JP4388689B2 - 新規なセルロースエーテル及びその製造法 - Google Patents
新規なセルロースエーテル及びその製造法 Download PDFInfo
- Publication number
- JP4388689B2 JP4388689B2 JP2000503113A JP2000503113A JP4388689B2 JP 4388689 B2 JP4388689 B2 JP 4388689B2 JP 2000503113 A JP2000503113 A JP 2000503113A JP 2000503113 A JP2000503113 A JP 2000503113A JP 4388689 B2 JP4388689 B2 JP 4388689B2
- Authority
- JP
- Japan
- Prior art keywords
- cellulose
- solution
- reaction
- nmmno
- cellulose 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 abstract description 17
- 238000000034 method Methods 0.000 title claims description 16
- 229920002678 cellulose Polymers 0.000 claims abstract description 62
- 239000001913 cellulose Substances 0.000 claims abstract description 60
- 238000006467 substitution reaction Methods 0.000 claims abstract description 14
- TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical group O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 20
- 239000007790 solid phase Substances 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 239000003381 stabilizer Substances 0.000 claims description 10
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 7
- WAZPLXZGZWWXDQ-UHFFFAOYSA-N 4-methyl-4-oxidomorpholin-4-ium;hydrate Chemical compound O.C[N+]1([O-])CCOCC1 WAZPLXZGZWWXDQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 235000010980 cellulose Nutrition 0.000 description 59
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 50
- 239000000243 solution Substances 0.000 description 41
- LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 238000003756 stirring Methods 0.000 description 15
- 239000007864 aqueous solution Substances 0.000 description 14
- 238000006266 etherification reaction Methods 0.000 description 13
- 239000004793 Polystyrene Substances 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 11
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 9
- 238000009826 distribution Methods 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 8
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 8
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 8
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 235000011121 sodium hydroxide Nutrition 0.000 description 8
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
- 150000001450 anions Chemical class 0.000 description 6
- 230000015556 catabolic process Effects 0.000 description 6
- 238000006731 degradation reaction Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 229940075579 propyl gallate Drugs 0.000 description 5
- 235000010388 propyl gallate Nutrition 0.000 description 5
- 239000000473 propyl gallate Substances 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 4
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 4
- 229940008309 acetone / ethanol Drugs 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 4
- 229960004592 isopropanol Drugs 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- KXJGSNRAQWDDJT-UHFFFAOYSA-N 1-acetyl-5-bromo-2h-indol-3-one Chemical compound BrC1=CC=C2N(C(=O)C)CC(=O)C2=C1 KXJGSNRAQWDDJT-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- 150000001350 alkyl halides Chemical class 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000007278 cyanoethylation reaction Methods 0.000 description 2
- 238000001212 derivatisation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- GJOWSEBTWQNKPC-UHFFFAOYSA-N 3-methyloxiran-2-ol Chemical compound CC1OC1O GJOWSEBTWQNKPC-UHFFFAOYSA-N 0.000 description 1
- FNWWXCLMWLVPJX-UHFFFAOYSA-N 4-hydroxy-3-methylmorpholine Chemical compound CC1COCCN1O FNWWXCLMWLVPJX-UHFFFAOYSA-N 0.000 description 1
- MELDBFYJFQCSFP-UHFFFAOYSA-N 5-(4-carboxy-3-hydroxybutoxy)-3-hydroxypentanoic acid Chemical group OC(=O)CC(O)CCOCCC(O)CC(O)=O MELDBFYJFQCSFP-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 229920000057 Mannan Polymers 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- -1 cyclic amine Chemical class 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical compound CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 description 1
- 150000004986 phenylenediamines Chemical class 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
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000003385 ring cleavage reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical group [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 239000002023 wood 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
-
- 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
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- B01J31/08—Ion-exchange resins
-
- 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
- C08B11/04—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals
-
- 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
- C08B11/193—Mixed ethers, i.e. ethers with two or more different etherifying groups
-
- 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
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
-
- 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
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/48—Ring-opening reactions
-
- 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
- B01J2531/90—Catalytic systems characterized by the solvent or solvent system used
- B01J2531/98—Phase-transfer catalysis in a mixed solvent system containing at least 2 immiscible solvents or solvent phases
- B01J2531/985—Phase-transfer catalysis in a mixed solvent system containing at least 2 immiscible solvents or solvent phases in a water / organic solvent system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19730090A DE19730090A1 (de) | 1997-07-14 | 1997-07-14 | Neuartige Celluloseether und Verfahren zu deren Herstellung |
| DE19730090.1 | 1997-07-14 | ||
| PCT/EP1998/004061 WO1999003891A1 (de) | 1997-07-14 | 1998-07-01 | Neuartige celluloseether und verfahren zu deren herstellung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2001510207A JP2001510207A (ja) | 2001-07-31 |
| JP2001510207A5 JP2001510207A5 (enExample) | 2006-01-05 |
| JP4388689B2 true JP4388689B2 (ja) | 2009-12-24 |
Family
ID=7835638
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000503113A Expired - Lifetime JP4388689B2 (ja) | 1997-07-14 | 1998-07-01 | 新規なセルロースエーテル及びその製造法 |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US6482940B1 (enExample) |
| EP (1) | EP0996641B1 (enExample) |
| JP (1) | JP4388689B2 (enExample) |
| KR (1) | KR100477017B1 (enExample) |
| AT (1) | ATE202572T1 (enExample) |
| AU (1) | AU8854498A (enExample) |
| BR (1) | BR9810718A (enExample) |
| DE (2) | DE19730090A1 (enExample) |
| TR (1) | TR200000085T2 (enExample) |
| WO (1) | WO1999003891A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19730090A1 (de) * | 1997-07-14 | 1999-01-21 | Wolff Walsrode Ag | Neuartige Celluloseether und Verfahren zu deren Herstellung |
| DE19817454A1 (de) * | 1998-04-20 | 1999-10-21 | Wolff Walsrode Ag | Verfahren zur Aktivierung und Derivatisierung von Cellulose |
| US6933381B2 (en) * | 2001-02-02 | 2005-08-23 | Charles B. Mallon | Method of preparing modified cellulose ether |
| CN101171264B (zh) * | 2005-03-02 | 2012-01-11 | 赫尔克里士公司 | 水溶性低取代的羟乙基纤维素、其衍生物、其制备方法和用途 |
| US20090084509A1 (en) * | 2007-09-28 | 2009-04-02 | Weyerhaeuser Company | Dissolution of Cellulose in Mixed Solvent Systems |
| EP2098539B1 (en) | 2008-03-03 | 2017-05-10 | SE Tylose GmbH & Co.KG | Homogeneous synthesis of cellulose ethers in ionic liquids |
| JP5362483B2 (ja) * | 2008-08-27 | 2013-12-11 | 三洋化成工業株式会社 | アルキルエーテル化カルボキシアルキルセルロースの製造方法 |
| JP2010163485A (ja) * | 2009-01-13 | 2010-07-29 | Teijin Ltd | カルボキシ多糖類の溶液 |
| US8980050B2 (en) | 2012-08-20 | 2015-03-17 | Celanese International Corporation | Methods for removing hemicellulose |
| CN103619884B (zh) * | 2011-06-14 | 2016-06-29 | 陶氏环球技术有限责任公司 | 包括纤维素醚的食品组合物 |
| US20140048221A1 (en) | 2012-08-20 | 2014-02-20 | Celanese International Corporation | Methods for extracting hemicellulose from a cellulosic material |
| KR101549729B1 (ko) * | 2012-12-27 | 2015-09-11 | 제일모직주식회사 | 셀룰로오스계 수지 및 그 제조방법 |
| CN105461812A (zh) * | 2015-07-01 | 2016-04-06 | 四川大学 | 一种均相反应制备纤维素醚的方法 |
| CN107949577B (zh) * | 2015-09-07 | 2021-04-06 | 花王株式会社 | 改性纤维素纤维 |
| EP3521317A4 (en) * | 2016-09-29 | 2020-05-20 | Sumitomo Seika Chemicals Co. Ltd. | PROCESS FOR PRODUCING WATER-SOLUBLE HYDROXYETHYL CELLULOSE |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE207380C (enExample) | 1907-06-12 | |||
| US3447939A (en) | 1966-09-02 | 1969-06-03 | Eastman Kodak Co | Compounds dissolved in cyclic amine oxides |
| FR1546858A (fr) * | 1966-11-17 | 1968-11-22 | Bexford Ltd | Feuilles pour diazotypie |
| US4196282A (en) | 1977-11-25 | 1980-04-01 | Akzona Incorporated | Process for making a shapeable cellulose and shaped cellulose products |
| US4145532A (en) | 1977-11-25 | 1979-03-20 | Akzona Incorporated | Process for making precipitated cellulose |
| DD207380A1 (de) * | 1982-11-02 | 1984-02-29 | Adw Inst Polymerenchemie | Verfahren zur herstellung hochquellender carboxymethylcellulose |
| JPS6094401A (ja) * | 1983-10-31 | 1985-05-27 | Asahi Chem Ind Co Ltd | 吸液特性のすぐれたセルロース誘導体およびその製造方法 |
| DE3417952A1 (de) * | 1984-05-15 | 1985-11-21 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von wasserloeslichen cellulosemischethern |
| JPS59230001A (ja) * | 1984-05-19 | 1984-12-24 | Kohjin Co Ltd | カルボキシエチルエチルセルロ−スの製造方法 |
| JPH0674281B2 (ja) * | 1985-11-16 | 1994-09-21 | 旭化成工業株式会社 | アルカリ可溶セルロ−スおよびそのド−プ |
| ATA92690A (de) | 1990-04-20 | 1992-06-15 | Chemiefaser Lenzing Ag | Verfahren zur herstellung einer loesung von cellulose in n-methylmorpholin-n-oxid und wasser |
| US5437899A (en) * | 1992-07-14 | 1995-08-01 | Composite Development Corporation | Structural element formed of a fiber reinforced thermoplastic material and method of manufacture |
| AT400581B (de) | 1993-10-19 | 1996-01-25 | Chemiefaser Lenzing Ag | Verfahren zur herstellung von lösungen von cellulose |
| DE19730090A1 (de) * | 1997-07-14 | 1999-01-21 | Wolff Walsrode Ag | Neuartige Celluloseether und Verfahren zu deren Herstellung |
-
1997
- 1997-07-14 DE DE19730090A patent/DE19730090A1/de not_active Withdrawn
-
1998
- 1998-07-01 JP JP2000503113A patent/JP4388689B2/ja not_active Expired - Lifetime
- 1998-07-01 US US09/446,998 patent/US6482940B1/en not_active Expired - Lifetime
- 1998-07-01 EP EP98940105A patent/EP0996641B1/de not_active Expired - Lifetime
- 1998-07-01 BR BR9810718-6A patent/BR9810718A/pt not_active IP Right Cessation
- 1998-07-01 AU AU88544/98A patent/AU8854498A/en not_active Abandoned
- 1998-07-01 AT AT98940105T patent/ATE202572T1/de not_active IP Right Cessation
- 1998-07-01 KR KR10-2000-7000359A patent/KR100477017B1/ko not_active Expired - Lifetime
- 1998-07-01 TR TR2000/00085T patent/TR200000085T2/xx unknown
- 1998-07-01 DE DE59800943T patent/DE59800943D1/de not_active Expired - Lifetime
- 1998-07-01 WO PCT/EP1998/004061 patent/WO1999003891A1/de not_active Ceased
-
2002
