JPH0126636B2 - - Google Patents
Info
- Publication number
- JPH0126636B2 JPH0126636B2 JP24536486A JP24536486A JPH0126636B2 JP H0126636 B2 JPH0126636 B2 JP H0126636B2 JP 24536486 A JP24536486 A JP 24536486A JP 24536486 A JP24536486 A JP 24536486A JP H0126636 B2 JPH0126636 B2 JP H0126636B2
- Authority
- JP
- Japan
- Prior art keywords
- fulgide
- dicarboxylic acid
- mol
- formula
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 claims description 3
- 150000003443 succinic acid derivatives Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- HMKCSFHWMJHMTG-UHFFFAOYSA-N bis(furan-2-yl)methanone Chemical compound C=1C=COC=1C(=O)C1=CC=CO1 HMKCSFHWMJHMTG-UHFFFAOYSA-N 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-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
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical class O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- SXGUHJLRKQCPBN-UHFFFAOYSA-N dotriacontanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(Cl)=O SXGUHJLRKQCPBN-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- -1 furyl heptadecyl ketone Chemical compound 0.000 description 1
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical group O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 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)
- Furan Compounds (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の製造法に関す
る。DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to a method for producing photochromic materials.
従来技術
フルギドは、下記に示す一般式を持つ、可逆的
な色の変化を生ずるフオトクロミツク材料の一つ
である（但し、R1からR4のうち少なくとも一つ
は芳香族、Ｙ＝Ｏ、Ｎ−Ｒ）。フルギドのこの性
質を用いて、光記憶媒体、光量子検知素子、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。Prior Art Fulgide is one of the photochromic materials that produces a reversible color change and has the general formula shown below (provided that at least one of R 1 to R 4 is aromatic, Y=O, N -R). Using this property of fulgide, research is being carried out to apply it to optical storage media, photon detection devices, optical energy conversion devices, etc.
発明が解決しようとする問題点
代表的なフルギドのひとつである下記の(1)に
は、フオトクロミズムを示さない位置異性体(2)が
ある。以下(1)のタイプのフルギドをＥ体、その位
置異性体である(2)のタイプの化合物をＺ体と呼
ぶ。 Problems to be Solved by the Invention The following (1), which is one of the typical fulgides, has a positional isomer (2) that does not exhibit photochromism. Hereinafter, the fulgide of the type (1) will be referred to as the E-form, and its positional isomer, the compound of the type (2), will be referred to as the Z-form.
従来の合成法では、最終生成物はこのＥ体とＺ
体との混合物で、両者を分離して、フルギドを得
ていた（米国特許第4220708号）。 In conventional synthesis methods, the final product consists of this E form and Z form.
Fulgide was obtained by separating the two (US Pat. No. 4,220,708).
しかしこの方法では、まず、Ｚ体の副生のため
目的とするフルギド（Ｅ体）自身の収率が下が
る。さらに、Ｅ体とＺ体とは非常に似た構造をし
ているため、両者を完成に分離することは非常に
困難である。従来は分別結晶法を用いて分離を行
つているが、この方法では純度の高いフルギドを
得ることは、きわめて困難である。 However, in this method, first, the yield of the desired fulgide (E-form) itself decreases due to the by-production of the Z-form. Furthermore, since the E-form and the Z-form have very similar structures, it is extremely difficult to completely separate them. Conventionally, separation has been carried out using a fractional crystallization method, but it is extremely difficult to obtain highly pure fulgide using this method.
問題点を解決するための手段
下記の式（ただし、ＲはＣ＝５から31のアルキ
ル鎖を表すものとする）で表される構造を持つフ
リルケトンと、
下記の式
で表される構造を持つ、イソプロピリデン基を有
するコハク酸誘導体とをストツベ縮合で縮合さ
せ、生ずる半エステルを加水分解してジカルボン
酸とし、このジカルボン酸を脱水してフオトクロ
ミツク化合物を得る。Means for solving the problem A furyl ketone having a structure represented by the following formula (wherein R represents an alkyl chain of C=5 to 31), The formula below A succinic acid derivative having an isopropylidene group having the structure represented by is condensed by Stotube condensation, the resulting half ester is hydrolyzed to form a dicarboxylic acid, and this dicarboxylic acid is dehydrated to obtain a photochromic compound.
作 用
本製法は、従来の下記フリルフルギド(3)におい
て、置換基の組合せを工夫した特定の構造を選択
することによつて、これまで問題であつたＺ体の
副生がなく、目的のフルギドのみの合成が容易に
おこなえるということを特徴としている。その組
合せは(3)において、Ra、Rbはメチル、RcはＣ＝
５から31の炭化水素である。Effect This production method eliminates the by-product of the Z-form, which has been a problem in the past, by selecting a specific structure with a devised combination of substituents in the conventional furylfulgide (3) below, and produces the desired fulgide. It is characterized by the fact that it can be easily synthesized. The combination is (3), where R a and R b are methyl, and R c is C=
5 to 31 hydrocarbons.
生成物がＥ体になるかＺ体になるかは、フラン
環部と無水こはく酸部とのカツプリング反応のと
きに決定される。Ra、Rbにメチル基よりも立体
障害の大きな基を導入したものについては、こは
く酸誘導体との間に、カツプリングがうまく起こ
らず、生成物を与えない。またメチル基の代わり
に、水素を導入したものについては、次に示す立
体制御が効かず、Ｚ体が混入する。 Whether the product will be the E-form or the Z-form is determined during the coupling reaction between the furan ring moiety and the succinic anhydride moiety. If R a or R b has a group with greater steric hindrance than a methyl group, coupling with the succinic acid derivative will not occur well and no product will be produced. Furthermore, when hydrogen is introduced instead of a methyl group, the following steric control is not effective, and the Z form is mixed.
Ra、Rbがメチル基の時、RcをＣ＝５から31の
範囲に設定すると、相互に適当な立体障害が生
じ、Ｅ体を優先的に生成させることができる。し
かし、RbがＣ＝５より小さいときには、立体障
害が小さいため、Ｚ体が副生した。また、Ｃ＝33
以上の場合は、原料の入手が困難であつた。 When R a and R b are methyl groups, when R c is set in the range of C=5 to 31, appropriate steric hindrance occurs between them, and the E form can be preferentially produced. However, when R b was smaller than C=5, Z-form was produced as a by-product due to small steric hindrance. Also, C=33
In the above cases, it was difficult to obtain raw materials.
この様に、Ra、Rb、Rcの大きさのバランスに
より、目的とするフルギドを収率よくしかも容易
に合成することが可能となる。 In this way, the balance of the sizes of R a , R b , and R c makes it possible to easily synthesize the desired fulgide in good yield.
実施例
水素化ナトリウム1.2モルに石油エーテルを加
え５分間撹拌した。静置して上澄みを除いた後、
フリルヘプタデシルケトン0.8モルと、コハク酸
の誘導体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
ーテルを加え更に撹拌を続けた。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。Example Petroleum ether was added to 1.2 mol of sodium hydride and stirred for 5 minutes. After letting it stand and removing the supernatant,
A mixture of 0.8 mol of furyl heptadecyl ketone and 0.8 mol of a derivative of succinic acid, dissolved in as little petroleum ether as possible, was added. When one drop of ethanol was added thereto, the reaction started and hydrogen was violently generated. After hydrogen generation had stopped, 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.
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。 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, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and concentrated to obtain 0.3 mol of dicarboxylic acid. I got it.
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分間撹拌した。そのの
ち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。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0.1モルを得た。 Further, 100 ml of acetyl chloride was added to 0.3 mol of this dicarboxylic acid, and the mixture was stirred at room temperature for 10 minutes. Thereafter, the reaction mixture was concentrated, and the residue was separated and purified using silica gel column chromatography. To further increase purity, recrystallize from methanol for 1
By recrystallizing twice from hexane, 0.1 mol of the desired fulgide was obtained.
最終生成物の液体クロマトグラフイーによるビ
ークは単一で、そのピークは、紫外光の照射によ
つて完全に消失し、代わりにベンゾフラン形に相
当するピークが現れた。もしフオトクロミズムを
示さないＺ体の生成があれば、紫外光の照射前と
照射後とで不変のピークがあるはずである。した
がつて、この最終生成物は、Ｅ体のみであること
が確認された。従来法においてカツプリング反応
で得られるのは、Ｅ体とＺ体の混合物であり、こ
のステツプの後にＥ体とＺ体の分離という操作が
あつた。しかし本方法では純粋なＥ体のみが得ら
れ、Ｚ体は得られなかつた。 The final product had a single peak in liquid chromatography, which completely disappeared upon irradiation with ultraviolet light, and a peak corresponding to the benzofuran form appeared instead. If a Z-form that does not exhibit photochromism is produced, there should be an unchanged peak before and after irradiation with ultraviolet light. Therefore, it was confirmed that this final product was only the E form. In the conventional method, a mixture of the E-form and the Z-form is obtained by the coupling reaction, and this step is followed by an operation for separating the E-form and the Z-form. However, in this method, only the pure E form was obtained, and the Z form was not obtained.
なお、塩化ステアロイルのかわりに塩化ヘキサ
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、同様の結果が得られた（Ｃ＝５）。し
かし、塩化ペンタノイルを用いたフルギドの合成
では、Ｅ体とＺ体との混合物が得られた。 When fulgide was synthesized in the same manner using hexanoyl chloride instead of stearoyl chloride, similar results were obtained (C=5). However, in the synthesis of fulgide using pentanoyl chloride, a mixture of E and Z forms was obtained.
さらに、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、同様の結果が得られた（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。 Furthermore, when fulgide was synthesized in a similar manner using dotriacontanoyl chloride instead of stearoyl chloride, similar results were obtained (C
=31). However, for compounds with longer chains than this, it is difficult to obtain the raw acid chloride.
発明の効果
本発明により、フオトクロミズムを示すフルギ
ドのみを、難しい分離操作なしで、容易にしかも
大量に得ることが可能になり、その波及効果は大
である。Effects of the Invention According to the present invention, only fulgide exhibiting photochromism can be easily obtained in large quantities without difficult separation operations, and its ripple effects are large.
Claims (1)
キル鎖を表すものとする）で表されるフリルケト
ンと、 下記の式 で表される、イソプロピリデン基を有するコハク
酸誘導体とをストツベ縮合で縮合させ、生ずる半
エステルを加水分解してジカルボン酸とし、この
ジカルボン酸を脱水することを特徴とするフオト
クロミツク化合物の製造法。[Scope of Claims] 1 Furyl ketone represented by the following formula (wherein R represents an alkyl chain of C=5 to 31); The formula below A method for producing a photochromic compound, which comprises condensing a succinic acid derivative having an isopropylidene group represented by the formula by Stotube condensation, hydrolyzing the resulting half ester to form a dicarboxylic acid, and dehydrating this dicarboxylic acid.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24536486A JPS63101475A (en) | 1986-10-17 | 1986-10-17 | Production of photochromic material |
| 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 |
|---|---|---|---|
| JP24536486A JPS63101475A (en) | 1986-10-17 | 1986-10-17 | Production of photochromic material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63101475A JPS63101475A (en) | 1988-05-06 |
| JPH0126636B2 true JPH0126636B2 (en) | 1989-05-24 |
Family
ID=17132564
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24536486A Granted JPS63101475A (en) | 1986-04-16 | 1986-10-17 | Production of photochromic material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63101475A (en) |
-
1986
- 1986-10-17 JP JP24536486A patent/JPS63101475A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63101475A (en) | 1988-05-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |