NO327596B1 - Fremgangsmate for fremstilling av peroksidikarbonater og deres anvendelse i radikal polymerisasjon av monomerer - Google Patents
Fremgangsmate for fremstilling av peroksidikarbonater og deres anvendelse i radikal polymerisasjon av monomerer Download PDFInfo
- Publication number
- NO327596B1 NO327596B1 NO20021934A NO20021934A NO327596B1 NO 327596 B1 NO327596 B1 NO 327596B1 NO 20021934 A NO20021934 A NO 20021934A NO 20021934 A NO20021934 A NO 20021934A NO 327596 B1 NO327596 B1 NO 327596B1
- Authority
- NO
- Norway
- Prior art keywords
- peroxydicarbonate
- container
- alkali metal
- peroxide
- polymerization
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 78
- 239000000178 monomer Substances 0.000 title claims abstract description 59
- 125000005634 peroxydicarbonate group Chemical group 0.000 title claims abstract description 42
- 238000002360 preparation method Methods 0.000 title description 4
- 238000010526 radical polymerization reaction Methods 0.000 title 1
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 claims abstract description 87
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 72
- 238000006243 chemical reaction Methods 0.000 claims abstract description 71
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 56
- 150000004973 alkali metal peroxides Chemical class 0.000 claims abstract description 51
- 229920000642 polymer Polymers 0.000 claims abstract description 39
- 239000002270 dispersing agent Substances 0.000 claims abstract description 38
- 239000000203 mixture Substances 0.000 claims abstract description 23
- 150000002978 peroxides Chemical class 0.000 claims abstract description 16
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 12
- 239000004014 plasticizer Substances 0.000 claims abstract description 9
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 39
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 24
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 24
- CWINGZLCRSDKCL-UHFFFAOYSA-N ethoxycarbonyloxy ethyl carbonate Chemical group CCOC(=O)OOC(=O)OCC CWINGZLCRSDKCL-UHFFFAOYSA-N 0.000 claims description 22
- 238000002156 mixing Methods 0.000 claims description 19
- -1 peroxide dicarbonate Chemical class 0.000 claims description 19
- 238000001816 cooling Methods 0.000 claims description 18
- 229920002689 polyvinyl acetate Polymers 0.000 claims description 11
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical group ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 239000011118 polyvinyl acetate Substances 0.000 claims description 10
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical group [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 229920000609 methyl cellulose Polymers 0.000 claims description 5
- 239000001923 methylcellulose Substances 0.000 claims description 5
- 235000010981 methylcellulose Nutrition 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
- ZACVGCNKGYYQHA-UHFFFAOYSA-N 2-ethylhexoxycarbonyloxy 2-ethylhexyl carbonate Chemical compound CCCCC(CC)COC(=O)OOC(=O)OCC(CC)CCCC ZACVGCNKGYYQHA-UHFFFAOYSA-N 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 108010010803 Gelatin Proteins 0.000 claims description 3
- 229920001213 Polysorbate 20 Polymers 0.000 claims description 3
- 229920002125 Sokalan® Polymers 0.000 claims description 3
- ZGPBOPXFOJBLIV-UHFFFAOYSA-N butoxycarbonyloxy butyl carbonate Chemical compound CCCCOC(=O)OOC(=O)OCCCC ZGPBOPXFOJBLIV-UHFFFAOYSA-N 0.000 claims description 3
- LQKBKHFGCGFBAF-UHFFFAOYSA-N butyl carboxyoxy carbonate Chemical group CCCCOC(=O)OOC(O)=O LQKBKHFGCGFBAF-UHFFFAOYSA-N 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000008273 gelatin Substances 0.000 claims description 3
- 229920000159 gelatin Polymers 0.000 claims description 3
- 235000019322 gelatine Nutrition 0.000 claims description 3
- 235000011852 gelatine desserts Nutrition 0.000 claims description 3
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 3
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 3
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 3
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- MMCOUVMKNAHQOY-UHFFFAOYSA-L oxido carbonate Chemical compound [O-]OC([O-])=O MMCOUVMKNAHQOY-UHFFFAOYSA-L 0.000 claims description 3
- 239000004584 polyacrylic acid Substances 0.000 claims description 3
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 claims description 3
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 claims description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 3
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 claims description 3
- YPVDWEHVCUBACK-UHFFFAOYSA-N propoxycarbonyloxy propyl carbonate Chemical compound CCCOC(=O)OOC(=O)OCCC YPVDWEHVCUBACK-UHFFFAOYSA-N 0.000 claims description 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 claims description 2
- ZURDIGGQEBJLQG-UHFFFAOYSA-M [Cl+].[O-]C=O Chemical compound [Cl+].[O-]C=O ZURDIGGQEBJLQG-UHFFFAOYSA-M 0.000 claims description 2
- 238000007599 discharging Methods 0.000 claims description 2
- 150000004972 metal peroxides Chemical class 0.000 claims 1
- 239000003999 initiator Substances 0.000 abstract description 21
- 150000003254 radicals Chemical class 0.000 abstract description 12
- 239000004800 polyvinyl chloride Substances 0.000 description 28
- 229920000915 polyvinyl chloride Polymers 0.000 description 27
- 239000004615 ingredient Substances 0.000 description 14
- 239000000376 reactant Substances 0.000 description 14
- 238000000265 homogenisation Methods 0.000 description 11
- 239000011347 resin Substances 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 6
- 238000010557 suspension polymerization reaction Methods 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 239000007900 aqueous suspension Substances 0.000 description 4
- NSGQRLUGQNBHLD-UHFFFAOYSA-N butan-2-yl butan-2-yloxycarbonyloxy carbonate Chemical compound CCC(C)OC(=O)OOC(=O)OC(C)CC NSGQRLUGQNBHLD-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 150000004978 peroxycarbonates Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-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
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- AEPWOCLBLLCOGZ-UHFFFAOYSA-N 2-cyanoethyl prop-2-enoate Chemical compound C=CC(=O)OCCC#N AEPWOCLBLLCOGZ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- JDDQLBKEPJXSJL-UHFFFAOYSA-N C(O)(O)=O.C(C)OOCC Chemical compound C(O)(O)=O.C(C)OOCC JDDQLBKEPJXSJL-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000318 alkali metal phosphate Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 229920013820 alkyl cellulose Polymers 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- NJRWLESRYZMVRW-UHFFFAOYSA-N carboxy carboxyoxycarbonyl carbonate Chemical class OC(=O)OC(=O)OC(=O)OC(O)=O NJRWLESRYZMVRW-UHFFFAOYSA-N 0.000 description 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229920013821 hydroxy alkyl cellulose Polymers 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010667 large scale reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical group C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940065472 octyl acrylate Drugs 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 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
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- C08F4/00—Polymerisation catalysts
- C08F4/28—Oxygen or compounds releasing free oxygen
- C08F4/32—Organic compounds
- C08F4/34—Per-compounds with one peroxy-radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
-
- 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
- C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/91—Suspending agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/911—Emulsifying agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/932—Thickener or dispersant for aqueous system
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Polymerization Catalysts (AREA)
- Polymerisation Methods In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/433,907 US6433208B1 (en) | 1999-11-04 | 1999-11-04 | Method for producing stable, dilute, aqueous, emulsified peroxydicarbonates by homogenization |
| PCT/GB2000/004230 WO2001032613A1 (en) | 1999-11-04 | 2000-11-03 | Method for producing peroxydicarbonates and their use in the radical polymerization of monomers |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20021934L NO20021934L (no) | 2002-04-24 |
