JPH0481998B2 - - Google Patents
Info
- Publication number
- JPH0481998B2 JPH0481998B2 JP60012192A JP1219285A JPH0481998B2 JP H0481998 B2 JPH0481998 B2 JP H0481998B2 JP 60012192 A JP60012192 A JP 60012192A JP 1219285 A JP1219285 A JP 1219285A JP H0481998 B2 JPH0481998 B2 JP H0481998B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- alkyl group
- group
- solvent
- 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
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 150000004893 oxazines Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 21
- 239000000463 material Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
- YXAOOTNFFAQIPZ-UHFFFAOYSA-N 1-nitrosonaphthalen-2-ol Chemical class C1=CC=CC2=C(N=O)C(O)=CC=C21 YXAOOTNFFAQIPZ-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012769 display material Substances 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000000873 masking effect Effects 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 108091008695 photoreceptors Proteins 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- -1 p-toluenesulfonic acid ester Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- G03C1/685—Compositions containing spiro-condensed pyran compounds or derivatives thereof, as photosensitive substances
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)
- Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Description
〔産業上の利用分野〕
本発明は、新規な3,3−ジメチル−スピロ
〔インドリノー2,3′−ナフト〔2,1−b〕
(1,4)オキサジン〕
誘導体に関するものである。
詳しくは、各種の記録・記憶材料、複写材料、
印刷感光体、レーザー用感光材料、写真植写用感
光材料あるいは光学フイルター、マスキング用材
料、光量計、デイスプレイ用材料として使用し得
るフオトクロミツク性を有する新規な化合物に関
するものである。
〔従来の技術〕
スピロナフトオキサジン化合物が光の照射によ
り発色又は消色するフオトクロミツク性を有する
ことは知られており、それを使用したフオトクロ
ミツク感光材料が種々提案されている。
例えば、特公昭45−28892号には、次式の様な
スピロナフトオキサジン系化合物を含有するフオ
トクロミツク材料が提案されている。
(式中、Raは水素原子、ハロゲン原子、シアン
基、炭素数1〜8のアルキル基またはアルコキシ
基を示す。)
また、特公昭49−48631号には、次式の様なス
ピロナフトオキサジン系化合物を高分子物質中に
分散させたフオトクロミツク感光材料が提案され
ている。
(式中、Rbは―(CH2)―oCOOH、―(CH2)―oCNま
たは―(CH2)―oCOOR(Rは炭素数1〜5のアルキ
ル基);RcおよびRdは炭素数1〜5のアルキル
基;Reは水素原子、炭素数1〜5個のアルキル
基、ハロゲン原子、ニトロ基、シアノ基、炭素数
2〜6個のアルコキシカルボニル基または炭素数
1〜5個のアルコキシ基を示す。)
また、特開昭55−36284号には、次式の様なフ
オトクロミツク化合物が提案されている。
(式中、RfとRgの一つはハロゲン又は低級アル
コキシで他の一つは水素、又RhとRiは水素、低
級アルキル、低級アルコキシ、又はハロゲンを示
す。)
また、U.S.P.4342668には、次式の様なフオト
クロミツク化合物が提案されている。
(式中、RjとRkの一つはハロゲン又は低級アル
コキシで、他の一つは水素、またRlとRmは水素、
低級アルキル、低級アルコキシ、又はハロゲンを
示し、Rnは炭素数2から10までのアルキル基を
示す。)
近年、有機超薄膜に対する関心が高揚しつつあ
り、このような薄膜の一つとして、特に、ラング
ミユア膜が注目されている。ラングミユア膜の作
製法は単分子累積法とも言い、水面上に形成した
単分子膜を固体表面に1枚ずつ重ねて超薄膜を作
る方法であるが、最近、フオトクロミツク化合物
を使用し、このようなラングミユア膜による有機
超薄膜を作製することが検討されている。
〔従来技術の問題点〕
しかし、上述の様な従来のスピロナフトオキサ
ジン化合物の場合、上記の手法を用い、紫外線照
射下、製膜するも十分な膜が得られない。
〔問題点を解決するための手段〕
すなわち、本発明は、一般式〔〕
(式中、R1はC16〜24のアルキル基を示し、R2、
R3、R4、R5は水素原子、ハロゲン原子、アルキ
ル基、アルコキシ基またはアルコキシカルボニル
基を示す。)
で表わされる3,3−ジメチル−スピロ〔インド
リノー2,3′−ナフト〔2,1−b〕(1,4)
オキサジン〕誘導体を要旨とする。
本発明のスピロナフトオキサジン化合物は前記
一般式〔〕で表わされるものである。
式中、R2、R3、R4、R5は水素原子;塩素原
子、臭素原子、ヨウ素原子等のハロゲン原子;
C1〜6のアルキル基等のアルキル基;C1〜6のアル
コキシ基等のアルコキシ等、または、C1〜6のア
ルコキシカルボニル基等のアルコキシカルボニル
基を示す。
本発明の化合物は、例えば、次のようにして製
造することができる。すなわち、下記一般式
〔〕
(式中、R2及びR3は前記定義に同じ。)で表わさ
れる2,3,3−トリメチルインドレニン誘導体
に下記一般式〔〕
(式中、R1は前記定義に同じ。)で表わされるp
−トルエンスルホン酸エステル類あるいは下記一
般式〔〕
X−R1 ……〔〕
(式中、R1は前記定義に同じ。Xはハロゲン原
子を示す。)で表わされるアルキルハライド類を
反応させ、次いで下記一般式〔〕
(式中、R4及びR5は前記定義に同じ。)で表わさ
れる1−ニトロリ−2−ナフトール誘導体を反応
させることによつて製造することができる。
p−トルエンスルホン酸エステルあるいはアル
キルハライドによるアルキル化反応は無溶媒ある
いはクロロベンゼン、ジクロロベンゼンなどの芳
香族系溶媒などの非極性溶媒中、80〜200℃の反
応温度で実施される。好ましくは無溶媒で130〜
150℃で円滑に実施できる。
次いで、1−ニトロソ−2−ナフトール誘導体
との反応は、ピペリジン、ピペラジン、モルホリ
ン等の塩基性触媒の存在下、メタノール、エタノ
ール、プロパノール、ブタノールなどのアルコー
ル系溶媒、アセトン、メチルエチルケトンなどの
ケトン系溶媒、ジクロロメタン、トリクロロエタ
ンなどのハロゲン化炭化水素系溶媒などの極性又
は非極性の溶媒の存在下に実施される。反応温度
は0〜200℃の範囲で実施される。好ましくは、
エタノール、メチルエチルケトン、アセトン中、
ピペリジン触媒の存在下40℃〜120℃で円滑に実
施できる。
本発明の化合物は、例えば、次のようにしても
製造することができる。すなわち、下記一般式
〔〕
(式中、R1、R2及びR3は前記定義に同じ。)で表
わされる化合物と下記一般式〔〕
(式中、R4及びR5は前記定義に同じ。)で表わさ
れる1−ニトロリ−2−ナフトール誘導体を反応
させることによつて製造することができる。
反応は通常、メタノール、エタノール、プロパ
ノール、ブタノールなどのアルコール系溶媒、ア
セトン、メチルエチルケトンなどのケトン系溶
媒、ジクロロメタン、トリクロロエタンなどのハ
ロゲン化炭化水素系溶媒などの極性又は非極性溶
媒の存在下に実施される。反応温度は、0℃〜
200℃の範囲で実施され、好ましくは、40℃〜120
℃で円滑に実施できる。
〔作用〕
本発明のスピロナフトオキサジン化合物は、上
記一般式〔〕において、Nの置換基として長鎖
のアルキル基(C16〜C24)を有するため、良好な
発色濃度を示し、またラングミユア膜の作製法に
おいて製膜性にすぐれ、そしてフオトクロミツク
性の良好な有機超薄膜を作成することができる。
〔実施例〕
次に、本発明を実施例により、更に具体的に説
明する。
実施例 1
下記構造式
で表わされる化合物21.6gに、下記構造式
で表わされる化合物1−ニトロソ−2−ナフトー
ル7gおよびエタノール100mlを加え、更にトリ
エチルアミン4gを加えた後、窒素雰囲気下2時
間撹拌反応させた。冷却後、溶媒を留去し、カラ
ムクロマトグラフイー(使用溶媒ベンゼン:n−
ヘキサン=1:1)で分離・精製し、融点64〜66
℃の無色の結晶を得た。元素分析結果も下記第1
表の通り、計算値とよく合致した。
[Industrial Application Field] The present invention relates to a novel 3,3-dimethyl-spiro[indolino-2,3'-naphtho[2,1-b]
(1,4) Oxazine] This relates to derivatives. For details, see various recording/memory materials, copying materials,
The present invention relates to a novel compound having photochromic properties that can be used as a printing photoreceptor, a light-sensitive material for lasers, a light-sensitive material for photosetting, an optical filter, a masking material, a photometer, and a display material. [Prior Art] It is known that spironaphthoxazine compounds have photochromic properties that develop or discolor when irradiated with light, and various photochromic light-sensitive materials using them have been proposed. For example, Japanese Patent Publication No. 45-28892 proposes a photochromic material containing a spironaphthoxazine compound as shown in the following formula. (In the formula, R a represents a hydrogen atom, a halogen atom, a cyan group, an alkyl group having 1 to 8 carbon atoms, or an alkoxy group.) In addition, in Japanese Patent Publication No. 49-48631, spironaphthoxazines such as the following formula are described. Photochromic light-sensitive materials have been proposed in which a type compound is dispersed in a polymeric substance. (In the formula, R b is -(CH 2 ) - o COOH, - (CH 2 ) - o CN or - (CH 2 ) - o COOR (R is an alkyl group having 1 to 5 carbon atoms); R c and R d is an alkyl group having 1 to 5 carbon atoms; R e is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a halogen atom, a nitro group, a cyano group, an alkoxycarbonyl group having 2 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms; 5 alkoxy groups) Further, in JP-A-55-36284, a photochromic compound as shown in the following formula is proposed. (In the formula, one of R f and R g is halogen or lower alkoxy and the other is hydrogen, and R h and R i represent hydrogen, lower alkyl, lower alkoxy, or halogen.) A photochromic compound of the following formula has been proposed. (In the formula, one of R j and R k is halogen or lower alkoxy, the other is hydrogen, and R l and R m are hydrogen,
It represents lower alkyl, lower alkoxy, or halogen, and R n represents an alkyl group having 2 to 10 carbon atoms. ) In recent years, interest in organic ultra-thin films has been increasing, and Langmiur films are attracting particular attention as one such thin film. The Langmiur film production method is also called the monomolecular accumulation method, and is a method in which a monomolecular film formed on a water surface is layered one by one on a solid surface to create an ultra-thin film. The fabrication of ultra-thin organic films using Langmiur films is being considered. [Problems with the Prior Art] However, in the case of the conventional spironaphthoxazine compound as described above, even if a film is formed using the above method under ultraviolet irradiation, a sufficient film cannot be obtained. [Means for Solving the Problems] That is, the present invention solves the general formula [] (In the formula, R 1 represents a C 16-24 alkyl group, R 2 ,
R 3 , R 4 and R 5 represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or an alkoxycarbonyl group. ) 3,3-dimethyl-spiro[indolino 2,3'-naphtho[2,1-b] (1,4)
oxazine] derivatives. The spironaphthoxazine compound of the present invention is represented by the general formula []. In the formula, R 2 , R 3 , R 4 , and R 5 are hydrogen atoms; halogen atoms such as chlorine atoms, bromine atoms, and iodine atoms;
An alkyl group such as a C1-6 alkyl group; an alkoxy group such as a C1-6 alkoxy group; or an alkoxycarbonyl group such as a C1-6 alkoxycarbonyl group . The compound of the present invention can be produced, for example, as follows. In other words, the following general formula [] (In the formula, R 2 and R 3 are the same as defined above.) The following general formula [] (In the formula, R 1 is the same as defined above.) p
-Toluenesulfonic acid esters or alkyl halides represented by the following general formula [ ] Then the following general formula [] It can be produced by reacting a 1-nitroly-2-naphthol derivative represented by the formula (wherein R 4 and R 5 are the same as defined above). The alkylation reaction using p-toluenesulfonic acid ester or alkyl halide is carried out without a solvent or in a nonpolar solvent such as an aromatic solvent such as chlorobenzene or dichlorobenzene at a reaction temperature of 80 to 200°C. Preferably 130~ without solvent
Can be carried out smoothly at 150℃. Next, the reaction with the 1-nitroso-2-naphthol derivative is carried out in the presence of a basic catalyst such as piperidine, piperazine, or morpholine, using an alcoholic solvent such as methanol, ethanol, propanol, or butanol, or a ketone solvent such as acetone or methyl ethyl ketone. , dichloromethane, trichloroethane, and other halogenated hydrocarbon solvents. The reaction temperature is carried out in the range of 0 to 200°C. Preferably,
in ethanol, methyl ethyl ketone, acetone,
It can be carried out smoothly at 40°C to 120°C in the presence of a piperidine catalyst. The compound of the present invention can also be produced, for example, as follows. In other words, the following general formula [] (In the formula, R 1 , R 2 and R 3 are the same as defined above.) and the following general formula [] It can be produced by reacting a 1-nitroly-2-naphthol derivative represented by the formula (wherein R 4 and R 5 are the same as defined above). The reaction is usually carried out in the presence of a polar or non-polar solvent such as an alcoholic solvent such as methanol, ethanol, propanol or butanol, a ketone solvent such as acetone or methyl ethyl ketone, or a halogenated hydrocarbon solvent such as dichloromethane or trichloroethane. Ru. The reaction temperature is 0℃~
Conducted in the range of 200°C, preferably 40°C to 120°C
Can be carried out smoothly at ℃. [Function] The spironaphthoxazine compound of the present invention has a long-chain alkyl group (C 16 to C 24 ) as a substituent for N in the above general formula [], so it exhibits good coloring density and has a good color density. By this method, an organic ultra-thin film with excellent film forming properties and good photochromic properties can be produced. [Example] Next, the present invention will be explained in more detail with reference to Examples. Example 1 The following structural formula 21.6g of the compound represented by the following structural formula After adding 7 g of the compound 1-nitroso-2-naphthol and 100 ml of ethanol, and further adding 4 g of triethylamine, the mixture was reacted with stirring under a nitrogen atmosphere for 2 hours. After cooling, the solvent was distilled off and column chromatography (solvent used: benzene: n-
Separated and purified with hexane = 1:1), melting point 64-66
C. colorless crystals were obtained. Elemental analysis results are also shown below.
As shown in the table, the results agreed well with the calculated values.
【表】
実施例 2
実施例1に於ける下記構造式
で表わされる化合物21.6gの代りに、下記構造式
で表わされる化合物20.4gを用い、他の実施例1
と同様にして、下記化合物を得た。
実施例 3
実施例1〜2に準じた方法により、下記一般式
〔〕で示される化合物を合成した。トルエン溶
液中で紫外線照射したところ、各々第2表に示す
色調、λmaxに発色した。[Table] Example 2 The following structural formula in Example 1 Instead of 21.6g of the compound represented by the following structural formula Other Example 1 using 20.4 g of the compound represented by
The following compound was obtained in the same manner as above. Example 3 A compound represented by the following general formula [] was synthesized by a method similar to Examples 1 and 2. When irradiated with ultraviolet rays in a toluene solution, each color developed to the color tone λmax shown in Table 2.
【表】【table】
【表】【table】
【表】【table】
【表】【table】
本発明の化合物は新規な色素であり、ホトクロ
ミズムを示す化合物である。すなわち、本化合物
は紫外線照射により発色し、次に可視光を照射す
るか、あるいは50℃以上に加熱すると元の無色の
状態になり、この変化をくり返すことができる。
このような本化合物は各種の記録・記憶材料、
複写材料、印刷感光体、レーザー用感光材料、写
真植字用感光材料あるいは光学フイルター、マス
キング用材料、光量計、デイスプレイ用材料とし
て使用される。
The compound of the present invention is a novel dye and a compound exhibiting photochromism. That is, this compound develops a color when irradiated with ultraviolet rays, then returns to its original colorless state when irradiated with visible light or heated to 50°C or higher, and this change can be repeated. This compound can be used in various recording/memory materials,
It is used as a copying material, a printing photoreceptor, a light-sensitive material for lasers, a light-sensitive material for phototypesetting, an optical filter, a masking material, a photometer, and a display material.
Claims (1)
R3、R4、R5は水素原子、ハロゲン原子、アルキ
ル基、アルコキシ基またはアルコキシカルボニル
基を示す。) で表わされる3,3−ジメチル−スピロ〔インド
リノー2,3′−ナフト〔2,1−b〕(1,4)
オキサジン〕誘導体。[Claims] 1. General formula [] (In the formula, R 1 represents a C 16-24 alkyl group, R 2 ,
R 3 , R 4 and R 5 represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or an alkoxycarbonyl group. ) 3,3-dimethyl-spiro[indolino 2,3'-naphtho[2,1-b] (1,4)
Oxazine] derivative.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP60012192A JPS61263983A (en) | 1985-01-25 | 1985-01-25 | 3,3-dimethyl-spiro(indolino-2,3'-naphtho(2,1-b)-(1,4) oxazine)derivative |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP60012192A JPS61263983A (en) | 1985-01-25 | 1985-01-25 | 3,3-dimethyl-spiro(indolino-2,3'-naphtho(2,1-b)-(1,4) oxazine)derivative |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS61263983A JPS61263983A (en) | 1986-11-21 |
JPH0481998B2 true JPH0481998B2 (en) | 1992-12-25 |
Family
ID=11798536
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP60012192A Granted JPS61263983A (en) | 1985-01-25 | 1985-01-25 | 3,3-dimethyl-spiro(indolino-2,3'-naphtho(2,1-b)-(1,4) oxazine)derivative |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS61263983A (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63305181A (en) * | 1987-06-08 | 1988-12-13 | Nissan Motor Co Ltd | Thermal transfer recording ink |
JP5206045B2 (en) * | 2008-03-17 | 2013-06-12 | 株式会社リコー | Photochromic composition, image display medium, image forming apparatus, and image erasing apparatus |
JP5206046B2 (en) * | 2008-03-17 | 2013-06-12 | 株式会社リコー | Photochromic composition, image display medium, image forming apparatus, and image erasing apparatus |
JP5459528B2 (en) * | 2008-09-02 | 2014-04-02 | 株式会社リコー | Photochromic composition, image display medium, and image forming apparatus |
JP5645045B2 (en) * | 2008-09-02 | 2014-12-24 | 株式会社リコー | Photochromic composition, image display medium, and image forming apparatus |
-
1985
- 1985-01-25 JP JP60012192A patent/JPS61263983A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS61263983A (en) | 1986-11-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JPH0481996B2 (en) | ||
US5252742A (en) | Spiropyran compounds | |
EP0350009B1 (en) | Photochromic compound and photochromic composition | |
JPH0481998B2 (en) | ||
JPH02101080A (en) | Spiroxazine-based compound | |
EP0483542B1 (en) | A photochromic material and an optical storage medium using the same | |
US4078934A (en) | Photosensitive, image-forming composition containing a leuco 2,3-disubstituted-1-indanone and a photooxidant | |
JP3196383B2 (en) | Squarylium compounds | |
JPH06263732A (en) | Cyclobutene compound and its production and production of squarylium compound | |
JP2775879B2 (en) | Method for producing photochromic material | |
JPS62153292A (en) | Spirobenzoxazine based compound | |
EP0411157A1 (en) | Spiropyran compounds | |
JP2591042B2 (en) | Naphthacene derivatives | |
JPS61263935A (en) | Diallylethene derivative | |
JP3132549B2 (en) | Lightfast photochromic material | |
JPH02243694A (en) | Spiroxazine-based compound and photosensitive material using thereof | |
JPH0413354B2 (en) | ||
JPH0586955B2 (en) | ||
JPS6330487A (en) | Spiroooxazine compound and sensitized material using said compound | |
JPS6330488A (en) | Spirooxazine derivative and sensitized material using said derivative | |
JPH0739420B2 (en) | Spirooxazine compound and photosensitive material using the compound | |
JPS6118782A (en) | 3,3-dimethyl-6'-nitrospiro(indoline-2,2'-2h-benzopyran) derivative | |
JPH0645623B2 (en) | Spirooxazine compound and method for producing the same | |
JPH0549717B2 (en) | ||
JPS62164684A (en) | Photochromic compound |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
LAPS | Cancellation because of no payment of annual fees |