NO313050B1 - Kontinuerlig fremstilling av hydroksylerte addisjonspolymerer med redusert gelinnhold - Google Patents
Kontinuerlig fremstilling av hydroksylerte addisjonspolymerer med redusert gelinnhold Download PDFInfo
- Publication number
- NO313050B1 NO313050B1 NO19971818A NO971818A NO313050B1 NO 313050 B1 NO313050 B1 NO 313050B1 NO 19971818 A NO19971818 A NO 19971818A NO 971818 A NO971818 A NO 971818A NO 313050 B1 NO313050 B1 NO 313050B1
- Authority
- NO
- Norway
- Prior art keywords
- solvent
- monomers
- reactor
- solvents
- gel
- Prior art date
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 96
- 238000002360 preparation method Methods 0.000 title claims description 10
- 239000002904 solvent Substances 0.000 claims abstract description 146
- 239000000178 monomer Substances 0.000 claims abstract description 114
- 238000000034 method Methods 0.000 claims abstract description 59
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 58
- 239000000203 mixture Substances 0.000 claims abstract description 43
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 42
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000000376 reactant Substances 0.000 claims abstract description 33
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 26
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000007342 radical addition reaction Methods 0.000 claims abstract description 16
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000007788 liquid Substances 0.000 claims abstract description 14
- 239000011877 solvent mixture Substances 0.000 claims abstract description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 44
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- 230000000694 effects Effects 0.000 claims description 11
- -1 hydroxyalkyl acrylates Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 6
- 238000001879 gelation Methods 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 abstract description 29
- 239000007863 gel particle Substances 0.000 abstract description 22
- 238000010924 continuous production Methods 0.000 abstract description 21
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract description 16
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 abstract description 15
- 150000003254 radicals Chemical class 0.000 abstract description 10
- 239000000499 gel Substances 0.000 description 74
- 238000002474 experimental method Methods 0.000 description 50
- 239000011541 reaction mixture Substances 0.000 description 26
- 238000004140 cleaning Methods 0.000 description 25
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 18
- 229940044192 2-hydroxyethyl methacrylate Drugs 0.000 description 13
- 102100026735 Coagulation factor VIII Human genes 0.000 description 12
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 12
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 11
- 239000012969 di-tertiary-butyl peroxide Substances 0.000 description 11
- 239000007791 liquid phase Substances 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 229920000058 polyacrylate Polymers 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- 239000005977 Ethylene Substances 0.000 description 5
- 238000004364 calculation method Methods 0.000 description 5
- 238000011109 contamination Methods 0.000 description 5
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 5
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 4
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 150000005690 diesters Chemical class 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 239000012808 vapor phase Substances 0.000 description 4
- ZAXXZBQODQDCOW-UHFFFAOYSA-N 1-methoxypropyl acetate Chemical compound CCC(OC)OC(C)=O ZAXXZBQODQDCOW-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000008961 swelling Effects 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 2
- IEVADDDOVGMCSI-UHFFFAOYSA-N 2-hydroxybutyl 2-methylprop-2-enoate Chemical compound CCC(O)COC(=O)C(C)=C IEVADDDOVGMCSI-UHFFFAOYSA-N 0.000 description 2
- NJRHMGPRPPEGQL-UHFFFAOYSA-N 2-hydroxybutyl prop-2-enoate Chemical compound CCC(O)COC(=O)C=C NJRHMGPRPPEGQL-UHFFFAOYSA-N 0.000 description 2
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 2
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 238000012644 addition polymerization Methods 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HHQAGBQXOWLTLL-UHFFFAOYSA-N (2-hydroxy-3-phenoxypropyl) prop-2-enoate Chemical group C=CC(=O)OCC(O)COC1=CC=CC=C1 HHQAGBQXOWLTLL-UHFFFAOYSA-N 0.000 description 1
- DDKMFQGAZVMXQV-UHFFFAOYSA-N (3-chloro-2-hydroxypropyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CCl DDKMFQGAZVMXQV-UHFFFAOYSA-N 0.000 description 1
- POTYORUTRLSAGZ-UHFFFAOYSA-N (3-chloro-2-hydroxypropyl) prop-2-enoate Chemical compound ClCC(O)COC(=O)C=C POTYORUTRLSAGZ-UHFFFAOYSA-N 0.000 description 1
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 1
- HGOUNPXIJSDIKV-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butyl 2-methylprop-2-enoate Chemical compound CCC(CO)(CO)COC(=O)C(C)=C HGOUNPXIJSDIKV-UHFFFAOYSA-N 0.000 description 1
- SYENVBKSVVOOPS-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butyl prop-2-enoate Chemical compound CCC(CO)(CO)COC(=O)C=C SYENVBKSVVOOPS-UHFFFAOYSA-N 0.000 description 1
- OLQFXOWPTQTLDP-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCO OLQFXOWPTQTLDP-UHFFFAOYSA-N 0.000 description 1
- RWXMAAYKJDQVTF-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl prop-2-enoate Chemical compound OCCOCCOC(=O)C=C RWXMAAYKJDQVTF-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
- CHNGPLVDGWOPMD-UHFFFAOYSA-N 2-ethylbutyl 2-methylprop-2-enoate Chemical compound CCC(CC)COC(=O)C(C)=C CHNGPLVDGWOPMD-UHFFFAOYSA-N 0.000 description 1
- VWJAVBOLCVPIAK-UHFFFAOYSA-N 2-methoxybutyl 2-methylprop-2-enoate Chemical compound CCC(OC)COC(=O)C(C)=C VWJAVBOLCVPIAK-UHFFFAOYSA-N 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 1
- ILZXXGLGJZQLTR-UHFFFAOYSA-N 2-phenylethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=CC=C1 ILZXXGLGJZQLTR-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- NWKKCUWIMOZYOO-UHFFFAOYSA-N 3-methoxybutyl 2-methylprop-2-enoate Chemical compound COC(C)CCOC(=O)C(C)=C NWKKCUWIMOZYOO-UHFFFAOYSA-N 0.000 description 1
- HAUXPEUSOPGTJM-UHFFFAOYSA-N 5,6-dihydroxyhexyl prop-2-enoate Chemical compound OCC(O)CCCCOC(=O)C=C HAUXPEUSOPGTJM-UHFFFAOYSA-N 0.000 description 1
- WSHAORDFOHWQPS-UHFFFAOYSA-N 5-bicyclo[2.2.1]hept-2-enylmethanol;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.C1C2C(CO)CC1C=C2 WSHAORDFOHWQPS-UHFFFAOYSA-N 0.000 description 1
- VIJJINVORKTGLO-UHFFFAOYSA-N 5-bicyclo[2.2.1]hept-2-enylmethanol;prop-2-enoic acid Chemical compound OC(=O)C=C.C1C2C(CO)CC1C=C2 VIJJINVORKTGLO-UHFFFAOYSA-N 0.000 description 1
- XFOFBPRPOAWWPA-UHFFFAOYSA-N 6-hydroxyhexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCO XFOFBPRPOAWWPA-UHFFFAOYSA-N 0.000 description 1
- OCIFJWVZZUDMRL-UHFFFAOYSA-N 6-hydroxyhexyl prop-2-enoate Chemical compound OCCCCCCOC(=O)C=C OCIFJWVZZUDMRL-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000467686 Eschscholzia lobbii Species 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 101100074988 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) nmp-1 gene Proteins 0.000 description 1
- RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical class OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- AFSQFGXTYWXFPP-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1(CO)CCCCC1 AFSQFGXTYWXFPP-UHFFFAOYSA-N 0.000 description 1
- KKVKUNIBLLLFHA-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methyl prop-2-enoate Chemical compound C=CC(=O)OCC1(CO)CCCCC1 KKVKUNIBLLLFHA-UHFFFAOYSA-N 0.000 description 1
- APZPSKFMSWZPKL-UHFFFAOYSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)(CO)CO APZPSKFMSWZPKL-UHFFFAOYSA-N 0.000 description 1
- ZCZFEIZSYJAXKS-UHFFFAOYSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] prop-2-enoate Chemical compound OCC(CO)(CO)COC(=O)C=C ZCZFEIZSYJAXKS-UHFFFAOYSA-N 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000012864 cross contamination Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- FWLDHHJLVGRRHD-UHFFFAOYSA-N decyl prop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C=C FWLDHHJLVGRRHD-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 229940117927 ethylene oxide Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- AWJZTPWDQYFQPQ-UHFFFAOYSA-N methyl 2-chloroprop-2-enoate Chemical compound COC(=O)C(Cl)=C AWJZTPWDQYFQPQ-UHFFFAOYSA-N 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
- ZZSKMNCIAKKVRB-UHFFFAOYSA-N morpholin-4-yl-(2-nitrophenyl)methanone Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)N1CCOCC1 ZZSKMNCIAKKVRB-UHFFFAOYSA-N 0.000 description 1
- OVHHHVAVHBHXAK-UHFFFAOYSA-N n,n-diethylprop-2-enamide Chemical compound CCN(CC)C(=O)C=C OVHHHVAVHBHXAK-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
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- ULDDEWDFUNBUCM-UHFFFAOYSA-N pentyl prop-2-enoate Chemical compound CCCCCOC(=O)C=C ULDDEWDFUNBUCM-UHFFFAOYSA-N 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 238000004184 polymer manufacturing process Methods 0.000 description 1
- 238000010094 polymer processing Methods 0.000 description 1
- 229920001291 polyvinyl halide Polymers 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-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
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005156 substituted alkylene group Chemical group 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920003169 water-soluble 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
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)
- Colloid Chemistry (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/325,001 US5508366A (en) | 1994-10-18 | 1994-10-18 | Continuous production of reduced gel content hydroxylated addition polymers |
| PCT/US1995/012836 WO1996011957A1 (fr) | 1994-10-18 | 1995-10-13 | Production en continu de polymeres d'addition hydroxyles a teneur reduite en gel |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO971818D0 NO971818D0 (no) | 1997-04-18 |
| NO971818L NO971818L (no) | 1997-06-17 |
| NO313050B1 true NO313050B1 (no) | 2002-08-05 |
Family
ID=23266019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19971818A NO313050B1 (no) | 1994-10-18 | 1997-04-18 | Kontinuerlig fremstilling av hydroksylerte addisjonspolymerer med redusert gelinnhold |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US5508366A (fr) |
| EP (1) | EP0787154B1 (fr) |
| JP (1) | JP3550152B2 (fr) |
| KR (1) | KR100350338B1 (fr) |
| CN (1) | CN1083456C (fr) |
| AT (1) | ATE182154T1 (fr) |
| AU (1) | AU703253B2 (fr) |
| CA (1) | CA2202902C (fr) |
| DE (1) | DE69510813T2 (fr) |
| DK (1) | DK0787154T3 (fr) |
| ES (1) | ES2134500T3 (fr) |
| FI (1) | FI971636A7 (fr) |
| GR (1) | GR3031056T3 (fr) |
| NO (1) | NO313050B1 (fr) |
| SG (1) | SG50359A1 (fr) |
| WO (1) | WO1996011957A1 (fr) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3516035B2 (ja) | 1997-05-13 | 2004-04-05 | 綜研化学株式会社 | 粘着剤組成物 |
| US5986020A (en) * | 1997-08-05 | 1999-11-16 | Campbell; J. David | Process for producing hyperbranched polymers |
| WO2000002932A1 (fr) * | 1998-07-10 | 2000-01-20 | S. C. Johnson Commercial Markets, Inc. | Processus de production de polymeres par polymerisation radicalaire et reaction de condensation, et appareil et produits y relatifs |
| ES2340174T3 (es) | 1999-07-14 | 2010-05-31 | Basf Corporation | Proceso para la produccion continua de polimeros de epoxi-(met)acrilico estireno y su uso en recubrimientos. |
| CN1198850C (zh) * | 1999-07-14 | 2005-04-27 | 约翰逊聚合物公司 | 连续生产不含凝胶聚合物的方法,及含有不含凝胶聚合物的粉末和液体涂料应用 |
| US6653427B2 (en) | 2000-03-31 | 2003-11-25 | Avery Dennison Corporation | Hydrophilic polymers, pressure sensitive adhesives and coatings |
| US6743880B2 (en) * | 2000-03-31 | 2004-06-01 | Avery Denison Corporation | Hydrophilic polymers and methods of preparation |
| US6706836B1 (en) * | 2000-03-31 | 2004-03-16 | Avery Dennison Corporation | Hydrophilic polymers, pressure sensitive adhesives and coatings |
| US6605681B1 (en) | 2000-07-12 | 2003-08-12 | Johnson Polymer, Inc. | Process for the continuous production of epoxylated addition polymers, and powder and liquid coating applications containing epoxylated addition polymers |
| JP4769408B2 (ja) | 2000-11-03 | 2011-09-07 | ジヨンソン・アンド・ジヨンソン・ビジヨン・ケア・インコーポレーテツド | 親水性および疎水性モノマーを含有するポリマーの調製に有用な溶媒 |
| US7315896B2 (en) * | 2002-06-06 | 2008-01-01 | International Business Machines Corporation | Server network controller including packet forwarding and method therefor |
| US20040029757A1 (en) * | 2002-08-08 | 2004-02-12 | Ecolab Inc. | Hand dishwashing detergent composition and methods for manufacturing and using |
| US20070066777A1 (en) * | 2004-09-03 | 2007-03-22 | Bzowej Eugene I | Methods for producing crosslinkable oligomers |
| KR20120089857A (ko) | 2009-09-30 | 2012-08-14 | 바스프 에스이 | 알콕실화 중합체 |
| CN102295513A (zh) * | 2010-06-25 | 2011-12-28 | 中国石油化工股份有限公司 | 萃取精馏法精制异戊二烯的方法 |
| JP5751055B2 (ja) * | 2010-11-30 | 2015-07-22 | Jnc株式会社 | 光ナノインプリント用硬化性組成物および硬化性組成物から得られた硬化膜 |
| US9540513B2 (en) | 2012-11-21 | 2017-01-10 | Basf Se | Lignocellulosic article and method of producing same |
| SG11201700953QA (en) | 2014-08-15 | 2017-03-30 | Basf Se | Composition comprising silver nanowires and dispersed polymer beads for the preparation of electroconductive transparent layers |
| CA2957837A1 (fr) | 2014-08-15 | 2016-02-18 | Basf Se | Composition comprenant des nanofils d'argent et des copolymeres styrene/(meth)acryliques permettant la preparation de couches transparentes electroconductrices |
| JP6832850B2 (ja) | 2014-08-15 | 2021-02-24 | ビーエイエスエフ・ソシエタス・エウロパエアBasf Se | 導電性透明層の製造のための銀ナノワイヤーおよび結晶性セルロースの繊維を含む組成物 |
| CN107429095A (zh) | 2015-04-09 | 2017-12-01 | 巴斯夫欧洲公司 | 用于制备透明导电层的含有处于醇/水混合物中的银纳米线和分散的苯乙烯/(甲基)丙烯酸类共聚物的组合物 |
| WO2018007355A1 (fr) | 2016-07-06 | 2018-01-11 | Basf Se | Revêtement contenant des particules métalliques |
| WO2018019813A1 (fr) | 2016-07-29 | 2018-02-01 | Basf Se | Couche électro-conductrice transparente et encre pour sa production |
| CN108610447B (zh) * | 2016-12-09 | 2021-02-05 | 中国石油化工股份有限公司 | 适于烯烃共聚的物料混合方法及混合装置和烯烃共聚方法 |
| CN110167985A (zh) | 2017-01-12 | 2019-08-23 | 巴斯夫欧洲公司 | 聚氨酯的物理性能改进 |
| CN111933974B (zh) * | 2020-07-31 | 2021-09-07 | 广东国鸿氢能科技有限公司 | 一种燃料电池增湿反应气体的露点温度的测试方法 |
| KR20250025848A (ko) * | 2023-08-16 | 2025-02-25 | 에스케이이노베이션 주식회사 | 에틸렌-아크릴산 공중합체 제조공정의 플러깅 억제방법 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4351931A (en) * | 1961-06-26 | 1982-09-28 | E. I. Du Pont De Nemours And Company | Polyethylene copolymers |
| CH532090A (de) * | 1966-05-24 | 1972-12-31 | Ceskoslovenska Akademie Ved | Verfahren zur Herstellung von löslichen Polymeren bzw. Copolymeren von Glykolmonomethacrylaten bzw. -acrylaten |
| US3764384A (en) * | 1970-07-24 | 1973-10-09 | Gaf Corp | Process for removing polyvinyl halide residues from processing equipment |
| US3988213A (en) * | 1972-09-25 | 1976-10-26 | Nippon Shokubai Kagaku Kogyo Co., Ltd. | Method of distilling vinyl compounds |
| US4276432A (en) * | 1973-07-18 | 1981-06-30 | Celanese Corporation | Low molecular weight acrylates or methacrylates and methods for their preparation |
| FR2295972A1 (fr) * | 1974-12-23 | 1976-07-23 | Michelin & Cie | Polymerisation ou copolymerisation en solution d'un ou plusieurs dienes conjugues avec eventuellement un ou plusieurs composes vinylaromatiques |
| US4014754A (en) * | 1975-04-25 | 1977-03-29 | Gaf Corporation | Recovery of lactam solvent from vinyl polymer solution |
| US4172177A (en) * | 1975-06-17 | 1979-10-23 | Kyowa Gas Chemical Industry Co., Ltd. | Water insoluble hydrophilic polymer composition |
| DE2757329C2 (de) * | 1977-12-22 | 1980-02-07 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von Polymerisaten der Acrylsäure oder Methacrylsäure |
| DE2850872A1 (de) * | 1978-11-24 | 1980-06-04 | Bayer Ag | Wasserverduennbare lackbindemittel fuer chemikalienfeste beschichtungen |
| US4324868A (en) * | 1979-06-19 | 1982-04-13 | Mitsubishi Rayon Co., Ltd. | Process and apparatus for preparation of vinyl polymers |
| US4414370A (en) * | 1981-01-09 | 1983-11-08 | S. C. Johnson & Son, Inc. | Process for continuous bulk copolymerization of vinyl monomers |
| DE3271521D1 (en) * | 1981-03-25 | 1986-07-10 | Ciba Geigy Ag | Composition for fixing the hair, its preparation and its use in aerosol sprays |
| CA1215495A (fr) * | 1981-07-28 | 1986-12-16 | Kenji Satoh | Copolymerisation continue de l'ethylene et de l'acetate de vinyle |
| US4529787A (en) * | 1982-06-15 | 1985-07-16 | S. C. Johnson & Son, Inc. | Bulk polymerization process for preparing high solids and uniform copolymers |
| US4728701A (en) * | 1983-09-19 | 1988-03-01 | Jarvis Marvin A | Process for the polymerization of acrylates |
| US4546160A (en) * | 1984-02-29 | 1985-10-08 | S. C. Johnson & Son, Inc. | Bulk polymerization process for preparing high solids and uniform copolymers |
| DE3628119A1 (de) * | 1986-08-19 | 1988-02-25 | Herberts Gmbh | Fremdvernetzende bindemittelkombination, diese enthaltende waessriges ueberzugsmittel und dessen verwendung |
| US5003021A (en) * | 1988-03-22 | 1991-03-26 | Asahi Kasei Kogyo Kabushiki Kaisha | Process for producing an aromatic vinyl compound-vinyl cyanide compound copolymer |
| US4921755A (en) * | 1988-03-23 | 1990-05-01 | Eastman Kodak Company | Coating composition and coated article |
| IT1241155B (it) * | 1990-05-18 | 1993-12-29 | Vedril | Procedimento per la produzione di polimeri acrilici in massa continua |
| US5028674A (en) * | 1990-06-06 | 1991-07-02 | E. I. Du Pont De Nemours And Company | Methanol copolymerization of ethylene |
| US5057593A (en) * | 1990-06-11 | 1991-10-15 | E. I. Du Pont De Nemours And Company | Free radical copolymerization of ethylene and CO with acetone |
| US5064557A (en) * | 1990-10-15 | 1991-11-12 | Isp Investments Inc. | Resin cleaner composition |
| US5210111A (en) * | 1991-08-22 | 1993-05-11 | Ciba-Geigy Corporation | Crosslinked hydrogels derived from hydrophilic polymer backbones |
-
1994
- 1994-10-18 US US08/325,001 patent/US5508366A/en not_active Expired - Lifetime
-
1995
- 1995-10-13 DK DK95935727T patent/DK0787154T3/da active
- 1995-10-13 KR KR1019970702537A patent/KR100350338B1/ko not_active Expired - Lifetime
- 1995-10-13 ES ES95935727T patent/ES2134500T3/es not_active Expired - Lifetime
- 1995-10-13 AT AT95935727T patent/ATE182154T1/de not_active IP Right Cessation
- 1995-10-13 JP JP51331696A patent/JP3550152B2/ja not_active Expired - Lifetime
