DE1568804A1 - Wasserloesliche AEther-Ester von Cellulose - Google Patents
Wasserloesliche AEther-Ester von CelluloseInfo
- Publication number
- DE1568804A1 DE1568804A1 DE19661568804 DE1568804A DE1568804A1 DE 1568804 A1 DE1568804 A1 DE 1568804A1 DE 19661568804 DE19661568804 DE 19661568804 DE 1568804 A DE1568804 A DE 1568804A DE 1568804 A1 DE1568804 A1 DE 1568804A1
- Authority
- DE
- Germany
- Prior art keywords
- cellulose
- water
- product
- minutes
- control
- 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.)
- Pending
Links
- 229920002678 cellulose Polymers 0.000 title claims description 10
- 239000001913 cellulose Substances 0.000 title claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 229920003086 cellulose ether Polymers 0.000 claims description 17
- 239000006260 foam Substances 0.000 claims description 14
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 13
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 13
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 6
- -1 methylhydroxypropyl Chemical group 0.000 claims description 6
- 238000004090 dissolution Methods 0.000 claims description 5
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 3
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 3
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 3
- 229920000609 methyl cellulose Polymers 0.000 claims description 3
- 239000001923 methylcellulose Substances 0.000 claims description 3
- 235000010981 methylcellulose Nutrition 0.000 claims description 3
- 229920003090 carboxymethyl hydroxyethyl cellulose Polymers 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 229920013821 hydroxy alkyl cellulose Polymers 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 238000009423 ventilation Methods 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 48
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
- 239000003054 catalyst Substances 0.000 description 18
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 15
- 150000008064 anhydrides Chemical class 0.000 description 12
- 230000010933 acylation Effects 0.000 description 9
- 238000005917 acylation reaction Methods 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 230000021736 acetylation Effects 0.000 description 7
- 238000006640 acetylation reaction Methods 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- FFQQCJGNKKIRMD-UHFFFAOYSA-N methyl n-(3-hydroxyphenyl)carbamate Chemical compound COC(=O)NC1=CC=CC(O)=C1 FFQQCJGNKKIRMD-UHFFFAOYSA-N 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
- 125000002252 acyl group Chemical group 0.000 description 5
- 239000001632 sodium acetate Substances 0.000 description 5
- 235000017281 sodium acetate Nutrition 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 239000005060 rubber Substances 0.000 description 4
- 241000282376 Panthera tigris Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- WVJVHUWVQNLPCR-UHFFFAOYSA-N octadecanoyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCC WVJVHUWVQNLPCR-UHFFFAOYSA-N 0.000 description 3
- 230000036961 partial effect Effects 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- MOMFXATYAINJML-UHFFFAOYSA-N 2-Acetylthiazole Chemical group CC(=O)C1=NC=CS1 MOMFXATYAINJML-UHFFFAOYSA-N 0.000 description 2
- AURKDQJEOYBJSQ-UHFFFAOYSA-N 2-hydroxypropanoyl 2-hydroxypropanoate Chemical compound CC(O)C(=O)OC(=O)C(C)O AURKDQJEOYBJSQ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- 241000940612 Medina Species 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000004872 foam stabilizing agent Substances 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241001669573 Galeorhinus galeus Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229920013820 alkyl cellulose Polymers 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229920006184 cellulose methylcellulose Polymers 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000007922 dissolution test Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229940071826 hydroxyethyl cellulose Drugs 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 235000011962 puddings Nutrition 0.000 description 1
