ES2242974T3 - Fenil-alquil-cetona sustituida con amina ciclica, y procedimiento parasu utilizacion. - Google Patents

Fenil-alquil-cetona sustituida con amina ciclica, y procedimiento parasu utilizacion.

Info

Publication number: ES2242974T3
Authority: ES; Spain
Prior art keywords: alkyl; phenyl; formula; och; substituted
Prior art date: 1996-05-03
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

Application number

ES97810255T

Other languages

English (en)

Spanish (es)

Inventor

Rinaldo Husler

Rudolf Schwabe

Reto Luisoli

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF Schweiz AG

Original Assignee

Ciba Spezialitaetenchemie Holding AG

Ciba SC Holding AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1996-05-03

Filing date

1997-04-24

Publication date

2005-11-16

1997-04-24 Application filed by Ciba Spezialitaetenchemie Holding AG, Ciba SC Holding AG filed Critical Ciba Spezialitaetenchemie Holding AG

2005-11-16 Application granted granted Critical

2005-11-16 Publication of ES2242974T3 publication Critical patent/ES2242974T3/es

2017-04-24 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

-1 CYCLINE AMINE Chemical group 0.000 title claims abstract description 97
238000000034 method Methods 0.000 title claims abstract description 24
125000000217 alkyl group Chemical group 0.000 claims abstract description 65
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 35
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 26
150000002576 ketones Chemical class 0.000 claims abstract description 23
238000004519 manufacturing process Methods 0.000 claims abstract description 14
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 8
238000007098 aminolysis reaction Methods 0.000 claims abstract description 6
238000006243 chemical reaction Methods 0.000 claims description 42
150000001875 compounds Chemical class 0.000 claims description 27
229910052739 hydrogen Inorganic materials 0.000 claims description 21
239000001257 hydrogen Substances 0.000 claims description 15
125000003545 alkoxy group Chemical group 0.000 claims description 14
229910052799 carbon Inorganic materials 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 14
125000003884 phenylalkyl group Chemical group 0.000 claims description 12
150000002367 halogens Chemical class 0.000 claims description 10
125000002947 alkylene group Chemical group 0.000 claims description 9
150000001412 amines Chemical class 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
125000002757 morpholinyl group Chemical group 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
125000004193 piperazinyl group Chemical group 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 7
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 5
238000005658 halogenation reaction Methods 0.000 claims description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
125000002541 furyl group Chemical group 0.000 claims description 3
230000026030 halogenation Effects 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
125000001544 thienyl group Chemical group 0.000 claims description 3
230000017105 transposition Effects 0.000 claims description 3
PCDHSSHKDZYLLI-UHFFFAOYSA-N butan-1-one Chemical compound CCC[C]=O PCDHSSHKDZYLLI-UHFFFAOYSA-N 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 8
125000001589 carboacyl group Chemical group 0.000 claims 2
125000003342 alkenyl group Chemical group 0.000 abstract 1
125000001475 halogen functional group Chemical group 0.000 abstract 1
239000000203 mixture Substances 0.000 description 17
239000000047 product Substances 0.000 description 17
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
239000002253 acid Substances 0.000 description 12
239000003054 catalyst Substances 0.000 description 11
239000000049 pigment Substances 0.000 description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
238000004821 distillation Methods 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000000975 dye Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
239000000178 monomer Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 7
JKVSAZTYCZKNDX-UHFFFAOYSA-N 1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C1=CC(C(=O)CCC)=CC=C1N1CCOCC1 JKVSAZTYCZKNDX-UHFFFAOYSA-N 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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 description 6
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
238000009835 boiling Methods 0.000 description 6
239000013078 crystal Substances 0.000 description 6
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
235000011121 sodium hydroxide Nutrition 0.000 description 6
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
229910052802 copper Inorganic materials 0.000 description 5
239000010949 copper Substances 0.000 description 5
239000008367 deionised water Substances 0.000 description 5
229910021641 deionized water Inorganic materials 0.000 description 5
239000004922 lacquer Substances 0.000 description 5
238000006116 polymerization reaction Methods 0.000 description 5
239000000843 powder Substances 0.000 description 5
XLCJPQYALLFIPW-UHFFFAOYSA-N 1-(4-chlorophenyl)butan-1-one Chemical compound CCCC(=O)C1=CC=C(Cl)C=C1 XLCJPQYALLFIPW-UHFFFAOYSA-N 0.000 description 4
JUVLPJNXBKOSFH-UHFFFAOYSA-N 2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C1=CC(C(=O)C(N(C)C)CC)=CC=C1N1CCOCC1 JUVLPJNXBKOSFH-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
239000000976 ink Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
BUZYGTVTZYSBCU-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1 BUZYGTVTZYSBCU-UHFFFAOYSA-N 0.000 description 3
UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 3
MBSNWZTZDWVIDP-UHFFFAOYSA-N 2-bromo-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C1=CC(C(=O)C(Br)CC)=CC=C1N1CCOCC1 MBSNWZTZDWVIDP-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
239000012965 benzophenone Substances 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000012467 final product Substances 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000003973 paint Substances 0.000 description 3
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
230000005855 radiation Effects 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
230000019635 sulfation Effects 0.000 description 3
238000005670 sulfation reaction Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
125000006755 (C2-C20) alkyl group Chemical group 0.000 description 2
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
HOIDKJFWEVIJAT-UHFFFAOYSA-N 1-(4-bromophenyl)butan-1-one Chemical compound CCCC(=O)C1=CC=C(Br)C=C1 HOIDKJFWEVIJAT-UHFFFAOYSA-N 0.000 description 2
TZDJIQPAOYGOTB-UHFFFAOYSA-M 1-phenyl-2-thieno[3,2-c]pyridin-5-ium-5-ylethanone;chloride Chemical compound [Cl-].C=1C=C2SC=CC2=C[N+]=1CC(=O)C1=CC=CC=C1 TZDJIQPAOYGOTB-UHFFFAOYSA-M 0.000 description 2
WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 2
239000005751 Copper oxide Substances 0.000 description 2
IAFWKKMDMCQMSP-UHFFFAOYSA-N FC1=C(C(=CC=C1N1C(=CC=C1C)C)F)[Ti] Chemical compound FC1=C(C(=CC=C1N1C(=CC=C1C)C)F)[Ti] IAFWKKMDMCQMSP-UHFFFAOYSA-N 0.000 description 2
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
238000005727 Friedel-Crafts reaction Methods 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
230000001133 acceleration Effects 0.000 description 2
239000000654 additive Substances 0.000 description 2
238000005576 amination reaction Methods 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
150000008366 benzophenones Chemical class 0.000 description 2
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
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 2
244000309464 bull Species 0.000 description 2
229910000431 copper oxide Inorganic materials 0.000 description 2
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
PESYEWKSBIWTAK-UHFFFAOYSA-N cyclopenta-1,3-diene;titanium(2+) Chemical class [Ti+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 PESYEWKSBIWTAK-UHFFFAOYSA-N 0.000 description 2
125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 2
UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000008030 elimination Effects 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
FWCHISPFSGCORQ-UHFFFAOYSA-N morpholine;hydrate Chemical compound O.C1COCCN1 FWCHISPFSGCORQ-UHFFFAOYSA-N 0.000 description 2
150000002780 morpholines Chemical class 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000003504 photosensitizing agent Substances 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
229920000647 polyepoxide Polymers 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000002994 raw material Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
238000010186 staining Methods 0.000 description 2
239000010936 titanium Substances 0.000 description 2
229910052719 titanium Inorganic materials 0.000 description 2
229920006337 unsaturated polyester resin Polymers 0.000 description 2
PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-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
KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 1
RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 1
XMUGWCSIQUJOFA-UHFFFAOYSA-N 1-(4-chlorophenyl)pentan-1-one Chemical compound CCCCC(=O)C1=CC=C(Cl)C=C1 XMUGWCSIQUJOFA-UHFFFAOYSA-N 0.000 description 1
JCMZZYSPSGHBNM-UHFFFAOYSA-N 1-(4-piperidin-1-ylphenyl)ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N1CCCCC1 JCMZZYSPSGHBNM-UHFFFAOYSA-N 0.000 description 1
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
YSDVERQJWQAOEO-UHFFFAOYSA-N 1-phosphanylprop-2-en-1-one Chemical compound PC(=O)C=C YSDVERQJWQAOEO-UHFFFAOYSA-N 0.000 description 1
OXEMYLNXNAJPGY-UHFFFAOYSA-N 2-(2,2-diphenylpropoxy)ethyl prop-2-enoate Chemical compound C(C=C)(=O)OCCOCC(C)(C1=CC=CC=C1)C1=CC=CC=C1 OXEMYLNXNAJPGY-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 1
QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
ISULZYQDGYXDFW-UHFFFAOYSA-N 3-methylbutanoyl chloride Chemical compound CC(C)CC(Cl)=O ISULZYQDGYXDFW-UHFFFAOYSA-N 0.000 description 1
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
ULVDMKRXBIKOMK-UHFFFAOYSA-N 4,5,6,7-tetrachloro-2,3-dihydroisoindol-1-one Chemical compound ClC1=C(Cl)C(Cl)=C2CNC(=O)C2=C1Cl ULVDMKRXBIKOMK-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
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125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
239000012071 phase Substances 0.000 description 1
IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
229960005323 phenoxyethanol Drugs 0.000 description 1
229940067107 phenylethyl alcohol Drugs 0.000 description 1
150000003018 phosphorus compounds Chemical class 0.000 description 1
IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
125000003367 polycyclic group Chemical group 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920001721 polyimide Polymers 0.000 description 1
229920001228 polyisocyanate Polymers 0.000 description 1
239000005056 polyisocyanate Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
239000003223 protective agent Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000005057 refrigeration Methods 0.000 description 1
230000001850 reproductive effect Effects 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000004071 soot Substances 0.000 description 1
238000009331 sowing Methods 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
LPWCRLGKYWVLHQ-UHFFFAOYSA-N tetradecanoyl chloride Chemical compound CCCCCCCCCCCCCC(Cl)=O LPWCRLGKYWVLHQ-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
DAPQZEJYVJVIPD-UHFFFAOYSA-N trioxan-4-one Chemical compound O=C1CCOOO1 DAPQZEJYVJVIPD-UHFFFAOYSA-N 0.000 description 1
AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
235000013799 ultramarine blue Nutrition 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
239000011800 void material Substances 0.000 description 1
239000002699 waste material Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/112—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Physics & Mathematics (AREA)
Spectroscopy & Molecular Physics (AREA)
General Physics & Mathematics (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Hydrogenated Pyridines (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Polymerisation Methods In General (AREA)

ES97810255T 1996-05-03 1997-04-24 Fenil-alquil-cetona sustituida con amina ciclica, y procedimiento parasu utilizacion. Expired - Lifetime ES2242974T3 (es)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH113896		1996-05-03
CH1138/96		1996-05-03

Publications (1)

Publication Number	Publication Date
ES2242974T3 true ES2242974T3 (es)	2005-11-16

Family

ID=4203382

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
ES97810255T Expired - Lifetime ES2242974T3 (es)	1996-05-03	1997-04-24	Fenil-alquil-cetona sustituida con amina ciclica, y procedimiento parasu utilizacion.
ES04102145T Expired - Lifetime ES2356448T3 (es)	1996-05-03	1997-04-24	Proceso para la preparación de fenil-alquil-cetonas sustituidas con amina cíclica.

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
ES04102145T Expired - Lifetime ES2356448T3 (es)	1996-05-03	1997-04-24	Proceso para la preparación de fenil-alquil-cetonas sustituidas con amina cíclica.

Country Status (14)

Country	Link
US (3)	US5795985A (2)
EP (2)	EP0805152B1 (2)
JP (1)	JP4545835B2 (2)
KR (2)	KR100507664B1 (2)
CN (2)	CN1168700C (2)
AT (2)	ATE489373T1 (2)
BR (1)	BR9703050A (2)
CA (1)	CA2204200C (2)
DE (2)	DE59713049D1 (2)
DK (2)	DK1468994T3 (2)
ES (2)	ES2242974T3 (2)
ID (1)	ID16845A (2)
TW (1)	TW455592B (2)
ZA (1)	ZA973797B (2)

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CN108358871B (zh) *	2018-02-01	2020-05-22	浙江扬帆新材料股份有限公司	一种2-苄基-2-二甲基氨基-1-(4-吗啉苯基)丁酮的合成方法
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1997
- 1997-04-21 US US08/847,519 patent/US5795985A/en not_active Expired - Lifetime
- 1997-04-24 ES ES97810255T patent/ES2242974T3/es not_active Expired - Lifetime
- 1997-04-24 DE DE59713049T patent/DE59713049D1/de not_active Expired - Lifetime
- 1997-04-24 DK DK04102145.2T patent/DK1468994T3/da active
- 1997-04-24 EP EP97810255A patent/EP0805152B1/de not_active Expired - Lifetime
- 1997-04-24 DK DK97810255T patent/DK0805152T3/da active
- 1997-04-24 DE DE59712337T patent/DE59712337D1/de not_active Expired - Lifetime
- 1997-04-24 AT AT04102145T patent/ATE489373T1/de active
- 1997-04-24 AT AT97810255T patent/ATE297387T1/de not_active IP Right Cessation
- 1997-04-24 ES ES04102145T patent/ES2356448T3/es not_active Expired - Lifetime
- 1997-04-24 EP EP04102145A patent/EP1468994B1/de not_active Expired - Lifetime
- 1997-04-29 ID IDP971429A patent/ID16845A/id unknown
- 1997-04-30 CN CNB00135342XA patent/CN1168700C/zh not_active Expired - Lifetime
- 1997-04-30 CN CN97110835A patent/CN1072662C/zh not_active Expired - Lifetime
- 1997-05-01 TW TW086105781A patent/TW455592B/zh not_active IP Right Cessation
- 1997-05-01 CA CA002204200A patent/CA2204200C/en not_active Expired - Lifetime
- 1997-05-01 JP JP12794597A patent/JP4545835B2/ja not_active Expired - Lifetime
- 1997-05-02 ZA ZA9703797A patent/ZA973797B/xx unknown
- 1997-05-02 KR KR1019970017007A patent/KR100507664B1/ko not_active Expired - Lifetime
- 1997-05-05 BR BR9703050A patent/BR9703050A/pt not_active IP Right Cessation
1998
- 1998-06-01 US US09/088,218 patent/US5977357A/en not_active Expired - Lifetime
1999
- 1999-06-10 US US09/329,833 patent/US6191182B1/en not_active Expired - Lifetime
2004
- 2004-09-24 KR KR1020040077005A patent/KR100479989B1/ko not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CN1168700C (zh)	2004-09-29
JP4545835B2 (ja)	2010-09-15
CN1166487A (zh)	1997-12-03
US5795985A (en)	1998-08-18
DK0805152T3 (da)	2005-08-08
EP0805152A2 (de)	1997-11-05
ATE489373T1 (de)	2010-12-15
CA2204200A1 (en)	1997-11-03
US5977357A (en)	1999-11-02
CN1309116A (zh)	2001-08-22
ZA973797B (en)	1997-12-01
ATE297387T1 (de)	2005-06-15
EP0805152A3 (de)	1998-01-28
BR9703050A (pt)	1998-09-01
ES2356448T3 (es)	2011-04-08
DK1468994T3 (da)	2011-02-21
MX9703235A (es)	1997-11-29
CA2204200C (en)	2007-04-10
TW455592B (en)	2001-09-21
ID16845A (id)	1997-11-13
JPH1087643A (ja)	1998-04-07
KR100507664B1 (ko)	2005-11-22
US6191182B1 (en)	2001-02-20
CN1072662C (zh)	2001-10-10
KR100479989B1 (ko)	2005-03-31
DE59713049D1 (de)	2011-01-05
DE59712337D1 (de)	2005-07-14
EP0805152B1 (de)	2005-06-08
EP1468994A1 (de)	2004-10-20
EP1468994B1 (de)	2010-11-24
KR970074775A (ko)	1997-12-10

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