BR0215285B1 - métodos para preparar uma dispersão aquosa de partículas de polímero, e para preparar uma tinta, carga, adesivo, revestimento base ou selante. - Google Patents
métodos para preparar uma dispersão aquosa de partículas de polímero, e para preparar uma tinta, carga, adesivo, revestimento base ou selante. Download PDFInfo
- Publication number
- BR0215285B1 BR0215285B1 BRPI0215285-1A BR0215285A BR0215285B1 BR 0215285 B1 BR0215285 B1 BR 0215285B1 BR 0215285 A BR0215285 A BR 0215285A BR 0215285 B1 BR0215285 B1 BR 0215285B1
- Authority
- BR
- Brazil
- Prior art keywords
- optionally substituted
- raft agent
- mmol
- polymerization
- amphiphilic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 123
- 239000002245 particle Substances 0.000 title claims description 116
- 229920000642 polymer Polymers 0.000 title claims description 106
- 239000006185 dispersion Substances 0.000 title claims description 63
- 239000003973 paint Substances 0.000 title claims description 11
- 239000000853 adhesive Substances 0.000 title claims description 7
- 230000001070 adhesive effect Effects 0.000 title claims description 7
- 239000000565 sealant Substances 0.000 title claims description 7
- 239000000945 filler Substances 0.000 title claims description 6
- 239000002585 base Substances 0.000 title description 8
- 239000012987 RAFT agent Substances 0.000 claims description 240
- 239000000178 monomer Substances 0.000 claims description 174
- AISZNMCRXZWVAT-UHFFFAOYSA-N 2-ethylsulfanylcarbothioylsulfanyl-2-methylpropanenitrile Chemical compound CCSC(=S)SC(C)(C)C#N AISZNMCRXZWVAT-UHFFFAOYSA-N 0.000 claims description 131
- 238000006116 polymerization reaction Methods 0.000 claims description 126
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 112
- 239000000203 mixture Substances 0.000 claims description 71
- 239000012074 organic phase Substances 0.000 claims description 38
- 239000003381 stabilizer Substances 0.000 claims description 20
- 239000008346 aqueous phase Substances 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 238000009472 formulation Methods 0.000 claims description 12
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000003107 substituted aryl group Chemical group 0.000 claims description 9
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 7
- 230000007246 mechanism Effects 0.000 claims description 7
- 125000004442 acylamino group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 238000013467 fragmentation Methods 0.000 claims description 5
- 238000006062 fragmentation reaction Methods 0.000 claims description 5
- 230000000379 polymerizing effect Effects 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 230000009257 reactivity Effects 0.000 claims description 5
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 4
- 125000000962 organic group Chemical group 0.000 claims description 4
- 229910006069 SO3H Inorganic materials 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 238000007342 radical addition reaction Methods 0.000 claims description 3
- 229910004727 OSO3H Inorganic materials 0.000 claims description 2
- 125000001165 hydrophobic group Chemical group 0.000 claims description 2
- 230000000979 retarding effect Effects 0.000 claims description 2
- -1 cyano, silyl Chemical group 0.000 description 123
- 239000000243 solution Substances 0.000 description 118
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 106
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 72
- 238000006243 chemical reaction Methods 0.000 description 68
- 238000007792 addition Methods 0.000 description 61
