JP5875854B2 - ポリイソブチレンエマルジョン - Google Patents
ポリイソブチレンエマルジョン Download PDFInfo
- Publication number
- JP5875854B2 JP5875854B2 JP2011279953A JP2011279953A JP5875854B2 JP 5875854 B2 JP5875854 B2 JP 5875854B2 JP 2011279953 A JP2011279953 A JP 2011279953A JP 2011279953 A JP2011279953 A JP 2011279953A JP 5875854 B2 JP5875854 B2 JP 5875854B2
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- JP
- Japan
- Prior art keywords
- emulsion
- meth
- polyisobutylene
- copolymer
- acrylate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000839 emulsion Substances 0.000 title claims description 125
- 229920002367 Polyisobutene Polymers 0.000 title claims description 68
- 229920001577 copolymer Polymers 0.000 claims description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- 239000003995 emulsifying agent Substances 0.000 claims description 22
- 239000002245 particle Substances 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 16
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 15
- 229920002126 Acrylic acid copolymer Polymers 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000003973 paint Substances 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- 239000000853 adhesive Substances 0.000 claims description 4
- 239000002612 dispersion medium Substances 0.000 claims description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 48
- 239000000178 monomer Substances 0.000 description 46
- -1 sucrose fatty acid ester Chemical class 0.000 description 35
- 238000000034 method Methods 0.000 description 32
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical group CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 26
- 239000004372 Polyvinyl alcohol Substances 0.000 description 21
- 229920002451 polyvinyl alcohol Polymers 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 17
- 238000006116 polymerization reaction Methods 0.000 description 13
- 238000003860 storage Methods 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 235000014113 dietary fatty acids Nutrition 0.000 description 12
- 239000000194 fatty acid Substances 0.000 description 12
- 229930195729 fatty acid Natural products 0.000 description 12
- 239000004094 surface-active agent Substances 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 239000003960 organic solvent Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 230000002209 hydrophobic effect Effects 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 238000004945 emulsification Methods 0.000 description 7
- 238000007127 saponification reaction Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 229920001451 polypropylene glycol Polymers 0.000 description 6
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000003431 cross linking reagent Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- 230000000274 adsorptive effect Effects 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 230000003111 delayed effect Effects 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 230000035699 permeability Effects 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000010526 radical polymerization reaction Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229920001214 Polysorbate 60 Polymers 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N butyl vinyl ether Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 2
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 125000005702 oxyalkylene group Chemical group 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920002689 polyvinyl acetate Polymers 0.000 description 2
- 239000011118 polyvinyl acetate Substances 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 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
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 1
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 1
- KKLSEIIDJBCSRK-UHFFFAOYSA-N 1-(chloromethyl)-2-ethenylbenzene Chemical compound ClCC1=CC=CC=C1C=C KKLSEIIDJBCSRK-UHFFFAOYSA-N 0.000 description 1
- HMDQPBSDHHTRNI-UHFFFAOYSA-N 1-(chloromethyl)-3-ethenylbenzene Chemical compound ClCC1=CC=CC(C=C)=C1 HMDQPBSDHHTRNI-UHFFFAOYSA-N 0.000 description 1
- ZRZHXNCATOYMJH-UHFFFAOYSA-N 1-(chloromethyl)-4-ethenylbenzene Chemical compound ClCC1=CC=C(C=C)C=C1 ZRZHXNCATOYMJH-UHFFFAOYSA-N 0.000 description 1
- PHQVPLFRGMMSCP-UHFFFAOYSA-N 1-chlorocycloocta-1,5-diene Chemical compound ClC1=CCCC=CCC1 PHQVPLFRGMMSCP-UHFFFAOYSA-N 0.000 description 1
- LAYAKLSFVAPMEL-UHFFFAOYSA-N 1-ethenoxydodecane Chemical compound CCCCCCCCCCCCOC=C LAYAKLSFVAPMEL-UHFFFAOYSA-N 0.000 description 1
- QJJDJWUCRAPCOL-UHFFFAOYSA-N 1-ethenoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOC=C QJJDJWUCRAPCOL-UHFFFAOYSA-N 0.000 description 1
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical compound CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 description 1
- LTGJSMARDKHZOY-UHFFFAOYSA-N 1-ethenyl-3-[(2-methylpropan-2-yl)oxy]benzene Chemical compound CC(C)(C)OC1=CC=CC(C=C)=C1 LTGJSMARDKHZOY-UHFFFAOYSA-N 0.000 description 1
- PECUPOXPPBBFLU-UHFFFAOYSA-N 1-ethenyl-3-methoxybenzene Chemical compound COC1=CC=CC(C=C)=C1 PECUPOXPPBBFLU-UHFFFAOYSA-N 0.000 description 1
- SDXHBDVTZNMBEW-UHFFFAOYSA-N 1-ethoxy-2-(2-hydroxyethoxy)ethanol Chemical compound CCOC(O)COCCO SDXHBDVTZNMBEW-UHFFFAOYSA-N 0.000 description 1
- NKVCQMYWYHDOOF-UHFFFAOYSA-N 1-phenoxyethane-1,2-diol Chemical compound OCC(O)OC1=CC=CC=C1 NKVCQMYWYHDOOF-UHFFFAOYSA-N 0.000 description 1
- ZMYIIHDQURVDRB-UHFFFAOYSA-N 1-phenylethenylbenzene Chemical group C=1C=CC=CC=1C(=C)C1=CC=CC=C1 ZMYIIHDQURVDRB-UHFFFAOYSA-N 0.000 description 1
- HKNNAYPWWDWHFR-UHFFFAOYSA-N 1-sulfanylbutan-1-ol Chemical compound CCCC(O)S HKNNAYPWWDWHFR-UHFFFAOYSA-N 0.000 description 1
- AKIZPWSPNKVOMT-UHFFFAOYSA-N 1-sulfanylhexan-1-ol Chemical compound CCCCCC(O)S AKIZPWSPNKVOMT-UHFFFAOYSA-N 0.000 description 1
- AEUVIXACNOXTBX-UHFFFAOYSA-N 1-sulfanylpropan-1-ol Chemical compound CCC(O)S AEUVIXACNOXTBX-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-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
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-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
- PGYJSURPYAAOMM-UHFFFAOYSA-N 2-ethenoxy-2-methylpropane Chemical compound CC(C)(C)OC=C PGYJSURPYAAOMM-UHFFFAOYSA-N 0.000 description 1
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
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- 238000006068 polycondensation reaction Methods 0.000 description 1
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
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- 238000002360 preparation method Methods 0.000 description 1
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- 239000000600 sorbitol Substances 0.000 description 1
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- 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
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
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- 238000004383 yellowing Methods 0.000 description 1
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Landscapes
- Compositions Of Macromolecular Compounds (AREA)
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Description
本発明に係るポリイソブチレンは、イソブチレンの重合体であり、イソブテンを原料とした公知の方法、例えば、フッ化ホウ素や塩化アルミニウムなどのフリーデルクラフト触媒を用いる重合方法によって得られるものである。このようなポリイソブチレンとしては、グリソパールV190、グリソパールV500、グリソパールV1500、オパノールB10N、B−10SFN、B11N、B−11SFN、B12N、B−12SFN、B13N、B−13SFN、B14N、B−14SFN、B15N、B−15SFN、B−30SF、B−50SF、B−80、B−100、B−150、B−200(商品名、BASF社製)等が挙げられる。ポリイソブチレンは、1種又は2種以上の組合せを使用することができる。
本発明に係る水は、エマルジョンの安定性を阻害する成分を含まないものが好ましく、例えば、イオン交換水、蒸留水、水道水である。
本発明に係る乳化剤は、ポリイソブチレン100重量部に対して1〜30重量部であるのが好ましい。より好ましくは、3〜15重量部であり、さらに好ましくは、3〜10重量部である。乳化剤がポリイソブチレン100重量部に対して1重量部より少ない場合には、ポリイソブチレンを分散することができず、エマルジョンが得られない。一方、乳化剤がポリイソブチレン100重量部に対して30重量部より多い場合には、ポリイソブチレンの特性を著しく損なう。
スチレン系モノマーとしては、スチレン、ビニルナフタレン、α―メチルスチレン、t−ブチルスチレン、p−メチルスチレン、o−メトキシスチレン、m−メトキシスチレン、p−メトキシスチレン、o−t−ブトキシスチレン、m−t−ブトキシスチレン、p−t−ブトキシスチレン、o−クロロメチルスチレン、m−クロロメチルスチレン、p−クロロメチルスチレン、ビニルトルエン、エチルビニルベンゼン、4−ビニルビフェニル、1,1−ジフェニルエチレンなどが挙げられる。好ましくは、スチレン、α―メチルスチレンである。これらのスチレン系モノマーは単独で用いてもよいが二種以上を併用してもよい。
(メタ)アクリル酸エステルモノマーとしては、芳香環を有する(メタ)アクリル酸エステルモノマー、脂肪族炭化水素基を有する(メタ)アクリル酸エステルモノマーが挙げられる。
カルボン酸系モノマー;イタコン酸、マレイン酸、フマル酸、あるいはこれらの塩など。
本発明に係るポリビニルアルコールは、通常公知の方法、例えば酢酸ビニルの重合体であるポリ酢酸ビニルをケン化することにより得られる。ケン化度とは、ポリ酢酸ビニルにおけるアセトキシ基(−OCOCH3)が水酸基(−OH)に変わっている割合を意味し、具体的には、ポリビニルアルコール中のアセトキシ基と水酸基の合計数に対する水酸基の数の百分率で表される。ポリビニルアルコール中のアセトキシ基が疎水性を示し、疎水性であるポリイソブチレンに吸着することによって、ポリイソブチレンを水中に安定に分散させることができたと考えられる。
本発明に係るエマルジョンの平均粒径は、0.03〜500μmである。好ましくは0.1〜10μmである。平均粒径が10μmより大きい場合には、エマルジョンのクリーミングが激しく、著しくエマルジョンの安定性を損なう。また、他の材料と混和しにくく、粘着性、防湿性等の特性が得られない。なお、エマルジョンの平均粒径は、SEMやTEM等の電子顕微鏡を用いて測定するか、市販のレーザ回折/散乱式粒子径分布測定装置や動的光散乱測定装置を使用して測定することができる。
本発明に係るエマルジョンは、環境に配慮して、有機溶媒を使用せず、溶媒は水のみを使用して製造するのが好ましい。しかし、ポリイソブチレンの高分子量体は非常に粘度が高く、取り扱いやすさや乳化装置の制約の点から、あらかじめ有機溶媒にポリイソブチレンを溶解させてから、有機溶媒を水に置換する方法でもよい。例えば、以下の2つの方法がある。
以下、実施例1〜6、比較例1、比較例2について、エマルジョンを作製した。エマルジョンの物性評価は以下のとおりである。
粒径測定:レーザ回折/散乱式粒子径分布測定装置LA-950(堀場製作所製)を使用し、水媒体中で測定した。
粘度測定:B型粘度計(BL型)(東洋計器社製)を使用した。200mlトールビーカーにエマルジョンを入れ、25℃に調整し、1号ローターを用い60rpmにて30秒後の数値を測定した。
ポリイソブチレン(粘度平均分子量40000mPa・s)500g、スチレン-アクリル酸系共重合体(分子量16000、酸価240mgKOH/g)の30%水溶液80g、水420gを二軸ニーダー式攪拌機に攪拌しながら加えて、濃度50wt%のエマルジョンを得た。得られたエマルジョンの粒径は0.3μm、粘度50mPa・s/25℃であった。
ポリイソブチレン(粘度平均分子量400000mPa・s)125gをトルエン375gに溶解した溶液と、スチレン-アクリル酸系共重合体(分子量16000、酸価240mgKOH/g)の30%水溶液40g、水500gを、ホモミキサーを用いて混合攪拌後、ホモジナイザー処理を行い、乳化物を得た。次に、ロータリーエバポレータを用いて50℃に加温しながら、トルエンと水の一部を減圧留去し、濃度50wt%のエマルジョンを得た。得られたエマルジョンの粒径は0.3μm、粘度50mPa・s/25℃であった。
ポリイソブチレン(粘度平均分子量55000mPa・s)500g、ポリビニルアルコール(ケン化度82mol%(中心値)、重合度500)25g、水475gを二軸ニーダー式攪拌機に攪拌しながら加え、濃度50wt%のエマルジョンを得た。得られたエマルジョンの粒径は0.4μm、粘度30mPa・s/25℃であった。
ポリイソブチレン(粘度平均分子量200000mPa・s)150gをトルエン350gに溶解した溶液と、ポリビニルアルコール(ケン化度82mol%(中心値)、重合度500)15g、水500gを、ホモミキサーを用いて混合攪拌後、ホモジナイザー処理を行い、乳化物を得た。次に、ロータリーエバポレータを用いて50℃に加温しながら、トルエンと水の一部を減圧留去し、濃度50wt%のエマルジョンを得た。得られたエマルジョンの粒径は1.0μm、粘度30mPa・s/25℃であった。
ポリイソブチレン(粘度平均分子量55000mPa・s)500g、ロジン石鹸(カリウム塩)30g、ドデシルベンゼンスルホン酸カリウム塩5g、水465gを、二軸ニーダー式攪拌機に攪拌しながら加え、エマルジョンを得た。得られたエマルジョンの粒径は1.0μm、粘度20mPa・s/25℃であった。
実施例1のエマルジョンと、スチレンアクリルエマルジョンA(酸価:60、Tg:−10℃)を固形分が1:1となるように混合した。
実施例3のエマルジョンと、スチレンアクリルエマルジョンA(酸価:60、Tg:−10℃)を固形分が1:1となるように混合した。
比較例1のエマルジョンと、スチレンアクリルエマルジョンA(酸価:60、Tg:−10℃)を固形分が1:1となるように混合した。
<保存安定性の試験方法>
100mlガラス瓶にエマルジョンを入れ、室温下、密栓状態で一定時間保管後、目視でエマルジョンの分離の有無を観察した。また、粒径測定装置にて、一定時間保管後のエマルジョンの粒径を測定し、保管前のエマルジョンに対する粒径変化の有無を確認した。目視でエマルジョンが分離していないもの、及び、粒径変化がないものを、保存安定性がよいエマルジョンと評価した。一方、目視でエマルジョンが分離しているか、粒径変化があったものについては、保存安定性が悪いエマルジョンと評価した。
<タック試験>
OPPフィルム(パイレンP2111)に、乾燥膜厚が5μmになるように、エマルジョンを塗工し、45℃で乾燥させた。その後、室温にして、指触により、タックの有無を判断した。室温時のタックがない場合を○とし、タックが少しある場合は△、タックがある場合を×とした。
<ヒートシール試験>
OPPフィルムの塗工面の上に紙をおき、80℃、10秒間、1Kg/cm2で、ヒートシールをする。紙とOPPフィルムをはがし、紙が破れたらヒートシール性があると判断した。ヒートシール性がある場合を○、ヒートシール性がやや劣る場合を△とした。
<防湿性の試験方法>
JIS−Z−0208による防湿包装材料の透湿度試験方法(カップ法)に準ずる方法で行った。具体的には、エマルジョンをバーコーター#50にて、マリコート紙に塗工し、110℃、150秒乾燥した。その後、各試料の防湿面が外側になるように、恒温高湿槽(温度40℃、相対湿度90%)に入れ、24時間後の重量変化を測定し、透湿度を算出した。透湿度の単位はg/m2である。
Claims (6)
- ポリイソブチレン100重量部に対して乳化剤を1〜30重量部含む、水を分散媒とするエマルジョンであって、
前記乳化剤が、スチレン−(メタ)アクリル酸系共重合体の水溶性塩であることを特徴とする、エマルジョン。 - 前記エマルジョンの平均粒径が0.1〜10μmであることを特徴とする、請求項1に記載のエマルジョン。
- 前記スチレン−(メタ)アクリル酸系共重合体の重量平均分子量が1800〜100000g/molであり、酸価が50〜300mgKOH/gであることを特徴とする、請求項1または2に記載のエマルジョン。
- 前記ポリイソブチレンの粘度平均分子量が1000〜400000g/molであることを特徴とする、請求項1〜3のいずれか1項に記載のエマルジョン。
- 請求項1〜4のいずれか1項に記載のエマルジョンを含むことを特徴とする、粘接着剤。
- 請求項1〜4のいずれか1項に記載のエマルジョンを含むことを特徴とする、防湿塗料。
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