JPS62236812A - Moisture-curable composition - Google Patents
Moisture-curable compositionInfo
- Publication number
- JPS62236812A JPS62236812A JP8144186A JP8144186A JPS62236812A JP S62236812 A JPS62236812 A JP S62236812A JP 8144186 A JP8144186 A JP 8144186A JP 8144186 A JP8144186 A JP 8144186A JP S62236812 A JPS62236812 A JP S62236812A
- Authority
- JP
- Japan
- Prior art keywords
- meth
- compound
- ketone
- ketimine
- group
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 150000004658 ketimines Chemical group 0.000 claims abstract description 20
- 229920000768 polyamine Polymers 0.000 claims abstract description 17
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims abstract description 14
- 150000002576 ketones Chemical class 0.000 claims abstract description 9
- 238000013008 moisture curing Methods 0.000 claims 1
- 229920005862 polyol Polymers 0.000 abstract description 10
- 150000003077 polyols Chemical class 0.000 abstract description 10
- -1 aliphatic diamine Chemical class 0.000 abstract description 7
- 238000002156 mixing Methods 0.000 abstract description 6
- 229920000058 polyacrylate Polymers 0.000 abstract description 6
- 229920000728 polyester Polymers 0.000 abstract description 5
- 125000002723 alicyclic group Chemical group 0.000 abstract description 2
- 238000006297 dehydration reaction Methods 0.000 abstract description 2
- 229920000193 polymethacrylate Polymers 0.000 description 16
- 238000000576 coating method Methods 0.000 description 15
- 239000011248 coating agent Substances 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 239000004593 Epoxy Substances 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 7
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 150000005846 sugar alcohols Polymers 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 150000007513 acids 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
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000005187 foaming Methods 0.000 description 5
- 229920000647 polyepoxide Polymers 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- 229920002635 polyurethane Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical class NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 230000008719 thickening Effects 0.000 description 3
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241000238557 Decapoda Species 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229910001209 Low-carbon steel Inorganic materials 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000003944 halohydrins Chemical class 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-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
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000004570 mortar (masonry) Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
- 239000000758 substrate Substances 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
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 1
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- 241001082241 Lythrum hyssopifolia Species 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- XXKOQQBKBHUATC-UHFFFAOYSA-N cyclohexylmethylcyclohexane Chemical compound C1CCCCC1CC1CCCCC1 XXKOQQBKBHUATC-UHFFFAOYSA-N 0.000 description 1
- 229940075894 denatured ethanol Drugs 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000009413 insulation Methods 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
- 239000005453 ketone based solvent Substances 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
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint 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
- 150000002989 phenols Chemical class 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は湿気硬化性組成物に関する。[Detailed description of the invention] [Industrial application field] The present invention relates to moisture curable compositions.
従来、湿気硬化性組成物としては遊離“イソシアネート
基を含有したー液性ウレタン塗料が使用されている。Conventionally, liquid urethane paints containing free isocyanate groups have been used as moisture-curable compositions.
しかしこのものは、硬化する時炭酸ガスが発生するため
、特に高湿度の環境下では厚膜が得られない問題点があ
った。However, this method has the problem that a thick film cannot be obtained especially in a high humidity environment because carbon dioxide gas is generated during curing.
本発明者らは高湿度の環境下でも発泡のない厚膜が得ら
れる湿気硬化性組成物について研究を重ねた結果、本発
明に到達した。The present inventors have conducted extensive research on moisture-curable compositions that can form thick films without foaming even in high-humidity environments, and have thus arrived at the present invention.
すなわち、本発明は分子中にすくなくとも２個の（メタ
）アクリロイル基を持つ多官能化合物（Ｂ）およびポリ
アミンとケトン類からのケチミン基を含有する化合物（
６）とから成ることを特徴とする湿気硬化性組成物であ
る。That is, the present invention provides polyfunctional compounds (B) having at least two (meth)acryloyl groups in the molecule and compounds containing ketimine groups from polyamines and ketones (
6) A moisture-curable composition comprising:
分子中にすくなくとも２個の（メタ）アクリロイル基（
アクリロイル基および／またはメタクリロイル基をいう
。以下同様の記載を用いる）を持つ多官能化合物（Ｂ）
としては次に記すものがあげられる。At least two (meth)acryloyl groups in the molecule (
Refers to an acryloyl group and/or a methacryloyl group. Polyfunctional compound (B) with the same description below)
Examples include the following:
（１）ポリオールポリ（メタ）アクリレート；多価アル
コール（エチレングリコール、プロピ、レンゲリコール
、ネオペンチルグリコール、ヘキサンジオール、グリセ
リン、トリメチロールプロパン。(1) Polyol poly(meth)acrylate; polyhydric alcohol (ethylene glycol, propylene glycol, neopentyl glycol, hexanediol, glycerin, trimethylolpropane).
ペンタエリスリトール、ソルビトール、およびポリブタ
ジェンポリオールなどのポリオールなど）と（メタ）ア
クリル酸とのポリ（メタ）アクリレート。Poly(meth)acrylates with (meth)acrylic acid (such as polyols such as pentaerythritol, sorbitol, and polybutadiene polyols) and (meth)acrylic acid.
（２）ポリエーテルポリ（メタ）アクリレート；ポリエ
ーテルポリオール〔ポリエチレングリコール。(2) Polyether poly(meth)acrylate; polyether polyol [polyethylene glycol.
ポリプロピレングリコール、ポリテトラメチレングリコ
ール、ビスフェノールＡのアルキレンオキサイド（エチ
レンオキサイド、プロピレンオキサイドなど）付加物、
前記（１）の項で例示した多価アルコールのアルキレン
オキサイド付加物など〕のポリ（メタ）アクリレート。Polypropylene glycol, polytetramethylene glycol, alkylene oxide (ethylene oxide, propylene oxide, etc.) adducts of bisphenol A,
Poly(meth)acrylates such as alkylene oxide adducts of polyhydric alcohols exemplified in the above (1).
（３）ポリエステルポリ（メタ）アクリレート；ポリカ
ルボン酸（マレイン酸、コハク酸、グルタル酸、アジピ
ン酸、フタル酸、テレフタル酸、イソフタル酸、テトラ
ヒドロフタル酸、ヘキサヒドロフタル酸、トリメリット
酸、ピロメリット酸など）と前記（１）または／および
前記（２）で例示の多価アルコールまたは／およびポリ
エーテルポリオールとのポリエステルポリオールおよび
ω−カプロラクトン、ω−ヒドロキシカルボン酸などの
重合により得られるポリエステルポリオールと（メタ）
アクリル酸のポリ（メタ）アクリレート。(3) Polyester poly(meth)acrylate; polycarboxylic acids (maleic acid, succinic acid, glutaric acid, adipic acid, phthalic acid, terephthalic acid, isophthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, trimellitic acid, pyromellitic acid) polyester polyols obtained by polymerizing ω-caprolactone, ω-hydroxycarboxylic acids, etc.) and polyhydric alcohols and/or polyether polyols as exemplified in (1) and/or (2) above; (meta)
Poly(meth)acrylate of acrylic acid.
（Ａ）ポリウレタンポリ（メタ）アクリレート；有機ポ
リイソシアネート（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、ジフェニルメタンジイソシアネ
ート、ヘキサメチレンジイソシアネート、イソホロンジ
イソシアネート、水素添加トリレンジイソシアネート、
水素添加ジフェニルメタンジイソシアネートおよびこ
れらの混合物など）とヒドロキシアルキル（エチル、プ
ロピルなど）（メタ）アクリレートとのポリウレタンま
たは有機ポリイソシアネートと前記（１）から（３）に
例示した多価アルコール、ポリエーテルポリオールまた
はポリエステルポリオールとの末端イソシアネート基残
存するポリウレタンとヒドロキシアルキル（メタ）アク
リレートとのポリウレタンのポリ（メタ）アクリレート
。(A) Polyurethane poly(meth)acrylate; organic polyisocyanate (tolylene diisocyanate, xylylene diisocyanate, diphenylmethane diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, hydrogenated tolylene diisocyanate,
hydrogenated diphenylmethane diisocyanate and mixtures thereof) and hydroxyalkyl (ethyl, propyl, etc.) (meth)acrylate or organic polyisocyanate and the polyhydric alcohols, polyether polyols, or organic polyisocyanates exemplified in (1) to (3) above. Poly(meth)acrylate of polyurethane with polyester polyol and polyurethane with residual terminal isocyanate groups and hydroxyalkyl(meth)acrylate.
