KR102479521B1 - Composition for manufacturing polymer bead and process for manufacturing polymer bead using same - Google Patents
Composition for manufacturing polymer bead and process for manufacturing polymer bead using same Download PDFInfo
- Publication number
- KR102479521B1 KR102479521B1 KR1020220044652A KR20220044652A KR102479521B1 KR 102479521 B1 KR102479521 B1 KR 102479521B1 KR 1020220044652 A KR1020220044652 A KR 1020220044652A KR 20220044652 A KR20220044652 A KR 20220044652A KR 102479521 B1 KR102479521 B1 KR 102479521B1
- Authority
- KR
- South Korea
- Prior art keywords
- polymer
- weight
- polymer bead
- parts
- bead composition
- Prior art date
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 151
- 239000011324 bead Substances 0.000 title claims abstract description 100
- 239000000203 mixture Substances 0.000 title claims abstract description 65
- 238000000034 method Methods 0.000 title claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 16
- 239000000178 monomer Substances 0.000 claims abstract description 52
- 239000012986 chain transfer agent Substances 0.000 claims abstract description 30
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 23
- -1 methacrylic acid fluoroalkyl ester Chemical class 0.000 claims abstract description 23
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 21
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 18
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000011248 coating agent Substances 0.000 claims abstract description 16
- 239000003431 cross linking reagent Substances 0.000 claims description 28
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 22
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 18
- 238000006116 polymerization reaction Methods 0.000 claims description 17
- 239000002245 particle Substances 0.000 claims description 15
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 12
- 230000000379 polymerizing effect Effects 0.000 claims description 11
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 7
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical group C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000002202 Polyethylene glycol Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229920001223 polyethylene glycol Polymers 0.000 claims description 6
- XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 claims description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 5
- 229910000077 silane Inorganic materials 0.000 claims description 5
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 claims description 4
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 4
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 claims description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 4
- 229920001748 polybutylene Polymers 0.000 claims description 4
- 229920005651 polypropylene glycol dimethacrylate Polymers 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 3
- VDYWHVQKENANGY-UHFFFAOYSA-N 1,3-Butyleneglycol dimethacrylate Chemical compound CC(=C)C(=O)OC(C)CCOC(=O)C(C)=C VDYWHVQKENANGY-UHFFFAOYSA-N 0.000 claims description 2
- KFQPRNVTVMCYEH-UHFFFAOYSA-N 1-amino-3-(4-methoxyphenoxy)propan-2-ol Chemical compound COC1=CC=C(OCC(O)CN)C=C1 KFQPRNVTVMCYEH-UHFFFAOYSA-N 0.000 claims description 2
- OYKPJMYWPYIXGG-UHFFFAOYSA-N 2,2-dimethylbutane;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(C)(C)C OYKPJMYWPYIXGG-UHFFFAOYSA-N 0.000 claims description 2
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 claims description 2
- JJBFVQSGPLGDNX-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)COC(=O)C(C)=C JJBFVQSGPLGDNX-UHFFFAOYSA-N 0.000 claims description 2
- ASZWPJNAVQTHGP-UHFFFAOYSA-N 2-(hydroxymethyl)propane-1,3-diol prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)CO ASZWPJNAVQTHGP-UHFFFAOYSA-N 0.000 claims description 2
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 claims description 2
- ZJCZFAAXZODMQT-UHFFFAOYSA-N 2-methylpentadecane-2-thiol Chemical compound CCCCCCCCCCCCCC(C)(C)S ZJCZFAAXZODMQT-UHFFFAOYSA-N 0.000 claims description 2
- VFZKVQVQOMDJEG-UHFFFAOYSA-N 2-prop-2-enoyloxypropyl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(=O)C=C VFZKVQVQOMDJEG-UHFFFAOYSA-N 0.000 claims description 2
- HTWRFCRQSLVESJ-UHFFFAOYSA-N 3-(2-methylprop-2-enoyloxy)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCOC(=O)C(C)=C HTWRFCRQSLVESJ-UHFFFAOYSA-N 0.000 claims description 2
- FQMIAEWUVYWVNB-UHFFFAOYSA-N 3-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OC(C)CCOC(=O)C=C FQMIAEWUVYWVNB-UHFFFAOYSA-N 0.000 claims description 2
- GFLJTEHFZZNCTR-UHFFFAOYSA-N 3-prop-2-enoyloxypropyl prop-2-enoate Chemical compound C=CC(=O)OCCCOC(=O)C=C GFLJTEHFZZNCTR-UHFFFAOYSA-N 0.000 claims description 2
- SAPGBCWOQLHKKZ-UHFFFAOYSA-N 6-(2-methylprop-2-enoyloxy)hexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCOC(=O)C(C)=C SAPGBCWOQLHKKZ-UHFFFAOYSA-N 0.000 claims description 2
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 claims description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 2
- BVVRPVFKRUVCJX-UHFFFAOYSA-N OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)CO Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)CO BVVRPVFKRUVCJX-UHFFFAOYSA-N 0.000 claims description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- ZPOLOEWJWXZUSP-WAYWQWQTSA-N bis(prop-2-enyl) (z)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C/C(=O)OCC=C ZPOLOEWJWXZUSP-WAYWQWQTSA-N 0.000 claims description 2
- 125000004386 diacrylate group Chemical group 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 2
- 229920005650 polypropylene glycol diacrylate Polymers 0.000 claims description 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 description 2
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 claims description 2
- MZGMQAMKOBOIDR-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCO MZGMQAMKOBOIDR-UHFFFAOYSA-N 0.000 claims 1
- XAMCLRBWHRRBCN-UHFFFAOYSA-N 5-prop-2-enoyloxypentyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCOC(=O)C=C XAMCLRBWHRRBCN-UHFFFAOYSA-N 0.000 claims 1
- WOSHQKYMJRBBMW-UHFFFAOYSA-N C(C=C)(=O)O.C(C(=C)C)(=O)O.C(C(=C)C)(=O)O.C(CCCO)O Chemical compound C(C=C)(=O)O.C(C(=C)C)(=O)O.C(C(=C)C)(=O)O.C(CCCO)O WOSHQKYMJRBBMW-UHFFFAOYSA-N 0.000 claims 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims 1
- PLGOYNXHSRQDOG-UHFFFAOYSA-N OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCCC(CO)(CO)CO Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCCC(CO)(CO)CO PLGOYNXHSRQDOG-UHFFFAOYSA-N 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 abstract description 19
- 239000000126 substance Substances 0.000 abstract description 5
- 239000003999 initiator Substances 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- 238000005979 thermal decomposition reaction Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000003381 stabilizer Substances 0.000 description 8
- 239000004793 Polystyrene Substances 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229920002223 polystyrene Polymers 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000002411 thermogravimetry Methods 0.000 description 7
- QSRJVOOOWGXUDY-UHFFFAOYSA-N 2-[2-[2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoyloxy]ethoxy]ethoxy]ethyl 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C)=CC(CCC(=O)OCCOCCOCCOC(=O)CCC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 QSRJVOOOWGXUDY-UHFFFAOYSA-N 0.000 description 6
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000009826 distribution Methods 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 238000002156 mixing Methods 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- XFTALRAZSCGSKN-UHFFFAOYSA-M sodium;4-ethenylbenzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=C(C=C)C=C1 XFTALRAZSCGSKN-UHFFFAOYSA-M 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- BITHHVVYSMSWAG-KTKRTIGZSA-N (11Z)-icos-11-enoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCC(O)=O BITHHVVYSMSWAG-KTKRTIGZSA-N 0.000 description 2
- KXVFBCSUGDNXQF-DZDBOGACSA-N (2z,4z,6z,8z,10z)-tetracosa-2,4,6,8,10-pentaenoic acid Chemical compound CCCCCCCCCCCCC\C=C/C=C\C=C/C=C\C=C/C(O)=O KXVFBCSUGDNXQF-DZDBOGACSA-N 0.000 description 2
- DQGMPXYVZZCNDQ-KBPWROHVSA-N (8E,10E,12Z)-octadecatrienoic acid Chemical compound CCCCC\C=C/C=C/C=C/CCCCCCC(O)=O DQGMPXYVZZCNDQ-KBPWROHVSA-N 0.000 description 2
- CUXYLFPMQMFGPL-UHFFFAOYSA-N (9Z,11E,13E)-9,11,13-Octadecatrienoic acid Natural products CCCCC=CC=CC=CCCCCCCCC(O)=O CUXYLFPMQMFGPL-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- DQGMPXYVZZCNDQ-UVZPLDOLSA-N Calendinsaeure Natural products CCCCCC=C/C=C/C=C/CCCCCCC(=O)O DQGMPXYVZZCNDQ-UVZPLDOLSA-N 0.000 description 2
- CUXYLFPMQMFGPL-WJTNUVGISA-N Catalpic acid Chemical compound CCCC\C=C/C=C/C=C/CCCCCCCC(O)=O CUXYLFPMQMFGPL-WJTNUVGISA-N 0.000 description 2
- DEQQJCLFURALOA-UHFFFAOYSA-N Heptatriacontanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O DEQQJCLFURALOA-UHFFFAOYSA-N 0.000 description 2
- LRKATBAZQAWAGV-UHFFFAOYSA-N Hexatriacontylic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O LRKATBAZQAWAGV-UHFFFAOYSA-N 0.000 description 2
- AJQRZOBUACOSBG-UHFFFAOYSA-N Octatriacontanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O AJQRZOBUACOSBG-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- HQRWEDFDJHDPJC-UHFFFAOYSA-N Psyllic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O HQRWEDFDJHDPJC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 2
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 description 2
- XMHIUKTWLZUKEX-UHFFFAOYSA-N hexacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O XMHIUKTWLZUKEX-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- ISYWECDDZWTKFF-UHFFFAOYSA-N nonadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCCC(O)=O ISYWECDDZWTKFF-UHFFFAOYSA-N 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- UTOPWMOLSKOLTQ-UHFFFAOYSA-N octacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTOPWMOLSKOLTQ-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
- IJTNSXPMYKJZPR-UHFFFAOYSA-N parinaric acid Chemical compound CCC=CC=CC=CC=CCCCCCCCC(O)=O IJTNSXPMYKJZPR-UHFFFAOYSA-N 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- VHOCUJPBKOZGJD-UHFFFAOYSA-N triacontanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O VHOCUJPBKOZGJD-UHFFFAOYSA-N 0.000 description 2
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 2
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 125000002348 vinylic group Chemical group 0.000 description 2
- XSXIVVZCUAHUJO-AVQMFFATSA-N (11e,14e)-icosa-11,14-dienoic acid Chemical compound CCCCC\C=C\C\C=C\CCCCCCCCCC(O)=O XSXIVVZCUAHUJO-AVQMFFATSA-N 0.000 description 1
- GWHCXVQVJPWHRF-KTKRTIGZSA-N (15Z)-tetracosenoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCCCC(O)=O GWHCXVQVJPWHRF-KTKRTIGZSA-N 0.000 description 1
- VJILEYKNALCDDV-OIISXLGYSA-N (1S,4aS,10aR)-1,2,3,4,4a,9,10,10a-octahydro-6-hydroxy-1,4a-dimethylphenanthrene-1-carboxylic acid Chemical compound C1=C(O)C=C2[C@@]3(C)CCC[C@@](C(O)=O)(C)[C@@H]3CCC2=C1 VJILEYKNALCDDV-OIISXLGYSA-N 0.000 description 1
- SZQQHKQCCBDXCG-BAHYSTIISA-N (2e,4e,6e)-hexadeca-2,4,6-trienoic acid Chemical compound CCCCCCCCC\C=C\C=C\C=C\C(O)=O SZQQHKQCCBDXCG-BAHYSTIISA-N 0.000 description 1
- BBWMTEYXFFWPIF-CJBMEHDJSA-N (2e,4e,6e)-icosa-2,4,6-trienoic acid Chemical compound CCCCCCCCCCCCC\C=C\C=C\C=C\C(O)=O BBWMTEYXFFWPIF-CJBMEHDJSA-N 0.000 description 1
- HPSWUFMMLKGKDS-DNKOKRCQSA-N (2e,4e,6e,8e,10e,12e)-tetracosa-2,4,6,8,10,12-hexaenoic acid Chemical compound CCCCCCCCCCC\C=C\C=C\C=C\C=C\C=C\C=C\C(O)=O HPSWUFMMLKGKDS-DNKOKRCQSA-N 0.000 description 1
- HXQHFNIKBKZGRP-URPRIDOGSA-N (5Z,9Z,12Z)-octadecatrienoic acid Chemical compound CCCCC\C=C/C\C=C/CC\C=C/CCCC(O)=O HXQHFNIKBKZGRP-URPRIDOGSA-N 0.000 description 1
- YUFFSWGQGVEMMI-JLNKQSITSA-N (7Z,10Z,13Z,16Z,19Z)-docosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O YUFFSWGQGVEMMI-JLNKQSITSA-N 0.000 description 1
- TWSWSIQAPQLDBP-CGRWFSSPSA-N (7e,10e,13e,16e)-docosa-7,10,13,16-tetraenoic acid Chemical compound CCCCC\C=C\C\C=C\C\C=C\C\C=C\CCCCCC(O)=O TWSWSIQAPQLDBP-CGRWFSSPSA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- HVGRZDASOHMCSK-UHFFFAOYSA-N (Z,Z)-13,16-docosadienoic acid Natural products CCCCCC=CCC=CCCCCCCCCCCCC(O)=O HVGRZDASOHMCSK-UHFFFAOYSA-N 0.000 description 1
- IJBFSOLHRKELLR-BQYQJAHWSA-N (e)-dodec-5-enoic acid Chemical compound CCCCCC\C=C\CCCC(O)=O IJBFSOLHRKELLR-BQYQJAHWSA-N 0.000 description 1
- ZVXDGKJSUPWREP-BQYQJAHWSA-N (e)-tetradec-7-enoic acid Chemical compound CCCCCC\C=C\CCCCCC(O)=O ZVXDGKJSUPWREP-BQYQJAHWSA-N 0.000 description 1
- VOYADQIFGGIKAT-UHFFFAOYSA-N 1,3-dibutyl-4-hydroxy-2,6-dioxopyrimidine-5-carboximidamide Chemical compound CCCCn1c(O)c(C(N)=N)c(=O)n(CCCC)c1=O VOYADQIFGGIKAT-UHFFFAOYSA-N 0.000 description 1
- DREPONDJUKIQLX-UHFFFAOYSA-N 1-[ethenyl(ethoxy)phosphoryl]oxyethane Chemical compound CCOP(=O)(C=C)OCC DREPONDJUKIQLX-UHFFFAOYSA-N 0.000 description 1
- CQCXMYUCNSJSKG-UHFFFAOYSA-N 1-dimethoxyphosphorylethene Chemical compound COP(=O)(OC)C=C CQCXMYUCNSJSKG-UHFFFAOYSA-N 0.000 description 1
- SZSSMFVYZRQGIM-UHFFFAOYSA-N 2-(hydroxymethyl)-2-propylpropane-1,3-diol Chemical compound CCCC(CO)(CO)CO SZSSMFVYZRQGIM-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QOZGSMHGXZMADD-UHFFFAOYSA-N 3-diethoxyphosphoryl-2-methylprop-1-ene Chemical compound CCOP(=O)(CC(C)=C)OCC QOZGSMHGXZMADD-UHFFFAOYSA-N 0.000 description 1
- YPJHXRAHMUKXAE-UHFFFAOYSA-N 3-diethoxyphosphorylprop-1-ene Chemical compound CCOP(=O)(CC=C)OCC YPJHXRAHMUKXAE-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- PIFPCDRPHCQLSJ-WYIJOVFWSA-N 4,8,12,15,19-Docosapentaenoic acid Chemical compound CC\C=C\CC\C=C\C\C=C\CC\C=C\CC\C=C\CCC(O)=O PIFPCDRPHCQLSJ-WYIJOVFWSA-N 0.000 description 1
- DQGMPXYVZZCNDQ-KDQYYBQISA-N 8Z,10E,12Z-octadecatrienoic acid Chemical compound CCCCC\C=C/C=C/C=C\CCCCCCC(O)=O DQGMPXYVZZCNDQ-KDQYYBQISA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- HVUCKZJUWZBJDP-UHFFFAOYSA-N Ceroplastic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O HVUCKZJUWZBJDP-UHFFFAOYSA-N 0.000 description 1
- PIFPCDRPHCQLSJ-UHFFFAOYSA-N Clupanodonic acid Natural products CCC=CCCC=CCC=CCCC=CCCC=CCCC(O)=O PIFPCDRPHCQLSJ-UHFFFAOYSA-N 0.000 description 1
- 235000021294 Docosapentaenoic acid Nutrition 0.000 description 1
- 235000021292 Docosatetraenoic acid Nutrition 0.000 description 1
- 235000021297 Eicosadienoic acid Nutrition 0.000 description 1
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 1
- OPGOLNDOMSBSCW-CLNHMMGSSA-N Fursultiamine hydrochloride Chemical compound Cl.C1CCOC1CSSC(\CCO)=C(/C)N(C=O)CC1=CN=C(C)N=C1N OPGOLNDOMSBSCW-CLNHMMGSSA-N 0.000 description 1
- ONLMUMPTRGEPCH-UHFFFAOYSA-N Hentriacontanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O ONLMUMPTRGEPCH-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- DQGMPXYVZZCNDQ-XUAYTHHASA-N Jacaric acid Natural products CCCCCC=C/C=C/C=CCCCCCCC(=O)O DQGMPXYVZZCNDQ-XUAYTHHASA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 235000021353 Lignoceric acid Nutrition 0.000 description 1
- CQXMAMUUWHYSIY-UHFFFAOYSA-N Lignoceric acid Natural products CCCCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 CQXMAMUUWHYSIY-UHFFFAOYSA-N 0.000 description 1
- XJXROGWVRIJYMO-SJDLZYGOSA-N Nervonic acid Natural products O=C(O)[C@@H](/C=C/CCCCCCCC)CCCCCCCCCCCC XJXROGWVRIJYMO-SJDLZYGOSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000021319 Palmitoleic acid Nutrition 0.000 description 1
- 239000005643 Pelargonic acid Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- VJILEYKNALCDDV-UHFFFAOYSA-N Podocarpic acid Natural products C1=C(O)C=C2C3(C)CCCC(C(O)=O)(C)C3CCC2=C1 VJILEYKNALCDDV-UHFFFAOYSA-N 0.000 description 1
- HXQHFNIKBKZGRP-UHFFFAOYSA-N Ranuncelin-saeure-methylester Natural products CCCCCC=CCC=CCCC=CCCCC(O)=O HXQHFNIKBKZGRP-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
- 235000021355 Stearic acid Nutrition 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- TWSWSIQAPQLDBP-UHFFFAOYSA-N adrenic acid Natural products CCCCCC=CCC=CCC=CCC=CCCCCCC(O)=O TWSWSIQAPQLDBP-UHFFFAOYSA-N 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- IJTNSXPMYKJZPR-WVRBZULHSA-N alpha-parinaric acid Natural products CCC=C/C=C/C=C/C=CCCCCCCCC(=O)O IJTNSXPMYKJZPR-WVRBZULHSA-N 0.000 description 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 238000010504 bond cleavage reaction Methods 0.000 description 1
- UOKRBSXOBUKDGE-UHFFFAOYSA-N butylphosphonic acid Chemical compound CCCCP(O)(O)=O UOKRBSXOBUKDGE-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
- GWHCXVQVJPWHRF-UHFFFAOYSA-N cis-tetracosenoic acid Natural products CCCCCCCCC=CCCCCCCCCCCCCCC(O)=O GWHCXVQVJPWHRF-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- DZQISOJKASMITI-UHFFFAOYSA-N decyl-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound CCCCCCCCCCP(O)(O)=O DZQISOJKASMITI-UHFFFAOYSA-N 0.000 description 1
- GZNJJEODYYLYSA-UHFFFAOYSA-N diethyl prop-2-enyl phosphate Chemical compound CCOP(=O)(OCC)OCC=C GZNJJEODYYLYSA-UHFFFAOYSA-N 0.000 description 1
- KPGGPQIHJCHVLZ-UHFFFAOYSA-N docos-15-enoic acid Chemical compound CCCCCCC=CCCCCCCCCCCCCCC(O)=O KPGGPQIHJCHVLZ-UHFFFAOYSA-N 0.000 description 1
- CVCXSNONTRFSEH-UHFFFAOYSA-N docosa-2,4-dienoic acid Chemical compound CCCCCCCCCCCCCCCCCC=CC=CC(O)=O CVCXSNONTRFSEH-UHFFFAOYSA-N 0.000 description 1
- 235000020669 docosahexaenoic acid Nutrition 0.000 description 1
- 229940090949 docosahexaenoic acid Drugs 0.000 description 1
- SVMUEEINWGBIPD-UHFFFAOYSA-N dodecylphosphonic acid Chemical compound CCCCCCCCCCCCP(O)(O)=O SVMUEEINWGBIPD-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 1
- 229960005135 eicosapentaenoic acid Drugs 0.000 description 1
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 1
- IQLUYYHUNSSHIY-HZUMYPAESA-N eicosatetraenoic acid Chemical compound CCCCCCCCCCC\C=C\C=C\C=C\C=C\C(O)=O IQLUYYHUNSSHIY-HZUMYPAESA-N 0.000 description 1
- PRHHYVQTPBEDFE-UHFFFAOYSA-N eicosatrienoic acid Natural products CCCCCC=CCC=CCCCCC=CCCCC(O)=O PRHHYVQTPBEDFE-UHFFFAOYSA-N 0.000 description 1
- 229940108623 eicosenoic acid Drugs 0.000 description 1
- BITHHVVYSMSWAG-UHFFFAOYSA-N eicosenoic acid Natural products CCCCCCCCC=CCCCCCCCCCC(O)=O BITHHVVYSMSWAG-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- FARYTWBWLZAXNK-WAYWQWQTSA-N ethyl (z)-3-(methylamino)but-2-enoate Chemical compound CCOC(=O)\C=C(\C)NC FARYTWBWLZAXNK-WAYWQWQTSA-N 0.000 description 1
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 235000021299 gondoic acid Nutrition 0.000 description 1
- YEXZTHNGURCFSJ-UHFFFAOYSA-N henicosa-2,4,6,8,10-pentaenoic acid Chemical compound CCCCCCCCCCC=CC=CC=CC=CC=CC(O)=O YEXZTHNGURCFSJ-UHFFFAOYSA-N 0.000 description 1
- VXZBFBRLRNDJCS-UHFFFAOYSA-N heptacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O VXZBFBRLRNDJCS-UHFFFAOYSA-N 0.000 description 1
- JDPSFRXPDJVJMV-UHFFFAOYSA-N hexadecylphosphonic acid Chemical compound CCCCCCCCCCCCCCCCP(O)(O)=O JDPSFRXPDJVJMV-UHFFFAOYSA-N 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N hexanedioic acid Natural products OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- GJWAEWLHSDGBGG-UHFFFAOYSA-N hexylphosphonic acid Chemical compound CCCCCCP(O)(O)=O GJWAEWLHSDGBGG-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- SDEZNODBTRWJQZ-UHFFFAOYSA-N n,n'-dibenzylhexane-1,6-diamine Chemical compound C=1C=CC=CC=1CNCCCCCCNCC1=CC=CC=C1 SDEZNODBTRWJQZ-UHFFFAOYSA-N 0.000 description 1
- 235000021290 n-3 DPA Nutrition 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- IHEJEKZAKSNRLY-UHFFFAOYSA-N nonacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O IHEJEKZAKSNRLY-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- NJGCRMAPOWGWMW-UHFFFAOYSA-N octylphosphonic acid Chemical compound CCCCCCCCP(O)(O)=O NJGCRMAPOWGWMW-UHFFFAOYSA-N 0.000 description 1
- 229960002969 oleic acid Drugs 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012788 optical film Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000307 polymer substrate Polymers 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
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- JBYXPOFIGCOSSB-UQGDGPGGSA-N rumenic acid Chemical compound CCCCCC\C=C/C=C/CCCCCCCC(O)=O JBYXPOFIGCOSSB-UQGDGPGGSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- JIWBIWFOSCKQMA-UHFFFAOYSA-N stearidonic acid Natural products CCC=CCC=CCC=CCC=CCCCCC(O)=O JIWBIWFOSCKQMA-UHFFFAOYSA-N 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- OGQIJHRKHPDBAV-UHFFFAOYSA-N tetracos-17-enoic acid Chemical compound CCCCCCC=CCCCCCCCCCCCCCCCC(O)=O OGQIJHRKHPDBAV-UHFFFAOYSA-N 0.000 description 1
- RZHACVKGHNMWOP-ZWZRQGCWSA-N tetracosatetraenoic acid n-6 Chemical compound CCCCCCCCCCCCCCC\C=C\C=C\C=C\C=C\C(O)=O RZHACVKGHNMWOP-ZWZRQGCWSA-N 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- ALVYUZIFSCKIFP-UHFFFAOYSA-N triethoxy(2-methylpropyl)silane Chemical compound CCO[Si](CC(C)C)(OCC)OCC ALVYUZIFSCKIFP-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- UMFJXASDGBJDEB-UHFFFAOYSA-N triethoxy(prop-2-enyl)silane Chemical compound CCO[Si](CC=C)(OCC)OCC UMFJXASDGBJDEB-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- NKLYMYLJOXIVFB-UHFFFAOYSA-N triethoxymethylsilane Chemical compound CCOC([SiH3])(OCC)OCC NKLYMYLJOXIVFB-UHFFFAOYSA-N 0.000 description 1
- XYJRNCYWTVGEEG-UHFFFAOYSA-N trimethoxy(2-methylpropyl)silane Chemical compound CO[Si](OC)(OC)CC(C)C XYJRNCYWTVGEEG-UHFFFAOYSA-N 0.000 description 1
- UBMUZYGBAGFCDF-UHFFFAOYSA-N trimethoxy(2-phenylethyl)silane Chemical compound CO[Si](OC)(OC)CCC1=CC=CC=C1 UBMUZYGBAGFCDF-UHFFFAOYSA-N 0.000 description 1
- RKLXSINPXIQKIB-UHFFFAOYSA-N trimethoxy(oct-7-enyl)silane Chemical compound CO[Si](OC)(OC)CCCCCCC=C RKLXSINPXIQKIB-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- TUQLLQQWSNWKCF-UHFFFAOYSA-N trimethoxymethylsilane Chemical compound COC([SiH3])(OC)OC TUQLLQQWSNWKCF-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Images
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
- C08F257/00—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- 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
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
-
- 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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
-
- 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
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/02—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of acids, salts or anhydrides
-
- 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
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
- C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/12—Powdering or granulating
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/12—Powdering or granulating
- C08J3/128—Polymer particles coated by inorganic and non-macromolecular organic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2500/00—Characteristics or properties of obtained polyolefins; Use thereof
- C08F2500/24—Polymer with special particle form or size
Landscapes
- Chemical & Material Sciences (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)
- Inorganic Chemistry (AREA)
Abstract
Description
본 명세서는 폴리머 비드 조성물 및 이를 이용한 폴리머 비드의 제조방법에 관한 것이다. The present specification relates to a polymer bead composition and a method for manufacturing a polymer bead using the same.
여기서는, 본 개시에 관한 배경기술이 제공되며, 이들이 반드시 공지기술을 의미하는 것은 아니다.BACKGROUND OF THE INVENTION Here, background art related to the present disclosure is provided, and they are not necessarily meant to be prior art.
고분자 소재 기반의 폴리머 비드는 활용성이 높은 입자로써 전기, 전자 분야를 비롯한 화학, 바이오 분야 등에서 여러 용도로 사용되고 있다. 현재 디스플레이, 조명기구 등에서는 광확산제의 용도로 사용되고 있으며, 그 외에도 도료, 플라스틱 성형품, 화장품 등의 다양한 산업분야에서 첨가제 용도로서 광범위하게 사용되고 있다. 사용되는 용도에 따라 다양한 물성이 요구된다.Polymer beads based on polymer materials are highly usable particles and are used for various purposes in chemical and bio fields, including electrical and electronic fields. Currently, it is used as a light diffusing agent in displays and lighting fixtures, and is also widely used as an additive in various industrial fields such as paints, plastic molded products, and cosmetics. Various physical properties are required depending on the use.
폴리머 비드의 열분해는 온도 구간에 따라서 250~300℃에서의 Chain end unzipping와 300℃이상에서 Unzipping by random scission으로 구분되며, 300℃전후에서의 Chain end unzipping에 의한 열분해는 현탁 중합으로 제조되는 폴리머 비드의 라디칼 중합의 특성상 종결반응시 발생되는 고분자 사슬 말단에 불포화 결합을 가지고 있는 비닐기가 포함되는 불균등 반응을 수반하고, 라디칼을 생성하여 사슬 말단으로부터의 unzipping을 발생시켜 열분해를 일으키므로 내열성이 저하된다. Thermal decomposition of polymer beads is divided into chain end unzipping at 250~300℃ and unzipping by random scission at 300℃ or higher depending on the temperature range, and thermal decomposition by chain end unzipping at around 300℃ is polymer beads produced by suspension polymerization. Due to the nature of the radical polymerization of , heat resistance is lowered because it involves an unequal reaction in which a vinyl group having an unsaturated bond is included at the end of the polymer chain, which occurs during the termination reaction, and generates radicals to cause thermal decomposition by generating unzipping from the end of the chain.
한국공개특허 제2012-0010366호에서는 특정 비닐계 단량체를 포함하는 조성물에 사슬 이동제 및 실란 단량체를 첨가하고 교반 조건을 조절하여 현탁액을 제조한 다음, 이를 이용하여 중합을 진행함으로써 열중량 분석(TGA: Thermogravimetric Analysis) 조건 300 ℃에서 10분 정치시 20% 이내의 중량 감소율을 보이며, 600℃에서 폴리머 비드의 잔량이 3% 이상인 폴리머 비드를 개시하고 있다. Korean Patent Publication No. 2012-0010366 discloses that a suspension is prepared by adding a chain transfer agent and a silane monomer to a composition containing a specific vinylic monomer and adjusting agitation conditions, and then performing polymerization using the same to prepare a thermogravimetric analysis (TGA: Thermogravimetric Analysis) Discloses a polymer bead having a weight loss rate of less than 20% when left at 300 ° C for 10 minutes and a residual amount of polymer beads of 3% or more at 600 ° C.
다만, 상기의 폴리머 비드는 320℃에서의 내열성이 다소 미흡하였으며, 내열성 향상을 위해 첨가되는 실란의 공중합으로 인해 굴절율과 같은 광특성이 변화되어, 광학 필름이나 확산판에 적용했을 때 굴절율 변화에 의해 휘도 및 은폐성의 차이가 발생할 수 있다.However, the above-described polymer beads had somewhat insufficient heat resistance at 320 ° C, and optical properties such as refractive index were changed due to copolymerization of silane added to improve heat resistance. Differences in brightness and concealment may occur.
이에, 본 발명자는 특정 단량체, 사슬이동제, 페놀계 화합물 및 표면 코팅제를 포함하는 폴리머 비드 조성물을 구현함으로써, 310 ℃ 이상의 온도에서 내열성을 향상시키면서 무게 감량이 적은 고내열성 폴리머 비드가 제조되는 것을 확인하고, 본 발명을 완성하게 되었다.Therefore, the present inventors confirmed that high heat resistance polymer beads with low weight loss while improving heat resistance at a temperature of 310 ° C. or higher were prepared by implementing a polymer bead composition containing a specific monomer, a chain transfer agent, a phenolic compound and a surface coating agent, and , which led to the completion of the present invention.
본 발명의 일 실시상태는 폴리머 비드 조성물 및 이를 이용한 폴리머 비드의 제조방법을 제공한다.One embodiment of the present invention provides a polymer bead composition and a method for producing a polymer bead using the same.
본 발명의 일 실시상태는 방향족 비닐계 단량체, 탄소수 1 내지 20개의 아크릴산 또는 메타크릴산 알킬에스테르 단량체, 및 탄소수 1 내지 20개의 아크릴산 또는 메타크릴산 플루오로알킬에스테르 단량체로 이루어진 군에서 선택되는 1종 이상의 비닐계 단량체로부터 유래된 폴리머 시드;An exemplary embodiment of the present invention is one selected from the group consisting of an aromatic vinyl monomer, an acrylic acid or methacrylic acid alkyl ester monomer having 1 to 20 carbon atoms, and an acrylic acid or methacrylic acid fluoroalkyl ester monomer having 1 to 20 carbon atoms polymer seeds derived from the above vinyl-based monomers;
하기 화학식 1의 사슬이동제;A chain transfer agent represented by Formula 1 below;
하기의 화학식 2를 양말단에 포함하고, 중간 사슬에 하기의 화학식 3 및 하기의 화학식 4를 포함하는 페놀계 화합물; 및A phenolic compound including Formula 2 below at both ends and Formula 3 below and Formula 4 below in the middle chain; and
표면 코팅제를 포함하는 폴리머 비드 조성물을 제공한다.Provided is a polymer bead composition comprising a surface coating agent.
[화학식 1][Formula 1]
R-SHR-SH
(상기 식에서, R은 탄소수 10 내지 30의 직쇄 또는 측쇄의 알킬기임)(Wherein, R is a linear or branched alkyl group having 10 to 30 carbon atoms)
[화학식 2] [Formula 2]
[화학식 3][Formula 3]
[화학식 4][Formula 4]
또한, 본 발명의 일 실시상태는 상술한 폴리머 비드 조성물을 준비하는 단계; 및 상기 폴리머 비드 조성물을 중합하는 단계를 포함하는 것인 폴리머 비드의 제조방법을 제공한다.In addition, an exemplary embodiment of the present invention comprises the steps of preparing the polymer bead composition described above; And it provides a method for producing a polymer bead comprising the step of polymerizing the polymer bead composition.
본 발명의 일 실시상태는 310 ℃ 이상의 온도에서 내열성이 우수하며 색상 변화가 없고 폴리머 비드 조성물을 제공하고자 한다.An exemplary embodiment of the present invention is to provide a polymer bead composition having excellent heat resistance at a temperature of 310 ° C. or higher and no color change.
본 발명의 일 실시상태는 균일한 입도 분포를 갖는 폴리머 비드 조성물을 제공하고자 한다.One embodiment of the present invention is to provide a polymer bead composition having a uniform particle size distribution.
본 발명의 다른 실시상태는 상기 폴리머 비드 조성물을 이용하여 폴리머 비드를 제조하는 방법을 제공하고자 한다.Another embodiment of the present invention is to provide a method for producing a polymer bead using the polymer bead composition.
도 1은 본 발명의 실시예 2에 따른 폴리머 비드의 입자 형태를 도시한 것이다.
도 2는 비교예 1에 따른 폴리머 비드를 TGA 분석한 결과를 도시한 것이다.
도 3 내지 도 6은 본 발명의 실시예 1 내지 4에 따른 폴리머 비드를 TGA 분석한 결과를 도시한 것이다.Figure 1 shows the particle shape of the polymer beads according to Example 2 of the present invention.
Figure 2 shows the results of TGA analysis of the polymer beads according to Comparative Example 1.
3 to 6 show the results of TGA analysis of the polymer beads according to Examples 1 to 4 of the present invention.
이하에 본 발명을 상세하게 설명하기에 앞서, 본 명세서에 사용된 용어는 특정의 실시예를 기술하기 위한 것일 뿐 첨부하는 특허청구의 범위에 의해서만 한정되는 본 발명의 범위를 한정하려는 것은 아님을 이해하여야 한다. Prior to describing the present invention in detail below, it is understood that the terms used herein are intended to describe specific embodiments and are not intended to limit the scope of the present invention, which is limited only by the appended claims. shall.
그리고 본 명세서 및 청구범위에 사용된 용어나 단어는 통상적이거나 사전적인 의미로 한정해서 해석되어서는 아니 되며, 발명자는 자신의 발명을 가장 최선의 방법으로 설명하기 위해 용어의 개념을 적절하게 정의할 수 있다는 원칙에 입각하여 본 발명의 기술적 사상에 부합하는 의미와 개념으로 해석되어야 한다. 다만, 본 명세서에 사용되는 모든 기술용어 및 과학용어는 다른 언급이 없는 한은 기술적으로 통상의 기술을 가진 자에게 일반적으로 이해되는 것과 동일한 의미를 가진다.And the terms or words used in this specification and claims should not be construed as being limited to the usual or dictionary meaning, and the inventor may properly define the concept of the term in order to explain his/her invention in the best way. It should be interpreted as a meaning and concept consistent with the technical idea of the present invention based on the principle that there is. However, all technical and scientific terms used in this specification have the same meaning as commonly understood by those of ordinary skill in the art unless otherwise specified.
본 명세서 및 청구범위의 전반에 걸쳐, 다른 언급이 없는 한 포함(comprise, comprises, comprising)이라는 용어는 언급된 물건, 단계 또는 일군의 물건, 및 단계를 포함하는 것을 의미하고, 임의의 어떤 다른 물건, 단계 또는 일군의 물건 또는 일군의 단계를 배제하는 의미로 사용된 것은 아니다.Throughout this specification and claims, the terms "comprise", "comprise" and "comprising", unless stated otherwise, are meant to include a stated object, step or group of objects, and steps, and any other object However, it is not used in the sense of excluding a step or a group of objects or a group of steps.
한편, 본 발명의 여러 가지 실시예들은 명확한 반대의 지적이 없는 한 그 외의 어떤 다른 실시예들과 결합될 수 있다. 특히 바람직하거나 유리하다고 지시하는 어떤 특징도 바람직하거나 유리하다고 지시한 그 외의 어떤 특징 및 특징들과 결합될 수 있다.On the other hand, various embodiments of the present invention can be combined with any other embodiments unless clearly indicated to the contrary. Any feature indicated as being particularly desirable or advantageous may be combined with any other features and characteristics indicated as being particularly desirable or advantageous.
본 발명의 일 실시상태는 방향족 비닐계 단량체, 탄소수 1 내지 20개의 아크릴산 또는 메타크릴산 알킬에스테르 단량체, 및 탄소수 1 내지 20개의 아크릴산 또는 메타크릴산 플루오로알킬에스테르 단량체로 이루어진 군에서 선택되는 1종 이상의 비닐계 단량체로부터 유래된 폴리머 시드; 하기 화학식 1의 사슬이동제; 하기의 화학식 2를 양말단에 포함하고, 중간 사슬에 하기의 화학식 3 및 하기의 화학식 4를 포함하는 페놀계 화합물; 및 표면 코팅제를 포함하는 폴리머 비드 조성물을 제공한다.An exemplary embodiment of the present invention is one selected from the group consisting of an aromatic vinyl monomer, an acrylic acid or methacrylic acid alkyl ester monomer having 1 to 20 carbon atoms, and an acrylic acid or methacrylic acid fluoroalkyl ester monomer having 1 to 20 carbon atoms polymer seeds derived from the above vinyl-based monomers; A chain transfer agent represented by Formula 1 below; A phenolic compound including Formula 2 below at both ends and Formula 3 below and Formula 4 below in the middle chain; And it provides a polymer bead composition comprising a surface coating agent.
[화학식 1][Formula 1]
R-SHR-SH
(상기 식에서, R은 탄소수 10 내지 30의 직쇄 또는 측쇄의 알킬기임)(Wherein, R is a linear or branched alkyl group having 10 to 30 carbon atoms)
[화학식 2] [Formula 2]
[화학식 3][Formula 3]
[화학식 4][Formula 4]
종래의 폴리머 비드는 비닐계 단량체를 포함하는 조성물에 사슬 이동제 및 실란 단량체를 첨가하여 제조된다. 그러나, 종래의 제조방법으로 제조된 폴리머 비드는 입자 사이즈가 수마이크로 이상이며, 입도 분포가 중분산 이상을 나타내며, 특히 고분자 콜로이드 용액이 필름의 블로킹 방지 용도 등에 적용되는 경우, 필름 가공 온도에서 우수한 내열특성을 가져야 하는데 종래의 방법으로는 고온에서 가공 시 물성이 변하거나 황변이 발생하는 등 내열특성을 확보하지 못하였고, 입도분포가 단분산하지 못해 그 적용 범위가 제한이 되는 문제점이 제기되었다.Conventional polymer beads are prepared by adding a chain transfer agent and a silane monomer to a composition comprising a vinylic monomer. However, the polymer beads produced by the conventional manufacturing method have a particle size of several microns or more, and a particle size distribution of more than medium dispersion. It should have characteristics, but in the conventional method, it was not possible to secure heat resistance properties such as change in physical properties or yellowing during processing at high temperatures, and the particle size distribution was not monodispersed, so the application range was limited.
이에 본 발명자들은 상술한 폴리머 비드 조성물이 상기 조성을 갖는 경우 이를 폴리머 비드 제조에 사용 시 가교 정도가 조절되어, 내열 특성이 우수하며 균일한 입도 분포를 갖는 것을 확인하고 본 발명을 완성하였다.Accordingly, the inventors of the present invention completed the present invention by confirming that, when the above-described polymer bead composition has the above composition, the degree of crosslinking is controlled when used in the manufacture of polymer beads, the heat resistance property is excellent, and the particle size distribution is uniform.
본 발명의 일 실시상태에 있어서, 상기 비닐계 단량체는 방향족 비닐계 단량체, 탄소수 1 내지 20개의 아크릴산 또는 메타크릴산 알킬에스테르 단량체, 및 탄소수 1 내지 20개의 아크릴산 또는 메타크릴산 플루오로알킬에스테르 단량체로 이루어진 군에서 선택되는 1종 이상이 사용될 수 있다.In one embodiment of the present invention, the vinyl-based monomer is an aromatic vinyl-based monomer, an acrylic acid or methacrylic acid alkyl ester monomer having 1 to 20 carbon atoms, and an acrylic acid or methacrylic acid fluoroalkyl ester monomer having 1 to 20 carbon atoms. One or more selected from the group consisting of may be used.
본 발명의 일 실시상태에 있어서, 상기 비닐계 단량체는 스타이렌, 메틸메타크릴레이트, 디비닐벤젠, 부틸메타크릴레이트, 트리메틸올메탄 테트라아크릴레이트, 트리메틸올메탄 트리아크릴레이트, 트리메틸올부탄 트리아크릴레이트 및 에틸렌글리콜디메타크릴레이트로 이루어진 군에서 선택되는 1종 이상을 포함될 수 있다. 바람직하게는 비닐계 단량체로서 스타이렌을 사용할 수 있다.In one embodiment of the present invention, the vinyl-based monomer is styrene, methyl methacrylate, divinylbenzene, butyl methacrylate, trimethylolmethane tetraacrylate, trimethylolmethane triacrylate, trimethylolbutane triacryl It may include at least one selected from the group consisting of late and ethylene glycol dimethacrylate. Preferably, styrene may be used as the vinyl monomer.
본 발명의 일 실시상태에 있어서, 상기 폴리머 시드는 물 등의 용매를 더 포함할 수 있다. In one embodiment of the present invention, the polymer seed may further include a solvent such as water.
본 발명의 일 실시상태에 있어서, 상기 폴리머 시드는 물 등의 용매를 더 포함하는 상태일 수 있다. 구체적인 일 예로, 상기 폴리머 시드는 상기 비닐계 단량체로부터 유래된 폴리머 시드 및 상기 용매가 혼합된 상태일 수 있다. 이때, 상기 비닐계 단량체로부터 유래된 폴리머 시드 및 상기 용매는 각각 40 내지 60 중량부 및 60 내지 40 중량부로 포함된다.In one embodiment of the present invention, the polymer seed may be in a state further including a solvent such as water. As a specific example, the polymer seed may be a mixture of the polymer seed derived from the vinyl-based monomer and the solvent. At this time, the polymer seed derived from the vinyl-based monomer and the solvent are included in 40 to 60 parts by weight and 60 to 40 parts by weight, respectively.
본 발명의 일 실시상태에 있어서, 상기 사슬이동제(Chain Transfer Agent, CTA)는 화학식 1로 표시되는 것으로서, 말단 비닐기의 불포화 결합에서 발생하는 라디칼을 제거하여 말단 비닐기의 불균등 종결 반응 및 미반응 단량체를 감소시킴에 따라, 고온에서 분해되는 단량체를 제거하여 내열성이 향상될 수 있다.In an exemplary embodiment of the present invention, the chain transfer agent (CTA) is represented by Formula 1, and removes radicals generated from unsaturated bonds of terminal vinyl groups to react and unreact uneven termination of terminal vinyl groups. As the monomers are reduced, heat resistance can be improved by removing monomers that are decomposed at high temperatures.
[화학식 1][Formula 1]
R-SHR-SH
(상기 식에서, R은 탄소수 10 내지 30의 직쇄 또는 측쇄의 알킬기임)상기 사슬이동제로서, 1-도데칸티올, t-도데실머켑탄 및 t-헥사데실머켑탄으로 이루어지는 군으로부터 선택되는 1종 이상의 것을 포함할 수 있다.(Wherein, R is a linear or branched alkyl group having 10 to 30 carbon atoms) As the chain transfer agent, at least one selected from the group consisting of 1-dodecanethiol, t-dodecylmercaptan and t-hexadecylmercaptan may include
본 발명의 일 실시상태에 있어서, 상기 R은 탄소수 10 내지 30의 직쇄의 알킬기일 수 있다. 상기 R이 직쇄의 알킬기인 경우. 사슬이동제의 반응성이 높아 사슬 이동 반응(chain transfer)의 유도가 용이한 효과가 있다. 이러한 사슬이동제를 이용하여 제조된 폴리머 비드는 내열성이 우수한 장점을 갖는다.In an exemplary embodiment of the present invention, R may be a straight chain alkyl group having 10 to 30 carbon atoms. When the said R is a straight-chain alkyl group. The reactivity of the chain transfer agent is high, and the chain transfer reaction is easily induced. Polymer beads prepared using such a chain transfer agent have excellent heat resistance.
본 발명의 일 실시상태에 있어서, 상기 사슬 이동제는 대표적인 예로 CAS 112-55-0 일 수 있다. 또는 상기 사슬이동제는 1-도데칸티올일 수 있다.In one embodiment of the present invention, the chain transfer agent may be CAS 112-55-0 as a representative example. Alternatively, the chain transfer agent may be 1-dodecanethiol.
상기 사슬이동제는 과량으로 사용될 경우 적은 분자량을 가진 폴리머가 많이 생성이 되어 반응 완결도를 높이지만, 내용제성이 떨어져서 광학 필름을 제조할 시 공정에 어려움을 줄 수 있다. 이에 내열성을 주면서 내용제성도 같이 가지게 하기 위해 적당한 양의 사슬 이동제를 사용하는 것이 중요하다.When the chain transfer agent is used in excess, a lot of polymers having a low molecular weight are generated to increase the degree of completeness of the reaction, but poor solvent resistance may cause difficulties in the manufacturing process of an optical film. Therefore, it is important to use an appropriate amount of chain transfer agent in order to have both heat resistance and solvent resistance.
본 발명의 일 실시상태에 있어서, 상기 사슬이동제는 상기 폴리머 시드 100 중량부에 대하여 0.1 내지 0.8 중량부, 바람직하게는 0.3 내지 0.5 중량부로 사용될 수 있다. 상기 사슬 이동제 함량이 0.1 중량부 이하가 될 경우 내열성 강화를 위하여 첨가하는 효과가 미미하고, 0.8 중량부 이상이면 중합 안정성을 저해하여 반응물이 응집될 염려가 있다. In one embodiment of the present invention, the chain transfer agent may be used in an amount of 0.1 to 0.8 parts by weight, preferably 0.3 to 0.5 parts by weight, based on 100 parts by weight of the polymer seed. When the content of the chain transfer agent is 0.1 parts by weight or less, the effect of adding the chain transfer agent to enhance heat resistance is insignificant, and when the content is 0.8 parts by weight or more, polymerization stability is inhibited and there is a risk of aggregation of the reactants.
본 발명의 일 실시상태에 있어서, 상기 사슬이동제는 특히 본 발명의 페놀계 화합물과 동시에 사용됨으로써, 310℃ 이상에서의 열분해 개시가 방지되어 작업 효율이 향상되며, 내열성 향상, 및 무게 감량이 저하될 수 있다. 다만, 상기 사슬이동제는 본 발명의 페놀계 화합물 대신 인계, 아민계, 힌더드 아민계, 황계 화합물 등의 산화방지제와 동시에 사용될 경우 내열성 및 반응성이 저하되는 경향을 보인다. In one embodiment of the present invention, the chain transfer agent is used simultaneously with the phenolic compound of the present invention, thereby preventing the initiation of thermal decomposition at 310 ° C. or higher, thereby improving work efficiency, improving heat resistance, and reducing weight loss. can However, when the chain transfer agent is used simultaneously with an antioxidant such as a phosphorus-based, amine-based, hindered amine-based, or sulfur-based compound instead of the phenolic compound of the present invention, heat resistance and reactivity tend to decrease.
본 발명의 일 실시상태에 있어서, 상기 페놀계 화합물은 화학식 2를 양말단에 포함하고, 중간 사슬에 화학식 3 및 화학식 4를 포함한다. 또한, 상기 중간 사슬은 8 내지 15의 탄소수를 포함하며 직쇄형으로 형성될 수 있다.In one embodiment of the present invention, the phenolic compound includes Formula 2 at both ends and
[화학식 2] [Formula 2]
[화학식 3][Formula 3]
[화학식 4][Formula 4]
본 발명의 일 실시상태에 있어서, 상기 페놀계 화합물은 화학식 2의 OH기가 라디칼 금지제로 작용하여 폴리머 비드 조성물에 단독으로 사용 시 반응을 저하할 수 있으나, 상기 사슬이동제와 동시에 사용됨으로써 고분자 분해 반응시 생성되는 과산화물 라디칼만 쉽게 포착 및 제거하여 내열성이 향상될 수 있다. 즉, 상기 페놀계 화합물은 산화방지제로 사용될 수 있다.In one embodiment of the present invention, the phenol-based compound may reduce the reaction when used alone in the polymer bead composition because the OH group of Formula 2 acts as a radical inhibitor, but when used simultaneously with the chain transfer agent, polymer decomposition reaction Heat resistance can be improved by easily trapping and removing only the peroxide radicals generated. That is, the phenolic compound may be used as an antioxidant.
상기 페놀계 화합물은 화학식 2를 양말단에 포함하고, 중간 사슬에 화학식 3 및 화학식 4를 포함하고, 상기 중간 사슬은 8 내지 15의 탄소수를 포함하며 직쇄형 구조로 형성됨에 따라, 고분자 분해 반응시 생성되는 과산화물 라디칼이 제거된 고분자가 페놀계 화합물의 양 말단에 위치하여 열분해 개시를 방지하여 흄 발생, 내열성 향상 및 색상변화 억제 및 무게 감량이 억제될 수 있는 것으로 예상된다.The phenolic compound includes Formula 2 at both ends,
본 발명의 일 실시상태에 있어서, 상기 페놀계 화합물은 상기 폴리머 시드 100 중량부에 대하여 0.1 내지 1 중량부, 나아가 0.4 내지 0.8 중량부로 사용될 수 있다. 상기 페놀계 화합물 함량이 0.1 중량부 이하가 될 경우 내열성 강화를 위하여 첨가하는 효과가 미미하고, 1 중량부 이상이면 중합 안정성을 저해하여 반응물이 응집될 염려가 있다.In one embodiment of the present invention, the phenolic compound may be used in an amount of 0.1 to 1 part by weight, and further 0.4 to 0.8 part by weight based on 100 parts by weight of the polymer seed. When the content of the phenolic compound is 0.1 part by weight or less, the effect of adding to enhance heat resistance is insignificant, and when the content is 1 part by weight or more, polymerization stability is inhibited, and reactants may aggregate.
본 발명의 일 실시상태에 있어서, 상기 페놀계 화합물은 대표적인 예로 antioxidant 245가 있고, CAS No.는 36443-68-2이다.In one embodiment of the present invention, a representative example of the phenolic compound is antioxidant 245, and CAS No. is 36443-68-2.
본 발명의 일 실시상태에 있어서, 상기 표면 코팅제로는 아크릴레이트계 화합물, 실란계 화합물, 실리케이트계 화합물, 포스포네이트계 화합물, 포스페이트계 화합물 및 산성 화합물로 이루어진 군으로부터 선택되는 1종 이상이 사용될 수 있다. 구체적인 예로, 3-트리메톡시실릴 프로필 메타크릴레이트, 실리카, 테트라에틸 오르쏘실리케이트, 비닐트리메톡시실란, 비닐트리에톡시실란, 알릴트리메톡시실란, 알릴트리에톡시실란, 트리에톡시비닐실란, 3-(트리메톡시실릴)프로필 아크릴레이트, 트리메톡시(7-옥텐-1-일)실란, 트리메톡시메틸실란, 트리에톡시메틸실란, 에틸트리메톡시실란, 트리에톡시(에틸)실란, 트리메톡시페닐실란, 트리메톡시(2-페닐에틸)실란 트리메톡시(프로필)실란, n-프로필트리에톡시실란, 이소부틸(트리메톡시)실란, 이소부틸트리에톡시실란, 비닐포스폰산, 디메틸 비닐포스포네이트, 디에틸 비닐포스포네이트, 디에틸 알릴포스포네이트, 디에틸 알릴 포스페이트, 디에틸 (2-메틸알릴)포스포네이트, 옥틸포스폰산, 부틸포스폰산, 데실포스폰산, 헥실포스폰산, 헥사데실포스폰산, n-도데실포스폰산, 라우르산, 미리스트산, 팔미트산, 스테아르산, 아라키드산, 프로피온산, 부티르산, 발레르산, 카프로산, 에난트산, 카프릴산, 펠라르곤산, 카프르산, 운데실산, 트리데실산, 펜타데실산, 마르가르산, 노나데실산, 헨아이코실산, 베헨산, 트리코실산, 리그노세르산, 펜타코실산, 세로트산, 헵타코실산, 몬탄산, 노나코실산, 멜리스산, 헤나트리아콘틸산, 락세로산, 프실산, 게드산, 세로플라스트산, 헥사트리아콘틸산, 헵타트리아콘탄산, 옥타트리아콘탄산, 올레산, 리놀레산, 리놀렌산, 아라키돈산, 헥사데카트리엔산, 스테아리돈산, 아이코사트리엔산, 아이코사테트라엔산, 아이코사펜타엔산 헨아이코사펜타엔산, 도코사펜타엔산, 클루파노돈산, 도코사헥사엔산, 테트라코사펜타엔산, 테트라코사헥사엔산, 칼렌드산, 아이코사디엔산, 도코사디엔산, 아드렌산, 도코사펜타엔산, 테트라코사테트라에노산, 테트라코사펜타엔산, 5-도데센산, 7-테트라데센산, 팔미톨레산, 바센산, 파울린산, 15-도코센산, 17-테트라코센산, 엘라이드산, 곤도산, 매드산, 에루크산, 네르본산, 루멘산, 칼렌드산, 자카르산, 엘레오스테아르산, 카탈프산, 푸니크산, 루멜렌산, 파리나르산, 보세오펜타엔산, 피놀렌산 및 포도카르프산으로 이루어진 군으로부터 선택되는 1종 이상이 사용될 수 있다. 상기 표면 코팅제의 함량은 상기 폴리머 100 중량부에 대하여 10 내지 35 중량부; 18 내지 35 중량부; 18 내지 30 중량부; 또는 20 내지 25 중량부일 수 있다. 상기 표면 코팅제를 포함함으로써 다양한 용도로 사용될 수 있는 폴리머 기재의 안정성 및 분산성을 향상시킬 수 있다.In one embodiment of the present invention, at least one selected from the group consisting of acrylate-based compounds, silane-based compounds, silicate-based compounds, phosphonate-based compounds, phosphate-based compounds and acidic compounds may be used as the surface coating agent. can Specific examples include 3-trimethoxysilyl propyl methacrylate, silica, tetraethyl orthosilicate, vinyltrimethoxysilane, vinyltriethoxysilane, allyltrimethoxysilane, allyltriethoxysilane, triethoxyvinyl Silane, 3-(trimethoxysilyl)propyl acrylate, trimethoxy(7-octen-1-yl)silane, trimethoxymethylsilane, triethoxymethylsilane, ethyltrimethoxysilane, triethoxy( Ethyl)silane, trimethoxyphenylsilane, trimethoxy(2-phenylethyl)silane, trimethoxy(propyl)silane, n-propyltriethoxysilane, isobutyl(trimethoxy)silane, isobutyltriethoxysilane , vinylphosphonic acid, dimethyl vinylphosphonate, diethyl vinylphosphonate, diethyl allylphosphonate, diethyl allyl phosphate, diethyl (2-methylallyl) phosphonate, octylphosphonic acid, butylphosphonic acid, Decylphosphonic acid, hexylphosphonic acid, hexadecylphosphonic acid, n-dodecylphosphonic acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, propionic acid, butyric acid, valeric acid, caproic acid, enan Triacic acid, Caprylic acid, Pelargonic acid, Capric acid, Undecylic acid, Tridecylic acid, Pentadecylic acid, Margaric acid, Nonadecylic acid, Henicosylic acid, Behenic acid, Trichosyllic acid, Lignoceric acid, Pentaco Silicic acid, cerotic acid, heptacosylic acid, montanic acid, nonacosylic acid, melissic acid, henatriacontylic acid, laxeroic acid, psyllic acid, gedic acid, ceroplastic acid, hexatriacontanoic acid, heptatriacontanoic acid, octa Triacontanoic Acid, Oleic Acid, Linoleic Acid, Linolenic Acid, Arachidonic Acid, Hexadecatrienoic Acid, Stearidonic Acid, Eicosatrienoic Acid, Eicosatetraenoic Acid, Eicosapentaenoic Acid Henicosapentaenoic Acid, Docosapenta Enic acid, Clupanodonic acid, Docosahexaenoic acid, Tetracosapentaenoic acid, Tetracosahexaenoic acid, Calendic acid, Eicosadienoic acid, Docosadienoic acid, Adrenic acid, Docosapentaenoic acid, Tetracosa Tetraenoic acid, tetracosapentaenoic acid, 5-dodecenoic acid, 7-tetradecenoic acid, palmitoleic acid, basenic acid, foulic acid, 15-docosenic acid, 17-tetracosenoic acid, elaidic acid, gondoic acid, Madic acid, erucic acid, nervonic acid, rumenic acid, calendic acid, jacaric acid, eleostearic acid, catalpic acid, funic acid, rumlenic acid, parinaric acid, boseopentaene At least one selected from the group consisting of acid, pinolenic acid, and podocarpic acid may be used. The amount of the surface coating agent is 10 to 35 parts by weight based on 100 parts by weight of the polymer; 18 to 35 parts by weight; 18 to 30 parts by weight; Or it may be 20 to 25 parts by weight. Stability and dispersibility of a polymer substrate that can be used for various purposes can be improved by including the surface coating agent.
본 발명의 일 실시상태에 따르면, 상기 폴리머 비드 조성물은 스타이렌 화합물을 더 포함한다. 이때, 상기 스타이렌 화합물은 상기 폴리머 시드 100 중량부에 대하여 10 내지 40 중량부 포함된다. 바람직하게, 상기 폴리머 시드 100 중량부에 대하여 10 내지 35 중량부 포함된다.According to an exemplary embodiment of the present invention, the polymer bead composition further includes a styrene compound. In this case, the styrene compound is included in an amount of 10 to 40 parts by weight based on 100 parts by weight of the polymer seed. Preferably, 10 to 35 parts by weight is included based on 100 parts by weight of the polymer seed.
본 발명의 일 실시상태에 따르면, 상기 폴리머 비드 조성물은 가교제 및 가교제 중 적어도 하나를 더 포함한다. 일 예로서, 상기 폴리머 비드 조성물은 가교제 및 가교제를 모두 포함한다. 다른 일 예로서, 상기 폴리머 비드 조성물은 가교제를 포함한다. 또 다른 일 예로서, 상기 폴리머 비드 조성물은 개시제를 포함한다.According to an exemplary embodiment of the present invention, the polymer bead composition further includes at least one of a crosslinking agent and a crosslinking agent. As an example, the polymer bead composition includes both a crosslinking agent and a crosslinking agent. As another example, the polymer bead composition includes a crosslinking agent. As another example, the polymer bead composition includes an initiator.
본 발명의 일 실시상태에 있어서, 상기 가교제는 2개 이상의 불포화 탄소를 포함한 화합물을 사용할 수 있다. 상기 가교제의 예에는 1,2-에탄디올디아크릴레이트, 1,3-프로판디올디아크릴레이트, 1,3-부탄디올디아크릴레이트, 1,4-부탄디올디아크릴레이트, 1,5-펜탄디올디아크릴레이트, 1,6-헥산디올디아크릴레이트, 디비닐벤젠, 에틸렌그리콜디아크릴레이트, 프로필렌글리콜디아크릴레이트, 부틸렌글리콜디아크릴레이트, 트리에틸렌글리콜디아크릴레이트, 폴리에틸렌글리콜디아크릴레이트, 폴리프로필렌글리콜디아크릴레이트, 폴리부틸렌글리콜디아크릴레이트, 알릴아크릴레이트, 1,2-에탄디올디메타그릴레이트, 1,3-프로판디올디메타크릴레이트, 1,3-부탄디올디메타크릴레이트, 1,4-부탄디올디메타크릴레이트, 1,5-펜탄디올디메타크릴레이트, 1,6-헥산디올디메타크릴레이트, 에틸렌글리콜디메타크릴레이트, 프로필렌글리콜디메타크릴레이트, 부틸렌글리콜디메타크릴레이트, 트리에틸렌글리콜디메타크릴레이트, 트리메틸프로판 트리아크릴레이트, 폴리에틸렌글리콜디메타크릴레이트, 트리메틸올프로판 트리아크릴레이트, 폴리프로필렌글리콜디메타크릴레이트, 부틸렌글리콜디메타크릴레이트, 트리에틸렌글리콜메타크릴레이트, 폴리에틸렌글리콜디메타크릴레이트, 폴리프로필렌글리콜디메타크릴레이트, 폴리부틸렌글리콜디메타크릴레이트, 알릴메타크릴레이트 및 디알릴말리에이트(diallyl maleate)로 이루어진 군에서 선택된 1종 이상이 포함될 수 있다.In one embodiment of the present invention, the crosslinking agent may use a compound containing two or more unsaturated carbons. Examples of the crosslinking agent include 1,2-ethanediol diacrylate, 1,3-propanediol diacrylate, 1,3-butanediol diacrylate, 1,4-butanediol diacrylate, and 1,5-pentanedioldi. Acrylate, 1,6-hexanediol diacrylate, divinylbenzene, ethylene glycol diacrylate, propylene glycol diacrylate, butylene glycol diacrylate, triethylene glycol diacrylate, polyethylene glycol diacrylate, Polypropylene glycol diacrylate, polybutylene glycol diacrylate, allyl acrylate, 1,2-ethanediol dimethacrylate, 1,3-propanediol dimethacrylate, 1,3-butanediol dimethacrylate , 1,4-butanediol dimethacrylate, 1,5-pentanediol dimethacrylate, 1,6-hexanediol dimethacrylate, ethylene glycol dimethacrylate, propylene glycol dimethacrylate, butylene glycol Dimethacrylate, triethylene glycol dimethacrylate, trimethylpropane triacrylate, polyethylene glycol dimethacrylate, trimethylolpropane triacrylate, polypropylene glycol dimethacrylate, butylene glycol dimethacrylate, tri One selected from the group consisting of ethylene glycol methacrylate, polyethylene glycol dimethacrylate, polypropylene glycol dimethacrylate, polybutylene glycol dimethacrylate, allyl methacrylate and diallyl maleate Abnormalities may be included.
본 발명의 일 실시상태에 있어서, 상기 가교제는 서로 상이한 제1 가교제 및 제2 가교제를 포함하고, 상기 제1 가교제 및 제2 가교제의 중량비는 1:2 내지 2:1일 수 있다. In one embodiment of the present invention, the crosslinking agent may include a first crosslinking agent and a second crosslinking agent that are different from each other, and the weight ratio of the first crosslinking agent and the second crosslinking agent may be 1:2 to 2:1.
본 발명의 일 실시상태에 있어서, 상기 가교제의 함량은 상기 폴리머 시드 100 중량부에 대하여 15 내지 75 중량부로 사용할 수 있다. 바람직하게는 20 내지 72 중량부로 사용할 수 있다. 상기 가교제의 함량이 15 중량부 미만이면 가교제로서의 역할을 기대할 수 없고, 75 중량부를 초과하면 반응열 조절에 어려움이 발생할 수 있고, 입자의 가교도가 높아지면 발열반응으로 인해 반응이 저하될 수 있다.In one embodiment of the present invention, the cross-linking agent may be used in an amount of 15 to 75 parts by weight based on 100 parts by weight of the polymer seed. Preferably, it may be used in an amount of 20 to 72 parts by weight. If the content of the crosslinking agent is less than 15 parts by weight, the role of the crosslinking agent cannot be expected, and if it exceeds 75 parts by weight, difficulty in controlling the heat of reaction may occur, and if the degree of crosslinking of the particles increases, the reaction may decrease due to exothermic reaction.
본 발명의 일 실시상태에 있어서, 상기 개시제는 라디칼 개시제를 포함한다. 라디칼 개시제는 지용성 개시제 또는 수용성 개시제일 수 있다. 상기 지용성 개시제에는 벤조일퍼옥사이드, 아조비스이소부티로니트릴, 아조비스페닐부티로니트릴 및 아조비스시클로헥산카르보니트릴로 이루어진 군에서 선택된 1종 이상이 포함될 수 있다. 상기 수용성 개시제에는 칼륨설페이트, 나트륨설페이트, 암모늄퍼설페이트 및 아조계 수용성 개시제로 이루어진 군에서 선택된 1종 이상이 포함된다.In one embodiment of the present invention, the initiator includes a radical initiator. The radical initiator may be a fat soluble initiator or a water soluble initiator. The fat-soluble initiator may include at least one selected from the group consisting of benzoyl peroxide, azobisisobutyronitrile, azobisphenylbutyronitrile, and azobiscyclohexanecarbonitrile. The water-soluble initiator includes at least one selected from the group consisting of potassium sulfate, sodium sulfate, ammonium persulfate, and an azo-based water-soluble initiator.
본 발명의 일 실시상태에 있어서, 상기 개시제의 함량은 상기 폴리머 시드 100 중량부에 대하여 0.1 내지 3 중량부일 수 있다. 개시제의 함량이 0.1 중량부 미만이면 반응완결도가 저하될 수 있으며, 3 중량부를 초과하면 반응열의 조절이 어려울 수 있다.In one embodiment of the present invention, the content of the initiator may be 0.1 to 3 parts by weight based on 100 parts by weight of the polymer seed. If the content of the initiator is less than 0.1 parts by weight, reaction completeness may be lowered, and if it exceeds 3 parts by weight, it may be difficult to control the heat of reaction.
본 발명의 일 실시상태에 있어서, 상기 폴리머 시드의 입경이 100nm 내지 1,000nm일 수 있다. 구체적으로, 100nm이상, 200nm이상, 300nm이상, 400nm이상, 500nm이상, 600nm이상, 700nm이상, 800nm이상, 900nm이상, 1000nm이상 일 수 있다. 상기 범위에서, 폴리머 시드의 구조적 안정성이 개선되며 입경의 분포가 균일하게 유지될 수 있다.In one embodiment of the present invention, the particle diameter of the polymer seed may be 100 nm to 1,000 nm. Specifically, it may be 100 nm or more, 200 nm or more, 300 nm or more, 400 nm or more, 500 nm or more, 600 nm or more, 700 nm or more, 800 nm or more, 900 nm or more, or 1000 nm or more. Within this range, the structural stability of the polymer seed may be improved and the particle size distribution may be maintained uniformly.
본 발명의 일 실시상태에 있어서, 상기 폴리머 비드 조성물은 분산안정제를 더 포함할 수 있다. 상기 분산안정제는 분산안정제로는 1,1-디클로로에탄, 수산화칼륨, 수산화나트륨, 아디핀산염계 화합물, 아마이드계 화합물, 설포네이트계 화합물 또는 이들의 혼합물이 사용될 수 있다. 구체적으로, 상기 분산안정제는 1,1-디클로로에탄, 수산화칼륨, 수산화나트륨, 폴리(1,6-헥사메틸렌 아디페이트)(poly(1,6-hexamethylene adipate)), N,N'-디벤질-1,6-디아미노헥산(N,N'-dibenzyl-1,6-diaminohexane), 소듐 4-비닐벤젠설포네이트 또는 이들의 혼합물 이 사용될 수 있다. 보다 구체적으로, 상기 분산안정제는 1,1-디클로로에탄, 수산화칼륨, 수산화나트륨, 폴리(1,6-헥사메틸렌 아디페이트), N,N'-디벤질-1,6-디아미노헥산, 소듐 4-비닐벤젠설포네이트 등이 사용될 수 있다. 상기 분산안정제의 함량은 상기 폴리머 시드 100 중량부에 대하여 0.01 내지 1 중량부일 수 있다.In one embodiment of the present invention, the polymer bead composition may further include a dispersion stabilizer. As the dispersion stabilizer, 1,1-dichloroethane, potassium hydroxide, sodium hydroxide, an adipic acid compound, an amide compound, a sulfonate compound, or a mixture thereof may be used as the dispersion stabilizer. Specifically, the dispersion stabilizer is 1,1-dichloroethane, potassium hydroxide, sodium hydroxide, poly(1,6-hexamethylene adipate), N,N'-dibenzyl -1,6-diaminohexane (N,N'-dibenzyl-1,6-diaminohexane), sodium 4-vinylbenzenesulfonate, or mixtures thereof may be used. More specifically, the dispersion stabilizer is 1,1-dichloroethane, potassium hydroxide, sodium hydroxide, poly(1,6-hexamethylene adipate), N,N'-dibenzyl-1,6-diaminohexane, sodium 4-vinylbenzenesulfonate and the like can be used. The content of the dispersion stabilizer may be 0.01 to 1 part by weight based on 100 parts by weight of the polymer seed.
본 발명의 일 실시상태에 따르면, 상기 폴리머 비드 조성물은 콜로이드 상태이다. 이때 상기 콜로이드 상태는 상기 폴리머 비드 조성물에 포함되는 구성들이 나노 입자 크기(1 마이크로미터 내지 100 마이크로미터)로 존재하는 것을 의미한다. 구체적인 예로서, 방향족 비닐계 단량체, 탄소수 1 내지 20개의 아크릴산 또는 메타크릴산 알킬에스테르 단량체, 및 탄소수 1 내지 20개의 아크릴산 또는 메타크릴산 플루오로알킬에스테르 단량체로 이루어진 군에서 선택되는 1종 이상의 비닐계 단량체로부터 유래된 폴리머 시드, 사슬이동제, 페놀계 화합물 또는 표면 코팅제 등이 나노 입자 크기이고, 용매에 균일하게 퍼진 상태로 존재하는 것을 의미한다.According to an exemplary embodiment of the present invention, the polymer bead composition is in a colloidal state. At this time, the colloidal state means that the constituents included in the polymer bead composition exist in nanoparticle sizes (1 micrometer to 100 micrometers). As a specific example, at least one vinyl-based monomer selected from the group consisting of an aromatic vinyl monomer, an acrylic acid or methacrylic acid alkyl ester monomer having 1 to 20 carbon atoms, and an acrylic acid or methacrylic acid fluoroalkyl ester monomer having 1 to 20 carbon atoms It means that a polymer seed derived from a monomer, a chain transfer agent, a phenolic compound, or a surface coating agent is nanoparticle-sized and exists in a state of being uniformly spread in a solvent.
본 발명의 다른 실시상태는 상기 폴리머 비드 조성물을 이용한 폴리머 비드의 제조방법을 제공한다.Another embodiment of the present invention provides a method for producing a polymer bead using the polymer bead composition.
구체적으로, 본 발명의 일 구현예는 폴리머 비드 조성물을 준비하는 단계; 및 상기 폴리머 비드 조성물을 중합하는 단계를 포함하는 것인 폴리머 비드의 제조방법을 제공한다. Specifically, one embodiment of the present invention is to prepare a polymer bead composition; And it provides a method for producing a polymer bead comprising the step of polymerizing the polymer bead composition.
본 발명의 일 실시상태에 있어서, 상기 폴리머 비드 조성물을 준비하는 단계는 방향족 비닐계 단량체, 탄소수 1 내지 20개의 아크릴산 또는 메타크릴산 알킬에스테르 단량체, 및 탄소수 1 내지 20개의 아크릴산 또는 메타크릴산 플루오로알킬에스테르 단량체로 이루어진 군에서 선택되는 1종 이상의 비닐계 단량체를 중합하여 폴리머 시드를 제조하는 단계를 포함할 수 있다. 이때, 상기 비닐계 단량체, 탄소수 1 내지 20개의 아크릴산 또는 메타크릴산 알킬에스테르 단량체, 및 탄소수 1 내지 20개의 아크릴산 또는 메타크릴산 플루오로알킬에스테르 단량체로 이루어진 군에서 선택되는 1종 이상의 비닐계 단량체 및 상기 폴리머 시드는 전술한 폴리머 비드 조성물에 기재된 내용이 적용될 수 있다.In one embodiment of the present invention, the step of preparing the polymer bead composition is an aromatic vinyl monomer, a C 1 to
본 발명의 일 실시상태에 있어서, 상기 비닐계 단량체를 중합하여 폴리머 시드를 제조하는 단계는 50℃ 내지 90℃에서 5 내지 48 시간 동안 중합 반응시키는 단계를 포함할 수 있다. 상기 범위에서, 제조된 폴리머 시드의 형상이 유지되며, 중합 반응이 원활히 개시될 수 있다. In one embodiment of the present invention, preparing a polymer seed by polymerizing the vinyl-based monomer may include polymerization at 50 °C to 90 °C for 5 to 48 hours. Within this range, the shape of the prepared polymer seed is maintained, and the polymerization reaction can be smoothly initiated.
상기 제조방법에 있어서, 상기 각 성분의 함량은 상기 폴리머 비드 조성물에서 전술한 내용이 적용될 수 있다.In the manufacturing method, the content of each component may be applied to the above-described content in the polymer bead composition.
본 발명의 일 실시상태에 있어서, 상기 폴리머 비드 조성물을 중합하는 단계는 50℃ 내지 90℃에서 5 내지 48 시간 동안 중합 반응시키는 단계를 포함할 수 있다. 상기 중합 온도 범위는 60℃ 내지 80℃이고, 중합 반응 시간은 12 내지 30 시간일 수 있다.In one embodiment of the present invention, the polymerization of the polymer bead composition may include polymerization at 50 °C to 90 °C for 5 to 48 hours. The polymerization temperature range is 60 ℃ to 80 ℃, the polymerization reaction time may be 12 to 30 hours.
상기 중합하는 단계는 유화액이 포함되는 반응기의 온도를 질소 분위기하에서 상기 온도범위에서 중합을 진행함으로써, 반응기의 온도를 올리면서 중합하는 경우보다 상기 사슬이동제가 상기 페놀계 화합물보다 중합 시에 먼저 반응할 수 있다. 이에 310 ℃ 이상에서의 열분해 개시를 방지하여 내열성이 향상될 수 있다.In the polymerization step, the temperature of the reactor containing the emulsion is polymerized in the above temperature range under a nitrogen atmosphere, so that the chain transfer agent reacts earlier than the phenolic compound during polymerization, rather than polymerization while raising the temperature of the reactor. can Accordingly, heat resistance may be improved by preventing the initiation of thermal decomposition at 310° C. or higher.
본 발명의 일 실시상태에 있어서, 상기 폴리머 비드 조성물을 중합하는 단계는 100 rpm 내지 1,000 rpm의 교반 속도로 교반하는 단계를 포함할 수 있다. 상기 교반 속도는 200 rpm 내지 800 rpm 또는 300 rpm 내지 600 rpm일 수 있다. 상기 범위에서 중합 안정성이 우수하며 제조되는 폴리머 비드의 물성이 우수하다.In one embodiment of the present invention, polymerizing the polymer bead composition may include stirring at a stirring speed of 100 rpm to 1,000 rpm. The stirring speed may be 200 rpm to 800 rpm or 300 rpm to 600 rpm. Polymerization stability is excellent in the above range, and the physical properties of the polymer beads produced are excellent.
이하, 본 발명의 이해를 돕기 위하여 바람직한 실시예를 제시하나, 하기 실시예는 본 발명을 예시하는 것일 뿐 발명의 범위가 하기 실시예에 한정되는 것은 아니다.Hereinafter, preferred examples are presented to aid understanding of the present invention, but the following examples are merely illustrative of the present invention, and the scope of the present invention is not limited to the following examples.
<비교예 및 실시예><Comparative Examples and Examples>
비교예 1Comparative Example 1
원통형 반응기에 폴리머 시드 100 중량부를 기준으로 메틸알코올(methyl alcohol)을 11 중량부, 안정제로써 소듐 4-비닐벤젠설포네이트를 0.2 중량부, 중합 개시제로써 포타슘퍼설페이트(Potassium persulfate) 0.1 중량부를 수상(폴리머 시드 100 중량부를 기준으로 물 76.7 중량부)에 질소 분위기 하에 상온에서 280 rpm으로 교반시켜 용해시켰다. 상기 용해된 물질에 폴리머 시드 100 중량부를 기준으로 스타이렌(Styrene) 모노머 12 중량부를 혼합하여 교반시킨 후 70 ℃에서 24시간 중합시켜 폴리스타이렌 폴리머 시드를 제조하였다.In a cylindrical reactor, 11 parts by weight of methyl alcohol based on 100 parts by weight of the polymer seed, 0.2 parts by weight of sodium 4-vinylbenzenesulfonate as a stabilizer, and 0.1 part by weight of potassium persulfate as a polymerization initiator. 76.7 parts by weight of water based on 100 parts by weight of the polymer seed) was dissolved by stirring at 280 rpm at room temperature under a nitrogen atmosphere. The dissolved material was mixed with 12 parts by weight of a styrene monomer based on 100 parts by weight of the polymer seed, stirred, and then polymerized at 70 ° C. for 24 hours to prepare a polystyrene polymer seed.
상기 중합 결과로 얻어진 폴리스타이렌 폴리머 시드 45 중량부 및 물 55 중량부를 혼합하였다.45 parts by weight of the polystyrene polymer seed obtained as a result of the polymerization and 55 parts by weight of water were mixed.
상기 혼합된 물질 100 중량부를 기준으로 스타이렌(Styrene) 33 중량부, 표면 코팅제로써 3-트리메톡시실릴 프로필 아크릴레이트(3-(trimethoxysilyl) propyl acrylate) 22 중량부, 개시제로써 아조비스아이소부티로나이트라일(Azobisisobutyronitrile) 0.6 중량부, 가교제로써 트리메틸올프로판 트리아크릴레이트(Trimethylolprapane triacrylate) 및 디비닐벤젠(Divinylbenzene)을 각각 22.2 중량부씩 총 44.4 중량부를 혼합하여 폴리머 비드 조성물을 제조하였다.Based on 100 parts by weight of the mixed material, 33 parts by weight of styrene, 22 parts by weight of 3-(trimethoxysilyl) propyl acrylate as a surface coating agent, and azobisisobuty as an initiator A polymer bead composition was prepared by mixing 0.6 parts by weight of nitrile (Azobisisobutyronitrile) and 22.2 parts by weight of each of trimethylolprapane triacrylate and divinylbenzene as a crosslinking agent for a total of 44.4 parts by weight.
실시예 1Example 1
상기 비교예 1에서 제조된 폴리스타이렌 폴리머 시드 45 중량부 및 물 55 중량부를 혼합하였다. 상기 혼합된 물질 100 중량부를 기준으로 스타이렌(Styrene) 32 중량부, 사슬이동제로 CAS 112-55-0 0.4 중량부 및 페놀계 화합물로 CAS 36443-68-2 0.6 중량부, 표면 코팅제로써 3-트리메톡시실릴 프로필 아크릴레이트(3-(trimethoxysilyl) propyl acrylate) 22 중량부, 개시제로써 아조비스아이소부티로나이트라일(Azobisisobutyronitrile) 0.6 중량부, 가교제로써 트리메틸올프로판 트리아크릴레이트(Trimethylolprapane triacrylate) 및 디비닐벤젠(Divinylbenzene)을 각각 22.2 중량부씩 총 44.4 중량부를 혼합하여 폴리머 비드 조성물을 제조하였다.45 parts by weight of the polystyrene polymer seed prepared in Comparative Example 1 and 55 parts by weight of water were mixed. Based on 100 parts by weight of the above mixed material, 32 parts by weight of styrene, 0.4 parts by weight of CAS 112-55-0 as a chain transfer agent, and 0.6 parts by weight of CAS 36443-68-2 as a phenolic compound, 3-part by weight as a surface coating agent 22 parts by weight of trimethoxysilyl propyl acrylate (3-(trimethoxysilyl) propyl acrylate), 0.6 parts by weight of azobisisobutyronitrile as an initiator, trimethylolprapane triacrylate and dimethylolprapane triacrylate as a crosslinking agent A polymer bead composition was prepared by mixing 44.4 parts by weight of each 22.2 parts by weight of Divinylbenzene.
실시예 2Example 2
원통형 반응기에 폴리머 시드 100 중량부를 기준으로 메틸알코올(methyl alcohol)을 19 중량부, 안정제로써 소듐 4-비닐벤젠설포네이트를 0.08 중량부, 중합 개시제로써 포타슘퍼설페이트(Potassium persulfate) 0.1 중량부를 수상(폴리머 시드 100 중량부를 기준으로 물 68.82 중량부)에 질소 분위기 하에 상온에서 280 rpm으로 교반시켜 용해시켰다. 상기 용해된 물질에 폴리머 시드 100 중량부를 기준으로 스타이렌(Styrene) 모노머 12 중량부를 혼합하여 교반시킨 후 70 ℃에서 24시간 중합시켜 폴리스타이렌 폴리머 시드를 제조하였다.In a cylindrical reactor, 19 parts by weight of methyl alcohol based on 100 parts by weight of polymer seed, 0.08 parts by weight of sodium 4-vinylbenzenesulfonate as a stabilizer, and 0.1 part by weight of potassium persulfate as a polymerization initiator. 68.82 parts by weight of water based on 100 parts by weight of the polymer seed) was dissolved by stirring at 280 rpm at room temperature under a nitrogen atmosphere. The dissolved material was mixed with 12 parts by weight of a styrene monomer based on 100 parts by weight of the polymer seed, stirred, and then polymerized at 70 ° C. for 24 hours to prepare a polystyrene polymer seed.
상기 중합 결과로 얻어진 폴리스타이렌 폴리머 시드 45 중량부 및 물 55 중량부를 혼합하였다.45 parts by weight of the polystyrene polymer seed obtained as a result of the polymerization and 55 parts by weight of water were mixed.
상기 혼합된 물질 100 중량부를 기준으로 스타이렌(Styrene) 32 중량부, 사슬이동제로 CAS 112-55-0 0.4 중량부 및 페놀계 화합물로 CAS 36443-68-2 0.6 중량부, 표면 코팅제로써 3-트리메톡시실릴 프로필 아크릴레이트(3-(trimethoxysilyl) propyl acrylate) 14 중량부, 개시제로써 아조비스아이소부티로나이트라일(Azobisisobutyronitrile) 0.6 중량부, 가교제로써 트리메틸올프로판 트리아크릴레이트(Trimethylolprapane triacrylate) 및 디비닐벤젠(Divinylbenzene)을 각각 26.2 중량부씩 총 52.4 중량부를 혼합하여 폴리머 비드 조성물을 제조하였다.Based on 100 parts by weight of the above mixed material, 32 parts by weight of styrene, 0.4 parts by weight of CAS 112-55-0 as a chain transfer agent, and 0.6 parts by weight of CAS 36443-68-2 as a phenolic compound, 3-part by weight as a surface coating agent 14 parts by weight of trimethoxysilyl propyl acrylate (3-(trimethoxysilyl) propyl acrylate), 0.6 parts by weight of azobisisobutyronitrile as an initiator, trimethylolprapane triacrylate and dimethylolprapane triacrylate as a crosslinking agent A polymer bead composition was prepared by mixing 52.4 parts by weight of each 26.2 parts by weight of Divinylbenzene.
실시예 3Example 3
상기 실시예 2에서 제조된 폴리스타이렌 폴리머 시드 45 중량부 및 물 55 중량부를 혼합하였다. 상기 혼합된 물질 100 중량부를 기준으로 스타이렌(Styrene) 13 중량부, 사슬이동제로 CAS 112-55-0 0.4 중량부 및 페놀계 화합물로 CAS 36443-68-2 0.6 중량부, 표면 코팅제로써 3-트리메톡시실릴 프로필 아크릴레이트(3-(trimethoxysilyl) propyl acrylate) 14 중량부, 개시제로써 아조비스아이소부티로나이트라일(Azobisisobutyronitrile) 0.6 중량부, 가교제로써 트리메틸올프로판 트리아크릴레이트(Trimethylolprapane triacrylate) 및 디비닐벤젠(Divinylbenzene)을 각각 35.7 중량부씩 총 71.4 중량부를 혼합하여 폴리머 비드 조성물을 제조하였다.45 parts by weight of the polystyrene polymer seed prepared in Example 2 and 55 parts by weight of water were mixed. Based on 100 parts by weight of the above mixed material, 13 parts by weight of styrene, 0.4 parts by weight of CAS 112-55-0 as a chain transfer agent and 0.6 parts by weight of CAS 36443-68-2 as a phenolic compound, 3-part by weight as a surface coating agent 14 parts by weight of trimethoxysilyl propyl acrylate (3-(trimethoxysilyl) propyl acrylate), 0.6 parts by weight of azobisisobutyronitrile as an initiator, trimethylolprapane triacrylate and dimethylolprapane triacrylate as a crosslinking agent A polymer bead composition was prepared by mixing a total of 71.4 parts by weight of 35.7 parts by weight of each of Divinylbenzene.
실시예 4Example 4
상기 실시예 2에서 제조된 폴리스타이렌 폴리머 시드 45 중량부 및 물 55 중량부를 혼합하였다. 상기 혼합된 물질 100 중량부를 기준으로 스타이렌(Styrene) 32 중량부, 사슬이동제로 CAS 112-55-0 0.4 중량부 및 페놀계 화합물로 CAS 36443-68-2 0.6 중량부, 표면 코팅제로써 3-트리메톡시실릴 프로필 아크릴레이트(3-(trimethoxysilyl) propyl acrylate) 14 중량부, 개시제로써 아조비스아이소부티로나이트라일(Azobisisobutyronitrile) 0.6 중량부, 가교제로써 디비닐벤젠(Divinylbenzene)을 52.4 중량부를 혼합하여 폴리머 비드 조성물을 제조하였다.45 parts by weight of the polystyrene polymer seed prepared in Example 2 and 55 parts by weight of water were mixed. Based on 100 parts by weight of the above mixed material, 32 parts by weight of styrene, 0.4 parts by weight of CAS 112-55-0 as a chain transfer agent, and 0.6 parts by weight of CAS 36443-68-2 as a phenolic compound, 3-part by weight as a surface coating agent 14 parts by weight of trimethoxysilyl propyl acrylate (3-(trimethoxysilyl) propyl acrylate), 0.6 parts by weight of Azobisisobutyronitrile as an initiator, and 52.4 parts by weight of divinylbenzene as a crosslinking agent were mixed. A polymer bead composition was prepared.
<폴리머 비드의 제조><Preparation of polymer beads>
상기 비교예 및 실시예의 폴리머 비드 조성물을 이용하여 폴리머 비드를 각각 제조하였다.Polymer beads were prepared using the polymer bead compositions of Comparative Examples and Examples, respectively.
구체적으로, 각각의 폴리머 비드 조성물을 질소 분위기 하에 70℃에서 280rpm으로 24시간 동안 중합하여 폴리머 비드를 제조하였다. 각각 비교 폴리머 비드 및 폴리머 비드 1 내지 4이다.Specifically, polymer beads were prepared by polymerizing each polymer bead composition under a nitrogen atmosphere at 70° C. at 280 rpm for 24 hours. Comparative polymer beads and polymer beads 1 to 4, respectively.
<실험예><Experimental example>
실험예 1 : 외관 평가Experimental Example 1: Appearance evaluation
상기 비교예 및 실시예의 폴리머 비드 조성물을 이용하여 제조된 폴리머 비드를 건조하고, 고형분 샘플을 채취한 후, 전자주사현미경(SEM, scanning electron microscopy, COXEM)를 통해 입자 형태를 분석하였다.After drying the polymer beads prepared using the polymer bead compositions of the comparative examples and examples, and taking a solid sample, the particle shape was analyzed through a scanning electron microscope (SEM, COXEM).
도 1은 본 발명의 실시예 2에 따른 폴리머 비드의 입자 형태를 도시한 것이다. 구체적으로, 본 발명의 실시예 2에 따른 폴리머 비드는 균일한 입자 크기를 갖고 표면이 매끈한 것을 확인할 수 있다.Figure 1 shows the particle shape of the polymer beads according to Example 2 of the present invention. Specifically, it can be seen that the polymer beads according to Example 2 of the present invention have a uniform particle size and a smooth surface.
실험예 2 : 내열성 평가Experimental Example 2: Evaluation of heat resistance
상기 비교예 및 실시예의 폴리머 비드 조성물을 이용하여 제조된 폴리머 비드에 대해서, 구체적으로 비교 폴리머 비드 및 폴리머 비드 1 내지 4에 대해서 열중량분석기(TGA, thermogravimetric analysis)를 통해 입자의 내열성을 평가하였다.Regarding the polymer beads prepared using the polymer bead compositions of the comparative examples and examples, specifically, the heat resistance of the particles was evaluated for the comparative polymer beads and polymer beads 1 to 4 through thermogravimetric analysis (TGA).
비교예 1에서 제조된 비교 폴리머 비드는 열분해온도가 상대적으로 낮게 나타났으나(도 2), 실시예 1(도 3), 실시예 2(도 4), 실시예 3(도 5) 및 실시예 4(도 6)에서 제조된 각각 폴리머 비드 1 내지 4의 열분해온도는 높게 나타난 것을 확인하였다. 구체적으로, 도 2를 보면 비교예 1에서 제조된 비교 폴리머 비드는 307℃ 부근에서 열분해가 진행되는 반면, 도 3 내지 6을 보면 실시예 1 내지 4에서 제조된 폴리머 비드 1 내지 4는 최소 314 ℃ 이상에서 열분해가 진행되는 것을 확인할 수 있으며, 실시예 4의 경우 330 ℃ 부근에서 열분해가 진행되는 것을 확인할 수 있다. 다시 말하여, 본원 발명에 따른 폴리머 비드는 우수한 열안정성, 즉 우수한 내열성을 갖는 것을 확인할 수 있다.Comparative polymer beads prepared in Comparative Example 1 showed a relatively low thermal decomposition temperature (Fig. 2), but Example 1 (Fig. 3), Example 2 (Fig. 4), Example 3 (Fig. 5) and Examples It was confirmed that the thermal decomposition temperature of each of the polymer beads 1 to 4 prepared in 4 (FIG. 6) was high. Specifically, in FIG. 2, the comparative polymer beads prepared in Comparative Example 1 undergo thermal decomposition at around 307° C., whereas in FIGS. From the above, it can be confirmed that thermal decomposition proceeds, and in the case of Example 4, it can be confirmed that thermal decomposition proceeds at around 330 ° C. In other words, it can be confirmed that the polymer beads according to the present invention have excellent thermal stability, that is, excellent heat resistance.
Claims (20)
하기 화학식 1의 사슬이동제;
하기의 화학식 2를 양말단에 포함하고, 중간 사슬에 하기의 화학식 3 및 하기의 화학식 4를 포함하는 페놀계 화합물; 및
표면 코팅제를 포함하는 폴리머 비드 조성물로서,
상기 폴리머 시드는 상기 1종 이상의 비닐계 단량체 및 포타슘퍼설페이트를 포함하여 중합한 것이고,
상기 폴리머 비드 조성물은 스타이렌 화합물을 더 포함하고,
상기 스타이렌 화합물은 상기 폴리머 시드 100 중량부에 대하여 10 내지 40 중량부 포함되는 것이고,
상기 폴리머 비드 조성물은 상기 폴리머 시드, 상기 스타이렌 화합물, 아조비스아이소부티로나이트라일 및 가교제를 포함하여 중합한 것인 폴리머 비드 조성물:
[화학식 1]
R-SH
(상기 식에서, R은 탄소수 10 내지 30의 직쇄 또는 측쇄의 알킬기임)
[화학식 2]
[화학식 3]
[화학식 4]
A chain transfer agent represented by Formula 1 below;
a phenol-based compound including Formula 2 below at both ends and Formula 3 below and Formula 4 below in the middle chain; and
A polymer bead composition comprising a surface coating agent,
The polymer seed is polymerized by including the at least one vinyl-based monomer and potassium persulfate,
The polymer bead composition further comprises a styrene compound,
The styrene compound is included in 10 to 40 parts by weight based on 100 parts by weight of the polymer seed,
The polymer bead composition is polymerized by including the polymer seed, the styrene compound, azobisisobutyronitrile and a crosslinking agent:
[Formula 1]
R-SH
(Wherein, R is a linear or branched alkyl group having 10 to 30 carbon atoms)
[Formula 2]
[Formula 3]
[Formula 4]
상기 비닐계 단량체는 스타이렌, 메틸메타크릴레이트, 디비닐벤젠, 부틸메타크릴레이트, 트리메틸올메탄 테트라아크릴레이트, 트리메틸올메탄 트리아크릴레이트, 트리메틸올프로판 트리아크릴레이트, 트리메틸올부탄 트리아크릴레이트 및 에틸렌글리콜디메타크릴레이트로 이루어진 군에서 선택되는 1종 이상을 포함하는 것인 폴리머 비드 조성물.The method of claim 1,
The vinyl monomers include styrene, methyl methacrylate, divinylbenzene, butyl methacrylate, trimethylolmethane tetraacrylate, trimethylolmethane triacrylate, trimethylolpropane triacrylate, trimethylolbutane triacrylate, and A polymer bead composition comprising at least one member selected from the group consisting of ethylene glycol dimethacrylate.
상기 사슬이동제는 1-도데칸티올, t-도데실머켑탄 및 t-헥사데실머켑탄으로 이루어지는 군으로부터 선택되는 1종 이상인 것인 폴리머 비드 조성물.The method of claim 1,
The chain transfer agent is at least one polymer bead composition selected from the group consisting of 1-dodecanethiol, t-dodecylmercaptan and t-hexadecylmercaptan.
상기 사슬이동제는 상기 폴리머 시드 100 중량부에 대하여 0.1 내지 0.8 중량부로 포함되는 것인 폴리머 비드 조성물.The method of claim 1,
The chain transfer agent is a polymer bead composition that is included in 0.1 to 0.8 parts by weight based on 100 parts by weight of the polymer seed.
상기 페놀계 화합물은 상기 폴리머 시드 100 중량부에 대하여 0.1 내지 1 중량부로 포함되는 것인 폴리머 비드 조성물.The method of claim 1,
The phenol-based compound is a polymer bead composition that is contained in 0.1 to 1 part by weight based on 100 parts by weight of the polymer seed.
상기 표면 코팅제는 아크릴레이트계 화합물, 실란계 화합물, 실리케이트계 화합물, 포스포네이트계 화합물, 포스페이트계 화합물 및 산성 화합물로 이루어진 군으로부터 선택되는 1종 이상인 것인 폴리머 비드 조성물.The method of claim 1,
The surface coating agent is at least one polymer bead composition selected from the group consisting of acrylate-based compounds, silane-based compounds, silicate-based compounds, phosphonate-based compounds, phosphate-based compounds and acidic compounds.
상기 표면 코팅제는 상기 폴리머 시드 100 중량부에 대하여 10 내지 35 중량부로 포함되는 것인 폴리머 비드 조성물.The method of claim 1,
The surface coating agent is a polymer bead composition that is included in 10 to 35 parts by weight based on 100 parts by weight of the polymer seed.
상기 가교제는 1,2-에탄디올디아크릴레이트, 1,3-프로판디올디아크릴레이트, 1,3-부탄디올디아크릴레이트, 1,4-부탄디올디아크릴레이트, 1,5-펜탄디올디아크릴레이트, 1,6-헥산디올디아크릴레이트, 디비닐벤젠, 에틸렌그리콜디아크릴레이트, 프로필렌글리콜디아크릴레이트, 부틸렌글리콜디아크릴레이트, 트리에틸렌글리콜디아크릴레이트, 폴리에틸렌글리콜디아크릴레이트, 폴리프로필렌글리콜디아크릴레이트, 폴리부틸렌글리콜디아크릴레이트, 알릴아크릴레이트, 1,2-에탄디올디메타그릴레이트, 1,3-프로판디올디메타크릴레이트, 1,3-부탄디올디메타크릴레이트, 1,4-부탄디올디메타크릴레이트, 1,5-펜탄디올디메타크릴레이트, 1,6-헥산디올디메타크릴레이트, 에틸렌글리콜디메타크릴레이트, 프로필렌글리콜디메타크릴레이트, 부틸렌글리콜디메타크릴레이트, 트리에틸렌글리콜디메타크릴레이트, 트리메틸프로판 트리아크릴레이트, 폴리에틸렌글리콜디메타크릴레이트, 폴리프로필렌글리콜디메타크릴레이트, 부틸렌글리콜디메타크릴레이트, 트리에틸렌글리콜메타크릴레이트, 폴리에틸렌글리콜디메타크릴레이트, 폴리프로필렌글리콜디메타크릴레이트, 폴리부틸렌글리콜디메타크릴레이트, 알릴메타크릴레이트 및 디알릴말리에이트로 이루어진 군에서 선택된 1종 이상인 것인 폴리머 비드 조성물.The method of claim 1,
The crosslinking agent is 1,2-ethanediol diacrylate, 1,3-propanediol diacrylate, 1,3-butanediol diacrylate, 1,4-butanediol diacrylate, 1,5-pentanediol diacrylate , 1,6-hexanediol diacrylate, divinylbenzene, ethylene glycol diacrylate, propylene glycol diacrylate, butylene glycol diacrylate, triethylene glycol diacrylate, polyethylene glycol diacrylate, polypropylene Glycol diacrylate, polybutylene glycol diacrylate, allyl acrylate, 1,2-ethanediol dimethacrylate, 1,3-propanediol dimethacrylate, 1,3-butanediol dimethacrylate, 1 ,4-butanediol dimethacrylate, 1,5-pentanediol dimethacrylate, 1,6-hexanediol dimethacrylate, ethylene glycol dimethacrylate, propylene glycol dimethacrylate, butylene glycol dimethacrylate Acrylate, triethylene glycol dimethacrylate, trimethylpropane triacrylate, polyethylene glycol dimethacrylate, polypropylene glycol dimethacrylate, butylene glycol dimethacrylate, triethylene glycol methacrylate, polyethylene glycol dimethacrylate A polymer bead composition comprising at least one member selected from the group consisting of methacrylate, polypropylene glycol dimethacrylate, polybutylene glycol dimethacrylate, allyl methacrylate and diallyl maleate.
상기 가교제는 상기 폴리머 시드 100 중량부에 대하여 15 내지 75 중량부로 포함되는 것인 폴리머 비드 조성물.The method of claim 1,
Wherein the crosslinking agent is contained in 15 to 75 parts by weight based on 100 parts by weight of the polymer seed.
상기 가교제는 서로 상이한 제1 가교제 및 제2 가교제를 포함하고, 상기 제1 가교제 및 제2 가교제의 중량비는 1:2 내지 2:1인 것인 폴리머 비드 조성물.The method of claim 1,
The crosslinking agent includes a first crosslinking agent and a second crosslinking agent that are different from each other, and the weight ratio of the first crosslinking agent and the second crosslinking agent is 1:2 to 2:1.
상기 폴리머 시드의 입경이 100 nm 내지 1,000 nm인 것인 폴리머 비드 조성물.The method of claim 1,
The polymer bead composition of which the particle size of the polymer seed is 100 nm to 1,000 nm.
상기 폴리머 비드 조성물은 콜로이드 상태인 것인 폴리머 비드 조성물.The method of claim 1,
The polymer bead composition is a polymer bead composition in a colloidal state.
상기 폴리머 비드 조성물을 중합하는 단계를 포함하는 것인 폴리머 비드의 제조방법.Preparing a polymer bead composition according to any one of claims 1, 4 to 9 and 11 to 15; and
Method for producing a polymer bead comprising the step of polymerizing the polymer bead composition.
상기 폴리머 비드 조성물을 준비하는 단계는
방향족 비닐계 단량체, 탄소수 1 내지 20개의 아크릴산 또는 메타크릴산 알킬에스테르 단량체, 및 탄소수 1 내지 20개의 아크릴산 또는 메타크릴산 플루오로알킬에스테르 단량체로 이루어진 군에서 선택되는 1종 이상의 비닐계 단량체를 중합하여 폴리머 시드를 제조하는 단계를 포함하는 것인 폴리머 비드의 제조방법.The method of claim 16
Preparing the polymer bead composition
By polymerizing at least one vinyl-based monomer selected from the group consisting of an aromatic vinyl monomer, an acrylic acid or methacrylic acid alkyl ester monomer having 1 to 20 carbon atoms, and an acrylic acid or methacrylic acid fluoroalkyl ester monomer having 1 to 20 carbon atoms A method for producing a polymer bead comprising the step of preparing a polymer seed.
상기 비닐계 단량체를 중합하여 폴리머 시드를 제조하는 단계는 50℃ 내지 90℃에서 5 내지 48 시간 동안 중합 반응시키는 단계를 포함하는 것인 폴리머 비드의 제조방법.The method of claim 17
The step of preparing a polymer seed by polymerizing the vinyl-based monomer comprises a polymerization reaction at 50 ° C. to 90 ° C. for 5 to 48 hours.
상기 폴리머 비드 조성물을 중합하는 단계는 50℃ 내지 90℃에서 5 내지 48 시간 동안 중합 반응시키는 단계를 포함하는 것인 폴리머 비드의 제조방법.The method of claim 16
The step of polymerizing the polymer bead composition is a method for producing a polymer bead comprising the step of polymerization for 5 to 48 hours at 50 ℃ to 90 ℃.
상기 폴리머 비드 조성물을 중합하는 단계는 100rpm 내지 1,000rpm의 교반 속도로 교반하는 단계를 포함하는 것인 폴리머 비드의 제조방법.The method of claim 16
Polymerizing the polymer bead composition comprises stirring at a stirring speed of 100 rpm to 1,000 rpm.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020220044652A KR102479521B1 (en) | 2022-04-11 | 2022-04-11 | Composition for manufacturing polymer bead and process for manufacturing polymer bead using same |
| KR1020220168279A KR102509422B1 (en) | 2022-04-11 | 2022-12-06 | Composition for manufacturing polymer bead and process for manufacturing polymer bead using same |
| PCT/KR2023/004804 WO2023200200A1 (en) | 2022-04-11 | 2023-04-10 | Polymer bead composition and method for manufacturing polymer beads by using same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020220044652A KR102479521B1 (en) | 2022-04-11 | 2022-04-11 | Composition for manufacturing polymer bead and process for manufacturing polymer bead using same |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020220168279A Division KR102509422B1 (en) | 2022-04-11 | 2022-12-06 | Composition for manufacturing polymer bead and process for manufacturing polymer bead using same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR102479521B1 true KR102479521B1 (en) | 2022-12-20 |
Family
ID=84539269
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020220044652A KR102479521B1 (en) | 2022-04-11 | 2022-04-11 | Composition for manufacturing polymer bead and process for manufacturing polymer bead using same |
| KR1020220168279A KR102509422B1 (en) | 2022-04-11 | 2022-12-06 | Composition for manufacturing polymer bead and process for manufacturing polymer bead using same |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020220168279A KR102509422B1 (en) | 2022-04-11 | 2022-12-06 | Composition for manufacturing polymer bead and process for manufacturing polymer bead using same |
Country Status (2)
| Country | Link |
|---|---|
| KR (2) | KR102479521B1 (en) |
| WO (1) | WO2023200200A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023200200A1 (en) * | 2022-04-11 | 2023-10-19 | (주)에이에스피 | Polymer bead composition and method for manufacturing polymer beads by using same |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20120010366A (en) | 2010-07-26 | 2012-02-03 | 울산대학교 산학협력단 | Pharmaceutical composition for treating and preventing chronic obstructive pulmonary disease comprising grape seed proanthocyanidin extract |
| KR20130089033A (en) * | 2012-02-01 | 2013-08-09 | 코오롱인더스트리 주식회사 | Spherical polymeric powder having a good thermal stability and preparation method thereof |
| KR20220020793A (en) * | 2020-08-12 | 2022-02-21 | (주)에이에스피 | Composition for manufacturing polymer bead and process for manufacturing polymer bead using same |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100725306B1 (en) * | 2001-01-10 | 2007-06-07 | 주식회사 코오롱 | Manufacturing method of polymer bead |
| GB0907372D0 (en) * | 2009-04-29 | 2009-06-10 | Invitrogen Dynal As | Particles |
| KR20210067411A (en) * | 2019-11-29 | 2021-06-08 | (주)에이에스피 | Polymer bead and the manufacturing method thereof |
| KR102479521B1 (en) * | 2022-04-11 | 2022-12-20 | (주)에이에스피 | Composition for manufacturing polymer bead and process for manufacturing polymer bead using same |
-
2022
- 2022-04-11 KR KR1020220044652A patent/KR102479521B1/en active IP Right Grant
- 2022-12-06 KR KR1020220168279A patent/KR102509422B1/en active IP Right Grant
-
2023
- 2023-04-10 WO PCT/KR2023/004804 patent/WO2023200200A1/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20120010366A (en) | 2010-07-26 | 2012-02-03 | 울산대학교 산학협력단 | Pharmaceutical composition for treating and preventing chronic obstructive pulmonary disease comprising grape seed proanthocyanidin extract |
| KR20130089033A (en) * | 2012-02-01 | 2013-08-09 | 코오롱인더스트리 주식회사 | Spherical polymeric powder having a good thermal stability and preparation method thereof |
| KR20220020793A (en) * | 2020-08-12 | 2022-02-21 | (주)에이에스피 | Composition for manufacturing polymer bead and process for manufacturing polymer bead using same |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023200200A1 (en) * | 2022-04-11 | 2023-10-19 | (주)에이에스피 | Polymer bead composition and method for manufacturing polymer beads by using same |
Also Published As
| Publication number | Publication date |
|---|---|
| KR102509422B1 (en) | 2023-03-14 |
| WO2023200200A1 (en) | 2023-10-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR102509422B1 (en) | Composition for manufacturing polymer bead and process for manufacturing polymer bead using same | |
| CA1051284A (en) | Process for coating pigment particles with organic polymers | |
| JP3727980B2 (en) | Encapsulated hydrophilic polymer and process for producing the same | |
| EP1926778B1 (en) | Vibration damping composition | |
| US5916963A (en) | Water-based resin dispersion and process for the production thereof | |
| DE102005000824A1 (en) | Nanoparticle-containing organocopolymers | |
| WO2009127433A1 (en) | Inorganic nanoparticles and polymer composite produced therefrom | |
| CN108290979B (en) | Vinyl chloride-based polymer composite material, method for producing same, and vinyl chloride-based polymer composite material composition | |
| JPH0333162B2 (en) | ||
| KR102456256B1 (en) | Composition for manufacturing polymer bead and process for manufacturing polymer bead using same | |
| KR20210067411A (en) | Polymer bead and the manufacturing method thereof | |
| KR101853926B1 (en) | Spherical polymeric powder having a good thermal stability and preparation method thereof | |
| JP5017847B2 (en) | Method for producing silica particle-containing methacrylic resin | |
| KR20210136868A (en) | Method for preparing vinylchloride-based polymer composite, vinylchloride-based polymer composite and vinylchloride-based polymer composite composition comprising the same | |
| CN111072316A (en) | PMMA-aluminum hydroxide-organophosphorus acrylic composite base material and preparation method thereof | |
| JPH08319303A (en) | Aqueous polymer dispersion, thickening agent for aqueous system, oil-in-water emulsion and production of aqueous polymer dispersion | |
| JP4314392B2 (en) | Method for producing polymer particles | |
| JP6282104B2 (en) | Polymer particles | |
| JPH0987120A (en) | Monomer having antimicrobial property, its production and polymer therefrom | |
| CN115746224B (en) | Polyethylene wax modified acrylic emulsion and preparation method thereof | |
| CN114599688B (en) | Method for preparing vinyl chloride polymer composite material, vinyl chloride polymer composite material and composition comprising the same | |
| KR20150028016A (en) | Process for producing fluorine-containing particles having functionality using polymerization process in suspension, and fluorine-containing particles having functionality produced by the same | |
| JP5595365B2 (en) | Novel polymer bead composition | |
| KR20170001403A (en) | Preparing method of polymer particle | |
| JP4857728B2 (en) | Method for producing methacrylic resin containing inorganic particles |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AMND | Amendment | ||
| X091 | Application refused [patent] | ||
| AMND | Amendment | ||
| X701 | Decision to grant (after re-examination) | ||
| A107 | Divisional application of patent | ||
| GRNT | Written decision to grant |