| NO20021934D0 NO20021934D0 (no) | 2002-04-24 |
| NO327596B1 true NO327596B1 (no) | 2009-08-31 |
Family
ID=23722021
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20021934A NO327596B1 (no) | 1999-11-04 | 2002-04-24 | Fremgangsmate for fremstilling av peroksidikarbonater og deres anvendelse i radikal polymerisasjon av monomerer |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US6433208B1 (sh) |
| EP (1) | EP1226118B1 (sh) |
| JP (2) | JP5031962B2 (sh) |
| KR (1) | KR100732660B1 (sh) |
| CN (1) | CN1387511A (sh) |
| AT (1) | ATE258546T1 (sh) |
| CA (1) | CA2389728C (sh) |
| CZ (1) | CZ302981B6 (sh) |
| DE (1) | DE60008012T2 (sh) |
| DK (1) | DK1226118T3 (sh) |
| ES (1) | ES2215078T3 (sh) |
| HU (1) | HU228803B1 (sh) |
| IL (2) | IL149332A0 (sh) |
| MX (1) | MXPA02003996A (sh) |
| NO (1) | NO327596B1 (sh) |
| PL (1) | PL202098B1 (sh) |
| PT (1) | PT1226118E (sh) |
| WO (1) | WO2001032613A1 (sh) |
| YU (1) | YU32602A (sh) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6995221B2 (en) * | 1999-11-04 | 2006-02-07 | Oxy Vinyls, L.P. | Method for producing organic peroxides and their use in the radical polymerization of monomers |
| US6433208B1 (en) * | 1999-11-04 | 2002-08-13 | Oxy Vinyls Lp | Method for producing stable, dilute, aqueous, emulsified peroxydicarbonates by homogenization |
| PL371120A1 (en) | 2002-03-01 | 2005-06-13 | Akzo Nobel N.V. | Polymerization process involving diacyl peroxides |
| EP1593695B1 (de) * | 2004-05-05 | 2008-07-02 | VESTOLIT GmbH & Co. KG | Verfahren zur Herstellung von Polymeren und Copolymeren |
| EP1849804A1 (en) * | 2006-04-27 | 2007-10-31 | Arkema France | Process of free-radical polymerization or crosslinking in the presence of an organic peroxide by an ex situ process |
| EP1852418A1 (en) * | 2006-04-27 | 2007-11-07 | Arkema France | Process for synthesizing selected organic peroxides |
| CN101619035B (zh) * | 2009-05-06 | 2012-06-06 | 淄博正华助剂股份有限公司 | 2.4-二氯过氧化苯甲酰的制造方法 |
| CN102442932A (zh) * | 2010-10-08 | 2012-05-09 | 淄博正华助剂股份有限公司 | 溶剂型过氧化二碳酸双（2-乙氧基）乙酯的制备方法 |
| FR2968660B1 (fr) * | 2010-12-14 | 2014-03-07 | Solvay | Procede de preparation d'une solution organique d'un peroxydicarbonate de dialkyle |
| CN102584663A (zh) * | 2011-12-26 | 2012-07-18 | 淄博正华助剂股份有限公司 | 溶剂型质量分数75%过氧化二碳酸二（2-乙基己基）酯的制法 |
| CN102659960B (zh) * | 2011-12-26 | 2014-08-20 | 淄博正华助剂股份有限公司 | 溶剂型质量分数60%过氧化二碳酸二（2-乙基己基）酯的制法 |
| JP2017206439A (ja) * | 2014-08-27 | 2017-11-24 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ホモジナイザーを用いる抗腫瘍剤の製造方法 |
| FR3027236B1 (fr) | 2014-10-17 | 2020-01-03 | Arkema France | Emulsion aqueuse de peroxyde de dialkyle |
| CN109134334A (zh) * | 2018-09-11 | 2019-01-04 | 蓝凤祥 | 一种过氧化新癸酸异丙苯酯引发剂的安全生产工艺 |
| CN114149355A (zh) * | 2021-12-27 | 2022-03-08 | 兰州助剂厂有限责任公司 | 一种过氧化二碳酸双十六酯的制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2370588A (en) * | 1942-10-22 | 1945-02-27 | Pittsburgh Plate Glass Co | Organic percarbonates |
| US2661363A (en) | 1952-01-18 | 1953-12-01 | Shell Dev | Peresters of peroxycarboxylic acids |
| AT243234B (de) | 1962-10-06 | 1965-10-25 | Hoechst Ag | Verfahren zur Herstellung von Lösungen von Peroxydikohlensäureestern |
| DE1259325B (de) * | 1964-05-22 | 1968-01-25 | Hoechst Ag | Verfahren zur kontinuierlichen Herstellung von Loesungen von Peroxydikohlensaeureestern |
| DE1265154B (de) * | 1965-11-15 | 1968-04-04 | Hoechst Ag | Verfahren zur kontinuierlichen Herstellung von Loesungen von Peroxydikohlensaeureestern |
| IL29131A (en) | 1967-12-14 | 1971-01-28 | Kreisel M | Process for the polymerization of vinyl compounds |
| US3736344A (en) * | 1967-12-26 | 1973-05-29 | Argus Chem | Low molecular weight acyl peroxycarbonic esters |
| US3799966A (en) * | 1971-12-17 | 1974-03-26 | Pennwalt Corp | Di-(2-phenoxyethyl)peroxydicarbonate |
| US3825509A (en) * | 1972-11-13 | 1974-07-23 | Goodrich Co B F | Initiator emulsion for olefinic polymerization reactions |
| NL7303315A (sh) * | 1973-03-09 | 1974-09-11 | ||
| US3935243A (en) * | 1973-09-17 | 1976-01-27 | The Dow Chemical Company | Method for preparing polyperoxydicarbonate esters |
| FR2253760B1 (sh) | 1973-12-05 | 1976-10-08 | Solvay | |
| US3950375A (en) * | 1973-12-10 | 1976-04-13 | Pennwalt Corporation | Continuous manufacture of peroxydicarbonates |
| US3988261A (en) * | 1975-07-28 | 1976-10-26 | Ppg Industries, Inc. | Frozen organic peroxide emulsion |
| JPS5272790A (en) * | 1975-12-15 | 1977-06-17 | Sumitomo Chem Co Ltd | Suspension polymerization of vinyl chloride |
| JPS5287119A (en) * | 1976-01-12 | 1977-07-20 | Pennwalt Corp | Process for continuously manufacturing peroxydicarbonate |
| JPS559067A (en) * | 1978-06-30 | 1980-01-22 | Ppg Industries Inc | Manufacture of peroxydicarbonates |
| DE3038164A1 (de) * | 1980-10-09 | 1982-05-06 | Peroxid-Chemie GmbH, 8023 Höllriegelskreuth | Verfahren zur kontinuierlichen herstellung von dialkylperoxydicarbonaten |
| US4359427A (en) | 1981-07-27 | 1982-11-16 | The B. F. Goodrich Company | Process for producing peroxydicarbonates |
| JPS5869864A (ja) * | 1981-10-20 | 1983-04-26 | Kayaku Nuurii Kk | パ−オキシジカ−ボネ−ト類の製造方法 |
| JPH0776207B2 (ja) * | 1988-01-29 | 1995-08-16 | 三建化工株式会社 | 新規なフッ素含有ペルオキシジカーボネート |
| JP3165454B2 (ja) * | 1991-02-23 | 2001-05-14 | 化薬アクゾ株式会社 | 有機過酸化物の製造方法 |
| SE9101674L (sv) | 1991-05-31 | 1992-12-01 | Berol Nobel Ab | Dispersion |
| JPH06157629A (ja) * | 1992-07-31 | 1994-06-07 | Geon Co | ビニル単量体を重合する方法 |
| AU713659B2 (en) * | 1995-04-17 | 1999-12-09 | Procter & Gamble Company, The | Preparation and use of composite particles containing diacyl peroxide |
| BE1009969A3 (fr) * | 1996-01-25 | 1997-11-04 | Solvay | Procede pour la polymerisation en suspension aqueuse du chlorure de vinyle a l'intervention de peroxydicarbonates de dialkyle. |
| JPH10338701A (ja) * | 1997-04-08 | 1998-12-22 | Shin Etsu Chem Co Ltd | 塩化ビニル系重合体の製造方法 |
| EP0908450B1 (en) * | 1997-09-24 | 2003-05-07 | Nof Corporation | Novel polyfunctional peroxides, vinyl monomer polymerization initiators comprising the same and process for polymerizing vinyl monomers employing the same |
| US6242562B1 (en) * | 1998-12-28 | 2001-06-05 | Shin-Etsu Chemical Co., Ltd. | Process for producing vinyl chloride polymer |
| US6995221B2 (en) * | 1999-11-04 | 2006-02-07 | Oxy Vinyls, L.P. | Method for producing organic peroxides and their use in the radical polymerization of monomers |
| US6433208B1 (en) * | 1999-11-04 | 2002-08-13 | Oxy Vinyls Lp | Method for producing stable, dilute, aqueous, emulsified peroxydicarbonates by homogenization |
-
1999
- 1999-11-04 US US09/433,907 patent/US6433208B1/en not_active Expired - Lifetime
-
2000
- 2000-11-03 YU YU32602A patent/YU32602A/sh unknown
- 2000-11-03 EP EP00973042A patent/EP1226118B1/en not_active Expired - Lifetime
- 2000-11-03 DE DE60008012T patent/DE60008012T2/de not_active Expired - Lifetime
- 2000-11-03 PL PL354581A patent/PL202098B1/pl unknown
- 2000-11-03 JP JP2001534766A patent/JP5031962B2/ja not_active Expired - Lifetime
- 2000-11-03 CA CA002389728A patent/CA2389728C/en not_active Expired - Lifetime
- 2000-11-03 IL IL14933200A patent/IL149332A0/xx active IP Right Grant
- 2000-11-03 AT AT00973042T patent/ATE258546T1/de active
- 2000-11-03 KR KR1020027005722A patent/KR100732660B1/ko not_active IP Right Cessation
- 2000-11-03 PT PT00973042T patent/PT1226118E/pt unknown
- 2000-11-03 HU HU0203775A patent/HU228803B1/hu not_active IP Right Cessation
- 2000-11-03 WO PCT/GB2000/004230 patent/WO2001032613A1/en active IP Right Grant
- 2000-11-03 ES ES00973042T patent/ES2215078T3/es not_active Expired - Lifetime
- 2000-11-03 CZ CZ20021527A patent/CZ302981B6/cs not_active IP Right Cessation
- 2000-11-03 CN CN00815360A patent/CN1387511A/zh active Pending
- 2000-11-03 MX MXPA02003996A patent/MXPA02003996A/es active IP Right Grant
- 2000-11-03 DK DK00973042T patent/DK1226118T3/da active
-
2002
- 2002-04-24 IL IL149332A patent/IL149332A/en not_active IP Right Cessation
- 2002-04-24 NO NO20021934A patent/NO327596B1/no not_active IP Right Cessation
- 2002-04-25 US US10/132,582 patent/US6770719B2/en not_active Expired - Lifetime
-
2004
- 2004-05-18 US US10/847,954 patent/US7763690B2/en not_active Expired - Fee Related
-
2011
- 2011-09-16 JP JP2011203038A patent/JP5581288B2/ja not_active Expired - Lifetime
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