CN1745151A - Nonaromatic solvent type coating resin composition - Google Patents
Nonaromatic solvent type coating resin composition Download PDFInfo
- Publication number
- CN1745151A CN1745151A CN 200480003393 CN200480003393A CN1745151A CN 1745151 A CN1745151 A CN 1745151A CN 200480003393 CN200480003393 CN 200480003393 CN 200480003393 A CN200480003393 A CN 200480003393A CN 1745151 A CN1745151 A CN 1745151A
- Authority
- CN
- China
- Prior art keywords
- solvent
- composition
- resin composition
- epoxy
- coating resin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000002904 solvent Substances 0.000 title claims abstract description 155
- 238000000576 coating method Methods 0.000 title claims abstract description 78
- 239000011248 coating agent Substances 0.000 title claims abstract description 74
- 239000011342 resin composition Substances 0.000 title claims abstract description 25
- 239000000203 mixture Substances 0.000 claims abstract description 105
- 239000012046 mixed solvent Substances 0.000 claims abstract description 50
- 239000007787 solid Substances 0.000 claims abstract description 41
- 238000001704 evaporation Methods 0.000 claims abstract description 39
- 230000008020 evaporation Effects 0.000 claims abstract description 39
- 239000003822 epoxy resin Substances 0.000 claims abstract description 31
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 31
- 229920005989 resin Polymers 0.000 claims description 116
- 239000011347 resin Substances 0.000 claims description 116
- 239000004593 Epoxy Substances 0.000 claims description 70
- 150000001412 amines Chemical class 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 36
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 22
- 238000007605 air drying Methods 0.000 claims description 18
- 150000002148 esters Chemical class 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000003700 epoxy group Chemical group 0.000 claims description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 8
- 238000007865 diluting Methods 0.000 claims description 8
- 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 claims description 7
- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 claims description 7
- 229920006334 epoxy coating Polymers 0.000 claims description 5
- 230000007797 corrosion Effects 0.000 abstract description 2
- 238000005260 corrosion Methods 0.000 abstract description 2
- 239000000758 substrate Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 description 72
- -1 turps Chemical compound 0.000 description 28
- 239000000243 solution Substances 0.000 description 21
- 238000000034 method Methods 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- 238000012360 testing method Methods 0.000 description 17
- 230000003628 erosive effect Effects 0.000 description 15
- 239000002994 raw material Substances 0.000 description 14
- 238000011156 evaluation Methods 0.000 description 13
- 239000007858 starting material Substances 0.000 description 12
- 229910000831 Steel Inorganic materials 0.000 description 10
- 239000010959 steel Substances 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 8
- 239000000049 pigment Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
- 238000001879 gelation Methods 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 230000000007 visual effect Effects 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- 208000037656 Respiratory Sounds Diseases 0.000 description 4
- 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 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 150000002466 imines Chemical class 0.000 description 4
- RMIODHQZRUFFFF-UHFFFAOYSA-M methoxyacetate Chemical compound COCC([O-])=O RMIODHQZRUFFFF-UHFFFAOYSA-M 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000004576 sand Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- NIJJYAXOARWZEE-UHFFFAOYSA-N Valproic acid Chemical compound CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 description 3
- 239000004411 aluminium Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 3
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 3
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 3
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- 239000005022 packaging material Substances 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 3
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 2
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- 229910001335 Galvanized steel Inorganic materials 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 241000863032 Trieres Species 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000002390 adhesive tape Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 2
- PGEAEAYLSCKCCO-UHFFFAOYSA-N benzene;n-methylmethanamine Chemical compound CNC.C1=CC=CC=C1 PGEAEAYLSCKCCO-UHFFFAOYSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 239000010960 cold rolled steel Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical compound C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 description 2
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 2
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 150000007520 diprotic acids Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229950011333 edamine Drugs 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000008397 galvanized steel Substances 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000003607 modifier 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
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 2
- IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920001021 polysulfide Polymers 0.000 description 2
- 238000002203 pretreatment Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 238000007665 sagging Methods 0.000 description 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- NVKTUNLPFJHLCG-UHFFFAOYSA-N strontium chromate Chemical compound [Sr+2].[O-][Cr]([O-])(=O)=O NVKTUNLPFJHLCG-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 2
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 2
- 239000005028 tinplate Substances 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 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 2
- 239000002966 varnish Substances 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- 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 2
- 229910000165 zinc phosphate Inorganic materials 0.000 description 2
- FZENGILVLUJGJX-NSCUHMNNSA-N (E)-acetaldehyde oxime Chemical compound C\C=N\O FZENGILVLUJGJX-NSCUHMNNSA-N 0.000 description 1
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-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
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 1
- XSXWOBXNYNULJG-UHFFFAOYSA-N 2-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=CC=C1O XSXWOBXNYNULJG-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- HHAPGMVKBLELOE-UHFFFAOYSA-N 2-(2-methylpropoxy)ethanol Chemical compound CC(C)COCCO HHAPGMVKBLELOE-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- SKIIKRJAQOSWFT-UHFFFAOYSA-N 2-[3-[1-(2,2-difluoroethyl)piperidin-4-yl]oxy-4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound FC(CN1CCC(CC1)OC1=NN(C=C1C=1C=NC(=NC=1)NC1CC2=CC=CC=C2C1)CC(=O)N1CC2=C(CC1)NN=N2)F SKIIKRJAQOSWFT-UHFFFAOYSA-N 0.000 description 1
- VPSXHKGJZJCWLV-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(1-ethylpiperidin-4-yl)oxypyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)OC1CCN(CC1)CC VPSXHKGJZJCWLV-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
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- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
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- 238000005516 engineering process Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
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- 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 1
- 238000009998 heat setting Methods 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
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- 229940051250 hexylene glycol Drugs 0.000 description 1
- JUMYIBMBTDDLNG-OJERSXHUSA-N hydron;methyl (2r)-2-phenyl-2-[(2r)-piperidin-2-yl]acetate;chloride Chemical compound Cl.C([C@@H]1[C@H](C(=O)OC)C=2C=CC=CC=2)CCCN1 JUMYIBMBTDDLNG-OJERSXHUSA-N 0.000 description 1
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- 229940117955 isoamyl acetate Drugs 0.000 description 1
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- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 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
- NFIDBGJMFKNGGQ-UHFFFAOYSA-N isopropylmethylphenol Natural products CC(C)CC1=CC=CC=C1O NFIDBGJMFKNGGQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 229940087305 limonene Drugs 0.000 description 1
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- 238000005259 measurement Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
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- DNYZBFWKVMKMRM-UHFFFAOYSA-N n-benzhydrylidenehydroxylamine Chemical compound C=1C=CC=CC=1C(=NO)C1=CC=CC=C1 DNYZBFWKVMKMRM-UHFFFAOYSA-N 0.000 description 1
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- YNOGYQAEJGADFJ-UHFFFAOYSA-N oxolan-2-ylmethanamine Chemical compound NCC1CCCO1 YNOGYQAEJGADFJ-UHFFFAOYSA-N 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
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- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
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- 231100000719 pollutant Toxicity 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
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- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
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Landscapes
- Paints Or Removers (AREA)
- Epoxy Resins (AREA)
Abstract
The invention aims at providing a nonaromatic solvent type coating resin composition which is excellent in tight adhesion to a substrate, corrosion resistance, processability, scratch resistance, solvent resistance, and so on, and is well balanced among them. In the invention, the nonaromatic solvent constituting the composition is selected with attention paid to the evaporation rate and SP value of a mixed solvent and the viscosity of a solution of an epoxy resin therein having a solid content of 40 %. The invention relates to a nonaromatic solvent type coating epoxy resin composition characterized by consisting of a solution which is obtained by dissolving an epoxy resin composition in a specific nonaromatic solvent (i) and has a solid content of 60 % or below: (i) a mixed solvent which consists of nonaromatic solvents satisfying the relationship (1) and a solution in which of a modified epoxy resin composition exhibits a viscosity of 10,000mPa.s or below when the solid content of the solution is 40%: 9.0 < SP < 11.0 (wherein SP = SigmaCiSPi) (1).
Description
Technical field
The present invention relates to a kind of remarkably and can obtain equilibrated Nonaromatic solvent type coating resin combination between these performances for raw-material adhesivity, erosion resistance, solvent resistance, scuff resistance, processibility, it goes in pre-matel coated, material of construction usefulness gluing (sizing) material, the auto parts etc.
Background technology
The aromatic series series solvent is described in PRTR (pollutant Release and Transfer Register) the method object chemical substance.Can cause environmental pollution etc. if in its treating processes, be released in the atmosphere, therefore require to abandon the use of aromatic series series solvent is also become social concern.With regard to these aromatic series series solvents, not only it is restricted on handling, and might be very limited in the use in the future.Therefore, promptly do not use the research and development of coating resin composition of PRTR method objectification compound very active to only containing non-aromatic compounds in recent years.
Under such environment, when in coating resin composition, only using the non-aromatic series solvent and replacing the aromatic series series solvent, be necessary solvent to be selected, and change is about the design of resin according to purposes with this.
For example, what use in single component (one pack) Thermocurable coating resin is, makes the carbamate blocking modification Resins, epoxy that remix end-blocking isocyanic ester forms after the Resins, epoxy generation modification.So, very extensive to the application that these resins carry out the modified epoxy coating that solubilisate forms with the mixed solvent that contains the aromatic series series solvent.When using the non-aromatic series solvent, it is of crucial importance that dissolving resin and being used to is coated with the velocity of evaporation of the solvent under the baking-curing temperature of membranization.When the mutual solubility of all kinds of SOLVENTS and Resins, epoxy lower, even its soltion viscosity that dissolves each other in addition also has when significantly increasing, as coating resin, its operation existing problems.
In addition, with regard to single component Air drying type coating resin, very extensive to the application that the Resins, epoxy of modification carries out the modified epoxy coating aspect that solubilisate forms with the mixed solvent that contains the aromatic series series solvent.In the past as being used for the solvent of the resin of this system, use be can stablize dissolving as the Resins, epoxy of raw material and dope viscosity suitably, when coated article is coated with its film-forming properties good, form and can disperse fast after filming and can not remain in fragrant family mixed solvent in filming.As the aromatic series series solvent, for example can use toluene, dimethylbenzene.They have suitable velocity of evaporation at normal temperatures, so can control the velocity of evaporation of mixed solvent, under the situation of dissolved epoxy, can improve the mutual solubility of mixed solvent and resin in addition, realize the lowering viscousity of coating.So when using the non-aromatic series solvent, the velocity of evaporation of the solvent after dissolving resin and the coating is equally also very important.
Summary of the invention
The inventor etc. are in order to address these problems, concentrate on studies, the velocity of evaporation of the mixed solvent when finally being conceived to select the non-aromatic series solvent, SP value and the soltion viscosity when being 40% concentration dissolved epoxy with solid state component have been finished the present invention.Promptly
[1] a kind of Nonaromatic solvent type modified epoxy coating resin composition is characterized in that, is that concentration below 60% is dissolved in the non-aromatic series solvent of selecting according to condition (i) with resin combination with solid state component.
Condition (i): be a kind of mixed solvent, selected solvent all is a non-aromatic system, and satisfies following (formula-1), and the soltion viscosity when the solid state component of the modified epoxy resin composition that is dissolved in this solvent is 40% is below the 10000mPas.
(formula-1) SP=∑ CiSPi is 9.0≤SP≤11.0
Wherein, Ci (wet%): the content of selected solvent in whole solvents
SPi: the SP value of selected solvent
[2] a kind of single component thermo-setting coating resin composition, it is characterized in that, in [1], mix the B composition of the A composition of 95～70 weight parts (solid state component) and 5～30 weight parts (solid state component) and make its total amount reach 100 weight parts (solid state component), and be that concentration below 60% is dissolved in the non-aromatic series solvent of (ii) selecting according to condition with solid state component.
A composition: be a kind of modified epoxy resin composition, contain Resins, epoxy that epoxy equivalent (weight) is 300～3000g/eq (a) and polyfunctional amine (b), with respect to epoxy equivalent (weight) 1.0 equivalents in (a) composition, (b) active hydrogen in the composition is 1.10～1.80 equivalents.
B composition: end-blocking isocyanic ester.
Condition is (ii): selected solvent all is a non-aromatic, and satisfies following (formula-2).
(formula-2) V=∑ CiVi is 18≤V≤100
Wherein, Ci (wet%): the content of selected solvent in whole solvents
Vi: the velocity of evaporation of selected solvent (is made as 100 with N-BUTYL ACETATE
The time speed of relative movement)
[3] a kind of Air drying type coating resin composition, it is characterized in that, in [1], modified epoxy resin composition satisfies condition (iii), wherein, described modified epoxy resin composition is that to carry out number-average molecular weight that addition obtains be that 4000～10000 amine-modified epoxy resin is formed for the Resins, epoxy (a) of 200～1000g/eq and polyfunctional amine (b) by making epoxy equivalent (weight), and with respect to epoxy group(ing) 1.00 equivalents in (a) composition, (b) active hydrogen in the composition is 1.10～1.60 equivalents.
Condition is (iii): selected solvent all is a non-aromatic, satisfies following (formula-3).
(formula-3) V=∑ CiVi is 100≤V≤300
Wherein, Ci (wet%): the content of selected solvent in whole solvents
Vi: the velocity of evaporation of selected solvent (is made as 100 with N-BUTYL ACETATE
The time speed of relative movement)
[4] the Air drying type coating resin composition of record in [3] is characterized in that polyfunctional amine (b) is multifunctional alkanolamine (b1).
[5] the Air drying type coating resin composition of record in [3] or [4], it is characterized in that, polyfunctional amine (b) is the mixture of multifunctional alkanolamine (b1) and polyfunctional amine in addition (b2), and the equivalence ratio of these compositions is 0.70～1.00/0～0.30 (total amount of two kinds of compositions is 1.00 equivalents).
[6] the single component thermo-setting coating resin composition of each record or Air drying type coating resin composition in [2-5] is characterized in that, Resins, epoxy (a) is bisphenol A diglycidyl ether and/or Bisphenol F diglycidylether.
[7] be a kind of Air drying type coating resin composition, it is characterized in that, and with [3～6] described Air drying type coating resin composition and the diluting solvent selected according to condition (iv-1) as adding the solvent in this Air drying type coating resin composition to.
Condition (iv-1): in solvent, contain the pimelinketone of 20wt% at least.
Embodiment
As the non-aromatic series solvent that uses in the present invention, can be exemplified as normal heptane, normal hexane, do not contain aromatic mineral turpentine (mineral spirit), limonene, turps, hexanaphthene, methylcyclohexane, ethylcyclohexane, non-aromatic hydrocarbon system solvents such as isoparaffin series solvent, methyl alcohol, ethanol, n-propyl alcohol, Virahol, propyl carbinol, isopropylcarbinol, sec-butyl alcohol, the trimethyl carbinol, Pentyl alcohol, primary isoamyl alcohol, 2-Ethylhexyl Alcohol, methyl isobutyl carbinol, pure series solvent such as benzylalcohol, methylcyclohexane, the cellosolve solvent, ethylene glycol butyl ether, ethylene glycol monoisobutyl ether, tertiary butyl cellosolve, ispropyl cellosolve, the hexyl cellosolve, methoxybutanol, 3-methyl-3-methoxybutanol, methyl carbitol, Trivalin SF, diethylene glycol monobutyl ether, the propylene glycol monomethyl ether, the dipropylene glycol monomethyl ether, propylene glycol n-butyl ether, the propylene glycol positive propyl ether, dipropylene glycol positive propyl ether diox, ether alcohol and ether series solvents such as propyl cellosolve, ritalin, vinyl acetic monomer, n-propyl acetate, Iso Butyl Acetate, n-butyl acetate, isobutyl acetate, isoamyl acetate, acetic acid methyl glycol monoethyl ether ester, acetic acid glycol monoethyl ether ester, acetic acid butyl glycol monoethyl ether ester, acetic acid methoxyl group propyl ester, acetic acid methoxyl group butyl ester, the acetic acid carbitol ester, acetic acid diethylene glycol monobutyl ether ester, acetic acid 3-methyl 3-methoxyl group butyl ester, propionic acid 3-ethoxy ethyl ester, 2,2,4-trimethylammonium-1, the 3-pentanediol mono isobutyrate, ester and ether-ether series solvents such as diester, acetone, methylethylketone, mibk, diisobutyl ketone, methyl n hexyl ketone, Methyl amyl ketone, pimelinketone, Pyranton, ketone series solvents such as isophorone, tetrahydrofuran (THF), dimethyl formamide etc.They can use separately, also can be with the multiple mixed solvent that is combined into.
The invention is characterized in that the SP that uses following (formula-1) is the non-aromatic series solvent of 9.0≤SP≤11.0.Here the SP value of Ding Yi solvent is meant the value that calculates according to the calculating of the chemical constitution in " coating basic science " (former rugged brave time work, p51 (1977) Omaki bookstore).
(formula-1): SP=∑ CiSPi
Wherein, Ci (wet%): the content of selected solvent in whole solvents
SPi: the SP value of selected solvent
In addition, described solvent is that the solid state component of dissolved modified epoxy resin composition in this solvent is that 40% o'clock soltion viscosity is the mixed solvent below the 10000mPas.
＜single component thermo-setting coating resin 〉
As single component thermo-setting coating resin, what used is so-called carbamate blocking modification Resins, epoxy in the past, this modified resin is, compound with phenol hydroxyl and Epicholorohydrin are reacted and obtain after the Resins, epoxy, utilize wherein contained reactive epoxy group(ing) that is rich in, adopt amine, polymeric amide, diprotic acid etc. to make it that cross-linked polymerization take place, remix end-blocking isocyanic ester forms afterwards.So widely used is with the mixed solvent that contains the aromatic series series solvent modified epoxy coating with its solubilisate.As require the performance that possesses, erosion resistance, adhesivity, workability, scuff resistance etc. are arranged.
But, there are the following problems for the resin of this system, promptly, when the dissolving under the baking-curing temperature is inappropriate as the velocity of evaporation of all kinds of SOLVENTS of the Resins, epoxy of raw material, if it is slower to be coated with the velocity of evaporation of the solvent after the membranization, during then solvent can remain in and film and the rerum natura of filming behind the baking-curing is descended, on the contrary when velocity of evaporation is too fast, can occurs breaking and cause paint film defect.In addition, even when all kinds of SOLVENTS when lower or miscible solutions viscosity is also higher for the mutual solubility of Resins, epoxy, even with solid state component be adjusted to can complete operation as coating resin state, also have the problem that can't be coated with.
Up to now, usually use velocity of evaporation suitably and the suitable aromatic series series solvent of velocity of evaporation that do not rise of the soltion viscosity after, the dissolving good as the part of mixed solvent with the mutual solubility of Resins, epoxy, be specially toluene or dimethylbenzene, control the velocity of evaporation of solvent thus or improved the mutual solubility of resin and mixed solvent, perhaps carried out lowering viscousity.Therefore, be the velocity of evaporation of the solvent that uses in the single component thermo-setting coating resin at non-aromatic, satisfy 10≤V≤100 when representing with the velocity of evaporation shown in following (formula-2).Here the velocity of evaporation of Ding Yi solvent be to use be shown in Tanaka zhang it: the calculating formula of " coating and coating " No339, p45 (1981) " evaporation of solvent " calculates that the velocity of evaporation that converts to after the velocity of evaporation N-BUTYL ACETATE is made as 100 o'clock relative velocity of evaporation and the value that obtains.
(formula-2) V=∑ CiVi
Wherein, Ci (wet%): the content of selected solvent in whole solvents
Vi: the velocity of evaporation of selected solvent (is made as 100 with N-BUTYL ACETATE
The time speed of relative movement)
When V is in this scope, there is not dissolvent residual in the filming behind the baking-curing, the rerum natura of filming does not worsen, and in addition, can not occur during baking-curing breaking, and can not produce paint film defect etc. yet, is preferred from these aspects.Preferred V is 30≤V≤70.
In addition, the SP value of (formula-1) is in the scope of 9.0≤SP≤11.0.When in this scope, good with the mutual solubility of modified epoxy, can obtain the stabilized uniform lacquer.Be preferably 9.50≤SP≤10.50.
At non-aromatic of the present invention is that the resin combination that uses in the single component thermo-setting coating resin is characterised in that, mix following (A) composition 95～70 weight parts (solid state component) and B composition 5～30 weight parts (solid state component) and make its total amount reach 100 weight parts (solid state component), and be that concentration below 60% is dissolved in the selected non-aromatic series solvent with solid state component.Here, the A composition contains Resins, epoxy (a) and the polyfunctional amine (b) of epoxy equivalent (weight) 300～3000g/eq, be with respect to epoxy equivalent (weight) 1.0 equivalents in (a) composition, (b) active hydrogen in the composition is the modified epoxy of 1.10～1.80 normal high moleculars, and the B composition is the end-blocking isocyanic ester.
Below to describing as the Resins, epoxy (a) and the polyfunctional amine (b) that are used for A composition of the present invention.
In the present invention, Resins, epoxy (a) is meant bisphenol A diglycidyl ether, the Bisphenol F diglycidylether, the phenolic varnish glycidyl ether, hexahydrobenzene dioctyl phthalate glycidyl ester, the dimeracid glycidyl ester, the four glycidyl group aminodiphenylmethane, 3,4-epoxy-6-methylcyclohexyl methyl carboxylic acids ester, the triglycidyl group isocyanuric acid ester, 3,4-epoxycyclohexyl methyl carboxylic acids ester, polypropylene glycol diglycidyl ether, two terminal diglycidylether modifiers of polyhutadiene or polysulphide etc., preferred bisphenol A diglycidyl ether, the Bisphenol F diglycidylether.They can use more than a kind or 2 kinds.
In addition, its epoxy equivalent (weight) is in the scope of 300～3000g/eq.When in this scope, comparatively desirable from the viewpoint of erosion resistance, workability.
In the present invention, polyfunctional amine (b) is the amine that has 2 above active hydrogens in 1 molecule.Can specifically be exemplified as Yi Bingchunan, single Propanolamine, only son's hydramine, monoethanolamine, Diethylenetriaminee (DETA), Edamine, propylamine, butylamine, isophorone diamine, tetrahydrofurfuryl amine, benzene dimethylamine, diaminodiphenylmethane, diamino sulfone, octylame, mphenylenediamine, amylamine, hexylamine, nonyl amine, decyl amine, triethylenetetramine, the tetramethylene amylamine, TEPA, dimethylaminopropylamine, diethylaminopropylamine, N-aminoethyl piperazine, methacene diamine, diamino diphenyl sulfone etc.
In the present invention, with regard to the cooperation ratio of above-mentioned (b) composition, with respect to total 1.0 equivalents of the epoxy group(ing) of (a) composition, (b) active hydrogen in the composition need reach 1.10～1.80 equivalents.
When in this scope,, preferred from viewpoints such as the gelation of resin solution, water tolerance.
Then, the method to the modified epoxy of making A composition of the present invention describes.Epoxy group(ing) 1.0 equivalents with respect to (a) composition, with its active hydrogen is that 1.10～1.80 normal ratios cooperate polyfunctional amine (b), in all or part of solvent of mixed solvent solvent-free or that select according to condition (formula-1) (formula-2), Resins, epoxy (a) and polyfunctional amine (b) are reacted, thereby obtain modified epoxy.
Below, to describing as the end-blocking isocyanic ester that is used for B composition of the present invention.In the present invention, the end-blocking isocyanic ester is by known method isocyanate compound and active dydrogen compounds to be reacted, obtain the carbamate prepolymer that end has the isocyanato-base, itself and end-capping reagent are reacted and the material of isocyanato-base end-blockingization.These reactions can be carried out in the solvent that does not have active hydrogen or under solvent-free, at this moment, can use known catalyzer such as tertiary amine, organo-metallic.Above-mentioned solvent also is selected solvent.
In the present invention, as above-mentioned isocyanate compound, can enumerate the aliphatic isocyanates class of hexamethylene diisocyanate, trimethyl hexamethylene diisocyanate and so on, xylylene vulcabond, 2,4-tolylene diisocyanate, 2, the aromatic diisocyanate class of 6-tolylene diisocyanate and so on, the ester ring type diisocyanates of isophorone diisocyanate and so on, and their diisocyanates mixture, polymer etc.
In the present invention, as above-mentioned active dydrogen compounds, can enumerate ethylene glycol, propylene glycol, 1, the 2-butyleneglycol, 1, the 3-butyleneglycol, 1, the 6-hexylene glycol, glycol ether, dipropylene glycol, neopentyl glycol, hydroxyl trimethylacetic acid ester, triglycol, xylyl alcohol, 1, dibasic alcohol such as 4-butyleneglycol, glycerine, trimethylolethane, TriMethylolPropane(TMP), 1,2, trivalent alcohols such as 6-hexanetriol, low molecular weight polyols such as tetramethylolmethane, polyether polyols such as the propylene oxide of these polyvalent alcohols or ethylene oxide adduct have carried out high molecular polyvalent alcohol such as fatty acid modified material etc. when making polyester polyol low molecular weight polyols and dicarboxylic acid are reacted and obtain.They can be used alone or as a mixture.
In the present invention, as above-mentioned end-capping reagent, can use in the materials such as phenol system, lactan system, oxime system, imines system, active methylene group system, acid amides system, imide series, sulphite system any, but the end-capping reagent of preferred phenol system, lactan system, oxime system, imines system.As their concrete example; can enumerate phenol; cresols; xylenol; nitrophenol; chlorophenol; ethylphenol; parazon; tert.-butyl phenol; o-isopropyl phenol; o-sec-butyl phenol; to nonylphenol; to tert-octyl phenol; hydroxy-benzoic acid; phenol such as hydroxybenzoate are end-capping reagent; ε-Ji Neixianan; the 6-Valerolactim; butyrolactam; lactan such as azetidinone are end-capping reagent; formamidoxime; ethylidenehydroxylamine; acetoxime; methyl ethyl ketoxime; the diacetyl monoxime; diphenylketoxime; oximes such as cyclohexanone-oxime are end-capping reagent, and second is embraced imines; imines such as trimethylene imines are end-capping reagent etc.
In the present invention, with regard to the cooperation ratio of above-mentioned A composition and B composition, be necessary that making the total amount of A composition 95～70 weight parts (solid state component) and B composition 5～30 weight parts (solid state component) is 100 weight parts (solid state components).When the solid state component amount of B composition during less than 5 weight parts, when thermofixation, filming is not easy to solidify, and can not show film performance, and in addition, when this amount surpassed 30 weight parts, filming became really up to the mark, phenomenons such as crackle can occur.
And then in the present invention, representational embodiment by A composition and B composition manufacturing resin combination is as described below.Bisphenol A type epoxy resin or bisphenol F epoxy resin and polyfunctional amine (b) are dissolved in the selected solvent, under nitrogen environment, under 70～150 ℃, make its reaction 4～10 hours, make its high molecular, obtain resin solution (A composition).
On the other hand, modulate end-blocking isocyanic ester (B composition) as stated above separately.In the A composition, mix the B composition, use solvent cut to become about 3～50 pools, obtain resin combination.Wherein, the solvent that is used for the dilution of the dissolving of A composition and resin combination is the solvent of selecting according to condition (formula-1) (formula-2).
Inflation method as using selected solvent can adopt following method: at synthetic A composition and B composition under the solvent-free state and after mixing, it is dissolved in selected solvent and obtains the inflation method of resin solution; After the synthetic A composition, mix under the state in being dissolved in selected solvent, and directly or further add selected solvent and obtain the inflation method of resin solution with synthetic B composition under solvent-free state; Behind the synthetic B composition, be dissolved in synthetic A composition under the solvent-free state under the state in being dissolved in selected solvent, and directly or further add selected solvent and obtain the inflation method of resin solution; Under the state in being dissolved in selected solvent behind synthetic A composition and the B composition, directly or or further add selected solvent and obtain any inflation method such as inflation method of resin solution.
And then the solvent of Xuan Zeing is in the present invention, and the solid state component that is dissolved in the modified epoxy resin composition of this solvent is that 40% o'clock soltion viscosity is the following mixed solvent of 10000mPas.Even dissolve, if but surpass 10000mPas, even then carrying out coatingization by solvent cut is adjusted in the manipulable range of viscosities, when needs obtain the thick dry coating of number μ m～tens of μ m, still need repeatedly to repeat coating, sagging, depression perhaps appearred before baking-curing easily, and perhaps can residual a large amount of solvent in dry coating.
In the present invention, can adopt known method as the method for making coating.That is, in above-mentioned resin combination, add use behind rust-stabilising pigment, filler pigment, flow agent and the various additive dispersion machine, sand mill, ball mill etc. carry out mixing, disperse to get final product.In addition,, can utilize general methods such as brush applies, spraying, various coating machine coatings as coating method, be applied directly to the coating that obtains as described above on the starting material or coated pre-treatment after be coated on the starting material again.As adaptable starting material, can enumerate various raw material metals for example cold-rolled steel sheet, steel plate galvanized, alloy galvanized steel plate, chromium plating steel plate, Aludip, tin plate, lead-coated steel plate, Nickeled Steel Plate, aluminium sheet, titanium plate, stainless steel plate, raw materials for plastics production, inanimate matter starting material etc.
In addition, with after above-mentioned applying coating is to starting material, end-capping reagent in the B composition is dissociated make the regeneration of isocyanato-base, the hydroxyl in this regeneration isocyanato-base and the A composition formation cured coating film that reacts by heating.At this moment, Heating temperature is about 130～350 ℃ because of the differences such as kind of end-capping reagent, and its time is 20 seconds～tens of minutes in addition.
＜single component Air drying type coating resin 〉
In single component Air drying type coating resin, what used is to make the compound with phenol hydroxyl and Epicholorohydrin reacts and utilize polymeric amide, diprotic acid etc. to make the Resins, epoxy of its cross-linked polymerization after obtaining being rich in reactive epoxy group(ing) in the past.But, be difficult to obtain aspect its erosion resistance of filming or the solvent resistance and the same outstanding material of two-pack epoxy resin with the resin of this system.At first, in the modified epoxy of above-mentioned amine etc., when use had the multifunctional alkanol of primary hydroxyl, though raw-material adhesivity and solvent resistance are accessed improvement, wet fastness can variation, and erosion resistance is also abundant inadequately.In addition, when using the bigger Resins, epoxy of epoxy equivalent (weight), when perhaps increasing the molecular-weight average of modified epoxy, though can improve erosion resistance, wet fastness and solvent resistance, can variation to raw-material adhesivity.
The performance that aforesaid modified epoxy or its are filmed may depend primarily on character (covalency bonding force, wetting ability, polarity etc.) or its amount of the primary hydroxyl in this resin.That is, when the primary hydroxyl in the increase resin, the water on this resin and starting material surface forms covalent linkage, so can improve to raw-material adhesivity, but opposite, because of this resin is wetting ability, so can introduce outside water, cause this wet fastness of filming or erosion resistance to descend.And then, because this resin has polarity, thus be that so-called mutual solubility can descend to the solvability of organic solvent, but this solvent resistance of filming can raise.
Up to now, usually used velocity of evaporation suitably and the suitable aromatic series series solvent of velocity of evaporation that do not rise of the soltion viscosity after, the dissolving good as the part of mixed solvent with the mutual solubility of Resins, epoxy, be specially toluene or dimethylbenzene, control the velocity of evaporation of solvent thus or improved the mutual solubility of resin and mixed solvent, perhaps carried out lowering viscousity.Therefore, be the velocity of evaporation of the solvent that uses in the single component ambient cure coating resin at non-aromatic, satisfy 100≤V≤300 when representing with the velocity of evaporation shown in following (formula-3).Here the velocity of evaporation of Ding Yi solvent be to use be shown in Tanaka zhang it: the calculating formula of " coating and coating " No339, p45 (1981) " evaporation of solvent " calculates that the velocity of evaporation that converts to after the velocity of evaporation N-BUTYL ACETATE is made as 100 o'clock relative velocity of evaporation and the value that obtains.
(formula-3) V=∑ CiVi
Wherein, Ci (wet%): the content of selected solvent in whole solvents
Vi: the velocity of evaporation of selected solvent (is made as 100 with N-BUTYL ACETATE
The time speed of relative movement)
When V is in this scope, in dried coating, there is not dissolvent residual, so the rerum natura of filming does not worsen, in addition, solvent does not sharply disperse when dry, so appearance of film is not chapped, paint film defect etc. do not occur yet, so preferred.Preferred V is 150≤V≤250.
In addition, the SP value of (formula-1) is in the scope of 9.0≤SP≤11.0.When in this scope, good with the mutual solubility of modified epoxy, can obtain the stabilized uniform lacquer.Be preferably 9.50≤SP≤10.50.
At non-aromatic of the present invention is that the resin combination that uses in the single component ambient cure coating resin is effective in the following cases, promptly in the Resins, epoxy of specific epoxy equivalent (weight), cooperate nettedization agent with specific ratio, and agent is mainly used as nettedization is multifunctional alkanolamine, in addition, make the molecular weight of the amine-modified epoxy resin that obtains thus in specified range.
Promptly, the present invention is a kind of Air drying type coating resin composition, it is characterized in that, is that concentration below 60% is dissolved in the selected non-aromatic series solvent with modified epoxy with solid state component, wherein, the number-average molecular weight that described modified epoxy resin composition is obtained by the Resins, epoxy that makes epoxy equivalent (weight) 200～1000g/eq (a) and polyfunctional amine (b) addition is that 4000～10000 amine-modified epoxy resin constitutes, with respect to epoxy group(ing) 1.00 equivalents in (a) composition, (b) active hydrogen in the composition is 1.10～1.60 equivalents.
At first, to being used for Resins, epoxy of the present invention (a) and polyfunctional amine (b) describes.
In the present invention, Resins, epoxy (a) is meant bisphenol A diglycidyl ether, the Bisphenol F diglycidylether, the phenolic varnish glycidyl ether, hexahydrobenzene dioctyl phthalate glycidyl ester, the dimeracid glycidyl ester, the four glycidyl group aminodiphenylmethane, 3,4-epoxy-6-methylcyclohexyl methyl carboxylic acids ester, the triglycidyl group isocyanuric acid ester, 3,4-epoxycyclohexyl methyl carboxylic acids ester, polypropylene glycol diglycidyl ether, two terminal diglycidylether modifiers of polyhutadiene or polysulphide etc., preferred bisphenol A diglycidyl ether, the Bisphenol F diglycidylether.They can use more than a kind or 2 kinds.
In addition, this epoxy equivalent (weight) is in the scope of 200～1000g/eq, preferably in the scope of 450～1000g/eq.When in this scope, the mutual solubility of the resin solution that obtains, the erosion resistance of filming, solvent resistance, adhesivity are good, therefore preferred.
In the present invention, polyfunctional amine (b) is the amine that has 2 above active hydrogens in 1 molecule, and they can be divided into multifunctional alkanolamine (b1) and polyfunctional amine in addition (b2).As the former multifunctional alkanolamine (b1), can enumerate Yi Bingchunan, single Propanolamine, only son's hydramine, monoethanolamine, 2-N-aminoethyl ethanolamine etc., wherein, preferred monoethanolamine.In addition, as the polyfunctional amine (b2) outside the latter (b1), can enumerate Diethylenetriaminee (DETA), Edamine, butylamine, propylamine, isophorone diamine, benzene dimethylamine, diaminodiphenylmethane, diamino sulfone, octylame, mphenylenediamine, butylamine, amylamine, hexylamine, octylame, nonyl amine, decyl amine, triethylenetetramine, TEPA, diethylaminopropylamine, N-aminoethyl piperazine, mencene diamine, diamino diphenyl sulfone etc.
In the present invention, can only use above-mentioned multifunctional alkanolamine (b1) separately as polyfunctional amine (b), perhaps can and with (b1) with the polyfunctional amine (b2) (b1), preferably only select in the multifunctional alkanolamine (b1) one or more for use.In addition, when and with multifunctional alkanolamine (b1) with during the polyfunctional amine (b2) (b1), the equivalence ratio of their composition is preferably 0.70～1.00/0～0.30 (two kinds of compositions add up to 1.00 equivalents).When this equivalence ratio was 0～0.70/0.30～1.00, the erosion resistance of filming that obtains can variation, in addition, and its solvent resistance or raw-material adhesivity also had a declining tendency.
In the present invention, need cooperate above-mentioned Resins, epoxy (a) and polyfunctional amine (b), and the molecular weight that makes the amine-modified epoxy resin that obtains is in specific scope with specific equivalence ratio.(a) composition and (b) use level of composition be that with respect to 1.00 equivalent epoxy group(ing) in (a) composition, (b) active hydrogen in the composition is in 1.10～1.60 normal scopes, preferably in 1.10～1.40 normal scopes.When in this scope, from the gelation of resin solution, and viewpoint such as water tolerance preferred.In addition, the number-average molecular weight of amine-modified epoxy resin is in 4000～10000 scope.When this molecular weight less than 4000 the time, filming of obtaining can hardening, its workability or shock-resistance can variation.When surpassing 10000, the primary hydroxyl deficiency in the resin that obtains can variation to raw-material adhesivity so film.
In the present invention, in order to make this amine-modified epoxy resin, (a) is dissolved in the solvent with Resins, epoxy, and in this solution, add polyfunctional amine (b) afterwards, under nitrogen environment, under 70～150 ℃, make it to take place addition reaction in 4～10 hours, to finish high molecular, with selected solvent with its be diluted to viscosity be 5～70 the pool about solution, thereby obtain resin solution.These resin solutions that obtain can by and adjust with diluting solvent, this diluting solvent is as the solvent that adds in order to improve operability and appearance of film and selected.
And then the solvent of Xuan Zeing is in the present invention, and the solid state component that is dissolved in the modified epoxy resin composition of this solvent is that 40% o'clock soltion viscosity is the following mixed solvent of 10000mPas.Even can dissolve, when the soltion viscosity when the solid state component of modified epoxy resin composition is 40% surpasses 10000mPas, be adjusted to manipulable range of viscosities even carry out coatingization by solvent cut, if will obtain the dry coating of number μ m～tens of μ m, still need repeatedly to repeat coating, sagging, depression perhaps appearred easily before baking-curing, perhaps can be in dry coating residual a large amount of solvent.
In the present invention, for the solvent that improves the operable operability of filming and appearance of film and add, be according to condition (iv-1): the non-aromatic that contains the pimelinketone of 20wt% in solvent at least is the solvent that mixed solvent is selected, and preferably according to condition (iv-2): the non-aromatic that contains the pimelinketone of 40wt% in solvent at least is the non-aromatic series solvent that mixed solvent is selected.When the content of the pimelinketone in the mixed solvent during less than 20wt%, after mixing, can occur separating with resin solution, perhaps muddiness can appear in resin solution, can't obtain the stabilized resins composition.Adjust the thinner of usefulness before these solvents can be made as coating, also can be used as the thinner of adjusting usefulness after the thinner of coating in making, the coating manufacturing and use.
In the present invention, in the manufacturing of coating, can adopt known method, that is, in above-mentioned resin combination, add use behind rust-stabilising pigment, filler pigment, flow agent and the various additive dispersion machine, sand mill, ball mill etc. carry out mixing, disperse to get final product.In addition,, can utilize general methods such as brush applies, spraying, various coating machine coatings as coating method, be applied directly to the coating that obtains as described above on the starting material or coated pre-treatment after be coated on the starting material again.As adaptable starting material, can enumerate various raw material metals for example cold-rolled steel sheet, steel plate galvanized, alloy galvanized steel plate, chromium plating steel plate, Aludip, tin plate, lead-coated steel plate, Nickeled Steel Plate, aluminium sheet, titanium plate, stainless steel plate, raw materials for plastics production, inanimate matter starting material etc.
According to the present invention, can provide raw-material adhesivity, solidity to corrosion, workability, scuff resistance and solvent resistance etc. are obtained equilibrated Nonaromatic solvent type coating resin combination between these performances remarkably and.
Embodiment
Below, describe the present invention in detail by Production Example, embodiment, comparative example.In following, " part " and " % " is benchmark with weight, and in addition, (b) polyfunctional amine in the composition and partial solvent are represented with following abbreviation.
IPA: Yi Bingchunan
IPA: Virahol
MEA: monoethanolamine
PA: propylamine
BA: butylamine
MBA: only son's hydramine
N-BA: propyl carbinol
PMA: propylene glycol monomethyl ether acetate
MA (methoxy acetate): 3-methoxyacetic acid ester
MEK: methyl ethyl ketone
MCH: methylcyclohexane
PM: propylene glycol monomethyl ether
Sec-BuOH: sec-butyl alcohol
N-BA: propyl carbinol
PEAC: propylene glycol monoethyl ether acetate
Also have, (a) kind of the Resins, epoxy of composition is represented with following abbreviation.
BP-A: bisphenol A diglycidyl ether is a Resins, epoxy
BP-F: the Bisphenol F diglycidylether is a Resins, epoxy
＜molecular weight measurement method 〉
The modified epoxy that to make in Production Example is dissolved in tetrahydrofuran (THF), uses clear and electrician's corporate system " Shodex GPC-101 ", by comparing with the known polystyrene of molecular weight, adopts the RI method to measure molecular weight.
The film method of rerum natura of evaluation is as follows.
＜the evaluation of physical property of filming 〉
(1) resin outward appearance: at preceding half section of Production Example, synthetic epoxy resin solution (solid state component 40%) is put in the vial with cover of 100cc, preserves 24 hours visual observation resin outward appearance in 25 ℃ thermostatic chamber.
Zero ... transparent, * ... exist and become muddiness, resin and separated from solvent, gelation etc. unusually.
(2) resin viscosity:, use Brookfield viscometers that synthetic epoxy resin solution (solid state component 40%) is carried out viscosity measurement down at 25 ℃ according to JIS-K-6901 preceding half section of Production Example.
(3) erosion resistance: with cutting out the cruciform otch on the cutting knife test board face, until arriving the starting material face.Brine spray laboratory method with JIS-Z-2371 is a benchmark, and this test board is carried out test in 1000 hours.Subsequently, peel off otch, measure filming of this moment and peel off width, divide 5 level evaluation erosion resistances with self adhesive tape (ニ チ バ Application corporate system).
◎ ... 0～less than 1mm, zero ... 1～less than 2mm, △ ... 2～less than 3mm, * ... 3～less than 5mm, * * ... more than the 5mm.
(4) wet fastness: moistening trier (49 ℃ * put into test board in 98%RH) were placed 1000 hours.Subsequently, the bubble of visual observation coated surface produces state, divides 5 level evaluation wet fastnesss.
◎ ... no abnormal, zero ... 1～5, △ ... 5～10, * ... 10～20, * * ... bubble appears comprehensively.
(5) workability: make coated surface be positioned at the crooked test board in back, the outside, the resistivity of the crackle that the difference by the top and following extensibility of filming of research generation this moment causes.Peel off curved part with self adhesive tape (ニ チ バ Application corporate system), the visual observation state of peeling off at this moment divides 5 level evaluation workabilitys.
◎ ... do not peel off zero fully ... peel off △ a little ... peel off about 1/3, * ... over half peeling off, * * ... almost all peel off.
(6) scratch property: with 45 ° angles untapped coin is pressed on the coated surface, in face of firmly moving to.Visual observation remains in the state of the damage on the coated surface at this moment, divides 5 level evaluation scratch property.
◎ ... not damage, zero ... damage is arranged slightly, △ ... be damaged to undercoat, * ... be damaged to a raw-material part, * * ... film and peel off, starting material sustain damage.
(7) shock-resistance: use the shock-produced deformation trier of JIS-K-5400.6.13.3B method, the test impact.Punch die uses the mould of radius as 6.35mm * 0.03mm, and the coated surface that makes test board is clipped in therebetween down.(quality 1000 ± 1g) drops on the punch die from the height of 50cm, and the collapse state that visual observation is filmed divides 5 level evaluation shock-resistance to make sliding weight of steelyard.
◎ ... not unusual, zero ... crackle is arranged a little, △ ... integral body all has crackle, * ... part is peeled off, * * ... peel off comprehensively.
(8) pencil hardness: the pencil test with JIS-K-5400.6.14 is a benchmark, the hardness of filming of evaluation test plate.
(9) adhesivity: the netted line test with JIS-K-5400.6.15 is a benchmark, divides the adhesivity of filming of 5 level evaluation test boards.
◎ ... 100/100, zero ... 99/100～80/100, △ ... 79/100～50/100, * ... 49/100～30/100, * * ... below 29/100.
Production Example 1～7 (manufacturing of mixed solvent)
Obtain mixed solvent according to (weight %) mixed solvent of the ratio shown in the table 1.
Table-1 (mixed solvent manufacturing prescription)
| The solvent name | Velocity of evaporation (Vi) | Sp value (SPi) | Production Example 1 | Production Example 2 | Production Example 3 | Production Example 4 | Production Example 5 | Production Example 6 | Production Example 7 |
| PMA | 34 | 9.2 | 5 | 30 | 15 | 5 | 5 | 5 | |
| N-BUTYL ACETATE | 100 | 8.5 | 30 | ||||||
| Pimelinketone | 25 | 9.9 | 35 | 30 | 15 | 10 | 5 | 5 | |
| n-BA | 45 | 11.4 | 20 | 25 | 25 | 30 | 85 | ||
| MA | 15 | 8.9 | 10 | 13 | 15 | 5 | 85 | 30 | 5 |
| Vinyl acetic monomer | 525 | 9.1 | 30 | 5 | |||||
| PM | 66 | 10.2 | 30 | ||||||
| MEK | 465 | 9.3 | 30 | ||||||
| MCH | 320 | 8.2 | 30 | ||||||
| PEAC | 30 | ||||||||
| The rerum natura of mixed solvent | Velocity of evaporation (V) | 51.0 | 30.9 | 42.2 | 313.0 | 17.0 | 134.6 | 42.0 | |
| Sp value (SP) | 9.6 | 9.7 | 10.1 | 9.8 | 9.0 | 8.7 | 11.1 | ||
Production Example 8 (manufacturing of end-blocking isocyanic ester)
Make 2,4-tolylene diisocyanate and polypropylene glycol (number-average molecular weight 2000) react and carry out urethane, with ε-Ji Neixianan the isocyanato-base carry out end-blockingization, it is dissolved in the mixed solvent shown in the table 1, modulation end-blocking isocyanic ester (solid state component 70%).
Production Example 9 (manufacturing of modified epoxy resin composition)
In glass four-hole boiling flask (band stirrer, thermometer, external heater, cooling tube, condenser and nitrogen ingress pipe), put into 1200 parts of the mixed solvents shown in the table 1, and-2 put into 1000 parts of bisphenol A type epoxy resins (epoxy equivalent (weight) 1000g/eq), dissolving according to table.
In this solution, add 67 parts of iPA (Ahew 37.5g/eq), under 100 ℃, make its reaction 5 hours.After the reaction, be cooled to below 60 ℃, the mixed solvent shown in the interpolation table 1 dilutes for 400 parts, obtains solid state component and be 40% resin solution.Afterwards, add 217 parts of the mixed solvents shown in the table 1 again, making solid state component is 37%, is blended in 337 parts of the end-blocking isocyanic ester (solid state component 70%) that obtain in the above-mentioned Production Example, obtains solid state component and be 40% resin combination.
Then, in 200 parts of each resin combinations, cooperate titanium oxide (R-920: trade(brand)name as pigment, Du Pont's system) 72 parts and strontium yellow (Kikuchi pigment industrial system) are 24 parts, use sand mill to carry out mixing, dispersion, the mixed solvent shown in the interpolation table-1 dilutes for 60 parts, obtains coating.At this moment, the total amount of pigment and the ratio of the solid state component in the resin combination are the 1.2/1.0 weight ratio, the ratio of titanium oxide and strontium yellow is 75/25 weight ratio, and in addition, the amount of adjusting solvent is so that the viscosity of the coating that obtains is 90～110 seconds (Ford cup: Ford cup#4).
Production Example 10～15 is also carried out according to table, below identical.
Table-2 (Resins, epoxy manufacturing prescriptions)
| Production Example | 9 | 10 | 11 | 12 | 13 | 14 | 15 |
| (a) Resins, epoxy epoxy equivalent (weight) (g/eq) amount (part) | BP-A 1000 1000 | BP-F 1000 1000 | BP-A 2500 1000 | BP-F 2500 1000 | BP-A 400 1000 | BP-A 1000 1000 | BP-F 1000 1000 |
| (b) polyfunctional amine Ahew (g/eq) amount (part) | IPA 37.5 67 | PA 29.5 53 | MEA 30.5 21.4 | BA 36.5 18.3 | iPA 37.5 140 | iPA 37.5 72 | PA 29.5 30.7 |
| (b) epoxy group(ing) in the composition of the active hydrogen in the composition/(a) | 1.79 | 1.80 | 1.75 | 1.25 | 1.49 | 1.92 | 1.04 |
Embodiment 1
Be coated with machine with rod this applying coating is handled on the steel plate (150mm * 70mm * 0.8mm is thick) at zinc phosphate, its thickness adjustment is become 5 μ m.In addition, being coated with machine with rod, commercially available coiled material is coated with that application coating carries out surface applied and make its thickness is 15 μ m.After the coating, be that 210 ℃ * 45 seconds, surface applied are to carry out this steel plate of baking-curing under 210 ℃ * 60 seconds the condition to carry out drying in primary coat, as test board.Estimate the rerum natura of filming of this test board by above-mentioned method, they the results are shown in table 3.
Embodiment 2～9, comparative example 1～9
Use the mixed solvent shown in the table 1, change kind, the amount of each composition as shown in table 2ly, in addition, operate identically, obtain resin combination (Production Example 10～15) respectively with Production Example 9.Then, except using these resin combinations, operate identically, obtain coating, and then obtain test board, they are estimated with embodiment 1.It the results are shown in table 3 and table 4.
Table-3 (embodiment)
| Embodiment | ||||||||||
| 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | ||
| The mixed solvent Production Example | 1 | 1 | 1 | 1 | 1 | 2 | 2 | 3 | 3 | |
| The Resins, epoxy Production Example | 9 | 10 | 11 | 12 | 13 | 9 | 10 | 11 | 12 | |
| A composition/B composition (solid state component weight ratio) | 85/15 | 85/15 | 85/15 | 85/15 | 85/15 | 85/15 | 87/13 | 90/10 | 75/25 | |
| The evaluation result of filming | The resin outward appearance | Well | Well | Well | Well | Well | Well | Well | Well | Well |
| Resin viscosity (mPas) | 1000 | 700 | 1100 | 800 | 1000 | 900 | 600 | 800 | 900 | |
| Erosion resistance | ◎ | ◎ | ◎ | ◎ | ○ | ◎ | ○ | ◎ | ○ | |
| Wet fastness | ◎ | ◎ | ◎ | ◎ | ◎ | ◎ | ◎ | ◎ | ◎ | |
| Workability | ◎ | ○ | ◎ | ○ | ○ | ◎ | ○ | ◎ | ○ | |
| Scratch property | ○ | ◎ | ○ | ○ | ◎ | ○ | ○ | ○ | ◎ | |
| Shock-resistance | ◎ | ◎ | ◎ | ○ | ○ | ◎ | ◎ | ◎ | ○ | |
| Pencil hardness | 2H | 2H | 2H | 2H | 2H | 2H | 2H | 2H | 2H | |
| Adhesivity | ◎ | ◎ | ◎ | ◎ | ◎ | ◎ | ◎ | ◎ | ◎ | |
Table-4 (comparative examples)
| Comparative example | ||||||||||
| 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | ||
| The mixed solvent Production Example | 4 | 5 | 6 | 7 | 1 | 1 | 1 | 1 | 1 | |
| The Resins, epoxy Production Example | 9 | 9 | 9 | 9 | 14 | 15 | 9 | 9 | 9 | |
| A composition/B composition (solid state component weight ratio) | 85/15 | 85/15 | 85/15 | 85/15 | 85/15 | 85/15 | 65/35 | 96/4 | 100/0 | |
| The evaluation result of filming | The resin outward appearance | Well | Well | Separate | Separate | Gel | Gelation | Well | Well | Well |
| Resin viscosity (mPas) | 500 | 600 | Immeasurability | Immeasurability | 600 | 1000 | 600 | |||
| Erosion resistance | × | × | Can not estimate | Can not estimate | Can not estimate | Can not estimate | ×× | ○ | △ | |
| Wet fastness | ○ | × | ×× | ○ | × | |||||
| Workability | × | ○ | ○ | ×× | ×× | |||||
| Scratch property | × | × | ×× | △ | × | |||||
| Shock-resistance | ○ | ○ | △ | × | △ | |||||
| Pencil hardness | B | B | B | 2H | 2H | |||||
| Adhesivity | △ | △ | △ | ○ | ○ | |||||
Production Example 16～23 (manufacturing of mixed solvent)
Obtain mixed solvent according to (weight %) mixed solvent of the ratio shown in the table 5.
Table-5 (mixed solvent manufacturing prescriptions)
| The solvent name | Velocity of evaporation (Vi) | Sp value (SPi) | Production Example 16 | Production Example 17 | Production Example 18 | Production Example 19 | Production Example 20 | Production Example 21 | Production Example 22 | Production Example 23 |
| PMA | 34 | 9.2 | 15 | 15 | 15 | 15 | 55 | 10 | 15 | |
| N-BUTYL ACETATE | 100 | 8.5 | 5 | 20 | ||||||
| n-BA | 45 | 11.4 | 40 | |||||||
| MA | 15 | 8.9 | 5 | 5 | 10 | |||||
| Vinyl acetic monomer | 525 | 9.1 | 30 | 25 | 30 | 30 | 5 | 50 | 5 | |
| PM | 66 | 10.2 | 30 | 20 | 25 | 15 | 20 | |||
| sec-BuOH | 115 | 10.8 | 20 | 15 | 20 | 15 | 10 | 5 | ||
| Isobutyl acetate | 152 | 8.3 | 20 | 5 | 20 | 5 | 10 | 20 | ||
| PEAC | 22 | 8.6 | 5 | 5 | 5 | 20 | ||||
| IPA | 205 | 11.5 | 5 | 45 | ||||||
| MEK | 465 | 9.3 | 20 | |||||||
| MCH | 320 | 8.2 | 10 | 10 | ||||||
| The rerum natura of mixed solvent | Velocity of evaporation (V) | 206 | 198 | 211 | 221 | 78 | 418 | 119 | 120 | |
| Sp value (SP) | 9.78 | 9.42 | 9.67 | 9.35 | 9.48 | 9.18 | 11.1 | 8.63 | ||
Production Example 24,25 (manufacturing of diluting solvent)
Obtain mixed solvent according to (weight %) mixed solvent of the ratio shown in the table 6.
Table 6 (diluting solvent manufacturing prescription)
| The solvent name | Production Example 24 | Production Example 25 |
| Pimelinketone | 50 | 10 |
| Vinyl acetic monomer | 50 | 90 |
Production Example 26 (manufacturing of modified epoxy)
At glass four-hole boiling flask (band stirrer, thermometer, external heater, cooling tube, condenser and nitrogen ingress pipe) in, put into 1000 parts of BP-A (epoxy equivalent (weight) 450g/eq), add selected mixed solvent (table 5, Production Example 16) 1000 parts dissolve, after the reflux dewatering, add i-PA95 part, it was reacted 5 hours down at 100 ℃, after the reaction, be cooled to below 60 ℃, add selected mixed solvent (table 5, Production Example 16) and dilute for 500 parts, obtain number-average molecular weight and be 7000 and solid state component be 40%, viscosity is the resin solution of 30 pools.Then, in 200 parts of this resin solutions, cooperate titanium oxide (R-920: trade(brand)name, Du Pont's system) 60 parts, 20 parts in phospho-molybdic acid aluminium (Kikuchi pigment industrial system) and selected mixed solvent (table 6, Production Example 24), use sand mill to carry out mixing, dispersion, obtaining viscosity is 90～110 seconds (Ford cup: coating Fordcup#4).
Production Example 27～32 is also carried out according to table, below identical.
Table-7 (Resins, epoxy manufacturing prescriptions)
| Production Example | Production Example 26 | Production Example 27 | Production Example 28 | Production Example 29 | Production Example 30 | Production Example 31 | Production Example 32 | ||
| A Resins, epoxy | BP-A BP-F epoxy equivalent (weight) (g/eq) | 1000 - 450 | - 1000 450 | 1000 - 650 | - 1000 650 | 1000 - 650 | - 1000 550 | 1000 - 550 | |
| The b polyfunctional amine | b1 | I-PA MEA Ahew (g/eq) | 95 - 37.5 | 79 - 37.5 | - 43 30.5 | - 58 30.5 | - 40 30.5 | - 50 30.5 | 1300 - 37.5 |
| b2 | PA BA Ahew (g/eq) | - - - | 12 - 29.5 | - 43 30.5 | - - - | - 26 36.5 | 5 - 29.5 | - - - | |
| B1 composition/b2 composition (equivalence ratio) | 1.0 | 0.84/ 0.16 | 0.80/ 0.20 | 1.0 | 0.65/ 0.35 | 0.91/ 0.09 | 1.0 | ||
| Epoxy group(ing) (equivalence ratio) in active hydrogen in the b composition/a composition | 1.14 | 1.13 | 1.15 | 1.23 | 1.29 | 1.00 | 1.70 | ||
| The number-average molecular weight of amine-modified epoxy resin | 7000 | 7000 | 9000 | 6000 | 9000 | Gelation | 8500 | ||
Embodiment 10
With the aerial spraying machine this applying coating is handled on the steel plate (150mm * 70mm * 0.8mm is thick) at zinc phosphate, its thickness adjustment is become 20 μ m.After the coating, steel plate was placed 7 days down at 20 ℃, made its drying, as test board.Estimate the rerum natura of filming of this test board by above-mentioned method, they the results are shown in table 8.
Embodiment 11～19, comparative example 10～19
In Production Example 26, use the mixed solvent shown in the table 5, dilute with the mixed solvent shown in the table 6, change kind, the amount of each composition as shown in table 7ly, in addition, other operations are identical, obtain resin combination respectively.Then, in the second half section of Production Example 26, except using these resin combinations, other operations are identical, obtain coating, and then obtain test board, and they are estimated.It the results are shown in table 8 and table 9.
Table-8 (embodiment)
| Embodiment | |||||||||||
| 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | ||
| The mixed solvent Production Example | 1 | 1 | 1 | 1 | 1 | 1 | 2 | 2 | 3 | 4 | |
| The diluting solvent Production Example | - | 9 | - | 9 | - | - | - | 9 | - | - | |
| The Resins, epoxy Production Example | 11 | 11 | 12 | 12 | 13 | 14 | 11 | 11 | 11 | 11 | |
| The evaluation result of filming | The resin outward appearance | Well | Well | Well | Well | Well | Well | Well | Well | Well | Well |
| Resin viscosity (mPas) | 3000 | 2500 | 2700 | 2200 | 3300 | 2800 | 2900 | 2300 | 3100 | 3000 | |
| Erosion resistance | ◎ | ◎ | ◎ | ◎ | ◎ | ◎ | ◎ | ◎ | ◎ | ◎ | |
| Wet fastness | ◎ | ◎ | ◎ | ◎ | ◎ | ◎ | ◎ | ◎ | ◎ | ◎ | |
| Workability | ◎ | ◎ | ◎ | ◎ | ◎ | ◎ | ◎ | ◎ | ◎ | ◎ | |
| Scratch property | ○ | ○ | ○ | ○ | ○ | ○ | ○ | ○ | ○ | ○ | |
| Shock-resistance | ◎ | ◎ | ◎ | ◎ | ○ | ○ | ○ | ○ | ◎ | ◎ | |
| Pencil hardness | 2H | 2H | 2H | 2H | H | H | 2H | 2H | 2H | 2H | |
| Adhesivity | ○ | ○ | ○ | ○ | ○ | ○ | ○ | ○ | ○ | ○ | |
Table-9 (comparative examples)
| Comparative example | |||||||||||
| 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | ||
| The mixed solvent Production Example | 5 | 5 | 6 | 7 | 8 | 1 | 2 | 1 | 1 | 1 | |
| The diluting solvent Production Example | - | 10 | - | - | - | 10 | 10 | - | - | - | |
| The Resins, epoxy Production Example | 11 | 11 | 11 | 11 | 11 | 11 | 11 | 15 | 16 | 17 | |
| The evaluation result of filming | The resin outward appearance | Well | The muddy separation | Well | Separate | Separate | The muddy separation | The muddy separation | Well | The gelation immeasurability | Well |
| Resin viscosity (mPas) | 10000 | Immeasurability | 2700 | Immeasurability | Immeasurability | Immeasurability | Immeasurability | 2300 | 3000 | ||
| Erosion resistance | ×× | ×× | ×× | △ | |||||||
| Wet fastness | ×× | × | × | ×× | |||||||
| Workability | △ | ◎ | × | △ | |||||||
| Scratch property | × | ○ | × | △ | |||||||
| Shock-resistance | △ | ◎ | × | △ | |||||||
| Pencil hardness | H | 2H | H | H | |||||||
| Adhesivity | ×× | ○ | × | ◎ | |||||||
Claims (7)
1. a Nonaromatic solvent type modified epoxy coating resin composition is characterized in that, is that concentration below 60% is dissolved in the non-aromatic series solvent of selecting according to condition (i) with resin combination with solid state component,
Condition (i): be a kind of mixed solvent, selected solvent all is a non-aromatic system, and satisfies following (formula-1), and the solid state component that is dissolved in the modified epoxy resin composition of this solvent is that 40% o'clock soltion viscosity is below the 10000mPas,
(formula-1) SP=∑ CiSPi is 9.0≤SP≤11.0
Wherein, Ci (wet%): the content of selected solvent in whole solvents,
SPi: the SP value of selected solvent.
2. single component thermo-setting coating resin composition, it is characterized in that, in claim 1, mix the B composition of the A composition of 95～70 weight parts (solid state component) and 5～30 weight parts (solid state component) and make its total amount reach 100 weight parts (solid state component), and be that concentration below 60% is dissolved in the non-aromatic series solvent of (ii) selecting according to condition with solid state component with it
The A composition: be a kind of modified epoxy resin composition, contain Resins, epoxy that epoxy equivalent (weight) is 300～3000g/eq (a) and polyfunctional amine (b), with respect to epoxy equivalent (weight) 1.0 equivalents in (a) composition, (b) active hydrogen in the composition is 1.10～1.80 equivalents,
The B composition: the end-blocking isocyanic ester,
Condition is (ii): selected solvent all is a non-aromatic, and satisfies following (formula-2),
(formula-2) V=∑ CiVi is 18≤V≤100
Wherein, Ci (wet%): the content of selected solvent in whole solvents,
Vi: the velocity of evaporation of selected solvent (is made as 100 with N-BUTYL ACETATE
The time speed of relative movement).
3. Air drying type coating resin composition, it is characterized in that, in claim 1, modified epoxy resin composition satisfies condition, (iii), wherein, described modified epoxy resin composition is the Resins, epoxy of 200～1000g/eq by making epoxy equivalent (weight), (a) and polyfunctional amine, (b) carry out addition and the number-average molecular weight that obtains to be 4000～10000 amine-modified epoxy resin form, and with respect to, (a) 1.00 equivalents of the epoxy group(ing) in the composition, (b) active hydrogen in the composition is 1.10～1.60 equivalents
Condition is (iii): selected solvent all is a non-aromatic, satisfies following (formula-3),
(formula-3) V=∑ CiVi is 100≤V≤300
Wherein, Ci (wet%): the content of selected solvent in whole solvents,
Vi: the velocity of evaporation of selected solvent (is made as 100 with N-BUTYL ACETATE
The time speed of relative movement).
4. Air drying type coating resin composition as claimed in claim 3 is characterized in that, polyfunctional amine (b) is multifunctional alkanolamine (b1).
5. as claim 3 or 4 described Air drying type coating resin compositions, it is characterized in that,
Polyfunctional amine (b) is the mixture of multifunctional alkanolamine (b1) and polyfunctional amine in addition (b2), and the equivalence ratio of these compositions is 0.70～1.00/0～0.30 (total amount of two kinds of compositions is 1.00 equivalents).
6. as any described single component thermo-setting coating resin composition or Air drying type coating resin composition in the claim 2～5, it is characterized in that,
Resins, epoxy (a) is bisphenol A diglycidyl ether or Bisphenol F diglycidylether.
7. an Air drying type coating resin composition is characterized in that,
And with Air drying type coating resin composition described in the claim 3～6 and the diluting solvent selected according to condition (iv-1) as adding the solvent in this Air drying type coating resin composition to,
Condition (iv-1): in solvent, contain the pimelinketone of 20wt% at least.
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| JPH08183834A (en) * | 1994-12-28 | 1996-07-16 | Dainippon Ink & Chem Inc | Self-curing epoxy resin composition |
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| WO2016188369A1 (en) * | 2015-05-22 | 2016-12-01 | Ppg涂料(天津)有限公司 | Single-component high-anticorrosion quick-drying epoxy coating composition |
| AU2016269294B2 (en) * | 2015-05-22 | 2019-02-14 | Ppg Coatings (Tianjin) Co., Ltd. | Single-component high-anticorrosion quick-drying epoxy coating composition |
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