DE1495651B1 - Verfahren zur Herstellung von Polyvinylacetessigestern - Google Patents
Verfahren zur Herstellung von PolyvinylacetessigesternInfo
- Publication number
- DE1495651B1 DE1495651B1 DE19611495651D DE1495651DA DE1495651B1 DE 1495651 B1 DE1495651 B1 DE 1495651B1 DE 19611495651 D DE19611495651 D DE 19611495651D DE 1495651D A DE1495651D A DE 1495651DA DE 1495651 B1 DE1495651 B1 DE 1495651B1
- Authority
- DE
- Germany
- Prior art keywords
- weight
- acetic acid
- polyvinyl
- polyvinyl alcohols
- units
- 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
- 238000000034 method Methods 0.000 title claims description 15
- 229920002554 vinyl polymer Polymers 0.000 title claims description 15
- 235000019439 ethyl acetate Nutrition 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 20
- 235000019422 polyvinyl alcohol Nutrition 0.000 claims description 20
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims description 16
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 9
- 150000002168 ethanoic acid esters Chemical class 0.000 claims description 8
- 239000004593 Epoxy Substances 0.000 claims description 4
- 229920000578 graft copolymer Polymers 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- 238000007127 saponification reaction Methods 0.000 claims description 4
- 229920001567 vinyl ester resin Polymers 0.000 claims description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims 1
- 229920001400 block copolymer Polymers 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- 238000005809 transesterification reaction Methods 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 59
- 229960000583 acetic acid Drugs 0.000 description 21
- 239000000047 product Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 6
- 239000004372 Polyvinyl alcohol Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- -1 chlorinated carbon diketene Chemical class 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- ZEYMDLYHRCTNEE-UHFFFAOYSA-N ethenyl 3-oxobutanoate Chemical group CC(=O)CC(=O)OC=C ZEYMDLYHRCTNEE-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 235000015110 jellies Nutrition 0.000 description 2
- 239000008274 jelly Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 229920001290 polyvinyl ester Polymers 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KRIUXIBKTKZYHV-UHFFFAOYSA-N 3-oxohex-5-enoic acid Chemical compound OC(=O)CC(=O)CC=C KRIUXIBKTKZYHV-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000006701 autoxidation reaction Methods 0.000 description 1
- PVEOYINWKBTPIZ-UHFFFAOYSA-N but-3-enoic acid Chemical compound OC(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010559 graft polymerization reaction Methods 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000036633 rest Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000010792 warming Methods 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/14—Esterification
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0034533 | 1961-07-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1495651B1 true DE1495651B1 (de) | 1969-09-04 |
Family
ID=7095593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19611495651D Pending DE1495651B1 (de) | 1961-07-26 | 1961-07-26 | Verfahren zur Herstellung von Polyvinylacetessigestern |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT240599B (enrdf_load_stackoverflow) |
| BE (1) | BE620711A (enrdf_load_stackoverflow) |
| CH (1) | CH425234A (enrdf_load_stackoverflow) |
| DE (1) | DE1495651B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1009473A (enrdf_load_stackoverflow) |
| NL (1) | NL281042A (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3609928A1 (de) * | 1985-03-27 | 1986-10-09 | Hoechst Gosei K.K., Tokio/Tokyo | Waessrige gelzusammensetzung, verfahren zu ihrer herstellung und ihre verwendung in der metallbearbeitung |
| DE3661834D1 (en) * | 1985-03-29 | 1989-02-23 | Akzo Nv | A liquid coating composition and a process for coating a substrate with such coating composition |
| JP2854039B2 (ja) * | 1989-10-23 | 1999-02-03 | 三菱化学株式会社 | 粉粒体の造粒方法 |
| WO2000031196A1 (en) | 1998-11-20 | 2000-06-02 | The Sherwin-Williams Company | Curable compositions comprising acetoacetoxy and imine functionality |
-
0
- NL NL281042D patent/NL281042A/xx unknown
- BE BE620711D patent/BE620711A/xx unknown
-
1961
- 1961-07-26 DE DE19611495651D patent/DE1495651B1/de active Pending
-
1962
- 1962-07-24 AT AT598262A patent/AT240599B/de active
- 1962-07-24 CH CH885362A patent/CH425234A/de unknown
- 1962-07-26 GB GB28842/62A patent/GB1009473A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL281042A (enrdf_load_stackoverflow) | |
| GB1009473A (en) | 1965-11-10 |
| AT240599B (de) | 1965-06-10 |
| BE620711A (enrdf_load_stackoverflow) | |
| CH425234A (de) | 1966-11-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE743698C (de) | Verfahren zur Herstellung von estergruppenhaltigen Harzen | |
| DE1094457B (de) | Verfahren zur Herstellung modifizierter Polyvinylalkohole | |
| DE1125181B (de) | Verfahren zur Herstellung von hochmolekularen Polymerisaten der Alkylenoxyde sowie von Styroloxyd in Gegenwart von Metallverbindungen | |
| DE4223471C2 (de) | Stärkezwischenprodukt, Verfahren zu dessen Herstellung sowie Verfahren zu dessen Weiterverarbeitung | |
| DE1495651B1 (de) | Verfahren zur Herstellung von Polyvinylacetessigestern | |
| EP0394884B1 (de) | Neue Polyvinylacetale und ihre Verwendung | |
| DE69120360T2 (de) | Verfahren zur herstellung von celluloseestern unter verwendung von carbonsäuren | |
| DE3110563A1 (de) | Verfahren zur herstellung von hochmolekularen lacton-plymerisaten | |
| DE1520166B1 (de) | Verfahren zur Herstellung stickstoffhaltiger Polyvinylalkoholderivate | |
| US3068220A (en) | Water insoluble cyanoethyl sucrose ethers | |
| DE1214879B (de) | Verfahren zur Herstellung von Polyvinylalkohol | |
| DE1956509A1 (de) | Verfahren zur Herstellung von Latices | |
| DE575750C (de) | Verfahren zur Herstellung von Polyglyciden | |
| DE1136109B (de) | Verfahren zum Stabilisieren von Polyoxymethylenen | |
| DE940680C (de) | Verfahren zur Herstellung von Polyvinylestern aus hydroxylgruppen-haltigen Polyvinylverbindungen und Diketen | |
| DE681346C (de) | Verfahren zur Herstellung von Kondensationsprodukten | |
| DE2607849A1 (de) | Verfahren zur gelatisation von glykolen | |
| DE878861C (de) | Verfahren zur Herstellung von Polyvinylformalen | |
| DE1495053A1 (de) | Verfahren zur Herstellung von Poly-Delta-valerolactonderivaten | |
| DE679792C (de) | Verfahren zur Herstellung von Kondensationsprodukten aus Polyvinylalkohol | |
| DE1300301B (de) | Verfahren zur Herstellung linearer, gesaettigter Polyester | |
| DE1125167B (de) | Verfahren zur Herstellung von Urethangruppen aufweisenden, gegebenenfalls verschaeumten Kunststoffen | |
| DE527617C (de) | Verfahren zur Herstellung von primaeren acetonloeslichen Celluloseoxyalkylatacetatengeringer Wasserempfindlichkeit | |
| DE635280C (de) | Verfahren zur Herstellung leicht loeslicher Acetylcellulose mit einer im Vergleich zur Viscositaet in Ameisensaeure besonders hohen Viscositaet in Aceton | |
| DE2827935C2 (de) | Verfahren zur Herstellung von 7,3',4'-Tri-O-β-hydroxyäthyl-rutosid |