GB1568445A - Free radical polymerisation of ethylenically unsaturated mnomers - Google Patents
Free radical polymerisation of ethylenically unsaturated mnomers Download PDFInfo
- Publication number
- GB1568445A GB1568445A GB13447/77A GB1344777A GB1568445A GB 1568445 A GB1568445 A GB 1568445A GB 13447/77 A GB13447/77 A GB 13447/77A GB 1344777 A GB1344777 A GB 1344777A GB 1568445 A GB1568445 A GB 1568445A
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- GB
- United Kingdom
- Prior art keywords
- acid
- solution
- water
- salt
- compound
- Prior art date
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- Expired
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- 150000003254 radicals Chemical class 0.000 title claims description 19
- 239000000243 solution Substances 0.000 claims description 59
- 239000003999 initiator Substances 0.000 claims description 55
- 239000000178 monomer Substances 0.000 claims description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 38
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 28
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 18
- -1 -alkoxy Chemical group 0.000 claims description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 14
- 238000010992 reflux Methods 0.000 claims description 14
- 239000000523 sample Substances 0.000 claims description 14
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- NPKSPKHJBVJUKB-UHFFFAOYSA-N N-phenylglycine Chemical compound OC(=O)CNC1=CC=CC=C1 NPKSPKHJBVJUKB-UHFFFAOYSA-N 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 8
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 8
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 8
- ZXEYBCPCSGTHNM-UHFFFAOYSA-N acetic acid;4-methylaniline Chemical compound CC(O)=O.CC(O)=O.CC1=CC=C(N)C=C1 ZXEYBCPCSGTHNM-UHFFFAOYSA-N 0.000 claims description 8
- 230000000977 initiatory effect Effects 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 239000011780 sodium chloride Substances 0.000 claims description 7
- 159000000000 sodium salts Chemical class 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 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 claims description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 claims description 6
- 239000002244 precipitate Substances 0.000 claims description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 239000011521 glass Substances 0.000 claims description 5
- 238000005286 illumination Methods 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 5
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 4
- 238000001879 gelation Methods 0.000 claims description 4
- 230000020477 pH reduction Effects 0.000 claims description 4
- 229920002401 polyacrylamide Polymers 0.000 claims description 4
- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 claims description 3
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims description 3
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 claims description 3
- KZVOCQVRCSRWCQ-UHFFFAOYSA-N 2-[4-butyl-n-(carboxymethyl)anilino]acetic acid Chemical compound CCCCC1=CC=C(N(CC(O)=O)CC(O)=O)C=C1 KZVOCQVRCSRWCQ-UHFFFAOYSA-N 0.000 claims description 3
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 3
- OGKCEFPDNBSRSV-UHFFFAOYSA-N methyl 2-(n-(2-methoxy-2-oxoethyl)-4-methylanilino)acetate Chemical compound COC(=O)CN(CC(=O)OC)C1=CC=C(C)C=C1 OGKCEFPDNBSRSV-UHFFFAOYSA-N 0.000 claims description 3
- 150000004702 methyl esters Chemical class 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 claims description 2
- GMDJMLOOHULQEV-UHFFFAOYSA-N 2-(n-ethylanilino)acetic acid Chemical compound OC(=O)CN(CC)C1=CC=CC=C1 GMDJMLOOHULQEV-UHFFFAOYSA-N 0.000 claims description 2
- MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 claims description 2
- QWFVBTNOBWBCFH-UHFFFAOYSA-N 2-[n-(carboxymethyl)-4-methylanilino]acetic acid Chemical compound CC1=CC=C(N(CC(O)=O)CC(O)=O)C=C1 QWFVBTNOBWBCFH-UHFFFAOYSA-N 0.000 claims description 2
- GQBWTAGIANQVGB-UHFFFAOYSA-N 2-[n-(carboxymethyl)anilino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)C1=CC=CC=C1 GQBWTAGIANQVGB-UHFFFAOYSA-N 0.000 claims description 2
- OGIQUQKNJJTLSZ-UHFFFAOYSA-N 4-butylaniline Chemical compound CCCCC1=CC=C(N)C=C1 OGIQUQKNJJTLSZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000008346 aqueous phase Substances 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 238000010790 dilution Methods 0.000 claims description 2
- 239000012895 dilution Substances 0.000 claims description 2
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 239000002585 base Substances 0.000 claims 3
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 239000013068 control sample Substances 0.000 claims 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 2
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- POCFBDFTJMJWLG-UHFFFAOYSA-N dihydrosinapic acid methyl ester Natural products COC(=O)CCC1=CC(OC)=C(O)C(OC)=C1 POCFBDFTJMJWLG-UHFFFAOYSA-N 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- 238000010979 pH adjustment Methods 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 238000010526 radical polymerization reaction Methods 0.000 description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- BDDLHHRCDSJVKV-UHFFFAOYSA-N 7028-40-2 Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O BDDLHHRCDSJVKV-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- 229940048053 acrylate Drugs 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 229940116441 divinylbenzene Drugs 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- ZGHFDIIVVIFNPS-UHFFFAOYSA-N 3-Methyl-3-buten-2-one Chemical compound CC(=C)C(C)=O ZGHFDIIVVIFNPS-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- SRSIOYSKLXAFHK-UHFFFAOYSA-N acetic acid;4-butylaniline Chemical compound CC(O)=O.CC(O)=O.CCCCC1=CC=C(N)C=C1 SRSIOYSKLXAFHK-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012457 nonaqueous media Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229920001897 terpolymer Polymers 0.000 description 2
- 229920001567 vinyl ester resin Polymers 0.000 description 2
- LAJWBKLWYSLRLM-UHFFFAOYSA-N (4-methylphenyl)azanium;acetate Chemical compound CC(O)=O.CC1=CC=C(N)C=C1 LAJWBKLWYSLRLM-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- PQUXFUBNSYCQAL-UHFFFAOYSA-N 1-(2,3-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1F PQUXFUBNSYCQAL-UHFFFAOYSA-N 0.000 description 1
- VZUXYAAGABUBPZ-UHFFFAOYSA-N 1-ethenyl-1H-indene hydrochloride Chemical compound Cl.C1=CC=C2C(C=C)C=CC2=C1 VZUXYAAGABUBPZ-UHFFFAOYSA-N 0.000 description 1
- HNXMKNMCALMEPP-UHFFFAOYSA-N 1-ethenylsulfinylethane Chemical compound CCS(=O)C=C HNXMKNMCALMEPP-UHFFFAOYSA-N 0.000 description 1
- ZPQFAVDVWVKUOJ-UHFFFAOYSA-N 1-ethenylsulfonylbutane Chemical compound CCCCS(=O)(=O)C=C ZPQFAVDVWVKUOJ-UHFFFAOYSA-N 0.000 description 1
- RKYJPYDJNQXILT-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxycarbonyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)OCCOC(=O)C=C RKYJPYDJNQXILT-UHFFFAOYSA-N 0.000 description 1
- FWALJUXKWWBNEO-UHFFFAOYSA-N 2-(4-chloroanilino)acetic acid Chemical compound OC(=O)CNC1=CC=C(Cl)C=C1 FWALJUXKWWBNEO-UHFFFAOYSA-N 0.000 description 1
- TUIOBJXCHIWUJY-UHFFFAOYSA-N 2-(4-phenylphenyl)iminoacetic acid Chemical compound C1(=CC=C(C=C1)N=CC(=O)O)C1=CC=CC=C1 TUIOBJXCHIWUJY-UHFFFAOYSA-N 0.000 description 1
- FBAUCMKMNKVWFW-UHFFFAOYSA-N 2-[(4-tert-butylphenyl)azaniumyl]acetate Chemical compound CC(C)(C)C1=CC=C([NH2+]CC([O-])=O)C=C1 FBAUCMKMNKVWFW-UHFFFAOYSA-N 0.000 description 1
- YROBTZHPVSYLJJ-UHFFFAOYSA-N 2-[4-benzyl-n-(carboxymethyl)anilino]acetic acid Chemical compound C1=CC(N(CC(O)=O)CC(=O)O)=CC=C1CC1=CC=CC=C1 YROBTZHPVSYLJJ-UHFFFAOYSA-N 0.000 description 1
- ITTNNPDTZIPTIN-UHFFFAOYSA-N 2-[N-(carboxymethyl)-2,4-diethylanilino]acetic acid Chemical compound C(C)C1=C(N(CC(=O)O)CC(=O)O)C=CC(=C1)CC ITTNNPDTZIPTIN-UHFFFAOYSA-N 0.000 description 1
- SLLJUCNVXFCPSR-UHFFFAOYSA-N 2-[carboxymethyl(naphthalen-1-yl)amino]acetic acid Chemical compound C1=CC=C2C(N(CC(O)=O)CC(=O)O)=CC=CC2=C1 SLLJUCNVXFCPSR-UHFFFAOYSA-N 0.000 description 1
- BIFSQUDZXUVCRE-UHFFFAOYSA-N 2-[carboxymethyl(naphthalen-2-yl)amino]acetic acid Chemical compound C1=CC=CC2=CC(N(CC(O)=O)CC(=O)O)=CC=C21 BIFSQUDZXUVCRE-UHFFFAOYSA-N 0.000 description 1
- GMSDQQKCMMYISK-UHFFFAOYSA-N 2-[n-(carboxymethyl)-2,4-dimethoxyanilino]acetic acid Chemical compound COC1=CC=C(N(CC(O)=O)CC(O)=O)C(OC)=C1 GMSDQQKCMMYISK-UHFFFAOYSA-N 0.000 description 1
- KBTIEFNBFDDQIC-UHFFFAOYSA-N 2-[n-(carboxymethyl)-2,4-dimethylanilino]acetic acid Chemical compound CC1=CC=C(N(CC(O)=O)CC(O)=O)C(C)=C1 KBTIEFNBFDDQIC-UHFFFAOYSA-N 0.000 description 1
- WMBYHFQQLOEIHJ-UHFFFAOYSA-N 2-[n-(carboxymethyl)-4-chloroanilino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)C1=CC=C(Cl)C=C1 WMBYHFQQLOEIHJ-UHFFFAOYSA-N 0.000 description 1
- CTYYYHKWHMXUNB-UHFFFAOYSA-N 2-[n-(carboxymethyl)-4-hydroxyanilino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)C1=CC=C(O)C=C1 CTYYYHKWHMXUNB-UHFFFAOYSA-N 0.000 description 1
- HYKNZBZFSXYENS-UHFFFAOYSA-N 2-anilinoacetic acid Chemical compound OC(=O)CNC1=CC=CC=C1.OC(=O)CNC1=CC=CC=C1 HYKNZBZFSXYENS-UHFFFAOYSA-N 0.000 description 1
- OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 1
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- QGIAGMJBLZRSJH-UHFFFAOYSA-N 2-naphthalen-1-yliminoacetic acid Chemical compound OC(=O)C=NC1=CC=CC2=CC=CC=C12 QGIAGMJBLZRSJH-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- BUPLCMMXKFWTTA-UHFFFAOYSA-N 4-methylidene-1,3-dioxetan-2-one Chemical compound C=C1OC(=O)O1 BUPLCMMXKFWTTA-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- WRUZLCLJULHLEY-UHFFFAOYSA-N N-(p-hydroxyphenyl)glycine Chemical compound OC(=O)CNC1=CC=C(O)C=C1 WRUZLCLJULHLEY-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
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- WTHXTWHYLIZJBH-UHFFFAOYSA-N acetic acid;azane Chemical compound N.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O WTHXTWHYLIZJBH-UHFFFAOYSA-N 0.000 description 1
- ZPUKWLNGBYOBGD-UHFFFAOYSA-N acetic acid;benzene-1,3-diamine Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.NC1=CC=CC(N)=C1 ZPUKWLNGBYOBGD-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012986 chain transfer agent Substances 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
- 238000009795 derivation 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
- 229920001971 elastomer Polymers 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- WNMORWGTPVWAIB-UHFFFAOYSA-N ethenyl 2-methylpropanoate Chemical compound CC(C)C(=O)OC=C WNMORWGTPVWAIB-UHFFFAOYSA-N 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005865 ionizing radiation Effects 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-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
- 150000002825 nitriles Chemical class 0.000 description 1
- RPMXALUWKZHYOV-UHFFFAOYSA-N nitroethene Chemical group [O-][N+](=O)C=C RPMXALUWKZHYOV-UHFFFAOYSA-N 0.000 description 1
- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- FHSWXOCOMAVQKE-UHFFFAOYSA-N phenylazanium;acetate Chemical compound CC([O-])=O.[NH3+]C1=CC=CC=C1 FHSWXOCOMAVQKE-UHFFFAOYSA-N 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002028 premature Effects 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
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229940047670 sodium acrylate Drugs 0.000 description 1
- GRONZTPUWOOUFQ-UHFFFAOYSA-M sodium;methanol;hydroxide Chemical compound [OH-].[Na+].OC GRONZTPUWOOUFQ-UHFFFAOYSA-M 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 238000004260 weight control Methods 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
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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerization Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/673,539 US4095019A (en) | 1976-04-05 | 1976-04-05 | Free radical polymerization process utilizing novel initiators |
| US05/673,938 US4058656A (en) | 1976-04-05 | 1976-04-05 | Free radical polymerization process employing substituted amino acetic acid derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1568445A true GB1568445A (en) | 1980-05-29 |
Family
ID=27100962
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB13447/77A Expired GB1568445A (en) | 1976-04-05 | 1977-03-30 | Free radical polymerisation of ethylenically unsaturated mnomers |
Country Status (12)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114292354A (zh) * | 2021-11-01 | 2022-04-08 | 深圳市森若新材科技有限公司 | 一种可应用于空调蓄冷的聚合物相变材料 |
| WO2024107086A1 (en) * | 2022-11-14 | 2024-05-23 | Public Joint Stock Company "Sibur Holding" (Pjsc "Sibur Holding") | Procatalyst for olefin polymerization and use thereof |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04161143A (ja) * | 1990-10-25 | 1992-06-04 | Masahiko Shimizu | 身体運動記録装置 |
| US5324747A (en) * | 1992-07-15 | 1994-06-28 | Hoffmann-La Roche Inc. | N-substituted anilines, inhibitors of phospholipases A2 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3746611A (en) * | 1970-10-21 | 1973-07-17 | Union Carbide Corp | Silyl acyl peroxide and acyl peroxy polysiloxane binders |
-
1977
- 1977-03-30 GB GB13447/77A patent/GB1568445A/en not_active Expired
- 1977-03-30 IT IT48730/77A patent/IT1116418B/it active
- 1977-03-31 AU AU23840/77A patent/AU509532B2/en not_active Expired
- 1977-04-01 DE DE19772715328 patent/DE2715328A1/de active Granted
- 1977-04-01 CA CA275,313A patent/CA1097845A/en not_active Expired
- 1977-04-01 CA CA275,314A patent/CA1097846A/en not_active Expired
- 1977-04-04 MX MX168624A patent/MX150556A/es unknown
- 1977-04-04 BR BR7702112A patent/BR7702112A/pt unknown
- 1977-04-04 SE SE7703931A patent/SE7703931L/xx unknown
- 1977-04-04 NL NL7703677A patent/NL7703677A/xx not_active Application Discontinuation
- 1977-04-05 CH CH428077A patent/CH610912A5/xx not_active IP Right Cessation
- 1977-04-05 FR FR7710315A patent/FR2347384A1/fr active Granted
- 1977-04-05 JP JP3894177A patent/JPS52121086A/ja active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114292354A (zh) * | 2021-11-01 | 2022-04-08 | 深圳市森若新材科技有限公司 | 一种可应用于空调蓄冷的聚合物相变材料 |
| CN114292354B (zh) * | 2021-11-01 | 2023-06-16 | 深圳市森若新材科技有限公司 | 一种可应用于空调蓄冷的聚合物相变材料 |
| WO2024107086A1 (en) * | 2022-11-14 | 2024-05-23 | Public Joint Stock Company "Sibur Holding" (Pjsc "Sibur Holding") | Procatalyst for olefin polymerization and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2347384B1 (enrdf_load_stackoverflow) | 1981-02-13 |
| JPS52121086A (en) | 1977-10-12 |
| NL7703677A (nl) | 1977-10-07 |
| CH610912A5 (en) | 1979-05-15 |
| SE7703931L (sv) | 1977-10-06 |
| MX150556A (es) | 1984-05-30 |
| DE2715328C2 (enrdf_load_stackoverflow) | 1987-08-20 |
| CA1097845A (en) | 1981-03-17 |
| JPS6154802B2 (enrdf_load_stackoverflow) | 1986-11-25 |
| BR7702112A (pt) | 1978-01-10 |
| FR2347384A1 (fr) | 1977-11-04 |
| CA1097846A (en) | 1981-03-17 |
| IT1116418B (it) | 1986-02-10 |
| AU2384077A (en) | 1978-10-05 |
| DE2715328A1 (de) | 1977-10-27 |
| AU509532B2 (en) | 1980-05-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |