JP2015078381A - 水性放射線硬化性ポリウレタン組成物 - Google Patents
水性放射線硬化性ポリウレタン組成物 Download PDFInfo
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Abstract
【解決手段】本発明の組成物は、少なくとも1個のポリイソシアネート化合物(i)と、場合により少なくとも1個のポリオール(ii)と、イソシアネート基と反応できる少なくとも1個の反応基を含有し、直接又は中和剤との反応後に水性媒質中でポリウレタンプレポリマーを分散可能にし、塩を提供することができる少なくとも1個の親水性化合物(iii)と、イソシアネート基と反応できる少なくとも2個の反応基を含有する(メト)アクリル化化合物(iv)と、イソシアネート基と反応できる基本的に1個の反応基を含有する少なくとも1個の(メト)アクリル化化合物(v)の反応から得られる少なくとも1個の(メト)アクリル化ポリウレタンプレポリマー(A)と、場合により少なくとも1個のエチレン不飽和化合物(B)を含み、重合性のエチレン不飽和基の所定総量を含む。
【選択図】なし
Description
−少なくとも1個の(メト)アクリル化ポリウレタンプレポリマー(A)であって、
−少なくとも1個のポリイソシアネート化合物(i)と、
−場合により、少なくとも1個のポリオール(ii)と、
−イソシアネート基と反応できる少なくとも1個の反応基を含有し、直接又は中和剤との反応後に水性媒質中でポリウレタンプレポリマーを分散可能にし、塩を提供することができる少なくとも1個の親水性化合物(iii)と、
−イソシアネート基と反応できる少なくとも2個の反応基を含有する少なくとも1個の(メト)アクリル化化合物(iv)と、
−イソシアネート基と反応できる基本的に1個の反応基を含有する少なくとも1個の(メト)アクリル化化合物(v)の前記化合物(i)、(ii)、(iii)、(iv)及び(v)の反応から得られる少なくとも1個の(メト)アクリル化ポリウレタンプレポリマー(A)と、
−場合により、少なくとも1個のエチレン不飽和化合物(B)
を含み、
前記組成物が、(i)、(ii)、(iii)、(iv)、(v)及び(B)の総重量(g)当り少なくとも3meqの(メト)アクリル化及び、場合により、重合性のエチレン不飽和基の総量を含む水性放射線硬化性組成物に関する。
−化合物(i)、(iii)及び(iv)、及び、場合により、化合物(ii)の反応を含む第一段階と、
−前記第一段階の生成物の、化合物(v)との反応を含み、当該反応によって、末端封鎖(メト)アクリル化ポリウレタンプレポリマーが得られる第二段階と、
−前記第二段階後に得られる前記末端封鎖(メト)アクリル化ポリウレタンプレポリマーの水性媒質への分散の段階と、
−場合により、中和剤との反応を含み、化合物(iii)によって提供される親水基を、陰イオン塩に転換する段階と、
−場合により、前記第二段階後に得られる(メト)アクリル化ポリウレタンプレポリマーが連鎖延長剤(vii)と反応する段階と、
−場合により、エチレン不飽和化合物(B)の添加の段階を
含むプロセスによって得られる。
−化合物(i)、(iii)及び(iv)、かつ、場合により、化合物(ii)の反応を含む第一段階と、
−化合物(v)との前記第一段階の生成物との反応を含み、それによって、末端封鎖(メト)アクリル化ポリウレタンプレポリマーが得られる第二段階と、
−前記第二段階後に得られた前記末端封鎖(メト)アクリル化ポリウレタンプレポリマーの水性媒質中への分散の段階と、
−場合により、化合物(iii)によって提供される親水基を陰イオン塩に転換することを目的に中和剤との反応を含む段階と、
−場合により、前記第二段階後に得られる(メト)アクリル化ポリウレタンプレポリマーが、連鎖延長剤(vii)と反応する段階と、
−場合により、エチレン不飽和化合物(B)の添加を含む段階
を含む、放射線硬化性組成物を調製するプロセスにも関する。
機械式攪拌棒、熱電対、蒸気冷却器及び滴下漏斗を備えた二重壁ガラス反応器に、平均分子量670、167mg KOH/gのヒドロキシル価を有し、アジピン酸とイソフタル酸の重量比1:1混合物とネオペンチルグリコールの重縮合から入手された45.3gのポリエステルポリオール、109.2gのビスフェノールAジグリシジルエーテルのアクリル酸付加物(BPAAA)、34.3gのジメチロールプロピオン酸(DMPA)、231.3gの1,1−メチレンビス(4−イソシアネートシクロへキサン)(H12MDI)、279gのアセトン、3.1gのTINUVIN(登録商標)622及び0.6gのジブチル錫ラウレートがアセトン中10%溶液として投入された。当該反応混合物は、攪拌下で60℃まで加熱され、イソシアネート含量が1.09meg/gの数値に達するまで還流下で保持された。次いで、207.1gのDTMPTA(ジトリメチロールプロパントリアクリレートとジトリメチロールプロパンテトラアクリレートの混合物を含み、KOH/g 137mgのヒドロキシル価を有する生成物)に溶解された0.4gの4−メトキシフェノールが、前記反応器にゆっくりと添加され、イソシアネート含量が0.19meq/gの数値に達するまで、還流下で保持された。次いで、6官能性脂肪族ウレタンアクリレートである209gのEBECRYL(登録商標)1290が、当該反応混合物に添加され、均質混合物が得られるまで攪拌された。次いで、この混合物は、45℃まで冷却され、25.8gのトリエチルアミンが、攪拌下で添加された。次いで、生じた混合物は、安定な分散物が得られるまで、高速剪断攪拌下、室温で1268gの水にゆっくりと添加された。真空下、50℃の温度で、アセトンが、ガスクロマトグラフィー測定でそのレベルが0.15%よりも低くなるまで、ストリップされた。次いで、当該ポリマー分散物は、30℃よりも低い温度まで冷却され、2.3gの殺生物剤(Acticide(登録商標)MBS)が添加された。当該分散物は、100μ篩で濾過され、その固形分は、水を添加して40%に調整された。乾燥含量は、重量法で測定された。
実施例2〜5及び7〜16では、表1の規定どおりに異なる量及び異なる成分が使用された点を除いて、実施例1に記載のプロセスが繰り返された。他で規定されない限り、各種化合物の量は、g表示である。
Claims (11)
- 水性放射線硬化性組成物において、
−少なくとも1個の(メト)アクリル化ポリウレタンプレポリマー(A)であって、
−少なくとも1個のポリイソシアネート化合物(i)と、
−場合により、少なくとも1個のポリオール(ii)と、
−イソシアネート基と反応できる少なくとも1個の反応基を含有し、直接又は中和剤との反応後に、水性媒質中でポリウレタンプレポリマーを分散可能にし、塩を提供することができる少なくとも1個の親水性化合物(iii)と、
−イソシアネート基と反応できる少なくとも2個の反応基を含有する少なくとも1個の(メト)アクリル化化合物(iv)と、
−イソシアネート基と反応できる基本的に1個の反応基を含有する少なくとも1個の(メト)アクリル化化合物(v)の
前記5種類の化合物の反応から得られる(メト)アクリル化ポリウレタンプレポリマー(A)と、
−場合により、少なくとも1個のエチレン不飽和化合物(B)
を含み、
前記組成物が、(i)、(ii)、(iii)、(iv)、(v)及び(B)の総重量(g)当り少なくとも3meqの(メト)アクリル化基及び場合により、重合性のエチレン不飽和基の総量を含む、
水性放射線硬化性組成物。 - 放射線硬化性組成物であって、
−化合物(i)、(iii)及び(iv)及び場合により、化合物(ii)の反応を含む第一段階と、
−前記第一段階の生成物の、化合物(v)との反応を含み、前記反応によって、末端封鎖(メト)アクリル化ポリウレタンプレポリマーが得られる第二段階と、
−前記第二段階後に得られる前記末端封鎖(メト)アクリル化ポリウレタンプレポリマーの水性媒質への分散の段階と、
−場合により、中和剤との反応を含み、化合物(iii)によって提供される親水基を、陰イオン塩に転換する段階と、
−場合により、前記第二段階後に得られる(メト)アクリル化ポリウレタンプレポリマーが連鎖延長剤(vii)と反応する段階と、
−場合により、エチレン不飽和化合物(B)の添加の段階
を含むプロセスによって得られる、請求項1に記載の放射線硬化性組成物。 - 前記ポリイソシアネート(i)が、脂肪族及び脂環式ポリイソシアネートから選択される、請求項1〜2のいずれかに記載の放射線硬化性組成物。
- 前記ポリオール(ii)が、少なくとも400の数平均分子量を有するポリエステルポリオールである、請求項1および3のいずれかに記載の放射線硬化性組成物。
- 前記親水性化合物(iii)が、一般式(HO)xR(COOH)yで表され、式中、Rが炭素原子1〜12個を有する直鎖もしくは枝分れ炭化水素残基で、x及びyが独立して1〜3までの整数であるヒドロキシカルボン酸から選択される、請求項1〜4のいずれかに記載の放射線硬化性組成物。
- 前記(メト)アクリル化化合物(iv)が、(メト)アクリル酸とのジグリシジル化合物の反応生成物から選択される、請求項1から5までのいずれかに記載の放射線硬化性組成物。
- 前記(メト)アクリル化化合物(iv)が、ビスフェノールAジグリシジルエーテルのジアクリレートエステルである、請求項6に記載の放射線硬化性組成物。
- 前記(メト)アクリル化化合物(v)が、残存平均ヒドロキシル官能価約1を有する、脂肪族及び/又は芳香族ポリオールの(メト)アクリル酸とのエステル化生成物から選択される、請求項1〜7のいずれかに記載の放射線硬化性組成物。
- (メト)アクリル酸の、三価−、四価−、五価及び/又は六価ポリアルコール及びそれらの混合物のエステル化生成物から選択されるエチレン不飽和化合物を含む、請求項1〜8のいずれかに記載の放射線硬化性組成物。
- 放射線硬化性組成物の調製プロセスであって、
−化合物(i)、(iii)及び(iv)及び任意に化合物(ii)の反応を含む第一段階と、
−化合物(v)との前記第一段階の生成物の反応を含み、それによって、末端封鎖(メト)アクリル化ポリウレタンプレポリマーが得られる第二段階と、
−前記第二段階後に得られた前記末端封鎖(メト)アクリル化ポリウレタンプレポリマーの水性媒質中への分散の段階と、
−場合により、化合物(iii)によって提供される親水基を陰イオン塩に転換することを目的に中和剤との反応を含む段階と、
−場合により、前記第二段階後に得られた(メト)アクリル化ポリウレタンプレポリマーが、連鎖延長剤(vii)と反応する段階と、
−場合により、エチレン不飽和化合物(B)の添加を含む段階
を含む、請求項1〜9のいずれかに記載の、放射線硬化性組成物の調製プロセス。 - コーティング用品を調製するプロセスであって、前記用品が、請求項1〜9のいずれかに記載の放射線硬化性組成物でコートされる段階を含む、コーティング用品の調製プロセス。
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EP1584636A1 (de) * | 2004-04-08 | 2005-10-12 | Surface Specialties Austria GmbH | Wässrige Bindemittel für strahlenhärtbare Lacke |
US20070149704A1 (en) | 2005-06-17 | 2007-06-28 | Reichhold, Inc. | Radiation curable polyurethane dispersions |
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2006
- 2006-04-14 EP EP06007921A patent/EP1845143A1/en not_active Withdrawn
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2007
- 2007-03-30 KR KR1020087024973A patent/KR101498294B1/ko active IP Right Grant
- 2007-03-30 CN CN2007800134413A patent/CN101421368B/zh active Active
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2015
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JPH0217973A (ja) * | 1988-05-18 | 1990-01-22 | Roehm Gmbh | 耐引掻性被覆加工を施したプラスチツク成形体の製法 |
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