JPH06130546A - Optical recording medium - Google Patents
Optical recording mediumInfo
- Publication number
- JPH06130546A JPH06130546A JP4281448A JP28144892A JPH06130546A JP H06130546 A JPH06130546 A JP H06130546A JP 4281448 A JP4281448 A JP 4281448A JP 28144892 A JP28144892 A JP 28144892A JP H06130546 A JPH06130546 A JP H06130546A
- Authority
- JP
- Japan
- Prior art keywords
- optical recording
- recording medium
- phenol derivative
- derivative
- compd
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Landscapes
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Optical Record Carriers And Manufacture Thereof (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、書き込みおよび消去が
可能な光ディスクなどに適用可能な光記録媒体に関す
る。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an optical recording medium applicable to writable and erasable optical disks and the like.
【０００２】[0002]
【従来の技術および発明が解決しようとする課題】近時
の光記録システムにおいては、消去不可能な１回書き込
み型光記録媒体のほか、書き込みと消去とが可能な光記
録媒体の開発が種々行われている。かかる消去可能な可
逆的な光記録媒体においては、光照射により発色または
消色するフォトクロミック化合物を記録材料として用い
ることが種々研究されている。2. Description of the Related Art In recent optical recording systems, in addition to non-erasable one-time write type optical recording media, various developments have been made on writable and erasable optical recording media. Has been done. In such an erasable reversible optical recording medium, various studies have been conducted on the use of a photochromic compound which develops or disappears by irradiation with light as a recording material.
【０００３】しかしながら、光記録システムにおいて
は、通常、半導体レーザーによる書き込み・消去が行わ
れるため、従来の種々のフォトクロミック化合物を含有
した光記録媒体では、半導体レーザーに対する感受性が
大きな問題となっていた。このような問題を解決し、半
導体レーザーへの感受性向上、すなわち発色時の可視域
吸収ピークの長波長化を行うために、フォトクロミック
化合物の基本構造に対する置換基の影響を考慮して、分
子軌道法に基づく分子設計およびそれに基づく化合物の
再合成が行われているが、このような分子設計および化
合物の再合成は多大の時間と技術を要するため、実用的
なフォトクロミック化合物の開発が容易でなかった。However, since writing and erasing are usually performed by a semiconductor laser in an optical recording system, the sensitivity to the semiconductor laser has been a serious problem in conventional optical recording media containing various photochromic compounds. In order to solve these problems and improve the sensitivity to semiconductor lasers, that is, to increase the wavelength of the visible absorption peak at the time of color development, the molecular orbital method is considered in consideration of the effect of the substituent on the basic structure of the photochromic compound. Although the molecular design based on the above and the resynthesis of the compound based on it have been carried out, such a molecular design and the resynthesis of the compound require a great deal of time and technique, so that it was not easy to develop a practical photochromic compound. .
【０００４】本発明の主たる目的は、フォトクロミック
化合物の分子設計および再合成を行うことなく、通常の
フォトクロミック化合物を用いて、発色時の可視域吸収
ピークの長波長化を可能にした光記録媒体を提供するこ
とである。The main object of the present invention is to provide an optical recording medium capable of extending the wavelength of the visible absorption peak at the time of color development by using a normal photochromic compound without performing molecular design and resynthesis of the photochromic compound. Is to provide.
【０００５】[0005]
【課題を解決するための手段および作用】上記課題を解
決すべく、本発明者らは鋭意研究を重ねた結果、波長の
異なる２種類の光照射により可逆的に発色と消色とを繰
り返すフォトクロミック化合物と、フェノール誘導体
と、結着樹脂とからなる記録層を基板上に設けた光記録
媒体を使用するときは、可視域吸収ピークの長波長化を
行えるという新たな事実を見出し、本発明を完成するに
至った。Means and Actions for Solving the Problems As a result of intensive studies conducted by the present inventors in order to solve the above problems, as a result, a photochromic that reversibly repeats color development and decolorization by irradiation with two kinds of light having different wavelengths. When an optical recording medium having a recording layer comprising a compound, a phenol derivative, and a binder resin provided on a substrate is used, the present invention has been found to find a new fact that the visible absorption peak can be lengthened. It came to completion.
