JPH07188188A - １、３、５−トリアジンの製造方法 - Google Patents
１、３、５−トリアジンの製造方法Info
- Publication number
- JPH07188188A JPH07188188A JP6231956A JP23195694A JPH07188188A JP H07188188 A JPH07188188 A JP H07188188A JP 6231956 A JP6231956 A JP 6231956A JP 23195694 A JP23195694 A JP 23195694A JP H07188188 A JPH07188188 A JP H07188188A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- benzonitrile
- compound
- reaction
- alkyl
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 title 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical class N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims abstract description 44
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 229940100198 alkylating agent Drugs 0.000 claims abstract description 6
- 239000002168 alkylating agent Substances 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 239000007858 starting material Substances 0.000 claims abstract description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 230000029936 alkylation Effects 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims 2
- 150000008050 dialkyl sulfates Chemical class 0.000 claims 1
- CHZCERSEMVWNHL-UHFFFAOYSA-N 2-hydroxybenzonitrile Chemical class OC1=CC=CC=C1C#N CHZCERSEMVWNHL-UHFFFAOYSA-N 0.000 abstract description 5
- 239000006096 absorbing agent Substances 0.000 abstract description 3
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 description 10
- -1 tert-amyl Chemical group 0.000 description 9
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- VCZNNAKNUVJVGX-UHFFFAOYSA-N 4-methylbenzonitrile Chemical compound CC1=CC=C(C#N)C=C1 VCZNNAKNUVJVGX-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 150000003918 triazines Chemical class 0.000 description 3
- YOUGCCFMALFZJW-UHFFFAOYSA-N 2-[4-(2-hydroxyphenyl)-1,3,5-triazin-2-yl]phenol Chemical compound OC1=CC=CC=C1C1=NC=NC(C=2C(=CC=CC=2)O)=N1 YOUGCCFMALFZJW-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- FSTPMFASNVISBU-UHFFFAOYSA-N 2-methoxybenzonitrile Chemical compound COC1=CC=CC=C1C#N FSTPMFASNVISBU-UHFFFAOYSA-N 0.000 description 1
- NWPNXBQSRGKSJB-UHFFFAOYSA-N 2-methylbenzonitrile Chemical compound CC1=CC=CC=C1C#N NWPNXBQSRGKSJB-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000008359 benzonitriles Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- ATLPLEZDTSBZQG-UHFFFAOYSA-L dioxido-oxo-propan-2-yl-$l^{5}-phosphane Chemical compound CC(C)P([O-])([O-])=O ATLPLEZDTSBZQG-UHFFFAOYSA-L 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002960 margaryl 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])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 125000005447 octyloxy group Chemical group [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])O* 0.000 description 1
- 125000000913 palmityl 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])[H] 0.000 description 1
- 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
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 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
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH02913/93-6 | 1993-09-28 | ||
| CH291393A CH686305A5 (de) | 1993-09-28 | 1993-09-28 | Verfahren zur Herstellung von 1,3,5-Triazinen. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH07188188A true JPH07188188A (ja) | 1995-07-25 |
Family
ID=4244441
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6231956A Pending JPH07188188A (ja) | 1993-09-28 | 1994-09-28 | １、３、５−トリアジンの製造方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5545836A (OSRAM) |
| EP (1) | EP0648753B1 (OSRAM) |
| JP (1) | JPH07188188A (OSRAM) |
| KR (1) | KR100343054B1 (OSRAM) |
| CA (1) | CA2132907A1 (OSRAM) |
| CH (1) | CH686305A5 (OSRAM) |
| DE (1) | DE59402292D1 (OSRAM) |
| ES (1) | ES2100658T3 (OSRAM) |
| TW (1) | TW283706B (OSRAM) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0648754B1 (de) * | 1993-10-15 | 2000-07-12 | Ciba SC Holding AG | Verfahren zur Herstellung von Hydroxyphenyl-1,3,5-Triazinen |
| ES2205008T3 (es) * | 1995-05-18 | 2004-05-01 | Ciba Specialty Chemicals Holding Inc. | O-hidroxifenil-s-triazinas como estabilizadores de uv. |
| GB2319523B (en) | 1996-11-20 | 2000-11-08 | Ciba Sc Holding Ag | Hydroxyphenyltriazines |
| FR2757163B1 (fr) * | 1996-12-13 | 1999-02-05 | Oreal | Nouveaux derives insolubles de s-triazine, leur procede de preparation, compositions les contenant et leurs utilisations |
| US6117997A (en) * | 1997-11-19 | 2000-09-12 | Ciba Specialty Chemicals Corporation | Hydroxyphenyltriazines |
| CN1314897A (zh) | 1998-09-04 | 2001-09-26 | 西巴特殊化学品控股有限公司 | 制备2－羟基－4－烷氧苯基或2,4－二羟基苯基取代的1,3,5－三嗪uv吸收剂 |
| AU5704099A (en) | 1998-09-04 | 2000-03-27 | Cytec Technology Corp. | Process for making 2- (2,4- dihydroxyphenyl) or 2- (2,4- dialkoxyphenyl)- 4,6- bisaryl- 1,3,5- triazines |
| TWI259182B (en) | 1998-11-17 | 2006-08-01 | Cytec Tech Corp | Process for preparing triazines using a combination of Lewis acids with reaction promoters |
| WO2003037346A1 (en) * | 2001-10-31 | 2003-05-08 | Cell Therapeutics, Inc. | 6-phenyl-n-phenyl-(1,3,5) -triazine-2,4-diamine derivatives and related compounds with lysophphosphatidic acid acyltransferase beta (lpaat-beta) inhibitory activity for use in the treatment of cancer |
| US7419984B2 (en) * | 2002-10-17 | 2008-09-02 | Cell Therapeutics, Inc. | Pyrimidines and uses thereof |
| CN1738592A (zh) * | 2003-01-20 | 2006-02-22 | 西巴特殊化学品控股有限公司 | 作为uv吸收剂的三嗪衍生物 |
| US6875781B2 (en) * | 2003-04-04 | 2005-04-05 | Cell Therapeutics, Inc. | Pyridines and uses thereof |
| EP1630600A3 (en) * | 2004-07-29 | 2006-03-22 | Rohm and Haas Electronic Materials, L.L.C. | Hot melt composition and method involving forming a masking pattern |
| JP4148951B2 (ja) * | 2005-01-12 | 2008-09-10 | 株式会社東芝 | 磁気記録再生装置 |
| EP2387600B1 (en) | 2009-01-19 | 2014-04-02 | Basf Se | Organic black pigments and their preparation |
| JP5613481B2 (ja) * | 2009-07-29 | 2014-10-22 | 富士フイルム株式会社 | 新規なトリアジン誘導体、紫外線吸収剤 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3113940A (en) * | 1961-07-13 | 1963-12-10 | Monsanto Res Corp | Aromatic partial ethers of tris (2-hydroxyphenyl) triazine |
| US3113942A (en) * | 1961-07-13 | 1963-12-10 | Monsanto Res Corp | Mono-alkyl ethers of tris (2-hydroxyphenyl) triazines |
| CH480090A (de) * | 1962-10-30 | 1969-10-31 | Ciba Geigy | Verwendung von neuen Hydroxyphenyl-1,3,5-triazinen als Ultraviolettschutzmittel ausserhalb der Textilindustrie |
| US3294798A (en) * | 1964-12-14 | 1966-12-27 | American Cyanamid Co | Process for the preparation of s-triazines |
| GB1294322A (en) * | 1969-02-14 | 1972-10-25 | Ici Ltd | Colouring of polymeric materials and metal complexes therefor |
| US3932402A (en) * | 1974-06-24 | 1976-01-13 | Phillips Petroleum Company | Preparation of sym-triazines by trimerization of nitriles in trifluoromethanesulfonic acid |
| US4061856A (en) * | 1974-10-10 | 1977-12-06 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Trimerization of aromatic nitriles |
| EP0555180A1 (de) * | 1992-02-04 | 1993-08-11 | Ciba-Geigy Ag | Verfahren zur Herstellung von 2-Hydroxy-4,6-diaryl-1,3,5-triazinen |
| ATE143363T1 (de) * | 1992-02-13 | 1996-10-15 | Ciba Geigy Ag | Verfahren zur herstellung von 2-hydroxy-4,6- diaryl-1,3,5-triazin |
| US5298030A (en) * | 1992-02-21 | 1994-03-29 | Ciba-Geigy Corporation | Process for the photochemical and thermal stabilization of undyed and dyed or printed polyester fiber materials |
| JP3800344B2 (ja) * | 1992-09-07 | 2006-07-26 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | ヒドロキシフェニル−ｓ−トリアジン |
-
1993
- 1993-09-28 CH CH291393A patent/CH686305A5/de not_active IP Right Cessation
-
1994
- 1994-09-03 TW TW083108119A patent/TW283706B/zh active
- 1994-09-20 EP EP94810540A patent/EP0648753B1/de not_active Expired - Lifetime
- 1994-09-20 DE DE59402292T patent/DE59402292D1/de not_active Expired - Fee Related
- 1994-09-20 ES ES94810540T patent/ES2100658T3/es not_active Expired - Lifetime
- 1994-09-26 CA CA002132907A patent/CA2132907A1/en not_active Abandoned
- 1994-09-26 KR KR1019940024113A patent/KR100343054B1/ko not_active Expired - Fee Related
- 1994-09-27 US US08/312,597 patent/US5545836A/en not_active Expired - Lifetime
- 1994-09-28 JP JP6231956A patent/JPH07188188A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CH686305A5 (de) | 1996-02-29 |
| DE59402292D1 (de) | 1997-05-07 |
| TW283706B (OSRAM) | 1996-08-21 |
| CA2132907A1 (en) | 1995-03-29 |
| KR100343054B1 (ko) | 2002-11-27 |
| EP0648753A1 (de) | 1995-04-19 |
| US5545836A (en) | 1996-08-13 |
| EP0648753B1 (de) | 1997-04-02 |
| ES2100658T3 (es) | 1997-06-16 |
| KR950008489A (ko) | 1995-04-17 |
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