ES2537821T3 - Oligómeros con unidades terminales de di-feniletinilo - Google Patents
Oligómeros con unidades terminales de di-feniletinilo Download PDFInfo
- Publication number
- ES2537821T3 ES2537821T3 ES10704619.5T ES10704619T ES2537821T3 ES 2537821 T3 ES2537821 T3 ES 2537821T3 ES 10704619 T ES10704619 T ES 10704619T ES 2537821 T3 ES2537821 T3 ES 2537821T3
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- Spain
- Prior art keywords
- sulfone
- oligomer
- formula
- imide
- nhco
- Prior art date
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- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims abstract description 104
- -1 ether sulfone Chemical class 0.000 claims abstract description 90
- 239000000203 mixture Substances 0.000 claims abstract description 77
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 55
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 52
- 229920000642 polymer Polymers 0.000 claims abstract description 46
- 150000003949 imides Chemical class 0.000 claims abstract description 37
- 239000011157 advanced composite material Substances 0.000 claims abstract description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 34
- 239000000178 monomer Substances 0.000 claims abstract description 27
- 150000001408 amides Chemical class 0.000 claims abstract description 22
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims abstract description 19
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 18
- 150000001412 amines Chemical class 0.000 claims abstract description 14
- 239000000126 substance Substances 0.000 claims abstract description 14
- 150000002148 esters Chemical class 0.000 claims abstract description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims abstract description 11
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims abstract description 10
- KVEZIRCKNOTGKY-UHFFFAOYSA-N thiazosulfone Chemical compound S1C(N)=NC=C1S(=O)(=O)C1=CC=C(N)C=C1 KVEZIRCKNOTGKY-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229950009928 thiazosulfone Drugs 0.000 claims abstract description 8
- 150000004985 diamines Chemical class 0.000 claims description 62
- 125000003118 aryl group Chemical group 0.000 claims description 52
- 238000009833 condensation Methods 0.000 claims description 23
- 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 21
- 230000005494 condensation Effects 0.000 claims description 20
- 125000001931 aliphatic group Chemical group 0.000 claims description 12
- 150000003457 sulfones Chemical group 0.000 claims description 12
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 229920001601 polyetherimide Polymers 0.000 claims description 9
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 76
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 56
- 150000003254 radicals Chemical class 0.000 description 50
- 238000006243 chemical reaction Methods 0.000 description 35
- 239000002131 composite material Substances 0.000 description 33
- 239000000463 material Substances 0.000 description 28
- 150000001875 compounds Chemical class 0.000 description 26
- 238000004132 cross linking Methods 0.000 description 25
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 24
- 241000670727 Amida Species 0.000 description 21
- 239000000543 intermediate Substances 0.000 description 21
- 239000000376 reactant Substances 0.000 description 21
- 238000003786 synthesis reaction Methods 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 19
- 239000002904 solvent Substances 0.000 description 19
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 17
- 239000002253 acid Substances 0.000 description 17
- 150000004820 halides Chemical class 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 14
- 239000002585 base Substances 0.000 description 13
- 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 13
- 239000012298 atmosphere Substances 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 230000009021 linear effect Effects 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- 150000008065 acid anhydrides Chemical class 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 244000257039 Duranta repens Species 0.000 description 8
