JP5237518B2 - 良好に湿潤し得る、少なくともアルキル化された水溶性で粉末状の非イオン性セルロースエーテルを製造する方法 - Google Patents
良好に湿潤し得る、少なくともアルキル化された水溶性で粉末状の非イオン性セルロースエーテルを製造する方法 Download PDFInfo
- Publication number
- JP5237518B2 JP5237518B2 JP2001575653A JP2001575653A JP5237518B2 JP 5237518 B2 JP5237518 B2 JP 5237518B2 JP 2001575653 A JP2001575653 A JP 2001575653A JP 2001575653 A JP2001575653 A JP 2001575653A JP 5237518 B2 JP5237518 B2 JP 5237518B2
- Authority
- JP
- Japan
- Prior art keywords
- cellulose
- surfactant
- water
- cellulose ether
- ether
- 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
- 229920003086 cellulose ether Polymers 0.000 title claims description 71
- 238000000034 method Methods 0.000 title claims description 20
- 239000004094 surface-active agent Substances 0.000 claims description 64
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 46
- 229920002678 cellulose Polymers 0.000 claims description 24
- 239000001913 cellulose Substances 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 230000002776 aggregation Effects 0.000 claims description 16
- 239000006185 dispersion Substances 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 8
- 239000006227 byproduct Substances 0.000 claims description 7
- 238000004220 aggregation Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 5
- 239000013543 active substance Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 230000003113 alkalizing effect Effects 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 230000021962 pH elevation Effects 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 230000003213 activating effect Effects 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000006266 etherification reaction Methods 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 238000009736 wetting Methods 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000243 solution Substances 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 11
- 239000002245 particle Substances 0.000 description 11
- 238000005054 agglomeration Methods 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- 239000012043 crude product Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000009826 distribution Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- -1 Ether sulfates Chemical class 0.000 description 4
- 229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 description 4
- 229920001131 Pulp (paper) Polymers 0.000 description 4
- 239000003945 anionic surfactant Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000003093 cationic surfactant Substances 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 241000737241 Cocos Species 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- DHIXFTVGHROZHD-UHFFFAOYSA-N 2-ethylhexane-1-sulfonic acid Chemical compound CCCCC(CC)CS(O)(=O)=O DHIXFTVGHROZHD-UHFFFAOYSA-N 0.000 description 1
- SNKZJIOFVMKAOJ-UHFFFAOYSA-N 3-Aminopropanesulfonate Chemical compound NCCCS(O)(=O)=O SNKZJIOFVMKAOJ-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 229920000896 Ethulose Polymers 0.000 description 1
- 239000001859 Ethyl hydroxyethyl cellulose Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000007580 dry-mixing Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 235000019326 ethyl hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000416 hydrocolloid Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- AIGJXJOKJZSSLT-UHFFFAOYSA-N methyl-dioctadecyl-(3-sulfopropyl)azanium;hydroxide Chemical compound [OH-].CCCCCCCCCCCCCCCCCC[N+](C)(CCCS(O)(=O)=O)CCCCCCCCCCCCCCCCCC AIGJXJOKJZSSLT-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B11/00—Preparation of cellulose ethers
- C08B11/02—Alkyl or cycloalkyl ethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B11/00—Preparation of cellulose ethers
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10018155.4 | 2000-04-12 | ||
| DE10018155A DE10018155A1 (de) | 2000-04-12 | 2000-04-12 | Verfahren zur Herstellung von gut benetzbaren, wasserlöslichen, pulverförmigen, mindestens alkylierten, nicht-ionischen Celluloseethern |
| PCT/EP2001/004260 WO2001077183A1 (de) | 2000-04-12 | 2001-04-12 | Verfahren zur herstellung von gut benetzbaren, wasserlöslichen, pulverförmigen, mindestens alkylierten, nicht-ionischen celluloseethern |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003530466A JP2003530466A (ja) | 2003-10-14 |
| JP2003530466A5 JP2003530466A5 (cg-RX-API-DMAC7.html) | 2008-05-08 |
| JP5237518B2 true JP5237518B2 (ja) | 2013-07-17 |
Family
ID=7638486
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001575653A Expired - Lifetime JP5237518B2 (ja) | 2000-04-12 | 2001-04-12 | 良好に湿潤し得る、少なくともアルキル化された水溶性で粉末状の非イオン性セルロースエーテルを製造する方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7361753B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1278779B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP5237518B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR100782644B1 (cg-RX-API-DMAC7.html) |
| DE (2) | DE10018155A1 (cg-RX-API-DMAC7.html) |
| MX (1) | MXPA02010035A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2001077183A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5706344B2 (ja) | 2009-03-05 | 2015-04-22 | ダウ グローバル テクノロジーズ エルエルシー | アルカリセルロース及びセルロース誘導体の改良された製造方法 |
| FR2967682B1 (fr) | 2010-11-23 | 2012-12-21 | Michelin Soc Tech | Composition contenant un elastomere dienique particulier et un noir de carbone de surface specifique particuliere |
| JP6034365B2 (ja) | 2011-04-06 | 2016-11-30 | ダウ グローバル テクノロジーズ エルエルシー | 高い嵩密度、良好な流動性及び改善された冷水分散性を有するセルロース誘導体の製造方法。 |
| KR102171570B1 (ko) | 2012-09-25 | 2020-10-29 | 다우 글로벌 테크놀로지스 엘엘씨 | 높은 벌크 밀도, 우수한 유동성 및/또는 우수한 냉수 분산성 및 약한 용액 색을 갖는 셀룰로스 유도체의 제조 방법 |
| KR102687046B1 (ko) * | 2016-07-13 | 2024-07-23 | 롯데정밀화학 주식회사 | 셀룰로오스 에테르의 제조방법, 상기 방법에 의해 제조된 셀룰로오스 에테르 및 이를 포함하는 건축 마감재 |
| WO2020241756A1 (ja) * | 2019-05-29 | 2020-12-03 | 花王株式会社 | 改質セルロースの製造方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2647064A (en) * | 1949-11-25 | 1953-07-28 | Dow Chemical Co | Method of improving the cold-water solubility of a fibrous cellulose ether |
| US2720464A (en) * | 1952-10-24 | 1955-10-11 | Dow Chemical Co | Method of preparing cold-water-soluble powdered cellulose ethers |
| US3619451A (en) * | 1967-09-29 | 1971-11-09 | Ici Ltd | Powdered cellulose ether |
| FI53144C (cg-RX-API-DMAC7.html) | 1976-03-10 | 1978-02-10 | Kemira Oy | |
| DE2750148A1 (de) * | 1977-11-09 | 1979-05-10 | Svenska Traeforskningsinst | Verfahren zur herstellung von alkalizellulose |
| DE3147434A1 (de) * | 1981-11-30 | 1983-06-09 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von celluloseethern mit dimethoxyethan als dispergierhilfsmittel |
| JPS5975902A (ja) * | 1982-10-22 | 1984-04-28 | Daicel Chem Ind Ltd | ヒドロキシエチルセルロ−スの製造法 |
| DE3306621A1 (de) * | 1983-02-25 | 1984-08-30 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von celluloseethern mit einem dimethoxyethan enthaltenden dispergierhilfsmittel |
| DD258613A1 (de) * | 1985-02-22 | 1988-07-27 | Schwarza Chemiefaser | Verfahren zur herstellung von wasserloeslicher alkalicarboxymethylcellulose |
| US4845206A (en) * | 1987-05-21 | 1989-07-04 | The Dow Chemical Company | Production of cellulose ethers using a premix of alkali and etherifying agent |
| AT394859B (de) * | 1988-12-16 | 1992-07-10 | Brigl & Bergmeister | Bodenverbesserungsmittel |
| JPH03279471A (ja) * | 1990-03-22 | 1991-12-10 | Toyobo Co Ltd | 超吸水短繊維の製造法 |
| DE4112849A1 (de) * | 1990-04-26 | 1991-10-31 | Hoechst Ag | Verfahren zum abtrennen und reinigen von celluloseethern aus einer celluloseethersuspension |
| US6146570A (en) | 1998-03-20 | 2000-11-14 | Rhodia Inc. | Process for producing extruded hydrocolloid granules |
| JP4073080B2 (ja) * | 1998-05-20 | 2008-04-09 | 信越化学工業株式会社 | セルロースエーテル粉末およびその製造方法 |
| US6197100B1 (en) * | 1998-12-04 | 2001-03-06 | Hercules Incorporated | Dispersible water soluble polymers |
-
2000
- 2000-04-12 DE DE10018155A patent/DE10018155A1/de not_active Withdrawn
-
2001
- 2001-04-12 EP EP01931601A patent/EP1278779B1/de not_active Expired - Lifetime
- 2001-04-12 US US10/257,434 patent/US7361753B2/en not_active Expired - Lifetime
- 2001-04-12 KR KR1020027013669A patent/KR100782644B1/ko not_active Expired - Fee Related
- 2001-04-12 WO PCT/EP2001/004260 patent/WO2001077183A1/de not_active Ceased
- 2001-04-12 DE DE50106637T patent/DE50106637D1/de not_active Expired - Lifetime
- 2001-04-12 MX MXPA02010035A patent/MXPA02010035A/es active IP Right Grant
- 2001-04-12 JP JP2001575653A patent/JP5237518B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA02010035A (es) | 2003-04-25 |
| KR20020089452A (ko) | 2002-11-29 |
| WO2001077183A1 (de) | 2001-10-18 |
| EP1278779A1 (de) | 2003-01-29 |
| JP2003530466A (ja) | 2003-10-14 |
| EP1278779B1 (de) | 2005-06-29 |
| DE10018155A1 (de) | 2001-10-25 |
| US7361753B2 (en) | 2008-04-22 |
| KR100782644B1 (ko) | 2007-12-06 |
| US20040110942A1 (en) | 2004-06-10 |
| DE50106637D1 (de) | 2005-08-04 |
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