DD211790A5 - Verfahren zur herstellung von celluloseethern aus mit ammoniak aktivierter cellulose - Google Patents
Verfahren zur herstellung von celluloseethern aus mit ammoniak aktivierter cellulose Download PDFInfo
- Publication number
- DD211790A5 DD211790A5 DD83256547A DD25654783A DD211790A5 DD 211790 A5 DD211790 A5 DD 211790A5 DD 83256547 A DD83256547 A DD 83256547A DD 25654783 A DD25654783 A DD 25654783A DD 211790 A5 DD211790 A5 DD 211790A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- cellulose
- ammonia
- organic solvent
- etherification
- activated
- Prior art date
Links
- 229920002678 cellulose Polymers 0.000 title claims abstract description 80
- 239000001913 cellulose Substances 0.000 title claims abstract description 79
- 238000000034 method Methods 0.000 title claims abstract description 39
- 230000008569 process Effects 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 229920003086 cellulose ether Polymers 0.000 title claims description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 84
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 36
- 239000003960 organic solvent Substances 0.000 claims abstract description 28
- 238000006266 etherification reaction Methods 0.000 claims abstract description 27
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 23
- 230000004913 activation Effects 0.000 claims abstract description 19
- 239000003513 alkali Substances 0.000 claims abstract description 13
- 230000003113 alkalizing effect Effects 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 54
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 9
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 235000010980 cellulose Nutrition 0.000 description 65
- 239000000243 solution Substances 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- 239000007795 chemical reaction product Substances 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- -1 aralkyl halides Chemical class 0.000 description 12
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 3
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 3
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 229920000896 Ethulose Polymers 0.000 description 2
- 239000001859 Ethyl hydroxyethyl cellulose Substances 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 235000019326 ethyl hydroxyethyl cellulose Nutrition 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920001425 Diethylaminoethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- 238000006959 Williamson synthesis reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 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
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229940093476 ethylene glycol Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 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
- C08B1/00—Preparatory treatment of cellulose for making derivatives thereof, e.g. pre-treatment, pre-soaking, activation
- C08B1/08—Alkali cellulose
-
- 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)
- Investigating Or Analysing Biological Materials (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823241720 DE3241720A1 (de) | 1982-11-11 | 1982-11-11 | Verfahren zur herstellung von celluloseethern aus mit ammoniak aktivierter cellulose |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD211790A5 true DD211790A5 (de) | 1984-07-25 |
Family
ID=6177868
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD83256547A DD211790A5 (de) | 1982-11-11 | 1983-11-10 | Verfahren zur herstellung von celluloseethern aus mit ammoniak aktivierter cellulose |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4491661A (pt) |
| EP (1) | EP0108991B1 (pt) |
| JP (1) | JPS5996101A (pt) |
| AT (1) | ATE21397T1 (pt) |
| BR (1) | BR8306178A (pt) |
| CA (1) | CA1194863A (pt) |
| DD (1) | DD211790A5 (pt) |
| DE (2) | DE3241720A1 (pt) |
| FI (1) | FI74025C (pt) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4329937C1 (de) * | 1993-09-04 | 1994-11-24 | Rhodia Ag Rhone Poulenc | Verfahren zur Behandlung von Cellulose zu deren Aktivierung für nachfolgende chemische Reaktionen |
| JP3390015B2 (ja) * | 1995-03-25 | 2003-03-24 | ローネ−ポウレンク ローディア アクチェン ゲゼルシャフト | 活性化しているポリサッカライドを得るためのプロセス、このプロセスによって作られるポリサッカライドおよびそれらの使用方法 |