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 8
- 229910052763 palladium Inorganic materials 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- ROFZMKDROVBLNY-UHFFFAOYSA-N 4-nitro-2-benzofuran-1,3-dione Chemical compound [O-][N+](=O)C1=CC=CC2=C1C(=O)OC2=O ROFZMKDROVBLNY-UHFFFAOYSA-N 0.000 description 7
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 238000012545 processing Methods 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- 101150003085 Pdcl gene Proteins 0.000 description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
- 240000001987 Pyrus communis Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical group CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- QPVSUHKCAMOJER-UHFFFAOYSA-N 1-phenoxy-2-(2-phenoxyphenyl)sulfonylbenzene Chemical compound C=1C=CC=C(OC=2C=CC=CC=2)C=1S(=O)(=O)C1=CC=CC=C1OC1=CC=CC=C1 QPVSUHKCAMOJER-UHFFFAOYSA-N 0.000 description 5
- 229930185605 Bisphenol Natural products 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 description 5
- 150000002009 diols Chemical class 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 239000004642 Polyimide Substances 0.000 description 4
- 229910006124 SOCl2 Inorganic materials 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 229940106691 bisphenol a Drugs 0.000 description 4
- 230000002860 competitive effect Effects 0.000 description 4
- 229920001721 polyimide Polymers 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- 235000015320 potassium carbonate Nutrition 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 3
- GPAPPPVRLPGFEQ-UHFFFAOYSA-N 4,4'-dichlorodiphenyl sulfone Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 GPAPPPVRLPGFEQ-UHFFFAOYSA-N 0.000 description 3
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 239000002262 Schiff base Substances 0.000 description 3
- 150000004753 Schiff bases Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000001588 bifunctional effect Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- 229960001553 phloroglucinol Drugs 0.000 description 3
- 239000011160 polymer matrix composite Substances 0.000 description 3
- 229920013657 polymer matrix composite Polymers 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 2
- KFIRODWJCYBBHY-UHFFFAOYSA-N 3-nitrophthalic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1C(O)=O KFIRODWJCYBBHY-UHFFFAOYSA-N 0.000 description 2
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 2
- URFNSYWAGGETFK-UHFFFAOYSA-N 4,4'-Dihydroxybibenzyl Chemical compound C1=CC(O)=CC=C1CCC1=CC=C(O)C=C1 URFNSYWAGGETFK-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- 241000207447 Estrella Species 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-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
- 229920000877 Melamine resin Polymers 0.000 description 2
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 101100417089 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) ROY1 gene Proteins 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910003074 TiCl4 Inorganic materials 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001499 aryl bromides Chemical class 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 230000001976 improved effect Effects 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 210000004742 mc(tc) Anatomy 0.000 description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
- 238000003541 multi-stage reaction Methods 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 150000002916 oxazoles Chemical class 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 108010014374 puros Proteins 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
- 238000001721 transfer moulding Methods 0.000 description 2
- DVRFSTRQFBKZKA-UHFFFAOYSA-N (2,3-dibromonaphthalene-1-carbonyl) 2,3-dibromonaphthalene-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OC(=O)C=3C4=CC=CC=C4C=C(C=3Br)Br)=C(Br)C(Br)=CC2=C1 DVRFSTRQFBKZKA-UHFFFAOYSA-N 0.000 description 1
- XHCGTVHIQUXPRM-SSIREWOPSA-N (2s)-n-[(2r,4s,7r)-7-acetamido-2-amino-4-[[(2s)-2-amino-6-[(5-amino-1h-1,2,4-triazol-3-yl)amino]hexanoyl]-[(2s)-2-[[(2r)-2-amino-6-[(5-amino-1h-1,2,4-triazol-3-yl)amino]hexanoyl]amino]-4-methylpentanoyl]carbamoyl]-1-(4-chlorophenyl)-8-naphthalen-2-yl-3,6- Chemical compound C([C@@H](N)C(=O)N[C@@H](CC(C)C)C(=O)N(C(=O)[C@@H](N)CCCCNC=1N=C(N)NN=1)C(=O)[C@@](CC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)(N(C(=O)[C@H](CO)NC(=O)[C@H](N)CC=1C=NC=CC=1)C(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CCCCNC(C)C)C(=O)[C@H](N)CC=1C=CC(Cl)=CC=1)CCCNC1=NNC(N)=N1 XHCGTVHIQUXPRM-SSIREWOPSA-N 0.000 description 1
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 1
- GMVJKSNPLYBFSO-UHFFFAOYSA-N 1,2,3-tribromobenzene Chemical compound BrC1=CC=CC(Br)=C1Br GMVJKSNPLYBFSO-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-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
- QBNABJXQGRVIRA-UHFFFAOYSA-N 1-bromo-4-(4-bromophenyl)sulfonylbenzene Chemical compound C1=CC(Br)=CC=C1S(=O)(=O)C1=CC=C(Br)C=C1 QBNABJXQGRVIRA-UHFFFAOYSA-N 0.000 description 1
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical class C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- GLEDYULDQVJLBE-UHFFFAOYSA-N 1h-imidazole;1,3-thiazole Chemical compound C1=CNC=N1.C1=CSC=N1 GLEDYULDQVJLBE-UHFFFAOYSA-N 0.000 description 1
- MQCPOLNSJCWPGT-UHFFFAOYSA-N 2,2'-Bisphenol F Chemical compound OC1=CC=CC=C1CC1=CC=CC=C1O MQCPOLNSJCWPGT-UHFFFAOYSA-N 0.000 description 1
- FXGQUGCFZKMIJW-UHFFFAOYSA-N 2,4,5,6-tetrafluorobenzene-1,3-diamine Chemical compound NC1=C(F)C(N)=C(F)C(F)=C1F FXGQUGCFZKMIJW-UHFFFAOYSA-N 0.000 description 1
- VXYNSDMTSYLLLX-UHFFFAOYSA-N 2-chloro-4-[1-(3-chloro-4-hydroxyphenyl)ethyl]phenol Chemical compound C=1C=C(O)C(Cl)=CC=1C(C)C1=CC=C(O)C(Cl)=C1 VXYNSDMTSYLLLX-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- CKNCVRMXCLUOJI-UHFFFAOYSA-N 3,3'-dibromobisphenol A Chemical compound C=1C=C(O)C(Br)=CC=1C(C)(C)C1=CC=C(O)C(Br)=C1 CKNCVRMXCLUOJI-UHFFFAOYSA-N 0.000 description 1
- ZBMISJGHVWNWTE-UHFFFAOYSA-N 3-(4-aminophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(N)=C1 ZBMISJGHVWNWTE-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
- ACEMPBSQAVZNEJ-UHFFFAOYSA-N 4-[(4-hydroxy-3-methoxy-2,6-dimethylphenyl)methyl]-2-methoxy-3,5-dimethylphenol Chemical compound C1=C(O)C(OC)=C(C)C(CC=2C(=C(OC)C(O)=CC=2C)C)=C1C ACEMPBSQAVZNEJ-UHFFFAOYSA-N 0.000 description 1
- RSSGMIIGVQRGDS-UHFFFAOYSA-N 4-[(4-hydroxyphenyl)-phenylmethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C1=CC=CC=C1 RSSGMIIGVQRGDS-UHFFFAOYSA-N 0.000 description 1
- HWBVOOWDSUQMHR-UHFFFAOYSA-N 4-[1-(3,4-dicarboxyphenyl)-1,2,2,3,3,3-hexafluoropropyl]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(F)(C(F)(F)C(F)(F)F)C1=CC=C(C(O)=O)C(C(O)=O)=C1 HWBVOOWDSUQMHR-UHFFFAOYSA-N 0.000 description 1
- WZDLEYNMGWZAEJ-UHFFFAOYSA-N 4-[1-(4-hydroxy-3,5-dimethylphenyl)ethyl]-2,6-dimethylphenol Chemical compound C=1C(C)=C(O)C(C)=CC=1C(C)C1=CC(C)=C(O)C(C)=C1 WZDLEYNMGWZAEJ-UHFFFAOYSA-N 0.000 description 1
- BKTRENAPTCBBFA-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-phenylphenyl)propan-2-yl]-2-phenylphenol Chemical compound C=1C=C(O)C(C=2C=CC=CC=2)=CC=1C(C)(C)C(C=1)=CC=C(O)C=1C1=CC=CC=C1 BKTRENAPTCBBFA-UHFFFAOYSA-N 0.000 description 1
- LENWAARDNHJYQO-UHFFFAOYSA-N 4-[2-(4-hydroxynaphthalen-1-yl)propan-2-yl]naphthalen-1-ol;4-[2-(4-hydroxyphenyl)pentan-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)(CCC)C1=CC=C(O)C=C1.C1=CC=C2C(C(C)(C=3C4=CC=CC=C4C(O)=CC=3)C)=CC=C(O)C2=C1 LENWAARDNHJYQO-UHFFFAOYSA-N 0.000 description 1
- QCRWJMVAYBEVGO-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)-1,2-diphenylethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC=CC=1)C(C=1C=CC(O)=CC=1)C1=CC=CC=C1 QCRWJMVAYBEVGO-UHFFFAOYSA-N 0.000 description 1
- ZQTPHEAGPRFALE-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)hexan-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)(CCCC)C1=CC=C(O)C=C1 ZQTPHEAGPRFALE-UHFFFAOYSA-N 0.000 description 1
