JP2007531955A - 限定再生型光記憶媒体及びその製造方法 - Google Patents
限定再生型光記憶媒体及びその製造方法 Download PDFInfo
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Abstract
【選択図】 図1
Description
次に、例示的であって限定的ではない図面について述べる。
透過率及び反射率測定のためのCIE1976又はCIELab系(即ち、L*a*b*座標)、並びに
透過率及び反射率測定のためのCIE1976LCh系(即ち、明度(L*)、彩度(C*)及び色相(h°)座標)。
A=吸光度
B=cm単位の光路長
C=濃度(モル/リットル単位のモル濃度)
実施例1
この実施例では、1,5−ビス(イソプロピルアミノ)アントラキノンの合成を詳述する。3.00グラム(g)(0.011モル(mol))の1,5−ジクロロアントラキノン、30ミリグラム(mg)の銅粉末、30mgのヨウ化銅(I)及び20ミリリットル(ml)(0.235モル)のイソプロピルアミンを30mlのエチレングリコールに添加し、得られた懸濁液を油浴中に保持した密封容器内で160℃に加熱した。加熱を160℃で16時間続けた後、加熱を停止し、室温に達するまで容器を放置した。その後、20mlのメタノールを容器に添加し、内容物を室温で30分間攪拌した。次いで、得られた混合物を50グラム(g)の15%(重量/体積(wt/vol))氷冷(即ち、約5℃の)HCl溶液中にゆっくりと注ぎ込んだ。次いで、沈殿を濾別し、水を用いて酸を含まないように洗い、100℃で真空乾燥した。収量は3.00gであった。こうして得られた粗生成物を、80%のn−ヘキサン及び20%の酢酸エチルを含む溶離剤系を用いるカラムクロマトグラフィーで精製した。HPLCを用いて測定したところ、80%の純度が得られた。プロトンNMR(1H NMR)分光法(300メガヘルツ(MHz)、重水素化クロロホルム(CDCl3))を用いて生成物の特性決定を行ったところ、化学シフト(δ)1.36(二重線(d),12プロトン(H))、δ3.86(多重線(m),2H)、δ6.99(d,2H)、δ7.53(m,4H)、δ9.75(窒素に結合したプロトン(NH))であった。
この実施例では、1,5−ビス(2−N,N−ジエチルアミノ−エチルアミノ)アントラキノンの合成を詳述する。5.50g(0.02モル)の1,5−ジクロロアントラキノン、60mgの銅粉末及び20g(0.17モル)のN,N−ジエチルエチレンジアミンを含む混合物を、大気圧(約105パスカル(Pa))下で約120〜約125℃に5時間加熱した。次いで、得られた溶液を50℃に冷却した後、40mlのメタノールでトリチュレートし、50℃でさらに1時間攪拌した。次いで、こうして得られた生成物塊を100mlの氷冷水中にゆっくりと注ぎ込んだ。次いで、沈殿を濾別し、水で洗い、50℃で1晩乾燥した。収量は6.50gであった。HPLCを用いて測定したところ、98%の純度が得られた。1H NMR分光法(300MHz、CDCl3)で生成物の特性決定を行ったところ、δ1.08(三重線(t),12H)、δ2.65(四重線(q),8H)、δ2.82(m,4H)、δ3.40(m,4H)、δ6.98(d,2H)、δ7.54(m,4H)、δ9.75(NH)であった。
この実施例では、1,8−ビス(シクロヘキシルアミノ)アントラキノンの合成を詳述する。28.00g(0.101モル)の1,8−ジクロロアントラキノン、0.3gの銅粉末及び280ml(2.45モル)のシクロヘキシルアミンを含む混合物を、大気圧下で160℃に15時間加熱した。次いで、得られた溶液を60℃に冷却した後、150mlのメタノールでトリチュレートし、その温度でさらに1時間攪拌した。次いで、こうして得られた生成物塊を1000mlの15%(wt/vol)氷冷HCl溶液中にゆっくりと注ぎ込んだ。次いで、沈殿した生成物を濾別し、水を用いて酸を含まないように洗い、100℃で真空乾燥した。収量は37.00gであった。
この実施例では、1,8−ビス(イソプロピルアミノ)アントラキノンの合成を詳述する。3.00g(0.011モル)の1,8−ジクロロアントラキノン、30mgの銅粉末、30mgのヨウ化銅(I)及び25ml(0.29モル)のイソプロピルアミンを含む混合物を20ml(0.34モル)のエチレングリコールに添加し、得られた懸濁液を密封容器内で160℃に15時間加熱した。次いで、得られた溶液を室温(約23℃)に冷却し、内容物を100mlの15%氷冷酢酸溶液中にゆっくりと注ぎ込んだ。次いで、沈殿した生成物を濾別し、酸を含まないように洗い、100℃で真空乾燥した。収量は3.00gであった。次いで、試料の一部に対し、80体積パーセント(vol%)のn−ヘキサン及び20vol%の酢酸エチルを含む混合溶媒を溶離剤系として用いるカラムクロマトグラフィーを施すことで、純粋な状態の生成物を得た。HPLCで測定して93%の純度で34gの収量が得られた。1H NMR分光法(300MHz、CDCl3)で生成物の特性決定を行ったところ、δ1.39(d,12H)、δ3.86(m,2H)、δ7.07(d,2H)、δ7.50(m,4H)、δ9.73(NH)であった。
この実施例では、1,8−ビス(2−エチルヘキシルアミノ)アントラキノンの合成を詳述する。4.00g(0.014モル)の1,8−ジクロロアントラキノン、60mgの銅粉末及び10g(0.077モル)の2−エチルヘキシルアミンをフラスコ内で35mlのエチレングリコールに添加し、得られた懸濁液を160℃に16時間加熱した。次いで、フラスコの内容物を室温に放冷した後、30mlのメタノールを添加して30分間攪拌した。次いで、得られた混合物を50gの15%氷冷HCl溶液中にゆっくりと注ぎ込んだ。生じた沈殿を濾別し、酸を含まないように洗い、100℃で真空乾燥した。収量は3.50gであった。次いで粗生成物を、80vol%のn−ヘキサン及び20vol%の酢酸エチルからなる溶離剤系を用いるカラムクロマトグラフィーで精製した。HPLCを用いて測定したところ、93%の純度が得られた。1H NMR分光法(300MHz、重水素化ジメチルスルホキシド(DMSOD6))で生成物の特性決定を行ったところ、δ0.95(m,12H)、δ1.35〜1.72(m,18H)、δ3.22(m,4H)、δ7.05(d,2H)、δ7.50(m,4H)、δ9.73(NH)であった。
この実施例では、1,8−ビス(3−N,N−ジメチルアミノ−プロピルアミノ)アントラキノンの合成を詳述する。5.00g(0.018モル)の1,8−ジクロロアントラキノン、50mgの銅粉末及び40g(0.39モル)のN,N−ジメチルアミノ−3−プロピルアミンを含む混合物を、大気圧下で120℃に3時間加熱した。次いで、得られた溶液を60℃に冷却し、20mlのメタノールを用いてトリチュレートし、その温度で1時間攪拌した。次いで、こうして得られた生成物塊を200mlの氷冷水中にゆっくりと注ぎ込んだ。次いで、生じた沈殿を濾別して2gの生成物を得た。次いで、粗試料の一部に対し、80vol%のn−ヘキサン及び20vol%の酢酸エチルを含む混合溶媒を溶離剤系として用いるカラムクロマトグラフィーを施すことで、純粋な状態の生成物を得た。HPLCで測定したところ、98%の純度が得られた。1H NMR分光法(300MHz、CDCl3)で生成物の特性決定を行ったところ、δ1.94(m,4H)、δ2.29(一重線(s),12H)、δ2.46(t,4H)、δ3.40(m,4H)、δ7.07(d,2H)、δ7.52(m,4H)、δ9.75(NH)であった。
この実施例では、1,8−ビス(2−N,N−ジエチルアミノ−エチルアミノ)アントラキノンの合成を詳述する。10.00g(0.036モル)の1,8−ジクロロアントラキノン、0.3gの銅粉末及び60g(0.51モル)のN,N−ジエチルエチレンジアミンを含む混合物を、大気圧下で130℃に5時間加熱した。次いで、得られた溶液を60℃に冷却した後、25mlのメタノールでトリチュレートし、その温度でさらに1時間攪拌した。次いで、こうして得られた生成物塊を100mlの氷冷水中にゆっくりと注ぎ込んだ。次いで、沈殿した生成物を濾別し、水で洗い、50℃で1晩乾燥した。全収量は8.00gであった。HPLCを用いて測定したところ、97%の純度が得られた。1H NMR分光法(300MHz、CDCl3)で生成物の特性決定を行ったところ、δ1.11(t,12H)、δ2.65(q,8H)、δ2.82(t,4H)、δ3.40(m,4H)、δ7.03(d,2H)、δ7.51(m,4H)、δ9.72(NH)であった。
この実施例では、ベンゾピランレッドの合成を詳述する。下記の式(XXIV)のイミノ化合物9.00g(0.017モル)を、30分間攪拌することで150mlのピリジンに溶解した。
実施例9
この実施例では、数種のアントラキノン誘導体を製造し、複光束UV/VIS Perkin−Elmer Lambda900 UV/VIS/NIR分光光度計を用いて300〜800nmの波長域内におけるそのUV−VISスペクトル特性を塩化メチレン溶液中で測定した。アントラキノン誘導体の構造を表4に示すが、光学的性質は上記表1に示されている。
表1からわかる通り、すべてのアントラキノン類は600nm/365nmの波長で約1.5以上の吸光度比を示す。しかし、600nm/365nmの波長で約3以上の吸光度比を示すのは、1,5−アントラキノン類の一部にすぎない。1,8−アントラキノン類は一般に600nm/365nmの波長で約3以上の吸光度比を示すので、レーザービーム又は任意の他の光源(例えば、発光ダイオード)が通過する層上にUV硬化性接着剤が位置している光記憶媒体(非限定再生型)及びセンサー用途(例えば、センサー窓)のような、高い吸光度比の値を要求する特定の専門用途では、これらの1,8−アントラキノン類が1,5−アントラキノン類より好ましい場合がある。600nm及び365nmは波長の例である。異なる硬化装置及び読出装置では、異なる波長が要求されることがある。この点で、600nm/365nmの波長でそれぞれ22.4及び16.3の高い吸光度比を示す試料No.7及び4はさらに好ましい。
この実施例では、表5に示す処方を用いて光学品質の組成物(試料9〜12)を製造した。1,8−アントラキノン誘導体は、前述の実験手順に従って合成した。1,5−アントラキノン誘導体の一部は、前節に記載したようにして合成した。1,5−ビス(シクロヘキシルアミノ)アントラキノンだけは、Keystone Aniline社(米国)からソルベントレッド207のカラーインデックス名で購入した。建染紫色染料も、Keystone Aniline社からバットバイオレット3のカラーインデックス名で入手した。試料12中では、実施例8からのベンゾピランレッドを使用した。ホスファイト系安定剤はDover Chemicals社から入手したDoverphos S−9228であり、離型剤はMitsubishi International社から入手したグリセロールモノステアレートであった。
ソルベントレッド52及びディスパースオレンジ47は、Bayer社(米国ペンシルバニア州ピッツバーグ)からそれぞれMacrolex Red 5B及びOrange Rの商品名で入手した。次いで、表5に示す組成物を押し出して、±10%の相対厚さ許容差を有する厚さ0.60ミリメートルのフィルムを形成し、これらを基板として使用した。基板の光学的性質は、Varian社(米国カリフォルニア州パロアルト)製のUV−可視複光束分光光度計(モデルCary 300 BIO)を透過モードで用いて測定した。性質(即ち、パーセント透過率(%T)及び吸光度(Abs)比)を表6に示す。これらの試料については、キセノン硬化指数及び光漂白濾光指数も計算し、表6中に報告する。
キセノン電球及び典型的なIrgacure光開始剤(Ciba Specialty Chemicals社(米国ニューヨーク州ターリータウン)製)に関し、硬化指数(上記式(1))の計算のための基準を表7に示す。Irgacure光開始剤の吸光度は、330〜450nmの範囲内で和が合計100になるように正規化した。この波長範囲を選択したのは、ポリカーボネートのような透明ポリマー母材を通して接着剤層の硬化を行う場合にそれが普通だからである。キセノンランプに関する330〜450nmでの典型的な分光照度分布(出力)を表7に示す。接着剤の硬化のために適したキセノンランプは、Xenon社(米国マサチューセッツ州ウォーバーン)から入手できる。有効ランプエネルギーは、各波長についてランプ出力に開始剤の正規化効率(吸光度)を掛けることで計算される。開始剤の効率が不明の場合には、330〜450nmで等しい感度を有する光開始剤をシミュレートするため、各波長について0.82645の正規化効率値を使用すべきである。さらに、硬化ランプのランプ出力に関するデータが存在しない場合には、表7に示すキセノンランプ出力エネルギーを有効ランプエネルギーの計算のためのデフォルト値として使用すべきである。
表6からわかる通り、すべての試料について、600nm/365nm又は600nm/400nmの波長での吸光度比は約2以上である。実際には、約2.5以上であると共に、約5以上が好ましくて達成されている。650nm/600nmの波長での吸光度比は、すべての試料について約0.15以下である。実際には、約0.10以下であると共に、約0.075以下が好ましくて達成されている。すべての試料は、650nmの波長で70%を超える透過率、600ナノメートルの波長で約30%未満(実際には約10%以下)の透過率、及び550ナノメートルの波長で約5%未満(実際には約2%以下)の透過率を示している。試料9〜13は、約0.5以上のキセノン硬化指数を示していることに注意されたい。硬化指数は、実際にはすべての試料について5を超えており、10を超える値さえ好ましくて達成されている。さらに、試料9〜13は約2.5以上の光漂白濾光指数(上記式(2)も参照されたい)を示しており、約4.0以上が好ましくて達成されており、約5.0超がさらに好ましくて達成されている。
この実施例では、光情報記憶媒体(DVD)基板を成形するのに適した真の光学品質樹脂を高収量で製造するため、制御雰囲気(「クラス100」清浄度等級)を有する施設内において10マイクロメートルの細孔を有するフィルターを備えた溶融濾過ライン上で実施例10からの試料No.10を押し出した。押出機は、Werner and Pfleiderer社(米国ニュージャージー州)から商業的に入手できるタイプZSK−30(即ち、30mm押出機)であった。押出条件は、区画1=480°F/区画2=500°F/区画3=520°F/区画4=540°F/区画5=550°F/ダイヘッド=550°F/スクリュー速度=400〜450回転/分(rpm)であった。
表8中に示したパラメーターは、Industry Standard ECMA出版物番号267(www.ecma−inernational.orgからオンラインで入手できる「120mm DVD Read Only disk 3rd edition」、2001年4月)中に詳述されている通り、DVDディスクに関して規定された標準的なパラメーターに対応している。光学的/機械的パラメーターは、Dr.Schenk PROmeteus MT136を用いて測定した。電気的パラメーターは、AudioDev DVDPro SA300 Pulsetech driveを用いて測定した。
Dr Schenk Prometheus 136(Dr Schenk社(米国ミネソタ州ウッドベリー)から市販)を用いて、650nmでのディスク反射率を測定した。参照ディスクの反射率は、W−o−M内でのわずか20時間の暴露後に650nmの波長で約22%に達した。試料9〜12の組成物で保護された光情報記憶ディスクに関しては、対照試料で保護されたディスクと同じレベルの反射率に到達するのに(即ち、反射率が650nmの波長で約22%に増加した点まで光漂白されるのに)約80時間を要した。最も高感度のDVDプレーヤーは10%という低い反射率値を有するディスクを読み出し得ることを知れば、かかる組成物は2週間以上のフロリダでの日光暴露に相当する光漂白に対しての顕著な追加の保護をもたらすことができる(即ち、14日間のフロリダでの南面日光暴露又は(例えば、表9に示す条件下にあるW−o−M内での)約40時間の促進暴露と同等以上の処理を施しても、ディスクは読出し不可能のままである(10%未満の反射率(90%を超える吸光度)を有している)。さらに、制御部分及び好ましくは吸光物質が最初は650nmで約70%以上の光透過率を有するが、160時間の促進暴露後には650nmでの初期光透過率が約5%以上減少し、好ましくは約10%以上減少することも注目される。また、最初の80時間の促進暴露後にも650nmでの光透過率が2%以上減少することが好ましく、約5%以上がさらに好ましく、約10%以上がさらに好ましい。
記憶媒体の限定再生機能性は、様々な方法で決定できる。記憶媒体の限定再生機能性を測定する1つの方法は、パッケージからディスクを取り出し、DVDの場合であればPROMeteus DVDテスター(例えば、Dr.Schenk社から入手できるPROMeteusモデル146)のような光媒体検査装置を用いてレーザー波長(例えば、DVDに関しては650nm)での初期反射率を測定することを含んでいる。次いで、漸増的な酸素暴露後にディスク反射率を時間の関数として測定できる。ディスク反射率が酸素暴露の増加と共に低下するならば、それはディスク上でデータにアクセスできる時間を限定する反応層の存在を示している。光媒体検査装置を用いてディスク反射率を測定できるという事実は、ディスクが反射層を含むことを示している。
3 基板
5 基板
7 データ層
8 反射層
9 反応層
11 基板表面
Claims (15)
- 反射層(8)と、
光学的に透明なポリマー樹脂と吸光物質を含む制御部分であって、当該制御部分が650nmで約70%以上の光透過率、約0.1以上の硬化指数、及び約2.5以上の濾光指数を有すると共に、吸光物質が(CH2Cl2溶液中で測定して)600nmで1500mol−1・cm−1・L以上の最小吸光係数、(CH2Cl2溶液中で測定して)650nmで約1000mol−1・cm−1・L未満の最大吸光係数、及び650nm/600nmで約0.1未満の吸光係数比を有する、制御部分と、
反射層(8)と制御部分との間に配設された反応層(9)であって、酸素暴露後に(反応層(9)の制御部分とは反対側に配設された)媒体上のデータにアクセスできる時間を限定するように設計された反応層(9)と
を含んでなるデータ用限定再生型光記憶媒体。 - 吸光物質が(600nm/365nm)又は(600nm/400nm)で約5以上の吸光度比の1以上を有する、請求項1記載の記憶媒体。
- 反応層(9)が酸化された場合の媒体は、約20時間以上の促進暴露後に再生不可能であるという特性を有する、請求項1又は請求項2記載の記憶媒体。
- 制御部分が約4.0以上の濾光指数を有する、請求項1乃至請求項3のいずれか1項記載の記憶媒体。
- 制御部分が約5以上の硬化指数を有する、請求項1乃至請求項4のいずれか1項記載の記憶媒体。
- 吸光物質が、アントラキノン誘導体、ベンソピラン誘導体、建染紫色染料、及びこれらの吸光物質の1種以上を含む組合せからなる群から選択される、請求項1乃至請求項5のいずれか1項記載の記憶媒体。
- 吸光物質が、それぞれ下記の式(IX)、(X)及び(XI)を有する1,4−、1,5−及び1,8−アントラキノン誘導体並びにこれらのアントラキノン誘導体の1種以上を含む組合せからなる群から選択されるアントラキノン誘導体を含む、請求項1乃至請求項6のいずれか1項記載の記憶媒体。
- 吸光物質が1,8−ビス(シクロヘキシルアミノ)アントラキノンを含む、請求項7記載の記憶媒体。
- 吸光物質が下記の式(XV)のアントラキノン誘導体を含む、請求項6乃至請求項10のいずれか1項記載の記憶媒体。
- 制御部分が550nmの波長で約0.1%以下の透過率を有する、請求項1乃至請求項11のいずれか1項記載の記憶媒体。
- 限定再生型光記憶媒体の製造方法であって、
ポリマー樹脂と吸光物質とを混合して制御組成物を形成し、
制御組成物から、650nmで約70%以上の光透過率、約0.1以上の硬化指数、及び約2.5以上の濾光指数を有する制御部分であって、吸光物質が(CH2Cl2溶液中で測定して)600nmで1500mol−1・cm−1・L以上の最小吸光係数、(CH2Cl2溶液中で測定して)650nmで約1000mol−1・cm−1・L未満の最大吸光係数、及び650nm/600nmで約0.1未満の吸光係数比を有する制御部分を形成し、
制御部分の一方の側に反射層(8)及び反応層(9)を配設すると共に、反応層(9)が制御部分と反射層(8)との間に配設され、反応層(9)が酸素暴露後に(反応層(9)の制御部分とは反対側に配設された)媒体上のデータにアクセスできる時間を限定するように設計される
ことを含んでなる方法。 - 反射層(8)と、
光学的に透明なポリマー樹脂と吸光物質を含む制御部分であって、当該制御部分が最初は650nmで約70%以上の光透過率を有するが、160時間の促進暴露後には光透過率が650nmでの初期光透過率から約5%以上減少する、制御部分と、
反射層(8)と制御部分との間に配設された反応層(9)であって、酸素暴露後に(反応層(9)の制御部分とは反対側に配設された)媒体上のデータにアクセスできる時間を限定するように設計された反応層(9)と
を含んでなるデータ用限定再生型光記憶媒体。 - 80時間の促進暴露後に光透過率が約10%以上減少する、請求項14記載の記憶媒体。
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US10/619,642 US7087282B2 (en) | 2003-07-15 | 2003-07-15 | Limited play optical storage medium, method for making the same |
PCT/US2004/022482 WO2005010872A1 (en) | 2003-07-15 | 2004-07-14 | Limited play optical storage medium, method for making the same |
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US (1) | US7087282B2 (ja) |
EP (1) | EP1647011A1 (ja) |
JP (1) | JP2007531955A (ja) |
KR (1) | KR20060037357A (ja) |
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-
2003
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-
2004
- 2004-07-06 TW TW093120270A patent/TW200515408A/zh unknown
- 2004-07-14 JP JP2006520282A patent/JP2007531955A/ja not_active Ceased
- 2004-07-14 CN CNB2004800261932A patent/CN100385514C/zh not_active Expired - Fee Related
- 2004-07-14 WO PCT/US2004/022482 patent/WO2005010872A1/en active Application Filing
- 2004-07-14 KR KR1020067000940A patent/KR20060037357A/ko not_active Application Discontinuation
- 2004-07-14 EP EP04778140A patent/EP1647011A1/en not_active Withdrawn
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KR20060037357A (ko) | 2006-05-03 |
TW200515408A (en) | 2005-05-01 |
US7087282B2 (en) | 2006-08-08 |
CN1849650A (zh) | 2006-10-18 |
EP1647011A1 (en) | 2006-04-19 |
CN100385514C (zh) | 2008-04-30 |
US20050013232A1 (en) | 2005-01-20 |
WO2005010872A1 (en) | 2005-02-03 |
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