JP2014518909A - 多官能一級アミン、その調製方法、及びその使用 - Google Patents
多官能一級アミン、その調製方法、及びその使用 Download PDFInfo
- Publication number
- JP2014518909A JP2014518909A JP2014508808A JP2014508808A JP2014518909A JP 2014518909 A JP2014518909 A JP 2014518909A JP 2014508808 A JP2014508808 A JP 2014508808A JP 2014508808 A JP2014508808 A JP 2014508808A JP 2014518909 A JP2014518909 A JP 2014518909A
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- Prior art keywords
- amine
- group
- groups
- polyfunctional
- compound
- 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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- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 title claims abstract description 49
- 238000000034 method Methods 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title abstract description 10
- 230000008569 process Effects 0.000 title abstract description 4
- 150000001412 amines Chemical class 0.000 claims abstract description 85
- 239000003822 epoxy resin Substances 0.000 claims abstract description 71
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 71
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims abstract description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- 230000002378 acidificating effect Effects 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 150000001408 amides Chemical group 0.000 claims abstract description 7
- 125000004185 ester group Chemical group 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims abstract description 6
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000000542 sulfonic acid group Chemical group 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000006185 dispersion Substances 0.000 claims description 43
- 150000001875 compounds Chemical class 0.000 claims description 37
- 239000003795 chemical substances by application Substances 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 35
- 150000002118 epoxides Chemical group 0.000 claims description 28
- 239000000126 substance Substances 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- -1 oxypropylene moiety Chemical group 0.000 claims description 18
- 150000003141 primary amines Chemical class 0.000 claims description 17
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims description 16
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 15
- 239000000049 pigment Substances 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 239000004593 Epoxy Substances 0.000 claims description 13
- 150000004820 halides Chemical class 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 9
- 150000004658 ketimines Chemical class 0.000 claims description 9
- 239000000758 substrate Substances 0.000 claims description 9
- 239000002981 blocking agent Substances 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 150000002576 ketones Chemical class 0.000 claims description 7
- 230000004048 modification Effects 0.000 claims description 6
- 238000012986 modification Methods 0.000 claims description 6
- 150000002989 phenols Chemical class 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- ZAXCZCOUDLENMH-UHFFFAOYSA-N 3,3,3-tetramine Chemical compound NCCCNCCCNCCCN ZAXCZCOUDLENMH-UHFFFAOYSA-N 0.000 claims description 3
- 239000002262 Schiff base Substances 0.000 claims description 3
- 150000004753 Schiff bases Chemical class 0.000 claims description 3
- 150000004705 aldimines Chemical class 0.000 claims description 3
- MRNZSTMRDWRNNR-UHFFFAOYSA-N bis(hexamethylene)triamine Chemical compound NCCCCCCNCCCCCCN MRNZSTMRDWRNNR-UHFFFAOYSA-N 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 239000002518 antifoaming agent Substances 0.000 claims description 2
- 150000001541 aziridines Chemical group 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- 230000004927 fusion Effects 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000006353 oxyethylene group Chemical group 0.000 claims description 2
- 230000007480 spreading Effects 0.000 claims description 2
- 238000003892 spreading Methods 0.000 claims description 2
- 239000004034 viscosity adjusting agent Substances 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims 1
- 150000001244 carboxylic acid anhydrides Chemical group 0.000 claims 1
- 239000012948 isocyanate Chemical group 0.000 claims 1
- 150000002513 isocyanates Chemical group 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims 1
- 125000003700 epoxy group Chemical group 0.000 abstract description 3
- 239000003973 paint Substances 0.000 description 36
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 28
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 17
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 17
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 12
- 238000001035 drying Methods 0.000 description 11
- 239000004848 polyfunctional curative Substances 0.000 description 11
- 230000007797 corrosion Effects 0.000 description 10
- 238000005260 corrosion Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 229920001223 polyethylene glycol Polymers 0.000 description 8
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 7
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 7
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 7
- 239000002202 Polyethylene glycol Substances 0.000 description 7
- 239000008199 coating composition Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229920003986 novolac Polymers 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 5
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- CUFXMPWHOWYNSO-UHFFFAOYSA-N 2-[(4-methylphenoxy)methyl]oxirane Chemical compound C1=CC(C)=CC=C1OCC1OC1 CUFXMPWHOWYNSO-UHFFFAOYSA-N 0.000 description 4
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 238000009408 flooring Methods 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- HHRACYLRBOUBKM-UHFFFAOYSA-N 2-[(4-tert-butylphenoxy)methyl]oxirane Chemical compound C1=CC(C(C)(C)C)=CC=C1OCC1OC1 HHRACYLRBOUBKM-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229910015900 BF3 Inorganic materials 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical group ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- OTBHHUPVCYLGQO-UHFFFAOYSA-N bis(3-aminopropyl)amine Chemical compound NCCCNCCCN OTBHHUPVCYLGQO-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 2
- YTTWDTVYXAEAJA-UHFFFAOYSA-N 2,2-dimethyl-hexanoic acid Chemical compound CCCCC(C)(C)C(O)=O YTTWDTVYXAEAJA-UHFFFAOYSA-N 0.000 description 2
- VUAXHMVRKOTJKP-UHFFFAOYSA-N 2,2-dimethylbutyric acid Chemical compound CCC(C)(C)C(O)=O VUAXHMVRKOTJKP-UHFFFAOYSA-N 0.000 description 2
- QRMMMWOSHHVOCJ-UHFFFAOYSA-N 2,2-dimethylheptanoic acid Chemical compound CCCCCC(C)(C)C(O)=O QRMMMWOSHHVOCJ-UHFFFAOYSA-N 0.000 description 2
- IKNDGHRNXGEHTO-UHFFFAOYSA-N 2,2-dimethyloctanoic acid Chemical compound CCCCCCC(C)(C)C(O)=O IKNDGHRNXGEHTO-UHFFFAOYSA-N 0.000 description 2
- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- KRIMXCDMVRMCTC-UHFFFAOYSA-N 2-methylhexan-2-ol Chemical compound CCCCC(C)(C)O KRIMXCDMVRMCTC-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- ZRYCZAWRXHAAPZ-UHFFFAOYSA-N alpha,alpha-dimethyl valeric acid Chemical compound CCCC(C)(C)C(O)=O ZRYCZAWRXHAAPZ-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229920006334 epoxy coating Polymers 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 2
- QQWAKSKPSOFJFF-UHFFFAOYSA-N oxiran-2-ylmethyl 2,2-dimethyloctanoate Chemical compound CCCCCCC(C)(C)C(=O)OCC1CO1 QQWAKSKPSOFJFF-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- UODZHRGDSPLRMD-UHFFFAOYSA-N sym-homospermidine Chemical compound NCCCCNCCCCN UODZHRGDSPLRMD-UHFFFAOYSA-N 0.000 description 2
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- DEQUKPCANKRTPZ-UHFFFAOYSA-N (2,3-dihydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1O DEQUKPCANKRTPZ-UHFFFAOYSA-N 0.000 description 1
- KMOUUZVZFBCRAM-UHFFFAOYSA-N 1,2,3,6-tetrahydrophthalic anhydride Chemical compound C1C=CCC2C(=O)OC(=O)C21 KMOUUZVZFBCRAM-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- AOFRNZNXMCOXHP-UHFFFAOYSA-N 2-(2-carboxyphenyl)sulfonylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1C(O)=O AOFRNZNXMCOXHP-UHFFFAOYSA-N 0.000 description 1
- QUWAJPZDCZDTJS-UHFFFAOYSA-N 2-(2-hydroxyphenyl)sulfonylphenol Chemical compound OC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1O QUWAJPZDCZDTJS-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- OAOABCKPVCUNKO-UHFFFAOYSA-N 8-methyl Nonanoic acid Chemical compound CC(C)CCCCCCC(O)=O OAOABCKPVCUNKO-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 229910001018 Cast iron Inorganic materials 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 229910001208 Crucible steel Inorganic materials 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- VYKBVDDGORZEQF-UHFFFAOYSA-N N'-[2-[2-(2-aminoethylamino)ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCN.NCCNCCNCCNCCN VYKBVDDGORZEQF-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000000539 amino acid group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- AMEDKBHURXXSQO-UHFFFAOYSA-N azonous acid Chemical class ONO AMEDKBHURXXSQO-UHFFFAOYSA-N 0.000 description 1
- 239000010953 base metal Substances 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 150000003818 basic metals Chemical class 0.000 description 1
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- YUSYSJSHVJULID-UHFFFAOYSA-N combretastatin A1 Z Natural products OC1=C(O)C(OC)=CC=C1C=CC1=CC(OC)=C(OC)C(OC)=C1 YUSYSJSHVJULID-UHFFFAOYSA-N 0.000 description 1
- HRRAOGKGGZFKSW-UHFFFAOYSA-N combretastatin A2 Natural products COc1ccc(C=C/c2cc(O)c3OCOc3c2)cc1OC HRRAOGKGGZFKSW-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical group C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000000383 hazardous chemical Substances 0.000 description 1
- 231100000206 health hazard Toxicity 0.000 description 1
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- GRUKDYYUQCLECD-UHFFFAOYSA-N n'-(2-azanylethyl)ethane-1,2-diamine Chemical compound NCCNCCN.NCCNCCN GRUKDYYUQCLECD-UHFFFAOYSA-N 0.000 description 1
- HTKHOGUGJYFTHN-UHFFFAOYSA-N n'-[2-(2-aminoethylamino)ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCN.NCCNCCNCCN HTKHOGUGJYFTHN-UHFFFAOYSA-N 0.000 description 1
- RPSHOHKFHRFBAZ-UHFFFAOYSA-N n'-[4-(4-aminobutylamino)butyl]butane-1,4-diamine Chemical compound NCCCCNCCCCNCCCCN RPSHOHKFHRFBAZ-UHFFFAOYSA-N 0.000 description 1
- 239000012875 nonionic emulsifier Substances 0.000 description 1
- 235000019645 odor Nutrition 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- RVEZZJVBDQCTEF-UHFFFAOYSA-N sulfenic acid Chemical group SO RVEZZJVBDQCTEF-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical group SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- NTKBNCABAMQDIG-UHFFFAOYSA-N trimethylene glycol-monobutyl ether Natural products CCCCOCCCO NTKBNCABAMQDIG-UHFFFAOYSA-N 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical group OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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Abstract
Description
を有する樹脂物質として定義される。
−[−O−CH2−CH(OH)−CH2−OAr−]n− (式II)
(式中Arは二価の、芳香族又は芳香族−脂肪族混合ラジカルを表し、例示すると、ビスフェノールAの場合は
−C6H4−C(CH3)2−C6H4− (式III)
である)の形成下反応させることにより、又は、例えばビスフェノールAのジエーテルとグリシドールを、更なるビスフェノールA(又は他の多価フェノール性化合物)と反応させる、いわゆる促進反応により、作られる。ここで詳述した低モル質量エポキシ樹脂は、本発明に対して好ましい成分Cである。
の形成下、常に、一級アミノ基が消費された反応生成物をもたらす。この反応は、おそらく全ての一級アミノ基を消費し、所望の官能性をもたらさないであろう。この理由から、アミンAをエポキシ官能化合物と反応させるときは、一級アミノ基を、エポキシド基との反応から保護しなければならない。これは、アミンAと多官能化合物Cの間の反応生成物の形成後に除去、又は分離できる、ブロッキング剤Bで成すことができる。
H2N−(CH2)n−NH−(CH2)n’−NH2
のジ一級モノ二級アミンの使用が好ましく、n、n’及びn”は、独立に、2〜12、好ましくは3〜8の整数である。アルキレン鎖中の1以上の炭素原子が、炭素原子1〜4個を有するアルキル基、又は炭素原子1〜4個を有するアルコキシ基によって置換されていてよい。式
H2N−(CH2)n−[NH−(CH2)n’]n”−NH2
のアミンを使用することも可能である。好ましくは、ジエチレントリアミン(l,5−ジアミノ−3−アザペンタン)、トリエチレンテトラミン(1,8−ジアミノ−3,6−ジアザオクタン)、テトラエチレンペンタミン(1,11−ジアミノ−3,6,9−トリアザウンデカン)、ジプロピレントリアミン(l,7−ジアミノ−4−アザヘプタン)、トリプロピレンテトラミン(1,11−ジアミノ−4,8−ジアザウンデカン)、ジブチレントリアミン(l,9−ジアミノ−5−アザノナン)、トリブチレンテトラミン(1,14−ジアミノ−5,10−ジアザテトラデカン)、ジヘキシレントリアミン(l,13−ジアミノ−7−アザトリデカン)、及びトリヘキシレンテトラミン(l,20−ジアミノ−7,14−ジアザエイコサン)、並びにこれらの混合物である。
H2N−CH(CH3)−CH2−[O−CH(CH3)−CH2−]p−NH−CO−NH−[CH2−CH(CH3)−O−]p−CH2−CH(CH3)−NH2
(式中pは1〜6の範囲でよい)
の使用も可能である。この様なアミンは、これらがすでに十分な親水性を備えているという利点を有し、多官能化合物CはアミンACに更に親水性を追加する必要が無く、必要なのは、尿素由来の部分中のアミド性基に対して反応性があることだけである。
Gly−O−Ar−[−O−CH2−CH(OH)−CH2−O−Ar−]n−O−Gly (式IV)
(式中nは少なくとも0の整数であり、Gly−はグリシジル
を示す)
に従う少なくとも一つの繰り返し単位を有するエポキシ樹脂のグリシジルエーテルが好ましい。
ジエチレントリアミン(DETA)103g(1モル)及びメチルイソブチルケトン(MIBK)300g(3モル)を、機械的撹拌機、ディーン・スターク・トラップ及び気体導入口を備えた四つ口フラスコ中に充填し、窒素流の下、加熱して8時間還流させた。水が最早回収されないとき、過剰のMIBKを除去して純粋なDETA−MIBK−ケチミンを産出させた。
ビスフェノールAジグリシジルエーテル(BADGE)2546g、平均モル質量1500g/molであるポリエチレングリコール450g及びメトキシプロパノール941gを、機械的撹拌機を備えた四つ口フラスコ中に充填し、撹拌下、100℃に加熱した。この温度に到達したとき、三フッ化ホウ素アミン(BF3−NH3)3gをこのフラスコ中に充填し、この混合物を130℃に加熱し、この温度に2時間保持してエポキシド基の比含量を3.24モル/kgに到達させた。反応混合物を、次いで、100℃に冷却し、ビスフェノールA776gとトリフェニルホスフィン3gを反応フラスコ中に充填した。反応混合物を、次いで、撹拌下、130℃に再度加熱し、この温度に2時間保持して反応混合物中のエポキシド基の比含量を1.27モル/kgに到達させた。次に、メトキシプロパノール380gを添加し、反応混合物を80℃に冷却した。この温度で、例1のケチミンK1を1335g添加し、混合物を20分間撹拌した。混合物を、次いで、90℃に加熱し、撹拌下、ジエタノールアミン84gを添加し、混合物を90℃で20分間保持した。次いで、ジメチルアミノプロピルアミン10.2gを添加し、反応混合物を100℃に加熱して2時間撹拌した。BADGE95gを添加して未反応の自由アミンを捕集し、混合物を、100℃で更に1時間撹拌した。室温(23℃)に冷却後、固体の質量比が80%であることが決定され、また、23℃、剪断速度25s−1で測定した動的粘度は5000mPa−sであった。
例2のエポキシアミン付加物A1の6624gを95℃に加熱し、乳酸の強度50%水溶液429gで中和し、引き続き水6700gを加えた。溶媒のメトキシプロパノールとMIBKを、100hPaの減圧下、60℃で留去した。溶媒の蒸留が止まったとき、クレジルグリシジルエーテル821gを分散物に添加し、混合物を2時間撹拌した。分散物の固体の質量比を、水1500gを添加して、35%に調整した。分散物の粘度は、23℃、剪断速度100s−1で20mPa−s、アミン水素元素の比含量は0.88モル/kg、そのZ−平均粒径は150nm、及びその酸価は24mg/gであった。
ケチミンK2を、例1と同様にして、ビス(6−アミノヘキシル)−アミン1モルとメチルイソブチルケトン3モルから調製した。
例3及び4に記載した分散物D1〜D5を、2パックエポキシ−アミン塗料に対する硬化剤として使用した。これらの分散物を例5の顔料ペーストと混合して2バック系の成分1を得た。塗料を基板に塗布する直前に、成分2−親水性に修飾されたエポキシ樹脂−を、機械的撹拌機で成分1に混合した。エポキシド基の物質量nEPに対する活性N−H基の物質量nNHの比nNH/nEPを0.7モル/1モルに設定した。顔料ペーストの質量を、バインダーの質量に対する顔料の質量の比が塗料中で1.5/1となる様に選んだ。
分散物D1の100gを、例5の顔料ペースト70gと脱イオン水35gと混合した。混合物を、機械的撹拌機で30分間撹拌した後、ビスフェノールAジグリシジルエーテル“BADGE”618g及びビスフェノールFジグリシジルエーテル262gと、平均モル質量1kg/molのポリエチレングリコール385gとBADGE612g及び三フッ化ホウ素−ベンジルアミン錯体2gとを反応させて作製した乳化剤119g(EP0000605B1参照)との混合物として調製した、乳化したエポキシ樹脂Elの25gを、撹拌した混合物に添加した。膜形成を向上させるため、n−ブトキシプロパノール2gを添加した。得られた塗料は、固体の質量比48.5%、及び23℃、剪断速度25s−1で測定した粘度300mPa−sを有していた。
上述した手順に従って、2パック塗料を、上述した乳化したエポキシ樹脂Elと共に、硬化剤分散物D2及びD3から調製した。
例6.1及び6.2の着色塗料P1、P2及びP3から、塗料膜を、未乾燥の層厚200μmに塗布した。膜を、いずれの場合も、室温(23℃)で6時間硬化させた。乾燥後の表面は、全ての場合において滑らかであり、エポキシ樹脂と硬化剤の良好な相溶性を示していた。
耐食塗料における新規製品の能力を評価するために、それぞれ、分散物中の固体の質量比53%と、エポキシ基の比含量1.92モル/kg(“エポキシ当量”520g/mol)、後者は固体樹脂の質量に基づく、とを有する固体エポキシ樹脂E2の水系エポキシ分散物と組み合わせて、これらを最先端のエポキシ硬化剤、CA2及びCA1と比較した。
上述の表5のように、本発明に係る硬化剤分散物D3、並びに硬化剤CA1及びCA2と、ビスフェノールA及びビスフェノールFの混合物に基づく液体エポキシ樹脂L1、更にポリエチレングリコールとビスフェノールAジグリシジルエーテルの反応生成物に基づく乳化剤、及び反応性希釈剤としてビスフェノールAジグリシジルエーテル70%とtert−ブチルフェニルグリシジルエーテル30%の質量比の混合物を含む液体エポキシ樹脂L2のそれぞれと、例5の顔料ペーストとの混合物を調製し、表に示したように、これらの混合物をエポキシ樹脂と組み合わせて、エポキシド基の物質量nEPに対するアミン水素原子N−Hの物質量nNHの比nNH/nEPが0.7モル/1モルである2パック塗装組成物を提供した。例5の顔料ペーストの質量は、バインダーの質量に対する顔料の質量の比が塗料中で1.5/1となるように選んだ。
Claims (15)
- 1分子あたり1個を超える一級アミノ基、並びに、1分子あたり少なくとも1個の、エポキシド基と、二級アミノ基>NH、水酸基−OH、メルカプタン基−SH、アミド基−CO−NHR(式中Rは水素又は1〜12個の炭素原子を有するアルキル基であって良い)、ヒドロキシエステル基、及び酸性基、特にカルボキシル基−COOH、スルホン酸基−SO3H及びホスホン酸基−PO3H2から成る群から選択される反応性基との反応に由来する基、並びに好ましくはエポキシ樹脂と相溶性の部分も有する、親水性に修飾された多官能アミンAC。
- 1分子あたり少なくとも2個の一級アミノ基を有する、請求項1に記載の親水性に修飾された多官能アミンAC。
- 親水化修飾がオキシエチレン若しくはオキシプロピレン部分、又はこれらのこれらの混合物由来の部分によって提供される、請求項1又は2に記載の親水性に修飾された多官能アミンAC。
- 第一工程において、1分子あたり少なくとも1個の一級アミノ基、並びに、好ましくは二級アミノ基>NH、水酸基−OH、メルカプタン基−SH、アミド基−CO−NHR(式中Rは水素又は1〜12個の炭素原子を有するアルキル基であって良い)、ヒドロキシエステル基、及び酸性基、特にカルボキシル基−COOH、スルホン酸基−SO3H及びホスホン酸基−PO3H2から成る群から選択される更なる反応性基を有するアミンAと、前記一級アミノ基に対するブロッキング剤B、好ましくはアルデヒド又はケトンとの反応により、残留一級アミノ基を有しない化合物、好ましくはアルジミン又はケチミンであってよいシッフ塩基を形成させて、ブロックされた一級アミノ基を有するアミノ官能化合物ABを形成させる工程、及び
第二工程において、前記ブロックされた一級アミノ基及び上に詳述した更なる反応性基を有する前記アミノ官能化合物ABと、前記アミンAの更なる反応性基と反応する官能基を有し、同様に親水性であり、好ましくは同様にエポキシ樹脂と相溶性である多官能化合物Cとを反応させて、ブロックされた一級アミノ基を有するアミノ官能化合物ABCを形成させる工程、及び
加熱により、又は、ブロック化一級アミノ基を解放する脱ブロッキング化合物Dの添加により、前記化合物ABCから前記ブロッキング剤Bを取り除く工程、
を含む、請求項1〜3のいずれか一項に記載の親水性に修飾された多官能アミンACの作成方法。 - 前記化合物Cが、ハロゲン化カルボニル、無水カルボン酸、イソシアネート、エポキシド、及びアジリジンから成る群から選択される、少なくとも2個の官能基を有する請求項4に記載の方法。
- 前記アミンAが2個の一級アミノ基及び少なくとも1個の二級アミノ基を有し、並びに前記多官能化合物Cが二官能性である、請求項4〜5のいずれか一項に記載の方法。
- 前記アミンAがジエチレントリアミン、トリエチレンテトラミン、テトラエチレンペンタミン、ジプロピレントリアミン、トリプロピレンテトラミン、ジブチレントリアミン、トリブチレンテトラミン、ジヘキシレントリアミン、及びトリヘキシレンテトラミン、並びにこれらの任意の混合物から成る群から選択される、請求項6に記載の方法。
- 前記アミンAと共にアミンA’が使用され、前記アミンA’の物質量は前記アミンAの物質量以下であり、及び、前記アミンA’は少なくとも1個の二級アミノ基を有し、かつ一級アミノ基を有しない、請求項7に記載の方法。
- 前記多官能化合物Cが、少なくとも二塩基性の芳香族又は脂肪族又は脂環式酸のハロゲン化物、少なくとも二塩基性の芳香族又は脂肪族又は脂環式酸のグリシジルエステルのハロゲン化物、少なくとも二価のフェノールのグリシジルエーテルのハロゲン化物、少なくとも二価の脂肪族又は脂環式アルコールのグリシジルエーテルのハロゲン化物、及びN,O−グリシジルヒドロキシ芳香族アミンのハロゲン化物から成る群から選択される、請求項4〜8の1以上に記載の方法。
- 前記多官能化合物Cが、少なくとも1個の繰り返し単位を有するエポキシ樹脂のグリシジルエーテルである請求項9に記載の方法。
- 前記アミンAが1個の一級アミノ基と1個の二級アミノ基を有し、及び前記多官能化合物Cが少なくとも三官能性である、請求項4〜5のいずれか一項に記載の方法。
- 請求項4の最後の工程において形成された前記アミンACに、モノ−エポキシ官能化合物を添加する、請求項4〜11のいずれか一項に記載の方法。
- 多官能一級アミンACを水に分散する工程、随意に、酸の添加により前記多官能一級アミンACを少なくとも部分的に中和する工程、前記多官能一級アミンACの前記水性分散物にエポキシド樹脂Eを添加する工程、この様に形成された混合物ACEを均質化する工程、及び、前記混合物ACEを基板表面に塗布する工程を含む、請求項4〜12のいずれか一項に従って調製された前記多官能一級アミンACの、エポキシド樹脂Eに対する硬化剤としての使用方法。
- 前記エポキシド樹脂Eが、ジ−エポキシド官能化合物と、モノ−エポキシド官能化合物の少なくとも1個と、少なくとも3の官能性を有するエポキシド官能化合物との混合物である、請求項13に記載の使用方法。
- 前記多官能一級アミンACの前記水性分散物に、顔料、充填剤、消泡剤、展着剤、沈降防止剤、粘度調整剤、及び融合助剤の少なくとも1種を添加する、請求項13又は14に記載の使用方法。
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2018012604A1 (ja) * | 2016-07-13 | 2018-01-18 | 関西ペイント株式会社 | 水性防食塗料組成物及び防食塗装方法 |
JP2020521012A (ja) * | 2017-05-16 | 2020-07-16 | エボニック オペレーションズ ゲーエムベーハー | エポキシ硬化剤、組成物およびその使用 |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2520599A1 (en) | 2011-05-05 | 2012-11-07 | Cytec Austria GmbH | Multifunctional primary amine, process for its preparation, and use thereof |
EP2727968A1 (en) * | 2012-11-06 | 2014-05-07 | ALLNEX AUSTRIA GmbH | Multifunctional primary amine, process for its preparation, and use thereof |
EP3118234A1 (en) * | 2015-07-15 | 2017-01-18 | ALLNEX AUSTRIA GmbH | Coating compositions |
EP3219740A1 (en) * | 2016-03-18 | 2017-09-20 | ALLNEX AUSTRIA GmbH | Hardener composition for epoxy resin based coating compositions, process for their preparation and use thereof |
CN106245035A (zh) * | 2016-08-11 | 2016-12-21 | 上海电力学院 | 一种多胺类铜缓蚀剂 |
EP3492507A1 (en) | 2017-11-29 | 2019-06-05 | ALLNEX AUSTRIA GmbH | Hardener composition for aqueous epoxy resin based coating compositions, process for their preparation, and use thereof |
WO2019097002A1 (en) | 2017-11-19 | 2019-05-23 | Allnex Austria Gmbh | Hardener composition for aqueous epoxy resin based coating compositions, process for its preparation and use thereof |
CN107987693B (zh) * | 2017-12-15 | 2019-12-17 | 中山市钧纬新材料科技有限公司 | 一种持久抗菌型水性醇酸涂料 |
JP7368938B2 (ja) * | 2017-12-22 | 2023-10-25 | 関西ペイント株式会社 | 防食性に優れた水性塗料組成物 |
JP7118014B2 (ja) * | 2018-01-16 | 2022-08-15 | 関西ペイント株式会社 | 防食塗装方法 |
WO2020074627A1 (en) | 2018-10-12 | 2020-04-16 | Allnex Austria Gmbh | Two-pack epoxy paints with improved corrosion protection |
WO2020190277A1 (en) | 2019-03-18 | 2020-09-24 | Hewlett-Packard Development Company, L.P. | Three-dimensional printing with epoxy and amine compounds |
CN112126318A (zh) * | 2020-09-29 | 2020-12-25 | 肇庆亿图化工有限公司 | 一种用于金属包装容器的新型不含双酚a的罐内防腐涂料 |
CN114561177B (zh) * | 2022-02-17 | 2022-09-02 | 交通运输部公路科学研究所 | 一种混凝土潮湿裂缝修补用环氧灌注胶及其制备方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS59174656A (ja) * | 1983-03-21 | 1984-10-03 | デソト,インコ−ポレ−テツド | 水性塗料組成物 |
JPH1095954A (ja) * | 1996-09-25 | 1998-04-14 | Fuji Kasei Kogyo Kk | 塗装剤用エポキシ樹脂組成物 |
JPH11228807A (ja) * | 1998-02-13 | 1999-08-24 | Asahi Denka Kogyo Kk | 水系樹脂組成物 |
JP2008248227A (ja) * | 2007-02-07 | 2008-10-16 | Air Products & Chemicals Inc | 硬化剤組成物 |
Family Cites Families (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4197389A (en) | 1977-07-18 | 1980-04-08 | Hoechst Aktiengesellschaft | Hardening agent for aqueous epoxy resin compositions |
US4198331A (en) | 1978-08-28 | 1980-04-15 | Ppg Industries, Inc. | Resinous coating compositions curable by Michael adduct exchange |
DE3643751A1 (de) | 1986-12-20 | 1988-06-23 | Hoechst Ag | Stabile waessrige epoxidharz-dispersionen, verfahren zu deren herstellung und deren verwendung |
EP0301716A3 (en) * | 1987-07-27 | 1991-01-30 | Texaco Development Corporation | Polyamidopolyamines |
DE3820301A1 (de) | 1988-06-15 | 1989-12-21 | Hoechst Ag | Stabile waessrige epoxidharz-dispersion, verfahren zu deren herstellung und deren verwendung |
US5097070A (en) | 1989-11-03 | 1992-03-17 | Texaco Chemical Company | High molecular weight trifunctional polyoxyethylene amines |
DE4206392A1 (de) * | 1992-02-29 | 1993-09-02 | Hoechst Ag | Haertungsmittel fuer epoxidharze |
US5288802A (en) | 1993-01-25 | 1994-02-22 | Ppg Industries, Inc. | Automotive refinish primer surfacer containing acetoacetate functional polyesterpolyol, a polyacrylate, and an amine functional epoxy resin |
US5527839A (en) * | 1994-12-13 | 1996-06-18 | Air Products And Chemicals, Inc. | Self-emulsifying epoxy curing agent based on the reaction product of epoxy resin and polyether polyol |
JP3988086B2 (ja) * | 1996-03-11 | 2007-10-10 | バンティコ アクチエンゲゼルシャフト | 水で加工可能なポリアミン硬化剤を含有する硬化性エポキシ樹脂組成物 |
DE19616020A1 (de) * | 1996-04-23 | 1997-10-30 | Huels Chemische Werke Ag | Neue Polyamine sowie ein Verfahren zu ihrer Herstellung |
DE10128889A1 (de) | 2001-06-15 | 2002-12-19 | Solutia Austria Gmbh Werndorf | Wasserverdünnbare Aminhärter für wäßrige Zweikomponenten-Epoxidharz-Systeme |
EP2028244A1 (en) * | 2007-08-02 | 2009-02-25 | Cytec Surface Specialties Austria GmbH | Water-borne paints based on epoxy resins |
DE202007015652U1 (de) | 2007-11-09 | 2009-03-26 | Komptech Gmbh | Laderaumaufbau und Transportwagen |
WO2010035641A1 (ja) | 2008-09-29 | 2010-04-01 | 日本ペイント株式会社 | 水性塗料組成物 |
CN102031051B (zh) * | 2009-09-24 | 2012-09-19 | 广州骏丰医疗器械有限公司 | 频谱发生器及其制备方法和远红外辐射涂料的制备方法 |
CN101735706B (zh) * | 2010-01-07 | 2012-02-29 | 同济大学 | 一种水性聚氨酯改性环氧钢结构防腐涂料及其制备方法 |
WO2011118792A1 (ja) | 2010-03-26 | 2011-09-29 | 日本ペイント株式会社 | 水性塗料組成物および塗膜形成方法 |
EP2520599A1 (en) | 2011-05-05 | 2012-11-07 | Cytec Austria GmbH | Multifunctional primary amine, process for its preparation, and use thereof |
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Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS59174656A (ja) * | 1983-03-21 | 1984-10-03 | デソト,インコ−ポレ−テツド | 水性塗料組成物 |
JPH1095954A (ja) * | 1996-09-25 | 1998-04-14 | Fuji Kasei Kogyo Kk | 塗装剤用エポキシ樹脂組成物 |
JPH11228807A (ja) * | 1998-02-13 | 1999-08-24 | Asahi Denka Kogyo Kk | 水系樹脂組成物 |
JP2008248227A (ja) * | 2007-02-07 | 2008-10-16 | Air Products & Chemicals Inc | 硬化剤組成物 |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2018012604A1 (ja) * | 2016-07-13 | 2018-01-18 | 関西ペイント株式会社 | 水性防食塗料組成物及び防食塗装方法 |
JPWO2018012604A1 (ja) * | 2016-07-13 | 2019-04-25 | 関西ペイント株式会社 | 水性防食塗料組成物及び防食塗装方法 |
JP2021185231A (ja) * | 2016-07-13 | 2021-12-09 | 関西ペイント株式会社 | 水性防食塗料組成物及び防食塗装方法 |
JP7104841B2 (ja) | 2016-07-13 | 2022-07-21 | 関西ペイント株式会社 | 水性防食塗料組成物及び防食塗装方法 |
JP2020521012A (ja) * | 2017-05-16 | 2020-07-16 | エボニック オペレーションズ ゲーエムベーハー | エポキシ硬化剤、組成物およびその使用 |
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MX355323B (es) | 2018-04-16 |
EP2520599A1 (en) | 2012-11-07 |
BR112013027837B1 (pt) | 2021-05-18 |
MX2013012739A (es) | 2013-12-02 |
KR101948349B1 (ko) | 2019-04-22 |
ES2615254T3 (es) | 2017-06-06 |
EP2705069B1 (en) | 2017-01-18 |
CN103502300A (zh) | 2014-01-08 |
US9440911B2 (en) | 2016-09-13 |
ZA201308180B (en) | 2015-04-29 |
CN103502300B (zh) | 2016-11-02 |
KR20140043341A (ko) | 2014-04-09 |
US20140350141A1 (en) | 2014-11-27 |
JP6053193B2 (ja) | 2016-12-27 |
WO2012150312A1 (en) | 2012-11-08 |
EP2705069A1 (en) | 2014-03-12 |
US20160347729A1 (en) | 2016-12-01 |
US10023547B2 (en) | 2018-07-17 |
CA2831971A1 (en) | 2012-11-08 |
CA2831971C (en) | 2019-01-08 |
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