KR910004671A - 알파-올레핀류의 중합반응 및 공중합반응촉매와 그 방법 - Google Patents
알파-올레핀류의 중합반응 및 공중합반응촉매와 그 방법 Download PDFInfo
- Publication number
- KR910004671A KR910004671A KR1019900011924A KR900011924A KR910004671A KR 910004671 A KR910004671 A KR 910004671A KR 1019900011924 A KR1019900011924 A KR 1019900011924A KR 900011924 A KR900011924 A KR 900011924A KR 910004671 A KR910004671 A KR 910004671A
- Authority
- KR
- South Korea
- Prior art keywords
- component
- catalyst
- group
- cyclopentadienyl
- bis
- Prior art date
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- 238000000034 method Methods 0.000 title claims 5
- 238000007334 copolymerization reaction Methods 0.000 title claims 3
- 239000004711 α-olefin Substances 0.000 title claims 3
- 238000006116 polymerization reaction Methods 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims 10
- -1 ethylene-bis (indenyl ) Chemical class 0.000 claims 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 2
- 239000005977 Ethylene Substances 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims 2
- 229910052735 hafnium Inorganic materials 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 2
- 229910052726 zirconium Inorganic materials 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical group C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 1
- QUUNIIZGAURLKQ-UHFFFAOYSA-N C(CCCCCCC)Cl.C1(C=CC=C1)[Zr]C1C=CC=C1 Chemical compound C(CCCCCCC)Cl.C1(C=CC=C1)[Zr]C1C=CC=C1 QUUNIIZGAURLKQ-UHFFFAOYSA-N 0.000 claims 1
- 239000004698 Polyethylene Substances 0.000 claims 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims 1
- PGOXJIBERNIRFR-UHFFFAOYSA-L [Cl-].[Cl-].C(C)(C)[Hf+2]C1=C(C=CC=2C3=CC=CC=C3CC1=2)C1C=CC=C1 Chemical compound [Cl-].[Cl-].C(C)(C)[Hf+2]C1=C(C=CC=2C3=CC=CC=C3CC1=2)C1C=CC=C1 PGOXJIBERNIRFR-UHFFFAOYSA-L 0.000 claims 1
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 150000001343 alkyl silanes Chemical class 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- QRUYYSPCOGSZGQ-UHFFFAOYSA-L cyclopentane;dichlorozirconium Chemical compound Cl[Zr]Cl.[CH]1[CH][CH][CH][CH]1.[CH]1[CH][CH][CH][CH]1 QRUYYSPCOGSZGQ-UHFFFAOYSA-L 0.000 claims 1
- 150000001993 dienes Chemical class 0.000 claims 1
- UBHZUDXTHNMNLD-UHFFFAOYSA-N dimethylsilane Chemical compound C[SiH2]C UBHZUDXTHNMNLD-UHFFFAOYSA-N 0.000 claims 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 1
- 239000007788 liquid Substances 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
- 239000000178 monomer Substances 0.000 claims 1
- 230000000737 periodic effect Effects 0.000 claims 1
- 229920000573 polyethylene Polymers 0.000 claims 1
- 230000000379 polymerizing effect Effects 0.000 claims 1
- 229910052719 titanium Inorganic materials 0.000 claims 1
- 239000010936 titanium Substances 0.000 claims 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 claims 1
Classifications
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- 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
- C08F4/00—Polymerisation catalysts
-
- 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
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/65912—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an organoaluminium compound
-
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/6592—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
- C08F4/65922—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/943—Polymerization with metallocene catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (13)
- a) 다음 구조식의 화합물과(여기서, M은 원소주기율의 4b 족 금속을 나타내고, 각 R은 독립적으로 할로겐 원자나 직쇄 혹은 측쇄 C1-C10알킬기나 또는 아릴기를 나타내고, 또한 각 Cp는 독립적으로 하나나 그이상의 직쇄나 측쇄 C1-C10알킬 치환물을 갖고 있는 시클로펜타디에닐, 인데닐 또는 플루오레닐기를 나타내고 Cp기는 또한 탄소원자나 알킬실란 가교구조와 함께 연결할수 있다).b) 다음 구조식의 트리알킬알루미늄과(여기서, 각 R′는 독립적으로 직쇄나 측쇄 C1-C10알킬기 혹은 아릴기를 나타낸다).또한 c) 다음 구조식의 디스탄옥산과 접촉시켜서 제조하고,(여기서, 각 R″는 독립적으로 직쇄나 측쇄의 C1-C10알킬기나 아릴기를 나타낸다). 이때의 성분 (a)에 대한 성분(b)의 몰비율이 약 100/1 내지 700,000/1 이고 또한 성분(b)에 대한 성분(c)이 몰비율이 1/1 이하인 것으로된 알파-올레핀 중합반응 및 공중합반응용촉매.
