CH424259A - Verfahren zur Herstellung von Polyamiden mit freien Carboxylgruppen - Google Patents

Verfahren zur Herstellung von Polyamiden mit freien Carboxylgruppen

Info

Publication number: CH424259A
Authority: CH; Switzerland
Prior art keywords: dianhydride; solution; carbon atoms; solvent; mol
Prior art date: 1958-09-19

Application number

CH7836059A

Other languages

German (de)

English (en)

Inventor

Edwards Walter Murray

Original Assignee

Du Pont

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.)

1958-09-19

Filing date

1959-09-18

Publication date

1966-11-15

1959-09-18 Application filed by Du Pont filed Critical Du Pont

1966-11-15 Publication of CH424259A publication Critical patent/CH424259A/de

Links

238000000034 method Methods 0.000 title claims description 29
239000004952 Polyamide Substances 0.000 title claims description 23
229920002647 polyamide Polymers 0.000 title claims description 23
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 title claims description 6
238000002360 preparation method Methods 0.000 title description 2
GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 50
238000006243 chemical reaction Methods 0.000 claims description 49
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 claims description 42
239000002904 solvent Substances 0.000 claims description 38
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 34
238000003756 stirring Methods 0.000 claims description 22
229910052757 nitrogen Inorganic materials 0.000 claims description 21
150000001412 amines Chemical class 0.000 claims description 20
125000004432 carbon atom Chemical group C* 0.000 claims description 18
239000000203 mixture Substances 0.000 claims description 17
239000000376 reactant Substances 0.000 claims description 17
239000002798 polar solvent Substances 0.000 claims description 12
-1 tetracarboxylic acid dianhydride Chemical class 0.000 claims description 11
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 7
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 6
HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
GEYAGBVEAJGCFB-UHFFFAOYSA-N 4-[2-(3,4-dicarboxyphenyl)propan-2-yl]phthalic acid Chemical compound C=1C=C(C(O)=O)C(C(O)=O)=CC=1C(C)(C)C1=CC=C(C(O)=O)C(C(O)=O)=C1 GEYAGBVEAJGCFB-UHFFFAOYSA-N 0.000 claims description 5
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 4
CBLAIDIBZHTGLV-UHFFFAOYSA-N dodecane-2,11-diamine Chemical compound CC(N)CCCCCCCCC(C)N CBLAIDIBZHTGLV-UHFFFAOYSA-N 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
238000006068 polycondensation reaction Methods 0.000 claims description 4
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 3
125000003277 amino group Chemical group 0.000 claims description 3
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 158
239000000243 solution Substances 0.000 description 83
229920005575 poly(amic acid) Polymers 0.000 description 73
229920000642 polymer Polymers 0.000 description 44
239000002253 acid Substances 0.000 description 31
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
239000011521 glass Substances 0.000 description 29
239000000047 product Substances 0.000 description 24
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
229940018564 m-phenylenediamine Drugs 0.000 description 16
WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 15
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
238000006116 polymerization reaction Methods 0.000 description 11
VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 10
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 10
238000007792 addition Methods 0.000 description 9
150000004985 diamines Chemical class 0.000 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 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
238000005266 casting Methods 0.000 description 7
239000000126 substance Substances 0.000 description 7
239000008399 tap water Substances 0.000 description 7
235000020679 tap water Nutrition 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 6
125000006159 dianhydride group Chemical group 0.000 description 5
238000001035 drying Methods 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
239000007787 solid Substances 0.000 description 5
125000001931 aliphatic group Chemical group 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
ZYEDGEXYGKWJPB-UHFFFAOYSA-N 4-[2-(4-aminophenyl)propan-2-yl]aniline Chemical compound C=1C=C(N)C=CC=1C(C)(C)C1=CC=C(N)C=C1 ZYEDGEXYGKWJPB-UHFFFAOYSA-N 0.000 description 3
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 3
238000013019 agitation Methods 0.000 description 3
125000003368 amide group Chemical group 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
239000011248 coating agent Substances 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000000178 monomer Substances 0.000 description 3
235000020075 ouzo Nutrition 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
SGEWZUYVXQESSB-UHFFFAOYSA-N 3-methylheptane-1,7-diamine Chemical compound NCCC(C)CCCCN SGEWZUYVXQESSB-UHFFFAOYSA-N 0.000 description 2
ZWIBGDOHXGXHEV-UHFFFAOYSA-N 4,4-dimethylheptane-1,7-diamine Chemical compound NCCCC(C)(C)CCCN ZWIBGDOHXGXHEV-UHFFFAOYSA-N 0.000 description 2
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
LBNFPUAJWZYIOQ-UHFFFAOYSA-N 4-n-(4-aminophenyl)-4-n-methylbenzene-1,4-diamine Chemical compound C=1C=C(N)C=CC=1N(C)C1=CC=C(N)C=C1 LBNFPUAJWZYIOQ-UHFFFAOYSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
229910000831 Steel Inorganic materials 0.000 description 2
238000000862 absorption spectrum Methods 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
150000008064 anhydrides Chemical group 0.000 description 2
239000000470 constituent Substances 0.000 description 2
239000010949 copper Substances 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 2
STZIXLPVKZUAMV-UHFFFAOYSA-N cyclopentane-1,1,2,2-tetracarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCC1(C(O)=O)C(O)=O STZIXLPVKZUAMV-UHFFFAOYSA-N 0.000 description 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000004508 fractional distillation Methods 0.000 description 2
238000010528 free radical solution polymerization reaction Methods 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
239000000499 gel Substances 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
239000000155 melt Substances 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
YKWNDAOEJQMLGH-UHFFFAOYSA-N phenyl 2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)C(=O)OC1=CC=CC=C1 YKWNDAOEJQMLGH-UHFFFAOYSA-N 0.000 description 2
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
RTHVZRHBNXZKKB-UHFFFAOYSA-N pyrazine-2,3,5,6-tetracarboxylic acid Chemical compound OC(=O)C1=NC(C(O)=O)=C(C(O)=O)N=C1C(O)=O RTHVZRHBNXZKKB-UHFFFAOYSA-N 0.000 description 2
VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
239000002002 slurry Substances 0.000 description 2
238000009987 spinning Methods 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
239000010959 steel Substances 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
XGKKWUNSNDTGDS-UHFFFAOYSA-N 2,5-dimethylheptane-1,7-diamine Chemical compound NCC(C)CCC(C)CCN XGKKWUNSNDTGDS-UHFFFAOYSA-N 0.000 description 1
YXOKJIRTNWHPFS-UHFFFAOYSA-N 2,5-dimethylhexane-1,6-diamine Chemical compound NCC(C)CCC(C)CN YXOKJIRTNWHPFS-UHFFFAOYSA-N 0.000 description 1
IUQJDHJVPLLKFL-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)acetate;dimethylazanium Chemical compound CNC.OC(=O)COC1=CC=C(Cl)C=C1Cl IUQJDHJVPLLKFL-UHFFFAOYSA-N 0.000 description 1
RPNMGUBLKCLAEK-UHFFFAOYSA-N 2-(4-chlorophenyl)sulfanyl-n,n-diethylethanamine;hydrochloride Chemical compound [Cl-].CC[NH+](CC)CCSC1=CC=C(Cl)C=C1 RPNMGUBLKCLAEK-UHFFFAOYSA-N 0.000 description 1
DZLUPKIRNOCKJB-UHFFFAOYSA-N 2-methoxy-n,n-dimethylacetamide Chemical compound COCC(=O)N(C)C DZLUPKIRNOCKJB-UHFFFAOYSA-N 0.000 description 1
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 description 1
NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical compound C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-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
SOYBEXQHNURCGE-UHFFFAOYSA-N 3-ethoxypropan-1-amine Chemical compound CCOCCCN SOYBEXQHNURCGE-UHFFFAOYSA-N 0.000 description 1
YEEIWUUBRYZFEH-UHFFFAOYSA-N 3-methoxyhexane-1,6-diamine Chemical compound NCCC(OC)CCCN YEEIWUUBRYZFEH-UHFFFAOYSA-N 0.000 description 1
AIVVXPSKEVWKMY-UHFFFAOYSA-N 4-(3,4-dicarboxyphenoxy)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=C(C(O)=O)C(C(O)=O)=C1 AIVVXPSKEVWKMY-UHFFFAOYSA-N 0.000 description 1
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 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
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 description 1
YAAFQELLFJHAHD-UHFFFAOYSA-N 4-diethylsilylaniline Chemical compound CC[SiH](CC)c1ccc(N)cc1 YAAFQELLFJHAHD-UHFFFAOYSA-N 0.000 description 1
AQVOMFPTJXMAQE-UHFFFAOYSA-N 4-propylphthalic acid Chemical compound CCCC1=CC=C(C(O)=O)C(C(O)=O)=C1 AQVOMFPTJXMAQE-UHFFFAOYSA-N 0.000 description 1
101100243399 Caenorhabditis elegans pept-2 gene Proteins 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000282320 Panthera leo Species 0.000 description 1
239000004642 Polyimide Substances 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-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
238000010521 absorption reaction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
238000007605 air drying Methods 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
XSEKDPDUVUFJBL-UHFFFAOYSA-N azane propane Chemical compound N.N.CCC XSEKDPDUVUFJBL-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229930188620 butyrolactone Natural products 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000013065 commercial product Substances 0.000 description 1
239000012084 conversion product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
WOSVXXBNNCUXMT-UHFFFAOYSA-N cyclopentane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)C(C(O)=O)C1C(O)=O WOSVXXBNNCUXMT-UHFFFAOYSA-N 0.000 description 1
YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
229940113088 dimethylacetamide Drugs 0.000 description 1
ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
AIJZIRPGCQPZSL-UHFFFAOYSA-N ethylenetetracarboxylic acid Chemical compound OC(=O)C(C(O)=O)=C(C(O)=O)C(O)=O AIJZIRPGCQPZSL-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000011888 foil Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002156 mixing Methods 0.000 description 1
LFBJWQBNKOIOMJ-UHFFFAOYSA-N n,n'-dimethylheptane-1,7-diamine Chemical compound CNCCCCCCCNC LFBJWQBNKOIOMJ-UHFFFAOYSA-N 0.000 description 1
AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
OBKARQMATMRWQZ-UHFFFAOYSA-N naphthalene-1,2,5,6-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 OBKARQMATMRWQZ-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
DOBFTMLCEYUAQC-UHFFFAOYSA-N naphthalene-2,3,6,7-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 DOBFTMLCEYUAQC-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
VQXBKCWOCJSIRT-UHFFFAOYSA-N octadecane-1,12-diamine Chemical compound CCCCCCC(N)CCCCCCCCCCCN VQXBKCWOCJSIRT-UHFFFAOYSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052698 phosphorus Chemical group 0.000 description 1
239000011574 phosphorus Chemical group 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229920001721 polyimide Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000001294 propane Substances 0.000 description 1
YKWDNEXDHDSTCU-UHFFFAOYSA-N pyrrolidine-2,3,4,5-tetracarboxylic acid Chemical compound OC(=O)C1NC(C(O)=O)C(C(O)=O)C1C(O)=O YKWDNEXDHDSTCU-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Chemical group 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000006158 tetracarboxylic acid group Chemical group 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 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
- 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

