond T., Muangsin N., Zhou S., Kawasaki Y., Zhu L., Zhou Z., Takaya N., Kaneko T. - Ultrastrong, Transparent Polytruxillamides Derived from Microbial Photodimers, Macromolecules 49 (9) (2016) 3336-3342. https://doi.org/10.1021/acs. macromol.6b00220.
DOI: https://doi.org/10.1021/acs.macromol.6b00220
https://doi.org/10.1021/acs. macromol.6b00220.">
Kawasaki Y., Aniruddha N., Minakawa H., Masuo S., Kaneko T., Takaya N. - Novel Polycondensed Biopolyamide Generated from Biomass-Derived 4-Aminohydrocinnamic Acid, Applied Microbiology and Biotechnology 102 (2) (2018) 631-639. https://doi.org/ 10.1007/s00253-017-8617-6.
DOI: https://doi.org/10.1007/s00253-017-8617-6
https://doi.org/ 10.1007/s00253-017-8617-6.">
Tachibana Y., Masuda T., Funabashi M., Kunioka M. - Chemical Synthesis of Fully Biomass-Based Poly(Butylene Succinate) from Inedible-Biomass-Based Furfural and Evaluation of Its Biomass Carbon Ratio, Biomacromolecules 11(10) (2010) 2760-2765. https://doi.org/10.1021/bm100820y.
DOI: https://doi.org/10.1021/bm100820y
https://doi.org/10.1021/bm100820y.">
Wang C., Ming W., Yan D., Zhang C., Yang M., Liu Y., Zhang Y., Guo B., Wan Y., Xing J. - Novel Membrane-Based Biotechnological Alternative Process for Succinic Acid Production and Chemical Synthesis of Bio-Based Poly (Butylene Succinate), Bioresource Technology 156 (2014) 6-13. https://doi.org/10.1016/j.biortech.2013.12.043.
DOI: https://doi.org/10.1016/j.biortech.2013.12.043
https://doi.org/10.1016/j.biortech.2013.12.043.">
Vardon D. R., Rorrer N. A., Salvachúa D., Settle A. E., Johnson C. W., Menart M. J., Cleveland N. S., Ciesielski P. N., Steirer K. X., Dorgan J. R., Beckham G. T. - Cis,Cis-Muconic Acid: Separation and Catalysis to Bio-Adipic Acid for Nylon-6,6 Polymerization, Green Chemistry 18 (11) (2016) 3397-3413. https://doi.org/10.1039/C5GC02844B.
DOI: https://doi.org/10.1039/C5GC02844B
https://doi.org/10.1039/C5GC02844B.">
Han J. - A Bio-Based ‘Green’ Process for Catalytic Adipic Acid Production from Lignocellulosic Biomass Using Cellulose and Hemicellulose Derived γ-Valerolactone. Energy Conversion and Management 129 (2016) 75-80. https://doi.org/10.1016/ j.enconman.2016.10.019.
DOI: https://doi.org/10.1016/j.enconman.2016.10.019
https://doi.org/10.1016/ j.enconman.2016.10.019.">
Suzuki H., Ohnishi Y., Furusho Y., Sakuda S., Horinouchi S. - Novel Benzene Ring Biosynthesis from C(3) and C(4) Primary Metabolites by Two Enzymes. Journal of Biological Chemistry 281 (48) (2006) 36944-36951. https://doi.org/10.1074/jbc. M608103200.
DOI: https://doi.org/10.1074/jbc.M608103200
https://doi.org/10.1074/jbc. M608103200.">
Suzuki H., Ohnishi Y., Horinouchi S. - GriC and GriD Constitute a Carboxylic Acid Reductase Involved in Grixazone Biosynthesis in Streptomyces Griseus, The Journal of Antibiotics 60 (6) (2007) 380-387. https://doi.org/10.1038/ja.2007.52.
DOI: https://doi.org/10.1038/ja.2007.52
https://doi.org/10.1038/ja.2007.52.">
Shozui F., Tajima Y. - Escherichia Coli Capable of Producing 3-Amino-4-Hydroxybenzoic Acid, US9587259B2, March 7, 2017.
Kawaguchi H., Ogino C., Kondo A. - Microbial Conversion of Biomass into Bio-Based Polymers, Bioresource Technology 245 (2017) 1664-1673. https://doi.org/10.1016/ j.biortech.2017.06.135.
