Soluble polyimides from unsymmetrical diamine containing benzimidazole ring and trifluoromethyl pendent group
New unsymmetrical diamine monomer containing both the benzimidazole ring and trifluoromethyl group, 6,4′-diamino-2′-trifluoromethyl-2-phenylbenzimidazole, was prepared from 2-bromo-5-nitrobenzotrifluoride and 4-nitro-1,2-phenylenediamine. The monomer was polymerized with ODPA, BTDA and 6FDA by using...
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Veröffentlicht in: | Polymer (Guilford) 2008-05, Vol.49 (11), p.2644-2649 |
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creator | Choi, Hyungsam Chung, Im Sik Hong, Kipyo Park, Chan Eon Kim, Sang Youl |
description | New unsymmetrical diamine monomer containing both the benzimidazole ring and trifluoromethyl group, 6,4′-diamino-2′-trifluoromethyl-2-phenylbenzimidazole, was prepared from 2-bromo-5-nitrobenzotrifluoride and 4-nitro-1,2-phenylenediamine. The monomer was polymerized with ODPA, BTDA and 6FDA by using one-pot synthetic method to obtain corresponding polyimides. All the prepared polyimides were soluble in aprotic polar solvents. Incorporation of trifluoromethyl groups unsymmetrically in the rigid polyimides improves their solubility without decreasing their physical properties. The polymers showed high glass transition temperature (Tg=289–352°C), high thermal stability (Td10>500°C), and relatively low coefficient of thermal expansion (CTE=26.1–46.4ppm/°C) because of their rigid-rod like structure. Also, they showed low refractive indexes (n=1.46–1.68) and low birefringence (Δ≈0.02) due to the trifluoromethyl pendent groups that interrupt chain packing and increase free volume. |
doi_str_mv | 10.1016/j.polymer.2008.04.019 |
format | Article |
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The monomer was polymerized with ODPA, BTDA and 6FDA by using one-pot synthetic method to obtain corresponding polyimides. All the prepared polyimides were soluble in aprotic polar solvents. Incorporation of trifluoromethyl groups unsymmetrically in the rigid polyimides improves their solubility without decreasing their physical properties. The polymers showed high glass transition temperature (Tg=289–352°C), high thermal stability (Td10>500°C), and relatively low coefficient of thermal expansion (CTE=26.1–46.4ppm/°C) because of their rigid-rod like structure. 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The monomer was polymerized with ODPA, BTDA and 6FDA by using one-pot synthetic method to obtain corresponding polyimides. All the prepared polyimides were soluble in aprotic polar solvents. Incorporation of trifluoromethyl groups unsymmetrically in the rigid polyimides improves their solubility without decreasing their physical properties. The polymers showed high glass transition temperature (Tg=289–352°C), high thermal stability (Td10>500°C), and relatively low coefficient of thermal expansion (CTE=26.1–46.4ppm/°C) because of their rigid-rod like structure. Also, they showed low refractive indexes (n=1.46–1.68) and low birefringence (Δ≈0.02) due to the trifluoromethyl pendent groups that interrupt chain packing and increase free volume.</description><subject>Applied sciences</subject><subject>Benzimidazole ring</subject><subject>Exact sciences and technology</subject><subject>Organic polymers</subject><subject>Physicochemistry of polymers</subject><subject>Polymers with particular properties</subject><subject>Preparation, kinetics, thermodynamics, mechanism and catalysts</subject><subject>Soluble polyimides</subject><subject>Trifluoromethyl pendent group</subject><issn>0032-3861</issn><issn>1873-2291</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><recordid>eNqFkE1r3DAQhkVoodu0P6HgS3uzM5Isf5xKCW0TCPTQ9iz0MU60yJIr2YXNr6_MLr3mNDC8zzvMQ8gHCg0F2t0cmyX604ypYQBDA20DdLwiBzr0vGZspK_IAYCzmg8dfUPe5nwEACZYeyDzz-g37bHaK9zsLOZqSnGutpBP84xrckb5yjo1u4CViWFVLrjwWGkMzzugnmPB075SwVYFmPwWSwWuTydfLRgshrV6THFb3pHXk_IZ31_mNfn97euv27v64cf3-9svD7XhPay1NWCACzapgY9WlKfoMI4oRDf0oDvRWtQ9HyeutYJOMzEJzc2EKHrdA7X8mnw69y4p_tkwr3J22aD3KmDcsuS87YuAvgTFOWhSzDnhJJfkZpVOkoLc5cqjvMiVu1wJrSxyC_fxckDl4mdKKhiX_8MMeMcY33Ofzzks3_51pSUbh8GgdQnNKm10L1z6B3FIlk8</recordid><startdate>20080527</startdate><enddate>20080527</enddate><creator>Choi, Hyungsam</creator><creator>Chung, Im Sik</creator><creator>Hong, Kipyo</creator><creator>Park, Chan Eon</creator><creator>Kim, Sang Youl</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>F28</scope><scope>FR3</scope><scope>JG9</scope></search><sort><creationdate>20080527</creationdate><title>Soluble polyimides from unsymmetrical diamine containing benzimidazole ring and trifluoromethyl pendent group</title><author>Choi, Hyungsam ; Chung, Im Sik ; Hong, Kipyo ; Park, Chan Eon ; Kim, Sang Youl</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c370t-dc0c0352fa839d50081899e556870b654deb739f3bba06b25f5b3cfee57b701d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Applied sciences</topic><topic>Benzimidazole ring</topic><topic>Exact sciences and technology</topic><topic>Organic polymers</topic><topic>Physicochemistry of polymers</topic><topic>Polymers with particular properties</topic><topic>Preparation, kinetics, thermodynamics, mechanism and catalysts</topic><topic>Soluble polyimides</topic><topic>Trifluoromethyl pendent group</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Choi, Hyungsam</creatorcontrib><creatorcontrib>Chung, Im Sik</creatorcontrib><creatorcontrib>Hong, Kipyo</creatorcontrib><creatorcontrib>Park, Chan Eon</creatorcontrib><creatorcontrib>Kim, Sang Youl</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Technology Research Database</collection><collection>ANTE: Abstracts in New Technology & Engineering</collection><collection>Engineering Research Database</collection><collection>Materials Research Database</collection><jtitle>Polymer (Guilford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Choi, Hyungsam</au><au>Chung, Im Sik</au><au>Hong, Kipyo</au><au>Park, Chan Eon</au><au>Kim, Sang Youl</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Soluble polyimides from unsymmetrical diamine containing benzimidazole ring and trifluoromethyl pendent group</atitle><jtitle>Polymer (Guilford)</jtitle><date>2008-05-27</date><risdate>2008</risdate><volume>49</volume><issue>11</issue><spage>2644</spage><epage>2649</epage><pages>2644-2649</pages><issn>0032-3861</issn><eissn>1873-2291</eissn><coden>POLMAG</coden><abstract>New unsymmetrical diamine monomer containing both the benzimidazole ring and trifluoromethyl group, 6,4′-diamino-2′-trifluoromethyl-2-phenylbenzimidazole, was prepared from 2-bromo-5-nitrobenzotrifluoride and 4-nitro-1,2-phenylenediamine. The monomer was polymerized with ODPA, BTDA and 6FDA by using one-pot synthetic method to obtain corresponding polyimides. All the prepared polyimides were soluble in aprotic polar solvents. Incorporation of trifluoromethyl groups unsymmetrically in the rigid polyimides improves their solubility without decreasing their physical properties. The polymers showed high glass transition temperature (Tg=289–352°C), high thermal stability (Td10>500°C), and relatively low coefficient of thermal expansion (CTE=26.1–46.4ppm/°C) because of their rigid-rod like structure. Also, they showed low refractive indexes (n=1.46–1.68) and low birefringence (Δ≈0.02) due to the trifluoromethyl pendent groups that interrupt chain packing and increase free volume.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><doi>10.1016/j.polymer.2008.04.019</doi><tpages>6</tpages></addata></record> |
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subjects | Applied sciences Benzimidazole ring Exact sciences and technology Organic polymers Physicochemistry of polymers Polymers with particular properties Preparation, kinetics, thermodynamics, mechanism and catalysts Soluble polyimides Trifluoromethyl pendent group |
title | Soluble polyimides from unsymmetrical diamine containing benzimidazole ring and trifluoromethyl pendent group |
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