JPH01131284A - Heavy duty corrosionproof coating resin - Google Patents
Heavy duty corrosionproof coating resinInfo
- Publication number
- JPH01131284A JPH01131284A JP28755587A JP28755587A JPH01131284A JP H01131284 A JPH01131284 A JP H01131284A JP 28755587 A JP28755587 A JP 28755587A JP 28755587 A JP28755587 A JP 28755587A JP H01131284 A JPH01131284 A JP H01131284A
- Authority
- JP
- Japan
- Prior art keywords
- epoxy
- resin
- reaction
- alcohol
- coating
- 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.)
- Pending
Links
- 229920005989 resin Polymers 0.000 title claims abstract description 28
- 239000011347 resin Substances 0.000 title claims abstract description 28
- 238000000576 coating method Methods 0.000 title claims abstract description 22
- 239000011248 coating agent Substances 0.000 title claims description 21
- 239000004593 Epoxy Substances 0.000 claims abstract description 32
- 239000003822 epoxy resin Substances 0.000 claims abstract description 26
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
- 229920005862 polyol Polymers 0.000 claims description 22
- 150000003077 polyols Chemical class 0.000 claims description 22
- 238000005260 corrosion Methods 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 17
- 230000007797 corrosion Effects 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 abstract description 18
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 abstract description 4
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 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 13
- 229920000768 polyamine Polymers 0.000 description 13
- -1 hydroxy glycidyl ether compound Chemical class 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 239000005056 polyisocyanate Substances 0.000 description 10
- 229920001228 polyisocyanate Polymers 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000001035 drying Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229910000831 Steel Inorganic materials 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 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 5
- 239000012948 isocyanate Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000003973 paint Substances 0.000 description 5
- 239000010959 steel Substances 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 239000008199 coating composition Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- 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 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 229910001209 Low-carbon steel Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XBTRYWRVOBZSGM-UHFFFAOYSA-N (4-methylphenyl)methanediamine Chemical compound CC1=CC=C(C(N)N)C=C1 XBTRYWRVOBZSGM-UHFFFAOYSA-N 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
- FMMUNDXXVADKHS-UHFFFAOYSA-N 1,3-dimethylpiperazine Chemical compound CC1CN(C)CCN1 FMMUNDXXVADKHS-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- PSABUFWDVWCFDP-UHFFFAOYSA-N 2,2-dimethylheptane Chemical compound CCCCCC(C)(C)C PSABUFWDVWCFDP-UHFFFAOYSA-N 0.000 description 1
- CQOZJDNCADWEKH-UHFFFAOYSA-N 2-[3,3-bis(2-hydroxyphenyl)propyl]phenol Chemical compound OC1=CC=CC=C1CCC(C=1C(=CC=CC=1)O)C1=CC=CC=C1O CQOZJDNCADWEKH-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- RKOGJKGQMPZCGG-UHFFFAOYSA-N 2-methoxypropane-1,3-diol Chemical compound COC(CO)CO RKOGJKGQMPZCGG-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- XYUINKARGUCCQJ-UHFFFAOYSA-N 3-imino-n-propylpropan-1-amine Chemical compound CCCNCCC=N XYUINKARGUCCQJ-UHFFFAOYSA-N 0.000 description 1
- AHHQDHCTHYTBSV-UHFFFAOYSA-N 3-methylpentane-1,3,5-triol Chemical compound OCCC(O)(C)CCO AHHQDHCTHYTBSV-UHFFFAOYSA-N 0.000 description 1
- MUNOBADFTHUUFG-UHFFFAOYSA-N 3-phenylaniline Chemical compound NC1=CC=CC(C=2C=CC=CC=2)=C1 MUNOBADFTHUUFG-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- HDPBBNNDDQOWPJ-UHFFFAOYSA-N 4-[1,2,2-tris(4-hydroxyphenyl)ethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 HDPBBNNDDQOWPJ-UHFFFAOYSA-N 0.000 description 1
- NIGUEHDUHKOJOP-UHFFFAOYSA-N 5-(2-aminoethyl)pyrimidine-2,4-diamine Chemical compound NCCC1=CN=C(N)N=C1N NIGUEHDUHKOJOP-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical class COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
- IPTNXMGXEGQYSY-UHFFFAOYSA-N acetic acid;1-methoxybutan-1-ol Chemical compound CC(O)=O.CCCC(O)OC IPTNXMGXEGQYSY-UHFFFAOYSA-N 0.000 description 1
- 239000012615 aggregate Substances 0.000 description 1
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000000805 composite resin Substances 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229940105990 diglycerin Drugs 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- KIQKWYUGPPFMBV-UHFFFAOYSA-N diisocyanatomethane Chemical compound O=C=NCN=C=O KIQKWYUGPPFMBV-UHFFFAOYSA-N 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000009408 flooring Methods 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000009863 impact test Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical class IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 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 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 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
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- KYCGURZGBKFEQB-UHFFFAOYSA-N n',n'-dibutylpropane-1,3-diamine Chemical compound CCCCN(CCCC)CCCN KYCGURZGBKFEQB-UHFFFAOYSA-N 0.000 description 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- OKBVMLGZPNDWJK-UHFFFAOYSA-N naphthalene-1,4-diamine Chemical compound C1=CC=C2C(N)=CC=C(N)C2=C1 OKBVMLGZPNDWJK-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 238000005488 sandblasting Methods 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 239000010454 slate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 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 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Epoxy Resins (AREA)
- Paints Or Removers (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は重防食被覆用のエポキシポリオール樹脂に関す
る。更に詳しくはエポキシ樹脂と３価アルコールもしく
は４価アルコールの単独又はそれらの混合物を反応させ
て得られる重防食被覆用のエポキシポリオール樹脂に関
する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to an epoxy polyol resin for heavy corrosion protection coating. More specifically, the present invention relates to an epoxy polyol resin for heavy corrosion protection coating obtained by reacting an epoxy resin with a trihydric alcohol or a tetrahydric alcohol, or a mixture thereof.