- 239000004816 latex Substances 0.000 description 59
- 229920000126 latex Polymers 0.000 description 59
- 229910052757 nitrogen Inorganic materials 0.000 description 59
- 239000007787 solid Substances 0.000 description 57
- 238000002360 preparation method Methods 0.000 description 56
- 238000007720 emulsion polymerization reaction Methods 0.000 description 51
- 230000002209 hydrophobic effect Effects 0.000 description 47
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- 150000001875 compounds Chemical class 0.000 description 40
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 36
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- VFXXTYGQYWRHJP-UHFFFAOYSA-N 4,4'-azobis(4-cyanopentanoic acid) Chemical compound OC(=O)CCC(C)(C#N)N=NC(C)(CCC(O)=O)C#N VFXXTYGQYWRHJP-UHFFFAOYSA-N 0.000 description 33
- 239000000839 emulsion Substances 0.000 description 33
- 239000004094 surface-active agent Substances 0.000 description 33
- 230000008569 process Effects 0.000 description 32
- 238000003756 stirring Methods 0.000 description 32
- 230000015572 biosynthetic process Effects 0.000 description 31
- 150000003254 radicals Chemical class 0.000 description 30
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 29
- 229920002125 Sokalan® Polymers 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 26
- 229920001971 elastomer Polymers 0.000 description 25
- 238000010438 heat treatment Methods 0.000 description 23
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 23
- 239000003921 oil Substances 0.000 description 23
- 235000019198 oils Nutrition 0.000 description 23
- 239000003999 initiator Substances 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 20
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 19
- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- 239000003795 chemical substances by application Substances 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- 239000004793 Polystyrene Substances 0.000 description 14
- 229920002223 polystyrene Polymers 0.000 description 14
- 125000003396 thiol group Chemical group [H]S* 0.000 description 14
- 230000000977 initiatory effect Effects 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- 238000010557 suspension polymerization reaction Methods 0.000 description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 238000012546 transfer Methods 0.000 description 12
- GKLXTCVSRPGPBH-UHFFFAOYSA-N 2-(2-phenylethanethioyl)sulfanylbutanedioic acid Chemical compound OC(=O)CC(C(O)=O)SC(=S)CC1=CC=CC=C1 GKLXTCVSRPGPBH-UHFFFAOYSA-N 0.000 description 11
- 125000002252 acyl group Chemical group 0.000 description 11
- 239000003153 chemical reaction reagent Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 10
- 125000001072 heteroaryl group Chemical group 0.000 description 10
- 230000002829 reductive effect Effects 0.000 description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- 239000000693 micelle Substances 0.000 description 9
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 9
- DEDBHVFXKCVOCV-UHFFFAOYSA-N 2-butylsulfanylcarbothioylsulfanylbutanedioic acid Chemical compound CCCCSC(=S)SC(C(O)=O)CC(O)=O DEDBHVFXKCVOCV-UHFFFAOYSA-N 0.000 description 8
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 238000010526 radical polymerization reaction Methods 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- MONMFXREYOKQTI-UHFFFAOYSA-N 2-bromopropanoic acid Chemical compound CC(Br)C(O)=O MONMFXREYOKQTI-UHFFFAOYSA-N 0.000 description 7
- YGQPVBKYIVLGEE-UHFFFAOYSA-N 2-butylsulfanylcarbothioylsulfanylpropanamide Chemical compound CCCCSC(=S)SC(C)C(N)=O YGQPVBKYIVLGEE-UHFFFAOYSA-N 0.000 description 7