- 238000000746 purification Methods 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
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 235000012045 salad Nutrition 0.000 description 1
- 235000015067 sauces Nutrition 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar 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
- C08B13/00—Preparation of cellulose ether-esters
-
- 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
- C08B11/20—Post-etherification treatments of chemical or physical type, e.g. mixed etherification in two steps, including purification
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51356265A | 1965-12-13 | 1965-12-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1568804A1 true DE1568804A1 (de) | 1970-07-30 |
Family
ID=24043792
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661568804 Pending DE1568804A1 (de) | 1965-12-13 | 1966-12-09 | Wasserloesliche AEther-Ester von Cellulose |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3435027A (cg-RX-API-DMAC10.html) |
| DE (1) | DE1568804A1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1126244A (cg-RX-API-DMAC10.html) |
| NL (1) | NL6617513A (cg-RX-API-DMAC10.html) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3004161A1 (de) * | 1979-02-12 | 1980-08-21 | Hercules Inc | Cellulosederivate |
| DE3020689A1 (de) * | 1979-06-06 | 1981-01-22 | Hercules Inc | Celluloseaether |
| WO2002046239A1 (de) * | 2000-12-05 | 2002-06-13 | Wolff Cellulosics Gmbh & Co. Kg | Thermoplastische und wasserlösliche celluloseether-ester |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3940384A (en) * | 1973-08-13 | 1976-02-24 | Anheuser-Busch, Incorporated | Methyl hydroxypropyl cellulose acetate and process |
| US3870701A (en) * | 1973-10-15 | 1975-03-11 | Anheuser Busch | Benzyl hydroxypropyl cellulose acetate and process |
| PH18436A (en) * | 1980-11-07 | 1985-07-08 | Unilever Nv | A fabric softening composition and a process for preparing it |
| US4520192A (en) * | 1984-07-03 | 1985-05-28 | Daicel Chemical Industries Ltd. | Carboxyalkyl acetyl celluloses, their salts and a process for the preparation of them |
| US4939192A (en) * | 1987-06-17 | 1990-07-03 | Aqualon Company | Building composition containing 3-alkoxy-2-hydroxypropylhydroxyethyl cellulose |
| US4845207A (en) * | 1987-06-17 | 1989-07-04 | Aqualon Company | 3-alkoxy-2-hydroxypropylhydroxyethylcellulose and building composition containing the same |
| EP0781780B1 (en) * | 1995-12-27 | 2002-05-29 | Kao Corporation | Polysaccharide derivative, and preparation process and use thereof |
| US5668273A (en) * | 1996-01-29 | 1997-09-16 | Eastman Chemical Company | Carboxyalkyl cellulose esters |
| DE19618826A1 (de) * | 1996-05-10 | 1997-11-13 | Wolff Walsrode Ag | Kompostierbare und thermoplastisch verarbeitbare Celluloseether-2-Hydroxycarbonsäureester und Mischester |
| US6417268B1 (en) | 1999-12-06 | 2002-07-09 | Hercules Incorporated | Method for making hydrophobically associative polymers, methods of use and compositions |
| WO2002036637A1 (en) | 2000-11-01 | 2002-05-10 | Eastman Chemical Company | Use of carboxymethyl cellulose acetate butyrate |
| US8627828B2 (en) | 2003-11-07 | 2014-01-14 | U.S. Smokeless Tobacco Company Llc | Tobacco compositions |
| BRPI0415741B1 (pt) | 2003-11-07 | 2013-07-23 | composições de tabaco e métodos de fabricação de uma composição de tabaco | |
| JP5371473B2 (ja) * | 2008-06-30 | 2013-12-18 | 富士フイルム株式会社 | セルロース誘導体、樹脂組成物、成形体並びに電気・電子機器用筺体 |
| WO2010001864A1 (ja) * | 2008-06-30 | 2010-01-07 | 富士フイルム株式会社 | セルロース誘導体及びその製造方法、セルロース樹脂組成物、成形体及びその製造方法、並びに電気電子機器用筐体 |
| JP2010241848A (ja) * | 2009-03-31 | 2010-10-28 | Fujifilm Corp | セルロース樹脂組成物、成形体及び電気電子機器用筺体 |
| JP2011225786A (ja) * | 2010-04-22 | 2011-11-10 | Fujifilm Corp | セルロース誘導体、樹脂組成物、成形材料、成形体、成形体の製造方法、及び電気電子機器用筐体 |
| JP2012167155A (ja) * | 2011-02-10 | 2012-09-06 | Fujifilm Corp | セルロース誘導体、樹脂組成物、成形体及びその製造方法並びに電気電子機器用筐体 |
| US9453081B2 (en) | 2012-03-27 | 2016-09-27 | Dow Global Technologies Llc | Process of preparing an ester of a cellulose ether |
| US9320799B2 (en) | 2012-04-11 | 2016-04-26 | Dow Global Technologies Llc | Esterified cellulose ethers having a specific substituent distribution |
| EP2888291A1 (en) | 2012-08-24 | 2015-07-01 | Dow Global Technologies LLC | Process for preparing an ester of a cellulose ether in the presence of an aliphatic carboxylic acid |
| MX2015002426A (es) | 2012-08-24 | 2015-06-22 | Dow Global Technologies Llc | Procedimiento para preparar un eter de celulosa esterificado en presencia de un carboxilato de metal alcalino y un acido carboxilico alifatico. |
| CN105829352B (zh) | 2013-09-23 | 2018-04-10 | 陶氏环球技术有限责任公司 | 用于从反应产物混合物中回收酯化纤维素醚的方法 |
| EP3186285B1 (en) | 2014-08-27 | 2022-04-13 | Nutrition & Biosciences USA 1, LLC | Esterified cellulose ethers of low acetone-insoluble content |
| CN113735982A (zh) | 2015-01-08 | 2021-12-03 | 陶氏环球技术有限责任公司 | 用于生产具有降低含量的水不溶性颗粒的水溶性纤维素衍生物的方法 |
| MX2017011092A (es) | 2015-03-16 | 2017-11-10 | Dow Global Technologies Llc | Proceso para fraccionar un eter esterificado de celulosa. |
| JP6356923B2 (ja) | 2015-03-16 | 2018-07-11 | ダウ グローバル テクノロジーズ エルエルシー | 水溶性エステル化セルロースエーテル |
| EP3596132B1 (en) | 2017-03-17 | 2021-05-05 | Nutrition & Biosciences USA 1, LLC | Process for recovering an esterified cellulose ether from a reaction product mixture |
| WO2018170060A1 (en) | 2017-03-17 | 2018-09-20 | Dow Global Technologies Llc | Process for recovering an esterified cellulose ether from a reaction product mixture |
| WO2018170083A1 (en) | 2017-03-17 | 2018-09-20 | Dow Global Technologies Llc | Process for recovering an esterified cellulose ether from a reaction product mixture |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2748111A (en) * | 1956-05-29 | Preparation of cellulose ether | ||
| US1994038A (en) * | 1929-11-19 | 1935-03-12 | Ig Farbenindustrie Ag | Hydroxyalkylcellulose ester |
| US2055892A (en) * | 1933-02-16 | 1936-09-29 | Dreyfus Henry | Manufacture of derivatives of cellulose and other carbohydrates |
| US2327397A (en) * | 1939-11-18 | 1943-08-24 | Carbide & Carbon Chem Corp | Process for making esters of hydroxyalkyl celluloses and product produced thereby |
| US2330263A (en) * | 1940-09-10 | 1943-09-28 | Carbide & Carbon Chem Corp | Esterification of hydroxyalkyl celluloses |
-
1965
- 1965-12-13 US US513562A patent/US3435027A/en not_active Expired - Lifetime
-
1966
- 1966-11-18 GB GB51741/66A patent/GB1126244A/en not_active Expired
- 1966-12-09 DE DE19661568804 patent/DE1568804A1/de active Pending
- 1966-12-13 NL NL6617513A patent/NL6617513A/xx unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3004161A1 (de) * | 1979-02-12 | 1980-08-21 | Hercules Inc | Cellulosederivate |
| DE3020689A1 (de) * | 1979-06-06 | 1981-01-22 | Hercules Inc | Celluloseaether |
| WO2002046239A1 (de) * | 2000-12-05 | 2002-06-13 | Wolff Cellulosics Gmbh & Co. Kg | Thermoplastische und wasserlösliche celluloseether-ester |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6617513A (cg-RX-API-DMAC10.html) | 1967-06-14 |
| US3435027A (en) | 1969-03-25 |
| GB1126244A (en) | 1968-09-05 |
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