| DE19646213C2 (de) * | 1996-11-08 | 1999-02-18 | Rhodia Acetow Ag | Verfahren zur Herstellung von Cellulosederivaten |
| FR2762603B1 (fr) * | 1997-04-25 | 1999-07-16 | Rhodia Ag Rhone Poulenc | Cellulose reactive et procede de fabrication de cette cellulose |
| US6686464B1 (en) | 1999-04-26 | 2004-02-03 | Bki Holding Corporation | Cellulose ethers and method of preparing the same |
| EP1334132A1 (en) * | 2000-11-01 | 2003-08-13 | BKI Holding Corporation | Cellulose ethers and method of preparing the same |
| JP2004026861A (ja) * | 2002-06-21 | 2004-01-29 | Shin Etsu Chem Co Ltd | 濾過性に優れる水溶性セルロースエーテル及びその選定方法 |
| EP1764373B1 (de) * | 2005-09-17 | 2016-04-27 | Dow Global Technologies LLC | Verfahren zur Herstellung von Methylhydroxyalkylcellulose mit einer geringen Anzahl gefärbter Partikel |
| US8519120B2 (en) * | 2006-08-08 | 2013-08-27 | Shin-Etsu Chemical Co., Ltd. | Methods for producing a low-substituted hydroxypropylcellulose powder |
| WO2019111939A1 (ja) | 2017-12-07 | 2019-06-13 | 日本製紙株式会社 | カルボキシメチル化セルロースナノファイバー |
| WO2019111934A1 (ja) | 2017-12-07 | 2019-06-13 | 日本製紙株式会社 | カルボキシメチル化セルロース |
| US11591412B2 (en) | 2017-12-07 | 2023-02-28 | Nippon Paper Industries Co., Ltd. | Carboxymethylated cellulose nanofibers |
| EP3722327B1 (en) * | 2017-12-07 | 2022-11-02 | Nippon Paper Industries Co., Ltd. | Method for manufacturing carboxymethylated cellulose nanofiber |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA546633A (en) * | 1957-09-24 | R. Grassie Vernon | Alkali cellulose preparation | |
| US1682294A (en) * | 1928-08-28 | chemistry | ||
| US2290888A (en) * | 1932-01-30 | 1942-07-28 | North American Rayon Corp | Cellulose activated by liquid ammonia |
| GB463056A (en) * | 1934-09-19 | 1937-03-19 | Du Pont | Improvements in or relating to the production of alkali cellulose particularly useful for making cellulose esters or ethers |
| US2110526A (en) * | 1937-01-09 | 1938-03-08 | Hercules Powder Co Ltd | Method for the preparation of cellulose ethers |
| US2294924A (en) * | 1937-11-30 | 1942-09-08 | North American Rayon Corp | Treatment of cellulose with alkali metal amides in anhydrous liquid ammonia |
| US2145273A (en) * | 1938-01-29 | 1939-01-31 | Dow Chemical Co | Preparation of cellulose ethers |
| US2157083A (en) * | 1938-01-29 | 1939-05-02 | Dow Chemical Co | Preparation of cellulose ethers |
| US2294925A (en) * | 1939-03-29 | 1942-09-08 | Clemmy O Miller | Manufacture of reactive forms of cellulose and the like |
| US2308692A (en) * | 1941-03-06 | 1943-01-19 | Dow Chemical Co | Greaseproof paper |
| US2296829A (en) * | 1941-03-22 | 1942-09-29 | Dow Chemical Co | Making alkali cellulose of low water content |
| US2671780A (en) * | 1948-08-31 | 1954-03-09 | Univ Ohio State Res Found | Processes for the preparation of new carbohydrate compounds and products thereof |
| US2729535A (en) * | 1949-06-22 | 1956-01-03 | Balassa Leslie L | Process of making alkali-insoluble cellulose glycolic acid ether fabric |
| US3069409A (en) * | 1958-06-12 | 1962-12-18 | Hercules Powder Co Ltd | Process of preparing carboxyalkyl cellulose ethers |
-
1982
- 1982-11-11 DE DE19823241720 patent/DE3241720A1/de not_active Withdrawn
-
1983
- 1983-10-26 CA CA000439735A patent/CA1194863A/en not_active Expired
- 1983-10-27 US US06/546,044 patent/US4491661A/en not_active Expired - Fee Related
- 1983-10-31 AT AT83110871T patent/ATE21397T1/de active
- 1983-10-31 JP JP58202916A patent/JPS5996101A/ja active Pending
- 1983-10-31 DE DE8383110871T patent/DE3365338D1/de not_active Expired
- 1983-10-31 EP EP83110871A patent/EP0108991B1/de not_active Expired
- 1983-11-09 FI FI834117A patent/FI74025C/fi not_active IP Right Cessation
- 1983-11-10 DD DD83256547A patent/DD211790A5/de unknown
- 1983-11-10 BR BR8306178A patent/BR8306178A/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI74025B (fi) | 1987-08-31 |
| EP0108991B1 (de) | 1986-08-13 |
| ATE21397T1 (de) | 1986-08-15 |
| FI834117L (fi) | 1984-05-12 |
| EP0108991A1 (de) | 1984-05-23 |
| CA1194863A (en) | 1985-10-08 |
| FI834117A0 (fi) | 1983-11-09 |
| FI74025C (fi) | 1987-12-10 |
| DE3241720A1 (de) | 1984-05-17 |
| DE3365338D1 (en) | 1986-09-18 |
| JPS5996101A (ja) | 1984-06-02 |
| US4491661A (en) | 1985-01-01 |
| BR8306178A (pt) | 1984-07-31 |
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