GB1188635A - Process for the Copolymerisation of Olefinic Compounds - Google Patents
Process for the Copolymerisation of Olefinic CompoundsInfo
- Publication number
- GB1188635A GB1188635A GB5809668A GB5809668A GB1188635A GB 1188635 A GB1188635 A GB 1188635A GB 5809668 A GB5809668 A GB 5809668A GB 5809668 A GB5809668 A GB 5809668A GB 1188635 A GB1188635 A GB 1188635A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen
- vinyl
- sulphonate
- palladium
- ethylene
- 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
- 150000001875 compounds Chemical class 0.000 title abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 9
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 5
- 229910052763 palladium Inorganic materials 0.000 abstract 5
- 239000004160 Ammonium persulphate Substances 0.000 abstract 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 abstract 4
- 235000019395 ammonium persulphate Nutrition 0.000 abstract 4
- IMBKASBLAKCLEM-UHFFFAOYSA-L ferrous ammonium sulfate (anhydrous) Chemical compound [NH4+].[NH4+].[Fe+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O IMBKASBLAKCLEM-UHFFFAOYSA-L 0.000 abstract 4
- -1 ethylene, propylene Chemical group 0.000 abstract 3
- 239000000178 monomer Substances 0.000 abstract 3
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 abstract 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 2
- 239000005977 Ethylene Substances 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 2
- 150000004996 alkyl benzenes Chemical class 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 abstract 2
- 239000000084 colloidal system Substances 0.000 abstract 2
- 238000007334 copolymerization reaction Methods 0.000 abstract 2
- 229920000609 methyl cellulose Polymers 0.000 abstract 2
- 239000001923 methylcellulose Substances 0.000 abstract 2
- 235000010981 methylcellulose Nutrition 0.000 abstract 2
- 229910000510 noble metal Inorganic materials 0.000 abstract 2
- 150000002978 peroxides Chemical class 0.000 abstract 2
- 230000001681 protective effect Effects 0.000 abstract 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 abstract 1
- 229910052684 Cerium Inorganic materials 0.000 abstract 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 abstract 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 abstract 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 abstract 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 abstract 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 abstract 1
- 239000004372 Polyvinyl alcohol Substances 0.000 abstract 1
- 239000004159 Potassium persulphate Substances 0.000 abstract 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000001336 alkenes Chemical class 0.000 abstract 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 abstract 1
- 229910052804 chromium Inorganic materials 0.000 abstract 1
- 239000011651 chromium Substances 0.000 abstract 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical class OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 abstract 1
- 229910017052 cobalt Inorganic materials 0.000 abstract 1
- 239000010941 cobalt Substances 0.000 abstract 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 1
- 238000001246 colloidal dispersion Methods 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 abstract 1
- 239000002270 dispersing agent Substances 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 abstract 1
- 150000002500 ions Chemical class 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 229910021645 metal ion Inorganic materials 0.000 abstract 1
- 125000005395 methacrylic acid group Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910052750 molybdenum Inorganic materials 0.000 abstract 1
- 239000011733 molybdenum Substances 0.000 abstract 1
- 150000005673 monoalkenes Chemical class 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 abstract 1
- 239000012188 paraffin wax Substances 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 229920002451 polyvinyl alcohol Polymers 0.000 abstract 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 abstract 1
- 235000019394 potassium persulphate Nutrition 0.000 abstract 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 abstract 1
- FODHIQQNHOPUKH-UHFFFAOYSA-N tetrapropylene-benzenesulfonic acid Chemical compound CC1CC11C2=C3S(=O)(=O)OC(C)CC3=C3C(C)CC3=C2C1C FODHIQQNHOPUKH-UHFFFAOYSA-N 0.000 abstract 1
- 229910052720 vanadium Inorganic materials 0.000 abstract 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 abstract 1
- 229920001567 vinyl ester resin Polymers 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 abstract 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
- C08F4/00—Polymerisation catalysts
- C08F4/40—Redox systems
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymerization Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Abstract
1,188,635. Copolymerization. WACKERCHEMIE G.m.b.H. 6 Dec., 1968 [7 Dec., 1967], No. 58096/68. Heading C3P. Mono-olefins containing 2 to 6 carbon atoms are copolymerized with other monomers in aqueous dispersion by a free radical mechanism at -50‹ to + 50‹ C., using a catalyst comprising (a) a peroxide (b) hydrogen or a hydrogenliberating compound, (c) a colloidally distributed Group VIII noble metal in amount of 0.000001 to 0À01 weight per cent based on the monomers, and (d) ions of iron, copper, nickel, cobalt, chromium, molybdenum, vanadium or cerium in amount of 0À1 to 10 gm. atom per gram atom of noble metal, and not exceeding 0À001 weight per cent based on the monomers. Preferred olefins are ethylene, propylene and isobutylene. Many suitable comonomers are listed including vinyl and vinylidene halides; vinyl esters; acrylic, methacrylic, maleic, fumaric, itaconic and citraconic acids and esters; N-vinyl compounds; unsaturated alcohols; acrylamide and N-methylol acrylamide and vinyl sulphonate. The colloidal dispersion may be prepared in the presence of the additional metal ions, or added to the polymerization mix separately, and may be stabilized with protective colloids. Many suitable peroxides, dispersing and emulsifying agents and protective colloids are listed and examples describe the copolymerization of vinyl chloride with (1 and 2) ethylene, (3) propylene and (4) isobutylene in the presence of sodium paraffin sulphonate, hydrogen, palladium, potassium persulphate and ferrous ammonium sulphate; and of ethylene and vinyl acetate in the presence of (5 and 6) methanol, methyl cellulose, alkylbenzene sulphonate, hydrogen, palladium, ammonium persulphate and ferrous ammonium sulphate, (7) methanol, polyvinyl alcohol, alkyl benzene sulphonate, hydrogen, palladium, ammonium persulphate and copper sulphate, (10) hydroxyethyl cellulose, nonylphenol/ethylene oxide condensate, tetrapropylene benzene sulphonate, sodium vinyl sulphonate, hydrogen, palladium, ammonium persulphate and ferrous ammonium sulphate, (8) and together with butyl acrylate (9) methanol, methyl cellulose, alkyl benzene sulphonate, hydrogen, palladium, ammonium persulphate and ferrous ammonium sulphate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19671745567 DE1745567C3 (en) | 1967-12-07 | 1967-12-07 | Process for the copolymerization of olefinic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1188635A true GB1188635A (en) | 1970-04-22 |
Family
ID=5691398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5809668A Expired GB1188635A (en) | 1967-12-07 | 1968-12-06 | Process for the Copolymerisation of Olefinic Compounds |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH515941A (en) |
| FR (1) | FR1597733A (en) |
| GB (1) | GB1188635A (en) |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4692366A (en) * | 1986-09-08 | 1987-09-08 | National Starch And Chemical Corporation | Flocking adhesives based on eva-maleate copolymers |
| US4702957A (en) * | 1986-09-08 | 1987-10-27 | National Starch And Chemical Corporation | Binders for nonwovens based on EVA-maleate copolymers |
| US4737386A (en) * | 1986-09-08 | 1988-04-12 | National Starch And Chemical Corporation | Textile coating composition and textiles coated therewith |
| US4740394A (en) * | 1986-09-08 | 1988-04-26 | National Starch And Chemical Corporation | Textile coatings based on eva-maleate copolymers |
| US4753846A (en) * | 1987-02-02 | 1988-06-28 | National Starch And Chemical Corporation | Adhesive compositions for use on vinyl substrates |
| US4812547A (en) * | 1985-12-11 | 1989-03-14 | National Starch & Chemical Corp. | Pressure sensitive adhesives comprising ethylene vinyl acetate dioctyl maleate terpolymers |
| US4866119A (en) * | 1986-09-08 | 1989-09-12 | National Starch And Chemical Corporation | Textile coatings based on eva-maleate copolymers |
| US4892917A (en) * | 1987-02-02 | 1990-01-09 | National Starch And Chemical Corporation | Adhesive compositions for use on vinyl substrates |
| EP0296141A3 (en) * | 1987-05-13 | 1990-02-07 | Monsanto Company | Allyloxy activated surface coatings |
| EP0296140A3 (en) * | 1987-05-13 | 1990-02-14 | Monsanto Company | Allyloxy-activated surface coatings |
| US4908268A (en) * | 1988-03-17 | 1990-03-13 | National Starch And Chemical Corporation | Ethylene vinyl acetate-dioctyl maleate-2-ethylhexyl acrylate interpolymers |
| US4911960A (en) * | 1988-01-19 | 1990-03-27 | National Starch And Chemical Corporation | Laminating adhesive for film/paper microwavable products |
| US4939220A (en) * | 1988-03-17 | 1990-07-03 | National Starch And Chemical Investment Holding Corporation | Ethylene vinyl acetate-dioctyl maleate-2-ethylhexyl acrylate interpolymers |
| US4961993A (en) * | 1988-03-17 | 1990-10-09 | National Starch And Chemical Investment Holding Corporation | Ethylene vinyl acetate-dioctyl maleate-2-ethylhexyl acrylate interpolymers |
| US4963422A (en) * | 1987-10-28 | 1990-10-16 | National Starch And Chemical Investment Holding Corporation | Ethylene vinyl acetate alkyl acrylate compositions for flocking adhesives |
-
1968
- 1968-12-06 GB GB5809668A patent/GB1188635A/en not_active Expired
- 1968-12-06 CH CH1827068A patent/CH515941A/en not_active IP Right Cessation
- 1968-12-06 FR FR1597733D patent/FR1597733A/fr not_active Expired
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4812547A (en) * | 1985-12-11 | 1989-03-14 | National Starch & Chemical Corp. | Pressure sensitive adhesives comprising ethylene vinyl acetate dioctyl maleate terpolymers |
| US4866119A (en) * | 1986-09-08 | 1989-09-12 | National Starch And Chemical Corporation | Textile coatings based on eva-maleate copolymers |
| US4737386A (en) * | 1986-09-08 | 1988-04-12 | National Starch And Chemical Corporation | Textile coating composition and textiles coated therewith |
| US4740394A (en) * | 1986-09-08 | 1988-04-26 | National Starch And Chemical Corporation | Textile coatings based on eva-maleate copolymers |
| US4702957A (en) * | 1986-09-08 | 1987-10-27 | National Starch And Chemical Corporation | Binders for nonwovens based on EVA-maleate copolymers |
| US4692366A (en) * | 1986-09-08 | 1987-09-08 | National Starch And Chemical Corporation | Flocking adhesives based on eva-maleate copolymers |
| US4753846A (en) * | 1987-02-02 | 1988-06-28 | National Starch And Chemical Corporation | Adhesive compositions for use on vinyl substrates |
| US4892917A (en) * | 1987-02-02 | 1990-01-09 | National Starch And Chemical Corporation | Adhesive compositions for use on vinyl substrates |
| EP0296141A3 (en) * | 1987-05-13 | 1990-02-07 | Monsanto Company | Allyloxy activated surface coatings |
| EP0296140A3 (en) * | 1987-05-13 | 1990-02-14 | Monsanto Company | Allyloxy-activated surface coatings |
| US4963422A (en) * | 1987-10-28 | 1990-10-16 | National Starch And Chemical Investment Holding Corporation | Ethylene vinyl acetate alkyl acrylate compositions for flocking adhesives |
| US4911960A (en) * | 1988-01-19 | 1990-03-27 | National Starch And Chemical Corporation | Laminating adhesive for film/paper microwavable products |
| US4908268A (en) * | 1988-03-17 | 1990-03-13 | National Starch And Chemical Corporation | Ethylene vinyl acetate-dioctyl maleate-2-ethylhexyl acrylate interpolymers |
| US4939220A (en) * | 1988-03-17 | 1990-07-03 | National Starch And Chemical Investment Holding Corporation | Ethylene vinyl acetate-dioctyl maleate-2-ethylhexyl acrylate interpolymers |
| US4961993A (en) * | 1988-03-17 | 1990-10-09 | National Starch And Chemical Investment Holding Corporation | Ethylene vinyl acetate-dioctyl maleate-2-ethylhexyl acrylate interpolymers |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1597733A (en) | 1970-06-29 |
| CH515941A (en) | 1971-11-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |