ES2170604A1 - Procedimiento para polimerizar polialquilpiperidinas insaturadas. - Google Patents
Procedimiento para polimerizar polialquilpiperidinas insaturadas.Info
- Publication number
- ES2170604A1 ES2170604A1 ES009901358A ES9901358A ES2170604A1 ES 2170604 A1 ES2170604 A1 ES 2170604A1 ES 009901358 A ES009901358 A ES 009901358A ES 9901358 A ES9901358 A ES 9901358A ES 2170604 A1 ES2170604 A1 ES 2170604A1
- Authority
- ES
- Spain
- Prior art keywords
- novel
- polyalkylpiperidines
- hals
- polymerizing unsaturated
- unsaturated
- 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.)
- Granted
Links
- 230000000379 polymerizing effect Effects 0.000 title abstract 2
- 150000001412 amines Chemical class 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 230000000254 damaging effect Effects 0.000 abstract 1
- 239000012968 metallocene catalyst Substances 0.000 abstract 1
- 239000011368 organic material Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 230000000087 stabilizing effect Effects 0.000 abstract 1
Classifications
-
- 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
- C08F26/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F26/06—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/12—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with only hydrogen atoms attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
-
- 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
- C08F210/00—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
- C08F4/65908—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an ionising compound other than alumoxane, e.g. (C6F5)4B-X+
-
- 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
- C08F4/65916—Component covered by group C08F4/64 containing a transition metal-carbon bond supported on a carrier, e.g. silica, MgCl2, polymer
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
Procedimiento para polimerizar polialquilpiperidinas insaturadas. Se describe un proceso de polimerización de aminas insaturadas e impedidas estéricamente del tipo de las polialquilpiperidinas (HALS) con intervención de un catalizador metaloceno, nuevos polímeros resultantes de dicho proceso y nuevas HALS insaturadas. Los nuevos compuestos monoméricos o copolímeros pueden emplearse con ventaja para la estabilización de materiales orgánicos contra el deterioro provocado por la luz, el oxígeno y/o el calor.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH132398 | 1998-06-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES2170604A1 true ES2170604A1 (es) | 2002-08-01 |
| ES2170604B1 ES2170604B1 (es) | 2004-01-16 |
Family
ID=4207764
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES009901358A Expired - Lifetime ES2170604B1 (es) | 1998-06-19 | 1999-06-18 | Procedimiento para polimerizar polialquilpiperidinas insaturadas. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20020128406A1 (es) |
| JP (1) | JP2000143730A (es) |
| BE (1) | BE1013051A3 (es) |
| CA (1) | CA2275381A1 (es) |
| DE (1) | DE19927492A1 (es) |
| ES (1) | ES2170604B1 (es) |
| FR (1) | FR2780064A1 (es) |
| GB (1) | GB2338489B (es) |
| IT (1) | IT1312353B1 (es) |
| NL (1) | NL1012219C2 (es) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1184442A1 (en) | 2000-08-30 | 2002-03-06 | Clariant International Ltd. | Liquid crystal mixture |
| CZ2006196A3 (cs) * | 2006-03-23 | 2008-04-23 | Ústav makromolekulární chemie AV CR | Kopolymerní stabilizátor obsahující derivát piperidinu a derivát fenolu, zpusob jeho výroby a použití |
| CN102241623A (zh) * | 2010-05-13 | 2011-11-16 | 上海医药工业研究院 | 一类n-取代-4-卤代烷基哌啶醇类衍生物及其应用 |
| CN102241622A (zh) * | 2010-05-13 | 2011-11-16 | 上海医药工业研究院 | 一种制备盐酸替罗非班的方法 |
| WO2014148136A1 (ja) * | 2013-03-19 | 2014-09-25 | 岐阜市 | 抗アレルギー活性化合物及びその用途 |
| JP6192566B2 (ja) * | 2014-02-21 | 2017-09-06 | 日本ポリプロ株式会社 | ポリオレフィン中に含まれるソルビトール系化合物を定量分析する方法 |
| JP6310282B2 (ja) * | 2014-03-11 | 2018-04-11 | 日本ポリエチレン株式会社 | 極性基含有オレフィン共重合体、その製造方法及び光安定化剤、並びにそれを用いた樹脂組成物、成形品及び農業用フィルム |
| CN112239458B (zh) * | 2020-10-20 | 2022-10-14 | 天津利安隆新材料股份有限公司 | 受阻胺光稳定剂中间体及受阻胺光稳定剂的制备方法 |
| CN115677565A (zh) * | 2022-10-17 | 2023-02-03 | 南通大学 | 一种受阻胺类光稳定剂中间体的制备方法 |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1502557A (en) * | 1975-05-28 | 1978-03-01 | Ciba Geigy Ag | Stabilisation of light sensitive polymers |
| US4294949A (en) * | 1977-07-19 | 1981-10-13 | Ciba-Geigy Corporation | Novel polymeric compounds |
| US4369274A (en) * | 1981-07-20 | 1983-01-18 | American Cyanamid Company | Hindered amine light stabilizers for polymers |
| GB2105731A (en) * | 1981-08-12 | 1983-03-30 | Ciba Geigy Ag | Copolymeric polyalkylpiperidines |
| EP0192987A2 (en) * | 1985-01-30 | 1986-09-03 | Himont Incorporated | A process for preparing thermically stable olefinic polymers |
| EP0811638A2 (en) * | 1996-06-06 | 1997-12-10 | Union Carbide Chemicals & Plastics Technology Corporation | Process for controlling static in polymerizations utilizing metallocene catalysts |
| US5703149A (en) * | 1995-06-29 | 1997-12-30 | Ciba Specialty Chemicals Corporation | Process for the preparation of stabilized olefin polymers |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4582881A (en) * | 1981-06-10 | 1986-04-15 | Ciba-Geigy Corporation | 2-substituted 5-vinylpyrimidines, polymer obtainable therefrom and preparation thereof |
| DE58909021D1 (de) * | 1988-06-30 | 1995-03-30 | Ciba Geigy Ag | Verfahren zur Herstellung von thermisch stabilen Olefinpolymeren. |
| US5616636A (en) * | 1992-03-11 | 1997-04-01 | Sandoz Ltd. | Phosphonite-hals and phosphite-hals compounds as stabilizers |
| JP3307704B2 (ja) * | 1993-02-19 | 2002-07-24 | 三菱化学株式会社 | α‐オレフィン重合体の製造法 |
| JP3293927B2 (ja) * | 1993-02-19 | 2002-06-17 | 三菱化学株式会社 | α‐オレフィン重合用触媒成分およびそれを用いたα‐オレフィン重合体の製造法 |
| TW270131B (es) * | 1993-07-13 | 1996-02-11 | Ciba Geigy |
-
1999
- 1999-06-02 NL NL1012219A patent/NL1012219C2/nl not_active IP Right Cessation
- 1999-06-14 GB GB9913587A patent/GB2338489B/en not_active Expired - Fee Related
- 1999-06-15 IT IT1999MI001331A patent/IT1312353B1/it active
- 1999-06-15 BE BE9900415A patent/BE1013051A3/fr not_active IP Right Cessation
- 1999-06-16 US US09/334,081 patent/US20020128406A1/en active Pending
- 1999-06-16 DE DE19927492A patent/DE19927492A1/de not_active Withdrawn
- 1999-06-17 CA CA002275381A patent/CA2275381A1/en not_active Abandoned
- 1999-06-17 FR FR9907665A patent/FR2780064A1/fr not_active Withdrawn
- 1999-06-18 ES ES009901358A patent/ES2170604B1/es not_active Expired - Lifetime
- 1999-06-21 JP JP11173931A patent/JP2000143730A/ja active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1502557A (en) * | 1975-05-28 | 1978-03-01 | Ciba Geigy Ag | Stabilisation of light sensitive polymers |
| US4294949A (en) * | 1977-07-19 | 1981-10-13 | Ciba-Geigy Corporation | Novel polymeric compounds |
| US4369274A (en) * | 1981-07-20 | 1983-01-18 | American Cyanamid Company | Hindered amine light stabilizers for polymers |
| GB2105731A (en) * | 1981-08-12 | 1983-03-30 | Ciba Geigy Ag | Copolymeric polyalkylpiperidines |
| EP0192987A2 (en) * | 1985-01-30 | 1986-09-03 | Himont Incorporated | A process for preparing thermically stable olefinic polymers |
| US5703149A (en) * | 1995-06-29 | 1997-12-30 | Ciba Specialty Chemicals Corporation | Process for the preparation of stabilized olefin polymers |
| EP0811638A2 (en) * | 1996-06-06 | 1997-12-10 | Union Carbide Chemicals & Plastics Technology Corporation | Process for controlling static in polymerizations utilizing metallocene catalysts |
Non-Patent Citations (1)
| Title |
|---|
| C.-E. WILEN et al. "Preparation of hindered piperidine and its copolymerization with propylene over a supported high activity Ziegler-Natta catalyst", J. Polym. Sci. Part A. Polym. Chem., 1992, Vol. 30, paginas 1163-1170. * |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1312353B1 (it) | 2002-04-15 |
| US20020128406A1 (en) | 2002-09-12 |
| ITMI991331A0 (it) | 1999-06-15 |
| BE1013051A3 (fr) | 2001-08-07 |
| NL1012219A1 (nl) | 1999-12-21 |
| GB9913587D0 (en) | 1999-08-11 |
| ITMI991331A1 (it) | 2000-12-15 |
| GB2338489B (en) | 2000-09-13 |
| ES2170604B1 (es) | 2004-01-16 |
| JP2000143730A (ja) | 2000-05-26 |
| GB2338489A (en) | 1999-12-22 |
| CA2275381A1 (en) | 1999-12-19 |
| FR2780064A1 (fr) | 1999-12-24 |
| NL1012219C2 (nl) | 2000-04-13 |
| DE19927492A1 (de) | 1999-12-23 |
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