JPH01260360A - Packing agent for reverse phase chromatography - Google Patents
Packing agent for reverse phase chromatographyInfo
- Publication number
- JPH01260360A JPH01260360A JP63088155A JP8815588A JPH01260360A JP H01260360 A JPH01260360 A JP H01260360A JP 63088155 A JP63088155 A JP 63088155A JP 8815588 A JP8815588 A JP 8815588A JP H01260360 A JPH01260360 A JP H01260360A
- Authority
- JP
- Japan
- Prior art keywords
- copolymer
- group
- phase chromatography
- reverse phase
- packing agent
- 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.)
- Pending
Links
- 238000004366 reverse phase liquid chromatography Methods 0.000 title claims abstract description 10
- 238000012856 packing Methods 0.000 title claims abstract description 9
- 229920001577 copolymer Polymers 0.000 claims abstract description 36
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 2
- 239000000463 material Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000005846 sugar alcohols Polymers 0.000 claims description 2
- 239000002253 acid Substances 0.000 abstract description 7
- 239000002245 particle Substances 0.000 abstract description 7
- 238000006116 polymerization reaction Methods 0.000 abstract description 6
- 238000001179 sorption measurement Methods 0.000 abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 abstract description 4
- 230000002159 abnormal effect Effects 0.000 abstract description 4
- 239000003513 alkali Substances 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 4
- 238000003756 stirring Methods 0.000 abstract description 4
- 239000003431 cross linking reagent Substances 0.000 abstract description 3
- 229920000642 polymer Polymers 0.000 abstract description 3
- 125000003010 ionic group Chemical group 0.000 abstract description 2
- 229920002554 vinyl polymer Polymers 0.000 abstract description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 238000004140 cleaning Methods 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- -1 vinyl compound Chemical class 0.000 description 14
- 230000014759 maintenance of location Effects 0.000 description 9
- 238000010828 elution Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 125000005372 silanol group Chemical group 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 238000010557 suspension polymerization reaction Methods 0.000 description 3
- 229960000834 vinyl ether Drugs 0.000 description 3
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- UZILCZKGXMQEQR-UHFFFAOYSA-N decyl-Benzene Chemical compound CCCCCCCCCCC1=CC=CC=C1 UZILCZKGXMQEQR-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229910017053 inorganic salt Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- WVAFEFUPWRPQSY-UHFFFAOYSA-N 1,2,3-tris(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1C=C WVAFEFUPWRPQSY-UHFFFAOYSA-N 0.000 description 1
- XDWRKTULOHXYGN-UHFFFAOYSA-N 1,3-bis(ethenoxy)-2,2-bis(ethenoxymethyl)propane Chemical compound C=COCC(COC=C)(COC=C)COC=C XDWRKTULOHXYGN-UHFFFAOYSA-N 0.000 description 1
- LBNXAWYDQUGHGX-UHFFFAOYSA-N 1-Phenylheptane Chemical compound CCCCCCCC1=CC=CC=C1 LBNXAWYDQUGHGX-UHFFFAOYSA-N 0.000 description 1
- PAOHAQSLJSMLAT-UHFFFAOYSA-N 1-butylperoxybutane Chemical compound CCCCOOCCCC PAOHAQSLJSMLAT-UHFFFAOYSA-N 0.000 description 1
- NBJZEUQTGLSUOB-UHFFFAOYSA-N 1-chloro-4-isocyanato-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(N=C=O)=CC=C1Cl NBJZEUQTGLSUOB-UHFFFAOYSA-N 0.000 description 1
- QJJDJWUCRAPCOL-UHFFFAOYSA-N 1-ethenoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOC=C QJJDJWUCRAPCOL-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 101100433727 Caenorhabditis elegans got-1.2 gene Proteins 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 125000002511 behenyl group Chemical group [H]C([*])([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])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])[H] 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 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
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 125000000853 cresyl group Chemical group C1(=CC=C(C=C1)C)* 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 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
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([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
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([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])C([H])([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
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- VXNSQGRKHCZUSU-UHFFFAOYSA-N octylbenzene Chemical compound [CH2]CCCCCCCC1=CC=CC=C1 VXNSQGRKHCZUSU-UHFFFAOYSA-N 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([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])[H] 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DBSDMAPJGHBWAL-UHFFFAOYSA-N penta-1,4-dien-3-ylbenzene Chemical compound C=CC(C=C)C1=CC=CC=C1 DBSDMAPJGHBWAL-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 238000011176 pooling Methods 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004381 surface treatment Methods 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
- 238000010998 test method Methods 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は逆相クロマトグラフィー用充填剤に関し、詳し
くはビニルエーテル系共重合体からなる逆相クロマトグ
ラフィー用高分子充填剤に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a packing material for reversed phase chromatography, and more particularly to a polymer packing material for reversed phase chromatography comprising a vinyl ether copolymer.
