DE3238278C2 - - Google Patents
Info
- Publication number
- DE3238278C2 DE3238278C2 DE19823238278 DE3238278A DE3238278C2 DE 3238278 C2 DE3238278 C2 DE 3238278C2 DE 19823238278 DE19823238278 DE 19823238278 DE 3238278 A DE3238278 A DE 3238278A DE 3238278 C2 DE3238278 C2 DE 3238278C2
- Authority
- DE
- Germany
- Prior art keywords
- range
- carboxymethyl
- alkali
- excess
- polysaccharide
- 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 32
- 229920001282 polysaccharide Polymers 0.000 claims description 30
- 239000005017 polysaccharide Substances 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 25
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 21
- 150000004676 glycans Chemical class 0.000 claims description 20
- 239000003513 alkali Substances 0.000 claims description 17
- 238000006467 substitution reaction Methods 0.000 claims description 17
- -1 carboxymethyl polysaccharide ethers Chemical class 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 14
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 13
- 238000006266 etherification reaction Methods 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 150000002170 ethers Chemical class 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 5
- 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 4
- 238000006386 neutralization reaction Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000001350 alkyl halides Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000003113 alkalizing effect Effects 0.000 claims description 2
- 238000010586 diagram Methods 0.000 claims description 2
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims 2
- 239000000047 product Substances 0.000 description 24
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- 229920002678 cellulose Polymers 0.000 description 18
- 235000010980 cellulose Nutrition 0.000 description 18
- 239000001913 cellulose Substances 0.000 description 16
- 229960004592 isopropanol Drugs 0.000 description 10
- 235000011121 sodium hydroxide Nutrition 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 7
- 241000218657 Picea Species 0.000 description 7
- 229920002472 Starch Polymers 0.000 description 7
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 7
- 235000019698 starch Nutrition 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 230000008961 swelling Effects 0.000 description 6
- 230000006872 improvement Effects 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 125000001033 ether group Chemical group 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 240000000731 Fagus sylvatica Species 0.000 description 2
- 235000010099 Fagus sylvatica Nutrition 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 229920003086 cellulose ether Polymers 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229940050176 methyl chloride Drugs 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N n-propyl alcohol Natural products CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 244000303965 Cyamopsis psoralioides Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-N methyl hydrogen carbonate Chemical group COC(O)=O CXHHBNMLPJOKQD-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229940045681 other alkylating agent in atc Drugs 0.000 description 1
- 150000004804 polysaccharides Polymers 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000000063 preceeding effect Effects 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 229920003169 water-soluble 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
- C08B11/193—Mixed ethers, i.e. ethers with two or more different etherifying groups
-
- 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
- C08B11/10—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals substituted with acid radicals
- C08B11/12—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals substituted with acid radicals substituted with carboxylic radicals, e.g. carboxymethylcellulose [CMC]
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B31/00—Preparation of derivatives of starch
- C08B31/08—Ethers
- C08B31/12—Ethers having alkyl or cycloalkyl radicals substituted by heteroatoms, e.g. hydroxyalkyl or carboxyalkyl starch
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)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823238278 DE3238278A1 (de) | 1982-10-15 | 1982-10-15 | Verfahren zur herstellung von niedrigsubstituierten, gut wasserloeslichen carboxyalkyl-polysaccharid-(misch-)ethern sowie entsprechende polysaccharid-mischether |
| BE0/211690A BE897979A (fr) | 1982-10-15 | 1983-10-13 | Procede de preparation de carboxyalcoyl-polysaccharide-ethers (mixtes) faiblement substitues et a bonne solubilite dans l'eau, ainsi que les polysaccharide-ethers mixtes correspondants |
| FR8316411A FR2534590B1 (fr) | 1982-10-15 | 1983-10-14 | Procede de preparation de carboxyalcoyl-polysaccharide-ethers (mixtes) faiblement substitues et a bonne solubilite dans l'eau, ainsi que les polysaccharide-ethers mixtes correspondants |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823238278 DE3238278A1 (de) | 1982-10-15 | 1982-10-15 | Verfahren zur herstellung von niedrigsubstituierten, gut wasserloeslichen carboxyalkyl-polysaccharid-(misch-)ethern sowie entsprechende polysaccharid-mischether |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3238278A1 DE3238278A1 (de) | 1984-04-19 |
| DE3238278C2 true DE3238278C2 (enrdf_load_stackoverflow) | 1991-07-11 |
Family
ID=6175817
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823238278 Granted DE3238278A1 (de) | 1982-10-15 | 1982-10-15 | Verfahren zur herstellung von niedrigsubstituierten, gut wasserloeslichen carboxyalkyl-polysaccharid-(misch-)ethern sowie entsprechende polysaccharid-mischether |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE897979A (enrdf_load_stackoverflow) |
| DE (1) | DE3238278A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2534590B1 (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102007015282B4 (de) * | 2007-03-29 | 2017-10-05 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Viskositätsregulator, Verfahren zu dessen Herstellung und dessen Verwendung |
| CN110590965A (zh) * | 2019-10-28 | 2019-12-20 | 山东一滕新材料股份有限公司 | 一种提升瓷砖胶开放时间的改性淀粉醚的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1222031B (de) * | 1962-10-26 | 1966-08-04 | Hercules Powder Co Ltd | Verfahren zur Herstellung von Cellulose- oder Staerkeaethern |
| US2618632A (en) * | 1949-04-05 | 1952-11-18 | Hercules Powder Co Ltd | Mixed cellulose ether and preparation thereof |
| US3085087A (en) * | 1956-09-13 | 1963-04-09 | Hercules Powder Co Ltd | Preparation of carboxyalkyl cellulose ethers |
| GB928792A (en) * | 1959-10-23 | 1963-06-12 | Hercules Powder Co Ltd | Improvements in or relating to alkali cellulose and preparation of cellulose ethers therefrom which give smooth solutions |
| DE1543136C3 (de) * | 1965-12-30 | 1980-04-17 | Hoechst Ag, 6000 Frankfurt | Verfahren zur kontinuierlichen Herstellung von Methylcellulose oder Methylhydroxyalkylcellulose |
| BE703740A (enrdf_load_stackoverflow) * | 1967-09-11 | 1968-03-11 |
-
1982
- 1982-10-15 DE DE19823238278 patent/DE3238278A1/de active Granted
-
1983
- 1983-10-13 BE BE0/211690A patent/BE897979A/fr not_active IP Right Cessation
- 1983-10-14 FR FR8316411A patent/FR2534590B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE3238278A1 (de) | 1984-04-19 |
| BE897979A (fr) | 1984-01-30 |
| FR2534590A1 (fr) | 1984-04-20 |
| FR2534590B1 (fr) | 1986-12-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8363 | Opposition against the patent | ||
| 8330 | Complete disclaimer |