JPH06116555A - Bisphenol-based light stabilizer for cyanine dye and optical recording medium containing the same light stabilizer - Google Patents
Bisphenol-based light stabilizer for cyanine dye and optical recording medium containing the same light stabilizerInfo
- Publication number
- JPH06116555A JPH06116555A JP27147392A JP27147392A JPH06116555A JP H06116555 A JPH06116555 A JP H06116555A JP 27147392 A JP27147392 A JP 27147392A JP 27147392 A JP27147392 A JP 27147392A JP H06116555 A JPH06116555 A JP H06116555A
- Authority
- JP
- Japan
- Prior art keywords
- light stabilizer
- cyanine dye
- recording medium
- light
- bisphenol
- 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
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明はシアニン色素の光安定化
剤及びそれを含有する光記録媒体に関するものである。FIELD OF THE INVENTION The present invention relates to a light stabilizer for a cyanine dye and an optical recording medium containing the light stabilizer.
【０００２】[0002]
【従来の技術】光記録媒体いわゆる光ディスクにおいて
シアニン色素の薄膜を記録層として用いたものが実用化
されている。ここで用いられるシアニン色素は単独では
光安定性が悪く、光安定化剤を添加して使用する必要が
ある。2. Description of the Related Art Optical recording media, so-called optical discs, using a thin film of a cyanine dye as a recording layer have been put into practical use. The cyanine dye used here has poor light stability by itself, and it is necessary to add a light stabilizer for use.
【０００３】光安定化剤としてチオ配位子を有するニッ
ケル化合物などの金属錯体を用いた方法が、特開昭５９
−２１９８５２号、特開昭６２−１９３８９１号、特開
昭６２−２０７６８８号、特開昭６３−１９２９３号、
特開昭６３−１９９２４８号に示されている。この方法
は光によって生成する反応性の高い一重項酸素を失活さ
せ、三重項酸素に戻す機構を利用したものであるが、長
時間光にさらされるとシアニン色素の分解がかなり進行
するという問題点を有する。A method using a metal complex such as a nickel compound having a thio ligand as a light stabilizer is disclosed in JP-A-59 / 59.
-2119852, JP-A-62-193891, JP-A-62-207688, JP-A-63-19293,
It is shown in JP-A-63-199248. This method utilizes a mechanism that deactivates highly reactive singlet oxygen generated by light and returns it to triplet oxygen, but the problem is that decomposition of the cyanine dye proceeds considerably when exposed to light for a long time. Have a point.
【０００４】また、他の光安定化剤として、ニトロソ化
合物を用いた方法が、特開平２−３００２８７号、特開
平２−３００２８８号、特開平２−３００２８９号に示
されている。しかし、このニトロソ化合物類は、それ自
体毒性が強いか、あるいは光分解物の毒性が強い等の問
題を有しているものが多く、ニトロソ化合物を使用する
上で人体に対する安全対策が必要である等、好ましくな
い性質を有している。Further, a method using a nitroso compound as another light stabilizer is shown in JP-A-2-300287, JP-A-2-300288 and JP-A-2-300289. However, many of these nitroso compounds have a problem that they are highly toxic or photolysates are toxic themselves, and it is necessary to take safety measures for the human body when using nitroso compounds. Etc. have unfavorable properties.
【０００５】さらに、光安定化剤としてトリニトロフェ
ニルヒドラジル遊離基を有する化合物を用いる方法が、
特開平２−３０４０５５号に示されている。しかし、ト
リニトロフェニルヒドラジル遊離基を有する化合物は、
爆発性を有しており、取り扱い上、非常に問題である。Further, a method using a compound having a trinitrophenylhydrazyl free radical as a light stabilizer is
It is shown in JP-A-2-304055. However, a compound having a trinitrophenylhydrazyl radical is
It is explosive and is a very problematic handling.
【０００６】[0006]
【発明が解決しようとする課題】本発明の目的は、これ
らの問題点を解決した光安定化剤、すなわちシアニン色
素の光安定性を向上させ、取り扱いが簡単で、しかも安
全性の高い光安定化剤を提供することである。また、本
発明の別の目的は、該光安定化剤を含んだ耐光性に優れ
た光記録媒体を提供することである。An object of the present invention is to improve the photostability of a photostabilizer which solves these problems, that is, a cyanine dye, and is easy to handle and highly safe photostabilization. To provide an agent. Another object of the present invention is to provide an optical recording medium containing the light stabilizer and having excellent light resistance.
【０００７】[0007]
【発明を解決するための手段】本発明者らは、上記課題
を解決すべく鋭意検討した結果、一般式（１）（化２）DISCLOSURE OF THE INVENTION As a result of intensive studies made by the present inventors to solve the above-mentioned problems, the general formula (1) (formula 2)
【０００８】[0008]
【化２】 [Chemical 2]
【０００９】〔式中、Ｒ1〜Ｒ4は水素原子またはアルキ
ル基を示し、Ｒ5およびＲ6は水素原子、アルキル基また
はペルフルオロアルキル基を示し、Ｒ5とＲ6はお互いに
結合して環を形成していてもよい。〕で表されるビスフ
ェノール誘導体がシアニン色素の光安定性を極めて向上
させ、しかも取り扱いが簡単でかつ安全性の高い性質を
有すること、また、該光安定化剤をシアニン色素を含有
する光記録媒体に適用した場合にも、極めて効果的であ
ることを見い出し、本発明を完成した。すなわち、本発
明は一般式（１）（化３）[Wherein R 1 to R 4 represent a hydrogen atom or an alkyl group, R 5 and R 6 represent a hydrogen atom, an alkyl group or a perfluoroalkyl group, and R 5 and R 6 are bonded to each other. It may form a ring. ] The bisphenol derivative represented by the following formula has an extremely improved photostability of the cyanine dye, and has a property of being easy to handle and highly safe, and an optical recording medium containing the cyanine dye as the light stabilizer. The present invention has been completed by finding that it is also extremely effective when applied to. That is, the present invention is represented by the general formula (1)
【００１０】[0010]
【化３】 [Chemical 3]
【００１１】〔式中、Ｒ1〜Ｒ4は水素原子またはアルキ
ル基を示し、Ｒ5およびＲ6は水素原子、アルキル基また
はペルフルオロアルキル基を示し、Ｒ5とＲ6はお互いに
結合して環を形成していてもよい。〕で表されるビスフ
ェノール系シアニン色素の光安定化剤及び該光安定化剤
を含有する光記録媒体である。[Wherein R 1 to R 4 represent a hydrogen atom or an alkyl group, R 5 and R 6 represent a hydrogen atom, an alkyl group or a perfluoroalkyl group, and R 5 and R 6 are bonded to each other. It may form a ring. ] A light stabilizer for a bisphenol cyanine dye represented by the following and an optical recording medium containing the light stabilizer.
【００１２】以下、本発明を詳しく説明する。本発明の
一般式（１）（化３）におけるＲ1〜Ｒ4の具体例として
は、水素原子、メチル基、エチル基、ｎ−プロピル基、
ｉ−プロピル基、ｎ−ブチル基、ｉ−ブチル基、ｔ−ブ
チル基、ｎ−ペンチル基、２−メチル−ブチル基、ｎ−
ヘキシル基、２，３−ジメチルブチル基、３，５，５−
トリメチルヘキシル基、ｎ−オクチル基、ｎ−ドデシル
基、ｎ−オクタデシル基などのアルキル基が挙げられ、
またＲ5、Ｒ6の具体例としては、水素原子、メチル基、
エチル基、プロピル基、ｎ−ブチル基等のアルキル基、
トリフルオロメチル基、ペンタフルオロエチル基、ペン
タフルオロプロピル基などのペンタフルオロアルキル
基、およびＲ5とＲ6が結合し、シクロペンタン環、シク
ロヘキサン環、シクロオクタン環を形成した化合物など
を挙げることができる。中でも水酸基のオルト位である
Ｒ1または、Ｒ1およびＲ3にかさ高い置換基であるｔ−
ブチル基を有するビスフェノール誘導体が好ましく用い
られる。本発明の光安定化剤の具体的代表例を第１表
（表１〜２）に示す。これらの光安定化剤は、一種類も
しくは二種類以上の組み合わせによっても使用できる。The present invention will be described in detail below. Specific examples of R 1 to R 4 in the general formula (1) (formula 3) of the present invention include a hydrogen atom, a methyl group, an ethyl group, an n-propyl group,
i-propyl group, n-butyl group, i-butyl group, t-butyl group, n-pentyl group, 2-methyl-butyl group, n-
Hexyl group, 2,3-dimethylbutyl group, 3,5,5-
Alkyl groups such as trimethylhexyl group, n-octyl group, n-dodecyl group, n-octadecyl group, and the like,
Specific examples of R 5 and R 6 include a hydrogen atom, a methyl group,
Alkyl groups such as ethyl group, propyl group, n-butyl group,
Examples include pentafluoroalkyl groups such as trifluoromethyl group, pentafluoroethyl group, pentafluoropropyl group, and compounds in which R 5 and R 6 are bonded to form a cyclopentane ring, a cyclohexane ring, or a cyclooctane ring. it can. Among them, R 1 at the ortho position of the hydroxyl group or t- which is a bulky substituent at R 1 and R 3.
A bisphenol derivative having a butyl group is preferably used. Specific representative examples of the light stabilizer of the present invention are shown in Table 1 (Tables 1 and 2). These light stabilizers can be used alone or in combination of two or more.
