JP4984587B2 - 水性エポキシ樹脂組成物、その硬化物、新規2官能性ヒドロキシ化合物、新規2官能性エポキシ樹脂、及びそれらの製造方法 - Google Patents
水性エポキシ樹脂組成物、その硬化物、新規2官能性ヒドロキシ化合物、新規2官能性エポキシ樹脂、及びそれらの製造方法 Download PDFInfo
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- JP4984587B2 JP4984587B2 JP2006076387A JP2006076387A JP4984587B2 JP 4984587 B2 JP4984587 B2 JP 4984587B2 JP 2006076387 A JP2006076387 A JP 2006076387A JP 2006076387 A JP2006076387 A JP 2006076387A JP 4984587 B2 JP4984587 B2 JP 4984587B2
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- 239000003822 epoxy resin Substances 0.000 title claims description 232
- 229920000647 polyepoxide Polymers 0.000 title claims description 232
- 230000001588 bifunctional effect Effects 0.000 title claims description 102
- 239000000203 mixture Substances 0.000 title claims description 99
- 150000002440 hydroxy compounds Chemical class 0.000 title claims description 74
- 238000004519 manufacturing process Methods 0.000 title claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 83
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 63
- 238000006243 chemical reaction Methods 0.000 claims description 57
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 53
- 125000004432 carbon atom Chemical group C* 0.000 claims description 51
- 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 claims description 47
- -1 isocyanate compound Chemical class 0.000 claims description 47
- 239000004593 Epoxy Substances 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- 239000003795 chemical substances by application Substances 0.000 claims description 28
- 229910052801 chlorine Inorganic materials 0.000 claims description 28
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 23
- 125000002947 alkylene group Chemical group 0.000 claims description 20
- 150000001412 amines Chemical class 0.000 claims description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 19
- 229930185605 Bisphenol Natural products 0.000 claims description 19
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 19
- 229910052740 iodine Inorganic materials 0.000 claims description 19
- 150000001768 cations Chemical group 0.000 claims description 16
- 125000003700 epoxy group Chemical group 0.000 claims description 16
- 239000012948 isocyanate Substances 0.000 claims description 15
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000003973 paint Substances 0.000 claims description 11
- 125000002091 cationic group Chemical group 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 229920003180 amino resin Polymers 0.000 claims description 6
- 238000005956 quaternization reaction Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 238000000034 method Methods 0.000 description 32
- 239000003054 catalyst Substances 0.000 description 30
- 239000000047 product Substances 0.000 description 29
- 238000001723 curing Methods 0.000 description 24
- 239000003960 organic solvent Substances 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- 238000005260 corrosion Methods 0.000 description 18
- 229920005989 resin Polymers 0.000 description 18
- 239000011347 resin Substances 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 17
- 238000000576 coating method Methods 0.000 description 17
- 230000007797 corrosion Effects 0.000 description 17
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000007864 aqueous solution Substances 0.000 description 15
- 239000000835 fiber Substances 0.000 description 15
- 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 15
- 239000002994 raw material Substances 0.000 description 15
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- 239000011248 coating agent Substances 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- 150000002989 phenols Chemical class 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- 229910001873 dinitrogen Inorganic materials 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 10
- 239000004094 surface-active agent Substances 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- 239000000049 pigment Substances 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 7
- 238000005342 ion exchange Methods 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 6
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 6
- 230000001070 adhesive effect Effects 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 6
- 125000005442 diisocyanate group Chemical group 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- 229920003986 novolac Polymers 0.000 description 6
- 229920001451 polypropylene glycol Polymers 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 5
- 239000004567 concrete Substances 0.000 description 5
- 238000010790 dilution Methods 0.000 description 5
- 239000012895 dilution Substances 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000005011 phenolic resin Substances 0.000 description 5
- 239000002798 polar solvent Substances 0.000 description 5
- 229920000768 polyamine Polymers 0.000 description 5
- 238000004513 sizing Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 230000008961 swelling Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 4
- HHAPGMVKBLELOE-UHFFFAOYSA-N 2-(2-methylpropoxy)ethanol Chemical compound CC(C)COCCO HHAPGMVKBLELOE-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- BDLXTDLGTWNUFM-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxy]ethanol Chemical compound CC(C)(C)OCCO BDLXTDLGTWNUFM-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VKOUCJUTMGHNOR-UHFFFAOYSA-N Diphenolic acid Chemical compound C=1C=C(O)C=CC=1C(CCC(O)=O)(C)C1=CC=C(O)C=C1 VKOUCJUTMGHNOR-UHFFFAOYSA-N 0.000 description 4
- 239000004606 Fillers/Extenders Substances 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
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- 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 3
- FVCSARBUZVPSQF-UHFFFAOYSA-N 5-(2,4-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1C(=O)COC1=O FVCSARBUZVPSQF-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
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- 239000002202 Polyethylene glycol Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 3
- 150000008041 alkali metal carbonates Chemical class 0.000 description 3
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- 239000000539 dimer Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
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- 150000002460 imidazoles Chemical class 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
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- 238000012545 processing Methods 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- MWGRRMQNSQNFID-UHFFFAOYSA-N 1-(2-methylpropoxy)propan-2-ol Chemical compound CC(C)COCC(C)O MWGRRMQNSQNFID-UHFFFAOYSA-N 0.000 description 2
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 2
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 2
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- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- CZAZXHQSSWRBHT-UHFFFAOYSA-N 2-(2-hydroxyphenyl)-3,4,5,6-tetramethylphenol Chemical compound OC1=C(C)C(C)=C(C)C(C)=C1C1=CC=CC=C1O CZAZXHQSSWRBHT-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
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- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical compound COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 2
- CCTFMNIEFHGTDU-UHFFFAOYSA-N 3-methoxypropyl acetate Chemical compound COCCCOC(C)=O CCTFMNIEFHGTDU-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
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 0 CNCCC(*(C(*)*)C1*CC1)*=C Chemical compound CNCCC(*(C(*)*)C1*CC1)*=C 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
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- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 1
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- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
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- QFFVPLLCYGOFPU-UHFFFAOYSA-N barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 1
- 229940083898 barium chromate Drugs 0.000 description 1
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- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
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- WQHCGPGATAYRLN-UHFFFAOYSA-N chloromethane;2-(dimethylamino)ethyl prop-2-enoate Chemical compound ClC.CN(C)CCOC(=O)C=C WQHCGPGATAYRLN-UHFFFAOYSA-N 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
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- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
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- LTRVAZKHJRYLRJ-UHFFFAOYSA-N lithium;butan-1-olate Chemical compound [Li+].CCCC[O-] LTRVAZKHJRYLRJ-UHFFFAOYSA-N 0.000 description 1
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
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- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
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- 238000000465 moulding Methods 0.000 description 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- VSWALKINGSNVAR-UHFFFAOYSA-N naphthalen-1-ol;phenol Chemical compound OC1=CC=CC=C1.C1=CC=C2C(O)=CC=CC2=C1 VSWALKINGSNVAR-UHFFFAOYSA-N 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- FZZQNEVOYIYFPF-UHFFFAOYSA-N naphthalene-1,6-diol Chemical compound OC1=CC=CC2=CC(O)=CC=C21 FZZQNEVOYIYFPF-UHFFFAOYSA-N 0.000 description 1
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 description 1
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- GJYCVCVHRSWLNY-UHFFFAOYSA-N ortho-butylphenol Natural products CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 1
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- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
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- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
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- 239000010935 stainless steel Substances 0.000 description 1
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- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
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- SZWHXXNVLACKBV-UHFFFAOYSA-N tetraethylphosphanium Chemical compound CC[P+](CC)(CC)CC SZWHXXNVLACKBV-UHFFFAOYSA-N 0.000 description 1
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- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
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- 239000011592 zinc chloride Substances 0.000 description 1
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- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
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Description
で表される構造を有し、且つ分子両末端がエポキシ基である2官能性エポキシ樹脂を含有する水性エポキシ樹脂組成物、及びその硬化物を提供するものである。
で表される新規2官能性エポキシ樹脂を提供するものである。
で表される新規2官能性ヒドロキシ化合物をも提供するものである。
本発明で用いる2官能性エポキシ樹脂(A)は、下記一般式(1)
で表される構造を有し、且つ分子両末端がエポキシ基であることを特徴とする。
で表される化合物を挙げることができる。
本発明の製造方法は、まず、本発明の下記一般式(5)
で表される、本発明の新規カチオン基含有2官能性ヒドロキシ化合物(a1)を合成することから始めることが好ましい。本発明の2官能性ヒドロキシ化合物としては、特に得られるエポキシ樹脂が低粘度であって、且つ水性エポキシ樹脂組成物としたときの保存安定性に優れる点から、前記一般式(5)中のR1、R2、R3、R4が水素原子であり、R5、R6、R7、R8がメチル基であり、Qが窒素原子であり、Yが塩素原子又は水酸基であることが好ましい。
で表される水酸基とカルボキシル基とを有する化合物(x1)と、四級オニウム塩含有エポキシ化合物(x2)とを反応させることによって製造することが好ましい。
で表される化合物が挙げられる。
まず、前記一般式(3)で表される2官能性エポキシ樹脂を得る方法としては、
(I)前記2官能性ヒドロキシ化合物(a1)とエピハロヒドリン(a2)とを反応させる方法(いわゆる一段法)、
(II)(I)で得られた2官能性エポキシ樹脂を、更に前記2官能性ヒドロキシ化合物(a1)を用いて伸長反応させる方法(いわゆる2段法)、
が挙げられる。
(III)前記2官能性ヒドロキシ化合物(a1)と、前記(a1)以外の、ビスフェノール類(a3)との混合物と、エピハロヒドリン(a2)と、を反応させる方法(共縮反応)、
(IV)(I)で得られた2官能性エポキシ樹脂を、前記(a1)以外の、ビスフェノール類(a3)を用いて伸長反応させる方法、
(V)本発明の2官能性エポキシ樹脂以外の2官能性エポキシ樹脂〔カチオン基不含2官能性エポキシ樹脂(a4)〕を、前記2官能性ヒドロキシ化合物(a1)を用いて伸長反応させる方法、
が挙げられる。
温度計、撹拌装置、滴下ロート、冷却管、窒素ガス導入管、下部に分液コックが装着された4つ口フラスコに、ジフェノール酸(水酸基当量143g/eq、カルボキシル当量286g/eq、大塚化学株式会社製)286gとSY−GTA80(グリシジル基含有4級オニウム塩−80%水溶液、阪本薬品工業株式会社製)227gとイソプロピルアルコール120gを仕込み、50℃まで加熱撹拌することによって、均一溶液とした。更に同温度で4時間反応させることによって、カチオン基含有2官能性ヒドロキシ化合物(a1−1)を得た。該化合物(a1−1)は、図1の13C−NMRスペクトル及び図2のマススペクトル(マトリックスとして1,4−ジフェニル−1,3−ブタジエンを使用)で理論構造に相当するM+=402のピークが得られたことから、下記構造式(7)のカチオン基含有2官能性ヒドロキシ化合物を含有することが確認された。
実施例1で得たヒドロキシ化合物(a1−1)のフラスコに、エピクロルヒドリン370g(4モル)を仕込み、40℃まで加熱攪拌しながら溶解させた。その後、窒素ガスパージを施しながら、49%水酸化ナトリウム水溶液8g(0.1モル)を添加し4時間反応させた。次いで50℃まで加熱し、49%水酸化ナトリウム水溶液100g(1.2モル)を5時間かけて滴下した。その後、水157gを添加し、生成した塩を溶解した後、下部の分液用コックより飽和食塩水を棄却した。未反応のエピクロロヒドリンを常圧条件下でフラスコ温度130℃まで蒸留して留去後、反応液に残った塩をろ別した。ろ液から、更に減圧条件下フラスコ温度130℃で未反応のエピクロロヒドリンを留去することによってエポキシ当量403g/eqのエポキシ樹脂(A−1)を得た。このエポキシ樹脂(A−1)は、マススペクトル(マトリックスとして1,1,4,4−テトラ−1,3−ブタジエンを使用)でn=0の理論構造に相当するM+=514のピーク、n=1の理論構造に相当するM+=969のピークが得られたことから、下記構造式(8)で表されるエポキシ樹脂を含有することが確認された。ここにイオン交換水233gを加える事によって、不揮発分60%の白色液体状の水性エポキシ樹脂組成物を得た。これを水性エポキシ樹脂組成物(E−1)とする。
温度計、撹拌装置、滴下ロート、冷却管、窒素ガス導入管が装着された4つ口フラスコに実施例2で得られたエポキシ樹脂(A−1)300部、ジフェノール酸20部、メトキシプロパノール36部を加え、50℃に昇温し攪拌均一化した。更に、90℃で2時間攪拌する事によって、エポキシ当量560g/eqのエポキシ樹脂(A−2)を得た。エポキシ樹脂(A−2)に、イオン交換水284部を加え均一溶解させることによって、不揮発分50%の白色液体状の水性エポキシ樹脂組成物(E−2)を得た。
実施例1で得た(a1−1)のフラスコに、ビスフェノールA228g、エピクロルヒドリン1480g(4モル)を仕込み、40℃まで加熱攪拌しながら溶解させた。その後、窒素ガスパージを施しながら、49%水酸化ナトリウム水溶液33g(0.1モル)を添加し4時間反応させた。次いで50℃まで加熱し、49%水酸化ナトリウム水溶液400g(1.2モル)を5時間かけて滴下した。その後、水564部を添加し、生成した塩を溶解した後、下部の分液用コックより飽和食塩水を棄却した。未反応のエピクロロヒドリンを常圧条件下でフラスコ温度130℃まで蒸留して留去後、反応液に残った塩をろ別した。ろ液から、更に減圧条件下フラスコ温度130℃で未反応のエピクロロヒドリンを留去したのちプロピルセロソルブ99gを加え攪拌均一化する事によって、不揮発分90%、エポキシ当量277g/eqのエポキシ樹脂(A−3)を得た。エポキシ樹脂(A−3)にイオン交換水788部を加え、攪拌均一化することによって、不揮発分50%の水性エポキシ樹脂組成物(E−3)を得た。
温度計、撹拌装置、滴下ロート、冷却管、窒素ガス導入管が装着された4つ口フラスコに、実施例2で得たエポキシ樹脂(A−1)300部、ビスフェノールA16.7部、メトキシプロパノール35部を仕込み、50℃に昇温し攪拌均一化させた。その後、100℃に昇温し3時間攪拌する事によって、エポキシ当量551g/eqのエポキシ樹脂(A−4)を得た。エポキシ樹脂(A−4)に、イオン交換水282部を加え攪拌均一化することによって、不揮発分50%の水性エポキシ樹脂組成物(E−4)を得た。
実施例1で得た(a1−1)のフラスコに、ビスフェノールA456g、エピクロルヒドリン2220g(4モル)を仕込み、40℃まで加熱攪拌しながら溶解させた。その後、窒素ガスパージを施しながら、49%水酸化ナトリウム水溶液58.8g(0.1モル)を添加し4時間反応させた。次いで50℃まで加熱し、49%水酸化ナトリウム水溶液705g(1.2モル)を5時間かけて滴下した。その後、水800gを添加し、生成した塩を溶解した後、下部の分液用コックより飽和食塩水を棄却した。未反応のエピクロロヒドリンを常圧条件下でフラスコ温度130℃まで蒸留して留去後、反応液に残った塩をろ別した。ろ液から、更に減圧条件下フラスコ温度130℃で未反応のエピクロロヒドリンを留去した後、プロピルセロソルブ134gを加え攪拌均一化する事によって、不揮発分90%、エポキシ当量 298g/eqのエポキシ樹脂(A−5)を得た。エポキシ樹脂(A−5)にイオン交換水1077gを加え、攪拌均一化することによって不揮発分50%の水性エポキシ樹脂組成物(E−6)を得た。
温度計、撹拌装置、滴下ロート、冷却管、窒素ガス導入管が装着された4つ口フラスコに、EPICLON850−S(ビスフェノールA型液状エポキシ樹脂、エポキシ当量188g/eq、大日本インキ化学工業株式会社製)300部、実施例1で得られたカチオン基含有2官能性ヒドロキシ化合物(a1−1)184部、メトキシプロパノール48部を仕込み、50℃に昇温、攪拌均一化した。更に100℃に昇温し(a1−1)中のイソプロパノールを留去しながら攪拌を3時間継続する事によってエポキシ当量480g/eqのエポキシ樹脂(A−6)を得た。エポキシ樹脂(A−6)にイオン交換水375部を加え、攪拌均一化することによって不揮発分50%の水性エポキシ樹脂組成物(E−7)を得た。
温度計、撹拌装置、滴下ロート、冷却管、窒素ガス導入管が装着された4つ口フラスコに、実施例4で得られたエポキシ樹脂(A−3)300部、ビスフェノールA102部、ブチルセロソルブ63部を仕込み、70℃に昇温、攪拌均一化した。更に140℃に昇温後5時間攪拌し、ブチルセロソルブ66部を加え攪拌均一化することによって、エポキシ当量5100g/eqのエポキシ樹脂(A−7)を得た。このエポキシ樹脂(A−7)に対し、イオン交換水532部を加え、攪拌均一化することによって、不揮発分35%の水性エポキシ樹脂組成物(E−7)を得た。
温度計、撹拌装置、滴下ロート、冷却管、窒素ガス導入管が装着された4つ口フラスコに、実施例2で得たエポキシ樹脂(A−1)300部、ビスフェノールA76部、メトキシプロパノール66部を仕込み、50℃に昇温し攪拌均一化させた。その後、140℃に昇温し4時間攪拌した後、ブチルセロソルブ41部を加え攪拌均一化する事によって、エポキシ当量5300g/eqのエポキシ樹脂(A−8)を得た。エポキシ樹脂(A−8)に、イオン交換水591部を加え攪拌均一化することによって、不揮発分35%の水性エポキシ樹脂組成物(E−8)を得た。
温度計、撹拌装置、滴下ロート、冷却管、窒素ガス導入管が装着された4つ口フラスコに、EPICLON 1055(ビスフェノールA型固形エポキシ樹脂、エポキシ当量475g/eq、大日本インキ化学工業株式会社製)300部、ブチルセロソルブ135部を仕込み、100℃に昇温して攪拌均一化後、モノエタノールアミン(アルカノールアミン、日本触媒株式会社製)4部、ジェファーミンM−1000(ポリオキシアルキレン化合物、ピー・ティー・アイジャパン株式会社製)101部を発熱に注意しながら順次仕込み、130℃において溶液粘度が飽和するまで反応を行う事によってエポキシ樹脂(A’−1)を得た。エポキシ樹脂(A’−1)に対し、イオン交換水360部を添加し、攪拌均一化することによって、不揮発分45%の水性エポキシ樹脂組成物(E’−1)を得た。
温度計、撹拌装置、滴下ロート、冷却管、窒素ガス導入管が装着された4つ口フラスコに、EPICLON 2055(ビスフェノールA型固形エポキシ樹脂、エポキシ当量625g/eq、大日本インキ化学工業株式会社製)300部、ジグライム180部を仕込み、70℃に昇温して攪拌均一化後、モノエタノールアミン21部、を加え、100℃にて7時間反応させた。70℃に冷却後、無水コハク酸59部を添加し95℃に昇温し1時間反応させた。次に、反応液を60℃に冷却し、29%アンモニア水35部を添加、攪拌均一化後にイオン交換水527部を加え、攪拌均一化させることによって不揮発分33%の水性エポキシ樹脂組成物(E’−2)を得た。
〇:沈殿、分離なし、×:分離または凝集物が確認される
また、安定性試験3ヵ月後のマヨネーズ瓶を開け、アミン臭気について官能試験を行った。
○:アミン臭気無、×:アミン臭気有
次に、得られた水性エポキシ樹脂組成物を用いて表2、3の配合比で水性塗料を作成し、#400のサンドペーバーで表面処理を行った冷却圧延鋼板に対しバーコーターにて塗布した後、塗膜物性評価を行った。なお、表2記載の塗料はPWC=50%、塗膜物性は膜厚60μm、25℃×7日養生後の試験結果であり、表3記載の塗料はPWC=55%、塗膜物性は膜厚15μm、焼付条件160℃×20分の試験結果である。尚、各試験方法及び評価基準は下記の通りである。
〇:50cmで亀裂等の発生無し。×:50cmで亀裂等の発生が認められる。
〇:剥がれなし。×:剥がれが見られる。
〇:膨れ発生せず。×:膨れ発生。
〇:膨れ発生せず。×:膨れ発生。
8290Y60:ジャパンエポキシエジン社製 ポリアミン樹脂「EPICURE 8290Y60」活性水素当量(溶液値=272g/eq)
K−White:テイカ株式会社製 防錆顔料
CR−97:石原産業株式会社製 酸化チタン タイペークCR−97
SNデフォーマー777:サンノプコ株式会社製 消泡剤
BYK−341:ビックケミー社製 添加剤
S−695:大日本インキ化学工業株式会社製 水溶性メチルエーテル化メラミン樹脂ウォーターゾールS−695」不揮発分65%
硬化触媒 :大日本インキ化学工業株式会社製 ベッカミンP−198
DNW−500:大日本インキ化学工業株式会社製 水溶性イソシアネート「バーノックDNW−500」不揮発分80%、NCO含有量13.5%
NS−100:日東粉化株式会社 炭酸カルシウム
Claims (20)
- 前記一般式(3)中のR1、R2、R3、R4が水素原子であり、R5、R6、R7、R8がメチル基であり、Yが塩素原子又は水酸基である請求項3記載の水性エポキシ樹脂組成物。
- 前記一般式(4)中のqとrとの比q/rが、20/80〜95/5である請求項5記載の水性エポキシ樹脂組成物。
- 前記一般式(4)中のR1、R2、R3、R4が水素原子であり、R5、R6、R7、R8がメチル基であり、Yが塩素原子又は水酸基である請求項5記載の水性エポキシ樹脂組成物。
- 更に硬化剤(C)を含有する請求項1〜7の何れか1項記載の水性エポキシ樹脂組成物。
- 硬化剤(C)がアミン系硬化剤、アミノ樹脂又はイソシアネート化合物である請求項8記載の水性エポキシ樹脂組成物。
- 水性塗料用組成物である請求項8記載の水性エポキシ樹脂組成物。
- 請求項1〜10の何れか1項記載の水性エポキシ樹脂組成物を硬化させて得られることを特徴とする硬化物。
- 前記一般式(5)中のR1、R2、R3、R4が水素原子であり、R5、R6、R7、R8がメチル基であり、Yが塩素原子又は水酸基である請求項12記載の新規カチオン基含有2官能性ヒドロキシ化合物。
- 下記一般式(3)
又は下記一般式(4)
で表されることを特徴とする新規カチオン基含有2官能性エポキシ樹脂。 - 前記一般式(3)中のR1、R2、R3、R4が水素原子であり、R5、R6、R7、R8がメチル基であり、Yが塩素原子又は水酸基である、又は前記一般式(4)中のR1、R2、R3、R4が水素原子であり、R5、R6、R7、R8がメチル基であり、Yが塩素原子又は水酸基であり、Aがビスフェノール類の残基である請求項14記載の新規カチオン基含有2官能性エポキシ樹脂。
- 下記一般式(2)
で表される水酸基とカルボキシル基とを有する化合物(x1)と一般式(6)
で表される四級オニウム塩含有エポキシ化合物(x2)とを反応させて得られるカチオン基含有2官能性ヒドロキシ化合物(a1)と、エピハロヒドリン(a2)と、を反応させることを特徴とする下記一般式(1)
で表される構造を有し、且つ分子両末端がエポキシ基である2官能性エポキシ樹脂(A)の製造方法。 - 下記一般式(2)
で表される水酸基とカルボキシル基とを有する化合物(x1)と一般式(6)
で表される四級オニウム塩含有エポキシ化合物(x2)とを反応させて得られるカチオン基含有2官能性ヒドロキシ化合物(a1)と、ビスフェノール類(a3)と、エピハロヒドリン(a2)と、を反応させることを特徴とする下記一般式(1)
で表される構造を有し、且つ分子両末端がエポキシ基である2官能性エポキシ樹脂(A)の製造方法。 - 下記一般式(2)
で表される水酸基とカルボキシル基とを有する化合物(x1)と一般式(6)
で表される四級オニウム塩含有エポキシ化合物(x2)とを反応させて得られるカチオン基含有2官能性ヒドロキシ化合物(a1)と、ビスフェノール類(a3)と、エピハロヒドリン(a2)と、を反応させて得られるカチオン基含有2官能性エポキシ樹脂を用いて、更に、下記一般式(2)
で表される水酸基とカルボキシル基とを有する化合物(x1)と前記一般式(6)で表される四級オニウム塩含有エポキシ化合物(x2)とを反応させて得られるカチオン基含有2官能性ヒドロキシ化合物(a1)と、を用いて伸長反応を行うことを特徴とする下記一般式(1)
で表される構造を有し、且つ分子両末端がエポキシ基である2官能性エポキシ樹脂(A)の製造方法。 - カチオン基不含2官能性エポキシ樹脂(a4)と、下記一般式(2)
で表される水酸基とカルボキシル基とを有する化合物(x1)と一般式(6)
で表される四級オニウム塩含有エポキシ化合物(x2)とを反応させて得られるカチオン基含有2官能性ヒドロキシ化合物(a1)と、を用いて伸長反応を行うことを特徴とする下記一般式(1)
で表される構造を有し、且つ分子両末端がエポキシ基である2官能性エポキシ樹脂(A)の製造方法。 - 下記一般式(2)
で表される水酸基とカルボキシル基とを有する化合物(x1)と一般式(6)
で表される四級オニウム塩含有エポキシ化合物(x2)とを反応させて得られるカチオン基含有2官能性ヒドロキシ化合物(a1)と、エピハロヒドリン(a2)とを反応させた後、カチオン基不含2官能性ヒドロキシ化合物及び/又はカチオン基不含2官能性カルボキシル基含有化合物(a5)を用いて伸長反応を行うことを特徴とする下記一般式(1)
で表される構造を有し、且つ分子両末端がエポキシ基である2官能性エポキシ樹脂(A)の製造方法。
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JP2005239928A (ja) * | 2004-02-27 | 2005-09-08 | Dainippon Ink & Chem Inc | 水性エポキシ樹脂組成物 |
JP2005298727A (ja) * | 2004-04-14 | 2005-10-27 | Dainippon Ink & Chem Inc | 水性樹脂組成物及びこれを用いた水性塗料 |
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