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)
Polyamides (AREA)

CH7836059A 1958-09-19 1959-09-18 Verfahren zur Herstellung von Polyamiden mit freien Carboxylgruppen CH424259A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US76196858A	1958-09-19	1958-09-19

Publications (1)

Publication Number	Publication Date
CH424259A true CH424259A (de)	1966-11-15

Family

ID=25063747

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH7836059A CH424259A (de)	1958-09-19	1959-09-18	Verfahren zur Herstellung von Polyamiden mit freien Carboxylgruppen

Country Status (5)

Country	Link
CH (1)	CH424259A (da)
DE (2)	DE1420706C3 (da)
DK (1)	DK107258C (da)
GB (1)	GB898651A (da)
NL (1)	NL120084C (da)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3349061A (en) *	1964-01-10	1967-10-24	Du Pont	Amide-ester isomers
US4269968A (en) *	1979-11-13	1981-05-26	International Business Machines Corporation	Synthesis of polyamic acid
JPS58145419A (ja) *	1982-02-23	1983-08-30	Toray Ind Inc	芳香族ポリイミドフイルムの製造方法
DE19705882A1 (de) *	1997-02-15	1998-08-20	Beck & Co Ag Dr	Mischungen aus Lösungen von Polyamidocarbonsäuren und Lösungen von polyimidbildenden Ausgangsstoffen
RU2352595C2 (ru) *	2007-04-11	2009-04-20	Евгений Львович Вулах	Способ получения раствора полиамидокислоты на основе 4,4'-диаминотрифениламина
DE102014104223A1 (de)	2014-03-26	2015-10-01	Elantas Italia S.R.L.	Neues Lösemittel für Polyamidimide und Polyimide
DE102017119280A1 (de)	2017-08-23	2019-02-28	Heraeus Noblelight Gmbh	Verfahren und Vorrichtung zur Herstellung einer Polyimidschicht auf einem Substrat

1959
- 1959-09-17 DE DE1420706A patent/DE1420706C3/de not_active Expired
- 1959-09-17 DE DE1795611*CA patent/DE1795611C3/de not_active Expired
- 1959-09-18 GB GB31811/59A patent/GB898651A/en not_active Expired
- 1959-09-18 NL NL243489A patent/NL120084C/nl active
- 1959-09-18 DK DK334859AA patent/DK107258C/da active
- 1959-09-18 CH CH7836059A patent/CH424259A/de unknown

Also Published As

Publication number	Publication date
DE1795611A1 (de)	1972-01-27
DE1795611B2 (de)	1975-03-06
NL120084C (nl)	1964-11-16
DE1795611C3 (de)	1975-11-06
DE1420706A1 (de)	1968-10-10
DE1420706B2 (de)	1971-08-19
NL243489A (da)	1964-01-27
DK107258C (da)	1967-05-08
GB898651A (en)	1962-06-14
DE1420706C3 (de)	1974-05-09

Publication	Publication Date	Title
DE2604265C3 (de)	1981-09-10	Wässrige Polyamidsäurelösung
DE2363784C2 (de)	1985-08-29	Verfahren zum Herstellen von Polyätherimiden
CH457850A (de)	1968-06-15	Verfahren zur Herstellung von Amidgruppen aufweisenden Polyimiden und Anwendung des Verfahrens
DE1770866B2 (de)	1974-11-07	Verfahren zur Herstellung von Polyimiden und deren Verwendung
DE3486367T2 (de)	1995-09-28	Verwendung fluorhaltiger Polyimide für Orientierungsschichten von Flüssigkristall-Anzeigevorrichtungen.
DE2357297C3 (de)	1978-09-21	Verfahren zur Herstellung von Polyamidcarbonsäuren
DE69702717T2 (de)	2001-03-29	Polyimide mit hohem tg, hoher oxidativer thermischer stabilität und niedriger wasseraufnahmefähigkeit
DE1202981C2 (de)	1975-06-12	Verfahren zur herstellung von aromatischen polyimidformkoerpern
DE1720835B2 (de)	1979-05-31	Verfahren zur Herstellung von homogenen wäßrigen Polymidsäurelösungen
DE2363785C2 (de)	1985-05-09	Polyätherimide
CH463779A (de)	1968-10-15	Stabilisierte Polyamidsäurelösung mit verbesserten Viskositätseigenschaften und Verfahren zur Herstellung derselben
CH424259A (de)	1966-11-15	Verfahren zur Herstellung von Polyamiden mit freien Carboxylgruppen
DE2257996A1 (de)	1973-06-14	Loesliche polyimide
DE1520620B2 (de)	1971-10-28	Verfahren zur herstellung von formkoerpern und ueberzuegen aus polyimiden
DE2005587B2 (de)	1979-07-19	Aromatische Polyimide mit Karbüiolkettenverknüpfung sowie deren Anwendung
DE1901292A1 (de)	1970-04-23	Verfahren zur Herstellung von Amidsaeureoligomermassen
DE1902875A1 (de)	1970-08-06	Verfahren zur Herstellung eines thermisch stabilen Polymers
DE2429695C2 (de)	1985-09-26	Verfahren zum Herstellen von Polyätherimiden
DE2537305A1 (de)	1976-03-04	Polythioaetherimide
DE1720837A1 (de)	1971-07-22	Verfahren zur Herstellung von Polyamidsaeureloesungen
EP0260709B1 (de)	1991-07-24	Neue lösliche und/oder schmelzbare Polyamidimid-Polyimid-Blockcopolymere
DE2230121A1 (de)	1974-01-17	Polyamidimide und verfahren zu ihrer herstellung
DE1745130C3 (de)	1974-03-21	Verfahren zur Herstellung von Polyimiden
DE1804461B2 (de)	1971-09-16	Verfahren zur herstellung von copolymeren und deren verwendung
DE1645501C (de)	1973-08-23	Verfahren zur Herstellung von ther misch stabilen Polykondensaten und deren Verwendung