TWI731151B - 羥丙基甲基纖維素酞酸酯及羥丙基甲基纖維素酞酸酯之製造方法 - Google Patents
羥丙基甲基纖維素酞酸酯及羥丙基甲基纖維素酞酸酯之製造方法 Download PDFInfo
- Publication number
- TWI731151B TWI731151B TW106129097A TW106129097A TWI731151B TW I731151 B TWI731151 B TW I731151B TW 106129097 A TW106129097 A TW 106129097A TW 106129097 A TW106129097 A TW 106129097A TW I731151 B TWI731151 B TW I731151B
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- Prior art keywords
- hpmcp
- methyl cellulose
- suspension
- hydroxypropyl methyl
- phthalate
- Prior art date
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- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 title claims abstract description 31
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 title claims abstract description 31
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 14
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 title claims abstract description 11
- 229960003943 hypromellose Drugs 0.000 title abstract 10
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 claims abstract description 129
- 239000002245 particle Substances 0.000 claims abstract description 97
- 239000000725 suspension Substances 0.000 claims abstract description 53
- 239000007788 liquid Substances 0.000 claims abstract description 43
- 238000001035 drying Methods 0.000 claims abstract description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 238000005886 esterification reaction Methods 0.000 claims abstract description 11
- 230000032050 esterification Effects 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 6
- 239000012374 esterification agent Substances 0.000 claims abstract description 6
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 claims description 26
- 230000000694 effects Effects 0.000 claims description 17
- 238000005406 washing Methods 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 14
- 238000001556 precipitation Methods 0.000 claims description 13
- 238000000926 separation method Methods 0.000 claims description 13
- 239000007787 solid Substances 0.000 claims description 11
- 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 claims description 10
- -1 phthalate ester Chemical class 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 4
- 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
- 238000007599 discharging Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 abstract description 6
- 238000010298 pulverizing process Methods 0.000 abstract description 6
- 239000000843 powder Substances 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 13
- 239000012065 filter cake Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 11
- 238000007561 laser diffraction method Methods 0.000 description 8
- 230000000704 physical effect Effects 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000003513 alkali Substances 0.000 description 5
- 229920002678 cellulose Polymers 0.000 description 5
- 239000001913 cellulose Substances 0.000 description 5
- 238000007906 compression Methods 0.000 description 5
- 230000006835 compression Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 238000007873 sieving Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 4
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 4
- 238000009474 hot melt extrusion Methods 0.000 description 4
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 230000001186 cumulative effect Effects 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 230000002093 peripheral effect Effects 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000006266 etherification reaction Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000007962 solid dispersion Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- HSNHZGKSAZOEPE-SOFGYWHQSA-N (e)-3-(4-hydroxy-3-methoxyphenyl)-1-piperidin-1-ylprop-2-en-1-one Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)N2CCCCC2)=C1 HSNHZGKSAZOEPE-SOFGYWHQSA-N 0.000 description 1
- 101100287622 Haloarcula marismortui (strain ATCC 43049 / DSM 3752 / JCM 8966 / VKM B-1809) katG2 gene Proteins 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
- 229940005991 chloric acid Drugs 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000012812 general test Methods 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000003116 impacting effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010079 rubber tapping Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B3/00—Preparation of cellulose esters of organic acids
- C08B3/12—Preparation of cellulose esters of organic acids of polybasic organic acids
-
- 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
- C08B11/02—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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B3/00—Preparation of cellulose esters of organic acids
- C08B3/22—Post-esterification treatments, including purification
- C08B3/26—Isolation of the cellulose ester
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- 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)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2016166957A JP6742197B2 (ja) | 2016-08-29 | 2016-08-29 | ヒプロメロースフタル酸エステルの製造方法 |
| JP2016-166957 | 2016-08-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201825527A TW201825527A (zh) | 2018-07-16 |
| TWI731151B true TWI731151B (zh) | 2021-06-21 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW106129097A TWI731151B (zh) | 2016-08-29 | 2017-08-28 | 羥丙基甲基纖維素酞酸酯及羥丙基甲基纖維素酞酸酯之製造方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US10961323B2 (enExample) |
| EP (1) | EP3290443B1 (enExample) |
| JP (1) | JP6742197B2 (enExample) |
| KR (1) | KR102436733B1 (enExample) |
| CN (1) | CN107793487B (enExample) |
| TW (1) | TWI731151B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6644656B2 (ja) * | 2016-08-29 | 2020-02-12 | 信越化学工業株式会社 | ヒプロメロース酢酸エステルコハク酸エステルの製造方法 |
| EP3567058B1 (en) * | 2018-05-11 | 2023-09-20 | Shin-Etsu Chemical Co., Ltd. | Hypromellose phthalate and method for producing the same |
| JP7013343B2 (ja) * | 2018-07-25 | 2022-01-31 | 信越化学工業株式会社 | ヒプロメロースフタル酸エステルの製造方法 |
| JP7252882B2 (ja) | 2019-11-01 | 2023-04-05 | 信越化学工業株式会社 | ヒドロキシプロピルメチルセルロースアセテートサクシネートの製造方法 |
| JP7273691B2 (ja) * | 2019-11-01 | 2023-05-15 | 信越化学工業株式会社 | ヒドロキシプロピルメチルセルロースフタレートの製造方法 |
| JP7399061B2 (ja) * | 2020-10-01 | 2023-12-15 | 信越化学工業株式会社 | ヒドロキシプロピルメチルセルロースフタレートの製造方法 |
| US20240124690A1 (en) * | 2021-02-22 | 2024-04-18 | Asahi Kasei Kabushiki Kaisha | Composition Containing Cellulose Nanofibers |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW546305B (en) * | 2001-04-19 | 2003-08-11 | Samsung Fine Chemicals Co Ltd | Purification method of hydroxypropylmethyl cellulose phthalate |
| CN105829352A (zh) * | 2013-09-23 | 2016-08-03 | 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 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3043621A1 (de) | 1980-11-19 | 1982-07-08 | Bayer Ag, 5090 Leverkusen | Reinigung von cellulose- und staerkeethern |
| SE509400C2 (sv) | 1996-01-02 | 1999-01-25 | Noxon Ab | Dekanteringscentrifug |
| GB2357617A (en) | 1999-12-23 | 2001-06-27 | Mars Inc | Methods for detecting surfaces in vending machines |
| GB0102342D0 (en) * | 2001-01-30 | 2001-03-14 | Smithkline Beecham Plc | Pharmaceutical formulation |
| AU2003290060A1 (en) * | 2002-12-17 | 2004-07-09 | Abbott Gmbh & Co. Kg | Formulation comprising fenofibric acid, a physiologically acceptable salt or derivative thereof |
| US7514552B2 (en) * | 2003-05-30 | 2009-04-07 | Asahi Kasei Chemicals Corporation | Cellulose powder |
| JP4692330B2 (ja) * | 2006-02-28 | 2011-06-01 | 日本ゼオン株式会社 | 重合トナーの製造方法 |
| CN102215823A (zh) * | 2008-11-20 | 2011-10-12 | 安万托特性材料股份有限公司 | 直接可压制的基于高功能性颗粒磷酸氢钙的共处理的赋形剂 |
| EP2831121B1 (en) * | 2012-03-27 | 2018-10-10 | Dow Global Technologies LLC | A process of preparing an ester of a cellulose ether |
| EP2837391B1 (en) * | 2013-08-12 | 2017-05-10 | Shin-Etsu Chemical Co., Ltd. | Hypromellose acetate succinate for use as hot-melt extrusion carrier, hot-melt extrusion composition, and method for producing hot-melt extrudate |
| CN105126110B (zh) * | 2015-07-29 | 2018-04-06 | 中山大学 | 伊曲康唑的固体分散体及其制备方法和应用 |
-
2016
- 2016-08-29 JP JP2016166957A patent/JP6742197B2/ja active Active
-
2017
- 2017-08-22 US US15/683,032 patent/US10961323B2/en active Active
- 2017-08-24 EP EP17187784.8A patent/EP3290443B1/en active Active
- 2017-08-24 KR KR1020170106980A patent/KR102436733B1/ko active Active
- 2017-08-28 TW TW106129097A patent/TWI731151B/zh active
- 2017-08-29 CN CN201710758835.7A patent/CN107793487B/zh active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW546305B (en) * | 2001-04-19 | 2003-08-11 | Samsung Fine Chemicals Co Ltd | Purification method of hydroxypropylmethyl cellulose phthalate |
| CN105829352A (zh) * | 2013-09-23 | 2016-08-03 | 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP3290443B1 (en) | 2021-12-15 |
| KR102436733B1 (ko) | 2022-08-26 |
| CN107793487B (zh) | 2022-04-01 |
| US10961323B2 (en) | 2021-03-30 |
| TW201825527A (zh) | 2018-07-16 |
| JP6742197B2 (ja) | 2020-08-19 |
| US20180057613A1 (en) | 2018-03-01 |
| EP3290443A1 (en) | 2018-03-07 |
| CN107793487A (zh) | 2018-03-13 |
| JP2018035216A (ja) | 2018-03-08 |
| KR20180025208A (ko) | 2018-03-08 |
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