液体クロマトグラフィーにおいて、試料の疎水性の度合
による保持の強弱に基づいて分離する逆相クロマトグラ
フィーが行われている。In liquid chromatography, reversed phase chromatography is used to separate samples based on the strength of retention depending on the degree of hydrophobicity of the sample.
一般に、逆相クロマトグラフィーに用いられる充填剤は
、高速かつ高い分離効率を達成させるために、従来より
非極性化したシリカゲル系充填剤が広く利用されてきた
。しかしながら、シリカゲルはもともとアルカリに対し
て加水分解を受けやすく、またシランカップラーなどの
表面処理により非極性化された゛ものは酸による加水分
解を受けやすい欠点があり、逆相クロマトグラフィーに
おける適用ｐＨ範囲は３〜８に限られていた。In general, non-polarized silica gel-based packing materials have been widely used as packing materials for reversed-phase chromatography in order to achieve high speed and high separation efficiency. However, silica gel is inherently susceptible to hydrolysis by alkalis, and silica gels made non-polarized by surface treatments such as silane couplers have the disadvantage of being susceptible to hydrolysis by acids, so the applicable pH range for reversed-phase chromatography is limited. It was limited to 3-8.
また、シリカゲルの非極性化は主にシリカゲル表面のシ
ラ／−ル基の反応性を利用し【行なわれるが、シラノー
ル基をすべて反応させることは難しくて未反応のシラノ
ール基が残存する。この残存シラノール基は逆相クロマ
トグラフィーにとって不都合なイオン吸着やテーリング
現象の原因となっている。Furthermore, non-polarization of silica gel is carried out mainly by utilizing the reactivity of the silanol groups on the surface of the silica gel, but it is difficult to react all of the silanol groups, and unreacted silanol groups remain. These residual silanol groups cause ion adsorption and tailing phenomena, which are disadvantageous for reversed phase chromatography.
これらの欠点を改善するために、従来より有機ポリマー
充填剤の開発が試みられてきたが、満足な結果は得られ
【いない。たとえば、スチレン−ジビニルベンゼン共重
合体やその誘導体では、疎水性が高すぎるために強い吸
着を生じ、また理論段数の低下を防ぐことはできなかっ
た。また、ポリビニルアルコールやポリアクリルアミド
ゲルの部分アルキル化も行なわれているが１反応条件が
難しくて部分アルキル化度も低く、その調節も困難であ
った。In order to improve these drawbacks, attempts have been made to develop organic polymer fillers, but no satisfactory results have been obtained. For example, styrene-divinylbenzene copolymer and its derivatives have too high hydrophobicity, resulting in strong adsorption, and it has not been possible to prevent a decrease in the number of theoretical plates. Furthermore, partial alkylation of polyvinyl alcohol or polyacrylamide gel has been carried out, but the reaction conditions are difficult and the degree of partial alkylation is low, making it difficult to control.
〔発明が解決しよ５とする課題〕
本発明は、上記の欠点を解決するためのもので、化学的
、物理的にも安定で、異常なイオン吸着を起こさない逆
相りｐマドグラフィー用充填剤を提供することを目的と
する。[Problems to be solved by the invention] The present invention is intended to solve the above-mentioned drawbacks, and is aimed at solving the above-mentioned drawbacks. The purpose is to provide fillers.
〔課題を解決するための手段〕
本発明は、〔Ｉ〕式で示される化合物４０〜９−用充填
剤である。[Means for Solving the Problems] The present invention is a filler for compounds 40 to 9- represented by the formula [I].
ＣＨ２＝ＣＨ−（ＩＲ（１）
ＣＨ２＝ＣＨ−（Ｘ）−（ＣＨ＝ＣＨ２）、、 （
Ｅｌ ）ここで、Ｒは炭素数１〜２４の炭化水素基、ｍ
は１〜３の整数、Ｘは酸素原子、芳香族炭化水素基、多
価アルコールの残基または下記（１）式で尽
鼻される基である。CH2=CH-(IR(1) CH2=CH-(X)-(CH=CH2), (
El) Here, R is a hydrocarbon group having 1 to 24 carbon atoms, m
is an integer of 1 to 3, and X is an oxygen atom, an aromatic hydrocarbon group, a residue of a polyhydric alcohol, or a group represented by the following formula (1).
０（ＣＨｚ）、０ （＊ ）〔Ｉ
〕式中ａはＸ〜２２の整数を示す。0 (CHz), 0 (*) [I
] In the formula, a represents an integer from X to 22.
本発明で用いる共重合体は〔Ｉ〕式で示されるビニル系
の化合物と架橋剤として（ＩＩ）式で示される化合物と
を懸濁重合して得られる共重合体である。The copolymer used in the present invention is a copolymer obtained by suspension polymerization of a vinyl compound represented by formula [I] and a compound represented by formula (II) as a crosslinking agent.
（１）式において、Ｒで示される炭素数１ない（−２４
の炭化水素基としては、メチル基、エチル基、アリル基
、プロピル基、イソプルピル基、ブチル基、インブチル
基、ターシャリブチル基、アミル基、イソアミル基、ヘ
キシル基、ヘプチル基、２−、−ｘ−チルヘキシル基、
オクチル基、／ニル基、デシル基、ウンデシル基、ドデ
シル基、トリデシル基、テトラデシル基、ヘキサデシル
基、インヘキサデシル基、オクタデシル基、インオクタ
デシル基、オレイル基、オクチルドデシル基、ベヘニル
基、デシルテトラデシル基、ベンジル基、クレジル基、
ブチルフェニル基、ジブチルフェニル基、オクチルフェ
ニル基、ノニルフェニル基、ドテシルフェニル基、ジオ
クチルフェニル基、ジノニルフェニル嬶、スチレン化フ
ェニル基等があげられろ。In formula (1), the number of carbon atoms represented by R is 1 (-24
Hydrocarbon groups include methyl group, ethyl group, allyl group, propyl group, isopropyl group, butyl group, inbutyl group, tert-butyl group, amyl group, isoamyl group, hexyl group, heptyl group, 2-, -x -tylhexyl group,
Octyl group, /nyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, hexadecyl group, inhexadecyl group, octadecyl group, inoctadecyl group, oleyl group, octyldodecyl group, behenyl group, decyltetradecyl group group, benzyl group, cresyl group,
Examples include butylphenyl group, dibutylphenyl group, octylphenyl group, nonylphenyl group, dotecylphenyl group, dioctylphenyl group, dinonylphenyl group, styrenated phenyl group, and the like.
（ＩＩ）式で示される化合物の代表的な例としては、ジ
ビニルエーテル、ジビニルベンゼン、ジビニルトルエン
、ジビニルエーテル、トリビニルベンゼン、ジビニルメ
タン、ジビニルメタン、グリセリルトリビニルエーテル
、ペンタエリスリトールテトラビニルエーテル等が挙げ
られる。Representative examples of the compound represented by formula (II) include divinyl ether, divinylbenzene, divinyltoluene, divinyl ether, trivinylbenzene, divinylmethane, divinylmethane, glyceryl trivinyl ether, pentaerythritol tetravinyl ether, etc. .
〔■〕式においてＸが（１）式で示される基の場合にａ
が２２以下に限定される理由は、２３以上になると合成
が困難となるためである。[■] In the formula, when X is a group represented by the formula (1), a
The reason why is limited to 22 or less is that when it is 23 or more, synthesis becomes difficult.
共重合体における（１）式及びＣＨ’Ｊ式化合物の比率
が限定されるのは、（ｎ）式化合物が１０グラフイー用
充填剤として好ましくなく、また６０モルチ″を越える
と共重合反応が困難で均一の共重合体粒子が得られない
からである。The reason why the ratio of the formula (1) and CH'J compounds in the copolymer is limited is that the compound of the formula (n) is not preferred as a filler for 10 graphite, and if it exceeds 60 molar ratio, the copolymerization reaction is difficult. This is because uniform copolymer particles cannot be obtained.
共重合方法は、水溶液中においてカルボキシメチルセル
ツース、ポリビニアルコール等を分散安定剤として用い
、懸濁重合を行なう。重合開始剤としてはベンゾイルペ
ルオキシド、ブチルペルオキシド、クミルペルオキシド
等の有機過酸化物、アゾビスイソブチｑ二）リル等のア
ゾ化合物などを用いることができる。In the copolymerization method, suspension polymerization is carried out in an aqueous solution using carboxymethyl cellulose, polyvinyl alcohol, or the like as a dispersion stabilizer. As the polymerization initiator, organic peroxides such as benzoyl peroxide, butyl peroxide, and cumyl peroxide, and azo compounds such as azobisisobutyq-di)lyl can be used.
重合に当た；ては、希釈剤として脂肪族アルコールのｎ
−ブタノール、ｎ−ペンタノール、ｎ−ヘキサノール、
ｎ−へ（タノール、ｎ−才クタノール、ｎ−ノナノール
、ｎ−デカノール、インプロパツール、インブタノール
など、芳香族炭化水素のベンゼン、トルエン、キシレン
ナト、ケトンの３−ペンタノン、２−ペンタノン、２−
ヘキサノン、２−へブタノンなどを加えても良い。During polymerization, an aliphatic alcohol is used as a diluent.
-butanol, n-pentanol, n-hexanol,
n-(tanol, n-old ethanol, n-nonanol, n-decanol, impropatol, imbutanol, etc., aromatic hydrocarbons benzene, toluene, xylenato, ketones 3-pentanone, 2-pentanone, 2-
Hexanone, 2-hebutanone, etc. may be added.
また場合によっては、〔Ｉ〕式および（Ｅｌ）式化合物
等のモノマーがともに溶解しない濃度の。In some cases, the concentration is such that monomers such as compounds of formula [I] and formula (El) are not dissolved together.
たとえば１５〜４０重量係の無機塩を加えてもよい。こ
の無機塩としては、硫酸ナトリウム、硫酸カリウム、塩
化ナトリウム、塩化カリウム、リン醗ナトリウム、リン
酸カリウムなどが挙げられる。For example, 15 to 40 parts by weight of an inorganic salt may be added. Examples of the inorganic salt include sodium sulfate, potassium sulfate, sodium chloride, potassium chloride, sodium phosphate, and potassium phosphate.
重合は一般に温度３０−１００’Ｃで１〜３０時間程度
行なう。Polymerization is generally carried out at a temperature of 30-100'C for about 1-30 hours.
重合の際Ｋ（ｎ）式化合物が架橋剤となって粒状の共■
合体が生成するが、重合時のかき混ぜ速度を変えること
により共重合体の粒度な調節することができる。生成し
た共重合体の粒子はア七ｌ。During polymerization, the K(n) formula compound acts as a crosslinking agent, forming particulate co-organic
Although coalescence is produced, the particle size of the copolymer can be controlled by changing the stirring speed during polymerization. The particles of the copolymer produced are A7L.
ン等により未反応または１１生成物等を洗浄後、さらに
温水で洗浄して製品とされる。After washing unreacted products or products of No. 11 with water, etc., the product is further washed with warm water to obtain a product.
物の極性が七ツマ−の選択および反応組成比によって容
易に制御でき、またイオン性基を持たないので異常なイ
オン吸着をまったく起こさな（・。さらに、酸およびア
ルカリに対して安定であるので、ｐＨが１〜１４の広い
範囲で使用でき、実鹸用分析、工業用精製等に広く利用
できる。The polarity of the substance can be easily controlled by the selection of the 7-mer and the reaction composition ratio, and since it does not have ionic groups, it does not cause any abnormal ion adsorption (・Furthermore, it is stable against acids and alkalis, so It can be used in a wide range of pH from 1 to 14, and can be widely used for analysis of actual soaps, industrial purification, etc.
以下、本発明の実施例について説明する。 Examples of the present invention will be described below.
実施例１（共重合体の製造）
還流冷却器つきの三つロセパラズルフラスコに、１．５
％（Ｗ／Ｗ％）のポリビニルアルコール本合成化学工業
（掬、ゴーセノールＧＨ−２０）の水浴液５００１１／
をとり、攪拌しながら重合開始剤として過酸化ベンゾイ
ル０．６７’を溶解したｎ−オクタデシルビニルエーテ
ル３．８７’（２０モル％）。Example 1 (Production of copolymer) In a three-row parasol flask equipped with a reflux condenser, 1.5
% (W/W%) of polyvinyl alcohol Honsei Kagaku Kogyo (Kiku, Gohsenol GH-20) water bath liquid 50011/
and n-octadecyl vinyl ether 3.87' (20 mol %) in which 0.67' benzoyl peroxide was dissolved as a polymerization initiator while stirring.
ｎ−ブチルビニルエーテル３． ７ ７ （ ５ ０モ
ル係）、およびジビニルベンゼン′Ｌ５７’（３０モル
％）を加え、粒子の大きさを攪拌速度で調節しながら、
７５’Ｃ，３６００ｒｐｍで２４時間懸濁重合を行なっ
た。得られた共重合体粒子は、７セトンでソックスレー
抽出器にかけて６時間抽出したのち、約５０°Ｃの温水
で十分に洗浄して直径約１５μｍの共重合体粒子９．５
１を得た。n-butyl vinyl ether3. 77 (50 mol%) and divinylbenzene 'L57' (30 mol%), and while adjusting the particle size by stirring speed,
Suspension polymerization was carried out at 75'C and 3600 rpm for 24 hours. The obtained copolymer particles were extracted with 7 setson using a Soxhlet extractor for 6 hours, and then thoroughly washed with warm water at about 50°C to obtain copolymer particles with a diameter of about 15 μm.
I got 1.
以下衣１に示す条件により、同様の方法を用いて共重合
体温２〜／１６１３を合成した。なお、合成の際に希釈
剤および無機塩を使用したものくついては表１に記載し
た。A copolymer with a temperature of 2 to 1613 was synthesized using the same method under the conditions shown in Cloth 1 below. Note that Table 1 lists the cases in which diluents and inorganic salts were used during the synthesis.
表１の共重合体Ａ１〜／に９については、いづれも強度
が大きくて均一状態の共重合体が得られたが、比較の共
重合体４１０と／Ｉ６１１については強度が低く、Ａ１
２と／ＶＬ１３については球形の共重合体が得られず、
液体りｐマドグラフィー用充填剤としては不適当であっ
た。For copolymers A1 to /I9 in Table 1, copolymers with high strength and a uniform state were obtained, but comparative copolymers 410 and /I611 had low strength and A1
For 2 and /VL13, spherical copolymers were not obtained,
It was unsuitable as a filler for liquid pomaography.
また共重合体應１〜腐９は各種の溶媒に不溶で、膨潤す
ることもなかった。Further, copolymers 1 to 9 were insoluble in various solvents and did not swell.
実施例２（脂肪族炭化水素類の溶出特性）金属カラム（
１５ｃｔｕ ｘ Ｏ，４ｔｘ ） Ｋ共重合体高１およ
び鷹２をそれぞれ充填して脂肪族炭化水素類の保持容量
（溶出容ｔ／カラム容−１Ｘ１００）を調べ、公知のオ
クタデシル化シリカゲル（ＯＤＳ ）を充填した場合と
比較した結果を図ＩＫ示す。なお、脂肪族炭化水素とし
てはｎ−へキサン、ｎ−オクタン、ｎ−ツカ？？よびｎ
−デカンを用い、溶離液としてはアセトニトリル−水（
８／２（Ｖ／Ｖ））を用いた。 ・
図１から共重合体高１と魔２はＯＤＳと類似した保持挙
動を示して見・ることかわかる。また、ＯＤＳが共重合
体高１と應２の中間の保持挙動を示すことから、本発明
品の極性は２種類のビニルエーテルの組合せにより調整
することができ、市販のＯＤＳと同様な極性をもつ共重
合体も得ることが可能である。Example 2 (Elution characteristics of aliphatic hydrocarbons) Metal column (
15ctu x O, 4tx) K copolymer High 1 and Taka 2 were respectively packed to check the retention capacity of aliphatic hydrocarbons (elution volume t/column volume - 1X100), and the well-known octadecylated silica gel (ODS) was packed. Figure IK shows the results compared to the case where In addition, examples of aliphatic hydrocarbons include n-hexane, n-octane, and n-tuka? ? and n
-Decane was used, and the eluent was acetonitrile-water (
8/2 (V/V)) was used. - From Figure 1, it can be seen that copolymers High 1 and High 2 exhibit retention behavior similar to ODS. Furthermore, since ODS exhibits a retention behavior intermediate between copolymer height 1 and copolymer height 2, the polarity of the product of the present invention can be adjusted by a combination of two types of vinyl ethers, and a copolymer with a polarity similar to that of commercially available ODS can be adjusted. It is also possible to obtain polymers.
実施例３（芳香族炭化水素類の溶出特性）実施例２と同
様にし【共重合体／１６１およびＯＤＳの芳香族炭化水
Ｘ類の保持容量を調べた結果な図２に示す。ここで、芳
香族炭化水素としては、ベンゼン、ｎ−７’チルベンゼ
ン、ｎ−ヘキシルベンゼン、ｎ−ヘプチルベンゼン、ｎ
−オクチルベンゼンおよびｎ−デシルベンゼンを用い、
溶離液としてアセトニトリルー水（８／ ２ （Ｖ／Ｖ
） ）を用いた。Example 3 (Elution characteristics of aromatic hydrocarbons) The retention capacity of aromatic hydrocarbons X of copolymer/161 and ODS was investigated in the same manner as in Example 2. The results are shown in FIG. Here, as aromatic hydrocarbons, benzene, n-7' thylbenzene, n-hexylbenzene, n-heptylbenzene, n-
- using octylbenzene and n-decylbenzene,
Acetonitrile-water (8/2 (V/V
) ) was used.
図２より共重合体／１６１はＯＤＳと同様な保持挙動を
示すことがわかる。It can be seen from FIG. 2 that copolymer/161 exhibits retention behavior similar to ODS.
実施例４（安息香酸エステル類の溶出特性）実施例２と
同様にして調べた安息香酸エステル類（メチル、エチル
、ブチルおよびヘキシルエステル）の保持容量を図３に
示す。溶離液としてはアセトニトリル−水（８／ ２
（ｖ／Ｖ））を用いた。Example 4 (Elution characteristics of benzoic acid esters) The retention capacity of benzoic acid esters (methyl, ethyl, butyl and hexyl esters) investigated in the same manner as in Example 2 is shown in FIG. The eluent was acetonitrile-water (8/2
(v/V)) was used.
図３から共重合体／１６１はＯＤＳと同様な保持挙動を
示すことがわかる。It can be seen from FIG. 3 that copolymer/161 exhibits retention behavior similar to ODS.
実施例５（塩基性物質の溶出特性）
共重合体高１とＯＤＳにおける塩基性物質〔ピリジン、
キノリンおよびベンジルアミン、溶離液アセトニトリル
−水（８／２ （Ｖ／Ｖ）） ）の保持容量を表２に示
す。Example 5 (Elution characteristics of basic substances) Basic substances [pyridine,
The retention capacities of quinoline and benzylamine, eluent acetonitrile-water (8/2 (V/V)) are shown in Table 2.
表２から明らかなように、ＯＤＳでは異常なイオン吸着
を起こす原因となる残存シラノール基が存在するために
、ピリジンとキノリンはかなり多く保持され、溶出ピー
クにもプーリング現象が見られ、またベンジルアミンは
吸着されてしまりで溶出されなかった。これに対して、
共重合体層１は塩基性物質とイオン的な相互作用をする
官能基を持たないためにＯＤＳのような異常な現象は起
こさなかった。As is clear from Table 2, in ODS, due to the presence of residual silanol groups that cause abnormal ion adsorption, a considerable amount of pyridine and quinoline is retained, a pooling phenomenon is also observed in the elution peak, and benzylamine was adsorbed and was not eluted. On the contrary,
Since the copolymer layer 1 does not have a functional group that interacts ionicly with a basic substance, an abnormal phenomenon such as ODS did not occur.
実施例６（耐酸性および耐アルカリ性試験）共重合体層
１の共重合体の耐酸性および耐アルカリ性試験の結果を
表３に示した。この試験方法は、０．ｌＮ−ＮａＯＨお
よび０．ＩＮ−ＨＣノ水溶液に共重合体を浸し、元素分
析により炭素原子の含有率の変化を調べたものである。Example 6 (Acid resistance and alkali resistance test) The results of the acid resistance and alkali resistance test of the copolymer of copolymer layer 1 are shown in Table 3. This test method is 0. 1N-NaOH and 0. The copolymer was immersed in an aqueous solution of IN-HC, and changes in the carbon atom content were investigated by elemental analysis.
共重合体／１６１は、５０日後においてもほとんど炭素
原子の含有率に変化は見られず、耐酸性および耐アルカ
リ性に優れていることが分かる。また、共重合体４２〜
Ａ９についても同様に炭素原子の含有率に変化は見られ
なかった。Copolymer/161 shows almost no change in the carbon atom content even after 50 days, indicating that it has excellent acid resistance and alkali resistance. In addition, copolymer 42-
Similarly, no change was observed in the carbon atom content of A9.
表 ３ 帳）Table 3 book)
芳香族炭化水素類の溶出特性を示した図、図３は安、！
、奎酸エステル類の溶出特性を示した図である。
特許出厘人 日本油脂株式会社
炭化水素類の炭素数
図 １
図 ２Figure 3 shows the elution characteristics of aromatic hydrocarbons.
, is a diagram showing the elution characteristics of chilic acid esters. Patent agent Nippon Oil & Fats Co., Ltd. Carbon number diagram of hydrocarbons 1 Figure 2
Claims (1)
び〔 I 〕式で示される化合物１０〜６０モル％の共重
合体からなる逆相クロマトグラフィー用充填剤。 ＣＨ＿２＝ＣＨ−ＯＲ〔 I 〕 ＣＨ＿２＝ＣＨ−（Ｘ）−〔ＣＨ＝ＣＨ＿２〕＿ｍ〔I
I〕ここで、Ｒは炭素数１〜２４の炭化水素基、ｍは１
〜３の整数、Ｘは酸素原子、芳香族炭化水素基、多価ア
ルコールの残基または下記〔III〕式で示される基であ
る。 Ｏ（ＣＨ＿２）＿ａＯ〔III〕 〔III〕式中ａは２〜２２の整数を示す。[Scope of Claims] 1. A packing material for reverse phase chromatography comprising a copolymer of 40 to 90 mol% of a compound represented by formula [I] and 10 to 60 mol% of a compound represented by formula [I]. CH_2=CH-OR [I] CH_2=CH-(X)-[CH=CH_2]_m[I
I] Here, R is a hydrocarbon group having 1 to 24 carbon atoms, m is 1
The integer of ~3, X is an oxygen atom, an aromatic hydrocarbon group, a residue of a polyhydric alcohol, or a group represented by the following formula [III]. O(CH_2)_aO [III] [III] In the formula, a represents an integer of 2 to 22.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63088155A JPH01260360A (en) | 1988-04-12 | 1988-04-12 | Packing agent for reverse phase chromatography |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63088155A JPH01260360A (en) | 1988-04-12 | 1988-04-12 | Packing agent for reverse phase chromatography |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01260360A true JPH01260360A (en) | 1989-10-17 |
Family
ID=13935035
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63088155A Pending JPH01260360A (en) | 1988-04-12 | 1988-04-12 | Packing agent for reverse phase chromatography |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01260360A (en) |
Cited By (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005531651A (en) * | 2002-05-30 | 2005-10-20 | アメルシャム・バイオサイエンシーズ・アクチボラグ | Macroporous crosslinked polymer particles |
| WO2015084120A1 (en) * | 2013-12-06 | 2015-06-11 | 주식회사 엘지화학 | Monomer and block copolymer |
| US10081698B2 (en) | 2013-12-06 | 2018-09-25 | Lg Chem, Ltd. | Block copolymer |
| US10087276B2 (en) | 2013-12-06 | 2018-10-02 | Lg Chem, Ltd. | Block copolymer |
| US10150832B2 (en) | 2013-12-06 | 2018-12-11 | Lg Chem, Ltd. | Block copolymer |
| US10184021B2 (en) | 2013-12-06 | 2019-01-22 | Lg Chem, Ltd. | Block copolymer |
| US10196475B2 (en) | 2013-12-06 | 2019-02-05 | Lg Chem, Ltd. | Block copolymer |
| US10196474B2 (en) | 2013-12-06 | 2019-02-05 | Lg Chem, Ltd. | Block copolymer |
| US10202480B2 (en) | 2013-12-06 | 2019-02-12 | Lg Chem, Ltd. | Block copolymer |
| US10202481B2 (en) | 2013-12-06 | 2019-02-12 | Lg Chem, Ltd. | Block copolymer |
| US10227436B2 (en) | 2013-12-06 | 2019-03-12 | Lg Chem, Ltd. | Block copolymer |
| US10227437B2 (en) | 2013-12-06 | 2019-03-12 | Lg Chem, Ltd. | Block copolymer |
| US10227438B2 (en) | 2013-12-06 | 2019-03-12 | Lg Chem, Ltd. | Block copolymer |
| US10239980B2 (en) | 2013-12-06 | 2019-03-26 | Lg Chem, Ltd. | Block copolymer |
| US10240035B2 (en) | 2014-09-30 | 2019-03-26 | Lg Chem, Ltd. | Block copolymer |
| US10253130B2 (en) | 2013-12-06 | 2019-04-09 | Lg Chem, Ltd. | Block copolymer |
| US10281820B2 (en) | 2014-09-30 | 2019-05-07 | Lg Chem, Ltd. | Block copolymer |
| US10287429B2 (en) | 2014-09-30 | 2019-05-14 | Lg Chem, Ltd. | Block copolymer |
| US10287430B2 (en) | 2014-09-30 | 2019-05-14 | Lg Chem, Ltd. | Method of manufacturing patterned substrate |
| US10295908B2 (en) | 2014-09-30 | 2019-05-21 | Lg Chem, Ltd. | Block copolymer |
| US10310378B2 (en) | 2014-09-30 | 2019-06-04 | Lg Chem, Ltd. | Block copolymer |
| US10370529B2 (en) | 2014-09-30 | 2019-08-06 | Lg Chem, Ltd. | Method of manufacturing patterned substrate |
| US10377894B2 (en) | 2014-09-30 | 2019-08-13 | Lg Chem, Ltd. | Block copolymer |
| US10633533B2 (en) | 2014-09-30 | 2020-04-28 | Lg Chem, Ltd. | Block copolymer |
| US10703897B2 (en) | 2014-09-30 | 2020-07-07 | Lg Chem, Ltd. | Block copolymer |
-
1988
- 1988-04-12 JP JP63088155A patent/JPH01260360A/en active Pending
Cited By (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005531651A (en) * | 2002-05-30 | 2005-10-20 | アメルシャム・バイオサイエンシーズ・アクチボラグ | Macroporous crosslinked polymer particles |
| US10227436B2 (en) | 2013-12-06 | 2019-03-12 | Lg Chem, Ltd. | Block copolymer |
| US10081698B2 (en) | 2013-12-06 | 2018-09-25 | Lg Chem, Ltd. | Block copolymer |
| US10227438B2 (en) | 2013-12-06 | 2019-03-12 | Lg Chem, Ltd. | Block copolymer |
| US10239980B2 (en) | 2013-12-06 | 2019-03-26 | Lg Chem, Ltd. | Block copolymer |
| US10150832B2 (en) | 2013-12-06 | 2018-12-11 | Lg Chem, Ltd. | Block copolymer |
| US10160822B2 (en) | 2013-12-06 | 2018-12-25 | Lg Chem, Ltd. | Monomer and block copolymer |
| US10184021B2 (en) | 2013-12-06 | 2019-01-22 | Lg Chem, Ltd. | Block copolymer |
| US10196475B2 (en) | 2013-12-06 | 2019-02-05 | Lg Chem, Ltd. | Block copolymer |
| US10196474B2 (en) | 2013-12-06 | 2019-02-05 | Lg Chem, Ltd. | Block copolymer |
| US10202480B2 (en) | 2013-12-06 | 2019-02-12 | Lg Chem, Ltd. | Block copolymer |
| US10202481B2 (en) | 2013-12-06 | 2019-02-12 | Lg Chem, Ltd. | Block copolymer |
| WO2015084120A1 (en) * | 2013-12-06 | 2015-06-11 | 주식회사 엘지화학 | Monomer and block copolymer |
| US10227437B2 (en) | 2013-12-06 | 2019-03-12 | Lg Chem, Ltd. | Block copolymer |
| CN105980342A (en) * | 2013-12-06 | 2016-09-28 | 株式会社Lg化学 | Monomer and block copolymer |
| US10087276B2 (en) | 2013-12-06 | 2018-10-02 | Lg Chem, Ltd. | Block copolymer |
| US10253130B2 (en) | 2013-12-06 | 2019-04-09 | Lg Chem, Ltd. | Block copolymer |
| US10240035B2 (en) | 2014-09-30 | 2019-03-26 | Lg Chem, Ltd. | Block copolymer |
| US10281820B2 (en) | 2014-09-30 | 2019-05-07 | Lg Chem, Ltd. | Block copolymer |
| US10287429B2 (en) | 2014-09-30 | 2019-05-14 | Lg Chem, Ltd. | Block copolymer |
| US10287430B2 (en) | 2014-09-30 | 2019-05-14 | Lg Chem, Ltd. | Method of manufacturing patterned substrate |
| US10295908B2 (en) | 2014-09-30 | 2019-05-21 | Lg Chem, Ltd. | Block copolymer |
| US10310378B2 (en) | 2014-09-30 | 2019-06-04 | Lg Chem, Ltd. | Block copolymer |
| US10370529B2 (en) | 2014-09-30 | 2019-08-06 | Lg Chem, Ltd. | Method of manufacturing patterned substrate |
| US10377894B2 (en) | 2014-09-30 | 2019-08-13 | Lg Chem, Ltd. | Block copolymer |
| US10633533B2 (en) | 2014-09-30 | 2020-04-28 | Lg Chem, Ltd. | Block copolymer |
| US10703897B2 (en) | 2014-09-30 | 2020-07-07 | Lg Chem, Ltd. | Block copolymer |
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