ZA200201638B - Method for producing polyamides from dinitriles and diamines. - Google Patents
Method for producing polyamides from dinitriles and diamines. Download PDFInfo
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- ZA200201638B ZA200201638B ZA200201638A ZA200201638A ZA200201638B ZA 200201638 B ZA200201638 B ZA 200201638B ZA 200201638 A ZA200201638 A ZA 200201638A ZA 200201638 A ZA200201638 A ZA 200201638A ZA 200201638 B ZA200201638 B ZA 200201638B
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- ZA
- South Africa
- Prior art keywords
- weight
- liquid
- catalyst
- pressure
- mixture
- Prior art date
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- 150000004985 diamines Chemical class 0.000 title claims description 50
- 239000004952 Polyamide Substances 0.000 title claims description 34
- 229920002647 polyamide Polymers 0.000 title claims description 34
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 148
- 239000000203 mixture Substances 0.000 claims description 100
- 239000003054 catalyst Substances 0.000 claims description 95
- 239000007790 solid phase Substances 0.000 claims description 71
- 239000007788 liquid Substances 0.000 claims description 59
- 239000004408 titanium dioxide Substances 0.000 claims description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 46
- 239000012071 phase Substances 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 36
- 239000007791 liquid phase Substances 0.000 claims description 35
- 239000007789 gas Substances 0.000 claims description 30
- 230000008569 process Effects 0.000 claims description 28
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 22
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 claims description 21
- 229910001930 tungsten oxide Inorganic materials 0.000 claims description 21
- 239000010457 zeolite Substances 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 239000007792 gaseous phase Substances 0.000 claims description 18
- 229910021536 Zeolite Inorganic materials 0.000 claims description 17
- 239000011541 reaction mixture Substances 0.000 claims description 16
- 239000007848 Bronsted acid Substances 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 13
- 229910052774 Proactinium Inorganic materials 0.000 claims description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 12
- 229910021529 ammonia Inorganic materials 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 claims description 8
- 125000005219 aminonitrile group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 238000010924 continuous production Methods 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 230000000737 periodic effect Effects 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052768 actinide Inorganic materials 0.000 claims description 3
- 150000001255 actinides Chemical class 0.000 claims description 3
- 239000002638 heterogeneous catalyst Substances 0.000 claims description 3
- 150000003951 lactams Chemical class 0.000 claims description 3
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 3
- 150000002602 lanthanoids Chemical class 0.000 claims description 3
- 229910052814 silicon oxide Inorganic materials 0.000 claims description 3
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 claims description 3
- 229910001887 tin oxide Inorganic materials 0.000 claims description 3
- 230000007704 transition Effects 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 229910052615 phyllosilicate Inorganic materials 0.000 claims description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims 2
- 239000003377 acid catalyst Substances 0.000 claims 1
- 238000010923 batch production Methods 0.000 claims 1
- 239000008247 solid mixture Substances 0.000 claims 1
- -1 alkylaryl diamines Chemical class 0.000 description 22
- 230000015572 biosynthetic process Effects 0.000 description 21
- 238000003786 synthesis reaction Methods 0.000 description 20
- 150000001735 carboxylic acids Chemical class 0.000 description 16
- 150000001412 amines Chemical class 0.000 description 13
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 12
- 125000003277 amino group Chemical group 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 229920001971 elastomer Polymers 0.000 description 12
- 239000000049 pigment Substances 0.000 description 12
- 125000002560 nitrile group Chemical group 0.000 description 11
- 125000002843 carboxylic acid group Chemical group 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 10
- 239000005060 rubber Substances 0.000 description 10
- 239000000470 constituent Substances 0.000 description 8
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 8
- 239000000178 monomer Substances 0.000 description 7
- 239000011148 porous material Substances 0.000 description 7
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- 239000001361 adipic acid Substances 0.000 description 6
- 235000011037 adipic acid Nutrition 0.000 description 6
- 239000008188 pellet Substances 0.000 description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 4
- 229920001169 thermoplastic Polymers 0.000 description 4
- 239000004416 thermosoftening plastic Substances 0.000 description 4
- KBMSFJFLSXLIDJ-UHFFFAOYSA-N 6-aminohexanenitrile Chemical compound NCCCCCC#N KBMSFJFLSXLIDJ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000011258 core-shell material Substances 0.000 description 3
- 238000005520 cutting process Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- SZVJSHCCFOBDDC-UHFFFAOYSA-N ferrosoferric oxide Chemical compound O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 150000003949 imides Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000003018 phosphorus compounds Chemical class 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- JJMDCOVWQOJGCB-UHFFFAOYSA-N 5-aminopentanoic acid Chemical compound [NH3+]CCCCC([O-])=O JJMDCOVWQOJGCB-UHFFFAOYSA-N 0.000 description 2
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- 239000004609 Impact Modifier Substances 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- 229960002684 aminocaproic acid Drugs 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- HSJPMRKMPBAUAU-UHFFFAOYSA-N cerium(3+);trinitrate Chemical compound [Ce+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O HSJPMRKMPBAUAU-UHFFFAOYSA-N 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 229910000423 chromium oxide Inorganic materials 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000000412 dendrimer Substances 0.000 description 2
- 229920000736 dendritic polymer Polymers 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 230000001050 lubricating effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- YSRFBCIGFNFMPS-UHFFFAOYSA-N naphthalene-1,3,5,7-tetracarboxylic acid Chemical compound C1=C(C(O)=O)C=C(C(O)=O)C2=CC(C(=O)O)=CC(C(O)=O)=C21 YSRFBCIGFNFMPS-UHFFFAOYSA-N 0.000 description 2
- LKKPNUDVOYAOBB-UHFFFAOYSA-N naphthalocyanine Chemical compound N1C(N=C2C3=CC4=CC=CC=C4C=C3C(N=C3C4=CC5=CC=CC=C5C=C4C(=N4)N3)=N2)=C(C=C2C(C=CC=C2)=C2)C2=C1N=C1C2=CC3=CC=CC=C3C=C2C4=N1 LKKPNUDVOYAOBB-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 230000005501 phase interface Effects 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 150000004763 sulfides Chemical class 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- BHHYHSUAOQUXJK-UHFFFAOYSA-L zinc fluoride Chemical compound F[Zn]F BHHYHSUAOQUXJK-UHFFFAOYSA-L 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 description 1
- SKJCKYVIQGBWTN-UHFFFAOYSA-N (4-hydroxyphenyl) methanesulfonate Chemical compound CS(=O)(=O)OC1=CC=C(O)C=C1 SKJCKYVIQGBWTN-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- FTVFPPFZRRKJIH-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(N)CC(C)(C)N1 FTVFPPFZRRKJIH-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
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- 229910052718 tin Inorganic materials 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- ITRNXVSDJBHYNJ-UHFFFAOYSA-N tungsten disulfide Chemical compound S=[W]=S ITRNXVSDJBHYNJ-UHFFFAOYSA-N 0.000 description 1
- ISIQQQYKUPBYSL-UHFFFAOYSA-N undecanedinitrile Chemical compound N#CCCCCCCCCCC#N ISIQQQYKUPBYSL-UHFFFAOYSA-N 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 239000012463 white pigment Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- IPCAPQRVQMIMAN-UHFFFAOYSA-L zirconyl chloride Chemical compound Cl[Zr](Cl)=O IPCAPQRVQMIMAN-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/04—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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/28—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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/38—Polyamides prepared from aldehydes and polynitriles
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19935398A DE19935398A1 (de) | 1999-07-30 | 1999-07-30 | Verfahren zur Herstellung von Polyamiden aus Dinitrilen und Diaminen |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200201638B true ZA200201638B (en) | 2003-04-30 |
Family
ID=7916325
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200201638A ZA200201638B (en) | 1999-07-30 | 2002-02-27 | Method for producing polyamides from dinitriles and diamines. |
Country Status (22)
Country | Link |
---|---|
US (1) | US6699960B1 (fr) |
EP (1) | EP1198491B1 (fr) |
JP (1) | JP3462868B2 (fr) |
KR (1) | KR100610728B1 (fr) |
CN (1) | CN1175029C (fr) |
AR (1) | AR024799A1 (fr) |
AT (1) | ATE251194T1 (fr) |
AU (1) | AU6691700A (fr) |
BG (1) | BG106341A (fr) |
BR (1) | BR0012774B1 (fr) |
CA (1) | CA2386888C (fr) |
CZ (1) | CZ2002188A3 (fr) |
DE (2) | DE19935398A1 (fr) |
ES (1) | ES2209950T3 (fr) |
HU (1) | HUP0202105A3 (fr) |
IL (1) | IL147297A0 (fr) |
MX (1) | MXPA02001054A (fr) |
PL (1) | PL353271A1 (fr) |
SK (1) | SK1492002A3 (fr) |
TW (1) | TW593433B (fr) |
WO (1) | WO2001009224A1 (fr) |
ZA (1) | ZA200201638B (fr) |
Families Citing this family (90)
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US7068724B1 (en) | 1999-10-20 | 2006-06-27 | Prime Research Alliance E., Inc. | Method and apparatus for inserting digital media advertisements into statistical multiplexed streams |
DE10021191A1 (de) * | 2000-05-03 | 2001-11-08 | Basf Ag | Verfahren zur Herstellung eines Polymers unter Verwendung von Caprolactam |
DE10058292A1 (de) * | 2000-11-23 | 2002-05-29 | Basf Ag | Polyamide |
DE10217439A1 (de) | 2002-04-18 | 2003-10-30 | Basf Ag | Verfahren zur Herstellung von Polyamiden |
BRPI0720299A2 (pt) | 2006-12-13 | 2014-02-04 | Basf Se | Composição de moldagem termoplástica, uso mesma, e, moldagem |
DE102008038411A1 (de) | 2007-09-11 | 2009-03-12 | Basf Se | Flammgeschützte Polyamide |
US8309221B2 (en) * | 2007-10-01 | 2012-11-13 | Jay Plaehn | Reinforced foam panel |
MY150256A (en) | 2007-12-18 | 2013-12-31 | Basf Se | Thermoplastic polyamides having polyether amines |
DE102009011668A1 (de) | 2008-03-05 | 2009-09-10 | Basf Se | Polyamid und hyperverzweigte Polyesster enthaltende Formmasse |
WO2009156342A1 (fr) | 2008-06-27 | 2009-12-30 | Basf Se | Polyamide thermoconducteur avec terre de diatomées |
BRPI0913866A2 (pt) * | 2008-07-02 | 2015-10-20 | Basf Se | processo para a produção de espumas poliméricas, espumas poliméricas, elemento de reforço para perfis de ocos na carroceria de veículos a motor, e, perfil de conexão ou de reforço para elemento de janela |
DE102008058246A1 (de) | 2008-11-19 | 2010-05-20 | Basf Se | Hochmolekulare Polyamide |
US8268920B2 (en) | 2008-12-16 | 2012-09-18 | Basf Se | Heat aging resistant polyamides |
EP2264093A1 (fr) | 2009-06-16 | 2010-12-22 | THOR GmbH | Masses à mouler en polyamide ignifugées |
US9080259B2 (en) | 2009-06-30 | 2015-07-14 | Basf Se | Polyamide fibers with dyeable particles and production thereof |
WO2011000816A1 (fr) | 2009-07-03 | 2011-01-06 | Basf Se | Mélanges nanocomposites contenant des polyamides et des polyoléfines |
EP2456816A1 (fr) | 2009-07-21 | 2012-05-30 | Basf Se | Mélanges nanocomposites à base de polyamides et de polyarylène éther sulfones |
WO2011009877A1 (fr) | 2009-07-24 | 2011-01-27 | Basf Se | Matériaux de moulage polyamides ignifuges |
CN102597080A (zh) | 2009-10-27 | 2012-07-18 | 巴斯夫欧洲公司 | 耐热老化的聚酰胺 |
CN102666693A (zh) | 2009-10-27 | 2012-09-12 | 巴斯夫欧洲公司 | 具有阻燃性的耐热老化性聚酰胺 |
WO2011069942A1 (fr) | 2009-12-08 | 2011-06-16 | Basf Se | Matières à mouler constituées de copolyamide partiellement aromatique à base d'octaméthylène diamine |
MY155949A (en) | 2009-12-09 | 2015-12-31 | Basf Se | Semi-aromatic, semi-crystalline copolyamides |
DE102010062886A1 (de) | 2009-12-16 | 2011-06-22 | Basf Se, 67063 | Polyarylenethersulfone als Schlagzähmodifier |
US8466221B2 (en) | 2010-03-09 | 2013-06-18 | Basf Se | Polyamides that resist heat-aging |
BR112012020874A2 (pt) | 2010-03-09 | 2016-05-03 | Basf Se | composição de moldagem termoplástica, uso das composições de moldagem termoplásticas, e, fibra, folha, ou peça de moldagem |
WO2011134930A1 (fr) | 2010-04-30 | 2011-11-03 | Basf Se | Polyamides renforcés par des fibres longues comportant des polyoléfines |
DE102010023770A1 (de) | 2010-06-15 | 2011-12-15 | Basf Se | Glühdrahtbeständige Formmassen |
US8563680B2 (en) | 2010-06-15 | 2013-10-22 | Basf Se | Heat-aging-resistant polyamides |
BR112012031898B1 (pt) | 2010-06-15 | 2019-12-24 | Basf Se | composição de moldagem termoplástica, uso das composições de moldagem, e, fibra, folha metálica ou peça moldada |
WO2012013564A1 (fr) | 2010-07-30 | 2012-02-02 | Basf Se | Matières moulables ignifugées |
EP2415827A1 (fr) | 2010-08-04 | 2012-02-08 | Basf Se | Polyamides ignifuges dotés de silicate en couche |
WO2012062594A1 (fr) | 2010-11-11 | 2012-05-18 | Basf Se | Polyamides résistant au vieillissement thermique |
ES2555128T3 (es) | 2010-11-18 | 2015-12-29 | Styrolution Europe Gmbh | Masas de moldeo termoplásticas a base de copolímeros de estireno y poliamidas; procedimiento para su producción y su utilización |
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US8653168B2 (en) | 2011-05-10 | 2014-02-18 | Basf Se | Flame-retardant thermoplastic molding composition |
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US8883904B2 (en) | 2011-09-15 | 2014-11-11 | Basf Se | Mixtures of silver and zinc oxide as stabilizer for flame-retardant polyamides |
