JP5361883B2 - 親水性被覆剤、親水性被膜、及び親水性基材 - Google Patents
親水性被覆剤、親水性被膜、及び親水性基材 Download PDFInfo
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- JP5361883B2 JP5361883B2 JP2010514406A JP2010514406A JP5361883B2 JP 5361883 B2 JP5361883 B2 JP 5361883B2 JP 2010514406 A JP2010514406 A JP 2010514406A JP 2010514406 A JP2010514406 A JP 2010514406A JP 5361883 B2 JP5361883 B2 JP 5361883B2
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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
- 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
-
- 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
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4063—Mixtures of compounds of group C08G18/62 with other macromolecular compounds
-
- 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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4269—Lactones
- C08G18/4277—Caprolactone and/or substituted caprolactone
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- 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
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- 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
- C08G18/625—Polymers of alpha-beta ethylenically unsaturated carboxylic acids; hydrolyzed polymers of esters of these acids
- C08G18/6254—Polymers of alpha-beta ethylenically unsaturated carboxylic acids and of esters of these acids containing hydroxy groups
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- 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
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Description
(合成例1)
反応容器中に、溶媒としてメチルエチルケトン(MEK)233部を仕込み、60℃まで昇温した。
モノマー成分として、MA−50Aからなるモノマー100部を用い、連鎖移動剤として2−メルカプトメタノール 1部を配合した以外は合成例1と同様にして、水酸基価55で、重量平均分子量(Mw)8000のアクリルポリマーを含有する樹脂溶液を製造した。
モノマー成分として、MMA 50部、N,N−ジメチルアクリルアミド(DMAA) 30部、及び2−ヒドロキシエチルアクリレート(2−HEA)20部からなるモノマーを用いた以外は合成例1と同様にして、水酸基とアミド基とを有する水酸基価31で、重量平均分子量(Mw)14000のアクリルポリマーを含有する樹脂溶液を製造した。
モノマー成分として、MMA 85部、及び、MA−50A 15部からなるモノマーを用いた以外は合成例1と同様と同様にして、水酸基価15で、重量平均分子量(Mw)26000のアクリルポリマーを含有する樹脂溶液を製造した。
モノマー成分として、MMA50部、及びポリカプロラクトンオリゴマーにラジカル重合性を有する不飽和二重結合と第一級水酸基とを1個ずつ導入したマクロモノマー(プラクセルFM5,ダイセル化学工業(株)製)50部からなるモノマーを用いた以外は合成例1と同様にして、水酸基価65で、重量平均分子量(Mw)30000のアクリルポリマーを含有する樹脂溶液を製造した。
モノマー成分として、MA−50Aからなるモノマー100部を用い、重合触媒としてABN−E 6部を用い、さらに、2−メルカプトメタノール 2部を配合した以外は合成例1と同様にして、水酸基価55で、重量平均分子量(Mw)4000のアクリルポリマーを含有する樹脂溶液を製造した。
重合触媒(ABN−E)の添加量を4部から0.5部に変更した以外は合成例1と同様にして、水酸基価25で、重量平均分子量(Mw)250000のアクリルポリマーを含有する樹脂溶液を製造した。
合成例1〜7で得られたアクリルポリマーを用いて以下のように親水性被覆剤を製造した。
(A)コロイダルシリカゾル
・MEK−ST(日産化学(株)製、スノーテックシリーズ):分散粒径10〜15nm、不揮発分30%
(C)シランカップリング剤
・S−510溶液:グリシドキシプロピルトリメトキシシラン(サイラプレーンS−510、チッソ(株)製)のMEK溶液、不揮発分30%
・KBE−9007溶液:イソシアネートプロピルトリエトキシシラン(KBE−9007、信越化学工業(株)製)のMEK溶液、不揮発分30%
(D)ポリラクトンポリオール
・プラクセル303溶液:ポリカプロラクトントリオール(プラクセル303溶液、ダイセル化学工業(株)製)のMEK溶液、不揮発分30%
(E)硬化剤
・WB40−100溶液:デュラネートWB40−100(旭化成ケミカルズ(株)製の親水基付与変性ヘキサメチレンジイソシアネート(HDI)のビュレット型水分散ポリウレタン樹脂)のMEK溶液、不揮発分30%
・D−165N溶液:タケネートD−165N(三井武田ケミカルズ(株)製のヘキサメチレンジイソシアネート(HDI)のビュレット型ポリレタン樹脂)のMEK溶液、不揮発分30%
・
D−170N溶液:タケネートD−170N(三井武田ケミカルズ(株)製のヘキサメチレンジイソシアネート(HDI)のヌレート型ポリレタン樹脂)のMEK溶液、不揮発分30%
・
D−178N溶液:タケネートD−178N(三井武田ケミカルズ(株)製のヘキサメチレンジイソシアネート(HDI)のアロファネート型ポリレタン樹脂)のMEK溶液、不揮発分30%
(F)界面活性剤
・エバンU105溶液:ポリオキシエチレンポリオキシプロピレングリコールエーテル(第一工業製薬(株)製エバンU105)のMEK溶液、不揮発分30%
(G)硬化触媒
・TN−12溶液:ジブチル錫ラウレート(堺化学工業(株)製TN−12)のMEK溶液、不揮発分30%
表2に示すような組成により、以下の方法により親水性被覆剤を調製した。
表2の組成に従って調製した以外は、実施例1と同様にして親水性被覆剤を得た。
表3の組成に従って調製した以外は、実施例1と同様にして親水性被覆剤を得た。
上記実施例1〜14、及び比較例1〜10で得られた主剤に硬化剤(E)を配合し、撹拌混合して親水性被覆剤を調製した。そして、アプリケーター4milで150mm×70mm×0.5mm(厚み)のガラス板に得られた被覆剤を塗布した後、120℃、20分の条件で乾燥して試験板を作成した。このとき、厚み約15μmの被膜が得られた。そして、得られた試験板を用いて、下記評価試験に供した。
JIS K 5600−1−1の4.4「塗膜の外観」の試験法に準拠して、下記の基準により透明性及びクラックの有無を判定した。
優:無色透明であり、クラックなし。
劣:白濁し、またはクラックが発生した。
JIS K 5600−5−4「引っ掻き硬度(鉛筆法)」の試験法に準拠して、鉛筆硬度試験を実施した。鉛筆硬度試験においては、硬度が低い方から高いほうにB、HB、F、Hの順に並べられる。また、「H」の前に付く数字が大きいほど硬度が高く、「B」の前に付く数字が大きいほど硬度が低い。
JIS K 5600−5−6の「クロスカット法」の試験法に準拠して、密着性試験を実施した。具体的には、試験板に塗布した塗膜をカッターナイフで縦横方向に切断して基材に達するような100個のクロスカット(切断片)を形成した。そして、クロスカット上にセロハン粘着テープ(例えば、ニチバン(株)製、品番 ニチバンテープ1号)を貼り付けた。そして、貼り付けられたセロハン粘着テープを剥離した後に、剥離せずに残ったクロスカットの数を数えた。
JISK−6911の試験法に準拠して、デジタル高抵抗計(三菱化学(株)製 ハイレスタUP MCP-HT450)を用いて試験板表面の表面抵抗値[Ω]を測定した。なお、表面抵抗値[Ω]の乗数が小さい程、帯電防止性が高いことを示す。