（５）エポキシポリ（メタ）アクリレート；多価エポキ
シ化合物と（メタ）アクリル酸または末端カルボキシ（
メタ）アクリレート〔フタル酸モノ（メタ）アクリロイ
ルオキシエチルエステルなど〕とのポリ（メタ）アクリ
レート。(5) Epoxy poly(meth)acrylate; polyvalent epoxy compound and (meth)acrylic acid or terminal carboxylic acid (
Poly(meth)acrylates with meth)acrylates [such as phthalic acid mono(meth)acryloyloxyethyl ester].
多価エポキシ化合物としてはビスフェノールＡ。Bisphenol A is a polyvalent epoxy compound.
ハロゲン化ビスフェノールＡ、フェノールあるいはブレ
ゾールとホルマリンとの縮合物であるノボラック型多価
フェノール化合物などのグリシジルエーテル型ポリエポ
キサイド、前記（１）または（２）に例示した多価アル
コールまたはポリエーテルポリオールなどのグリシジル
エーテル型ポリエポキサイド、重合脂肪酸や前記（３）
に例示したようなポリカルボン酸などとエビハロヒドリ
ンから得られるグリシジルエステル型ポリエポキサイド
、アニリンやジアミノジフェニルメタンなどのアミン類
とエビハロヒドリンから得られるグリシジルアミ・ン型
ポリエポキサイド、二重結合を過酸などから得られるエ
ポキサイド（ビニルシクロヘキセンジオキサイド、エポ
キシ化ポリブタジェン、エポキシ化植物油など）、ある
いはこれら多価エポキサイドと多価アルコールまたはポ
リカルボン酸との反応によって得られるエポキシ基含有
の多価エポキシ化合物などである。Glycidyl ether type polyepoxides such as halogenated bisphenol A, novolak type polyhydric phenol compounds which are condensates of phenol or bresol and formalin, polyhydric alcohols or polyether polyols as exemplified in (1) or (2) above, etc. Glycidyl ether type polyepoxide, polymerized fatty acid and the above (3)
Glycidyl ester type polyepoxide obtained from shrimp halohydrin and polycarboxylic acids such as those exemplified in , glycidyl amine type polyepoxide obtained from shrimp halohydrin and amines such as aniline or diaminodiphenylmethane, and epoxides (vinyl cyclohexene dioxide, epoxidized polybutadiene, epoxidized vegetable oil, etc.), or epoxy group-containing polyepoxy compounds obtained by reacting these polyhydric epoxides with polyhydric alcohols or polycarboxylic acids.
（６）リン酸エステル基含有ポリ（メタ）アクリレート
；ヒドロキシアルキル（メタ）アクリレートと五酸化リ
ンとの反応物、あるいはこれに多価アルコールあるいは
ｍ個アルコール（ブタノール。(6) Phosphate group-containing poly(meth)acrylate; a reaction product of hydroxyalkyl (meth)acrylate and phosphorus pentoxide, or a polyhydric alcohol or m-alcohol (butanol).
２エチルヘキサノールなど）を併用して得られるポリ（
メタ）アクリレート。Poly(2-ethylhexanol, etc.)
Meta) acrylate.
（７）その他１重合脂肪酸系のオキシアルキレンエーテ
ルのポリ（メタ）アクリレート、メラミンの初期縮合物
のポリ（メタ）アクリレート、オルガノポリシロキサン
型ポリオールのポリ（メタ）アクリレート、ビニル共重
合体オリゴマー（たとえばヒドロキシエチルメタクリレ
ートと他のアクリレートとの共重合物など）のポリ（メ
タ）アクリレートなど。(7) Other monopolymerized fatty acid-based oxyalkylene ether poly(meth)acrylates, melamine initial condensate poly(meth)acrylates, organopolysiloxane-type polyol poly(meth)acrylates, vinyl copolymer oligomers (e.g. Poly(meth)acrylates such as copolymers of hydroxyethyl methacrylate and other acrylates).
これら（１）から（７）に記載の化合物のうち好ましい
ものはポリオールポリアクリレート、ポリエステルポリ
アクリレート、ポリウレタンポリアクリレートおよびエ
ポキシポリアクリレートであって１分子中に２個以上の
アクリロイル基を含有する化合物で分子量は通常５００
０以下、好ましくは２５００以下のものである。Among the compounds described in (1) to (7), preferred are polyol polyacrylate, polyester polyacrylate, polyurethane polyacrylate, and epoxy polyacrylate, which are compounds containing two or more acryloyl groups in one molecule. Molecular weight is usually 500
It is 0 or less, preferably 2500 or less.
ポリアミンとケトン類からのケチミン基を含有する化合
物（Ｂ）としてはすくなくとも２個の第一級アミノ基を
有するポリアミン化合物のアミノ基のすくなくとも１個
がケトン類との反応（下記反応式）によって得られるケ
チミン基含有化合物があげられる。The compound (B) containing a ketimine group derived from a polyamine and a ketone is a compound in which at least one amino group of a polyamine compound having at least two primary amino groups is obtained by reaction with a ketone (reaction formula below). Examples include ketimine group-containing compounds.
（式中Ｒはアミノ基の残基 Ｒ／ 、 Ｒ＃はアルキル
基を示す）
これらの具体例としては、たとえば脂肪族ジアミン（エ
チレンジアミン、プロピレンジアミン。(In the formula, R is a residue of an amino group, R/, and R# is an alkyl group.) Specific examples of these include aliphatic diamines (ethylene diamine, propylene diamine, etc.).
テトラメチレンジアミン、ヘキサメチレンジアミン、ノ
ナメチルジアミンなど）、ポリアルキレンポリアミン（
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、ペンタエチレンへキサミン、ジ
プロピレントリアミン。tetramethylene diamine, hexamethylene diamine, nonamethyl diamine, etc.), polyalkylene polyamine (
Diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, dipropylenetriamine.
ジヘキサメチレントリアミンなど）、脂環式ポリアミン
（イソホロンジアミン、４４′−ビスアミノジシクロヘ
キシルメタン、４４′−ビスアミノエチルシクロヘキサ
ン、水素化キシリレンジアミンなど）、芳香環含有脂肪
族ポリアミン（キシリレンジアミンなど）とケトン類（
アセトン、メチルエチルケトン、メチルイソブチルケト
ン、シクロヘキサノン、イソホロンなど）の脱水反応に
よるケチミン基を含有する化合物があげられる。dihexamethylenetriamine, etc.), alicyclic polyamines (isophoronediamine, 44'-bisamino dicyclohexylmethane, 44'-bisaminoethylcyclohexane, hydrogenated xylylene diamine, etc.), aromatic ring-containing aliphatic polyamines (xylylene diamine, etc.) ) and ketones (
Examples include compounds containing a ketimine group resulting from the dehydration reaction of acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, isophorone, etc.).
コノ場合、ポリアミン中の第一級アミノ基の全部がケチ
ミン化していることが好ましいが、分子中のすくなくと
も１つの第一級アミノ基がケチミン化している化合物で
もよい。またポリアミンのうち、前記ポリアミンとアジ
ピン酸、フタル酸。In this case, it is preferable that all of the primary amino groups in the polyamine are ketiminated, but a compound in which at least one primary amino group in the molecule is ketiminated may also be used. Among the polyamines, the above-mentioned polyamines, adipic acid, and phthalic acid.
重合脂肪酸などのポリカルボン酸および前記エポキシポ
リ（メタ）アクリレートの項に記載のエポキシ化合物と
の反応により得られるアミノ基が残存するポリアミドポ
リアミンおよびエポキシ付加ポリアミンも含まれる。Also included are polyamide polyamines and epoxy-added polyamines in which amino groups remain, obtained by reaction with polycarboxylic acids such as polymerized fatty acids and the epoxy compounds described in the section of epoxy poly(meth)acrylates.
これらのうち好ましいものはエチレンジアミン。Among these, ethylenediamine is preferred.
プロピレンジアミン、ヘキサメチレンジアミンおよびジ
エチレントリアミンからの少くとも１種とメチルエチル
ケトンおよびメチルイソブチルケトンからの少くとも１
種とのケチミン基含有化合物で原料ポリアミン中の第一
級アミノ基の８０％以上がケチミン基となっている化合
物である。At least one from propylene diamine, hexamethylene diamine and diethylene triamine and at least one from methyl ethyl ketone and methyl isobutyl ketone
This is a ketimine group-containing compound in which 80% or more of the primary amino groups in the raw material polyamine are ketimine groups.
（メタ）アクリロイル基を持つ多官能化合物（Ｂ）とケ
チミン基を含有する化合物の）との割合は（メタ）アク
リロイル基とケチミン基の当量比で通常１：０．２〜１
： １．５好ましくは１ ： ０．４〜１：１．１の範
囲である。The ratio of the polyfunctional compound (B) having a (meth)acryloyl group to the compound containing a ketimine group is usually 1:0.2 to 1 in terms of the equivalent ratio of the (meth)acryloyl group to the ketimine group.
: 1.5, preferably in the range of 1:0.4 to 1:1.1.
本発明の組成物は通常（Ｂ）との）を使用直前に混合し
て用いることも、あらかじめ（６）と（６）を混合して
おいたものを使用することもできる。ただし後者の場合
ＣＢ）中にケチミン基以外に第一級アミノ基および／ま
たは第二級アミノ基が残存する場合はあらかじめ回申の
（メタ）アクリロイル基とＣＢ）中の第一級アミノ基お
よび／または第二級アミノ基を反応させておくことが好
ましい。この反応の条件は（Ｂ）と（６）を混合し０℃
から８０℃で１時間から１２時間である。The composition of the present invention can be used by mixing (B) and () immediately before use, or it can be used by mixing (6) and (6) in advance. However, in the latter case, if a primary amino group and/or a secondary amino group remains in CB) in addition to the ketimine group, the (meth)acryloyl group and the primary amino group in CB) and It is preferable to react with/or a secondary amino group. The conditions for this reaction are to mix (B) and (6) at 0°C.
to 80°C for 1 to 12 hours.
本発明の組成物は通常（３）との）から成ることを必須
とするが、これに水を含有しない有機溶剤を加えて使用
することもできる。有機溶剤としては広く使用すること
ができ、炭化水素系溶剤（トルエン、キシレン、石油エ
ーテル１、ミネラルスピリットナト）、ケトン系溶剤（
アセトン、メチルエチルケトン、メチルイソブチルケト
ン、シクロヘキサノンなど）、アルコール系溶剤（変性
エタノール、イソプロパツール、ブタノールなト）、エ
ステル系溶剤（酢酸エチル、酢酸ブチルなど）、セロソ
ルブ系溶剤（エチルセロソルブ、ブチルセロソルブなど
）、セロソルブアセテート系溶剤（エチルセロソルブア
セテート、ブチルセロソルブアセテートなど）、カルピ
トール系溶剤（エチルカルピトール、ブチルカルピトー
ルなど）などである。The composition of the present invention usually essentially consists of (3) and (3), but it can also be used by adding an organic solvent that does not contain water. Organic solvents can be widely used, including hydrocarbon solvents (toluene, xylene, petroleum ether 1, mineral spirit), ketone solvents (
acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.), alcohol solvents (denatured ethanol, isopropanol, butanol, etc.), ester solvents (ethyl acetate, butyl acetate, etc.), cellosolve solvents (ethyl cellosolve, butyl cellosolve, etc.) , cellosolve acetate solvents (ethyl cellosolve acetate, butyl cellosolve acetate, etc.), carpitol solvents (ethyl carpitol, butyl carpitol, etc.).
またそのほか、本発明の組成物は着色顔料（二酸化チタ
ン、酸化鉄、カーボンブラック、フタロシアニンブルー
など）、充填剤（炭酸カルシウム。In addition, the composition of the present invention contains colored pigments (titanium dioxide, iron oxide, carbon black, phthalocyanine blue, etc.), fillers (calcium carbonate, etc.).
硫酸バリウム、タルク、シリカ、アルミナ、ガラス繊維
、ベントナイトなど）、更に必要に応じてレベリング剤
、消泡剤１分散剤などの添加剤も混合使用できる。barium sulfate, talc, silica, alumina, glass fiber, bentonite, etc.), and further additives such as a leveling agent, an antifoaming agent, a dispersing agent, etc. can be mixed and used as necessary.
本発明の組成物は、木、金属、プラスチック、セメント
、モルタル、各種電気電子部品、センサーや光ディスク
、磁気ディスクなどのコーティングあるいは接着剤に適
用できる。The composition of the present invention can be applied to coatings or adhesives for wood, metals, plastics, cement, mortar, various electrical and electronic parts, sensors, optical disks, magnetic disks, etc.
適用する場合の塗布法としては、へヶ塗り、スプレー塗
り、ローラー塗り、ディッピング塗り、ヘラ付け、コー
キング、コテ塗りなどであり、通常５μ〜２ｍｍの膜厚
に塗布し使用する。When applied, coating methods include spacing, spraying, roller coating, dipping, spatula coating, caulking, and trowel coating, and the coating is usually applied to a film thickness of 5 μm to 2 mm.
硬化方法は塗布後たとえば大気中で常温〜１２０℃で５
分間〜７日間位で完了する。また急速に硬化させるため
に７０％以上の湿度の雰囲気中で硬化させることや、塗
布直前に水を入れて塗布する方法も可能である。
□
〔実施例〕
以下、実施例により本発明を更に詳細に説明するが、本
発明はこれに限定されるものではない。The curing method is, for example, after coating at room temperature to 120°C in the atmosphere.
It can be completed within minutes to 7 days. Furthermore, in order to cure rapidly, it is possible to cure the coating in an atmosphere with a humidity of 70% or more, or to add water immediately before coating.
□ [Examples] Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited thereto.
参考例１
〔（メタ）アクリロイル基を持つ多官能化合物（６）の
調製〕
下記（１）に示す調製例イル二は攪拌機および温度計を
備えた反応器にポリエステルジオール（例イ＼ウレタン
プレポリマー（側口）、あるいはエポキシ樹脂（例ハ、
二）を入れ、それぞれに対応する量のアクリル酸あるい
はメタクリル酸およびアクリル酸ヒドロキシエチルを入
れ、メチルハイドロキノンを全体量ｉこ対し２００ｐｐ
ｍ添加し例イは１００〜１２０℃、その他は８０〜９０
℃で攪拌不反応させた。Reference Example 1 [Preparation of polyfunctional compound (6) having (meth)acryloyl group] In the preparation example shown in (1) below, a polyester diol (e.g. urethane prepolymer) was placed in a reactor equipped with a stirrer and a thermometer. (side port), or epoxy resin (e.g.
2), add corresponding amounts of acrylic acid or methacrylic acid and hydroxyethyl acrylate, and add 200 pp of methylhydroquinone to the total amount i.
Example A is 100-120℃, others are 80-90℃.
The mixture was stirred at ℃ to incubate the reaction.
反応終点は内容物の酸価が５以下になった時点とした。The end point of the reaction was defined as the point at which the acid value of the contents became 5 or less.
〔ケチミン基を含有する化合物の）の調製〕下記（２）
に示す調製ａ Ｎｄの各々のポリアミンおよびケトンを
攪拌機、水分離装置付き凝縮器および温度計を備えた反
応器ｌこ入れ、ａｓｂ％ｄは１１０〜１４５℃、６時間
でメチルイソブチルケトンを還流し、生成水を凝縮器よ
り除き、Ｃについては無水炭酸カリウムを全体量と同量
を入れて７５〜９０℃、１２時間で還流し反応した。[Preparation of compound containing ketimine group] Following (2)
Preparation a Each polyamine and ketone of Nd were placed in a reactor equipped with a stirrer, a condenser with a water separator and a thermometer, and the methyl isobutyl ketone was refluxed at 110-145°C for 6 hours. The produced water was removed from the condenser, and as for C, anhydrous potassium carbonate was added in the same amount as the total amount, and the mixture was refluxed and reacted at 75 to 90°C for 12 hours.
反応率はａｓ ｂｓ ｄでは生成水の量、Ｃについては
核磁気共鳴分析により測定しＴこ。The reaction rate is measured by the amount of water produced using ASBSD, and C is measured by nuclear magnetic resonance analysis.
（１）；（メタ）アクリロイル基を持つ多官能化合物イ
：アジピン酸とエチレングリコールからのポリエステル
ジオール（分子量：約９００ ） １モルとアクリル酸
２モルとの反応物（分子量：約１００５ 、酸価： ２
．９ ） 、 （０，２０）ロ：ポリプロピレントリオ
ール（分子量： ７５０゜８官能）とキシリレンジイソ
シアネートのプレポリマー（ＮＧＯ含量： ４４０ ）
１モルとアクリル酸ヒドロキシエチル８モルとの反応
物（分子量： １６７０） 、 （０，１８）ハ：エピ
コート８２８（エポキシ当量： １８７ 、油化シェル
エポキシ社製）１モルとメタクリル酸２モルとの反応物
（分子量： ５４５ ） 。(1); Polyfunctional compound with (meth)acryloyl group A: Reaction product of 1 mole of polyester diol (molecular weight: approximately 900) from adipic acid and ethylene glycol and 2 moles of acrylic acid (molecular weight: approximately 1005, acid value : 2
．． 9), (0,20) B: Prepolymer of polypropylene triol (molecular weight: 750°, 8 functional) and xylylene diisocyanate (NGO content: 440)
A reaction product of 1 mole and 8 moles of hydroxyethyl acrylate (molecular weight: 1670), (0,18) C: A reaction product of 1 mole of Epicote 828 (epoxy equivalent: 187, manufactured by Yuka Shell Epoxy Co., Ltd.) and 2 moles of methacrylic acid. Reactant (molecular weight: 545).
