JP2014037454A - 二液硬化型被覆剤 - Google Patents
二液硬化型被覆剤 Download PDFInfo
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- JP2014037454A JP2014037454A JP2012178954A JP2012178954A JP2014037454A JP 2014037454 A JP2014037454 A JP 2014037454A JP 2012178954 A JP2012178954 A JP 2012178954A JP 2012178954 A JP2012178954 A JP 2012178954A JP 2014037454 A JP2014037454 A JP 2014037454A
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Classifications
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Abstract
【解決手段】 本発明の二液硬化型被覆剤は、側鎖に光重合性基及び水酸基を有し且つ水酸基価が30〜350mgKOH/g、重量平均分子量Mwが5000〜200000であるアクリル系ポリマー100重量部と、シランカップリング剤0.3〜35重量部と、ポリエーテルポリオール0.3〜35重量部と、ポリラクトンポリオール3〜70重量部と、一分子中に二以上の光重合性基を有する光重合性多官能化合物6〜500重量部とを含む主剤と、ポリイソシアネートを含む硬化剤3〜100重量部とを含むことを特徴とする。
【選択図】 なし
Description
Xn−Si−Y(4−n) ・・・式(1)
但し、Xは、アクリル系ポリマーの水酸基、ポリエーテルポリオールの水酸基又はポリラクトンポリオールの水酸基と反応性を有する水酸基反応性官能基であり、Yは、加水分解性基であり、nは、1〜3の整数である。nが2又は3の場合、複数あるXは互いに同一であっても相違していてもよい。nが1又は2の場合、複数あるYは互いに同一であっても相違していてもよい。
H[O(CH2)5(C=O)]mO-R-O[(C=O)(CH2)5O]n-H ・・・式(2)
但し、式(2)中、Rは、−C2H4−、−C2H4OC2H4−、−C(CH3)2C2H4−などの炭素数が2〜18のアルキレンであり、m及びnはそれぞれ正の整数であって、m+nは4〜35の整数である。
R1−(O[(C=O)−(CH2)5O]pH)3 ・・・式(3)
但し、式(3)中、R1は、
などの炭素数が2〜18の三価の炭化水素基であり、pは、1〜30の整数である。
反応容器中に、溶媒としてメチルイソブチルケトン(MIBK)233重量部を供給して88℃まで加熱し維持した。
得られたアクリル系ポリマーからサンプルとして約0.2mgを採取し、これをテトラヒドロフラン10ミリリットルに溶解させ、示差屈折率検出器(RID)を装備したゲルパーミエーションクロマトグラフ(GPC)によって測定し、サンプルの分子量分布を得た。
データ処理装置:品番HLC−8220GPC(東ソー社製)
示差屈折率検出器:品番HLC−8220GPCに内蔵されたRI検出器
カラム:品番TSKgel GMHXL(東ソー社製)3本
移動相:テトラヒドロフラン
カラム流量:0.5mL/min
注入量:20μL
測定温度:40℃
標準ポリスチレン分子量:1250、3250、9200、28500、68000、165000、475000、950000、1900000
得られたアクリル系ポリマーの25℃における粘度をコーン・プレート粘度計を用いてJIS K 5600−2−3:1999に準拠して測定した。
得られたアクリル系ポリマーの水酸基価を、JIS K 1557−1:2007(ISO 14900:2001)「プラスチック−ポリウレタン原料ポリオール試験方法−第1部:水酸基価の求め方」の4.2 B法に準拠して測定した。
反応容器中に、溶媒として表4〜6に示した所定量のメチルイソブチルケトン(MIBK)を供給して80℃まで加熱し維持した。
表7〜11に示した所定量のγ−イソシアネートプロピルトリエトキシシラン(信越化学工業(株)製の商品名「KBE−9007」)、N−2−(アミノエチル)−3−アミノプロピルトリエトキシシラン(信越化学工業(株)製の商品名「KBE−603」)、グリシドキシトリメトキシシラン(信越化学工業(株)製の商品名「KBM−403」、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)社の商品名「エパンU105」、水酸基価:19mgKOH/g、平均官能基数:2、重量平均分子量:6400)、ポリオキシプロピレングリコールエーテル(三洋化成工業(株)製の商品名「サンニックスPP−1000」、水酸基価:112mgKOH/g、平均官能基数:2、重量平均分子量:1000)、ポリカプロラクトントリオール(ダイセル化学工業(株)社の商品名「プラクセル303」)、ポリカプロラクトンジオール(ダイセル化学工業(株)社の商品名「プラクセル205」)、ペンタエリスリトールトリアクリレートヘキサメチレンジイソシアネートウレタンプレポリマー(共栄社化学(株)の商品名「UA−306H」)、フェニルグリシジルエーテルアクリレートヘキサメチレンジイソシアネートプレポリマー(共栄社化学(株)の商品名「AH−600」)、コロイダルシリカ(日産化学工業(株)の商品名「MIBK−ST」)及びメチルイソブチルケトンを均一に混合して予備混合液を作製した。予備混合液にアクリル系ポリマーB1〜15を含むアクリル系ポリマー溶液をアクリル系ポリマーB1〜15が表7〜11に示した量(固形分)となるように10分かけて徐々に滴下した。予備混合液へのアクリル系ポリマー溶液の滴下が終了した後に予備混合液を30℃で30〜60分間に亘って攪拌して二液硬化型被覆剤の主剤を作製した。次いで、二液硬化型被覆剤の主剤に表7〜11に示した所定量の2−ヒドロキシ−2−メチル−1−フェニル−プロパン−1−オン(BASF社の製品名「DAROCUR 1173」)を添加した。二液硬化型被覆剤の主剤の固形分濃度は30重量%であった。
コーティング層のヘーズをJIS K 7136の「プラスチック・透明材料のヘーズの求め方」の試験法に準拠して、ヘーズメーター(日本電色工業(株)の商品名「NDH5000」)を用いて測定した。なお、ヘーズは、値が小さい程、透明性に優れている。
コーティング層の鉛筆硬度をJIS K 5600−5−4:1999に準拠して鉛筆硬度試験を実施して測定した。なお、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。鉛筆硬度は、「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ことを示す。
コーティング層の密着性をJIS K 5600−5−6:1999に準拠して測定した。具体的には、コーティング層にポリエチレンテレフタレートフィルムに達する切り込みを格子状に形成した。コーティング層は、格子状の切り込みによって100個の分割片に分割された。分割片は、一辺が1.0mmの平面正方形状であった。分割片の全体に粘着テープ(ニチバン社製 商品名「ニチバンテープ1号」)を貼り付けた。そして、貼り付けられた粘着テープをポリエチレンテレフタレートフィルムから剥離し、ポリエチレンテレフタレートフィルム上に残存した分割片の数を数えた。密着性を(ポリエチレンテレフタレートフィルム上に残存した分割片の数/ポリエチレンテレフタレートフィルム上に形成した分割片の数)として評価した。なお、ポリエチレンテレフタレートフィルム上に残存した分割片の数が多いほど、密着性に優れていることを示す。
コーティング層の表面にノルマルヘキサデカンを0.1g垂らした。そして、コーティング層の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(旭化成(株)の商品名「ベンコットM−3」)で300gの荷重を掛けて10回拭き取った。
コーティング層の表面に、スチールウール(ボンスター販売(株)製の品番#0000)を1cm2当たり300gの荷重を負荷しながらコーティング層の表面に沿って50往復させた。ヘーズメーター(日本電色工業(株)製の商品名「NDH5000」)を用いて試験前及び試験後のコーティング層表面のヘーズ(濁度)を測定した。そして、試験前及び試験後のコーティング層のヘーズの差ΔEを算出した。なお、ΔEの値が小さいほど耐傷付き性が良好である。
コーティング層が形成されたポリエチレンテレフタレートフィルムを40℃±2℃の5重量%水酸化ナトリウム水溶液中に3日間に亘って浸漬した。ヘーズメーター(日本電色工業(株)製の商品名「NDH5000」)を用いて浸漬前及び浸漬後のコーティング層表面のヘーズ(濁度)を測定した。そして、浸漬前及び浸漬後のコーティング層のヘーズの差ΔEを算出した。なお、ΔEの値が小さいほど耐アルカリ性が良好である。
コーティング層の表面にアセトンを滴下した後、荷重100gをかけて100回ラビング試験を行った。ヘーズメーター(日本電色工業(株)製の商品名「NDH5000」)を用いて試験前及び試験後のコーティング層表面のヘーズ(濁度)を測定した。そして、試験前及び試験後のコーティング層のヘーズの差ΔEを算出した。なお、ΔEの値が小さいほど耐溶剤性が良好である。
二液硬化型被覆剤の主剤に硬化剤として添加後、直ちに二液硬化型被覆剤を乾燥膜厚が30μmになるようにバーコーターNo.10を用いて厚みが188μmのポリエチレンテレフタレート(PET)フィルム上に塗布した。
引張伸度(%)=100×(L−115)
コーティング層表面に0.4マイクロリットルの水滴を垂らし、接触角計(協和界面科学(株)製の商品名「Drop Master500」)により接触角を測定した。なお、水接触角が低いほど、油分拭き取り性に優れていることを示す。
コーティング層表面に0.4マイクロリットルのオレイン酸を垂らし、接触角計(協和界面科学(株)製の商品名「Drop Master500」)により接触角を測定した。なお、水接触角が低いほど、油分拭き取り性に優れていることを示す。
Claims (2)
- 側鎖に光重合性基及び水酸基を有し且つ水酸基価が30〜350mgKOH/g、重量平均分子量が5000〜200000であるアクリル系ポリマー100重量部と、シランカップリング剤0.3〜35重量部と、ポリエーテルポリオール0.3〜35重量部と、ポリラクトンポリオール3〜70重量部と、一分子中に二以上の光重合性基を有する光重合性多官能化合物6〜500重量部とを含み又は反応させて得られた主剤と、ポリイソシアネートを含む硬化剤3〜100重量部とを含むことを特徴とする二液硬化型被覆剤。
- 硬化剤がポリイソシアネート誘導体を含むことを特徴とする請求項1に記載の二液硬化型被覆剤。
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- 2013-07-24 WO PCT/JP2013/070115 patent/WO2014024686A1/ja active Application Filing
- 2013-07-24 CN CN201380042565.XA patent/CN104540908B/zh active Active
- 2013-07-24 KR KR1020157000470A patent/KR101726201B1/ko active IP Right Grant
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WO2015198787A1 (ja) * | 2014-06-26 | 2015-12-30 | Dic株式会社 | 活性エネルギー線硬化型樹脂組成物、塗料、塗膜、及び積層フィルム |
JPWO2015198787A1 (ja) * | 2014-06-26 | 2017-04-20 | Dic株式会社 | 活性エネルギー線硬化型樹脂組成物、塗料、塗膜、及び積層フィルム |
JP2017082035A (ja) * | 2015-10-23 | 2017-05-18 | 三菱レイヨン株式会社 | 硬化性組成物及び塗装物品 |
JPWO2017150663A1 (ja) * | 2016-03-04 | 2018-12-27 | 三菱ケミカル株式会社 | 活性エネルギー線硬化型被覆材組成物及び積層体 |
US11072849B2 (en) | 2016-03-04 | 2021-07-27 | Mitsubishi Chemical Corporation | Actinic-ray-curable coating material composition and layered product |
JP2021181567A (ja) * | 2016-03-04 | 2021-11-25 | 三菱ケミカル株式会社 | 活性エネルギー線硬化型被覆材組成物及び積層体 |
JP7081151B2 (ja) | 2016-03-04 | 2022-06-07 | 三菱ケミカル株式会社 | 活性エネルギー線硬化型被覆材組成物及び積層体 |
JP2020522402A (ja) * | 2017-06-02 | 2020-07-30 | ピーピージー・インダストリーズ・オハイオ・インコーポレイテッドPPG Industries Ohio,Inc. | ポリマー、そのようなポリマーを含有するコーティング組成物、およびその組成物から形成された防指紋コーティング |
KR20200004731A (ko) | 2018-07-04 | 2020-01-14 | 후지제롯쿠스 가부시끼가이샤 | 표면 보호 수지 부재 형성용 용액, 표면 보호 수지 부재 형성용 용액 세트, 및 표면 보호 수지 부재 |
WO2020067459A1 (ja) * | 2018-09-28 | 2020-04-02 | 大日本塗料株式会社 | 塗料組成物、塗膜の形成方法、及び塗装体 |
JP2020055900A (ja) * | 2018-09-28 | 2020-04-09 | 大日本塗料株式会社 | 塗料組成物 |
Also Published As
Publication number | Publication date |
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KR20150023683A (ko) | 2015-03-05 |
TW201418380A (zh) | 2014-05-16 |
TWI519613B (zh) | 2016-02-01 |
JP5921986B2 (ja) | 2016-05-24 |
CN104540908B (zh) | 2017-01-25 |
WO2014024686A1 (ja) | 2014-02-13 |
CN104540908A (zh) | 2015-04-22 |
KR101726201B1 (ko) | 2017-04-12 |
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