DE1720806C2 - Verfahren zur kontinuierlichen Polymerisation von Vinylestern - Google Patents
Verfahren zur kontinuierlichen Polymerisation von VinylesternInfo
- Publication number
- DE1720806C2 DE1720806C2 DE1720806A DE1720806A DE1720806C2 DE 1720806 C2 DE1720806 C2 DE 1720806C2 DE 1720806 A DE1720806 A DE 1720806A DE 1720806 A DE1720806 A DE 1720806A DE 1720806 C2 DE1720806 C2 DE 1720806C2
- Authority
- DE
- Germany
- Prior art keywords
- polymerization
- alcohol
- methanol
- vinyl
- weight
- 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
Links
- 238000006116 polymerization reaction Methods 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 17
- 229920001567 vinyl ester resin Polymers 0.000 title claims description 12
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 14
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 13
- 229920002689 polyvinyl acetate Polymers 0.000 claims description 11
- 239000011118 polyvinyl acetate Substances 0.000 claims description 11
- 239000003999 initiator Substances 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- -1 aliphatic alcohols Chemical class 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 229920001290 polyvinyl ester Polymers 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 238000010526 radical polymerization reaction Methods 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 235000019441 ethanol Nutrition 0.000 claims 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- 150000002978 peroxides Chemical class 0.000 claims 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 235000019400 benzoyl peroxide Nutrition 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 claims 1
- NWJTZFZQVYJIHU-UHFFFAOYSA-N ethenyl nonanoate Chemical compound CCCCCCCCC(=O)OC=C NWJTZFZQVYJIHU-UHFFFAOYSA-N 0.000 claims 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- RGBXDEHYFWDBKD-UHFFFAOYSA-N propan-2-yl propan-2-yloxy carbonate Chemical compound CC(C)OOC(=O)OC(C)C RGBXDEHYFWDBKD-UHFFFAOYSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 description 14
- 238000007127 saponification reaction Methods 0.000 description 11
- 229920002451 polyvinyl alcohol Polymers 0.000 description 10
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 8
- 229940117958 vinyl acetate Drugs 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 239000004372 Polyvinyl alcohol Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910016455 AlBN Inorganic materials 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- QLVHFTGKDGTJDH-UHFFFAOYSA-N acetic acid;ethenyl acetate Chemical compound CC(O)=O.CC(=O)OC=C QLVHFTGKDGTJDH-UHFFFAOYSA-N 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- FJOPOOBDMDAVIW-UHFFFAOYSA-N ethenyl acetate;hydrate Chemical compound O.CC(=O)OC=C FJOPOOBDMDAVIW-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000001291 vacuum drying 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
- C08F18/00—Homopolymers and copolymers 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 acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F18/02—Esters of monocarboxylic acids
- C08F18/04—Vinyl esters
Landscapes
- 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)
- Polymerisation Methods In General (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BR20716769A BR6907167D0 (pt) | 1968-03-19 | 1969-03-14 | Processo para a polimerizacao continua em solucao de esteres vinilicos |
| CH398469A CH512525A (de) | 1968-03-19 | 1969-03-17 | Verfahren zur kontinuierlichen Lösungspolymerisation von Vinylestern |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0055101 | 1968-03-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1720806A1 DE1720806A1 (de) | 1971-07-22 |
| DE1720806C2 true DE1720806C2 (de) | 1982-09-23 |
Family
ID=7107561
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1720806A Expired DE1720806C2 (de) | 1968-03-19 | 1968-03-19 | Verfahren zur kontinuierlichen Polymerisation von Vinylestern |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3607852A (enExample) |
| AT (1) | AT293724B (enExample) |
| BE (1) | BE730095A (enExample) |
| DE (1) | DE1720806C2 (enExample) |
| FR (1) | FR2004240A1 (enExample) |
| GB (1) | GB1224113A (enExample) |
| NL (1) | NL160290C (enExample) |
| SE (1) | SE362653B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1102671B (de) * | 1959-06-16 | 1961-03-23 | Renate Skiebe Geb Altrock | Lampenschirm |
| IT1189869B (it) * | 1986-01-28 | 1988-02-10 | Paolo Carlin | Procedimento per la produzione in alcool etilico di un polivinile acetato |
| DE19602901A1 (de) | 1996-01-27 | 1997-08-07 | Hoechst Ag | Verfahren zur Herstellung von Polyvinylalkohol |
| US5728788A (en) * | 1996-03-29 | 1998-03-17 | Kuraray Co., Ltd. | Process of producing vinyl acetate polymer |
| EP2655447B1 (en) | 2010-12-22 | 2015-06-10 | Sekisui Specialty Chemicals America, LLC | Cold water soluble polyvinyl alcohol/alkyl acrylate copolymers and films thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1126613B (de) * | 1957-01-02 | 1962-03-29 | Bayer Ag | Verfahren zur Herstellung von Mischpolymerisaten aus AEthylen und Vinylestern |
| GB883263A (en) * | 1959-03-20 | 1961-11-29 | Kurashiki Rayon Co | Method of polymerization of vinyl esters |
| GB872773A (en) * | 1959-06-05 | 1961-07-12 | Kurashiki Rayon Kk | A method of manufacturing polyvinyl acetate |
-
1968
- 1968-03-19 DE DE1720806A patent/DE1720806C2/de not_active Expired
-
1969
- 1969-03-05 NL NL6903401.A patent/NL160290C/xx not_active IP Right Cessation
- 1969-03-06 US US804933A patent/US3607852A/en not_active Expired - Lifetime
- 1969-03-17 GB GB03868/69A patent/GB1224113A/en not_active Expired
- 1969-03-18 SE SE03722/69A patent/SE362653B/xx unknown
- 1969-03-19 FR FR6907876A patent/FR2004240A1/fr not_active Withdrawn
- 1969-03-19 BE BE730095D patent/BE730095A/xx not_active IP Right Cessation
- 1969-03-19 AT AT269569A patent/AT293724B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1224113A (en) | 1971-03-03 |
| US3607852A (en) | 1971-09-21 |
| FR2004240A1 (enExample) | 1969-11-21 |
| DE1720806A1 (de) | 1971-07-22 |
| AT293724B (de) | 1971-10-25 |
| SE362653B (enExample) | 1973-12-17 |
| BE730095A (enExample) | 1969-09-19 |
| NL160290C (nl) | 1979-10-15 |
| NL6903401A (enExample) | 1969-09-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| D2 | Grant after examination |