CH620937A5 - - Google Patents
Download PDFInfo
- Publication number
- CH620937A5 CH620937A5 CH1458474A CH1458474A CH620937A5 CH 620937 A5 CH620937 A5 CH 620937A5 CH 1458474 A CH1458474 A CH 1458474A CH 1458474 A CH1458474 A CH 1458474A CH 620937 A5 CH620937 A5 CH 620937A5
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- ether
- glycol
- soluble
- soluble solvent
- Prior art date
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 32
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 31
- 229920001721 polyimide Polymers 0.000 claims description 29
- 239000004642 Polyimide Substances 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 17
- 150000001412 amines Chemical class 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 239000002243 precursor Substances 0.000 claims description 15
- 239000003021 water soluble solvent Substances 0.000 claims description 15
- RLHGFJMGWQXPBW-UHFFFAOYSA-N 2-hydroxy-3-(1h-imidazol-5-ylmethyl)benzamide Chemical compound NC(=O)C1=CC=CC(CC=2NC=NC=2)=C1O RLHGFJMGWQXPBW-UHFFFAOYSA-N 0.000 claims description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 13
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical group CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 10
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 9
- 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 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 5
- -1 4,4-dimethylheptamethylenediamine oxyheptamethylene diamine Chemical class 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- GXVUZYLYWKWJIM-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanamine Chemical compound NCCOCCN GXVUZYLYWKWJIM-UHFFFAOYSA-N 0.000 claims description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- 150000001334 alicyclic compounds Chemical class 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 3
- 230000008030 elimination Effects 0.000 claims description 3
- 238000003379 elimination reaction Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 2
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 claims description 2
- IKSUMZCUHPMCQV-UHFFFAOYSA-N 2-(3-aminophenyl)-1,3-benzoxazol-5-amine Chemical compound NC1=CC=CC(C=2OC3=CC=C(N)C=C3N=2)=C1 IKSUMZCUHPMCQV-UHFFFAOYSA-N 0.000 claims description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 2
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- ZBMISJGHVWNWTE-UHFFFAOYSA-N 3-(4-aminophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(N)=C1 ZBMISJGHVWNWTE-UHFFFAOYSA-N 0.000 claims description 2
- ICNFHJVPAJKPHW-UHFFFAOYSA-N 4,4'-Thiodianiline Chemical compound C1=CC(N)=CC=C1SC1=CC=C(N)C=C1 ICNFHJVPAJKPHW-UHFFFAOYSA-N 0.000 claims description 2
- TYNNEOUATWMCIY-UHFFFAOYSA-N 4-(4-aminophenyl)phosphonoylaniline Chemical compound C1=CC(N)=CC=C1P(=O)C1=CC=C(N)C=C1 TYNNEOUATWMCIY-UHFFFAOYSA-N 0.000 claims description 2
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 claims description 2
- OSGFBINRYVUILV-UHFFFAOYSA-N 4-[(4-aminophenyl)-diethylsilyl]aniline Chemical compound C=1C=C(N)C=CC=1[Si](CC)(CC)C1=CC=C(N)C=C1 OSGFBINRYVUILV-UHFFFAOYSA-N 0.000 claims description 2
- HSBOCPVKJMBWTF-UHFFFAOYSA-N 4-[1-(4-aminophenyl)ethyl]aniline Chemical compound C=1C=C(N)C=CC=1C(C)C1=CC=C(N)C=C1 HSBOCPVKJMBWTF-UHFFFAOYSA-N 0.000 claims description 2
- WUPRYUDHUFLKFL-UHFFFAOYSA-N 4-[3-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(OC=2C=CC(N)=CC=2)=C1 WUPRYUDHUFLKFL-UHFFFAOYSA-N 0.000 claims description 2
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 claims description 2
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 claims description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 2
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 claims description 2
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 2
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 claims description 2
- CBLAIDIBZHTGLV-UHFFFAOYSA-N dodecane-2,11-diamine Chemical compound CC(N)CCCCCCCCC(C)N CBLAIDIBZHTGLV-UHFFFAOYSA-N 0.000 claims description 2
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 claims description 2
- 229940018564 m-phenylenediamine Drugs 0.000 claims description 2
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 3
- 239000003960 organic solvent Substances 0.000 claims 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 claims 1
- HRWADRITRNUCIY-UHFFFAOYSA-N 2-(2-propan-2-yloxyethoxy)ethanol Chemical compound CC(C)OCCOCCO HRWADRITRNUCIY-UHFFFAOYSA-N 0.000 claims 1
- JCRRFJIVUPSNTA-UHFFFAOYSA-N 4-[4-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 JCRRFJIVUPSNTA-UHFFFAOYSA-N 0.000 claims 1
- WTQZEAGJBQQLQQ-UHFFFAOYSA-N 4-ethoxyhexan-3-ol Chemical compound C(C)OC(C(CC)O)CC WTQZEAGJBQQLQQ-UHFFFAOYSA-N 0.000 claims 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 1
- 239000002202 Polyethylene glycol Substances 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 claims 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims 1
- 125000003827 glycol group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 claims 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 description 30
- 239000002904 solvent Substances 0.000 description 11
- 229910021529 ammonia Inorganic materials 0.000 description 10
- 150000003863 ammonium salts Chemical class 0.000 description 10
- 239000007858 starting material Substances 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- 235000011114 ammonium hydroxide Nutrition 0.000 description 8
- 210000003298 dental enamel Anatomy 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 5
- 238000004804 winding Methods 0.000 description 5
- 230000002411 adverse Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000005299 abrasion Methods 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000013007 heat curing Methods 0.000 description 3
- 125000000962 organic group Chemical group 0.000 description 3
- 229920005575 poly(amic acid) Polymers 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 230000035939 shock Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- GGAUUQHSCNMCAU-ZXZARUISSA-N (2s,3r)-butane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C[C@H](C(O)=O)[C@H](C(O)=O)CC(O)=O GGAUUQHSCNMCAU-ZXZARUISSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000007824 aliphatic compounds Chemical class 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BJINVQNEBGOMCR-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl acetate Chemical compound COCCOCCOC(C)=O BJINVQNEBGOMCR-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical class CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 1
- RYYUUQPLFHRZOY-UHFFFAOYSA-N 4-[2-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC=C1OC1=CC=C(N)C=C1 RYYUUQPLFHRZOY-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000003915 air pollution Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000009615 deamination Effects 0.000 description 1
- 238000006481 deamination reaction Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008236 heating water Substances 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-COJKEBBMSA-N octanoic acid Chemical class CCCCCCC[11C](O)=O WWZKQHOCKIZLMA-COJKEBBMSA-N 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
- 238000003911 water pollution Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 150000003755 zirconium compounds Chemical class 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
- C08G73/1032—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous characterised by the solvent(s) used
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)
- Paints Or Removers (AREA)
- Organic Insulating Materials (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12658773A JPS533796B2 (en, 2012) | 1973-11-09 | 1973-11-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH620937A5 true CH620937A5 (en, 2012) | 1980-12-31 |
Family
ID=14938854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1458474A CH620937A5 (en, 2012) | 1973-11-09 | 1974-10-31 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3925313A (en, 2012) |
| JP (1) | JPS533796B2 (en, 2012) |
| CA (1) | CA1042579A (en, 2012) |
| CH (1) | CH620937A5 (en, 2012) |
| DE (1) | DE2434176C3 (en, 2012) |
| FR (1) | FR2250791B1 (en, 2012) |
| GB (1) | GB1439881A (en, 2012) |
| IT (1) | IT1019302B (en, 2012) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4189518A (en) * | 1969-05-08 | 1980-02-19 | General Electric Company | Cured polymeric coating material, coated substrate, and process of forming |
| JPS5137297B2 (en, 2012) * | 1974-09-26 | 1976-10-14 | ||
| US4066593A (en) * | 1975-10-23 | 1978-01-03 | Standard Oil Company (Indiana) | Water soluble wire enamels |
| JPS5271530A (en) * | 1975-12-11 | 1977-06-15 | Showa Electric Wire & Cable Co Ltd | Method of manufacturing of electric insulating paint having water as m edium |
| JPS5342241A (en) * | 1976-09-29 | 1978-04-17 | Nitto Electric Ind Co Ltd | Stabilization of water-soluble compositions |
| JPS5345352A (en) * | 1976-10-06 | 1978-04-24 | Nitto Electric Ind Co Ltd | Resin compositions solubilized in water |
| DE2651194A1 (de) * | 1976-11-10 | 1978-05-18 | Basf Ag | Waessrige polyimiddispersionen |
| JPS543300A (en) * | 1977-06-09 | 1979-01-11 | Nitto Electric Ind Co | Heat resistant electric insulating film |
| CA1096712A (en) * | 1977-12-19 | 1981-03-03 | Douglas W.T. Beattie | Pigment compositions and methods of preparation |
| ZA796150B (en) * | 1978-12-07 | 1980-10-29 | Ici Ltd | Chlorination process |
| US4290929A (en) * | 1979-07-13 | 1981-09-22 | Essex Group, Inc. | Aqueous solutions of polyesterimides and methods of making the same |
| DE3037269A1 (de) * | 1980-10-02 | 1982-06-16 | Dr. Beck & Co Ag, 2000 Hamburg | Hitzehaertbare, amid- und imidgruppen enthaltende polykondensationsprodukte |
| US4389510A (en) * | 1981-04-17 | 1983-06-21 | United Technologies Corporation | Water soluble polyimide prepared from 1,2,3,4 butane tetracarboxylic acid and method of preparation |
| JPS58162659A (ja) * | 1982-03-19 | 1983-09-27 | Nitto Electric Ind Co Ltd | 水溶性樹脂組成物の製造方法 |
| US4418190A (en) * | 1982-04-09 | 1983-11-29 | Essex Group, Inc. | Dielectric films from water soluble polyimides |
| US4480088A (en) * | 1983-10-20 | 1984-10-30 | United Technologies Corporation | Water soluble polyimide resin system |
| JPS61155448A (ja) * | 1984-12-27 | 1986-07-15 | New Japan Chem Co Ltd | 水系ポリイミド樹脂組成物 |
| US4670342A (en) * | 1985-04-08 | 1987-06-02 | General Electric Company | Method of making electrical inductive devices for use in hermetic refrigerant atmospheres |
| JP2727185B2 (ja) * | 1987-08-27 | 1998-03-11 | 宇部興産株式会社 | 芳香族ポリイミド多層フィルムの製造方法 |
| US5096932A (en) * | 1990-01-16 | 1992-03-17 | Ethyl Corporation | Polyimide foam products and methods |
| JPH07102196A (ja) * | 1993-10-01 | 1995-04-18 | Nitto Denko Corp | 電着塗装剤および電着塗装方法 |
| AT411529B (de) * | 1996-11-29 | 2004-02-25 | Dupont Performance Coatings Au | Überzugsmittel zur herstellung einer elektrisch isolierenden beschichtung auf elektrostahlblech |
| US6479581B1 (en) | 1999-03-12 | 2002-11-12 | Solvay Advanced Polymers, Llc | Aqueous-based polyamide-amic acid compositions |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3179632A (en) * | 1962-01-26 | 1965-04-20 | Du Pont | Process for preparing polyimides by treating polyamide-acids with aromatic monocarboxylic acid anhydrides |
| US3440196A (en) * | 1966-05-05 | 1969-04-22 | Gen Electric | Coating solutions and methods for preparing and using the same |
| US3448068A (en) * | 1966-05-05 | 1969-06-03 | Gen Electric | Polymer solutions and methods for preparing and using the same |
| US3573132A (en) * | 1967-10-30 | 1971-03-30 | Rhone Poulenc Sa | Process for the preparation of polyimides |