- 1995-10-13 EP EP95935727A patent/EP0787154B1/fr not_active Expired - Lifetime
- 1995-10-13 WO PCT/US1995/012836 patent/WO1996011957A1/fr not_active Ceased
- 1995-10-13 AU AU37636/95A patent/AU703253B2/en not_active Ceased
- 1995-10-13 CN CN95196326A patent/CN1083456C/zh not_active Expired - Lifetime
- 1995-10-13 CA CA002202902A patent/CA2202902C/fr not_active Expired - Fee Related
- 1995-10-13 DE DE69510813T patent/DE69510813T2/de not_active Expired - Lifetime
- 1995-10-17 SG SG1995001570A patent/SG50359A1/en unknown
-
1997
- 1997-04-17 FI FI971636A patent/FI971636A7/fi unknown
- 1997-04-18 NO NO19971818A patent/NO313050B1/no not_active IP Right Cessation
-
1999
- 1999-08-23 GR GR990402135T patent/GR3031056T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU703253B2 (en) | 1999-03-25 |
| SG50359A1 (en) | 1998-07-20 |
| ATE182154T1 (de) | 1999-07-15 |
| MX9702860A (es) | 1997-07-31 |
| FI971636A0 (fi) | 1997-04-17 |
| DE69510813T2 (de) | 1999-11-04 |
| JPH10511992A (ja) | 1998-11-17 |
| CN1164239A (zh) | 1997-11-05 |
| EP0787154A1 (fr) | 1997-08-06 |
| CA2202902C (fr) | 2000-06-20 |
| CA2202902A1 (fr) | 1996-04-25 |
| NO971818D0 (no) | 1997-04-18 |
| ES2134500T3 (es) | 1999-10-01 |
| CN1083456C (zh) | 2002-04-24 |
| AU3763695A (en) | 1996-05-06 |
| JP3550152B2 (ja) | 2004-08-04 |
| US5508366A (en) | 1996-04-16 |
| FI971636A7 (fi) | 1997-06-16 |
| MX199818B (fr) | 2000-11-27 |
| KR970707167A (ko) | 1997-12-01 |
| DE69510813D1 (de) | 1999-08-19 |
| WO1996011957A1 (fr) | 1996-04-25 |
| EP0787154B1 (fr) | 1999-07-14 |
| NO971818L (no) | 1997-06-17 |
| GR3031056T3 (en) | 1999-12-31 |
| DK0787154T3 (da) | 1999-12-06 |
| KR100350338B1 (ko) | 2003-02-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO313050B1 (no) | Kontinuerlig fremstilling av hydroksylerte addisjonspolymerer med redusert gelinnhold | |
| US5093427A (en) | Copolymers of vinylidene fluoride and hexafluoropropylene and process for preparing the same | |
| US5028674A (en) | Methanol copolymerization of ethylene | |
| US4181788A (en) | Process for the production of thermoplastic molding materials based on vinyl polymers | |
| US3311583A (en) | Terpolymer acrylates-acrylic acid-hydroxyalkyl esters of acrylic acid | |
| JPH0757796B2 (ja) | エチレンの連続共重合法 | |
| US20110124829A1 (en) | Synthesis of acrylic or methacrylic acid/acrylate or methacrylate ester polymers using pervaporation | |
| NO174425B (no) | Fremgangsmaate til fremstilling av polymerer som omfatter sidekjedegrupper avledet fra to funksjonelle grupper | |
| CN1113848C (zh) | 设备部件的清洗方法 | |
| JP4676687B2 (ja) | (メタ)アクリル系重合体の製造方法 | |
| GB2181735A (en) | Maleic acid polymer for use as scale inhibitor | |
| NO157732B (no) | Middel og fremgangsmte for hindre oppbygning av belegg og avsetninger i vann og vandige media. | |
| MXPA97002860A (en) | Continuous production of hydroxylated addition polymers with reduced content of | |
| JPH03185007A (ja) | 水性懸濁媒質中での弗化ビニリデン重合中の反応器内におけるビルドアップ形成の減少方法 | |
| EP0225809B1 (fr) | Procédé pour la production de résines acryliques et leur utilisation | |
| WO2009006396A2 (fr) | Formation d'intermédiaires polymères radicalisés et compositions d'intermédiaires polymères radicalisés | |
| AU2005201143B2 (en) | A continuous process for preparing polymers | |
| JP4242267B2 (ja) | ビニル系重合体組成物の製造方法 | |
| JPH0539323A (ja) | アクリロニトリル‐スチレン系共重合体樹脂及びその製造方法 | |
| JP4468251B2 (ja) | ポリマーの製造方法 | |
| KR100187694B1 (ko) | 중합용기용 부착방지제 및 이것을 사용한 비닐계 단량체의 중합방법 | |
| JP4279166B2 (ja) | ビニル系重合体の製造方法 | |
| JPH10513486A (ja) | ポリエチレンコポリマー類の改良製造方法 | |
| MXPA06005974A (en) | Method of making copolymers containing olefinic type monomers | |
| JPH03227306A (ja) | 高ニトリル共重合体の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |