WO1995002627A1 - Melanges et stratifies de polyimide thermoresistants - Google Patents

Melanges et stratifies de polyimide thermoresistants Download PDF

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Publication number
WO1995002627A1
WO1995002627A1 PCT/US1994/004147 US9404147W WO9502627A1 WO 1995002627 A1 WO1995002627 A1 WO 1995002627A1 US 9404147 W US9404147 W US 9404147W WO 9502627 A1 WO9502627 A1 WO 9502627A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
solvent
radical
polyimide
formula
Prior art date
Application number
PCT/US1994/004147
Other languages
English (en)
Inventor
Frank W. Harris
Hiroyuki Furutani
Original Assignee
The University Of Akron
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
Priority claimed from US08/092,225 external-priority patent/US5397847A/en
Application filed by The University Of Akron filed Critical The University Of Akron
Priority to EP94916533A priority Critical patent/EP0708795A4/fr
Priority to JP7504521A priority patent/JPH10503221A/ja
Publication of WO1995002627A1 publication Critical patent/WO1995002627A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
    • C08J3/091—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids characterised by the chemical constitution of the organic liquid
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • 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
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
    • D06N3/00—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof
    • D06N3/12—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. gelatine proteins
    • D06N3/125—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. gelatine proteins with polyamides
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H19/00—Coated paper; Coating material
    • D21H19/10—Coatings without pigments
    • D21H19/14—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12
    • D21H19/24—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12 comprising macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D21H19/30—Polyamides; Polyimides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2379/00—Characterised by the use 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 C08J2361/00 - C08J2377/00
    • C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K1/00—Printed circuits
    • H05K1/02—Details
    • H05K1/03—Use of materials for the substrate
    • H05K1/0313—Organic insulating material
    • H05K1/032—Organic insulating material consisting of one material
    • H05K1/0346—Organic insulating material consisting of one material containing N

Definitions

  • polyester imides produced are usually lower in thermal softening points, than the polyimide alone, and additionally are inferior in their heat resistance when compared to the polyimide.
  • the polyester imides do however, have good fluidity.
  • Fig. 4 illustrates the glass transition point (T g ) as a function of the weight percent of added thermid.
  • thermoplastic polyimide represented by formula (I) represents the polycondensation reaction of at least one dianhydride of formula (IN)
  • One method of manufacturing a novel thermoplastic polyimide of formula (VI) comprises dissolving an organic diamine represented by formula (VII)
  • dehydrating imidization agent examples include organic carboxylic acid anhydrides, N,N'-dialkyl carbodiimide, lower fatty acid halides, lower halo-fatty acid anhydrides, alkylsulfonic acid dihalides and thionyl halides as well as mixtures of these compounds.
  • Acetic acid anhydride is a preferred embodiment.
  • Other preferred reagents would include ketene and benzoic acid anhydride.
  • the dianhydride component comprises, as its essential component, an organic dianhydride represented by formula (IV), but it is possible to copolymerize with a dianhydride wherein Z in formula (IN) is replaced by Z', but being selected however, from the same Markush group as that previously designated for Z.
  • Z in formula (IN) is replaced by Z'
  • Z' is replaced by Z'
  • ⁇ 1.10 (s, 6H, -CH 3 ), 3.40 (bs, 4H, -NH 2 ), 3.80 (s, 4H, -CH 2 -O-),
  • a blend solution was obtained in the manner as shown in Example 3 except for using 20.8816 g (0.09574 mol) of PMDA, 44.5310 g (0.14356 mol) of ODPA, 66.4659 g (0.23883 mol) of BAPDMP and 57 g of "Thermid IP-600".
  • the resin viscosity of the obtained resin solution was measured and found to be 28 poise.
  • thermoplastic polyimide powder comprising ODPA and BAPDMP, synthesized according to the thermal imidization process detailed in Example #9, and 11.2 g of "Thermid IP-600" (Kanebo NSC) dissolved in 200 ml of m-cresol.
  • the system was stirred at 120°C for 18 hours to obtain a homogeneous solution which was processed according to the procedure outlined for the polymer solution in Example #9, thereby obtaining 28.29 g (yield 55.8%) of the blended powder.
  • Example 13 Under the same conditions used in Example 13, except for using 10.45 g of thermoplastic polyimide powder synthesized by the thermal imidization process of Example #10, 5.05 g of "Thermid IP-600" and 200 ml of m-cresol yielded 7.36 g (56.1%) of the blend composition.
  • Example #13 Under the same conditions used in Example #13, except for using 12.38 g of thermoplastic polyimide powder synthesized by the thermal imidization process of Example #10, 4.05 g of "Thermid IP-600" and 250 ml of m-cresol yielded 7.50 g (43.9%) of the blend composition.
  • Example #13 Under the same conditions used in Example #13, except for using 9.24 g of thermoplastic polyimide powder synthesized by the thermal imidization process of Example #11, 3.56 g of "Thermid IP-600" and 250 ml of m-cresol yielded 12.50 g (93.2%) of the blend composition.
  • thermoplastic polyimide prepared from ODPA, PMDA and BAPDMP
  • thermosetting imide oligomer "Thermid IP-600” in a ratio of 3/1.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dispersion Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

Cette invention concerne des mélanges de polyimide thermorésistants et des éléments moulés réalisés avec ceux-ci. Ces mélanges ont une excellente résistance à la chaleur et à l'humidité, ils sont relativement solubles dans les solvants organiques, et ils se prêtent facilement aux transformations telles que la formation de stratifiés et le moulage. Les mélanges contiennent un composant polyimide thermoplastique et un oligomère d'imide thermodurcissant. Le rapport pondéral entre le composant thermoplastique et le composant thermodurcissant est choisi dans la plage 99/1 à 5/95. Le composant polyimide thermoplastique a une masse moléculaire moyenne au nombre de 10.000 ou plus.
PCT/US1994/004147 1993-07-15 1994-04-15 Melanges et stratifies de polyimide thermoresistants WO1995002627A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP94916533A EP0708795A4 (fr) 1993-07-15 1994-04-15 Melanges et stratifies de polyimide thermoresistants
JP7504521A JPH10503221A (ja) 1993-07-15 1994-04-15 耐熱ポリイミド系ブレンド組成物及び積層物

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US9222693A 1993-07-15 1993-07-15
US08/092,225 1993-07-15
US08/092,225 US5397847A (en) 1992-10-20 1993-07-15 Heat-resistant laminate materials and preparation thereof
US08/092,226 1993-07-15

Publications (1)

Publication Number Publication Date
WO1995002627A1 true WO1995002627A1 (fr) 1995-01-26

Family

ID=26785413

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1994/004147 WO1995002627A1 (fr) 1993-07-15 1994-04-15 Melanges et stratifies de polyimide thermoresistants

Country Status (4)

Country Link
EP (1) EP0708795A4 (fr)
JP (1) JPH10503221A (fr)
CA (1) CA2144324A1 (fr)
WO (1) WO1995002627A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0869151A2 (fr) * 1997-04-04 1998-10-07 Nitto Denko Corporation Composition de résine thermodurcissable
WO2007041782A1 (fr) * 2005-10-11 2007-04-19 Crc For Advanced Composite Structures Limited Procede de liaison de fibres de renfort seches
RU2532514C1 (ru) * 2013-09-19 2014-11-10 Закрытое акционерное общество "Институт новых углеродных материалов и технологий" (ЗАО "ИНУМиТ") Связующее, способ его изготовления и препрег на его основе
WO2015069966A1 (fr) * 2013-11-07 2015-05-14 Georgia-Pacific Chemicals Llc Adhésifs de crêpage et leurs procédés de fabrication et d'utilisation
CN105398136A (zh) * 2015-12-29 2016-03-16 广东生益科技股份有限公司 一种二层法双面挠性覆铜板
US9416229B2 (en) 2014-05-28 2016-08-16 Industrial Technology Research Institute Dianhydride and polyimide
CN113172959A (zh) * 2021-04-23 2021-07-27 中国科学院化学研究所 一种高韧性、耐高温聚酰亚胺复合材料及其制备方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4553648B2 (ja) * 2004-07-02 2010-09-29 日本化薬株式会社 エポキシ樹脂組成物及びその硬化物

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4996101A (en) * 1988-08-08 1991-02-26 Lockheed Corporation Processible polyimide blends
US5059273A (en) * 1989-10-26 1991-10-22 E. I. Du Pont De Nemours And Company Process for preparing polyimide composites
US5155179A (en) * 1990-04-25 1992-10-13 Hoechst Celanese Corp. Miscible blends of polyimide polymers
US5175242A (en) * 1989-02-24 1992-12-29 The University Of Akron Phenylated polyimides prepared from 3,6-diarylpyromellitic dianhydride and aromatic diamines

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02222451A (ja) * 1989-02-23 1990-09-05 Toray Ind Inc 芳香族ポリイミド樹脂組成物
US5391183A (en) * 1990-09-21 1995-02-21 Datascope Investment Corp Device and method sealing puncture wounds

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4996101A (en) * 1988-08-08 1991-02-26 Lockheed Corporation Processible polyimide blends
US5175242A (en) * 1989-02-24 1992-12-29 The University Of Akron Phenylated polyimides prepared from 3,6-diarylpyromellitic dianhydride and aromatic diamines
US5059273A (en) * 1989-10-26 1991-10-22 E. I. Du Pont De Nemours And Company Process for preparing polyimide composites
US5155179A (en) * 1990-04-25 1992-10-13 Hoechst Celanese Corp. Miscible blends of polyimide polymers

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP0708795A4 *

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0869151A2 (fr) * 1997-04-04 1998-10-07 Nitto Denko Corporation Composition de résine thermodurcissable
EP0869151A3 (fr) * 1997-04-04 1998-11-18 Nitto Denko Corporation Composition de résine thermodurcissable
US6068932A (en) * 1997-04-04 2000-05-30 Nitto Denko Corporation Thermosetting resin composition
CN1113937C (zh) * 1997-04-04 2003-07-09 日东电工株式会社 热固性树脂组合物
WO2007041782A1 (fr) * 2005-10-11 2007-04-19 Crc For Advanced Composite Structures Limited Procede de liaison de fibres de renfort seches
RU2532514C1 (ru) * 2013-09-19 2014-11-10 Закрытое акционерное общество "Институт новых углеродных материалов и технологий" (ЗАО "ИНУМиТ") Связующее, способ его изготовления и препрег на его основе
WO2015069966A1 (fr) * 2013-11-07 2015-05-14 Georgia-Pacific Chemicals Llc Adhésifs de crêpage et leurs procédés de fabrication et d'utilisation
US9416229B2 (en) 2014-05-28 2016-08-16 Industrial Technology Research Institute Dianhydride and polyimide
CN105398136A (zh) * 2015-12-29 2016-03-16 广东生益科技股份有限公司 一种二层法双面挠性覆铜板
CN113172959A (zh) * 2021-04-23 2021-07-27 中国科学院化学研究所 一种高韧性、耐高温聚酰亚胺复合材料及其制备方法
CN113172959B (zh) * 2021-04-23 2022-12-16 中国科学院化学研究所 一种高韧性、耐高温聚酰亚胺复合材料及其制备方法

Also Published As

Publication number Publication date
CA2144324A1 (fr) 1995-01-26
JPH10503221A (ja) 1998-03-24
EP0708795A1 (fr) 1996-05-01
EP0708795A4 (fr) 1996-08-07

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