KR20050038012A - 베타-인산화된 니트록시드로부터 유래되는 알콕시아민 및라디칼 중합화에서 그의 용도 - Google Patents
베타-인산화된 니트록시드로부터 유래되는 알콕시아민 및라디칼 중합화에서 그의 용도 Download PDFInfo
- Publication number
- KR20050038012A KR20050038012A KR1020057002339A KR20057002339A KR20050038012A KR 20050038012 A KR20050038012 A KR 20050038012A KR 1020057002339 A KR1020057002339 A KR 1020057002339A KR 20057002339 A KR20057002339 A KR 20057002339A KR 20050038012 A KR20050038012 A KR 20050038012A
- Authority
- KR
- South Korea
- Prior art keywords
- methacrylate
- acrylate
- ethyl
- glycol
- monomers
- Prior art date
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- 125000005262 alkoxyamine group Chemical group 0.000 title claims abstract description 48
- -1 nitroxides Chemical class 0.000 title claims abstract description 46
- 239000000178 monomer Substances 0.000 claims abstract description 48
- 150000001875 compounds Chemical class 0.000 claims abstract description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 25
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 24
- 229920000642 polymer Polymers 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 20
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 16
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 14
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000003999 initiator Substances 0.000 claims description 9
- 229910052708 sodium Inorganic materials 0.000 claims description 9
- 239000011734 sodium Substances 0.000 claims description 9
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 8
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 7
- 229910052744 lithium Inorganic materials 0.000 claims description 7
- 229920001451 polypropylene glycol Polymers 0.000 claims description 7
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 claims description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 6
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 6
- 229920001577 copolymer Polymers 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- UZNHKBFIBYXPDV-UHFFFAOYSA-N trimethyl-[3-(2-methylprop-2-enoylamino)propyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)NCCC[N+](C)(C)C UZNHKBFIBYXPDV-UHFFFAOYSA-N 0.000 claims description 6
- YPAURZBMECSUPE-UHFFFAOYSA-N 1-(2-hydroxyethyl)imidazolidin-2-one;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.OCCN1CCNC1=O YPAURZBMECSUPE-UHFFFAOYSA-N 0.000 claims description 5
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 claims description 5
- LHCFAZQDKKRUDE-UHFFFAOYSA-N 2-[tert-butyl-(1-diethoxyphosphoryl-2,2-dimethylpropyl)amino]oxy-2-methylpropanoic acid Chemical compound CCOP(=O)(OCC)C(C(C)(C)C)N(C(C)(C)C)OC(C)(C)C(O)=O LHCFAZQDKKRUDE-UHFFFAOYSA-N 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 238000010494 dissociation reaction Methods 0.000 claims description 5
- 230000005593 dissociations Effects 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-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
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 150000001993 dienes Chemical class 0.000 claims description 4
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 230000037361 pathway Effects 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 claims description 3
- PFPUZMSQZJFLBK-UHFFFAOYSA-N 2-(2-oxoimidazolidin-1-yl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCN1CCNC1=O PFPUZMSQZJFLBK-UHFFFAOYSA-N 0.000 claims description 3
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 3
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 3
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 claims description 3