優:表面抵抗値[Ω]の乗数が1012以上
劣:表面抵抗値[Ω]の乗数が1013以上
試験板の表面にノルマルヘキサデカンを0.1g垂らした。そして、試験板表面に付着したノルマルヘキサデカンをセルロース製不織布(ペンコットM−3:旭化成(株)製)により、300gの荷重を掛けて10回拭き取った。ヘーズメーターNDH5000(日本電色工業社製)を用いて試験前および試験後の試験板表面のヘーズ(濁度)を測定した。そして、ΔEを算出した。このΔEの値が小さいほど、油性汚れの拭き取り性が良好であり、すなわち、防汚性が良好であることを示す。
優:ΔEが0〜1
普通:ΔEが1〜3
劣:ΔEが3以上
試験板を23℃±2℃の水中に3日間浸漬した。そして浸漬後の試験片の外観を観察して、JIS K 5600−1−1の4.4「塗膜の外観」の試験法に準拠して、耐水性を判定した。
優:無色透明であった。
普通:半透明であった
劣:白化或は溶解した。
試験板を23℃±2℃の5%水酸化ナトリウム水溶液中に3日間浸漬した。そして浸漬後の試験片の外観を観察して、JIS K 5600−1−1の4.4「塗膜の外観」の試験法に準拠して、耐アルカリ性を判定した。
優:無色透明であった。
普通:半透明であった
劣:白化或は溶解した。
試験板表面に形成された被膜の表面にアセトンを滴下した後、荷重100gをかけて50回ラビング試験を行った。そして、JIS K 5600−1−1の4.4「塗膜の外観」の試験法に準拠して、耐溶剤性を判定した。
優:明らかに無色透明であった。
普通:半透明であった
劣:白化或は溶解した。
試験板表面で、スチールウール(ボンスター販売(株)製 品番#0000)を1cm2当たり300gの荷重を負荷しながら、水平方向に50往復させた。そして、そのときに発生した傷の本数を目視観察した。
優:傷の本数が0〜2本であった。
普通:傷の本数が2〜4本であった。
劣:傷の本数が5本以上であった。
50℃の温水の表面に1cmの間隔を空けて試験板の塗布面を対向させ、被膜の表面が曇り始めるまでの時間を測定した。
優:曇り始めるまでの時間に2分以上を要した。
普通:曇り始めるまでの時間が1分以上、2分未満であった。
劣:曇り始めるまでの時間が1分未満であった。
試験板表面に0.4μLの水滴を垂らし、接触角計(協和界面科学社製、Drop Master500)により接触角を測定した。
Claims (14)
- (A)コロイダルシリカゾルと、
(B)活性水素を有する重量平均分子量(Mw)5千〜20万のアクリルポリマーと、
(C)一末端に(B)成分と結合する官能基を有し、他の末端に(A)成分と結合するアルコキシシリル基を有するシランカップリング剤と、
(D)ポリラクトンポリオールと、
(F)活性水素を有する界面活性剤、を含有する主剤と、
(E)硬化剤と、を含有する親水性被覆剤であり、
(A)成分と(B)成分との質量比[(A)/(B)]が5/95〜95/5であり、
(A)成分及び(B)成分の合計と(C)成分との質量比[(A+B)/(C)]が70/30〜80/20であり、
(B)成分と(D)成分との質量比[(B)/(D)]が90/10〜10/90であり、
(F)活性水素を有する界面活性剤の含有割合が(B)成分と(F)成分との合計量に対して0〜30質量%であり、
前記主剤の不揮発成分中における(C)成分の含有割合が、10〜20質量%である、ことを特徴とする親水性被覆剤。 - アクリルポリマー(B)の水酸基価が10〜70である請求項1に記載の親水性被覆剤。
- 硬化剤(E)が、ヌレート型ポリウレタン樹脂、ビュレット型ポリウレタン樹脂、及びアロファネート型ポリウレタン樹脂からなる群から選ばれる少なくとも1種を含有する請求項1または2に記載の親水性被覆剤。
- 硬化金属触媒(G)をさらに含有する請求項1〜3のいずれか1項に記載の親水性被覆剤。
- (A)コロイダルシリカゾルと、
(B)活性水素を有する重量平均分子量(Mw)5千〜20万のアクリルポリマーと、
(C)一末端に(B)成分と結合する官能基を有し、他の末端に(A)成分と結合するアルコキシシリル基を有するシランカップリング剤と、
(D)ポリラクトンポリオールと、
(F)活性水素を有する界面活性剤、を含有する主剤と、
(E)硬化剤と、を含有する親水性被覆剤であり、
前記主剤の不揮発成分中における、
前記コロイダルシリカゾル(A)の含有割合が5〜60質量%であり、
前記アクリルポリマー(B)の含有割合が10〜60質量%であり、
前記シランカップリング剤(C)の含有割合が10〜20質量%であり、
前記ポリラクトンポリオール(D)の含有割合が5〜75質量%であり、
