JPS6311933A - Optical recording medium - Google Patents
Optical recording mediumInfo
- Publication number
- JPS6311933A JPS6311933A JP61155113A JP15511386A JPS6311933A JP S6311933 A JPS6311933 A JP S6311933A JP 61155113 A JP61155113 A JP 61155113A JP 15511386 A JP15511386 A JP 15511386A JP S6311933 A JPS6311933 A JP S6311933A
- Authority
- JP
- Japan
- Prior art keywords
- fulgide
- film
- compd
- recording medium
- optical recording
- 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
- 230000003287 optical effect Effects 0.000 title claims description 10
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 1
- 239000010408 film Substances 0.000 abstract description 9
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- 238000006317 isomerization reaction Methods 0.000 abstract description 5
- 239000010409 thin film Substances 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 230000002209 hydrophobic effect Effects 0.000 abstract description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 1
- 244000201986 Cassia tora Species 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 229940038384 octadecane Drugs 0.000 description 1
- NCAIGTHBQTXTLR-UHFFFAOYSA-N phentermine hydrochloride Chemical compound [Cl-].CC(C)([NH3+])CC1=CC=CC=C1 NCAIGTHBQTXTLR-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/004—Recording, reproducing or erasing methods; Read, write or erase circuits therefor
- G11B7/0045—Recording
- G11B7/00455—Recording involving reflectivity, absorption or colour changes
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/004—Recording, reproducing or erasing methods; Read, write or erase circuits therefor
- G11B7/005—Reproducing
- G11B7/0052—Reproducing involving reflectivity, absorption or colour changes
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/004—Recording, reproducing or erasing methods; Read, write or erase circuits therefor
- G11B7/0055—Erasing
- G11B7/00552—Erasing involving colour change media
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
- G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Optical Record Carriers And Manufacture Thereof (AREA)
Abstract
Description
【発明の詳細な説明】 産業上の利用分野 本発明は書き換え可能な光学記録媒体に関する。[Detailed description of the invention] Industrial applications The present invention relates to a rewritable optical recording medium.
従来の技術
従来、波長の異なる２種類の光源により、可逆的な色の
変化を生ずる材料としてフォトクロミック材料が知られ
ている。フォトクロミック材料の一つとしてフルギドが
挙げられる。（１）がフルギドの一般式である。つまり
フルギドは、無水こはく酸あるいはその誘導体の二つの
メチレン炭素に、それぞれアルキリデン基がついている
化合物であ（ただしＲ１−Ｒ４のうち少なくとも一つは
芳香環、Ｘ＝ｏ、Ｎ−Ｒ）
フルギドは、他のフォトクロミック化合物と比較して繰
り返し寿命が長いと報告されている。しかし現在までに
光学記録媒体として利用することを目的とした実施例は
、ポリマーマトリックス（米国特許第４２２０７０８号
）、あるいは粘土中（米国特許第４５０３１７７号）で
のフォトクロミズムの報告例があるにすぎない。2. Description of the Related Art Photochromic materials have been known as materials that can reversibly change color when exposed to two types of light sources with different wavelengths. Fulgide is one of the photochromic materials. (1) is the general formula of fulgide. In other words, fulgide is a compound in which an alkylidene group is attached to each of the two methylene carbons of succinic anhydride or its derivatives (at least one of R1-R4 is an aromatic ring, X=o, N-R). , it has been reported that it has a long cycle life compared to other photochromic compounds. However, to date, there have only been reports of photochromism in polymer matrices (US Pat. No. 4,220,708) or clay (US Pat. No. 4,503,177) for use as optical recording media. .
発明が解決しようとする問題点
フルギドを光学記録媒体として利用するための問題点は
二つある。一つは異性化反応である。フルギドはフォト
クロミズムを示さない位置異性体をもっている。これま
でのフルギドはこの位置異性体への副反応が、本反応の
変換率を低下させていた。もう一つの問題は、薄膜化で
ある。均一な薄膜を作成するためｋは、ＬＢ法が最も優
れているわけだが、これまでフルギドを用いてＬＢ膜を
形成したという例はない。これは、フルギドが疎水性の
長鎖を持たず、したがって気水界面上に展開し、ＬＢ膜
を作成するのが困難なためである。Problems to be Solved by the Invention There are two problems in using fulgide as an optical recording medium. One is an isomerization reaction. Fulgide has positional isomers that do not exhibit photochromism. Until now, fulgide had a side reaction to form this positional isomer, which lowered the conversion rate of this reaction. Another problem is thinning the film. The LB method is the best method for producing a uniform thin film, but to date there has been no example of forming an LB film using fulgide. This is because fulgide does not have long hydrophobic chains and therefore is difficult to spread on the air-water interface and create an LB film.
本発明は、フルギドに長鎖を導入することにより立体障
害を付与し、異性化反応を抑えることを目的とする。ま
た、それと同時にＬＢ法を用いて薄膜を形成し、フルギ
ドのフォトクロミズムを薄膜上に付与することを目的と
する。The purpose of the present invention is to impart steric hindrance to fulgide by introducing a long chain to suppress the isomerization reaction. Moreover, at the same time, the purpose is to form a thin film using the LB method and impart fulgide photochromism onto the thin film.
問題点を解決するための手段
下記一般式で示されるフォトクロミック化合物を用いて
光学記録媒体を構成する。Means for Solving the Problems An optical recording medium is constructed using a photochromic compound represented by the following general formula.
Ｑ
なお、ここでＲは、Ｃ＝６からＣ＝３１４での炭化水素
である〇
作 用
上記の化合物に導入された炭化水素の長鎖によって立体
障害が付与され、異性化による変換率の低下を防ぐこと
ができる◇
また、フルギド骨格自体は長鎖部分に比べて、親水性が
高いので、ＬＢ膜を形成する＠これによりフルギドの性
質をもった薄膜を容易に得ることができる〇
実施例
原料が工業的に容易に手にはいるのはＣ＝３１までの炭
化水素である。また、Ｃ＝ｓ未満の炭化水素では、合成
に際して、立体異性体の分離操作を必要とする。好まし
くは、Ｃ＝１３からＣ＝２３までの炭化水素で、親水性
と疎水性のバランスが良く、したがって、取り扱いが簡
単で、単独でのＬＢ膜の形成も容易である。Q Here, R is a hydrocarbon with C=6 to C=314 〇 Effect The long chain of hydrocarbon introduced into the above compound imparts steric hindrance, reducing the conversion rate due to isomerization. ◇ In addition, since the fulgide skeleton itself is more hydrophilic than the long chain portion, it forms an LB film.@Thus, a thin film with the properties of fulgide can be easily obtained〇Example The raw materials that are easily available industrially are hydrocarbons up to C=31. Furthermore, hydrocarbons with C=s less than s require separation of stereoisomers during synthesis. Preferably, it is a hydrocarbon of C=13 to C=23, which has a good balance between hydrophilicity and hydrophobicity, and is therefore easy to handle and easy to form an LB film by itself.
さらに、炭化水素との混合物を用いてＬＢ膜を形成する
ことによって、フルギドの長鎖の部分の充填率が高くな
り、より安定なＬＢ膜の形成が可能となる。Furthermore, by forming an LB film using a mixture with a hydrocarbon, the filling rate of the long chain portion of fulgide increases, making it possible to form a more stable LB film.
実施例１
下記の構造で示されるフルギド（以下ＦＦ−１０と略す
）を用いた。Example 1 Fulgide (hereinafter abbreviated as FF-10) having the structure shown below was used.
！康
６００ｒｐｍ で６０秒スピンコードを行って記録１
：層内で速やかに反応し、着色形に変化し、赤色に発色
した（Ａｍａ工＝６００ｎｍ）。さらにこの着色形は可
視光（λ工、、＝５００ｎｍ）照射によシ、同じ〈記録
層内で速やかに元のＦＦ−１０に戻った。! Record 1 by performing a spin code for 60 seconds at 600 rpm.
: Reacted rapidly within the layer, changed to a colored form, and developed a red color (Ama = 600 nm). Furthermore, upon irradiation with visible light (λ = 500 nm), this colored form quickly returned to the original FF-10 within the same recording layer.
実施例２
ＦＦ−１ｏをベンゼン溶液にし、ＬＢ法を用いて以下の
条件で基板上に記録層を作成また。Example 2 A recording layer was prepared on a substrate using the LB method using FF-1o as a benzene solution under the following conditions.
基 板 ニジリカガラスをクロルトリメチルシランの
１０％トルエン溶液に１０
分間浸せきした後、トリクロルエ
タンで洗浄したもの
ト ラ ７ ： １４０ｗＸ６００ｍサブフ
ェーズ ： ｐＨ７，０１Ｊン酸バッファー５：Ｇ屋１
８°０
圧縮速度：１ｏＴｌｌＩ／ｍ１ｎ
累積圧： １５ ｍＮ／ｍ
累積数：１６層
この記録層も実施例１における記録層と同様に、波長の
異なる２種類の光源により、可逆的に反応が進行した。Substrate Nijirica glass immersed in a 10% toluene solution of chlorotrimethylsilane for 10 minutes and then washed with trichloroethane.Tora 7: 140w x 600m Subphase: pH 7,01 J acid buffer 5: Gya 1
8°0 Compression speed: 1oTllI/m1n Cumulative pressure: 15 mN/m Cumulative number: 16 layers Similar to the recording layer in Example 1, this recording layer also undergoes a reversible reaction using two types of light sources with different wavelengths. did.
実施例３
ＦＦ−１ｏ／オクタデカン＝Ｈの混合比のベンゼン溶液
を調整し、実施例１と同様の方法で記録層を形成した。Example 3 A benzene solution having a mixing ratio of FF-1o/octadecane=H was prepared, and a recording layer was formed in the same manner as in Example 1.
この記録層も実施例１における記録層と同様に、波長の
異なる２種類の光源により、可逆的に反応が進行した。Similar to the recording layer in Example 1, this recording layer also underwent a reversible reaction using two types of light sources with different wavelengths.
さらにこの場合、暗所室温において、ＦＦ−１０で半減
期は１週間、及び着色形で半減期は１日以上と実施例２
で示したＦＦ−１０単独の場合（半減期は１時間程度）
よりも安定性は著しく向上した。Furthermore, in this case, at room temperature in the dark, FF-10 has a half-life of one week, and the colored form has a half-life of one day or more.
In the case of FF-10 alone as shown in (half-life is about 1 hour)
The stability was significantly improved.
それぞれの場合の吸収スペクトルを曲線Ａ、Ｂとして図
に示す。The absorption spectra in each case are shown as curves A and B in the figure.
発明の効果
本発明により、記録寿命の長い光学記録媒体の提供が可
能となシ、その波及効果は大である。Effects of the Invention The present invention makes it possible to provide an optical recording medium with a long recording life, and its ripple effects are significant.
図は本発明の実施例における光学記録媒体の記録層の吸
収スペクトル図である。
特許出願人 工業技術院長崎←←←−−−達負東偉巳
３００ 幼Ｏ５ｔ）０ ６００
νθ浪 長 （割The figure is an absorption spectrum diagram of a recording layer of an optical recording medium in an example of the present invention. Patent applicant: Agency of Industrial Science and Technology, Nagasaki
νθlong (wari)
Claims (3)
用いた光学記録媒体。 （ただしＲはＣ＝５〜３１のアルキル鎖） ▲数式、化学式、表等があります▼(1) An optical recording medium using a photochromic compound represented by the following general formula. (However, R is an alkyl chain with C=5 to 31) ▲There are mathematical formulas, chemical formulas, tables, etc.▼
を有することを特徴とする特許請求の範囲第１項記載の
光学記録媒体。(2) The optical recording medium according to claim 1, which has a recording layer made of an LB film of a photochromic compound.
ＬＢ膜からなる記録層を有することを特徴とする特許請
求の範囲第１項記載の光学記録媒体。(3) The optical recording medium according to claim 1, which has a recording layer made of an LB film of a mixture of a photochromic compound and a hydrocarbon.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61155113A JPS6311933A (en) | 1986-07-03 | 1986-07-03 | Optical recording medium |
| US07/023,253 US4803287A (en) | 1986-04-16 | 1987-03-09 | Certain photochromic fulgide compounds and method for their synthesis |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61155113A JPS6311933A (en) | 1986-07-03 | 1986-07-03 | Optical recording medium |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6311933A true JPS6311933A (en) | 1988-01-19 |
Family
ID=15598872
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61155113A Pending JPS6311933A (en) | 1986-04-16 | 1986-07-03 | Optical recording medium |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6311933A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5061582A (en) * | 1987-06-17 | 1991-10-29 | Plessey Overseas Limited | Optical data storage |
| US5989671A (en) * | 1989-11-22 | 1999-11-23 | Sharp Kabushiki Kaisha | Optical recording medium and manufacturing method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4220708A (en) * | 1977-07-22 | 1980-09-02 | Heller Harold G | Photochromic compounds |
| JPS61138236A (en) * | 1984-12-10 | 1986-06-25 | Agency Of Ind Science & Technol | Display element |
-
1986
- 1986-07-03 JP JP61155113A patent/JPS6311933A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4220708A (en) * | 1977-07-22 | 1980-09-02 | Heller Harold G | Photochromic compounds |
| JPS61138236A (en) * | 1984-12-10 | 1986-06-25 | Agency Of Ind Science & Technol | Display element |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5061582A (en) * | 1987-06-17 | 1991-10-29 | Plessey Overseas Limited | Optical data storage |
| US5989671A (en) * | 1989-11-22 | 1999-11-23 | Sharp Kabushiki Kaisha | Optical recording medium and manufacturing method thereof |
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