JPH01282270A - Urethane-based resin composition for paint - Google Patents
Urethane-based resin composition for paintInfo
- Publication number
- JPH01282270A JPH01282270A JP63112969A JP11296988A JPH01282270A JP H01282270 A JPH01282270 A JP H01282270A JP 63112969 A JP63112969 A JP 63112969A JP 11296988 A JP11296988 A JP 11296988A JP H01282270 A JPH01282270 A JP H01282270A
- Authority
- JP
- Japan
- Prior art keywords
- weight
- polyisocyanate
- copolymer
- urethane
- resin composition
- 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 8
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims description 5
- 239000003973 paint Substances 0.000 title description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 17
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 16
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 16
- 229920001577 copolymer Polymers 0.000 claims abstract description 14
- 239000000178 monomer Substances 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 239000000126 substance Substances 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 3
- 238000000576 coating method Methods 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 9
- 239000000203 mixture Substances 0.000 abstract description 5
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 abstract description 4
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 abstract description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 abstract description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 abstract description 3
- 238000002156 mixing Methods 0.000 abstract description 2
- UFLXKQBCEYNCDU-UHFFFAOYSA-N (2,2,6,6-tetramethylpiperidin-4-yl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CC(C)(C)NC(C)(C)C1 UFLXKQBCEYNCDU-UHFFFAOYSA-N 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- -1 acrylic polyols Chemical class 0.000 description 6
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 5
- 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 4
- 229920000178 Acrylic resin Polymers 0.000 description 4
- 239000004925 Acrylic resin Substances 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000005856 abnormality Effects 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012860 organic pigment Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- 239000004640 Melamine resin Substances 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- 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 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000000466 oxiranyl group Chemical group 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 125000003386 piperidinyl group Chemical group 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 229920002050 silicone resin Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 235000010215 titanium dioxide Nutrition 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 2
- NWPIOULNZLJZHU-UHFFFAOYSA-N (1,2,2,6,6-pentamethylpiperidin-4-yl) 2-methylprop-2-enoate Chemical compound CN1C(C)(C)CC(OC(=O)C(C)=C)CC1(C)C NWPIOULNZLJZHU-UHFFFAOYSA-N 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- PAOHAQSLJSMLAT-UHFFFAOYSA-N 1-butylperoxybutane Chemical compound CCCCOOCCCC PAOHAQSLJSMLAT-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical class ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- NJRHMGPRPPEGQL-UHFFFAOYSA-N 2-hydroxybutyl prop-2-enoate Chemical compound CCC(O)COC(=O)C=C NJRHMGPRPPEGQL-UHFFFAOYSA-N 0.000 description 1
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-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
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 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
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 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
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
- HDONYZHVZVCMLR-UHFFFAOYSA-N N=C=O.N=C=O.CC1CCCCC1 Chemical compound N=C=O.N=C=O.CC1CCCCC1 HDONYZHVZVCMLR-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical class CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- CJOBVZJTOIVNNF-UHFFFAOYSA-N cadmium sulfide Chemical compound [Cd]=S CJOBVZJTOIVNNF-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-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
- 239000011261 inert gas Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical class C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、耐候性に優れ、常温又は低温硬化可能な塗料
用ウレタン系樹脂組成物に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a urethane resin composition for paints that has excellent weather resistance and can be cured at room temperature or low temperature.
近年、塗料業界においては、省資源、省エネルギーとい
う観点から耐候性に優れ（従って、塗膜のメンテナンス
が不要であり）、常温又は低温硬化性の塗料が要望され
ている。従来、耐候性が要求される用途には、アクリル
樹脂が一般的に使用されているが、より一層のレベルア
ップが望まれている。BACKGROUND ART In recent years, in the paint industry, there has been a demand for paints that are excellent in weather resistance (therefore, maintenance of the paint film is not required) and can be cured at room temperature or at low temperatures, from the viewpoint of saving resources and energy. Conventionally, acrylic resins have been commonly used for applications that require weather resistance, but there is a desire for further improvements.
また、常温若しくは低温硬化可能な塗料としては、アク
リル樹脂とメラミン樹脂、アルキド樹脂とメラミン樹脂
、アクリル樹脂とエポキシ樹脂、アクリル樹脂とシリコ
ン樹脂等の主剤と硬化剤の組み合わせが知られているが
、低温硬化性及び塗膜性能の点から硬化剤としてポリイ
ソシアネート化合物を使用するウレタン系塗料が有望で
ある。In addition, as paints that can be cured at room temperature or low temperature, combinations of base materials and curing agents, such as acrylic resin and melamine resin, alkyd resin and melamine resin, acrylic resin and epoxy resin, acrylic resin and silicone resin, are known. Urethane-based paints that use polyisocyanate compounds as curing agents are promising in terms of low-temperature curability and coating performance.
なかでもアクリルポリオールとポリイソシアネートを反
応させるアクリルウレタン塗料は乾燥性、耐溶剤性、光
沢等に優れている。Among them, acrylic urethane paints made by reacting acrylic polyols with polyisocyanates have excellent drying properties, solvent resistance, gloss, and the like.
一方、最近になって超耐候性塗料用樹脂として、特公昭
６１−１５８９１号公報に見られるような溶剤可溶型弗
素樹脂が用いられるようになった。On the other hand, recently, solvent-soluble fluororesins such as those disclosed in Japanese Patent Publication No. 61-15891 have come to be used as resins for super weather-resistant paints.
〔発明が解決しようとする課題］
上記のような溶剤可溶型の弗素樹脂は従来の分散型の弗
素樹脂に比べ、塗装作業性は改良され、しかも耐候性は
優れているものの、顔料分散性、耐汚染性が悪い等の欠
点がある。[Problems to be Solved by the Invention] Although the solvent-soluble fluororesin described above has improved coating workability and excellent weather resistance than conventional dispersion-type fluororesin, it has poor pigment dispersibility. , has drawbacks such as poor stain resistance.
従って、本発明は、アクリルウレタン塗料の耐候性を、
弗素樹脂やシリコン樹脂に匹敵するまで向上させ、かつ
、耐汚染性、耐水性、耐薬品性とのバランスのとれた常
温又は低温硬化可能な塗料用ウレタン系樹脂組成物を提
供することを目的とするものである。Therefore, the present invention improves the weather resistance of acrylic urethane paint.
The purpose of the present invention is to provide a urethane resin composition for paints that can be cured at room temperature or low temperature and has improved properties comparable to fluororesins and silicone resins, and has well-balanced stain resistance, water resistance, and chemical resistance. It is something to do.
本発明は、特定のアクリルポリオール成分を用いること
によって上記の課題を解決したものである。The present invention solves the above problems by using a specific acrylic polyol component.
即ち、本発明は、
（Ａ）一般式：
〔式中、Ｒ１は水素又はメチル基を表し、Ｒ２、Ｒ１、
Ｒ４及びＲ１はそれぞれ独立に炭素原子数１〜１８のア
ルキル基を表し、Ｒ８は水素又は炭素原子数１〜１８の
アルキル基を表す。〕で表される２、２，６．６−チト
ラアルキルピベリジン化合物０．１〜１０重量％、
（Ｂ）水酸基を有するモノエチレン性不飽和単量体０〜
５０重量％及び
（Ｃ）他の共重合可能な不飽和単量体９９．９〜４０重
量％を、全体が１００重量％になるよう配合したものを
必須成分とする成分を重合させて得られた水酸基価２０
〜１５０の共重合体（１）並びに
ポリイソシアネート（Ｉ［）
を含有してなる塗料用ウレタン系樹脂組成物に関する。That is, the present invention provides (A) general formula: [wherein R1 represents hydrogen or a methyl group, R2, R1,
R4 and R1 each independently represent an alkyl group having 1 to 18 carbon atoms, and R8 represents hydrogen or an alkyl group having 1 to 18 carbon atoms. ] 0.1 to 10% by weight of a 2,2,6.6-titraalkylpiveridine compound represented by (B) 0 to 10% of a monoethylenically unsaturated monomer having a hydroxyl group
Obtained by polymerizing a component whose essential components are 50% by weight and (C) 99.9 to 40% by weight of other copolymerizable unsaturated monomers so that the total is 100% by weight. Hydroxyl value 20
-150 copolymer (1) and polyisocyanate (I[).
本発明において（１）の共重合体は、前記のような（Ａ
）〜（Ｃ）を必須成分とする成分から構成されるもので
ある。使用する（Ａ）成分は、紫外線吸収能をもつピペ
リジン基及び他の（Ｂ）及び（Ｃ）成分と共重合可能な
ようにエチレン性の不飽和二重結合を同一分子内に有す
る化合物である。ピペリジン基の２位及び６位（一般式
においてＲ２とＲ１及びＲ４とＲ２の全て）には、炭素
原子数が１〜１８のアルキル基が存在することが必須で
あり、これにより十分な耐候性を得ることができる。（
Ａ）成分の化合物としては、例えば４−メタクリロイル
オキシ−１，２，２，６，６−ペンタメチルピペリジン
、４−メタクリロイルオキシ−２，２，６，６−チトラ
メチルピベリジン、４−アクリロイルオキシ−１，２，
２，６゜６−ペンタメチルピペリジン、４−アクリロイ
ルオキシ−２，２，６，６−チトラメチルビベリジン、
４−メタクリロイルオキシ−２，２，６，６−チトラメ
チルピペリジン等が挙げられる。（Ａ）成分の使用量は
０．１〜１０重量％、好ましくは０．５〜５重量％であ
る。この使用量が０．１重量％未満では、本発明の目的
である耐候性が不充分であり、１０重量％を超えると、
塗膜の耐水性、耐薬品性が低下する。In the present invention, the copolymer (1) is the above-mentioned (A
) to (C) as essential components. The component (A) used is a compound that has a piperidine group with ultraviolet absorbing ability and an ethylenically unsaturated double bond in the same molecule so that it can be copolymerized with the other components (B) and (C). . It is essential that an alkyl group having 1 to 18 carbon atoms be present in the 2nd and 6th positions of the piperidine group (all of R2 and R1 and R4 and R2 in the general formula), which provides sufficient weather resistance. can be obtained. (
Examples of the compound of component A) include 4-methacryloyloxy-1,2,2,6,6-pentamethylpiperidine, 4-methacryloyloxy-2,2,6,6-titramethylpiperidine, 4-acryloyl Oxy-1,2,
2,6゜6-pentamethylpiperidine, 4-acryloyloxy-2,2,6,6-titramethylbiveridine,
Examples include 4-methacryloyloxy-2,2,6,6-titramethylpiperidine. The amount of component (A) used is 0.1 to 10% by weight, preferably 0.5 to 5% by weight. If the amount used is less than 0.1% by weight, the weather resistance, which is the objective of the present invention, is insufficient, and if it exceeds 10% by weight,
The water resistance and chemical resistance of the coating film decreases.
（Ｂ）成分としては、２−ヒドロキシエチルアクリレー
ト、２−ヒドロキシプロピルアクリレート、２−ヒドロ
キシブチルアクリレート等のヒドロキシアルキルアクリ
レート類、同様のヒドロキシアルキルメタクリレート類
、グリセリン、トリメチロールプロパン等の多価アルコ
ールのモノアクリレート又はモノメタクリレート類、Ｎ
−メチロールアクリルアミド、Ｎ−メチロールメタクリ
ルアミド等がある。（Ｂ）成分の使用量は５０重量％以
下である必要がある。５０重１％を超えると、共重合体
（１）とポリイソシアネート（ＩＩ）を配合した後の可
使時間が短くなり好ましくない。Component (B) includes hydroxyalkyl acrylates such as 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, and 2-hydroxybutyl acrylate, similar hydroxyalkyl methacrylates, and polyhydric alcohol monomers such as glycerin and trimethylolpropane. Acrylates or monomethacrylates, N
-Methylol acrylamide, N-methylol methacrylamide, etc. The amount of component (B) used must be 50% by weight or less. If it exceeds 50% by weight, the pot life after blending the copolymer (1) and the polyisocyanate (II) becomes short, which is not preferable.
（Ｃ）成分としては、メチルアクリレート、エチルアク
リレート、ブチルアクリレート、イソプロピルアクリレ
ート、２−エチルへキシルアクリレート等のアルキルア
クリレート、同様のアルキルメタクリレート、スチレン
若しくはビニルトルエン、α−メチルスチレン、クロロ
スチレン等の置換スチレン、アクリロニトリル、メタク
リレートリル、塩化ビニル、酢酸ビニル、マレイン酸ジ
アルキルエステルを使用することができる。Component (C) includes alkyl acrylates such as methyl acrylate, ethyl acrylate, butyl acrylate, isopropyl acrylate, and 2-ethylhexyl acrylate, similar alkyl methacrylates, substituted styrene or vinyltoluene, α-methylstyrene, chlorostyrene, etc. Styrene, acrylonitrile, methacrylate trile, vinyl chloride, vinyl acetate, maleic acid dialkyl esters can be used.
また、必要に応じてアクリルアミド、メタクリルアミド
等の不飽和アミド、グリシジルメタクリレート、グリシ
ジルアクリレート等のオキシラン基を有する重合性単量
体、アクリル酸、メタクリル酸、マレイン酸モノアルキ
ルエステル等のα。In addition, if necessary, unsaturated amides such as acrylamide and methacrylamide, polymerizable monomers having an oxirane group such as glycidyl methacrylate and glycidyl acrylate, and α such as acrylic acid, methacrylic acid, and maleic acid monoalkyl ester.
β−不飽和カルボン酸を用いることができる。不飽和ア
ミド及びオキシラン基を含有する重合性単量体は多すぎ
ると、塗膜の耐水性が低下したり、反応溶媒が限定され
たりする傾向が生じるため、（Ａ）、（Ｂ）及び（Ｃ）
成分の総量に対して３０重量％以下で使用するのが好ま
しく、α、β−不飽和カルボン酸が多すぎると、塗膜の
耐水性が低下する傾向があるため、１０重量％以下で使
用するのが好ましい。β-unsaturated carboxylic acids can be used. If the amount of polymerizable monomers containing unsaturated amide and oxirane groups is too large, the water resistance of the coating film tends to decrease or the reaction solvent is limited, so (A), (B) and ( C)
It is preferably used in an amount of 30% by weight or less based on the total amount of components, and if the amount of α,β-unsaturated carboxylic acid is too large, the water resistance of the coating film tends to decrease, so it is used in an amount of 10% by weight or less. is preferable.
また、本発明に用いる共重合体（１）は、水酸基価が２
０〜１５０、好ましくは３５〜１００とされる。水酸基
価が２０未満では、水酸基が少なすぎるために、ポリ、
イソシアネート（ｎ）と反応させても、架橋密度が不充
分になり、耐候性、耐溶剤性が劣る。逆に、水酸基価が
１５０を超えると、ポリイソシアネート（ＩＩ）と混合
した時の可使時間が短くなり、実用上の障害となる。共
重合体（１）の水酸基価は（Ｂ）成分である、水酸基を
有するモノエチレン性不飽和単量体の種類、使用量によ
って調整できる。Further, the copolymer (1) used in the present invention has a hydroxyl value of 2.
0 to 150, preferably 35 to 100. If the hydroxyl value is less than 20, there are too few hydroxyl groups, so poly,
Even if it is reacted with isocyanate (n), the crosslinking density will be insufficient and the weather resistance and solvent resistance will be poor. On the other hand, when the hydroxyl value exceeds 150, the pot life when mixed with polyisocyanate (II) becomes short, which poses a practical problem. The hydroxyl value of the copolymer (1) can be adjusted by the type and amount of the monoethylenically unsaturated monomer having a hydroxyl group, which is the component (B).
また、共重合体（１）は、酸価が０．５〜２０であるも
のが好ましく、特に１〜１５であるものが好ましい。こ
れによりポリイソシアネート（■）との硬化反応を促進
させることができる。酸価は大きすぎると、可使時間が
短くなるので、注意を要する。酸価の調整は、上記（Ｃ
）成分として使用できるα、β−不飽和カルボン酸の使
用量を調整して行うことができる。Further, the copolymer (1) preferably has an acid value of 0.5 to 20, particularly preferably 1 to 15. This can accelerate the curing reaction with polyisocyanate (■). If the acid value is too high, the pot life will be shortened, so care must be taken. Adjustment of acid value is as described above (C
) The amount of α,β-unsaturated carboxylic acid used as the component can be adjusted.
（Ａ）、（Ｂ）及び（Ｃ）を必須成分とする成分を共重
合して共重合体（１）を製造するには、必要に応じてト
ルエン、キシレン、メチルイソブチルケトン、酢酸ブチ
ル、酢酸エチル、酢酸セロソルブ、ブチルセロソルブ、
１−ブタノール、２−７’タノール、１−プロパツール
、２−プロパツール等の有機溶剤を反応溶媒とし、重合
触媒として過酸化ベンゾイル、ジーｔｅｒ ｔ−ブチル
ペルオキシド、クメンヒドロペルオキシド等の過酸化物
、アゾビスイソブチロニトリル等のアゾビス系化合物を
用い、５０〜２００°Ｃで１〜１０時間加熱反応させれ
ばよい。この反応は、窒素ガス等の不活性ガスの雰囲気
又は気流下に行うのが好ましい。To produce copolymer (1) by copolymerizing components containing (A), (B), and (C) as essential components, toluene, xylene, methyl isobutyl ketone, butyl acetate, acetic acid may be used as necessary. Ethyl, cellosolve acetate, butyl cellosolve,
Organic solvents such as 1-butanol, 2-7'tanol, 1-propanol, and 2-propanol are used as reaction solvents, and peroxides such as benzoyl peroxide, di-tert-butyl peroxide, and cumene hydroperoxide are used as polymerization catalysts. The reaction may be carried out by heating at 50 to 200°C for 1 to 10 hours using an azobis-based compound such as azobisisobutyronitrile. This reaction is preferably carried out in an atmosphere or stream of an inert gas such as nitrogen gas.
残存上ツマ−を少なくするためには、アゾビス系化合物
と過酸化物を併用するのが好ましい。In order to reduce the residual residual amount, it is preferable to use an azobis compound and a peroxide in combination.
本発明に用いるポリイソシアネート（■）としては、ヘ
キサメチレンジイソシアネート、トリレンジイソシアネ
ート、キシリレンジイソシアネート、イソホロンジイソ
シアネート、リジ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、２．２．４−トリメチルヘキシル
メタンジイソシアネート、メチルシクロヘキサンジイソ
シアネート、イソプロピリデンビス（４−シクロヘキシ
ルイソシアネート）、ヘキサメチレンジイソシアネート
のビウレット体、イソシアヌレート環を含むイソホロン
ジイソシアネートの三量体等、これらのポリイソシアネ
ート類とプロパンジオール、ヘキサンジオール、ポリエ
チレングリコール、トリメチロールプロパン、ペンタエ
リトリット等の多価アルコールとの反応により生成され
、２個以上のイソシアネート基の残存する化合物等があ
る。The polyisocyanates (■) used in the present invention include hexamethylene diisocyanate, tolylene diisocyanate, xylylene diisocyanate, isophorone diisocyanate, lysine diisocyanate, diphenylmethane diisocyanate, 2.2.4-trimethylhexylmethane diisocyanate, methylcyclohexane diisocyanate, isopropylidene Biuret form of bis(4-cyclohexyl isocyanate), hexamethylene diisocyanate, trimer of isophorone diisocyanate containing an isocyanurate ring, etc., these polyisocyanates and propanediol, hexanediol, polyethylene glycol, trimethylolpropane, pentaerythritol. There are compounds that are produced by reaction with polyhydric alcohols such as, and have two or more remaining isocyanate groups.
共重合体（１）とポリイソシアネート（ＩＩ）は、水酸
基／イソシアネート基（当量比）が、０．６／１〜１．
２ ／ １になるように配合されるのが好ましく、はぼ
１／１になるように配合されるのが特に好ましい。０．
６ ／ １未満では、未反応ボリイソシアネートが増え
、また、１．２ ／ １を超えると、架橋密度が低くな
り、若しくは残存水酸基が多くなることにより、耐水性
、その他の塗膜性能が低下する傾向にある。The copolymer (1) and polyisocyanate (II) have a hydroxyl group/isocyanate group (equivalent ratio) of 0.6/1 to 1.
It is preferred that the ratio be 2/1, and it is particularly preferred that the ratio be approximately 1/1. 0.
If it is less than 6/1, the amount of unreacted polyisocyanate will increase, and if it exceeds 1.2/1, the crosslinking density will decrease or the number of residual hydroxyl groups will increase, resulting in a decrease in water resistance and other coating film performance. There is a tendency.
共重合体（Ｉ）及びポリイソシアネート（ＩＩ）は、本
発明に係るウレタン系樹脂組成物の使用直前に配合して
使用することができる。Copolymer (I) and polyisocyanate (II) can be blended and used immediately before use of the urethane resin composition according to the present invention.
また、共重合体（Ｉ）及びポリイソシアネート（ＩＩ）
はトルエン、キシレン、メチルイソブ、チルケトン、酢
酸ブチル、酢酸セロソルブ等の適当な有機溶剤に溶解さ
せて使用することができる。Also, copolymer (I) and polyisocyanate (II)
can be used by dissolving it in an appropriate organic solvent such as toluene, xylene, methyl isobu, tyl ketone, butyl acetate, and cellosolve acetate.
本発明に係るウレタン系樹脂組成物は、チタン白、カド
ミウムイエロー、カーボンブラック等の無機顔料、フタ
ロシアニン系、アゾ系等の有機顔料、その他の添加剤を
含有することができる。無機顔料及び有機顔料は、必要
量を適宜決定して使用されるが、使用量を例示すると、
本発明に係るウレタン系樹脂組成物の樹脂固形分に対し
て有機顔料は、約５〜２０重量％、チタン白は約５０〜
１００重量％、カーボンブラックは約１〜１０重量％の
割合で使用するのが好ましい。The urethane resin composition according to the present invention can contain inorganic pigments such as titanium white, cadmium yellow, and carbon black, organic pigments such as phthalocyanine pigments and azo pigments, and other additives. Inorganic pigments and organic pigments are used by appropriately determining the necessary amounts, but examples of the amounts used are as follows:
The organic pigment is about 5 to 20% by weight, and the titanium white is about 50 to 20% by weight based on the resin solid content of the urethane resin composition according to the present invention.
Preferably, carbon black is used in a proportion of about 1 to 10% by weight.
顔料及びその他の添加剤は、予め共重合体（Ｉ）と混練
して使用するのが好ましい。It is preferable that the pigment and other additives are used after being kneaded with the copolymer (I) in advance.
その他の添加剤としては、例えば紫外線吸収剤、酸化防
止剤、難燃剤、滑剤等が挙げられる。Examples of other additives include ultraviolet absorbers, antioxidants, flame retardants, and lubricants.
次に、実施例により本発明を更に詳細に説明する。以下
、部とあるのは重量部を意味する。Next, the present invention will be explained in more detail with reference to Examples. Hereinafter, parts refer to parts by weight.
実施例１
温度計、撹拌機、窒素ガス吹き込み管及び還流冷却器を
備えたフラスコにキシレン５０部及び酢酸ブチル１−０
部を仕込み、撹拌しながら窒素気流下に１１０°Ｃまで
昇温した。１１０°Ｃに保温したまま、下記の混合液を
２時間かけて均一に滴下した。Example 1 50 parts of xylene and 1-0 butyl acetate were placed in a flask equipped with a thermometer, stirrer, nitrogen gas blowing tube, and reflux condenser.
The temperature was raised to 110°C under a nitrogen stream while stirring. While keeping the temperature at 110°C, the following liquid mixture was uniformly added dropwise over 2 hours.
４−メタクリロイルオキシ−１，２，２，６゜６−ペン
タメチルビペラジン １部アクリル酸２−ヒ
ドロキシエチル １５，５部スチレン
１０．０部メタクリル酸メチル
４４．５部メタクリル酸ブチル
２８部メタクリル酸 １部
アゾビスイソブチロニトリル ２．６部ジｔ−
ブチルペルオキシド ０．１部滴下終了後、
１１０°Ｃの保温を１時間、更に１３０ ’Ｃの保温を
３時間継続し、重合を完結させた。重合終了後、酢酸ブ
チルを３０部加え、加熱残分５４．５％、粘度（ガード
ナー法、２５°Ｃ）Ｕ−■、酸価３．５、水酸基価３７
．８の樹脂を得た。4-Methacryloyloxy-1,2,2,6゜6-pentamethylbiperazine 1 part 2-hydroxyethyl acrylate 15.5 parts Styrene
10.0 parts methyl methacrylate
44.5 parts Butyl methacrylate
28 parts methacrylic acid 1 part azobisisobutyronitrile 2.6 parts di-t-
After finishing dropping 0.1 part of butyl peroxide,
The polymerization was completed by keeping the temperature at 110°C for 1 hour and then keeping it at 130'C for 3 hours. After the polymerization was completed, 30 parts of butyl acetate was added, and the heating residue was 54.5%, viscosity (Gardner method, 25°C) U-■, acid value 3.5, hydroxyl value 37.
．． Resin No. 8 was obtained.
実施例２〜４及び比較例１〜４
滴下する混合液を変えた以外は、実施例１と同様の操作
を行い、樹脂を得た。混合液の組成及び樹脂の特性を第
１表に示す。Examples 2 to 4 and Comparative Examples 1 to 4 Resins were obtained by carrying out the same operation as in Example 1, except that the liquid mixture to be dropped was changed. Table 1 shows the composition of the mixed liquid and the properties of the resin.
比較例５
比較例１で製造した樹脂１００部に対して、２部の１．
２，２．６．６−ペンタメチルピペリジンを添加し、均
一に混合した。Comparative Example 5 For 100 parts of the resin produced in Comparative Example 1, 2 parts of 1.
2,2.6.6-pentamethylpiperidine was added and mixed uniformly.
実施例１〜４及び比較例１〜５で製造した樹脂を塗料化
して塗膜の性能評価試験を行った。ポリイソシアネート
として、コロネートＥＨ０（日本ポリウレタン社製）を
使用し、樹脂水酸基とコロネ−１−ＥＨのイソシアネー
ト基が当モルになるように配合した。ボンデライト＃１
４４処理鋼板に乾燥膜厚が３０μになるようにバーコー
ダで塗布し、８０ ’ＣＸ ９０分の焼付を行い、更に
室温で３日間乾燥させ、塗膜性能を評価した。その結果
を第２表に示す。The resins produced in Examples 1 to 4 and Comparative Examples 1 to 5 were made into paints, and a performance evaluation test of the paint films was conducted. Coronate EH0 (manufactured by Nippon Polyurethane Co., Ltd.) was used as the polyisocyanate, and the resin hydroxyl groups and the isocyanate groups of Coronate-1-EH were mixed in equimolar amounts. Bonderite #1
44 treated steel plate using a barcoder so that the dry film thickness was 30 μm, baked at 80'CX for 90 minutes, and further dried at room temperature for 3 days to evaluate the film performance. The results are shown in Table 2.
（以下余白） 上記の試験は下記の方法で行った。(Margin below) The above test was conducted in the following manner.
（１）促進耐候性試験
作製した試験板をＱ−ＵＶ促進耐候性試験機（米国、Ｑ
−ｐａｎｅ１社製）を使用し、紫外線照射６０°Ｃで６
時間〜結露５０″Ｃで６時間のサイクル条件下に所定時
間曝露した後、６０°鏡面反射率を測定した。(1) Accelerated weathering test
60°C under UV irradiation.
The 60° specular reflectance was measured after exposure for a specified period of time under cycle conditions of 6 hours at 50''C with condensation.
（２）耐薬品性
耐酸性は、５％塩酸溶液中に、耐アルカリ性は５％水酸
化ナトリウム溶液中に１６８時間浸漬し、塗膜の状態を
目視で観察した。(2) Chemical resistance Acid resistance was determined by immersion in a 5% hydrochloric acid solution, and alkali resistance was determined by immersion in a 5% sodium hydroxide solution for 168 hours, and the condition of the coating film was visually observed.
Ｏ：塗膜に異常が認められない。O: No abnormality is observed in the coating film.
△：塗膜がやや艶消しされているものの、ブリスターの
発生なし。△: Although the coating film was slightly matte, no blisters were generated.
×：艶消し、かつブリスターが発生している。×: Matte and blisters are generated.
（３）耐水性
２０°Ｃの水中に、１４日間浸漬し、塗膜の状態を目視
で観察する。(3) Water resistance Immerse in water at 20°C for 14 days and visually observe the condition of the coating film.
○：塗膜に異常が認められない。○: No abnormality is observed in the coating film.
×：塗膜に、艶消し、ブリスター発生等の異常が認めら
れる。×: Abnormalities such as matting and blistering are observed in the coating film.
（４）ポットライフ
塗膜性能評価試験用に塗料を作成したと同様に、樹脂の
水酸基とコロネートＥＨのイソシアネート基が等モルに
なるように配合し、トルエン／キシレン／酢酸ブチル＝
５０／２５／２５のシンナーで塗料粘度がフォードカッ
プ＃４（２５°Ｃ）で１４±１秒になるように希釈した
。２３°Ｃ１７０％ＲＨの養生室に放置し、塗料粘度が
２８秒になるまでに要した時間をポットライフとした。(4) In the same way as the paint was created for the pot-life coating film performance evaluation test, the hydroxyl groups of the resin and the isocyanate groups of Coronate EH were mixed in equal moles, and toluene/xylene/butyl acetate =
The paint was diluted with 50/25/25 thinner to a paint viscosity of 14±1 seconds in a Ford Cup #4 (25°C). It was left in a curing room at 23°C and 170% RH, and the time required for the paint viscosity to reach 28 seconds was defined as the pot life.
（発明の効果）
本発明の塗料用ウレタン系樹脂組成物の使用により耐候
性の優れた、耐汚染性、耐水性及び耐薬品性においてバ
ランスのとれた塗膜を得ることができる。(Effects of the Invention) By using the urethane resin composition for paints of the present invention, it is possible to obtain a coating film that has excellent weather resistance and is well-balanced in stain resistance, water resistance, and chemical resistance.
Claims (1)
＿３、Ｒ＿４及びＲ＿５はそれぞれ独立に炭素原子数１
〜１８のアルキル基を表し、Ｒ＿６は水素又は炭素原子
数１〜１８のアルキル基を表す。〕で表される２，２，
６，６−テトラアルキルピペリジン化合物０．１〜１０
重量％、 （Ｂ）水酸基を有するモノエチレン性不飽和単量体０〜
５０重量％及び （Ｃ）他の共重合可能な不飽和単量体９９．９〜４０重
量％を、全体が１００重量％になるよう配合したものを
必須成分とする成分を重合させて得られた水酸基価２０
〜１５０の共重合体（ I ）並びに ポリイソシアネート（II） を含有してなる塗料用ウレタン系樹脂組成物。[Claims] 1. (A) General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, R_1 represents hydrogen or a methyl group, R_2, R
_3, R_4 and R_5 each independently have a carbon atom number of 1
~18 alkyl group, and R_6 represents hydrogen or an alkyl group having 1 to 18 carbon atoms. ] 2, 2,
6,6-tetraalkylpiperidine compound 0.1-10
Weight %, (B) monoethylenically unsaturated monomer having hydroxyl group 0 to
Obtained by polymerizing a component whose essential components are 50% by weight and (C) 99.9 to 40% by weight of other copolymerizable unsaturated monomers so that the total is 100% by weight. Hydroxyl value 20
A urethane-based resin composition for coatings comprising a copolymer (I) of 150 to 150 and a polyisocyanate (II).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63112969A JPH01282270A (en) | 1988-05-10 | 1988-05-10 | Urethane-based resin composition for paint |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63112969A JPH01282270A (en) | 1988-05-10 | 1988-05-10 | Urethane-based resin composition for paint |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01282270A true JPH01282270A (en) | 1989-11-14 |
Family
ID=14600083
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63112969A Pending JPH01282270A (en) | 1988-05-10 | 1988-05-10 | Urethane-based resin composition for paint |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01282270A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0291170A (en) * | 1988-09-29 | 1990-03-30 | Mitsubishi Rayon Co Ltd | Thermosetting coating composition |
| JP2012167245A (en) * | 2010-09-29 | 2012-09-06 | Tokuyama Corp | Photochromic composition |
-
1988
- 1988-05-10 JP JP63112969A patent/JPH01282270A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0291170A (en) * | 1988-09-29 | 1990-03-30 | Mitsubishi Rayon Co Ltd | Thermosetting coating composition |
| JP3166772B2 (en) * | 1988-09-29 | 2001-05-14 | 三菱レイヨン株式会社 | Coating method |
| JP2012167245A (en) * | 2010-09-29 | 2012-09-06 | Tokuyama Corp | Photochromic composition |
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