CN103298844A - 可共聚的表面活性剂 - Google Patents
可共聚的表面活性剂 Download PDFInfo
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- CN103298844A CN103298844A CN201180064626.3A CN201180064626A CN103298844A CN 103298844 A CN103298844 A CN 103298844A CN 201180064626 A CN201180064626 A CN 201180064626A CN 103298844 A CN103298844 A CN 103298844A
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- Prior art keywords
- compound
- emulsifying agent
- phosphate groups
- oxyethane
- sulfuric ester
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- 239000004094 surface-active agent Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 30
- 239000000178 monomer Substances 0.000 claims abstract description 21
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims abstract description 19
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 15
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims abstract description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 30
- 238000007334 copolymerization reaction Methods 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 15
- 239000000839 emulsion Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000006386 neutralization reaction Methods 0.000 claims description 5
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000007720 emulsion polymerization reaction Methods 0.000 abstract description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 16
- 239000004816 latex Substances 0.000 description 11
- 229920000126 latex Polymers 0.000 description 11
- 239000006185 dispersion Substances 0.000 description 8
- 239000012634 fragment Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000008569 process Effects 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- -1 allyl ethers Chemical class 0.000 description 6
- 239000007957 coemulsifier Substances 0.000 description 6
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical group CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000000084 colloidal system Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- 150000003839 salts Chemical group 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- KGWDUNBJIMUFAP-KVVVOXFISA-N Ethanolamine Oleate Chemical compound NCCO.CCCCCCCC\C=C/CCCCCCCC(O)=O KGWDUNBJIMUFAP-KVVVOXFISA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 239000004159 Potassium persulphate Substances 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 150000003818 basic metals Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical class [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 2
- 235000012254 magnesium hydroxide Nutrition 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
- 235000019394 potassium persulphate Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 2
- 238000010008 shearing Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 239000004160 Ammonium persulphate Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 150000004808 allyl alcohols Chemical class 0.000 description 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
- 235000019395 ammonium persulphate Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 229910001038 basic metal oxide Inorganic materials 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000012928 buffer substance Substances 0.000 description 1
- SIIVGPQREKVCOP-UHFFFAOYSA-N but-1-en-1-ol Chemical compound CCC=CO SIIVGPQREKVCOP-UHFFFAOYSA-N 0.000 description 1
- XZKRXPZXQLARHH-UHFFFAOYSA-N buta-1,3-dienylbenzene Chemical compound C=CC=CC1=CC=CC=C1 XZKRXPZXQLARHH-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical class NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- IGBZOHMCHDADGY-UHFFFAOYSA-N ethenyl 2-ethylhexanoate Chemical group CCCCC(CC)C(=O)OC=C IGBZOHMCHDADGY-UHFFFAOYSA-N 0.000 description 1
- GLVVKKSPKXTQRB-UHFFFAOYSA-N ethenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=C GLVVKKSPKXTQRB-UHFFFAOYSA-N 0.000 description 1
- 125000005670 ethenylalkyl group Chemical group 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- HXHCOXPZCUFAJI-UHFFFAOYSA-N prop-2-enoic acid;styrene Chemical class OC(=O)C=C.C=CC1=CC=CC=C1 HXHCOXPZCUFAJI-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65502—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a three-membered ring
-
- 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
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
- C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
- C08F2/26—Emulsion polymerisation with the aid of emulsifying agents anionic
-
- 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
- C08F224/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a heterocyclic ring containing oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
本发明涉及式(I)化合物R-CH(O-(AO)mX)-CH2-O(AO)n-CH2-CH=CH2作为烯属不饱和单体的乳液聚合中的可共聚乳化剂的用途,其中R是8至18个碳原子的烷基,其可以是饱和或不饱和的、直链或支链的;X是硫酸酯或磷酸酯基团或氢;(AO)是选自环氧乙烷、环氧丙烷和环氧丁烷的烯化氧单元;n是0至50;并且m是0或1至30。
Description
发明领域
本发明属于聚合物领域并且涉及具有特定结构的烯丙基醚,并且还涉及其用作乳液聚合的乳化剂的用途,以及利用本发明的烯丙基醚(它们有利地是可共聚的乳化剂)通过乳液聚合制备聚合物的方法。
现有技术
乳液聚合是一种特定的聚合方法,其中将在水中溶解度低的烯属不饱和单体在水中通过乳化剂乳化,然后利用水溶性引发剂例如过硫酸钾或氧化还原引发剂进行聚合。阴离子和/或非离子型表面活性剂是其中的关键成分,因为它们确保在水溶液中通过胶束构建进行乳液聚合的过程。
可共聚的乳化剂在工业中有巨大的需求,因为它们可全部或部分地掺入到生长中的聚合物链中,由此减少了游离的乳化剂分子向最终产品的迁移。可共聚的乳化剂介于单体和常规乳化剂之间。它们的反应性必须进行调整以适应所用的单体体系,并且它们不能对所形成的聚合物的性能有不利影响。同时,它们不能因反应性基团的存在而失去其乳化性能。鉴于该特殊性能的组合,新的可共聚的乳化剂在工业中是倍受追捧的。
德国公开说明书DE-A-10340081描述了下式的可共聚的表面活性剂:HOOC-CH=CH-COO-(BO)z(PO)y(EO)xR1,其中R1是具有8至24个碳原子的烷基或烷基苯酚基团,BO是环氧丁烷单元,PO是环氧丙烷单元且EO是环氧乙烷单元,并且x、y和z彼此独立地是0或1至50,条件是x、y和z中的至少一个不是0,其中羧基可以全部或部分以中和形式存在,并且C=C双键可以是顺式或反式构型。
EP-A-1,825,908描述了结构式(A)的特定化合物
其中R1是C8-20烃基,R2和R3都是氢或甲基,(AO)是C2-4烯化氧基团,X是离子型亲水基团,n是0至12,m是0至100。这些化合物(A)可与某些含氮化合物(B)组合使用,并且包含(A)和(B)的特定组合物据说可用作乳液聚合的乳化剂。
发明描述
本发明要解决的问题是提供可单独或与其它化合物相混合而用作乳液聚合的乳化剂的化合物。
用作乳液聚合的乳化剂,它们应该具有能使凝结最小化的特定效果。此外,这些可共聚的乳化剂在水性供应系统中应该是可流动或可泵送的。
最后,在乳液聚合中用作乳化剂应该能够提供胶乳,该胶乳与利用相当的不可共聚的乳化剂所得到的胶乳相比,在由其得到的聚合物薄膜的耐水性和耐刮擦性方面具有改进的性能。
本发明首先提供了通式(I)化合物
R-CH(O-(AO)mX)-CH2-O-(AO)n-CH2-CH=CH2
(I)
其中
·R是8至18个碳原子的烷基,其可以是饱和或不饱和的、直链或支链的,
·X是硫酸酯或磷酸酯基团或氢,
·(AO)是选自环氧乙烷、环氧丙烷和环氧丁烷的烯化氧单元,
·n是0至50,并且
·m是0或1至30。
本发明进一步提供了通式(I)化合物用作烯属不饱和单体的乳液聚合中的可共聚乳化剂的用途,
R-CH(O-(AO)mX),CH2-O-(AO)n-CH2-CH=CH2
(I)
其中
·R是8至18个碳原子的烷基,其可以是饱和或不饱和的、直链或支链的,
·X是硫酸酯或磷酸酯基团或氢,
·(AO)是选自环氧乙烷、环氧丙烷和环氧丁烷的烯化氧单元,
·n是0至50,并且
·m是0或1至30。
在该乳液聚合中,所述的化合物(I)可单独使用或彼此混合使用,并且还可以与常规乳化剂组合使用,如果需要的话。
在所述的式(I)中,构件(AO)是选自环氧乙烷、环氧丙烷和环氧丁烷的烯化氧单元。在所述的式(I)中,指数n和m与结构构件(AO)n和(AO)m一起表示烯化氧构件的平均数。
所述的化合物(I)可通过本领域技术人员已知的任何方法得到。其通常包括将α-烯烃环氧化物与环氧乙烷、环氧丙烷和/或环氧丁烷通过打开环氧化物的环氧乙烷环与烯丙基醇形成的加成产物反应。如果需要的话,在开环过程中形成的OH基团可转化成硫酸酯或磷酸酯基团;如果需要的话,该向硫酸酯或磷酸酯基团的转化可通过烷氧基化来进行。
环氧乙烷或环氧丙烷和/或环氧丁烷与烯丙基醇的加成产物可通过将烯丙基醇与环氧乙烷、环氧丙烷和/或环氧丁烷在烷氧基化催化剂的存在下反应来得到,这对于本领域技术人员来说是已知的;这可利用如下流程式来举例说明,其中(AO)和n具有与式(I)中相同的含义:
CH2=CH-CH2-OH+n(AO)→CH2=CH-CH2-O-(AO)n-H
烷氧基化可单独利用环氧乙烷、环氧丙烷和环氧丁烷进行或将其彼此混合而进行。指数n是(统计意义上的)平均值;因此在CH2=CH-CH2-O-(AO)n-H的情况下,表述n=1的含义是指1mol烯丙基醇与1mol烯化氧发生了反应,而n=2的含义是指1mol烯丙基醇与2mol烯化氧发生了反应,n=6的含义是指1mol烯丙基醇与6mol烯化氧发生了反应等等。因此,指数n代表烯丙基醇和所用的烯化氧的摩尔反应比率,然而,烯丙基醇烷氧基化物可以在其同系物分布中有所不同,这取决于所用的催化剂。
在所述的式(I)中的指数n是0至50。优选它是1至30,特别是3至10。由于n指的是烯化氧单元(AO)n的数目并且烯化氧单元选自环氧乙烷、环氧丙烷和环氧丁烷,因此应明确指出的是,应将n理解为是指整个(AO)n片段(其应理解为是指通过(AO)n表示的整体)中所有环氧乙烷、环氧丙烷和环氧丁烷单元的总和。整个(AO)n片段可以仅由环氧乙烷、环氧丙烷或环氧丁烷单元构成,或以混合形式包含这些单元–随机分布或以嵌段的形式。优选化合物(I)的整个(AO)n片段仅由环氧乙烷和/或环氧丙烷单元构成。更具体地,化合物(I)的整个(AO)n片段仅由环氧乙烷单元构成。
在所述的式(I)中的指数m是0或1至30。在一种实施方案中,m是0。在另一个实施方案中,m是1至10,特别是3至10。由于m指的是烯化氧单元(AO)m的数目并且烯化氧单元选自环氧乙烷、环氧丙烷和环氧丁烷,因此应明确指出的是,应将m理解为是指整个(AO)m片段(其应理解为是指通过(AO)m表示的整体)中所有环氧乙烷、环氧丙烷和环氧丁烷单元的总和。整个(AO)m片段可以仅由环氧乙烷、环氧丙烷或环氧丁烷单元构成,或以混合形式包含这些单元–随机分布或以嵌段的形式。优选化合物(I)的整个(AO)m片段仅由环氧乙烷和/或环氧丙烷单元构成。更具体地,化合物(I)的整个(AO)m片段仅由环氧乙烷单元构成。
基团X是硫酸酯或磷酸酯基团或氢。
在一种实施方案中,基团X是氢。
在一种实施方案中,基团X是硫酸酯或磷酸酯基团。化合物(I)中的硫酸酯和/或磷酸酯基团X是部分或全部中和的形式。硫酸酯或磷酸酯基团可以用例如碱金属或碱土金属氢氧化物例如氢氧化钠、氢氧化钾、氢氧化钙或氢氧化镁或用胺例如氨水或乙醇胺中和。化合物(I)的盐形式的显著特点是良好的水溶性。
式(I)化合物可通过例如将烷氧基化的烯丙基醇与α-烯烃氧化物反应来得到,并且,如果需要的话,硫酸化或磷酸化所得到的产物(其中X=H)。
本发明所用的化合物(I)可容易地且完全地与其它不同的烯属不饱和单体一起聚合,并促进无泡沫且匀质的乳液的形成。
其中的X是硫酸酯或磷酸酯基团的化合物(I)是优选的。它们优选以部分或全部中和的形式(硫酸酯或磷酸酯基团的“盐形式”)用于乳液聚合。该部分或全部中和的形式可以容易地通过以常规方式部分或全部中和所述的化合物(I)来得到,例如用碱金属或碱土金属氢氧化物例如氢氧化钠、氢氧化钾、氢氧化钙或氢氧化镁或用胺例如氨水或乙醇胺中和。化合物(I)的盐形式的显著特点是良好的水溶性。
本发明进一步提供了通过烯属不饱和单体的乳液聚合制备聚合物的方法,其中使用上述的化合物(I)作为可共聚的乳化剂。
利用化合物(I)、尤其是其盐形式的本发明的方法提供了具有独特的剪切力和电解质稳定性以及低凝块含量的聚合物。
本发明的一种实施方案提供了胶乳,该胶乳对温度波动具有显著的稳定性并且不会产生任何明显的乳化剂向薄膜内的迁移。
本发明方法的另一个优点是几乎没有泡沫并且可靠地避免了挥发性有机化合物的形成。由于聚合物中乳化剂(I)的掺入实质上是定量的,因此它的使用也不会带来任何生物降解性的问题。烯属不饱和的化合物(I)还从实质上避免了任何均聚的倾向。
已发现,与利用相当的不可共聚的乳化剂所得到的胶乳相比,在乳液聚合中利用化合物(I)作为乳化剂提供了在由此得到的聚合物薄膜的耐水性和耐刮擦性方面具有改进性能的胶乳。还可使用化合物(I)与不同于化合物(I)的非离子型或阴离子型表面活性剂的组合,其同样可以表现出有利的性能。
本发明的胶乳可用于例如涂料行业。已发现,利用本发明的胶乳获得的涂料比常规涂料具有更高的防腐蚀性。
此外还发现,利用通式(I)化合物作为乳化剂得到的胶乳比用常规乳化剂得到的胶乳具有改进的冻融稳定性。
单体
本发明所用的通式(I)的烯属不饱和酯可在几乎所有工业上重要的、基本上不溶于水的单体、优选(甲基)丙烯酸类、苯乙烯类和乙烯基类化合物的乳液聚合中用作乳化剂。
这些单体的常见例子是乙烯基芳香族化合物,例如苯乙烯、二乙烯基苯或乙烯基甲苯、可聚合的烯烃和二烯烃例如丙烯、丁二烯或异戊二烯、丙烯酸或甲基丙烯酸与具有1至18个碳原子的直链或支链醇、更优选具有1至8个碳原子的醇的酯–尤其优选其甲酯、乙酯和丁酯、具有2至12个碳原子的酸的乙烯基酯、尤其是乙酸乙烯酯、丙酸乙烯酯、2-乙基己酸乙烯酯和月桂酸乙烯酯、具有1至8个碳原子的烷基的乙烯基烷基醚、氯乙烯、二氯乙烯等。
选自丙烯酸烷基酯、丙烯酸苯乙烯酯、VeoVa化合物或其混合物(加入或未加入丙烯酸或甲基丙烯酸)的单体在本发明的上下文中是特别优选的。
在本发明所用的可共聚的乳化剂(I)的存在下,可将单体均聚或将它们与以上列表所述的其它化合物共聚。还可以进行涉及高达50wt%不同于本发明的化合物(I)的其它部分或完全水溶性单体的共聚合,所述单体的例子是丙烯腈、甲基丙烯腈、马来酸和/或富马酸与1至8个碳原子的单酯、丙烯酸、甲基丙烯酸、马来酸、富马酸、巴豆酸和/或衣康酸。
