JP7392462B2 - 活性エネルギー線硬化型コーティング剤組成物、硬化物、積層体及び成型物 - Google Patents
活性エネルギー線硬化型コーティング剤組成物、硬化物、積層体及び成型物 Download PDFInfo
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- JP7392462B2 JP7392462B2 JP2019235044A JP2019235044A JP7392462B2 JP 7392462 B2 JP7392462 B2 JP 7392462B2 JP 2019235044 A JP2019235044 A JP 2019235044A JP 2019235044 A JP2019235044 A JP 2019235044A JP 7392462 B2 JP7392462 B2 JP 7392462B2
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- 239000008199 coating composition Substances 0.000 title claims description 27
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 132
- -1 alicyclic diol Chemical class 0.000 claims description 53
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 23
- 239000010419 fine particle Substances 0.000 claims description 22
- 239000011248 coating agent Substances 0.000 claims description 17
- 125000002947 alkylene group Chemical group 0.000 claims description 15
- 229910044991 metal oxide Inorganic materials 0.000 claims description 14
- 150000004706 metal oxides Chemical class 0.000 claims description 14
- 125000000524 functional group Chemical group 0.000 claims description 13
- 239000004814 polyurethane Substances 0.000 claims description 12
- 229920002635 polyurethane Polymers 0.000 claims description 12
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 12
- 125000005442 diisocyanate group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
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- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 claims description 9
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- 125000005375 organosiloxane group Chemical group 0.000 claims description 7
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- 238000006243 chemical reaction Methods 0.000 claims description 6
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- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
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- 230000035897 transcription Effects 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229940042596 viscoat Drugs 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Macromonomer-Based Addition Polymer (AREA)
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Description
アルキレンオキシド変性(メタ)アクリレート(B)並びに、
有機官能基を微粒子表面に有する金属酸化物微粒子(C)を含み、
(A)成分の重量平均分子量が1500~4000である活性エネルギー線硬化型コーティング剤組成物。
・(A)成分:好ましくは70~95重量部、より好ましくは80~95重量部
・(B)成分:好ましくは5~30重量部、より好ましくは5~20重量部
ゲルパーメーションクロマトグラフィー法(GPC法)により、以下の条件でポリウレタン(メタ)アクリレートの重量平均分子量を測定した。
・分子量測定機(製品名:『HLC-8220』、東ソー(株)製)
・カラム(製品名:『TSKgel superHZ2000』、『TSKgel superHZM-M』、東ソー(株)製)
