JPS60364B2 - イミド基を含む重付加物の製法 - Google Patents

イミド基を含む重付加物の製法

Info

Publication number: JPS60364B2
Authority: JP; Japan
Prior art keywords: bis; formula; reaction; maleimide; mixture
Prior art date: 1973-12-21
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

JP58063527A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5941332A (ja

Inventor

イムレ・フオルゴ

ブル−ノ・シユライバ−

アルフレツト・レンナ−

テオバルト・ハウク

アンドレ・シユミツテル

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.)

Novartis AG

Original Assignee

Ciba Geigy AG

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.)

1973-12-21

Filing date

1983-04-11

Publication date

1985-01-08

1983-04-11 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1984-03-07 Publication of JPS5941332A publication Critical patent/JPS5941332A/ja

1985-01-08 Publication of JPS60364B2 publication Critical patent/JPS60364B2/ja

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 11
125000005462 imide group Chemical group 0.000 title claims description 5
229920000768 polyamine Polymers 0.000 claims description 19
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 17
239000000126 substance Substances 0.000 claims description 15
239000003054 catalyst Substances 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
150000007514 bases Chemical class 0.000 claims description 3
238000000034 method Methods 0.000 description 34
238000006243 chemical reaction Methods 0.000 description 24
229910052757 nitrogen Inorganic materials 0.000 description 21
239000000203 mixture Substances 0.000 description 20
150000002989 phenols Chemical class 0.000 description 11
239000000047 product Substances 0.000 description 11
239000000243 solution Substances 0.000 description 11
239000006260 foam Substances 0.000 description 10
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
239000000843 powder Substances 0.000 description 9
239000007858 starting material Substances 0.000 description 9
238000010438 heat treatment Methods 0.000 description 8
238000002360 preparation method Methods 0.000 description 8
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 7
150000001412 amines Chemical class 0.000 description 7
150000001875 compounds Chemical class 0.000 description 7
229930003836 cresol Natural products 0.000 description 7
229920003986 novolac Polymers 0.000 description 7
229920000642 polymer Polymers 0.000 description 7
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
239000000463 material Substances 0.000 description 6
239000000155 melt Substances 0.000 description 6
239000000376 reactant Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 4
239000004604 Blowing Agent Substances 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
-1 aliphatic dithiols Chemical class 0.000 description 4
150000003949 imides Chemical class 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000000758 substrate Substances 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
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 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-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
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000003118 aryl 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
238000005266 casting Methods 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
230000006835 compression Effects 0.000 description 3
238000007906 compression Methods 0.000 description 3
238000001723 curing Methods 0.000 description 3
150000004985 diamines Chemical class 0.000 description 3
238000005187 foaming Methods 0.000 description 3
239000003365 glass fiber Substances 0.000 description 3
238000000227 grinding Methods 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
235000006408 oxalic acid Nutrition 0.000 description 3
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
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 description 3
USVVENVKYJZFMW-ONEGZZNKSA-N (e)-carboxyiminocarbamic acid Chemical compound OC(=O)\N=N\C(O)=O USVVENVKYJZFMW-ONEGZZNKSA-N 0.000 description 2
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
150000003923 2,5-pyrrolediones Chemical class 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
239000004642 Polyimide Substances 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
238000005452 bending Methods 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
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
230000001588 bifunctional effect Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000004132 cross linking Methods 0.000 description 2
150000004662 dithiols Chemical class 0.000 description 2
239000000835 fiber Substances 0.000 description 2
239000000945 filler Substances 0.000 description 2
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
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 2
238000000465 moulding Methods 0.000 description 2
235000019645 odor Nutrition 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
229920001721 polyimide Polymers 0.000 description 2
150000008442 polyphenolic compounds Chemical class 0.000 description 2
235000013824 polyphenols Nutrition 0.000 description 2
150000003141 primary amines Chemical class 0.000 description 2
WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
150000003335 secondary amines Chemical class 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
239000004071 soot Substances 0.000 description 2
150000003457 sulfones Chemical class 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
229920001187 thermosetting polymer Polymers 0.000 description 2
239000002759 woven fabric Substances 0.000 description 2
VSQMMINOLMZQMO-UHFFFAOYSA-N (3-aminophenyl)-(3,3,5-triaminocyclohexa-1,5-dien-1-yl)methanone Chemical compound NC1=CC(C(=O)C2=CC(=CC=C2)N)=CC(C1)(N)N VSQMMINOLMZQMO-UHFFFAOYSA-N 0.000 description 1
FXZCCINCKDATPA-UHFFFAOYSA-L (4-aminophenyl) phosphate Chemical compound NC1=CC=C(OP([O-])([O-])=O)C=C1 FXZCCINCKDATPA-UHFFFAOYSA-L 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
WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-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
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
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-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
KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-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
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
VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 1
NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 1
RQCACQIALULDSK-UHFFFAOYSA-N 4-(4-hydroxyphenyl)sulfinylphenol Chemical compound C1=CC(O)=CC=C1S(=O)C1=CC=C(O)C=C1 RQCACQIALULDSK-UHFFFAOYSA-N 0.000 description 1
DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
AWFMZJOSCOBYOQ-UHFFFAOYSA-N 4-[5-(3,4-diaminophenyl)pyridin-3-yl]benzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1C1=CN=CC(C=2C=C(N)C(N)=CC=2)=C1 AWFMZJOSCOBYOQ-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
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 description 1
ICGLPKIVTVWCFT-UHFFFAOYSA-N 4-methylbenzenesulfonohydrazide Chemical compound CC1=CC=C(S(=O)(=O)NN)C=C1 ICGLPKIVTVWCFT-UHFFFAOYSA-N 0.000 description 1
229930185605 Bisphenol Natural products 0.000 description 1
NKFPZVKGICCRPO-UHFFFAOYSA-N C1(=CC=C(C=C1)N1C(C=CC1=O)=O)N1C(C=CC1=O)=O.C1(=CC(=CC=C1)N1C(C=CC1=O)=O)N1C(C=CC1=O)=O.C1(C=CC(N1CCCCCCN1C(C=CC1=O)=O)=O)=O.C(CN1C(C=CC1=O)=O)N1C(C=CC1=O)=O Chemical compound C1(=CC=C(C=C1)N1C(C=CC1=O)=O)N1C(C=CC1=O)=O.C1(=CC(=CC=C1)N1C(C=CC1=O)=O)N1C(C=CC1=O)=O.C1(C=CC(N1CCCCCCN1C(C=CC1=O)=O)=O)=O.C(CN1C(C=CC1=O)=O)N1C(C=CC1=O)=O NKFPZVKGICCRPO-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-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
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
229920002323 Silicone foam Polymers 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-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
230000002378 acidificating effect Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
ANUAIBBBDSEVKN-UHFFFAOYSA-N benzene-1,2,4,5-tetramine Chemical compound NC1=CC(N)=C(N)C=C1N ANUAIBBBDSEVKN-UHFFFAOYSA-N 0.000 description 1
GGNQRNBDZQJCCN-UHFFFAOYSA-N benzene-1,2,4-triol Chemical compound OC1=CC=C(O)C(O)=C1 GGNQRNBDZQJCCN-UHFFFAOYSA-N 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
VJRITMATACIYAF-UHFFFAOYSA-N benzenesulfonohydrazide Chemical compound NNS(=O)(=O)C1=CC=CC=C1 VJRITMATACIYAF-UHFFFAOYSA-N 0.000 description 1
HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
238000009835 boiling Methods 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
239000006229 carbon black Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229940075614 colloidal silicon dioxide Drugs 0.000 description 1
238000002485 combustion reaction Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000000039 congener Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000010276 construction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
150000001896 cresols Chemical class 0.000 description 1
VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
229910000071 diazene Inorganic materials 0.000 description 1
150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
238000009826 distribution Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
238000004870 electrical engineering Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000003063 flame retardant Substances 0.000 description 1
NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
238000010097 foam moulding Methods 0.000 description 1
239000004088 foaming agent Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
239000008240 homogeneous mixture Substances 0.000 description 1
238000007731 hot pressing Methods 0.000 description 1
229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
235000011167 hydrochloric acid Nutrition 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000003475 lamination Methods 0.000 description 1
229940018564 m-phenylenediamine Drugs 0.000 description 1
FSQQTNAZHBEJLS-UPHRSURJSA-N maleamic acid Chemical class NC(=O)\C=C/C(O)=O FSQQTNAZHBEJLS-UPHRSURJSA-N 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
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
238000003801 milling Methods 0.000 description 1
239000006082 mold release agent Substances 0.000 description 1
239000012170 montan wax Substances 0.000 description 1
OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 1
JOJOPWYLFLOFAE-UHFFFAOYSA-N naphthalene-1,3,7-triamine Chemical compound C1=C(N)C=C(N)C2=CC(N)=CC=C21 JOJOPWYLFLOFAE-UHFFFAOYSA-N 0.000 description 1
PCILLCXFKWDRMK-UHFFFAOYSA-N naphthalene-1,4-diol Chemical group C1=CC=C2C(O)=CC=C(O)C2=C1 PCILLCXFKWDRMK-UHFFFAOYSA-N 0.000 description 1
KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
DKYADULMEONPQX-UHFFFAOYSA-N naphthalene-2,3,6,7-tetramine Chemical compound NC1=C(N)C=C2C=C(N)C(N)=CC2=C1 DKYADULMEONPQX-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000003921 oil Substances 0.000 description 1
230000008520 organization Effects 0.000 description 1
239000002245 particle Substances 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
239000005011 phenolic resin Substances 0.000 description 1
QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
229960001553 phloroglucinol Drugs 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
238000006068 polycondensation reaction Methods 0.000 description 1
239000011148 porous material Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000003825 pressing Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
150000003142 primary aromatic amines Chemical class 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
229940079877 pyrogallol Drugs 0.000 description 1
239000010453 quartz Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
229960001755 resorcinol Drugs 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000013514 silicone foam Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical group O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
150000003463 sulfur Chemical class 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000009182 swimming Effects 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000012719 thermal polymerization Methods 0.000 description 1
RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 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
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
SCNCNRSYYOCCEC-UHFFFAOYSA-N tris(4-aminophenyl) phosphite Chemical compound C1=CC(N)=CC=C1OP(OC=1C=CC(N)=CC=1)OC1=CC=C(N)C=C1 SCNCNRSYYOCCEC-UHFFFAOYSA-N 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000008096 xylene 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

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
- C08G73/12—Unsaturated polyimide precursors
- C08G73/126—Unsaturated polyimide precursors the unsaturated precursors being wholly aromatic
- C08G73/127—Unsaturated polyimide precursors the unsaturated precursors being wholly aromatic 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
- C08G73/12—Unsaturated 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
- C08G73/12—Unsaturated polyimide precursors
- C08G73/125—Unsaturated polyimide precursors the unsaturated precursors containing atoms other than carbon, hydrogen, oxygen or nitrogen 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)

JP58063527A 1973-12-21 1983-04-11 イミド基を含む重付加物の製法 Expired JPS60364B2 (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
CH1804773A CH586246A5 (en)	1973-12-21	1973-12-21	Heat stable polymers for paint, electrical and building inds. - and comprising addn. prods. of polyimides, polyphenols and amines
CH18048/73		1973-12-21
CH18047/73		1973-12-21

Publications (2)

Publication Number	Publication Date
JPS5941332A JPS5941332A (ja)	1984-03-07
JPS60364B2 true JPS60364B2 (ja)	1985-01-08

Family

ID=4430028

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP58063527A Expired JPS60364B2 (ja)	1973-12-21	1983-04-11	イミド基を含む重付加物の製法

Country Status (4)

Country	Link
JP (1)	JPS60364B2 (fr)
BE (1)	BE823720A (fr)
CH (1)	CH586246A5 (fr)
ZA (1)	ZA748135B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH01136966A (ja) *	1987-11-24	1989-05-30	Kobe Steel Ltd	物理蒸着装置

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP5549329B2 (ja) *	2010-04-02	2014-07-16	住友ベークライト株式会社	回路基板用熱硬化性組成物

1973
- 1973-12-21 CH CH1804773A patent/CH586246A5/de not_active IP Right Cessation
1974
- 1974-12-20 BE BE151824A patent/BE823720A/fr unknown
- 1974-12-20 ZA ZA00748135A patent/ZA748135B/xx unknown
1983
- 1983-04-11 JP JP58063527A patent/JPS60364B2/ja not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH01136966A (ja) *	1987-11-24	1989-05-30	Kobe Steel Ltd	物理蒸着装置

Also Published As

Publication number	Publication date
ZA748135B (en)	1976-01-28
JPS5941332A (ja)	1984-03-07
CH586246A5 (en)	1977-03-31
BE823720A (fr)	1975-06-20

Publication	Publication Date	Title
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
JPS63295523A (ja)	1988-12-01	新規なプロペニル置換多価フェノール
US4525572A (en)	1985-06-25	Heat-curable mixtures, stable on storage, based on polyimides and containing polymerization catalysts
US4026871A (en)	1977-05-31	Chain-extending phenolic end-capped polyimides
JPS6160096B2 (fr)	1986-12-19
US4076697A (en)	1978-02-28	Process for the manufacture of polyaddition products containing imide groups
US4026833A (en)	1977-05-31	Chain-extending polyimides with aromatic polyisocyanates
US4065433A (en)	1977-12-27	Process for the manufacture of polyaddition products containing imide groups
EP0078039B1 (fr)	1986-01-22	Composition de résine thermodurcissable, son prépolymère, et article durci fabriqué à partir de celle-ci
JPS583493B2 (ja)	1983-01-21	コウオンドジユウゴウタイノセイゾウホウホウ
JPS591297B2 (ja)	1984-01-11	チヨゾウアンテイセイネツコウカセイソセイブツ
JPS60364B2 (ja)	1985-01-08	イミド基を含む重付加物の製法
US5041528A (en)	1991-08-20	New dimer for synthesis of high performance polymer matrix composites
US4066621A (en)	1978-01-03	Curable mixtures based on polyimides of unsaturated dicarboxylic acids and indole compounds
US4954601A (en)	1990-09-04	Polyimide precursors and method for preparing crosslinked polyimides using said precursors
US4247672A (en)	1981-01-27	Heat-curable mixtures based on polyimides and poly-β-iminocrotononitriles
US4046777A (en)	1977-09-06	Fluorine substituted maleimides
JPS595134B2 (ja)	1984-02-02	ハツポウプラスチツクセイゾウヨウソセイブツ
JPS62177033A (ja)	1987-08-03	耐熱積層板の製造方法
JPH0291153A (ja)	1990-03-30	ビスマレイミド樹脂水性分散液及びその製造方法
JPS593485B2 (ja)	1984-01-24	ハツポウプラスチツクセイゾウヨウソセイブツ
JPH0559933B2 (fr)	1993-09-01
CA1270592A (fr)	1990-06-19	Polymeres thermodurcissables a teneur de groupes imides, et leur production
JPS6368637A (ja)	1988-03-28	耐熱性樹脂組成物
KR820002316B1 (ko)	1982-12-17	비스이미드-에테르 화합물의 제조방법

JPS60364B2 - イミド基を含む重付加物の製法 - Google Patents

Info

Links

Classifications

Landscapes

Applications Claiming Priority (3)

Publications (2)

Family

ID=4430028

Family Applications (1)

Country Status (4)

Cited By (1)

Families Citing this family (1)

Cited By (1)

Also Published As

Similar Documents