JPH0364745A - Manufacture of optical recording medium - Google Patents
Manufacture of optical recording mediumInfo
- Publication number
- JPH0364745A JPH0364745A JP1201589A JP20158989A JPH0364745A JP H0364745 A JPH0364745 A JP H0364745A JP 1201589 A JP1201589 A JP 1201589A JP 20158989 A JP20158989 A JP 20158989A JP H0364745 A JPH0364745 A JP H0364745A
- Authority
- JP
- Japan
- Prior art keywords
- optical recording
- recording medium
- photochromic compound
- compound
- air
- 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.)
- Granted
Links
- 230000003287 optical effect Effects 0.000 title claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000003093 cationic surfactant Substances 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 7
- 239000012528 membrane Substances 0.000 abstract description 4
- 239000010410 layer Substances 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- OGQYPPBGSLZBEG-UHFFFAOYSA-N dimethyl(dioctadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC OGQYPPBGSLZBEG-UHFFFAOYSA-N 0.000 description 1
- 239000004815 dispersion polymer Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
Abstract
Description
【発明の詳細な説明】
産業上の利用分野
本発明は、データ、画像等の情報を、高密度に記録する
媒体としての光ディスクなどに利用される光学記録媒体
に関する。DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to an optical recording medium used for optical disks and the like as a medium for recording information such as data and images with high density.
従来の技術
従来、有機化合物を用いた書換え可能な光学記録媒体と
してフォトクロミック化合物を用いるものが知られてい
る。2. Description of the Related Art Conventionally, rewritable optical recording media using organic compounds have been known to use photochromic compounds.
この光学記録媒体の動作原理は、波長の異なる２種類の
光源によって可逆的な色の変化を生じるフォトクロミッ
ク化合物のもつ特性を利用して、吸光嵐 透過域 ある
いは反射率の変化を２値記憶するものであも
有機フォトクロミック化合物を光学記録媒体の記録層と
して基板上へ形成する光学記録媒体の製造方法としては
キャスト嵐 高分子分散キャスト法 真空蒸着浪 お
よびラングミュア−プロジェット法（以下、ＬＢ法と略
も ）などが知られていも
特に ＬＢ法は記録層のフォトクロミック反応の制御性
や底膜の際の膜厚安定性などに優れていも
発明が解決しようとする課題
従ｉ ＬＢ法が適用されているフォトクロミック化合
物Ｃヨ 気水界面において単分子膜を形成する界面活
性を化合物に付与するた△ そのフォトクロミック反応
を示す分子構造に長鎖炭化水素鎖を置換基として有する
必要があａ
そのために ＬＢ法を光学記録媒体の製造方法として利
用する場合に（友 長鎖炭化水素鎖を有さないフォトク
ロミック化合物負 水溶性のフォトクロミック化合物（
友 気水界面において安定な単分子膜の形成ができない
たべ 記録層の製造に対して材料的な制限が存在した
ＬＢ法の適用のできない化合物を底膜する手段として（
よ 安定な単分子膜を形成するマトリクス分子と、その
化合物との混合膜として作製する方法があも
しかし この方法ではフォトクロミック化合物はマトリ
クス分子によって希釈されるた△ 単位面積当りの光学
密度が小さくなってしま１．％ 大きな光学密度を必
要とする光記録媒体の製造には効率的ではない課題があ
った
また この方法はマトリクス間に化合物を閉じこめるた
△ フォトクロミック化合物が凝集したり、化合物相と
マトリクス相との相分離を生じたりする課題もありｔら
また 水溶性のフォトクロミック化合物の場合に１よ
混合単分子膜中から溶解してしまう。そのた△ 混合膜
形成によるＬＢ法では均質な記録層の製造ができ哄 上
記の材料的な制限を解決できない課題があった
課題を解決するための手段
カルボキシル基を有するフォトクロミック化合物と、長
鎖炭化水素鎖を有するカチオン性界面活性物質とを塩形
成させて、気水界面において単分子膜の形成を行なう。The operating principle of this optical recording medium is to use the properties of photochromic compounds that produce reversible color changes when exposed to two types of light sources with different wavelengths to store binary information about changes in light absorption, transmission range, or reflectance. Methods for manufacturing optical recording media in which an organic photochromic compound is formed on a substrate as a recording layer of an optical recording medium include Cast Arashi, polymer dispersion casting method, vacuum evaporation method, and Langmuir-Prodgett method (hereinafter abbreviated as LB method). Although methods such as ) are known, the LB method in particular has excellent controllability of the photochromic reaction of the recording layer and stability of the film thickness when forming the bottom film, but there are still problems to be solved by the invention. In order to impart surface activity to the compound that forms a monomolecular film at the air-water interface, it is necessary for the photochromic compound C to have a long hydrocarbon chain as a substituent in the molecular structure that exhibits the photochromic reaction.For this purpose, the LB method is used. When using photochromic compounds as a manufacturing method for optical recording media (photochromic compounds without long hydrocarbon chains) water-soluble photochromic compounds (negative)
As a means of forming a bottom film with a compound that cannot be applied to the LB method due to material limitations in the production of the recording layer, it is not possible to form a stable monomolecular film at the air-water interface.
However, in this method, the photochromic compound is diluted by the matrix molecules, so the optical density per unit area becomes smaller. Teshima 1. % In the production of optical recording media that require a high optical density, there was an issue of inefficiency.In addition, this method traps the compound between the matrices, resulting in agglomeration of the photochromic compound and the possibility of agglomeration of the compound phase and the matrix phase. There are also problems such as separation, etc. In the case of water-soluble photochromic compounds,
It dissolves from within the mixed monolayer. On the other hand, the LB method by forming a mixed film can produce a homogeneous recording layer.Means to solve the problem that the above-mentioned material limitations could not be overcome A monomolecular film is formed at the air-water interface by forming a salt with a cationic surfactant having a hydrogen chain.
作用
カチオン性界面活性物質との塩形成を行なうことによっ
て、本来界面活性を持たないフォトクロミック化合物に
界面活性を付与することが可能になり、気水界面におい
て安定なフォトクロミック化合物の単分子膜を形成でき
も
それによって、適用した化合物の持つ光学密度を有効に
利用することができ、ＬＢ法を利用して均質な記録層の
形成が可能になん
実施例
使用したフォトクロミック化合物は 下記化学構造式で
示すスピロピラン化合物Ａであり、ピラン環の８位にカ
ルボキシル基を有していもこの分子は、長鎖炭化水素鎖
を持たず、従来はＬＢ法の適用ができなかった。さらに
、カルボキシル基を有するため、水溶性であり、着色体
が安定なフォトクロミック反応を示す。By forming a salt with a cationic surfactant, it is possible to impart surface activity to a photochromic compound that originally does not have surface activity, and it is possible to form a stable monomolecular film of the photochromic compound at the air-water interface. By doing so, it is possible to effectively utilize the optical density of the applied compound, and it is possible to form a homogeneous recording layer using the LB method. Although Compound A has a carboxyl group at the 8-position of the pyran ring, this molecule does not have a long hydrocarbon chain, and the LB method could not previously be applied to this molecule. Furthermore, since it has a carboxyl group, it is water-soluble and exhibits a stable photochromic reaction as a colored body.
他にピラン環の８位、インドリン環の５．６位、Ｎ位に
カルボキシル基やアルキル基を介したカルボキシル基で
置換された構造のスピロピラン化合物も本発明を適用で
きる。In addition, the present invention can also be applied to spiropyran compounds having a structure in which the 8-position of the pyran ring, the 5.6-position, and the N-position of the indoline ring are substituted with a carboxyl group or a carboxyl group via an alkyl group.
直鎖飽和炭化水素鎖を有するカチオン性界面活性物質と
して、下記化学構造式のジオクタデシル−ジメチル−ア
ンモニウムＢを用いた。他の物質としては、炭素数１２
から２４の長鎖炭化水素鎖をもつアルキルアミンや、２
分子膜形成能を有するカチオン性界面活性分子が適して
いる。Dioctadecyl-dimethyl-ammonium B having the following chemical structural formula was used as a cationic surfactant having a linear saturated hydrocarbon chain. Other substances include carbon number 12
Alkylamines with long hydrocarbon chains from 24 to 24,
Cationic surfactant molecules having the ability to form molecular membranes are suitable.
以下に本発明の実施例を示す。Examples of the present invention are shown below.
実施例１
等モル量のスピロピラン化合物Ａと界面活性物質Ｂを有
機溶媒中で混合するここで塩形成を行なった。Example 1 Salt formation was carried out in which equimolar amounts of spiropyran compound A and surfactant B were mixed in an organic solvent.
有機溶媒としては、等量のメチルアルコールとベンゼン
の混合溶媒を用いた。As the organic solvent, a mixed solvent of equal amounts of methyl alcohol and benzene was used.
この溶液を展開溶液として使用し、単分子膜を形成した
。This solution was used as a developing solution to form a monomolecular film.
水相は、イオン交換水を１回蒸留した純水を用１、＜
水温１６℃とし７’−。For the aqueous phase, pure water obtained by distilling ion-exchanged water once was used.
Water temperature is 16℃ and 7'-.
気水界面における単分子膜の形成（上 圧縮速度１０ｍ
ｍ／ｍｉｎで行なｌ、′Ｘ、単分子膜の形成の確認は表
面圧−面積特帳 および気水界面での単分子膜の吸収ス
ペクトルを測定して行なっｔもスピロピラン化合物Ａ（
友 単独では水溶性であるために単分子膜を形成するこ
とができない戟本発明によるカチオン性界面活性物質Ｂ
との塩形成によって単分子膜の作製が可能になも気水界
面に形成した単分子膜は液体凝縮膜であり、暗所で着色
体安定な吸収極大波長４２０ ｎｍのピークを示しｔも
ＬＢ法による記録層の形成６上 累積時の表面圧２０ｒ
ｎＮ／ｍ 累積速度１０ｍｍ／ｍｉｎの条件で、石英
板基板上に累積を行なっ九
この製造方法によって、吸収極大波長約４２０ｎｍの着
色体安定な光学記録媒体が得られた発明の効果
本発明のカルボキシル基を有するフォトクロミック化合
物をカチオン性界面活性物質ε塩形成させることによっ
て、安定な気水界面単分子膜を形成させるこｋができ、
均質な光学記録媒体を提供でき厄
すなわち本発明の製造方法を用いると、水溶性であった
り、長鎖がないためにＬＢ法を適用できなかったカルボ
キシル基を有するフォトクロミック化合物について、Ｌ
Ｂ法による記録層形成を可能にする効果があも
それ故ζ、、ＬＢ法によって製造できる光学記録媒体と
しての適用が可能なフォトクロミック化合物の種類を増
やすことができる。Formation of a monomolecular film at the air-water interface (top compression speed 10 m)
The formation of a monomolecular film was confirmed by measuring the absorption spectrum of the monomolecular film at the surface pressure-area interface and the air-water interface.
Cationic surfactant B according to the present invention cannot form a monomolecular film alone because it is water-soluble.
However, the monomolecular film formed at the air-water interface is a liquid condensation film, exhibiting a peak absorption maximum wavelength of 420 nm that is stable as a colored substance in the dark, and t of LB. Formation of recording layer by method 6, cumulative surface pressure 20r
nN/m Accumulation was carried out on a quartz plate substrate at an accumulation rate of 10 mm/min. By this manufacturing method, a colored stable optical recording medium with a maximum absorption wavelength of about 420 nm was obtained. Effects of the Invention Carboxyl of the present invention By forming a cationic surfactant ε salt of a photochromic compound having a group, a stable monomolecular film at the air-water interface can be formed.
In other words, when using the production method of the present invention, it is difficult to provide a homogeneous optical recording medium, and the L
Since the effect of making it possible to form a recording layer by the B method is ζ, it is possible to increase the types of photochromic compounds that can be used as optical recording media that can be manufactured by the LB method.
Claims (4)
と、直鎖飽和炭化水素鎖を有するカチオン性界面活性物
質とを塩形成させることによって、気水界面において単
分子膜を形成させることを特徴とする光学記録媒体の製
造方法。(1) An optical recording medium characterized by forming a monomolecular film at an air-water interface by forming a salt between a photochromic compound having a carboxyl group and a cationic surfactant having a linear saturated hydrocarbon chain. manufacturing method.
物質とを有機溶媒中で混合し、塩形成させることを特徴
とする請求項１に記載の光学記録媒体の製造方法。(2) The method for producing an optical recording medium according to claim 1, characterized in that the photochromic compound and the cationic surfactant are mixed in an organic solvent to form a salt.
て薄膜化することを特徴とする請求項１に記載の光学記
録媒体の製造方法。(3) The method for manufacturing an optical recording medium according to claim 1, characterized in that the monomolecular film is thinned using the Langmuir-Prodgett method.
ピロピラン化合物であることを特徴とする請求項１に記
載の光学記録媒体の製造方法。 ▲数式、化学式、表等があります▼(4) The method for producing an optical recording medium according to claim 1, wherein the photochromic compound is a spiropyran compound having the following chemical structural formula. ▲Contains mathematical formulas, chemical formulas, tables, etc.▼
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1201589A JP2589818B2 (en) | 1989-08-03 | 1989-08-03 | Manufacturing method of optical recording medium |
| US07/561,632 US5252437A (en) | 1989-08-03 | 1990-08-02 | Photochromic materials having a thin photochromic film and a method for fabricating the same |
| DE69008965T DE69008965T2 (en) | 1989-08-03 | 1990-08-03 | Photochromic materials made of a thin photochromic film and method for producing the same. |
| EP90308562A EP0411957B1 (en) | 1989-08-03 | 1990-08-03 | Photochromic materials having a thin photochromic film and a method for fabricating the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1201589A JP2589818B2 (en) | 1989-08-03 | 1989-08-03 | Manufacturing method of optical recording medium |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0364745A true JPH0364745A (en) | 1991-03-20 |
| JP2589818B2 JP2589818B2 (en) | 1997-03-12 |
Family
ID=16443563
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1201589A Expired - Fee Related JP2589818B2 (en) | 1989-08-03 | 1989-08-03 | Manufacturing method of optical recording medium |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2589818B2 (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62164684A (en) * | 1986-01-17 | 1987-07-21 | Sony Corp | Photochromic compound |
| JPS6422811A (en) * | 1987-07-15 | 1989-01-25 | Kanebo Ltd | Skin cosmetic |
| JPS6426848A (en) * | 1987-07-23 | 1989-01-30 | Agency Ind Science Techn | Optical recording medium |
-
1989
- 1989-08-03 JP JP1201589A patent/JP2589818B2/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62164684A (en) * | 1986-01-17 | 1987-07-21 | Sony Corp | Photochromic compound |
| JPS6422811A (en) * | 1987-07-15 | 1989-01-25 | Kanebo Ltd | Skin cosmetic |
| JPS6426848A (en) * | 1987-07-23 | 1989-01-30 | Agency Ind Science Techn | Optical recording medium |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2589818B2 (en) | 1997-03-12 |
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