EP2573138A1 (fr) | 2011-09-21 | 2013-03-27 | Basf Se | Masses de moulage en polyamide |
EP2782964B1 (fr) | 2011-11-25 | 2018-04-11 | Basf Se | Matières polyamides moulables par soufflage |
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EP2641939A1 (fr) | 2012-03-21 | 2013-09-25 | Basf Se | Polyamide ignifuge teinté en nuances claires |
EP2650331A1 (fr) | 2012-04-11 | 2013-10-16 | Basf Se | Polyamide pour utilisations en rapport avec l'eau potable |
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EP2986673B1 (fr) | 2013-04-15 | 2017-03-08 | Basf Se | Polyamide résistant au filament incandescent |
DE102014215370A1 (de) | 2013-09-05 | 2015-03-05 | Basf Se | Langfaserverstärkte flammgeschützte Polyamide |
EP3060597A4 (fr) * | 2013-10-22 | 2017-06-14 | Empire Technology Development LLC | Composés et procédés pour produire du nylon 6 |
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WO2016087324A1 (fr) | 2014-12-01 | 2016-06-09 | Basf Se | Polyamides ignifugés comportant des sels d'acide sulfonique |
WO2016166140A1 (fr) | 2015-04-16 | 2016-10-20 | Basf Se | Polyamides présentant des propriétés optiques améliorées |
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EP3118247A1 (fr) | 2015-07-15 | 2017-01-18 | Basf Se | Polyamide présentant des caractéristiques optiques ameliorées |
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US11193020B2 (en) | 2017-02-01 | 2021-12-07 | Basf Se | Polyarylene ether sulfone comprising naphthalic acid anhydride endgroups |
KR102524256B1 (ko) | 2017-03-01 | 2023-04-20 | 바스프 에스이 | 난연성 pvp 함유 폴리아미드 |
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CN113423784B (zh) | 2019-02-20 | 2023-12-22 | 巴斯夫欧洲公司 | 热塑性模塑复合物 |
US20220145046A1 (en) | 2019-02-25 | 2022-05-12 | Basf Se | Thermoplastic molding composition |
BR112022001111A2 (pt) | 2019-09-05 | 2022-03-15 | Basf Se | Composição termoplástica de moldagem, uso de pelo menos um composto de carbazol, uso de composições termoplásticas de moldagem e fibra |
EP3808810B1 (fr) | 2019-10-16 | 2023-03-29 | INEOS Styrolution Group GmbH | Matières de moulage thermoplastiques pour un procédé de rotomoulage |
JP2023516255A (ja) | 2020-01-27 | 2023-04-19 | ビーエーエスエフ ソシエタス・ヨーロピア | 耐熱性を有する熱可塑性ポリアミド成形用組成物 |
CA3169428A1 (fr) | 2020-02-26 | 2021-09-02 | Basf Se | Compositions de moulage de polyamide resistantes au vieillissement thermique |
MX2022011626A (es) | 2020-03-20 | 2022-10-13 | Basf Se | Composiciones de moldeo de poliamida plastificada. |
BR112022019115A2 (pt) | 2020-03-25 | 2022-11-08 | Basf Se | Composição de modelagem termoplástica, processo de preparação da composição, uso da composição e fibra, folha ou modelagem |
WO2022180221A1 (fr) | 2021-02-25 | 2022-09-01 | Basf Se | Polymères ayant une conductivité thermique améliorée |
WO2022238213A1 (fr) | 2021-05-11 | 2022-11-17 | Basf Se | Corps moulés à marquage laser et soudés au laser et leur fabrication |
WO2022254022A1 (fr) | 2021-06-04 | 2022-12-08 | Basf Se | Composition de moulage thermoplastique conservant un brillant élevé |
WO2023237603A1 (fr) | 2022-06-08 | 2023-12-14 | Basf Se | Procédé de recyclage pour production de composé de polyamide |
WO2024068509A1 (fr) | 2022-09-27 | 2024-04-04 | Basf Se | Compositions de moulage thermoplastiques à stabilité de couleur-1 améliorée |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3429095B2 (ja) * | 1994-05-27 | 2003-07-22 | ツイマー・アクチェンゲゼルシャフト | α,ω−ジニトリルに基づくポリアミドの製造方法 |
DE4430480A1 (de) * | 1994-08-27 | 1996-02-29 | Basf Ag | Hochmolekulare Polyamide aus Nitrilen |
EP0922065B1 (fr) * | 1996-08-30 | 2002-11-20 | Basf Aktiengesellschaft | Procede pour la preparation de polyamides a partir d'aminonitriles |
DE19804020A1 (de) * | 1998-02-02 | 1999-08-05 | Basf Ag | Verfahren zur Herstellung von Polyamiden aus Aminonitrilen |
DE19804014A1 (de) * | 1998-02-02 | 1999-08-05 | Basf Ag | Diskontinuierliches Verfahren zur Herstellung von Polyamiden aus Aminonitrilen |
DE19804023A1 (de) * | 1998-02-02 | 1999-08-05 | Basf Ag | Kontinuierliches Verfahren zur Herstellung von Polyamiden aus Aminonitrilen |
US6509439B1 (en) * | 2000-04-14 | 2003-01-21 | E. I. Du Pont De Nemours And Company | Process for the production of polyamides from dinitriles and diamines |
-
1999
- 1999-07-30 DE DE19935398A patent/DE19935398A1/de not_active Withdrawn
-
2000
- 2000-06-23 TW TW089112399A patent/TW593433B/zh not_active IP Right Cessation
- 2000-07-11 IL IL14729700A patent/IL147297A0/xx unknown
- 2000-07-11 PL PL00353271A patent/PL353271A1/xx not_active Application Discontinuation
- 2000-07-11 CN CNB00810817XA patent/CN1175029C/zh not_active Expired - Lifetime
- 2000-07-11 MX MXPA02001054A patent/MXPA02001054A/es active IP Right Grant
- 2000-07-11 CZ CZ2002188A patent/CZ2002188A3/cs unknown
- 2000-07-11 KR KR1020027001283A patent/KR100610728B1/ko not_active IP Right Cessation
- 2000-07-11 ES ES00954469T patent/ES2209950T3/es not_active Expired - Lifetime
- 2000-07-11 CA CA002386888A patent/CA2386888C/fr not_active Expired - Fee Related
- 2000-07-11 AU AU66917/00A patent/AU6691700A/en not_active Abandoned
- 2000-07-11 SK SK149-2002A patent/SK1492002A3/sk unknown
- 2000-07-11 WO PCT/EP2000/006566 patent/WO2001009224A1/fr not_active Application Discontinuation
- 2000-07-11 JP JP2001514028A patent/JP3462868B2/ja not_active Expired - Fee Related
- 2000-07-11 HU HU0202105A patent/HUP0202105A3/hu unknown
- 2000-07-11 US US10/048,246 patent/US6699960B1/en not_active Expired - Lifetime
- 2000-07-11 EP EP00954469A patent/EP1198491B1/fr not_active Expired - Lifetime
- 2000-07-11 DE DE50003919T patent/DE50003919D1/de not_active Expired - Lifetime
- 2000-07-11 AT AT00954469T patent/ATE251194T1/de not_active IP Right Cessation
- 2000-07-11 BR BRPI0012774-4A patent/BR0012774B1/pt not_active IP Right Cessation
- 2000-07-19 AR ARP000103716A patent/AR024799A1/es unknown
-
2002
- 2002-01-22 BG BG106341A patent/BG106341A/xx unknown
- 2002-02-27 ZA ZA200201638A patent/ZA200201638B/en unknown
Also Published As
Publication number | Publication date |
---|---|
HUP0202105A2 (en) | 2002-10-28 |
JP2003506509A (ja) | 2003-02-18 |
TW593433B (en) | 2004-06-21 |
DE19935398A1 (de) | 2001-02-01 |
CN1364178A (zh) | 2002-08-14 |
HUP0202105A3 (en) | 2003-10-28 |
EP1198491B1 (fr) | 2003-10-01 |
CN1175029C (zh) | 2004-11-10 |
JP3462868B2 (ja) | 2003-11-05 |
AU6691700A (en) | 2001-02-19 |
PL353271A1 (en) | 2003-11-03 |
KR20020016927A (ko) | 2002-03-06 |
MXPA02001054A (es) | 2002-08-20 |
AR024799A1 (es) | 2002-10-23 |
CZ2002188A3 (cs) | 2002-05-15 |
BG106341A (en) | 2002-11-29 |
BR0012774A (pt) | 2002-12-17 |
DE50003919D1 (de) | 2003-11-06 |
IL147297A0 (en) | 2002-08-14 |
EP1198491A1 (fr) | 2002-04-24 |
KR100610728B1 (ko) | 2006-08-09 |
ES2209950T3 (es) | 2004-07-01 |
ATE251194T1 (de) | 2003-10-15 |
BR0012774B1 (pt) | 2011-03-22 |
CA2386888C (fr) | 2009-03-03 |
SK1492002A3 (en) | 2002-10-08 |
WO2001009224A1 (fr) | 2001-02-08 |
CA2386888A1 (fr) | 2001-02-08 |
US6699960B1 (en) | 2004-03-02 |
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