CA1276746C - Copolyimides a combinaison de groupes d'assouplissement - Google Patents

Copolyimides a combinaison de groupes d'assouplissement

Info

Publication number: CA1276746C
Authority: CA; Canada
Prior art keywords: formula; copolyimide; amide; acid; poly
Prior art date: 1985-06-20
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 - Lifetime

Application number

CA000511903A

Other languages

English (en)

Inventor

Harold David Burks

Terry Lee St. Clair

Donald Joseph Progar

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.)

National Aeronautics and Space Administration NASA

Original Assignee

National Aeronautics and Space Administration NASA

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.)

1985-06-20

Filing date

1986-06-19

Publication date

1990-11-20

1986-06-19 Application filed by National Aeronautics and Space Administration NASA filed Critical National Aeronautics and Space Administration NASA

1990-11-20 Application granted granted Critical

1990-11-20 Publication of CA1276746C publication Critical patent/CA1276746C/fr

2007-11-20 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

125000003118 aryl group Chemical group 0.000 claims abstract description 31
150000004985 diamines Chemical class 0.000 claims abstract description 13
125000006159 dianhydride group Chemical group 0.000 claims abstract description 4
229920001721 polyimide Polymers 0.000 claims description 32
239000004642 Polyimide Substances 0.000 claims description 31
238000000034 method Methods 0.000 claims description 26
239000002253 acid Substances 0.000 claims description 25
HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 claims description 23
239000002904 solvent Substances 0.000 claims description 21
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 19
239000000853 adhesive Substances 0.000 claims description 16
230000001070 adhesive effect Effects 0.000 claims description 16
229920001577 copolymer Polymers 0.000 claims description 14
238000010438 heat treatment Methods 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 13
239000011521 glass Substances 0.000 claims description 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
239000000463 material Substances 0.000 claims description 10
WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 9
VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 claims description 9
239000007787 solid Substances 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 8
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 description 7
239000000203 mixture Substances 0.000 claims description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 4
239000007795 chemical reaction product Substances 0.000 claims description 2
238000001816 cooling Methods 0.000 claims description 2
IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 claims description 2
238000001704 evaporation Methods 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
150000002430 hydrocarbons Chemical class 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims 4
125000001246 bromo group Chemical group Br* 0.000 claims 3
239000012024 dehydrating agents‎ Substances 0.000 claims 2
239000011877 solvent mixture Substances 0.000 claims 2
150000001298 alcohols Chemical class 0.000 claims 1
238000005266 casting Methods 0.000 claims 1
229940113088 dimethylacetamide Drugs 0.000 claims 1
238000001035 drying Methods 0.000 claims 1
238000001914 filtration Methods 0.000 claims 1
239000004615 ingredient Substances 0.000 claims 1
230000001376 precipitating effect Effects 0.000 claims 1
238000003825 pressing Methods 0.000 claims 1
238000003756 stirring Methods 0.000 claims 1
229920000642 polymer Polymers 0.000 abstract description 42
238000010348 incorporation Methods 0.000 abstract description 5
229920001169 thermoplastic Polymers 0.000 abstract description 5
239000004416 thermosoftening plastic Substances 0.000 abstract description 5
239000004831 Hot glue Substances 0.000 abstract description 4
150000004986 phenylenediamines Chemical class 0.000 abstract description 4
150000004984 aromatic diamines Chemical class 0.000 abstract description 3
239000010936 titanium Substances 0.000 description 13
238000012360 testing method Methods 0.000 description 12
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 9
239000002390 adhesive tape Substances 0.000 description 9
238000000576 coating method Methods 0.000 description 9
239000004744 fabric Substances 0.000 description 9
229910052719 titanium Inorganic materials 0.000 description 9
239000011248 coating agent Substances 0.000 description 7
230000009477 glass transition Effects 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
229920005575 poly(amic acid) Polymers 0.000 description 5
230000000694 effects Effects 0.000 description 4
238000004381 surface treatment Methods 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
230000003247 decreasing effect Effects 0.000 description 3
229920001601 polyetherimide Polymers 0.000 description 3
229920005989 resin Polymers 0.000 description 3
239000011347 resin Substances 0.000 description 3
VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
239000004697 Polyetherimide Substances 0.000 description 2
239000004698 Polyethylene Substances 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
-1 polyethylene Polymers 0.000 description 2
229920000573 polyethylene Polymers 0.000 description 2
229920006254 polymer film Polymers 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
239000003039 volatile agent Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
NAMDIHYPBYVYAP-UHFFFAOYSA-N 1-methoxy-2-(2-methoxyethoxy)ethane Chemical compound COCCOCCOC.COCCOCCOC NAMDIHYPBYVYAP-UHFFFAOYSA-N 0.000 description 1
MRTAEHMRKDVKMS-UHFFFAOYSA-N 4-[4-[4-(3,4-dicarboxyphenoxy)phenyl]sulfanylphenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC(C=C1)=CC=C1SC(C=C1)=CC=C1OC1=CC=C(C(O)=O)C(C(O)=O)=C1 MRTAEHMRKDVKMS-UHFFFAOYSA-N 0.000 description 1
OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical group C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 1
102100036848 C-C motif chemokine 20 Human genes 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
101000713099 Homo sapiens C-C motif chemokine 20 Proteins 0.000 description 1
VZUHQRBBQSLSHS-SSZFMOIBSA-N Isoimide Chemical compound C1=CC(Br)=CC=C1\N=C/1C(CCCC2)=C2C(=O)O\1 VZUHQRBBQSLSHS-SSZFMOIBSA-N 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
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 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
230000000052 comparative effect Effects 0.000 description 1
239000002131 composite material Substances 0.000 description 1
238000007334 copolymerization reaction Methods 0.000 description 1
238000012937 correction Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000004427 diamine group Chemical group 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000003733 fiber-reinforced composite Substances 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000005357 flat glass Substances 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
239000012943 hotmelt Substances 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
238000011835 investigation Methods 0.000 description 1
238000010030 laminating Methods 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000000465 moulding Methods 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000012545 processing Methods 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
239000011253 protective coating Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
238000009864 tensile test Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1

Landscapes

Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Indole Compounds (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Adhesives Or Adhesive Processes (AREA)

CA000511903A 1985-06-20 1986-06-19 Copolyimides a combinaison de groupes d'assouplissement Expired - Lifetime CA1276746C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US74690185A	1985-06-20	1985-06-20
US746,901		1985-06-20

Publications (1)

Publication Number	Publication Date
CA1276746C true CA1276746C (fr)	1990-11-20

Family

ID=25002842

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000511903A Expired - Lifetime CA1276746C (fr)	1985-06-20	1986-06-19	Copolyimides a combinaison de groupes d'assouplissement

Country Status (2)

Country	Link
JP (1)	JPS61296031A (fr)
CA (1)	CA1276746C (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN119931041A (zh) *	2024-12-31	2025-05-06	中国航空制造技术研究院	一种亲疏一体热塑性聚酰亚胺树脂增韧剂及其制备方法

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4794157A (en) *	1987-03-25	1988-12-27	General Electric Company	Polyetherimide copolymers, and method for making
GB8809231D0 (en) *	1988-04-19	1988-05-25	Raychem Ltd	Polyetherketoneimides
US5202411A (en) *	1990-04-06	1993-04-13	W. R. Grace & Co.-Conn.	Tri-component polyimide composition and preparation thereof
JPH0586348A (ja) *	1991-09-26	1993-04-06	Sumitomo Bakelite Co Ltd	熱圧着可能なフイルム状接着剤
JPH0598234A (ja) *	1991-10-14	1993-04-20	Sumitomo Bakelite Co Ltd	熱圧着可能なフイルム状接着剤
JP2716609B2 (ja) *	1991-10-14	1998-02-18	住友ベークライト株式会社	熱圧着可能なフィルム状接着剤
JPH0598235A (ja) *	1991-10-14	1993-04-20	Sumitomo Bakelite Co Ltd	熱圧着可能なフイルム状接着剤
JPH05117598A (ja) *	1991-10-29	1993-05-14	Sumitomo Bakelite Co Ltd	熱圧着可能な高熱伝導性フイルム状接着剤
JPH05117596A (ja) *	1991-10-29	1993-05-14	Sumitomo Bakelite Co Ltd	熱圧着可能な高熱伝導性フイルム状接着剤
JPH05125332A (ja) *	1991-11-01	1993-05-21	Sumitomo Bakelite Co Ltd	熱圧着可能な導電性フイルム状接着剤
JPH05125337A (ja) *	1991-11-01	1993-05-21	Sumitomo Bakelite Co Ltd	熱圧着可能な導電性フイルム状接着剤

