WO2002094885A1 - Verwendung von estern des polyglycerins und deren alkoxylierten und anionischen derivaten als emulgatoren in der emulsionspolymerisation - Google Patents
Verwendung von estern des polyglycerins und deren alkoxylierten und anionischen derivaten als emulgatoren in der emulsionspolymerisation Download PDFInfo
- Publication number
- WO2002094885A1 WO2002094885A1 PCT/EP2002/005008 EP0205008W WO02094885A1 WO 2002094885 A1 WO2002094885 A1 WO 2002094885A1 EP 0205008 W EP0205008 W EP 0205008W WO 02094885 A1 WO02094885 A1 WO 02094885A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- sodium
- esters
- acid
- potassium
- polyglycerol
- Prior art date
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- 150000002148 esters Chemical class 0.000 title claims abstract description 30
- 239000003995 emulsifying agent Substances 0.000 title claims abstract description 23
- 125000000129 anionic group Chemical group 0.000 title claims description 17
- 239000000839 emulsion Substances 0.000 title abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229920000223 polyglycerol Polymers 0.000 claims description 25
- 239000011734 sodium Substances 0.000 claims description 24
- 229910052708 sodium Inorganic materials 0.000 claims description 24
- -1 Sodium alkyl sulfonates Chemical class 0.000 claims description 21
- 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 claims description 19
- 239000000178 monomer Substances 0.000 claims description 17
- 239000002202 Polyethylene glycol Substances 0.000 claims description 15
- 229920001223 polyethylene glycol Polymers 0.000 claims description 15
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 13
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 13
- 239000011591 potassium Substances 0.000 claims description 13
- 229910052700 potassium Inorganic materials 0.000 claims description 13
- 239000004815 dispersion polymer Substances 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 10
- 238000006116 polymerization reaction Methods 0.000 claims description 10
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 9
- 239000000194 fatty acid Substances 0.000 claims description 9
- 229930195729 fatty acid Natural products 0.000 claims description 9
- 150000004665 fatty acids Chemical class 0.000 claims description 9
- 150000003863 ammonium salts Chemical class 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 7
- 150000001735 carboxylic acids Chemical class 0.000 claims description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000004908 Emulsion polymer Substances 0.000 claims description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 150000005690 diesters Chemical class 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 150000005691 triesters Chemical class 0.000 claims description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 claims description 2
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims 2
- 239000012736 aqueous medium Substances 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 230000000379 polymerizing effect Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000006185 dispersion Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 6
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 4
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- OGELJRHPEZALCC-UHFFFAOYSA-N [3-(2,3-dihydroxypropoxy)-2-hydroxypropyl] dodecanoate Chemical class CCCCCCCCCCCC(=O)OCC(O)COCC(O)CO OGELJRHPEZALCC-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000001447 alkali salts Chemical class 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000003460 sulfonic acids Chemical class 0.000 description 3
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 241000233803 Nypa Species 0.000 description 2
- 235000005305 Nypa fruticans Nutrition 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910021538 borax Inorganic materials 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
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- GADGVXXJJXQRSA-UHFFFAOYSA-N ethenyl 8-methylnonanoate Chemical compound CC(C)CCCCCCC(=O)OC=C GADGVXXJJXQRSA-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- UTOPWMOLSKOLTQ-UHFFFAOYSA-N octacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTOPWMOLSKOLTQ-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 229920001515 polyalkylene glycol Polymers 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000004328 sodium tetraborate Substances 0.000 description 2
- 235000010339 sodium tetraborate Nutrition 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
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- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 1
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- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 1
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- 150000001298 alcohols Chemical class 0.000 description 1
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- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
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- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
- 239000012935 ammoniumperoxodisulfate Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- ROPXFXOUUANXRR-YPKPFQOOSA-N bis(2-ethylhexyl) (z)-but-2-enedioate Chemical compound CCCCC(CC)COC(=O)\C=C/C(=O)OCC(CC)CCCC ROPXFXOUUANXRR-YPKPFQOOSA-N 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical group OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium 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
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 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
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- QMCVOSQFZZCSLN-QXMHVHEDSA-N dihexyl (z)-but-2-enedioate Chemical compound CCCCCCOC(=O)\C=C/C(=O)OCCCCCC QMCVOSQFZZCSLN-QXMHVHEDSA-N 0.000 description 1
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 1
- NFCMRHDORQSGIS-KTKRTIGZSA-N dipentyl (z)-but-2-enedioate Chemical compound CCCCCOC(=O)\C=C/C(=O)OCCCCC NFCMRHDORQSGIS-KTKRTIGZSA-N 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 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
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 150000002763 monocarboxylic acids Chemical group 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- SWPMNMYLORDLJE-UHFFFAOYSA-N n-ethylprop-2-enamide Chemical compound CCNC(=O)C=C SWPMNMYLORDLJE-UHFFFAOYSA-N 0.000 description 1
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 description 1
- WDFKEEALECCKTJ-UHFFFAOYSA-N n-propylprop-2-enamide Chemical compound CCCNC(=O)C=C WDFKEEALECCKTJ-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 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
- 229960002446 octanoic acid Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 125000004817 pentamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- ULDDEWDFUNBUCM-UHFFFAOYSA-N pentyl prop-2-enoate Chemical compound CCCCCOC(=O)C=C ULDDEWDFUNBUCM-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920001521 polyalkylene glycol ether Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920000417 polynaphthalene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000002087 whitening effect Effects 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
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
- C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
Definitions
- esters of polyglycerol and their alkoxylated and anionic derivatives as emulsifiers in emulsion polymerization
- the present invention relates to the use of fatty acid polyglycerol esters and their alkoxylated and anionic derivatives as emulsifiers in emulsion polymerizations.
- the emulsifiers used for the emulsion polymerization according to the prior art are mostly anionic and nonionic emulsifiers.
- Common anionic emulsifiers are sodium, potassium and ammonium salts of fatty acids, sodium alkylbenzenesulfonates, sodium alkylsulfonates, sodium olefin sulfonates, sodium polynaphthalene sulfonates, sodium dialkyldiphenylether disulfonates, sodium, potassium and ammonium alkyl sulfates, sodium, potassium and ammonium alkyl sulfates, glycol ether sulfates, sodium, potassium and ammonium mono- and dialkyl sulfosuccinates and monoalkylpolyoxethyl sulfosuccinates, as well as alkyl polyethylene glycol ether phosphoric acid mono-, di- and triesters and their mixtures and alkylphenol polyethylene glycol ether phosphoric acid mono-, di- and triester and their mixtures, as well as their sodium, potassium and ammonium salts.
- Alkylphenol polyethylene glycol ether, alkyl polyethylene glycol ether, fatty acid polyethylene glycol ether, ethylene / propylene glycol block polymers and sorbitan ester polyethylene glycol ether are usually used as nonionic emulsifiers.
- Emulsion polymerizations using anionic and nonionic emulsifiers are usually carried out in the total batch or in Feed process carried out, in which only a small part of the monomers to be polymerized is placed in the polymerization vessel and the larger part (50 to 100% by weight) is added as the polymerization progresses.
- the anionic or nonionic emulsifiers are optionally used in the feed or in the reactor receiver during the emulsion polymerization, or are added subsequently to the polymer dispersion prepared for stabilization.
- the invention thus relates to the use of esters between polyglycerol with 2 to 100 glycerol units and at least one carboxylic acid with 6 to 42 carbon atoms as an emulsifier in the emulsion polymerization.
- Polyglycerols are compounds of the formula (1)
- n is the degree of condensation. n is between 2 and 100, preferably between 3 and 20.
- the polyglycerol esters are preferably prepared with carboxylic acids of 6 to 26, in particular 8 to 18, carbon atoms.
- the carboxylic acids can be aliphatic, aliphatic-unsaturated, cycloaliphatic, cycloaliphatic-unsaturated or aromatic. It is preferably monocarboxylic acids.
- the carboxylic acids are native saturated fatty acids such as caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, hexosanoic acid and montanic acid, native unsaturated carboxylic acids such as oleic acid, linoleic acid, linolenic acid, rapeseed oil fatty acid and erucic acid, synthetic saturated carboxylic acid such as margaric acid, cyclic carboxylic acids such as naphthenic acid, benzoic acid, phenylacetic acid and resin acids such as abietic acid, levopimaric acid and neoabietic acid.
- native saturated fatty acids such as caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, hexosanoic acid and montanic acid
- native unsaturated carboxylic acids such as oleic acid, lin
- the esters preferably contain polyglycerol and the carboxylic acid in a molar ratio of at least 1: 1, in particular in a ratio of 1: 1 to 1:10, especially 1: 1 to 1: 5.
- esters are used in alkoxylated form.
- the alkoxylated esters of polyglycerols contain alkoxy groups on one or more of the free OH groups of the polyglycerol, which can optionally be derivatized.
- A is C 2 - to C 4 -alkylene
- x is a number from 1 to 500, in particular 2 to 100
- B is hydrogen or the remainder of a di- or polyvalent inorganic or organic acid which, in addition to oxygen atoms, also has at least one phosphorus - or has a sulfur atom.
- inorganic acids which are suitable for the formation of the alkoxylated esters are sulfuric acid and phosphoric acid.
- the organic or inorganic acids used to esterify the alkoxy groups according to formula (2) are divalent or trivalent.
- the organic acids are di-, tri- or polyvalent carboxylic acids, i.e. Compounds which contain 2, 3 or more carboxyl groups and which additionally have at least one functional group containing sulfur or phosphorus. Sulfur-containing functional groups, especially sulfonate groups, are particularly preferred.
- the particularly preferred sulfonic acids / sulfonates can be aliphatic or aromatic compounds.
- Preferred sulfonic acids / sulfonates contain 2 or 3 carboxyl groups and, including the carboxyl groups, 3 to 6 carbon atoms.
- a particularly preferred sulfonic acid is sulfosuccinic acid.
- the units (A-O) can be unitary or mixed alkoxy units.
- Mixed alkoxy units can be in a random or block arrangement.
- radicals of the formula (2) can be, for example:
- R 3 represents a methyl group or ethyl group
- b represents a number from 1 to 500
- c represents a number from 1 to 100
- the ethylene glycol, propylene glycol and butylene glycol units are random or blockwise in the
- Polyalkylene glycol ether residue are distributed, e) a polyethylene glycol ether sulfuric acid ester of the formula (6)
- a number from 1 to 500 and Me represent a sodium, potassium or ammonium ion, f) or a polyethylene glycol ether phosphoric acid ester of the formula (7)
- b represents a number from 1 to 500, g) a polyethylene glycol ether sulfosuccinic acid semi-ester (Polyethylene glycol ether sulfosuccinate) of the formula (8)
- b is a number from 1 to 500.
- the alkoxylated esters of polyglycerol can be prepared by reacting such an ester with a C 2 -C 4 -alkylene oxide in the presence of an alkaline catalyst such as KOH, NaOH, potassium methylate or sodium methylate at temperatures between 120 and 200 ° C.
- an alkaline catalyst such as KOH, NaOH, potassium methylate or sodium methylate at temperatures between 120 and 200 ° C.
- the anionically derivatized esters of polyglycerol can be prepared by reacting the alkoxylated esters of polyglycerol with suitable acids.
- the production of sulfate esters is preferably carried out with amidosulfonic acid instead of with sulfuric acid.
- Phosphoric acid esters phosphoric acid can be used.
- Organic acids are preferably reacted in the form of their anhydrides with the alcohols of the formula 1.
- Functional groups are preferably inserted after the ester of the non-functionalized acid has been prepared.
- the preparation of the sulfosuccinic acid ester can be carried out by producing the corresponding
- the invention further relates to a process for the preparation of polymer dispersions in which olefinically unsaturated monomers are polymerized in the presence of the esters of polyglycerol.
- the monomers used for the production of polymer dispersions by the emulsion polymerization process are, for example, vinyl monomers, such as carboxylic acid esters of vinyl alcohol, for example Vinyl acetate, vinyl propionate, vinyl ether of isononanoic acid or
- Aryl-substituted olefins such as styrene and stilbene, olefinically unsaturated carboxylic acid esters, such as methyl acrylate, ethyl acrylate, propyl acrylate, n-butyl acrylate, i-butyl acrylate, pentyl acrylate, hexyl acrylate,
- Methacrylic acid esters olefinically unsaturated dicarboxylic acid esters, such as dimethyl maleate,
- Methacrylic acid methacrylic acid, itaconic acid, maleic acid and fumaric acid and their
- the above-mentioned monomers are mixed with further comonomers, preferably olefins or halogenated olefins having 2 to 8 carbon atoms, e.g. Polymerized ethylene, propene, butenes, pentenes, 1, 3-butadiene, chloroprene, vinyl chloride, vinylidene chloride, vinylidene fluoride and tetrafluoroethylene.
- further comonomers preferably olefins or halogenated olefins having 2 to 8 carbon atoms, e.g. Polymerized ethylene, propene, butenes, pentenes, 1, 3-butadiene, chloroprene, vinyl chloride, vinylidene chloride, vinylidene fluoride and tetrafluoroethylene.
- the water-immiscible monomers are generally used with the aid of the emulsifiers according to the invention in the finely divided aqueous phase in the form of micelles and the radical polymerization reaction started by initiators such as ammonium, sodium and potassium peroxodisulfate.
- auxiliaries and additives for use with the emulsifiers according to the invention can be protective colloids such as carboxymethyl cellulose, hydroxyethyl cellulose, methyl hydroxypropyl cellulose, and partially and fully hydrolyzed polyvinyl alcohol.
- the fatty acid polyglycerol esters according to the invention and their alkoxylated and anionic derivatives can be used during the emulsion polymerization by placing them in the reaction vessel before the start of the polymerization reaction or adding them to the reaction vessel during the polymerization reaction.
- Another variant is the addition after completion of the polymerization reaction to improve the stability of the polymer dispersion.
- the fatty acid polyglycerol esters according to the invention and their alkoxylated and anionic derivatives can be used both alone and in combination with other already known anionic and nonionic emulsifiers of the prior art, as described at the beginning.
- the amount of the anionic and nonionic emulsifiers of the prior art is then preferably 0.05 to 5, in particular 0.08 to 3% and particularly preferably 0.1 to 2% by weight, based on the weight of the water-insoluble or slightly water-soluble monomers.
- esters of polyglycerol and their alkoxylated and anionic derivatives according to the invention in amounts of 0.1 to 10, preferably 0.2 to 5, in particular 0.4 to 4 wt .-%, based on the weight of the for Preparation of the polymer dispersion used non or slightly water-soluble monomers used as emulsifiers.
- the polymer dispersions prepared with the esters of polyglycerol and their alkoxylated and anionic derivatives according to the invention show low coagulum formation during and after the polymerization and an improvement in the shear, temperature and storage stability, the freeze / thaw stability and the electrolyte stability compared to divalent and trivalent cations such as Calcium, barium and aluminum. An improvement in the film properties of the polymer films produced from the polymer dispersions can also be observed.
- the polymer dispersions prepared with the polyglycerol esters according to the invention form films. low water absorption, a low whitening on contact with water and good wet and dry rub fastness.
- the reaction temperature was kept constant at 79 to 81 ° C by cooling or heating over the water bath. After 15 minutes, the remaining 1530 g of the monomer emulsion were added over a period of 3 hours. To initiate the radical polyaddition reaction, the remaining 215.7 g of the initiator solution were added over a period of 3 hours and 15 minutes via a second feed. The reaction mixture was then stirred for a further 2 hours at 80 ° C. with stirring and under a nitrogen atmosphere and then cooled to room temperature. For the preservation of the polymer dispersion produced were 3.6 g ® Nipacide CI15 (Nipa Laboratories Ltd.) was added.
- the resulting polymer dispersion had a solids content of 50% and a coagulate of ⁇ 0.010% over a 100 ⁇ m sieve and of ⁇ 0.015% over a 40 ⁇ m sieve.
- the resulting polymer dispersion had a solids content of 65% and a coagulum of ⁇ 0.050% over a 100 ⁇ m sieve and of ⁇ 0.080% over a 40 ⁇ m sieve.
- the dosage of the aqueous potassium peroxodisulfate solution lasted 175 minutes.
- the polymerization mixture was tempered at 80 ° C. by cooling or by supplying heat. After a post-polymerization time of one hour at 80 ° C., the polymer dispersion was cooled to room temperature. For the preservation of the prepared polymer dispersion, 3.3 g of ® Nipacide CI15 (Nipa Laboratories Ltd.) was added.
- the resulting polymer dispersion had a solids content of 54% and a coagulum of ⁇ 0.10% over a 100 ⁇ m sieve.
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/478,152 US20040143057A1 (en) | 2001-05-19 | 2002-05-07 | Use of polyglycerine esters and the alkoxylated and anionic derivatives thereof as emulsifiers in emulsions polymerisation |
EP02753044A EP1401878A1 (de) | 2001-05-19 | 2002-05-07 | Verwendung von estern des polyglycerins und deren alkoxylierten und anionischen derivaten als emulgatoren in der emulsionspolymerisation |
JP2002592359A JP2004526851A (ja) | 2001-05-19 | 2002-05-07 | ポリグリセロールのエステルおよびそれのアルコキシル化されたおよびアニオン性誘導体の、乳化重合において乳化剤としての用途 |
BR0209289-1A BR0209289A (pt) | 2001-05-19 | 2002-05-07 | Aplicação de ésteres da poliglicerina e seus derivados alcoxilados e aniÈnicos como emulsificantes na polimerização em emulsão |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10124547.5 | 2001-05-19 | ||
DE10124547A DE10124547A1 (de) | 2001-05-19 | 2001-05-19 | Verwendung von Estern des Polyglycerins und deren alkoxylierten und anionischen Derivaten als Emulgatoren in der Emulsionspolymerisation |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2002094885A1 true WO2002094885A1 (de) | 2002-11-28 |
Family
ID=7685468
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/EP2002/005008 WO2002094885A1 (de) | 2001-05-19 | 2002-05-07 | Verwendung von estern des polyglycerins und deren alkoxylierten und anionischen derivaten als emulgatoren in der emulsionspolymerisation |
Country Status (6)
Country | Link |
---|---|
US (1) | US20040143057A1 (de) |
EP (1) | EP1401878A1 (de) |
JP (1) | JP2004526851A (de) |
BR (1) | BR0209289A (de) |
DE (1) | DE10124547A1 (de) |
WO (1) | WO2002094885A1 (de) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
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DE10211801B4 (de) | 2002-03-16 | 2004-09-30 | Clariant Gmbh | Kosmetische und pharmazeutische Zubereitungen enthaltend einen oxalkylierten Polyglycerinester |
DE10307171B4 (de) * | 2003-02-20 | 2009-04-16 | Clariant Produkte (Deutschland) Gmbh | Copolymere enthaltende landwirschaftliche Mittel |
DE10342870A1 (de) | 2003-09-15 | 2005-05-12 | Clariant Gmbh | Flüssige Zusammensetzungen enthaltend oxalkylierte Polyglycerinester |
US10370493B2 (en) | 2016-01-29 | 2019-08-06 | Evonik Degussa Gmbh | Polyglycerol alkoxylate esters and preparation and use thereof |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS54163984A (en) * | 1978-06-16 | 1979-12-27 | Shinetsu Chemical Co | Production of vinyl chloride polymer |
EP0349240A2 (de) * | 1988-06-28 | 1990-01-03 | Nippon Shokubai Co., Ltd. | Wasserabsorbierendes Harz und seine Herstellung |
Family Cites Families (6)
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US4158092A (en) * | 1974-07-25 | 1979-06-12 | Hoechst Aktiengesellschaft | Process for the manufacture of vinyl chloride polymer dispersions with a low monomer content |
DE2509937C3 (de) * | 1975-03-07 | 1981-04-16 | Hoechst Ag, 6000 Frankfurt | Vorrichtung zur Nachbehandlung von Homo- und Copolymerisaten des Vinylchlorids |
US4650827A (en) * | 1983-11-02 | 1987-03-17 | Allied Corporation | Stable water-in-oil emulsions |
US4581413A (en) * | 1984-12-24 | 1986-04-08 | The B. F. Goodrich Company | Vinyl dispersion resins |
US4797458A (en) * | 1986-09-02 | 1989-01-10 | The B.F. Goodrich Company | Colloidal stable vinyl halide polymerizations with mercaptan chain transfer agents |
DE69306839T2 (de) * | 1992-03-30 | 1997-06-26 | Sumitomo Chemical Co | Methode zur Herstellung von Vinylchlorid-Harzen |
-
2001
- 2001-05-19 DE DE10124547A patent/DE10124547A1/de not_active Withdrawn
-
2002
- 2002-05-07 WO PCT/EP2002/005008 patent/WO2002094885A1/de not_active Application Discontinuation
- 2002-05-07 JP JP2002592359A patent/JP2004526851A/ja not_active Withdrawn
- 2002-05-07 US US10/478,152 patent/US20040143057A1/en not_active Abandoned
- 2002-05-07 BR BR0209289-1A patent/BR0209289A/pt not_active Application Discontinuation
- 2002-05-07 EP EP02753044A patent/EP1401878A1/de not_active Withdrawn
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS54163984A (en) * | 1978-06-16 | 1979-12-27 | Shinetsu Chemical Co | Production of vinyl chloride polymer |
EP0349240A2 (de) * | 1988-06-28 | 1990-01-03 | Nippon Shokubai Co., Ltd. | Wasserabsorbierendes Harz und seine Herstellung |
Non-Patent Citations (1)
Title |
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DATABASE WPI Week 198006, Derwent World Patents Index; AN 10408C, XP002216223 * |
Also Published As
Publication number | Publication date |
---|---|
US20040143057A1 (en) | 2004-07-22 |
EP1401878A1 (de) | 2004-03-31 |
JP2004526851A (ja) | 2004-09-02 |
BR0209289A (pt) | 2004-07-13 |
DE10124547A1 (de) | 2002-11-28 |
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