CN116635493A - 具有黏弹性和悬浮性的共聚物 - Google Patents
具有黏弹性和悬浮性的共聚物 Download PDFInfo
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- CN116635493A CN116635493A CN202180082246.6A CN202180082246A CN116635493A CN 116635493 A CN116635493 A CN 116635493A CN 202180082246 A CN202180082246 A CN 202180082246A CN 116635493 A CN116635493 A CN 116635493A
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- Prior art keywords
- copolymer
- acrylate
- group
- compound
- meth
- Prior art date
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- 229920001577 copolymer Polymers 0.000 title claims abstract description 85
- 239000000725 suspension Substances 0.000 title claims abstract description 9
- 239000000203 mixture Substances 0.000 claims abstract description 95
- 239000000178 monomer Substances 0.000 claims abstract description 66
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 32
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims description 74
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 44
- -1 alkyl methacrylates Chemical class 0.000 claims description 30
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 21
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 18
- 230000009477 glass transition Effects 0.000 claims description 18
- 239000011230 binding agent Substances 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000002245 particle Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 10
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000002966 varnish Substances 0.000 claims description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000004132 cross linking Methods 0.000 claims description 8
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 8
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 7
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- 239000004641 Diallyl-phthalate Substances 0.000 claims description 6
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 claims description 6
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 claims description 6
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 claims description 5
- 239000002202 Polyethylene glycol Substances 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 230000002209 hydrophobic effect Effects 0.000 claims description 5
- 239000004816 latex Substances 0.000 claims description 5
- 229920000126 latex Polymers 0.000 claims description 5
- 229920001223 polyethylene glycol Polymers 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- FYRWKWGEFZTOQI-UHFFFAOYSA-N 3-prop-2-enoxy-2,2-bis(prop-2-enoxymethyl)propan-1-ol Chemical compound C=CCOCC(CO)(COCC=C)COCC=C FYRWKWGEFZTOQI-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- 125000005907 alkyl ester group Chemical group 0.000 claims description 4
- 150000003863 ammonium salts Chemical class 0.000 claims description 4
- 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 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 150000002170 ethers Chemical class 0.000 claims description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
- 125000005394 methallyl group Chemical group 0.000 claims description 4
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 claims description 4
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- JHSWSKVODYPNDV-UHFFFAOYSA-N 2,2-bis(prop-2-enoxymethyl)propane-1,3-diol Chemical compound C=CCOCC(CO)(CO)COCC=C JHSWSKVODYPNDV-UHFFFAOYSA-N 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- JQRRFDWXQOQICD-UHFFFAOYSA-N biphenylen-1-ylboronic acid Chemical compound C12=CC=CC=C2C2=C1C=CC=C2B(O)O JQRRFDWXQOQICD-UHFFFAOYSA-N 0.000 claims description 3
- ZPOLOEWJWXZUSP-AATRIKPKSA-N bis(prop-2-enyl) (e)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C\C(=O)OCC=C ZPOLOEWJWXZUSP-AATRIKPKSA-N 0.000 claims description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 3
- VVYDVQWJZWRVPE-UHFFFAOYSA-L dimethyltin(2+);diiodide Chemical compound C[Sn](C)(I)I VVYDVQWJZWRVPE-UHFFFAOYSA-L 0.000 claims description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 3
- BKZFVHIMLVBUGP-UHFFFAOYSA-N (2-prop-2-enoyloxyphenyl) prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1OC(=O)C=C BKZFVHIMLVBUGP-UHFFFAOYSA-N 0.000 claims description 2
- WVAFEFUPWRPQSY-UHFFFAOYSA-N 1,2,3-tris(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1C=C WVAFEFUPWRPQSY-UHFFFAOYSA-N 0.000 claims description 2
- KTRQRAQRHBLCSQ-UHFFFAOYSA-N 1,2,4-tris(ethenyl)cyclohexane Chemical compound C=CC1CCC(C=C)C(C=C)C1 KTRQRAQRHBLCSQ-UHFFFAOYSA-N 0.000 claims description 2
- QLLUAUADIMPKIH-UHFFFAOYSA-N 1,2-bis(ethenyl)naphthalene Chemical compound C1=CC=CC2=C(C=C)C(C=C)=CC=C21 QLLUAUADIMPKIH-UHFFFAOYSA-N 0.000 claims description 2
- HSOOIVBINKDISP-UHFFFAOYSA-N 1-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(CCC)OC(=O)C(C)=C HSOOIVBINKDISP-UHFFFAOYSA-N 0.000 claims description 2
- PRAMZQXXPOLCIY-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethanesulfonic acid Chemical compound CC(=C)C(=O)OCCS(O)(=O)=O PRAMZQXXPOLCIY-UHFFFAOYSA-N 0.000 claims description 2
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 claims description 2
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 claims description 2
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 claims description 2
- CEXQWAAGPPNOQF-UHFFFAOYSA-N 2-phenoxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC1=CC=CC=C1 CEXQWAAGPPNOQF-UHFFFAOYSA-N 0.000 claims description 2
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 claims description 2
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-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
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 2
- 229930006000 Sucrose Natural products 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical compound C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 claims description 2
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 claims description 2
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 claims description 2
- 239000002537 cosmetic Substances 0.000 claims description 2
- 125000004386 diacrylate group Chemical group 0.000 claims description 2
- 239000006185 dispersion Substances 0.000 claims description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 2
- 239000003337 fertilizer Substances 0.000 claims description 2
- 125000003827 glycol group Chemical group 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000003973 paint Substances 0.000 claims description 2
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 claims description 2
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 claims description 2
- 125000005498 phthalate group Chemical class 0.000 claims description 2
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 2
- 229920001281 polyalkylene Polymers 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- OCAAZRFBJBEVPS-UHFFFAOYSA-N prop-2-enyl carbamate Chemical compound NC(=O)OCC=C OCAAZRFBJBEVPS-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
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 claims description 2
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 claims description 2
- SZHIIIPPJJXYRY-UHFFFAOYSA-M sodium;2-methylprop-2-ene-1-sulfonate Chemical compound [Na+].CC(=C)CS([O-])(=O)=O SZHIIIPPJJXYRY-UHFFFAOYSA-M 0.000 claims description 2
- 230000000087 stabilizing effect Effects 0.000 claims description 2
- 239000005720 sucrose Substances 0.000 claims description 2
- 150000003673 urethanes Chemical class 0.000 claims description 2
- UBTYFVJZTZYJHZ-UHFFFAOYSA-N n-[2-(prop-2-enoylamino)propyl]prop-2-enamide Chemical compound C=CC(=O)NC(C)CNC(=O)C=C UBTYFVJZTZYJHZ-UHFFFAOYSA-N 0.000 claims 1
- 150000007519 polyprotic acids Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 15
- 229920006243 acrylic copolymer Polymers 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000008367 deionised water Substances 0.000 description 7
- 229910021641 deionized water Inorganic materials 0.000 description 7
- 238000012512 characterization method Methods 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 229940059574 pentaerithrityl Drugs 0.000 description 6
- 238000000518 rheometry Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002023 wood Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-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
- 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 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 2
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000013016 damping Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- ZWUBFMWIQJSEQS-UHFFFAOYSA-N 1,1-bis(ethenyl)cyclohexane Chemical compound C=CC1(C=C)CCCCC1 ZWUBFMWIQJSEQS-UHFFFAOYSA-N 0.000 description 1
- TYMYJUHDFROXOO-UHFFFAOYSA-N 1,3-bis(prop-2-enoxy)-2,2-bis(prop-2-enoxymethyl)propane Chemical compound C=CCOCC(COCC=C)(COCC=C)COCC=C TYMYJUHDFROXOO-UHFFFAOYSA-N 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- JOLVYUIAMRUBRK-UHFFFAOYSA-N 11',12',14',15'-Tetradehydro(Z,Z-)-3-(8-Pentadecenyl)phenol Natural products OC1=CC=CC(CCCCCCCC=CCC=CCC=C)=C1 JOLVYUIAMRUBRK-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 1
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 1
- QENRKQYUEGJNNZ-UHFFFAOYSA-N 2-methyl-1-(prop-2-enoylamino)propane-1-sulfonic acid Chemical compound CC(C)C(S(O)(=O)=O)NC(=O)C=C QENRKQYUEGJNNZ-UHFFFAOYSA-N 0.000 description 1
- YLKVIMNNMLKUGJ-UHFFFAOYSA-N 3-Delta8-pentadecenylphenol Natural products CCCCCCC=CCCCCCCCC1=CC=CC(O)=C1 YLKVIMNNMLKUGJ-UHFFFAOYSA-N 0.000 description 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
- MKTOIPPVFPJEQO-UHFFFAOYSA-N 4-(3-carboxypropanoylperoxy)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)OOC(=O)CCC(O)=O MKTOIPPVFPJEQO-UHFFFAOYSA-N 0.000 description 1
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- JOLVYUIAMRUBRK-UTOQUPLUSA-N Cardanol Chemical compound OC1=CC=CC(CCCCCCC\C=C/C\C=C/CC=C)=C1 JOLVYUIAMRUBRK-UTOQUPLUSA-N 0.000 description 1
