JP4744871B2 - 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 - Google Patents
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 Download PDFInfo
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- JP4744871B2 JP4744871B2 JP2004370987A JP2004370987A JP4744871B2 JP 4744871 B2 JP4744871 B2 JP 4744871B2 JP 2004370987 A JP2004370987 A JP 2004370987A JP 2004370987 A JP2004370987 A JP 2004370987A JP 4744871 B2 JP4744871 B2 JP 4744871B2
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- coating film
- acrylic resin
- containing acrylic
- clear
- coating composition
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- 239000002023 wood Substances 0.000 description 1
- 230000037303 wrinkles Effects 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
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/14—Esterification
- C08F8/16—Lactonisation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
- C08G18/6225—Polymers of esters of acrylic or methacrylic acid
- C08G18/6229—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
- C08G18/6233—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols the monomers or polymers being esterified with carboxylic acids or lactones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/7806—Nitrogen containing -N-C=0 groups
- C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
- C08G18/7831—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing biuret groups
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- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/062—Copolymers with monomers not covered by C09D133/06
- C09D133/066—Copolymers with monomers not covered by C09D133/06 containing -OH groups
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- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
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- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/06—Unsaturated polyesters having carbon-to-carbon unsaturation
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
Description
前記水酸基含有アクリル樹脂が、少なくとも一部のモノマーとして4−ヒドロキシブチル(メタ)アクリレートを用いて得た水酸基含有アクリル樹脂であり、
前記多官能イソシアネート化合物がイソシアヌレート型イソシアネート化合物であり、
前記クリヤー塗料組成物は、下記一般式(1):
−(CH2)n− (1)
(式中、nは4〜9の整数を表す。)
で表されかつ前記クリヤー塗料組成物を加熱硬化して得られる硬化塗膜の主鎖中又は架橋結合鎖中に存在す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、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するラクトン含有モノマー由来のソフトセグメント部の割合を4.5質量%以下とし、かつ、得られる硬化塗膜の動的ガラス転移温度が30〜60℃の範囲となるように調製され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、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するラクトン含有モノマー由来のソフトセグメント部の割合を4.5質量%以下とし、かつ、得られる硬化塗膜の動的ガラス転移温度が30〜60℃の範囲となるように調製され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200.0g、アクリル酸−n−ブチル288.5g、メタクリル酸−2−エチルヘキシル74.5g、アクリル酸−4−ヒドロキシブチル437.0g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〜h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−2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1:2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1〜5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を用いた。
実施例1〜4及び比較例1〜5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。
○:スポット部異常なし。
○△:○の場合と△の場合との双方が認められたもの。
△:スポット部に膨潤及びチジミが認められるが、塗膜のハガレは認められないもの。
×:スポット部の塗膜がハガレているもの。
実施例1〜4及び比較例1〜5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。
実施例1〜4及び比較例1〜5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引っ掻き傷性の評価を行った。
◎:殆ど引っ掻き傷がついていない。
○:やや引っ掻き傷がついている。
△:引っ掻き傷が目立つ。
×:引っ掻き傷がかなり目立つ。
Claims (5)
- 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クリヤー塗料組成物であって、
前記水酸基含有アクリル樹脂が、少なくとも一部のモノマーとして4−ヒドロキシブチル(メタ)アクリレートを用いて得た水酸基含有アクリル樹脂であり、
前記多官能イソシアネート化合物がイソシアヌレート型イソシアネート化合物であり、
前記クリヤー塗料組成物は、下記一般式(1):
−(CH2)n− (1)
(式中、nは4〜9の整数を表す。)
で表されかつ前記クリヤー塗料組成物を加熱硬化して得られる硬化塗膜の主鎖中又は架橋結合鎖中に存在す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、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するラクトン含有モノマー由来のソフトセグメント部の割合を4.5質量%以下とし、かつ、得られる硬化塗膜の動的ガラス転移温度が30〜60℃の範囲となるように調製されていることを特徴とする自動車用クリヤー塗料組成物。 - 前記水酸基含有アクリル樹脂に由来するソフトセグメント部の割合が、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7〜17質量%であることを特徴とする請求項1に記載の自動車用クリヤー塗料組成物。
- 前記水酸基含有アクリル樹脂におけるソフトセグメント部の含有割合が、前記水酸基含有アクリル樹脂の固形分全量に対して7〜30質量%であり、
前記多官能イソシアネート化合物におけるソフトセグメント部の含有割合が、前記多官能イソシアネート化合物の固形分全量に対して60質量%以下である、
ことを特徴とする請求項1又は2に記載の自動車用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1〜3のうちのいずれか一項に記載の自動車用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自動車用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4に記載の複層塗膜の形成方法。
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GB0526080A GB2421734B (en) | 2004-12-22 | 2005-12-21 | Clear coating composition and method of forming a multi-layer coating film using the same |
US11/313,786 US8138258B2 (en) | 2004-12-22 | 2005-12-22 | Clear coating composition for an automobile and method of forming a multi-layer coating film using the same |
CN200510132165.5A CN1800282B (zh) | 2004-12-22 | 2005-12-22 | 汽车用透明涂料组合物和使用它的多层涂膜的形成方法 |
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JPH0245577A (ja) | 1988-08-04 | 1990-02-15 | Nippon Paint Co Ltd | 熱硬化性組成物 |
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US5849835A (en) * | 1995-12-19 | 1998-12-15 | Ppg Industries, Inc. | Polyisocyanate cured ultradurable glossy coating compositions |
DE19828935A1 (de) * | 1998-06-29 | 1999-12-30 | Basf Ag | Hochviskose Polyisocyanate enthaltende Zusammensetzungen |
ATE249506T1 (de) * | 1998-11-17 | 2003-09-15 | Vantico Ag | Zusammensetzung zum vernetzen von carboxyl- haltigen polymeren in thermisch härtbaren systemen |
JP2003082031A (ja) * | 2001-09-13 | 2003-03-19 | Kansai Paint Co Ltd | 共重合体およびこの重合体を用いた耐擦り傷性塗料組成物 |
JP2003253191A (ja) * | 2002-02-28 | 2003-09-10 | Nippon Paint Co Ltd | クリヤー塗料組成物及び複層塗膜形成方法 |
US7157536B2 (en) * | 2004-01-19 | 2007-01-02 | E. I. Du Pont De Nemours And Company | Coating composition for ambient cure containing an alkoxylated amine |
JP4477483B2 (ja) * | 2004-12-22 | 2010-06-09 | 日本ペイント株式会社 | 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 |
JP4902115B2 (ja) * | 2004-12-22 | 2012-03-21 | 日本ペイント株式会社 | 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 |
JP2007196982A (ja) | 2005-12-26 | 2007-08-09 | Bridgestone Corp | ストラットマウント |
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2004
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2005
- 2005-12-21 GB GB0526080A patent/GB2421734B/en active Active
- 2005-12-22 US US11/313,786 patent/US8138258B2/en not_active Expired - Fee Related
- 2005-12-22 CN CN200510132165.5A patent/CN1800282B/zh not_active Expired - Fee Related
- 2005-12-22 FR FR0513117A patent/FR2879615B1/fr not_active Expired - Fee Related
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GB2421734A (en) | 2006-07-05 |
GB0526080D0 (en) | 2006-02-01 |
CN1800282A (zh) | 2006-07-12 |
GB2421734B (en) | 2008-08-20 |
US20060147639A1 (en) | 2006-07-06 |
US8138258B2 (en) | 2012-03-20 |
CN1800282B (zh) | 2010-05-12 |
FR2879615B1 (fr) | 2014-07-25 |
JP2006176634A (ja) | 2006-07-06 |
FR2879615A1 (fr) | 2006-06-23 |
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