JPH0223563B2 - - Google Patents
Info
- Publication number
- JPH0223563B2 JPH0223563B2 JP61145943A JP14594386A JPH0223563B2 JP H0223563 B2 JPH0223563 B2 JP H0223563B2 JP 61145943 A JP61145943 A JP 61145943A JP 14594386 A JP14594386 A JP 14594386A JP H0223563 B2 JPH0223563 B2 JP H0223563B2
- Authority
- JP
- Japan
- Prior art keywords
- emulsifier
- emulsion
- group
- present
- emulsifiers
- 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.)
- Expired
Links
- 239000003995 emulsifying agent Substances 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 29
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000005156 substituted alkylene group Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 23
- 239000000839 emulsion Substances 0.000 description 17
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 16
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 15
- 239000000178 monomer Substances 0.000 description 14
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 12
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
- -1 alkyl sulfate salts Chemical class 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 8
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 8
- 150000005690 diesters Chemical class 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 229920006254 polymer film Polymers 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 239000011591 potassium Substances 0.000 description 6
- 239000003518 caustics Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 4
- 229910015900 BF3 Inorganic materials 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-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
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- JKTAIYGNOFSMCE-UHFFFAOYSA-N 2,3-di(nonyl)phenol Chemical compound CCCCCCCCCC1=CC=CC(O)=C1CCCCCCCCC JKTAIYGNOFSMCE-UHFFFAOYSA-N 0.000 description 1
- NSENZNPLAVRFMJ-UHFFFAOYSA-N 2,3-dibutylphenol Chemical compound CCCCC1=CC=CC(O)=C1CCCC NSENZNPLAVRFMJ-UHFFFAOYSA-N 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
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-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
- CDMGNVWZXRKJNS-UHFFFAOYSA-N 2-benzylphenol Chemical class OC1=CC=CC=C1CC1=CC=CC=C1 CDMGNVWZXRKJNS-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- WJORGWQDTVMZDR-UHFFFAOYSA-N 2-methyloxirane;phenol Chemical class CC1CO1.OC1=CC=CC=C1 WJORGWQDTVMZDR-UHFFFAOYSA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- CYYZDBDROVLTJU-UHFFFAOYSA-N 4-n-Butylphenol Chemical compound CCCCC1=CC=C(O)C=C1 CYYZDBDROVLTJU-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- CXBBTDFFSDZASM-UHFFFAOYSA-N C1C(C)O1.C(CCC)C1=C(C=CC=C1)O Chemical compound C1C(C)O1.C(CCC)C1=C(C=CC=C1)O CXBBTDFFSDZASM-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 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
- 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 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 125000001204 arachidyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- KQNZLOUWXSAZGD-UHFFFAOYSA-N benzylperoxymethylbenzene Chemical compound C=1C=CC=CC=1COOCC1=CC=CC=C1 KQNZLOUWXSAZGD-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=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])[H] 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
- 150000001993 dienes Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- IMBKASBLAKCLEM-UHFFFAOYSA-L ferrous ammonium sulfate (anhydrous) Chemical compound [NH4+].[NH4+].[Fe+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O IMBKASBLAKCLEM-UHFFFAOYSA-L 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 125000002960 margaryl 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])[H] 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000001196 nonadecyl 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])C([H])([H])[H] 0.000 description 1
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- 125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 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
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl 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])[H] 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 125000002958 pentadecyl 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])[H] 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000000865 phosphorylative effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 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
- 238000003860 storage Methods 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
- 125000005040 tridecenyl group Chemical group C(=CCCCCCCCCCCC)* 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Landscapes
- Polyethers (AREA)
- Polymerisation Methods In General (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Detergent Compositions (AREA)
- Liquid Carbonaceous Fuels (AREA)
Description
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The present invention relates to an emulsifier for emulsion polymerization, and in particular to a novel emulsifier for use in aqueous emulsion polymerization of ethylenically unsaturated monomers.
and useful emulsifiers. Conventionally, as emulsifiers for emulsion polymerization, alkyl sulfate salts, alkylbenzene sulfonate salts,
Anionic surfactants such as dialkyl sulfosuccinate salts, polyoxyalkylene alkyl (aryl) ether sulfate salts, polyoxyalkylene alkyl (aryl) ethers, polyoxyethylene polyoxypropylene block copolymers, polyoxyethylene sorbitan fatty acids Nonionic surfactants such as esters are used alone or in combination, but the stability of emulsions and the properties of films produced from emulsions are not always fully satisfactory, and many There are still issues to be resolved. That is, there are problems with the polymerization stability of the emulsion, the mechanical stability, chemical stability, freeze-thaw stability, pigment miscibility, storage stability, etc. of the obtained emulsion, and in particular, the mechanical stability should be improved. Problems remain. Furthermore, when a polymer film is made from an emulsion, the emulsifier used remains in the polymer film in a free state, resulting in problems such as poor water resistance and adhesive properties of the film. Furthermore, when the emulsion is destroyed by means such as salting out to extract the polymer, a large amount of emulsifier is contained in the wastewater, which causes river pollution, and therefore a great deal of effort is required to remove the emulsifier. From this point of view, a number of patents relating to new emulsifiers, generally referred to as reactive emulsifiers, have been proposed in order to solve the problems of conventional emulsifiers.
For example, as an anionic reactive emulsifier,
â34894, JP 56-29657, JP 51-
30285, Japanese Patent Publication No. 49-46291, etc., and as nonionic reactive emulsifiers, there are JP-A No. 56-28208, JP-A No. 50-98484, etc., which were tried as emulsifiers for emulsion polymerization of various monomers. Although it is
When these reactive emulsifiers are used alone as emulsifiers, they often have insufficient stability during emulsion polymerization, and when used in combination with conventional emulsifiers, polymerization may not proceed smoothly, resulting in poor performance. The problem is that it cannot fully demonstrate its capabilities. As mentioned above, various attempts have been made, but
At present, the above-mentioned problems have not yet been fully solved. The present inventor has arrived at the present invention as a result of intensive research to solve these problems. That is, the present invention has the following general formula: general formula [However, in the above formula, R is an alkyl group, alkenyl group, alkylaryl group, or aralkylaryl group having 8 to 30 carbon atoms, A is an alkylene group having 2 to 4 carbon atoms, or a substituted alkylene group, and n is 0
is an integer of ~100, m is an integer of 1 to 200,
M is an alkali metal atom, NH 4 , an alkanolamine residue, or a hydrogen atom. ] It provides an emulsifier for emulsion polymerization characterized by containing a mixture of compounds represented by the following. In the general formula, R is an alkyl group, alkenyl group, alkylaryl group, or aralkylaryl group having 8 to 30 carbon atoms, and examples of the alkyl group include octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, and tetradecyl. ,
Examples include pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, and the like. Examples of alkenyl groups include octenyl,
Examples include nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, and the like. Examples of the alkylaryl group include monobutylphenol, dibutylphenol, sec.butylphenol, disec.butylphenol, tert.butylphenol, octylphenol, nonylphenol, dinonylphenol, and the like. Examples of the aralkyl phenol include mono-, di-, and tri-styrylated phenols, benzylphenols, cumylphenols, and the like, or mixtures thereof, and may be mixtures of these alkyl groups. Further, A is an alkylene group or substituted alkylene group having 2 to 4 carbon atoms, such as ethylene, propylene, butylene, isobutylene, etc., and may be a single group or a block or random mixture thereof. n is an integer of 0 to 100, m is an integer of 1 to 200, more preferably n is 0 or 1 to 50, m is 2
~100 range. In addition, M is a hydrogen atom, an alkali metal atom such as sodium or potassium, NH 4 , or
monoethanolamine, triethanolamine,
It is an alkanolamine residue such as, and a mixture thereof may be used. Furthermore, the emulsifier of the present invention can be easily produced industrially, and can be produced, for example, as follows. That is, nonylphenol or lauryl alcohol is used as a raw material, alkylene oxide is added if necessary, allyl glycidyl ether is heated and reacted in the presence of a catalyst, and alkylene oxide is further added to the resulting reaction composition by a conventional method. Add it at . Next, the emulsifier of the present invention can be obtained by phosphoric acid esterification using a phosphorylating agent such as phosphoric anhydride or phosphorus oxychloride, and neutralization with a basic substance if necessary. Various monomers can be mentioned as monomers for emulsion polymerization to which the emulsifier of the present invention is applied.
For example, acrylic monomers such as acrylic acid, methyl acrylate, butyl acrylate, 2-ethylhexyl acrylate, methyl methacrylate, acrylonitrile, acrylamide, acrylic acid hydroxyethyl ester, aromatic monomers such as styrene, divinylbenzene, and acetic acid. Examples include vinyl ester monomers such as vinyl, halogen-containing monomers such as vinyl chloride and vinylidene chloride, conjugated diolefin monomers such as butadiene, isoprene, and chloroprene, and others such as ethylene, maleic anhydride, and methyl maleate. The emulsifier of the present invention can be used for emulsion polymerization of one or more of these monomers. As the polymerization initiator, conventionally known ones may be used.
Examples include hydrogen peroxide, potassium persulfate, azobisisobutylnitrile, and benzyl peroxide. Examples of the polymerization accelerator include sodium hydrogen sulfite and ferrous ammonium sulfate. The emulsifier of the present invention typically has a
It is 0.1 to 20% by weight, more preferably 0.2 to 5.0% by weight. Although a good emulsion polymerization emulsion can be obtained using the emulsifier of the present invention alone, other emulsifiers or protective colloids may be used in combination, if necessary. The emulsion polymerization emulsion obtained by applying the emulsifier of the present invention can be applied to wood, metal, paper, cloth, concrete, etc., as an adhesive, a coating agent, an impregnation reinforcing agent, etc., for example. The present invention will be specifically explained below using examples. [% and parts indicate weight basis. ] Production Example 1 220 g of nonylphenol and 1.5 g of triethylamine as a catalyst were placed in a reaction vessel equipped with a stirrer, a thermometer, and a reflux tube. Next, 120 g of allyl glycidyl ether was added dropwise, and the mixture was reacted with stirring at 80°C for 5 hours. The mixture was heated to 0.degree. C. and excess allyl glycidyl ether was removed under reduced pressure. Next, the obtained reaction composition was transferred to an autoclave, and caustic potassium was used as a catalyst to
2 moles and 10 moles of ethylene oxide were added to the reaction composition under conditions of cm 2 and temperature of 130°C. Next, add 2 moles of the above ethylene oxide adduct to a reaction vessel equipped with a stirrer, thermometer, and reflux tube.
211 g of phosphoric anhydride and 23 g of phosphoric anhydride were charged, and a phosphoric acid esterification reaction was carried out at 80° C. for 5 hours. The resulting composition was designated as the emulsifier [A] of the present invention. Emulsifier of the present invention [A]
The mixing molar ratio of monoester and diester is 55/
It was 45. Ethylene oxide 10 obtained by similar operation
The phosphoric acid esterified product of the molar adduct was used as the emulsifier [B] of the present invention. The mixing molar ratio of monoester and diester in the emulsifier [B] of the present invention was 60/40. Production Example 2 186 g of lauryl alcohol and 0.5 g of boron trifluoride ether complex as a catalyst were placed in a reaction vessel equipped with a stirrer, a thermometer, and a reflux tube, and then 130 g of allyl glycidyl ether was added dropwise and stirred at 80°C for 5 hours. After the reaction, the mixture was heated to 120°C and excess allyl glycidyl ether was removed under reduced pressure. Next, the obtained reaction composition was transferred to an autoclave, and caustic potassium was used as a catalyst to
5 mol of propylene oxide was added to the reaction composition under conditions of cm 2 and temperature of 130°C. Next, add 5 moles of the above propylene oxide adduct to a reaction vessel equipped with a stirrer, thermometer, and reflux tube.
295 g and 23 g of phosphoric anhydride were charged and a phosphoric acid esterification reaction was carried out at 80° C. for 5 hours, and the obtained composition was designated as the emulsifier [C] of the present invention. The mixing molar ratio of monoester and diester was 62/38. Production Example 3 In a reaction vessel equipped with a stirrer, a thermometer, and a reflux tube, 2 moles of distyrenated phenol propylene oxide and 5 moles of ethylene oxide block adduct were added.
636g, 2g of boron trifluoride ether complex as a catalyst, then allyl glycidyl ether
After dropping 130g and reacting with stirring at 80â for 5 hours,
The mixture was heated to 120°C and excess allyl glycidyl ether was removed under reduced pressure. Next, the obtained reaction composition was transferred to an autoclave, and caustic potassium was used as a catalyst to
30 moles and 10 moles of ethylene oxide were added to the reaction composition under conditions of cm 2 and temperature of 130°C. Next, add 30 moles of the above ethylene oxide adduct to a reaction vessel equipped with a stirrer, thermometer, and reflux tube.
1,035 g of phosphoric acid anhydride and 30 g of phosphoric anhydride were charged, and a phosphoric acid esterification reaction was carried out at 80° C. for 5 hours, and the obtained composition was designated as the emulsifier [D] of the present invention. The mixing molar ratio of monoester and diester was 75/25.
Ethylene oxide 100 obtained by similar operation
The phosphoric acid esterified product of the molar adduct was designated as the emulsifier [E] of the present invention. The mixing molar ratio of monoester and diester was 80/20. Production Example 4 Into a reaction vessel equipped with a stirrer, a thermometer, and a reflux tube, 2468 g of oleyl alcohol ethylene oxide 50 mole adduct and 5 g of boron trifluoride ether complex as a catalyst were charged, and then 130 g of allyl glycidyl ether was added dropwise at 80°C. After stirring for 5 hours, the mixture was heated to 120°C, and excess allyl glycidyl ether was removed under reduced pressure. Next, the obtained reaction composition was transferred to an autoclave, and caustic potassium was used as a catalyst to
cm 2 and ethylene oxide 40 at a temperature of 130°C.
40 moles of propylene oxide were randomly added to the reaction composition. Next, in a reaction vessel equipped with a stirrer, a thermometer, and a reflux tube, 40 moles of ethylene oxide, 655 g of the random adduct of 40 moles of propylene oxide, and 5 g of phosphoric anhydride were charged, and phosphoric acid esterification was carried out at 80°C for 5 hours. The reaction was carried out and neutralized with 8 g of 48% caustic soda, and the resulting composition was designated as the emulsifier [F] of the present invention. The mixing molar ratio of the monoester and diester was 58/42. Production Example 5 A reaction vessel equipped with a stirrer, a thermometer, and a reflux tube was
sec. 786 g of a 10 mole adduct of butylphenol propylene oxide and 4 g of boron trifluoride ether complex as a catalyst were charged, and then 130 g of allyl glycidyl ether was added dropwise and reacted with stirring at 80°C for 5 hours, followed by heating to 120°C. Excess allyl glycidyl ether was removed under reduced pressure. Next, the obtained reaction composition was transferred to an autoclave, and ethylene oxide was applied to the reaction composition using caustic potassium as a catalyst at a pressure of 1.5 Kg/cm 2 and a temperature of 130°C.
Added 20 moles. Next, add 20 moles of the above ethylene oxide adduct to a reaction vessel equipped with a stirrer, thermometer, and reflux tube.
890 g and 23 g of phosphoric anhydride were charged, a phosphoric acid esterification reaction was carried out at 80° C. for 5 hours, and the resulting composition was neutralized with 50 g of dietaleramine, and the resulting composition was designated as the emulsifier [G] of the present invention. The mixing molar ratio of monoester and diester was 50/50. Example 1 Emulsion polymerization was carried out using the emulsifiers [A] to [E] of the present invention according to the following emulsion polymerization recipe, and the physical properties of the obtained emulsion and the polymer film obtained from the emulsion were tested. For comparison, examples of conventional emulsifiers were also tested. The results are shown in Table 1. [Emulsion polymerization recipe] Dissolve 295 g of water and 5 parts of emulsifier, and raise the temperature to 70°C. Next, 20 parts of monomer and 0.5 part of ammonium persulfate were added for preliminary polymerization, and 180 parts were added over a period of 3 hours starting 10 minutes after the start of polymerization to carry out polymerization. Then, at the polymerization temperature, 1
After aging for a time, it was cooled and the emulsion was taken out and used as a test sample. Next, this test sample was applied to a glass plate and dried for 24 hours at room temperature, and the dried coating film was
A polymer film was prepared by heat curing at 110°C for 3 minutes. Example 2 295 parts of water and 5 parts of various combination emulsifiers shown in Table 2 as emulsifiers were dissolved, heated to 80°C, and n-butyl acrylate/styrene = 7/3 as monomers.
20 parts of mixed monomers and 0.3 parts of ammonium persulfate
The above mixed monomer 180
After that, the emulsion was aged at 80° C. for 1 hour, cooled, and the emulsion was taken out and used as a test sample. Further, this test sample was applied to a glass plate, dried at room temperature for 24 hours, and the dried coating film was heat cured at 110° C. for 3 minutes to prepare a polymer film. Table 2 shows the physical properties of the emulsion obtained as described above and the polymer film obtained from the emulsion. In addition, examples of conventional emulsifiers are also shown in Table 2 as comparative products. Example 3 The emulsifiers [A], [F], and [G] of the present invention were prepared in Example 1.
Emulsion polymerization was carried out using the following emulsion polymerization formulation, and the physical properties of the resulting emulsion and the polymer film obtained from the emulsion were tested. The results are shown in Table 3.
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Claims (1)
åºãã¢ã«ã±ãã«åºãã¢ã«ãã«ã¢ãªãŒã«åºãããã
ã¯ã¢ã©ã«ãã«ã¢ãªãŒã«åºãã¯ççŽ æ°ïŒãïŒã®ã¢
ã«ãã¬ã³åºããããã¯çœ®æã¢ã«ãã¬ã³åºãïœã¯ïŒ
ã100ã®æŽæ°ã§ãããïœã¯ïŒã200ã®æŽæ°ã§ããã
ïŒã¯ã¢ã«ã«ãªéå±ååãNH4ãã¢ã«ã«ããŒã«ã¢
ãã³æ®åºããŸãã¯æ°ŽçŽ ååã§ããã ã§è¡šããããååç©ã®æ··åç©ãå«æããããšãç¹
城ãšããä¹³åéåçšä¹³åå€ã[Claims] 1 General formula, general formula, [However, in the above formula, R is an alkyl group, alkenyl group, alkylaryl group, or aralkylaryl group having 8 to 30 carbon atoms, A is an alkylene group having 2 to 4 carbon atoms, or a substituted alkylene group, and n is 0
is an integer of ~100, m is an integer of 1 to 200,
M is an alkali metal atom, NH 4 , an alkanolamine residue, or a hydrogen atom. ] An emulsifier for emulsion polymerization characterized by containing a mixture of compounds represented by the following.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61145943A JPS6312334A (en) | 1986-06-20 | 1986-06-20 | Emulsifying agent for aqueous resin dispersion |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61145943A JPS6312334A (en) | 1986-06-20 | 1986-06-20 | Emulsifying agent for aqueous resin dispersion |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6312334A JPS6312334A (en) | 1988-01-19 |
| JPH0223563B2 true JPH0223563B2 (en) | 1990-05-24 |
Family
ID=15396629
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61145943A Granted JPS6312334A (en) | 1986-06-20 | 1986-06-20 | Emulsifying agent for aqueous resin dispersion |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6312334A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022054640A1 (en) | 2020-09-08 | 2022-03-17 | åžçå°å·æ ªåŒäŒç€Ÿ | Organic conductive film manufacturing method, organic conductive film, and laminate |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1330134C (en) * | 1988-08-09 | 1994-06-07 | Kenji Yamamoto | Finely divided gelled polymer and process for producing the same |
| GB0101771D0 (en) | 2001-01-24 | 2001-03-07 | Ici Plc | Anionic surfactants |
| CN104011088A (en) * | 2011-12-20 | 2014-08-27 | 第äžå·¥äžå¶è¯æ ªåŒäŒç€Ÿ | Emulsifying agent for emulsion polymerization, and emulsion polymerization method using same |
| JP7680868B2 (en) * | 2020-04-10 | 2025-05-21 | æ±éŠååŠå·¥æ¥æ ªåŒäŒç€Ÿ | Emulsifier for emulsion polymerization and method for producing emulsion polymerization latex |
-
1986
- 1986-06-20 JP JP61145943A patent/JPS6312334A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022054640A1 (en) | 2020-09-08 | 2022-03-17 | åžçå°å·æ ªåŒäŒç€Ÿ | Organic conductive film manufacturing method, organic conductive film, and laminate |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6312334A (en) | 1988-01-19 |
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