JP2012517493A - 分岐したコポリマー、組成物および使用 - Google Patents
分岐したコポリマー、組成物および使用 Download PDFInfo
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- JP2012517493A JP2012517493A JP2011548775A JP2011548775A JP2012517493A JP 2012517493 A JP2012517493 A JP 2012517493A JP 2011548775 A JP2011548775 A JP 2011548775A JP 2011548775 A JP2011548775 A JP 2011548775A JP 2012517493 A JP2012517493 A JP 2012517493A
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- JP
- Japan
- Prior art keywords
- hydrophilic
- monomer
- vinyl
- branched copolymer
- monomers
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 229920005605 branched copolymer Polymers 0.000 title claims abstract description 64
- 239000000203 mixture Substances 0.000 title claims abstract description 26
- 239000000178 monomer Substances 0.000 claims abstract description 227
- 229920001577 copolymer Polymers 0.000 claims abstract description 68
- -1 vinyl aryl compound Chemical class 0.000 claims abstract description 62
- 239000012986 chain transfer agent Substances 0.000 claims abstract description 57
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 55
- 238000000034 method Methods 0.000 claims abstract description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 35
- 239000003999 initiator Substances 0.000 claims abstract description 30
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 28
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 20
- 230000008569 process Effects 0.000 claims abstract description 17
- 150000002148 esters Chemical class 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 13
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 11
- 238000012644 addition polymerization Methods 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 claims abstract description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 5
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
- 229920000642 polymer Polymers 0.000 claims description 59
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 55
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 40
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 34
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 17
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 16
- 150000001408 amides Chemical class 0.000 claims description 16
- 238000010526 radical polymerization reaction Methods 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 230000002209 hydrophobic effect Effects 0.000 claims description 13
- 239000000243 solution Substances 0.000 claims description 13
- 239000000839 emulsion Substances 0.000 claims description 12
- 150000003573 thiols Chemical class 0.000 claims description 12
- 238000000576 coating method Methods 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 8
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 239000000976 ink Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 238000010276 construction Methods 0.000 claims description 6
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 6
- 150000002978 peroxides Chemical class 0.000 claims description 6
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 5
- 150000002170 ethers Chemical class 0.000 claims description 5
- 239000000446 fuel Substances 0.000 claims description 5
- 239000000314 lubricant Substances 0.000 claims description 5
- 150000008378 aryl ethers Chemical class 0.000 claims description 4
- DGAODIKUWGRDBO-UHFFFAOYSA-N butanethioic s-acid Chemical compound CCCC(O)=S DGAODIKUWGRDBO-UHFFFAOYSA-N 0.000 claims description 4
- 239000013078 crystal Substances 0.000 claims description 4
- 238000004090 dissolution Methods 0.000 claims description 4
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical class NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 claims description 4
- 230000008014 freezing Effects 0.000 claims description 4
- 238000007710 freezing Methods 0.000 claims description 4
- 238000010550 living polymerization reaction Methods 0.000 claims description 4
- 238000007151 ring opening polymerisation reaction Methods 0.000 claims description 4
- 238000004513 sizing Methods 0.000 claims description 4
- 239000000080 wetting agent Substances 0.000 claims description 4
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 4
- QLOMMFARVWCHAZ-UHFFFAOYSA-N 2-phenylpropan-2-yl 2-phenylethanedithioate Chemical compound C=1C=CC=CC=1C(C)(C)SC(=S)CC1=CC=CC=C1 QLOMMFARVWCHAZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000012988 Dithioester Substances 0.000 claims description 3
- 239000013466 adhesive and sealant Substances 0.000 claims description 3
- 239000003905 agrochemical Substances 0.000 claims description 3
- 150000005215 alkyl ethers Chemical class 0.000 claims description 3
- 150000001350 alkyl halides Chemical class 0.000 claims description 3
- 239000004815 dispersion polymer Substances 0.000 claims description 3
- 125000005022 dithioester group Chemical group 0.000 claims description 3
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003966 growth inhibitor Substances 0.000 claims description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 3
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 claims description 3
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims description 3
- 229920001296 polysiloxane Polymers 0.000 claims description 3
- 239000012966 redox initiator Substances 0.000 claims description 3
- 239000012991 xanthate Substances 0.000 claims description 3
- YFKBXYGUSOXJGS-UHFFFAOYSA-N 1,3-Diphenyl-2-propanone Chemical compound C=1C=CC=CC=1CC(=O)CC1=CC=CC=C1 YFKBXYGUSOXJGS-UHFFFAOYSA-N 0.000 claims description 2
- 239000003125 aqueous solvent Substances 0.000 claims description 2
- MGFFVSDRCRVHLC-UHFFFAOYSA-N butyl 3-sulfanylpropanoate Chemical compound CCCCOC(=O)CCS MGFFVSDRCRVHLC-UHFFFAOYSA-N 0.000 claims description 2
- 239000006185 dispersion Substances 0.000 claims description 2
- LWNSNYBMYBWJDN-UHFFFAOYSA-N octyl 3-sulfanylpropanoate Chemical compound CCCCCCCCOC(=O)CCS LWNSNYBMYBWJDN-UHFFFAOYSA-N 0.000 claims description 2
- 239000004848 polyfunctional curative Substances 0.000 claims description 2
- KOODSCBKXPPKHE-UHFFFAOYSA-N propanethioic s-acid Chemical compound CCC(S)=O KOODSCBKXPPKHE-UHFFFAOYSA-N 0.000 claims description 2
- 239000012266 salt solution Substances 0.000 claims description 2
- BGPJLYIFDLICMR-UHFFFAOYSA-N 1,4,2,3-dioxadithiolan-5-one Chemical compound O=C1OSSO1 BGPJLYIFDLICMR-UHFFFAOYSA-N 0.000 claims 1
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 claims 1
- 125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 description 15
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 6
- SLBOQBILGNEPEB-UHFFFAOYSA-N 1-chloroprop-2-enylbenzene Chemical compound C=CC(Cl)C1=CC=CC=C1 SLBOQBILGNEPEB-UHFFFAOYSA-N 0.000 description 5
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 5
- 235000018417 cysteine Nutrition 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 239000012736 aqueous medium Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 125000005353 silylalkyl group Chemical group 0.000 description 4
- 239000004971 Cross linker Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 3
- 239000006085 branching agent Substances 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 229960003151 mercaptamine Drugs 0.000 description 3
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229940035024 thioglycerol Drugs 0.000 description 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- FMFHUEMLVAIBFI-UHFFFAOYSA-N 2-phenylethenyl acetate Chemical compound CC(=O)OC=CC1=CC=CC=C1 FMFHUEMLVAIBFI-UHFFFAOYSA-N 0.000 description 2
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001356 alkyl thiols Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 238000007323 disproportionation reaction Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical group C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- 125000004438 haloalkoxy group Chemical group 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- HOGDNTQCSIKEEV-UHFFFAOYSA-N n'-hydroxybutanediamide Chemical compound NC(=O)CCC(=O)NO HOGDNTQCSIKEEV-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229940071127 thioglycolate Drugs 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- ZOKCNEIWFQCSCM-UHFFFAOYSA-N (2-methyl-4-phenylpent-4-en-2-yl)benzene Chemical compound C=1C=CC=CC=1C(C)(C)CC(=C)C1=CC=CC=C1 ZOKCNEIWFQCSCM-UHFFFAOYSA-N 0.000 description 1
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N 2-mercaptoethanol Substances OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 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
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 241000694440 Colpidium aqueous Species 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229920000028 Gradient copolymer Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical group 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000000746 allylic group Chemical group 0.000 description 1
- 229920005603 alternating copolymer Polymers 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000005135 aryl sulfinyl group Chemical group 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- SNBMGLUIIGFNFE-UHFFFAOYSA-N benzyl n,n-diethylcarbamodithioate Chemical compound CCN(CC)C(=S)SCC1=CC=CC=C1 SNBMGLUIIGFNFE-UHFFFAOYSA-N 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000013626 chemical specie Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 239000011243 crosslinked material Substances 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 239000003599 detergent Substances 0.000 description 1
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- 239000003085 diluting agent Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
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- 229930195733 hydrocarbon Natural products 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 239000007764 o/w emulsion Substances 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
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- 239000000575 pesticide Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 1
- 125000005499 phosphonyl group Chemical group 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 230000015843 photosynthesis, light reaction Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-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
- 238000007342 radical addition reaction Methods 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
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- 238000010992 reflux Methods 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229920006301 statistical copolymer Polymers 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 229940035658 visco-gel Drugs 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 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
- C08F2/38—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
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1802—C2-(meth)acrylate, e.g. ethyl (meth)acrylate
-
- 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
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
-
- 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
- C08F212/34—Monomers containing two or more unsaturated aliphatic radicals
- C08F212/36—Divinylbenzene
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)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0902052.0A GB0902052D0 (en) | 2009-02-09 | 2009-02-09 | Polymers,composition and use |
| GB0902052.0 | 2009-02-09 | ||
| PCT/GB2010/000232 WO2010089575A1 (en) | 2009-02-09 | 2010-02-09 | Branched copolymers, composition and uses |
Publications (2)
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| JP2012517493A true JP2012517493A (ja) | 2012-08-02 |
| JP2012517493A5 JP2012517493A5 (enExample) | 2013-03-28 |
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| US (3) | US20120108679A1 (enExample) |
| EP (3) | EP2393841A1 (enExample) |
| JP (1) | JP2012517493A (enExample) |
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| GB (1) | GB0902052D0 (enExample) |
| TW (1) | TW201043659A (enExample) |
| WO (3) | WO2010089575A1 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012530836A (ja) * | 2009-06-22 | 2012-12-06 | ユニリーバー・ピーエルシー | 分岐ポリマー分散剤 |
| WO2021131996A1 (ja) * | 2019-12-25 | 2021-07-01 | ダイキン工業株式会社 | フルオロポリマーの製造方法 |
| JP2022505544A (ja) * | 2018-10-31 | 2022-01-14 | ザ ユニバーシティ オブ リバプール | 分岐ポリマー |
| US12448467B2 (en) | 2017-04-26 | 2025-10-21 | The University Of Liverpool | Branched polymers |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2419496B1 (en) | 2009-04-17 | 2019-07-31 | California Institute of Technology | Associative polymers for mist-control |
| GB0910750D0 (en) * | 2009-06-22 | 2009-08-05 | Unilever Plc | Branched polymer dispersants |
| GB0910722D0 (en) * | 2009-06-22 | 2009-08-05 | Unilever Plc | Branched polymer dispersants |
| GB0916337D0 (en) * | 2009-09-17 | 2009-10-28 | Unilever Plc | Branched addition polymers for use in membranes |
| GB0916338D0 (en) * | 2009-09-17 | 2009-10-28 | Unilever Plc | Branched addition copolymers in curing systems |
| JP2016501312A (ja) * | 2012-12-18 | 2016-01-18 | ヘンケル アイピー アンド ホールディング ゲゼルシャフト ミット ベシュレンクテル ハフツング | 分岐ポリアクリレートの制御ラジカル重合プロセス |
| EP2970672A4 (en) | 2013-03-15 | 2016-08-24 | California Inst Of Techn | Associative polymers and related compositions, methods and systems |
| GB201405624D0 (en) | 2014-03-28 | 2014-05-14 | Synthomer Uk Ltd | Method of making a branched polymer, a branched polymer and uses of such a polymer |
| WO2016044803A1 (en) * | 2014-09-18 | 2016-03-24 | California Institute Of Technology | Associative polymers and related compositions, methods and systems |
