KR920004329A - 유기 에스테르 및 아미드의 제조방법 및 이를 위한 촉매계 - Google Patents
유기 에스테르 및 아미드의 제조방법 및 이를 위한 촉매계 Download PDFInfo
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- KR920004329A KR920004329A KR1019910013307A KR910013307A KR920004329A KR 920004329 A KR920004329 A KR 920004329A KR 1019910013307 A KR1019910013307 A KR 1019910013307A KR 910013307 A KR910013307 A KR 910013307A KR 920004329 A KR920004329 A KR 920004329A
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- South Korea
- Prior art keywords
- alcohol
- inorganic compound
- basic inorganic
- hydrogen
- amine
- Prior art date
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- 238000000034 method Methods 0.000 title claims 20
- 150000002895 organic esters Chemical class 0.000 title claims 3
- 150000001408 amides Chemical class 0.000 title claims 2
- 239000003054 catalyst Substances 0.000 title claims 2
- -1 aliphatic alcohols Chemical class 0.000 claims 7
- 150000002484 inorganic compounds Chemical class 0.000 claims 7
- 229910010272 inorganic material Inorganic materials 0.000 claims 7
- 150000001412 amines Chemical class 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 3
- 229910052783 alkali metal Inorganic materials 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical group NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 claims 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims 2
- 150000002894 organic compounds Chemical class 0.000 claims 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 claims 2
- 239000000376 reactant Substances 0.000 claims 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims 2
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 claims 2
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 claims 1
- XQQZRZQVBFHBHL-UHFFFAOYSA-N 12-crown-4 Chemical compound C1COCCOCCOCCO1 XQQZRZQVBFHBHL-UHFFFAOYSA-N 0.000 claims 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims 1
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 claims 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims 1
- 150000008046 alkali metal hydrides Chemical class 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 239000008139 complexing agent Substances 0.000 claims 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000011261 inert gas Substances 0.000 claims 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 claims 1
- 229910000103 lithium hydride Inorganic materials 0.000 claims 1
- JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 claims 1
- AZVCGYPLLBEUNV-UHFFFAOYSA-N lithium;ethanolate Chemical compound [Li+].CC[O-] AZVCGYPLLBEUNV-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 claims 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims 1
- 229940117969 neopentyl glycol Drugs 0.000 claims 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 claims 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 1
- 229910000104 sodium hydride Inorganic materials 0.000 claims 1
- 239000012312 sodium hydride Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/18—Preparation of carboxylic acid esters by conversion of a group containing nitrogen into an ester group
- C07C67/20—Preparation of carboxylic acid esters by conversion of a group containing nitrogen into an ester group from amides or lactams
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Measurement Of Radiation (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (18)
- (a)하기 일반식(I)의 유기 에스테르 5내지 60과 몰%를 극성 비양성자성 유기 화합물 및 염기성 무기 화합물 촉매계의 존재하에서 (b)(i)하이드록실 그룹 1개 이상을 갖는 직쇄 또는 측쇄 C4-20지방족 알콜 또는 티오에테르 알콜, 또는 (ii)하기 일반식(II)의 아민과 반응시켜 유기 에스테르 및 아미드를 제조하는 방법;(R"')2N(CH2)nR"" (II)상기식에서 R 및 R1는 동일할 수 있거나 상이할 수 있는 C1-2직쇄 또는 측쇄 알킬, C5-12사이클로알킬, C6-12또는 C7-12알크아릴 또는 아르알킬이며; A는 C1-6직쇄 또는 측쇄 알킬렌 또는 직접적인 단일결합이고; R"는 메틸 또는 에틸이며; R"'는 둘중의 1개는 수소이고; 나머지 1개의 R"'는 수소, C1-7알킬, C5-12사이클로알킬 또는 C6-12아릴이고; R""는 수소 또는 N(R"')2이고; 여기;서, R"'는 상기에서 정의한 바와 같으며; n는 0내지 8중의 하나이다.
- 제1항에 있어서, 반응물(b)가 (i)알콜인 방법.
- 제2항에 있어서, 지방족 알콜올 n-헥실 알콜, n-옥틸 알콜, 스테아릴 알콜, 1,6-헥산디올, 네오펜틸글리콜, 펜타에리트톨 및 디펜타에리트리톨 중에서 선택하는 방법.
