CA1270592A - Polymeres thermodurcissables a teneur de groupes imides, et leur production - Google Patents

Polymeres thermodurcissables a teneur de groupes imides, et leur production

Info

Publication number: CA1270592A
Authority: CA; Canada
Prior art keywords: bis; diamine; mixture; alkenylphenol; polyimide
Prior art date: 1985-01-29
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

CA000500395A

Other languages

English (en)

Inventor

Donna M.B. Tuttle

Steven L. Peake

Robert G. Lees

Dalip K. Kohli

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.)

Wyeth Holdings LLC

Original Assignee

American Cyanamid 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.)

1985-01-29

Filing date

1986-01-27

Publication date

1990-06-19

1986-01-27 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1990-06-19 Application granted granted Critical

1990-06-19 Publication of CA1270592A publication Critical patent/CA1270592A/fr

Status Expired - Fee Related legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 40
230000008569 process Effects 0.000 title claims abstract description 34
125000005462 imide group Chemical group 0.000 title claims description 4
229920000642 polymer Polymers 0.000 title abstract description 4
239000000203 mixture Substances 0.000 claims abstract description 99
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 39
XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 claims abstract description 32
-1 e.g. Chemical compound 0.000 claims abstract description 31
229920000768 polyamine Polymers 0.000 claims abstract description 30
238000006243 chemical reaction Methods 0.000 claims abstract description 10
239000003795 chemical substances by application Substances 0.000 claims abstract description 8
239000002685 polymerization catalyst Substances 0.000 claims abstract description 6
229920001721 polyimide Polymers 0.000 claims description 52
239000004642 Polyimide Substances 0.000 claims description 44
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 36
229910052757 nitrogen Inorganic materials 0.000 claims description 28
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 24
125000004432 carbon atom Chemical group C* 0.000 claims description 22
239000001294 propane Substances 0.000 claims description 20
150000003254 radicals Chemical class 0.000 claims description 20
150000001875 compounds Chemical class 0.000 claims description 19
150000004985 diamines Chemical class 0.000 claims description 16
150000002170 ethers Chemical class 0.000 claims description 15
YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 claims description 13
239000003054 catalyst Substances 0.000 claims description 11
239000009719 polyimide resin Substances 0.000 claims description 11
150000001299 aldehydes Chemical class 0.000 claims description 10
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
150000002576 ketones Chemical class 0.000 claims description 9
125000004430 oxygen atom Chemical group O* 0.000 claims description 9
239000004215 Carbon black (E152) Substances 0.000 claims description 8
229930195733 hydrocarbon Natural products 0.000 claims description 8
VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 claims description 7
230000009471 action Effects 0.000 claims description 7
150000004984 aromatic diamines Chemical class 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
ZETYUTMSJWMKNQ-UHFFFAOYSA-N n,n',n'-trimethylhexane-1,6-diamine Chemical compound CNCCCCCCN(C)C ZETYUTMSJWMKNQ-UHFFFAOYSA-N 0.000 claims description 7
ZYEMGPIYFIJGTP-UHFFFAOYSA-N O-methyleugenol Chemical compound COC1=CC=C(CC=C)C=C1OC ZYEMGPIYFIJGTP-UHFFFAOYSA-N 0.000 claims description 6
RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims description 6
239000000376 reactant Substances 0.000 claims description 6
MBUAAMOJATXYKR-UHFFFAOYSA-N 4-bis(4-aminophenoxy)phosphinothioyloxyaniline Chemical compound C1=CC(N)=CC=C1OP(=S)(OC=1C=CC(N)=CC=1)OC1=CC=C(N)C=C1 MBUAAMOJATXYKR-UHFFFAOYSA-N 0.000 claims description 5
229910019142 PO4 Inorganic materials 0.000 claims description 5
150000005840 aryl radicals Chemical class 0.000 claims description 5
229920006037 cross link polymer Polymers 0.000 claims description 5
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 5
239000010452 phosphate Substances 0.000 claims description 5
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 4
239000005770 Eugenol Substances 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
125000000732 arylene group Chemical group 0.000 claims description 4
229940106691 bisphenol a Drugs 0.000 claims description 4
229960002217 eugenol Drugs 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
238000003860 storage Methods 0.000 claims description 4
ZYPZVOKVDNSKLP-UHFFFAOYSA-N tris(4-aminophenyl) phosphate Chemical compound C1=CC(N)=CC=C1OP(=O)(OC=1C=CC(N)=CC=1)OC1=CC=C(N)C=C1 ZYPZVOKVDNSKLP-UHFFFAOYSA-N 0.000 claims description 4
IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 3
NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 claims description 3
UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 claims description 3
229960001867 guaiacol Drugs 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
238000002844 melting Methods 0.000 claims description 3
230000008018 melting Effects 0.000 claims description 3
150000004986 phenylenediamines Chemical class 0.000 claims description 3
238000010526 radical polymerization reaction Methods 0.000 claims description 3
229910052723 transition metal Inorganic materials 0.000 claims 2
RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 claims 1
229920003192 poly(bis maleimide) Polymers 0.000 abstract description 6
239000000853 adhesive Substances 0.000 abstract description 5
230000001070 adhesive effect Effects 0.000 abstract description 5
239000006260 foam Substances 0.000 abstract description 3
150000003949 imides Chemical group 0.000 abstract description 3
238000003878 thermal aging Methods 0.000 abstract description 3
PADSMSXOUQYFSZ-UHFFFAOYSA-N 1-[(2,5-dioxopyrrol-1-yl)-diphenylmethyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)N1C(=O)C=CC1=O PADSMSXOUQYFSZ-UHFFFAOYSA-N 0.000 abstract 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 17
239000000835 fiber Substances 0.000 description 14
229910002804 graphite Inorganic materials 0.000 description 14
239000010439 graphite Substances 0.000 description 14
229920005989 resin Polymers 0.000 description 10
239000011347 resin Substances 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
230000032798 delamination Effects 0.000 description 7
150000001412 amines Chemical class 0.000 description 6
239000000126 substance Substances 0.000 description 6
QIRNGVVZBINFMX-UHFFFAOYSA-N 2-allylphenol Chemical compound OC1=CC=CC=C1CC=C QIRNGVVZBINFMX-UHFFFAOYSA-N 0.000 description 5
239000002131 composite material Substances 0.000 description 5
239000000155 melt Substances 0.000 description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
150000002989 phenols Chemical class 0.000 description 5
238000012360 testing method Methods 0.000 description 5
ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 4
238000005266 casting Methods 0.000 description 4
239000008119 colloidal silica Substances 0.000 description 4
230000002787 reinforcement Effects 0.000 description 4
230000035882 stress Effects 0.000 description 4
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 3
150000003923 2,5-pyrrolediones Chemical class 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000003342 alkenyl group Chemical group 0.000 description 3
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000004744 fabric Substances 0.000 description 3
238000009472 formulation Methods 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
239000000463 material Substances 0.000 description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000010453 quartz Substances 0.000 description 3
239000011342 resin composition Substances 0.000 description 3
150000003335 secondary amines Chemical class 0.000 description 3
238000007493 shaping process Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
229920000271 Kevlar® Polymers 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
125000005595 acetylacetonate group Chemical group 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
JSYBAZQQYCNZJE-UHFFFAOYSA-N benzene-1,2,4-triamine Chemical compound NC1=CC=C(N)C(N)=C1 JSYBAZQQYCNZJE-UHFFFAOYSA-N 0.000 description 2
239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
229940012017 ethylenediamine Drugs 0.000 description 2
239000000945 filler Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
238000009863 impact test Methods 0.000 description 2
239000004761 kevlar Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
125000005394 methallyl group Chemical group 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
239000006082 mold release agent Substances 0.000 description 2
238000000465 moulding Methods 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
230000000704 physical effect Effects 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
238000012545 processing Methods 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
DWKAPMCNLMAQRI-UHFFFAOYSA-N (3-aminophenyl)-(3,5,5-triaminocyclohexa-1,3-dien-1-yl)methanone Chemical compound NC1=CC(N)(N)CC(C(=O)C=2C=C(N)C=CC=2)=C1 DWKAPMCNLMAQRI-UHFFFAOYSA-N 0.000 description 1
NPSMSOMZCHVSSW-UHFFFAOYSA-N (4-aminophenyl)-(2,4-diaminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(N)C=C1N NPSMSOMZCHVSSW-UHFFFAOYSA-N 0.000 description 1
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 1
WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
PUKLCKVOVCZYKF-UHFFFAOYSA-N 1-[2-(2,5-dioxopyrrol-1-yl)ethyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CCN1C(=O)C=CC1=O PUKLCKVOVCZYKF-UHFFFAOYSA-N 0.000 description 1
IPJGAEWUPXWFPL-UHFFFAOYSA-N 1-[3-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC(N2C(C=CC2=O)=O)=C1 IPJGAEWUPXWFPL-UHFFFAOYSA-N 0.000 description 1
AQGZJQNZNONGKY-UHFFFAOYSA-N 1-[4-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=C(N2C(C=CC2=O)=O)C=C1 AQGZJQNZNONGKY-UHFFFAOYSA-N 0.000 description 1
PYVHLZLQVWXBDZ-UHFFFAOYSA-N 1-[6-(2,5-dioxopyrrol-1-yl)hexyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CCCCCCN1C(=O)C=CC1=O PYVHLZLQVWXBDZ-UHFFFAOYSA-N 0.000 description 1
LYCKDYZIIOVFCX-UHFFFAOYSA-N 1-[[3-[(2,5-dioxopyrrol-1-yl)methyl]phenyl]methyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC1=CC=CC(CN2C(C=CC2=O)=O)=C1 LYCKDYZIIOVFCX-UHFFFAOYSA-N 0.000 description 1
XFRPTDABLAIJMY-UHFFFAOYSA-N 1-[[4-[(2,5-dioxopyrrol-1-yl)methyl]phenyl]methyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC(C=C1)=CC=C1CN1C(=O)C=CC1=O XFRPTDABLAIJMY-UHFFFAOYSA-N 0.000 description 1
AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
YYDRNPOEMZZTPM-UHFFFAOYSA-N 2,4,6-triaminotoluene Chemical compound CC1=C(N)C=C(N)C=C1N YYDRNPOEMZZTPM-UHFFFAOYSA-N 0.000 description 1
SBLBKLRRAALOAA-UHFFFAOYSA-N 2,4,6-trimethylbenzene-1,3,5-triamine Chemical compound CC1=C(N)C(C)=C(N)C(C)=C1N SBLBKLRRAALOAA-UHFFFAOYSA-N 0.000 description 1
NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
HSTOKWSFWGCZMH-UHFFFAOYSA-N 3,3'-diaminobenzidine Chemical compound C1=C(N)C(N)=CC=C1C1=CC=C(N)C(N)=C1 HSTOKWSFWGCZMH-UHFFFAOYSA-N 0.000 description 1
HWYQOMOHBPPWSI-UHFFFAOYSA-N 3,5-diamino-n-(4-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC(N)=CC(N)=C1 HWYQOMOHBPPWSI-UHFFFAOYSA-N 0.000 description 1
LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
SEZLVNATVKZSQO-UHFFFAOYSA-N 3-methyl-1-[3-(3-methyl-2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C(C)=CC(=O)N1C1=CC=CC(N2C(C(C)=CC2=O)=O)=C1 SEZLVNATVKZSQO-UHFFFAOYSA-N 0.000 description 1
ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
JNRLEMMIVRBKJE-UHFFFAOYSA-N 4,4'-Methylenebis(N,N-dimethylaniline) Chemical compound C1=CC(N(C)C)=CC=C1CC1=CC=C(N(C)C)C=C1 JNRLEMMIVRBKJE-UHFFFAOYSA-N 0.000 description 1
JKETWUADWJKEKN-UHFFFAOYSA-N 4-(3,4-diaminophenyl)sulfonylbenzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1S(=O)(=O)C1=CC=C(N)C(N)=C1 JKETWUADWJKEKN-UHFFFAOYSA-N 0.000 description 1
DLYLVPHSKJVGLG-UHFFFAOYSA-N 4-(cyclohexylmethyl)cyclohexane-1,1-diamine Chemical compound C1CC(N)(N)CCC1CC1CCCCC1 DLYLVPHSKJVGLG-UHFFFAOYSA-N 0.000 description 1
HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
ADUMIBSPEHFSLA-UHFFFAOYSA-N 4-[bis(4-aminophenyl)methyl]aniline Chemical compound C1=CC(N)=CC=C1C(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 ADUMIBSPEHFSLA-UHFFFAOYSA-N 0.000 description 1
SNLFYGIUTYKKOE-UHFFFAOYSA-N 4-n,4-n-bis(4-aminophenyl)benzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1N(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 SNLFYGIUTYKKOE-UHFFFAOYSA-N 0.000 description 1
OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
229920000049 Carbon (fiber) Polymers 0.000 description 1
229920013683 Celanese Polymers 0.000 description 1
238000005821 Claisen rearrangement reaction Methods 0.000 description 1
MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
229920000877 Melamine resin Polymers 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000032683 aging Effects 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910001514 alkali metal chloride Inorganic materials 0.000 description 1
150000001339 alkali metal compounds Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000004760 aramid Substances 0.000 description 1
229920006231 aramid fiber Polymers 0.000 description 1
229920003235 aromatic polyamide Polymers 0.000 description 1
239000002585 base Substances 0.000 description 1
RPHKINMPYFJSCF-UHFFFAOYSA-N benzene-1,3,5-triamine Chemical compound NC1=CC(N)=CC(N)=C1 RPHKINMPYFJSCF-UHFFFAOYSA-N 0.000 description 1
SMTUJUHULKBTBS-UHFFFAOYSA-N benzyl(trimethyl)azanium;methanolate Chemical compound [O-]C.C[N+](C)(C)CC1=CC=CC=C1 SMTUJUHULKBTBS-UHFFFAOYSA-N 0.000 description 1
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
239000004917 carbon fiber Substances 0.000 description 1
239000000919 ceramic Substances 0.000 description 1
229940000425 combination drug Drugs 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
230000003750 conditioning effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229930003836 cresol Natural products 0.000 description 1
VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
230000002950 deficient Effects 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000004870 electrical engineering Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
239000011953 free-radical catalyst Substances 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
150000002432 hydroperoxides Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
238000010030 laminating Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229940018564 m-phenylenediamine Drugs 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
238000002156 mixing Methods 0.000 description 1
OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 1
RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
229940075566 naphthalene Drugs 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
235000019645 odor Nutrition 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
150000008379 phenol ethers Chemical class 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920006216 polyvinyl aromatic Polymers 0.000 description 1
150000003142 primary aromatic amines Chemical class 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
CZIIDUIQNLSXOJ-UHFFFAOYSA-N pyridine-2,4,5-triamine Chemical compound NC1=CC(N)=C(N)C=N1 CZIIDUIQNLSXOJ-UHFFFAOYSA-N 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
230000003014 reinforcing effect Effects 0.000 description 1
238000010125 resin casting Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229920002545 silicone oil Polymers 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000010998 test method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
150000003682 vanadium compounds Chemical class 0.000 description 1
239000001993 wax Substances 0.000 description 1
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1

Landscapes

Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CA000500395A 1985-01-29 1986-01-27 Polymeres thermodurcissables a teneur de groupes imides, et leur production Expired - Fee Related CA1270592A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US69599285A	1985-01-29	1985-01-29
US695,992		1985-01-29

Publications (1)

Publication Number	Publication Date
CA1270592A true CA1270592A (fr)	1990-06-19

Family

ID=24795283

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000500395A Expired - Fee Related CA1270592A (fr)	1985-01-29	1986-01-27	Polymeres thermodurcissables a teneur de groupes imides, et leur production

Country Status (1)

Country	Link
CA (1)	CA1270592A (fr)

1986
- 1986-01-27 CA CA000500395A patent/CA1270592A/fr not_active Expired - Fee Related

Legal Events

Date	Code	Title	Description
1994-12-19	MKLA	Lapsed

Publication	Publication Date	Title
CA1263495A (fr)	1989-11-28	Composition de resine de bis-maleimide
US4100140A (en)	1978-07-11	Process for the manufacture of crosslinked polymers which contain imide groups
US4463147A (en)	1984-07-31	Heat-curable mixtures, stable on storage, based on polyimides and containing polymerization catalysts
US4038251A (en)	1977-07-26	Process for the manufacture of polyaddition products containing imide groups by reaction of polymaleimides with polyhydric phenols using amine catalyst
US4220741A (en)	1980-09-02	Curable mixtures based on maleimide prepolymers and acetone-anil
US4888407A (en)	1989-12-19	Imide compound and composition containing the same
EP0078039B1 (fr)	1986-01-22	Composition de résine thermodurcissable, son prépolymère, et article durci fabriqué à partir de celle-ci
JPS62253607A (ja)	1987-11-05	置換ビシクロ〔２．２．１〕−ヘプト−５−エン−２，３−ジカルボキシイミド及びポリマレイミドを含有する熱硬化性混合物
US4238591A (en)	1980-12-09	Novel copolymers of imido monomer/hydroxylated organosilicon comonomer
US4361690A (en)	1982-11-30	Novel imido/hydroxylate organosilicon copolymers
US4486583A (en)	1984-12-04	Heat-resistant resin from aromatic cyanamide compound and aromatic amine compound
JPH02158626A (ja)	1990-06-19	ヒンダードジアミンから製造したイミド基含有ポリマー製造用混合物
US4066621A (en)	1978-01-03	Curable mixtures based on polyimides of unsaturated dicarboxylic acids and indole compounds
CA1270592A (fr)	1990-06-19	Polymeres thermodurcissables a teneur de groupes imides, et leur production
JPH03139524A (ja)	1991-06-13	立体障害ジアミンから製造したイミド基含有ポリマー製造用混合物
US4296219A (en)	1981-10-20	Bismide-ether compounds, compositions thereof, and method of producing same
KR0177039B1 (ko)	1999-05-15	장애된 디아민류로부터 제조된 이미드기를 함유하는 중합체
US5329047A (en)	1994-07-12	Aromatic allyl amine thermosetting resin composition
JP2776056B2 (ja)	1998-07-16	ポリアミノビスマレイミド樹脂組成物及びそれを用いた銅張積層板の製造方法
US5198516A (en)	1993-03-30	Thermally stable bisimido/p-allylaniline copolymers
JPH0689118B2 (ja)	1994-11-09	エポキシ樹脂組成物
KR100204326B1 (ko)	1999-06-15	난연성 폴리이미드 조성물
JPS5817532B2 (ja)	1983-04-07	耐熱性樹脂組成物
JPH01279926A (ja)	1989-11-10	変性ビスマレイミド樹脂及びその製造方法
JPS60133033A (ja)	1985-07-16	低流動性プリプレグの製法