CA2319338A1 - Low-toxicity, high-temperature polyimides - Google Patents

Low-toxicity, high-temperature polyimides Download PDF

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Publication number
CA2319338A1
CA2319338A1 CA002319338A CA2319338A CA2319338A1 CA 2319338 A1 CA2319338 A1 CA 2319338A1 CA 002319338 A CA002319338 A CA 002319338A CA 2319338 A CA2319338 A CA 2319338A CA 2319338 A1 CA2319338 A1 CA 2319338A1
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CA
Canada
Prior art keywords
polyimide
bisaniline
diamine
bis
derivative
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
CA002319338A
Other languages
French (fr)
Other versions
CA2319338C (en
Inventor
Robert A. Gray
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.)
Maverick Corp
Original Assignee
Maverick Corporation
Robert A. Gray
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 Maverick Corporation, Robert A. Gray filed Critical Maverick Corporation
Publication of CA2319338A1 publication Critical patent/CA2319338A1/en
Application granted granted Critical
Publication of CA2319338C publication Critical patent/CA2319338C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • 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
    • C08G73/1028—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous
    • C08G73/1032—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous characterised by the solvent(s) used
    • 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
    • C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
    • 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
    • C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
    • 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

Abstract

The present invention is directed to polyimide systems which simultaneously offer low toxicity, a high glass transition temperature, excellent thermal oxidative stability, and desirable processing characteristics. These various polyimide systems include mixtures of monomeric reactants, polyimide-precursor reaction products, polyimides, and polyimide-containing articles. In one aspect of the invention, the mixture of monomeric reactants includes at least one dianhydride or a derivative thereof, and at least one diamine. The diamine may be 4,4'-[1,4-phenylene-bis(1-methylethylidene)]bisaniline, 4,4'-[1,3-phenylene-bis(1-methylethylidene)]bisaniline, and/or a derivative thereof. The diamine also may include a phenylenediamine, 2,2-bis[4-(4-aminophenoxyl)phenyl]propane, 4,4' (1,4-pheny-lene-bismethylene)bisaniline, and/or a derivative thereof. In addition, the mixture may include a reactive end-capping agent and/or a non-reactive end-capping agent. Also, if desired, the mixture of monomeric reactants may be a dry mix or a solution. The invention also is directed to articles formed from mixtures of monomeric reactants, articles formed from polyimide-precursor reaction products, and articles formed from polyimides themselves. Non-limiting examples include a powder, a neat resin, a coating, a film, a membrane, a foam, an adhesive, a fiber, a composite, a laminate, a prepreg, a part, and bushing.
CA002319338A 1998-01-16 1999-01-15 Low-toxicity, high-temperature polyimides Expired - Lifetime CA2319338C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US7159998P 1998-01-16 1998-01-16
US60/071,599 1998-01-16
PCT/US1999/000898 WO1999036462A1 (en) 1998-01-16 1999-01-15 Low-toxicity, high-temperature polyimides
US09/232,271 1999-01-15
US09/232,271 US6184333B1 (en) 1998-01-16 1999-01-15 Low-toxicity, high-temperature polyimides

Publications (2)

Publication Number Publication Date
CA2319338A1 true CA2319338A1 (en) 1999-07-22
CA2319338C CA2319338C (en) 2008-10-07

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
CA002319338A Expired - Lifetime CA2319338C (en) 1998-01-16 1999-01-15 Low-toxicity, high-temperature polyimides

Country Status (7)

Country Link
US (1) US6184333B1 (en)
EP (1) EP1051440B1 (en)
AU (1) AU2230499A (en)
CA (1) CA2319338C (en)
DE (1) DE69933011T2 (en)
ES (1) ES2268848T3 (en)
WO (1) WO1999036462A1 (en)

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Also Published As

Publication number Publication date
EP1051440A1 (en) 2000-11-15
ES2268848T3 (en) 2007-03-16
US6184333B1 (en) 2001-02-06
WO1999036462A1 (en) 1999-07-22
DE69933011D1 (en) 2006-10-12
DE69933011T2 (en) 2007-04-12
AU2230499A (en) 1999-08-02
CA2319338C (en) 2008-10-07
EP1051440B1 (en) 2006-08-30

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