JP5666316B2 - 有機金属化合物を含む陰極電着塗料 - Google Patents
有機金属化合物を含む陰極電着塗料 Download PDFInfo
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- JP5666316B2 JP5666316B2 JP2010548026A JP2010548026A JP5666316B2 JP 5666316 B2 JP5666316 B2 JP 5666316B2 JP 2010548026 A JP2010548026 A JP 2010548026A JP 2010548026 A JP2010548026 A JP 2010548026A JP 5666316 B2 JP5666316 B2 JP 5666316B2
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- Prior art keywords
- paint
- substrate
- electrodeposition
- cathodic electrodeposition
- metal substrate
- Prior art date
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- 238000004070 electrodeposition Methods 0.000 title claims description 93
- 239000003973 paint Substances 0.000 title claims description 44
- 150000002902 organometallic compounds Chemical class 0.000 title description 5
- 239000000758 substrate Substances 0.000 claims description 49
- 239000000463 material Substances 0.000 claims description 38
- 238000000576 coating method Methods 0.000 claims description 37
- 239000011248 coating agent Substances 0.000 claims description 29
- 239000011230 binding agent Substances 0.000 claims description 25
- 229910052751 metal Inorganic materials 0.000 claims description 22
- 239000002184 metal Substances 0.000 claims description 22
- 239000007787 solid Substances 0.000 claims description 19
- 239000003446 ligand Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 239000003054 catalyst Substances 0.000 claims description 16
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- 229920000647 polyepoxide Polymers 0.000 claims description 16
- 229910052726 zirconium Inorganic materials 0.000 claims description 13
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 12
- 229910000831 Steel Inorganic materials 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 239000010959 steel Substances 0.000 claims description 11
- 238000004132 cross linking Methods 0.000 claims description 10
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- YOBOXHGSEJBUPB-MTOQALJVSA-N (z)-4-hydroxypent-3-en-2-one;zirconium Chemical compound [Zr].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O YOBOXHGSEJBUPB-MTOQALJVSA-N 0.000 claims description 4
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Classifications
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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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/44—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/44—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications
- C09D5/4419—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications with polymers obtained otherwise than by polymerisation reactions only involving carbon-to-carbon unsaturated bonds
- C09D5/443—Polyepoxides
- C09D5/4434—Polyepoxides characterised by the nature of the epoxy binder
- C09D5/4438—Binder based on epoxy/amine adducts, i.e. reaction products of polyepoxides with compounds containing amino groups only
-
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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Description
a)カルボキシル基を含有する化合物、例えば飽和もしくは不飽和モノカルボン酸(例えば、安息香酸、2−エチルヘキサン酸、バーサチック酸)、様々な鎖長の脂肪族、脂環式および/または芳香族ジカルボン酸(例えば、アジピン酸、セバシン酸、イソフタル酸または二量体脂肪酸)、ヒドロキシアルキルカルボン酸(例えば、乳酸、ジメチロールプロピオン酸)、およびまたカルボキシル含有ポリエステルなど、あるいは
b)アミノ基を含有する化合物、例えば第二級アミノ基を有するジエチルアミンまたはエチルヘキシルアミンもしくはジアミンなど、例えば、N,N’−ジアルキルアルキレンジアミン類、例えばジメチルエチレンジアミンなど、N,N’−ジアルキルポリオキシアルキレンアミン類、例えばN,N’−ジメチルポリオキシプロピレンジアミンなど、シアノアルキル化アルキレンジアミン類、例えばN,N’−ビス(シアノエチル)エチレンジアミンなど、シアノアルキル化ポリオキシアルキレンアミン類、例えばN,N’−ビス(シアノエチル)ポリオキシプロピレンジアミン、ポリアミノアミド類、例えばVersamide、例として、より詳しくはジアミンのアミノ末端反応生成物(例えば、ヘキサメチレンジアミン)、ポリカルボン酸、より詳しくは二量体脂肪酸、およびモノカルボン酸、より詳しくは脂肪酸、あるいは、1モルのジアミノヘキサンと2モルのモノグリシジルエーテルもしくはモノグリシジルエステルの反応生成物、特にバーサチック酸などのα分枝脂肪酸のグリシジルエステルなど、あるいは、
c)ヒドロキシル基を含有する化合物、例えばネオペンチルグリコール、ビスエトキシル化ネオペンチルグリコール、ネオペンチルグリコールヒドロキシピバレート、ジメチルヒダントイン−N,N’−ジエタノール、ヘキサン−1,6−ジオール、ヘキサン−2、5−ジオール、1,4−ビス(ヒドロキシメチル)シクロヘキサン、1,1−イソプロピリデンビス(p−フェノキシ)−2−プロパノール、トリメチロールプロパン、ペンタエリトリトールなど、またはアミノアルコール、例えばトリエタノールアミン、メチルジエタノールアミンまたはヒドロキシル含有アルキルケチミン、例えばアミノメチルプロパン−1,3−ジオールメチルイソブチルケチミンまたはトリス(ヒドロキシメチル)アミノメタンシクロヘキサノンケチミンなど、およびまた、様々な官能価および分子量のポリグリコールエーテル、ポリエステルポリオール、ポリエーテルポリオール、ポリカプロラクトンポリオール、およびポリカプロラクタムポリオール、あるいは
d)ナトリウムメトキシドの存在下でエポキシ樹脂の水酸基とエステル交換する飽和もしくは不飽和脂肪酸メチルエステル。
i)1)ホスフィンおよび/またはホスフィン塩を触媒として添加して、a)ジエポキシド化合物またはジエポキシド化合物の混合物およびb)モノフェノール、ジフェノールまたはモノフェノールとジフェノールの混合物から調製できる前駆体と
2)1以上の有機アミンを、60〜130℃に低下させた添加温度で反応させて、エポキシド−アミン付加物を得ること、
ii)続いてまたは同時に、成分a)およびb)の反応において形成されていた第二級ヒドロキシル基を、段階i)で調製したエポキシド−アミン付加物のエポキシド基と110〜150℃の温度で反応させること、
iii)1種類の架橋剤または様々な架橋剤の混合物を150℃より低い温度で添加すること、
iv)中和させること、ならびに
v)段階i)〜iv)で得た混合物を水中に分散させること、
により得られる、水性結合剤分散体中に存在する少なくとも1種の結合剤(A)を使用することである。
調製例1(架橋剤)
欧州特許第0961797B1号(6頁43〜52行)の架橋剤を使用する。攪拌器、還流冷却器、内部温度計、および不活性ガス入口ラインを装備した反応器に、窒素雰囲気下、NCO当量135の4,4’−ジフェニルメタンジイソシアネートに基づく1084gの異性体および多官能性オリゴマーを装入する(Basonat(登録商標)A270、BASF;NCO官能価約2.7;ジフェニルメタン2,2’−および2,4’−ジイソシアネート含量5%未満)。2gのジブチル錫ラウレートを添加し、1314gのブチルジグリコールを生成物の温度が70℃より低いままであるような速度で滴加する。冷却は必要であってもよい。添加の終わりに、温度を70℃にてさらに120分間保つ。その後の確認で、NCO基はもう検出されない。バッチを65℃に冷却する。
固形分は97%より大きい(130℃にて1時間)。
欧州特許第0961797B1号(7頁4〜30行)の結合剤分散体Aを使用する。熱媒油で加熱し、攪拌器、還流冷却器、温度計および不活性ガス入口管を装備した実験用反応器に、エポキシド当量(EEW)が188のビスフェノールAに基づく市販のエポキシ樹脂1128部、262部のドデシルフェノール、31.4部のキシレン、および228部のビスフェノールAを装入し、この初期装入を窒素下127℃まで加熱する。攪拌しながら、1.6gのトリフェニルホスフィンを添加するとすぐ発熱反応があり、温度は160℃まで上昇する。この反応混合物を再び130℃に冷却した後、そのエポキシド含量を確認する。EEWは532で、98%より多くのフェノールのOH基が反応したことを示している。次に、297.5部のPluriol P900(ポリプロピレングリコール、MW900、BASF)を添加すると同時に冷却する。5分後、120℃にてさらに冷却して、105部のジエタノールアミンを添加する。短時間の発熱の後(Tmax127℃)、温度が110℃に下がったときに(30分)、51部のN,N−ジメチルアミノプロピルアミンを添加する。短時間の発熱の後(Tmax140℃)、バッチをさらに130℃にて2時間、粘度が一定となるまで反応させる(1.8dPas、23℃のコーン/プレート粘度計、Solvenon PM(BASF)中40%強度)。その時点で、同時に冷却しながら、58.5部のブチルグリコールおよび887.8部の架橋剤(調製例1)を添加し、生成物を105℃にて排出する。まだ熱い混合物2100部を、強く攪拌しながら、事前に調製した1945部の完全脱イオン水(FD水)と33.1部の氷酢酸の混合物中に速やかに分散させる。短時間均質化した後、生成物をさらなる1404部のFD水で希釈し、K900プレートフィルター(Seitz)で濾過する。この分散体の特徴は以下の通りである:
固形分(130℃にて1時間):35.7%
MEQ塩基=0.657meq/g樹脂固形分
MEQ酸=0.283meq/g樹脂固形分
pH=5.4
平均粒度=1250?(光散乱法)
沈降安定性=室温にて3ヶ月の貯蔵期間後の沈降なし
粘度=14秒(23℃のDIN4カップ)
欧州特許第0961797号(9頁17〜21行)の練磨型樹脂を使用する。攪拌機構、内部温度計、窒素入口、および、還流冷却器を含む水分離器を装備した反応器に、ビスフェノールAに基づくエポキシド当量(EEW)が188のエポキシ樹脂30.29部、9.18部のビスフェノールA、7.04部のドデシルフェノール、および2.37部のブチルグリコールを装入する。この初期装入を110℃に加熱し、1.85部のキシレンを添加し、可能な限り微量の水とともに弱真空下で再び蒸留する。次に、0.07部のトリフェニルホスフィンを添加し、混合物を130℃に加熱する。発熱により温度が150℃に上昇した後、130℃にて1時間反応を継続する。その時点の反応混合物のEEWは860である。それを冷却し、冷却の間に、9.91部のブチルグリコールおよびEEWが333の17.88部のポリプロピレングリコールジグリシジルエーテル(DER 732、Dow Chemicals社)と混合する。90℃にて4.23部の2−(2’−アミノエトキシ)エタノール(H2N−CH2−CH2−O−CH2−CH2−OH)を、そして10分後に、1.37部のN,N−ジメチルアミノプロピルアミンを添加する。短時間の発熱の後、反応混合物を粘度が一定になるまで90℃にて2時間保持し、次に17.66部のブチルグリコールで希釈する。この樹脂の固形分は69.8%(130℃にて1時間測定)であり、粘度は5.5dPas(23℃のコーン/プレート粘度計でプロピレングリコールモノメチルエーテル(Solvenon PM,BASF)を用いて40%強度に希釈した樹脂溶液で測定)である。
欧州特許第0505445B1号(10頁35〜41行)に記載される方法に従って、水性顔料ペーストを、欧州特許第0961797号(9頁、表1、顔料ペーストB)に列挙される出発物質から調製する。この目的のため、まず第一に、27.1部の脱イオン水および25部の調製例3の練磨型樹脂をプレミックスに形成する。次に、6部のケイ酸アルミニウム、0.6部のカーボンブラック(ビーズ状)、38.1部の二酸化チタン、および2.7部のジブチル錫オキシドを添加し、この系を高速溶解槽攪拌機(dissolver stirrer)下で30分間混合する。その後、混合物を小型の実験用ミルでヘグマン粉末度が12よりも低くなるまで1〜1.5時間分散させる。
従来型(比較例1)および本発明(本発明の実施例1)の陰極電着塗料を調製するため、2006部の調製例2の結合剤分散体、603部の調製例4の水性顔料ペースト、および2391部の脱イオン水を合わせて電着浴を形成する。ここでの手順は結合剤分散体を最初に導入して、それを脱イオン水で希釈することである。その後、顔料ペーストを攪拌しながら導入する。報告される値は重量分率(g)である。さらに、本発明の電着材料を調製するために、電着材料全体に基づいて100ppm、200ppmまたは300ppm、のジルコニウム(IV)アセチルアセトナートを電着材料に添加する。
比較例1の試験パネルの塗装後、比較例1の陰極電着材料を100ppmのリン酸水素二ナトリウムと混合し、24時間攪拌する。次に、ギ酸を用いてpHを5.5に調節する。本発明の電着材料を調製するため、電着材料全体に基づいて100ppm、200ppmまたは300ppm、のジルコニウム(IV)アセチルアセトナートを電着材料にさらに添加する。その後、従来型の電着材料および本発明の電着材料を、上記の塗料膜の付着に先立って再び24時間攪拌する。焼付け後、陰極電着浴中で水平に備え付けた試験パネルの一部の10×10cmの面積のクレーターの数を評価する。結果を表1に示す。
Claims (15)
- 陰極電着塗料であって、
(A)陽性基を含有する少なくとも1種の水分散性有機結合剤としての水分散性アミン変性エポキシ樹脂、
を含み、及び陰極電着塗料の固形分に基づいて、0.005質量%〜0.15質量%の、(B)1以上の酸素含有配位子を有する四価の有機ジルコニウム錯体としてのジルコニウムアセチルアセトナートと混合されている、塗料。 - 少なくとも1つの酸素含有配位子が、二座非配位子または多座配位子である、請求項1に記載の塗料。
- 少なくとも1つの酸素含有配位子が、アルカノラートまたはエノラートである、請求項1に記載の塗料。
- 少なくとも1つの配位子が、β−ジケトンから誘導されるエノラートである、請求項3に記載の塗料。
- 陰極電着塗料に適した少なくとも1種の錫含有架橋触媒とさらに混合されている、請求項1〜4のいずれか一項に記載の塗料。
- さらなる架橋触媒が、ジブチル錫オキシドまたはジオクチル錫オキシドである、請求項5に記載の塗料。
- i)陽性基を含有する少なくとも1種の水分散性有機結合剤(A)としての水分散性アミン変性エポキシ樹脂を水溶液中に分散させて、水性結合剤分散体を得る工程と、
ii)水性結合剤分散体と(B)陰極電着塗料の固形分に基づいて0.005質量%〜0.15質量%の、1以上の酸素含有配位子を有する四価の有機ジルコニウム錯体としてのジルコニウムアセチルアセトナートを混合する工程と、
iii)所望であれば、さらなる添加剤を導入する工程と、
を含む、請求項1〜6のいずれか一項に記載の陰極電着塗料を調製するための方法。 - 導電性金属基材を陰極電着塗装によって塗装するために、請求項1〜6のいずれか一項に記載の陰極電着塗料を使用する方法であって、
電着浴内で塗装を行う塗装工程を含み、
前記電着浴の温度は、15〜40℃の範囲に設定され、更に
前記塗装工程で前記導電性金属基材に付着した塗料膜が、130〜220℃の温度範囲で、焼き付けられることを特徴とする方法。 - 基材が、リン酸化金属基材、より詳しくはリン酸化鋼基材である、請求項8に記載の使用方法。
- 基材が自動車の車体またはその部品である、請求項8または9に記載の使用方法。
- 請求項1〜6のいずれか一項に記載の塗料で塗装された塗装金属基材。
- 基材が自動車の車体またはその部品である、請求項11に記載の塗装基材。
- 最初に金属基材をリン酸化し、その後にリン酸化処理した金属基材を請求項1〜6のいずれか一項に記載の塗料で塗装することを含む、請求項1〜6のいずれか一項に記載の塗料で塗装された金属基材を製造する方法。
- 基材がリン酸化鋼である、請求項13に記載の方法。
- 基材が自動車の車体またはその部品である、請求項13または14に記載の方法。
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PCT/EP2009/001402 WO2009106337A1 (de) | 2008-02-29 | 2009-02-27 | Kathodischer elektrotauchlack enthaltend metallorganische verbindung |
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CN (1) | CN101959975B (ja) |
DE (1) | DE102008012085A1 (ja) |
WO (1) | WO2009106337A1 (ja) |
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EP2405031A1 (de) | 2010-07-07 | 2012-01-11 | Mattthias Koch | Verfahren zur Beschichtung von Formkörpern sowie beschichteter Formkörper |
DE102011078032A1 (de) * | 2011-06-24 | 2012-12-27 | Aleris Aluminum Koblenz Gmbh | Fahrzeugbauteil und Verfahren zu seiner Herstellung |
US20150008125A1 (en) * | 2012-02-21 | 2015-01-08 | Nitto Kasei Co., Ltd. | Electrodeposition coating composition, and catalyst for electrodeposition coating composition |
WO2015166745A1 (ja) | 2014-04-28 | 2015-11-05 | 日東化成株式会社 | 電着塗料組成物、電着塗料組成物用触媒 |
WO2023117915A1 (en) | 2021-12-21 | 2023-06-29 | Basf Se | Inbound chemical product with environmental attributes |
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AU528342B2 (en) * | 1978-12-11 | 1983-04-28 | Shell Internationale Research Maatschappij B.V. | Thermosetting resinous binder compositions |
JPS64167A (en) * | 1987-02-25 | 1989-01-05 | Kansai Paint Co Ltd | Water-based coating composition |
AT390621B (de) * | 1988-05-13 | 1990-06-11 | Vianova Kunstharz Ag | Kathodisch abscheidbare elektrotauchlacke |
JPH02135266A (ja) * | 1988-11-16 | 1990-05-24 | Kansai Paint Co Ltd | カチオン型電着塗料 |
JP2679740B2 (ja) * | 1989-03-17 | 1997-11-19 | 関西ペイント株式会社 | カチオン電着塗料用樹脂 |
DE3915080A1 (de) | 1989-05-09 | 1990-11-15 | Basf Lacke & Farben | Verfahren zur beschichtung elektrisch leitfaehiger substrate |
DE3942766A1 (de) | 1989-12-23 | 1991-06-27 | Basf Lacke & Farben | Verfahren zum beschichten elektrisch leitfaehiger substrate, waessriger lack, epoxid-aminaddukt und verwendung des epoxid-aminadduktes als reibharz zur herstellung von pigmentpasten |
AT393510B (de) * | 1990-02-12 | 1991-11-11 | Vianova Kunstharz Ag | Verfahren zur herstellung von kationischen lackbindemitteln zur formulierung von pigmentpasten fuer kathodisch abscheidbare elektrotauchlacke |
US5283124A (en) * | 1990-03-02 | 1994-02-01 | Kansai Paint Co., Ltd. | Coating resin composition |
JP3356302B2 (ja) * | 1992-04-24 | 2002-12-16 | 関西ペイント株式会社 | 水性塗料用樹脂組成物 |
JPH0610189A (ja) * | 1992-06-26 | 1994-01-18 | Kansai Paint Co Ltd | 塗膜形成方法 |
JPH06210414A (ja) | 1993-01-19 | 1994-08-02 | Nippon Steel Corp | 溶鋼の誘導加熱装置におけるアース循環電流発生防止方法 |
DE4303787C1 (de) | 1993-02-10 | 1994-03-24 | Herberts Gmbh | Verfahren zur Herstellung von Elektrotauchlacküberzügen, die frei von Oberflächenstörungen sind und Verwendung von wäßrigen Polyvinylalkohollösungen zur Nachbehandlung von elektrophoretisch abgeschiedenen Überzügen |
JP2809592B2 (ja) * | 1994-06-08 | 1998-10-08 | 大日本塗料株式会社 | 耐食性塗料組成物 |
DE19703869A1 (de) | 1997-02-03 | 1998-08-06 | Basf Coatings Ag | Wäßrige Bindemitteldispersion für kationische Elektrotauchlacke |
US5846897A (en) | 1997-03-19 | 1998-12-08 | King Industries, Inc. | Zirconium urethane catalysts |
DE19856878A1 (de) | 1998-12-10 | 2000-06-15 | Inst Polymerforschung Dresden | Härtbare uretdiongruppenhaltige Massen und ein Verfahren zu ihrer Herstellung und Verarbeitung sowie ihre Verwendung |
US6132581A (en) | 1999-04-22 | 2000-10-17 | Ppg Industries Ohio, Inc. | Electrocoating compositions containing polyvinylpyrrolidone crater control agents |
AU2003277236B2 (en) * | 2002-10-01 | 2007-02-08 | Ppg Industries Ohio, Inc. | Electrodepositable coating compositions and related methods |
DE10308106A1 (de) | 2003-02-26 | 2004-09-09 | Bayer Aktiengesellschaft | Neue 2K-PUR-Systeme |
US7449095B2 (en) * | 2004-03-04 | 2008-11-11 | Kansai Paint Co., Ltd | Coating film-forming method |
US20070010644A1 (en) | 2005-07-08 | 2007-01-11 | Basf Corporation. | Elastomeric urethane composition |
JP4719546B2 (ja) * | 2005-10-04 | 2011-07-06 | 日本パーカライジング株式会社 | 陽極電解用処理液、電解処理方法及び電解処理金属材 |
CN100575428C (zh) * | 2007-04-30 | 2009-12-30 | 袁兴 | 低温固化环保型阴极电泳涂料的制备方法 |
JP5989995B2 (ja) * | 2011-02-04 | 2016-09-07 | 日東電工株式会社 | 剥離剤、離型材および粘着テープ |
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2009
- 2009-02-27 CN CN200980106908.8A patent/CN101959975B/zh active Active
- 2009-02-27 EP EP09715959.4A patent/EP2250224B1/de active Active
- 2009-02-27 JP JP2010548026A patent/JP5666316B2/ja active Active
- 2009-02-27 KR KR1020107020775A patent/KR20100130194A/ko not_active Application Discontinuation
- 2009-02-27 US US12/919,870 patent/US8617373B2/en active Active
- 2009-02-27 WO PCT/EP2009/001402 patent/WO2009106337A1/de active Application Filing
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Publication number | Publication date |
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WO2009106337A1 (de) | 2009-09-03 |
CN101959975A (zh) | 2011-01-26 |
DE102008012085A1 (de) | 2009-09-10 |
EP2250224B1 (de) | 2017-04-26 |
KR20100130194A (ko) | 2010-12-10 |
EP2250224A1 (de) | 2010-11-17 |
JP2011513525A (ja) | 2011-04-28 |
US20110042222A1 (en) | 2011-02-24 |
CN101959975B (zh) | 2014-03-05 |
US8617373B2 (en) | 2013-12-31 |
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