前記活性水素を有する界面活性剤(F)の含有割合が0〜15質量%であり、
前記コロイダルシリカゾル(A)及び前記アクリルポリマー(B)の合計と前記シランカップリング剤(C)との質量比[(A+B)/(C)]が70/30〜80/20であることを特徴とする親水性被覆剤。 - 前記主剤の不揮発成分中における、
前記コロイダルシリカゾル(A)の含有割合が10〜30質量%であり、
前記アクリルポリマー(B)の含有割合が30〜45質量%であり、
前記シランカップリング剤(C)の含有割合が10〜20質量%であり、
前記(D)ポリラクトンポリオールの含有割合が15〜30質量%であり、
前記(F)活性水素を有する界面活性剤の含有割合が0〜15質量%であることを特徴とする請求項5に記載の親水性被覆剤。 - (A)成分と(B)成分との質量比[(A)/(B)]が5/95〜95/5であり、
(A)成分及び(B)成分の合計と(C)成分との質量比[(A+B)/(C)]が70/30〜80/20であり、
(B)成分と(D)成分との質量比[(B)/(D)]が90/10〜10/90であることを特徴とする請求項5または6に記載の親水性被覆剤。 - アクリルポリマー(B)の水酸基価が10〜70である請求項5〜7のいずれか1項に記載の親水性被覆剤。
- 硬化剤(E)が、ヌレート型ポリウレタン樹脂、ビュレット型ポリウレタン樹脂、及びアロファネート型ポリウレタン樹脂からなる群から選ばれる少なくとも1種を含有する請求項5〜8のいずれか1項に記載の親水性被覆剤。
- 硬化金属触媒(G)をさらに含有する請求項5〜9のいずれか1項に記載の親水性被覆剤。
- 請求項1〜4のいずれか1項に記載の親水性被覆剤を基材に塗布し、硬化させて得られることを特徴とする親水性被膜。
- 請求項5〜10のいずれか1項に記載の親水性被覆剤を基材に塗布し、硬化させて得られることを特徴とする親水性被膜。
- 請求項11に記載の親水性被膜で被覆されたことを特徴とする親水性基材。
- 請求項12に記載の親水性被膜で被覆されたことを特徴とする親水性基材。
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EP2570419A4 (en) * | 2010-05-14 | 2013-12-25 | Kri Inc | MODIFIED METAL OXIDE SOIL |
WO2012035939A1 (ja) * | 2010-09-14 | 2012-03-22 | コニカミノルタオプト株式会社 | 樹脂フィルム、樹脂フィルムの製造方法、偏光板、及び液晶表示装置 |
JP5686480B2 (ja) * | 2012-03-29 | 2015-03-18 | 大日本塗料株式会社 | 水系塗料組成物、該水系塗料組成物の製造方法及びショッププライマー |
DE102012009691B4 (de) | 2012-05-15 | 2021-12-09 | Carl Zeiss Vision International Gmbh | Antifog-Beschichtung auf einer Optikkomponente, Optikkomponente mit dieser Antifog-Beschichtung sowie Verfahren zur Herstellung dieser Antifog-Beschichtung |
JP5975216B2 (ja) * | 2012-06-22 | 2016-08-23 | 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 | 耐汚染性に優れた塗料組成物及びこれを塗装して得られる塗膜 |
JP5921986B2 (ja) | 2012-08-10 | 2016-05-24 | ハリマ化成株式会社 | 二液硬化型被覆剤 |
WO2014084219A1 (ja) * | 2012-11-29 | 2014-06-05 | 大阪有機化学工業株式会社 | 親水性コート剤 |
JP6043663B2 (ja) | 2013-03-21 | 2016-12-14 | 日本パーカライジング株式会社 | 付着汚れに対する自己洗浄能力に優れた皮膜を形成する水系親水性塗料組成物並びに付着汚れに対する自己洗浄能力に優れた皮膜を形成した表面処理材 |
CN103468213B (zh) * | 2013-08-28 | 2016-04-27 | 奇瑞汽车股份有限公司 | 一种防雾组成物及防雾汽车玻璃制备方法 |
JP6662601B2 (ja) * | 2015-10-09 | 2020-03-11 | セコ コーポレイション リミテッド | 防曇剤 |
JP7026446B2 (ja) * | 2017-03-31 | 2022-02-28 | 旭化成株式会社 | 防曇塗膜およびコーティング組成物 |
EP3630895B1 (en) * | 2017-06-02 | 2022-03-02 | PPG Industries Ohio, Inc. | Polymers, coating compositions containing such polymers, and anti-fingerprint coatings formed therefrom |
JP6996199B2 (ja) * | 2017-09-29 | 2022-01-17 | 三菱ケミカル株式会社 | ウレタン塗料組成物及び成形体 |
JP7358030B2 (ja) * | 2018-01-31 | 2023-10-10 | 住友ゴム工業株式会社 | 親水性基材 |
CN109021729B (zh) * | 2018-06-27 | 2020-08-07 | 江苏美的清洁电器股份有限公司 | 涂料、过滤件与吸尘器 |
US11518906B2 (en) * | 2018-08-02 | 2022-12-06 | Akzo Nobel Coatings International B.V. | Coating composition comprising polysiloxane-modified polyurethane for soft-feel, stain resistant coatings |
WO2021182331A1 (ja) * | 2020-03-10 | 2021-09-16 | 日油株式会社 | 防曇剤組成物、該組成物から形成される防曇膜を有する防曇性物品 |
CN113008973A (zh) * | 2021-01-29 | 2021-06-22 | 融智生物科技(青岛)有限公司 | 一种适用于低丰度蛋白检测的蛋白芯片及其制备方法和应用 |
JP2022127163A (ja) * | 2021-02-19 | 2022-08-31 | 藤倉化成株式会社 | 防曇塗料 |
JP7071606B1 (ja) * | 2021-03-08 | 2022-05-19 | 関西ペイント株式会社 | アクリル樹脂変性シリカ粒子、塗料組成物及び複層塗膜形成方法 |
CN113999599B (zh) * | 2021-10-11 | 2022-05-24 | 华南理工大学 | 一种水性聚氨酯-硅溶胶防雾涂料及其制备方法和应用 |
CN114437626B (zh) * | 2021-12-09 | 2022-10-04 | 科顺防水科技股份有限公司 | 聚氨酯防水涂料及其制备方法 |
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- 2009-03-25 JP JP2010514406A patent/JP5361883B2/ja active Active
- 2009-03-25 CN CN2009801015942A patent/CN101910334B/zh not_active Expired - Fee Related
- 2009-03-25 WO PCT/JP2009/055931 patent/WO2009144999A1/ja active Application Filing
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JP2001019874A (ja) * | 1999-07-09 | 2001-01-23 | Nof Corp | 被覆剤組成物及びそれを硬化させた被覆物 |
JP2002355916A (ja) * | 2001-03-27 | 2002-12-10 | Toto Ltd | 親水性材及び親水性部材と、それらの製造方法並びに親水性コーティング剤セット |
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KR20100092025A (ko) | 2010-08-19 |
JPWO2009144999A1 (ja) | 2011-10-06 |
KR101234133B1 (ko) | 2013-02-19 |
CN101910334A (zh) | 2010-12-08 |
CN101910334B (zh) | 2012-11-21 |
WO2009144999A1 (ja) | 2009-12-03 |
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