CA1087177A - Process for the synthesis of hydroxyethyl cellulose with improved resistance to enzyme catalyzed hydrolysis - Google Patents
Process for the synthesis of hydroxyethyl cellulose with improved resistance to enzyme catalyzed hydrolysisInfo
- Publication number
- CA1087177A CA1087177A CA289,615A CA289615A CA1087177A CA 1087177 A CA1087177 A CA 1087177A CA 289615 A CA289615 A CA 289615A CA 1087177 A CA1087177 A CA 1087177A
- Authority
- CA
- Canada
- Prior art keywords
- cellulose
- slurry
- caustic
- water
- stage
- 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
Links
- 238000000034 method Methods 0.000 title claims abstract description 59
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 title claims abstract description 47
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 title claims abstract description 47
- 239000004354 Hydroxyethyl cellulose Substances 0.000 title claims abstract description 46
- 230000008569 process Effects 0.000 title claims abstract description 35
- 230000015572 biosynthetic process Effects 0.000 title abstract description 28
- 238000003786 synthesis reaction Methods 0.000 title abstract description 28
- 108090000790 Enzymes Proteins 0.000 title abstract description 12
- 102000004190 Enzymes Human genes 0.000 title abstract description 12
- 230000007062 hydrolysis Effects 0.000 title abstract description 5
- 238000006460 hydrolysis reaction Methods 0.000 title abstract description 5
- 229920002678 cellulose Polymers 0.000 claims abstract description 66
- 239000001913 cellulose Substances 0.000 claims abstract description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 57
- 239000003518 caustics Substances 0.000 claims abstract description 48
- 239000000543 intermediate Substances 0.000 claims description 30
- 239000002002 slurry Substances 0.000 claims description 28
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 20
- 238000006386 neutralization reaction Methods 0.000 claims description 20
- 239000002270 dispersing agent Substances 0.000 claims description 19
- 238000006467 substitution reaction Methods 0.000 claims description 15
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims description 14
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical group CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 13
- 239000006227 byproduct Substances 0.000 claims description 13
- 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 description 12
- 230000036961 partial effect Effects 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- 229940015043 glyoxal Drugs 0.000 claims description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 5
- 230000006872 improvement Effects 0.000 claims description 4
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 229940071826 hydroxyethyl cellulose Drugs 0.000 claims 2
- 238000004132 cross linking Methods 0.000 claims 1
- 238000007046 ethoxylation reaction Methods 0.000 abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 11
- 239000012429 reaction media Substances 0.000 abstract description 4
- 230000008961 swelling Effects 0.000 abstract 1
- 235000010980 cellulose Nutrition 0.000 description 55
- 239000000047 product Substances 0.000 description 21
- 238000006266 etherification reaction Methods 0.000 description 18
- 230000009257 reactivity Effects 0.000 description 18
- 238000000605 extraction Methods 0.000 description 15
- 229920003086 cellulose ether Polymers 0.000 description 14
- 150000003839 salts Chemical class 0.000 description 14
- 239000003513 alkali Substances 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 12
- 230000007071 enzymatic hydrolysis Effects 0.000 description 12
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 230000000717 retained effect Effects 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- 229940088598 enzyme Drugs 0.000 description 9
- 239000003973 paint Substances 0.000 description 9
- 230000002255 enzymatic effect Effects 0.000 description 8
- -1 hydroxyethyl groups Chemical group 0.000 description 8
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 7
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 7
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 description 5
- 239000013067 intermediate product Substances 0.000 description 5
- 238000004088 simulation Methods 0.000 description 5
- 241000228245 Aspergillus niger Species 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 238000011081 inoculation Methods 0.000 description 4
- 230000000087 stabilizing effect Effects 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000004816 latex Substances 0.000 description 3
- 229920000126 latex Polymers 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000012066 reaction slurry Substances 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000002860 competitive effect Effects 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical group 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 244000144992 flock Species 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 230000011987 methylation Effects 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HPUZPAIWNCLQGV-UHFFFAOYSA-N 1-(2-butoxyethoxy)propan-1-ol Chemical compound CCCCOCCOC(O)CC HPUZPAIWNCLQGV-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 108010059892 Cellulase Proteins 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000006811 Samuelson reaction Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229910002026 crystalline silica Inorganic materials 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000007515 enzymatic degradation Effects 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000011850 initial investigation Methods 0.000 description 1
- 229910001502 inorganic halide Inorganic materials 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- UKHVLWKBNNSRRR-TYYBGVCCSA-M quaternium-15 Chemical compound [Cl-].C1N(C2)CN3CN2C[N+]1(C/C=C/Cl)C3 UKHVLWKBNNSRRR-TYYBGVCCSA-M 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007665 sagging Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- FVEFRICMTUKAML-UHFFFAOYSA-M sodium tetradecyl sulfate Chemical compound [Na+].CCCCC(CC)CCC(CC(C)C)OS([O-])(=O)=O FVEFRICMTUKAML-UHFFFAOYSA-M 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- LDDXKZHJNJUZNQ-UHFFFAOYSA-M sodium;phthalic acid;hydroxide Chemical compound [OH-].[Na+].OC(=O)C1=CC=CC=C1C(O)=O LDDXKZHJNJUZNQ-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000012430 stability testing Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- C08B11/04—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals
- C08B11/08—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals with hydroxylated hydrocarbon radicals; Esters, ethers, or acetals thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US742,885 | 1976-11-18 | ||
| US05/742,885 US4084060A (en) | 1976-11-18 | 1976-11-18 | Process for the synthesis of hydroxyethyl cellulose with improved resistance to enzyme catalyzed hydrolysis |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1087177A true CA1087177A (en) | 1980-10-07 |
Family
ID=24986641
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA289,615A Expired CA1087177A (en) | 1976-11-18 | 1977-10-26 | Process for the synthesis of hydroxyethyl cellulose with improved resistance to enzyme catalyzed hydrolysis |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4084060A (enExample) |
| JP (1) | JPS5386750A (enExample) |
| BE (1) | BE860904A (enExample) |
| BR (1) | BR7707649A (enExample) |
| CA (1) | CA1087177A (enExample) |
| DE (1) | DE2751411C2 (enExample) |
| GB (1) | GB1553317A (enExample) |
| NL (1) | NL189134C (enExample) |
| SE (1) | SE432768B (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3151681A1 (de) | 1981-12-28 | 1983-07-07 | Henkel KGaA, 4000 Düsseldorf | "hydroxyalkylcellulosen mit verbesserter stabilitaet gegen abbau, verfahren zu ihrer herstellung und ihre verwendung" |
| JPS59120987U (ja) * | 1983-02-02 | 1984-08-15 | 水谷 仁司 | 線香立 |
| JPS61118566U (enExample) * | 1985-11-14 | 1986-07-26 | ||
| GB8704938D0 (en) * | 1987-03-03 | 1987-04-08 | Bp Chem Int Ltd | Cables |
| EP0384167B1 (en) | 1989-01-31 | 1994-07-06 | Union Carbide Chemicals And Plastics Company, Inc. | Polysaccharides with alkaryl or aralkyl hydrophobes and latex compositions containing same |
| US5124445A (en) * | 1989-10-30 | 1992-06-23 | Aqualon Company | Alkylaryl hydrophobically modified cellulose ethers |
| US5120838A (en) * | 1989-10-30 | 1992-06-09 | Aqualon Company | Alkylaryl hydrophobically modified cellulose ethers |
| US5493013A (en) * | 1992-04-23 | 1996-02-20 | Hoechst Aktiengesellschaft | Process for preparing cellulose ethers with cyclic ethers as suspending agents |
| US5504123A (en) * | 1994-12-20 | 1996-04-02 | Union Carbide Chemicals & Plastics Technology Corporation | Dual functional cellulosic additives for latex compositions |
| US5788987A (en) | 1997-01-29 | 1998-08-04 | Poli Industria Chimica Spa | Methods for treating early morning pathologies |
| US5879440A (en) * | 1997-07-28 | 1999-03-09 | Hercules Incorporated | Biostable water-borne paints and processes for their preparation |
| US6686464B1 (en) * | 1999-04-26 | 2004-02-03 | Bki Holding Corporation | Cellulose ethers and method of preparing the same |
| CA2427698A1 (en) * | 2000-11-01 | 2002-05-10 | Bki Holding Corporation | Cellulose ethers and method of preparing the same |
| US6405801B1 (en) * | 2000-12-08 | 2002-06-18 | Halliburton Energy Services, Inc. | Environmentally acceptable well cement fluid loss control additives, compositions and methods |
| EP1666075A1 (en) | 2004-10-04 | 2006-06-07 | Switch Biotech Aktiengesellschaft | Wound dressing compositions, especially for delivery of protease inhibitors |
| KR100654421B1 (ko) * | 2004-12-07 | 2006-12-06 | 삼성정밀화학 주식회사 | 효소분해 저항성 향상된 히드록시알킬셀룰로오스 유도체의제조방법 |
| CN101160350B (zh) | 2005-02-17 | 2011-06-22 | 赫尔克里士公司 | 不均匀取代的羟乙基纤维素、其衍生物、制备方法及其使用 |
| KR101321301B1 (ko) * | 2005-03-02 | 2013-10-30 | 허큘레스 인코포레이티드 | 수용성 저치환 히드록시에틸셀룰로스, 이의 유도체, 이의제조 방법, 및 용도 |
| DE102010022463A1 (de) | 2010-06-02 | 2011-12-08 | Se Tylose Gmbh & Co. Kg | Biostabile Celluloseether in nicht-wäßriger Dispersion und damit hergestellte Dispersionsfarbe |
| ES2683390T3 (es) * | 2012-12-06 | 2018-09-26 | Kao Corporation | Procedimiento para producir hidroxialquilcelulosas |
| KR102033179B1 (ko) * | 2012-12-28 | 2019-10-16 | 롯데정밀화학 주식회사 | 스킴코트 모르타르용 첨가제 및 이를 포함하는 스킴코트 모르타르 조성물 |
| CN109790226B (zh) * | 2016-09-29 | 2022-05-03 | 住友精化株式会社 | 水溶性羟乙基纤维素的制造方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2388764A (en) * | 1938-10-20 | 1945-11-13 | Sylvania Ind Corp | Cellulose ethers and process for producing the same |
| US2667481A (en) * | 1949-07-28 | 1954-01-26 | American Viscose Corp | Process for making water-soluble hydroxyalkyl cellulose ethers |
| US2687411A (en) * | 1952-03-15 | 1954-08-24 | American Viscose Corp | Production of water soluble cellulose ethers |
| US2744894A (en) * | 1952-09-08 | 1956-05-08 | Union Carbide & Carbon Corp | Hydroxyalkylation of polysaccharides |
| US3131176A (en) * | 1960-04-13 | 1964-04-28 | Hercules Powder Co Ltd | Manufacture of water-soluble hydroxyalkyl cellulose ethers |
| US3131177A (en) * | 1960-04-13 | 1964-04-28 | Hercules Powder Co Ltd | Manufacture of water-soluble hydroxyalkyl cellulose ethers |
| US3278521A (en) * | 1963-02-08 | 1966-10-11 | Hercules Inc | Hydroxypropyl cellulose and process |
| US3388082A (en) * | 1965-11-01 | 1968-06-11 | Dow Chemical Co | Novel hydroxypropyl methyl cellulose ethers, a process for preparing the same, and compositions utilizing such ethers |
| US3652539A (en) * | 1970-03-09 | 1972-03-28 | Nippon Soda Co | Process for the production of hydroxypropyl cellulose |
| US3709876A (en) * | 1972-04-10 | 1973-01-09 | Dow Chemical Co | Water soluble hydroxyethyl methyl cellulose ether thickener for latex paint |
| US3769247A (en) * | 1972-04-10 | 1973-10-30 | Dow Chemical Co | Cellulose ether thickener for latex paint |
| US3873518A (en) * | 1973-12-14 | 1975-03-25 | Dow Chemical Co | Water soluble ternary cellulose ethers |
-
1976
- 1976-11-18 US US05/742,885 patent/US4084060A/en not_active Expired - Lifetime
-
1977
- 1977-10-26 CA CA289,615A patent/CA1087177A/en not_active Expired
- 1977-11-17 DE DE2751411A patent/DE2751411C2/de not_active Expired
- 1977-11-17 BR BR7707649A patent/BR7707649A/pt unknown
- 1977-11-17 BE BE182678A patent/BE860904A/xx not_active IP Right Cessation
- 1977-11-17 JP JP13840077A patent/JPS5386750A/ja active Granted
- 1977-11-17 NL NLAANVRAGE7712688,A patent/NL189134C/xx not_active IP Right Cessation
- 1977-11-17 GB GB47799/77A patent/GB1553317A/en not_active Expired
- 1977-11-17 SE SE7713015A patent/SE432768B/sv not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2751411C2 (de) | 1984-03-15 |
| NL189134B (nl) | 1992-08-17 |
| BE860904A (fr) | 1978-05-17 |
| US4084060A (en) | 1978-04-11 |
| JPS5644081B2 (enExample) | 1981-10-17 |
| SE7713015L (sv) | 1978-05-19 |
| BR7707649A (pt) | 1978-06-13 |
| NL189134C (nl) | 1993-01-18 |
| GB1553317A (en) | 1979-09-26 |
| SE432768B (sv) | 1984-04-16 |
| JPS5386750A (en) | 1978-07-31 |
| NL7712688A (nl) | 1978-05-22 |
| DE2751411A1 (de) | 1978-05-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1087177A (en) | Process for the synthesis of hydroxyethyl cellulose with improved resistance to enzyme catalyzed hydrolysis | |
| US4243802A (en) | Surfactant-soluble cellulose derivatives | |
| EP0307915B1 (en) | Carboxymethyl hydrophobically modified hydroxyethylcellulose (cmhmhec) and use of cmhmhec in protective coating compositions | |
| CA1140541A (en) | Modified nonionic cellulose ethers | |
| US3709876A (en) | Water soluble hydroxyethyl methyl cellulose ether thickener for latex paint | |
| US4904772A (en) | Mixed hydrophobe polymers | |
| DE69820933T2 (de) | Biostabile, wässrige Lacke und Verfahren zur deren Herstellung | |
| EP0382150B1 (de) | Verfahren zur Herstellung von aktivierten Chitosanen und deren Verwendung bei der Herstellung von Chitosanderivaten | |
| US5140099A (en) | Water soluble nonionic cellulose ethers and their use in paints | |
| JPS63227601A (ja) | 疎水化非イオン系ポリガラクトマンナンエーテル | |
| US5120838A (en) | Alkylaryl hydrophobically modified cellulose ethers | |
| EP3981798B1 (en) | Modified chitosan, preparation method thereof, and additive for tile adhesive and use thereof | |
| DE69810472T2 (de) | Hydrophob modifizierte anionische celluloseether | |
| US4456751A (en) | Multiple stage process for preparing mixed hydroxyalkylcellulose ethers | |
| CA1060439A (en) | Bioresistant cellulose ethers | |
| US4306061A (en) | Preparation of CMC with improved substituent uniformity using borax | |
| KR20050094470A (ko) | 비이온성 셀룰로스 에테르와 이의 용도 | |
| US5124445A (en) | Alkylaryl hydrophobically modified cellulose ethers | |
| DE69320515T2 (de) | Hydrophobe Perfluoralkylhydroxyalkylcellulose als assoziatives Verdichungsmittel | |
| US5801239A (en) | Process for the preparation of alkali salt of carboxy alkyl cellulose | |
| EP0471866A1 (en) | Modified water-soluble cellulose ether | |
| CN1016786B (zh) | 一步法合成交联羧甲基羟丙基纤维素复合醚工艺 | |
| KR102453976B1 (ko) | 다당류 유도체 및 이의 제조 방법 | |
| JPH0643442B2 (ja) | 改良されたセルロースエーテル及びその製造 | |
| JPH0676441B2 (ja) | キトサンのカルボキシメチルエーテル塩の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |