JP2017536442A - リン酸エステル変性アクリルポリオール - Google Patents
リン酸エステル変性アクリルポリオール Download PDFInfo
- Publication number
- JP2017536442A JP2017536442A JP2017518782A JP2017518782A JP2017536442A JP 2017536442 A JP2017536442 A JP 2017536442A JP 2017518782 A JP2017518782 A JP 2017518782A JP 2017518782 A JP2017518782 A JP 2017518782A JP 2017536442 A JP2017536442 A JP 2017536442A
- Authority
- JP
- Japan
- Prior art keywords
- acrylate
- acrylic polyol
- methacrylate
- phosphate ester
- modified acrylic
- 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.)
- Granted
Links
- -1 Phosphate ester-modified acrylic polyol Chemical class 0.000 title claims abstract description 205
- 229920005862 polyol Polymers 0.000 title claims abstract description 170
- 229910019142 PO4 Inorganic materials 0.000 title claims description 115
- 239000010452 phosphate Substances 0.000 title claims description 115
- 239000000203 mixture Substances 0.000 claims abstract description 108
- 229920000137 polyphosphoric acid Polymers 0.000 claims abstract description 61
- 230000004048 modification Effects 0.000 claims abstract description 57
- 238000012986 modification Methods 0.000 claims abstract description 57
- 239000000178 monomer Substances 0.000 claims description 50
- 239000003054 catalyst Substances 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 37
- 239000012948 isocyanate Substances 0.000 claims description 36
- 239000002904 solvent Substances 0.000 claims description 34
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 33
- 150000002513 isocyanates Chemical class 0.000 claims description 31
- 238000000576 coating method Methods 0.000 claims description 24
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 24
- 239000000758 substrate Substances 0.000 claims description 24
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 23
- 239000011248 coating agent Substances 0.000 claims description 23
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 23
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 20
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 claims description 17
- 239000007795 chemical reaction product Substances 0.000 claims description 16
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 239000003999 initiator Substances 0.000 claims description 13
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 12
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 12
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 11
- 239000013638 trimer Substances 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 8
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 8
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 claims description 7
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 claims description 7
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical group CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 7
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 7
- 235000010290 biphenyl Nutrition 0.000 claims description 7
- 239000004305 biphenyl Substances 0.000 claims description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 7
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 7
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 claims description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 6
- 239000008096 xylene Substances 0.000 claims description 6
- JIABEENURMZTTI-UHFFFAOYSA-N 1-isocyanato-2-[(2-isocyanatophenyl)methyl]benzene Chemical class O=C=NC1=CC=CC=C1CC1=CC=CC=C1N=C=O JIABEENURMZTTI-UHFFFAOYSA-N 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 5
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 5
- 229920000642 polymer Polymers 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 5
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims description 5
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 claims description 4
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 4
- XQBCVRSTVUHIGH-UHFFFAOYSA-L [dodecanoyloxy(dioctyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCCCCCCC XQBCVRSTVUHIGH-UHFFFAOYSA-L 0.000 claims description 4
- 239000011111 cardboard Substances 0.000 claims description 4
- 239000004568 cement Substances 0.000 claims description 4
- 239000000919 ceramic Substances 0.000 claims description 4
- 239000011521 glass Substances 0.000 claims description 4
- 239000011087 paperboard Substances 0.000 claims description 4
- 239000004033 plastic Substances 0.000 claims description 4
- 229920003023 plastic Polymers 0.000 claims description 4
- ZHXAZZQXWJJBHA-UHFFFAOYSA-N triphenylbismuthane Chemical compound C1=CC=CC=C1[Bi](C=1C=CC=CC=1)C1=CC=CC=C1 ZHXAZZQXWJJBHA-UHFFFAOYSA-N 0.000 claims description 4
- 239000002023 wood Substances 0.000 claims description 4
- 229910052726 zirconium Inorganic materials 0.000 claims description 4
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical group OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 3
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- 238000007865 diluting Methods 0.000 claims description 3
- 125000005474 octanoate group Chemical group 0.000 claims description 3
- 150000002978 peroxides Chemical class 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 claims description 3
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 claims description 3
- CXOOGGOQFGCERQ-UHFFFAOYSA-N (2-methyl-2-nitropropyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)(C)[N+]([O-])=O CXOOGGOQFGCERQ-UHFFFAOYSA-N 0.000 claims description 2
- FDPPXZRLXIPXJB-UHFFFAOYSA-N (2-methyl-2-nitropropyl) prop-2-enoate Chemical compound [O-][N+](=O)C(C)(C)COC(=O)C=C FDPPXZRLXIPXJB-UHFFFAOYSA-N 0.000 claims description 2
- MNSWITGNWZSAMC-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl prop-2-enoate Chemical compound FC(F)(F)C(C(F)(F)F)OC(=O)C=C MNSWITGNWZSAMC-UHFFFAOYSA-N 0.000 claims description 2
- LMAUULKNZLEMGN-UHFFFAOYSA-N 1-ethyl-3,5-dimethylbenzene Chemical compound CCC1=CC(C)=CC(C)=C1 LMAUULKNZLEMGN-UHFFFAOYSA-N 0.000 claims description 2
- QTKPMCIBUROOGY-UHFFFAOYSA-N 2,2,2-trifluoroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)F QTKPMCIBUROOGY-UHFFFAOYSA-N 0.000 claims description 2
- VBHXIMACZBQHPX-UHFFFAOYSA-N 2,2,2-trifluoroethyl prop-2-enoate Chemical compound FC(F)(F)COC(=O)C=C VBHXIMACZBQHPX-UHFFFAOYSA-N 0.000 claims description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 2
- PTJDGKYFJYEAOK-UHFFFAOYSA-N 2-butoxyethyl prop-2-enoate Chemical compound CCCCOCCOC(=O)C=C PTJDGKYFJYEAOK-UHFFFAOYSA-N 0.000 claims description 2
- GPOGMJLHWQHEGF-UHFFFAOYSA-N 2-chloroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCl GPOGMJLHWQHEGF-UHFFFAOYSA-N 0.000 claims description 2
- FWWXYLGCHHIKNY-UHFFFAOYSA-N 2-ethoxyethyl prop-2-enoate Chemical compound CCOCCOC(=O)C=C FWWXYLGCHHIKNY-UHFFFAOYSA-N 0.000 claims description 2
- CHNGPLVDGWOPMD-UHFFFAOYSA-N 2-ethylbutyl 2-methylprop-2-enoate Chemical compound CCC(CC)COC(=O)C(C)=C CHNGPLVDGWOPMD-UHFFFAOYSA-N 0.000 claims description 2
- JGRXEBOFWPLEAV-UHFFFAOYSA-N 2-ethylbutyl prop-2-enoate Chemical compound CCC(CC)COC(=O)C=C JGRXEBOFWPLEAV-UHFFFAOYSA-N 0.000 claims description 2
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 claims description 2
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 claims description 2
- FURRSXHPLKQVIR-UHFFFAOYSA-N 2-methoxybutyl prop-2-enoate Chemical compound CCC(OC)COC(=O)C=C FURRSXHPLKQVIR-UHFFFAOYSA-N 0.000 claims description 2
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 claims description 2
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 claims description 2
- CEXQWAAGPPNOQF-UHFFFAOYSA-N 2-phenoxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC1=CC=CC=C1 CEXQWAAGPPNOQF-UHFFFAOYSA-N 0.000 claims description 2
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical group C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 claims description 2
- ILZXXGLGJZQLTR-UHFFFAOYSA-N 2-phenylethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=CC=C1 ILZXXGLGJZQLTR-UHFFFAOYSA-N 0.000 claims description 2
- HPSGLFKWHYAKSF-UHFFFAOYSA-N 2-phenylethyl prop-2-enoate Chemical compound C=CC(=O)OCCC1=CC=CC=C1 HPSGLFKWHYAKSF-UHFFFAOYSA-N 0.000 claims description 2
- NWKKCUWIMOZYOO-UHFFFAOYSA-N 3-methoxybutyl 2-methylprop-2-enoate Chemical compound COC(C)CCOC(=O)C(C)=C NWKKCUWIMOZYOO-UHFFFAOYSA-N 0.000 claims description 2
- NPYMXLXNEYZTMQ-UHFFFAOYSA-N 3-methoxybutyl prop-2-enoate Chemical compound COC(C)CCOC(=O)C=C NPYMXLXNEYZTMQ-UHFFFAOYSA-N 0.000 claims description 2
- ZVYGIPWYVVJFRW-UHFFFAOYSA-N 3-methylbutyl prop-2-enoate Chemical compound CC(C)CCOC(=O)C=C ZVYGIPWYVVJFRW-UHFFFAOYSA-N 0.000 claims description 2
- MUPJJZVGSOUSFH-UHFFFAOYSA-N 4-(2-cyanoethyl)-4-nitroheptanedinitrile Chemical compound N#CCCC([N+](=O)[O-])(CCC#N)CCC#N MUPJJZVGSOUSFH-UHFFFAOYSA-N 0.000 claims description 2
- YGQURMQHUGDYAO-UHFFFAOYSA-N 4-[2-[2-(4-nitrophenyl)imidazo[2,1-b][1,3]benzothiazol-6-yl]oxyethyl]morpholine Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=CN2C3=CC=C(OCCN4CCOCC4)C=C3SC2=N1 YGQURMQHUGDYAO-UHFFFAOYSA-N 0.000 claims description 2
- NUXLDNTZFXDNBA-UHFFFAOYSA-N 6-bromo-2-methyl-4h-1,4-benzoxazin-3-one Chemical compound C1=C(Br)C=C2NC(=O)C(C)OC2=C1 NUXLDNTZFXDNBA-UHFFFAOYSA-N 0.000 claims description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 2
- QMEMFEMQJJOZGM-RMKNXTFCSA-N [(e)-3-phenylprop-2-enyl] prop-2-enoate Chemical compound C=CC(=O)OC\C=C\C1=CC=CC=C1 QMEMFEMQJJOZGM-RMKNXTFCSA-N 0.000 claims description 2
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 claims description 2
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 claims description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 2
- FCSHDIVRCWTZOX-DVTGEIKXSA-N clobetasol Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CCl)(O)[C@@]1(C)C[C@@H]2O FCSHDIVRCWTZOX-DVTGEIKXSA-N 0.000 claims description 2
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 claims description 2
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 claims description 2
- WRAABIJFUKKEJQ-UHFFFAOYSA-N cyclopentyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCC1 WRAABIJFUKKEJQ-UHFFFAOYSA-N 0.000 claims description 2
- BTQLDZMOTPTCGG-UHFFFAOYSA-N cyclopentyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCC1 BTQLDZMOTPTCGG-UHFFFAOYSA-N 0.000 claims description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 2
- FKIRSCKRJJUCNI-UHFFFAOYSA-N ethyl 7-bromo-1h-indole-2-carboxylate Chemical compound C1=CC(Br)=C2NC(C(=O)OCC)=CC2=C1 FKIRSCKRJJUCNI-UHFFFAOYSA-N 0.000 claims description 2
- DWXAVNJYFLGAEF-UHFFFAOYSA-N furan-2-ylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CO1 DWXAVNJYFLGAEF-UHFFFAOYSA-N 0.000 claims description 2
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 claims description 2
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000005641 methacryl group Chemical group 0.000 claims description 2
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 claims description 2
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 claims description 2
- QHGUPRQTQITEPO-UHFFFAOYSA-N oxan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCO1 QHGUPRQTQITEPO-UHFFFAOYSA-N 0.000 claims description 2
- FGWRVVZMNXRWDQ-UHFFFAOYSA-N oxan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCO1 FGWRVVZMNXRWDQ-UHFFFAOYSA-N 0.000 claims description 2
- GYDSPAVLTMAXHT-UHFFFAOYSA-N pentyl 2-methylprop-2-enoate Chemical compound CCCCCOC(=O)C(C)=C GYDSPAVLTMAXHT-UHFFFAOYSA-N 0.000 claims description 2
- ULDDEWDFUNBUCM-UHFFFAOYSA-N pentyl prop-2-enoate Chemical compound CCCCCOC(=O)C=C ULDDEWDFUNBUCM-UHFFFAOYSA-N 0.000 claims description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 2
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 claims description 2
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 claims description 2
- WPBNLDNIZUGLJL-UHFFFAOYSA-N prop-2-ynyl prop-2-enoate Chemical compound C=CC(=O)OCC#C WPBNLDNIZUGLJL-UHFFFAOYSA-N 0.000 claims description 2
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 claims description 2
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 claims description 2
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 claims description 2
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 claims description 2
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 claims description 2
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 claims description 2
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims description 2
- WDHYRUBXLGOLKR-UHFFFAOYSA-N phosphoric acid;prop-2-enoic acid Chemical compound OC(=O)C=C.OP(O)(O)=O WDHYRUBXLGOLKR-UHFFFAOYSA-N 0.000 claims 1
- 239000012528 membrane Substances 0.000 description 15
- 150000003077 polyols Chemical class 0.000 description 15
- 238000009472 formulation Methods 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
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Abstract
Description
本出願は、2014年10月8日に出願された米国仮特許出願第62/061,558号の利益を主張し、その開示全体はあらゆる全ての目的のために参照により本明細書に組み込まれる。
スキーム1:
次の文字が付けられた項目(「項」)を本出願のいくつかの非限定的実施形態を説明するために提供する。
Claims (38)
- リン酸エステル変性アクリルポリオールを含む組成物であって、前記リン酸エステル変性アクリルポリオールは、0を超えるが、1.0重量%未満のリン酸エステル変性を含む、組成物。
- 前記リン酸エステル変性アクリルポリオールが、0を超えるが、0.5重量%未満のリン酸エステル変性を含む、請求項1に記載の組成物。
- 前記リン酸エステル変性アクリルポリオールが、0を超えるが、0.3重量%未満のリン酸エステル変性を含む、請求項2に記載の組成物。
- 前記リン酸エステル変性アクリルポリオールが、0を超えるが、0.2重量%未満のリン酸エステル変性を含む、請求項3に記載の組成物。
- アクリルポリオールと前記アクリルポリオールを基準としてX重量%のポリリン酸との反応生成物を含む組成物であって、0.01≦X≦1.0である、組成物。
- 0.01≦X≦0.5である、請求項5に記載の組成物。
- 0.01≦X≦0.2である、請求項6に記載の組成物。
- 前記アクリルポリオールが、アクリル系、メタクリル系、もしくはスチレン系モノマー、またはこれらの任意の2つ以上の混合物と、ヒドロキシル化アクリル系、ヒドロキシル化メタクリル系モノマー、アリルアルコールモノマー、またはこれらの任意の2つ以上の混合物との反応生成物を含む、請求項1〜7のいずれか1項に記載の組成物。
- 前記アクリル系、メタクリル系、またはスチレン系モノマーは、アクリル酸、メタクリル酸、メタクリル酸メチル、アクリル酸エチル、メタクリル酸エチル、アクリル酸n−プロピル、メタクリル酸n−プロピル、アクリル酸n−ブチル、メタクリル酸n−ブチル、アクリル酸イソプロピル、メタクリル酸イソプロピル、アクリル酸イソブチル、メタクリル酸イソブチル、アクリル酸n−アミル、メタクリル酸n−アミル、アクリル酸n−ヘキシル、メタクリル酸n−ヘキシル、アクリル酸イソアミル、メタクリル酸イソアミル、アクリル酸トリフルオロエチル、メタクリル酸トリフルオロエチル、アクリル酸ベンジル、メタクリル酸ベンジル、アクリル酸2−n−ブトキシエチル、メタクリル酸2−n−ブトキシエチル、アクリル酸2−クロロエチル、メタクリル酸2−クロロエチル、アクリル酸sec−ブチル、メタクリル酸sec−ブチル、アクリル酸tert−ブチル、メタクリル酸tert−ブチル、アクリル酸2−エチルブチル、メタクリル酸2−エチルブチル、アクリル酸シンナミル、メタクリル酸シンナミル、アクリル酸シクロヘキシル、メタクリル酸シクロヘキシル、アクリル酸シクロペンチル、メタクリル酸シクロペンチル、アクリル酸2−エトキシエチル、メタクリル酸2−エトキシエチル、アクリル酸フルフリル、メタクリル酸フルフリル、アクリル酸ヘキサフルオロイソプロピル、メタクリル酸ヘキサフルオロイソプロピル、アクリル酸3−メトキシブチル、メタクリル酸3−メトキシブチル、アクリル酸2−メトキシブチル、メタクリル酸2−メトキシブチル、アクリル酸2−ニトロ−2−メチルプロピル、メタクリル酸2−ニトロ−2−メチルプロピル、アクリル酸n−オクチル、メタクリル酸n−オクチル、アクリル酸2−エチルヘキシル、メタクリル酸2−エチルヘキシル、アクリル酸2−フェノキシエチル、メタクリル酸2−フェノキシエチル、アクリル酸2−フェニルエチル、メタクリル酸2−フェニルエチル、アクリル酸フェニル、メタクリル酸フェニル、アクリル酸プロパルギル、メタクリル酸プロパルギル、アクリル酸テトラヒドロフルフリル、メタクリル酸テトラヒドロフルフリル、アクリル酸テトラヒドロピラニル、メタクリル酸テトラヒドロピラニル、スチレン、またはα−メチルスチレンを含む、請求項8に記載の組成物。