【００１３】光安定化剤の使用量はシアニン色素に対し
て、通常、０．０１〜３．０モル比である。さらに３．
０モル比以上を用いてもよいが、シアニン色素の色素濃
度が低くなり、吸光度が低くなるため、用途によっては
不都合を生じる場合がある。また、使用量が少ない場合
には効果が明確でないことがある。一方、光安定化の対
象となるシアニン色素は、特に限定されるものではない
が、下記に示される化合物（Ｃ−１〜Ｃ−２１）（化４
〜化６）が例示される。The amount of the light stabilizer used is usually 0.01 to 3.0 molar ratio with respect to the cyanine dye. Further 3.
Although a molar ratio of 0 or more may be used, the cyanine dye has a low dye concentration and a low absorbance, which may cause inconvenience in some applications. In addition, the effect may not be clear when the amount used is small. On the other hand, the cyanine dye to be light-stabilized is not particularly limited, but the compounds (C-1 to C-21) shown below (chemical formula 4)
[Chemical formula 6] is exemplified.
【００１４】[0014]
【化４】 [Chemical 4]
【００１５】[0015]
【化５】 [Chemical 5]
【００１６】[0016]
【化６】 [Chemical 6]
【００１７】本発明におけるビスフェノール誘導体は、
シアニン色素の薄膜を記録層として用いる光記録媒体中
に光安定化剤として添加使用することができる。これら
の光安定化剤を光記録媒体に適用する場合、色素ととも
に各種溶剤に溶解後、記録媒体の基盤に塗布し薄膜を形
成するなどの方法によって行うことができる。The bisphenol derivative in the present invention is
It can be added and used as a light stabilizer in an optical recording medium using a thin film of a cyanine dye as a recording layer. When these light stabilizers are applied to an optical recording medium, they can be dissolved in various solvents together with the dye and then applied to the base of the recording medium to form a thin film.
【００１８】[0018]
【実施例】以下、本発明を実施例によりさらに詳しく説
明する。実施例における被着色体としては、通常、光記
録媒体の基盤として用いるポリカーボネート板とした
が、ガラスやポリメタアクリレートなどの他の基盤を用
いても同様な結果が得られる。 実施例１ シアニン色素（Ｃ−１）３ｇおよび下記ビスフェノール
化合物（Ａ）（化７）EXAMPLES The present invention will now be described in more detail with reference to examples. A polycarbonate plate used as a base of an optical recording medium is usually used as the colored body in the examples, but similar results can be obtained by using other bases such as glass and polymethacrylate. Example 1 3 g of cyanine dye (C-1) and the following bisphenol compound (A) (Chemical formula 7)
【００１９】[0019]
【化７】 [Chemical 7]
【００２０】２ｇをエタノール１００ｇ中に入れ１時間
室温下で攪拌した後、メンブランフィルター（東洋濾紙
製ＰＴＥＥ，ポアーサイズ１．０μｍ）を用いて濾過
し、色素溶液を得た。本色素溶液をポリカーボネート板
基盤上にスピンコート法によって塗布した。この着色ポ
リカーボネート基盤を耐光試験器（入江製作所製 ＤＲ
４００Ｔ）内で２０ｃｍの距離から光照射した。１０時
間光照射後のシアニン色素の吸収極大波長７１５ｎｍに
おける退色率は１５．１％と良好な結果であった。2 g was put in 100 g of ethanol and stirred for 1 hour at room temperature, and then filtered using a membrane filter (PTEE, Toyo Roshi Kaisha, Ltd., pore size 1.0 μm) to obtain a dye solution. This dye solution was applied onto a polycarbonate plate substrate by spin coating. This colored polycarbonate substrate is a light resistance tester (DR manufactured by Irie Seisakusho).
Light was irradiated from a distance of 20 cm in 400 T). The fading rate at the absorption maximum wavelength of 715 nm of the cyanine dye after irradiation with light for 10 hours was 15.1%, which was a good result.
【００２１】実施例２〜２１ 実施例１と全く同様にして、シアニン色素とビスフェノ
ール化合物の組み合わせを代えて行った。結果を第１表
（表１〜表４）に示すが、いずれも実施例１同様、良好
な結果を得た。Examples 2 to 21 In exactly the same manner as in Example 1, the combination of the cyanine dye and the bisphenol compound was changed. The results are shown in Table 1 (Tables 1 to 4), and as in Example 1, good results were obtained.
【００２２】比較例１ 実施例１において、ビスフェノール化合物を全く添加せ
ずに行ったところ第１表（表４）に示すようにシアニン
色素がかなり分解した。Comparative Example 1 In Example 1, the procedure was carried out without adding any bisphenol compound, and as shown in Table 1 (Table 4), the cyanine dye was considerably decomposed.
【００２３】比較例２ 実施例１において、ビスフェノール化合物（Ａ）（化
７）の代わりに２，６−ジ−ｔ−ブチル−４−メチルフ
ェノールを用いて行ったところ、第１表（表４）に示す
ようにシアニン色素がかなり分解した。Comparative Example 2 In Example 1, 2,6-di-t-butyl-4-methylphenol was used in place of the bisphenol compound (A) (Chemical formula 7), and Table 1 (Table 4) was used. ), The cyanine dye was considerably decomposed.
【００２４】[0024]
【表１】 [Table 1]
【００２５】[0025]
【表２】 [Table 2]
【００２６】[0026]
【表３】 [Table 3]
【００２７】[0027]
【表４】 [Table 4]
【００２８】[0028]
【発明の効果】本発明のビスフェノール系化合物は、取
り扱いが簡単で安全性が高く、しかもシアニン色素に対
する光安定化効果が非常に優れた光安定化剤である。ま
た、近年需要の高い光記録媒体の光安定化剤としても有
効であるので、耐光性に優れた光記録媒体を提供するこ
とができる。INDUSTRIAL APPLICABILITY The bisphenol compound of the present invention is a photostabilizer which is easy to handle and highly safe, and has a very excellent photostabilizing effect on cyanine dyes. Further, since it is also effective as a light stabilizer for an optical recording medium which is in high demand in recent years, it is possible to provide an optical recording medium excellent in light resistance.
Claims (4)
Ｒ5およびＲ6は水素原子、アルキル基またはペルフルオ
ロアルキル基を示し、Ｒ5とＲ6はお互いに結合して環を
形成していてもよい。〕で表されるビスフェノール系シ
アニン色素の光安定化剤。1. General formula (1) (Chemical formula 1) [In the formula, R 1 to R 4 represent a hydrogen atom or an alkyl group,
R 5 and R 6 represent a hydrogen atom, an alkyl group or a perfluoroalkyl group, and R 5 and R 6 may combine with each other to form a ring. ] The light stabilizer of the bisphenol type cyanine dye represented by these.
のシアニン色素の光安定化剤。2. The light stabilizer for a cyanine dye according to claim 1, wherein R 1 is a t-butyl group.
請求項１記載のシアニン色素の光安定化剤。3. The light stabilizer for a cyanine dye according to claim 1, wherein R 1 and R 3 are both t-butyl groups.
表されるビスフェノール系シアニン色素の光安定化剤を
含有する光記録媒体。4. An optical recording medium containing a light stabilizer for a bisphenol cyanine dye represented by the general formula (1) (formula 1) according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27147392A JPH06116555A (en) | 1992-10-09 | 1992-10-09 | Bisphenol-based light stabilizer for cyanine dye and optical recording medium containing the same light stabilizer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27147392A JPH06116555A (en) | 1992-10-09 | 1992-10-09 | Bisphenol-based light stabilizer for cyanine dye and optical recording medium containing the same light stabilizer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH06116555A true JPH06116555A (en) | 1994-04-26 |
Family
ID=17500529
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27147392A Pending JPH06116555A (en) | 1992-10-09 | 1992-10-09 | Bisphenol-based light stabilizer for cyanine dye and optical recording medium containing the same light stabilizer |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH06116555A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001010805A1 (en) * | 1999-08-03 | 2001-02-15 | Daikin Industries, Ltd. | Bis(4-hydroxy-3-perfluoroalkylphenyl)fluoroalkane derivatives and process for the preparation thereof |
| US20120165575A1 (en) * | 2008-07-30 | 2012-06-28 | Sk Energy Co., Ltd. | Novel coordination complexes and process of producing polycarbonate by copolymerization of carbon dioxide and epoxide using the same as catalyst |
-
1992
- 1992-10-09 JP JP27147392A patent/JPH06116555A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001010805A1 (en) * | 1999-08-03 | 2001-02-15 | Daikin Industries, Ltd. | Bis(4-hydroxy-3-perfluoroalkylphenyl)fluoroalkane derivatives and process for the preparation thereof |
| US20120165575A1 (en) * | 2008-07-30 | 2012-06-28 | Sk Energy Co., Ltd. | Novel coordination complexes and process of producing polycarbonate by copolymerization of carbon dioxide and epoxide using the same as catalyst |
| US8507733B2 (en) * | 2008-07-30 | 2013-08-13 | Sk Innovation Co., Ltd. | Coordination complexes and process of producing polycarbonate by copolymerization of carbon dioxide and epoxide using the same as catalyst |
| TWI448467B (en) * | 2008-07-30 | 2014-08-11 | Sk Innovation Co Ltd | Novel coordination complexes and process of producing polycarbonate by copolymerization of carbon dioxide and epoxide using the same as catalyst |
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