JPH0314878B2 - - Google Patents
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- Publication number
- JPH0314878B2 JPH0314878B2 JP10897987A JP10897987A JPH0314878B2 JP H0314878 B2 JPH0314878 B2 JP H0314878B2 JP 10897987 A JP10897987 A JP 10897987A JP 10897987 A JP10897987 A JP 10897987A JP H0314878 B2 JPH0314878 B2 JP H0314878B2
- Authority
- JP
- Japan
- Prior art keywords
- mol
- fulgide
- added
- concentrated
- chloride
- 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.)
- Expired
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- 239000000463 material Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- GSNUFIFRDBKVIE-UHFFFAOYSA-N 2,5-dimethylfuran Chemical compound CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-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
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- -1 diethyl succinate anhydride Chemical class 0.000 description 1
- SXGUHJLRKQCPBN-UHFFFAOYSA-N dotriacontanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(Cl)=O SXGUHJLRKQCPBN-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
Landscapes
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Description
【発明の詳細な説明】 産業上の利用分野 本発明はフオトクロミツク材料に関する。[Detailed description of the invention] Industrial applications The present invention relates to photochromic materials.
従来の技術
従来、可逆的な色の変化を生ずる材料としてフ
オトクロミツク材料が知られている。フオトクロ
ミツ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
ている化合物である。BACKGROUND ART Conventionally, photochromic materials have been known as materials that produce reversible color changes. Fulgide is one of the photochromic materials.
(1) is the general formula of fulgide. In other words, fulgide is a compound in which alkylidene groups are attached to each of the two methylene carbons of succinic anhydride or its derivatives.
（ただしR2，R3のうち少なくとも一つは芳香環、
Ｘ＝Ｏ、Ｎ−Ｒ）
現在までに数多くのフルギドが発表されてい
る。例えば下記のフルギド（２）に337nmの紫外
光を照射すると、ベンゾフラン形（３）に変化
し、赤色を呈する。473nmの可視光をあてると再
び（２）に戻る。 (However, at least one of R 2 and R 3 is an aromatic ring,
X=O, N-R) Many fulgides have been announced so far. For example, when fulgide (2) shown below is irradiated with 337 nm ultraviolet light, it changes to benzofuran form (3) and exhibits a red color. When exposed to visible light of 473 nm, it returns to (2) again.
これらの性質を用いて、フルギドの光記憶媒
体、光エネルギー変換素子などへの応用研究が行
われている。 Using these properties, research is being carried out to apply fulgide to optical storage media, optical energy conversion devices, etc.
発明が解決しようとする問題点
フルギドを光記録媒体として利用するとき、着
色体の吸収波長の異なるフルギドが必要とされ
る。しかしながら、従来は、着色体の吸収極大波
長が、470nm以下（ヘキサン中）のものは見いだ
されていない。Problems to be Solved by the Invention When fulgides are used as optical recording media, fulgides with different absorption wavelengths of colored bodies are required. However, so far, no colored material has been found that has a maximum absorption wavelength of 470 nm or less (in hexane).
問題点を解決するための手段 下記一般式で示されるフオトクロミツク材料。Means to solve problems A photochromic material represented by the general formula below.
（ただしＲはＣ＝１〜31のアルキル基）
作 用
上記の構成をとることにより、フルギドの優れ
た記録特性を保持し、かつ、従来のフルギドより
も、着色体の吸収極大波長を短波長にすることが
可能となる。(However, R is an alkyl group with C=1 to 31) Effect By adopting the above configuration, it is possible to maintain the excellent recording properties of fulgide and to make the maximum absorption wavelength of the colored body shorter than that of conventional fulgide.
実施例
本発明におけるフルギドの一例（以下FaF−
1Oと称する。）の化学構造式を以下に示す。Example An example of fulgide in the present invention (hereinafter FaF-
It is called 1O. ) is shown below.
FaF−1Oの合成法を以下に示す。 The synthesis method of FaF-1O is shown below.
（ステツプ １）
２、５−ジメチルフラン１モルと塩化ステアロ
イル1.5モルのベンゼン溶液に、０℃で無水塩化
すず（IV）１モルのベンゼン溶液を、１時間か
けて加えた。数時間かくはんしたのち、氷（1.5
Kg）と、5Mの塩酸（500ml）にあけた。水層を酢
酸エチルで抽出し、あわせた有機層を水で洗浄
し、濃縮した。メタノールから再結晶することに
よつて、ケトフラン0.8モルを得た。(Step 1) To a benzene solution of 1 mol of 2,5-dimethylfuran and 1.5 mol of stearoyl chloride was added a benzene solution of 1 mol of anhydrous tin (IV) chloride over 1 hour at 0°C. After stirring for several hours, add ice (1.5
Kg) and poured into 5M hydrochloric acid (500ml). The aqueous layer was extracted with ethyl acetate, and the combined organic layers were washed with water and concentrated. 0.8 mol of ketofuran was obtained by recrystallization from methanol.
