DE69400514T2 - Verfahren zur Modifizierung von Polyvinylalkohol in der Festkörperphase, mittels Michael-Addition - Google Patents
Verfahren zur Modifizierung von Polyvinylalkohol in der Festkörperphase, mittels Michael-AdditionInfo
- Publication number
- DE69400514T2 DE69400514T2 DE69400514T DE69400514T DE69400514T2 DE 69400514 T2 DE69400514 T2 DE 69400514T2 DE 69400514 T DE69400514 T DE 69400514T DE 69400514 T DE69400514 T DE 69400514T DE 69400514 T2 DE69400514 T2 DE 69400514T2
- Authority
- DE
- Germany
- Prior art keywords
- polyvinyl alcohol
- monomer
- powder
- swollen
- sodium
- 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 - Fee Related
Links
- 229920002451 polyvinyl alcohol Polymers 0.000 title claims description 100
- 239000004372 Polyvinyl alcohol Substances 0.000 title claims description 94
- 238000000034 method Methods 0.000 title claims description 33
- 238000006845 Michael addition reaction Methods 0.000 title claims description 10
- 238000012986 modification Methods 0.000 title description 11
- 230000004048 modification Effects 0.000 title description 9
- 239000007790 solid phase Substances 0.000 title 1
- 239000000843 powder Substances 0.000 claims description 38
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 25
- 239000000178 monomer Substances 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 14
- 239000002245 particle Substances 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 7
- BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical group [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 claims description 6
- 239000002002 slurry Substances 0.000 claims description 6
- 229920002689 polyvinyl acetate Polymers 0.000 claims description 5
- 239000011118 polyvinyl acetate Substances 0.000 claims description 5
- DZSVIVLGBJKQAP-UHFFFAOYSA-N 1-(2-methyl-5-propan-2-ylcyclohex-2-en-1-yl)propan-1-one Chemical compound CCC(=O)C1CC(C(C)C)CC=C1C DZSVIVLGBJKQAP-UHFFFAOYSA-N 0.000 claims description 4
- JHUFGBSGINLPOW-UHFFFAOYSA-N 3-chloro-4-(trifluoromethoxy)benzoyl cyanide Chemical compound FC(F)(F)OC1=CC=C(C(=O)C#N)C=C1Cl JHUFGBSGINLPOW-UHFFFAOYSA-N 0.000 claims description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 3
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 claims description 3
- 238000005507 spraying Methods 0.000 claims 4
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims 2
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 73
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 230000007062 hydrolysis Effects 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000007127 saponification reaction Methods 0.000 description 6
- 238000007334 copolymerization reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- -1 propylene oxide sulfonate ethers Chemical class 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000002360 preparation method Methods 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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000004513 sizing Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241000287227 Fringillidae Species 0.000 description 1
- 239000004831 Hot glue Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229920006167 biodegradable resin Polymers 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- YKGMKSIHIVVYKY-UHFFFAOYSA-N dabrafenib mesylate Chemical compound CS(O)(=O)=O.S1C(C(C)(C)C)=NC(C=2C(=C(NS(=O)(=O)C=3C(=CC=CC=3F)F)C=CC=2)F)=C1C1=CC=NC(N)=N1 YKGMKSIHIVVYKY-UHFFFAOYSA-N 0.000 description 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-N hydroperoxyl Chemical compound O[O] OUUQCZGPVNCOIJ-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000005935 nucleophilic addition reaction Methods 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003746 solid phase reaction Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000010671 solid-state reaction Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000004354 sulfur functional group Chemical group 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F116/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F116/02—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an alcohol radical
- C08F116/04—Acyclic compounds
- C08F116/06—Polyvinyl alcohol ; Vinyl alcohol
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
- B01J20/04—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising compounds of alkali metals, alkaline earth metals or magnesium
- B01J20/041—Oxides or hydroxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/34—Introducing sulfur atoms or sulfur-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/02—Chemical treatment or coating of shaped articles made of macromolecular substances with solvents, e.g. swelling agents
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/089,067 US5350801A (en) | 1993-07-07 | 1993-07-07 | Solid state process for modification of polyvinyl alcohol using Michael-type addition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69400514D1 DE69400514D1 (de) | 1996-10-17 |
| DE69400514T2 true DE69400514T2 (de) | 1997-01-02 |
Family
ID=22215505
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69400514T Expired - Fee Related DE69400514T2 (de) | 1993-07-07 | 1994-07-05 | Verfahren zur Modifizierung von Polyvinylalkohol in der Festkörperphase, mittels Michael-Addition |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5350801A (enExample) |
| EP (1) | EP0633271B1 (enExample) |
| JP (1) | JP2720891B2 (enExample) |
| KR (1) | KR950003322A (enExample) |
| DE (1) | DE69400514T2 (enExample) |
| TW (1) | TW252120B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2893330B2 (ja) | 1995-12-19 | 1999-05-17 | 第一工業製薬株式会社 | 変性ポリビニルアルコールの製造方法 |
| EP0794198A1 (en) * | 1996-03-06 | 1997-09-10 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | Modified polyvinyl alcohol |
| US5783628A (en) * | 1996-03-07 | 1998-07-21 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | Modified polyvinyl alcohol |
| DE60308717T2 (de) * | 2002-10-30 | 2007-08-02 | The Lubrizol Corp., Wickliffe | Faserdispergiermittelhaltige systeme |
| US7323083B2 (en) * | 2002-10-30 | 2008-01-29 | The Lubrizol Corporation | Adhesion promoters for glass-containing systems |
| WO2006038668A1 (ja) * | 2004-10-07 | 2006-04-13 | Shiseido Co., Ltd. | 表面処理剤、表面処理粉体、及びこれを含有する化粧料 |
| US20080045654A1 (en) * | 2006-08-16 | 2008-02-21 | Boston Scientific Scimed, Inc. | Polymer particles including covalently bonded chemical species |
| CN112978942A (zh) * | 2019-12-17 | 2021-06-18 | 天津农学院 | 一种具有可控性的刷状结构环境友好型阻垢剂的制备方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3125556A (en) * | 1961-04-27 | 1964-03-17 | Process of making hydroxyalkylated | |
| DE2935712A1 (de) * | 1978-09-07 | 1980-03-20 | Sumitomo Chemical Co | Verfahren zum herstellen von stark absorbierenden polymerisaten |
| JPS5656196A (en) * | 1979-10-13 | 1981-05-18 | Mitsubishi Electric Corp | Excitation control device for rotary machine |
| JPS5673199A (en) * | 1979-11-15 | 1981-06-17 | Kuraray Co | Paper coating agent |
| JPS57134245A (en) * | 1981-02-12 | 1982-08-19 | Nippon Kokan Kk <Nkk> | Horizontal continuous casting method for steel |
| US4545911A (en) * | 1982-04-30 | 1985-10-08 | Mobil Oil Corporation | Polymeric pyrrolidinium methanesulfonate viscosifiers for aqueous fluids |
| US4529522A (en) * | 1982-09-30 | 1985-07-16 | Mobil Oil Corporation | Alkyl sulfonates of polyvinyl alcohol as viscosifiers in saline solutions |
| DE3316948A1 (de) * | 1983-05-09 | 1984-11-15 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von in waessrigen alkalien loeslichem polyvinylalkohol und seine verwendung |
| JPS59226026A (ja) * | 1983-06-07 | 1984-12-19 | Showa Denko Kk | 親水性、耐水性塗工層形成剤 |
| JPS6099104A (ja) * | 1983-11-01 | 1985-06-03 | Kuraray Co Ltd | 架橋性基を含む変性ポリビニルアルコ−ルおよびその製法 |
| GB8611454D0 (en) * | 1986-05-10 | 1986-06-18 | Autotype Int Ltd | Manufacture of polymeric materials |
| DE3626662C1 (de) * | 1986-08-07 | 1987-12-10 | Degussa | Verfahren zur Herstellung kationisierter Polyvinylalkohole |
| CA1328031C (en) * | 1986-12-22 | 1994-03-22 | Paul Shu | Preparation of copolymers of polyvinyl alcohols |
| US4775715A (en) * | 1987-07-23 | 1988-10-04 | E. I. Du Pont De Nemours And Company | Dry blending process for the quaternization of polyvinyl alcohol |
| JPS63270704A (ja) * | 1988-03-23 | 1988-11-08 | Nippon Synthetic Chem Ind Co Ltd:The | 高重合度スルホン酸基含有変性ポリビニルアルコール、その製造法及び用途 |
| SU1654301A1 (ru) * | 1988-10-18 | 1991-06-07 | Кировский Политехнический Институт | Способ получени привитых сополимеров |
| US5104933A (en) * | 1989-02-06 | 1992-04-14 | Mobil Oil Corp. | Preparation of copolymers of polyvinyl alcohols |
-
1993
- 1993-07-07 US US08/089,067 patent/US5350801A/en not_active Expired - Lifetime
- 1993-11-06 TW TW082109302A patent/TW252120B/zh active
-
1994
- 1994-07-05 EP EP94110459A patent/EP0633271B1/en not_active Expired - Lifetime
- 1994-07-05 DE DE69400514T patent/DE69400514T2/de not_active Expired - Fee Related
- 1994-07-06 JP JP6154058A patent/JP2720891B2/ja not_active Expired - Lifetime
- 1994-07-06 KR KR1019940016079A patent/KR950003322A/ko not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| DE69400514D1 (de) | 1996-10-17 |
| JP2720891B2 (ja) | 1998-03-04 |
| JPH0770230A (ja) | 1995-03-14 |
| EP0633271A1 (en) | 1995-01-11 |
| TW252120B (enExample) | 1995-07-21 |
| KR950003322A (ko) | 1995-02-16 |
| EP0633271B1 (en) | 1996-09-11 |
| US5350801A (en) | 1994-09-27 |
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