在一种实施方案中,用于本发明方法的单体是苯乙烯/丙烯酸丁酯、乙酸乙烯酯/丙烯酸丁酯或苯乙烯/丁二烯的组合。
共乳化剂
此外,还可以将本发明所用的化合物(I)和(II)与已知的非离子型和/或阴离子共乳化剂组合使用。这可产生例如对剪切力、温度的影响和电解质具有增强的稳定性的分散体。共乳化剂的加入量为0.5%至5%,优选1%至3wt%,基于所用的总单体计。可将共乳化剂在聚合开始时与乳化剂一起加入,或在聚合的过程中加入。在另一种方式中,使用或共同使用共乳化剂来制备预乳化液并在聚合的过程中加入。还可以将本发明的利用丙烯酸和/或甲基丙烯酸酯得到的分散液与共乳化剂相混合以用于后稳定化。
本发明所用的化合物(I)还可以与保护性胶体一起使用。该类型的保护性胶体的典型例子是全部或部分水解的乙酸乙烯酯的均聚物和/或共聚物,例如部分水解的聚乙酸乙烯酯,或全部水解的乙酸乙烯酯和乙烯基醚的共聚物。优选的共聚物在聚乙烯基醚的醚部分具有1至4个碳原子。其它的保护性胶体可衍生自多糖。尤其适宜的是纤维素醚例如羟乙基纤维素、羟丙基纤维素、羧甲基纤维素、甲基纤维素、乙基纤维素或纤维素混合醚。聚丙烯酰胺及其与丙烯酸、丙烯腈或丙烯酸酯的共聚物也是适宜的。同样可使用萘磺酸和甲醛的缩合产物或其它水溶性甲醛树脂,尤其是脲-甲醛树脂。最后,酪蛋白、明胶、阿拉伯胶以及天然淀粉和淀粉的取代衍生物例如羟乙基淀粉也是适当的保护性胶体。
乳液聚合
一种实施方案在乳液聚合中使用乳化剂(I)的用量是0.1%至25wt%,基于单体的总和计。
通常在使用化合物(I)的方法的第一步骤中制备水性分散液,在实践中,该分散液在水或水与水溶性有机溶剂的混合物中包含15%至75wt%的聚合单体(干物质)。20%至60wt%干物质是优选的;然而,对于特殊的应用也可得到含有小于15wt%干物质的水性分散液。上述的乳液聚合方法也可使用其它常规的聚合助剂,更确切地说是引发剂,例如无机过氧化物,例如过硫酸钾或过硫酸铵或过氧化氢;有机过氧化物或有机偶氮化合物(当其可用于乳液聚合时)。引发剂以常规量使用,即,0.05%至2wt%,优选0.1%至0.5wt%。适当的助剂还包括缓冲物质,例如碳酸氢钠、焦磷酸钠或乙酸钠,它们的用量均为至多2wt%。还可使用促进剂例如甲醛次硫酸氢钠。此外,还可以使用用于乳液聚合的常规分子量调节剂,例如丁烯醇或其它的有机硫醇化合物例如巯基乙醇、硫代乙醇酸、辛基硫醇或叔十二烷基硫醇。为了进行聚合过程,通常用于乳液聚合的各种方法均是可行的,例如将所有反应物在起始加料时全部加入、单体进料或乳液进料。通常,将聚合介质的温度保持在40至100,更优选50至90℃。将pH优选保持在3至9的范围内,尽管本发明化合物也可以容许在较低的pH值下进行乳液聚合。上述可能的各种乳液聚合方法优选在配备有搅拌器和温度测量装置的可冷却和可加热的容器、例如搅拌压力罐中进行。类似地还可以使用螺旋管式反应器或所谓的环管反应器。当聚合结束后,优选将聚合物分散体冷却并从反应器中通过筛分的方式除去。当需要将反应产物以固体产物的形式分离出来时,优选将聚合物分散体沉淀析出或喷雾干燥。然而,优选将聚合物分散体本身直接用作油漆的粘结剂、胶粘剂、纸张涂层爽滑剂或其它涂料。本领域的技术人员还可自由选择利用本发明所用化合物(I)进行乳液聚合过程的其它条件或按照常规方式进行调整以适应特定的需求。
Claims (7)
1.式(I)化合物
R-CH(O-(AO)mX)-CH2-O-(AO)n-CH2-CH=CH2
(I)
其中
·R是8至18个碳原子的烷基,其可以是饱和或不饱和的、直链或支链的,
·X是硫酸酯或磷酸酯基团或氢,
·(AO)是选自环氧乙烷、环氧丙烷和环氧丁烷的烯化氧单元,
·n是0至50,并且
·m是0或1至30。
2.式(I)化合物作为烯属不饱和单体的乳液聚合中的可共聚乳化剂的用途,
R-CH(O-(AO)mX)-CH2-O-(AO)n-CH2-CH=CH2
(I)
其中
·R是8至18个碳原子的烷基,其可以是饱和或不饱和的、直链或支链的,
·X是硫酸酯或磷酸酯基团或氢,
·(AO)是选自环氧乙烷、环氧丙烷和环氧丁烷的烯化氧单元,
·n是0至50,并且
·m是0或1至30。
3.根据权利要求2所述的用途,其中X是硫酸酯或磷酸酯基团。
4.根据权利要求3所述的用途,其中硫酸酯或磷酸酯基团是部分或全部中和的形式。
5.根据权利要求2至4中的任一项所述的用途,其中烷氧基化程度n是1至30。
6.根据权利要求2至4中的任一项所述的用途,其中烷氧基化程度n是3至10且(AO)是环氧乙烷单元。
7.通过烯属不饱和单体的乳液聚合制备聚合物的方法,该方法包括利用权利要求1所述的化合物(I)作为可共聚的乳化剂。
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CN103298844A true CN103298844A (zh) | 2013-09-11 |
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CN201180064626.3A Pending CN103298844A (zh) | 2011-01-18 | 2011-10-08 | 可共聚的表面活性剂 |
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US (1) | US20130317190A1 (zh) |
EP (1) | EP2476712A1 (zh) |
JP (1) | JP2014509331A (zh) |
CN (1) | CN103298844A (zh) |
WO (1) | WO2012097837A1 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN108779189A (zh) * | 2016-04-12 | 2018-11-09 | 花王株式会社 | 乳液聚合用阴离子性表面活性剂组合物 |
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EP0244841B1 (en) * | 1986-05-07 | 1992-03-18 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | Surface active compounds having a polymerizable moiety |
US5371159A (en) * | 1990-05-23 | 1994-12-06 | Asahi Denka Kogyo K.K. | Solution polymerization with reactive modifier |
US7098250B2 (en) * | 2000-09-11 | 2006-08-29 | Kao Corporation | Surfactant for emulsion polymerization |
DE10239932B4 (de) * | 2002-08-21 | 2006-12-07 | Clariant Produkte (Deutschland) Gmbh | Copolymere aus Alkylenoxiden und Glycidylethern und deren Verwendung als polymerisierbare Emulgatoren |
DE10340081A1 (de) | 2003-08-30 | 2005-03-31 | Cognis Deutschland Gmbh & Co. Kg | Copolymerisierbare Tenside |
JP4564809B2 (ja) | 2004-09-13 | 2010-10-20 | 株式会社Adeka | 界面活性剤組成物 |
US8592040B2 (en) * | 2008-09-05 | 2013-11-26 | Basf Se | Polymer emulsion coating or binding formulations and methods of making and using same |
EP2194069A1 (de) * | 2008-12-04 | 2010-06-09 | Cognis IP Management GmbH | Copolymerisierbare Tenside |
ES2391433T3 (es) * | 2009-06-27 | 2012-11-26 | Cognis Ip Management Gmbh | Agentes tensioactivos copolimerizables |
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- 2011-01-18 EP EP11151299A patent/EP2476712A1/de not_active Withdrawn
- 2011-10-08 WO PCT/EP2011/005040 patent/WO2012097837A1/de active Application Filing
- 2011-10-08 JP JP2013549720A patent/JP2014509331A/ja active Pending
- 2011-10-08 US US13/979,770 patent/US20130317190A1/en not_active Abandoned
- 2011-10-08 CN CN201180064626.3A patent/CN103298844A/zh active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN108779189A (zh) * | 2016-04-12 | 2018-11-09 | 花王株式会社 | 乳液聚合用阴离子性表面活性剂组合物 |
Also Published As
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WO2012097837A1 (de) | 2012-07-26 |
JP2014509331A (ja) | 2014-04-17 |
EP2476712A1 (de) | 2012-07-18 |
US20130317190A1 (en) | 2013-11-28 |
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