- 제3항에 있어서, 알콜이 펜타에리트리톨인 방법.
- 제1항에 있어서, 반응물(b)가 (ii)일반식 (II)의 아민인 방법;(R"')2N(CH2)7R"" (II)상기식에서 R"'는 둘중의 1개는 수소이고; 나머지 1개의 R"'는 수소, C1-7알킬, C5-12사이클로알킬 또는 C6-12아릴이고; R""는 수소 또는 N(R"')2이고; 여기;서, R"'는 상기에서 정의한 바와 같으며; n는 0내지 8중의 하나이다.
- 제5항에 있어서, 아민을 N-메틸 아민, N,N-디에틸아민, N-사이클로헥실아민, 에틸렌 디아민, 1,3-디아미노프로판, 테트라메틸렌디아민 및 헥사메틸렌디아민 중에서 선택하는 방법.
- 제6항에 있어서, 아민이 헥사메틸렌디아민인 방법.
- 제1항에 있어서, 극성 비양성자성 유기 화합물을 N-메틸피롤리디논, 1,2-디메톡시벤젠, N,N-디메틸아세트아미드, 헥사메틸트리포스포르아미드, 디메틸포름아미드, 디메틸아미노피리딘, 테트라메틸렌설폰, 테트라메틸 글리콜 디메틸에테르, 에틸렌 글리콜 디메틸에테르, N,N,N',N'- 테트라멜틸에틸렌디아민, 1,3-디메틸-2-이미다졸리디논, 디메틸설폭사이드, 테트라히이드록푸란 및 12-크라운-4중에서 선택하는 방법.
- 제8항에 있어서, 극성비양성자성 유기 화학물이 N-메틸피롤리돈인 방법.
- 제1항에 있어서, 염기성 무기 화합물을 알칼리 금속 수산화물, 알칼리 금속알콕사이드, 알칼리 금속 아미드, 알칼리금속 알킬 아미드 및 알칼리 금속 수소화물 중에서 선택하는 방법.
- 제10항에 있어서, 염기성 무기 화합물을 칼륨 메톡사이드, 나트륨 메톡사이드, 리튬 메톡사이드, 칼륨 에톡사이드, 나트륨 에톡사이드, 리튬 에톡사이드, 칼륨 3급-부톡사이드, 나트륨-3급-부톡사이드, 리튬 아미드, n-부틸리튬 아미드, 리튬 디이소프로필 아미드, 칼륨 아미드, 리튬 수소화물 및 나트륨 수소화물 중에서 선택하는 방법.
- 제11항에서 있어서, 염기성 무기 화합물이 리튬 아미드인 방법.
- 제1항에 있어서, 반응온도가 60내지 185℃인 방법.
- 제1항에 있어서, 진공하에 수행하는 방법.
- 제1항에 있어서, 불활성 기체의 유동하에서 수행하는 방법.
- 제1항에 있어서, 염기성 무기 화합물이 알콜 또는 아민 1몰당 내지 30몰%의 양으로 존재하는 방법.
- 제12항에 있어서, 염기성 무기 화합물이 알콜 또는 아민 1몰당 5내지 7몰%의 양으로 존재하는 방법.