【０００６】本発明において、フォトクロミック化合物
を含む記録層に、フェノール誘導体を添加することによ
り、可視域吸収ピークの長波長化が可能になる機構につ
いては必ずしも明らかではないが、両化合物が近接する
ことにより、何らかの電子授受が生じているのではない
かと推測される。本発明におけるフォトクロミック化合
物としては、例えば光照射により環化してシクロヘキサ
ジエン環を形成することによりフォトクロミック現象を
発現するフルギドやジアリールエテン誘導体、さらに公
知のスピロピラン誘導体などがあげられる。In the present invention, the mechanism by which the phenol derivative is added to the recording layer containing the photochromic compound to make the absorption peak in the visible region have a long wavelength is not necessarily clear, but the proximity of both compounds. It is speculated that some electronic transfer may have occurred. Examples of the photochromic compound in the present invention include fulgide and diarylethene derivatives that exhibit a photochromic phenomenon by cyclizing by irradiation with light to form a cyclohexadiene ring, and known spiropyran derivatives.
【０００７】フルギドとしては、例えばH. Durr and H.
Bovas-Laurent, Photo-chromism,Elsevier, 467 頁に
記載のものがあげられる。ジアリールエテン誘導体とし
ては、例えばProc. Int. Symp. on Optical Memory, 19
89 - Japanese Journal of applied Physics, Vol. 28
(1989) Supplement 28-3, pp. 215-219 に記載のものが
あげられる。この報告に記載のフォトクロミック化合物
は、温度に対する安定性および書き込み・消去の繰り返
しに対する耐久性にもすぐれている。Examples of fulgide include H. Durr and H.
Examples include those described in Bovas-Laurent, Photo-chromism, Elsevier, page 467. Examples of the diarylethene derivative include Proc. Int. Symp. On Optical Memory, 19
89-Japanese Journal of applied Physics, Vol. 28
(1989) Supplement 28-3, pp. 215-219. The photochromic compound described in this report is also excellent in stability against temperature and durability against repeated writing / erasing.
【０００８】ジアリールエテン誘導体の具体的な例を下
記に示す。Specific examples of the diarylethene derivative are shown below.
【０００９】[0009]
【化１】 [Chemical 1]
【００１０】( 式中、Ｍｅはメチル基を示す。）また、
可視域吸収ピークの長波長化を可能にするフェノール誘
導体としては、例えばビスフェノールＡなどがあげられ
る。かかるフェノール誘導体は、フォトクロミック化合
物に対して等モル量またはそれ以上の割合で添加するの
が好ましい。(In the formula, Me represents a methyl group.)
Examples of the phenol derivative capable of increasing the visible absorption peak wavelength include bisphenol A. Such a phenol derivative is preferably added in an equimolar amount or a ratio higher than that of the photochromic compound.
【００１１】前記フェノール誘導体は、通常、紫外線吸
収添加剤として、フォトクロミック化合物含有層の表面
に積層されることのある表面保護層に添加されるもので
ある。従って、かかるフェノール誘導体を記録層に添加
することにより、紫外線に対する保護機能をも有するこ
とになる。フォトクロミック化合物およびフェノール誘
導体を含有する結着樹脂としては、例えば従来公知の種
々のビニル系単量体、例えばスチレン、クロルスチレ
ン、α−メチルスチレンなどのスチレン類；メタクリル
酸メチル、メタクリル酸エチル、アクリル酸メチル、ア
クリル酸エチル、アクリルｎ−ブチル、アクリル酸ドデ
シル、アクリル酸２−クロルエチルなどのモノカルボン
酸エステル類；塩化ビニル、臭化ビニル、酢酸ビニル、
プロピオン酸ビニル、酪酸ビニル、安息香酸ビニルなど
のビニルエステル類；アクリロニトリル、メタクリロニ
トリル、アクリルアミドなどのアクリル酸もしくはメタ
クリル酸誘導体；ビニルメチルエーテル、ビニルエチル
エーテル、ビニルイソブチルエーテルなどのビニルエー
テル類；ビニルナフタリン類；ビニルメチルケトン、ビ
ニルヘキシルケトンなどのビニルケトン類；Ｎ−ビニル
ピロール、Ｎ−ビニルカルバゾール、Ｎ−ビニルインド
ール、Ｎ−ビニルピロリデンなどのＮ−ビニル化合物な
どの単独重合体または共重合体、例えばスチレン−アク
リル共重合体などがあげられる。The above-mentioned phenol derivative is usually added as an ultraviolet absorbing additive to the surface protective layer which may be laminated on the surface of the photochromic compound-containing layer. Therefore, by adding such a phenol derivative to the recording layer, it also has a protection function against ultraviolet rays. Examples of the binder resin containing a photochromic compound and a phenol derivative include various conventionally known vinyl monomers, for example, styrenes such as styrene, chlorostyrene and α-methylstyrene; methyl methacrylate, ethyl methacrylate and acryl. Monocarboxylic acid esters such as methyl acidate, ethyl acrylate, acrylic n-butyl, dodecyl acrylate, and 2-chloroethyl acrylate; vinyl chloride, vinyl bromide, vinyl acetate,
Vinyl esters such as vinyl propionate, vinyl butyrate, vinyl benzoate; acrylic acid or methacrylic acid derivatives such as acrylonitrile, methacrylonitrile, acrylamide; vinyl ethers such as vinyl methyl ether, vinyl ethyl ether, vinyl isobutyl ether; vinyl naphthalene Vinyl ketones such as vinyl methyl ketone and vinyl hexyl ketone; Homopolymers or copolymers of N-vinyl compounds such as N-vinylpyrrole, N-vinylcarbazole, N-vinylindole and N-vinylpyrrolidene, Examples thereof include styrene-acrylic copolymer.
【００１２】結着樹脂、フォトクロミック化合物および
フェノール誘導体はそれぞれの所定量を溶媒に溶解また
は分散し、これを基板上に塗布乾燥することにより、記
録層を得ることができる。溶媒としては、これらの成分
を均一に溶解または分散しうるものであれば使用可能で
あり、例えばトルエン、ベンゼン、テトラヒドロフラ
ン、メチルエチルケトン、四塩化炭素、アセトン、メタ
ノール、エタノール、ヘキサン、シクロヘキサンなどが
あげられる。A recording layer can be obtained by dissolving or dispersing a predetermined amount of each of the binder resin, the photochromic compound and the phenol derivative in a solvent, and coating and drying this on a substrate. As the solvent, any solvent that can uniformly dissolve or disperse these components can be used, and examples thereof include toluene, benzene, tetrahydrofuran, methyl ethyl ketone, carbon tetrachloride, acetone, methanol, ethanol, hexane, and cyclohexane. .
【００１３】各成分を溶媒に溶解または分散させた塗布
液は、基板上に塗布、乾燥される。基板としては、例え
ば透明ガラス板、透明プラスチック板などの厚さ１×１
０2〜５×１０3 μｍの基板があげられる。塗布手段と
しては、バーコート法、スピンコート法、ローラコート
法、スプレーコート法などがあげられ、とくに限定され
るものではない。A coating solution prepared by dissolving or dispersing each component in a solvent is coated on a substrate and dried. As the substrate, for example, a transparent glass plate, a transparent plastic plate, etc. having a thickness of 1 × 1
A substrate having a size of 0 2 to 5 × 10 3 μm can be used. Examples of the coating means include a bar coating method, a spin coating method, a roller coating method, and a spray coating method, and are not particularly limited.
