KR20120101660A - 고온 마모 용도를 위한 폴리이미드 수지 - Google Patents
고온 마모 용도를 위한 폴리이미드 수지 Download PDFInfo
- Publication number
- KR20120101660A KR20120101660A KR1020127013661A KR20127013661A KR20120101660A KR 20120101660 A KR20120101660 A KR 20120101660A KR 1020127013661 A KR1020127013661 A KR 1020127013661A KR 20127013661 A KR20127013661 A KR 20127013661A KR 20120101660 A KR20120101660 A KR 20120101660A
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- KR
- South Korea
- Prior art keywords
- polyimide
- weight
- carbon
- parts
- composition
- 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.)
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- 229920001721 polyimide Polymers 0.000 title claims abstract description 87
- 239000009719 polyimide resin Substances 0.000 title abstract description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 154
- 239000000203 mixture Substances 0.000 claims abstract description 99
- 239000004642 Polyimide Substances 0.000 claims abstract description 78
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 78
- 229910002804 graphite Inorganic materials 0.000 claims abstract description 34
- 239000010439 graphite Substances 0.000 claims abstract description 34
- 125000003118 aryl group Chemical group 0.000 claims abstract description 16
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 35
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical class C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 31
- -1 aromatic tetracarboxylic acid compound Chemical class 0.000 claims description 28
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 21
- 239000000463 material Substances 0.000 claims description 21
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 18
- 229910052742 iron Inorganic materials 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 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 claims description 15
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 10
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- 125000000217 alkyl group Chemical group 0.000 claims description 8
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- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 6
- 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 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 4
- 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 claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
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- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims description 3
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- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 2
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- 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 claims description 2
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- 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 claims description 2
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- NTNWKDHZTDQSST-UHFFFAOYSA-N naphthalene-1,2-diamine Chemical compound C1=CC=CC2=C(N)C(N)=CC=C21 NTNWKDHZTDQSST-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
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- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical group NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 claims description 2
- ABYXFACYSGVHCW-UHFFFAOYSA-N pyridine-3,5-diamine Chemical compound NC1=CN=CC(N)=C1 ABYXFACYSGVHCW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 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 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
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- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
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Classifications
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
- C08G73/101—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents
- C08G73/1014—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents in the form of (mono)anhydrid
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/04—Carbon
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K7/00—Use of ingredients characterised by shape
- C08K7/02—Fibres or whiskers
- C08K7/04—Fibres or whiskers inorganic
Landscapes
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
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| EP (1) | EP2493983A4 (enExample) |
| JP (1) | JP5701893B2 (enExample) |
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| CN (1) | CN102666728B (enExample) |
| WO (1) | WO2011056651A2 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2024071790A1 (ko) * | 2022-09-29 | 2024-04-04 | 주식회사 대림 | 내열성 및 산화 안정성이 우수한 폴리이미드 수지 및 이의 제조방법 |
| WO2025216613A1 (ko) * | 2024-04-11 | 2025-10-16 | 주식회사 대림 | 치수 안정성이 우수하고 굴곡 모듈러스가 높은 폴리이미드 수지 및 이의 제조방법 |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6032202B2 (ja) * | 2011-06-14 | 2016-11-24 | 宇部興産株式会社 | ポリイミド積層体の製造方法、およびポリイミド積層体 |
| WO2013003397A2 (en) * | 2011-06-28 | 2013-01-03 | E. I. Du Pont De Nemours And Company | Polyimide-coated fillers |
| CN103842422B (zh) * | 2011-07-21 | 2016-08-24 | 恩特格里公司 | 纳米管与细磨的碳纤维聚合物复合材料的组合物及其制造方法 |
| DE102011109578B4 (de) * | 2011-08-05 | 2015-05-28 | Heraeus Noblelight Gmbh | Verfahren zur Herstellung eines elektrisch leitenden Materials, elektrisch leitendes Material sowie Strahler mit elektrisch leitendem Material |
| KR20130137035A (ko) | 2011-10-31 | 2013-12-13 | 가부시끼가이샤 리켄 | 피스톤 링 |
| WO2014168979A1 (en) * | 2013-04-08 | 2014-10-16 | Vorbeck Materials | Use of graphene-containing polymer composites |
| CN103524767B (zh) * | 2013-10-30 | 2016-07-06 | 宏威高新材料有限公司 | 一种低线胀系数的新型电子级聚酰亚胺薄膜及其制造方法 |
| US9890298B2 (en) * | 2013-12-31 | 2018-02-13 | Saint-Gobain Performance Plastics Corporation | Composite bearings having a polyimide matrix |
| JP6499450B2 (ja) * | 2015-01-07 | 2019-04-10 | 株式会社日本触媒 | 酸化グラフェン複合組成物 |
| CN110494475B (zh) * | 2017-09-04 | 2022-09-20 | 株式会社Lg化学 | 用于柔性显示装置基底的聚酰亚胺膜 |
| CN110066407A (zh) * | 2019-04-22 | 2019-07-30 | 东华大学 | 一种高阻燃性树脂薄膜及其制备方法 |
| CN110016138B (zh) * | 2019-04-22 | 2021-11-09 | 东华大学 | 一种高阻燃性聚酰亚胺薄膜及其制备方法 |
| CN113258722B (zh) * | 2021-05-31 | 2022-06-10 | 哈尔滨工业大学 | 一种用于直驱式电液伺服作动器的自旋转石墨烯散热装置 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4835249A (en) * | 1986-12-31 | 1989-05-30 | General Electric Company | Process for preparing polyimides |
| JP2946510B2 (ja) * | 1987-09-04 | 1999-09-06 | 東レ株式会社 | ポリイミド樹脂組成物 |
| 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 |
| JPH07165913A (ja) * | 1993-12-17 | 1995-06-27 | Mitsui Toatsu Chem Inc | 熱酸化安定性良好なポリイミドおよびその製造方法 |
| JPH09508161A (ja) * | 1994-01-21 | 1997-08-19 | イー・アイ・デュポン・ドゥ・ヌムール・アンド・カンパニー | 改善された特性を有するポリイミド組成物 |
| DE69601519T2 (de) * | 1995-06-28 | 1999-08-19 | Mitsui Chemicals | Lineare Polyamidsäure, lineares Polyimid und wärmehärtbares Polyimid |
| 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 |
| 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 |
| JP2008545839A (ja) * | 2005-05-27 | 2008-12-18 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 低い熱膨張率を有する樹脂組成物およびそれから製造された物品 |
| US7745516B2 (en) * | 2005-10-12 | 2010-06-29 | E. I. Du Pont De Nemours And Company | Composition of polyimide and sterically-hindered hydrophobic epoxy |
| JP2009242656A (ja) * | 2008-03-31 | 2009-10-22 | Ube Ind Ltd | 摩擦材及び摩擦材用樹脂組成物 |
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2010
- 2010-10-27 EP EP10828889A patent/EP2493983A4/en not_active Withdrawn
- 2010-10-27 KR KR1020127013661A patent/KR20120101660A/ko not_active Withdrawn
- 2010-10-27 JP JP2012537002A patent/JP5701893B2/ja not_active Expired - Fee Related
- 2010-10-27 US US13/504,317 patent/US20120235071A1/en not_active Abandoned
- 2010-10-27 CN CN201080048382.5A patent/CN102666728B/zh not_active Expired - Fee Related
- 2010-10-27 WO PCT/US2010/054288 patent/WO2011056651A2/en not_active Ceased
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2024071790A1 (ko) * | 2022-09-29 | 2024-04-04 | 주식회사 대림 | 내열성 및 산화 안정성이 우수한 폴리이미드 수지 및 이의 제조방법 |
| WO2025216613A1 (ko) * | 2024-04-11 | 2025-10-16 | 주식회사 대림 | 치수 안정성이 우수하고 굴곡 모듈러스가 높은 폴리이미드 수지 및 이의 제조방법 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102666728B (zh) | 2015-03-25 |
| JP5701893B2 (ja) | 2015-04-15 |
| US20120235071A1 (en) | 2012-09-20 |
| JP2013508536A (ja) | 2013-03-07 |
| EP2493983A2 (en) | 2012-09-05 |
| WO2011056651A3 (en) | 2011-09-22 |
| EP2493983A4 (en) | 2013-03-13 |
| WO2011056651A2 (en) | 2011-05-12 |
| CN102666728A (zh) | 2012-09-12 |
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