- 2002-09-30 US US10/261,332 patent/US6939960B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| KR20010021795A (ko) | 2001-03-15 |
| WO1999003891A1 (de) | 1999-01-28 |
| JP2001510207A (ja) | 2001-07-31 |
| US20030032798A1 (en) | 2003-02-13 |
| TR200000085T2 (tr) | 2000-08-21 |
| US6939960B2 (en) | 2005-09-06 |
| US6482940B1 (en) | 2002-11-19 |
| DE59800943D1 (de) | 2001-08-02 |
| KR100477017B1 (ko) | 2005-03-18 |
| BR9810718A (pt) | 2000-08-08 |
| ATE202572T1 (de) | 2001-07-15 |
| AU8854498A (en) | 1999-02-10 |
| DE19730090A1 (de) | 1999-01-21 |
| EP0996641B1 (de) | 2001-06-27 |
| EP0996641A1 (de) | 2000-05-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100477017B1 (ko) | 신규한 셀룰로오스 에테르 및 그의 제조 방법 | |
| KR101611611B1 (ko) | 이온성 액체 중의 셀룰로스 에터의 균질 합성 | |
| US20070112185A1 (en) | Method for preparing a cellulose ether | |
| US7402668B2 (en) | Process of preparing alkylhydroxyalkylcellulose | |
| MXPA01008023A (es) | Procedimiento para la obtencion de alquilhidorxi-alquilcelulosas. | |
| JP2025063099A (ja) | 架橋セルロースエーテルを製造するためのプロセス | |
| US4250305A (en) | Process for preparing cellulose ether | |
| CA1194863A (en) | Process for the preparation of cellulose ethers from ammonia-activated cellulose | |
| FI100657B (fi) | Vesiliukoisia hydroksipropyylisulfoetyyliselluloosajohdannaisia (HPSES ), joilla on alhainen substituutioaste, ja menetelmä niiden valmistami seksi | |
| US11919976B1 (en) | Preparation and purification method for cationic quaternary ammonium salt of sodium hyaluronate in homogeneous medium | |
| JP2002512271A (ja) | セルロースの活性化及び誘導体化の方法 | |
| US5294702A (en) | Water-soluble polymerizable 3-allyloxy-2-hydroxypropylether of cellulose | |
| JP4950434B2 (ja) | メチルヒドロキシアルキルセルロースの製造方法 | |
| US4582899A (en) | Manufacturing method for cellulose ether having high degree of substitution | |
| Bert et al. | Substitution Patterns of Cellulose Ethers‐Influence of the Synthetic Pathway | |
| JPH0157681B2 (enExample) | ||
| KR19990057607A (ko) | 키토산 유도체 제조방법 | |
| MXPA00000503A (en) | Novel cellulose ethers and method for producing the same | |
| JP2000186101A (ja) | ヒドロキシプロピルセルロースの製造法 | |
| KR100348641B1 (ko) | 개선된카르복시메틸셀룰로오스의제조방법 | |
| JPH0681761B2 (ja) | セルロース誘導体の低分子化方法および低分子量セルロース誘導体のエーテル化方法 | |
| JPH09227601A (ja) | スルホン酸基含有セルロース誘導体の製造法 | |
| JPH0469161B2 (enExample) | ||
| US4111858A (en) | Process for the preparation of polyhydroxy methylene ethers and ion exchangers composed thereof | |
| KR20060086069A (ko) | 셀룰로오스 에테르 유도체의 제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20050516 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20050516 |
|
| A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A712 Effective date: 20080702 |
|
| RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20081006 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20090428 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20090727 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20090803 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20090821 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20090929 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20091005 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20121009 Year of fee payment: 3 |
|
| S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313113 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20121009 Year of fee payment: 3 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20121009 Year of fee payment: 3 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20131009 Year of fee payment: 4 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| EXPY | Cancellation because of completion of term |