US20020055595A1 - Beta-hydroxyalklyamides, process for their production and their use - Google Patents
Beta-hydroxyalklyamides, process for their production and their use Download PDFInfo
- Publication number
- US20020055595A1 US20020055595A1 US09/909,573 US90957301A US2002055595A1 US 20020055595 A1 US20020055595 A1 US 20020055595A1 US 90957301 A US90957301 A US 90957301A US 2002055595 A1 US2002055595 A1 US 2002055595A1
- Authority
- US
- United States
- Prior art keywords
- fact
- general formula
- hydroxyalkylamide
- carboxylic acid
- acid derivative
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims description 19
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 12
- 239000004971 Cross linker Substances 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 7
- 238000013019 agitation Methods 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 2
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 claims description 2
- 229940043276 diisopropanolamine Drugs 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 239000004593 Epoxy Substances 0.000 claims 1
- 125000003700 epoxy group Chemical group 0.000 claims 1
- 229920000647 polyepoxide Polymers 0.000 claims 1
- 0 [1*]C.[2*]C(O)CN(CC([2*])O)C(=O)c1ccccc1 Chemical compound [1*]C.[2*]C(O)CN(CC([2*])O)C(=O)c1ccccc1 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 229960004132 diethyl ether Drugs 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- HIXRCLYXOZHPNU-UHFFFAOYSA-N 2-(2-hydroxyethyl)hexanediamide Chemical compound NC(=O)CCCC(C(N)=O)CCO HIXRCLYXOZHPNU-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- XDYFZJHKTVRKHR-UHFFFAOYSA-N N[NH+](C1CC=CCC1)[O-] Chemical compound N[NH+](C1CC=CCC1)[O-] XDYFZJHKTVRKHR-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- -1 carboxylic acid halide Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229940052303 ethers for general anesthesia Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005496 tempering Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/67—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/68—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/69—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
Definitions
- This invention relates to novel ⁇ -hydroxyalkylamides, a method for their production and their use.
- ⁇ -hydroxyalkylamides are very important as intermediate products and as cross linkers for polymers.
- ⁇ -hydroxyalkylamides are conventionally produced by the aminolysis of alkyl esters with ⁇ -alkanol amines in the presence of basic catalysts.
- the a hydroxyalkylamides are isolated and purified either by crystallization in a solvent or, especially with solid ⁇ -hydroxyalkylamides, without the use of solvent in a slurry process.
- a process of the above referenced type is described in U.S. Pat. No. 5,101,073 and in EP 0 473 380 B1.
- the slurry process is based on the fact that the equilibrium reaction that occurs during the production of the ⁇ -hydroxyalkylamides is shifted toward the desired end product as a result of the fact that the desired ⁇ -hydroxyalkylamide is precipitated from the melt by tempering in a defined temperature range and the melt is then crystallized.
- a disadvantage of this method is the use of equimolar quantities of alkyl ester and ⁇ -hydroxyalkylamide.
- EP-A-322 834 describes a powder coating which contains a polyester and ⁇ -hydroxyalkylkamides as cross linkers (curing agents). Corresponding coatings with good characteristics can be produced with the formulation described in said document.
- the object of this invention is to propose new, previously unknown ⁇ -hydroxyalkylamides and a corresponding process for their production.
- the invention teaches that this object can be accomplished with regard to the ⁇ -hydroxyalkylamides by the characterizing features of claim 1 , and with regard to the process for their manufacture by the characterizing features of claim 4 .
- the subclaims describe advantageous developments of the invention.
- the use of the ⁇ -hydroxyalkylamides claimed by the invention is described in the characterizing portions of claims 11 to 14 .
- R 1 stands for hydrogen or a linear or branched C 1 to C 10 alkyl.
- R 2 is a linear or branched C 1 to C 5 alkyl.
- the ⁇ -hydroxyalkylamides claimed by the invention are characterized in particular by the substituted carbon atom next to the OH group. In the ⁇ -hydroxyalkylamides claimed by the invention, the R 2 group is located here.
- the ⁇ -hydroxyalkylamide is preferably constructed so that the RI group is H, tert-butyl, isopropyl or pentyl and is located in the para position to the CO group.
- R 1 group is hydrogen and the R 2 group is methyl.
- R 1 and R 2 groups thereby have the definitions presented above.
- the R 3 group can thereby be a halogen, preferably chlorine, or an OR 4 group. If there is an OR 4 group, R 4 is a linear C 1 to C 5 alkyl, preferably a —CH 3 group.
- the conversion of the carboxylic acid derivative and the alkanol amine preferably takes place in a solution.
- Preferred solvents include but are not restricted to: aromatic hydrocarbons such as benzene, toluene or xylene. Ethers such as diethylether or mixtures of the solvents listed above are also suitable.
- An essential feature of the process claimed by the invention is that the carboxylic acid derivative having the general Formula II and the alkanol amine having the general Formula III are reacted with vigorous agitation of stirring.
- the alkanol amine is thereby preferably presented first and the carboxylic acid derivative is then added by drops with vigorous agitation of stirring.
- the conversion takes place at ⁇ 10 to 25° C., preferably at 0 to 10° C.
- the reaction time is normally 0.5 to 5 hours. A reaction time of 2 hours is most advantageous.
- the reaction temperature at RT is up to 150° C.
- the ⁇ -hydroxyalkylamide is particularly well suited as a cross linker for polymers.
- ⁇ -hydroxyalkylamide is particularly preferred as a cross-linker for powder coats with polyesters or acrylates as the polymer.
- the ⁇ -hydroxyalkylamide can be used as a cross linker (curing agent) analogous to the ⁇ -hydroxyalkylamides cited in EP-A-322 A34.
- the ⁇ -hydroxyalkylamides taught by the invention can also be used in combination with other curing agents.
- One example of this usage is the curing agent sold under the name PRIMID® by EMS—CHEMIE AG, Domat/Ems.
- PRIMID® is N,N,N′,N′ 2-hydroxyethyladipamide.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paints Or Removers (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/866,979 US7030272B2 (en) | 2000-10-26 | 2004-06-12 | β-hydroxyalkylamides process for their production and their use |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10053194.6 | 2000-10-26 | ||
| DE10053194A DE10053194A1 (de) | 2000-10-26 | 2000-10-26 | ß-Hydroxyalkylamide, Verfahren zu ihrer Herstellung und deren Verwendung |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US10/866,979 Division US7030272B2 (en) | 2000-10-26 | 2004-06-12 | β-hydroxyalkylamides process for their production and their use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US20020055595A1 true US20020055595A1 (en) | 2002-05-09 |
Family
ID=7661187
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US09/909,573 Abandoned US20020055595A1 (en) | 2000-10-26 | 2001-07-20 | Beta-hydroxyalklyamides, process for their production and their use |
| US10/866,979 Expired - Lifetime US7030272B2 (en) | 2000-10-26 | 2004-06-12 | β-hydroxyalkylamides process for their production and their use |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US10/866,979 Expired - Lifetime US7030272B2 (en) | 2000-10-26 | 2004-06-12 | β-hydroxyalkylamides process for their production and their use |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US20020055595A1 (zh) |
| EP (1) | EP1203763B1 (zh) |
| JP (1) | JP2002145839A (zh) |
| KR (1) | KR100821024B1 (zh) |
| CN (1) | CN1315785C (zh) |
| AT (1) | ATE449063T1 (zh) |
| AU (1) | AU784957B2 (zh) |
| BR (1) | BR0104738A (zh) |
| CA (1) | CA2359768C (zh) |
| CZ (1) | CZ302774B6 (zh) |
| DE (2) | DE10053194A1 (zh) |
| ES (1) | ES2333643T3 (zh) |
| MX (1) | MXPA01010682A (zh) |
| NO (1) | NO328093B1 (zh) |
| NZ (1) | NZ514573A (zh) |
| PL (1) | PL204666B1 (zh) |
| TW (1) | TW574183B (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103641737A (zh) * | 2013-11-29 | 2014-03-19 | 六安市捷通达化工有限责任公司 | 一种羧酸改性的羟烷基酰胺固化剂的制备方法 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2284005B1 (en) | 2009-08-10 | 2012-05-02 | Eastman Kodak Company | Lithographic printing plate precursors with beta-hydroxy alkylamide crosslinkers |
| CN101704762B (zh) * | 2009-11-13 | 2013-01-09 | 六安市捷通达化工有限责任公司 | 一种β-羟烷基酰胺的生产工艺 |
| JP6283477B2 (ja) * | 2012-06-25 | 2018-02-21 | ローム アンド ハース エレクトロニック マテリアルズ エルエルシーＲｏｈｍ ａｎｄ Ｈａａｓ Ｅｌｅｃｔｒｏｎｉｃ Ｍａｔｅｒｉａｌｓ ＬＬＣ | アミド成分を含むフォトレジスト |
| CN106986786A (zh) * | 2017-02-27 | 2017-07-28 | 沈阳化工大学 | 一种合成β‑羟烷基酰胺的工艺方法 |
| CA3149863A1 (en) | 2019-09-03 | 2021-03-11 | Stefano MALACRIDA | Hydroxyalkylamide functionalized acrylic polymers and process for manufacturing them |
| EP4299656A1 (de) | 2022-07-01 | 2024-01-03 | Evonik Operations GmbH | Herstellung von propoxylierten benzoldicarbonsäureamiden und dem entsprechenden polyurethanschaum |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH472364A (de) * | 1966-12-22 | 1969-05-15 | Geigy Ag J R | Verfahren zur Herstellung eines neuen polycyclischen Amins |
| US3932324A (en) * | 1974-06-13 | 1976-01-13 | American Cyanamid Company | Light stabilizer compositions for polymers |
| US4801680A (en) * | 1987-12-30 | 1989-01-31 | Ppg Industries, Inc. | Hydroxyalkylamide powder coating curing system |
| US5101073A (en) * | 1990-08-27 | 1992-03-31 | Rohm And Haas Company | Production of β-hydroxyalkylamides |
| US5506224A (en) * | 1991-12-31 | 1996-04-09 | Lifegroup S.P.A. | N-acyl derivatives of aminoalcohols active as local autacoids and useful in the therapy of autoimmune processes |
| CN1057519C (zh) * | 1992-02-28 | 2000-10-18 | 罗姆和哈斯公司 | β－羟酰胺的制备 |
| US5216090A (en) * | 1992-07-27 | 1993-06-01 | Rohm And Haas Company | Fatty acid hydroxyalkylamides as coreactable stabilizers and flow aids for powder coatings |
| DE4230229A1 (de) * | 1992-09-10 | 1994-03-17 | Ge Polymertrend Gmbh | Beschichtungsmittel zur Beschichtung von Substraten aus thermoplastischem Kunststoff sowie Verfahren zum Aufbringen einer Schicht aus Pulverlack auf ein thermoplastisches Kunststoffsubstrat |
| DE19823925C2 (de) * | 1998-05-28 | 2001-01-11 | Inventa Ag | Verfahren zur Herstellung von beta-Hydroxyalkylamiden |
-
2000
- 2000-10-26 DE DE10053194A patent/DE10053194A1/de not_active Ceased
-
2001
- 2001-07-20 US US09/909,573 patent/US20020055595A1/en not_active Abandoned
- 2001-09-24 AT AT01122856T patent/ATE449063T1/de not_active IP Right Cessation
- 2001-09-24 DE DE50115225T patent/DE50115225D1/de not_active Expired - Lifetime
- 2001-09-24 ES ES01122856T patent/ES2333643T3/es not_active Expired - Lifetime
- 2001-09-24 EP EP01122856A patent/EP1203763B1/de not_active Expired - Lifetime
- 2001-09-26 AU AU76116/01A patent/AU784957B2/en not_active Ceased
- 2001-09-26 CZ CZ20013461A patent/CZ302774B6/cs not_active IP Right Cessation
- 2001-09-28 PL PL349933A patent/PL204666B1/pl unknown
- 2001-10-02 NZ NZ514573A patent/NZ514573A/xx not_active IP Right Cessation
- 2001-10-05 TW TW90124706A patent/TW574183B/zh not_active IP Right Cessation
- 2001-10-19 JP JP2001322105A patent/JP2002145839A/ja active Pending
- 2001-10-22 MX MXPA01010682A patent/MXPA01010682A/es active IP Right Grant
- 2001-10-23 CA CA2359768A patent/CA2359768C/en not_active Expired - Lifetime
- 2001-10-24 NO NO20015202A patent/NO328093B1/no not_active IP Right Cessation
- 2001-10-24 BR BR0104738-8A patent/BR0104738A/pt not_active IP Right Cessation
- 2001-10-26 CN CNB011375140A patent/CN1315785C/zh not_active Expired - Fee Related
- 2001-10-26 KR KR1020010066270A patent/KR100821024B1/ko not_active Expired - Fee Related
-
2004
- 2004-06-12 US US10/866,979 patent/US7030272B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103641737A (zh) * | 2013-11-29 | 2014-03-19 | 六安市捷通达化工有限责任公司 | 一种羧酸改性的羟烷基酰胺固化剂的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CZ20013461A3 (cs) | 2002-06-12 |
| CN1351008A (zh) | 2002-05-29 |
| KR20020032405A (ko) | 2002-05-03 |
| BR0104738A (pt) | 2002-06-25 |
| NO20015202D0 (no) | 2001-10-24 |
| CN1315785C (zh) | 2007-05-16 |
| CA2359768A1 (en) | 2002-04-26 |
| US7030272B2 (en) | 2006-04-18 |
| AU784957B2 (en) | 2006-08-10 |
| US20040260123A1 (en) | 2004-12-23 |
| ES2333643T3 (es) | 2010-02-25 |
| PL204666B1 (pl) | 2010-01-29 |
| EP1203763A2 (de) | 2002-05-08 |
| DE50115225D1 (de) | 2009-12-31 |
| PL349933A1 (en) | 2002-05-06 |
| CA2359768C (en) | 2010-05-11 |
| NZ514573A (en) | 2003-02-28 |
| EP1203763B1 (de) | 2009-11-18 |
| EP1203763A3 (de) | 2004-01-14 |
| TW574183B (en) | 2004-02-01 |
| ATE449063T1 (de) | 2009-12-15 |
| NO20015202L (no) | 2002-04-29 |
| CZ302774B6 (cs) | 2011-11-02 |
| JP2002145839A (ja) | 2002-05-22 |
| MXPA01010682A (es) | 2003-05-19 |
| AU7611601A (en) | 2002-05-02 |
| DE10053194A1 (de) | 2002-05-16 |
| KR100821024B1 (ko) | 2008-04-08 |
| NO328093B1 (no) | 2009-12-07 |
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