ES2278067T3 - Procedimientos para la fabricacion de polieterimidas. - Google Patents
Procedimientos para la fabricacion de polieterimidas. Download PDFInfo
- Publication number
- ES2278067T3 ES2278067T3 ES02784398T ES02784398T ES2278067T3 ES 2278067 T3 ES2278067 T3 ES 2278067T3 ES 02784398 T ES02784398 T ES 02784398T ES 02784398 T ES02784398 T ES 02784398T ES 2278067 T3 ES2278067 T3 ES 2278067T3
- Authority
- ES
- Spain
- Prior art keywords
- substituted
- group
- carbon atoms
- anhydride
- divalent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- 229920001601 polyetherimide Polymers 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title description 5
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 19
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 14
- 150000008064 anhydrides Chemical class 0.000 claims description 42
- 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 30
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical class CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 15
- 150000004985 diamines Chemical class 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- -1 4-substituted phthalic anhydride Chemical class 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 239000011737 fluorine Chemical group 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 7
- BTTRMCQEPDPCPA-UHFFFAOYSA-N 4-chlorophthalic anhydride Chemical group ClC1=CC=C2C(=O)OC(=O)C2=C1 BTTRMCQEPDPCPA-UHFFFAOYSA-N 0.000 claims description 6
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical group C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Chemical group 0.000 claims description 5
- 229910052801 chlorine Chemical group 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- HVZWVEKIQMJYIK-UHFFFAOYSA-N nitryl chloride Chemical compound [O-][N+](Cl)=O HVZWVEKIQMJYIK-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- KFDLHDGFDLHFRW-UHFFFAOYSA-N [O-][N+](Br)=O Chemical group [O-][N+](Br)=O KFDLHDGFDLHFRW-UHFFFAOYSA-N 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 60
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 12
- 238000006073 displacement reaction Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 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 9
- 238000000605 extraction Methods 0.000 description 9
- 239000006227 byproduct Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 238000005899 aromatization reaction Methods 0.000 description 7
- 238000006396 nitration reaction Methods 0.000 description 7
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 6
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 238000007654 immersion Methods 0.000 description 6
- 229930185605 Bisphenol Natural products 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 229910000619 316 stainless steel Inorganic materials 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000004566 IR spectroscopy Methods 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 3
- 239000004697 Polyetherimide Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- JBCHWGTZAAZJKG-UHFFFAOYSA-N 2-methyl-5-nitroisoindole-1,3-dione Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(C)C(=O)C2=C1 JBCHWGTZAAZJKG-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
- DCFSQEWFDPNDPQ-UHFFFAOYSA-N 5-chloro-2-methylisoindole-1,3-dione Chemical compound C1=C(Cl)C=C2C(=O)N(C)C(=O)C2=C1 DCFSQEWFDPNDPQ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-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
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 1
- ZXLYYQUMYFHCLQ-UHFFFAOYSA-N 2-methylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(C)C(=O)C2=C1 ZXLYYQUMYFHCLQ-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
- BYJQAPYDPPKJGH-UHFFFAOYSA-N 3-(2-carboxyethyl)-1h-indole-2-carboxylic acid Chemical compound C1=CC=C2C(CCC(=O)O)=C(C(O)=O)NC2=C1 BYJQAPYDPPKJGH-UHFFFAOYSA-N 0.000 description 1
- QPIOXOJERGNNMX-UHFFFAOYSA-N 3-(3-aminopropylsulfanyl)propan-1-amine Chemical compound NCCCSCCCN QPIOXOJERGNNMX-UHFFFAOYSA-N 0.000 description 1
- POTQBGGWSWSMCX-UHFFFAOYSA-N 3-[2-(3-aminopropoxy)ethoxy]propan-1-amine Chemical compound NCCCOCCOCCCN POTQBGGWSWSMCX-UHFFFAOYSA-N 0.000 description 1
- HPOCNCRMNUFSOQ-UHFFFAOYSA-N 3-[4-[2-[4-(3-hydroxyphenyl)phenyl]propan-2-yl]phenyl]phenol Chemical compound C=1C=C(C=2C=C(O)C=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1C1=CC=CC(O)=C1 HPOCNCRMNUFSOQ-UHFFFAOYSA-N 0.000 description 1
- GPXCORHXFPYJEH-UHFFFAOYSA-N 3-[[3-aminopropyl(dimethyl)silyl]oxy-dimethylsilyl]propan-1-amine Chemical compound NCCC[Si](C)(C)O[Si](C)(C)CCCN GPXCORHXFPYJEH-UHFFFAOYSA-N 0.000 description 1
- SGEWZUYVXQESSB-UHFFFAOYSA-N 3-methylheptane-1,7-diamine Chemical compound NCCC(C)CCCCN SGEWZUYVXQESSB-UHFFFAOYSA-N 0.000 description 1
- ICNFHJVPAJKPHW-UHFFFAOYSA-N 4,4'-Thiodianiline Chemical compound C1=CC(N)=CC=C1SC1=CC=C(N)C=C1 ICNFHJVPAJKPHW-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- ZWIBGDOHXGXHEV-UHFFFAOYSA-N 4,4-dimethylheptane-1,7-diamine Chemical compound NCCCC(C)(C)CCCN ZWIBGDOHXGXHEV-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- VIOMIGLBMQVNLY-UHFFFAOYSA-N 4-[(4-amino-2-chloro-3,5-diethylphenyl)methyl]-3-chloro-2,6-diethylaniline Chemical compound CCC1=C(N)C(CC)=CC(CC=2C(=C(CC)C(N)=C(CC)C=2)Cl)=C1Cl VIOMIGLBMQVNLY-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
- 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 1
- IPDXWXPSCKSIII-UHFFFAOYSA-N 4-propan-2-ylbenzene-1,3-diamine Chemical compound CC(C)C1=CC=C(N)C=C1N IPDXWXPSCKSIII-UHFFFAOYSA-N 0.000 description 1
- YFHLASGJCIMMIL-UHFFFAOYSA-N 5-chloro-2-methyl-3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C(Cl)C=CC2C(=O)N(C)C(=O)C21 YFHLASGJCIMMIL-UHFFFAOYSA-N 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 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
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- JRCQGEYYUGZNIL-UHFFFAOYSA-N [4-(3-hydroxyphenyl)phenyl]-[4-(4-hydroxyphenyl)phenyl]methanone Chemical compound C1=CC(O)=CC=C1C1=CC=C(C(=O)C=2C=CC(=CC=2)C=2C=C(O)C=CC=2)C=C1 JRCQGEYYUGZNIL-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
- 238000013019 agitation Methods 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- LYWKAJZTPLXHEM-UHFFFAOYSA-M bis(diethylamino)methylidene-diethylazanium;chloride Chemical compound [Cl-].CCN(CC)C(N(CC)CC)=[N+](CC)CC LYWKAJZTPLXHEM-UHFFFAOYSA-M 0.000 description 1
- RULTXLYCWSZPPJ-UHFFFAOYSA-N bis[4-(3-hydroxyphenyl)phenyl]methanone Chemical compound OC1=CC=CC(C=2C=CC(=CC=2)C(=O)C=2C=CC(=CC=2)C=2C=C(O)C=CC=2)=C1 RULTXLYCWSZPPJ-UHFFFAOYSA-N 0.000 description 1
- RXYHWBDYFPUZIB-UHFFFAOYSA-N bis[4-(4-hydroxyphenyl)phenyl]methanone Chemical compound C1=CC(O)=CC=C1C1=CC=C(C(=O)C=2C=CC(=CC=2)C=2C=CC(O)=CC=2)C=C1 RXYHWBDYFPUZIB-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- 125000006159 dianhydride group Chemical group 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 1
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- OLAPPGSPBNVTRF-UHFFFAOYSA-N naphthalene-1,4,5,8-tetracarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O OLAPPGSPBNVTRF-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
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- CJYCVQJRVSAFKB-UHFFFAOYSA-N octadecane-1,18-diamine Chemical compound NCCCCCCCCCCCCCCCCCCN CJYCVQJRVSAFKB-UHFFFAOYSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003462 sulfoxides Chemical group 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 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
- C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
- C08G73/1053—Polyimides containing oxygen in the form of ether bonds in the main chain with oxygen only in the tetracarboxylic moiety
-
- 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)
- Indole Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US683257 | 2001-12-05 | ||
| US09/683,257 US6498224B1 (en) | 2001-12-05 | 2001-12-05 | Methods for the preparation poly(etherimide)s |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2278067T3 true ES2278067T3 (es) | 2007-08-01 |
Family
ID=24743231
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES02784398T Expired - Lifetime ES2278067T3 (es) | 2001-12-05 | 2002-11-04 | Procedimientos para la fabricacion de polieterimidas. |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US6498224B1 (enExample) |
| EP (1) | EP1458791B1 (enExample) |
| JP (1) | JP2005511836A (enExample) |
| CN (1) | CN100469817C (enExample) |
| AU (1) | AU2002348176A1 (enExample) |
| DE (1) | DE60216507T2 (enExample) |
| ES (1) | ES2278067T3 (enExample) |
| WO (1) | WO2003050165A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6710187B2 (en) * | 2002-05-14 | 2004-03-23 | General Electric Company | Process to isolate dianhydrides |
| US6881815B2 (en) * | 2002-09-25 | 2005-04-19 | General Electric Company | Method for the preparation poly(etherimide)s |
| US6849706B1 (en) * | 2003-08-25 | 2005-02-01 | General Electric Company | Copolyetherimides |
| US6919418B2 (en) * | 2003-08-25 | 2005-07-19 | Farid Fouad Khouri | Approach to reduce cyclics formation in 3-CIPA based polyetherimide polymers |
| EP1776094A2 (en) * | 2004-08-06 | 2007-04-25 | Grain Processing Corporation | Tablet coating composition |
| JP2006065224A (ja) * | 2004-08-30 | 2006-03-09 | Jsr Corp | 光学フィルム、偏光板および液晶ディスプレイ |
| EP1785753A4 (en) * | 2004-08-30 | 2013-03-27 | Jsr Corp | OPTICAL FILM, POLARIZING PLATE AND LIQUID CRYSTAL DISPLAY |
| US8080671B2 (en) | 2008-05-23 | 2011-12-20 | Sabic Innovative Plastics Ip B.V. | Production of low color polyetherimides |
| ES2561152T3 (es) * | 2012-03-30 | 2016-02-24 | Sabic Global Technologies B.V. | Polieterimidas, procedimientos de fabricación y artículos moldeados a partir de las mismas |
| US10377860B2 (en) | 2013-09-13 | 2019-08-13 | Sabic Global Technologies B.V. | Polyetherimides, methods of manufacture, and articles formed therefrom |
| US9382382B2 (en) | 2013-09-13 | 2016-07-05 | Sabic Global Technologies B.V. | Polyetherimides, methods of manufacture, and articles formed therefrom |
| CN104529966A (zh) * | 2015-01-11 | 2015-04-22 | 景炜杰 | 一种双酚a二醚二酐的制备方法 |
| US10526449B2 (en) * | 2015-02-27 | 2020-01-07 | Sabic Global Technologies B.V. | Process to make low color polyetherimide by halo-displacement and low color polyetherimide |
| EP3448841A1 (en) * | 2016-04-27 | 2019-03-06 | SABIC Global Technologies B.V. | Method for isolation of a dianhydride and dianhydrides prepared by the method |
| CN110050014B (zh) * | 2016-12-31 | 2022-03-15 | 高新特殊工程塑料全球技术有限公司 | 制备聚醚酰亚胺的方法和由其生产的聚醚酰亚胺 |
| EP3790855B1 (en) | 2018-05-07 | 2024-06-19 | SHPP Global Technologies B.V. | Method for isolation of an aromatic dianhydride and aromatic dianhydrides prepared by the method |
| CN112074508B (zh) | 2018-05-14 | 2024-05-24 | 高新特殊工程塑料全球技术有限公司 | 用于分离二酐的方法及由该方法制备的二酐 |
| EP3802506B1 (en) | 2018-06-04 | 2022-06-08 | SHPP Global Technologies B.V. | Method for producing an aromatic dianhydride |
| CN112262131A (zh) | 2018-06-18 | 2021-01-22 | 沙特高性能聚合物和塑料全球技术公司 | 分离芳族二酐的方法和用该方法制备的芳族二酐 |
| CA3245629A1 (en) * | 2022-03-17 | 2023-09-21 | Dow Silicones Corporation | BROMINE POLYMER FIRE REFRESHING, COMPOSITION AND CABLE INCLUDING IT |
| CN115780487B (zh) * | 2023-01-05 | 2023-05-05 | 河北东丽新材料有限公司 | 一种萃取剂及利用其处理4,4`-联苯醚二酐生产固废的方法 |
Family Cites Families (77)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1891843A (en) | 1932-12-20 | Signobs to imperial chemical industries limited | ||
| US2391226A (en) | 1943-02-25 | 1945-12-18 | Wingfoot Corp | Method of preparing a cyclic dicarboxylic acid anhydride |
| US2764597A (en) | 1954-12-02 | 1956-09-25 | Du Pont | Isomerization of delta-cyclohexene 1, 2-dicarboxylic acid anhydride and esters |
| US3240792A (en) | 1961-03-22 | 1966-03-15 | Imp Smelting Corp Ltd | Tetrafluorophthalic acids and derivatives |
| US3346597A (en) | 1964-03-30 | 1967-10-10 | Shell Oil Co | Halogen-containing cyclic anhydrides |
| US3480667A (en) | 1965-04-28 | 1969-11-25 | Texaco Inc | Method of producing fluorinated compounds |
| DE1493217C3 (de) | 1965-08-16 | 1978-11-09 | Studiengesellschaft Kohle Mbh, 4330 Muelheim | Verfahren zur Herstellung von Pyromellithsäure bzw. deren Mono- und Dianhydrid |
| US3875116A (en) * | 1970-12-29 | 1975-04-01 | Gen Electric | Polyetherimides |
| US3972902A (en) | 1971-01-20 | 1976-08-03 | General Electric Company | 4,4'-Isopropylidene-bis(3- and 4-phenyleneoxyphthalic anhydride) |
| US3819658A (en) | 1971-03-10 | 1974-06-25 | Koppers Co Inc | Isomerization of tetrahydrophthalic anhydride |
| US3803085A (en) * | 1972-12-29 | 1974-04-09 | Gen Electric | Method for making polyetherimides |
| US3879428A (en) * | 1973-03-30 | 1975-04-22 | Gen Electric | Method for making aromatic bis(ether anhydride)s |
| US3983093A (en) * | 1975-05-19 | 1976-09-28 | General Electric Company | Novel polyetherimides |
| US4045408A (en) | 1976-03-19 | 1977-08-30 | The United States Of America As Represented By The Secretary Of The Navy | Fluoro-anhydride curing agents and precursors thereof for fluorinated epoxy resins |
| US4217281A (en) | 1976-10-04 | 1980-08-12 | General Electric Company | Imide carbonyl compounds and method for making |
| JPS5822460B2 (ja) | 1977-04-06 | 1983-05-09 | 三井東圧化学株式会社 | ４−メチルフタル酸の核塩素化物及びそれらの製造法 |
| US4257953A (en) | 1979-05-09 | 1981-03-24 | General Electric Company | Method for making bisphenoxide salts and bisimides derived therefrom |
| US4273712A (en) * | 1979-05-09 | 1981-06-16 | General Electric Company | Method for making aromatic ether imides |
| US4374267A (en) | 1980-12-29 | 1983-02-15 | Occidental Chemical Corporation | Fluorophthalamic acids and method of preparation |
| US4329291A (en) | 1981-04-03 | 1982-05-11 | General Electric Company | Method for making aromatic bis(ether anhydride)s |
| US4329292A (en) | 1981-04-16 | 1982-05-11 | General Electric Company | Continuous method for making aromatic bis(ether phthalic acid) or aromatic bis(ether anhydride) |
| US4329496A (en) | 1981-04-03 | 1982-05-11 | General Electric Company | Method for making aromatic bis(ether phthalic acid) or aromatic bis(ether anhydride) |
| US4318857A (en) | 1981-04-03 | 1982-03-09 | General Electric Company | Method for making aromatic bis (ether anhydrides) |
| US4340545A (en) | 1981-04-13 | 1982-07-20 | General Electric Company | Method for making aromatic bis(ether anhydrides) |
| US4455410A (en) | 1982-03-18 | 1984-06-19 | General Electric Company | Polyetherimide-polysulfide blends |
| US4417044A (en) | 1982-05-25 | 1983-11-22 | General Electric Company | Process for making polyetherimides |
| DE3303378A1 (de) | 1983-02-02 | 1984-08-02 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von fluorphthalsaeureanhydriden |
| US4520204A (en) * | 1983-04-25 | 1985-05-28 | General Electric Company | Method for preparation of aromatic ether imides and for catalyst recovery therein |
| US4517372A (en) | 1983-05-12 | 1985-05-14 | Occidental Chemical Corporation | Process for the preparation of 4-fluorophthalic anhydride |
| DE3320089A1 (de) | 1983-06-03 | 1984-12-06 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von fluorphtsaeureimiden |
| US4675376A (en) * | 1983-11-18 | 1987-06-23 | General Electric Company | Process for the preparation of n-alkylphthalimide and copolymer derived therefrom |
| US4599429A (en) | 1983-12-08 | 1986-07-08 | General Electric Company | Destruction of DNPI in an all nitric acid nitration process |
| US5155234A (en) | 1983-12-08 | 1992-10-13 | General Electric Company | Nitration of phthalic acid and phthalic anhydride using nitric acid |
| US4902809A (en) | 1983-12-08 | 1990-02-20 | General Electric Company | Method for making N-substituted nitrophthalimides |
| US4921970A (en) | 1984-01-03 | 1990-05-01 | General Electric Company | Nitration reactions with acid anhydride promoters |
| US4559405A (en) | 1984-04-16 | 1985-12-17 | Stauffer Chemical Company | Process for preparing substituted phthalic anhydrides |
| US4560773A (en) | 1984-04-16 | 1985-12-24 | Stauffer Chemical Company | Process for preparing substituted phthalic anhydrides |
| US4560772A (en) | 1984-10-22 | 1985-12-24 | Stauffer Chemical Company | Preparation of substituted phthalic anhydrides |
| US4584388A (en) | 1985-01-14 | 1986-04-22 | General Electric Company | Method and composition for preparing aromatic polycarboxylic acids and their anhydrides from polycarboximides |
| US5021588A (en) | 1985-01-18 | 1991-06-04 | E.I. Du Pont De Nemours And Company | Vapor phase catalytic oxidation of butane to maleic anhydride |
| US4571425A (en) | 1985-02-14 | 1986-02-18 | General Electric Company | Method for making aromatic bis(ether anhydride) |
| US4612361A (en) * | 1985-09-23 | 1986-09-16 | General Electric Company | Poly(etherimides) and compositions containing the same |
| US5068353A (en) * | 1986-12-31 | 1991-11-26 | General Electric Company | Synthesis of aromatic bis(ether phthalimide) compounds |
| US4965337A (en) * | 1987-12-31 | 1990-10-23 | General Electric Company | Very high heat thermoplastic polyetherimides containing aromatic structure |
| US4978760A (en) | 1988-02-24 | 1990-12-18 | Occidental Chemical Corporation | Preparation of halogen substituted phthalic anhydride |
| US5003088A (en) | 1988-02-24 | 1991-03-26 | Occidental Chemical Corporation | Method for the preparation of halophthalic anhydrides |
| US5206391A (en) | 1989-09-11 | 1993-04-27 | Occidental Chemical Corporation | Process for the preparation of halophthalic anhydrides |
| US5049682A (en) | 1989-09-11 | 1991-09-17 | Occidental Chemical Corporation | Process for the preparation of halophthalic anhydrides |
| US5233054A (en) | 1989-09-11 | 1993-08-03 | Occidental Chemical Corporation | Process for the preparation of halophthalic anhydrides |
| US4962206A (en) | 1989-11-20 | 1990-10-09 | Occidental Chemical Corporation | Process for the preparation of 4-bromophthalic anhydride |
| US5132423A (en) | 1990-02-05 | 1992-07-21 | General Electric Company | Method for conducting organic reactions using guanidinium salt as phase transfer catalyst |
| US5059697A (en) | 1990-06-14 | 1991-10-22 | Occidental Chemical Corporation | Preparation of halogenated phthalic anhydrides |
| US5229482A (en) | 1991-02-28 | 1993-07-20 | General Electric Company | Phase transfer catalyzed preparation of aromatic polyether polymers |
| US5300201A (en) | 1991-04-22 | 1994-04-05 | Occidental Chemical Corporation | Photochlorination of phthalic anhydride |
| US5235071A (en) | 1991-07-10 | 1993-08-10 | Nippon Shokubai Co., Ltd. | Catalyst for producing phthalic anhydride and process by using the same |
| US5266678A (en) | 1991-08-30 | 1993-11-30 | Eastman Kodak Company | Method for preparing polyamide-imides from (O, imide and polyamine |
| US5364824A (en) | 1992-12-08 | 1994-11-15 | Huntsman Specialty Chemicals Corporation | Catalysis for the production of maleic anhydride containing vanadium-phosphorus oxide with selected promoter elements |
| US5359084A (en) * | 1993-02-18 | 1994-10-25 | General Electric Company | Method of preparing aromatic ether bisimides |
| DE4313174A1 (de) | 1993-04-22 | 1994-10-27 | Hoechst Ag | Verfahren zur Herstellung von 3-Chloranthranilsäurealkylestern hoher Reinheit aus 3-Chloranthranilsäure |
| US5322954A (en) | 1993-05-28 | 1994-06-21 | Occidental Chemical Corporation | Synthesis of 4-substituted phthalic anhydrides |
| US5359092A (en) | 1993-06-02 | 1994-10-25 | Hay Allan S | Bis-N-aminoimides |
| US6008374A (en) * | 1994-05-27 | 1999-12-28 | General Electric Company | Process for preparing bis (ether anhydrides) using alkylamine derived bisimides having low melting temperatures |
| TW399043B (en) * | 1994-05-27 | 2000-07-21 | Gen Electric | Process for preparing bis (ether anhydrides) using alkylamine derived bisimides having low melting temperatures |
| US5536846A (en) * | 1994-05-27 | 1996-07-16 | General Electric Company | Process for preparing bis(ether anhydrides) using alkylamine derived bisimides having low melting temperatures |
| US5510308A (en) | 1994-10-19 | 1996-04-23 | E. I. Du Pont De Nemours And Company | Cation and vanadium substituted heteropolyacid catalysts for vapor phase oxidation |
| US5672750A (en) | 1994-12-16 | 1997-09-30 | Eastman Chemical Company | Preparation of aromatic amides from carbon monoxide, an amine and an aromatic chloride |
| FR2728898B1 (fr) | 1994-12-29 | 1997-01-31 | Rhone Poulenc Chimie | Procede de preparation d'acides carboxyliques par oxydation menagee des alcanes correspondants |
| DE19500031A1 (de) | 1995-01-02 | 1996-07-04 | Basf Ag | Verfahren zur Herstellung von 3-Chlorphthalsäureanhydrid |
| DE19519172A1 (de) | 1995-05-24 | 1996-11-28 | Consortium Elektrochem Ind | Trägerkatalysator für Gasphasenoxidationsreaktoren |
| US5705685A (en) | 1995-10-31 | 1998-01-06 | Sun Company, Inc. (R&M) | Conversion of alkanes to unsaturated carboxylic acids |
| US5872294A (en) | 1996-01-11 | 1999-02-16 | General Electric Company | Aqueous hexasubstituted guanidinium chlorides and methods for their preparation and use |
| JPH09194289A (ja) | 1996-01-12 | 1997-07-29 | Mitsubishi Materials Shilicon Corp | 単結晶引上装置 |
| JP3143598B2 (ja) | 1997-02-28 | 2001-03-07 | 株式会社日本触媒 | 高純度無水フタル酸の製造方法 |
| US5908915A (en) * | 1997-10-06 | 1999-06-01 | General Electric Company | Copolyetherimides and phase catalyzed method for their preparation |
| US6072010A (en) * | 1997-12-23 | 2000-06-06 | General Electric Co. | Polyetherimide resin compositions with improved ductility |
| US6235866B1 (en) * | 1999-10-06 | 2001-05-22 | General Electric Company | Slurry preparation of bis (halophthalimides) and of polyether polymers |
| US6265521B1 (en) * | 2000-08-07 | 2001-07-24 | General Electric Company | Method for preparing polyether polymers of predetermined molecular |
-
2001
- 2001-12-05 US US09/683,257 patent/US6498224B1/en not_active Expired - Lifetime
-
2002
- 2002-10-22 US US10/065,473 patent/US6590108B1/en not_active Expired - Lifetime
- 2002-11-04 CN CNB028274512A patent/CN100469817C/zh not_active Expired - Fee Related
- 2002-11-04 DE DE60216507T patent/DE60216507T2/de not_active Expired - Lifetime
- 2002-11-04 AU AU2002348176A patent/AU2002348176A1/en not_active Abandoned
- 2002-11-04 WO PCT/US2002/035522 patent/WO2003050165A1/en not_active Ceased
- 2002-11-04 ES ES02784398T patent/ES2278067T3/es not_active Expired - Lifetime
- 2002-11-04 JP JP2003551187A patent/JP2005511836A/ja active Pending
- 2002-11-04 EP EP02784398A patent/EP1458791B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1458791A1 (en) | 2004-09-22 |
| JP2005511836A (ja) | 2005-04-28 |
| CN100469817C (zh) | 2009-03-18 |
| WO2003050165A1 (en) | 2003-06-19 |
| EP1458791B1 (en) | 2006-11-29 |
| US6498224B1 (en) | 2002-12-24 |
| DE60216507D1 (de) | 2007-01-11 |
| AU2002348176A1 (en) | 2003-06-23 |
| DE60216507T2 (de) | 2007-10-04 |
| CN1615331A (zh) | 2005-05-11 |
| US6590108B1 (en) | 2003-07-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2278067T3 (es) | Procedimientos para la fabricacion de polieterimidas. | |
| US10829449B2 (en) | Methods of manufacture of bis(ether anhydride)s and polyetherimides | |
| ES2338872T3 (es) | Preparacion de suspension de bis(haloftalimidas) y de polimeros de polieter. | |
| US6689899B2 (en) | Diamine and acid anhydride | |
| Takekoshi | Polyimides | |
| EP0132547B1 (en) | Bisimides and method for their use in polyimide synthesis | |
| ES2331612T3 (es) | Nuevo enfoque para reducir la formacion de ciclicos en la produccion de polieterimidas. | |
| JPH07145172A (ja) | 置換ビス−フタルイミドからの大環状ポリエーテルイミドオリゴマーの製造法 | |
| JP6635506B2 (ja) | フルオレン骨格を有するジアミン、ポリアミック酸、及びポリイミド | |
| TWI284650B (en) | Novel polyimide compositions and novel acid dianhydrides to be used therein | |
| Yang et al. | Synthesis and properties of organosoluble polyimides based on 1, 1-bis [4-(4-amino-2-trifluoromethylphenoxy) phenyl] cyclohexane | |
| CN107278213B (zh) | 通过卤素置换制备低色聚醚酰亚胺的方法及低色聚醚酰亚胺 | |
| US10208163B2 (en) | Method of producing polyimide resin, method of producing polyimide coating, method of producing polyamic acid solution, polyimide coating, and polyamic acid solution | |
| CN112074508A (zh) | 用于分离二酐的方法及由该方法制备的二酐 | |
| ES2295564T3 (es) | Oxidacion en fase liquida de otro-xilenos halogenados. | |
| US11220480B2 (en) | Synthesis of reactive intermediates for polyetherimides, and uses thereof | |
| EP3807257A1 (en) | Method for isolation of an aromatic dianhydride and aromatic dianhydrides prepared by the method | |
| CN115667208A (zh) | 制备二酐的方法 | |
| EP3802506B1 (en) | Method for producing an aromatic dianhydride | |
| SU674677A3 (ru) | Способ получени полиэфиримидов | |
| CN108495883A (zh) | 在有机溶剂中的高固体含量聚醚酰亚胺和其组分以及制备方法 | |
| ES2298631T3 (es) | Preparacion de anhidrido ftalico sustituido, en particular anhidrido 4-cloroftalico. | |
| EP0185386B1 (en) | Polyimides and method for their preparation | |
| Ding et al. | The Strategy of Chlorophthalic Anhydride for Polyimides | |
| EP0126252A1 (en) | Sulfur-containing aromatic compositions and methods for their preparation and use |