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 3
- WIYVVIUBKNTNKG-UHFFFAOYSA-N 6,7-dimethoxy-3,4-dihydronaphthalene-2-carboxylic acid Chemical compound C1CC(C(O)=O)=CC2=C1C=C(OC)C(OC)=C2 WIYVVIUBKNTNKG-UHFFFAOYSA-N 0.000 claims description 3
- NUXLDNTZFXDNBA-UHFFFAOYSA-N 6-bromo-2-methyl-4h-1,4-benzoxazin-3-one Chemical compound C1=C(Br)C=C2NC(=O)C(C)OC2=C1 NUXLDNTZFXDNBA-UHFFFAOYSA-N 0.000 claims description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 3
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 claims description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- 150000003926 acrylamides Chemical class 0.000 claims description 3
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 3
- ZGCZDEVLEULNLJ-UHFFFAOYSA-M benzyl-dimethyl-(2-prop-2-enoyloxyethyl)azanium;chloride Chemical compound [Cl-].C=CC(=O)OCC[N+](C)(C)CC1=CC=CC=C1 ZGCZDEVLEULNLJ-UHFFFAOYSA-M 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- 239000011976 maleic acid Substances 0.000 claims description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 3
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 3
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 claims description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 3
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 claims description 3
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 claims description 3
- MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 claims description 3
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
- RRHXZLALVWBDKH-UHFFFAOYSA-M trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)OCC[N+](C)(C)C RRHXZLALVWBDKH-UHFFFAOYSA-M 0.000 claims description 3
- QTKPMCIBUROOGY-UHFFFAOYSA-N 2,2,2-trifluoroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)F QTKPMCIBUROOGY-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229920001427 mPEG Polymers 0.000 claims description 2
- FZGFBJMPSHGTRQ-UHFFFAOYSA-M trimethyl(2-prop-2-enoyloxyethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCOC(=O)C=C FZGFBJMPSHGTRQ-UHFFFAOYSA-M 0.000 claims description 2
- OEIXGLMQZVLOQX-UHFFFAOYSA-N trimethyl-[3-(prop-2-enoylamino)propyl]azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCCNC(=O)C=C OEIXGLMQZVLOQX-UHFFFAOYSA-N 0.000 claims description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims 6
- 229960000834 vinyl ether Drugs 0.000 claims 4
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims 2
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 claims 2
- SEILKFZTLVMHRR-UHFFFAOYSA-N 2-phosphonooxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOP(O)(O)=O SEILKFZTLVMHRR-UHFFFAOYSA-N 0.000 claims 2
- YFICSDVNKFLZRQ-UHFFFAOYSA-N 3-trimethylsilylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](C)(C)C YFICSDVNKFLZRQ-UHFFFAOYSA-N 0.000 claims 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims 2
- CRGOPMLUWCMMCK-UHFFFAOYSA-M benzyl-dimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)OCC[N+](C)(C)CC1=CC=CC=C1 CRGOPMLUWCMMCK-UHFFFAOYSA-M 0.000 claims 2
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 claims 2
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 claims 2
- 229920001223 polyethylene glycol Polymers 0.000 claims 2
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 claims 2
- HBAIZGPCSAAFSU-UHFFFAOYSA-N 1-(2-hydroxyethyl)imidazolidin-2-one Chemical compound OCCN1CCNC1=O HBAIZGPCSAAFSU-UHFFFAOYSA-N 0.000 claims 1
- 239000002202 Polyethylene glycol Substances 0.000 claims 1
- HPFVBGJFAYZEBE-XNBTXCQYSA-N [(8r,9s,10r,13s,14s)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] 3-cyclopentylpropanoate Chemical compound C([C@H]1[C@H]2[C@@H]([C@]3(CCC(=O)C=C3CC2)C)CC[C@@]11C)CC1OC(=O)CCC1CCCC1 HPFVBGJFAYZEBE-XNBTXCQYSA-N 0.000 claims 1
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 claims 1
- 235000011130 ammonium sulphate Nutrition 0.000 claims 1
- 239000004816 latex Substances 0.000 claims 1
- 229920000126 latex Polymers 0.000 claims 1
- 235000015250 liver sausages Nutrition 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000007334 copolymerization reaction Methods 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- 230000008878 coupling Effects 0.000 description 7
- 238000010168 coupling process Methods 0.000 description 7
- 238000005859 coupling reaction Methods 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 6
- 239000012429 reaction media Substances 0.000 description 6
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 238000010586 diagram Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- 238000010526 radical polymerization reaction Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000007112 amidation reaction Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 2
- 238000004435 EPR spectroscopy Methods 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000009435 amidation Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 230000005291 magnetic effect Effects 0.000 description 2
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- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- DWFKOMDBEKIATP-UHFFFAOYSA-N n'-[2-[2-(dimethylamino)ethyl-methylamino]ethyl]-n,n,n'-trimethylethane-1,2-diamine Chemical compound CN(C)CCN(C)CCN(C)CCN(C)C DWFKOMDBEKIATP-UHFFFAOYSA-N 0.000 description 1
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- 235000021317 phosphate Nutrition 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
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- 238000001394 phosphorus-31 nuclear magnetic resonance spectrum Methods 0.000 description 1
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- 238000002360 preparation method Methods 0.000 description 1
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- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
실시예 7 의 결과 | |||
시간 (시) | Dc M | Mn | PI |
2 | 0.13 | 11 800 | 1.9 |
4 | 0.14 | 12 900 | 1.8 |
21 | 0.16 | 14 800 | 1.7 |
29 | 0.18 | 17 500 | 1.6 |
45 | 0.20 | 19 600 | 1.5 |
69 | 0.22 | 20 700 | 1.4 |
실시예 8 의 결과 | |
시간 (분) | Dc M |
15 | 0.24 |
30 | 0.34 |
45 | 0.39 |
90 | 0.55 |
135 | 0.68 |
탄소 원자No. | δ |
3 및 6 | 60.28-63.32 |
9 | 69.86 |
12 | 63 |
13 | 28.51 |
14 | 36.04 |
15, 21 및 22 | 29.75 |
16 | 63.31 |
17, 23 및 24 | 28.74 |
18 | 24.08 |
19 | 176.70 |
탄소 원자 번호 | δ |
3 및 6 | 61.33 - 61,42 |
4 및 7 | 16.55 - 16.70 |
9 | 71.08 |
12 | 86.36 |
13 및 18 | 24 - 29.10 |
14 | 36.24 |
15, 21 및 22 | 30.23 |
16 | 62.42 |
17, 23 및 24 | 29.27 |
19 | 180.74 |
실시예 2의결과 | ||||||
t (s) | Dc | ln(1/(1-Dc)) | Mn(th) | Mn | Mw | PI |
0 | 0 | 0 | ||||
300 | 0.09 | 0.094 | 63 00 | 5 700 | 10 500 | 1.84 |
1 800 | 0.32 | 0.385 | 22 400 | 23 600 | 31 800 | 1.35 |
3 600 | 0.52 | 0.729 | 36 300 | 35 200 | 44 400 | 1.26 |
6 300 | 0.72 | 1.272 | 50 400 | 44 300 | 56 400 | 1.27 |
Claims (20)
- 하기 화학식 (I)의 알콕시아민:[식 중, R은 탄소수 1 내지 3의 직쇄 또는 분지쇄 알킬 라디칼을 나타내고, R1은 수소 원자 또는 하기 잔기를 나타내며;(식 중, R3는 탄소수 1 내지 20의 직쇄 또는 분지쇄 알킬 라디칼을 나타낸다);R2는 수소 원자, 탄소수 1 내지 8의 직쇄 또는 분지쇄 알킬 라디칼, 페닐 라디칼, Li, Na 또는 K와 같은 알칼리 금속, H4N+, Bu4N+ 또는 Bu3HN+을 나타내고, 단, 화학식 (I)의 알콕시아민 중, R1=H이고, R2가 탄소수 1 내지 6의 직쇄 또는 분지쇄 알킬 라디칼을 나타내는 것은 제외한다].
- 하기 화학식의 2-메틸-2-[N-(t-부틸)-N-(디에톡시포스포릴-2,2-디메틸프로필)아미녹시]프로피온산:
- 하기 화학식의 나트륨 2-메틸-2-[N-(tert-부틸)-N-(디에톡시포스포릴-2,2-디메틸프로필)아미녹시]프로피오네이트:.