DOI: https://doi.org/10.1016/j.biortech.2017.06.135
https://doi.org/10.1016/ j.biortech.2017.06.135.">
Liu R., Liang L., Li F., Wu M., Chen K., Ma J., Jiang M., Wei P., Ouyang P. - Efficient Succinic Acid Production from Lignocellulosic Biomass by Simultaneous Utilization of Glucose and Xylose in Engineered Escherichia Coli, Bioresource Technology 149 (2013) 84-91. https://doi.org/10.1016/j.biortech.2013.09.052.
DOI: https://doi.org/10.1016/j.biortech.2013.09.052
https://doi.org/10.1016/j.biortech.2013.09.052.">
Kawaguchi H., Hasunuma T., Ogino C., Kondo A. - Bioprocessing of Bio-Based Chemicals Produced from Lignocellulosic Feedstocks, Current Opinion in Biotechnology 42 (2016) 30-39. https://doi.org/10.1016/j.copbio.2016.02.031.
DOI: https://doi.org/10.1016/j.copbio.2016.02.031
https://doi.org/10.1016/j.copbio.2016.02.031.">
Anand J., Palaniappan S., Sathyanarayana D. N. - Conducting Polyaniline Blends and Composites, Progress in Polymer Science 23 (6) (1998) 993-1018. https://doi.org/ 10.1016/S0079-6700(97)00040-3.
DOI: https://doi.org/10.1016/S0079-6700(97)00040-3
https://doi.org/ 10.1016/S0079-6700(97)00040-3.">
Kulkarni V. G. - Polyanilines: Progress in Processing and Applications. In Semiconducting Polymers, ACS Symposium Series, American Chemical Society 735 (1999) 174-183. https://doi.org/10.1021/bk-1999-0735.ch012.
DOI: https://doi.org/10.1021/bk-1999-0735.ch012
https://doi.org/10.1021/bk-1999-0735.ch012.">
Armes S. P., Miller J. F. - Optimum Reaction Conditions for the Polymerization of Aniline in Aqueous Solution by Ammonium Persulphate, Synthetic Metals 22 (4) (1988) 385-393. https://doi.org/10.1016/0379-6779(88)90109-9.
DOI: https://doi.org/10.1016/0379-6779(88)90109-9
https://doi.org/10.1016/0379-6779(88)90109-9.">
Kan K., Yamamoto H., Kaneko D., Tateyama S., Kaneko T. - Novel π-Conjugated Bio-Based Polymer, Poly(3-Amino-4-Hydroxybenzoic Acid), and Its Solvatochromism, Pure and Applied Chemistry 86 (5) (2014) 685-690. https://doi.org/10.1515/pac-2013-1115.
DOI: https://doi.org/10.1515/pac-2013-1115
https://doi.org/10.1515/pac-2013-1115.">
Park G. T., Chang J.-H., Lim A. R. - Thermotropic Liquid Crystalline Polymers with Various Alkoxy Side Groups: Thermal Properties and Molecular Dynamics, Polymers 11 (6) (2019) 992. https://doi.org/10.3390/polym11060992.
DOI: https://doi.org/10.3390/polym11060992
https://doi.org/10.3390/polym11060992.">
Jackson W. J., Kuhfuss H. F. - Liquid Crystal Polymers. I. Preparation and Properties of p-Hydroxybenzoic Acid Copolyesters, Journal of Polymer Science: Polymer Chemistry Edition 14 (8) (1976) 2043-2058. https://doi.org/10.1002/pol.1976.170140820.
DOI: https://doi.org/10.1002/pol.1976.170140820
https://doi.org/10.1002/pol.1976.170140820.">
Ophir Z., Ide Y. - Injection Molding of Thermotropic Liquid Crystal Polymers, Polymer Engineering & Science 23 (14) (1983) 792-796. https://doi.org/10.1002/pen.760231409.
DOI: https://doi.org/10.1002/pen.760231409
https://doi.org/10.1002/pen.760231409.">
Uzman M., Kühnpast K., Springer J. - Orientational Behaviour of Polymer Blends Containing a Liquid-Crystalline Component, Die Makromolekulare Chemie 190 (12) (1989) 3185-3194. https://doi.org/10.1002/macp.1989.021901216.
DOI: https://doi.org/10.1002/macp.1989.021901216
https://doi.org/10.1002/macp.1989.021901216.">
Lenz R. W. - Synthesis and Properties of Thermotropic Liquid Crystal Polymers with Main Chain Mesogenic Units, Polymer Journal 17 (1) (1985) 105-115. https://doi.org/ 10.1295/polymj.17.105.
DOI: https://doi.org/10.1295/polymj.17.105
https://doi.org/ 10.1295/polymj.17.105.">
Zeng L., Li R., Chen P., Xu J., Liu P. - Synthesis and Characterization of Thermotropic Liquid Crystalline Polyarylate with Ether Ether Ketone Segments in the Main Chain, Journal of Applied Polymer Science 133 (32) (2016). https://doi.org/10.1002/app.43800.
DOI: https://doi.org/10.1002/app.43800
https://doi.org/10.1002/app.43800.">
Martínez-Gómez A., Encinar M., Fernández-Blázquez J. P., Rubio R. G., Pérez E. - Relationship Between Composition, Structure and Dynamics of Main-Chain Liquid Crystalline Polymers with Biphenyl Mesogens. In Liquid Crystalline Polymers: Volume 1–Structure and Chemistry, Thakur, V. K., Kessler M. R., Eds., Springer International Publishing: Cham, 2016, pp. 453-476. https://doi.org/10.1007/978-3-319-22894-5_15.
DOI: https://doi.org/10.1007/978-3-319-22894-5_15
https://doi.org/10.1007/978-3-319-22894-5_15.">
Damman S. B., Mercx F. P. M., Kootwijk-Damman C. M. - Liquid-Crystalline Main-Chain Polymers with a Poly(p-Phenylene Terephthalate) Backbone: 1. Synthesis, Characterization and Rheology of Polyesters with Alkoxy Side Chains, Polymer 34 (9) (1993) 1891-1897. https://doi.org/10.1016/0032-3861(93)90431-9.
DOI: https://doi.org/10.1016/0032-3861(93)90431-9
https://doi.org/10.1016/0032-3861(93)90431-9.">
Chang J. H., Jo B. W. - Blends of PBT with Rigid Thermotropic LCP Having Flexible Side Groups: Comparison of Their Tensile Properties with Semirigid Main-Chain TLCP Blends, Journal of Applied Polymer Science 60 (7) (1996) 939-946. https://doi.org/ 10.1002/(SICI)1097-4628(19960516)60:7<939::AID-APP3>3.0.CO,2-N.
DOI: https://doi.org/10.1002/(SICI)1097-4628(19960516)60:7<939::AID-APP3>3.0.CO;2-N
https://doi.org/ 10.1002/(SICI)1097-4628(19960516)60:7<939::AID-APP3>3.0.CO,2-N.">
Chung S. J., Kim K. K., Jin J. I. - Fluorescing Wholly Aromatic Polyesters Containing Diphenylanthracene Fluorophores, Polymer 40 (8) (1999) 1943-1953. https://doi.org/ 10.1016/S0032-3861(98)00420-0.
DOI: https://doi.org/10.1016/S0032-3861(98)00420-0
https://doi.org/ 10.1016/S0032-3861(98)00420-0.">
Mori T., Kijima M. - Synthesis and Electroluminescence Properties of Carbazole-Containing 2,6-Naphthalene-Based Conjugated Polymers, European Polymer Journal 45 (4) (2009) 1149-1157. https://doi.org/10.1016/j.eurpolymj.2008.12.042.
DOI: https://doi.org/10.1016/j.eurpolymj.2008.12.042
https://doi.org/10.1016/j.eurpolymj.2008.12.042.">
Lim W. L., Oo C. W., Kobayashi T. - Photoluminescent Enhancement of Polyesters via Photocrosslinking, Journal of Applied Polymer Science 132 (8) (2015). https://doi.org/ 10.1002/app.41504.
DOI: https://doi.org/10.1002/app.41504
https://doi.org/ 10.1002/app.41504.">
Gross R. A., Kalra B. - Biodegradable Polymers for the Environment, Science 297 (5582) (1997) 803-807. https://doi.org/10.1126/science.297.5582.803.
DOI: https://doi.org/10.1126/science.297.5582.803
https://doi.org/10.1126/science.297.5582.803.">
Ueda M., Sugita H., Sato M. - Synthesis of Poly(Benzoxazole)s by Direct Polycondensation of Dicarboxylic Acids with 3,3′-Dihydroxybenzidine Dihydrochloride Using Phosphorus Pentoxide/Methanesulfonic Acid as Condensing Agent and Solvent, Journal of Polymer Science Part A: Polymer Chemistry 24 (5) (1986) 1019-1026. https://doi.org/10.1002/pola.1986.080240517.
DOI: https://doi.org/10.1002/pola.1986.080240517
https://doi.org/10.1002/pola.1986.080240517.">
Imai Y., Taoka I., Uno K., Iwakura Y. - Polybenzoxazoles and Polybenzothiazoles, Die Makromolekulare Chemie 83 (1) (1965) 167-178. https://doi.org/10.1002/macp. 1965.020830114.
DOI: https://doi.org/10.1002/macp.1965.020830114
https://doi.org/10.1002/macp. 1965.020830114.">
Ohta Y., Niiyama T., Yokoyama A., Yokozawa T. - Chain-Growth Condensation Polymerization Approach to Synthesis of Well-Defined Polybenzoxazole: Importance of Higher Reactivity of 3-Amino-4-Hydroxybenzoic Acid Ester Compared to 4-Amino-3-Hydroxybenzoic Acid Ester, Journal of Polymer Science Part A: Polymer Chemistry 52 (12) (2014) 1730-1736. https://doi.org/10.1002/pola.27174.
DOI: https://doi.org/10.1002/pola.27174
https://doi.org/10.1002/pola.27174.">
Moyer W. W., Cole C., Anyos T. - Aromatic Polybenzoxazoles, Journal of Polymer Science Part A: General Papers 3 (6) (1965) 2107-2121. https://doi.org/10.1002/ pol.1965.100030603.
DOI: https://doi.org/10.1002/pol.1965.100030603
https://doi.org/10.1002/ pol.1965.100030603.">
Zhou C., Wang S., Zhuang Q., Han Z. - Enhanced Conductivity in Polybenzoxazoles Doped with Carboxylated Multi-Walled Carbon Nanotubes, Carbon 46 (9) (2008) 1232-1240. https://doi.org/10.1016/j.carbon.2008.05.005.
DOI: https://doi.org/10.1016/j.carbon.2008.05.005
https://doi.org/10.1016/j.carbon.2008.05.005.">
Ali M. A., Shimosegawa H., Nag A., Takada K., Kaneko T. - Synthesis of Thermotropic Polybenzoxazole Using 3-Amino-4-Hydroxybenzoic Acid, Journal of Polymer Research 24 (12) (2017) 214. https://doi.org/10.1007/s10965-017-1362-9.
DOI: https://doi.org/10.1007/s10965-017-1362-9
https://doi.org/10.1007/s10965-017-1362-9.">
Hsiao S. H., Chiou J. H. - Aromatic Polybenzoxazoles Containing Ether–Sulfone Linkages, Journal of Polymer Science Part A: Polymer Chemistry 39 (13) (2001) 2262-2270. https://doi.org/10.1002/pola.1203.
DOI: https://doi.org/10.1002/pola.1203
https://doi.org/10.1002/pola.1203.">
Hilborn J. G., Labadie J. W., Hedrick J. L. - Poly(Aryl ether-benzoxazoles), macromo-lecules 23 (11) (1990) 2854-2861. https://doi.org/10.1021/ma00213a006.
DOI: https://doi.org/10.1021/ma00213a006
https://doi.org/10.1021/ma00213a006.">
Smith J. G., Connell J. W., Hergenrother P. M. - Chemistry and Properties of Poly (Arylene Ether Benzoxazole), Polymer 33 (8) (1992) 1742-1747. https://doi.org/10.1016/ 0032-3861(92)91076-E.
DOI: https://doi.org/10.1016/0032-3861(92)91076-E
https://doi.org/10.1016/ 0032-3861(92)91076-E.">
Miyazaki T., Hasegawa M. - Highly Tough and Highly Transparent Soluble Polybenzoxazoles, High Performance Polymers 19 (3) (2007) 243-269. https://doi.org/ 10.1177/0954008306076265.
DOI: https://doi.org/10.1177/0954008306076265
https://doi.org/ 10.1177/0954008306076265.">
Oishi Y., Konnno A., Oravec J., Mori K. - Synthesis and Properties of Fluorine-Containing Polybenzoxazoles by In Situ Silylation Method, Journal of Photopolymer Science and Technology 19 (5) (2006) 669-672. https://doi.org/10.2494/ photopolymer.19.669.
DOI: https://doi.org/10.2494/photopolymer.19.669
https://doi.org/10.2494/ photopolymer.19.669.">
Feig V. R., Tran H., Bao Z. - Biodegradable Polymeric Materials in Degradable Electronic Devices, ACS Central Science 4 (3) (2018) 337-348. https://doi.org/10.1021/ acscentsci.7b00595.
DOI: https://doi.org/10.1021/acscentsci.7b00595
https://doi.org/10.1021/ acscentsci.7b00595.">
Kohl P. A. - Low-Dielectric Constant Insulators for Future Integrated Circuits and Packages, Annual Review of Chemical and Biomolecular Engineering 2 (2011) 379-401. https://doi.org/10.1146/annurev-chembioeng-061010-114137.
DOI: https://doi.org/10.1146/annurev-chembioeng-061010-114137
https://doi.org/10.1146/annurev-chembioeng-061010-114137.">
Volksen W., Miller R. D., Dubois G. - Low Dielectric Constant Materials, Chemical Reviews 110 (1) (2010) 56-110. https://doi.org/10.1021/cr9002819.
DOI: https://doi.org/10.1021/cr9002819
https://doi.org/10.1021/cr9002819.">
Lin Q., Cohen S. A., Gignac L., Herbst B., Klaus D., Simonyi E., Hedrick J., Warlaumont J., Lee H. J., Wu W. - Low Dielectric Constant Nanocomposite Thin Films Based on Silica Nanoparticle and Organic Thermosets, Journal of Polymer Science Part B: Polymer Physics 45 (12) (2007) 1482-1493. https://doi.org/10.1002/polb.21165.
DOI: https://doi.org/10.1002/polb.21165
https://doi.org/10.1002/polb.21165.">
Baik D., Lee W., Park Y. - Interfacial Characterization of polybenzoxazole/copper System, Molecular Crystals and Liquid Crystals 424 (1) (2004) 265-271. https://doi.org/ 10.1080/15421400490506270.
DOI: https://doi.org/10.1080/15421400490506270
https://doi.org/ 10.1080/15421400490506270.">
Hasegawa M., Kobayashi J., Vladimirov L. - Solution-processable low-CTE polybenzo-xazoles, Journal of Photopolymer Science and Technology 17 (2) (2004) 253-258. https://doi.org/10.2494/photopolymer.17.253.
DOI: https://doi.org/10.2494/photopolymer.17.253
https://doi.org/10.2494/photopolymer.17.253.">
Fukumaru T., Fujigaya T., Nakashima N. - Design and Preparation of Porous Polybenzoxazole Films Using the Tert-Butoxycarbonyl Group as a Pore Generator and Their Application for Patternable Low-k Materials, Polymer Chemistry 3 (2) (2012) 369-376. https://doi.org/10.1039/C1PY00470K.
DOI: https://doi.org/10.1039/C1PY00470K
https://doi.org/10.1039/C1PY00470K.">
MacDonald S. A., Ito H., Willson C. G. - Advances in the Design of Organic Resist Materials, Microelectronic Engineering 1 (4) (1983) 269-293. https://doi.org/ 10.1016/0167-9317(83)90017-5.
DOI: https://doi.org/10.1016/0167-9317(83)90017-5
https://doi.org/ 10.1016/0167-9317(83)90017-5.">
Wang Y., Yu J., Zhu J., Hu Z. - Hyperbranched Polybenzoxazoles Incorporated Polybenzoxazoles for High-Performance and Low-K Materials, Journal of Polymer Science Part A: Polymer Chemistry 54 (11) (2016) 1623-1632. https://doi.org/ 10.1002/pola.28018.
DOI: https://doi.org/10.1002/pola.28018
https://doi.org/ 10.1002/pola.28018.">
Fukukawa K., Shibasaki Y., Ueda M. - A Photosensitive Semi-Alicyclic Poly (Benzoxazole) with High Transparency and Low Dielectric Constant, Macromolecules 37 (22) (2004) 8256-8261. https://doi.org/10.1021/ma049063i.
DOI: https://doi.org/10.1021/ma049063i
https://doi.org/10.1021/ma049063i.">
Tsuchiya K., Ishii H., Shibasaki Y., Ando S., Ueda M. - Synthesis of a Novel Poly(Binaphthylene Ether) with a Low Dielectric Constant, Macromolecules 37 (13) (2004) 4794-4797. https://doi.org/10.1021/ma049390q.
DOI: https://doi.org/10.1021/ma049390q
https://doi.org/10.1021/ma049390q.">
Asensio J. A., Borrós S., Gómez-Romero P. - Enhanced Conductivity in Polyanion-Containing Polybenzimidazoles, Improved Materials for Proton-Exchange Membranes and PEM Fuel Cells, Electrochemistry Communications 5 (11) (2003) 967-972. https://doi.org/10.1016/j.elecom.2003.09.007.
DOI: https://doi.org/10.1016/j.elecom.2003.09.007
https://doi.org/10.1016/j.elecom.2003.09.007.">
He R., Li Q., Bach A., Jensen J. O., Bjerrum N. J. - Physicochemical Properties of Phosphoric Acid Doped Polybenzimidazole Membranes for Fuel Cells, Journal of Membrane Science 277 (1) (2006) 38-45. https://doi.org/10.1016/j.memsci.2005.10.005.
DOI: https://doi.org/10.1016/j.memsci.2005.10.005
https://doi.org/10.1016/j.memsci.2005.10.005.">
Sannigrahi A., Arunbabu D., Sankar, R. M., Jana T. - Tuning the Molecular Properties of Polybenzimidazole by Copolymerization, Journal of Physical Chemistry B111 (42) (2007) 12124-12132. https://doi.org/10.1021/jp073973v.
DOI: https://doi.org/10.1021/jp073973v
https://doi.org/10.1021/jp073973v.">
Asensio J. A., Borrós S., Gómez-Romero P. - Polymer Electrolyte Fuel Cells Based on Phosphoric Acid-Impregnated Poly(2,5-Benzimidazole) Membranes, Journal of the Electrochemical Society 151 (2) (2004) A304-A310. https://doi.org/10.1149/1.1640628.
DOI: https://doi.org/10.1149/1.1640628
https://doi.org/10.1149/1.1640628.">
Pahari S., Roy S. - Structural and Conformational Properties of Polybenzimidazoles in Melt and Phosphoric Acid Solution: A Polyelectrolyte Membrane for Fuel Cells, RSC Advances 6 (10) (2016) 8211-8221. https://doi.org/10.1039/C5RA22159E.
DOI: https://doi.org/10.1039/C5RA22159E
https://doi.org/10.1039/C5RA22159E.">
Omar N., Daowd M., Bossche P. van den Hegazy O., Smekens J., Coosemans T., Mierlo J. van - Rechargeable Energy Storage Systems for Plug-in Hybrid Electric Vehicles Assessment of Electrical Characteristics, Energies 5 (8) (2012) 2952-2988. https://doi.org/10.3390/en5082952.
DOI: https://doi.org/10.3390/en5082952
https://doi.org/10.3390/en5082952.">
Endo K. - Fluorinated Amorphous Carbon as a Low-Dielectric-Constant Interlayer Dielectric. MRS Bulletin 22 (10) (1997) 55-58. https://doi.org/10.1557/ S0883769400034217.
DOI: https://doi.org/10.1557/S0883769400034217
https://doi.org/10.1557/ S0883769400034217.">
Kloster G., Scherban T., Xu G., Blaine J., Sun B., Zhou Y. - Porosity Effects on Low-k Dielectric Film Strength and Interfacial Adhesion, In Proceedings of the IEEE 2002 International Interconnect Technology Conference (Cat. No.02EX519) 2002, pp. 242-244. https://doi.org/10.1109/IITC.2002.1014946.
DOI: https://doi.org/10.1109/IITC.2002.1014946
https://doi.org/10.1109/IITC.2002.1014946.">
Downloads
Published
How to Cite
Issue
Section
License
This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.
Vietnam Journal of Sciences and Technology (VJST) is an open access and peer-reviewed journal. All academic publications could be made free to read and downloaded for everyone. In addition, articles are published under term of the Creative Commons Attribution-ShareAlike 4.0 International (CC BY-SA) Licence which permits use, distribution and reproduction in any medium, provided the original work is properly cited & ShareAlike terms followed.
Copyright on any research article published in VJST is retained by the respective author(s), without restrictions. Authors grant VAST Journals System a license to publish the article and identify itself as the original publisher. Upon author(s) by giving permission to VJST either via VJST journal portal or other channel to publish their research work in VJST agrees to all the terms and conditions of https://creativecommons.org/licenses/by-sa/4.0/ License and terms & condition set by VJST.
Authors have the responsibility of to secure all necessary copyright permissions for the use of 3rd-party materials in their manuscript.
Vietnam Journal of Science and Technology (VJST) is pleased to notice: