JP2013508534A5 - - Google Patents
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- Publication number
- JP2013508534A5 JP2013508534A5 JP2012536986A JP2012536986A JP2013508534A5 JP 2013508534 A5 JP2013508534 A5 JP 2013508534A5 JP 2012536986 A JP2012536986 A JP 2012536986A JP 2012536986 A JP2012536986 A JP 2012536986A JP 2013508534 A5 JP2013508534 A5 JP 2013508534A5
- Authority
- JP
- Japan
- Prior art keywords
- polyimide
- weight
- parts
- aromatic
- phthalic anhydride
- 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.)
- Granted
Links
- 239000004642 Polyimide Substances 0.000 claims description 29
- 229920001721 polyimide Polymers 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 16
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 10
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- -1 aromatic tetracarboxylic acid compound Chemical class 0.000 claims description 6
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229920005575 poly(amic acid) Polymers 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910002804 graphite Inorganic materials 0.000 claims description 3
- 239000010439 graphite Substances 0.000 claims description 3
- 239000004113 Sepiolite Substances 0.000 claims description 2
- 150000004984 aromatic diamines Chemical group 0.000 claims description 2
- 229960000892 attapulgite Drugs 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052622 kaolinite Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910052625 palygorskite Inorganic materials 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- 229910052624 sepiolite Inorganic materials 0.000 claims description 2
- 235000019355 sepiolite Nutrition 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 description 6
- 0 *c(c(*)c(*)c(*)c1C(O2)=O)c1C2=O Chemical compound *c(c(*)c(*)c(*)c1C(O2)=O)c1C2=O 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 1
- NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical compound C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 1
- NBAUUNCGSMAPFM-UHFFFAOYSA-N 3-(3,4-dicarboxyphenyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=CC(C(O)=O)=C1C(O)=O NBAUUNCGSMAPFM-UHFFFAOYSA-N 0.000 description 1
- FYYYKXFEKMGYLZ-UHFFFAOYSA-N 4-(1,3-dioxo-2-benzofuran-5-yl)-2-benzofuran-1,3-dione Chemical compound C=1C=C2C(=O)OC(=O)C2=CC=1C1=CC=CC2=C1C(=O)OC2=O FYYYKXFEKMGYLZ-UHFFFAOYSA-N 0.000 description 1
- UITKHKNFVCYWNG-UHFFFAOYSA-N 4-(3,4-dicarboxybenzoyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 UITKHKNFVCYWNG-UHFFFAOYSA-N 0.000 description 1
- LFBALUPVVFCEPA-UHFFFAOYSA-N 4-(3,4-dicarboxyphenyl)phthalic acid Chemical group C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C(C(O)=O)=C1 LFBALUPVVFCEPA-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000004427 diamine group Chemical group 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- NTNWKDHZTDQSST-UHFFFAOYSA-N naphthalene-1,2-diamine Chemical compound C1=CC=CC2=C(N)C(N)=CC=C21 NTNWKDHZTDQSST-UHFFFAOYSA-N 0.000 description 1
- OLAPPGSPBNVTRF-UHFFFAOYSA-N naphthalene-1,4,5,8-tetracarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O OLAPPGSPBNVTRF-UHFFFAOYSA-N 0.000 description 1
- DOBFTMLCEYUAQC-UHFFFAOYSA-N naphthalene-2,3,6,7-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 DOBFTMLCEYUAQC-UHFFFAOYSA-N 0.000 description 1
- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 description 1
- DYFXGORUJGZJCA-UHFFFAOYSA-N phenylmethanediamine Chemical compound NC(N)C1=CC=CC=C1 DYFXGORUJGZJCA-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical group NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 description 1
- ABYXFACYSGVHCW-UHFFFAOYSA-N pyridine-3,5-diamine Chemical compound NC1=CN=CC(N)=C1 ABYXFACYSGVHCW-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25514509P | 2009-10-27 | 2009-10-27 | |
| US61/255,145 | 2009-10-27 | ||
| PCT/US2010/054226 WO2011056634A2 (en) | 2009-10-27 | 2010-10-27 | Polyimide resins for high temperature wear applications |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013508534A JP2013508534A (ja) | 2013-03-07 |
| JP2013508534A5 true JP2013508534A5 (https=) | 2013-12-12 |
| JP5604524B2 JP5604524B2 (ja) | 2014-10-08 |
Family
ID=43970678
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012536986A Expired - Fee Related JP5604524B2 (ja) | 2009-10-27 | 2010-10-27 | 高温摩耗用途向けポリイミド樹脂 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8507615B2 (https=) |
| EP (1) | EP2493961A4 (https=) |
| JP (1) | JP5604524B2 (https=) |
| KR (1) | KR20120113718A (https=) |
| CN (1) | CN102666660B (https=) |
| WO (1) | WO2011056634A2 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8824945B2 (en) * | 2011-02-09 | 2014-09-02 | Xerox Corporation | Metallic nanoparticle reinforced polyimide for fuser belt with high thermal conductivity |
| CN113685441B (zh) * | 2013-12-31 | 2023-08-15 | 美国圣戈班性能塑料公司 | 具有聚酰亚胺基质的复合轴承 |
| CA3059467A1 (en) | 2017-04-26 | 2018-11-01 | Henkel IP & Holding GmbH | Silane modified polymers with improved properties |
| PL3619254T3 (pl) | 2017-05-03 | 2023-10-02 | Henkel Ag & Co. Kgaa | Polimery zmodyfikowane silanem o udoskonalonej charakterystyce do kompozycji klejących |
| JP6938837B2 (ja) | 2017-09-04 | 2021-09-22 | エルジー・ケム・リミテッド | フレキシブルディスプレイ素子基板用ポリイミドフィルム |
| KR102202054B1 (ko) | 2018-01-22 | 2021-01-11 | 주식회사 엘지화학 | 액정 배향제 조성물, 이를 이용한 액정 배향막의 제조 방법, 및 이를 이용한 액정 배향막 |
| CN112601917B (zh) * | 2018-08-20 | 2025-05-27 | 大金工业株式会社 | 冷冻循环装置 |
| CN112223131A (zh) * | 2020-11-02 | 2021-01-15 | 惠州市新科磨具有限公司 | 耐磨薄片树脂切割片及其制备方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3179614A (en) * | 1961-03-13 | 1965-04-20 | Du Pont | Polyamide-acids, compositions thereof, and process for their preparation |
| US3998786A (en) * | 1973-05-25 | 1976-12-21 | University Of Notre Dame Du Lac | Process for preparing aromatic polyimides, polyimides prepared thereby |
| US4107125A (en) * | 1976-07-01 | 1978-08-15 | E. I. Du Pont De Nemours And Company | Crosslinked aromatic polyimides and articles made therefrom |
| US4552931A (en) * | 1984-09-11 | 1985-11-12 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Process of end-capping a polyimide system |
| US5116939A (en) * | 1987-08-11 | 1992-05-26 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Polyimide processing additives |
| US5055116A (en) * | 1989-05-22 | 1991-10-08 | Hoechst Celanese Corp. | Gas separation membranes comprising miscible blends of polyimide polymers |
| US5312866A (en) * | 1989-11-30 | 1994-05-17 | Mitsui Toatsu Chemicals, Incorporated | Polyimide based resin composition |
| JPH03215581A (ja) * | 1990-01-19 | 1991-09-20 | Daicel Chem Ind Ltd | ポリイミド塗膜の密着性改良方法 |
| US5115090A (en) * | 1990-03-30 | 1992-05-19 | Sachdev Krishna G | Viscosity stable, essentially gel-free polyamic acid compositions |
| US5886129A (en) * | 1997-07-01 | 1999-03-23 | E. I. Du Pont De Nemours And Company | Oxidatively stable rigid aromatic polyimide compositions and process for their preparation |
| US6501934B1 (en) * | 2000-10-26 | 2002-12-31 | Xerox Corporation | Transfer/transfuse member having increased durability |
| JP2004123857A (ja) * | 2002-10-01 | 2004-04-22 | Teijin Ltd | ポリアミド酸組成物およびポリアミド酸の製造方法 |
| US20050070658A1 (en) * | 2003-09-30 | 2005-03-31 | Soumyadeb Ghosh | Electrically conductive compositions, methods of manufacture thereof and articles derived from such compositions |
| US7265181B2 (en) * | 2004-07-09 | 2007-09-04 | E.I. Du Pont De Nemours And Company | Polyimide cross-linked polymer and shaped article thereof |
| JP5343561B2 (ja) * | 2006-07-23 | 2013-11-13 | 宇部興産株式会社 | 多成分ポリイミドからなるポリイミドフィルムの製造方法 |
| US20080119616A1 (en) * | 2006-11-22 | 2008-05-22 | General Electric Company | Polyimide resin compositions |
| JP4853534B2 (ja) * | 2009-03-13 | 2012-01-11 | 富士ゼロックス株式会社 | ポリアミック酸組成物、ポリイミド無端ベルト、定着装置および画像形成装置 |
-
2010
- 2010-10-27 EP EP10828880A patent/EP2493961A4/en not_active Withdrawn
- 2010-10-27 WO PCT/US2010/054226 patent/WO2011056634A2/en not_active Ceased
- 2010-10-27 US US13/503,378 patent/US8507615B2/en not_active Expired - Fee Related
- 2010-10-27 JP JP2012536986A patent/JP5604524B2/ja not_active Expired - Fee Related
- 2010-10-27 CN CN201080048378.9A patent/CN102666660B/zh not_active Expired - Fee Related
- 2010-10-27 KR KR1020127013659A patent/KR20120113718A/ko not_active Withdrawn
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