CA1319461C - Polyetherimides et precurseurs pour ces composes - Google Patents

Polyetherimides et precurseurs pour ces composes

Info

Publication number: CA1319461C
Authority: CA; Canada
Prior art keywords: phenylenediamine; reagent; mixture; ether; polyetherimide
Prior art date: 1987-09-14
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 - Fee Related

Application number

CA000598080A

Other languages

English (en)

Inventor

Donald Richard Berdahl

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.)

General Electric Co

Original Assignee

General Electric 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.)

1987-09-14

Filing date

1989-04-27

Publication date

1993-06-22

1988-06-03 Priority to US07/201,817 priority Critical patent/US4855391A/en

1988-07-15 Priority to US07/223,746 priority patent/US4874835A/en

1988-09-01 Priority to FR888811463A priority patent/FR2620453B1/fr

1988-09-03 Priority to DE3830064A priority patent/DE3830064A1/de

1988-09-08 Priority to JP63223677A priority patent/JPH01131245A/ja

1988-09-08 Priority to GB8821111A priority patent/GB2222409B/en

1989-04-27 Application filed by General Electric Co filed Critical General Electric Co

1989-04-27 Priority to CA000598080A priority patent/CA1319461C/fr

1993-06-22 Application granted granted Critical

1993-06-22 Publication of CA1319461C publication Critical patent/CA1319461C/fr

2010-06-22 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

229920001601 polyetherimide Polymers 0.000 title claims abstract description 22
239000002243 precursor Substances 0.000 title claims abstract description 16
239000000203 mixture Substances 0.000 claims abstract description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 18
239000004697 Polyetherimide Substances 0.000 claims abstract description 14
150000004985 diamines Chemical class 0.000 claims abstract description 14
WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims abstract description 11
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 claims abstract description 11
229940018564 m-phenylenediamine Drugs 0.000 claims abstract description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 10
230000032050 esterification Effects 0.000 claims abstract description 9
238000005886 esterification reaction Methods 0.000 claims abstract description 9
AIVVXPSKEVWKMY-UHFFFAOYSA-N 4-(3,4-dicarboxyphenoxy)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=C(C(O)=O)C(C(O)=O)=C1 AIVVXPSKEVWKMY-UHFFFAOYSA-N 0.000 claims abstract description 7
HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 claims abstract description 7
150000000000 tetracarboxylic acids Chemical class 0.000 claims abstract description 7
239000003153 chemical reaction reagent Substances 0.000 claims description 29
238000000034 method Methods 0.000 claims description 25
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 6
-1 tetracarboxylic acid diester Chemical class 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 5
238000002156 mixing Methods 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
239000004642 Polyimide Substances 0.000 abstract description 15
229920001721 polyimide Polymers 0.000 abstract description 13
230000015572 biosynthetic process Effects 0.000 abstract description 11
239000002131 composite material Substances 0.000 abstract description 10
238000010438 heat treatment Methods 0.000 abstract description 4
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 abstract 1
238000005755 formation reaction Methods 0.000 description 10
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
239000000010 aprotic solvent Substances 0.000 description 4
125000006159 dianhydride group Chemical group 0.000 description 4
239000011521 glass Substances 0.000 description 4
SMDGQEQWSSYZKX-UHFFFAOYSA-N 3-(2,3-dicarboxyphenoxy)phthalic acid Chemical class OC(=O)C1=CC=CC(OC=2C(=C(C(O)=O)C=CC=2)C(O)=O)=C1C(O)=O SMDGQEQWSSYZKX-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
230000009477 glass transition Effects 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
150000005690 diesters Chemical class 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
229920005575 poly(amic acid) Polymers 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
BTANRVKWQNVYAZ-SCSAIBSYSA-N (2R)-butan-2-ol Chemical compound CC[C@@H](C)O BTANRVKWQNVYAZ-SCSAIBSYSA-N 0.000 description 1
VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
239000004677 Nylon Substances 0.000 description 1
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
229920006397 acrylic thermoplastic Polymers 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
NIDNOXCRFUCAKQ-UHFFFAOYSA-N bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical class C1C2C=CC1C(C(=O)O)C2C(O)=O NIDNOXCRFUCAKQ-UHFFFAOYSA-N 0.000 description 1
239000005388 borosilicate glass Substances 0.000 description 1
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
239000003431 cross linking reagent Substances 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
230000003014 reinforcing effect Effects 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
150000005691 triesters Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
238000004260 weight control Methods 0.000 description 1
230000004580 weight loss Effects 0.000 description 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
- C08G73/1028—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous
- 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
- C08G73/1067—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

Landscapes

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

CA000598080A 1987-09-14 1989-04-27 Polyetherimides et precurseurs pour ces composes Expired - Fee Related CA1319461C (fr)

Priority Applications (7)

Application Number	Priority Date	Filing Date	Title
US07/201,817 US4855391A (en)	1987-09-14	1988-06-03	High temperature stable polyetherimides from oxydiphthalic dianhydride and a mixture of m- and p-phenylene diamines and diaminodiphenyl ether
US07/223,746 US4874835A (en)	1987-09-14	1988-07-15	Polyetherimides and precursors therefor from oxydiphtalic anhydride diester and a mixture of diamines
FR888811463A FR2620453B1 (fr)	1987-09-14	1988-09-01	Composition de precurseur de polyetherimide, polyetherimide et procedes pour leur preparation
DE3830064A DE3830064A1 (de)	1987-09-14	1988-09-03	Polyetherimide und deren vorstufen
JP63223677A JPH01131245A (ja)	1987-09-14	1988-09-08	ポリエーテルイミド及びその前駆物質
GB8821111A GB2222409B (en)	1987-09-14	1988-09-08	Polyetherimides and precursors therefor
CA000598080A CA1319461C (fr)	1987-09-14	1989-04-27	Polyetherimides et precurseurs pour ces composes

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US9598287A	1987-09-14	1987-09-14
CA000598080A CA1319461C (fr)	1987-09-14	1989-04-27	Polyetherimides et precurseurs pour ces composes

Publications (1)

Publication Number	Publication Date
CA1319461C true CA1319461C (fr)	1993-06-22

Family

ID=25672661

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000598080A Expired - Fee Related CA1319461C (fr)	1987-09-14	1989-04-27	Polyetherimides et precurseurs pour ces composes

Country Status (5)

Country	Link
JP (1)	JPH01131245A (fr)
CA (1)	CA1319461C (fr)
DE (1)	DE3830064A1 (fr)
FR (1)	FR2620453B1 (fr)
GB (1)	GB2222409B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4980389A (en) *	1990-04-03	1990-12-25	Irbit Research & Consulting Ag	Polyetherimide foam precursors and foams having improved physical properties and methods of making them
JP2748995B2 (ja) *	1990-11-26	1998-05-13	三井東圧化学株式会社	溶融成形用ポリイミドおよびその製造方法ならびにその樹脂組成物
US6222007B1 (en) *	1998-05-29	2001-04-24	The United States Of America As Represented By The National Aeronautics And Space Administration	Films, preimpregnated tapes and composites made from polyimide “Salt-like” Solutions
EP3494165A1 (fr)	2016-08-03	2019-06-12	SABIC Global Technologies B.V.	Procédé de fabrication d'une poudre et d'un vernis de prépolymère de poly(imide), poudre et vernis de prépolymère de poly(imide) préparé par ce procédé, et poly(imide) préparé à partir de cette poudre et de ce vernis

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3312663A (en) *	1963-06-17	1967-04-04	Du Pont	Polyamide esters
US3326851A (en) *	1963-12-23	1967-06-20	Du Pont	Process for producing aromatic polyamide-esters
US3349061A (en) *	1964-01-10	1967-10-24	Du Pont	Amide-ester isomers
US3376260A (en) *	1965-11-26	1968-04-02	Du Pont	Process for preparing polyimides from diamines and dianhydrides in the presence of abasic catalyst
US3700649A (en) *	1971-07-06	1972-10-24	Int Harvester Co	Polyimides of benzophenone tetracarboxylic acid esters and aromatic diamines having a basicity constant of less than 10-" and method of preparation
JPS60177659A (ja) *	1984-02-24	1985-09-11	Sumitomo Bakelite Co Ltd	半導体装置の製造方法
FR2568258B1 (fr) *	1984-07-25	1987-02-13	Inst Francais Du Petrole	Compositions de precurseurs de polyimides, leur preparation, les polyimides en derivant et leurs utilisations, notamment dans la fabrication de vernis d'emaillage pour conducteurs electriques
JPS62169853A (ja) *	1986-01-23	1987-07-27	Mitsui Toatsu Chem Inc	芳香族ポリアミツク酸溶液の調整方法
JPH0693984B2 (ja) *	1987-04-21	1994-11-24	宇部興産株式会社	ポリイミド気体分離膜

1988
- 1988-09-01 FR FR888811463A patent/FR2620453B1/fr not_active Expired - Fee Related
- 1988-09-03 DE DE3830064A patent/DE3830064A1/de not_active Withdrawn
- 1988-09-08 GB GB8821111A patent/GB2222409B/en not_active Expired - Lifetime
- 1988-09-08 JP JP63223677A patent/JPH01131245A/ja active Pending
1989
- 1989-04-27 CA CA000598080A patent/CA1319461C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
FR2620453A1 (fr)	1989-03-17
DE3830064A1 (de)	1989-03-23
FR2620453B1 (fr)	1993-08-13
JPH01131245A (ja)	1989-05-24
GB2222409A (en)	1990-03-07
GB8821111D0 (en)	1988-10-05
GB2222409B (en)	1991-10-16

Legal Events

Date	Code	Title	Description
1998-06-22	MKLA	Lapsed

Publication	Publication Date	Title
US4874835A (en)	1989-10-17	Polyetherimides and precursors therefor from oxydiphtalic anhydride diester and a mixture of diamines
US4485140A (en)	1984-11-27	Melt-fusible polyimides
US4299750A (en)	1981-11-10	Novel partially acetylene end-capped polyimide oligomers
US4794157A (en)	1988-12-27	Polyetherimide copolymers, and method for making
US5243023A (en)	1993-09-07	Polyimides containing amide and perfluoroisopropylidene connecting groups
US4588804A (en)	1986-05-13	Polyimide compositions
US5061784A (en)	1991-10-29	Polymers prepared from 4,4'-bis(3,4-dicarboxyphenyl) hexafluoroisopropyl) diphenyl dianhydride
US4935490A (en)	1990-06-19	Highly soluble aromatic polyimides
US4855391A (en)	1989-08-08	High temperature stable polyetherimides from oxydiphthalic dianhydride and a mixture of m- and p-phenylene diamines and diaminodiphenyl ether
US5484879A (en)	1996-01-16	Polyimides containing fluorine
US3705870A (en)	1972-12-12	Soluble polyimides from aromatic dianhydrides and 2,4-diaminodiphenylamines and 2,4-diaminodiphenyl sulfides
US5101005A (en)	1992-03-31	Crosslinkable polyimides from bis (aminophenoxy) benzonitriles
JPH0284434A (ja)	1990-03-26	３，５‐ジアミノベンゾトリフルオライドを用いたポリイミドポリマーおよびコポリマー
US4978737A (en)	1990-12-18	Copolyimides derived from 2,2-bis (amino phenyl) hexofluoropropane
US4634760A (en)	1987-01-06	Novel copolyimides and polyamic acid precursors therefor
US3705869A (en)	1972-12-12	Soluble polyimides
US5428102A (en)	1995-06-27	Low dielectric polyimides
CA1319461C (fr)	1993-06-22	Polyetherimides et precurseurs pour ces composes
US4956450A (en)	1990-09-11	Process for forming end-capped polyamic acids polyimides
US4960824A (en)	1990-10-02	Storage stable polyimide precursor solutions and method of preparation
US6060575A (en)	2000-05-09	1,4-bis(3,4-dicarboxyphenoxy)-2-tert-butylbenzene dianhydride and method of using the same
US4742153A (en)	1988-05-03	Process for preparing polyimides
US4973661A (en)	1990-11-27	Process for forming end capped polyamic acids polyimides
US4978742A (en)	1990-12-18	Polymers prepared from 2-(3-aminophenyl)-2-(4-aminophenyl) hexafluoro propane
US5025089A (en)	1991-06-18	Copolyimides derived from 2,2-bis (amino phenyl) hexafluoropropane