| EP3350291A4 (en) | 2015-09-18 | 2019-04-10 | California Institute of Technology | ASSOCIATIVE POLYMERS FOR USE IN A RIVER AND RELATED COMPOSITIONS, METHODS AND SYSTEMS |
| CN108603131B (zh) | 2016-02-05 | 2022-01-21 | 国际壳牌研究有限公司 | 燃料组合物 |
| CN107537059B (zh) * | 2017-10-01 | 2020-06-05 | 山东煜和堂药业有限公司 | 一种双组份可溶性两性离子水凝胶敷料及其制备方法 |
| US9988590B1 (en) * | 2017-11-10 | 2018-06-05 | Afton Chemical Corporation | Polydialkylsiloxane poly (meth)acrylate brush polymers for lubricant additive application |
| CN111085088B (zh) * | 2018-10-23 | 2022-04-05 | 中国石油化工股份有限公司 | 气体过滤用聚丙烯腈纤维及其制备方法和应用 |
| US10947473B2 (en) * | 2019-05-17 | 2021-03-16 | Vanderbilt Chemicals, Llc | Less corrosive organic compounds as lubricant additives |
| CN110205835A (zh) * | 2019-05-31 | 2019-09-06 | 南通东屹高新纤维科技有限公司 | 高强度服装防水面料的制备方法 |
| CN110205834A (zh) * | 2019-05-31 | 2019-09-06 | 南通东屹高新纤维科技有限公司 | 防水透气聚醚砜面料 |
| US12384945B2 (en) | 2020-05-04 | 2025-08-12 | Bvw Holding Ag | Expansion mediated adhesive device |
| CN115449017B (zh) * | 2022-10-09 | 2023-08-15 | 山东诺尔生物科技有限公司 | 一种星型聚合物降滤失剂及其制备方法 |
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| JPS61501922A (ja) * | 1984-04-04 | 1986-09-04 | ベ− ア− エス エフ フアルベン ウント フア−ゼルン アクチエンゲゼルシヤフト | ヒドロキシル基含有のアクリレート共重合体の製造法 |
| JP2003138183A (ja) * | 2001-11-07 | 2003-05-14 | Fuji Photo Film Co Ltd | 静電式インクジェット用油性インク |
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| DE10035119A1 (de) * | 2000-07-19 | 2002-01-31 | Basf Ag | Teilverzweigte Polymere |
| EP2102259B1 (en) * | 2006-12-12 | 2012-06-27 | Unilever PLC | Polymers |
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- 2009-02-09 GB GBGB0902052.0A patent/GB0902052D0/en not_active Ceased
-
2010
- 2010-02-09 CN CN2010800158316A patent/CN102395606A/zh active Pending
- 2010-02-09 WO PCT/GB2010/000232 patent/WO2010089575A1/en not_active Ceased
- 2010-02-09 EP EP10705623A patent/EP2393841A1/en not_active Withdrawn
- 2010-02-09 US US13/148,472 patent/US20120108679A1/en not_active Abandoned
- 2010-02-09 CN CN2010800158763A patent/CN102395607A/zh active Pending
- 2010-02-09 WO PCT/GB2010/000233 patent/WO2010089576A1/en not_active Ceased
- 2010-02-09 US US13/148,471 patent/US20120108678A1/en not_active Abandoned
- 2010-02-09 JP JP2011548775A patent/JP2012517493A/ja active Pending
- 2010-02-09 WO PCT/GB2010/000227 patent/WO2010089571A1/en not_active Ceased
- 2010-02-09 EP EP10705907A patent/EP2393853A1/en not_active Withdrawn
- 2010-02-09 US US13/148,470 patent/US20110313054A1/en not_active Abandoned
- 2010-02-09 EP EP10705906A patent/EP2393842A1/en not_active Withdrawn
- 2010-02-09 TW TW099104075A patent/TW201043659A/zh unknown
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| JPS61501922A (ja) * | 1984-04-04 | 1986-09-04 | ベ− ア− エス エフ フアルベン ウント フア−ゼルン アクチエンゲゼルシヤフト | ヒドロキシル基含有のアクリレート共重合体の製造法 |
| JP2003138183A (ja) * | 2001-11-07 | 2003-05-14 | Fuji Photo Film Co Ltd | 静電式インクジェット用油性インク |
| WO2008071661A1 (en) * | 2006-12-12 | 2008-06-19 | Unilever Plc | Polymers |
| JP2010512441A (ja) * | 2006-12-12 | 2010-04-22 | ユニリーバー・エヌ・ブイ | ポリマー |
| JP2010532402A (ja) * | 2007-07-06 | 2010-10-07 | ヨツン エーエス | 分岐重合体、及びその重合体を含む防汚塗料組成物 |
| WO2009058460A2 (en) * | 2007-11-01 | 2009-05-07 | General Electric Company | System and method for battery control of hybrid locomotrives |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012530836A (ja) * | 2009-06-22 | 2012-12-06 | ユニリーバー・ピーエルシー | 分岐ポリマー分散剤 |
| US12448467B2 (en) | 2017-04-26 | 2025-10-21 | The University Of Liverpool | Branched polymers |
| JP2022505544A (ja) * | 2018-10-31 | 2022-01-14 | ザ ユニバーシティ オブ リバプール | 分岐ポリマー |
| US12291590B2 (en) | 2018-10-31 | 2025-05-06 | The University Of Liverpool | Branched polymers |
| WO2021131996A1 (ja) * | 2019-12-25 | 2021-07-01 | ダイキン工業株式会社 | フルオロポリマーの製造方法 |
| JP2021102731A (ja) * | 2019-12-25 | 2021-07-15 | ダイキン工業株式会社 | フルオロポリマーの製造方法 |
| JP6989792B2 (ja) | 2019-12-25 | 2022-01-12 | ダイキン工業株式会社 | フルオロポリマーの製造方法 |
| CN114867756A (zh) * | 2019-12-25 | 2022-08-05 | 大金工业株式会社 | 含氟聚合物的制造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2393841A1 (en) | 2011-12-14 |
| TW201043659A (en) | 2010-12-16 |
| CN102395606A (zh) | 2012-03-28 |
| US20120108678A1 (en) | 2012-05-03 |
| EP2393853A1 (en) | 2011-12-14 |
| GB0902052D0 (en) | 2009-03-11 |
| CN102395607A (zh) | 2012-03-28 |
| EP2393842A1 (en) | 2011-12-14 |
| WO2010089571A1 (en) | 2010-08-12 |
| US20110313054A1 (en) | 2011-12-22 |
| US20120108679A1 (en) | 2012-05-03 |
| WO2010089575A1 (en) | 2010-08-12 |
| WO2010089576A1 (en) | 2010-08-12 |
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