- YZYGDZRBLOLVDY-UHFFFAOYSA-N 4-[cyclohexyl-(4-hydroxyphenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C1CCCCC1 YZYGDZRBLOLVDY-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- 229940073735 4-hydroxy acetophenone Drugs 0.000 description 1
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- 239000004970 Chain extender Substances 0.000 description 1
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- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
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- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000997826 Melanocetus johnsonii Species 0.000 description 1
- 101100005554 Mus musculus Ccl20 gene Proteins 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 description 1
- 101100114416 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) con-10 gene Proteins 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- KYPYTERUKNKOLP-UHFFFAOYSA-N Tetrachlorobisphenol A Chemical compound C=1C(Cl)=C(O)C(Cl)=CC=1C(C)(C)C1=CC(Cl)=C(O)C(Cl)=C1 KYPYTERUKNKOLP-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 150000001492 aromatic hydrocarbon derivatives Chemical class 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000005362 aryl sulfone group Chemical group 0.000 description 1
- 238000006254 arylation reaction Methods 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 108700022499 azaline Proteins 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical compound C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- LLCSWKVOHICRDD-UHFFFAOYSA-N buta-1,3-diyne Chemical group C#CC#C LLCSWKVOHICRDD-UHFFFAOYSA-N 0.000 description 1
- NQLJPVLOQMPBPE-UHFFFAOYSA-N buta-1,3-diynylbenzene Chemical group C#CC#CC1=CC=CC=C1 NQLJPVLOQMPBPE-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical class CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 150000003940 butylamines Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000009850 completed effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007596 consolidation process Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 125000004427 diamine group Chemical group 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
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- 238000004821 distillation Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000003733 fiber-reinforced composite Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
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- 238000005304 joining Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical compound N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 description 1
- 150000005338 nitrobenzoic acids Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 125000002444 phloroglucinyl group Chemical group [H]OC1=C([H])C(O[H])=C(*)C(O[H])=C1[H] 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 101150002764 purA gene Proteins 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006009 resin backbone Polymers 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004634 thermosetting polymer Substances 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- NRTLTGGGUQIRRT-UHFFFAOYSA-N triethylazanium;bromide Chemical compound [Br-].CC[NH+](CC)CC NRTLTGGGUQIRRT-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
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
- C08G73/101—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/20—Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive groups
- C08G63/21—Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive groups in the presence of unsaturated monocarboxylic acids or unsaturated monohydric alcohols or reactive derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/367,125 US8063168B2 (en) | 2009-02-06 | 2009-02-06 | Oligomers with di-phenylethynyl endcaps |
| US367125 | 2009-02-06 | ||
| PCT/US2010/021972 WO2010141106A1 (en) | 2009-02-06 | 2010-01-25 | Oligomers with di-phenylethynyl endcaps |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2537821T3 true ES2537821T3 (es) | 2015-06-12 |
Family
ID=42124601
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10704619.5T Active ES2537821T3 (es) | 2009-02-06 | 2010-01-25 | Oligómeros con unidades terminales de di-feniletinilo |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US8063168B2 (enExample) |
| EP (1) | EP2438106B1 (enExample) |
| JP (1) | JP2012530789A (enExample) |
| CN (1) | CN102307933B (enExample) |
| CA (1) | CA2751594C (enExample) |
| ES (1) | ES2537821T3 (enExample) |
| WO (1) | WO2010141106A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9505864B2 (en) | 2014-08-29 | 2016-11-29 | The Boeing Company | Nanomodified backbones for polyimides with difunctional and mixed-functionality endcaps |
| US9315633B2 (en) | 2014-08-29 | 2016-04-19 | The Boeing Company | Nanomodified backbones for polyimides with difunctional and mixed-functionality endcaps |
| CN106842819A (zh) * | 2016-12-28 | 2017-06-13 | 杭州福斯特光伏材料股份有限公司 | 一种含炔基单体封端且显影液选择灵活的正型感光性聚酰亚胺树脂组合物 |
Family Cites Families (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3988374A (en) | 1970-06-29 | 1976-10-26 | Union Carbide Corporation | Polyamide-imides |
| US3658938A (en) | 1970-12-30 | 1972-04-25 | Union Carbide Corp | Polyamide-imide/polysulfone composites |
| US3839287A (en) | 1971-09-21 | 1974-10-01 | Union Carbide Corp | Polyarylimides |
| US4058505A (en) | 1973-05-25 | 1977-11-15 | University Of Notre Dame Du Lac | Chain-extending amine end-capped polyimides |
| US3847869A (en) | 1973-09-28 | 1974-11-12 | Gen Electric | Method for preparing polyetherimides |
| US3933862A (en) | 1974-08-23 | 1976-01-20 | General Electric Company | Aromatic dithio dianhydrides |
| US4197397A (en) | 1975-03-14 | 1980-04-08 | University Of Notre Dame Du Lac | Chain-extending anhydride end-capped polyimides |
| US4107147A (en) | 1977-09-02 | 1978-08-15 | General Electric Company | Polysulfoneimides |
| US4215418A (en) | 1978-06-30 | 1980-07-29 | Trw Inc. | Integrated digital multiplier circuit using current mode logic |
| US4251420A (en) | 1979-04-23 | 1981-02-17 | Gulf Oil Corporation | End-capped polyimide oligomers |
| US4251417A (en) | 1979-04-25 | 1981-02-17 | Gulf Oil Corporation | Novel acetylene end-capped polyimide oligomers |
| US4251418A (en) | 1979-04-27 | 1981-02-17 | Gulf Oil Corporation | Polyimide oligomers |
| US4297474A (en) | 1980-02-29 | 1981-10-27 | General Electric Company | Polyetherimides prepared by self-condensation of hydroxyaryl phthalimide salts |
| US4331794A (en) | 1980-10-22 | 1982-05-25 | Plastics Engineering Company | Polymerization products of diimides having terminal diacetylene groups |
| US5969079A (en) | 1985-09-05 | 1999-10-19 | The Boeing Company | Oligomers with multiple chemically functional end caps |
| US5645925A (en) | 1988-03-14 | 1997-07-08 | Boeing Company | Advanced composite blends |
| US4576857A (en) | 1983-03-14 | 1986-03-18 | E. I. Du Pont De Nemours And Company | Melt-fusible polyimides |
| US4739030A (en) | 1983-06-17 | 1988-04-19 | The Boeing Company | Difunctional end-cap monomers |
| US4851501A (en) | 1983-06-17 | 1989-07-25 | The Boeing Company | Polyethersulfone prepregs, composites, and blends |
| US5071941A (en) | 1983-06-17 | 1991-12-10 | The Boeing Company | Multidimensional ether sulfone oligomers |
| DE3332031A1 (de) | 1983-09-06 | 1985-03-21 | Bayer Ag, 5090 Leverkusen | Verwendung von polyamidimiden als thermoplaste |
| US5654396A (en) | 1983-09-27 | 1997-08-05 | The Boeing Company | Polyimide oligomers |
| US4504632A (en) | 1983-12-30 | 1985-03-12 | General Electric Company | Amide ether imide block copolymers |
| JPS60229947A (ja) | 1984-04-28 | 1985-11-15 | Youbea Le-Ron Kogyo Kk | ポリアミドイミド系樹脂組成物 |
| US4574144A (en) | 1984-12-17 | 1986-03-04 | General Electric Company | Sulfonated polyimides and polyamic acids and method for their preparation |
| US4577034A (en) | 1985-02-14 | 1986-03-18 | The Dow Chemical Company | Autoxidation of bis(ortho dialkyl-phenoxy)benzophenones |
| US5610317A (en) | 1985-09-05 | 1997-03-11 | The Boeing Company | Multiple chemically functional end cap monomers |