（ステツプ ２）
水素化ナトリウム１モルに石油エーテルを加
え、５分間かくはんした。静置して上澄みを除い
た後、アセトン1.5モルと無水こはく酸ジエチル
１モルの混合物を加えた。そこへエタノールを１
滴加えると反応が始まり、激しく水素が発生し
た。水素発生がおさまつたのち、ジエチルエーテ
ルを加え更にかくはんした。１時間後反応混合物
を酢酸エチルで薄め、1Mの炭酸ナトリウム水溶
液で抽出して注意深く酸性にすると、有機層が遊
離してきた。それを酢酸エチルで抽出し、無水硫
酸マグネシウムで乾燥、濃縮してハーフエステル
0.8モルを得た。 (Step 2) Petroleum ether was added to 1 mol of sodium hydride and stirred for 5 minutes. After standing still and removing the supernatant, a mixture of 1.5 mol of acetone and 1 mol of diethyl succinate anhydride was added. Add 1 ethanol to it
When added dropwise, the reaction started and hydrogen was violently evolved. After hydrogen generation had subsided, diethyl ether was added and further stirred. After 1 hour, the reaction mixture was diluted with ethyl acetate and carefully acidified by extraction with 1M aqueous sodium carbonate solution to liberate the organic layer. It was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and concentrated to form a half ester.
0.8 mol was obtained.
（ステツプ ３）
ステツプ２で得たハーフエステル0.8モルをエ
タノール500mlに溶かし、濃硫酸50mlを加えて加
熱還流した。３時間後濃縮し、残査をエーテルで
薄めたものを炭酸水素ナトリウム水溶液で洗浄し
て、再び乾燥、濃縮した。得られた残査をカラム
クロマトグラフイーで分取することによつてジエ
ステル0.8モルを得た。 (Step 3) 0.8 mol of the half ester obtained in Step 2 was dissolved in 500 ml of ethanol, 50 ml of concentrated sulfuric acid was added, and the mixture was heated to reflux. After 3 hours, it was concentrated, and the residue was diluted with ether, washed with an aqueous sodium bicarbonate solution, dried and concentrated again. The resulting residue was fractionated by column chromatography to obtain 0.8 mol of diester.
（ステツプ ４）
水素化ナトリウム1.2モルに石油エーテルを加
え５分間かくはんした。静置して上澄みを除いた
後、ステツプ１で得たケトフラン0.8モルと、ス
テツプ３で得たジエステル0.8モルの混合物を、
できるだけ少量の石油エーテルに溶かして加え
た。そこへエタノールを１滴加えると反応が始ま
り、激しく水素が発生した。水素発生がおさまつ
たのち、ジエチルエーテルを加え更にかくはんを
続けた。１時間後反応混合物を酢酸エチルで薄
め、1Mの炭酸ナトリウム水溶液で抽出して注意
深く酸性にすると、有機層が遊離してきた。それ
を酢酸エチルで抽出し、無水硫酸マグネシウムで
乾燥、濃縮した。得られた残査をカラムクロマト
グラフイーで分取することによつて、ハーフエス
テル0.5モルを得た。 (Step 4) Petroleum ether was added to 1.2 mol of sodium hydride and stirred for 5 minutes. After leaving to stand still and removing the supernatant, add a mixture of 0.8 mol of ketofuran obtained in step 1 and 0.8 mol of diester obtained in step 3.
It was dissolved in as little petroleum ether as possible and added. When one drop of ethanol was added thereto, the reaction started and hydrogen was violently generated. After hydrogen generation had subsided, diethyl ether was added and stirring was continued. After 1 hour, the reaction mixture was diluted with ethyl acetate and carefully acidified by extraction with 1M aqueous sodium carbonate solution to liberate the organic layer. It was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was fractionated by column chromatography to obtain 0.5 mol of half ester.
（ステツプ ５）
得られたハーフエステル0.5モルを５％アルコ
ール性水酸化カリウムに溶かして15時間加熱還流
したのち、6N塩酸にあけて酢酸エチルで抽出し
無水硫酸ナトリウムで乾燥、濃縮することによ
り、ジカルボン酸0.3モルを得た。さらにこのジ
カルボン酸0.3モルに塩化アセチル100mlを加え、
室温で10分間かくはんした。その後反応混合物を
濃縮し、残査をシリカゲルカラムクロマトグラフ
イーを用いて分離精製した後、メタノールから再
結晶をすることによつて、酸無水物0.1モルを得
た。 (Step 5) 0.5 mol of the obtained half ester was dissolved in 5% alcoholic potassium hydroxide, heated under reflux for 15 hours, poured into 6N hydrochloric acid, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and concentrated. 0.3 mol of dicarboxylic acid was obtained. Furthermore, 100 ml of acetyl chloride was added to 0.3 mol of this dicarboxylic acid,
Stir for 10 minutes at room temperature. Thereafter, the reaction mixture was concentrated, and the residue was separated and purified using silica gel column chromatography, and then recrystallized from methanol to obtain 0.1 mol of acid anhydride.
（ステツプ ６）
酸無水物0.1モルと塩化アセチル0.1モルのベン
ゼン溶液に、塩化すず0.21モルのベンゼン溶液を
加え、室温で１時間かくはんした。氷（0.5Kg）
と、5Mの塩酸（100ml）にあけ、水層を酢酸エチ
ルで抽出し、あわせた有機層を水で洗浄、濃縮
し、カラムクロマトグラフイーで粗精製したの
ち、メタノールから再結晶を２回行うことによつ
て、目的のフルギドFaF−1Oを0.05モル得た。 (Step 6) A benzene solution of 0.21 mol of tin chloride was added to a benzene solution of 0.1 mol of acid anhydride and 0.1 mol of acetyl chloride, and the mixture was stirred at room temperature for 1 hour. Ice (0.5Kg)
Pour into 5M hydrochloric acid (100ml), extract the aqueous layer with ethyl acetate, wash the combined organic layers with water, concentrate, roughly purify by column chromatography, and recrystallize twice from methanol. As a result, 0.05 mol of the desired fulgide FaF-1O was obtained.
以上の方法で合成したフルギドFaF−1Oのヘ
キサン溶液の紫外可視吸収スペクトルを図の曲線
Ａに示す。この溶液にλ＝280nmの紫外光を照射
すると、閉環して黄色に着色した。この紫外可視
吸収スペクトルを第１図の曲線Ｂに示す。さらに
λ＝450nmの可視光を照射すると、再び開環して
無色形に戻つた。着色体の吸収極大値は、従来の
フルギドよりも短波長に吸収極大を持つている。 Curve A in the figure shows the ultraviolet-visible absorption spectrum of a hexane solution of fulgide FaF-1O synthesized by the above method. When this solution was irradiated with ultraviolet light of λ=280 nm, the ring was closed and colored yellow. This ultraviolet-visible absorption spectrum is shown as curve B in FIG. When further irradiated with visible light of λ = 450 nm, the ring opened again and returned to the colorless form. The absorption maximum value of the colored material is at a shorter wavelength than that of conventional fulgide.
なお、塩化ステアロイルの代わりに塩化ドトリ
アコンタノイルを用いて、同様の方法でフルギド
を合成したところ、着色体の吸収極大波長がほぼ
同じフルギドが得られた。（Ｃ＝31）。しかし、そ
れ以上の長鎖の化合物については、原料の酸塩化
物を得るのが困難である。 When fulgide was synthesized in a similar manner using dotriacontanoyl chloride instead of stearoyl chloride, fulgide with almost the same maximum absorption wavelength of the colored body was obtained. (C=31). However, for compounds with longer chains than this, it is difficult to obtain the raw acid chloride.
さらに、塩化ステアロイルの代わりに、塩化ア
セチルを用いて同様の方法でフルギドを合成した
ところ、着色体の吸収極大波長がほぼ同じフルギ
ドが得られた。この様に、アルキル鎖による影響
は見られなかつた。 Furthermore, when fulgide was synthesized in a similar manner using acetyl chloride instead of stearoyl chloride, fulgide with almost the same maximum absorption wavelength of the colored body was obtained. Thus, no influence by the alkyl chain was observed.
発明の効果
本発明により、吸収波長が短波長のフルギドの
提供が可能になり、その波乃効果は大である。Effects of the Invention According to the present invention, it is possible to provide fulgide whose absorption wavelength is short, and its wave effect is large.
１図は、本発明の実施例で用いたフルギド
（FaF−1O）と、その有色形のヘキサン中におけ
る紫外可視吸収スペクトル図である。
FIG. 1 is an ultraviolet-visible absorption spectrum diagram of fulgide (FaF-1O) used in an example of the present invention and its colored form in hexane.
Claims (1)
料。 （ただしＲはＣ＝１〜31のアルキル基） [Claims] 1. A photochromic material represented by the following general formula. (However, R is an alkyl group with C=1 to 31)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10897987A JPS63273688A (en) | 1987-05-06 | 1987-05-06 | Photochromic material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10897987A JPS63273688A (en) | 1987-05-06 | 1987-05-06 | Photochromic material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63273688A JPS63273688A (en) | 1988-11-10 |
| JPH0314878B2 true JPH0314878B2 (en) | 1991-02-27 |
Family
ID=14498503
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10897987A Granted JPS63273688A (en) | 1987-05-06 | 1987-05-06 | Photochromic material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63273688A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2763263B2 (en) * | 1992-12-31 | 1998-06-11 | 第一合纖株式會社 | Optical recording medium |
-
1987
- 1987-05-06 JP JP10897987A patent/JPS63273688A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63273688A (en) | 1988-11-10 |
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