- 제1항에 있어서, (a)성분중 금속(M)을 티타늄, 지르코늄, 또한 하프늄중에서 선택하고 또한 각 R이 염소원자나 C1-C8알킬기를 나타내는 것을 특징으로 하는 촉매.
- 제1항에 있어서, (a)성분중 Cp기를 직쇄나 측쇄 C1-C4알킬렌기 혹은 디알킬실릴기 특히 디메틸실란과 함께 연결하는 것을 특징으로 하는 촉매.
- 제1항에 있어서, 성분 (a)를 비스(시클로펜타디에닐) 지르코늄 디클로라이드, 비스(시클로펜타디에닐) 지르코늄 옥틸 클로라이드, 비스(시클로펜타디에닐), 하프늄 디메틸, 에틸렌-비스(인데닐) 지르코늄 디클로라이드, 에틸렌-비스(인데닐)하프늄 디클로라이드, 또한 이소프로필(시클로펜타디에닐-1-플루오레닐)하프늄 디클로라이드 중에서 선택하는 것을 특징으로 하는 촉매.
- 제1항에 있어서, 성분(b)중 각 R′이 C1-C4알킬기를 나타내는 것을 특징으로 하는 촉매.
- 제1항에 있어서, 성분(b)가 트리메틸알루미늄인 것을 특징으로하는 촉매.
- 제1항에 있어서, 성분(c)중 각 R″이 메틸기를 나타내는 것을 특징으로 하는 촉매.
- 제1항에 있어서, 성분(b)에 대한 성분(c)의 몰비율이 0.3/1 내지 0.9/1로 변하는 것을 특징으로 하는 촉매.
- 제1항에 있어서, 성분(a)에 대한 성분(b)의 몰비율이 약 300/1 내지 약 300,000/1 까지 변하는 성분(b)에 대한 성분(c)의 몰비율은 0.7/1내지 0.8/1 정도인 것을 특징으로 하는 촉매.
- 제1항 내지 제9항의 구성분(a), (b) 또한 (c)를 불활성 유기용매속에서 상호 접촉시키고 실온에서 조작하여 촉매를 제조하는 방법.
- 제10항에 있어서, 유기용매가 지방족 또는 방향족 탄화수소이고 특히 반응조건하에서 액상이거나 액화가능한 실제 단량체나 헥산, 헵탄, 또는 톨루엔인 것을 특징으로 하는 방법.
- 제1항 내지 제9항의 촉매가 존재하는 곳에서 실행하는 것을 특징으로 하는 알파-올레핀의 중합반응 또는 공중합 반응방법.
- 제12항에 있어서, 에틸렌을 중합하여 직쇄 폴리에틸렌을 만들거나, 프로필렌 혹은 그보다 큰 알파-올레핀을 중합하여 아택티, 신디오택틱 또는 이소택틱 이성핵을 만들거나, 혹은 에틸렌을 프로필렌과 또는 그보다 큰 알파-올레핀과 공중합 반응시켜 LLDPF로 만들거나 또는 에틸렌, 프로필렌과 디엔을 삼중중합반응시키는 것을 특징으로 하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT21439A/89 | 1989-08-03 | ||
| IT8921439A IT1231774B (it) | 1989-08-03 | 1989-08-03 | Catalizzatore e procedimento per la polimerizzazione e per la copolimerizzazione di alfa olefine. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR910004671A true KR910004671A (ko) | 1991-03-29 |
| KR930003690B1 KR930003690B1 (ko) | 1993-05-08 |
Family
ID=11181813
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019900011924A KR930003690B1 (ko) | 1989-08-03 | 1990-08-03 | 알파-올레핀류의 중합반응 및 공중합반응촉매와 그 방법 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5128295A (ko) |
| EP (1) | EP0422703B1 (ko) |
| JP (1) | JP2864158B2 (ko) |
| KR (1) | KR930003690B1 (ko) |
| CN (1) | CN1031580C (ko) |
| AT (1) | ATE91133T1 (ko) |
| BR (1) | BR9003903A (ko) |
| CA (1) | CA2022566C (ko) |
| DE (1) | DE69002094T2 (ko) |
| DK (1) | DK0422703T3 (ko) |
| ES (1) | ES2057359T3 (ko) |
| IT (1) | IT1231774B (ko) |
| NO (1) | NO174749C (ko) |
| ZA (1) | ZA906017B (ko) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5258475A (en) * | 1991-07-12 | 1993-11-02 | Mobil Oil Corporation | Catalyst systems for polymerization and copolymerization of olefins |
| US5594078A (en) * | 1991-07-23 | 1997-01-14 | Phillips Petroleum Company | Process for producing broad molecular weight polyolefin |
| US5326837A (en) * | 1992-11-20 | 1994-07-05 | Mobil Oil Corporation | Catalyst systems for syndiospecific polymerization of styrenes |
| IT1269805B (it) * | 1994-05-20 | 1997-04-15 | Enichem Spa | Catalizzatore per la (co)polimerizzazione dell'etilene e procedimento per il suo ottenimento |
| US5554775A (en) * | 1995-01-17 | 1996-09-10 | Occidental Chemical Corporation | Borabenzene based olefin polymerization catalysts |
| IT1277677B1 (it) * | 1995-12-21 | 1997-11-11 | Enichem Spa | Procedimento per la preparazione di polimeri vinilaromatici cristallini a struttura predominantemente sindiotattica |
| IT1282666B1 (it) | 1996-02-22 | 1998-03-31 | Enichem Spa | Catalizzatore metallocenico sostituito per la (co) polimerizzazione delle olefine |
| US20030069127A1 (en) * | 2000-12-26 | 2003-04-10 | Kazuo Takaoki | Modified particle,support, catalyst component for addition polymerization, catalyst for addition polymerization, and process for producing addition polymer |
| US20050076591A1 (en) * | 2003-10-08 | 2005-04-14 | David Koeller | Magnetic image assembly to mount on garage door panels and a system and a method for decorating a garage door |
| ITMI20122206A1 (it) | 2012-12-20 | 2014-06-21 | Versalis Spa | Procedimento per la preparazione di (co)polimeri di dieni coniugati in presenza di un sistema catalitico comprendente un complesso bis-immino-piridinico di cobalto |
| ITMI20122201A1 (it) | 2012-12-20 | 2014-06-21 | Versalis Spa | Complesso osso-azotato di cobalto, sistema catalitico comprendente detto complesso osso-azotato e procedimento per la (co)polimerizzazione di dieni coniugati |
| ITMI20122199A1 (it) | 2012-12-20 | 2014-06-21 | Versalis Spa | Procedimento per la preparazione di (co)polimeri di dieni coniugati in presenza di un sistema catalitico comprendente un complesso bis-imminico di cobalto |
| ITMI20122203A1 (it) | 2012-12-20 | 2014-06-21 | Versalis Spa | Procedimento per la preparazione di (co)polimeri di dieni coniugati in presenza di un sistema catalitico comprendente un complesso osso-azotato di cobalto |
| ITMI20131828A1 (it) | 2013-11-05 | 2015-05-06 | Versalis Spa | Polibutadieni di-blocco stereoregolari a struttura 1,4-cis/1,2 sindiotattica da polimerizzazione stereospecifica |
| ITMI20131830A1 (it) | 2013-11-05 | 2015-05-06 | Versalis Spa | Polibutadieni di-blocco stereoregolari a struttura 1,4-cis/1,2 sindiotattica da polimerizzazione stereospecifica |
| EP3194409B1 (en) | 2014-09-17 | 2019-09-11 | Versalis S.p.A. | Pyridine complex of zirconium, catalytic system comprising said pyridine complex of zirconium and process of (co)polymerization of conjugated dienes |
| ITUB20152581A1 (it) | 2015-07-29 | 2017-01-29 | Versalis Spa | Complesso azotato di titanio, sistema catalitico comprendente detto complesso azotato di titanio e procedimento per la (co)polimerizzazione di dieni coniugati |
| ITUA20163932A1 (it) | 2016-05-30 | 2017-11-30 | Versalis Spa | Complesso osso-azotato di ferro, sistema catalitico comprendente detto complesso osso-azotato di ferro e procedimento per la (co)polimerizzazione di dieni coniugati |
| IT201700059763A1 (it) | 2017-05-31 | 2018-12-01 | Versalis Spa | Copolimeri butadiene-isoprene di-blocco e procedimento per la loro preparazione |
| IT201700109176A1 (it) | 2017-09-29 | 2019-03-29 | Versalis Spa | Complesso bis-imminico di titanio, sistema catalitico comprendente detto complesso bis-imminico di titanio e procedimento per la (co)polimerizzazione di dieni coniugati |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL97329C (ko) * | 1955-12-28 | |||
| US3332927A (en) * | 1966-02-14 | 1967-07-25 | Cabot Corp | Process for polymerization |
| US3449263A (en) * | 1966-02-16 | 1969-06-10 | American Can Co | Olefin polymerization process |
| DE2123088A1 (ko) * | 1971-05-10 | 1972-11-23 | ||
| US3950268A (en) * | 1971-11-08 | 1976-04-13 | Standard Oil Company | Catalyst for the polymerization of olefins |
| US4931417A (en) * | 1987-11-09 | 1990-06-05 | Chisso Corporation | Transition-metal compound having a bis-substituted-cyclopentadienyl ligand of bridged structure |
-
1989
- 1989-08-03 IT IT8921439A patent/IT1231774B/it active
-
1990
- 1990-07-21 DK DK90202006.4T patent/DK0422703T3/da active
- 1990-07-21 ES ES90202006T patent/ES2057359T3/es not_active Expired - Lifetime
- 1990-07-21 DE DE90202006T patent/DE69002094T2/de not_active Expired - Lifetime
- 1990-07-21 EP EP90202006A patent/EP0422703B1/en not_active Expired - Lifetime
- 1990-07-21 AT AT90202006T patent/ATE91133T1/de not_active IP Right Cessation
- 1990-07-31 ZA ZA906017A patent/ZA906017B/xx unknown
- 1990-08-01 US US07/561,088 patent/US5128295A/en not_active Expired - Lifetime
- 1990-08-01 NO NO903380A patent/NO174749C/no not_active IP Right Cessation
- 1990-08-02 BR BR909003903A patent/BR9003903A/pt not_active IP Right Cessation
- 1990-08-02 CA CA002022566A patent/CA2022566C/en not_active Expired - Lifetime
- 1990-08-02 JP JP2204032A patent/JP2864158B2/ja not_active Expired - Fee Related
- 1990-08-03 KR KR1019900011924A patent/KR930003690B1/ko not_active IP Right Cessation
- 1990-08-03 CN CN90107351A patent/CN1031580C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| NO174749B (no) | 1994-03-21 |
| NO903380D0 (no) | 1990-08-01 |
| ZA906017B (en) | 1991-05-29 |
| US5128295A (en) | 1992-07-07 |
| KR930003690B1 (ko) | 1993-05-08 |
| CA2022566C (en) | 2001-10-09 |
| DK0422703T3 (da) | 1993-10-11 |
| JPH0370708A (ja) | 1991-03-26 |
| NO174749C (no) | 1994-06-29 |
| NO903380L (no) | 1991-02-04 |
| CN1031580C (zh) | 1996-04-17 |
| DE69002094D1 (de) | 1993-08-05 |
| JP2864158B2 (ja) | 1999-03-03 |
| BR9003903A (pt) | 1991-09-03 |
| IT8921439A0 (it) | 1989-08-03 |
| ES2057359T3 (es) | 1994-10-16 |
| EP0422703A1 (en) | 1991-04-17 |
| EP0422703B1 (en) | 1993-06-30 |
| CN1051363A (zh) | 1991-05-15 |
| CA2022566A1 (en) | 1991-02-04 |
| DE69002094T2 (de) | 1994-01-20 |
| ATE91133T1 (de) | 1993-07-15 |
| IT1231774B (it) | 1991-12-21 |
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