- VQUDUXBWOHBISV-UHFFFAOYSA-N 2-butylsulfanylcarbothioylsulfanylpropanoic acid Chemical compound CCCCSC(=S)SC(C)C(O)=O VQUDUXBWOHBISV-UHFFFAOYSA-N 0.000 description 7
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 7
- 238000005227 gel permeation chromatography Methods 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 230000000087 stabilizing effect Effects 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 239000004264 Petrolatum Substances 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 238000010923 batch production Methods 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 229920000359 diblock copolymer Polymers 0.000 description 6
- 239000000976 ink Substances 0.000 description 6
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 6
- 229940066842 petrolatum Drugs 0.000 description 6
- 235000019271 petrolatum Nutrition 0.000 description 6
- 230000001902 propagating effect Effects 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- BGQMOFGZRJUORO-UHFFFAOYSA-M tetrapropylammonium bromide Chemical compound [Br-].CCC[N+](CCC)(CCC)CCC BGQMOFGZRJUORO-UHFFFAOYSA-M 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 5
- 125000004423 acyloxy group Chemical group 0.000 description 5
- 229920001400 block copolymer Polymers 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 230000005012 migration Effects 0.000 description 5
- 238000013508 migration Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 239000001384 succinic acid Substances 0.000 description 5
- CFCFZJHCTNKHGJ-UHFFFAOYSA-N 2-dodecylsulfanylcarbothioylsulfanylpropanoic acid Chemical compound CCCCCCCCCCCCSC(=S)SC(C)C(O)=O CFCFZJHCTNKHGJ-UHFFFAOYSA-N 0.000 description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000002411 adverse Effects 0.000 description 4
- WFKAJVHLWXSISD-UHFFFAOYSA-N anhydrous dimethyl-acetamide Natural products CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 4
- 238000013459 approach Methods 0.000 description 4
- 239000012736 aqueous medium Substances 0.000 description 4
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000009563 continuous hemofiltration Methods 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- 239000011976 maleic acid Substances 0.000 description 4
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 4
- BUGISVZCMXHOHO-UHFFFAOYSA-N n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]-2-[[1-[[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCC(CO)(CO)NC(=O)C(C)(C)N=NC(C)(C)C(=O)NC(CO)(CO)CO BUGISVZCMXHOHO-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 229920002401 polyacrylamide Polymers 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 230000006641 stabilisation Effects 0.000 description 4
- 238000011105 stabilization Methods 0.000 description 4
- 125000000547 substituted alkyl group Chemical group 0.000 description 4
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- WMZLRCVBTNRMSP-UHFFFAOYSA-N 2-dodecylsulfanylcarbothioylsulfanylbutanedioic acid Chemical compound CCCCCCCCCCCCSC(=S)SC(C(O)=O)CC(O)=O WMZLRCVBTNRMSP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000004908 Emulsion polymer Substances 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000005587 bubbling Effects 0.000 description 3
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 3
- 239000012986 chain transfer agent Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 238000010505 homolytic fission reaction Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 229940047889 isobutyramide Drugs 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- WVFLGSMUPMVNTQ-UHFFFAOYSA-N n-(2-hydroxyethyl)-2-[[1-(2-hydroxyethylamino)-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCO WVFLGSMUPMVNTQ-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 239000012966 redox initiator Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000012712 reversible addition−fragmentation chain-transfer polymerization Methods 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000012989 trithiocarbonate Substances 0.000 description 3
- HIZCIEIDIFGZSS-UHFFFAOYSA-L trithiocarbonate Chemical compound [S-]C([S-])=S HIZCIEIDIFGZSS-UHFFFAOYSA-L 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- QTKPMCIBUROOGY-UHFFFAOYSA-N 2,2,2-trifluoroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)F QTKPMCIBUROOGY-UHFFFAOYSA-N 0.000 description 2
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 2
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- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- GYDSPAVLTMAXHT-UHFFFAOYSA-N pentyl 2-methylprop-2-enoate Chemical compound CCCCCOC(=O)C(C)=C GYDSPAVLTMAXHT-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920000352 poly(styrene-co-divinylbenzene) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000412 polyarylene Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000010094 polymer processing Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
- 229940099427 potassium bisulfite Drugs 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- XYVVNRCEUUMOAX-UHFFFAOYSA-N quinoline;quinoxaline Chemical compound N1=CC=CC2=CC=CC=C21.N1=CC=NC2=CC=CC=C21 XYVVNRCEUUMOAX-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000020095 red wine Nutrition 0.000 description 1
- 238000001448 refractive index detection Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- JJMIAJGBZGZNHA-UHFFFAOYSA-N sodium;styrene Chemical compound [Na].C=CC1=CC=CC=C1 JJMIAJGBZGZNHA-UHFFFAOYSA-N 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229950001150 surfomer Drugs 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 150000003564 thiocarbonyl compounds Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- CMWCOKOTCLFJOP-UHFFFAOYSA-N titanium(3+) Chemical compound [Ti+3] CMWCOKOTCLFJOP-UHFFFAOYSA-N 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 238000004627 transmission electron microscopy Methods 0.000 description 1
- BJAARRARQJZURR-UHFFFAOYSA-N trimethylazanium;hydroxide Chemical compound O.CN(C)C BJAARRARQJZURR-UHFFFAOYSA-N 0.000 description 1
- 125000000297 undecanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 229920003176 water-insoluble polymer Polymers 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
- C07C329/12—Dithiocarbonic acids; Derivatives thereof
- C07C329/14—Esters of dithiocarbonic acids
- C07C329/16—Esters of dithiocarbonic acids having sulfur atoms of dithiocarbonic groups bound to acyclic carbon atoms
-
- 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
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
- C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
-
- 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
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
- C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D157/00—Coating compositions based on unspecified polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
- C08F2438/00—Living radical polymerisation
