KR950008526A - 3가 인의 사이클릭 화합물 - Google Patents
3가 인의 사이클릭 화합물 Download PDFInfo
- Publication number
- KR950008526A KR950008526A KR1019940023934A KR19940023934A KR950008526A KR 950008526 A KR950008526 A KR 950008526A KR 1019940023934 A KR1019940023934 A KR 1019940023934A KR 19940023934 A KR19940023934 A KR 19940023934A KR 950008526 A KR950008526 A KR 950008526A
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- KR
- South Korea
- Prior art keywords
- compound
- different
- same
- radical
- hydrogen
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- -1 Phosphorus Cyclic Compounds Chemical class 0.000 title claims abstract 5
- 229910052698 phosphorus Inorganic materials 0.000 title 1
- 239000011574 phosphorus Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 12
- 239000003054 catalyst Substances 0.000 claims abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 150000003254 radicals Chemical class 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 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 claims 1
- 229910000799 K alloy Inorganic materials 0.000 claims 1
- 229910000528 Na alloy Inorganic materials 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000004957 naphthylene group Chemical group 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 150000002739 metals Chemical class 0.000 abstract 2
- 239000000470 constituent Substances 0.000 abstract 1
- 239000003446 ligand Substances 0.000 abstract 1
- 230000000737 periodic effect Effects 0.000 abstract 1
- 150000003018 phosphorus compounds Chemical group 0.000 abstract 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2442—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
- B01J31/2461—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as ring members in the condensed ring system or in a further ring
- B01J31/2471—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as ring members in the condensed ring system or in a further ring with more than one complexing phosphine-P atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
- C07F9/65683—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2419—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member
- B01J31/2428—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member with more than one complexing phosphine-P atom
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2442—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
- B01J31/2461—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as ring members in the condensed ring system or in a further ring
- B01J31/2471—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as ring members in the condensed ring system or in a further ring with more than one complexing phosphine-P atom
- B01J31/2476—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as ring members in the condensed ring system or in a further ring with more than one complexing phosphine-P atom comprising aliphatic or saturated rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/14—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the side-chain of aromatic compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/822—Rhodium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2419—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member
- B01J31/2428—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member with more than one complexing phosphine-P atom
- B01J31/2433—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member with more than one complexing phosphine-P atom comprising aliphatic or saturated rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Inorganic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Lubricants (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
본 발명은 신규 사이클릭 인(Ⅲ)화합물 및 이의 제조방법에 대해 기술하고 있다. 인 화합물은 두 자리 리간드로서 작용하여 금속, 특히 주기율표의 8족 금속과 함께 착화합물을 형성하며, 이 착화합물은 촉매 시스템의 성분으로서 사용될 수 있다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (12)
- 일반식(Ⅰ)의 화합물.상기식에서, 라디칼은 포화되거나, 단일 또는 다중 불포화되고, 5원 또는 6원 환이며, R1및 R2은 동일하거나 상이하며, 수소, 탄소수 1내지 5의 알킬, 아르알킬 또는 알콕시 라디칼이거나, 할로겐 원자 또는 어닐링된 (annelated)벤젠 환 또는 나프탈렌 환이고, R3및 R4는 동일하거나 상이하고, 수소 또는 메틸 라디칼이며, m 및 n은 동일하거나 상이하며, 0 또는 1이고, s 및 t는 동일하거나 상이하고, 4 또는 5이며, p, q 및 r은 동일하거나 상이하며, 0, 1, 2 또는 3이고, Ar은 탄소수 6 내지 18의 치환되거나 치환되지 않은 방향족 라디칼이다.
- 제1항에 있어서, 라디칼 R3및 R4가 H인 화합물.
- 제1항 또는 제2항에 있어서, 라디칼 R1및 R2가 수소 또는 메틸 라디칼인 화합물.
- 제1항 내지 제3항 중의 어느 한 항에 있어서, Ar이 페닐렌, 나프틸렌, 1, 1'-비페닐렌 또는 1, 1'-비나프틸렌 라디칼인 화합물.
- 제1항 내지 제4항 중의 어느 한 항에 있어서, s 및 t가 4인 화합물.
- 제1항 내지 제5항 중의 어느 한 항에 있어서, p 및 r이 동일하거나 상이하고 1인 화합물.
- 제1항 내지 제6항 중의 어느 한 항에 있어서, q가 O 또는 1인 화합물.
- 2, 2'-비스 (3, 4-디메틸포스폴메틸렌)-1, 1'-비페닐인 화합물.
- 2, 2'-비스 (3, 4-디메틸포스폴메틸렌)-1, 1'-비나프틸인 화합물.
- 일반식(Ⅱ)의 화합물을 알칼리 금속과 반응시킨 다음, 생성물을 일반식(Ⅲ)의 화합물과 반응시킴을 포함하는, 제1항 내지 제9항 중의 어느 한 항에서 청구한 화합물의 제조방법.상기식에서 R1, R2, R3,R4, m, n, p, q, r s, t x 및 Ar은 제1항에서 정의한 바와 같고, Hal은 할로겐, 특히 Cl 또는 Br이다.
- 제10항에 있어서, 사용되는 알칼리 금속이 나트륨/칼륨 알로이(alloy)인 제조방법.
- 제1항 내지 제9항 중의 어느 한 항에서 청구한 화합물의 균일 가용성 촉매 시스템의 성분으로서의 용도.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE?P4333307.9? | 1993-09-30 | ||
DE4333307A DE4333307A1 (de) | 1993-09-30 | 1993-09-30 | Cyclische Verbindungen des dreiwertigen Phosphors |
DEWPP4333307.9GH | 1993-09-30 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR950008526A true KR950008526A (ko) | 1995-04-19 |
KR100350814B1 KR100350814B1 (ko) | 2002-10-31 |
Family
ID=6499053
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019940023934A KR100350814B1 (ko) | 1993-09-30 | 1994-09-23 | 3가인의사이클릭화합물,이의제조방법및이를포함하는균질가용성촉매시스템 |
Country Status (13)
Country | Link |
---|---|
EP (1) | EP0646588B1 (ko) |
JP (1) | JP2644976B2 (ko) |
KR (1) | KR100350814B1 (ko) |
CN (1) | CN1106816A (ko) |
AT (1) | ATE189225T1 (ko) |
AU (1) | AU7430394A (ko) |
BR (1) | BR9403827A (ko) |
CA (1) | CA2132673A1 (ko) |
DE (2) | DE4333307A1 (ko) |
ES (1) | ES2143515T3 (ko) |
PL (1) | PL305159A1 (ko) |
TW (1) | TW283149B (ko) |
ZA (1) | ZA947456B (ko) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19621967A1 (de) * | 1996-05-31 | 1997-12-04 | Basf Ag | Verfahren zur Hydroformylierung und dafür geeignete Katalysatoren die Phosphorverbindungen als Liganden enthalten |
DE19702025A1 (de) * | 1997-01-23 | 1998-07-30 | Studiengesellschaft Kohle Mbh | Verwendung perfluoralkylsubstituierter Phosphorverbindungen als Liganden für die homogene Katalyse in überkritischem Kohlendioxid |
US7012162B2 (en) * | 2000-06-26 | 2006-03-14 | Basf Aktiengesellschaft | Phosphacyclohexanes and the use thereof in the hydroformylation of olefins |
WO2002000580A1 (de) * | 2000-06-26 | 2002-01-03 | Basf Aktiengesellschaft | Alkoholgemische mit 13 und 15 kohlenstoffatomen und deren verwendung in der herstellung von oberflächenaktiven substanzen |
DE10106348A1 (de) * | 2001-02-09 | 2002-08-14 | Basf Ag | Als Katalysator oder zur Herstellung eines Katalysatorsystems geeignete Verbindung |
US6794553B2 (en) * | 2001-11-09 | 2004-09-21 | Shell Oil Company | Process for the telomerization of a conjugated diene, catalyst and bidentate ligand useful therein |
DE102008044783B4 (de) | 2008-08-28 | 2012-05-16 | Oxea Gmbh | Verfahren zur Gewinnung von aliphatischen C3- bis C10- Aldehyden aus Hochsiedern durch thermische Behandlung |
DE102009004655B4 (de) | 2009-01-15 | 2013-02-14 | Oxea Gmbh | Verfahren zur Herstellung von Aldehyden |
DE102009016651B4 (de) | 2009-04-07 | 2011-11-17 | Oxea Gmbh | Verfahren zur Herstellung von Aldehyden |
CN106083551A (zh) * | 2016-06-30 | 2016-11-09 | 成都欣华源科技有限责任公司 | 一种丙烯氢甲酰化制备丁醛的方法 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1300164C (en) * | 1986-06-13 | 1992-05-05 | Thomas James Devon | Chelate ligands for low pressure hydroformylation catalyst and process employing same |
US5202493A (en) * | 1991-04-26 | 1993-04-13 | E. I. Du Pont De Nemours And Company | Chiral tridentate bis(phospholane) ligands |
US5171892A (en) * | 1991-07-02 | 1992-12-15 | E. I. Du Pont De Nemours And Company | Chiral phospholanes via chiral 1,4-diol cyclic sulfates |
ATE165361T1 (de) * | 1992-01-31 | 1998-05-15 | Hoffmann La Roche | Diphosphinliganden |
US5332846A (en) * | 1993-06-01 | 1994-07-26 | Eastman Kodak Company | Hydroformylation process using novel phosphine-rhodium catalyst system |
-
1993
- 1993-09-30 DE DE4333307A patent/DE4333307A1/de not_active Withdrawn
-
1994
- 1994-07-22 TW TW083106718A patent/TW283149B/zh active
- 1994-09-22 JP JP6228268A patent/JP2644976B2/ja not_active Expired - Lifetime
- 1994-09-22 CA CA002132673A patent/CA2132673A1/en not_active Abandoned
- 1994-09-23 BR BR9403827A patent/BR9403827A/pt not_active IP Right Cessation
- 1994-09-23 PL PL94305159A patent/PL305159A1/xx unknown
- 1994-09-23 ZA ZA947456A patent/ZA947456B/xx unknown
- 1994-09-23 KR KR1019940023934A patent/KR100350814B1/ko not_active IP Right Cessation
- 1994-09-26 EP EP94115104A patent/EP0646588B1/de not_active Expired - Lifetime
- 1994-09-26 AT AT94115104T patent/ATE189225T1/de not_active IP Right Cessation
- 1994-09-26 ES ES94115104T patent/ES2143515T3/es not_active Expired - Lifetime
- 1994-09-26 DE DE59409100T patent/DE59409100D1/de not_active Expired - Fee Related
- 1994-09-27 CN CN94116587A patent/CN1106816A/zh active Pending
- 1994-09-28 AU AU74303/94A patent/AU7430394A/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
EP0646588B1 (de) | 2000-01-26 |
JPH07173183A (ja) | 1995-07-11 |
AU7430394A (en) | 1995-04-13 |
CA2132673A1 (en) | 1995-03-31 |
DE59409100D1 (de) | 2000-03-02 |
EP0646588A1 (de) | 1995-04-05 |
ZA947456B (en) | 1995-05-15 |
BR9403827A (pt) | 1995-05-30 |
TW283149B (ko) | 1996-08-11 |
DE4333307A1 (de) | 1995-04-06 |
ES2143515T3 (es) | 2000-05-16 |
KR100350814B1 (ko) | 2002-10-31 |
JP2644976B2 (ja) | 1997-08-25 |
CN1106816A (zh) | 1995-08-16 |
PL305159A1 (en) | 1995-04-03 |
ATE189225T1 (de) | 2000-02-15 |
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