Solution-Processable Colorless Polyimides Derived from Hydrogenated Pyromellitic Dianhydride: Strategies to Reduce the Coefficients of Thermal Expansion by Maximizing the Spontaneous Chain Orientation Behavior during Solution Casting
In this study, practically useful colorless polyimides (PIs) with low coefficients of thermal expansion (CTEs) and other desirable properties were prepared from hydrogenated pyromellitic dianhydride (1-<i>exo</i>,2-<i>exo</i>,4-<i>exo</i>,5-<i>exo</i>-...
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MDPI AG
2022-03-01
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| Series: | Polymers |
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| Online Access: | https://www.mdpi.com/2073-4360/14/6/1131 |
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| author | Masatoshi Hasegawa Katsuki Ichikawa Shuichi Takahashi Junichi Ishii |
| author_facet | Masatoshi Hasegawa Katsuki Ichikawa Shuichi Takahashi Junichi Ishii |
| author_sort | Masatoshi Hasegawa |
| collection | DOAJ |
| description | In this study, practically useful colorless polyimides (PIs) with low coefficients of thermal expansion (CTEs) and other desirable properties were prepared from hydrogenated pyromellitic dianhydride (1-<i>exo</i>,2-<i>exo</i>,4-<i>exo</i>,5-<i>exo</i>-cyclohexanetetracarboxylic dianhydride, H-PMDA). A modified one-pot polymerization method afforded a high-molecular-weight PI with sufficient film-forming ability from 2,2′-bis(trifluoromethyl)benzidine (TFMB) with a rod-like structure and H-PMDA. However, the PI film cast from its homogeneous solution did not have low CTEs, similar to the analogous system using <i>meta</i>-tolidine. To solve this problem, a series of amide- and amide-imide-containing diamines were designed and synthesized. The modified one-pot polymerization of H-PMDA and the diamines in <i>γ</i>-butyrolactone produced homogeneous, viscous, and stable solutions of high-molecular-weight PIs with high solid contents. The cast films of certain systems examined in this study simultaneously achieved low CTEs, high optical transparency, considerably high glass transition temperatures (<i>T</i><sub>g</sub>s), and sufficient ductility. A possible mechanism for the generation of low CTEs, which is closely related to the spontaneous in-plane orientation behavior during solution casting, was proposed. Certain H-PMDA-based PIs developed in this study are promising colorless heat-resistant plastic substrates for use in image display devices and other optical applications. |
| first_indexed | 2024-03-09T12:53:31Z |
| format | Article |
| id | doaj.art-0c71247750224cec9c3002c096e8cdf9 |
| institution | Directory Open Access Journal |
| issn | 2073-4360 |
| language | English |
| last_indexed | 2024-03-09T12:53:31Z |
| publishDate | 2022-03-01 |
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| record_format | Article |
| series | Polymers |
| spelling | doaj.art-0c71247750224cec9c3002c096e8cdf92023-11-30T22:02:57ZengMDPI AGPolymers2073-43602022-03-01146113110.3390/polym14061131Solution-Processable Colorless Polyimides Derived from Hydrogenated Pyromellitic Dianhydride: Strategies to Reduce the Coefficients of Thermal Expansion by Maximizing the Spontaneous Chain Orientation Behavior during Solution CastingMasatoshi Hasegawa0Katsuki Ichikawa1Shuichi Takahashi2Junichi Ishii3Department of Chemistry, Faculty of Science, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, JapanDepartment of Chemistry, Faculty of Science, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, JapanDepartment of Chemistry, Faculty of Science, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, JapanDepartment of Chemistry, Faculty of Science, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, JapanIn this study, practically useful colorless polyimides (PIs) with low coefficients of thermal expansion (CTEs) and other desirable properties were prepared from hydrogenated pyromellitic dianhydride (1-<i>exo</i>,2-<i>exo</i>,4-<i>exo</i>,5-<i>exo</i>-cyclohexanetetracarboxylic dianhydride, H-PMDA). A modified one-pot polymerization method afforded a high-molecular-weight PI with sufficient film-forming ability from 2,2′-bis(trifluoromethyl)benzidine (TFMB) with a rod-like structure and H-PMDA. However, the PI film cast from its homogeneous solution did not have low CTEs, similar to the analogous system using <i>meta</i>-tolidine. To solve this problem, a series of amide- and amide-imide-containing diamines were designed and synthesized. The modified one-pot polymerization of H-PMDA and the diamines in <i>γ</i>-butyrolactone produced homogeneous, viscous, and stable solutions of high-molecular-weight PIs with high solid contents. The cast films of certain systems examined in this study simultaneously achieved low CTEs, high optical transparency, considerably high glass transition temperatures (<i>T</i><sub>g</sub>s), and sufficient ductility. A possible mechanism for the generation of low CTEs, which is closely related to the spontaneous in-plane orientation behavior during solution casting, was proposed. Certain H-PMDA-based PIs developed in this study are promising colorless heat-resistant plastic substrates for use in image display devices and other optical applications.https://www.mdpi.com/2073-4360/14/6/1131polyimideshydrogenated pyromellitic dianhydride (H-PMDA)optical transparencycoefficients of thermal expansion (CTE)toughnesssolution processability |
| spellingShingle | Masatoshi Hasegawa Katsuki Ichikawa Shuichi Takahashi Junichi Ishii Solution-Processable Colorless Polyimides Derived from Hydrogenated Pyromellitic Dianhydride: Strategies to Reduce the Coefficients of Thermal Expansion by Maximizing the Spontaneous Chain Orientation Behavior during Solution Casting Polymers polyimides hydrogenated pyromellitic dianhydride (H-PMDA) optical transparency coefficients of thermal expansion (CTE) toughness solution processability |
| title | Solution-Processable Colorless Polyimides Derived from Hydrogenated Pyromellitic Dianhydride: Strategies to Reduce the Coefficients of Thermal Expansion by Maximizing the Spontaneous Chain Orientation Behavior during Solution Casting |
| title_full | Solution-Processable Colorless Polyimides Derived from Hydrogenated Pyromellitic Dianhydride: Strategies to Reduce the Coefficients of Thermal Expansion by Maximizing the Spontaneous Chain Orientation Behavior during Solution Casting |
| title_fullStr | Solution-Processable Colorless Polyimides Derived from Hydrogenated Pyromellitic Dianhydride: Strategies to Reduce the Coefficients of Thermal Expansion by Maximizing the Spontaneous Chain Orientation Behavior during Solution Casting |
| title_full_unstemmed | Solution-Processable Colorless Polyimides Derived from Hydrogenated Pyromellitic Dianhydride: Strategies to Reduce the Coefficients of Thermal Expansion by Maximizing the Spontaneous Chain Orientation Behavior during Solution Casting |
| title_short | Solution-Processable Colorless Polyimides Derived from Hydrogenated Pyromellitic Dianhydride: Strategies to Reduce the Coefficients of Thermal Expansion by Maximizing the Spontaneous Chain Orientation Behavior during Solution Casting |
| title_sort | solution processable colorless polyimides derived from hydrogenated pyromellitic dianhydride strategies to reduce the coefficients of thermal expansion by maximizing the spontaneous chain orientation behavior during solution casting |
| topic | polyimides hydrogenated pyromellitic dianhydride (H-PMDA) optical transparency coefficients of thermal expansion (CTE) toughness solution processability |
| url | https://www.mdpi.com/2073-4360/14/6/1131 |
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