JPS6356549A - Curable resin composition having excellent weather resistance - Google Patents
Curable resin composition having excellent weather resistanceInfo
- Publication number
- JPS6356549A JPS6356549A JP20006686A JP20006686A JPS6356549A JP S6356549 A JPS6356549 A JP S6356549A JP 20006686 A JP20006686 A JP 20006686A JP 20006686 A JP20006686 A JP 20006686A JP S6356549 A JPS6356549 A JP S6356549A
- Authority
- JP
- Japan
- Prior art keywords
- polymer
- resin composition
- curable resin
- meth
- unsaturated monomer
- 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
- 239000011342 resin composition Substances 0.000 title claims description 13
- 229920000642 polymer Polymers 0.000 claims abstract description 33
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 239000000178 monomer Substances 0.000 claims abstract description 14
- 239000004593 Epoxy Substances 0.000 claims abstract description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 8
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 239000011347 resin Substances 0.000 claims abstract description 3
- 229920005989 resin Polymers 0.000 claims abstract description 3
- -1 alkylene imine Chemical class 0.000 claims description 7
- 238000000576 coating method Methods 0.000 abstract description 16
- 239000011248 coating agent Substances 0.000 abstract description 12
- 239000000203 mixture Substances 0.000 abstract description 10
- 238000001035 drying Methods 0.000 abstract description 8
- 239000002904 solvent Substances 0.000 abstract description 8
- 238000013329 compounding Methods 0.000 abstract 1
- 238000007334 copolymerization reaction Methods 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 239000003973 paint Substances 0.000 description 18
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 4
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000004923 Acrylic lacquer Substances 0.000 description 3
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 230000008439 repair process Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- OZDGMOYKSFPLSE-UHFFFAOYSA-N 2-Methylaziridine Chemical compound CC1CN1 OZDGMOYKSFPLSE-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000010422 painting Methods 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- LSDGFGPIFBOTJI-UHFFFAOYSA-N 2-(aziridin-1-yl)ethanamine Chemical compound NCCN1CC1 LSDGFGPIFBOTJI-UHFFFAOYSA-N 0.000 description 1
- HDPLHDGYGLENEI-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COCC1CO1 HDPLHDGYGLENEI-UHFFFAOYSA-N 0.000 description 1
- SEFYJVFBMNOLBK-UHFFFAOYSA-N 2-[2-[2-(oxiran-2-ylmethoxy)ethoxy]ethoxymethyl]oxirane Chemical compound C1OC1COCCOCCOCC1CO1 SEFYJVFBMNOLBK-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- CSWPOLMVXVBCSV-UHFFFAOYSA-N 2-ethylaziridine Chemical compound CCC1CN1 CSWPOLMVXVBCSV-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- VKEQBMCRQDSRET-UHFFFAOYSA-N Methylone Chemical compound CNC(C)C(=O)C1=CC=C2OCOC2=C1 VKEQBMCRQDSRET-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- LKYQLAWMNBFNJT-UHFFFAOYSA-N anileridine Chemical compound C1CC(C(=O)OCC)(C=2C=CC=CC=2)CCN1CCC1=CC=C(N)C=C1 LKYQLAWMNBFNJT-UHFFFAOYSA-N 0.000 description 1
- 229960002512 anileridine Drugs 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000005453 ketone based solvent 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
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 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
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
- Paints Or Removers (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、耐候性の優れた硬化性樹脂組成物に関するも
のである。更に詳しくは、低温で硬化し、乾燥性、硬度
、耐溶剤性、密着性が優れた塗膜を与える塗料、インキ
、接着剤等の用途に有用な耐候性の優れた硬化性樹脂組
成物に関するものである。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to a curable resin composition with excellent weather resistance. More specifically, it relates to a curable resin composition that cures at low temperatures and has excellent weather resistance and is useful for applications such as paints, inks, and adhesives that provide coatings with excellent drying properties, hardness, solvent resistance, and adhesion. It is something.
（従来の技術）
従来、建材、船舶、鉄道車輌、航空機、出動中補修等加
熱処理の適さない分野においては、防蝕性・美観などの
面により、優れた耐候性を有する樹脂組成物が望まれて
おり、これらの要望にこたえるために、ニトロセルロー
ス、セルロースアセテートブチレートなどを、加えた常
温乾燥型アクリルラッカーや常温硬化型二液ウレタン樹
脂を用いた塗料などが、広く用いられている。(Prior Art) Conventionally, in fields where heat treatment is not suitable, such as building materials, ships, railway vehicles, aircraft, and repairs during deployment, resin compositions with excellent weather resistance have been desired from the viewpoint of corrosion resistance and aesthetics. To meet these demands, room-temperature-drying acrylic lacquers containing nitrocellulose, cellulose acetate butyrate, etc., and room-temperature-curing two-component urethane resin paints are widely used.
（発明が解決しようとする問題点）
前者のアクリルラッカーは、低価格でかつ使用上の簡便
性に、又後者の二液ウレタン樹脂塗料はポリオールとポ
リイソシアネート化合物との架橋反応に起因する優れた
塗膜性能に特徴を有する反面、以下の如き欠点を有する
ものである。(Problems to be Solved by the Invention) The former acrylic lacquer is inexpensive and easy to use, while the latter two-component urethane resin paint has excellent properties due to the crosslinking reaction between polyol and polyisocyanate compound. Although it is characterized by its coating film performance, it has the following drawbacks.
すなわち、アクリルラッカーは目的とする性能を得る為
にポリマーの分子量を大きくしたり、ガラス転移温ｒ！
１（Ｔｏ）を高く（る必要があるが、その為に多量の有
機溶媒で希釈する事を必要とする。これは近年、省資源
、環境汚染等の観点から要求の強い塗料のハイソリッド
化にそぐわないものである。また、二液ウレタン樹脂塗
料は使用するポリソシアネート化合物に基づく毒性や価
格面に問題を有している。In other words, in order to achieve the desired performance, acrylic lacquers have to increase the molecular weight of the polymer and increase the glass transition temperature r!
1 (To), which requires dilution with a large amount of organic solvent.This is due to the high solids coatings that have been in high demand in recent years from the viewpoint of resource conservation and environmental pollution. In addition, two-component urethane resin paints have problems in terms of toxicity and cost due to the polysocyanate compounds used.
このような問題を解決すべく新しい硬化システムの開発
研究が種々なされているにもかかわらず、いまだに従来
の技術に変り得る性能を有する塗料を得られていないの
が現状である。Although various research and development efforts have been made to develop new curing systems to solve these problems, the current state of the art is that a paint with performance that can replace conventional technology has not yet been obtained.
（問題点を解決するための手段）
本発明は、カルボキシル基を含有する不飽和単量体（ａ
）と、その他の重合性不飽和単量体（ｂ）を共重合して
（７られる重合物のカルボキシ基をアルキレンイミン（
ｃ）と反応させてなる重合体（１）、ならびに、分子中
に、エポキシ基を少くとも２個以上含有するエポキシ化
合物（ｎ）を必須成分としてなる硬化性樹脂組成物に関
するものである。(Means for Solving the Problems) The present invention provides an unsaturated monomer containing a carboxyl group (a
) and another polymerizable unsaturated monomer (b) to convert the carboxy group of the resulting polymer into an alkyleneimine (
The present invention relates to a curable resin composition containing as essential components a polymer (1) obtained by reacting with c) and an epoxy compound (n) containing at least two or more epoxy groups in the molecule.
本発明の重合体（Ｉ）のｙ３ Ｂに用いられる単量体（
ａ）としては、例えば（メタ）アクリル酸、ケイ皮酸お
よびクロトン酸などの不飽和モノカルボン酸；マレイン
酸、イタコン酸およびノルマ酸などの不飽和ジカルボン
酸またはそのモノエステル類などを上げる事ができこれ
らの群から選ばれる１種または２種以上の混合物を使用
することができる。The monomer (
Examples of a) include unsaturated monocarboxylic acids such as (meth)acrylic acid, cinnamic acid and crotonic acid; unsaturated dicarboxylic acids such as maleic acid, itaconic acid and normic acid, or their monoesters. It is possible to use one kind or a mixture of two or more kinds selected from these groups.
本発明の重合体（Ｉ）の製造に用いられる単量体（ｂ）
としては、ｔｔＨａ体（ａ）と共重合しうるちのであれ
ば特に制限されず、例えば（メタ）アクリルアミド、Ｎ
−メチロール（メタ）アクリルアミド、２−ヒドロキシ
エチル（メタ）アクリレート、２−ヒドロキシプロピル
（メタ）アクリレート、メチル（メタ）アクリレート、
エチル、（メタ）アクリレート、ｎ−プロピル（メタ）
アクリレート、イソプロピル（メタ）アクリレート、ｎ
−ブチル（メタ）アクリレート、イソブチル（メタ）ア
クリレート、ｔ−ブチル（メタ）アクリレート、２−エ
チルヘキシル（メタ）アクリレート、シクロヘキシル（
メタ）アクリレート、（メタ）アクリロニトリル、スチ
レン、α−メチルスチレン、酢酸ビニル、ブＯピオン酸
ビニル、（メタ）アクロレイン、ジエチルアミノエチル
（メタ）アクリレートおよびジエチルアミノエチル（メ
タ）アクリレートなどを挙げることができ、これらの群
から選ばれる１種または２種以上の混合物を使用するこ
とができる。Monomer (b) used in the production of the polymer (I) of the present invention
There are no particular restrictions on the material as long as it can be copolymerized with the ttHa body (a), such as (meth)acrylamide, N
- Methylol (meth)acrylamide, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, methyl (meth)acrylate,
Ethyl, (meth)acrylate, n-propyl (meth)
acrylate, isopropyl (meth)acrylate, n
-Butyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, cyclohexyl (
Meth)acrylate, (meth)acrylonitrile, styrene, α-methylstyrene, vinyl acetate, vinyl pionate, (meth)acrolein, diethylaminoethyl (meth)acrylate and diethylaminoethyl (meth)acrylate. One type or a mixture of two or more types selected from these groups can be used.
本発明の重合体（Ｉ）を１＠るための前駆体の重合物は
１記単量体（ａ）および（ｂ）を公知の手順に従って共
重合してできる。例えば溶液重合法、塊状重合法、懸濁
重合法等の重合法を採用することができるが、本発明に
おいては溶液重合法により製造することがもつとも好ま
しい。該重合物を溶液重合以外の重合法によって製造し
た場合は、該重合物を溶解しうる有機溶媒に溶解する工
程を必要とする。A precursor polymer for producing the polymer (I) of the present invention can be obtained by copolymerizing the monomers (a) and (b) described in 1 above according to a known procedure. For example, a polymerization method such as a solution polymerization method, a bulk polymerization method, or a suspension polymerization method can be employed, but in the present invention, it is preferable to manufacture by a solution polymerization method. When the polymer is produced by a polymerization method other than solution polymerization, a step of dissolving the polymer in an organic solvent that can dissolve the polymer is required.
溶液重合法を採用する場合には使用できる溶媒としては
、例えばドレニン、キシレンやその他の高沸点の芳香族
溶剤：酢酸エチル、酢酸ブチルおよびセロソルブアセア
ートなどのエステル系溶剤；メチルアルコール、エチル
アルコール、ｒ）−ブチルアルコールおよびイソブチル
アルコールなどのアルコール系溶剤：メチルエチルケト
ンおよびメチルイソブチルケ１−ンなとのケトン係溶剤
などを挙げることができ、これらの群から選ばれる１種
または２種以上の混合物を使用することができる。When employing the solution polymerization method, solvents that can be used include, for example, dolenin, xylene, and other high-boiling aromatic solvents; ester solvents such as ethyl acetate, butyl acetate, and cellosolve acetate; methyl alcohol, ethyl alcohol, r) -Alcoholic solvents such as butyl alcohol and isobutyl alcohol: Examples include ketone solvents such as methyl ethyl ketone and methyl isobutyl ketone, and one or a mixture of two or more selected from these groups. can be used.
また、使用できる重合開始剤としてはアゾビスイソブヂ
ロニトリル、ベンゾイルパーオキサイドおよびジーｔｅ
ｒｔ−ブチルーパーオキサイドなどを挙げることができ
る。In addition, usable polymerization initiators include azobisisobutyronitrile, benzoyl peroxide, and di-tetra
Examples include rt-butyl peroxide.
単量体（ａ）および（ｂ）の重合温度は室温〜２００℃
、好ましくは４０〜１２０℃の範囲である。The polymerization temperature of monomers (a) and (b) is room temperature to 200°C
, preferably in the range of 40 to 120°C.
重合体（Ｉ）は、上記重合物を該重合物に含まれるカル
ボキシル基をアルキレンイミン（ｃ）と反応してなるア
ミノ化したものである。Polymer (I) is an aminated product obtained by reacting the carboxyl group contained in the above polymer with alkylene imine (c).
アミノ化反応は、例えば４０〜１５０℃、このましくは
５０〜１００℃の温度条件下に該重合物とアルキレンイ
ミンとを混合攪拌することによって達成される。The amination reaction is achieved by mixing and stirring the polymer and alkylene imine at a temperature of, for example, 40 to 150°C, preferably 50 to 100°C.
アルキレンイミン（ｃ）としては、例えばエチレンイミ
ン、プロピレンイミン及びブチレンイミン等が使用でき
る。また、Ｎ−（２−アミノエチル）アジリジン、Ｎ−
（３−アミノプロピル）アリジン、Ｎ−（２−アミノプ
ロピル）プロピレンイミンなどのＮ−（アミノアルキル
）置換アルキレンイミンも同様に使用できる。As the alkylene imine (c), for example, ethylene imine, propylene imine, butylene imine, etc. can be used. Also, N-(2-aminoethyl)aziridine, N-
N-(aminoalkyl)-substituted alkyleneimines such as (3-aminopropyl)alidine and N-(2-aminopropyl)propyleneimine can be used as well.
本発明に用いられるエポキシ化合物（ＩＩ＞は、分子中
にエポキシ基を少くとも２個含有する化合物であり、当
該エポキシ化合物（ＩＩ）としては、例えばビスフェノ
ールＡジグリシジルエーテル、水添ビスフェノールＡジ
グリシジルエーテル、エチレングリコールジグリシジル
エーテル、プロピレングリコールジグリシジルエーテル
、ジエチレングリコールジグリシジルエーテル、グリセ
ロールポリグリシジルエーテル、ソルビトールポリグリ
シジルエーテルおよびグリシジル（メタ）アクリレート
成分を含む共重合物などを挙げることができ、これらの
１種または２種以上の混合物を使用することができる。The epoxy compound (II) used in the present invention is a compound containing at least two epoxy groups in the molecule, and examples of the epoxy compound (II) include bisphenol A diglycidyl ether, hydrogenated bisphenol A diglycidyl ether, and hydrogenated bisphenol A diglycidyl ether. Examples include copolymers containing ether, ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, glycerol polyglycidyl ether, sorbitol polyglycidyl ether, and glycidyl (meth)acrylate components. Species or mixtures of two or more species can be used.
エポキシ化合物（ＩＩ）の使用量に特に制限はないが、
優れた耐候性を有し、且つ乾燥性、硬度、耐溶媒性等の
性能を必要かつ充分に発揮させるには、重合体（Ｉ）に
含まれるアミノ基１当ｍに対し、０．５〜３．０当量と
するのが好ましく、より好ましくは０．７〜会、０当岱
である。There is no particular restriction on the amount of epoxy compound (II) used, but
In order to have excellent weather resistance and to exhibit necessary and sufficient performance such as drying properties, hardness, and solvent resistance, the amount of amino groups contained in the polymer (I) should be 0.5 to 1 equivalent m. The amount is preferably 3.0 equivalents, more preferably 0.7 to 0 equivalents.
本発明を実施するにあたり、重合体（Ｉ）と、エポキシ
化合物（Ｉｔ）の樹脂分に対して含有される芳香族環の
重量が、１０重量％以以下あることが必須である。芳香
族環の重量が１０重量％を越えると、耐候性が劣ったも
のとなる。In carrying out the present invention, it is essential that the weight of the aromatic ring contained in the polymer (I) and the resin content of the epoxy compound (It) is 10% by weight or less. If the weight of the aromatic ring exceeds 10% by weight, the weather resistance will be poor.
本発明の硬化性樹脂組成物はそのまま、塗料、インキ、
接着剤等の用途に用いられるが、必要に応じて公知の充
填剤、レベリング剤、可塑剤、安定剤、染料、トナー、
顔料、帯電防止剤等の各種添加剤を適宜含んでいても良
い。The curable resin composition of the present invention can be used as it is in paints, inks, etc.
It is used for applications such as adhesives, but if necessary, known fillers, leveling agents, plasticizers, stabilizers, dyes, toners,
Various additives such as pigments and antistatic agents may be included as appropriate.
（作 用）
本発明の硬化性樹脂組成物は、耐候性が優れた塗膜を提
供する作用を有する。(Function) The curable resin composition of the present invention has the function of providing a coating film with excellent weather resistance.
また、本発明の硬化性樹脂組成物をビヒクル成分として
用いた塗料は、スプレー塗装、ロール塗装、ハケ塗りな
どの塗装法により、金属、無機材料、プラスチック、木
工製品などに塗装することができ、優れた耐候性を有し
、且つ、乾燥性、硬度、耐溶媒性、密着性の優れた塗膜
を形成する作用を有する。Furthermore, the paint using the curable resin composition of the present invention as a vehicle component can be applied to metals, inorganic materials, plastics, wood products, etc. by coating methods such as spray coating, roll coating, and brush coating. It has excellent weather resistance and has the ability to form a coating film with excellent drying properties, hardness, solvent resistance, and adhesion.
さらに、本発明の硬化性樹脂組成物を用いることによっ
て、他の塗料に見られる様なイソシアネートに基づく毒
性の心配もなく、上記特徴を有する塗料が簡便に製造で
きるため、構造物用、自動車補修用あるいは家具塗装等
木工用などの広い用途に使用できる作用を有する。Furthermore, by using the curable resin composition of the present invention, there is no need to worry about toxicity due to isocyanates as seen in other paints, and paints with the above characteristics can be easily produced, making it suitable for use in structures and automobile repair. It has an action that can be used for a wide range of purposes such as woodworking and furniture painting.
（実 施 例）
以下、実施例により本発明を具体的に説明するが、本発
明は以下の実施例によって制限されない。(Examples) Hereinafter, the present invention will be specifically explained with reference to Examples, but the present invention is not limited by the following Examples.
尚、例中の部および％は特にことわらない限り、それぞ
れｉ［部および重量％を示す。In addition, unless otherwise specified, parts and % in the examples indicate i[parts and weight %, respectively.
参考例 １
攪拌機、温度計、冷却器、滴下ロート及び窒素ガス導入
管のついた４つロフラスコにブ０ピレングリコールモノ
メチルアルコール５０部を仕込み、８０℃まで昇温した
。そこへ窒素ガスを吹き込みながらメタクリル酸４部、
メチルメタクリレート２０部、ブチルメタクリレ−１・
２１部、ブチルアクリレート５部およびアゾビスイソブ
チロニトリル０．５部からなる混合物を２時間に亘って
滴下ロートより滴下し、更に８０℃で６時間保持した後
、室温まで冷却してカルボキシル基を含有する混合物の
溶液を得た。次いで、上記のフラスコに更に５部のエチ
レンイミンを１０分間で滴下した。Reference Example 1 50 parts of pyrene glycol monomethyl alcohol was charged into a four-bottle flask equipped with a stirrer, a thermometer, a condenser, a dropping funnel, and a nitrogen gas introduction tube, and the temperature was raised to 80°C. 4 parts of methacrylic acid while blowing nitrogen gas into it,
20 parts of methyl methacrylate, 1 part of butyl methacrylate
A mixture consisting of 21 parts of butyl acrylate, 5 parts of azobisisobutyronitrile, and 0.5 parts of azobisisobutyronitrile was added dropwise from the dropping funnel over 2 hours, and after further holding at 80°C for 6 hours, the carboxyl group was cooled to room temperature. A solution of the mixture was obtained. Then, an additional 5 parts of ethyleneimine was added dropwise to the flask over 10 minutes.
滴下を終了して１時間後に７５℃まで胃温し同温度で５
時間保持した後、４つロフラスコに蒸留装置をセットし
、減圧下に加熱して流出分と同量のプロピレングリコー
ルモノメチルエーテルを補強しながら未反応のエチレン
イミンと共に系外に流出させ、残存のエチレンイミンを
完全に除去した。1 hour after finishing the instillation, warm the stomach to 75℃ and keep it at the same temperature for 5 minutes.
After holding for a period of time, a distillation device is set in a four-roof flask, heated under reduced pressure, and the same amount of propylene glycol monomethyl ether as the outflow is reinforced and flowed out of the system together with unreacted ethylene imine. Imine was completely removed.
最後に不揮発分を５０％に調整し重合体（１）の溶液を
１ｑた。Finally, the nonvolatile content was adjusted to 50%, and 1 q of the polymer (1) solution was prepared.
参考例２
参考例１において、重合性単量体の組成の量を、第１表
に示した通りとする他は、参考例１と同じ操作をくり返
して、重合体（２）の溶液を得た。Reference Example 2 A solution of polymer (2) was obtained by repeating the same operations as in Reference Example 1, except that the amount of the polymerizable monomer composition was as shown in Table 1. Ta.
参考例３
参考例１において、重合性単ｍ体の組成の量を、第１表
に示した通りとする他は、参考例１と同じ操作をくり返
して、重合体（３）の溶液を得た。Reference Example 3 A solution of polymer (3) was obtained by repeating the same operations as in Reference Example 1, except that the composition amount of the polymerizable monomer m was as shown in Table 1. Ta.
比較参考例１
参考例１において、重合性単量体の組成の量を、第１表
に示した通りとする他は、参考例１と同じ操作をくり返
して、比較用重合体（Ｉ）の溶液を得た・。Comparative Reference Example 1 In Reference Example 1, the same operation as in Reference Example 1 was repeated except that the composition amount of the polymerizable monomer was changed as shown in Table 1 to prepare Comparative Polymer (I). Obtained a solution.
第１表
実施例１〜４ 比較例１〜３
参考例１〜３及び比較参考例１で得た重合体（１）〜（
３）および比較用重合体（１）の１２０部と、酸化チタ
ン（デュポン製品Ｒ−９００）４０部とをサンドミルの
容器に仕込み、２０００ｒｐｍで３０分間高速攪拌して
不揮発分中顔料重量濃度が４０％の重合体の顔料分散液
を得た。この顔料分散液へ該分散液中の重合体に含まれ
るアミノ基に対しエポキシ基が当量となる爪のエポキシ
化合物を配合して、第２表に示したように、重合体（１
）〜（３）とエポキシ化合物からなる硬化性樹脂組成物
（１）〜（４）、重合体（３）および比較用重合体（１
）とエポキシ化合物からなる比較用組成物（１）〜（２
）をバインダーとする塗料（１）〜（４）および比較用
塗料（１）〜（２）を得た。さらに、比較用塗料（３）
として、市販アクリルウレタン塗料を調整した。Table 1 Examples 1 to 4 Comparative Examples 1 to 3 Polymers (1) to (1) obtained in Reference Examples 1 to 3 and Comparative Reference Example 1
3) and 120 parts of comparative polymer (1) and 40 parts of titanium oxide (DuPont product R-900) were placed in a sand mill container and stirred at high speed for 30 minutes at 2000 rpm until the pigment weight concentration in nonvolatile matter was 40. % of the polymer was obtained. A nail epoxy compound in which the epoxy group is equivalent to the amino group contained in the polymer in the dispersion is blended into this pigment dispersion, and as shown in Table 2, the polymer (1
) to (3) and epoxy compounds (1) to (4), polymer (3), and comparative polymer (1).
) and epoxy compounds (1) to (2)
) as a binder, paints (1) to (4) and comparative paints (1) to (2) were obtained. Furthermore, comparative paint (3)
A commercially available acrylic urethane paint was prepared as follows.
これらの塗料をリン酸亜鉛処理鋼板にスプレーで乾燥膜
厚が４０μとなるよう塗布したのち、（室温にて１週間
）乾燥して、各種試験用塗膜を得た。これらの塗膜の各
種試験結果は第３表に示した通りであった。These paints were applied by spray to a zinc phosphate-treated steel plate to a dry film thickness of 40 μm, and then dried (for one week at room temperature) to obtain various test paint films. The results of various tests on these coatings are shown in Table 3.
第２表
注−１エピコート８２８：油化シェル社製、ビスフェノ
ールＡジグリシジルエーテル
注−２ブナコールＥＸＱ１４ 、ナガセ化成工業社製
ソルビトール系多価グリシジルエーテル
第３表
［塗膜の性能試験方法およびその評価Ｅｅｌ（１）
乾燥性 二室温にて１時間乾燥後の指触で評価した。Table 2 Note-1 Epicoat 828: Bisphenol A diglycidyl ether Note-2 Bunacol EXQ14, manufactured by Yuka Shell Co., Ltd. Sorbitol-based polyglycidyl ether manufactured by Nagase Chemical Industries, Ltd. Table 3 [Coating film performance test method and its evaluation Eel(1)
Drying property Evaluation was made by touch after drying at room temperature for 1 hour.
◎・・・・・・・・・変化なし
Ｏ・・・・・・・・・少し跡がつく
Δ・・・・・・・・・跡がつく
×・・・・・・・・・粘着性強い
（２） 鉛筆硬度： ２５０Ｇ加重、三菱ユニで塗
膜の傷付硬度を調べた。◎・・・・・・・・・No change O・・・・・・Leaves a little mark Δ・・・・・・Leaves a mark ×・・・・・・Adhesive Strong (2) Pencil hardness: The scratch hardness of the paint film was examined using Mitsubishi Uni, under a 250G load.
（３） 耐溶剤性：ウレタン用シンナーのスポット
テストで塗膜の状態を観察した。(3) Solvent resistance: The state of the coating film was observed in a spot test using urethane thinner.
◎・・・・・・・・・変化なし
Ｏ・・・・・・・・・少し軟化した
Δ・・・・・・・・・軟化した
Ｘ・・・・・・・・・塗膜が溶解した
（４） 耐候性 ：サンシャイン型つエザオメータ
・−で３０００時間照（ト）した後の
塗膜の光沢９色差、密着性およ
び外観をみた。◎・・・・・・No change O・・・・・・Slightly softened Δ・・・・・・Softened X・・・・・・The coating film Dissolved (4) Weather resistance: The gloss, color difference, adhesion, and appearance of the coating film after being exposed to sunlight for 3,000 hours using a sunshine type weatherometer were observed.
（１） 光 沢：６０度鏡面反射率を測定した。(1) Gloss: 60 degree specular reflectance was measured.
（２） 色 差：カラーマシンにて、色差ΔＥを
測定した。(2) Color difference: Color difference ΔE was measured using a color machine.
（３） 密着性 ：１Ｍゴバン目セロテープ剥離で
塗膜の残存を調べた。(3) Adhesion: The remaining coating film was examined by peeling off with 1M cellophane tape.
◎・・・・・・・・・１００／１００
０・・・・・・・・・１００／１００〜９５／１００Δ
・・・・・・・・・９５／１００〜９０／１００×・・
・・・・・・・９０／１００＞
（発明の効果）
□本発明の硬化性樹脂組成物は、優れた耐候性を有し、
且つ、乾燥性、硬度、耐溶媒性、密着性の優れた塗膜を
形成する。さらに、本発明の硬化性樹脂組成物を用いる
ことによって、ウレタン系塗料に見られる様なイソシア
ネートに基づく毒性の心配もなく、上記特徴を有する塗
料が簡便に製造できる為、構造物用、自動車補修用ある
いは家具塗装等木工用などの広い用途に使用できる効果
を有するものである。◎・・・・・・・・・100/100 0・・・・・・・・・100/100～95/100Δ
・・・・・・・・・95/100～90/100×・・
...90/100> (Effects of the invention) □The curable resin composition of the present invention has excellent weather resistance,
In addition, it forms a coating film with excellent drying properties, hardness, solvent resistance, and adhesion. Furthermore, by using the curable resin composition of the present invention, there is no worry about toxicity due to isocyanates, which is found in urethane-based paints, and paints with the above characteristics can be easily produced, so they can be used for structures, automobile repair, etc. It has the effect that it can be used for a wide range of purposes, such as woodworking, furniture painting, etc.
Claims (2)
、その他の重合性不飽和単量体（ｂ）を共重合して得ら
れる重合物のカルボキシル基をアルキレンイミン（ｃ）
と反応させてなる重合体（ I ）ならびに、分子中にエ
ポキシ基を少なくとも２個以上含有するエポキシ化合物
（II）を必須成分とすることを特徴とする硬化性樹脂組
成物。(1) The carboxyl group of the polymer obtained by copolymerizing the unsaturated monomer (a) containing a carboxyl group and another polymerizable unsaturated monomer (b) is converted into an alkylene imine (c).
A curable resin composition comprising as essential components a polymer (I) obtained by reacting with a polymer (I) and an epoxy compound (II) containing at least two epoxy groups in the molecule.
脂分に対して含有される芳香族環の重量が１０重量％以
下である特許請求の範囲（１）項記載の硬化性樹脂組成
物。(2) The curable resin composition according to claim (1), wherein the weight of the aromatic ring contained based on the resin content of the polymer (I) and the epoxy compound (II) is 10% by weight or less. .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20006686A JPS6356549A (en) | 1986-08-28 | 1986-08-28 | Curable resin composition having excellent weather resistance |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20006686A JPS6356549A (en) | 1986-08-28 | 1986-08-28 | Curable resin composition having excellent weather resistance |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6356549A true JPS6356549A (en) | 1988-03-11 |
Family
ID=16418273
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20006686A Pending JPS6356549A (en) | 1986-08-28 | 1986-08-28 | Curable resin composition having excellent weather resistance |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6356549A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5391633A (en) * | 1989-11-20 | 1995-02-21 | Nippon Shokubai Co., Ltd. | Curable resin composition |
| US6441102B2 (en) | 2000-02-10 | 2002-08-27 | Nippon Shokubai Co., Ltd. | Amino-group-containing polymer (salt) and production process therefor |
-
1986
- 1986-08-28 JP JP20006686A patent/JPS6356549A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5391633A (en) * | 1989-11-20 | 1995-02-21 | Nippon Shokubai Co., Ltd. | Curable resin composition |
| US6441102B2 (en) | 2000-02-10 | 2002-08-27 | Nippon Shokubai Co., Ltd. | Amino-group-containing polymer (salt) and production process therefor |
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