- C08F2438/03—Use of a di- or tri-thiocarbonylthio compound, e.g. di- or tri-thioester, di- or tri-thiocarbamate, or a xanthate as chain transfer agent, e.g . Reversible Addition Fragmentation chain Transfer [RAFT] or Macromolecular Design via Interchange of Xanthates [MADIX]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Polymerisation Methods In General (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Sealing Material Composition (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Graft Or Block Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPR9708 | 2001-12-21 | ||
| AUPR9708A AUPR970801A0 (en) | 2001-12-21 | 2001-12-21 | Aqueous dispersions of polymer particles |
| AU2002950772A AU2002950772A0 (en) | 2002-08-14 | 2002-08-14 | Aqueous dispersions of polymer particles |
| AU2002/950772 | 2002-08-14 | ||
| PCT/AU2002/001735 WO2003055919A1 (en) | 2001-12-21 | 2002-12-20 | Aqueous dispersions of polymer particles |
Publications (2)
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| BR0215285A BR0215285A (pt) | 2004-11-16 |
| BR0215285B1 true BR0215285B1 (pt) | 2014-10-14 |
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| BRPI0215285-1A BR0215285B1 (pt) | 2001-12-21 | 2002-12-20 | métodos para preparar uma dispersão aquosa de partículas de polímero, e para preparar uma tinta, carga, adesivo, revestimento base ou selante. |
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| US (2) | US7745553B2 (enExample) |
| EP (1) | EP1463765B1 (enExample) |
| JP (2) | JP4405807B2 (enExample) |
| KR (2) | KR20100109960A (enExample) |
| CN (1) | CN1625571B (enExample) |
| AU (1) | AU2002350285B2 (enExample) |
| BR (1) | BR0215285B1 (enExample) |
| CA (1) | CA2470522C (enExample) |
| IL (2) | IL162557A0 (enExample) |
| MX (1) | MXPA04006145A (enExample) |
| NZ (1) | NZ533519A (enExample) |
| WO (1) | WO2003055919A1 (enExample) |
| ZA (1) | ZA200404992B (enExample) |
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| FR2868068B1 (fr) | 2004-03-29 | 2006-07-14 | Coatex Soc Par Actions Simplif | Nouveaux composes soufres : utilisation comme agent de transfert pour la polymerisation radicalaire controlee de l'acide acrylique, polymeres obtenus et leurs applications |
| EP1580206B1 (en) * | 2002-11-06 | 2010-06-16 | Kuraray Co., Ltd. | Thermoplastic polymer powder |
| US7851572B2 (en) | 2004-07-28 | 2010-12-14 | Coatex S.A.S. | Polymers produced by using sulphur compounds in the form of transfer agents for controlled radical polymerisation of acrylic acid and the use thereof |
| FR2868072B1 (fr) * | 2004-07-28 | 2006-06-30 | Coatex Soc Par Actions Simplif | Polymeres obtenus par l'utilisation de composes soufres comme agents de transfert pour la polymerisation radicalaire controlee de l'acide acrylique et leurs applications |
| WO2006023790A1 (en) * | 2004-08-20 | 2006-03-02 | Noveon, Inc. | Curable thiocarbonate compounds and compositions |
| CN101084241B (zh) * | 2004-10-04 | 2011-08-17 | 悉尼大学 | 使用raft试剂的表面聚合方法和聚合产物 |
| JP5362988B2 (ja) * | 2004-10-04 | 2013-12-11 | ザ ユニバーシティ オブ シドニー | 表面重合プロセスおよびｒａｆｔ剤を使用するポリマー生成物 |
| JP2007039654A (ja) * | 2005-07-08 | 2007-02-15 | Tosoh Corp | クロロプレン系ブロック共重合体及びその製造法 |
| DE112006001808T5 (de) * | 2005-07-08 | 2008-06-19 | Tosoh Corporation | Blockcopolymer auf Chloroprenbasis, seifenfreier Latex auf Polychloroprenbasis und Verfahren zur Herstellung derselbigen |
| US7230063B1 (en) * | 2005-12-22 | 2007-06-12 | The Goodyear Tire & Rubber Company | Functional trithiocarbonate RAFT agents |
| JP4978946B2 (ja) * | 2006-02-08 | 2012-07-18 | 株式会社 資生堂 | Ｇｐｃスタンダード用イオン性ポリマー |
| KR20070097742A (ko) * | 2006-03-29 | 2007-10-05 | 주식회사 엘지화학 | 염화비닐계 수지 제조용 분산제 및 이를 이용한 염화비닐계수지의 제조 방법 |
| BRPI0709848B1 (pt) * | 2006-04-03 | 2018-03-27 | The University Of Sydney | Métodos para polimerizar monômero para formar polímero na superfície de material particulado sólido, para preparar uma dispersão de material particulado sólido encapsulado em polímero em um líquido hidrofílico, para preparar um polímero e para preparar uma tinta, carga, adesivo, toner, tinta líquida, base de revestimento, selante, produto de diagnóstico ou produto terapêutico, tinta, carga, adesivo, toner, tinta líquida, base de revestimento, selante, produto diagnóstico ou produto terapêutico, material particulado sólido encapsulado em polímero, composição, e, dispersão líquida |
| DE602007011615D1 (de) | 2006-07-05 | 2011-02-10 | Solvay | Verfahren zur herstellung eines latex eines vinylchloridpolymers |
| WO2008046156A1 (en) * | 2006-10-20 | 2008-04-24 | The University Of Sydney | Vesiculated polymer particles |
| GB0624729D0 (en) * | 2006-12-12 | 2007-01-17 | Univ Leeds | Reversible micelles and applications for their use |
| US20100136353A1 (en) * | 2007-04-05 | 2010-06-03 | Michael Arnoldus Jacobus Schellekens | Aqueous oligomer / polymer emulsion with cationic functionality |
| JP5133606B2 (ja) * | 2007-06-04 | 2013-01-30 | Ａｇｃセイミケミカル株式会社 | 界面活性剤 |
| JP2009001776A (ja) | 2007-06-11 | 2009-01-08 | Rohm & Haas Co | 水性エマルジョンポリマー会合性増粘剤 |
| WO2009016239A1 (en) * | 2007-08-02 | 2009-02-05 | Dsm Ip Assets B.V. | Aqueous dispersions containing crystallisable block copolymers |
| CN101918465A (zh) * | 2008-01-17 | 2010-12-15 | 帝斯曼知识产权资产管理有限公司 | 利用raft得到的水性可交联嵌段共聚物 |
| EP2268758B1 (en) | 2008-03-20 | 2013-12-18 | Avery Dennison Corporation | Acrylic polymers having controlled placement of functional groups |
| FR2931154B1 (fr) * | 2008-05-14 | 2011-04-08 | Univ Paris Curie | Copolymere amphiphile a blocs, procede pour sa preparation |
| CA2764611C (en) | 2008-06-05 | 2017-11-21 | The Administrators Of The Tulane Educational Fund | Methods and instrumentation for during-synthesis monitoring of polymer functional evolution |
| EP2291413B1 (de) * | 2008-06-17 | 2012-11-14 | Basf Se | Verfahren zur herstellung einer wässrigen polymerisatdispersion |
| CN102076795B (zh) * | 2008-06-30 | 2015-05-13 | 帝斯曼知识产权资产管理有限公司 | 利用raft得到的嵌段共聚物对金属表面的粘附 |
| FR2934861B1 (fr) * | 2008-08-05 | 2012-12-28 | Arkema France | Nouveaux modifiants chocs du type coeur-ecorce pour matrices polymeres transparentes. |
| CN102232090A (zh) * | 2008-10-03 | 2011-11-02 | 凯米利克有限公司 | Ab双嵌段共聚物和使用它们的用途 |
| EP2182011A1 (de) | 2008-10-29 | 2010-05-05 | Basf Se | Verfahren zur Herstellung von wässrigen Polyacrylsäurelösungen mittels kontrollierter radikalischer Polymerisation |
| AU2010217189A1 (en) * | 2009-02-24 | 2011-09-08 | The University Of Sydney | Polymer particles |
| US20100315588A1 (en) * | 2009-06-16 | 2010-12-16 | Bausch & Lomb Incorporated | Biomedical devices |
| CN102741363A (zh) * | 2009-12-01 | 2012-10-17 | 悉尼大学 | 水可溶胀聚合物材料 |
| EP2530073A4 (en) * | 2010-01-27 | 2014-10-08 | Mitsubishi Rayon Co | NEW CHAIN TRANSFER AND EMULSION POLYMERIZATION THEREWITH |
| GB201003970D0 (en) * | 2010-03-10 | 2010-04-21 | Univ Sheffield | Polymer synthesis |
| ES2512440T3 (es) | 2010-05-19 | 2014-10-24 | Avery Dennison Corporation | Arquitecturas ordenadas en polímeros acrílicos |
| CN101864049A (zh) * | 2010-06-12 | 2010-10-20 | 陕西科技大学 | 一种高分子表面活性剂的制备方法 |
| CN101982478A (zh) * | 2010-09-26 | 2011-03-02 | 北京印刷学院 | 一种大分子表面活性剂和核-壳两亲型聚合物微球及其制备方法 |
| US9428649B2 (en) * | 2010-11-05 | 2016-08-30 | E Ink California, Llc | Electrophoretic dispersion |
| JP2012233147A (ja) * | 2011-03-31 | 2012-11-29 | Canon Inc | 高分子粒子の製造方法 |
| US9339781B2 (en) * | 2011-05-31 | 2016-05-17 | The University Of Sydney | Polymer particles |
| KR101887243B1 (ko) * | 2011-07-13 | 2018-08-09 | 에이지씨 세이미 케미칼 가부시키가이샤 | 경화성 수지 조성물 및 그 용도 |
| WO2013035206A1 (ja) * | 2011-09-09 | 2013-03-14 | ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェン | 電子装置用シール剤組成物 |
| EP2766404B1 (en) | 2011-10-14 | 2019-11-13 | Avery Dennison Corporation | Controlled architecture polymers |
| CN104271621B (zh) * | 2011-12-21 | 2017-09-05 | 索尔维公司 | 用于制备偏二氯乙烯聚合物的方法 |
| CN104125968B (zh) * | 2011-12-21 | 2017-10-13 | 索尔维公司 | 用于制备偏二氯乙烯聚合物/粘土复合材料的方法 |
| FR2986235B1 (fr) * | 2012-01-31 | 2015-02-06 | Rhodia Operations | Stabilisants reactifs poly(n-vinyl lactame) vivants pour polymerisation en phase dispersee |
| EP2809697B1 (fr) * | 2012-01-31 | 2017-07-19 | Rhodia Operations | Stabilisants réactifs poly(n-vinyl lactame) vivants pour polymérisation en phase dispersée |
| FR2986234B1 (fr) * | 2012-01-31 | 2014-06-13 | Rhodia Operations | Stabilisants reactifs poly(n-vinyl lactame) vivants pour polymerisation en phase dispersee |
| JP5805006B2 (ja) * | 2012-05-14 | 2015-11-04 | 株式会社クラレ | ビニルエステルとビニルエーテルの共重合体、およびその製造方法 |
| CN102690217B (zh) * | 2012-05-31 | 2014-04-16 | 同济大学 | 一种用于可逆加成断裂链转移聚合的高效链转移剂三硫酯的制备方法 |
| CN102746475B (zh) * | 2012-06-18 | 2014-04-23 | 浙江理工大学 | 含异氰酸酯基团的三硫代碳酸酯化合物及制备方法和应用 |
| CN102746478B (zh) * | 2012-07-13 | 2014-07-16 | 浙江大学 | 含玻璃化温度高于100℃嵌段的嵌段共聚物及制备方法 |
| JP5773087B2 (ja) * | 2012-10-11 | 2015-09-02 | 横浜ゴム株式会社 | 水系プライマー組成物 |
| JP6028093B2 (ja) * | 2013-05-07 | 2016-11-16 | 株式会社豊田自動織機 | ポリマーとその製造方法 |
| FR3012462B1 (fr) * | 2013-10-31 | 2016-01-01 | Arkema France | Compositions stables de poly (3,4-ethylenedioxythiophene) et de stabilisants anioniques a acidite limitee |
| ES2688148T3 (es) | 2014-03-28 | 2018-10-31 | Synthomer (Uk) Ltd. | Agente de suspensión secundario para reacción de polimerización en suspensión |
| US10647793B2 (en) | 2014-03-28 | 2020-05-12 | Synthomer (Uk) Limited | Use of a sulphur or phosphorous-containing polymer as a processing aid in a polyvinyl chloride polymer composition |
| US9732169B2 (en) | 2014-07-22 | 2017-08-15 | University Of South Carolina | Raft agents and their use in the development of polyvinylpyrrolidone grafted nanoparticles |
| KR20180005688A (ko) * | 2015-05-08 | 2018-01-16 | 더루브리졸코오퍼레이션 | 수용성 사슬 이동제 |
| CA2977932A1 (en) * | 2016-09-23 | 2018-03-23 | Rohm And Haas Company | Latex functionalized with structural units of an amino acid |
| JP7190433B2 (ja) | 2017-07-31 | 2022-12-15 | デンカ株式会社 | ブロック共重合体及びブロック共重合体の製造方法 |
| FR3071500B1 (fr) * | 2017-09-27 | 2020-05-15 | Arkema France | Synthese de latex de poly(fluorure de vinylidene) sans tensioactif par polymerisation en emulsion raft |
| AU2018359005A1 (en) * | 2017-10-31 | 2020-05-07 | The University Of Sydney | Novel polymer coated chlorothalonil particles |
| KR20190064794A (ko) * | 2017-12-01 | 2019-06-11 | 현대자동차주식회사 | 메타크릴계 블록 공중합체의 제조 방법 |
| TWI800575B (zh) * | 2017-12-20 | 2023-05-01 | 美商盧伯利索先進材料有限公司 | 苯乙烯馬來醯胺嵌段共聚物顏料分散劑及其形成方法 |
| KR101997538B1 (ko) * | 2017-12-29 | 2019-07-09 | 금호석유화학 주식회사 | Raft제 및 이를 이용한 공중합체의 제조방법 |
| EP3940010A1 (de) * | 2018-05-31 | 2022-01-19 | Sika Technology AG | Verfahren zur herstellung von wohldefinierten kammpolymeren |
| CN109867736B (zh) * | 2019-03-15 | 2022-01-04 | 重庆科技学院 | 一种可逆加成断裂链转移试剂及其制备方法和应用 |
| AU2020251047A1 (en) * | 2019-04-01 | 2021-10-28 | The University Of Sydney | Non-core-shell polymer particles |
| JP7465165B2 (ja) * | 2020-07-09 | 2024-04-10 | テクノＵｍｇ株式会社 | ポリマーを含む粒子の水分散体の製造方法、及びブロックポリマーの製造方法 |
| CN113463402B (zh) * | 2021-06-28 | 2024-04-02 | 深圳万知达科技有限公司 | 一种pH响应超疏水-亲水可逆转化材料表面的制备方法 |
| JP7405891B2 (ja) * | 2022-03-29 | 2023-12-26 | テクノＵｍｇ株式会社 | Ｒａｆｔ重合用反応液 |
| US12319769B2 (en) | 2022-03-29 | 2025-06-03 | Techno-Umg Co., Ltd. | Raft polymerization reaction solution and raft polymerization reaction solution production method |
| JP7405892B2 (ja) * | 2022-03-29 | 2023-12-26 | テクノＵｍｇ株式会社 | Ｒａｆｔ重合用反応液の製造方法 |
| CN115181276A (zh) * | 2022-08-26 | 2022-10-14 | 潍坊瑞通环保科技有限公司 | 改性环氧树脂及其制备方法、环氧树脂涂料及其制备方法、应用 |
| CN116496454B (zh) * | 2023-06-30 | 2023-09-26 | 河北合众建材有限公司 | 一种低温法合成多支化保坍型聚醚减水剂及制备方法 |
| CN116693906B (zh) * | 2023-07-07 | 2023-11-28 | 珠海嘉雄包装材料有限公司 | 一种高强度pe复合膜及其制备工艺 |
| WO2025064359A1 (en) * | 2023-09-20 | 2025-03-27 | Isp Investments Llc | Block copolymers with polyether moieties and applications thereof |
| CN117089315B (zh) * | 2023-10-19 | 2024-02-09 | 宁波长阳科技股份有限公司 | 一种水性锂电池聚酰亚胺粘合剂及制备方法、锂电池极片 |
| WO2025097130A1 (en) * | 2023-11-03 | 2025-05-08 | The Brigham And Women's Hospital, Inc. | Injectable in situ cross-linked depots for ultra-long-term delivery of hydrophilic drugs |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998001478A1 (en) * | 1996-07-10 | 1998-01-15 | E.I. Du Pont De Nemours And Company | Polymerization with living characteristics |
| AUPO669697A0 (en) * | 1997-05-08 | 1997-06-05 | Unisearch Limited | Polymerisation reactions under miniemulsion conditions |
| IL139666A0 (en) | 1997-07-21 | 2002-02-10 | Commw Scient Ind Res Org | Synthesis of dithioester chain transfer agents and use of bis (thioacyl) disulfides or dithioesters as chain transfer agents |
| CA2309279C (en) | 1997-12-18 | 2009-07-14 | E.I. Du Pont De Nemours And Company | Polymerization process with living characteristics and polymers made therefrom |
| AUPP337298A0 (en) * | 1998-05-07 | 1998-05-28 | University Of Melbourne, The | Process for microgel preparation |
| PT1123332E (pt) | 1998-07-10 | 2004-08-31 | Du Pont | Microgeis e processos para a sua preparacao |
| US7064151B1 (en) * | 2000-04-07 | 2006-06-20 | E. I. Du Pont De Nemours And Company | Process of microgel synthesis and products produced therefrom |
| AUPQ679400A0 (en) * | 2000-04-07 | 2000-05-11 | Commonwealth Scientific And Industrial Research Organisation | Microgel synthesis |
| ATE325144T1 (de) * | 2000-05-29 | 2006-06-15 | Bio Merieux | Biokompatible polymere für die bindung von biologischen liganden |
| US6458968B2 (en) * | 2000-06-09 | 2002-10-01 | Rensselaer Polytechnic Institute | Dithiocarboxylic ester synthetic process |
| EP1205492A1 (en) | 2000-11-08 | 2002-05-15 | ETHZ, Laboratorium für Technische Chemie LTC | Process for producing homo- and co-polymers by RAFT miniemulsion polymerization |
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- 2002-12-20 KR KR1020107018296A patent/KR20100109960A/ko not_active Withdrawn
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| US7745553B2 (en) | 2010-06-29 |
| BR0215285A (pt) | 2004-11-16 |
| KR101000839B1 (ko) | 2010-12-14 |
| EP1463765A1 (en) | 2004-10-06 |
| AU2002350285B2 (en) | 2008-02-28 |
| CA2470522C (en) | 2012-05-01 |
| JP2009173943A (ja) | 2009-08-06 |
| US20060223936A1 (en) | 2006-10-05 |
| CN1625571A (zh) | 2005-06-08 |
| MXPA04006145A (es) | 2005-03-31 |
| JP2005513252A (ja) | 2005-05-12 |
| ZA200404992B (en) | 2005-04-26 |
| KR20040076260A (ko) | 2004-08-31 |
| EP1463765B1 (en) | 2018-07-18 |
| WO2003055919A1 (en) | 2003-07-10 |
| AU2002350285A1 (en) | 2003-07-15 |
| JP4405807B2 (ja) | 2010-01-27 |
| CN1625571B (zh) | 2010-10-06 |
| US20100227975A1 (en) | 2010-09-09 |
| EP1463765A4 (en) | 2006-05-10 |
| JP5173914B2 (ja) | 2013-04-03 |
| IL162557A0 (en) | 2005-11-20 |
| KR20100109960A (ko) | 2010-10-11 |
| CA2470522A1 (en) | 2003-07-10 |
| NZ533519A (en) | 2007-07-27 |
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