JP2006176633A - 硬化性樹脂組成物、クリヤー塗料組成物及びそれを用いた複層塗膜の形成方法 - Google Patents
硬化性樹脂組成物、クリヤー塗料組成物及びそれを用いた複層塗膜の形成方法 Download PDFInfo
- Publication number
- JP2006176633A JP2006176633A JP2004370982A JP2004370982A JP2006176633A JP 2006176633 A JP2006176633 A JP 2006176633A JP 2004370982 A JP2004370982 A JP 2004370982A JP 2004370982 A JP2004370982 A JP 2004370982A JP 2006176633 A JP2006176633 A JP 2006176633A
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- JP
- Japan
- Prior art keywords
- coating film
- curable resin
- isocyanate compound
- resin composition
- clear
- 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
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- 238000000576 coating method Methods 0.000 title claims description 89
- 239000011248 coating agent Substances 0.000 title claims description 87
- 239000008199 coating composition Substances 0.000 title claims description 39
- 238000000034 method Methods 0.000 title claims description 32
- -1 isocyanate compound Chemical class 0.000 claims abstract description 57
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 56
- 239000012948 isocyanate Substances 0.000 claims abstract description 45
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- 239000004925 Acrylic resin Substances 0.000 claims abstract description 40
- 239000007787 solid Substances 0.000 claims abstract description 17
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 13
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- 239000000178 monomer Substances 0.000 description 39
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 23
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 20
- 238000001723 curing Methods 0.000 description 20
- 150000002596 lactones Chemical class 0.000 description 14
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- 238000003786 synthesis reaction Methods 0.000 description 5
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 5
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- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
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- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
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- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
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- 238000001816 cooling Methods 0.000 description 2
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- 238000001035 drying Methods 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
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- 239000011521 glass Substances 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
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- 239000010959 steel Substances 0.000 description 2
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- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 2
- 150000007970 thio esters Chemical class 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
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 1
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- PEZADNNPJUXPTA-UHFFFAOYSA-N 1,5-bis(isocyanatomethyl)-2,4-dimethylbenzene Chemical compound CC1=CC(C)=C(CN=C=O)C=C1CN=C=O PEZADNNPJUXPTA-UHFFFAOYSA-N 0.000 description 1
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
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- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical group CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- BYDRTKVGBRTTIT-UHFFFAOYSA-N 2-methylprop-2-en-1-ol Chemical compound CC(=C)CO BYDRTKVGBRTTIT-UHFFFAOYSA-N 0.000 description 1
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- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 1
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- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
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- 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
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Landscapes
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Abstract
【解決手段】 水酸基含有アクリル樹脂と多官能イソシアネート化合物とを含有する硬化性樹脂組成物であって、
前記多官能イソシアネート化合物のうちの少なくとも一部がイソシアヌレート型イソシアネート化合物であり、
前記硬化性樹脂組成物は、下記一般式(1):
−(CH2)n− (1)
(式中、nは4以上の整数を表す。)
で表されるソフトセグメント部を、前記水酸基含有アクリル樹脂及び多官能イソシアネート化合物の固形分全量に対して25〜50質量%有していることを特徴とする硬化性樹脂組成物。
【選択図】 なし
Description
前記多官能イソシアネート化合物のうちの少なくとも一部がイソシアヌレート型イソシアネート化合物であり、
前記硬化性樹脂組成物は、下記一般式(1):
−(CH2)n− (1)
(式中、nは4以上の整数を表す。)
で表されるソフトセグメント部を、前記水酸基含有アクリル樹脂及び多官能イソシアネート化合物の固形分全量に対して25〜50質量%有していることを特徴とするものである。
−(CH2)n− (1)
(式中、nは4以上の整数を表す。)
で表されるソフトセグメント部を、前記水酸基含有アクリル樹脂及び多官能イソシアネート化合物の固形分全量に対して25〜50質量%有していることを特徴とするものである。
E'=3nRT (n:架橋密度、R:気体定数、T:絶対温度)。
撹拌羽根、窒素導入管、冷却コンデンサー及び滴下ロートを備えた2Lのガラス容器に、プロピレングリコールモノメチルエーテルアセテート358.0g及びキシレン90.0gを加え、窒素雰囲気下130℃に加温した。その容器に、滴下ロートを用いてプロピレングリコールモノメチルエーテルアセテート100.0g、tert−ブチルパーオキシ−2−エチルヘキサノエート100.0g、スチレン140.0g、アクリル酸−n−ブチル85.4g、メタクリル酸−n−ブチル133.7g、メタクリル酸−2−エチルヘキシル35.0g、アクリル酸−4−ヒドロキシブチル305.9g、プラクセルFM−2(2−ヒドロキシエチルメタクリレートとε−カプロラクトンの1:2付加物、ダイセル工業社製)300.0gを3時間かけて等速滴下した。その後130℃で0.5時間保持し、50.0gのプロピレングリコールモノメチルエーテルアセテートに溶解したtert−ブチルパーオキシ−2−エチルヘキサノエート10.0gを30分で等速滴下した。更に、130℃で1.0時間加温を続けることによって、目的の水酸基含有アクリル樹脂aを得た。
表1に示すモノマー成分、溶媒及び重合開始剤を用い、それらの配合量を表1に示すようにした以外は合成例1と同様にして、水酸基含有アクリル樹脂b〜dをそれぞれ合成した。なお、プラクセルFM−1としては2−ヒドロキシエチルメタクリレートとε−カプロラクトンの1:1付加物(ダイセル工業社製)、プラクセルFM−5としては2−ヒドロキシエチルメタクリレートとε−カプロラクトンの1:5付加物(ダイセル工業社製)を用いた。
表2に示した配合に従い、各成分を混合し、ディスパーで攪拌することによって実施例1〜4及び比較例1〜4のクリヤー塗料組成物を得た。上記クリヤー塗料組成物を、プロピレングリコールモノメチルエーテルアセテート/3−エトキシプロピオン酸エチル=1/2(質量比)からなるシンナーによってNo.4フォードカップで25秒/20℃となるようにそれぞれ希釈した。なお、ビュレット型イソシアネート硬化剤としては、住化バイエルウレタン(株)社製スミジュールN−75を用い、イソシアヌレート型イソシアネート硬化剤としては、住化バイエルウレタン(株)社製スミジュールN3300を用い、アシンメトリー型イソシアネート硬化剤としては、住化バイエルウレタン(株)社製デスモジュールX2410を用いた。
実施例1〜4及び比較例1〜4のクリヤー塗料組成物を用いて得られた複層塗膜について、以下の評価方法によって40%硫酸水溶液による耐酸性の評価を行った。
○:スポット部に塗膜のハガレは認められないもの。
△:スポット部の塗膜の一部にハガレが認められたもの。
×:スポット部の塗膜が完全にハガレているもの。
実施例1〜4及び比較例1〜4のクリヤー塗料組成物を用いて得られた複層塗膜について、以下の評価方法によって耐擦り傷性の評価を行った。
Claims (4)
- 水酸基含有アクリル樹脂と多官能イソシアネート化合物とを含有する硬化性樹脂組成物であって、
前記多官能イソシアネート化合物のうちの少なくとも一部がイソシアヌレート型イソシアネート化合物であり、
前記硬化性樹脂組成物は、下記一般式(1):
−(CH2)n− (1)
(式中、nは4以上の整数を表す。)
で表されるソフトセグメント部を、前記水酸基含有アクリル樹脂及び多官能イソシアネート化合物の固形分全量に対して25〜50質量%有していることを特徴とする硬化性樹脂組成物。 - 請求項1に記載の硬化性樹脂組成物をバインダーとして含有することを特徴とするクリヤー塗料組成物。
- 被塗装物に対してトップコートを有する複層塗膜を形成する方法であって、請求項2に記載のクリヤー塗料組成物を前記トップコートとして塗装することを特徴とする複層塗膜の形成方法。
- 前記被塗装物にベース塗料組成物を塗布してベース未硬化塗膜を得た後、前記ベース未硬化塗膜に前記クリヤー塗料組成物を塗布してクリヤー未硬化塗膜を得、前記ベース未硬化塗膜及びクリヤー未硬化塗膜を同時に加熱して硬化させることを特徴とする請求項3に記載の複層塗膜の形成方法。
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JP2006176634A (ja) * | 2004-12-22 | 2006-07-06 | Nippon Paint Co Ltd | 自動車用クリヤー塗料組成物及びそれを用いた複層塗膜の形成方法 |
KR20170030554A (ko) | 2014-07-08 | 2017-03-17 | 바스프 코팅스 게엠베하 | 2성분 페인트 조성물 및 그를 사용한 다층 코팅 형성 방법 |
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JP2006176634A (ja) * | 2004-12-22 | 2006-07-06 | Nippon Paint Co Ltd | 自動車用クリヤー塗料組成物及びそれを用いた複層塗膜の形成方法 |
KR20170030554A (ko) | 2014-07-08 | 2017-03-17 | 바스프 코팅스 게엠베하 | 2성분 페인트 조성물 및 그를 사용한 다층 코팅 형성 방법 |
US10190016B2 (en) | 2014-07-08 | 2019-01-29 | Basf Coatings Gmbh | Two-component paint composition and multilayer coating formation method using this |
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