各種プラントのタンク、パイプ類、船舶等の被覆に使用
される重防食被１用材は、高度の防食性・防水性を必要
とする。従来利用されているものは常温硬化のエポキシ
系の被覆材で、その多くはエポキシ樹脂とポリアミン類
との組合せで用いら・れている。しかし、この系では低
温時における乾燥性が極めて遅く、長期の養生が必要で
、工程の合理化に不適で、特に冬季に問題が生じている
。Heavy-duty anti-corrosion coating materials used to cover tanks, pipes, ships, etc. in various plants require a high degree of anti-corrosion and waterproof properties. Conventionally used epoxy-based coating materials that cure at room temperature are often used in combination with epoxy resins and polyamines. However, this system has extremely slow drying properties at low temperatures, requires long-term curing, and is unsuitable for streamlining the process, causing problems particularly in winter.
一方、アルカノールアミン変性エポキシ樹脂とポリイソ
シアネートとの組合せでは、冬季の乾燥性を向上させ、
工程の合理化を達成しているが、夏季においては主剤と
硬化剤の混合後、比較的短時間にゲル化してしまい、使
用が困難になるという問題が生じてくる。On the other hand, the combination of alkanolamine-modified epoxy resin and polyisocyanate improves dryness in winter,
Although the process has been streamlined, the problem arises that in summer, after the base agent and curing agent are mixed, they gel in a relatively short period of time, making them difficult to use.
従って、長期の防食性・耐久性が必要とされる分野にお
いては、
（１）夏季にはエポキシ樹脂ポリアミン硬化システム（
以下、アミン硬化システムという）。Therefore, in fields where long-term corrosion resistance and durability are required, (1) In the summer, epoxy resin polyamine curing systems (
(hereinafter referred to as amine curing system).
（２）冬季にはアルカノールアミン変性エポキシ樹脂ポ
リイソシアネート硬化システム（以下、イソシアネート
硬化システムという）。(2) Alkanolamine modified epoxy resin polyisocyanate curing system (hereinafter referred to as isocyanate curing system) in winter.
（３）春・秋季には前記のシステムを使い分けることが
一般的に行われている。(3) It is common practice to use the above-mentioned systems differently in spring and autumn.
そのため夏季と冬季で別々の主剤・硬化剤を選択して使
用しなければならな（、被覆剤の製造・″販売・貯蔵を
行う上で非常に煩雑で経済的にも不合理となってい′る
。Therefore, it is necessary to select and use different base agents and hardeners for summer and winter (this is extremely complicated and economically unreasonable when manufacturing, selling, and storing coating materials). Ru.
そこで、主剤だけでも年間を通じ同一の物が使用できれ
ば、合理的な工程管理が可能で、経済的なメリットも大
きい。かかる問題を解決するために、特公昭５７−３３
３１０には多価アルコールとエビハロヒドリンとを反応
させて得られるヒドロキシ・グリシジルエーテル化合物
と多価フェノールのグリシジルエーテル化合物とからな
る混合物の多価フェノール変成物等が提案されているが
、この方法は合成工程が煩雑である上に、塗膜性能面で
劣るという欠点を有している。Therefore, if the same base ingredient could be used throughout the year, rational process control would be possible and there would be great economic benefits. In order to solve this problem,
No. 310 proposes a modified polyhydric phenol, which is a mixture of a hydroxy glycidyl ether compound obtained by reacting a polyhydric alcohol with ebihalohydrin, and a glycidyl ether compound of polyhydric phenol. It has the disadvantage that the process is complicated and the coating film performance is inferior.
〔問題点を解決するための手段］
本発明者らは、アミン硬化システム・イソシアネート硬
化システムの両方に使用でき、高度の防食性・耐薬品性
・耐水性等を持ったエポキシポリオール樹脂の開発に鋭
意注力した結果、本発明に至った。[Means for solving the problem] The present inventors have developed an epoxy polyol resin that can be used in both amine curing systems and isocyanate curing systems and has high corrosion resistance, chemical resistance, water resistance, etc. As a result of intensive efforts, the present invention was achieved.
すなわち本発明は、エポキシ樹脂と３価アルコールもし
くは４価アルコールの単独又はそれらの混合物を反応さ
せて得られる、エポキシ光層２００〜２０００ｇ／当量
、水酸基価３０〜６００ＫＯＩ（ｍｇ／ｇを有する重防
食被覆用エポキシポリオール樹脂である。That is, the present invention provides a heavy corrosion protection product having an epoxy light layer of 200 to 2000 g/equivalent and a hydroxyl value of 30 to 600 KOI (mg/g), which is obtained by reacting an epoxy resin with a trihydric alcohol or a tetrahydric alcohol, or a mixture thereof. This is an epoxy polyol resin for coating.
エポキシ樹脂としては、−殺伐（Ｉ）で示されるものが
挙げられる。Examples of epoxy resins include those represented by -Sakubatsu (I).
Ｒ４０−Ｒｚ−０−Ｅ％０−Ｒｚ−０−Ｅ （
＋ ）を表し、Ｒ，は水素原子又は低級アルキル基を表
す。R40-Rz-0-E%0-Rz-0-E (
+ ), and R represents a hydrogen atom or a lower alkyl group.
