JPS63142009A - Acrylpolyol and two-pack urethane resin coating composition containing same - Google Patents
Acrylpolyol and two-pack urethane resin coating composition containing sameInfo
- Publication number
- JPS63142009A JPS63142009A JP61288670A JP28867086A JPS63142009A JP S63142009 A JPS63142009 A JP S63142009A JP 61288670 A JP61288670 A JP 61288670A JP 28867086 A JP28867086 A JP 28867086A JP S63142009 A JPS63142009 A JP S63142009A
- Authority
- JP
- Japan
- Prior art keywords
- polymerizable unsaturated
- unsaturated monomer
- weight
- meth
- urethane resin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920002803 thermoplastic polyurethane Polymers 0.000 title claims abstract description 19
- 239000008199 coating composition Substances 0.000 title claims abstract description 10
- 239000000178 monomer Substances 0.000 claims abstract description 44
- 229920005862 polyol Polymers 0.000 claims abstract description 35
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 230000002378 acidificating effect Effects 0.000 claims abstract description 8
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 8
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 8
- -1 acrylic polyol Chemical class 0.000 claims description 30
- 125000000524 functional group Chemical group 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract description 23
- 238000000576 coating method Methods 0.000 abstract description 17
- 239000011248 coating agent Substances 0.000 abstract description 15
- 150000003077 polyols Chemical class 0.000 abstract description 12
- 239000002904 solvent Substances 0.000 abstract description 12
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 abstract description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract description 2
- 238000007334 copolymerization reaction Methods 0.000 abstract 2
- 239000003973 paint Substances 0.000 description 18
- 238000001035 drying Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-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
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 229940043232 butyl acetate Drugs 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 238000010422 painting Methods 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- IKYNWXNXXHWHLL-UHFFFAOYSA-N 1,3-diisocyanatopropane Chemical compound O=C=NCCCN=C=O IKYNWXNXXHWHLL-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-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
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-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
- 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical group CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 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
- 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
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 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
- 150000001412 amines Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000011109 contamination 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
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000002320 enamel (paints) Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 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
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000001023 inorganic pigment Substances 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
- 230000014759 maintenance of location Effects 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
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 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
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 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
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 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
- 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
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 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
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyurethanes Or Polyureas (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、アクリルポリオールおよびこれを含んでなる
二液ウレタン樹脂塗料用組成物に関するものである。更
に詳しくは塗料、インキ等各種用途に有用なアクリルポ
リオールおよびこれを含んでなる乾燥性、硬度、光沢、
肉持ち性、耐候性、耐溶剤性の優れた塗膜と優れた作業
性を有する二液ウレタン樹脂塗料用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 an acrylic polyol and a two-component urethane resin coating composition containing the same. More specifically, acrylic polyols useful for various uses such as paints and inks, and drying properties, hardness, gloss, and acrylic polyols containing the same.
The present invention relates to a two-component urethane resin coating composition that has a coating film with excellent durability, weather resistance, and solvent resistance, and excellent workability.
（従来の技術）
従来、二液ウレタン樹脂塗料に用いられるポリオールと
しては、アクリルポリオール、ポリエステルポリオール
、油変性アルキドポリオールなどが広く知られている。(Prior Art) Conventionally, acrylic polyols, polyester polyols, oil-modified alkyd polyols, and the like are widely known as polyols used in two-component urethane resin paints.
しかし、アクリルポリオールを用いたアクリルウレタン
樹脂塗料は、溶剤希釈性、スプレー適性が劣り、得られ
る塗膜は乾燥性を速くすれば塗装時のレベリングが悪く
なったり、光沢はあるが肉持ち性が劣ったり、更には硬
化初期の耐溶剤性や屋外暴露時の耐チヨーキング性にも
問題がある。また、ポリエステルポリオールや油変性ア
ルキドポリオールを用いたウレタン樹脂塗料は溶剤希釈
性、スプレー適性が良く、得られる塗膜は光沢、肉持ち
性は良いが、初期乾燥性、耐薬品性や屋外暴露時の食込
みによる汚染性などに欠点がある。However, acrylic urethane resin paints using acrylic polyols have poor solvent dilutability and sprayability, and the resulting paint film has poor leveling during painting if it dries quickly, and although it is glossy, it has poor durability. In addition, there are problems with solvent resistance in the initial stage of curing and yoking resistance during outdoor exposure. In addition, urethane resin paints using polyester polyols or oil-modified alkyd polyols have good solvent dilutability and sprayability, and the resulting paint films have good gloss and durability, but they also have poor initial drying properties, chemical resistance, and resistance to outdoor exposure. There are disadvantages such as contamination due to penetration.
（発明が解決しようとする問題点）
本発明者らは、これらの欠点を克服すべく鋭意研究を重
ねた結果、シクロアルキル基と特定の官能基を含有する
アクリルポリオールが塗料、インキ等各種用途に有用な
る性能を示し、特にこのアクリルポリオールを用いた二
液ウレタン樹脂塗料用組成物が、溶剤希釈性、スプレー
適性が良く、得られた塗膜は乾燥性とレベリング性のバ
ランスが良く、硬度、光沢、肉持ち性、耐候性、耐溶剤
性、耐ガソリン性に優れた塗膜を形成することを見出し
、本発明を完成するに至った。(Problems to be Solved by the Invention) As a result of intensive research to overcome these drawbacks, the present inventors have found that acrylic polyols containing cycloalkyl groups and specific functional groups have been developed for various uses such as paints and inks. In particular, a two-component urethane resin coating composition using this acrylic polyol has good solvent dilutability and sprayability, and the resulting coating film has a good balance between drying and leveling properties, and has low hardness. The present inventors have discovered that a coating film can be formed with excellent gloss, durability, weather resistance, solvent resistance, and gasoline resistance, and have completed the present invention.
（問題点を解決するための手段および作用）すなわち、
本発明は
（１１シクロアルキル基を含有する重合性不飽和単量体
（ａ） ５．０〜９７．９重量％、水酸基を含有する重
合性不飽和単量体（ｂ） ２．０〜３５．０重量％、酸
性官能基を含有する重合性不飽和単量体（ｃ） ０．１
〜５０重１％及びその他の重合性不飽和単量体（ｄ）
０．０〜９２．９重量％（但し、（ａｌ、（ｂ）、（ｃ
）及び（ｄｌの合計は１００重量％である。）を共重合
してなるシクロアルキル基を含有するアクリルポリオー
ル。(Means and actions for solving problems) That is,
The present invention consists of (11) 5.0 to 97.9% by weight of a polymerizable unsaturated monomer (a) containing a cycloalkyl group, and 2.0 to 35% by weight of a polymerizable unsaturated monomer (b) containing a hydroxyl group. .0% by weight, polymerizable unsaturated monomer containing acidic functional group (c) 0.1
~50% by weight and other polymerizable unsaturated monomers (d)
0.0 to 92.9% by weight (however, (al, (b), (c
) and (the total of dl is 100% by weight). An acrylic polyol containing a cycloalkyl group.
（２） シクロアルキル基を含有する重合性不飽和単
量体（ａ） ５．０〜９７．９重量％、水酸基を含有す
る重合性不飽和単量体（ｂ） ２．０〜３５．０重量％
、酸性官能基を含有する重合性不飽和単量体（ｃ） ０
．１〜５．０重量％及びその他の重合性不飽和単量体（
ｄ） ０．０〜９２．９重量％（但し、ｆａ）、ｆｂ）
、（ｃ）及び（ｄｌの合計は１００重量％である。）を
共重合してなるシクロアルキル基を含有するアクリルポ
リオールを含んでなる水酸基含有化合物並びにポリイソ
シアネート化合物
からなる二液ウレタン樹脂塗料用組成物。(2) Polymerizable unsaturated monomer containing cycloalkyl group (a) 5.0 to 97.9% by weight, polymerizable unsaturated monomer containing hydroxyl group (b) 2.0 to 35.0% by weight weight%
, polymerizable unsaturated monomer (c) containing an acidic functional group 0
．． 1 to 5.0% by weight and other polymerizable unsaturated monomers (
d) 0.0 to 92.9% by weight (fa), fb)
, (c) and (the total of dl is 100% by weight) for a two-component urethane resin paint comprising a hydroxyl group-containing compound comprising an acrylic polyol containing a cycloalkyl group and a polyisocyanate compound. Composition.
に関するものである。It is related to.
本発明に用いられるシクロアルキル基を含有する重合性
不飽和単量体（ａ）は、得られるアクリルポリオールを
二液ウレタン樹脂塗料用として使用する場合、塗膜の硬
度、光沢、肉持ち性、耐溶剤性、耐ガソリン性、耐候性
等の向上のために必須の成分である。シクロアルキル基
を含有する重合性不飽和単量体（ａ）としては、例えば
、シクロヘキシル（メタ）アクリレート、メチルシクロ
ヘキシル（メタ）アクリレート、ターシャリ−ブチルシ
クロヘキシル（メタ）アクリレート、シクロドデシル（
メタ）アクリレートなどを挙げることができ、これらの
１種又は２種以上を使用することができる。該単量体（
ａｌは５．０〜９７．９重量％の範囲で使用する。When the resulting acrylic polyol is used as a two-component urethane resin paint, the polymerizable unsaturated monomer (a) containing a cycloalkyl group used in the present invention improves the hardness, gloss, and durability of the coating film. It is an essential component for improving solvent resistance, gasoline resistance, weather resistance, etc. Examples of the polymerizable unsaturated monomer (a) containing a cycloalkyl group include cyclohexyl (meth)acrylate, methylcyclohexyl (meth)acrylate, tert-butylcyclohexyl (meth)acrylate, and cyclododecyl (
Examples include meth)acrylates, and one or more of these can be used. The monomer (
Al is used in a range of 5.0 to 97.9% by weight.
５．０重量％未満の場合は、塗膜の硬度、光沢、肉持ち
性、耐溶剤性、耐ガソリン性、耐候性等の性能が充分発
揮されず、逆に９７．９重量％を越えて多量を用いた場
合は、乾燥性及びレベリング性が両立し難くなるので好
ましくない。If it is less than 5.0% by weight, the hardness, gloss, durability, solvent resistance, gasoline resistance, weather resistance, etc. of the coating film will not be fully exhibited; on the other hand, if it exceeds 97.9% by weight, If a large amount is used, it becomes difficult to achieve both drying properties and leveling properties, which is not preferable.
本発明に用いられる水酸基を含有する重合性不飽和単量
体（ｂｌとしては、例えば、ヒドロキシエチル（メタ）
アクリレート、ヒドロキシプロピル（メタ）アクリレー
ト、カプロラクトン変性ヒドロキシ（メタ）アクリレー
ト（例えば、商品名プラクセルＦＭ、ダイセル化学工業
■製）、フタル酸とプロピレングリコールとから得られ
るポリエステルジオールのモノ（メタ）アクリレート、
コハク酸とプロピレングリコールとから得られるポリエ
ステルジオールのモノ（メタ）アクリレートなどの水酸
基を有する（メタ）アクリルモノマーを挙げることがで
き、これらの１種又は２種以上を使用することができる
。水酸基を含有する重合性単量体ｆｂｌは得られるアク
リルポリオールを二液ウレタン樹脂塗料用として使用す
る場合に、ポリイソシアネートとの反応に必須の成分で
あり、２．０〜３５０重量％、好ましくは３．５〜２３
．０重量りｂの範囲で使用する。２．０重量％未満の場
合は、得られるアクリルポリオールの活性水素量が少な
くなり、アクリルポリオールをウレタン樹脂塗料用とし
て使用する際、アクリルポリオールに対応して使用する
架橋剤のイソシアネート基含有化合物の量も少なくなり
、架橋密度が低くなりすぎて目的とする塗膜性能が得ら
れない。逆に３５重重量％超える多量では、架橋剤との
安定性が悪くなる。The polymerizable unsaturated monomer containing a hydroxyl group used in the present invention (bl is, for example, hydroxyethyl (meth)
Acrylate, hydroxypropyl (meth)acrylate, caprolactone-modified hydroxy (meth)acrylate (for example, trade name Plaxel FM, manufactured by Daicel Chemical Industries, Ltd.), mono(meth)acrylate of polyester diol obtained from phthalic acid and propylene glycol,
Examples include (meth)acrylic monomers having a hydroxyl group, such as mono(meth)acrylate of polyester diol obtained from succinic acid and propylene glycol, and one or more of these can be used. The polymerizable monomer fbl containing a hydroxyl group is an essential component for the reaction with polyisocyanate when the obtained acrylic polyol is used as a two-component urethane resin coating, and is preferably 2.0 to 350% by weight. 3.5-23
．． Use within the range of 0 weight b. If it is less than 2.0% by weight, the amount of active hydrogen in the resulting acrylic polyol will decrease, and when the acrylic polyol is used for urethane resin coatings, the isocyanate group-containing compound of the crosslinking agent used for the acrylic polyol will decrease. The amount becomes too small, and the crosslinking density becomes too low, making it impossible to obtain the desired coating film performance. On the other hand, if the amount exceeds 35% by weight, the stability with the crosslinking agent will deteriorate.
本発明に用いられる酸性官能基を含有する重合性不飽和
単量体（ｃ）としては、例えば、（メタ）アクリル酸、
クロトン酸、イタコン酸、マレイン酸及び無水マレイン
酸などの如きカルボキシル基含有不飽和単量体；ビニル
スルホン酸、スチレンスルホン酸及びスルホエチル（メ
タ）アクリレートなどの如きスルホン酸基含有不飽和単
量体；２−（メタ）アクリロイルオキシエチルアシッド
ホスフェート、２−（メタ）アクリロイルオキシプロピ
ルアシッドホスフェート、２−（メタ）アクリロイルオ
キシ−３−クロロ−プロピルアシッドホスフェート、２
−メタクロイルオキシエチルフェニルリン酸などの酸性
リン酸エステル系不飽和単量体などを挙げることができ
、これらの群から選ばれる１種又は２種以上を使用する
ことができる。Examples of the polymerizable unsaturated monomer (c) containing an acidic functional group used in the present invention include (meth)acrylic acid,
Carboxyl group-containing unsaturated monomers such as crotonic acid, itaconic acid, maleic acid and maleic anhydride; sulfonic acid group-containing unsaturated monomers such as vinylsulfonic acid, styrenesulfonic acid and sulfoethyl (meth)acrylate; 2-(meth)acryloyloxyethyl acid phosphate, 2-(meth)acryloyloxypropyl acid phosphate, 2-(meth)acryloyloxy-3-chloro-propyl acid phosphate, 2
- Acidic phosphoric acid ester unsaturated monomers such as methacroyloxyethyl phenyl phosphoric acid can be mentioned, and one or more types selected from these groups can be used.
該単量体（ｃ）はアクリルポリオール中の水酸基とポリ
イソシアネート化合物中のインシアネートとの反応の内
部触媒として作用するもので、０，１〜５．０重量％の
範囲で使用する。０，１重量％未満では、得られるアク
リルポリオールを二液ウレタン樹脂塗料用として使用す
る際、乾燥性に対して効果がなく、乾燥性を速めようと
する場合は水酸基とインシアネート基との反応を促進す
るだめの外部触媒を多量に必要とし、この場合にはポリ
イソシアネート化合物との安定性が悪く、塗装作業性を
著しく阻害する。逆に５．０重量％を超えて使用すると
、ヒドロキシル基とイソシアネート基との反応が著しく
促進され、外部触媒を多用した場合と同様に安定性が悪
くなり、塗装作業性も悪くなる。The monomer (c) acts as an internal catalyst for the reaction between the hydroxyl group in the acrylic polyol and the incyanate in the polyisocyanate compound, and is used in an amount of 0.1 to 5.0% by weight. If it is less than 0.1% by weight, it will have no effect on drying properties when the resulting acrylic polyol is used as a two-component urethane resin paint, and if drying is to be accelerated, the reaction between hydroxyl groups and incyanate groups will be insufficient. A large amount of external catalyst is required to promote the process, and in this case, the stability with the polyisocyanate compound is poor and the coating workability is significantly impaired. On the other hand, if it is used in an amount exceeding 5.0% by weight, the reaction between hydroxyl groups and isocyanate groups will be significantly accelerated, resulting in poor stability and poor coating workability, as in the case of extensive use of external catalysts.
本発明に用いられるその他の重合性不飽和単量体（ｄ）
としては、例えば、メチル（メタ）アクリレート、エチ
ル（メタ）アクリレート、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、ブチル（メタ
）アクリレート、イソブチル（メタ）アクリレート、タ
ーシャリ−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、ラウリル（メタ）アクリ
レート、ステアリル（メタ）アクリレートなどの（メタ
）アクリル酸アルキルエステル；グリシジル（メタ）ア
クリレートなどのエポキシ基含有不飽和単量体；（メタ
）アクリルアミド、Ｎ、Ｎ’−ジメチルアミノエチル（
メタ）アクリレート、ビニルピリジン、ビニルイミダゾ
ールなどの窒素含有不飽和単量体；塩化ビニル、塩化ビ
ニリデンなどのハロゲン含有不飽和単量体；スチレン、
α−メチルスチレン、ビニルトルエンなどの芳香族不飽
和単量体；酢酸ビニルなどのビニルエステル；ビニルエ
ーテル；（メタ）アクリロニトリルなどの不飽和シアン
化合物などを挙げることができ、これらの群から選ばれ
た１種又は２種以上を使用することができる。Other polymerizable unsaturated monomers (d) used in the present invention
Examples include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, 2 - (meth)acrylic acid alkyl esters such as ethylhexyl (meth)acrylate, lauryl (meth)acrylate, and stearyl (meth)acrylate; epoxy group-containing unsaturated monomers such as glycidyl (meth)acrylate; (meth)acrylamide, N , N'-dimethylaminoethyl (
Nitrogen-containing unsaturated monomers such as meth)acrylate, vinylpyridine, and vinylimidazole; Halogen-containing unsaturated monomers such as vinyl chloride and vinylidene chloride; styrene,
Aromatic unsaturated monomers such as α-methylstyrene and vinyltoluene; vinyl esters such as vinyl acetate; vinyl ethers; and unsaturated cyanide compounds such as (meth)acrylonitrile. One type or two or more types can be used.
その他の重合性不飽和単量体（ｄ）は、必要に応じて本
発明のアクリルポリオールの特徴を損わない範囲で使用
するもので、その使用量は０〜９２．９重量％とするこ
とができる。Other polymerizable unsaturated monomers (d) are used as necessary within a range that does not impair the characteristics of the acrylic polyol of the present invention, and the amount used is 0 to 92.9% by weight. I can do it.
本発明のアクリルポリオールは、前記のシクロアルキル
基を含有する重合性不飽和単量体（ａｌ、水酸基を含有
する重合性不飽和単量体ｆｂ）、酸性官能基を含有する
重合性不飽和単量体（ｃ）及びその他の重合性単量体（
ｄ）を従来公知の重合法によって重合して製造できる。The acrylic polyol of the present invention comprises a polymerizable unsaturated monomer containing the above-mentioned cycloalkyl group (al, a polymerizable unsaturated monomer fb containing a hydroxyl group), a polymerizable unsaturated monomer containing an acidic functional group, mer (c) and other polymerizable monomers (
It can be produced by polymerizing d) by a conventionally known polymerization method.
例えば溶液重合法を採用する際に使用できる溶剤として
は、例えば、トルエン、キシレンやその他の高沸点の芳
香族系溶剤；酢酸エチル、酢酸ブチルやセロソルブアセ
テートなどのエステル系溶剤；メチルエチルケトン、メ
チルイソブチルケトンなどのケトン系溶剤などを挙げる
ことができ、これらの１種又は２種以上の混合物を使用
することができる。また、重合開始剤としては、アゾビ
スイソブチルニトリル、ベンゾイルパーオキサイド、ジ
ーｔｅｒｔ−ブチルパーオキサイドなど通常のラジカル
重合開始剤を挙げることができる。For example, solvents that can be used when employing the solution polymerization method include toluene, xylene, and other high-boiling aromatic solvents; ester solvents such as ethyl acetate, butyl acetate, and cellosolve acetate; methyl ethyl ketone, methyl isobutyl ketone For example, ketone solvents such as these can be used, and one or a mixture of two or more of these can be used. Examples of the polymerization initiator include common radical polymerization initiators such as azobisisobutylnitrile, benzoyl peroxide, and di-tert-butyl peroxide.
反応温度は室温から２００°Ｃ１好ましくは４０〜１２
０℃の範囲である。The reaction temperature is room temperature to 200°C, preferably 40 to 12
It is in the range of 0°C.
また、本発明の二液ウレタン樹脂塗料用組成物を構成す
るポリインシアネート化合物としては、２個以上のイン
シアネート基を有するものであれば特に制限なく、例え
ば、トリメチレンジイソシアネート、１，６−へキサメ
チレンジイソシアネート、トリレンジイソシアネート、
ジフェニルメタンジイソシアネート、インホロンジイソ
シアネートなどのポリイソシアネート類を挙げることが
でき、１種又は２種以上の混合物として使用できる。Further, the polyinsyanate compound constituting the two-component urethane resin coating composition of the present invention is not particularly limited as long as it has two or more incyanate groups, such as trimethylene diisocyanate, 1,6- xamethylene diisocyanate, tolylene diisocyanate,
Examples include polyisocyanates such as diphenylmethane diisocyanate and inphorone diisocyanate, which can be used singly or as a mixture of two or more.
更に、本発明の二液ウレタン樹脂塗料用組成物は、水酸
基とインシアネート基とのウレタン化反応を促進させる
ための公知の触媒（例えばジラウリン酸ジーｎ−ブチル
スズなどの有機スズ化合物や第三級アミン）、有機溶剤
、充填剤、レベリング剤、可塑剤、安定剤、染料、顔料
など各種塗料用添加剤を適宜含んでいてもよい。Furthermore, the two-component urethane resin coating composition of the present invention can be prepared using a known catalyst (for example, an organic tin compound such as di-n-butyltin dilaurate or a tertiary It may contain various paint additives such as amines), organic solvents, fillers, leveling agents, plasticizers, stabilizers, dyes, and pigments.
（発明の効果）
本発明のポリオールは公知の顔料分散法により、種々の
無機顔料や有機顔料が容易に分散でき、着色エナメル塗
料として使用できる。また、本発明のポリオールは、架
橋成分としてポリイソシアネートを配合して、架橋硬化
型ウレタン樹脂塗料として使用できる。また、本発明の
ポリオールは、架橋成分としてメラミン樹脂を配合して
、熱硬化型メラミン変性樹脂塗料として使用できる。(Effects of the Invention) Various inorganic and organic pigments can be easily dispersed in the polyol of the present invention by a known pigment dispersion method, and it can be used as a colored enamel paint. Furthermore, the polyol of the present invention can be used as a crosslinked curable urethane resin paint by blending polyisocyanate as a crosslinking component. Furthermore, the polyol of the present invention can be used as a thermosetting melamine-modified resin paint by blending a melamine resin as a crosslinking component.
このようにして作製された塗料は、スプレー塗装、ロー
ル塗装、ハケ塗りなどの塗装法により、金属類、プラス
チック類、木工製品などに塗装することができる。The paint produced in this way can be applied to metals, plastics, wood products, etc. by a coating method such as spray coating, roll coating, or brush coating.
更に、本発明のポリオールを含んでなる本発明の二液ウ
レタン樹脂塗料用組成物は、乾燥性、硬度、光沢、肉持
ち性、耐候性、耐溶剤性の優れた塗膜と優れた作業性を
有するものであり、大型構造物用、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。Furthermore, the two-component urethane resin coating composition of the present invention containing the polyol of the present invention provides a coating film with excellent drying properties, hardness, gloss, durability, weather resistance, and solvent resistance, and excellent workability. It can be used for a wide range of applications such as large structures, automobile repair, and woodworking such as furniture painting.
（実施例） 以下、参考例および実施例で本発明を説明する。(Example) The present invention will be explained below with reference examples and examples.
なお、例中で部または係とあるのは特に断わりのないか
ぎりそれぞれ重量部または重量％である。In addition, unless otherwise specified, "part" or "part" in the examples means part by weight or weight %, respectively.
実施例１
撹拌機、温度計、冷却器、窒素ガス導入管のついた４つ
ロフラスコに窒素ガス気流下、トルエンル
２５部および酢酸ブチＦＰ２５部を仕込み、１００℃に
昇温した中に、ターシャリ−ブチルシクロへキシルメタ
クリレート１５部、ヒドロキシエチルメタクリレート９
部、スチレン５部、メチルメタクリレート１０部、ブチ
ルアクリレート５．５部、ブチルメタクリレート５部、
メタ＃クリル酸０．５部およびアゾビスイソブチルニト
リル０．５部からなる混合物を２時間かけて滴下し、更
に１００°Ｃで４時間保持して、本発明のアクリルポリ
オールを不揮発分５０．２％、粘度Ｕ−Ｖの溶液（以下
、アクリルポリオール溶液（１）という。）として得た
。Example 1 25 parts of toluene and 25 parts of butylacetate FP were charged under a nitrogen gas stream into a four-bottle flask equipped with a stirrer, a thermometer, a condenser, and a nitrogen gas inlet tube, and the temperature was raised to 100°C. 15 parts of butyl cyclohexyl methacrylate, 9 parts of hydroxyethyl methacrylate
parts, 5 parts of styrene, 10 parts of methyl methacrylate, 5.5 parts of butyl acrylate, 5 parts of butyl methacrylate,
A mixture consisting of 0.5 part of methacrylic acid and 0.5 part of azobisisobutylnitrile was added dropwise over 2 hours, and the mixture was further maintained at 100°C for 4 hours to reduce the non-volatile content of the acrylic polyol of the present invention to 50.2 parts. % and a viscosity of UV (hereinafter referred to as acrylic polyol solution (1)).
実施例２〜３、比較例１〜２
実施例１において、使用した重合性不飽和単量体及び重
合開始剤の組成を第１表に示した通りとする以外は同様
の操作をくり返してアクリルポリオール溶液（２）〜（
３）及び比較用ポリオール溶液（１１〜（２）を得た。Examples 2-3, Comparative Examples 1-2 The same operations as in Example 1 were repeated except that the compositions of the polymerizable unsaturated monomer and polymerization initiator used were as shown in Table 1. Polyol solution (2) - (
3) and comparative polyol solutions (11 to (2)) were obtained.
第 １ 表
実施例４〜６および比較例３〜４
実施例１〜３および比較例１〜２で得られたアクリルポ
リオール溶液（１１〜（３）および比較用ポリオール溶
液（１）〜（２）のそれぞれに、酸化チタン（タイベー
クＲ−８２０，５原産業（株製）を不揮発分中顔料濃度
が４０重量係となるように配合し、サンドミルでよく分
散した。得られた分散液（以下、■液という。）のそれ
ぞれに対し、多官能インシアネート（スミジュールＮ１
住友バイエルウレタン■製）を１液中のヒドロキシル基
に対してインシアネート基の轟景比が１＝１となる量だ
け秤取してａ液とした。このＩ液と■液を混合し、更に
エアースプレーの可能な粘度までトルエン：酢酸ブチル
−１：１のシンナーで希釈して、本発明の二液ウレタン
樹脂塗料用組成物をビヒクル成分として含む塗料（１）
〜（３）および比較用塗料（１）〜（２）を得た。Table 1 Examples 4-6 and Comparative Examples 3-4 Acrylic polyol solutions (11-(3) and comparative polyol solutions (1)-(2) obtained in Examples 1-3 and Comparative Examples 1-2 Titanium oxide (Tie Bake R-820, 5, manufactured by Hara Sangyo Co., Ltd.) was blended with each of the above so that the pigment concentration in nonvolatile matter was 40% by weight, and the mixture was well dispersed with a sand mill.The resulting dispersion (hereinafter referred to as ■ Multifunctional incyanate (sumidur N1)
(manufactured by Sumitomo Bayer Urethane ■) was weighed out in an amount such that the ratio of incyanate groups to hydroxyl groups in the liquid was 1=1 to prepare a liquid A. A paint containing the two-component urethane resin paint composition of the present invention as a vehicle component is prepared by mixing the liquid I and liquid (2) and diluting the mixture with a toluene:butyl acetate-1:1 thinner to a viscosity that allows air spraying. (1)
- (3) and comparative paints (1) - (2) were obtained.
ついで、エアースプレーでリン酸亜鉛処理板に乾燥膜厚
４０μになるように塗装したのち、６０℃で３０分間強
制乾燥して各種性能試験用の試験片を作成した。Next, the coating was applied to a zinc phosphate-treated board using air spray so that the dry film thickness was 40 μm, and then forced drying was performed at 60° C. for 30 minutes to prepare test pieces for various performance tests.
塗膜の性能を次に示す性能試験方法により鉛筆硬度以外
は◎〜○〜Δ〜×の４段階で評価した。The performance of the coating film was evaluated using the following performance test method, except for pencil hardness, on a four-level scale of ◎ to ○ to Δ to ×.
評価結果は第２表に示す。The evaluation results are shown in Table 2.
いて判定。Judgment.
スプレ４性； スプレ一時の作業性の良悪で判定。Spray quality: Judging by the quality of workability during the temporary spraying process.
乾 燥 性； 強制乾燥直後の指圧判定およびマスキン
グテストでの判定。Drying property: Judgment by finger pressure and masking test immediately after forced drying.
仕上シ感； 塗装皮膜の目視判定。Finish feel: Visual judgment of paint film.
光 沢； ６０度鏡面反射率測定値の比較。Light intensity: Comparison of 60 degree specular reflectance measurements.
密 着 性； 塗装基材に対する密着性で判定。Adhesion: Judged by adhesion to the painted base material.
鉛筆硬度； 三菱ユニでの傷付硬度。Pencil hardness: Scratch hardness at Mitsubishi Uni.
耐溶剤性； ウレタンシンナーでのラビング後の外観観
察で判定。Solvent resistance: Determined by observing the appearance after rubbing with urethane thinner.
耐 候 性； 屋外バクロ後の光沢保持率での評価。Weather resistance: Evaluation based on gloss retention after outdoor baking.
第 ２ 表Table 2
Claims (1)
ａ）５．０〜９７．９重量％、水酸基を含有する重合性
不飽和単量体（ｂ）２０〜３５．０重量％、酸性官能基
を含有する重合性不飽和単量体（ｃ）０．１〜５．０重
量％及びその他の重合性不飽和単量体（ｄ）０．０〜９
２．９重量％（但し、（ａ）、（ｂ）、（ｃ）及び（ｄ
）の合計は１００重量％である。）を共重合してなるシ
クロアルキル基を含有するアクリルポリオール。 ２、シクロアルキル基を含有する重合性不飽和単量体（
ａ）５．０〜９７．９重量％、水酸基を含有する重合性
不飽和単量体（ｂ）２．０〜３５．０重量％、酸性官能
基を含有する重合性不飽和単量体（ｃ）０．１〜５．０
重量％及びその他の重合性不飽和単量体（ｄ）０．０〜
９２．９重量％（但し、（ａ）、（ｂ）、（ｃ）及び（
ｄ）の合計は１００重量％である。）を共重合してなる
シクロアルキル基を含有するアクリルポリオールを含ん
でなる水酸基含有化合物 並びにポリイソシアネート化合物 からなる二液ウレタン樹脂塗料用組成物。[Claims] 1. Polymerizable unsaturated monomer containing a cycloalkyl group (
a) 5.0 to 97.9% by weight of a polymerizable unsaturated monomer containing a hydroxyl group (b) 20 to 35.0% by weight of a polymerizable unsaturated monomer containing an acidic functional group (c) 0.1-5.0% by weight and other polymerizable unsaturated monomers (d) 0.0-9
2.9% by weight (however, (a), (b), (c) and (d)
) is 100% by weight. ) is a cycloalkyl group-containing acrylic polyol. 2. Polymerizable unsaturated monomer containing a cycloalkyl group (
a) 5.0 to 97.9% by weight of a polymerizable unsaturated monomer containing a hydroxyl group (b) 2.0 to 35.0% by weight of a polymerizable unsaturated monomer containing an acidic functional group ( c) 0.1-5.0
Weight% and other polymerizable unsaturated monomers (d) 0.0~
92.9% by weight (however, (a), (b), (c) and (
The sum of d) is 100% by weight. 1. A two-component urethane resin coating composition comprising a hydroxyl group-containing compound comprising an acrylic polyol containing a cycloalkyl group obtained by copolymerizing ) and a polyisocyanate compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61288670A JPS63142009A (en) | 1986-12-05 | 1986-12-05 | Acrylpolyol and two-pack urethane resin coating composition containing same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61288670A JPS63142009A (en) | 1986-12-05 | 1986-12-05 | Acrylpolyol and two-pack urethane resin coating composition containing same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63142009A true JPS63142009A (en) | 1988-06-14 |
| JPH0528748B2 JPH0528748B2 (en) | 1993-04-27 |
Family
ID=17733158
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61288670A Granted JPS63142009A (en) | 1986-12-05 | 1986-12-05 | Acrylpolyol and two-pack urethane resin coating composition containing same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63142009A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995023832A1 (en) * | 1994-03-05 | 1995-09-08 | Basf Lacke + Farben Ag | Coating agent based on a poly(meth)acrylate resin which can be crosslinked and contains hydroxyl groups |
| WO1997022646A1 (en) * | 1995-12-19 | 1997-06-26 | Ppg Industries, Inc. | Polyisocyanate cured ultradurable glossy coating compositions |
| US5849835A (en) * | 1995-12-19 | 1998-12-15 | Ppg Industries, Inc. | Polyisocyanate cured ultradurable glossy coating compositions |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5058123A (en) * | 1973-09-22 | 1975-05-20 | ||
| JPS5117915A (en) * | 1974-08-05 | 1976-02-13 | Kansai Paint Co Ltd | NETSUKOKASEIKOKOKEIBUNGATATORYO |
| JPS55160009A (en) * | 1979-05-30 | 1980-12-12 | Asahi Chem Ind Co Ltd | Production of acrylic copolymer |
| JPS56133351A (en) * | 1980-03-24 | 1981-10-19 | Atom Kagaku Toryo Kk | Coating resin composition |
| JPS5817174A (en) * | 1981-07-23 | 1983-02-01 | Dainippon Ink & Chem Inc | Resin composition for coating |
-
1986
- 1986-12-05 JP JP61288670A patent/JPS63142009A/en active Granted
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5058123A (en) * | 1973-09-22 | 1975-05-20 | ||
| JPS5117915A (en) * | 1974-08-05 | 1976-02-13 | Kansai Paint Co Ltd | NETSUKOKASEIKOKOKEIBUNGATATORYO |
| JPS55160009A (en) * | 1979-05-30 | 1980-12-12 | Asahi Chem Ind Co Ltd | Production of acrylic copolymer |
| JPS56133351A (en) * | 1980-03-24 | 1981-10-19 | Atom Kagaku Toryo Kk | Coating resin composition |
| JPS5817174A (en) * | 1981-07-23 | 1983-02-01 | Dainippon Ink & Chem Inc | Resin composition for coating |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995023832A1 (en) * | 1994-03-05 | 1995-09-08 | Basf Lacke + Farben Ag | Coating agent based on a poly(meth)acrylate resin which can be crosslinked and contains hydroxyl groups |
| WO1997022646A1 (en) * | 1995-12-19 | 1997-06-26 | Ppg Industries, Inc. | Polyisocyanate cured ultradurable glossy coating compositions |
| US5849835A (en) * | 1995-12-19 | 1998-12-15 | Ppg Industries, Inc. | Polyisocyanate cured ultradurable glossy coating compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0528748B2 (en) | 1993-04-27 |
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