| US5594089A (en) | 1985-09-05 | 1997-01-14 | The Boeing Company | Heterocycle or heterocycle sulfone oligomers with multiple chemically functional end caps |
| US4935523A (en) | 1985-09-30 | 1990-06-19 | The Boeing Company | Crosslinking imidophenylamines |
| US5817744A (en) | 1988-03-14 | 1998-10-06 | The Boeing Company | Phenylethynyl capped imides |
| JPH03124714A (ja) * | 1989-09-19 | 1991-05-28 | Boeing Co:The | 共反応性オリゴマー混和物及びその製法 |
| US5412065A (en) | 1993-04-09 | 1995-05-02 | Ciba-Geigy Corporation | Polyimide oligomers |
| US5412066A (en) | 1994-03-03 | 1995-05-02 | Ther United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Phenylethynyl terminated imide oligomers |
| US5567800A (en) | 1994-10-28 | 1996-10-22 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Imide oligomers endcapped with phenylethynyl phthalic anhydrides and polymers therefrom |
| US5606014A (en) | 1995-08-04 | 1997-02-25 | The United States Of America As Represented By The United States National Aeronautics And Space Administration | Imide oligomers and co-oligomers containing pendent phenylethynyl groups and polymers therefrom |
| AUPO549397A0 (en) | 1997-03-07 | 1997-03-27 | Commonwealth Scientific And Industrial Research Organisation | Reduced temperature curing of acetylenic polymers |
| US5998550A (en) | 1998-07-30 | 1999-12-07 | The United States Of America As Represented By The Secretary Of The Air Force | Processing of thermoset rigid-rod molecular composites |
| US6136949A (en) | 1998-09-03 | 2000-10-24 | The Dow Chemical Company | Resins containing phenylethynl-terminated compounds |
| US6350817B1 (en) | 1999-04-13 | 2002-02-26 | The United States Of America As Represented By The United States National Aeronautics And Space Administration | Phenylethynyl containing reactive additives |
| US6124035A (en) | 1999-04-13 | 2000-09-26 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | High temperature transfer molding resins |
| US6395907B1 (en) | 1999-11-18 | 2002-05-28 | Virginia Commonwealth University | Preparation of polyaromatic-ethynyl thermal setting agents |
| WO2001058909A1 (en) | 2000-02-10 | 2001-08-16 | The Government Of The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration (Nasa) | Phenylethynyl-containing imide silanes |
| JP4586230B2 (ja) * | 2000-03-28 | 2010-11-24 | 住友ベークライト株式会社 | 絶縁膜用コーティングワニス及び絶縁膜 |
| US7635741B2 (en) | 2002-02-15 | 2009-12-22 | Dow Global Technologies Inc. | Multifunctional monomers and their use in making cross-linked polymers and porous films |
| US6911519B2 (en) | 2002-03-26 | 2005-06-28 | University Of Connecticut | Low viscosity melt processable high temperature polyimides |
| US20080300374A1 (en) | 2007-05-31 | 2008-12-04 | The Boeing Company | Dinadic phenyl amine reactive endcaps |
| JP2009013116A (ja) | 2007-07-05 | 2009-01-22 | Daicel Chem Ind Ltd | エチニルフェニルビアダマンタン誘導体 |
-
2009
- 2009-02-06 US US12/367,125 patent/US8063168B2/en not_active Expired - Fee Related
- 2009-10-20 US US12/582,394 patent/US8106142B2/en not_active Expired - Fee Related
-
2010
- 2010-01-25 JP JP2012513940A patent/JP2012530789A/ja active Pending
- 2010-01-25 EP EP10704619.5A patent/EP2438106B1/en not_active Not-in-force
- 2010-01-25 ES ES10704619.5T patent/ES2537821T3/es active Active
- 2010-01-25 CA CA2751594A patent/CA2751594C/en active Active
- 2010-01-25 CN CN201080006901.1A patent/CN102307933B/zh not_active Expired - Fee Related
- 2010-01-25 WO PCT/US2010/021972 patent/WO2010141106A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| CN102307933B (zh) | 2014-05-07 |
| US20100204485A1 (en) | 2010-08-12 |
| WO2010141106A1 (en) | 2010-12-09 |
| EP2438106A1 (en) | 2012-04-11 |
| US8106142B2 (en) | 2012-01-31 |
| CA2751594C (en) | 2013-09-17 |
| US20100204412A1 (en) | 2010-08-12 |
| EP2438106B1 (en) | 2015-03-11 |
| CN102307933A (zh) | 2012-01-04 |
| JP2012530789A (ja) | 2012-12-06 |
| CA2751594A1 (en) | 2010-12-09 |
| US8063168B2 (en) | 2011-11-22 |
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