【００１４】図１はかくして得られる本発明の光記録媒
体を示しており、基板１上に記録層２が形成されてい
る。この記録層２は厚さが１０〜１００μｍであるのが
適当である。本発明の光記録媒体は、例えば波長が３０
０〜４４０ｎｍの紫外線光で発色させ、波長が４５０〜
７００ｎｍの可視光線で消色させることができるので、
発色と消色を繰り返す光ディスクなどの光記録や表示に
好適に使用することができる。FIG. 1 shows an optical recording medium of the present invention thus obtained, in which a recording layer 2 is formed on a substrate 1. The recording layer 2 suitably has a thickness of 10 to 100 μm. The optical recording medium of the present invention has, for example, a wavelength of 30.
Colored with UV light of 0 to 440 nm, wavelength of 450 to
Since it can be erased with visible light of 700 nm,
It can be suitably used for optical recording and display of an optical disc or the like that repeats coloring and erasing.
【００１５】[0015]
【実施例】次に、実施例をあげて本発明の光記録媒体を
より詳細に説明する。実施例 スチレン−アクリル共重合体と、Ｅ−フルギドと、ビス
フェノールＡと、トルエンとを重量比で１０：１：２：
３０の割合で均一に混合した。このとき、ビスフェノー
ルＡはＥ−フルギドに対して１．５倍モル量となる。EXAMPLES Next, the optical recording medium of the present invention will be described in more detail with reference to examples. Example Styrene-acrylic copolymer, E-fulgide, bisphenol A and toluene in a weight ratio of 10: 1: 2 :.
The mixture was uniformly mixed at a ratio of 30. At this time, the amount of bisphenol A is 1.5 times the molar amount of E-fulgide.
【００１６】得られた塗布液を厚さ２×１０3 μｍのガ
ラス板上にバーコート法にて塗布し、２５℃で３６時間
乾燥させて、厚さ１００μｍの記録層を形成させ、光記
録媒体を得た。比較例 ビスフェノールＡを添加しなかったほかは、実施例と同
様にして、光記録媒体を得た。評価試験 消色状態にある各光記録媒体に紫外光（３５０ｎｍ）を
照射して発色させた。このとき、各光記録媒体の吸収ス
ペクトルを分光光度計（日立製作所製のＵ−３４１０）
を用いて透過率法にて測定した。その結果を図２および
図３に示す。図２はビスフェノールＡを添加した実施例
の光記録媒体、図３はビスフェノールＡを添加しない比
較例の光記録媒体をそれぞれ示している。The obtained coating solution was applied on a glass plate having a thickness of 2 × 10 3 μm by a bar coating method and dried at 25 ° C. for 36 hours to form a recording layer having a thickness of 100 μm, and optical recording was performed. The medium was obtained. Comparative Example An optical recording medium was obtained in the same manner as in Example except that bisphenol A was not added. Evaluation Test Each optical recording medium in the decolored state was irradiated with ultraviolet light (350 nm) to develop a color. At this time, the absorption spectrum of each optical recording medium was measured by a spectrophotometer (U-3410 manufactured by Hitachi, Ltd.).
Was measured by the transmittance method. The results are shown in FIGS. 2 and 3. FIG. 2 shows an optical recording medium of an example to which bisphenol A was added, and FIG. 3 shows an optical recording medium of a comparative example to which bisphenol A was not added.
【００１７】図２および図３から、スペクトルピーク
は、比較例の５００ｎｍから５３０ｎｍへ、また吸収端
は比較例の６００ｎｍから６５０ｎｍへと長波長側にシ
フトしていることがわかる。従って、発色した実施例の
光記録媒体に５５０ｎｍの可視光線を照射して消色させ
ることができたのに対して、比較例の光記録媒体では５
００ｎｍの可視光線を照射して初めて消色させることが
できた。From FIGS. 2 and 3, it can be seen that the spectrum peak is shifted from 500 nm in the comparative example to 530 nm, and the absorption edge is shifted from 600 nm in the comparative example to 650 nm on the long wavelength side. Therefore, the color-developed optical recording medium of the example could be irradiated with visible light of 550 nm to be erased, whereas the optical recording medium of the comparative example could give 5
It was possible to erase the color only by irradiating with a visible light of 00 nm.
【００１８】[0018]
【発明の効果】本発明の光記録媒体は、新たなフォトク
ロミック化合物の分子設計や合成を行うことなく、フォ
トクロミック化合物本来の可逆性を損なうことなく、可
視域吸収ピークの長波長化が行えるため、半導体レーザ
ーに対する感受性を高めることができるという効果があ
る。Industrial Applicability The optical recording medium of the present invention is capable of lengthening the wavelength of the absorption peak in the visible region without performing molecular design or synthesis of a new photochromic compound and without impairing the reversibility inherent in the photochromic compound. This has the effect of increasing the sensitivity to semiconductor lasers.
【図１】本発明の光記録媒体を示す断面図である。FIG. 1 is a cross-sectional view showing an optical recording medium of the present invention.
【図２】実施例で得た光記録媒体のスペクトルを示すグ
ラフである。FIG. 2 is a graph showing a spectrum of an optical recording medium obtained in an example.
【図３】比較例で得た光記録媒体のスペクトルを示すグ
ラフである。FIG. 3 is a graph showing a spectrum of an optical recording medium obtained in a comparative example.
１ 基板 ２ 記録層 1 substrate 2 recording layer
Claims (1)
に発色と消色とを繰り返すフォトクロミック化合物と、
フェノール誘導体と、結着樹脂とからなる記録層を基板
上に設けたことを特徴とする光記録媒体。1. A photochromic compound that reversibly repeats color development and decolorization by irradiation with two types of light having different wavelengths,
An optical recording medium having a recording layer comprising a phenol derivative and a binder resin provided on a substrate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4281448A JPH06130546A (en) | 1992-10-20 | 1992-10-20 | Optical recording medium |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4281448A JPH06130546A (en) | 1992-10-20 | 1992-10-20 | Optical recording medium |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH06130546A true JPH06130546A (en) | 1994-05-13 |
Family
ID=17639321
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4281448A Pending JPH06130546A (en) | 1992-10-20 | 1992-10-20 | Optical recording medium |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH06130546A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0780708A3 (en) * | 1995-12-19 | 1998-06-03 | Daimler-Benz Aktiengesellschaft | Layer comprising photochromic material, manufacturing method and use of said layer |
| WO2000045139A1 (en) * | 1999-01-26 | 2000-08-03 | Consiglio Nazionale Delle Ricerche | Fiber optic sensor with photochromic transducer, and corresponding method |
| USRE42343E1 (en) | 2002-06-28 | 2011-05-10 | Victor Company Of Japan | Optical storage medium |
| CN107033535A (en) * | 2017-03-20 | 2017-08-11 | 浙江森之物工艺品有限责任公司 | A kind of environment-friendly resin artwork and its handicraft preparation method with long-acting aromatic |
-
1992
- 1992-10-20 JP JP4281448A patent/JPH06130546A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0780708A3 (en) * | 1995-12-19 | 1998-06-03 | Daimler-Benz Aktiengesellschaft | Layer comprising photochromic material, manufacturing method and use of said layer |
| US5976717A (en) * | 1995-12-19 | 1999-11-02 | Daimlerchrysler Ag | Coating comprising a photochromic material, a method for its production as well as its use |
| WO2000045139A1 (en) * | 1999-01-26 | 2000-08-03 | Consiglio Nazionale Delle Ricerche | Fiber optic sensor with photochromic transducer, and corresponding method |
| US6567158B1 (en) | 1999-01-26 | 2003-05-20 | Consiglio Nazionale Delle Ricerche | Fiber optic sensor with photochromic transducer, and corresponding method |
| USRE42343E1 (en) | 2002-06-28 | 2011-05-10 | Victor Company Of Japan | Optical storage medium |
| CN107033535A (en) * | 2017-03-20 | 2017-08-11 | 浙江森之物工艺品有限责任公司 | A kind of environment-friendly resin artwork and its handicraft preparation method with long-acting aromatic |
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