KR890009850A - 불포화 카르본산 아미드의 제조방법 - Google Patents
불포화 카르본산 아미드의 제조방법 Download PDFInfo
- Publication number
- KR890009850A KR890009850A KR1019880016879A KR880016879A KR890009850A KR 890009850 A KR890009850 A KR 890009850A KR 1019880016879 A KR1019880016879 A KR 1019880016879A KR 880016879 A KR880016879 A KR 880016879A KR 890009850 A KR890009850 A KR 890009850A
- Authority
- KR
- South Korea
- Prior art keywords
- hydroxide
- alkali metal
- carboxylic acid
- potassium
- acid amide
- Prior art date
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 title claims 8
- 238000004519 manufacturing process Methods 0.000 title claims 4
- 238000000034 method Methods 0.000 claims 16
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical group [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 6
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 claims 6
- 229910052783 alkali metal Inorganic materials 0.000 claims 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 5
- 150000001340 alkali metals Chemical group 0.000 claims 5
- 239000003054 catalyst Substances 0.000 claims 5
- -1 cyclic amine Chemical class 0.000 claims 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 4
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 4
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 4
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 4
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 4
- CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 claims 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims 2
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 claims 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims 2
- 239000000920 calcium hydroxide Substances 0.000 claims 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims 2
- 239000000292 calcium oxide Substances 0.000 claims 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims 2
- 150000001733 carboxylic acid esters Chemical class 0.000 claims 2
- 238000003795 desorption Methods 0.000 claims 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical group [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims 2
- 239000000347 magnesium hydroxide Substances 0.000 claims 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims 2
- 239000000395 magnesium oxide Substances 0.000 claims 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical group [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 2
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 2
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 claims 2
- 229910001866 strontium hydroxide Inorganic materials 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 claims 1
- 229910001863 barium hydroxide Inorganic materials 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/09—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton
-
- 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
- C07D295/16—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 acylated on ring nitrogen atoms
- C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
-
- 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
- C07D295/16—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 acylated on ring nitrogen atoms
- C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (19)
- 하기 일반식(Ⅰ)의 β-알콕시 치환 카르본산 에스테르와 하기일반식(Ⅱ)의 환식 아민을 반응시켜서 β-알콕시 치환 카르본산 아미드 화합물을 합성하고, 이어서 염기성 촉매를 사용하여 알콜을 탈리함으로써 불포화기를 형성시킴을 특징으로 하는 하기 일반식(Ⅲ)의 불포화 카르본산 아미드의 제조 방법.[상기식중, R1은 수소 원자 또는 메틸기이고, R2및 R3는 탄소수 1~3의 알킬기이며, Y는 산소 원자 또는 N-메틸아미노기이고, m 및 n은 m+n이 3~5의 정수를 나타낸다.]
- 제 1 항에 있어서, 환식 아민이 모르폴린 또는 N-메틸피페라진인 방법.
- 제 1 항 또는 2항에 있어서, 염기성 촉매가 알칼리 금속 알콜레이트, 알칼리 금속 수산화물, 알칼리 토금속 수산화물, 알칼리 토금속 산화물 또는 알칼리 금속 탄산염인 방법.
- 제 3 항에 있어서, 알칼리 금속 알콜레이트가 나트륨 메틸레이트, 나트륨 에틸레이트, 칼륨 메틸레이트 또는 칼륨 에틸레이트인 방법.
- 제 3 항에 있어서, 알칼리 금속 수산화물이 수산화리튬, 수산화 나트륨, 수산화 칼륨, 수산화 루비듐 또는 수산화 세슘인 방법.
- 제 3 항에 있어서, 알칼리 토금속 수산화물이 수산화 마그네슘, 수산화 칼슘, 수산화 스트론튬 또는 산화 바륨인 방법.
- 제 3 항에 있어서, 알칼리 토금속 산화물이 산화 마그네슘, 산화 칼슘 또는 산화바륨인 방법.
- 제 3 항에 있어서, 알칼리 금속 탄산염이 탄산나트륨 또는 탄산 칼륨인 방법.
- 하기 일반식(Ⅳ)의 β-알콕시 치환 카르본산 에스테르와 하기 일반식 (Ⅴ)의 환식 아민을 반응시켜 β-알콕시 치환 카르본산 아미드 화합물을 합성하고, 이어서 염기성 촉매를 사용하여 알콜을 탈리함으로써 불포화기를 형성시킴을 특징으로 하는 하기 일반식(Ⅵ)의 불포화 카르본산 아미드의 제조방법[상기식중, R4는 수소 원자 또는 메틸기이고, R5및 R6는 탄소수 1~3의 알킬기이며, Y는 메틸렌기이고, m 및 n은 m+n이 3~5의 정수이다.]
- 제 9 항에 있어서, 환식 아민이 피롤피딘, 피페리딘 또는 헥사메틸렌이민인 방법.
- 제 9 또는 10항에 있어서, 염기성 촉매가 알칼리 금속 수산화물, 알칼리 토금속 수산화물, 알칼리 토금속 산화물 또는 알칼리 금속 탄산염인 방법.
- 제 11 항에 있어서, 알칼리 금속 수산화물이 수산화 리튬인 방법.
- 제 11항에 있어서, 알칼리 금속 수산화물이 수산화 나트륨, 수산화 칼륨, 수산화 루비듐 또는 수산화 세슘인 방법.
- 제 11 항에 있어서, 알칼리 토금속 수산화물이 수산화 마그네슘, 수산화 칼슘, 수산화 스트론튬 또는 수산화 바륨인 방법.
- 제 11 항에 있어서, 알칼리 토금속 산화물이 산화 마그네슘, 산화 칼슘 또는 산화바륨인 방법.
- 제 11 항에 있어서, 알칼리 금속 탄산염이 탄산 나트륨 또는 탄산 칼륨인 방법.
- 하기 일반식(Ⅶ)의 β-메톡시 치환 카르본산 에스테르와 하기 일반식(Ⅷ)의 환식 아민을 반응시켜서, β-메톡시 치환 카르본산 아미드 화합물을 합성하고, 이어서 하기 일반식(Ⅸ)의 알칼리 금속 알콜레이트를 촉매로서 사용하여 메탄올을 탈리하여 불포화기를 형성시킴을 특징으로 하는 하기 일반식(Ⅹ)의 불포화 카르본산 아미드의 제조 방법[R7은 수소원자 또는 메틸기이고, R8은 탄소수 1-3의 알킬기이며, Y는 메틸렌기이며, m 및 n은 m+n이 3~5의 정수이고, R9는 메틸기 또는 에틸기이고, M은 나트륨 또는 칼륨으로부터 선택되는 알칼리 금속이다.]
- 제 17 항에 있어서, 환식 아민이 피롤리딘, 피페리딘 또는 헥사메틸렌이민인 방법.
- 제 17 항에 있어서, 알칼리 금속 알콜레이트가 나트륨 메틸레이트, 나트륨 에틸레이트, 칼륨 메틸레이트 또는 칼륨 에틸레이트인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62-317450 | 1987-12-17 | ||
| JP31745087 | 1987-12-17 | ||
| JP63-194535 | 1988-08-05 | ||
| JP63194535A JPH01250371A (ja) | 1987-08-11 | 1988-08-05 | 不飽和カルボン酸アミドの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR890009850A true KR890009850A (ko) | 1989-08-04 |
| KR910003334B1 KR910003334B1 (ko) | 1991-05-27 |
Family
ID=26508557
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019880016879A KR910003334B1 (ko) | 1987-12-17 | 1988-12-17 | 불포화 카르본산 아미드의 제조방법 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4978754A (ko) |
| EP (1) | EP0321256A3 (ko) |
| KR (1) | KR910003334B1 (ko) |
| CA (1) | CA1322750C (ko) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5519086A (en) * | 1991-12-30 | 1996-05-21 | Bridgestone Corporation | Low-hysteresis elastomer compositions using amino-substituted aryllithium polymerization initiators |
| US5523371A (en) * | 1991-12-30 | 1996-06-04 | Bridgestone Corporation | Functionalized polymer of improved hysteresis properties prepared using amino-substituted aryllithium polymerization initiators |
| US5332810A (en) * | 1992-10-02 | 1994-07-26 | Bridgestone Corporation | Solubilized anionic polymerization initiator and preparation thereof |
| US5329005A (en) * | 1992-10-02 | 1994-07-12 | Bridgestone Corporation | Soluble anionic polymerization initiators and preparation thereof |
| US6025450A (en) * | 1992-10-02 | 2000-02-15 | Bridgestone Corporation | Amine containing polymers and products therefrom |
| US5552473A (en) * | 1992-10-02 | 1996-09-03 | Bridgestone Corporation | Functionalized polymer and rubber compositions produced from solubilized anionic polymerization initiators |
| US5393721A (en) * | 1992-10-16 | 1995-02-28 | Bridgestone Corporation | Anionic polymerization initiators and reduced hysteresis products therefom |
| US5674798A (en) * | 1992-10-16 | 1997-10-07 | Bridgestone Corporation | Hydrocarbon soluble anionic polymerization initiators |
| US5643848A (en) * | 1992-10-30 | 1997-07-01 | Bridgestone Corporation | Soluble anionic polymerization initiators and products therefrom |
| ES2110557T3 (es) * | 1992-10-30 | 1998-02-16 | Bridgestone Corp | Iniciadores de polimerizacion anionica solubles y productos de aquellos. |
| EP0622381B1 (en) * | 1993-04-30 | 1998-07-29 | Bridgestone Corporation | Anionic polymerization initiators and reduced hysteresis products therefrom |
| US5491230A (en) * | 1993-12-29 | 1996-02-13 | Bridgestone Corporation | Anionic polymerization initiators containing adducts of cyclic secondary amines and conjugated dienes, and products therefrom |
| US5521309A (en) * | 1994-12-23 | 1996-05-28 | Bridgestone Corporation | Tertiary-amino allyl-or xylyl-lithium initiators and method of preparing same |
| US5574109A (en) * | 1995-02-01 | 1996-11-12 | Bridgestone Corporation | Aminoalkyllithium compounds containing cyclic amines and polymers therefrom |
| US5785778A (en) * | 1995-02-01 | 1998-07-28 | Bridgestone Corporation | Aminoalkyllithium compounds containing cyclic amines and polymers therefrom |
| US6080835A (en) | 1995-02-01 | 2000-06-27 | Bridgestone Corporation | Aminoalkyllithium compounds containing cyclic amines and polymers therefrom |
| US5496940A (en) * | 1995-02-01 | 1996-03-05 | Bridgestone Corporation | Alkyllithium compounds containing cyclic amines and their use in polymerization |
| EP0818439B1 (en) * | 1996-07-02 | 1999-10-13 | Nisshin Flour Milling Co., Ltd. | Imide derivatives |
| WO2007010497A1 (en) * | 2005-07-21 | 2007-01-25 | The Procter & Gamble Company | A disposable mat, a container comprising a disposable mat, a method of promoting the sale of a disposable mat, and a process of manufacturing a disposable mat |
| JP6277806B2 (ja) | 2013-06-05 | 2018-02-14 | 株式会社リコー | インク |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2702822A (en) * | 1952-06-12 | 1955-02-22 | Hercules Powder Co Ltd | Production of unsaturated amides |
| US3914303A (en) * | 1972-09-01 | 1975-10-21 | Cpc International Inc | Preparation of N,N-dialkylacylamides |
| GB1438389A (en) * | 1972-10-31 | 1976-06-03 | Kohjin Co | N-substituted methacryl-or acrylamides |
| DE2623838A1 (de) * | 1976-05-28 | 1977-12-15 | Basf Ag | Verfahren zur herstellung von n-substituierten acrylamiden |
-
1988
- 1988-12-05 CA CA000585026A patent/CA1322750C/en not_active Expired - Fee Related
- 1988-12-12 US US07/282,687 patent/US4978754A/en not_active Expired - Fee Related
- 1988-12-16 EP EP19880311899 patent/EP0321256A3/en not_active Withdrawn
- 1988-12-17 KR KR1019880016879A patent/KR910003334B1/ko not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US4978754A (en) | 1990-12-18 |
| EP0321256A3 (en) | 1990-10-10 |
| EP0321256A2 (en) | 1989-06-21 |
| KR910003334B1 (ko) | 1991-05-27 |
| CA1322750C (en) | 1993-10-05 |
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