JP2005126453A - ハードコート剤組成物及びこれを用いた光情報媒体 - Google Patents
ハードコート剤組成物及びこれを用いた光情報媒体 Download PDFInfo
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- JP2005126453A JP2005126453A JP2003360123A JP2003360123A JP2005126453A JP 2005126453 A JP2005126453 A JP 2005126453A JP 2003360123 A JP2003360123 A JP 2003360123A JP 2003360123 A JP2003360123 A JP 2003360123A JP 2005126453 A JP2005126453 A JP 2005126453A
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Abstract
【解決手段】 パーフルオロポリエーテル単位、ウレタン結合及び活性エネルギー線反応性基を有するフッ素含有ポリエーテル化合物(A)と、分子内に2つ又は3つ以上の活性エネルギー線重合性基を有する硬化性化合物(B)とを含むハードコート剤組成物。支持基体20上に、少なくとも記録層4又は反射層を含む、1層又は複数層から構成される膜体を有する光情報媒体であって、支持基体20側表面及び前記膜体側表面のうちの少なくとも一方の表面が、前記ハードコート剤組成物の硬化物を含むハードコート層8によって形成されている光情報媒体。
【選択図】 図1
Description
(1) パーフルオロポリエーテル単位、ウレタン結合及び活性エネルギー線反応性基を有するフッ素含有ポリエーテル化合物(A)と、分子内に2つ又は3つ以上の活性エネルギー線重合性基を有する硬化性化合物(B)とを含むハードコート剤組成物。
不揮発分には、フッ素含有ポリエーテル化合物(A)及び硬化性化合物(B)の他、後述する無機微粒子(C)、光重合開始剤、各種添加剤等の任意成分が含まれる。
前記支持基体の前記膜体が形成された側とは反対側の面上、及び前記膜体面上のうちの少なくとも一方に、(1) 〜(12)のうちのいずれかに記載のハードコート剤組成物を塗布し、活性エネルギー線の照射によって硬化させハードコート層を形成することを含む、光情報媒体の製造方法。
F-[CF2CF2CF2O]l-CF2CF2CH2OH (Demnum-SA)
F-[CF(CF3)CF2O]l-CF(CF3)CH2OH (Krytox-OH)
HO(CH2CH2O)n-CH2-CF2O-[CF2CF2O]l-[CF2O]m-CF2CH2(OCH2CH2)nOH (Zdol-TX)
HOCH2CH(OH)CH2O-CH2-CF2O-[CF2CF2O]l-[CF2O]m-CF2CH2OCH2CH(OH)CH2OH (Z-Tetraol)
CH2=C(CH3)-COO-CH2CH2-NHCO-OCH2-CF2O-[CF2CF2O]l-[CF2O]m-CF2CH2O-CONH-CH2CH2-OCO-C(CH3)=CH2
Fomblin Z DOL 〔アルコール変性パーフルオロポリエーテル(アウジモント社製)〕の末端ヒドロキシル基にメタクリロイルオキシエチルイソシアネートを反応させることにより、ウレタン結合を介してメタクリロイル基を導入(MOI変性)したもの
まず、膜体側表面が記録/再生ビーム入射側表面とされる光情報媒体について説明する。
図2は、本発明の光ディスクの層構成の一例を示す概略断面図である。図2において、光ディスクは、支持基体(20)の情報ピットやプリグルーブ等の微細凹凸が形成されている側の面上に、反射層(3) 、第2誘電体層(52)、相変化記録材料層(4) 及び第1誘電体層(51)をこの順で有し、第1誘電体層(51)上に光透過層(7) を有し、光透過層(7) 上にハードコート層(8) を有する。この例では、反射層(3) 、第2誘電体層(52)、相変化記録材料層(4) 及び第1誘電体層(51)が情報記録層を構成する。また、前記情報記録層及び光透過層(7) が、記録又は再生のために必要な膜体を構成する。この光ディスクは、ハードコート層(8) 及び光透過層(7) を通して、すなわち膜体側から、記録又は再生のためのレーザー光が入射するように使用される。
次に、支持基体側表面が記録/再生ビーム入射側表面とされる光情報媒体について説明する。
攪拌機及びジムロートを取り付けた3つ口フラスコに、イソホロンジイソシアネート(85.0mL,0.401mol)、及びジラウリン酸ジブチル錫(0.2g)を仕込み、窒素気流下で70℃まで昇温した。次いで、パーフルオロポリエーテルジオール(アウジモント社製、Fomblin Z DOL TX1000)210.0g(約0.17mol)をゆっくり添加し、反応混合物を窒素気流下で70℃で4時間加熱した。次いで、反応混合物に、ジブチルヒドロキシトルエン(0.25g)及び2−ヒドロキシエチルアクリレート(大阪有機化学工業(株)製、HEA)49.0g(0.422mol)を加え、更に4時間反応させた。
このようにして、前記の化学構造式1で示されるフッ素化ウレタンアクリレート1を得た。
攪拌機及びジムロートを取り付けた3つ口フラスコに、イソホロンジイソシアネート(85.0mL,0.401mol)、及びジラウリン酸ジブチル錫(0.2g)を仕込み、窒素気流下で70℃まで昇温した。次いで、パーフルオロポリエーテルジオール(アウジモント社製、Fomblin Z DOL TX1000)210.0g(約0.17mol)をゆっくり添加し、反応混合物を窒素気流下で70℃で4時間加熱した。次いで、反応混合物に、ジブチルヒドロキシトルエン(0.25g)及びペンタエリスリトールトリアクリレート(日本化薬(株)製、PET−30、平均官能基数3.4)239.5gを加え、更に4時間反応させた。
このようにして、前記の化学構造式2で示されるフッ素化ウレタンアクリレート2を得た。
図2に示す層構成の光記録ディスクサンプルを次のように作製した。
情報記録のためにグルーブが形成されたディスク状支持基体(20)(ポリカーボネート製、直径120mm、厚さ1.1mm)のグルーブが形成された面上に、Al98Pd1 Cu1 (原子比)からなる厚さ100nmの反射層(3) をスパッタリング法により形成した。前記グルーブの深さは、波長λ=405nmにおける光路長で表してλ/6とした。グルーブ記録方式における記録トラックピッチは、0.32μmとした。
ウレタンアクリレートオリゴマー 50重量部
(三菱レイヨン(株)製、ダイヤビームUK6035)
イソシアヌル酸EO変性トリアクリレート 10重量部
(東亜合成(株)製、アロニックスM315)
イソシアヌル酸EO変性ジアクリレート 5重量部
(東亜合成(株)製、アロニックスM215)
テトラヒドロフルフリルアクリレート 25重量部
光重合開始剤(1−ヒドロキシシクロヘキシルフェニルケトン) 3重量部
反応性基修飾コロイダルシリカ(分散媒:プロピレングリコールモノメチルエーテルアセテート、不揮発分:40重量%) 100重量部
ジペンタエリスリトールヘキサアクリレート 48重量部
1,6-ヘキサンジオールジアクリレート 12重量部
プロピレングリコールモノメチルエーテルアセテート 40重量部
(非反応性希釈溶剤)
光重合開始剤(1−ヒドロキシシクロヘキシルフェニルケトン) 2.5重量部
前記フッ素化ウレタンアクリレート1 0.5重量部
ハードコート剤の組成における前記フッ素化ウレタンアクリレート1(0.5重量部)の代わりに、前記フッ素化ウレタンアクリレート2(0.5重量部)を用いた以外は、実施例1と同様にしてディスクサンプルを作製した。ハードコート層(8) の硬化後の厚さは2.4μmであった。
実施例1で用いたハードコート剤の代わりに、下記組成のハードコート剤を用いた以外は、実施例1と同様にしてディスクサンプルを作製した。このハードコート剤では、コロイダルシリカは含まれていなかった。ハードコート層(8) の硬化後の厚さは3.8μmであった。
ジペンタエリスリトールヘキサアクリレート 48重量部
1,6-ヘキサンジオールジアクリレート 12重量部
プロピレングリコールモノメチルエーテルアセテート 10重量部
(非反応性希釈溶剤)
光重合開始剤(1−ヒドロキシシクロヘキシルフェニルケトン) 2.5重量部
前記フッ素化ウレタンアクリレート2 0.3重量部
実施例1で用いたハードコート剤の代わりに、下記組成のハードコート剤を用いた以外は、実施例1と同様にしてディスクサンプルを作製した。このハードコート剤では、6官能のジペンタエリスリトールヘキサアクリレートが含まれておらず、2官能のジアクリレートが含まれていた。ハードコート層(8) の硬化後の厚さは2.8μmであった。
反応性基修飾コロイダルシリカ(分散媒:プロピレングリコールモノメチルエーテルアセテート、不揮発分:40重量%) 100重量部
EO変性ビスフェノールAジアクリレート 60重量部
(日本化薬(株)製、R−551)
プロピレングリコールモノメチルエーテルアセテート 6.7重量部
(非反応性希釈溶剤)
光重合開始剤(1−ヒドロキシシクロヘキシルフェニルケトン) 2.5重量部
前記フッ素化ウレタンアクリレート2 0.5重量部