- 前記ヒドロキシル化モノマーがヒドロキシル化アクリル系またはメタクリル系モノマーを含み、その際、前記ヒドロキシル化アクリル系またはメタクリル系モノマーがアクリル酸2−ヒドロキシエチル、メタクリル酸2−ヒドロキシエチル、アクリル酸2−ヒドロキシプロピル、メタクリル酸2−ヒドロキシプロピル、またはアリルアルコールを含む、請求項8に記載の組成物。
- 前記反応生成物が、アクリル系、メタクリル系、もしくはスチレン系モノマー、またはこれらの任意の2つ以上の混合物と、ヒドロキシル化アクリル系もしくはメタクリル系モノマーもしくはアリルアルコール、またはこれらの任意の2つ以上の混合物との反応において使用された開始剤の残基を更に含む、請求項8に記載の組成物。
- 前記開始剤が、ジアルキルパーオキサイド、アルキルパーオキシエステル、またはフリーラジカル、アゾ系開始剤である、請求項11に記載の組成物。
- イソシアネートを更に含む、請求項1〜12のいずれか1項に記載の組成物。
- 前記イソシアネートが、ジフェニルジイソシアネート、1,6−ヘキサメチレンジイソシアネート、イソホロンジイソシアネート、イソホロンジイソシアネートの三量体、2,4−トルエンジイソシアネート、2,6−トルエンジイソシアネート、メチレンジフェニルジイソシアネート、ポリマーのメチレンジフェニルジイソシアネート、メチレンビス−シクロヘキシルジイソシアネート、ナフタレンジイソシアネート、水素化メチレンジフェニルジイソシアネート、ヘキサメチレンジイソシアネートの三量体、アロファネート、ビウレット、またはこれらの任意の2つ以上の混合物を含む、請求項13に記載の組成物。
- 触媒を更に含む、請求項13に記載の組成物。
- 前記触媒が、有機スズ、有機ビスマス、有機亜鉛、金属オクトエート、または金属ジオネート触媒である、請求項15に記載の組成物。
- 前記触媒が、トリフェニルビスマス、ジブチルスズジラウレート、ジブチルスズジアセテート、ジオクチルスズジラウレート、亜鉛オクトエート、スズオクトエート、ジルコニウムジオネート、コバルトジオネート、またはこれらの任意の2つ以上の混合物を含む有機スズ触媒である、請求項15に記載の組成物。
- 非リン酸エステル変性アクリルポリオールの反応生成物を含む組成物よりも長いポットライフを示す、請求項15に記載の組成物。
- 非リン酸エステル変性アクリルポリオールの反応生成物を含む組成物と比較した場合、改善された接着性を示す、請求項15に記載の組成物。
- イソシアネートを含む第1の成分と、
ポリリン酸変性アクリルポリオールを含む第2の成分であって、前記ポリリン酸変性アクリルポリオールは、0を超えるが、1.0重量%未満のポリリン酸による変性を含む、第2の成分と、を含む、2成分コーティングパッケージ。 - 前記ポリリン酸変性アクリルポリオールが、0を超えるが、0.5重量%未満のポリリン酸による変性を含む、請求項20に記載の2成分コーティングパッケージ。
- 前記ポリリン酸変性アクリルポリオールが、0を超えるが、0.2重量%未満のポリリン酸による変性を含む、請求項21に記載の2成分コーティングパッケージ。
- 前記イソシアネートが、ジフェニルジイソシアネート、1,6−ヘキサメチレンジイソシアネート、イソホロンジイソシアネート、イソホロンジイソシアネートの三量体、2,4−トルエンジイソシアネート、2,6−トルエンジイソシアネート、メチレンジフェニルジイソシアネート、ポリマーのメチレンジフェニルジイソシアネート、メチレンビス−シクロヘキシルジイソシアネート、ナフタレンジイソシアネート、水素化メチレンジフェニルジイソシアネート、ヘキサメチレンジイソシアネートの三量体、アロファネート、ビウレット、またはこれらの任意の2つ以上の混合物を含む、請求項20〜22のいずれか1項に記載の2成分コーティングパッケージ。
- 前記第1の成分、前記第2の成分、または前記第1の成分及び前記第2の成分の両方に触媒を更に含む、請求項20〜22のいずれか1項に記載の2成分コーティングパッケージ。
- リン酸エステル変性アクリルポリオールの調製方法であって、
溶媒中にアクリルポリオールを提供することと、
前記アクリルポリオールを基準として最大1.0重量%のポリリン酸を添加することと、を含む、方法。 - 前記アクリルポリオールを基準として最大0.5重量%のポリリン酸を添加することを含む、請求項25に記載の方法。
- 前記溶媒が、メチルイソブチルケトン、メチルアミルケトン、n−ブチルアセテート、またはキシレンである、請求項25または26に記載の方法。
- 原料リン酸エステル変性アクリルポリオールの調製方法であって、
溶媒中にアクリルポリオールを提供することと、
前記アクリルポリオールを基準として最大10重量%のポリリン酸を添加して、前記原料リン酸エステル変性アクリルポリオールを形成することと、を含む、方法。 - 追加の溶媒、または非リン酸エステル変性アクリルポリオールとの混合により、前記原料リン酸エステル変性アクリルポリオールを希釈することを更に含む、請求項28に記載の方法。
- 前記溶媒がメチルイソブチルケトン、メチルアミルケトン、n−ブチルアセテート、またはキシレンである、請求項29に記載の方法。
- 前記非リン酸エステル変性アクリルポリオールが、前記アクリルポリオールである、請求項29または30に記載の方法。
- リン酸エステル変性アクリルポリオールの調製方法であって、
リン酸エステル変性モノマーを、アクリル系、メタクリル系、もしくはスチレン系モノマー、またはこれらの任意の2つ以上の混合物と溶媒中で混合することと、
前記モノマーを重合して前記リン酸エステル変性アクリルポリオールを形成することと、を含む、方法。 - 前記リン酸エステルモノマーが、2−ヒドロキシエチル(メタ)アクリレートリン酸エステルである、請求項32に記載の方法。
- コーティングされた基材であって、
基材の少なくとも一部に接着されかつそれをコーティングする膜であって、イソシアネート、触媒、及びリン酸エステル変性アクリルポリオールの反応生成物を含む、膜を備え、
前記リン酸エステル変性アクリルポリオールは、0を超えるが、1.0重量%未満の変性を含む、コーティングされた基材。 - 前記リン酸エステル変性アクリルポリオールが、0を超えるが、0.3重量%未満の変性を含む、請求項34に記載のコーティングされた基材。
- 前記リン酸エステル変性アクリルポリオールが、0を超えるが、0.2重量%未満の変性を含む、請求項35に記載のコーティングされた基材。
- 前記触媒が、有機スズまたは有機ビスマス触媒である、請求項34、35、または36に記載のコーティングされた基材。
- 前記基材が、ガラス、セラミック、木材、セメント、プラスチック、紙、またはボール紙を含む、請求項34、35、または36に記載のコーティングされた基材。
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