- 제8항에 있어서, 착화제가 1,2-디에촉시벤젠인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US562,515 | 1990-08-03 | ||
US07/562,515 US5136082A (en) | 1990-08-03 | 1990-08-03 | Process for preparing organic esters and amides and catalyst system therefor |
Publications (2)
Publication Number | Publication Date |
---|---|
KR920004329A true KR920004329A (ko) | 1992-03-27 |
KR100190784B1 KR100190784B1 (ko) | 1999-06-01 |
Family
ID=24246596
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019910013307A KR100190784B1 (ko) | 1990-08-03 | 1991-08-01 | 유기 에스테르 및 아미드의 제조방법 및 이를 위한 촉매계 |
Country Status (22)
Country | Link |
---|---|
US (1) | US5136082A (ko) |
EP (1) | EP0469331B1 (ko) |
JP (1) | JPH04234345A (ko) |
KR (1) | KR100190784B1 (ko) |
CN (1) | CN1032646C (ko) |
AT (1) | ATE142612T1 (ko) |
AU (1) | AU8143491A (ko) |
BR (1) | BR9103343A (ko) |
CA (1) | CA2045107C (ko) |
CS (1) | CS241291A3 (ko) |
DE (1) | DE69121998T2 (ko) |
DK (1) | DK0469331T3 (ko) |
ES (1) | ES2091266T3 (ko) |
FI (1) | FI913680A (ko) |
HU (1) | HUT62550A (ko) |
IL (1) | IL98548A0 (ko) |
MX (1) | MX9100190A (ko) |
NO (1) | NO912801L (ko) |
PT (1) | PT98568A (ko) |
RU (1) | RU2048465C1 (ko) |
YU (1) | YU130491A (ko) |
ZA (1) | ZA914726B (ko) |
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KR100813185B1 (ko) | 2000-06-23 | 2008-03-17 | 시바 스폐셜티 케미칼스 홀딩 인코포레이티드 | 히드록시페닐 카르복시산 에스테르의 제조방법 |
US7667066B2 (en) * | 2004-02-27 | 2010-02-23 | Albemarle Corporation | Preparation of sterically hindered hydroxyphenylcarboxylic acid esters |
US7432396B2 (en) * | 2004-06-25 | 2008-10-07 | Sumitomo Chemical Company, Limited | Process for producing (Z)-1-phenyl-1-diethylaminocarbonyl-2-hydroxymethylcyclopropane |
SA06270147B1 (ar) * | 2005-06-09 | 2009-12-22 | نوفارتيس ايه جي | عملية لتخليق 5-(مثيل–1h–إيميدازول–1-يل )–3-(ثلاثي فلـورو مثيل)–بنزامـين |
DE102005028293A1 (de) * | 2005-06-18 | 2007-01-04 | Bayer Cropscience Gmbh | Verfahren zum Herstellen von Carboxamiden |
DE102005044250A1 (de) * | 2005-09-15 | 2007-03-29 | Röhm Gmbh | Verfahren zur Herstellung von Methacrylaten mit reaktiven Doppelbindungen |
CN103508923B (zh) * | 2012-06-27 | 2016-06-29 | 中国石油化工股份有限公司 | 一种受阻酚类抗氧剂的制备方法 |
CN104496842B (zh) * | 2014-12-30 | 2017-01-25 | 天津利安隆新材料股份有限公司 | 受阻酚类抗氧剂1019的制备方法 |
CN105294441B (zh) * | 2015-12-10 | 2017-09-15 | 中国科学院新疆理化技术研究所 | 抗氧化剂八[β‑(3,5‑二叔丁基‑4‑羟基苯基)丙酸]三季戊四醇酯的合成方法 |
CN112661633A (zh) * | 2020-12-24 | 2021-04-16 | 青岛科技大学 | 一种连续制备抗氧剂1010的方法 |
CN114671777B (zh) * | 2022-03-18 | 2023-09-19 | 天津利安隆新材料股份有限公司 | 酰胺类抗氧剂的制备方法 |
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US3801540A (en) * | 1961-10-30 | 1974-04-02 | Geigy Ag J R | Dialkylhydroxyphenylalkanoic acid esters of di-and tripentaerythritol useful as polymer antioxidants |
US4228297A (en) * | 1972-12-27 | 1980-10-14 | Ciba-Geigy Corporation | Process for the production of hydroxyalkylphenyl derivatives |
DE2421309C2 (de) * | 1973-05-10 | 1983-02-24 | Sumitomo Chemical Co., Ltd., Osaka | Veresterte Isopropanolamine, Verfahren zu ihrer Herstellung und Verwendung derselben |
US3984460A (en) * | 1973-09-25 | 1976-10-05 | Ciba-Geigy Corporation | Esters of trisubstituted hydroxyphenylalkanoic acids |
US3988363A (en) * | 1973-09-25 | 1976-10-26 | Ciba-Geigy Corporation | 2,4,6-Trialkyl L-3-hydroxyphenylalkanoates |
