JPH049829B2 - - Google Patents
Info
- Publication number
- JPH049829B2 JPH049829B2 JP62163992A JP16399287A JPH049829B2 JP H049829 B2 JPH049829 B2 JP H049829B2 JP 62163992 A JP62163992 A JP 62163992A JP 16399287 A JP16399287 A JP 16399287A JP H049829 B2 JPH049829 B2 JP H049829B2
- Authority
- JP
- Japan
- Prior art keywords
- mol
- fulgide
- film
- added
- photochromic
- 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 - Lifetime
Links
- 239000000463 material Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 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 17
- 239000010408 film Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000010409 thin film Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- 238000003756 stirring Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- -1 diethyl succinate anhydride Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010898 silica gel chromatography 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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000001165 hydrophobic group Chemical group 0.000 description 2
- 150000003949 imides Chemical group 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 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
- 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
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-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
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- WFLJHDLVVWUGGZ-UHFFFAOYSA-N triacontan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCN WFLJHDLVVWUGGZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/72—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705
- G03C1/73—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705 containing organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (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 FIELD OF THE INVENTION This 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
ミツク材料の一としてフルギドが挙げられる。式
(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. formula
(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R1〜R4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。その一つとして式(2)のフルギドを例としてそ
のフオトクロミズムについて簡単に説明する。式
(2)のフルギドは、芳香環としてフラン環を用いた
もので、無色である。このフルギド(2)に337nｍ
の紫外光をあてると、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 R1 to R4 is an aromatic ring, X=O, N-R) Many fulgides have been announced so far. As one example, fulgide of formula (2) will be used as an example to briefly explain its photochromism. formula
Fulgide (2) uses a furan ring as an aromatic ring and is colorless. 337nm to this fulgide (2)
When exposed to ultraviolet light, it changes to the benzofuran form (3) and exhibits a red color. When exposed to visible light of 473 nm, it returns to (2) again.
なお、こようなフオトクロミズムは、他のフル
ギドについても、吸収波長が異なるだけで、ほぼ
共通している。 Note that this kind of photochromism is almost common to other fulgides, with the only difference being the absorption wavelength.
エレクトロニクス部品の小型化、高性能化に伴
い、このフオトクロミツク特性の光記録媒体、光
量子検知素子などへの応用を考えた場合、フルギ
ドを均一超薄膜化しなければならない。 As electronic components become smaller and more sophisticated, it is necessary to make fulgide into a uniform ultra-thin film in order to apply this photochromic property to optical recording media, photon detection devices, etc.
LB（ラングミユアブロジエツト）膜は、代表的
な有機化合物の均一超薄膜である。LB膜を形成
するためには、分子の中に、疎水性を有する基
（例えば、炭化水素鎖）及び、親水性を有する基
（例えば、カルボニル基）を含みしかも両者が、
適度なバランスを持つことが必要である。 LB (Langmiur Blossom) film is a uniform ultra-thin film made of a typical organic compound. In order to form an LB film, the molecule must contain a hydrophobic group (e.g., a hydrocarbon chain) and a hydrophilic group (e.g., a carbonyl group), and both of them must be
It is necessary to have an appropriate balance.
発明が解決しようとする問題点
従来のイミド環を有するフルギドは疎水基を有
しないか、有したとしても親水基とのバランスが
悪いため、LB膜の形成が困難であつた。Problems to be Solved by the Invention Conventional fulgide having an imide ring does not have a hydrophobic group, or even if it does have it, the balance with the hydrophilic group is poor, making it difficult to form an LB 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＝５〜30のアルキル鎖）
作 用
上記フオトクロミツク材料は、イミド環を有す
るフルギドの中において置換基の位置と場所を特
定した特別な材料である。本構成をとることによ
り、疎水性のないフルギド骨格に適当な疎水性を
付与することが可能であるため、フオトクロミツ
ク特性を全く損わない、均一な超薄膜（LB膜）
を得ることが可能である。(However, R is an alkyl chain with C=5 to 30) Function The above photochromic material is a special material in which the positions and locations of substituents in fulgide having an imide ring are specified. By adopting this configuration, it is possible to impart appropriate hydrophobicity to the non-hydrophobic fulgide skeleton, resulting in a uniform ultra-thin film (LB film) that does not impair photochromic properties at all.
It is possible to obtain
実施例
本発明におけるフルギドの一例（以下FF−N1
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 FF-N1
It is called. ) is shown below.
（ステツプ１）
２、５−ジメチルフラン１モルと無水酢酸1.5
モルのベンゼン溶液に、０℃で無水塩化すず
（）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（1.5Kg）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) 1 mol of 2,5-dimethylfuran and 1.5 mol of acetic anhydride
A 1 mol benzene solution of anhydrous tin chloride () was added to the 1 mol benzene solution at 0° C. over a period of 1 hour. After stirring for several hours, add ice (1.5 kg) and
Pour 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）
水素化ナトリムウ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
グネシムウで乾燥、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. 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 further stirred. After 1 hour, the reaction mixture was diluted with ethyl acetate and carefully acidified by extraction with 1M aqueous sodium carbonate to liberate the organic layer. It was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and concentrated to give a half ester of 0.8
Got a mole.
（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、農硫酸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 agricultural 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）
水素化ナトリムウ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
した後、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。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分間撹拌した。次に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。得られた酸無水物は、Ｅ体とＺ体
の混合物であつた。この混合物を、再結晶によつ
て分離し、フオトクロミズムを示すＥ体酸無水物
0.05モルを得た。 (Step 5) 0.5 mol of the obtained half ester was dissolved in 5% alcoholic potassium hydroxide and heated under reflux for 15 hours, then poured into 6N hydrochloric acid and extracted with ethyl acetate.
By drying and concentrating over anhydrous sodium sulfate, 0.3 mol of dicarboxylic acid was obtained. Add 100 ml of acetyl chloride to 0.3 mol of this dicarboxylic acid and let it cool at room temperature.
Stir for 10 minutes. Next, the reaction mixture was concentrated, and the residue was separated and purified using silica gel column chromatography. The obtained acid anhydride was a mixture of E-form and Z-form. This mixture was separated by recrystallization to form an E acid anhydride exhibiting photochromism.
0.05 mol was obtained.
（ステツプ６）
酸無水物0.1モルとオクタデシルアミン0.3モル
をピリジン20mlに溶かし、50℃に加熱して30分か
くはんする。反応終了後、ピリジンを留去し、残
査をシリカゲルカラムクロマトグラフイーを用い
て分離精製することにより、アミドカルボン酸
0.09モルを得た。 (Step 6) Dissolve 0.1 mol of acid anhydride and 0.3 mol of octadecylamine in 20 ml of pyridine, heat to 50°C, and stir for 30 minutes. After the reaction is complete, pyridine is distilled off and the residue is separated and purified using silica gel column chromatography to obtain the amide carboxylic acid.
0.09 mol was obtained.
（ステツプ７）
アミドカルボン酸0.09モルを塩化アセチルのジ
エチルエーテル溶液に加え、10分間かくはんし
た。炭端水素カルシム水溶液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。更に純度を上げるため、メタノ
ールからの再結晶を１回、ヘキサンからの再結晶
を２回行うことによつて、目的のフルギド0.08モ
ルを得た。 (Step 7) 0.09 mol of amidocarboxylic acid was added to the diethyl ether solution of acetyl chloride and stirred for 10 minutes. The mixture was poured into an aqueous solution of calcium carbonate hydrogen, extracted with ethyl acetate, dried over anhydrous sodium sulfate, concentrated, and the residue was separated and purified using silica gel column chromatography. In order to further increase the purity, 0.08 mol of the desired fulgide was obtained by recrystallizing once from methanol and twice from hexane.
以上の方法で合成したフルギドFF−N1を気水
界面に展開し、石英基板に累積することによつ
て、膜厚が100Aの均一超薄膜（LB膜）を得るこ
とができた。この超薄膜は、良好なフオトクロミ
ツク特性を示した。 By spreading the fulgide FF-N1 synthesized using the above method at the air-water interface and accumulating it on a quartz substrate, we were able to obtain a uniform ultra-thin film (LB film) with a film thickness of 100A. This ultra-thin film showed good photochromic properties.
なお、LB膜形成には、オクタデシルアミンを
用いた本実施例がもつとも望ましい。さらに、Ｒ
において、炭素数が14から22の場合、良好なLB
膜を形成し、その膜は良好なフオトクロミツク特
性を示した。 Note that this embodiment using octadecylamine is also desirable for forming the LB film. Furthermore, R
, good LB when carbon number is 14 to 22
A film was formed and the film showed good photochromic properties.
オクタデシルアミンのかわりにベンチルアミン
を用いて、同様の方法でフルギドを合成したとこ
ろ、LB膜を得ることができた（ＲはＣ＝５の炭
素鎖）。しかし、ブチルアミンを用いたフルギド
では、親水性と疎水性のバランスが悪いために、
LB膜を得ることができなかつた。 When fulgide was synthesized in a similar manner using benzylamine instead of octadecylamine, an LB film could be obtained (R is a carbon chain with C=5). However, fulgide using butylamine has an unbalanced hydrophilicity and hydrophobicity.
It was not possible to obtain an LB film.
さらに、オクタデシルアミンの代りにトリアコ
ンチルアミンを用いて、同様の方法でフルギドを
合成したところ、LB膜を得ることができ、その
膜は、フオトクロミツク特性を示した（ＲはＣ＝
30の炭素鎖）。しかし、それ以上の長鎖の化合物
については、原料のアミンを得るこのが困難であ
る。 Furthermore, when fulgide was synthesized in a similar manner using triacontylamine instead of octadecylamine, an LB film could be obtained, and the film showed photochromic properties (R is C=
30 carbon chains). However, for compounds with longer chains than this, it is difficult to obtain the raw material amine.
発明の効果
本発明によつて、フルギドの有するフオトクロ
ミツク特性を失うことなく、LB法による超薄膜
の提供が可能となり、その波及効果は大である。Effects of the Invention The present invention makes it possible to provide ultra-thin films by the LB method without losing the photochromic properties of fulgide, and its ripple effects are significant.
Claims (1)
料。 （ただしＲはＣ＝５〜30のアルキル鎖） [Claims] 1. A photochromic material represented by the following general formula. (However, R is an alkyl chain with C=5 to 30)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16399287A JPS649282A (en) | 1987-07-02 | 1987-07-02 | Photochromic material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16399287A JPS649282A (en) | 1987-07-02 | 1987-07-02 | Photochromic material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS649282A JPS649282A (en) | 1989-01-12 |
| JPH049829B2 true JPH049829B2 (en) | 1992-02-21 |
Family
ID=15784703
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16399287A Granted JPS649282A (en) | 1987-07-02 | 1987-07-02 | Photochromic material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS649282A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5644416A (en) * | 1991-11-26 | 1997-07-01 | Fuji Xerox Co., Ltd. | Light modulation device and method of light modulation using the same |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5331656A (en) * | 1976-08-31 | 1978-03-25 | Heller Harold G | Photochrome compound |
-
1987
- 1987-07-02 JP JP16399287A patent/JPS649282A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5331656A (en) * | 1976-08-31 | 1978-03-25 | Heller Harold G | Photochrome compound |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS649282A (en) | 1989-01-12 |
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