ハードコート剤の組成における前記フッ素化ウレタンアクリレート1(0.5重量部)の代わりに、パーフルオロポリエーテルジオール(アウジモント社製、Fomblin Z DOL TX1000)(0.5重量部)を用いた以外は、実施例1と同様にしてディスクサンプルを作製した。ハードコート層の硬化後の厚さは2.4μmであった。
ハードコート剤の組成における前記フッ素化ウレタンアクリレート2(0.5重量部)の代わりに、パーフルオロポリエーテルジオール(アウジモント社製、Fomblin Z DOL TX1000)(0.5重量部)を用いた以外は、実施例4と同様にしてディスクサンプルを作製した。ハードコート層の硬化後の厚さは2.4μmであった。
実施例1〜4及び比較例1〜2で作製した各ディスクサンプルについて、以下に示す性能試験を行った。
各ディスクサンプルのハードコート表面の接触角を測定した。測定液として純水を用い、協和界面科学(株)製の接触角計 FACE CONTACT-ANGLEMETER を用いて、静止接触角を測定した。測定環境は、温度20℃、相対湿度60%であった。まず、初期の接触角(a) を測定した。
実施例1で用いたのと同じ支持基体上に、直接、実施例1〜4及び比較例1〜2における各光透過層及び各ハードコート層の形成と全く同じ条件で、光透過層及びハードコート層をそれぞれ形成した。得られたハードコート層付き透明基板のハードコート層表面を、JIS K7204:1994に準拠したテーパー摩耗試験装置を用いて荷重4.9Nで100回摩耗させた。摩耗輪としてはCS−10Fを用いた。摩耗後のハードコート層表面の曇価をヘイズメーターTC−HIII DPK((株)東京電色技術センター製)で測定した。
表1から、実施例1〜4のディスクサンプルはいずれも、ハードコート表面の硬度を維持しつつ、防汚性及びその耐久性に優れていた。
(3) :反射層
(52):第2誘電体層
(4) :記録層
(51):第1誘電体層
(7) :光透過層
(8) :ハードコート層
Claims (16)
- パーフルオロポリエーテル単位、ウレタン結合及び活性エネルギー線反応性基を有するフッ素含有ポリエーテル化合物(A)と、分子内に2つ又は3つ以上の活性エネルギー線重合性基を有する硬化性化合物(B)とを含むハードコート剤組成物。
- 組成物中の不揮発分100重量部に対して、フッ素含有ポリエーテル化合物(A)0.01重量部以上3重量部以下を含む、請求項1に記載のハードコート剤組成物。
- 硬化性化合物(B)は、硬化性化合物(B)を基準として、分子内に3つ以上の活性エネルギー線重合性基を有する硬化性化合物(Bt)65〜100重量%、及び分子内に2つの活性エネルギー線重合性基を有する硬化性化合物(Bd)0〜35重量%を含む、請求項1又は2に記載のハードコート剤組成物。
- フッ素含有ポリエーテル化合物(A)の、GPC(ゲル浸透クロマトグラフィー)において測定されたポリスチレン換算の数平均分子量は500以上10,000以下である、請求項1〜3のうちのいずれか1項に記載のハードコート剤組成物。
- フッ素含有ポリエーテル化合物(A)は、分子内に2つ以上の活性エネルギー線反応性基を有する、請求項1〜4のうちのいずれか1項に記載のハードコート剤組成物。
- フッ素含有ポリエーテル化合物(A)が有する活性エネルギー線反応性基は、(メタ)アクリロイル基及びビニル基からなる群から選ばれる、請求項1〜5のうちのいずれか1項に記載のハードコート剤組成物。
- フッ素含有ポリエーテル化合物(A)は、末端にヒドロキシル基を有し且つパーフルオロポリエーテル単位を有するフッ素含有ポリエーテル化合物のヒドロキシル基に、ウレタン結合を介して(メタ)アクリロイル基が導入されたものである、請求項1〜6のうちのいずれか1項に記載のハードコート剤組成物。
- さらに平均粒子径100nm以下の無機微粒子(C)を含む、請求項1〜7のうちのいずれか1項に記載のハードコート剤組成物。
- 硬化性化合物(B)100重量部に対して、無機微粒子(C)5重量部以上500重量部以下を含む、請求項8に記載のハードコート剤組成物。
- 無機微粒子(C)が、金属(又は半金属)酸化物の微粒子、又は金属(又は半金属)硫化物の微粒子である、請求項8又は9に記載のハードコート剤組成物。
- 無機微粒子(C)が、シリカ微粒子である、請求項8〜10のうちのいずれか1項に記載のハードコート剤組成物。
- 無機微粒子(C)が、活性エネルギー線反応性基を有する加水分解性シラン化合物によって表面修飾されたものである、請求項8〜11のうちのいずれか1項に記載のハードコート剤組成物。
- 請求項1〜12のうちのいずれか1項に記載のハードコート剤組成物の硬化物を含むハードコート層が表面に付与された物体。
- 支持基体上に、少なくとも記録層又は反射層を含む、1層又は複数層から構成される膜体を有する光情報媒体であって、前記支持基体側表面及び前記膜体側表面のうちの少なくとも一方の表面が、請求項1〜12のうちのいずれか1項に記載のハードコート剤組成物の硬化物を含むハードコート層によって形成されている光情報媒体。
- 前記支持基体側表面及び前記膜体側表面のうちの光入射側とされる表面が、前記ハードコート層によって形成されている、請求項14に記載の光情報媒体。
- 支持基体上に情報記録層と、情報記録層上の光透過層とを有し、光透過層上に、請求項1〜12のうちのいずれか1項に記載のハードコート剤組成物の硬化物を含むハードコート層を有する光情報媒体。
Priority Applications (6)
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JP2003360123A JP4779293B2 (ja) | 2003-10-21 | 2003-10-21 | ハードコート剤組成物及びこれを用いた光情報媒体 |
DE112004001978.8T DE112004001978B4 (de) | 2003-10-21 | 2004-10-21 | Hartbeschichtungsmittel-Zusammensetzung und deren Verwendung |
PCT/JP2004/015953 WO2005049687A1 (en) | 2003-10-21 | 2004-10-21 | Hardcoat agent composition and optical information medium thereof |
CN200480031208.4A CN100484982C (zh) | 2003-10-21 | 2004-10-21 | 硬涂层剂组合物及由其生产的光学信息介质 |
US10/576,195 US7632874B2 (en) | 2003-10-21 | 2004-10-21 | Hardcoat agent composition and optical information medium thereof |
US12/581,958 US7838097B2 (en) | 2003-10-21 | 2009-10-20 | Hardcoat agent composition and optical information medium thereof |
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JP2003360123A JP4779293B2 (ja) | 2003-10-21 | 2003-10-21 | ハードコート剤組成物及びこれを用いた光情報媒体 |
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JP4779293B2 JP4779293B2 (ja) | 2011-09-28 |
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JP2003360123A Expired - Lifetime JP4779293B2 (ja) | 2003-10-21 | 2003-10-21 | ハードコート剤組成物及びこれを用いた光情報媒体 |
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US (2) | US7632874B2 (ja) |
JP (1) | JP4779293B2 (ja) |
CN (1) | CN100484982C (ja) |
DE (1) | DE112004001978B4 (ja) |
WO (1) | WO2005049687A1 (ja) |
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US20070148596A1 (en) | 2007-06-28 |
US7632874B2 (en) | 2009-12-15 |
US20100040823A1 (en) | 2010-02-18 |
WO2005049687A8 (en) | 2006-01-12 |
WO2005049687A1 (en) | 2005-06-02 |
DE112004001978T5 (de) | 2013-10-10 |
DE112004001978B4 (de) | 2016-08-04 |
JP4779293B2 (ja) | 2011-09-28 |
US7838097B2 (en) | 2010-11-23 |
CN1871275A (zh) | 2006-11-29 |
CN100484982C (zh) | 2009-05-06 |
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