DE69519624T2 - Verfahren zur Polymerisation von monocyclischen Polyalkylendicarboxylat-Oligomeren - Google Patents
Verfahren zur Polymerisation von monocyclischen Polyalkylendicarboxylat-OligomerenInfo
- Publication number
- DE69519624T2 DE69519624T2 DE69519624T DE69519624T DE69519624T2 DE 69519624 T2 DE69519624 T2 DE 69519624T2 DE 69519624 T DE69519624 T DE 69519624T DE 69519624 T DE69519624 T DE 69519624T DE 69519624 T2 DE69519624 T2 DE 69519624T2
- Authority
- DE
- Germany
- Prior art keywords
- radical
- macrocyclic
- catalyst
- process according
- oligomers
- 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.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 24
- 238000006116 polymerization reaction Methods 0.000 title description 13
- 125000002950 monocyclic group Chemical group 0.000 title 1
- 229920001281 polyalkylene Polymers 0.000 title 1
- 229920000728 polyester Polymers 0.000 claims description 37
- 239000003054 catalyst Substances 0.000 claims description 36
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 27
- -1 alicyclic radical Chemical class 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- 229910052719 titanium Inorganic materials 0.000 claims description 10
- 239000010936 titanium Substances 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 229920001707 polybutylene terephthalate Polymers 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000002685 polymerization catalyst Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 2
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 17
- 239000007788 liquid Substances 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000012535 impurity Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- XRVCFZPJAHWYTB-UHFFFAOYSA-N prenderol Chemical compound CCC(CC)(CO)CO XRVCFZPJAHWYTB-UHFFFAOYSA-N 0.000 description 4
- 229950006800 prenderol Drugs 0.000 description 4
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000003413 spiro compounds Chemical class 0.000 description 2
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 1
- SZSSMFVYZRQGIM-UHFFFAOYSA-N 2-(hydroxymethyl)-2-propylpropane-1,3-diol Chemical compound CCCC(CO)(CO)CO SZSSMFVYZRQGIM-UHFFFAOYSA-N 0.000 description 1
- WOFPPJOZXUTRAU-UHFFFAOYSA-N 2-Ethyl-1-hexanol Natural products CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 description 1
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- KTXWGMUMDPYXNN-UHFFFAOYSA-N 2-ethylhexan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-] KTXWGMUMDPYXNN-UHFFFAOYSA-N 0.000 description 1
- JVZZUPJFERSVRN-UHFFFAOYSA-N 2-methyl-2-propylpropane-1,3-diol Chemical compound CCCC(C)(CO)CO JVZZUPJFERSVRN-UHFFFAOYSA-N 0.000 description 1
- WSQZNZLOZXSBHA-UHFFFAOYSA-N 3,8-dioxabicyclo[8.2.2]tetradeca-1(12),10,13-triene-2,9-dione Chemical compound O=C1OCCCCOC(=O)C2=CC=C1C=C2 WSQZNZLOZXSBHA-UHFFFAOYSA-N 0.000 description 1
- LLLVZDVNHNWSDS-UHFFFAOYSA-N 4-methylidene-3,5-dioxabicyclo[5.2.2]undeca-1(9),7,10-triene-2,6-dione Chemical compound C1(C2=CC=C(C(=O)OC(=C)O1)C=C2)=O LLLVZDVNHNWSDS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- YBKZDLRVPQIFPQ-UHFFFAOYSA-N O1CC2(C)CO[Ti]1(OCCCC)OC2 Chemical compound O1CC2(C)CO[Ti]1(OCCCC)OC2 YBKZDLRVPQIFPQ-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003733 fiber-reinforced composite Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 208000016261 weight loss Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/85—Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/003—Compounds containing elements of Groups 4 or 14 of the Periodic Table without C-Metal linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyesters Or Polycarbonates (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/371,715 US5527976A (en) | 1995-01-12 | 1995-01-12 | Method for polymerizing macrocyclic poly(alkylene dicarboxylate) oligomers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69519624D1 DE69519624D1 (de) | 2001-01-18 |
| DE69519624T2 true DE69519624T2 (de) | 2001-04-12 |
Family
ID=23465126
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69519624T Expired - Lifetime DE69519624T2 (de) | 1995-01-12 | 1995-10-26 | Verfahren zur Polymerisation von monocyclischen Polyalkylendicarboxylat-Oligomeren |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US5527976A (enExample) |
| EP (1) | EP0725098B1 (enExample) |
| JP (2) | JP3441272B2 (enExample) |
| DE (1) | DE69519624T2 (enExample) |
| ES (1) | ES2153018T3 (enExample) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6108704A (en) | 1995-09-25 | 2000-08-22 | Netspeak Corporation | Point-to-point internet protocol |
| US5661214A (en) * | 1996-08-05 | 1997-08-26 | General Electric Company | Titanate esters useful as polymerization initiators for macrocylic polyester oligomers |
| US6728784B1 (en) * | 1996-08-21 | 2004-04-27 | Netspeak Corporation | Collaborative multimedia architecture for packet-switched data networks |
| US7216348B1 (en) | 1999-01-05 | 2007-05-08 | Net2Phone, Inc. | Method and apparatus for dynamically balancing call flow workloads in a telecommunications system |
| US7256241B2 (en) | 2000-01-21 | 2007-08-14 | Cyclics Corporation | Methods for polymerizing macrocyclic polyester oligomers using catalyst promoters |
| US6369157B1 (en) | 2000-01-21 | 2002-04-09 | Cyclics Corporation | Blend material including macrocyclic polyester oligomers and processes for polymerizing the same |
| US6906147B2 (en) * | 2002-03-20 | 2005-06-14 | Cyclics Corporation | Catalytic systems |
| US7151143B2 (en) * | 2000-01-21 | 2006-12-19 | Cyclics Corporation | Blends containing macrocyclic polyester oligomer and high molecular weight polymer |
| US6420047B2 (en) * | 2000-01-21 | 2002-07-16 | Cyclics Corporation | Macrocyclic polyester oligomers and processes for polymerizing the same |
| US20050282952A1 (en) * | 2000-01-21 | 2005-12-22 | Cyclics Corporation | Graphite-polyester composites made from macrocyclic polyester oligomers |
| US6960626B2 (en) * | 2000-01-21 | 2005-11-01 | Cyclics Corporation | Intimate physical mixtures containing macrocyclic polyester oligomer and filler |
| DE60102079T2 (de) * | 2000-08-22 | 2004-12-09 | Mitsui Chemicals, Inc. | Katalysatoren für die herstellung von polyester, verfahren zur herstellung von polyester, und polyester |
| US7767781B2 (en) | 2000-09-01 | 2010-08-03 | Cyclics Corporation | Preparation of low-acid polyalkylene terephthalate and preparation of macrocyclic polyester oligomer therefrom |
| US7750109B2 (en) | 2000-09-01 | 2010-07-06 | Cyclics Corporation | Use of a residual oligomer recyclate in the production of macrocyclic polyester oligomer |
| JP2004507599A (ja) * | 2000-09-01 | 2004-03-11 | サイクリクス コーポレイション | 線形ポリエステルを、大環状オリゴエステル組成物および大環状オリゴエステルに変換する方法 |
| US6436548B1 (en) | 2000-09-12 | 2002-08-20 | Cyclics Corporation | Species modification in macrocyclic polyester oligomers, and compositions prepared thereby |