- EPR 에 의해 120℃ 에서 측정시 동적 해리 상수 kd 가 0.05 s-1 초과, 바람직하게는 0.1 s-1 초과를 나타내는 하기 화학식 (I) 의 알콕시아민의, 벌크, 용액, 에멀션, 서스펜션 또는 미니에멀션 조건 하에 라디칼 경로를 통해 중합될 수 있는 하나 이상의 단량체의 (공)중합을 위한 개시제로서의 용도:[식 중, R 은 탄소수 1 내지 3 의 직쇄 또는 분지쇄 알킬 라디칼을 나타내며, R1 은 수소 원자 또는 하기의 잔기를 나타내며:(식 중, R3 는 탄소수 1 내지 20 의 직쇄 또는 분지쇄 알킬 라디칼을 나타낸다)R2 는 수소 원자, 탄소수 1 내지 8 의 직쇄 또는 분지쇄 알킬 라디칼, 페닐 라디칼, 알칼리 금속, 예컨대 Li, Na 또는 K, H4N+, Bu4N+ 또는 Bu3HN+ 를 나타낸다].
- 제 4 항에 있어서, R= CH3- 이고, R1 = H 이고, R2 = H, CH3, (CH3)3C, Li 및 Na 인 화학식 (I) 의 알콕시아민의 용도.
- 제 4 항 또는 제 5 항에 있어서, 상기 알콕시아민이 2-메틸-2-[N-(tert-부틸)-N-(디에톡시포스포릴-2,2-디메틸프로필)아미녹시]프로피온산인 용도:.
- 제 4 항 또는 제 5 항에 있어서, 상기 알콕시아민이 메틸 2-메틸-2-[N-(tert-부틸)-N-(디에톡시포스포릴-2,2-디메틸프로필)아미녹시]프로피오네이트인 용도:.
- 제 4 항 내지 제 9 항 중 어느 한 항에 있어서, 라디칼 경로에 의해 중합될 수 있는 단량체(들)가, 비닐방향족 단량체, 예컨대 스티렌, α-메틸스티렌 또는 나트륨 스티렌술포네이트, 디엔, 예컨대 부타디엔 또는 이소프렌, (메트)아크릴 또는 (메트)아크릴레이트 단량체, 예컨대 아크릴산 또는 그의 염, 메틸 아크릴레이트, 에틸 아크릴레이트, 부틸 아크릴레이트, 에틸헥실 아크릴레이트, 페닐 아크릴레이트, 2-히드록시에틸 아크릴레이트, 2-메톡시에틸 아크릴레이트, 메톡시폴리에틸렌 글리콜 아크릴레이트, 에톡시폴리에틸렌 글리콜 아크릴레이트, 메톡시폴리프로필렌 글리콜 아크릴레이트, 메톡시폴리에틸렌 글리콜-폴리프로필렌 글리콜 아크릴레이트 또는 이들의 혼합물, 2-(디메틸아미노)에틸 아크릴레이트 (ADAME), [2-(아크릴로일옥시)에틸]-트리메틸암모늄 클로라이드 또는 설페이트, [2-(아크릴로일옥시)에틸]디메틸벤질암모늄 클로라이드 또는 설페이트, 메타크릴산 또는 그의 염, 메틸 메타크릴레이트, 라우릴 메타크릴레이트, 시클로헥실 메타크릴레이트, 알릴 메타크릴레이트, 페닐 메타크릴레이트, 2-히드록시에틸 메타크릴레이트, 2-히드록시프로필 메타크릴레이트, 2-에톡시에틸 메타크릴레이트, 메톡시폴리에틸렌 글리콜 메타크릴레이트, 에톡시폴리에틸렌 글리콜 메타크릴레이트, 메톡시폴리프로필렌 글리콜 메타크릴레이트, 메톡시폴리에틸렌 글리콜-폴리프로필렌 글리콜 메타크릴레이트 또는 이들의 혼합물, 2-(디메틸아미노)에틸 메타크릴레이트 (MADAME), [2-(메타크릴로일옥시)에틸]트리메틸암모늄 클로라이드 또는 설페이트, [2-(메타크릴로일옥시)에틸]디메틸벤질암모늄 클로라이드 또는 설페이트, 2,2,2-트리플루오로에틸 메타크릴레이트, 3-메타크릴로일옥시프로필트리메틸실란, 에틸렌 글리콜 메타크릴레이트 포스페이트, 히드록시에틸이미다졸리돈 메타크릴레이트, 히드록시에틸이미다졸리디논 메타크릴레이트, 2-(2-옥소-1-이미다졸리디닐)에틸 메타크릴레이트, 아크릴로니트릴, 임의치환된 (메트)아크릴아미드, 예컨대 아크릴아미드, 4-아크릴로일모르폴린, N-메틸롤아크릴아미드, 아크릴아미도프로필트리메틸암모늄 클로라이드 (APTAC), 아크릴아미도메틸프로판술폰산 (AMPS) 또는 그의 염, 메타크릴아미드, N-메틸롤메타크릴아미드 또는 메타크릴아미도프로필트리메틸암모늄 클로라이드 (MAPTAC), 이타콘산, 말레산 또는 그의 염, 말레산 무수물, 비닐피리딘, 비닐피롤리디논, (알콕시)폴리(알킬렌 글리콜)비닐 에테르 또는 디비닐 에테르, 예컨대 메톡시폴리(에틸렌 글리콜) 비닐 에테르 또는 폴리(에틸렌 글리콜)디비닐 에테르, 또는 상기 언급된 단량체의 2 가지 이상의 혼합물로부터 선택되는 것을 특징으로 하는 용도.
- 제 8 항에 있어서, 하나 이상의 단량체가 부틸 아크릴레이트인 것을 특징으로 하는 용도.
- 제 8 항 또는 제 9 항에 있어서, 하나 이상의 단량체가 메틸 메타크릴레이트인 것을 특징으로 하는 용도.
- 제 8 항에 있어서, 단량체의 혼합물이 부틸 아크릴레이트 및 메틸 메타크릴레이트로 이루어지는 것을 특징으로 하는 용도.
- EPR 에 의해 120 ℃ 에서 측정된, 0.05 초-1 초과, 바람직하게는 0.1 s-1 초과의 동적 해리 상수 kd 를 나타내는, 하기 화학식 (I) 의 알콕시아민의 존재 하에 벌크, 용액, 에멀션, 서스펜션 또는 미니에멀션 조건 하에서 라디칼 경로에 의해 중합될 수 있는 하나 이상의 단량체의 (공)중합으로 수득되는 (공)중합체:[식 중 R 은 탄소수 1 내지 3 의 직쇄 또는 분지쇄 알킬 라디칼을 나타내고, R1 은 수소 원자 또는 하기 잔기를 나타내며:(식 중 R3 은 탄소수 1 내지 20 의 직쇄 또는 분지쇄 알킬 라디칼을 나타낸다)R2 는 수소 원자, 탄소수 1 내지 8 의 직쇄 또는 분지쇄 알킬 라디칼, 페닐 라디칼, 알칼리 금속, 예컨대 Li, Na 또는 K, H4N+, Bu4N+ 또는 Bu3HN+ 를 나타낸다].
- 제 12 항에 있어서, 라디칼 경로에 의해 중합될 수 있는 단량체 또는 단량체들이, 비닐방향족 단량체, 예컨대 스티렌, α-메틸스티렌 또는 나트륨 스티렌술포네이트, 디엔, 예컨대 부타디엔 또는 이소프렌, (메트)아크릴 또는 (메트)아크릴레이트 단량체, 예컨대 아크릴산 또는 그의 염, 메틸 아크릴레이트, 에틸 아크릴레이트, 부틸 아크릴레이트, 에틸헥실 아크릴레이트, 페닐 아크릴레이트, 2-히드록시에틸 아크릴레이트, 2-메톡시에틸 아크릴레이트, 메톡시폴리에틸렌 글리콜 아크릴레이트, 에톡시폴리에틸렌 글리콜 아크릴레이트, 메톡시폴리프로필렌 글리콜 아크릴레이트, 메톡시폴리에틸렌 글리콜-폴리프로필렌 글리콜 아크릴레이트 또는 이들의 혼합물, 2-(디메틸아미노)에틸 아크릴레이트 (ADAME), [2-(아크릴로일옥시)에틸]-트리메틸암모늄 클로라이드 또는 설페이트, [2-(아크릴로일옥시)에틸]디메틸벤질암모늄 클로라이드 또는 설페이트, 메타크릴산 또는 그의 염, 메틸 메타크릴레이트, 라우릴 메타크릴레이트, 시클로헥실 메타크릴레이트, 알릴 메타크릴레이트, 페닐 메타크릴레이트, 2-히드록시에틸 메타크릴레이트, 2-히드록시프로필 메타크릴레이트, 2-에톡시에틸 메타크릴레이트, 메톡시폴리에틸렌 글리콜 메타크릴레이트, 에톡시폴리에틸렌 글리콜 메타크릴레이트, 메톡시폴리프로필렌 글리콜 메타크릴레이트, 메톡시폴리에틸렌 글리콜-폴리프로필렌 글리콜 메타크릴레이트 또는 이들의 혼합물, 2-(디메틸아미노)에틸 메타크릴레이트 (MADAME), [2-(메타크릴로일옥시)에틸]트리메틸암모늄 클로라이드 또는 설페이트, [2-(메타크릴로일옥시)에틸]디메틸벤질암모늄 클로라이드 또는 설페이트, 2,2,2-트리플루오로에틸 메타크릴레이트, 3-메타크릴로일옥시프로필트리메틸실란, 에틸렌 글리콜 메타크릴레이트 포스페이트, 히드록시에틸이미다졸리돈 메타크릴레이트, 히드록시에틸이미다졸리디논 메타크릴레이트, 2-(2-옥소-1-이미다졸리디닐)에틸 메타크릴레이트, 아크릴로니트릴, 임의치환된 (메트)아크릴아미드, 예컨대 아크릴아미드, 4-아크릴로일모르폴린, N-메틸롤아크릴아미드, 아크릴아미도프로필트리메틸암모늄 클로라이드 (APTAC), 아크릴아미도메틸프로판술폰산 (AMPS) 또는 그의 염, 메타크릴아미드, N-메틸롤메타크릴아미드 또는 메타크릴아미도프로필트리메틸암모늄 클로라이드 (MAPTAC), 이타콘산, 말레산 또는 그의 염, 말레산 무수물, 비닐피리딘, 비닐피롤리디논 또는 두 개 이상의 상기한 단량체의 혼합물로부터 선택되는 것을 특징으로 하는 (공)중합체.
- 제 13 항에 있어서, 하나 이상의 단량체가 부틸 아크릴레이트인 것을 특징으로 하는 중합체.
- 제 13 항 또는 제 14 항에 있어서, 하나 이상의 단량체가 메틸 아크릴레이트인 것을 특징으로 하는 중합체.
- 제 13 항에 있어서, 단량체의 혼합물이 부틸 아크릴레이트 및 메틸 메타크릴레이트로 이루어지는 것을 특징으로 하는 공중합체.
- 화학적 전환을 실시하기 위한 제 12 항 내지 제 16 항 중 어느 한 항에 따른 (공)중합체의 용도.
- 제 17 항에 있어서, 하기 구조를 갖는 중합체 P2:를 수득하기 위한 하기 구조의 중합체 P1 의 용도:
- 제 17 항에 있어서, 하기 구조를 갖는 중합체 P3:를 수득하기 위한 하기 구조의 중합체 P1 의 용도:
- 제 17 항에 있어서, 하기 구조를 갖는 중합체 P4:를 수득하기 위한 하기 구조의 중합체 P1 의 용도:
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