CN1024543C - 二环己基-3,4,3′,4′-四甲酸的制备方法 - Google Patents
二环己基-3,4,3′,4′-四甲酸的制备方法 Download PDFInfo
- Publication number
- CN1024543C CN1024543C CN 88109106 CN88109106A CN1024543C CN 1024543 C CN1024543 C CN 1024543C CN 88109106 CN88109106 CN 88109106 CN 88109106 A CN88109106 A CN 88109106A CN 1024543 C CN1024543 C CN 1024543C
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- China
- Prior art keywords
- acid
- tetracarboxylic acid
- polyimide
- dicyclohexyl
- polymeric amide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 239000002253 acid Substances 0.000 title abstract description 53
- 229920001721 polyimide Polymers 0.000 title abstract description 51
- 239000004642 Polyimide Substances 0.000 title abstract description 36
- 239000004962 Polyamide-imide Substances 0.000 title description 2
- 229920002312 polyamide-imide Polymers 0.000 title description 2
- 150000002148 esters Chemical class 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 150000000000 tetracarboxylic acids Chemical class 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 13
- 238000005984 hydrogenation reaction Methods 0.000 claims description 12
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 12
- 229910052703 rhodium Inorganic materials 0.000 claims description 11
- 239000010948 rhodium Substances 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 238000007086 side reaction Methods 0.000 claims description 2
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 21
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 abstract description 15
- 150000004985 diamines Chemical class 0.000 abstract description 15
- 238000006243 chemical reaction Methods 0.000 description 30
- -1 tetracarboxylic acid dianhydride Chemical class 0.000 description 30
- 239000000243 solution Substances 0.000 description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 17
- 229940124530 sulfonamide Drugs 0.000 description 17
- 239000004202 carbamide Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
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- 150000001875 compounds Chemical class 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
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- YVNRUPSDZZZUQJ-UHFFFAOYSA-N [O].NC1=CC=CC=C1 Chemical compound [O].NC1=CC=CC=C1 YVNRUPSDZZZUQJ-UHFFFAOYSA-N 0.000 description 7
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
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- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 4
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- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 4
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
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- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 102000002322 Egg Proteins Human genes 0.000 description 2
- 108010000912 Egg Proteins Proteins 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
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- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
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- 239000003513 alkali Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
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- 239000001110 calcium chloride Substances 0.000 description 2
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
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- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
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- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 2
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- 229920003223 poly(pyromellitimide-1,4-diphenyl ether) Polymers 0.000 description 2
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- FHBXQJDYHHJCIF-UHFFFAOYSA-N (2,3-diaminophenyl)-phenylmethanone Chemical compound NC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1N FHBXQJDYHHJCIF-UHFFFAOYSA-N 0.000 description 1
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- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- QBSMHWVGUPQNJJ-UHFFFAOYSA-N 4-[4-(4-aminophenyl)phenyl]aniline Chemical group C1=CC(N)=CC=C1C1=CC=C(C=2C=CC(N)=CC=2)C=C1 QBSMHWVGUPQNJJ-UHFFFAOYSA-N 0.000 description 1
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
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- OAPDPORYXWQVJE-UHFFFAOYSA-N 4-propylaniline Chemical compound CCCC1=CC=C(N)C=C1 OAPDPORYXWQVJE-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
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- 150000001298 alcohols Chemical class 0.000 description 1
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- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
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Images
Landscapes
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP254049/87 | 1987-10-08 | ||
JP25404987A JPH0723339B2 (ja) | 1987-10-08 | 1987-10-08 | 新規なジシクロヘキシル―3,4,3′,4′―テトラカルボン酸二無水物及びその製造法 |
JP319206/87 | 1987-12-17 | ||
JP112967/88 | 1988-05-10 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN93117739A Division CN1033858C (zh) | 1987-10-08 | 1993-09-15 | 二环己基-3,4,3′,4′-四甲酸二酐的制备方法 |
CN99124375A Division CN1258015A (zh) | 1987-10-08 | 1999-11-26 | 由聚酰亚胺制成的取向膜及含有该取向膜的液晶显示装置 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1034707A CN1034707A (zh) | 1989-08-16 |
CN1024543C true CN1024543C (zh) | 1994-05-18 |
Family
ID=17259520
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 88109106 Expired - Fee Related CN1024543C (zh) | 1987-10-08 | 1988-10-07 | 二环己基-3,4,3′,4′-四甲酸的制备方法 |
Country Status (2)
Country | Link |
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JP (1) | JPH0723339B2 (ja) |
CN (1) | CN1024543C (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105254884A (zh) * | 2011-03-11 | 2016-01-20 | 宇部兴产株式会社 | 聚酰亚胺前体和聚酰亚胺 |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4604380B2 (ja) * | 2001-04-03 | 2011-01-05 | 宇部興産株式会社 | cis‐ジシクロヘキシル‐3,3’4,4’‐テトラカルボン酸テトラメチルの分離法 |
CN100422243C (zh) * | 2006-09-05 | 2008-10-01 | 浙江大学 | 聚酰胺酯前体相转化制备超低介电常数聚酰亚胺膜的方法 |
CN114096508B (zh) * | 2021-08-23 | 2023-08-15 | 河北海力恒远新材料股份有限公司 | 一种3,3′,4,4′-二环己基四甲酸的制备方法、酸性废水的处理方法 |
CN114672022B (zh) * | 2022-02-27 | 2023-09-08 | 广东工业大学 | 半芳香族聚酰亚胺及其基于半芳香族聚酰亚胺基的颜色可调室温磷光材料及其制备方法 |
-
1987
- 1987-10-08 JP JP25404987A patent/JPH0723339B2/ja not_active Expired - Fee Related
-
1988
- 1988-10-07 CN CN 88109106 patent/CN1024543C/zh not_active Expired - Fee Related
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105254884A (zh) * | 2011-03-11 | 2016-01-20 | 宇部兴产株式会社 | 聚酰亚胺前体和聚酰亚胺 |
CN105254884B (zh) * | 2011-03-11 | 2018-05-29 | 宇部兴产株式会社 | 聚酰亚胺前体和聚酰亚胺 |
Also Published As
Publication number | Publication date |
---|---|
JPH0723339B2 (ja) | 1995-03-15 |
JPH0196147A (ja) | 1989-04-14 |
CN1034707A (zh) | 1989-08-16 |
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