CA1126449A - Method for the preparation of polyvinyl chloride resins - Google Patents
Method for the preparation of polyvinyl chloride resinsInfo
- Publication number
- CA1126449A CA1126449A CA297,336A CA297336A CA1126449A CA 1126449 A CA1126449 A CA 1126449A CA 297336 A CA297336 A CA 297336A CA 1126449 A CA1126449 A CA 1126449A
- Authority
- CA
- Canada
- Prior art keywords
- organic compound
- aqueous medium
- monomer
- polymerization
- group
- 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 abstract description 37
- 229920000915 polyvinyl chloride Polymers 0.000 title description 5
- 239000004800 polyvinyl chloride Substances 0.000 title description 5
- 238000002360 preparation method Methods 0.000 title description 3
- 229920005989 resin Polymers 0.000 title 1
- 239000011347 resin Substances 0.000 title 1
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 81
- 239000000178 monomer Substances 0.000 claims abstract description 74
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims abstract description 41
- 229920000642 polymer Polymers 0.000 claims abstract description 34
- 239000000203 mixture Substances 0.000 claims abstract description 29
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- 239000012736 aqueous medium Substances 0.000 claims abstract description 24
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 23
- 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 7
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 5
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 claims description 25
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 10
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 10
- 239000003505 polymerization initiator Substances 0.000 claims description 7
- -1 nitrile compounds Chemical class 0.000 claims description 6
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 5
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 5
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 claims description 4
- QNNVICQPXUUBSN-UHFFFAOYSA-N 2-sulfanylpropan-1-ol Chemical compound CC(S)CO QNNVICQPXUUBSN-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 230000000977 initiatory effect Effects 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 229920002472 Starch Polymers 0.000 claims description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 239000001530 fumaric acid Substances 0.000 claims description 2
- 229920000159 gelatin Polymers 0.000 claims description 2
- 235000019322 gelatine Nutrition 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- 229920000609 methyl cellulose Polymers 0.000 claims description 2
- 239000001923 methylcellulose Substances 0.000 claims description 2
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001451 organic peroxides Chemical class 0.000 claims description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 2
- 235000019698 starch Nutrition 0.000 claims description 2
- 239000008107 starch Substances 0.000 claims description 2
- 239000000375 suspending agent Substances 0.000 claims description 2
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 claims description 2
- 229920001567 vinyl ester resin Polymers 0.000 claims description 2
- FETFXNFGOYOOSP-UHFFFAOYSA-N 1-sulfanylpropan-2-ol Chemical compound CC(O)CS FETFXNFGOYOOSP-UHFFFAOYSA-N 0.000 claims 1
- 108010010803 Gelatin Proteins 0.000 claims 1
- 239000008273 gelatin Substances 0.000 claims 1
- 235000011852 gelatine desserts Nutrition 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 238000009826 distribution Methods 0.000 abstract description 9
- 239000002245 particle Substances 0.000 abstract description 9
- 239000012986 chain transfer agent Substances 0.000 description 39
- 238000002474 experimental method Methods 0.000 description 20
- 239000003795 chemical substances by application Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000008367 deionised water Substances 0.000 description 8
- 229910021641 deionized water Inorganic materials 0.000 description 8
- 238000012546 transfer Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 6
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 4
- 230000003028 elevating effect Effects 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 3
- 230000003111 delayed effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 238000010557 suspension polymerization reaction Methods 0.000 description 3
- HGXJDMCMYLEZMJ-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOOC(=O)C(C)(C)C HGXJDMCMYLEZMJ-UHFFFAOYSA-N 0.000 description 2
- 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
- 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 description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- SHLSSLVZXJBVHE-UHFFFAOYSA-N 3-sulfanylpropan-1-ol Chemical compound OCCCS SHLSSLVZXJBVHE-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- BSVQJWUUZCXSOL-UHFFFAOYSA-N cyclohexylsulfonyl ethaneperoxoate Chemical compound CC(=O)OOS(=O)(=O)C1CCCCC1 BSVQJWUUZCXSOL-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- YFQALGYGYQILDD-UHFFFAOYSA-N ethanol;ethene Chemical group C=C.CCO.CCO YFQALGYGYQILDD-UHFFFAOYSA-N 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 230000005802 health problem Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 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 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
- 230000000979 retarding effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- C08F14/00—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 a halogen
- C08F14/02—Monomers containing chlorine
- C08F14/04—Monomers containing two carbon atoms
- C08F14/06—Vinyl chloride
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP52-19691 | 1977-02-24 | ||
| JP1969177A JPS53104684A (en) | 1977-02-24 | 1977-02-24 | Preparation of vinyl chloride polymer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1126449A true CA1126449A (en) | 1982-06-22 |
Family
ID=12006260
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA297,336A Expired CA1126449A (en) | 1977-02-24 | 1978-02-20 | Method for the preparation of polyvinyl chloride resins |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS53104684A (is") |
| AT (1) | ATA126678A (is") |
| BE (1) | BE864149A (is") |
| BR (1) | BR7801118A (is") |
| CA (1) | CA1126449A (is") |
| CU (1) | CU34877A (is") |
| DE (1) | DE2807180A1 (is") |
| DK (1) | DK80978A (is") |
| ES (1) | ES467284A1 (is") |
| FR (1) | FR2381792A1 (is") |
| GB (1) | GB1596689A (is") |
| HU (1) | HU178740B (is") |
| IT (1) | IT1094154B (is") |
| NL (1) | NL181659C (is") |
| NO (1) | NO152754C (is") |
| PL (1) | PL107759B1 (is") |
| PT (1) | PT67691B (is") |
| SE (1) | SE440784C (is") |
| SU (1) | SU841592A3 (is") |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3029907A1 (de) | 1980-08-07 | 1982-03-18 | Hoechst Ag, 6000 Frankfurt | Kontinuierliches verfahren und vorrichtung zur herstellung eines vinylchlorid-polymerisates in waessriger suspension |
| JPS6248703A (ja) * | 1985-08-27 | 1987-03-03 | Chisso Corp | 低重合度塩化ビニル系重合体の製造方法 |
| US4797458A (en) * | 1986-09-02 | 1989-01-10 | The B.F. Goodrich Company | Colloidal stable vinyl halide polymerizations with mercaptan chain transfer agents |
| DE10309857A1 (de) * | 2003-03-06 | 2004-09-23 | Wacker Polymer Systems Gmbh & Co. Kg | Epoxy-modifizierte Vinylchlorid-Vinylester-Copolymer-Festharze |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB579353A (en) * | 1943-03-20 | 1946-07-31 | Du Pont | Polymerisation of unsaturated compounds in the presence of thiols and derivatives thereof |
| DE2051317A1 (en) * | 1970-10-20 | 1972-04-27 | Basf Ag | Radical polymerisation using regulator - of bifunctional mercaptan or organic sulphide type |
| JPS5233987A (en) * | 1975-09-11 | 1977-03-15 | Shin Etsu Chem Co Ltd | Preparation of vinyl chloride polymer |
| JPS52138583A (en) * | 1976-04-19 | 1977-11-18 | Mitsui Toatsu Chem Inc | Preparation of vinyl chloride polymers |
| JPS5372089A (en) * | 1976-12-09 | 1978-06-27 | Nippon Zeon Co Ltd | Preparation of polyvinyl chloride type resin |
-
1977
- 1977-02-24 JP JP1969177A patent/JPS53104684A/ja active Granted
-
1978
- 1978-02-20 DE DE19782807180 patent/DE2807180A1/de active Granted
- 1978-02-20 SE SE7801919A patent/SE440784C/sv not_active IP Right Cessation
- 1978-02-20 CA CA297,336A patent/CA1126449A/en not_active Expired
- 1978-02-21 GB GB6777/78A patent/GB1596689A/en not_active Expired
- 1978-02-21 NO NO780590A patent/NO152754C/no unknown
- 1978-02-21 BE BE185331A patent/BE864149A/xx not_active IP Right Cessation
- 1978-02-21 AT AT126678A patent/ATA126678A/de not_active IP Right Cessation
- 1978-02-22 IT IT20524/78A patent/IT1094154B/it active
- 1978-02-22 PT PT67691A patent/PT67691B/pt unknown
- 1978-02-23 PL PL1978204854A patent/PL107759B1/pl unknown
- 1978-02-23 FR FR7805167A patent/FR2381792A1/fr active Granted
- 1978-02-23 NL NLAANVRAGE7802025,A patent/NL181659C/xx not_active IP Right Cessation
- 1978-02-23 BR BR7801118A patent/BR7801118A/pt unknown
- 1978-02-23 DK DK80978A patent/DK80978A/da not_active Application Discontinuation
- 1978-02-23 HU HU78SI1620A patent/HU178740B/hu not_active IP Right Cessation
- 1978-02-24 ES ES467284A patent/ES467284A1/es not_active Expired
- 1978-02-24 SU SU782585304A patent/SU841592A3/ru active
- 1978-02-24 CU CU7834877A patent/CU34877A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL181659C (nl) | 1987-10-01 |
| BE864149A (fr) | 1978-06-16 |
| NO152754B (no) | 1985-08-05 |
| IT1094154B (it) | 1985-07-26 |
| IT7820524A0 (it) | 1978-02-22 |
| PT67691B (en) | 1979-07-23 |
| DE2807180A1 (de) | 1978-09-21 |
| SU841592A3 (ru) | 1981-06-23 |
| PL204854A1 (pl) | 1978-11-06 |
| NO152754C (no) | 1985-11-13 |
| GB1596689A (en) | 1981-08-26 |
| PL107759B1 (pl) | 1980-03-31 |
| SE7801919L (sv) | 1978-08-25 |
| HU178740B (en) | 1982-06-28 |
| SE440784B (sv) | 1985-08-19 |
| NL181659B (nl) | 1987-05-04 |
| CU34877A (es) | 1979-08-20 |
| DE2807180C2 (is") | 1991-12-05 |
| ES467284A1 (es) | 1978-10-16 |
| BR7801118A (pt) | 1978-10-10 |
| JPS5533804B2 (is") | 1980-09-03 |
| ATA126678A (de) | 1981-04-15 |
| FR2381792A1 (fr) | 1978-09-22 |
| SE440784C (sv) | 1989-12-04 |
| PT67691A (en) | 1978-03-01 |
| FR2381792B1 (is") | 1980-09-12 |
| NO780590L (no) | 1978-08-25 |
| NL7802025A (nl) | 1978-08-28 |
| DK80978A (da) | 1978-08-25 |
| JPS53104684A (en) | 1978-09-12 |
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