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- GQPVFBDWIUVLHG-UHFFFAOYSA-N [2,2-bis(hydroxymethyl)-3-(2-methylprop-2-enoyloxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)(CO)COC(=O)C(C)=C GQPVFBDWIUVLHG-UHFFFAOYSA-N 0.000 description 1
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- 229910001431 copper ion Inorganic materials 0.000 description 1
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
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- 230000007613 environmental effect Effects 0.000 description 1
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- XSXLCQLOFRENHC-UHFFFAOYSA-N ethyl n-benzylcarbamate Chemical compound CCOC(=O)NCC1=CC=CC=C1 XSXLCQLOFRENHC-UHFFFAOYSA-N 0.000 description 1
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- 238000001914 filtration Methods 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
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- KUQWZSZYIQGTHT-UHFFFAOYSA-N hexa-1,5-diene-3,4-diol Chemical compound C=CC(O)C(O)C=C KUQWZSZYIQGTHT-UHFFFAOYSA-N 0.000 description 1
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- 238000005259 measurement Methods 0.000 description 1
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- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
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- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
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- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明提供由至少四种单体在不存在甲基丙烯酸的情况下制备的交联磺化丙烯酸共聚物P。本发明还包括制备具有黏弹性和悬浮性并包含共聚物P的含水组合物C。
Description
本发明提供由至少四种单体在不存在甲基丙烯酸的情况下制备的交联磺化丙烯酸共聚物P。本发明还包括制备具有黏弹性和悬浮性并包含该共聚物P的含水组合物。
许多技术领域需要使用结合几种性质的试剂。特别地,一些技术领域需要控制组合物的流变性和质地。用于此目的的试剂还必须能够稳定这些组合物。
在涂料组合物领域,特别是对于木材染色剂组合物,所使用的试剂必须能够控制流变性,而且还能够对这些包含颗粒的组合物产生悬浮作用。木材染色剂组合物通常将溶剂,特别是水,与黏合剂例如丙烯酸黏合剂、醇酸黏合剂或醇酸-氨基甲酸乙酯黏合剂以及颜料颗粒结合。这些组合物使其能够保护在其上施用的基材,特别是木材或混凝土基材。因此,组合物的不同成分的相容性也是至关重要的。
特别地,组合物的流变性和质地控制试剂必须具有使它们能够有效地与这些组合物中存在的其他物质结合的玻璃化转变温度,特别是与通常为颗粒形式的黏合剂结合。
组合物所需的悬浮作用是在一段时间内例如在储存组合物时以稳定的方式将颗粒保持悬浮在连续相中的能力。颗粒通常是实心的、中空的或固体的。它们也可以是不能与连续相混合、也不能被包裹或以气态形式存在的液体实体。它们的形状、质地和结构可以有很大的变化,特别是取决于预期的最终性质。
悬浮性能可以通过确定弹性模量值G’、阻尼系数(Tanδ)和弹性强度值来进行评价。
此外,有必要控制这些组合物的黏度,无论是低剪切梯度或中等剪切梯度还是高剪切梯度的黏度。事实上,在其制备、储存、应用或干燥过程中,组合物可能受到许多需要特别复杂的流变性、特别是黏弹性的应力。
在流变学中,直线型黏弹性材料的性质介于以弹性模量E(或G)表示的理想弹性固体的性质和以黏滞阻尼系数表示的牛顿黏性液体的性质之间。材料的弹性反映了其在形变后保持和返还能量的能力。材料的黏性反映了其耗散能量的能力。
因此,还必须改善组合物的黏弹性,以使该组合物在形变时既具有黏性又具有弹性。黏性组分使这种组合物能够承受剪切流,并表现出当施加应力时形变随时间线性增加。弹性组分允许在施加应力时发生形变,然后一旦应力中止,就会恢复到原始状态。
因此,需要有能够向组合物提供黏弹性和悬浮性的试剂。
此外,特别是由于环境原因,还非常需要不含甲基丙烯酸的组合物,同时与现有技术中的组合物相比提供持续的或改进的性能。事实上,应尽可能限制甲基丙烯酸的使用,特别是由剧毒化合物丙酮氰醇制备的甲基丙烯酸。
文献US2017003717和US20190315897描述了用甲基丙烯酸制备的共聚物。文献US20080193405描述了含水组合物或含醇组合物的制备,该组合物包含与丙烯酸和交联化合物的混合物相关的共聚物的组合。文献WO2014185381涉及包含氟化共聚物的锂电池用黏合剂组合物。
因此,需要具有改进的性质的共聚物,其使得有可能为现有技术的聚合物的全部或部分问题提供解决方案。
因此,本发明提供了在不存在甲基丙烯酸的情况下通过以下物质的至少一种聚合反应制备的共聚物P:
a.至少一种阴离子单体(a),其选自丙烯酸、丙烯酸盐、丙烯酸低聚物、丙烯酸低聚物盐、及其组合;
b.至少一种非离子单体(b),其选自苯乙烯、选自丙烯酸、甲基丙烯酸的酸的C1-C8酯、及其组合;
c.至少一种化合物(c),其选自2-丙烯酰胺基-2-甲基丙磺酸、2-磺乙基甲基丙烯酸酯、甲基丙烯磺酸钠、苯乙烯磺酸酯、它们的盐类、及其组合;
d.至少一种交联化合物(d)或包含至少两个可聚合的烯属不饱和键的化合物(d)。
优选地,根据本发明,共聚物P可以单独由化合物a、b、c和d制备。
还优选地,根据本发明,单体(a)是丙烯酸或式(I)的丙烯酸低聚物的混合物:
其中m为1至10的整数或小数,优选为2至4的整数或小数。优选地,根据本发明,单体(a)为丙烯酸。
还优选地,根据本发明,单体(b)选自:
-丙烯酸烷基酯,特别是丙烯酸C1-C8烷基酯,优选丙烯酸C1-C4烷基酯,更优选丙烯酸甲酯、丙烯酸乙酯、丙烯酸丙酯、丙烯酸异丁酯、丙烯酸正丁酯,
-甲基丙烯酸烷基酯,特别是甲基丙烯酸C1-C8烷基酯,优选甲基丙烯酸C1-C4烷基酯,更优选甲基丙烯酸甲酯、甲基丙烯酸乙酯、甲基丙烯酸丙酯、甲基丙烯酸异丁酯、甲基丙烯酸正丁酯,
-丙烯酸芳基酯,优选丙烯酸苯酯、丙烯酸苄酯、丙烯酸苯氧基乙酯,
-甲基丙烯酸芳基酯,优选甲基丙烯酸苯酯、甲基丙烯酸苄酯、甲基丙烯酸苯氧基乙酯,以及
-其组合。
更优选地,根据本发明,单体(b)选自丙烯酸乙酯和丙烯酸丁酯,更优选丙烯酸乙酯。
优选地,根据本发明的单体(b)是非氟化单体,或者不同于甲基丙烯酸2,2,2-三氟乙酯的单体(b)。根据本发明,优选的单体(c)选自2-丙烯酰胺基-2-甲基丙磺酸(AMPS)及其钠盐或铵盐。
根据本发明,优选的化合物(d)选自多不饱和芳香族单体如二乙烯基苯、二乙烯基萘和三乙烯基苯,多不饱和脂环族单体如1,2,4-三乙烯基环己烷,二价邻苯二甲酸酯如邻苯二甲酸二烯丙酯,多烯基醚如三烯丙基季戊四醇、季戊四醇二烯丙基醚、蔗糖二烯丙基醚、蔗糖八烯丙基醚和三羟甲基丙烷二烯丙基醚,多不饱和多元醇酯或多元酸酯如1,6-己二醇二(甲基)丙烯酸酯、四亚甲基三(甲基)丙烯酸酯、丙烯酸烯丙酯、衣康酸二烯丙酯、富马酸二烯丙酯、马来酸二烯丙酯、三羟甲基丙烷三(甲基)丙烯酸酯、三羟甲基丙烷二(甲基)丙烯酸酯、聚亚烷基氧基二醇二(甲基)丙烯酸酯和聚乙二醇二(甲基)丙烯酸酯,亚烷基双丙烯酰胺如亚甲基双丙烯酰胺和亚丙基双丙烯酰胺,亚甲基双丙烯酰胺的羟基或羧基衍生物如Ν,Ν’-二羟甲基亚甲基双丙烯酰胺、多亚烷二醇二(甲基)丙烯酸酯如乙二醇二(甲基)丙烯酸酯、二乙二醇二(甲基)丙烯酸酯、三乙二醇二(甲基)丙烯酸酯、甲基丙烯酸烯丙酯、乙二醇二甲基丙烯酸酯、丁二醇二甲基丙烯酸酯、季戊四醇二丙烯酸酯、季戊四醇三丙烯酸酯和季戊四醇四丙烯酸酯,聚亚烷基氧基二醇二(甲基)丙烯酸酯如聚乙二醇二丙烯酸酯、双酚A二丙烯酸酯、丁二醇二甲基丙烯酸酯、2,2-二甲基丙二醇二甲基丙烯酸酯、亚苯基二丙烯酸酯、不对称交联化合物、及其混合物。
根据本发明的优选不对称交联化合物(d)选自:
式(II)的化合物:
其中:
-L1表示CH2、单烷氧基化的CH2或多烷氧基化的CH2,
-R1表示-C(H)=CH2、-C(CH3)=CH2、-C(H)=C(H)C(O)OH、-C(H)=C(H)CH3、-C(=CH2)CH2C(O)OH、-CH2C(=CH2)C(O)OH、Q1OQ2OC(O)C(CH3)=CH2或Q1OQ2OC(O)C(H)=CH2,
-Q1表示不对称二异氰酸酯化合物的二价残基,优选地选自甲苯基-1,3-二异氰酸酯(TDI)和异佛尔酮二异氰酸酯(IPDI),
-Q2表示CH2、CH2-CH2、单烷氧基化的CH2、单烷氧基化的CH2-CH2、多烷氧基化的CH2或多烷氧基化的CH2-CH2;优选式(II)的化合物,其中:
-L1表示CH2和
-R1表示-C(H)=CH2、-C(CH3)=CH2、-C(H)=C(H)C(O)OH、-C(H)=C(H)CH3、-C(=CH2)CH2C(O)OH、-CH2C(=CH2)C(O)OH或式(II)的化合物,其中:
-L1表示单烷氧基化的CH2或多烷氧基化的CH2,
-R1表示Q1OQ2OC(O)C(CH3)=CH2或Q1OQ2OC(O)C(H)=CH2,
-Q1表示不对称二异氰酸酯化合物的二价残基,优选地选自甲苯基-1,3-二异氰酸酯(TDI)和异佛尔酮二异氰酸酯(IPDI),
-Q2表示CH2、CH2-CH2、单烷氧基化的CH2、单烷氧基化的CH2-CH2、多烷氧基化的CH2或多烷氧基化的CH2-CH2;
式(III)的化合物:
其中:
-L2表示CH2、单烷氧基化的CH2或多烷氧基化的CH2,
-R2表示-C(H)=CH2、-C(CH3)=CH2、-C(H)=C(H)C(O)OH、-C(H)=C(H)CH3、-C(=CH2)CH2C(O)OH、-CH2C(=CH2)C(O)OH、Q3OQ4OC(O)C(CH3)=CH2或Q3OQ4OC(O)C(H)=CH2,
-Q3表示不对称二异氰酸酯化合物的二价残基,优选地选自甲苯基-1,3-二异氰酸酯(TDI)和异佛尔酮二异氰酸酯(IPDI),
-Q4表示CH2、CH2-CH2、单烷氧基化的CH2、单烷氧基化的CH2-CH2、多烷氧基化的CH2或多烷氧基化的CH2-CH2;优选式(III)的化合物,其中:
-L2表示CH2,
-R2表示-C(H)=CH2、-C(CH3)=CH2、-C(H)=C(H)C(O)OH、-C(H)=C(H)CH3、-C(=CH2)CH2C(O)OH、-CH2C(=CH2)C(O)OH或式(III)的化合物,其中:
-L2表示单烷氧基化的CH2或多烷氧基化的CH2,
-R2表示Q3OQ4OC(O)C(CH3)=CH2或Q3OQ4OC(O)C(H)=CH2,
-Q3表示不对称二异氰酸酯化合物的二价残基,优选地选自甲苯基-1,3-二异氰酸酯(TDI)和异佛尔酮二异氰酸酯(IPDI),
-Q4表示CH2、CH2-CH2、单烷氧基化的CH2、单烷氧基化的CH2-CH2、多烷氧基化的CH2或多烷氧基化的CH2-CH2;
式(IV)的化合物:
其中:
-R3独立地表示H或CH3,
-L3独立地表示直链或带支链的C1-C20亚烷基以及
-n独立地表示0或1至30的整数,例如1至20、特别地1至15、特别地1至10;
选自二(甲基)丙烯酸酯类如聚亚烷基二醇二(甲基)丙烯酸酯,特别是聚丙二醇二(甲基)丙烯酸酯、乙二醇二(甲基)丙烯酸酯、聚乙二醇二(甲基)丙烯酸酯、三乙二醇二(甲基)丙烯酸酯、1,3-丁二醇二(甲基)丙烯酸酯、1,6-丁二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、1,9-壬二醇二(甲基)丙烯酸酯、还有2,2’-双(4-(丙烯酰氧基-丙氧基苯基)丙烷、2,2’-双(4-(丙烯酰氧基二乙氧基苯基)丙烷、三(甲基)丙烯酸酯化合物如三羟甲基丙烷三(甲基)丙烯酸酯、乙氧基化的三羟甲基丙烷三(甲基)丙烯酸酯、三羟甲基乙烷三(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯和四羟甲基甲烷三(甲基)丙烯酸酯;四(甲基)丙烯酸酯化合物如二三羟甲基丙烷四(甲基)丙烯酸酯、四羟甲基甲烷四(甲基)丙烯酸酯、和季戊四醇四(甲基)丙烯酸酯;六(甲基)丙烯酸酯化合物如二季戊四醇六(甲基)丙烯酸酯;五(甲基)丙烯酸酯化合物如二季戊四醇五(甲基)丙烯酸酯;烯丙基化合物,例如(甲基)丙烯酸烯丙酯、邻苯二甲酸二烯丙酯、衣康酸二烯丙酯、富马酸二烯丙酯、马来酸二烯丙酯;每分子具有2个至8个基团的多烯丙基蔗糖醚,季戊四醇多烯丙基醚如季戊四醇二烯丙基醚、季戊四醇三烯丙基醚和季戊四醇四烯丙基醚;三羟甲基丙烷多烯丙基醚,如三羟甲基丙烷二烯丙基醚和三羟甲基丙烷三烯丙基醚的化合物;
选自多不饱和化合物,特别是二乙烯基二醇、二乙烯基苯、二乙烯基环己烷和亚甲基二丙烯酰胺的化合物;
选自三官能团交联单体,特别是三羟甲基丙烷三(甲基)丙烯酸酯(TMPTA)、乙氧基化的三羟甲基丙烷三(甲基)丙烯酸酯,例如TMPTA3EO的化合物;
选自乙二醇二(甲基)丙烯酸酯、亚甲基二丙烯酰胺、邻苯二甲酸二烯丙酯、马来酸二烯丙酯的化合物;
两种不同单体的混合物,例如EGDCPEA(乙二醇二环戊烯基醚丙烯酸酯)和TMPTA或EGDCPEA和TMPTA 3EO;
式(V)的化合物:
其中:
-R4独立地表示H或CH3,
-R5独立地表示-C(H)=CH2、-C(CH3)=CH2、-C(H)=C(H)C(O)OH、-C(H)=C(H)CH3、-C(=CH2)CH2C(O)OH、-CH2C(=CH2)C(O)OH,
-L4独立地表示亚乙基、亚丙基或亚丁基以及
-p独立地表示0或1至30的整数或小数,优选地p表示1至18、1至15或2至16或2至12的整数或小数;更优选地化合物选自式(V)的化合物(d1),其中R4表示H,R5表示-C(H)=CH2,L4表示CH2-CH2和p表示10(CAS号99742-80-0);还特别优选式(V)的化合物(d2),其中R4表示H、R5表示-C(CH3)=CH2、L4表示CH2-CH2和p表示3.5(CAS号121826-50-4);还特别优选式(V)的化合物(d3),其中R4表示H、L4表示CH2-CH2、R5表示-C(CH3)=CH2和p表示10(CAS号121826-50-4)。
在制备共聚物P时,所使用的化合物的量可以不同。优选地,根据本发明,共聚物P包含:
-25重量%至60重量%的单体(a),
-39.89重量%至59重量%的单体(b),
-0.1重量%至8重量%的单体(c)和
-0.01重量%至8重量%的单体(d)。
还优选地,根据本发明,共聚物P包含:
-25重量%至60重量%的单体(a),
-44.89重量%至59重量%的单体(b),
-0.1重量%至8重量%的单体(c)和
-0.01重量%至3重量%的单体(d)。
还优选地,根据本发明,共聚物P包含:
-30重量%至50重量%的单体(a),
-49.89重量%至54重量%的单体(b),
-0.1重量%至8重量%的单体(c)和
-0.01重量%至8重量%的单体(d)。
还优选地,根据本发明,共聚物P包含:
-25重量%至45重量%的单体(a),
-54.89重量%至59重量%的单体(b),
-0.1重量%至8重量%的单体(c)和
-0.01重量%至8重量%的单体(d)。
更优选地,根据本发明,相对于单体(a)、单体(c)和单体(d)的重量,共聚物P包含39.89重量%至59重量%的单体(b)。根据本发明,共聚物P不同于不含甲基丙烯酸而由30.0重量%的丙烯酸、58.2重量%的丙烯酸乙酯、7.5重量%的甲基丙烯酸-2,2,2-三氟乙酯、2.5重量%的丙烯酰胺基-2-甲基丙磺酸和0.8重量%的二甲基丙烯酸乙烯酯制备的共聚物。
根据本发明的共聚物P具有许多特别有利的性质。特别地,共聚物P具有特定的玻璃化转变温度(Tg)。优选地,使用Flory-Fox方程计算的根据本发明的聚合物P的玻璃化转变温度(Tg)小于60℃,优选小于30℃。Flory-Fox方程使得从用于制备共聚物的单体的参数计算共聚物的玻璃化转变温度成为可能,所使用的任何单体(e)除外。
还优选地,根据本发明的共聚物P被完全地或部分地中和,优选地使用选自NaOH、KOH、LiOH、铵衍生物、氨、胺类碱、及其组合的化合物完全地或部分地中和,胺类碱例如三乙醇胺、氨甲基丙醇或2-氨基-2-甲基-丙醇(AMP)。
除了化合物a、b、c和d之外,根据本发明的共聚物P可以通过还使用至少一种疏水性单体(e)、特别是疏水性缔合单体(e)的聚合反应制备。优选地根据本发明,单体(e)包含可聚合的烯属不饱和键、聚亚烷基二醇基团和疏水端基。优选地根据本发明,疏水端基是包含6个至40个碳原子的直链的、带支链的或环状的、饱和的、不饱和的或芳香族的烃基。优选地根据本发明,单体(e)为式(VI)的化合物:
R6-(OE)q-(OP)r-R7
(VI)
其中:
-q和r,相同或不同,独立地表示0或表示小于150的整数或小数,q+r的和为5至150,优选为10至150,有利地为10至100,更有利地为10至60,
-EO表示CH2CH2O基团,
-PO独立地表示选自CH(CH3)CH2O和CH2CH(CH3)O的基团,
-R6表示包含至少一个可聚合的烯属不饱和键的基团,优选选自丙烯酸酯基、甲基丙烯酸酯基、丙烯酸氨基甲酸酯基、甲基丙烯酸氨基甲酸酯基、乙烯基、烯丙基、甲基烯丙基、异戊二烯基、不饱和的氨基甲酸酯基,特别是丙烯酸氨基甲酸酯基、甲基丙烯酸氨基甲酸酯基、α-α’-二甲基异丙烯基苄基氨基甲酸酯基、烯丙基氨基甲酸酯的基团,更优选选自丙烯酸酯基、甲基丙烯酸酯基、丙烯酸氨基甲酸酯基、甲基丙烯酸氨基甲酸酯基、乙烯基、烯丙基、甲基烯丙基和异戊二烯基的基团,甚至更优选甲基丙烯酸酯基,
-R7独立地表示包含6个至40个、优选6个至32个、更优选8个至30个碳原子的直链的、带支链的或环状的、饱和的、不饱和的或芳香族的烃基。
优选地,R7表示衍生自式(VII)的格尔伯特醇的烷基:
其中R8和R9独立地表示C6-C40烷基,优选C6-C32烷基。
还优选地根据本发明,R7表示包含6个至40个碳原子的直链的烷基或烯基,特别是环己基。根据本发明,R7还可以表示衍生自通过氧代反应得到的醇的烷基。
根据本发明,R7可以表示包含6个至40个、优选6个至32个、更优选6个至30个碳原子的芳香族的基团。
根据本发明,R7可以表示式(VIII)的基团:
其中R10表示式C15H31-s的烃基团,其中s表示0、2、4或6;因此R10可以包括0个、1个、2个或3个亚乙基不饱和键(双键)。这种式(VIII)的基团有利地衍生自腰果酚,因此其是生物来源的。
根据本发明,R7可以表示包含2个至5个苯基的基团,如式(IX)的三苯乙烯基苯基(TSP):
或式(X)或式(XI)的二苯乙烯基苯基(DSP):
或五苯乙烯基枯基苯基。
特别地,R7独立地表示包含6个至40个碳原子的直链的、带支链的或环状的、饱和的、不饱和的或芳香族的烃基,优选直链或带支链的C6-C40烷基,优选直链或带支链的C8-C30烷基、C6-C40芳基,优选C8-C30芳基,优选包括2个至5个苯基,例如三苯乙烯基苯基。
优选地根据本发明,q表示整数或小数,有利地表示大于10或等于10的整数。
优选地根据本发明,q值严格大于r值。更优选地根据本发明,按重量计,q和r的量分别为(q=100和r=0)至(q=70和r=30)。
根据一种变型,r为零,q表示整数或小数,有利地为10至100的数,有利地10至60,更有利地20至60,甚至更有利地20至40。
根据另一种变型,r和q各自都不等于0。特别地,q和r,相同或不同,独立地表示整数或小数,有利地为5至100的整数或小数,q+r的和为10至150,有利地为10至100,更有利地为10至60。优选地根据本发明,q值严格大于r值。在该情况下,优选地根据本发明,按重量计,q和r的量分别为(q=90和r=10)至(q=70和r=30)。
更优选地根据本发明,n表示0。
有利地根据本发明,相对于单体的总量,共聚物P可以包含0.4重量%至30重量%的单体(e)。
根据本发明的共聚物P可以根据已知的方法制备。具体地,根据本发明的共聚物P通过使用不同化合物a、b、c和d、任选地化合物e的聚合反应,通过自由基聚合反应,例如乳液、分散体或溶液中的聚合反应来制备。有利地,共聚物P在水中制备,优选在至少一种表面活性剂化合物例如十二烷基硫酸钠或十二烷基月桂酸钠的存在下制备。
根据本发明共聚物P的制备还可以使用一种或多于一种化合物,特别是至少一种引发剂化合物单独使用或至少一种引发剂化合物与至少一种链转移剂结合使用。作为引发剂化合物的实例,可以使用选自偶氮型引发剂化合物(例如偶氮二异丁腈),过氧化物化合物,优选过氧化氢、过氧化苯甲酰、过氧化氢苯甲酰、及其混合物的一种化合物。也可以提及碱性金属过硫酸盐,特别是过硫酸钠和过硫酸钾、过硫酸铵,部分水溶性的过氧化物,特别是过氧化丁二酸、叔丁基过氧化氢、枯基过氧化氢,与铜离子、亚铁离子、亚硫酸根离子或亚硫酸氢根离子结合的过硫酸盐、及其混合物。作为链转移剂的实例,可以使用硫醇化合物,特别是包含至少4个碳原子的硫醇化合物,如丁基硫醇、正辛基硫醇、正十二烷基硫醇、叔十二烷基硫醇或巯基丙酸异辛酯。
根据本发明,引发自由基或产生自由基的化合物因此可以与至少一种受控的自由基聚合转移剂结合,特别是与RAFT(可逆加成-断裂链转移)转移剂结合。优选地,该反应是乳液中的自由基聚合反应。
因此,优选地根据本发明,在水中制备共聚物P使得有可能获得乳液形式的聚合物含水组合物。
根据本发明共聚物P特别有利的性质使得其能够用于许多技术领域。特别地,根据本发明的共聚物P可用于改善组合物、特别是含水组合物、优选包含颗粒的含水组合物的黏弹性和悬浮性。因此,除了共聚物P之外,本发明提供了包含至少一种根据本发明的共聚物P的含水组合物C。优选地,根据本发明的含水组合物C包含至少一种根据本发明的共聚物P和固体、液体或气体颗粒,以及任选地黏合剂化合物。
优选地,根据本发明的含水组合物C包含0.1重量%至5重量%的共聚物P。更优选地,根据本发明的组合物C包含0.5重量%至3重量%的共聚物P。
优选地,对于根据本发明的含水组合物C,颗粒是选自化妆品、植物检疫产品、肥料、涂料产品的产品的颗粒。更优选地,对于根据本发明的含水组合物C,含水组合物C是包含共聚物P、颜料颗粒和胶乳形式的黏合剂化合物的清漆组合物,其任选地包含颜料-分散化合物。优选地根据本发明,黏合剂化合物具有使用Flory-Fox方程计算的玻璃化转变温度,该温度与共聚物P的玻璃化转变温度+/-10℃相同。还优选地根据本发明,黏合剂化合物具有使用Flory-Fox方程计算的玻璃化转变温度,该温度与共聚物P的玻璃化转变温度+/-5℃相同。根据本发明,优选的黏合剂化合物是丙烯酸化合物、醇酸化合物或醇酸-氨基甲酸酯化合物,或者苯乙烯-丙烯酸化合物或苯乙烯-丁二烯化合物。
根据本发明的共聚物P的性质使得其能够在显著变化的条件下使用。特别地,共聚物P的性质可用于不同的pH值。优选地,根据本发明的含水组合物C的pH为3至13,优选地pH为5至13。还优选地,含水组合物C的pH为4至8或5至7。
本发明还涉及制备黏弹性和悬浮性含水组合物C的方法,包括引入至少一种根据本发明的共聚物P和搅拌组合物C。共聚物P使得改善根据本发明的组合物C的性质成为可能。特别地,共聚物P使得改善该组合物、特别是清漆组合物C的稳定性成为可能。因此,本发明还涉及稳定清漆组合物C的方法,方法包括将至少一种根据本发明的共聚物P引入含水清漆基组合物C中。优选地,清漆基组合物C包含胶乳形式的黏合剂化合物,其使用Flory-Fox方程计算的玻璃化转变温度与共聚物P的玻璃化转变温度+/-10℃相同。还优选地,对于该方法,黏合剂化合物的使用Flory-Fox方程计算的玻璃化转变温度与共聚物P的玻璃化转变温度+/-5℃相同。
根据本发明的共聚物P对于控制含水组合物的流变性的各种组分具有特别有利的性能。特别地,根据本发明的共聚物P使得控制含水组合物的流动阈值成为可能。
流动阈值对应于施加到含水组合物上使该组合物流动的剪切应力的值。在没有足够应力的情况下,这种含水组合物的黏度会阻止其在可接受的时间范围内自发流动。
因此,本发明还提供了控制含水组合物的流动阈值的方法,该方法包括将至少一种根据本发明的共聚物P引入含水组合物中。优选地,根据实施例中描述的方法测量的该含水组合物的流动阈值大于0.1Pa、更优选大于0.5Pa或大于2Pa、优选大于4Pa。
更优选地,根据本发明的组合物C包含0.1重量%至5重量%的共聚物P并具有大于0.1Pa、更优选大于0.5Pa、或大于2Pa、优选大于4Pa的流动阈值。还更优选地,根据本发明的组合物C包含0.5重量%至3重量%的共聚物P并具有大于0.1Pa、更优选大于0.5Pa、或大于2Pa、优选大于4Pa的流动阈值。
根据本发明,根据本发明的共聚物P的特定的、有利的或优选的特征限定了根据本发明的组合物和根据本发明的方法,根据本发明的组合物和根据本发明的方法也是特定的、有利的或优选的。
以下实施例说明了本发明的各个方面。
实施例
实施例1:根据本发明的共聚物的制备与表征
根据本发明的共聚物P的制备反应在装有机械锚式搅拌和油浴加热的可用体积为1升的圆柱形玻璃反应器中进行。搅拌在整个制备过程中保持不变。
使用了以下单体:
-单体a:
·化合物(a1)、丙烯酸(AA),
·化合物(a2)、甲基丙烯酸(MAA),
-单体b:化合物(b1)、丙烯酸乙酯(EA),
-化合物c:化合物(c1)、2-丙烯酰胺基-2-甲基丙磺酸(AMPS)钠盐,
-交联化合物d:
·化合物(d1)、乙二醇二甲基丙烯酸酯(EDMA),
·化合物(d2)、邻苯二甲酸二烯丙酯(DAP),
·化合物(d3),式IV化合物,其中R3表示H,L3表示CH2CH2基团,n表示1,
·化合物(d4)、三烯丙基季戊四醇(APE),
·化合物(d5)、三羟甲基丙烷三丙烯酸酯(TMPTA),
-疏水性单体e:式VI的化合物(e1),其中R6表示甲基丙烯酸酯基团,q表示25,EO表示CH2CH2O基团,r表示0,R7表示式VII的基团,其中R8表示直链的C6烷基,R9表示直链的C10烷基。
根据本发明的共聚物(P1)的制备与表征
在反应器中,引入460g去离子水和6.48g十二烷基硫酸钠。在第一个玻璃烧杯中,根据表1所示的比例,称量102.14g单体(a1)、160.20g单体(b1)、4.57g化合物(d1)、20.05g单体(e1)、3.38g十二烷基硫酸钠和124g去离子水。在第二个玻璃烧杯中,称量0.914g过硫酸铵,然后将其溶解在10g去离子水中。在第三个玻璃烧杯中,称量0.100g焦亚硫酸钠,然后将其溶解在10g去离子水中。在第四个容器中,如一次性注射器中,称量5.27g 50重量%的化合物(c1)水溶液。
将反应器内容物加热至76℃±2℃。
将4个容器中的试剂于76℃±2℃的温度下在2小时30分钟内引入聚合反应器中。用去离子水冲洗泵。然后,将0.3g过硫酸铵溶于20g去离子水中,并在1小时内引入反应器中。
然后,烘烤1小时,然后让介质冷却,然后过滤。
得到了固含量(SC,用微波秤测量)为30.6重量%的共聚物(P1)。使用Flory-Fox方程计算其玻璃化转变温度(Tg)。共聚物(P1)的组成和表征如表1所示。
根据本发明的共聚物(P2)至P(14)的制备与表征
这些聚合物的制备方法与共聚物(P1)类似。它们的组成与表征如表1所示。
表1
实施例2:根据本发明的含水组合物C1至C3的制备与性质表征
将根据实施例1制备的共聚物P1以1%干重的量与去离子水混合,然后加入氢氧化钠水溶液(50重量%)以完全中和组合物。得到根据本发明的含水组合物C1。类似地,根据本发明的含水组合物C2和C3由根据本发明的共聚物P2和P3制备。
然后使用Brookfield DV1黏度计在25℃和100rpm下测量这些组合物的Brookfield黏度,黏度计配有与组合物的黏度范围相适应的主轴。还测量了这些组合物的流动阈值,即所施加的导致含水组合物流动的应力。使用从0.01Pa到1000Pa的应力斜坡持续3000秒,每次测量之间的平衡时间为30秒。在25℃下使用具有CP60-1/S锥-平面几何形状(直径60mm,1°截断角)HAAKE MARS III施加应力流变仪(ThermoFisher Scientific)测量流动阈值应力,然后使用RheoWin Data Manager软件进行处理。所得结果如表2所示。
含水组合物 | 使用的共聚物 | Brookfield黏度(mPa.s) | 流动阈值(Pa) |
C1 | P1 | 1 800 | 19.4 |
C2 | P2 | 170 | 0.68 |
C3 | P3 | 390 | 0.65 |
表2
还基于具有低应变的频率来确定根据本发明的含水组合物C1、C2和C3的黏弹性。施加的应变是正弦的,形状为γ=γ0sin(ωt),γ0设置为1%。频率ω遵循从高频到低频(100HZ至0.01HZ)的对数变化。测得的应力响应类型为σ=σ0sin(ωt+δ),δ为相位偏移。如有必要,应力信号也可分为同相部分(固体响应)和反相部分(液体响应)。这两个贡献用公式σ=γ0G’sin(ωt)+γ0G”cos(ωt)表示,其中G’表示储能模量(或弹性模量),G”表示损耗模量(或黏性模量)。
因此确定了含水组合物样品的固体或液体性质。当G’>G”时,则样品是固体。当G”>G’时,则样品是液体。我们可以定义tanδ=G”/G’,其为损耗角。如果tanδ=0,则表现为固体弹性,如果tanδ=1,则表现为黏性。当0<tanδ<1时,评估组合物具有黏弹性。所得结果如
