JPS6154321B2 - - Google Patents
Info
- Publication number
- JPS6154321B2 JPS6154321B2 JP57184789A JP18478982A JPS6154321B2 JP S6154321 B2 JPS6154321 B2 JP S6154321B2 JP 57184789 A JP57184789 A JP 57184789A JP 18478982 A JP18478982 A JP 18478982A JP S6154321 B2 JPS6154321 B2 JP S6154321B2
- Authority
- JP
- Japan
- Prior art keywords
- bisulfite
- ketone
- reducing agent
- polymerization
- acetone
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 transition metal salt Chemical class 0.000 claims description 60
- 239000003638 chemical reducing agent Substances 0.000 claims description 48
- 238000006116 polymerization reaction Methods 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 25
- 239000000178 monomer Substances 0.000 claims description 21
- 239000007800 oxidant agent Substances 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 18
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- VSVCAMGKPRPGQR-UHFFFAOYSA-N propan-2-one;sulfurous acid Chemical group CC(C)=O.OS(O)=O VSVCAMGKPRPGQR-UHFFFAOYSA-N 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 12
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 11
- 239000005977 Ethylene Substances 0.000 claims description 11
- 150000002576 ketones Chemical class 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 9
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
- 229920002554 vinyl polymer Polymers 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 7
- 239000004816 latex Substances 0.000 claims description 5
- 229920000126 latex Polymers 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- 229910052723 transition metal Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000003381 stabilizer Substances 0.000 claims description 3
- 150000003624 transition metals Chemical class 0.000 claims description 3
- PWTKMURTWDVLCE-UHFFFAOYSA-N 3-oxobutanoic acid;sulfurous acid Chemical group OS(O)=O.CC(=O)CC(O)=O PWTKMURTWDVLCE-UHFFFAOYSA-N 0.000 claims 1
- PXKPKQCNEHVTMN-UHFFFAOYSA-N butan-2-one;sulfurous acid Chemical group OS(O)=O.CCC(C)=O PXKPKQCNEHVTMN-UHFFFAOYSA-N 0.000 claims 1
- QPFVCZRPJLXDJI-UHFFFAOYSA-N cyclohexanone;sulfurous acid Chemical group OS(O)=O.O=C1CCCCC1 QPFVCZRPJLXDJI-UHFFFAOYSA-N 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 23
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 23
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 19
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 15
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 14
- 239000000839 emulsion Substances 0.000 description 13
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 10
- 239000012153 distilled water Substances 0.000 description 9
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 230000009849 deactivation Effects 0.000 description 6
- HDERJYVLTPVNRI-UHFFFAOYSA-N ethene;ethenyl acetate Chemical group C=C.CC(=O)OC=C HDERJYVLTPVNRI-UHFFFAOYSA-N 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 238000007720 emulsion polymerization reaction Methods 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000012190 activator Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000003111 delayed effect Effects 0.000 description 3
- HRKQOINLCJTGBK-UHFFFAOYSA-L dioxidosulfate(2-) Chemical compound [O-]S[O-] HRKQOINLCJTGBK-UHFFFAOYSA-L 0.000 description 3
- BXUKAXFDABMVND-UHFFFAOYSA-L disodium;1,2-dihydroxyethane-1,2-disulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C(O)C(O)S([O-])(=O)=O BXUKAXFDABMVND-UHFFFAOYSA-L 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229920001038 ethylene copolymer Polymers 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical class C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical class OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000005038 ethylene vinyl acetate Substances 0.000 description 2
- 229940017705 formaldehyde sulfoxylate Drugs 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- SBGKURINHGJRFN-UHFFFAOYSA-N hydroxymethanesulfinic acid Chemical compound OCS(O)=O SBGKURINHGJRFN-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- SURQXAFEQWPFPV-UHFFFAOYSA-L iron(2+) sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Fe+2].[O-]S([O-])(=O)=O SURQXAFEQWPFPV-UHFFFAOYSA-L 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 2
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 2
- 239000012966 redox initiator Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- YNJORDSKPXMABC-UHFFFAOYSA-M sodium;2-hydroxypropane-2-sulfonate Chemical compound [Na+].CC(C)(O)S([O-])(=O)=O YNJORDSKPXMABC-UHFFFAOYSA-M 0.000 description 2
- 150000004764 thiosulfuric acid derivatives Chemical class 0.000 description 2