Ｉｌｌ ２ バーｏＲ、−Ｇ−１（ｉ＄Ｒ，（３、−６
−ｏ−（◇（）、６、−Ｄ で、上記の核置換化−５
Ｏ□−６またＲ１、Ｒ２、Ｒ３は同一であっても異なっ
ていてもよい。ｎは繰り返し単位の数で０≦ｎ≦４であ
る。）
一般式（１）に示されるエポキシ樹脂としては、具体的
にはエピコート８２８．１１１００１ （油化シェルエ
ポキシ株式会社製）、エボ） −） ＹＤ１２８（東部
化成株式会社製）、エピクロン８５０（大日本インキ化
学工業株式会社製）等のビスフェノールＡ型のエポキシ
樹脂、エピコート８０７（油化シェルエポキシ株式会社
製）、エピクロン８３０（大日本インキ化学工業株式会
社製）、アラルダイ） ＸＰＹ３０６ （チバガイギー
製）等のビスフェノールＦ型のエポキシ樹脂、ブナコー
ルＥＸ−２５１（ナガセ化成工業株式会社製）等のビス
フェノールＳ型のエポキシ樹脂等のビスフェノール型の
エポキシ樹脂の他、ビフェニル型エポキシ樹脂、レゾー
ル型エポキシ樹脂及び前記エポキシ樹脂の水添したエポ
キシ樹脂、メチル基等の核置換物、ハロゲン化物等が挙
げられる。Ill 2 baroR, -G-1(i$R, (3, -6
-o-(◇(), 6, -D, the above nuclear substitution -5
O□-6 Also, R1, R2, and R3 may be the same or different. n is the number of repeating units and satisfies 0≦n≦4. ) Epoxy resins represented by general formula (1) include Epicort 828.111001 (manufactured by Yuka Shell Epoxy Co., Ltd.), Evo) -) YD128 (manufactured by Tobu Kasei Co., Ltd.), and Epiclon 850 (Dainippon Kasei Co., Ltd.). Bisphenol A type epoxy resins such as (manufactured by Ink Kagaku Kogyo Co., Ltd.), Epicoat 807 (manufactured by Yuka Shell Epoxy Co., Ltd.), Epiclon 830 (manufactured by Dainippon Ink Kagaku Kogyo Co., Ltd.), XPY306 (manufactured by Ciba Geigy), etc. In addition to bisphenol type epoxy resins such as bisphenol F type epoxy resins and bisphenol S type epoxy resins such as Bunacol EX-251 (manufactured by Nagase Chemical Industries, Ltd.), biphenyl type epoxy resins, resol type epoxy resins and the above epoxy resins. Examples include hydrogenated epoxy resins, nuclear substitutes such as methyl groups, halides, and the like.
これらエポキシ樹脂と反応させる３価アルコールとして
は、例えばトリメチロールプロパン、トリメチロールエ
タン、トリエタノールメタン、３−メチル−１，３，５
−ペンタントリオール、１，１．１−１−リメチロール
イソブタン、グリセリン、２−メチルグリセリン等の一
種又は二種以上が挙げられる。また４価のアルコールと
しては、例えばペンタエリスリトール、ジグリセリン等
の一種又は二種以上が挙げられる。これらの３価アルコ
ールもしくは４価アルコールは単独又はそれらの混合物
として使用できる。Examples of trihydric alcohols to be reacted with these epoxy resins include trimethylolpropane, trimethylolethane, triethanolmethane, 3-methyl-1,3,5
-Pentanetriol, 1,1.1-1-limethylolisobutane, glycerin, 2-methylglycerin, etc., or one or more of them can be mentioned. Examples of the tetrahydric alcohol include one or more of pentaerythritol and diglycerin. These trihydric alcohols or tetrahydric alcohols can be used alone or as a mixture thereof.
また、本発明はエチレングリコール、プロピレングリコ
ール、１．４−ブタンジオール、１，３−ブタンジオー
ル、ベンタンジオール、１．６−ヘキサンジオール等の
２価アルコールの一種又は二種以上、更にビスフェノー
ルＡ１ビスフエノールＳ、ビスフェノールＦ１テトラフ
エノールエタン、トリフエノールプロパン等の多価フェ
ノール性水酸基を含む化合物との併用を妨げるものでは
ない。In addition, the present invention also relates to one or more dihydric alcohols such as ethylene glycol, propylene glycol, 1,4-butanediol, 1,3-butanediol, bentanediol, and 1,6-hexanediol, and furthermore, bisphenol A1 bis This does not preclude its use in combination with compounds containing polyhydric phenolic hydroxyl groups such as phenol S, bisphenol F1 tetraphenol ethane, and triphenol propane.
以下に上記反応の具体的条件について説明する。−殺伐
（１）で示されるエポキシ樹脂と３価アルコールもしく
は４価アルコールの単独又はそれらの混合物との反応は
触媒の存在下で６０〜２５０°Ｃ１好ましくは１２０〜
２００°Ｃの温度で行われる。反応温度が６０″Ｃ未満
であると反応速度が小さくなり過ぎるため好ましくな（
、また反応温度が２５０’Ｃを越えると、エポキシ樹脂
中の水酸基との開環反応或いはエポキシ基同士の開環反
応等が起こり、反応生成物のゲル化を招く可能性がある
ため好ましくない。The specific conditions for the above reaction will be explained below. - The reaction between the epoxy resin represented by (1) and trihydric alcohol or tetrahydric alcohol alone or a mixture thereof is carried out at 60 to 250°C, preferably 120 to 250°C, in the presence of a catalyst.
It is carried out at a temperature of 200°C. If the reaction temperature is less than 60"C, the reaction rate becomes too low, which is not preferable (
If the reaction temperature exceeds 250'C, ring-opening reactions with hydroxyl groups in the epoxy resin or ring-opening reactions between epoxy groups may occur, which is undesirable as it may result in gelation of the reaction product.
反応の触媒には、例えば水酸化ナトリウム、水酸化カリ
ウム等のアルカリ金属水酸化物、ナトリウムメチラート
、ナトリウムエチラート、カリウムメチラート、カリウ
ムエチラート等のアルカリ金属アルコラード、ジメチル
ベンジルアミン、ピリジン、トリメチルアミン、トリエ
チルアミン等の三級アミン、テトラメチルアンモニウム
クロライド、ベンジルトリメチルアンモニウムクロライ
ド等の四級アンモニウム塩、トリフェニルホスフィン、
トリエチルホスフィン、トリフェニルホスフィン等のを
機リン化合物の沃化メチル付加物、炭酸ナトリウム、塩
化リチウム等のアルカリ金属塩、三弗化硼素、塩化アル
ミニウム、四塩化錫、三弗化硼素のジメチルエーテル錯
体等のルイス酸類が用いられる。触媒の使用量は、反応
温度によって異なるが、通常、エポキシ樹脂とアルコー
ル類（２価のアルコールを使用するときはそれらも含む
）の総量に対して０．０１〜１１００００ｐｐ、好まし
くは０．１〜ｌｏｏｏｐｐｍが用いられる。Catalysts for the reaction include, for example, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal alcoholades such as sodium methylate, sodium ethylate, potassium methylate, and potassium ethylate, dimethylbenzylamine, pyridine, and trimethylamine. , tertiary amines such as triethylamine, quaternary ammonium salts such as tetramethylammonium chloride, benzyltrimethylammonium chloride, triphenylphosphine,
Methyl iodide adducts of phosphorus compounds such as triethylphosphine and triphenylphosphine, alkali metal salts such as sodium carbonate and lithium chloride, dimethyl ether complexes of boron trifluoride, aluminum chloride, tin tetrachloride, and boron trifluoride, etc. Lewis acids are used. The amount of catalyst used varies depending on the reaction temperature, but is usually 0.01 to 110,000 pp, preferably 0.1 to 110,000 pp, based on the total amount of epoxy resin and alcohol (including dihydric alcohol when used). loooppm is used.
反応は溶剤を使用せずに行うことができるが、溶剤を使
用する場合は、トルエン、キシレン等の炭化水素類、メ
チルイソブチルケトン、メチルエチルケトン、シクロヘ
キサノン等のケトン類、ｎ−プチルアセテート、メトキ
シブチルアセテート、セロソルブアセテート等の酢酸エ
ステル類等の活性水素を有しない溶剤が使用される。The reaction can be carried out without using a solvent, but if a solvent is used, hydrocarbons such as toluene and xylene, ketones such as methyl isobutyl ketone, methyl ethyl ketone, and cyclohexanone, n-butyl acetate, methoxybutyl acetate, etc. , a solvent without active hydrogen such as acetic acid esters such as cellosolve acetate is used.
−Ｓ式（１）で示されるエポキシ樹脂とアルキル基を含
む３価アルコールもしくは４価アルコールの単独又はそ
れらの混合物との当量比は、１００／１０〜１００１５
０であることが好ましい。-S The equivalent ratio of the epoxy resin represented by formula (1) to the trihydric alcohol or tetrahydric alcohol containing an alkyl group or a mixture thereof is 100/10 to 10015
Preferably, it is 0.
また、反応により得られるエポキシポリオール樹脂の水
酸基が３０ＫＯＨｍｇ／ｇより小さくなると、イソシア
ネート硬化の際に得られる塗膜の防食性及び耐薬品性が
低下し、また乾燥性も遅くなる欠点がある。逆に、水酸
基価が６００ＫＯＨｍｇ／ｇより大きくなるとアミン硬
化の際に得られる塗膜の耐水性が低下するため好ましく
ない。このため、水酸基価は３０〜６００ＫＯＨｍｇ／
ｇ、好ましくは１００〜３００ＫＯＨｍｇ／ｇの範囲に
あることが必要である。In addition, if the hydroxyl group of the epoxy polyol resin obtained by the reaction is less than 30 KOHmg/g, there is a drawback that the corrosion resistance and chemical resistance of the coating film obtained during isocyanate curing are reduced, and the drying property is also slow. On the other hand, if the hydroxyl value is greater than 600 KOHmg/g, the water resistance of the coating film obtained during amine curing will decrease, which is not preferable. Therefore, the hydroxyl value is 30 to 600 KOHmg/
g, preferably in the range of 100 to 300 KOHmg/g.
本発明のエポキシポリオール樹脂は硬化剤と組み合わせ
ることにより重防食被覆用の材料として使用される。硬
化剤としては同一分子内に一級もしくは二級のアミノ基
を２個以上有するポリアミン、又は同一分子内にイソシ
アネーシ基を２個以上有する有機ポリイソシアネートが
使用される。The epoxy polyol resin of the present invention can be used as a material for heavy-duty anti-corrosion coatings in combination with a curing agent. As the curing agent, polyamines having two or more primary or secondary amino groups in the same molecule, or organic polyisocyanates having two or more isocyanate groups in the same molecule are used.
−級もしくは二級アミノ基を２個以上有するポリアミン
としては、エチレンジアミン、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、ポリエチレンポリアミン、プロピレンジアミン、
ジプロピレントリアミン、ポリプロピレンポリアミン、
ブチレンジアミン、ペンチレンジアミン、ヘキシレンジ
アミン、オクチレンジアミン、ノニレンジアミン、デシ
レンジアミン、ジメチルウレア、１．３−ジアミン−２
−プロパツール、３，３°−イミノ−ビス−（プロピル
アミン）グアニジン、ジメチルアミノプロピルアミン、
ジエチルアミノプロピルアミン、ジブチルアミノプロピ
ルアミン、イミノビスプロピルアミン等の′・ごとき脂
肪酸ポリアミン、メタ、オルソ及びバラフエニルジアミ
ン、１，４−ナフタレンジアミン、１゜４−アンスラジ
アミン、３，３゛−ビフェニルジアミン、キシレンジア
ミン、３．４−ビフェニルアミン、３゜４−ドルオール
ジアミン、ｐ、ｐ’−メチレンジアニリン、１−メトキ
シ−６メチルメターフエニレンジアミン、ρ、ρ°−ス
ルフォニルジアミンのごとき芳香族ｉｔ級または第２級
ポリアミンまたはピペラジン、２．４−ジメチルピペラ
ジン、メラミン、２，４−ジアミノ−５−（アミノエチ
ル）ピリミジン、２，４．ｆｉ−トリアミノピリミジン
、３．９−ビス（アミノエチル）スピロビメタジオキサ
ン等のような複素環式第１級及び第２級ポリアミンが挙
げられる。さらにこれらポリアミン類と重合体脂肪酸又
は他のカルボン酸あるいはそれらのメチルエステル化物
から得られるポリアミドアミン類、あるいは前記ポリア
ミン類と各種エポキシ樹脂との付加ポリアミ曵ン類、あ
るいはそれらの組合せであるポリアミド・アダクト１１
も、−級もしくは二級アミノ基を２個以上有する限り、
硬化剤として使用することができる。これらのポリアミ
ンは特に夏季の使用に適している。Polyamines having two or more -class or secondary amino groups include ethylenediamine, diethylene, triamine, triethylenetetramine, tetraethylenepentamine, polyethylenepolyamine, propylenediamine,
dipropylene triamine, polypropylene polyamine,
Butylene diamine, pentylene diamine, hexylene diamine, octylene diamine, nonylene diamine, decylene diamine, dimethylurea, 1,3-diamine-2
-propanol, 3,3°-imino-bis-(propylamine)guanidine, dimethylaminopropylamine,
fatty acid polyamines such as diethylaminopropylamine, dibutylaminopropylamine, iminobispropylamine, meta, ortho and paraphenyldiamine, 1,4-naphthalenediamine, 1゜4-anthradiamine, 3,3゛-biphenyldiamine , xylene diamine, 3,4-biphenylamine, 3゜4-dolol diamine, p, p'-methylene dianiline, 1-methoxy-6 methylmethphenylene diamine, ρ, ρ°-sulfonyl diamine. Group it-class or secondary polyamines or piperazine, 2,4-dimethylpiperazine, melamine, 2,4-diamino-5-(aminoethyl)pyrimidine, 2,4. Included are heterocyclic primary and secondary polyamines such as fi-triaminopyrimidine, 3,9-bis(aminoethyl)spirobimetadioxane, and the like. Furthermore, polyamide amines obtained from these polyamines and polymeric fatty acids or other carboxylic acids or their methyl esters, addition polyamines obtained from the above polyamines and various epoxy resins, or polyamides which are a combination thereof. adduct 11
Also, as long as it has two or more -class or secondary amino groups,
Can be used as a hardening agent. These polyamines are particularly suitable for summer use.
また冬季における硬化剤として好適に使用される有機ポ
リイソシアネートとしては、フェニレンジイソシアネー
ト、トリレンジイソシアネート、キシリレンジイソシア
ネート、４．４°−メチレンビス（フェニルイソシアネ
ート）等の芳香族ジイソシアネート、ヘキサメチレンジ
イソシアネート、トリメチルヘキサンメチレンジイソシ
アネート、リジンジイソシアネー゛ト等の脂肪族ジイソ
シアネート等のようなポリイソシアネート化合物が挙げ
られる。またこれらのポリイソシアネート化合物ノ一種
又は二種以上とトリメチロールプロパン、トリエタノー
ルメタン等の多価アルコールとの末端イソシアネート付
加物も、さらにはこれらポリイソシアネート化合物の粗
生成物や蒸留残金等も使用できる。In addition, organic polyisocyanates suitably used as curing agents in winter include aromatic diisocyanates such as phenylene diisocyanate, tolylene diisocyanate, xylylene diisocyanate, 4.4°-methylenebis(phenylisocyanate), hexamethylene diisocyanate, and trimethylhexane. Examples include polyisocyanate compounds such as aliphatic diisocyanates such as methylene diisocyanate and lysine diisocyanate. Furthermore, terminal isocyanate adducts of one or more of these polyisocyanate compounds and polyhydric alcohols such as trimethylolpropane and triethanolmethane, as well as crude products and distillation residues of these polyisocyanate compounds, can also be used. .
エポキシポリオール樹脂と硬化剤との組成割合は、その
目的や要求される性能によって一義的には決められない
が、ごく−船釣にはエポキシポリオール樹脂のエポキシ
基１個当り化学当量的に硬化剤ポリアミンの活性水素０
．１〜２．０個、好ましくは０．３〜１．２個、または
エポキシポリオール樹脂の水酸基１個当り化学当量的に
硬化剤ポリイソシアネート０．１〜２．０個、好ましく
は０．３〜１．２個となるような割合にする。The composition ratio of the epoxy polyol resin and the curing agent cannot be determined uniquely depending on the purpose and required performance, but for boat fishing, the curing agent is chemically equivalent to each epoxy group in the epoxy polyol resin. Active hydrogen of polyamine 0
．． 1 to 2.0 pieces, preferably 0.3 to 1.2 pieces, or 0.1 to 2.0 pieces of curing agent polyisocyanate, preferably 0.3 to 2.0 pieces, chemically equivalent per 1 hydroxyl group of the epoxy polyol resin. The ratio should be 1.2 pieces.
本発明のエポキシポリオール樹脂と硬化剤よりなる組成
物は常温硬化性（乾燥性）であるので調製後は速やかに
使用すべきである。The composition comprising the epoxy polyol resin and curing agent of the present invention is curable (drying) at room temperature and should be used immediately after preparation.
このようにして得られた組成物は、それ自体で被覆剤と
して十分に有用であるが、さらに必要に応じて、ポリビ
ニルブチラール、ポリビニルホルマール、塩化ビニル、
酢酸ビニル、エポキシ樹脂、ポリヒドロキシ・ポリエー
テル樹脂、ポリヒドロキシ・ポリエステル樹脂、アクリ
ル樹脂又はアクリル樹脂、尿素ホルムアルデヒド樹脂又
は塩化ゴム等の合成樹脂類を併用しても差支えない。The composition obtained in this way is sufficiently useful as a coating agent by itself, but if necessary, polyvinyl butyral, polyvinyl formal, vinyl chloride,
Synthetic resins such as vinyl acetate, epoxy resin, polyhydroxy polyether resin, polyhydroxy polyester resin, acrylic resin or acrylic resin, urea formaldehyde resin or chlorinated rubber may be used in combination.
また、それぞれの目的、用途に応して、公知慣用の各種
の着色剤、充填剤、骨材、補強材、溶剤類、可撓性付与
剤、可塑剤、流動性調整剤、硬化促進剤、硬化遅延剤、
界面活性剤、増粘剤、難燃剤、揺変剤又は瀝青物質、そ
の他添加剤を加えてもよい。In addition, depending on the purpose and application, various known and commonly used colorants, fillers, aggregates, reinforcing materials, solvents, flexibility imparters, plasticizers, fluidity regulators, hardening accelerators, curing retarder,
Surfactants, thickeners, flame retardants, thixotropes or bituminous substances, and other additives may also be added.
上記添加剤はエポキシポリオール樹脂に予め混合してお
き、使用直前に硬化剤と混合して本組成物を調製するこ
とが一般的であり、この場合、本組成物は常温硬化性で
あるので経時的に硬化が進み、一定時間後には被覆作業
に供することができなくなるが、この一定時間のことを
可使時間と言い、可使時間がある程度確保されないと、
作業が逆に阻害されることになる。ところが、エポキシ
ポリオール樹脂と瀝青物質とを混合しておき、長期保存
すると、ポリイソシアネート硬化剤使用の場合、可使時
間が次第に短くなり作業性が悪くなる現象がみられる。The above additives are generally mixed with the epoxy polyol resin in advance and then mixed with a curing agent just before use to prepare the composition. In this case, the composition is curable at room temperature, so As the material hardens over time, it cannot be used for coating after a certain period of time, but this period of time is called the pot life, and unless a certain amount of pot life is secured,
On the contrary, work will be hindered. However, if an epoxy polyol resin and a bituminous material are mixed and stored for a long time, the pot life will gradually become shorter and workability will deteriorate if a polyisocyanate curing agent is used.
この現象は、一般の水酸基含有エポキシ樹脂と瀝青物質
との混合物−ポリイソシアネート硬化剤の系において、
既に知られている現象であり、この現象を防止するため
には酸性物質の添加が効果があることも知られている。This phenomenon occurs in a general mixture of hydroxyl group-containing epoxy resin and bituminous substance-polyisocyanate curing agent system.
This is a known phenomenon, and it is also known that adding an acidic substance is effective in preventing this phenomenon.
本組成物についても、このような現象を防止するには瀝
青物質１００重量部に対して０．５〜３．０重量部好ま
しくは１〜５重量部の酸性物質を添加すると良（、この
ような酸性物質として知られているものには、パラ−ト
ルエンスルホン酸、蓚酸等の有機酸、燐酸、塩酸等の無
機酸、活性白土、硫酸カルシウム、塩化カルシウム等の
固体酸がある。実際、本組成物の現実のタール・エポキ
シ塗料として使用するときには、これらの酸性物質の添
加は不可欠である。In order to prevent such a phenomenon in the present composition as well, it is recommended to add 0.5 to 3.0 parts by weight, preferably 1 to 5 parts by weight of an acidic substance per 100 parts by weight of the bituminous material. Examples of known acidic substances include organic acids such as para-toluenesulfonic acid and oxalic acid, inorganic acids such as phosphoric acid and hydrochloric acid, and solid acids such as activated clay, calcium sulfate, and calcium chloride. The addition of these acidic substances is essential when the composition is used as an actual tar-epoxy paint.
このようにして得られる組成物は金属、木材、プラスチ
ックス、石材、スレート、コンクリート又はモルタルを
はじめ、繊維、紙、陶器、ガラス、磁器、フィルム又は
ゴムその他の基材表面に刷毛塗り、スプレー、浸漬、ロ
ールコート、フローコートその他の方法で被覆又は浸ン
１して、これを自然乾燥ないしは場合によって加熱乾燥
その他の処理により乾燥硬化させて被覆製品となすこと
ができる。The composition obtained in this way can be applied by brushing, spraying, etc. onto the surface of metal, wood, plastics, stone, slate, concrete, mortar, fibers, paper, ceramics, glass, porcelain, film, rubber, or other substrates. A coated product can be obtained by coating or dipping by dipping, roll coating, flow coating or other methods, and then drying and curing by natural drying or, if necessary, heat drying or other treatments.
以下、本発明を実施例により具体的に説明するが、本発
明はこれらの例に限定されるものではない。EXAMPLES Hereinafter, the present invention will be specifically explained with reference to examples, but the present invention is not limited to these examples.
実施例１
攪拌装置、温度計及び冷却管を備えたフラスコにエポキ
シ当量１８８ｇ／当量のビスフェノールＡ型エポキシ樹
脂１０００．０ｇ 、 トリメチロールプロパン１１
８．８ｇ及び１０重量％水酸化カリウム水溶液０．２８
ｇを加えた後、系内を窒素ガスで置換した。続いて系を
オイルバスで昇温させ、攪拌下に反応温度１７５°Ｃで
エポキシ当量が４２１ｇ／当量になるまで反応を行った
。得られた樹脂Ｃ水酸基価は１６３ＫＯＨｍｇ／ｇであ
った０反応後トルエンで固形分量が約７５％になるよう
に系を希釈しエポキシポリオール樹脂を得た。Example 1 1000.0 g of bisphenol A epoxy resin with an epoxy equivalent of 188 g/equivalent and 11 trimethylolpropane were placed in a flask equipped with a stirrer, a thermometer, and a cooling tube.
8.8g and 10% by weight potassium hydroxide aqueous solution 0.28
After adding g, the inside of the system was replaced with nitrogen gas. Subsequently, the system was heated in an oil bath, and the reaction was carried out under stirring at a reaction temperature of 175°C until the epoxy equivalent weight reached 421 g/equivalent. The resulting resin C had a hydroxyl value of 163 KOHmg/g. After the reaction, the system was diluted with toluene to a solid content of about 75% to obtain an epoxy polyol resin.
実施例２〜７
実施例１と同様の方法により、表１に示すエポキシポリ
オール樹脂を得た。Examples 2 to 7 Epoxy polyol resins shown in Table 1 were obtained in the same manner as in Example 1.
比較例１
攪拌装置、温度計及び冷却管を備えたフラスコにエポキ
シ当量１８８ｇ／当量のビスフェノールＡ型エポキシ樹
脂１０００．０ｇ、 １．４−ブタンジオール１１９．
７ｇ及び１０重量％水酸化カリウム水溶液０．２８ｇを
加えた後、系内を窒素ガスで置換した。次いで系をオイ
ルバスで昇温させ、攪拌下に反応温度１７５°Ｃでエポ
キシ当量が４２１ｇ／当量になるまで反応を行った。得
られた樹脂の水酸基価は、１６３ＫＯＨｍｇ／ｇであっ
、た。反応後トルエンで固形分量が約７５％になるよう
に系を希釈し、エポキシポリオール樹脂を得た。Comparative Example 1 1000.0 g of bisphenol A epoxy resin with an epoxy equivalent of 188 g/equivalent and 119.0 g of 1,4-butanediol were placed in a flask equipped with a stirrer, a thermometer, and a cooling tube.
After adding 7 g and 0.28 g of a 10% by weight aqueous potassium hydroxide solution, the inside of the system was purged with nitrogen gas. Next, the system was heated in an oil bath, and the reaction was carried out under stirring at a reaction temperature of 175°C until the epoxy equivalent weight reached 421 g/equivalent. The resulting resin had a hydroxyl value of 163 KOHmg/g. After the reaction, the system was diluted with toluene to a solid content of about 75% to obtain an epoxy polyol resin.
比較例２．３
実施例１と同様の方法によるが、反応後トルエンで固形
分量が約４５％になるように系を希釈し、表１に示すエ
ポキシポリオール樹脂を得た。Comparative Example 2.3 The same method as in Example 1 was used, but after the reaction, the system was diluted with toluene so that the solid content was about 45%, and the epoxy polyol resin shown in Table 1 was obtained.
応用例１〜７及び比較応用例１〜３
次に、このようにして得られたエポキシポリオール樹脂
から、以下のようにして重防食用被覆組成物を調製し、
各種の性能評価を行った。それらの結果は表２に示す。Application Examples 1 to 7 and Comparative Application Examples 1 to 3 Next, from the epoxy polyol resin thus obtained, a heavy corrosion protection coating composition was prepared as follows,
Various performance evaluations were performed. The results are shown in Table 2.
（タール・エポキシポリオール樹脂塗料の調製方法）
エポキシポリオール樹脂１２．５重量部（但し、比較応
用例３については２０．８重量部）、タール（株式会社
吉田製油所製、タークロン２３０−２０Ｘ）３７．５重
量部、タルク（富士タルク工業株式会社製、ＰＫＰ ＃
５３）３７．５重量部、トルエン５重量部をデイスパー
によって混練し、タール・エポキシポリオール樹脂塗料
を調製した。(Preparation method of tar/epoxy polyol resin paint) 12.5 parts by weight of epoxy polyol resin (20.8 parts by weight for Comparative Application Example 3), tar (manufactured by Yoshida Refinery Co., Ltd., Takuron 230-20X) 37 .5 parts by weight, talc (manufactured by Fuji Talc Industrial Co., Ltd., PKP #
53) 37.5 parts by weight and 5 parts by weight of toluene were kneaded using a disper to prepare a tar-epoxy polyol resin paint.
このタール・エポキシポリオール樹脂塗料にアミン系硬
化剤（三井東圧化学株式会社製、エポキ−Ｈ１６２，活
性水素光１＝２６２）又はイソシアネート系硬化剤（三
井東圧化学株式会社製、オレスターＰ １０２Ｘ、ＮＣ
０％・１５）を混合して重防食用被覆組成物を調製した
。This tar/epoxy polyol resin paint is coated with an amine curing agent (Mitsui Toatsu Chemical Co., Ltd., Epokey-H162, active hydrogen light 1=262) or an isocyanate curing agent (Mitsui Toatsu Chemical Co., Ltd., Orester P 102X). , N.C.
A heavy corrosion protection coating composition was prepared by mixing 0% and 15).
（試験の方法）
前記重防食用被覆組成物を、次の処理鋼板に乾燥膜厚が
２００〜２５０μになるように塗布し、２０″Ｃ又は各
試験条件に合った養生期間の後、各試験に供した。(Test method) The above-mentioned heavy-duty anti-corrosion coating composition was applied to the following treated steel plate so that the dry film thickness was 200 to 250μ, and after a curing period of 20″C or according to each test condition, each test was carried out. Served.
・軟鋼板（ＪＩＳ Ｇ−３１４１）
０．３ Ｘ １００ Ｘ ２００ｍｍをサンドペーパー
で研磨したのち、水洗、アセトン洗浄、乾燥、石油ベン
ジンで脱脂したもの。- Mild steel plate (JIS G-3141) 0.3 x 100 x 200 mm, polished with sandpaper, washed with water, washed with acetone, dried, and degreased with petroleum benzine.
・サンドブラスト処理鋼板（ＪＩＳ Ｇ−３１４１）２
、ＯＸ５０Ｘ１００ｖａをＳＩＳ Ｓａ ２．５に素地
調整をしたもの。・Sandblasting steel plate (JIS G-3141) 2
, OX50X100va with substrate adjustment to SIS Sa 2.5.
Ｏボンドライフ
前記により調整した重防食用被覆組成物２５０ｍｊ２を
容量３００ＩＩＩＩｌ（内径７０ｍｍ） （Ｄ フリー
ｔ−缶ニ入れ、５°Ｃ５２０℃で使用できる時間が、２
時間以上であるものを合格とした。O Bond Life 250mj2 of the heavy-duty anti-corrosion coating composition prepared above was added in a capacity of 300IIIl (inner diameter 70mm) (D) in a free T-can, and the usable time at 5°C and 520°C was 2.
Those that exceeded the specified time were considered to have passed.
○歩行性の可否
前記重防食用液ｙ１組成物を塗布した鋼板を、２０“Ｃ
，５°Ｃで２４時間乾燥させた後、体重７０Ｋｇの人間
が踏み付は足跡の残らないものを合格とした。○Is walkability possible?The steel plate coated with the heavy corrosion protection liquid y1 composition was heated to 20"C.
, After drying at 5°C for 24 hours, a product that leaves no footprint when trampled by a person weighing 70 kg is considered to be passed.
０１０ｍｍ折り曲げ
前記軟鋼板に膜厚１５０μで塗布し、７！日間乾燥した
後、内径１ＯＩＩＩＩｌの丸棒にそって折り曲げ、塗膜
の割れ・剥がれの状態を判定した。010mm bending Apply to the mild steel plate with a film thickness of 150μ, 7! After drying for several days, it was bent along a round bar with an inner diameter of 1OIIII, and the state of cracking and peeling of the coating film was determined.
Ｏデュポン衝撃試験
デュポン衝撃試験機を用い、前記と同様に作成した試験
片にＩＫｇの重りを落とし、塗膜の割れ・剥がれの発生
する高さを測定した。O DuPont Impact Test Using a DuPont impact tester, a weight of I kg was dropped onto a test piece prepared in the same manner as above, and the height at which cracking or peeling of the coating film occurred was measured.
Ｏ耐食性
水道水、海水、塩水噴霧試験、５重量％水酸化ナトリウ
ム水溶液及び５重量％硫酸水溶液は、室温で３０日間浸
漬し、促進塩水りについては、６０°Ｃで２週間浸漬し
合否を判定した。O Corrosion resistance tap water, seawater, salt spray test, 5 wt % sodium hydroxide aqueous solution and 5 wt % sulfuric acid aqueous solution, immersed at room temperature for 30 days, accelerated salt water, immersed at 60 ° C for 2 weeks to judge pass/fail. did.
本１ 食塩 ５０ｇ 酢酸 １０＋ｗ ４２ 過酸化水素（３０χ） ５ｇ 水 １１ を水酸化ナトリウムでＰＨ・３．０に調節したもの。Book 1 Salt 50g Acetic acid 10+w 42 Hydrogen peroxide (30χ) 5g Water 11 adjusted to pH 3.0 with sodium hydroxide.
本発明の重防食被覆用組樹脂を使用して得られれた被覆
物は、優れた耐食性、耐久性、耐水性、及び密着性を示
す。The coating obtained using the composite resin for heavy corrosion protection coating of the present invention exhibits excellent corrosion resistance, durability, water resistance, and adhesion.
そのために各種のプラント、タンク、パイプ類、船舶、
橋梁、鉄骨、車両その他の大型構築物の被覆材のほか、
家庭用電気機器、スチール製機器、各種測定Ｒ器、販売
機、医療機器その他の金属製品の被覆材、床材、壁材、
磁性塗料、繊維処理剤、防水処理剤、絶縁処理剤、ガラ
ス用防曇剤、その他店範囲な応用分野に有効である。For this purpose, various plants, tanks, pipes, ships,
In addition to coating materials for bridges, steel frames, vehicles and other large structures,
Household electrical equipment, steel equipment, various measuring instruments, vending machines, medical equipment, and other metal products covering materials, flooring materials, wall materials,
It is effective in magnetic paints, fiber treatment agents, waterproof treatment agents, insulation treatment agents, antifogging agents for glass, and a wide range of other application fields.
特許出願人 三井東圧化学株式会社Patent applicant: Mitsui Toatsu Chemical Co., Ltd.
Claims (1)
の単独又はそれらの混合物を反応させて得られる、エポ
キシ当量２００〜２０００ｇ／当量、水酸基価３０〜６
００ＫＯＨｍｇ／ｇを有する重防食被覆用エポキシポリ
オール樹脂。Epoxy equivalent: 200 to 2000 g/equivalent, hydroxyl value: 30 to 6, obtained by reacting an epoxy resin with a trihydric alcohol or a tetrahydric alcohol, or a mixture thereof.
Epoxy polyol resin for heavy corrosion protection coating having 00KOHmg/g.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28755587A JPH01131284A (en) | 1987-11-16 | 1987-11-16 | Heavy duty corrosionproof coating resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28755587A JPH01131284A (en) | 1987-11-16 | 1987-11-16 | Heavy duty corrosionproof coating resin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01131284A true JPH01131284A (en) | 1989-05-24 |
Family
ID=17718860
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP28755587A Pending JPH01131284A (en) | 1987-11-16 | 1987-11-16 | Heavy duty corrosionproof coating resin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01131284A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0459592A2 (en) * | 1990-06-01 | 1991-12-04 | Shell Internationale Researchmaatschappij B.V. | Modified epoxy resin composition |
| US5407978A (en) * | 1993-05-07 | 1995-04-18 | Minnesota Mining And Manufacturing Company | Rapid curing powder epoxy coating compositions having increased flexibility, incorporating minor amounts of aliphatic triepoxides |
| CN105017927A (en) * | 2015-06-30 | 2015-11-04 | 苏州乔纳森新材料科技有限公司 | Medical magnetic red lead antirust paint and preparation method thereof |
| CN107163835A (en) * | 2017-06-15 | 2017-09-15 | 苏州莱特复合材料有限公司 | A kind of preparation method of metal fire resistant anticorrosive paint |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63230724A (en) * | 1987-03-06 | 1988-09-27 | シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ | Production of modified epoxy resin |
-
1987
- 1987-11-16 JP JP28755587A patent/JPH01131284A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63230724A (en) * | 1987-03-06 | 1988-09-27 | シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ | Production of modified epoxy resin |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0459592A2 (en) * | 1990-06-01 | 1991-12-04 | Shell Internationale Researchmaatschappij B.V. | Modified epoxy resin composition |
| US5407978A (en) * | 1993-05-07 | 1995-04-18 | Minnesota Mining And Manufacturing Company | Rapid curing powder epoxy coating compositions having increased flexibility, incorporating minor amounts of aliphatic triepoxides |
| CN105017927A (en) * | 2015-06-30 | 2015-11-04 | 苏州乔纳森新材料科技有限公司 | Medical magnetic red lead antirust paint and preparation method thereof |
| CN107163835A (en) * | 2017-06-15 | 2017-09-15 | 苏州莱特复合材料有限公司 | A kind of preparation method of metal fire resistant anticorrosive paint |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR102255314B1 (en) | Sprayable polyurethane coating | |
| US5369152A (en) | Urethane modified waterborne dispersions | |
| JPH0129389B2 (en) | ||
| KR100831205B1 (en) | A cathodic electrodeposition coating compositions having improved appearance, anti-corrosion resistance and flexibility | |
| US4148950A (en) | Epoxy surfacer cements containing polyamine-ketimine mixtures | |
| JP6348589B2 (en) | Curable polyurethane coating composition and method for preparing the same | |
| JPH10219185A (en) | Coating base component and heavy duty anticorrosive coating composition | |
| JP5024586B2 (en) | Aqueous resin composition | |
| JPH01131284A (en) | Heavy duty corrosionproof coating resin | |
| JP2005239928A (en) | Aqueous epoxy resin composition | |
| TW567197B (en) | Solventless reactive compositions and their uses | |
| JPH07305026A (en) | Polyester polyol two-pack curing type urethane coating composition | |
| JP3858184B2 (en) | Epoxy resin curing agent having self-emulsifying function and epoxy resin composition containing the curing agent | |
| RU2216561C1 (en) | Anticorrosion protective polymeric coating | |
| JPS6342945B2 (en) | ||
| CN115135690A (en) | Curing agent for epoxy resin coating | |
| KR100576800B1 (en) | Tar-free anti-corrosive resin and coating composition having fast-curable property at low temperature | |
| JPS62109868A (en) | Anticorrosive coating material for reinforced concrete | |
| JP4919040B2 (en) | Epoxy resin composition, cured product thereof, coating composition, and novel epoxy resin | |
| JP2006273913A (en) | Water-based epoxy resin composition | |
| JP5088600B2 (en) | Aqueous resin composition | |
| JP4807002B2 (en) | Water-based epoxy resin composition | |
| KR100204531B1 (en) | Process for preparing a thermosetting resin composition and a resin system for cathodic electrodeposition | |
| JPH0429710B2 (en) | ||
| JPH072930B2 (en) | Method of forming cured coating film |