・展開溶剤:テトラヒドロフラン
・流速:0.35mL/min、
・試料濃度:0.5g/L、
・標準物質:ポリスチレン(標準ポリスチレンキット、PStQuickA、B、C、東ソー(株)製)
撹拌機、温度計、還流冷却機を取り付けた三つ口フラスコに、トリシクロデカンジメタノール(以下、“TCD”という)16.7部、水添キシレンジイソシアネート(H-XDI)33.1部、酢酸ブチル30.0部、オクチル酸スズ0.01部を仕込み、80℃で反応させた。残存イソシアネート基が9.0%となった時点で2-ヒドロキシエチルアクリレート(HEA)20.2部、オクチル酸スズ0.02部、ハイドロキノンモノメチルエーテル0.07部を加え、残存イソシアネート基が0.1%以下になるまで反応を行い、固形分濃度70%のポリウレタン(メタ)アクリレート(A-1)を得た。
表1に示す組成で、製造例1と同様の方法にて合成し、ポリウレタン(メタ)アクリレート(A-2)~(A-7)、(E-1)~(E-5)をそれぞれ得た。
市販のポリエチレンテレフタレートフィルム(商品名:『コスモシャインA4100』、東洋紡(株)製)の表面に、製造例1のポリウレタン(メタ)アクリレート(A-1)をバーコーターで硬化物の層の厚さが5μmとなるように塗工し、温度150℃で40秒乾燥させた。その後、120Wの高圧水銀灯(1灯)を用いて、積算光量300mJ/cm2になるよう紫外線を照射して試験フィルムを作製した。製造例2~7、比較製造例1~5のポリウレタン(メタ)アクリレートについても同様に行った。
試験フィルムを6cm×6cmに切り出した。日焼け止めクリーム(商品名:『Neutrogena』、helioplex社製)を半径3cmの円になるように塗り広げた後、80℃の乾燥機で4時間放置させた。室温まで冷却して、洗剤と水で日焼け止めクリームを洗い流した。水分を拭き取って、試験フィルムの表面を目視で観察し、以下の基準で評価した。表1に結果を示す(以下同様)。
(評価基準)
◎:表面に全く筋も白化も見られない
○:表面の一部に若干筋が見られる
△:表面の一部分が白化している
×:表面の大部分が白化している
試験フィルムを幅1cm、長さ10cmに切り出した試験片を準備した。試験片を引張試験機(装置名:『RTM-500』、オリエンテック(株)製)にチャック間距離50mmでセットし、温度150℃で1分放置した後、引張速度20mm/分で試験片を引っ張った。硬化物の層にクラックが入ったときの試験片の長さを読み取り、50mmを100%として、伸び率を求めた。伸び率が150%以上のものを良好とした。
<ジオール>
・TCD:トリシクロデカンジメタノール
・1,1-CHDM:1,1-シクロヘキサンジメタノール
・1,4-CHDM:1,4-シクロヘキサンジメタノール
・PD-9:2,4-ジエチル-1,5-ペンタンジオール(商品名:『キョーワジオールPD-9』、KHネオケム(株)製)
<ジイソシアネート>
・H-XDI:m-キシリレンジイソシアネートの水素化物
・XDI:m-キシリレンジイソシアネート
・NBDI:ノルボルネンメタンジイソシアネート
・HDI:ヘキサメチレンジイソシアネート
<水酸基含有(メタ)アクリレート>
・HEA:2-ヒドロキシエチルアクリレート
・CHDMMA:1,4-シクロヘキサンジメタノールモノアクリレート(商品名:『CHDMMA』、三菱ケミカル(株)製)
乾燥空気中、メルカプトプロピルトリメトキシシラン80.6部及びジブチル錫ジラウレート1.8部の溶液に、イソホロンジイソシアネート210.2部を撹拌しながら、50℃で1時間かけて滴下後、60℃で3時間撹拌した。この溶液に、『NKエステルA-TMM-3LM-N』(ペンタエリスリトールトリアクリレート/ペンタエリスリトールテトラアクリレート=60/40(重量比率)の混合物、新中村化学工業(株)製)707.5部を30℃で1時間かけて滴下後、60℃で3時間撹拌することでシラン系中間体を得た。
次いで、上記シラン系中間体8.6部、メチルエチルケトンシリカゾル(商品名:『MEK-ST』、シリカ濃度:30%、日産化学工業(株)製)89.9部(固形分:27.0部)、イオン交換水0.1部の混合液を60℃で4時間撹拌した後、オルトギ酸メチルエステル1.4部を添加し、さらに1時間撹拌して分散液を得た。この分散液を、限外濾過でメチルイソブチルケトンに溶解した後、濃縮することにより、平均一次粒子径10nmのウレタン基を有するシリカのメチルイソブチルケトン分散液(C-3)を得た。
製造例1で得た(A-1)成分45.8部、エチレンオキシド15モル変性トリメチロールプロパンアクリレート3.5部(商品名:『Miramer M3150』、MIWON社製)、オルガノシロキサン基を有するアルミナ(商品名:『NANOBYK-3610』、平均一次粒子径:20nm、ビックケミー・ジャパン(株)製)11.5部、ペンタメチルピペリジルメタクリレ-ト(光安定剤、商品名:『FA-711MM』、日立化成(株)製)0.3部、シリコン系表面調整剤(商品名:『BYK-378』、ビックケミー・ジャパン(株)製)0.2部、1-ヒドロキシシクロヘキシルフェニルケトン(光重合開始剤、商品名:『OMNIRAD 184』、IGM Resins B.V.社製)1.7部、及びメチルエチルケトン(以下、MEK)37.0部を配合し、溶解するまで撹拌して活性エネルギー線硬化型コーティング剤組成物を調製した。
表2に示す組成で、実施例1と同様の方法にて行い、活性エネルギー線硬化型コーティング剤組成物をそれぞれ得た。
市販のポリエチレンテレフタレートフィルム(商品名:『コスモシャインA4100』、東洋紡(株)製)の表面に、実施例1の活性エネルギー線硬化型コーティング剤組成物をバーコーターで硬化物の層の厚さが5μmとなるように塗工し、温度150℃で40秒乾燥させた。その後、120Wの高圧水銀灯(1灯)を用いて、積算光量300mJ/cm2になるよう紫外線を照射して積層体を作製した。実施例2~14、比較例1~9の活性エネルギー線硬化型コーティング剤組成物についても同様に行った。
各積層体を用いて、前述と同様の方法で耐薬品性を評価した。表2に結果を示す(以下同様)。
各積層体を用いて、前述と同様の方法で、伸度を測定した。
スチールウール(#0000、10mm×10mm)を底に貼り付けた100gの重りで、各積層体の硬化膜の表面を10往復擦った。目視にて傷の本数を確認し、以下のように評価した。
○:傷が0本
△:傷が1本以上5本未満
×:傷が5本以上
予め積層体を直径11.5cmの円形に切り出した。ASTM-D-1044に従い、テーバー摩耗試験機(テスター産業(株)製)を用いて、摩耗輪CS-10F、荷重500g、回転速度60rpmで各積層体中の硬化物層側を500回ずつ摩耗させた。基材が露出する直前の摩耗回数を測定値とした。測定値が高いほど、耐摩耗性に優れることを意味する。
<多官能(メタ)アクリレート>
・B-1:エチレンオキシド15モル変性トリメチロールプロパントリアクリレート(商品名:『Miramer M3150』、MIWON社製)
・B-2:エチレンオキシド12モル変性ジペンタエリスリトールポリアクリレート(商品名:『NKエステルA-DPH-12E』、新中村化学工業(株)製)
・PETA:ペンタエリスリトールトリアクリレート及びペンタエリスリトールテトラアクリレートの混合物(商品名:『ビスコート#300』、大阪有機化学工業(株)製)
<金属酸化物微粒子>
・C-1:オルガノシロキサン基を有するアルミナ(商品名:『NANOBYK-3610』、ビックケミー・ジャパン(株)製、平均一次粒子径:20nm)
・C-2:メタクリロイル基を有するアルミナ(商品名:『ALMIBK30WT%-H06』、CIKナノテック(株)製、平均一次粒子径:15nm)
・C-3:ウレタン基を有するシリカ(段落[0073]参照)(平均一次粒子径:10nm)
・F-1:メチルエチルケトン分散系シリカゾル(商品名:『MEK-ST』、日産化学工業(株)製、平均一次粒子径:10~15nm)
<その他>
・FA-711MM:ペンタメチルピペリジルメタクリレート(光安定剤、日立化成(株)製)
・Omni184:1-ヒドロキシシクロヘキシルフェニルケトン(光重合開始剤、商品名:『OMNIRAD 184』、IGM Resins B.V.社製)
・BYK-378:シリコン系表面調整剤、ビックケミー・ジャパン(株)製
Claims (8)
- 脂環族ジオール(a1)、環状構造を有するジイソシアネート(a2)及び水酸基含有モノ(メタ)アクリレート(a3)を反応成分として含むポリウレタン(メタ)アクリレート(A)、
アルキレンオキシド変性(メタ)アクリレート(B)並びに、
有機官能基を微粒子表面に有する金属酸化物微粒子(C)を含み、
(A)成分の重量平均分子量が1500~4000であり、
(a1)成分が、トリシクロデカンジメタノール、1,1-シクロヘキサンジメタノール及び1,4-シクロヘキサンジメタノールからなる群より選ばれる1種以上であり、
(a2)成分が、ノルボルネンメタンジイソシアネート、m-キシリレンジイソシアネート及びm-キシリレンジイソシアネートの水素化物からなる群より選ばれる1種以上であり、
(B)成分が、エチレンオキシド変性(メタ)アクリレートであり、
(C)成分が、メタクリロイル基、アクリロイル基、ビニル基、エポキシ基、イソシアネート基、ウレタン基及びオルガノシロキサン基からなる群より選ばれる1種の有機官能基を有し、
金属酸化物微粒子が、シリカ、アルミナ、酸化ジルコニウム、酸化チタン、酸化アンチモン、酸化スズ、酸化インジウム及び酸化亜鉛からなる群より選ばれる1種であり、
(A)成分及び(B)成分の合計100重量部中、(A)成分が60~95重量部、かつ、(B)成分が5~40重量部であり、
(C)成分の含有量が、(A)成分及び(B)成分の合計100重量部に対して、5~40重量部である活性エネルギー線硬化型コーティング剤組成物。 - (C)成分における金属酸化物微粒子が、シリカ及び/又はアルミナである請求項1に記載の活性エネルギー線硬化型コーティング剤組成物。
- (C)成分が、メタクリロイル基、ウレタン基及びオルガノシロキサン基からなる群より選ばれる1種の有機官能基を有する、請求項1又は2に記載の活性エネルギー線硬化型コーティング剤組成物。
- (A)成分の含有量が、固形分重量で(A)成分及び(B)成分の合計100重量部中70~95重量部である請求項1~3のいずれかに記載の活性エネルギー線硬化型コーティング剤組成物。
- (C)成分の含有量が、固形分重量で(A)成分及び(B)成分の合計100重量部に対して、5~20重量部である請求項1~4のいずれかに記載の活性エネルギー線硬化型コーティング剤組成物。
- 請求項1~5のいずれかに記載の活性エネルギー線硬化型コーティング剤組成物の硬化物。
- 請求項6に記載の硬化物の層を有する積層体。
- 請求項6に記載の硬化物で表面が被覆された成型物。
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WO2012160891A1 (ja) | 2011-05-20 | 2012-11-29 | 関西ペイント株式会社 | 塗料組成物及び塗膜形成方法 |
JP2013166889A (ja) | 2012-02-16 | 2013-08-29 | Mitsubishi Chemicals Corp | 活性エネルギー線硬化性樹脂組成物およびそれを用いた積層体 |
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WO2012160891A1 (ja) | 2011-05-20 | 2012-11-29 | 関西ペイント株式会社 | 塗料組成物及び塗膜形成方法 |
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