表3所示。
表3
因此,根据本发明的共聚物能够显著增稠含水组合物。得到的含水组合物具有较高的流动阈值。此外,根据本发明的这些含水组合物的正切δ值系统地为0至1,因此证明了它们的黏弹性特征。这些性质是在根据本发明的共聚物的制备过程中不存在甲基丙烯酸的情况下获得的。
Claims (19)
1.一种共聚物P,其是在不存在甲基丙烯酸的情况下通过以下物质的至少一种聚合反应制备的:
a.至少一种阴离子单体(a),其选自丙烯酸、丙烯酸盐、丙烯酸低聚物、丙烯酸低聚物盐、及其组合;
b.至少一种非离子单体(b),其选自苯乙烯、选自丙烯酸、甲基丙烯酸的酸的C1-C8酯、及其组合;
c.至少一种化合物(c),其选自2-丙烯酰胺基-2-甲基丙磺酸、2-磺乙基甲基丙烯酸酯、甲基丙烯磺酸钠、苯乙烯磺酸盐/酯、它们的盐类、及其组合;
d.至少一种交联化合物(d)或包含至少两个可聚合的烯属不饱和键的化合物(d)。
2.根据权利要求1所述的共聚物P,其中单体(a)是丙烯酸或式(I)的丙烯酸低聚物的混合物:
其中m为1至10、优选2至4的整数或小数。
3.根据权利要求1或2中任一项所述的共聚物P,其中单体(b)选自:
-丙烯酸烷基酯,特别是丙烯酸C1-C8烷基酯,优选丙烯酸C1-C4烷基酯,更优选丙烯酸甲酯、丙烯酸乙酯、丙烯酸丙酯、丙烯酸异丁酯、丙烯酸正丁酯,
-甲基丙烯酸烷基酯,特别是甲基丙烯酸C1-C8烷基酯,优选甲基丙烯酸C1-C4烷基酯,更优选甲基丙烯酸甲酯、甲基丙烯酸乙酯、甲基丙烯酸丙酯、甲基丙烯酸异丁酯、甲基丙烯酸正丁酯,
-丙烯酸芳基酯,优选丙烯酸苯酯、丙烯酸苄酯、丙烯酸苯氧基乙酯,
-甲基丙烯酸芳基酯,优选甲基丙烯酸苯酯、甲基丙烯酸苄酯、甲基丙烯酸苯氧基乙酯,以及
-其组合。
4.根据权利要求1至3中任一项所述的共聚物P,其中单体(c)选自2-丙烯酰胺基-2-甲基丙磺酸(AMPS)及其钠盐或铵盐。
5.根据权利要求1至4中任一项所述的共聚物P,其中化合物(d)选自多不饱和芳香族单体如二乙烯基苯、二乙烯基萘和三乙烯基苯,多不饱和脂环族单体如1,2,4-三乙烯基环己烷,二价邻苯二甲酸酯如邻苯二甲酸二烯丙酯,多烯基醚如季戊四醇三烯丙基醚、季戊四醇二烯丙基醚、蔗糖二烯丙基醚、蔗糖八烯丙基醚和三羟甲基丙烷二烯丙基醚,多不饱和多元醇酯或多元酸酯如1,6-己二醇二(甲基)丙烯酸酯、四亚甲基三(甲基)丙烯酸酯、丙烯酸烯丙酯、衣康酸二烯丙酯、富马酸二烯丙酯、马来酸二烯丙酯、三羟甲基丙烷三(甲基)丙烯酸酯、三羟甲基丙烷二(甲基)丙烯酸酯、聚亚烷基氧基二醇二(甲基)丙烯酸酯和聚乙二醇二(甲基)丙烯酸酯,亚烷基双丙烯酰胺如亚甲基双丙烯酰胺和亚丙基双丙烯酰胺,亚甲基双丙烯酰胺的羟基或羧基衍生物如Ν,Ν’-二羟甲基亚甲基双丙烯酰胺,多亚烷基二醇二(甲基)丙烯酸酯如乙二醇二(甲基)丙烯酸酯、二乙二醇二(甲基)丙烯酸酯、三乙二醇二(甲基)丙烯酸酯、甲基丙烯酸烯丙酯、乙二醇二甲基丙烯酸酯、丁二醇二甲基丙烯酸酯、季戊四醇二丙烯酸酯、季戊四醇三丙烯酸酯和季戊四醇四丙烯酸酯,聚亚烷基氧基二醇二(甲基)丙烯酸酯如聚乙二醇二丙烯酸酯、双酚A二丙烯酸酯、丁二醇二甲基丙烯酸酯、2,2-二甲基丙二醇二甲基丙烯酸酯、亚苯基二丙烯酸酯、不对称交联化合物、及其混合物。
6.根据权利要求1至5中任一项所述的共聚物P,其包含:
-25重量%至60重量%的单体(a),
-39.89重量%至59重量%的单体(b),
-0.1重量%至8重量%的单体(c)和
-0.01重量%至8重量%的单体(d)。
7.根据权利要求1至6中任一项所述的共聚物P,其使用Flory-Fox方程计算的玻璃化转变温度(Tg)小于60℃,优选小于30℃。
8.根据权利要求1至7中任一项所述的共聚物P,其被完全地或部分地中和,优选地使用选自NaOH、KOH、LiOH、铵衍生物、氨、胺类碱、及其组合的化合物完全地或部分地中和,胺类碱例如三乙醇胺、氨甲基丙醇或2-氨基-2-甲基丙醇(AMP)。
9.根据权利要求1至8中任一项所述的共聚物P,其通过还使用至少一种疏水性单体(e)的聚合反应制备,所述疏水性单体(e)包含可聚合的烯属不饱和键、聚亚烷基二醇基团和疏水端基,疏水端基优选包含6个至40个碳原子的直链的、带支链的或环状的、饱和的、不饱和的或芳香族的烃基。
10.根据权利要求9所述的共聚物P,其中单体(e)是式(VI)的化合物:
R6-(oE)q-(op)r-R7
(VI)
其中:
-q和r,相同或不同,独立地表示0或小于150的整数或小数,q+r的和为5至150、优选为10至150,有利地为10至100,更有利地为10至60,
-EO表示CH2CH2O基团,
-PO独立地表示选自CH(CH3)CH2O和CH2CH(CH3)O的基团,
-R6表示包含至少一个可聚合的烯属不饱和键的基团,优选选自丙烯酸酯基、甲基丙烯酸酯基、丙烯酸氨基甲酸酯基、甲基丙烯酸氨基甲酸酯基、乙烯基、烯丙基、甲基烯丙基、异戊二烯基、不饱和的氨基甲酸酯基,特别是丙烯酸氨基甲酸酯基、甲基丙烯酸氨基甲酸酯基、α-α’-二甲基异丙烯基苄基氨基甲酸酯基、烯丙基氨基甲酸酯基的基团,更优选选自丙烯酸酯基、甲基丙烯酸酯基、丙烯酸氨基甲酸酯基、甲基丙烯酸氨基甲酸酯基、乙烯基、烯丙基、甲基烯丙基和异戊二烯基的基团,甚至更优选甲基丙烯酸酯基,
-R7独立地表示包含6个至40个、优选6个至32个、更优选8个至30个碳原子的直链的、带支链的或环状的、饱和的、不饱和的或芳香族的烃基。
11.根据权利要求1至10中任一项所述的共聚物P,相对于单体的总量,其包含0.4重量%至30重量%的单体(e)。
12.一种含水组合物C,其包含至少一种根据权利要求1至11中任一项所述的共聚物P和固体、液体或气体颗粒,以及任选地黏合剂化合物。
13.根据权利要求12所述的组合物C,其包含0.1重量%至5重量%、优选0.5重量%至3重量%的共聚物P。
14.根据权利要求12或13中任一项所述的组合物C,其中颗粒是选自化妆品、植物检疫产品、肥料、涂料产品的产品的颗粒。
15.根据权利要求12至14中任一项所述的组合物C,其是包含根据权利要求1至11中任一项所述的共聚物P、颜料颗粒和胶乳黏合剂化合物以及任选地颜料-分散化合物的含水清漆组合物C;优选使用Flory-Fox方程计算的玻璃化转变温度与共聚物P的玻璃化转变温度+/-10℃相同的黏合剂化合物。
16.根据权利要求12至15中任一项所述的组合物C,其pH为3至13,优选地pH为5至13或pH为4至8或pH为5至7。
17.一种制备具有黏弹性和悬浮性的含水组合物C的方法,其包括引入至少一种根据权利要求1至11中任一项所述的共聚物P,和搅拌组合物C。
18.一种用于稳定清漆组合物C的方法,其包括将至少一种根据权利要求1至11中任一项所述的共聚物P引入含水清漆基组合物C中,优选地引入包含胶乳黏合剂化合物的清漆基组合物C中,其中胶乳黏合剂化合物的使用Flory方程计算的玻璃化转变温度与共聚物P的玻璃化转变温度+/-10℃相同。
19.一种用于控制含水组合物的流动阈值的方法,其包括将至少一种根据权利要求1至11中任一项所述的共聚物P引入含水组合物中,优选地含水组合物的流动阈值大于0.1Pa、更优选大于0.5Pa或大于2Pa、优选大于4Pa,其中流动阈值根据包括在25℃下使用装备有CP60-1/S锥-平面几何形状(直径60mm,1°截断角)的Haake Mars III施加应力流变仪(ThermoFisher Scientific)测量流动阈值应力然后使用RheoWin Data Manager软件处理的方法测量。
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