（ｏ、ａｓ）
二二エポトートＹＤＣＮ−７０４（エポキシ当量： ２
１４゜東部化成社製）１当量とアクリル酸１モルとの反
応物、（０，８６）
〔〕内の数字は（メタ）アクリロイル基濃度ｍｏ＃／１
００ｇ を示す。(o, as) 22 Epotate YDCN-704 (Epoxy equivalent: 2
Reaction product of 1 equivalent (manufactured by Tobu Kasei Co., Ltd.) and 1 mole of acrylic acid, (0,86) The number in [ ] is the (meth)acryloyl group concentration mo#/1
00g is shown.
（２）；ケチミン基を含有する化合物（Ｂ）ａ：エチレ
ンジアミン６０ｇとメチルイソブチルケトン５００ｇと
の縮合物（濃度：４９％）。(2); Compound (B) a containing a ketimine group: a condensate of 60 g of ethylenediamine and 500 g of methyl isobutyl ketone (concentration: 49%).
＜９９％＞ 、（０，８８１
ｂ：ヘキサメチレンジアミン１１６ｇとメチルイソブチ
ルケトン５００ｇとの縮合物（濃度：５４％） 、 ＜
ｔａＳ％＞ 、 （０，８４３Ｃ：キシリレンジアミ
ン１８６ｇとメチルエチルケトン５００ｇとの縮合物（
濃度：４７％）。<99%>, (0,881 b: condensate of 116 g of hexamethylene diamine and 500 g of methyl isobutyl ketone (concentration: 54%), <
taS%>, (0,843C: condensate of 186 g of xylylene diamine and 500 g of methyl ethyl ketone (
Concentration: 47%).
＜９８％＞ 、 （０，８８）
ｄニジエチレントリアミン１０８ｇとメチルイソブチル
ケトン５００ｇとの縮合物（濃度：５８％）、 ＜９４
％＞ 、（０，８５）
く〉内の％はケチミン化率、（）内の
数値はケチミン基濃度ｍｏｇ／１００ｇ を示すＯ
実施例１〜７
参考例１で調製した（メタ）アクリロイル基を持つ多官
能化合物囚およびケチミン基を含有する化合物ＣＢ）を
表−１記載の重量比で混合し本発明の組成物を得１こ。<98%>, (0,88) d Condensate of 108 g of diethylene triamine and 500 g of methyl isobutyl ketone (concentration: 58%), <94
%> , (0,85) % in 〉 indicates the ketimine conversion rate, and the value in parentheses indicates the ketimine group concentration mog/100g. Examples 1 to 7 The (meth)acryloyl group prepared in Reference Example 1 was A composition of the present invention was obtained by mixing a polyfunctional compound containing a ketimine group and a compound CB containing a ketimine group in the weight ratio shown in Table 1.
この本発明の組成物の一部は粘度測定後密閉したガラス
容器に入れ、４０℃の雰囲気で１週間静置し、再び粘度
測定し静置前と後の粘度を比較し保存性を調べ丁こ。残
りの本発明の組成物は軟鋼板に７５μのフィルムアプリ
ケーターで塗布し湿度６５％、温度２５℃に静置し乾燥
時間を測定し、１週間後の硬化塗膜について発泡の有無
、および硬度、密着性、絶縁性を測定した。After measuring the viscosity, a part of the composition of the present invention was placed in a sealed glass container, left to stand for one week in an atmosphere of 40°C, the viscosity was measured again, and the viscosity before and after standing was compared to determine the shelf life. child. The remaining composition of the present invention was applied to a mild steel plate with a 75μ film applicator, left to stand at a humidity of 65% and a temperature of 25°C, and the drying time was measured.The cured coating after one week was evaluated for the presence or absence of foaming, hardness, Adhesion and insulation properties were measured.
同様に湿度８５％、温度８０℃の雰囲気中で１００μ、
２００μ、５００μの塗布軟鋼板を硬化させて、発泡の
有無を調べた。これらの結果を表−２に示す。Similarly, 100μ in an atmosphere with a humidity of 85% and a temperature of 80℃,
Mild steel sheets coated with 200μ and 500μ were hardened and examined for foaming. These results are shown in Table-2.
表−２かられかるようにいずれの実施例においても発泡
のない厚膜が得られ、保存性、乾燥性、硬度、密着性も
良好であった。As can be seen from Table 2, thick films without foaming were obtained in all Examples, and the storage stability, drying properties, hardness, and adhesion were also good.
表−１ 表−２ 刀 保存性：密閉４０℃保存−週間後判定。Table-1 Table-2 sword Storage: Stored in a sealed container at 40°C - Judgment after a week.
Ｏ；増粘なし
△；混混合−後後増粘るもその後増粘なし＊；５０ミク
ロン（ウェット）塗膜の湿度６５％。O: No thickening △: Mixing - Thickening after mixing, but no thickening afterwards *; Humidity of 50 micron (wet) coating film: 65%.
温度２５℃での硬化した。Cured at a temperature of 25°C.
＊＊；膜厚１００ 、１７５ 、２５０ミクロン（ウェ
ット）で鋼板に塗布し、湿度８５％、温度８０℃、８日
間硬化後の硬化塗膜を外観判定した。**; The coating was applied to a steel plate at a film thickness of 100, 175, or 250 microns (wet), and the appearance of the cured film was evaluated after curing for 8 days at a humidity of 85% and a temperature of 80°C.
本発明の組成物は厚塗りし１二り、高湿度の条件下にお
いても発泡のない塗膜が得られるという効果を奏する。The composition of the present invention has the effect of being able to be coated thickly and providing a coating film without foaming even under high humidity conditions.
その他、保存安定性がよく、短時間のうちに硬化し、硬
化塗膜は高い硬度を有し、基材との密着性にもすぐれて
いる。適用する基材の表面が湿潤している場合でも、高
い密着性と良好な硬化性を示すという特長をも併せ有し
ている。In addition, it has good storage stability, cures in a short time, has a cured coating film with high hardness, and has excellent adhesion to the substrate. It also has the advantage of exhibiting high adhesion and good curability even when the surface of the substrate to which it is applied is wet.
上記効果を奏することから、本発明の組成物は木、金属
、プラスチック、コンクリート、モルタル等のコーティ
ングや接着剤として、また各種電気電子部品の保護コー
チインク）センサーや光ディスク、磁気ディスク等のコ
ーティングなどに有用である。さらに接着、ポツティン
グ、シーリンスキャスティング用としても有用である。Because it exhibits the above effects, the composition of the present invention can be used as a coating or adhesive for wood, metal, plastic, concrete, mortar, etc., and as a protective coating ink for various electrical and electronic components), as a coating for sensors, optical disks, magnetic disks, etc. It is useful for Furthermore, it is useful for adhesion, potting, and sealing casting.
Claims (1)
基を持つ、多官能化合物（Ａ）およびポリアミンとケト
ン類からのケチミン基を含有する化合物（Ｂ）とから成
ることを特徴とする湿気硬化性組成物。1. Moisture-curing property characterized by comprising a polyfunctional compound (A) having at least two (meth)acryloyl groups in the molecule and a compound (B) containing a ketimine group from a polyamine and ketones. Composition.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8144186A JPS62236812A (en) | 1986-04-08 | 1986-04-08 | Moisture-curable composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8144186A JPS62236812A (en) | 1986-04-08 | 1986-04-08 | Moisture-curable composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62236812A true JPS62236812A (en) | 1987-10-16 |
Family
ID=13746481
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8144186A Pending JPS62236812A (en) | 1986-04-08 | 1986-04-08 | Moisture-curable composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62236812A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5198524A (en) * | 1991-04-22 | 1993-03-30 | W.R. Grace & Co.-Conn. | Moisture-curing acrylate/epoxy hybrid adhesives |
-
1986
- 1986-04-08 JP JP8144186A patent/JPS62236812A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5198524A (en) * | 1991-04-22 | 1993-03-30 | W.R. Grace & Co.-Conn. | Moisture-curing acrylate/epoxy hybrid adhesives |
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