JP5383494B2 - 金属と配位結合する被膜形成材料 - Google Patents
金属と配位結合する被膜形成材料 Download PDFInfo
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Description
X3−R4−X4
[式中、特に、X3及びX4の少なくとも1つが、樹脂に対して反応性を有しており、X3は、ヒドロキシル又はカルボキシルの一価の基であり、R4は、約90g/mol〜約5000g/molの分子量、及び非イオン性金属配位構造を有するアルキル又は芳香族の二価の基であり、並びにX4は、水素、ヒドロキシル又はカルボキシルの一価の基である]の求核試薬との反応による生成物を含む。
X5−R5−X6
[式中、X5は、エポキシド又はハライドの一価の基であり、R5は、アルキレン又はアリーレンの二価の基であり、好ましくは約90g/mol〜約5000g/molの分子量、及び非イオン性金属配位構造を有し、並びにX6は、水素、エポキシド、又はハライドの一価の基である]の求電子試薬との反応による生成物を含む。
実施例1Aから1Dは、記載のように、それぞれの表に示されているように製造する。実施例1Aは、連鎖停止配位子としてフェノールを用いており、この配位子は、ポリマーの総組成物の5質量%未満において添加される。実施例1Bでは、同じ配位子分子を用いており、この場合、末端基の代わりにエチルフェニルグリシデートを用いており、ビスフェノールAの量を増やして、アミンキャップ工程前のポリマーの高級化反応の完了後の未反応のエポキシの同等量が残るようにした。実施例1Cでは、キャップ基の半量の代わりにエチルフェニルグリシデートを用い、残りの半量の代わりに4−ヒドロキシ安息香酸エチルを用いる。もう一度、ポリマーの高級化反応の完了後に、ビスフェノールA及び液体エポキシを調整して、未反応エポキシの同等量が残るようにした。実施例1Dでは、キャップ基の代わりに、4−ヒドロキシ安息香酸エチルを用いる。
以下の材料を、マントルヒーターを備えた5Lフラスコ中で混合する:
ビスフェノールAのジグリシジルエーテル(DGEBA)、(652.05g、6.4エポキシ当量)
ビスフェノールA(BPA)、(148.27g、2.0OH当量)
フェノール
エチルフェニルグリシデート(34.14g、0.3当量)、及び
ブトキシプロパノール(25.16g)
以下の材料を、マントルヒーターを備えた5Lフラスコ中で混合する:
ビスフェノールAのジグリシジルエーテル(DGEBA)、(619.45g、6.4エポキシ当量)、
ビスフェノールA(BPA)、(258.24g、2.2OH当量)、
エチルフェニルグリシデート(108.12g、1.0当量)、及び
ブトキシプロパノール(23.90g)
以下の材料を、マントルヒーターを備えた5Lフラスコ中で混合する:
ビスフェノールAのジグリシジルエーテル(DGEBA)、(619.45g、6.4エポキシ当量)、
ビスフェノールA(BPA)、(258.24g、2.2OH当量)、
エチルフェニルグリシデート(54.06g、0.5当量)
4−ヒドロキシ安息香酸エチル(42.73g、0.5当量)、及び
ブトキシプロパノール(23.90g)
以下の材料を、マントルヒーターを備えた5Lフラスコ中で混合する:
ビスフェノールAのジグリシジルエーテル(DGEBA)、(619.45g、6.4エポキシ当量)、
ビスフェノールA(BPA)、(140.86g、1.2OH当量)、
4−ヒドロキシ安息香酸エチル(85.46g、0.5当量)、及び
ブトキシプロパノール(23.90g)
第三級アンモニウム基を有する粉砕樹脂溶液の製造:欧州特許第0505445号明細書の実施例1.3により、第1工程において、ビスフェノール−A−ジグリシジルエーテル(エポキシ当量(EEW)188g/eq)2598部、ビスフェノールA787部、ドデシルフェノール603部、及びブチルグリコール206部を、ステンレススチール反応器中において、トリフェニルホスフィン4部の存在下130℃で、EEWが865g/eqに達するまで反応させて、水性有機粉砕樹脂溶液を製造した。冷却中に、このバッチを、ブチルグリコール849部及びD.E.R.(登録商標)732(ポリプロピレングリコールジグリシジルエーテル、DOW Chemical、USA)1534部によって希釈し、さらに90℃で2,2’−アミノエトキシエタノール266部及びN、N−ジメチルアミノプロピルアミン212部と反応させた。2時間後、この樹脂溶液の粘度は一定であった(5.3dPa・s;Solvenon(登録商標)PM(メトキシプロパノール、BASF/ドイツ)中40%濃度;23℃で円錐平板粘度計)。この樹脂溶液をブチルグリコール1512部で希釈し、塩基性基を氷酢酸201部で部分的に中和して、その生成物をさらに脱イオン水1228部で希釈して、フラスコから取り出す。これにより、その10%希釈物がpH6.0の、60%濃度の水性有機樹脂溶液が得られた。この樹脂溶液を、そのままの形でペースト製造に使用した。
硬化を評価するための一次スクリーニングツールとして、メチルエチルケトン(MEK)による二重摩擦を実施した。パネルは、亜鉛リン酸処理の有無のCRSを用い、コーティング組成物でコーティングし、様々な時間及び温度で硬化させて、硬化コーティングを形成した。
未被覆CRSパネルを実施例1A〜1Dのウレタンコーティング組成物でコーティングして約0.4ミルのウレタン被膜を形成した。なお、3つのパネルは、それぞれの実施例のそれぞれの温度でコーティングした。これらのパネルを、約300°F、325°F、及び350°Fにて、約20分間硬化させた。
非イオン性金属配位構造を含む電解析出可能なアクリル性コーティング組成物
カチオン化樹脂の製造(成分A):(1)撹拌機、温度計、窒素導入口、及び還流冷却器を備えたフラスコに、ブチルセロソルブ541部を入れ、攪拌しながら120℃まで加熱した。温度を維持しながら、以下の化合物:スチレン(484部);2−アリルオキシテトラヒドロピラン(26部);2−ヒドロキシエチルメタクリレート(340部);n−ブチルアクリレート(114部);「FM−3」(113部)(FM−3は、ダイセル化学工業の製品であり、ε−カプロラクトンを2−ヒドロキシルエチルメタクリレートに付加させることにより製造したヒドロキシル基含有の重合性不飽和化合物である);アクリル酸(57部);及び、アゾイソブチロニトリル(68部)、の混合物を3時間かけて滴下して加えた。
Claims (4)
- 求電子試薬に対して反応性の少なくとも1つの基を有する樹脂と求電子性配位子との反応による生成物を有する被膜形成材料であって、前記求電子性配位子が、3−メチル−1−(オキシラン−2−イル)ブタ−3−エン−2−オン、エチルフェニルグリシデート及びそれらの組み合わせから成る群から選択される、前記被膜形成材料。
- 求電子性試薬に対して反応性の少なくとも1つの基が、ヒドロキシル基である、請求項1に記載の被膜形成材料。
- 前記反応は、さらに、ビスフェノールAのジグリシジルエーテル、フェノール、金属もしくは金属化合物、及びそれらの組合せから成る群から選択される材料を含む、請求項1に記載の被膜形成材料。
- 前記金属又は金属化合物が、前記非イオン性金属配位構造によって配位結合されている、請求項3に記載の被膜形成材料。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/553,185 US7759436B2 (en) | 2006-10-26 | 2006-10-26 | Film-former of resin with nonionic metal coordinating structure and crosslinker-reactive group |
US11/553,185 | 2006-10-26 | ||
PCT/US2007/075764 WO2008051648A1 (en) | 2006-10-26 | 2007-08-13 | Metal coordinating and film-forming materials |
Publications (3)
Publication Number | Publication Date |
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JP2010508396A JP2010508396A (ja) | 2010-03-18 |
JP2010508396A5 JP2010508396A5 (ja) | 2010-09-30 |
JP5383494B2 true JP5383494B2 (ja) | 2014-01-08 |
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Application Number | Title | Priority Date | Filing Date |
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JP2009534730A Expired - Fee Related JP5383494B2 (ja) | 2006-10-26 | 2007-08-13 | 金属と配位結合する被膜形成材料 |
Country Status (10)
Country | Link |
---|---|
US (1) | US7759436B2 (ja) |
EP (1) | EP2076555B1 (ja) |
JP (1) | JP5383494B2 (ja) |
KR (1) | KR20090080099A (ja) |
CN (1) | CN101528795B (ja) |
AT (1) | ATE494317T1 (ja) |
BR (1) | BRPI0718191A2 (ja) |
CA (1) | CA2629072A1 (ja) |
DE (1) | DE602007011794D1 (ja) |
WO (1) | WO2008051648A1 (ja) |
Families Citing this family (25)
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US7867570B2 (en) * | 2006-10-26 | 2011-01-11 | Basf Coatings Gmbh | Method of producing a coating having metal coordinating and film-forming materials |
US7772334B2 (en) * | 2006-10-26 | 2010-08-10 | Basf Coatings Gmbh | Crosslinker of reactive functional groups and nonionic metal coordinating structure-containing alkyl or aromatic compound |
US7674874B2 (en) * | 2007-02-08 | 2010-03-09 | Basf Coatings Ag | Methods of producing coating compositions containing phosphorous |
US20080194843A1 (en) * | 2007-02-08 | 2008-08-14 | Basf Corporation | Crosslinkers containing phosphorous |
US7671170B2 (en) * | 2007-02-08 | 2010-03-02 | Basf Coatings Ag | Film-forming material containing phosphorous |
US20100163423A1 (en) * | 2008-12-29 | 2010-07-01 | Basf Corporation | Electrocoat composition and process replacing phosphate pretreatment |
US8961768B2 (en) * | 2008-12-29 | 2015-02-24 | Basf Corporation | Metal containing integrated electrocoat for better corrosion resistance |
US8354471B2 (en) * | 2008-12-29 | 2013-01-15 | Basf Coatings Gmbh | Acrylic electrocoat composition and process replacing phosphate pretreatment |
JP5623423B2 (ja) | 2008-12-29 | 2014-11-12 | ビーエーエスエフ コーティングス ゲゼルシャフト ミット ベシュレンクテル ハフツングBASF Coatings GmbH | 水性の電着コーティング組成物、リン酸塩前処理の代用法を含む金属の自動車車体をコーティングするための方法、及び、該水性の電着コーティング組成物の製造方法 |
US8192603B2 (en) | 2008-12-29 | 2012-06-05 | Basf Coatings Gmbh | Electrocoat composition and process replacing phosphate pretreatment |
US9382638B2 (en) * | 2008-12-29 | 2016-07-05 | Basf Corporation | Electrocoat composition and process replacing phosphate pretreatment |
US9206284B2 (en) * | 2008-12-29 | 2015-12-08 | Basf Coatings Gmbh | Coating compositions with branched phosphorous-containing resin |
US8815066B2 (en) * | 2008-12-29 | 2014-08-26 | Basf Coatings Gmbh | Coating composition with phosphorous-containing resins and organometallic compounds |
US8702943B2 (en) * | 2008-12-29 | 2014-04-22 | Basf Coatings Gmbh | Electrocoat composition and process replacing phosphate pretreatment |
US20100167071A1 (en) * | 2008-12-29 | 2010-07-01 | Basf Corporation | Pyridine group-containing electrocoat composition with metal oxide |
JP5778954B2 (ja) | 2011-03-16 | 2015-09-16 | イビデン株式会社 | 排気管 |
US9062162B2 (en) * | 2013-03-15 | 2015-06-23 | Prc-Desoto International, Inc. | Metal ligand-containing prepolymers, methods of synthesis, and compositions thereof |
EP3063244A2 (en) * | 2013-10-29 | 2016-09-07 | PRC-Desoto International, Inc. | Adhesion promoting adducts containing metal ligands, compositions thereof, and uses thereof |
JP6436988B2 (ja) * | 2013-10-29 | 2018-12-12 | ピーアールシー−デソト インターナショナル,インコーポレイティド | 金属リガンド含有プレポリマー、その合成方法、及びその組成物 |
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-
2006
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2007
- 2007-08-13 EP EP07814009A patent/EP2076555B1/en not_active Not-in-force
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- 2007-08-13 BR BRPI0718191-4A patent/BRPI0718191A2/pt not_active IP Right Cessation
- 2007-08-13 JP JP2009534730A patent/JP5383494B2/ja not_active Expired - Fee Related
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US7759436B2 (en) | 2010-07-20 |
BRPI0718191A2 (pt) | 2013-11-05 |
WO2008051648A1 (en) | 2008-05-02 |
US20080103268A1 (en) | 2008-05-01 |
ATE494317T1 (de) | 2011-01-15 |
DE602007011794D1 (ja) | 2011-02-17 |
EP2076555A1 (en) | 2009-07-08 |
EP2076555B1 (en) | 2011-01-05 |
CA2629072A1 (en) | 2008-05-02 |
KR20090080099A (ko) | 2009-07-23 |
CN101528795B (zh) | 2012-02-29 |
CN101528795A (zh) | 2009-09-09 |
JP2010508396A (ja) | 2010-03-18 |
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