| US3663728A (en) * | 1968-07-25 | 1972-05-16 | Gen Electric | Process for producing polyamide acid and polyimides |
| GB1277824A (en) * | 1968-09-02 | 1972-06-14 | Toray Industries | Polyimides |
| US3766117A (en) * | 1970-03-12 | 1973-10-16 | Gen Electric | Method of making a dispersion from polyamide acid |
| US3810858A (en) * | 1971-12-13 | 1974-05-14 | Gen Electric | Method for recovering polyamide acid values from deteriorated dispersions of polyamide acid |
-
1973
- 1973-11-09 JP JP12658773A patent/JPS533796B2/ja not_active Expired
-
1974
- 1974-07-09 US US486932A patent/US3925313A/en not_active Expired - Lifetime
- 1974-07-09 GB GB3045974A patent/GB1439881A/en not_active Expired
- 1974-07-16 DE DE2434176A patent/DE2434176C3/de not_active Expired
- 1974-07-19 FR FR7425276A patent/FR2250791B1/fr not_active Expired
- 1974-09-10 CA CA209,016A patent/CA1042579A/en not_active Expired
- 1974-09-17 IT IT53055/74A patent/IT1019302B/it active
- 1974-10-31 CH CH1458474A patent/CH620937A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5076196A (en, 2012) | 1975-06-21 |
| AU7293874A (en) | 1976-03-11 |
| IT1019302B (it) | 1977-11-10 |
| JPS533796B2 (en, 2012) | 1978-02-09 |
| DE2434176B2 (de) | 1979-08-09 |
| DE2434176A1 (de) | 1975-05-15 |
| FR2250791B1 (en, 2012) | 1980-11-14 |
| GB1439881A (en) | 1976-06-16 |
| CA1042579A (en) | 1978-11-14 |
| FR2250791A1 (en, 2012) | 1975-06-06 |
| US3925313A (en) | 1975-12-09 |
| DE2434176C3 (de) | 1980-04-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH620937A5 (en, 2012) | ||
| DE2945139C2 (de) | Verfahren zur Herstellung einer homogenen Polyimidlösung | |
| DE1595092A1 (de) | Verfahren zur Herstellung von aromatischen Polyamidamiden | |
| DE1202981C2 (de) | Verfahren zur herstellung von aromatischen polyimidformkoerpern | |
| DE2439386C3 (de) | Wäßriger Einbrennlack und dessen Verwendung als Drahtlack | |
| DE3787990T2 (de) | Lösliche Polyimide. | |
| EP0049393B1 (de) | Hitzehärtbare, Amid- und Imidgruppen enthaltende Poly-Kondensationsprodukte und ihre Verwendung | |
| DE1720835B2 (de) | Verfahren zur Herstellung von homogenen wäßrigen Polymidsäurelösungen | |
| DE1720839A1 (de) | Verfahren zur Herstellung von homogenen waessrigen Polyamidsaeureloesungen | |
| DE1913280B2 (de) | Aromatische Polyimide | |
| CH463779A (de) | Stabilisierte Polyamidsäurelösung mit verbesserten Viskositätseigenschaften und Verfahren zur Herstellung derselben | |
| DE1770146A1 (de) | Verfahren zur Herstellung von Poly-(arylen-triketoimidazolidinen) | |
| DE1595005C3 (de) | Verfahren zur Herstellung von stabilen Polyamidsäurelösungen und deren Verwendung zum Überziehen von elektrischen Leitern | |
| DE2528251C2 (de) | Polyamidimid-Vorkondensate | |
| DE1793700C3 (de) | 4,4'- eckige Klammer auf p-Phenylenbis- eckige Klammer auf (phenylimino) carbamyl eckige Klammer zu eckige Klammer zu diphthalsäureanhydrid und Verfahren zu seiner Herstellung | |
| DE2714416A1 (de) | Verfahren zum stabilisieren einer wasserloeslichen zusammensetzung | |
| DE2519673A1 (de) | Loesungen eines waermebestaendigen harzes, verfahren zu deren herstellung und diese loesungen enthaltende drahtlacke | |
| DE1770522A1 (de) | Verfahren zur Herstellung gegen Hitze widerstandsfaehiger Polyimide | |
| DE1765738C3 (de) | Isolierender Überzug auf einem elektrischen Leiter | |
| DE2239611C3 (de) | Verfahren zur Herstellung von in Kresol löslichen Polyamidimidvorläufern | |
| DE1720837A1 (de) | Verfahren zur Herstellung von Polyamidsaeureloesungen | |
| EP0324315A2 (de) | Polyamid-Polyimid-Blockcopolymere | |
| AT209566B (de) | Verfahren zur Herstellung eines zähen, hochmolekularen Polymeren | |
| DE1520968C3 (de) | Verfahren zur Herstellung von aromatischen Polyamidocarbonsäuren auf Basis der Trimellithsäure | |
| DE1261672B (de) | Verfahren zur Herstellung von Polykondensationsprodukten |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |