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GB980274A - Preparation of polyimides - Google Patents

  • ️Wed Jan 13 1965

GB980274A - Preparation of polyimides - Google Patents

Preparation of polyimides

Info

Publication number
GB980274A
GB980274A GB2271/63A GB227163A GB980274A GB 980274 A GB980274 A GB 980274A GB 2271/63 A GB2271/63 A GB 2271/63A GB 227163 A GB227163 A GB 227163A GB 980274 A GB980274 A GB 980274A Authority
GB
United Kingdom
Prior art keywords
polyamide
carbon atoms
dianhydride
acid
polyimides
Prior art date
1962-01-26
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.)
Expired
Application number
GB2271/63A
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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.)
1962-01-26
Filing date
1963-01-18
Publication date
1965-01-13
1962-01-26 Priority claimed from US169120A external-priority patent/US3179634A/en
1962-01-26 Priority claimed from US169119A external-priority patent/US3179633A/en
1962-01-26 Priority claimed from US169106A external-priority patent/US3179630A/en
1963-01-18 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
1965-01-13 Publication of GB980274A publication Critical patent/GB980274A/en
Status Expired legal-status Critical Current

Links

  • 239000004642 Polyimide Substances 0.000 title abstract 5
  • 229920001721 polyimide Polymers 0.000 title abstract 5
  • 125000004432 carbon atom Chemical group C* 0.000 abstract 4
  • WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
  • 239000002253 acid Substances 0.000 abstract 3
  • 150000004985 diamines Chemical class 0.000 abstract 3
  • JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
  • 238000010438 heat treatment Methods 0.000 abstract 2
  • 238000000034 method Methods 0.000 abstract 2
  • 239000000376 reactant Substances 0.000 abstract 2
  • 238000006798 ring closing metathesis reaction Methods 0.000 abstract 2
  • -1 tetracarboxylic acid dianhydride Chemical class 0.000 abstract 2
  • VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 abstract 1
  • GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 abstract 1
  • QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 abstract 1
  • 239000004952 Polyamide Substances 0.000 abstract 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 abstract 1
  • 150000001718 carbodiimides Chemical class 0.000 abstract 1
  • 229910052799 carbon Inorganic materials 0.000 abstract 1
  • 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
  • 238000006243 chemical reaction Methods 0.000 abstract 1
  • 239000012024 dehydrating agents‎ Substances 0.000 abstract 1
  • 239000003960 organic solvent Substances 0.000 abstract 1
  • 229920002647 polyamide Polymers 0.000 abstract 1
  • 229920000642 polymer Polymers 0.000 abstract 1
  • UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
  • 239000002904 solvent Substances 0.000 abstract 1
  • 239000000126 substance Substances 0.000 abstract 1
  • 150000003512 tertiary amines Chemical class 0.000 abstract 1

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
    • 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
    • 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
    • C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen 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
    • C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
    • C08G73/106—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing silicon
    • 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
    • C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
    • 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
    • C08G73/1071—Wholly aromatic 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
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/02—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by the reacting monomers or modifying agents during the preparation or modification of macromolecules
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
    • H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
    • H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
    • H01B3/303—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 H01B3/38 or H01B3/302
    • H01B3/306—Polyimides or polyesterimides
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

A process for making polyimides comprises reacting at least one diamine of the formula H2N-R1-NH2 where R1 is a divalent radica containing at least 2 carbon atoms, the 2 amino groups of said diamine each being attached to separate carbon atoms of said divalent radical, with at least one tetracarboxylic acid dianhydride of the formula <FORM:0980274/C3/1> where R is a tetravalent radical containing at least 2 carbon atoms, no more than 2 carbonyl groups of said dianhydride being attached to any one carbon atom of said tetravalent radical, in an organic solvent for at least one of the reactants, the solvent being inert to the reactants, at a temperature of from 60 DEG C. to 175 DEG C. So as to form a polymer containing polyamide and having an inherent viscosity of at least 0.1 and then effecting ring closure of the latter to convert the polyamide-acid to the polyimide. The conversion of the polyamide-acid to polyimide may be effected by heating to a temperature of 300 DEG C. to 500 DEG C., by treating it with a dehydrating agent, e.g. acetic anhydride alone or in admixture with a tertiaryamine e.g. pyridine, by ring closure with a carbodiimide, e.g. dicyclohexyl carbodiimide, or by a combination of the foregoing methods. In the examples, polyamide-acids are made from 4:41-diamino diphenyl ether and pyromellitic dianhydride and converted to polyimides by:-(1) heating to 300 DEG C. and (2) chemical treatment. Many diamines and tetracarboxylic acid dianhydrides are specified. Specifications 903,272 and 980,273 also are referred to.

GB2271/63A 1962-01-26 1963-01-18 Preparation of polyimides Expired GB980274A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US169120A US3179634A (en) 1962-01-26 1962-01-26 Aromatic polyimides and the process for preparing them
US169119A US3179633A (en) 1962-01-26 1962-01-26 Aromatic polyimides from meta-phenylene diamine and para-phenylene diamine
US169106A US3179630A (en) 1962-01-26 1962-01-26 Process for preparing polyimides by treating polyamide-acids with lower fatty monocarboxylic acid anhydrides

Publications (1)

Publication Number Publication Date
GB980274A true GB980274A (en) 1965-01-13

Family

ID=27389608

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2271/63A Expired GB980274A (en) 1962-01-26 1963-01-18 Preparation of polyimides

Country Status (5)

Country Link
FR (1) FR83564E (en)
GB (1) GB980274A (en)
NL (1) NL288190A (en)
NO (1) NO115189B (en)
SE (1) SE324456B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2157303A (en) * 1984-03-05 1985-10-23 Rogers Corp Co-solvent accelerator and method for conversion of polyamide-acid, solution to polylmide
DE102010001991A1 (en) 2010-02-16 2011-08-18 Siemens Aktiengesellschaft, 80333 Flat conductor device i.e. flat wire, for use in motor of electric machine, during traction application, has insulating layer formed by covering of conductor with tape, and other insulating layer formed by covering of former layer with yarn

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2157303A (en) * 1984-03-05 1985-10-23 Rogers Corp Co-solvent accelerator and method for conversion of polyamide-acid, solution to polylmide
DE102010001991A1 (en) 2010-02-16 2011-08-18 Siemens Aktiengesellschaft, 80333 Flat conductor device i.e. flat wire, for use in motor of electric machine, during traction application, has insulating layer formed by covering of conductor with tape, and other insulating layer formed by covering of former layer with yarn
DE102010001991B4 (en) * 2010-02-16 2015-12-03 Siemens Aktiengesellschaft Flat conductor device with two braided insulating layers and manufacturing method

Also Published As

Publication number Publication date
NL288190A (en) 1965-03-10
NO115189B (en) 1968-08-26
FR83564E (en) 1964-09-04
SE324456B (en) 1970-06-01

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