FR2246545B1 (ko) * | 1973-10-04 | 1978-09-15 | Ile De France | |
JPS57197245A (en) * | 1981-05-28 | 1982-12-03 | Mitsui Petrochem Ind Ltd | Tetrakis(3-(3,5-dibutyl-4-hydroxyphenyl) propionyloxymethyl)methane |
US4536593A (en) * | 1982-07-13 | 1985-08-20 | Ciba-Geigy Corporation | Process for the preparation of sterically hindered hydroxphenylcarboxylic acid esters |
US4618700A (en) * | 1983-12-22 | 1986-10-21 | Ciba-Geigy Corporation | Process for the preparation of a hydroxyphenylcarboxylate |
EP0300056B1 (en) * | 1987-02-03 | 1992-01-29 | Yoshitomi Pharmaceutical Industries, Ltd. | Process for preparing tetrakis (3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyloxymethyl)methane |
-
1990
- 1990-08-03 US US07/562,515 patent/US5136082A/en not_active Expired - Fee Related
-
1991
- 1991-06-18 IL IL98548A patent/IL98548A0/xx unknown
- 1991-06-19 ZA ZA914726A patent/ZA914726B/xx unknown
- 1991-06-20 CA CA002045107A patent/CA2045107C/en not_active Expired - Fee Related
- 1991-07-05 ES ES91111181T patent/ES2091266T3/es not_active Expired - Lifetime
- 1991-07-05 AT AT91111181T patent/ATE142612T1/de not_active IP Right Cessation
- 1991-07-05 EP EP91111181A patent/EP0469331B1/en not_active Expired - Lifetime
- 1991-07-05 DK DK91111181.3T patent/DK0469331T3/da active
- 1991-07-05 DE DE69121998T patent/DE69121998T2/de not_active Expired - Fee Related
- 1991-07-08 CN CN91104729A patent/CN1032646C/zh not_active Expired - Fee Related
- 1991-07-12 MX MX9100190A patent/MX9100190A/es not_active IP Right Cessation
- 1991-07-17 NO NO91912801A patent/NO912801L/no unknown
- 1991-07-19 HU HU912429A patent/HUT62550A/hu unknown
- 1991-07-24 YU YU130491A patent/YU130491A/sh unknown
- 1991-07-29 AU AU81434/91A patent/AU8143491A/en not_active Abandoned
- 1991-08-01 FI FI913680A patent/FI913680A/fi not_active Application Discontinuation
- 1991-08-01 KR KR1019910013307A patent/KR100190784B1/ko not_active IP Right Cessation
- 1991-08-02 BR BR919103343A patent/BR9103343A/pt not_active IP Right Cessation
- 1991-08-02 CS CS912412A patent/CS241291A3/cs unknown
- 1991-08-02 RU SU915001199A patent/RU2048465C1/ru active
- 1991-08-02 PT PT98568A patent/PT98568A/pt not_active Application Discontinuation
- 1991-08-02 JP JP3194017A patent/JPH04234345A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
CS241291A3 (en) | 1992-02-19 |
CA2045107A1 (en) | 1992-02-04 |
KR100190784B1 (ko) | 1999-06-01 |
CN1032646C (zh) | 1996-08-28 |
CA2045107C (en) | 1997-12-09 |
BR9103343A (pt) | 1992-05-05 |
DE69121998D1 (de) | 1996-10-17 |
PT98568A (pt) | 1992-07-31 |
HUT62550A (en) | 1993-05-28 |
DK0469331T3 (da) | 1996-09-30 |
DE69121998T2 (de) | 1997-02-20 |
US5136082A (en) | 1992-08-04 |
ES2091266T3 (es) | 1996-11-01 |
IL98548A0 (en) | 1992-07-15 |
EP0469331B1 (en) | 1996-09-11 |
AU8143491A (en) | 1992-02-06 |
MX9100190A (es) | 1992-04-01 |
HU912429D0 (en) | 1991-12-30 |
RU2048465C1 (ru) | 1995-11-20 |
CN1058584A (zh) | 1992-02-12 |
EP0469331A1 (en) | 1992-02-05 |
NO912801D0 (no) | 1991-07-17 |
YU130491A (sh) | 1994-05-10 |
FI913680A0 (fi) | 1991-08-01 |
ATE142612T1 (de) | 1996-09-15 |
NO912801L (no) | 1992-02-04 |
FI913680A (fi) | 1992-02-04 |
JPH04234345A (ja) | 1992-08-24 |
ZA914726B (en) | 1992-05-27 |
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