| BR0115879A (pt) * | 2000-11-21 | 2005-02-01 | Ici Plc | Catalisador de esterificação, processo de poliéster e artigo de poliéster |
| US6420048B1 (en) | 2001-06-05 | 2002-07-16 | Cyclics Corporation | High molecular weight copolyesters from macrocyclic oligoesters and cyclic esters |
| JP2002363301A (ja) * | 2001-06-11 | 2002-12-18 | Toyobo Co Ltd | ポリエステル成形品 |
| JP2005515965A (ja) | 2001-06-27 | 2005-06-02 | サイクリクス コーポレイション | 大環状オリゴエステルの単離、処方、および成形 |
| US7304123B2 (en) | 2001-06-27 | 2007-12-04 | Cyclics Corporation | Processes for shaping macrocyclic oligoesters |
| US6436549B1 (en) | 2001-07-16 | 2002-08-20 | Cyclics Corporation | Block copolymers from macrocyclic oligoesters and dihydroxyl-functionalized polymers |
| US6787632B2 (en) * | 2001-10-09 | 2004-09-07 | Cyclics Corporation | Organo-titanate catalysts for preparing pure macrocyclic oligoesters |
| US6831138B2 (en) | 2002-01-07 | 2004-12-14 | Cyclics Corporation | Polymer-containing organo-metal catalysts |
| US6806346B2 (en) * | 2002-07-12 | 2004-10-19 | E. I. Du Pont De Nemours And Company | Copolymerization of cyclic ester oligomers |
| GB0226408D0 (en) * | 2002-11-13 | 2002-12-18 | Johnson Matthey Plc | Catalyst and process |
| US20040106713A1 (en) * | 2002-12-03 | 2004-06-03 | Avakian Roger W. | Use of additives in compounds containing macrocyclic poly(alkylene dicarboxylate) oligomers |
| GB0228267D0 (en) * | 2002-12-04 | 2003-01-08 | Johnson Matthey Plc | Catalyst and process |
| WO2004050734A1 (en) * | 2002-12-04 | 2004-06-17 | Johnson Matthey Plc | Organometallic catalyst composition and process for polyurethane manufacture using said catalyst |
| DE10393926T5 (de) * | 2002-12-20 | 2006-09-28 | Cyclics Corp. | Reinigung von makrocyclischen Oligoestern |
| KR20050093783A (ko) * | 2002-12-20 | 2005-09-23 | 다우 글로벌 테크놀로지스 인크. | 중합된 거대고리 올리고머 나노복합재 조성물 |
| DE602004025971D1 (de) * | 2003-12-19 | 2010-04-22 | Cyclics Corp | Verfahren zum dispergieren eines schlagzähigkeitsmodifikators in einem makrocyclischen polyesteroligomer |
| EP1794223A1 (en) * | 2004-09-30 | 2007-06-13 | Honeywell International Inc. | Thermally conductive composite and uses for microelectronic packaging |
| US20060067055A1 (en) * | 2004-09-30 | 2006-03-30 | Heffner Kenneth H | Thermally conductive composite and uses for microelectronic packaging |
| US20060098768A1 (en) * | 2004-11-09 | 2006-05-11 | Romero Gabriel L | Polymerization of macrocyclic polyester oligomers using N-heterocyclic carbene catalysts |
| WO2006053078A2 (en) * | 2004-11-09 | 2006-05-18 | E.I. Dupont De Nemours And Company | Polymerization of macrocyclic polyester oligomers using n-heterocyclic carbene and metal amide or metal alkoxide catalyst |
| AU2005339151B2 (en) * | 2005-12-15 | 2011-09-08 | Kimberly-Clark Worldwide, Inc. | Biodegradable multicomponent fibers |
| EP2004396B1 (en) | 2006-04-07 | 2011-11-02 | Kimberly-Clark Worldwide, Inc. | Biodegradable nonwoven laminate |
| MX2009000527A (es) * | 2006-07-14 | 2009-01-27 | Kimberly Clark Co | Acido polilactico biodegradable para su uso en telas no tejidas. |
| KR101297937B1 (ko) | 2006-07-14 | 2013-08-19 | 킴벌리-클라크 월드와이드, 인크. | 부직 웹에 사용하기 위한 생분해성 지방족 폴리에스테르 |
| WO2008008068A1 (en) | 2006-07-14 | 2008-01-17 | Kimberly-Clark Worldwide, Inc. | Biodegradable aliphatic-aromatic copolyester for use in nonwoven webs |
| JP5135740B2 (ja) * | 2006-09-04 | 2013-02-06 | 三菱化学株式会社 | ポリエステル及びその製造方法、並びにポリエステルブロック共重合体 |
| US8470222B2 (en) | 2008-06-06 | 2013-06-25 | Kimberly-Clark Worldwide, Inc. | Fibers formed from a blend of a modified aliphatic-aromatic copolyester and thermoplastic starch |
| US8841386B2 (en) | 2008-06-10 | 2014-09-23 | Kimberly-Clark Worldwide, Inc. | Fibers formed from aromatic polyester and polyether copolymer |
| BR112012000563A2 (pt) * | 2009-06-19 | 2016-11-16 | Polyone Corp | terpolímeros limpadores de oxigênio. |
| WO2013177266A1 (en) | 2012-05-25 | 2013-11-28 | Polyone Corporation | Oxygen scavenging copolymers made from cyclic aliphatic monomers |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB991020A (en) * | 1960-11-29 | 1965-05-05 | Martin Marietta Corp | Esterification of iso- and terephthalic acids |
| US5039783A (en) * | 1990-11-05 | 1991-08-13 | General Electric Company | Method for preparing and polymerizing macrocyclic poly(alkylene discarboxylate) oligomers |
| US5466744A (en) * | 1990-11-05 | 1995-11-14 | General Electric Company | Polymerization of macrocyclic poly(alkylene dicarboxylate) oligomers |
| US5191013A (en) * | 1991-05-16 | 1993-03-02 | General Electric Company | Macrocyclic filled compositions convertible to polyester composites |
| US5214158A (en) * | 1991-06-03 | 1993-05-25 | General Electric Company | Method for preparation of macrocyclic poly(alkylene dicarboxylate) oligomers |
| JPH0621873A (ja) * | 1992-07-02 | 1994-01-28 | Fujitsu Ltd | 移動通信システムにおける位相調整装置 |
| US5231161A (en) * | 1992-10-22 | 1993-07-27 | General Electric Company | Method for preparation of macrocyclic poly(alkylene dicarboxylate) oligomers from bis(hydroxyalkyl) dicarboxylates |
| US5321117A (en) * | 1992-11-19 | 1994-06-14 | General Electric Company | Macrocyclic polyester oligomer preparation with Lewis acid as catalyst |
| US5300590A (en) * | 1992-11-30 | 1994-04-05 | General Electric Company | Macrocyclic polyester compositions convertible to linear polyesters of improved integrity |
| US5389719A (en) * | 1994-06-20 | 1995-02-14 | General Electric Company | Method for polymerizing macrocyclic poly(alkylene dicarboxylate) oligomers |
| US5387666A (en) * | 1994-06-20 | 1995-02-07 | General Electric Company | Branched polyesters prepared from macrocyclic poly(Alkylene Dicarboxylate) oligomers |
| US5386037A (en) * | 1994-06-20 | 1995-01-31 | General Electric Company | Trisstannoxanes useful for polymerizing macrocyclic poly(alkylene dicarboxylate) oligomers |
-
1995
- 1995-01-12 US US08/371,715 patent/US5527976A/en not_active Expired - Lifetime
- 1995-10-26 EP EP95307616A patent/EP0725098B1/en not_active Expired - Lifetime
- 1995-10-26 ES ES95307616T patent/ES2153018T3/es not_active Expired - Lifetime
- 1995-10-26 DE DE69519624T patent/DE69519624T2/de not_active Expired - Lifetime
- 1995-11-09 JP JP29069695A patent/JP3441272B2/ja not_active Expired - Fee Related
- 1995-11-30 US US08/565,366 patent/US5591800A/en not_active Expired - Lifetime
-
2003
- 2003-05-13 JP JP2003134837A patent/JP4073822B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ES2153018T3 (es) | 2001-02-16 |
| JP4073822B2 (ja) | 2008-04-09 |
| JP2004002417A (ja) | 2004-01-08 |
| US5527976A (en) | 1996-06-18 |
| JPH08253573A (ja) | 1996-10-01 |
| EP0725098A2 (en) | 1996-08-07 |
| JP3441272B2 (ja) | 2003-08-25 |
| EP0725098B1 (en) | 2000-12-13 |
| US5591800A (en) | 1997-01-07 |
| DE69519624D1 (de) | 2001-01-18 |
| EP0725098A3 (enExample) | 1996-09-18 |
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