CA2480144A1 - Rtm and ri processable polymide resins - Google Patents

Rtm and ri processable polymide resins Download PDF

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Publication number
CA2480144A1
CA2480144A1 CA002480144A CA2480144A CA2480144A1 CA 2480144 A1 CA2480144 A1 CA 2480144A1 CA 002480144 A CA002480144 A CA 002480144A CA 2480144 A CA2480144 A CA 2480144A CA 2480144 A1 CA2480144 A1 CA 2480144A1
Authority
CA
Canada
Prior art keywords
rtm
resin
inventive
processable
resins
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
Application number
CA002480144A
Other languages
French (fr)
Other versions
CA2480144C (en
Inventor
Gary L. Deets
Jianming Xiong
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
I S T Corp
Original Assignee
I S T (MA) Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by I S T (MA) Corp filed Critical I S T (MA) Corp
Publication of CA2480144A1 publication Critical patent/CA2480144A1/en
Application granted granted Critical
Publication of CA2480144C publication Critical patent/CA2480144C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • 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
    • 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
    • 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
    • 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
    • C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
    • C08G73/1064—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing sulfur
    • 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
    • C08G73/1075—Partially aromatic polyimides
    • C08G73/1082—Partially aromatic polyimides wholly aromatic in the tetracarboxylic moiety
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31721—Of polyimide

Abstract

Polyimide resins that are suitable for processing by resin transfer molding (RTM) and resin infusion (RI) methods at reduced processing temperatures are provided. The inventive RTM and RI processable polyimide resins exhibit melting at temperatures of less than about 200 °C and melt viscosities at 200 °C of less than about 3000 centipoise. A process for synthesizing the inventive resins is also provided, as is a fiber-reinforced composite material. The fiber- reinforced composite material employs the inventive polyimide resin as its resin matrix and demonstrates good heat resistance and mechanical properties.
CA002480144A 2003-09-02 2004-09-02 Rtm and ri processable polymide resins Active CA2480144C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US49984903P 2003-09-02 2003-09-02
US60/499,849 2003-09-02

Publications (2)

Publication Number Publication Date
CA2480144A1 true CA2480144A1 (en) 2005-03-02
CA2480144C CA2480144C (en) 2009-04-21

Family

ID=34135363

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002480144A Active CA2480144C (en) 2003-09-02 2004-09-02 Rtm and ri processable polymide resins

Country Status (8)

Country Link
US (1) US7129318B2 (en)
EP (1) EP1514888B1 (en)
JP (1) JP4537158B2 (en)
CA (1) CA2480144C (en)
ES (1) ES2421646T3 (en)
MX (1) MXPA04008505A (en)
PL (1) PL1514888T3 (en)
PT (1) PT1514888E (en)

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US20070265417A1 (en) * 2006-05-12 2007-11-15 General Electric Company Crosslinked polyimide copolymer material
US20070265420A1 (en) * 2006-05-12 2007-11-15 General Electric Company fiber reinforced gas turbine engine component
US8030433B2 (en) 2006-05-12 2011-10-04 General Electric Company RTM and RI processible tailorable polyimide resin systems and composite articles formed therefrom
US8633284B2 (en) * 2006-05-12 2014-01-21 General Electric Company Tailorable polyimide prepolymer blends, crosslinked polymides and articles formed therefrom
US20070265416A1 (en) * 2006-05-12 2007-11-15 General Electric Company Polyimide blend with tailorable properties
US20070265421A1 (en) * 2006-05-12 2007-11-15 General Electric Company Method for making a prepolymer polyimide resin blend
US8030437B2 (en) 2006-05-12 2011-10-04 General Electric Company Methods for forming composite articles from tailorable polyimide resin systems using RTM and RI techniques
JPWO2008004615A1 (en) * 2006-07-07 2009-12-03 三菱瓦斯化学株式会社 Polyimide resin
EP2045295B1 (en) * 2006-07-20 2012-12-12 Mitsubishi Gas Chemical Company, Inc. Thermocurable polyimide resin composition
US8309663B2 (en) * 2007-05-31 2012-11-13 The Boeing Company Water-entrained-polyimide chemical compositions for use in high-performance composite fabrication
US20080300374A1 (en) * 2007-05-31 2008-12-04 The Boeing Company Dinadic phenyl amine reactive endcaps
US7825211B2 (en) * 2007-06-22 2010-11-02 The Boeing Company Single-step-processable polyimides
US20090112650A1 (en) * 2007-10-31 2009-04-30 Iwane Donna S Online method of procuring mortgage loans
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US20110003955A1 (en) * 2008-02-07 2011-01-06 Daiwa Can Company Imide Oligomer And Polyimide Resin Obtained By Thermal Curing Thereof
JP2010006983A (en) * 2008-06-27 2010-01-14 Hitachi Chem Co Ltd Sealing filler and semiconductor device
DE102008038295B4 (en) * 2008-08-18 2013-11-28 Eads Deutschland Gmbh Granulation and stabilization of resin systems for use in the manufacture of fiber composite components
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US8962890B1 (en) 2012-04-20 2015-02-24 The United States Of America As Represented By The Secretary Of The Air Force Multifunctional crosslinkers for shape-memory polyimides, polyamides and poly(amide-imides) and methods of making the same
US8791227B1 (en) * 2012-04-20 2014-07-29 The United States Of America As Represented By The Secretary Of The Air Force Crosslinked aromatic polyimides and methods of making the same
WO2013181333A1 (en) 2012-06-01 2013-12-05 E. I. Du Pont De Nemours And Company An electrochemical cell comprising a nanoweb comprising nanofibers of a cross-linked polyimide
US9085661B1 (en) 2012-10-26 2015-07-21 The United States Of America As Represented By The Secretary Of The Air Force Photomechanically active copolyimides derived from an azobenzenediamine, a rigid dianhydride, and a flexible dianhydride
US9139696B1 (en) 2014-03-28 2015-09-22 The United States Of America, As Represented By The Secretary Of The Air Force Aromatic diamines containing three ether-linked-benzonitrile moieties, polymers thereof, and methods of making the same
US9644071B1 (en) 2014-09-05 2017-05-09 The United States Of America As Represented By The Secretary Of The Air Force Bis(azobenzene) diamines and photomechanical polymers made therefrom
KR101841977B1 (en) 2015-03-19 2018-03-26 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 Polyimide resin
US10239254B1 (en) 2015-08-07 2019-03-26 The United States Of America As Represented By The Secretary Of The Air Force Method of fabricating shape memory films
US10294255B1 (en) 2015-08-07 2019-05-21 The United States Of America As Represented By The Secretary Of The Air Force Multifunctional crosslinking agent, crosslinked polymer, and method of making same
KR101786509B1 (en) 2016-02-04 2017-10-18 국방과학연구소 Resin composition for producing high temperature heat resistingprepreg and method for producing the same
WO2018180930A1 (en) 2017-03-30 2018-10-04 株式会社カネカ Semipreg, prepreg, resin composite material, and production methods thereof
KR102627227B1 (en) * 2017-08-23 2024-01-22 유비이 가부시키가이샤 Binder resin for electrodes, electrode mixture paste, electrode, and method for producing electrode
KR102521984B1 (en) * 2022-05-17 2023-04-27 주식회사 씨지피머트리얼즈 Method for manufacturing colorless and transparent polyimide film, and colorless and transparent polyimide film prepared by manufacturing method thereof

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Also Published As

Publication number Publication date
US20050080229A1 (en) 2005-04-14
EP1514888B1 (en) 2013-04-17
EP1514888A1 (en) 2005-03-16
JP4537158B2 (en) 2010-09-01
JP2005076032A (en) 2005-03-24
US7129318B2 (en) 2006-10-31
PT1514888E (en) 2013-06-28
PL1514888T3 (en) 2013-09-30
CA2480144C (en) 2009-04-21
ES2421646T3 (en) 2013-09-04
MXPA04008505A (en) 2005-11-17

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