1986
- 1986-06-19 CA CA000511903A patent/CA1276746C/fr not_active Expired - Lifetime
- 1986-06-20 JP JP61145967A patent/JPS61296031A/ja active Pending

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN119931041A (zh) *	2024-12-31	2025-05-06	中国航空制造技术研究院	一种亲疏一体热塑性聚酰亚胺树脂增韧剂及其制备方法

Also Published As

Publication number	Publication date
JPS61296031A (ja)	1986-12-26

Legal Events

Date	Code	Title	Description
2003-11-20	MKLA	Lapsed

Publication	Publication Date	Title
US4837300A (en)	1989-06-06	Copolyimide with a combination of flexibilizing groups
Hergenrother et al.	1994	Chemistry and properties of imide oligomers end-capped with phenylethynylphthalic anhydrides
CA1219398A (fr)	1987-03-17	Polyimides et leurs intermediaires, esters et acides polyamiques; nouvelles diamines pour les preparer
US5741883A (en)	1998-04-21	Tough, soluble, aromatic, thermoplastic copolyimides
US5147966A (en)	1992-09-15	Polyimide molding powder, coating, adhesive and matrix resin
US6133401A (en)	2000-10-17	Method to prepare processable polyimides with reactive endgroups using 1,3-bis (3-aminophenoxy) benzene
US5412066A (en)	1995-05-02	Phenylethynyl terminated imide oligomers
US4835197A (en)	1989-05-30	Aromatic polymer compositions
US5965687A (en)	1999-10-12	Method of preparing polymers with low melt viscosity
CA1276746C (fr)	1990-11-20	Copolyimides a combinaison de groupes d'assouplissement
US4624888A (en)	1986-11-25	Acetylene (ethynyl) terminated polyimide siloxane and process for preparation thereof
EP0210149A2 (fr)	1987-01-28	Copolyimides avec une association de groupes flexibilisants
EP0117359B1 (fr)	1986-09-17	Poly(éthers de phénylène) contenant des groupes imides dans la chaîne polymère
JPH02269742A (ja)	1990-11-05	フッ素含有結合基を有するポリアミドイミドポリマー
US5478916A (en)	1995-12-26	Solvent resistant copolyimide
St. Clair et al.	1975	Solvent and structure studies of novel polyimide adhesives
EP0486724B1 (fr)	1995-11-08	Feuille thermoplastique adhésive pour attacher des semi-conducteurs
US4920005A (en)	1990-04-24	Aromatic polymer compositions
Progar et al.	1990	A new flexible backbone polyimide adhesive
Jensen et al.	1995	Adhesive properties of cured phenylethynyl-terminated imide oligomers
EP0209546B1 (fr)	1990-10-03	Compositions polymeres aromatiques
JPH05179224A (ja)	1993-07-20	耐熱性接着剤
Maudgal et al.	1984	Preparation and characterization of siloxane-containing thermoplastic polymides
EP1348728B1 (fr)	2007-03-07	Copolymère de polyimide formant un film
EP0456515B1 (fr)	1995-11-08	Polyimides et compositions de résine thermodurcissable les contenant

CA1276746C - Copolyimides a combinaison de groupes d'assouplissement - Google Patents

Info

Links

Landscapes

Applications Claiming Priority (2)

Publications (1)

Family

ID=25002842

Family Applications (1)

Country Status (2)

Cited By (1)

Families Citing this family (11)

Cited By (1)

Also Published As

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