Novel degradable acetal-linkage-containing epoxy resins with high thermal stability: synthesis and application in carbon fiber-reinforced plastics
Two novel types of degradable acetal-linkage-containing epoxy resins were synthesized through the addition reaction of 2,2-bis(4-hydroxycyclohexyl)propane (HBA) or 2,2-bis[4-(2-hydroxyethoxy)phenyl]propane (HOBA) with cyclohexane dimethanol vinyl glycidyl ether (CHDMVG). The thermal decomposition te...
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| Veröffentlicht in: | Polymer journal 2022-03, Vol.54 (3), p.313-322 |
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| creator | Kuroyanagi, Mayo Yamaguchi, Ayaka Hashimoto, Tamotsu Urushisaki, Michio Sakaguchi, Toshikazu Kawabe, Kazumasa |
| description | Two novel types of degradable acetal-linkage-containing epoxy resins were synthesized through the addition reaction of 2,2-bis(4-hydroxycyclohexyl)propane (HBA) or 2,2-bis[4-(2-hydroxyethoxy)phenyl]propane (HOBA) with cyclohexane dimethanol vinyl glycidyl ether (CHDMVG). The thermal decomposition temperatures (
T
d
) of the cured HBA–CHDMVG (283 °C) and HOBA–CHDMVG (319 °C) epoxy resins indicated that they were more thermally stable than several previously reported acetal-linkage-containing epoxy resins. The Charpy impact test results demonstrated that the toughnesses of the HOBA–CHDMVG-based epoxy resin sheets and HOBA–CHDMVG-based carbon fiber-reinforced plastics (CFRPs) were higher than those of conventional bisphenol-A-based epoxy resin sheets and CFRPs. The HOBA–CHDMVG-based epoxy resin sheets were completely decomposed via hydrolysis under acidic conditions, and the hydrolysis products were soluble in a tetrahydrofuran–H
2
O mixed solvent. Furthermore, the carbon fibers of the HOBA–CHDMVG-based CFRPs were recovered via the decomposition of the matrix epoxy resin. In contrast, when H
2
O was the only solvent for the acid treatment, the HOBA–CHDMVG-based epoxy resin sheets and CFRPs did not undergo any changes. Therefore, we developed novel degradable epoxy resins, which easily decomposed in the presence of organic solvents, were stable in the absence of organic solvents and exhibited high thermal stability and remarkable toughness.
Novel alcohol-derived degradable acetal-linkage-containing epoxy resins HBA–CHDMVG and HOBA–CHDMVG were synthesized. The thermal decomposition temperature of HOBA–CHDMVG was higher than 300 °C; moreover, HOBA–CHDMVG exhibited excellent Charpy impact strength. The cured HOBA–CHDMVG was completely decomposed during the hydrolysis reaction under acidic conditions, and the reaction products were soluble in a tetrahydrofuran/H
2
O mixed solvent. Furthermore, the carbon fibers in the carbon-fiber-reinforced plastic with a HOBA–CHDMVG matrix were recovered via the complete decomposition of HOBA–CHDMVG. |
| doi_str_mv | 10.1038/s41428-021-00585-w |
| format | Article |
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T
d
) of the cured HBA–CHDMVG (283 °C) and HOBA–CHDMVG (319 °C) epoxy resins indicated that they were more thermally stable than several previously reported acetal-linkage-containing epoxy resins. The Charpy impact test results demonstrated that the toughnesses of the HOBA–CHDMVG-based epoxy resin sheets and HOBA–CHDMVG-based carbon fiber-reinforced plastics (CFRPs) were higher than those of conventional bisphenol-A-based epoxy resin sheets and CFRPs. The HOBA–CHDMVG-based epoxy resin sheets were completely decomposed via hydrolysis under acidic conditions, and the hydrolysis products were soluble in a tetrahydrofuran–H
2
O mixed solvent. Furthermore, the carbon fibers of the HOBA–CHDMVG-based CFRPs were recovered via the decomposition of the matrix epoxy resin. In contrast, when H
2
O was the only solvent for the acid treatment, the HOBA–CHDMVG-based epoxy resin sheets and CFRPs did not undergo any changes. Therefore, we developed novel degradable epoxy resins, which easily decomposed in the presence of organic solvents, were stable in the absence of organic solvents and exhibited high thermal stability and remarkable toughness.
Novel alcohol-derived degradable acetal-linkage-containing epoxy resins HBA–CHDMVG and HOBA–CHDMVG were synthesized. The thermal decomposition temperature of HOBA–CHDMVG was higher than 300 °C; moreover, HOBA–CHDMVG exhibited excellent Charpy impact strength. The cured HOBA–CHDMVG was completely decomposed during the hydrolysis reaction under acidic conditions, and the reaction products were soluble in a tetrahydrofuran/H
2
O mixed solvent. Furthermore, the carbon fibers in the carbon-fiber-reinforced plastic with a HOBA–CHDMVG matrix were recovered via the complete decomposition of HOBA–CHDMVG.</description><identifier>ISSN: 0032-3896</identifier><identifier>EISSN: 1349-0540</identifier><identifier>DOI: 10.1038/s41428-021-00585-w</identifier><language>eng</language><publisher>London: Nature Publishing Group UK</publisher><subject>639/166 ; 704/172 ; Acetal resins ; Biomaterials ; Bioorganic Chemistry ; Bisphenol A ; Carbon fiber reinforced plastics ; Carbon fiber reinforcement ; Carbon-epoxy composites ; Charpy impact test ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Cyclohexane ; Decomposition ; Decomposition reactions ; Degradation ; Epoxy resins ; Fiber reinforced polymers ; Hydrolysis ; Impact strength ; Original Article ; Polymer Sciences ; Propane ; Reaction products ; Sheets ; Solvents ; Surfaces and Interfaces ; Tetrahydrofuran ; Thermal decomposition ; Thermal stability ; Thin Films</subject><ispartof>Polymer journal, 2022-03, Vol.54 (3), p.313-322</ispartof><rights>The Author(s), under exclusive licence to The Society of Polymer Science, Japan 2021</rights><rights>The Author(s), under exclusive licence to The Society of Polymer Science, Japan 2021.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c249t-7666dd00f6c1575eb8103d8e76e5e67b00c011800763b430ab2493058d3fe4763</citedby><cites>FETCH-LOGICAL-c249t-7666dd00f6c1575eb8103d8e76e5e67b00c011800763b430ab2493058d3fe4763</cites><orcidid>0000-0002-9716-3281</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Kuroyanagi, Mayo</creatorcontrib><creatorcontrib>Yamaguchi, Ayaka</creatorcontrib><creatorcontrib>Hashimoto, Tamotsu</creatorcontrib><creatorcontrib>Urushisaki, Michio</creatorcontrib><creatorcontrib>Sakaguchi, Toshikazu</creatorcontrib><creatorcontrib>Kawabe, Kazumasa</creatorcontrib><title>Novel degradable acetal-linkage-containing epoxy resins with high thermal stability: synthesis and application in carbon fiber-reinforced plastics</title><title>Polymer journal</title><addtitle>Polym J</addtitle><description>Two novel types of degradable acetal-linkage-containing epoxy resins were synthesized through the addition reaction of 2,2-bis(4-hydroxycyclohexyl)propane (HBA) or 2,2-bis[4-(2-hydroxyethoxy)phenyl]propane (HOBA) with cyclohexane dimethanol vinyl glycidyl ether (CHDMVG). The thermal decomposition temperatures (
T
d
) of the cured HBA–CHDMVG (283 °C) and HOBA–CHDMVG (319 °C) epoxy resins indicated that they were more thermally stable than several previously reported acetal-linkage-containing epoxy resins. The Charpy impact test results demonstrated that the toughnesses of the HOBA–CHDMVG-based epoxy resin sheets and HOBA–CHDMVG-based carbon fiber-reinforced plastics (CFRPs) were higher than those of conventional bisphenol-A-based epoxy resin sheets and CFRPs. The HOBA–CHDMVG-based epoxy resin sheets were completely decomposed via hydrolysis under acidic conditions, and the hydrolysis products were soluble in a tetrahydrofuran–H
2
O mixed solvent. Furthermore, the carbon fibers of the HOBA–CHDMVG-based CFRPs were recovered via the decomposition of the matrix epoxy resin. In contrast, when H
2
O was the only solvent for the acid treatment, the HOBA–CHDMVG-based epoxy resin sheets and CFRPs did not undergo any changes. Therefore, we developed novel degradable epoxy resins, which easily decomposed in the presence of organic solvents, were stable in the absence of organic solvents and exhibited high thermal stability and remarkable toughness.
