A Novel Diamine Containing Ester and Diphenylethane Groups for Colorless Polyimide with a Low Dielectric Constant and Low Water Absorption
In this study, a novel diamine monomer containing ester and phenyl moieties, 1,2-diphenylethane-1,2-diyl bis(4-aminobenzoate) (1,2-DPEDBA), was synthesized through a three-step reaction. Using this diamine, a novel polyimide (PI) film was prepared with 4,4′-(hexafluoroisopropylidene)diphthalic anhyd...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-10-01
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| Series: | Polymers |
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| Online Access: | https://www.mdpi.com/2073-4360/14/21/4504 |
| _version_ | 1797466723378528256 |
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| author | Jun Seok Lee Yong-Zhu Yan Sung Soo Park Suk-kyun Ahn Chang-Sik Ha |
| author_facet | Jun Seok Lee Yong-Zhu Yan Sung Soo Park Suk-kyun Ahn Chang-Sik Ha |
| author_sort | Jun Seok Lee |
| collection | DOAJ |
| description | In this study, a novel diamine monomer containing ester and phenyl moieties, 1,2-diphenylethane-1,2-diyl bis(4-aminobenzoate) (1,2-DPEDBA), was synthesized through a three-step reaction. Using this diamine, a novel polyimide (PI) film was prepared with 4,4′-(hexafluoroisopropylidene)diphthalic anhydride (6-FDA) as a counter dianhydride through a typical two-step chemical imidization. For comparison, poly(pyromellitic dianhydride-co-4,4′-oxydianiline) (PMDA-ODA PI) was also synthesized via thermal imidization. The resulting 6-FDA-DPEDBA PI film was not only soluble in common polar solvents with high boiling points, such as N,N-dimethylacetamide (DMAc) and N,N-dimethylformamide (DMF), but also soluble in common low-boiling-point polar solvents, such as chloroform (CHCl<sub>3</sub>) and dichloromethane (CH<sub>2</sub>Cl<sub>2</sub>), at room temperature. The resulting novel PI showed a 5% weight loss temperature (T<sup>5</sup><sub>d</sub>) at 360 °C under a nitrogen atmosphere. The resulting PI film was colorless and transparent with a transmittance of 87.1% in the visible light region ranging from 400 to 760 nm. The water absorption of the novel PI film was of 1.78%. The PI film also possessed a good moisture barrier and hydrophobicity. Furthermore, the resulting PI film displayed a low dielectric constant of 2.17 at 10<sup>6</sup> Hz at room temperature. In conclusion, the novel PI film exhibited much better optical transparency, lower moisture absorption, and a lower dielectric constant as well as better solubility than the PMDA-ODA PI film, which is insoluble in any solvent, although its thermal stability is not better than that of PMDA-ODA PI. |
| first_indexed | 2024-03-09T18:43:46Z |
| format | Article |
| id | doaj.art-1ebd694ebeb94f5b96f79645d8f4516c |
| institution | Directory Open Access Journal |
| issn | 2073-4360 |
| language | English |
| last_indexed | 2024-03-09T18:43:46Z |
| publishDate | 2022-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Polymers |
| spelling | doaj.art-1ebd694ebeb94f5b96f79645d8f4516c2023-11-24T06:27:20ZengMDPI AGPolymers2073-43602022-10-011421450410.3390/polym14214504A Novel Diamine Containing Ester and Diphenylethane Groups for Colorless Polyimide with a Low Dielectric Constant and Low Water AbsorptionJun Seok Lee0Yong-Zhu Yan1Sung Soo Park2Suk-kyun Ahn3Chang-Sik Ha4Department of Polymer Science and Engineering, School of Chemical Engineering, Pusan National University, Busan 46241, KoreaDepartment of Polymer Science and Engineering, School of Chemical Engineering, Pusan National University, Busan 46241, KoreaDivision of Advanced Materials Engineering, Dong-Eui University, Busan 47340, KoreaDepartment of Polymer Science and Engineering, School of Chemical Engineering, Pusan National University, Busan 46241, KoreaDepartment of Polymer Science and Engineering, School of Chemical Engineering, Pusan National University, Busan 46241, KoreaIn this study, a novel diamine monomer containing ester and phenyl moieties, 1,2-diphenylethane-1,2-diyl bis(4-aminobenzoate) (1,2-DPEDBA), was synthesized through a three-step reaction. Using this diamine, a novel polyimide (PI) film was prepared with 4,4′-(hexafluoroisopropylidene)diphthalic anhydride (6-FDA) as a counter dianhydride through a typical two-step chemical imidization. For comparison, poly(pyromellitic dianhydride-co-4,4′-oxydianiline) (PMDA-ODA PI) was also synthesized via thermal imidization. The resulting 6-FDA-DPEDBA PI film was not only soluble in common polar solvents with high boiling points, such as N,N-dimethylacetamide (DMAc) and N,N-dimethylformamide (DMF), but also soluble in common low-boiling-point polar solvents, such as chloroform (CHCl<sub>3</sub>) and dichloromethane (CH<sub>2</sub>Cl<sub>2</sub>), at room temperature. The resulting novel PI showed a 5% weight loss temperature (T<sup>5</sup><sub>d</sub>) at 360 °C under a nitrogen atmosphere. The resulting PI film was colorless and transparent with a transmittance of 87.1% in the visible light region ranging from 400 to 760 nm. The water absorption of the novel PI film was of 1.78%. The PI film also possessed a good moisture barrier and hydrophobicity. Furthermore, the resulting PI film displayed a low dielectric constant of 2.17 at 10<sup>6</sup> Hz at room temperature. In conclusion, the novel PI film exhibited much better optical transparency, lower moisture absorption, and a lower dielectric constant as well as better solubility than the PMDA-ODA PI film, which is insoluble in any solvent, although its thermal stability is not better than that of PMDA-ODA PI.https://www.mdpi.com/2073-4360/14/21/4504polyimidea novel diaminelow water absorptionlow dielectric constanthigh transparencyhigh solubility |
| spellingShingle | Jun Seok Lee Yong-Zhu Yan Sung Soo Park Suk-kyun Ahn Chang-Sik Ha A Novel Diamine Containing Ester and Diphenylethane Groups for Colorless Polyimide with a Low Dielectric Constant and Low Water Absorption Polymers polyimide a novel diamine low water absorption low dielectric constant high transparency high solubility |
| title | A Novel Diamine Containing Ester and Diphenylethane Groups for Colorless Polyimide with a Low Dielectric Constant and Low Water Absorption |
| title_full | A Novel Diamine Containing Ester and Diphenylethane Groups for Colorless Polyimide with a Low Dielectric Constant and Low Water Absorption |
| title_fullStr | A Novel Diamine Containing Ester and Diphenylethane Groups for Colorless Polyimide with a Low Dielectric Constant and Low Water Absorption |
| title_full_unstemmed | A Novel Diamine Containing Ester and Diphenylethane Groups for Colorless Polyimide with a Low Dielectric Constant and Low Water Absorption |
| title_short | A Novel Diamine Containing Ester and Diphenylethane Groups for Colorless Polyimide with a Low Dielectric Constant and Low Water Absorption |
| title_sort | novel diamine containing ester and diphenylethane groups for colorless polyimide with a low dielectric constant and low water absorption |
| topic | polyimide a novel diamine low water absorption low dielectric constant high transparency high solubility |
| url | https://www.mdpi.com/2073-4360/14/21/4504 |
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