- CAAIULQYGCAMCD-UHFFFAOYSA-L zinc;hydroxymethanesulfinate Chemical compound [Zn+2].OCS([O-])=O.OCS([O-])=O CAAIULQYGCAMCD-UHFFFAOYSA-L 0.000 description 2
- ORJDWQVKIMZEMX-UHFFFAOYSA-N (2-nonylphenyl) hydrogen sulfate Chemical class CCCCCCCCCC1=CC=CC=C1OS(O)(=O)=O ORJDWQVKIMZEMX-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
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-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
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 239000004908 Emulsion polymer Substances 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- FEFXDRKSKRDAIN-UHFFFAOYSA-N S(O)(O)=O.CC(=O)C.S(O)O.CC(=O)C Chemical compound S(O)(O)=O.CC(=O)C.S(O)O.CC(=O)C FEFXDRKSKRDAIN-UHFFFAOYSA-N 0.000 description 1
- ZQRIKJMJOWMJGA-UHFFFAOYSA-L S([O-])[O-].CC(=O)C.[Na+].[Na+] Chemical compound S([O-])[O-].CC(=O)C.[Na+].[Na+] ZQRIKJMJOWMJGA-UHFFFAOYSA-L 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000003513 alkali Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-M chlorate Inorganic materials [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- SPTHWAJJMLCAQF-UHFFFAOYSA-M ctk4f8481 Chemical compound [O-]O.CC(C)C1=CC=CC=C1C(C)C SPTHWAJJMLCAQF-UHFFFAOYSA-M 0.000 description 1
- 150000003997 cyclic ketones Chemical class 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- NVJBFARDFTXOTO-UHFFFAOYSA-N diethyl sulfite Chemical compound CCOS(=O)OCC NVJBFARDFTXOTO-UHFFFAOYSA-N 0.000 description 1
- BDUPRNVPXOHWIL-UHFFFAOYSA-N dimethyl sulfite Chemical compound COS(=O)OC BDUPRNVPXOHWIL-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- IMBKASBLAKCLEM-UHFFFAOYSA-L ferrous ammonium sulfate (anhydrous) Chemical compound [NH4+].[NH4+].[Fe+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O IMBKASBLAKCLEM-UHFFFAOYSA-L 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical class O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- WARQUFORVQESFF-UHFFFAOYSA-N isocyanatoethene Chemical compound C=CN=C=O WARQUFORVQESFF-UHFFFAOYSA-N 0.000 description 1
- 239000012035 limiting reagent Substances 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
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical compound NCO XMYQHJDBLRZMLW-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
- 239000003607 modifier Substances 0.000 description 1
- UTSYWKJYFPPRAP-UHFFFAOYSA-N n-(butoxymethyl)prop-2-enamide Chemical compound CCCCOCNC(=O)C=C UTSYWKJYFPPRAP-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000002081 peroxide group Chemical group 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229940099427 potassium bisulfite Drugs 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- ZZMDMGNQUXYKQX-UHFFFAOYSA-L sodium;1-nonyl-2-(2-nonylphenoxy)benzene;sulfate Chemical compound [Na+].[O-]S([O-])(=O)=O.CCCCCCCCCC1=CC=CC=C1OC1=CC=CC=C1CCCCCCCCC ZZMDMGNQUXYKQX-UHFFFAOYSA-L 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000035892 strand transfer Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical class S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- 229910052815 sulfur oxide Inorganic materials 0.000 description 1
- 235000010269 sulphur dioxide Nutrition 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 150000003751 zinc Chemical class 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
- C08F4/40—Redox systems
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymerization Catalysts (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/314,318 US4360632A (en) | 1981-10-23 | 1981-10-23 | Ketone bisulfites as reducing agent for free radical polymerization |
| US314318 | 1981-10-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5880302A JPS5880302A (ja) | 1983-05-14 |
| JPS6154321B2 true JPS6154321B2 (enExample) | 1986-11-21 |
Family
ID=23219484
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57184789A Granted JPS5880302A (ja) | 1981-10-23 | 1982-10-22 | 遊離ラジカル重合用還元剤としてのケトンビサルフアイト |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4360632A (enExample) |
| JP (1) | JPS5880302A (enExample) |
| DE (1) | DE3239212C2 (enExample) |
| FR (1) | FR2515189B1 (enExample) |
| GB (1) | GB2108980B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020139276A3 (en) * | 2018-12-25 | 2020-08-13 | Tofas Turk Otomobil Fabrikasi Anonim Sirketi | A vehicle door having door plastic glass channel with lock engagement |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3834734A1 (de) * | 1988-10-12 | 1990-04-19 | Basf Ag | Verfahren zur herstellung von polymerisaten aus olefinisch ungesaettigten monomeren |
| US5415926A (en) * | 1993-02-25 | 1995-05-16 | National Starch And Chemical Investment Holding Corporation | Process for reducing the free aldehyde content in N-alkylol amide monomers |
| CN1120180C (zh) * | 1994-06-03 | 2003-09-03 | 巴斯福股份公司 | 聚合物水分散液的制备 |
| IT1276816B1 (it) | 1995-10-04 | 1997-11-03 | Atochem Elf Italia | Emulsione a basso voc |
| EP0771912B1 (en) * | 1995-11-02 | 2002-09-18 | Atofina | Antifragmentation plates of polymethylmethacrylate |
| DE19545609A1 (de) | 1995-12-07 | 1997-06-12 | Hoechst Ag | Redoxkatalysatorsystem zur Initiierung von Emulsionspolymerisationen |
| DE19741187A1 (de) | 1997-09-18 | 1999-03-25 | Basf Ag | Verfahren zur Verminderung des Restmonomerengehalts in wässrigen Polymerdispersionen |
| US6391992B1 (en) | 1998-09-18 | 2002-05-21 | Celanese International Corporation | Sulfonate-terminated oligomers of vinyl esters and their vinyl alcohol oligomer derivatives |
| US6787594B1 (en) * | 2000-10-30 | 2004-09-07 | Air Products Polymers, L.P. | Reduced formaldehyde nonwoven binders which contain polymerized units of N-methylolacrylamide |
| US8292863B2 (en) | 2009-10-21 | 2012-10-23 | Donoho Christopher D | Disposable diaper with pouches |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2383055A (en) * | 1941-03-28 | 1945-08-21 | Goodrich Co B F | Polymerization of conjugated dienes |
| CH251650A (de) * | 1945-02-09 | 1947-11-15 | Du Pont | Verfahren zur Polymerisation von Monoäthylenverbindungen. |
| US2560694A (en) * | 1950-07-15 | 1951-07-17 | Du Pont | Bromate ion-sulfoxy compound catalyst system in aqueous polymerization process |
| US2716107A (en) * | 1953-03-30 | 1955-08-23 | Us Rubber Co | Synthetic rubber emulsion polymerizations in the presence of an aldehyde or ketone sulfoxylate |
| US3637626A (en) * | 1968-04-03 | 1972-01-25 | Chatillon Italiana Fibre | Process for the polymerization of vinyl chloride |
| US3700456A (en) * | 1970-10-22 | 1972-10-24 | Eastman Kodak Co | Synthetic polymeric photographic emulsion vehicles |
| DE2456576C3 (de) * | 1974-11-29 | 1983-03-10 | Wacker-Chemie GmbH, 8000 München | Verfahren zur kontinuierlichen Herstellung von Äthylen-Vinylacetat-Copolymerdispersionen |
| JPS588410B2 (ja) * | 1975-11-04 | 1983-02-16 | 住友化学工業株式会社 | スイセイブンサンエキノ セイゾウホウホウ |
-
1981
- 1981-10-23 US US06/314,318 patent/US4360632A/en not_active Expired - Lifetime
-
1982
- 1982-10-22 JP JP57184789A patent/JPS5880302A/ja active Granted
- 1982-10-22 FR FR8217716A patent/FR2515189B1/fr not_active Expired
- 1982-10-22 DE DE3239212A patent/DE3239212C2/de not_active Expired
- 1982-10-22 GB GB08230207A patent/GB2108980B/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020139276A3 (en) * | 2018-12-25 | 2020-08-13 | Tofas Turk Otomobil Fabrikasi Anonim Sirketi | A vehicle door having door plastic glass channel with lock engagement |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2515189B1 (fr) | 1986-08-29 |
| GB2108980A (en) | 1983-05-25 |
| US4360632A (en) | 1982-11-23 |
| FR2515189A1 (fr) | 1983-04-29 |
| GB2108980B (en) | 1985-05-01 |
| DE3239212A1 (de) | 1983-05-26 |
| DE3239212C2 (de) | 1984-03-01 |
| JPS5880302A (ja) | 1983-05-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6444760B1 (en) | Method of reducing the content of residual monomers in aqueous polymer dispersions | |
| US4528315A (en) | Process for the preparation of polymer dispersions and their application | |
| JPS6154321B2 (enExample) | ||
| US4628071A (en) | Emulsion copolymerization process | |
| CA2201168A1 (en) | Process for preparing an aqueous polymer dispersion | |
| US4661557A (en) | Preparation of stable aqueous polymer dispersions which contain an alkenyl-aromatic compound as copolymerized units | |
| JPH0250923B2 (enExample) | ||
| US4331577A (en) | Latex polymerization process | |
| KR100249052B1 (ko) | 충분히가수분해된폴리(비닐알코올)존재하에제조되는아크릴계에멀션 | |
| EP0071116B1 (en) | Suspension polymerization with cosolvent partitioning | |
| GB940366A (en) | Process for preparing a freeze-thaw stable acrylate latex | |
| US5453485A (en) | Process for reducing the residual monomer content in aqueous plastics dispersions based on polyvinyl ester | |
| JPS588410B2 (ja) | スイセイブンサンエキノ セイゾウホウホウ | |
| US3453223A (en) | Process for the preparation of acrylonitrile graft copolymers | |
| JPH0119802B2 (enExample) | ||
| JPH11246629A (ja) | 高固形分エチレン―酢酸ビニルエマルション | |
| US4847341A (en) | Novel polymerization process | |
| JP2004536932A (ja) | 高固形分エチレン−酢酸ビニルラテックス | |
| US3669919A (en) | Polyacrylonitrile process | |
| JPH05320219A (ja) | ポリビニルアルコール系樹脂の製造法 | |
| JP2000256424A (ja) | ポリビニルアルコールを保護安定剤とするアクリルエマルジョンの製造方法およびその組成物 | |
| EP0026490B1 (en) | Latex polymerization process | |
| US3165500A (en) | Process for the production of acrylonitrile polymers | |
| US3697492A (en) | Acrylonitrile polymerization | |
| US3164574A (en) | Acrylonitrile vinylsulfonic acid copolymers |