Novel alcohol-derived degradable acetal-linkage-containing epoxy resins HBA–CHDMVG and HOBA–CHDMVG were synthesized. The thermal decomposition temperature of HOBA–CHDMVG was higher than 300 °C; moreover, HOBA–CHDMVG exhibited excellent Charpy impact strength. The cured HOBA–CHDMVG was completely decomposed during the hydrolysis reaction under acidic conditions, and the reaction products were soluble in a tetrahydrofuran/H
2
O mixed solvent. Furthermore, the carbon fibers in the carbon-fiber-reinforced plastic with a HOBA–CHDMVG matrix were recovered via the complete decomposition of HOBA–CHDMVG.</description><subject>639/166</subject><subject>704/172</subject><subject>Acetal resins</subject><subject>Biomaterials</subject><subject>Bioorganic Chemistry</subject><subject>Bisphenol A</subject><subject>Carbon fiber reinforced plastics</subject><subject>Carbon fiber reinforcement</subject><subject>Carbon-epoxy composites</subject><subject>Charpy impact test</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Cyclohexane</subject><subject>Decomposition</subject><subject>Decomposition reactions</subject><subject>Degradation</subject><subject>Epoxy resins</subject><subject>Fiber reinforced polymers</subject><subject>Hydrolysis</subject><subject>Impact strength</subject><subject>Original Article</subject><subject>Polymer Sciences</subject><subject>Propane</subject><subject>Reaction products</subject><subject>Sheets</subject><subject>Solvents</subject><subject>Surfaces and Interfaces</subject><subject>Tetrahydrofuran</subject><subject>Thermal decomposition</subject><subject>Thermal stability</subject><subject>Thin Films</subject><issn>0032-3896</issn><issn>1349-0540</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid>BENPR</sourceid><recordid>eNp9kMFO3DAQhq0KpC4LL8DJUs9ux7HjZHtDq0KREFzas-U4k6y3XifYpsu-Bk9cwyL1xmlGo__7R_oIueTwlYNovyXJZdUyqDgDqNua7T-RBRdyxaCWcEIWAKJiol2pz-QspS1ApWqQC_JyP_1FT3sco-lN55Eai9l45l34Y0ZkdgrZuODCSHGeng80YnIh0b3LG7px44bmDcad8TRl0znv8uE7TYdQrsklakJPzTx7Z012U6AuUGtiV7bBdRhZRBeGKVrs6exNys6mc3I6GJ_w4n0uye_rH7_WP9ndw83t-uqO2UquMmuUUn0PMCjL66bGri0m-hYbhTWqpgOwwHkL0CjRSQGmK5gocnoxoCzHJfly7J3j9PiEKevt9BRDeakrVbWy1HFeUtUxZeOUUsRBz9HtTDxoDvrVvT6618W9fnOv9wUSRyiVcBgx_q_-gPoHPsmKRQ</recordid><startdate>20220301</startdate><enddate>20220301</enddate><creator>Kuroyanagi, Mayo</creator><creator>Yamaguchi, Ayaka</creator><creator>Hashimoto, Tamotsu</creator><creator>Urushisaki, Michio</creator><creator>Sakaguchi, Toshikazu</creator><creator>Kawabe, Kazumasa</creator><general>Nature Publishing Group UK</general><general>Nature Publishing Group</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>ABJCF</scope><scope>AFKRA</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>HCIFZ</scope><scope>JG9</scope><scope>KB.</scope><scope>PDBOC</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><orcidid>https://orcid.org/0000-0002-9716-3281</orcidid></search><sort><creationdate>20220301</creationdate><title>Novel degradable acetal-linkage-containing epoxy resins with high thermal stability: synthesis and application in carbon fiber-reinforced plastics</title><author>Kuroyanagi, Mayo ; Yamaguchi, Ayaka ; Hashimoto, Tamotsu ; Urushisaki, Michio ; Sakaguchi, Toshikazu ; Kawabe, Kazumasa</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c249t-7666dd00f6c1575eb8103d8e76e5e67b00c011800763b430ab2493058d3fe4763</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>639/166</topic><topic>704/172</topic><topic>Acetal resins</topic><topic>Biomaterials</topic><topic>Bioorganic Chemistry</topic><topic>Bisphenol A</topic><topic>Carbon fiber reinforced plastics</topic><topic>Carbon fiber reinforcement</topic><topic>Carbon-epoxy composites</topic><topic>Charpy impact test</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Cyclohexane</topic><topic>Decomposition</topic><topic>Decomposition reactions</topic><topic>Degradation</topic><topic>Epoxy resins</topic><topic>Fiber reinforced polymers</topic><topic>Hydrolysis</topic><topic>Impact strength</topic><topic>Original Article</topic><topic>Polymer Sciences</topic><topic>Propane</topic><topic>Reaction products</topic><topic>Sheets</topic><topic>Solvents</topic><topic>Surfaces and Interfaces</topic><topic>Tetrahydrofuran</topic><topic>Thermal decomposition</topic><topic>Thermal stability</topic><topic>Thin Films</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kuroyanagi, Mayo</creatorcontrib><creatorcontrib>Yamaguchi, Ayaka</creatorcontrib><creatorcontrib>Hashimoto, Tamotsu</creatorcontrib><creatorcontrib>Urushisaki, Michio</creatorcontrib><creatorcontrib>Sakaguchi, Toshikazu</creatorcontrib><creatorcontrib>Kawabe, Kazumasa</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</collection><collection>SciTech Premium Collection</collection><collection>Materials Research Database</collection><collection>Materials Science Database</collection><collection>Materials Science Collection</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><jtitle>Polymer journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kuroyanagi, Mayo</au><au>Yamaguchi, Ayaka</au><au>Hashimoto, Tamotsu</au><au>Urushisaki, Michio</au><au>Sakaguchi, Toshikazu</au><au>Kawabe, Kazumasa</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Novel degradable acetal-linkage-containing epoxy resins with high thermal stability: synthesis and application in carbon fiber-reinforced plastics</atitle><jtitle>Polymer journal</jtitle><stitle>Polym J</stitle><date>2022-03-01</date><risdate>2022</risdate><volume>54</volume><issue>3</issue><spage>313</spage><epage>322</epage><pages>313-322</pages><issn>0032-3896</issn><eissn>1349-0540</eissn><abstract>Two novel types of degradable acetal-linkage-containing epoxy resins were synthesized through the addition reaction of 2,2-bis(4-hydroxycyclohexyl)propane (HBA) or 2,2-bis[4-(2-hydroxyethoxy)phenyl]propane (HOBA) with cyclohexane dimethanol vinyl glycidyl ether (CHDMVG). The thermal decomposition temperatures (
T
d
) of the cured HBA–CHDMVG (283 °C) and HOBA–CHDMVG (319 °C) epoxy resins indicated that they were more thermally stable than several previously reported acetal-linkage-containing epoxy resins. The Charpy impact test results demonstrated that the toughnesses of the HOBA–CHDMVG-based epoxy resin sheets and HOBA–CHDMVG-based carbon fiber-reinforced plastics (CFRPs) were higher than those of conventional bisphenol-A-based epoxy resin sheets and CFRPs. The HOBA–CHDMVG-based epoxy resin sheets were completely decomposed via hydrolysis under acidic conditions, and the hydrolysis products were soluble in a tetrahydrofuran–H
2
O mixed solvent. Furthermore, the carbon fibers of the HOBA–CHDMVG-based CFRPs were recovered via the decomposition of the matrix epoxy resin. In contrast, when H
2
O was the only solvent for the acid treatment, the HOBA–CHDMVG-based epoxy resin sheets and CFRPs did not undergo any changes. Therefore, we developed novel degradable epoxy resins, which easily decomposed in the presence of organic solvents, were stable in the absence of organic solvents and exhibited high thermal stability and remarkable toughness.
Novel alcohol-derived degradable acetal-linkage-containing epoxy resins HBA–CHDMVG and HOBA–CHDMVG were synthesized. The thermal decomposition temperature of HOBA–CHDMVG was higher than 300 °C; moreover, HOBA–CHDMVG exhibited excellent Charpy impact strength. The cured HOBA–CHDMVG was completely decomposed during the hydrolysis reaction under acidic conditions, and the reaction products were soluble in a tetrahydrofuran/H
2
O mixed solvent. Furthermore, the carbon fibers in the carbon-fiber-reinforced plastic with a HOBA–CHDMVG matrix were recovered via the complete decomposition of HOBA–CHDMVG.</abstract><cop>London</cop><pub>Nature Publishing Group UK</pub><doi>10.1038/s41428-021-00585-w</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0002-9716-3281</orcidid></addata></record> |
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| ispartof | Polymer journal, 2022-03, Vol.54 (3), p.313-322 |
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| subjects | 639/166 704/172 Acetal resins Biomaterials Bioorganic Chemistry Bisphenol A Carbon fiber reinforced plastics Carbon fiber reinforcement Carbon-epoxy composites Charpy impact test Chemistry Chemistry and Materials Science Chemistry/Food Science Cyclohexane Decomposition Decomposition reactions Degradation Epoxy resins Fiber reinforced polymers Hydrolysis Impact strength Original Article Polymer Sciences Propane Reaction products Sheets Solvents Surfaces and Interfaces Tetrahydrofuran Thermal decomposition Thermal stability Thin Films |
| title | Novel degradable acetal-linkage-containing epoxy resins with high thermal stability: synthesis and application in carbon fiber-reinforced plastics |
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