DE2206593C3 - Verfahren zur Herstellung von Vinylchlorid-Vinylester-Copolymerisaten - Google Patents
Verfahren zur Herstellung von Vinylchlorid-Vinylester-CopolymerisatenInfo
- Publication number
- DE2206593C3 DE2206593C3 DE2206593A DE2206593A DE2206593C3 DE 2206593 C3 DE2206593 C3 DE 2206593C3 DE 2206593 A DE2206593 A DE 2206593A DE 2206593 A DE2206593 A DE 2206593A DE 2206593 C3 DE2206593 C3 DE 2206593C3
- Authority
- DE
- Germany
- Prior art keywords
- weight
- monomers
- vinyl
- carbon atoms
- vinyl chloride
- 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
- 238000000034 method Methods 0.000 title claims description 8
- 229920001567 vinyl ester resin Polymers 0.000 title claims description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title claims description 7
- 229920002554 vinyl polymer Polymers 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000000178 monomer Substances 0.000 claims description 20
- 238000006116 polymerization reaction Methods 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 150000001735 carboxylic acids Chemical class 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 229920003086 cellulose ether Polymers 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 239000007900 aqueous suspension Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
- 150000005690 diesters Chemical class 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- -1 Silicon Peroxide Chemical class 0.000 description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 3
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 3
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- BSVQJWUUZCXSOL-UHFFFAOYSA-N cyclohexylsulfonyl ethaneperoxoate Chemical compound CC(=O)OOS(=O)(=O)C1CCCCC1 BSVQJWUUZCXSOL-UHFFFAOYSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 235000017858 Laurus nobilis Nutrition 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 240000007643 Phytolacca americana Species 0.000 description 1
- 244000125380 Terminalia tomentosa Species 0.000 description 1
- 235000005212 Terminalia tomentosa Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical group C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- HGAZMNJKRQFZKS-UHFFFAOYSA-N chloroethene;ethenyl acetate Chemical compound ClC=C.CC(=O)OC=C HGAZMNJKRQFZKS-UHFFFAOYSA-N 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- QWVBGCWRHHXMRM-UHFFFAOYSA-N hexadecoxycarbonyloxy hexadecyl carbonate Chemical compound CCCCCCCCCCCCCCCCOC(=O)OOC(=O)OCCCCCCCCCCCCCCCC QWVBGCWRHHXMRM-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- 150000002976 peresters Chemical class 0.000 description 1
- 125000005634 peroxydicarbonate group Chemical group 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- BWSZXUOMATYHHI-UHFFFAOYSA-N tert-butyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(C)(C)C BWSZXUOMATYHHI-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration 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
- C08F214/00—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 a halogen
- C08F214/02—Monomers containing chlorine
- C08F214/04—Monomers containing two carbon atoms
- C08F214/06—Vinyl chloride
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2206593A DE2206593C3 (de) | 1972-02-11 | 1972-02-11 | Verfahren zur Herstellung von Vinylchlorid-Vinylester-Copolymerisaten |
| NL7216481A NL7216481A (enExample) | 1972-02-11 | 1972-12-05 | |
| IT54635/72A IT974013B (it) | 1972-02-11 | 1972-12-12 | Procedimento per produrre copoli meri di cloruro di vinile ed esteri vinilici |
| GB415073A GB1415931A (en) | 1972-02-11 | 1973-01-26 | Process for the manufacture of copolymers of vinyl chloride and vinyl esters |
| US00330315A US3835105A (en) | 1972-02-11 | 1973-02-07 | Method for the polymerization of vinyl chloride/vinyl ester copolymers and the high bulk density copolymers of the process |
| BE795137D BE795137A (fr) | 1972-02-11 | 1973-02-08 | Procede de preparation de copolymeres a partir du chlorure de vinyle et d'esters vinyliques |
| FR7304675A FR2171372B1 (enExample) | 1972-02-11 | 1973-02-09 | |
| CA163,348A CA1010195A (en) | 1972-02-11 | 1973-02-09 | Polymerization of vinyl chloride/vinyl ester mixtures |
| JP48017366A JPS5026591B2 (enExample) | 1972-02-11 | 1973-02-12 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2206593A DE2206593C3 (de) | 1972-02-11 | 1972-02-11 | Verfahren zur Herstellung von Vinylchlorid-Vinylester-Copolymerisaten |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2206593A1 DE2206593A1 (de) | 1973-08-16 |
| DE2206593B2 DE2206593B2 (de) | 1979-11-22 |
| DE2206593C3 true DE2206593C3 (de) | 1980-07-03 |
Family
ID=5835778
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2206593A Expired DE2206593C3 (de) | 1972-02-11 | 1972-02-11 | Verfahren zur Herstellung von Vinylchlorid-Vinylester-Copolymerisaten |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3835105A (enExample) |
| JP (1) | JPS5026591B2 (enExample) |
| BE (1) | BE795137A (enExample) |
| CA (1) | CA1010195A (enExample) |
| DE (1) | DE2206593C3 (enExample) |
| FR (1) | FR2171372B1 (enExample) |
| GB (1) | GB1415931A (enExample) |
| IT (1) | IT974013B (enExample) |
| NL (1) | NL7216481A (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3025171A1 (de) * | 1980-07-03 | 1982-01-28 | Wacker-Chemie GmbH, 8000 München | Verfahren zur herstellung von vinylhalogenidpolymerisaten |
| DE102005041593A1 (de) | 2005-09-01 | 2007-03-08 | Wacker Polymer Systems Gmbh & Co. Kg | Verfahren zur Herstellung von Vinylchlorid-Vinylacetat-Mischpolymerisaten in Form deren Festharze |
| WO2016102558A1 (en) * | 2014-12-23 | 2016-06-30 | Ercros, S.A. | Process for the preparation of polymers based on vinyl halides with enhanced properties and productivity |
| ES2835787T3 (es) | 2017-08-07 | 2021-06-23 | Wacker Chemie Ag | Copolimeros de cloruro de vinilo, acetato de vinilo y ésteres vinílicos de cadena larga |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1306786A (fr) * | 1961-11-03 | 1962-10-19 | Ici Ltd | Production de polymères du chlorure de vinyle |
| US3244677A (en) * | 1962-08-17 | 1966-04-05 | Goodyear Tire & Rubber | Internally plasticized vinyl polymers |
-
1972
- 1972-02-11 DE DE2206593A patent/DE2206593C3/de not_active Expired
- 1972-12-05 NL NL7216481A patent/NL7216481A/xx not_active Application Discontinuation
- 1972-12-12 IT IT54635/72A patent/IT974013B/it active
-
1973
- 1973-01-26 GB GB415073A patent/GB1415931A/en not_active Expired
- 1973-02-07 US US00330315A patent/US3835105A/en not_active Expired - Lifetime
- 1973-02-08 BE BE795137D patent/BE795137A/xx unknown
- 1973-02-09 FR FR7304675A patent/FR2171372B1/fr not_active Expired
- 1973-02-09 CA CA163,348A patent/CA1010195A/en not_active Expired
- 1973-02-12 JP JP48017366A patent/JPS5026591B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2206593B2 (de) | 1979-11-22 |
| JPS5026591B2 (enExample) | 1975-09-02 |
| JPS4889288A (enExample) | 1973-11-21 |
| NL7216481A (enExample) | 1973-08-14 |
| FR2171372B1 (enExample) | 1976-06-11 |
| BE795137A (fr) | 1973-08-08 |
| US3835105A (en) | 1974-09-10 |
| IT974013B (it) | 1974-06-20 |
| CA1010195A (en) | 1977-05-10 |
| GB1415931A (en) | 1975-12-03 |
| FR2171372A1 (enExample) | 1973-09-21 |
| DE2206593A1 (de) | 1973-08-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8381 | Inventor (new situation) |
Free format text: BAUER, JOHANN, DR.-ING. FENDEL, KURT, DR., 8263 BURGHAUSEN, DE KOHL, JOHANN, DIPL.-CHEM. DR., 8000 MUENCHEN, DE |
|
| 8339 | Ceased/non-payment of the annual fee |