JPH02238059A - Stable type indoaniline-based leuco coloring matter - Google Patents
Stable type indoaniline-based leuco coloring matterInfo
- Publication number
- JPH02238059A JPH02238059A JP5882389A JP5882389A JPH02238059A JP H02238059 A JPH02238059 A JP H02238059A JP 5882389 A JP5882389 A JP 5882389A JP 5882389 A JP5882389 A JP 5882389A JP H02238059 A JPH02238059 A JP H02238059A
- Authority
- JP
- Japan
- Prior art keywords
- indoaniline
- based leuco
- stable
- oxidation
- coloring matter
- 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
- 238000004040 coloring Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 16
- 239000000463 material Substances 0.000 abstract description 5
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 abstract description 3
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 238000007254 oxidation reaction Methods 0.000 description 11
- 230000003647 oxidation Effects 0.000 description 8
- 238000000862 absorption spectrum Methods 0.000 description 7
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 230000009920 chelation Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- -1 probyl group Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B9/00—Esters or ester-salts of leuco compounds of vat dyestuffs
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B53/00—Quinone imides
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、記録材料として有用な新規な安定型インドア
ニリン系ロイコ色素に関するものである・．詳しくは、
本発明は酸化、酸化−キｌレート化による色変化を利用
するカラーフォーマーとじて使用されるロイコ色素に関
するものである。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a novel stable indoaniline-based leuco dye useful as a recording material. For more information,
The present invention relates to a leuco dye used as a color former that utilizes color changes due to oxidation and oxidation-chelation.
（従来の技術〕
ロイコ色素の酸化一還元挙動を利用して記録材料の研究
が行なわれ、これに使用できるキノン系ロイコ色素の開
発は重要な課題のひとつである。(Prior Art) Research on recording materials is conducted using the oxidation-reduction behavior of leuco dyes, and the development of quinone-based leuco dyes that can be used in this is one of the important issues.
しかしながら、このキノン系ロイコ体は不安定なものが
多く、その研究は進んでいない。However, many of these quinone-based leuco bodies are unstable, and their research has not progressed.
本発明は、酸化による色変化を利用するカラーフォーマ
ーとして有望な新規な安定型インドアニリン系ロイコ色
素を提供することを目的とするものである。An object of the present invention is to provide a novel stable indoaniline-based leuco dye that is promising as a color former that utilizes color change due to oxidation.
特に、本発明の安定型インドアニリン系ロイコ色素は安
定に単離でき、更に酸化反応の他、メタルキレート化反
応を行なわせることにより酸化反応のみの時より長波長
側の近赤外領域に強い吸収を持たせることができるとい
う特性を有する。In particular, the stable indoaniline-based leuco dye of the present invention can be stably isolated, and by performing a metal chelation reaction in addition to an oxidation reaction, it is stronger in the near-infrared region on the longer wavelength side than when only an oxidation reaction is used. It has the property of being able to absorb.
本発明は、一般式（Ｉ）
（式中、Ｒｌ は水素原子またはハロゲン原子を表わし
、Ｒ２およびＲ１は低級アルキル基を表わし、Ｘは水素
原子または低級アルキル基を表わす。）で示される安定
型インドアニリン系ロイコ色素をその要旨とするもので
ある。The present invention provides a stable type represented by the general formula (I) (wherein Rl represents a hydrogen atom or a halogen atom, R2 and R1 represent a lower alkyl group, and X represents a hydrogen atom or a lower alkyl group). Its gist is indoaniline-based leuco dyes.
以下、本発明を詳細に説明する．
一般式〔！］中、Ｒ１としては、水素原子：塩素原子、
臭素原子、フッ素原子、ヨウ素原子等のハロゲン原子が
挙げられ、特に水素原子が好ましい。Ｒｔ．Ｒ３として
は、メチル基、エチル基、プロビル基、プチル基、ペン
チル基、ヘプチル基等の直鎖状ないし分技状のＣ，〜Ｃ
，の低級アルキル基が挙げられ、Ｘとしては水素原子の
ばかメチル基、エチル基、プロビル基、プチル基等の直
鎖状ないし分枝状のＣ１〜Ｃ，の低級アルキル基が挙げ
られる．
本発明の一般式（１）で示される安定型インドアニリン
系ロイコ色素の合成は、例えば、下記一般式（ＩＩ）
Ｒ重
（式中、Ｒｌ ， Ｒｚ ． Ｒｘ及びＸは前記定義に
同じ．）
で示されるインドアニリン系化合物に亜ニチオン酸ナト
リウム等を反応させ、還元することにより製造すること
ができる．
本発明の安定型インドアニリン系ロイコ色素は、■酸化
剤が作用すると発色して５５０〜６５０ｎｍの波長帯域
に吸収を有するようになり、更に■金属塩の存在下に、
酸化剤が作用すると酸化−キレート化による発色が起こ
り、紫外部領域から近赤外領域（７００〜８５０ｎｍ）
へと吸収強度の著しい増大とともに大幅なスペクトル変
化を示す．〔実施例〕
以下実施例によりこの発明を具体的に説明するが、かか
る実施例は本発明を限定するものではない。The present invention will be explained in detail below. General formula [! ], R1 is hydrogen atom: chlorine atom,
Examples include halogen atoms such as bromine atom, fluorine atom, and iodine atom, with hydrogen atom being particularly preferred. Rt. R3 is a linear or branched C, ~C, such as a methyl group, ethyl group, probyl group, butyl group, pentyl group, heptyl group, etc.
, and X is a straight-chain or branched C1-C lower alkyl group such as a hydrogen atom, such as a methyl group, an ethyl group, a proyl group, or a butyl group. The stable indoaniline leuco dye represented by the general formula (1) of the present invention can be synthesized using, for example, the following general formula (II) R (wherein Rl, Rz, Rx and X are the same as defined above). It can be produced by reacting the indoaniline compound shown with sodium dithionite, etc., and reducing it. The stable indoaniline-based leuco dye of the present invention (1) develops color when acted upon by an oxidizing agent and absorbs in the wavelength band of 550 to 650 nm, and (2) in the presence of a metal salt,
When an oxidizing agent acts, color development occurs due to oxidation and chelation, and from the ultraviolet region to the near-infrared region (700 to 850 nm)
shows a significant spectral change with a significant increase in absorption intensity. [Examples] The present invention will be specifically explained below with reference to Examples, but these Examples are not intended to limit the present invention.
実施例１
（ａ） 合成例
下記構造式
水素ナトリウムで中和し、析出した黄色の沈殿を濾過し
た。得られた沈殿を減圧乾燥し、窒素ガス封入下にてカ
ラムクロマトグラフィー〔吸着剤；シリカゲル（商品名
ワコーゲルＣ−３ ０ ０．和光純薬■製造）、展開溶
媒：塩化メチレン〕にかけ、溶媒を減圧留去すると下記
構造式で示される安定型インドアニリン系ロイコ色素の
黄色の結晶が収率５１％で得られた．
本品は空気中で極めて安定に存在し、カラムクロマトに
より単離することができた。Example 1 (a) Synthesis Example A product having the following structural formula was neutralized with sodium hydrogen, and the precipitated yellow precipitate was filtered. The obtained precipitate was dried under reduced pressure and subjected to column chromatography [adsorbent: silica gel (trade name: Wakogel C-3 0 0. manufactured by Wako Pure Chemical Industries, Ltd.)] under nitrogen gas, developing solvent: methylene chloride] to remove the solvent. After distillation under reduced pressure, yellow crystals of a stable indoaniline leuco dye represented by the following structural formula were obtained in a yield of 51%. This product is extremely stable in air and could be isolated by column chromatography.
で示されるインドアニリン系化合物１ｇ（３．１ｍｍｏ
ｌｅ ）を９５％エタノールｌ ５ ０ｍｆｆｉに７ｏ
″Ｃにて溶解させ、アルゴンガス封入下で亜ニチオン酸
ナトリウム４９１■（２． ８ ２＋ｍａｏ）ｅ ）と
水酸化ナトリウム１ ８ ９ｍｇ （４． ７＋＊ｍｏ
ｌｅ ）を含む水溶液２０ｍ２を７０″Ｃにて滴下し、
同温にて１分間撹拌した後、酢酸１ｍｌを加えてｐ１１
４にした。その溶液を水４００ｍｊ！に注ぎ炭酸ナトリ
ウムと炭酸？ 紫外部吸収スペクトル（エタノール中）
λ．■３９７ｎｍ（ε．■２８５０）
○ 元素分析値
（ｂ） 特 性（酸化挙動）
（１）酸化
室温、エタノール中にて空気酸化を受け、図−１の吸収
スペクトルの変化で示したようにゆっくりと発色し、化
合物（１ａ）から（２ａ）へ変換した。1 g (3.1 mmo) of an indoaniline compound represented by
) to 95% ethanol l 50mffi 7o
Sodium dithionite 491 (2.8 2 + mao) e ) and sodium hydroxide 1 8 9 mg (4.7 + * mo ) were dissolved under argon gas.
20 m2 of an aqueous solution containing ) was dropped at 70″C,
After stirring for 1 minute at the same temperature, 1 ml of acetic acid was added and p11
I gave it a 4. Pour the solution into 400mj of water! Pour into sodium carbonate and carbonate? Ultraviolet absorption spectrum (in ethanol)
λ. ■397nm (ε.■2850) ○ Elemental analysis value (b) Characteristics (oxidation behavior) (1) Oxidation Under air oxidation in ethanol at room temperature, slowly as shown by the change in absorption spectrum in Figure 1. The compound (1a) was converted to (2a).
（２）酸化−キレート化
酸化剤でもあるＦｅＣｊ！ｉ？’ｔｌ液を化合物（１ａ
）のエタノール溶液に２５℃で添加すると、図−２に示
すようにただちに発色が起こり、化合物（１ａ）→（３
ａ）への変換により紫外部領域（３９７ｎｍ）から近赤
外領域（７ ５ ２ ｎｍ）へと大幅なスペクトル変化
（約３ ５ ０ ｎｍ）とともに吸収強度の著しく増大
することが見られた。(2) FeCj, which is also an oxidizing-chelating oxidizing agent! i? 'tl solution to compound (1a
) to an ethanol solution of compound (1a) at 25°C, color development occurs immediately as shown in Figure 2, and compound (1a)→(3
It was observed that the conversion to a) resulted in a significant spectral change (approximately 350 nm) from the ultraviolet region (397 nm) to the near-infrared region (752 nm) and a significant increase in absorption intensity.
図−３にストップトフ口一分光光度計を用いて、濃度比
（ＦｅＣｊ！ｓ ）／ （ｌａ）＝１００における（３
ａ）の生成速度を測定したものを示したが、発色濃度が
飽和するまでの時間は３秒であった．（条件：２５゜Ｃ
，（ｌａ）の濃度： ３． ８ ８ ＸＩＯ−’ｍｏｌ
／ｊ！）
実施例２
（ａ） 合成例
実施例１において、下記構造式
Ｃ２
Ｏ 元素分析値
で表わされる化合物の代りに、下記構造式で表わされる
化合物を用いた以外は実施例ｌと同様に行ない、下記構
造式で表わされる安定型インドアニリン系ロイコ色素を
得た。Figure 3 shows the concentration ratio (FeCj!s)/(la)=100 (3
The measurement of the production rate of a) is shown, and the time it took for the color density to become saturated was 3 seconds. (Condition: 25°C
, (la) concentration: 3. 8 8 XIO-'mol
/j! ) Example 2 (a) Synthesis Example The same procedure as Example 1 was carried out except that in Example 1, a compound represented by the following structural formula was used instead of the compound represented by the following structural formula C2O elemental analysis value, A stable indoaniline leuco dye represented by the following structural formula was obtained.
Ｏ 紫外部吸収スペクトル（エタノール中）λ６＠Ｘ
３９８ｎｍ Ｃｔｍａ＊ ３３１０）実施例３
（ａ） 合成例
実施例１において、下記構造式
で表わされる化合物の代りに、
下記構造式
Ｏ 紫外部吸収スペクトル（エタノール中）λｖａａ＊
４ ０ ４ ｎｍ （ｔｗｈｍＮ ２ ８ ３ ０
）実施例４
（ａ） 合成例
実施例ｌにおいて、下記構造式
で表わされる化合物を用いた以外は実施例１と同様に行
ない、下記構造式で表わされる安定型インドアニリン系
ロイコ色素を得た。O Ultraviolet absorption spectrum (in ethanol) λ6@X
398nm Ctma* 3310) Example 3 (a) Synthesis Example In Example 1, instead of the compound represented by the following structural formula, the following structural formula O Ultraviolet absorption spectrum (in ethanol) λvaa*
4 0 4 nm (twhmN 2 8 3 0
) Example 4 (a) Synthesis Example Example 1 was carried out in the same manner as in Example 1 except that a compound represented by the following structural formula was used to obtain a stable indoaniline-based leuco dye represented by the following structural formula. .
で表わされる化合物の代りに、
下記構造式
物性値
○ 元素分析値
で表わされる化合物を用いた以外は実施例ｌと同様に行
ない、下記構造式で表わされる安定型インドアニリン系
ロイコ色素を得た。A stable indoaniline-based leuco dye represented by the following structural formula was obtained in the same manner as in Example 1 except that a compound represented by the following structural formula and physical property values ○ elemental analysis values was used instead of the compound represented by the following structural formula. .
第
表
○
元素分析値
○ 紫外部吸収スペクトル（エタノール中）λｍｍｘ
４ ０ ４ ｎｍ （６ｓａｘ ２ ４ ２ ０）実施
例５
実施例１に準じた方法により、第１表に示すような安定
化インドアニリン系ロイコ色素を得た。Table ○ Elemental analysis values ○ Ultraviolet absorption spectrum (in ethanol) λmmx
4 0 4 nm (6sax 2 4 2 0) Example 5 By a method similar to Example 1, stabilized indoaniline leuco dyes as shown in Table 1 were obtained.
本発明は新規なインドアニリン系ロイコ色素に関し、安
定に単離でき酸化反応またはメタルキレート化と酸化と
を組み合せた反応により色変化を行なわせることができ
る。The present invention relates to a novel indoaniline-based leuco dye, which can be stably isolated and can undergo a color change through an oxidation reaction or a reaction combining metal chelation and oxidation.
従って本発明の色素はカラーフォーマーとしてバーコー
ド、複写紙をはじめとする各種記録材料に有用である。Therefore, the dye of the present invention is useful as a color former for various recording materials such as bar codes and copy paper.
図−１は、本発明の安定型インドアニリン系ロイコ色素
１例の酸化による吸収スペクトルおよび吸収強度の経時
的変化を表わすものであり、縦軸は吸光度、横軸は波長
（ｎｍ）を表わす。
図−２は、本発明の安定型インドアニリン系ロイコ色素
１例の酸化一キレート化における吸収スペクトルおよび
吸収強度の変化を表わすものであり、縦軸は吸光度、横
軸は波長（ｎｍ）を表わす。
図−３は、本発明の安定型インドアニリン系ロイコ色素
１例の酸化−キレート化における発色速度を表わしたも
のであり、縦軸は７２５ｎｍの吸光度、横軸は時間（秒
）
を表わす。
図−１
保Figure 1 shows the absorption spectrum and absorption intensity changes over time due to oxidation of one example of the stable indoaniline-based leuco dye of the present invention, where the vertical axis represents absorbance and the horizontal axis represents wavelength (nm). Figure 2 shows changes in absorption spectrum and absorption intensity upon oxidative monochelation of one example of the stable indoaniline-based leuco dye of the present invention, where the vertical axis represents absorbance and the horizontal axis represents wavelength (nm). . Figure 3 shows the color development rate during oxidation-chelation of one example of the stable indoaniline-based leuco dye of the present invention, where the vertical axis represents absorbance at 725 nm and the horizontal axis represents time (seconds). Figure-1
Claims (1)
、Ｒ＾２及びＲ＾３は低級アルキル基を表わし、Ｘは水
素原子または低級アルキル基を表わす。）で示される安
定型インドアニリン系ロイコ色素。(1) General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼... [I] (In the formula, R^1 represents a hydrogen atom or a halogen atom, and R^2 and R^3 are lower alkyl X represents a hydrogen atom or a lower alkyl group).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5882389A JPH02238059A (en) | 1989-03-11 | 1989-03-11 | Stable type indoaniline-based leuco coloring matter |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5882389A JPH02238059A (en) | 1989-03-11 | 1989-03-11 | Stable type indoaniline-based leuco coloring matter |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02238059A true JPH02238059A (en) | 1990-09-20 |
Family
ID=13095357
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5882389A Pending JPH02238059A (en) | 1989-03-11 | 1989-03-11 | Stable type indoaniline-based leuco coloring matter |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02238059A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5218120A (en) * | 1990-10-04 | 1993-06-08 | Basf Aktiengesellschaft | Quinolinemethine dyes |
| CN103319404A (en) * | 2013-05-30 | 2013-09-25 | 苏州康润医药有限公司 | Nitroxoline derivatives and use of the nitroxoline derivatives as angiogenesis inhibitors |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57212426A (en) * | 1981-06-08 | 1982-12-27 | Minnesota Mining & Mfg | Photsensitive/heat sensitive photographic material |
| JPS63227569A (en) * | 1987-03-14 | 1988-09-21 | Katsuhei Yoshida | Metal-containing indoaniline compound |
-
1989
- 1989-03-11 JP JP5882389A patent/JPH02238059A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57212426A (en) * | 1981-06-08 | 1982-12-27 | Minnesota Mining & Mfg | Photsensitive/heat sensitive photographic material |
| JPS63227569A (en) * | 1987-03-14 | 1988-09-21 | Katsuhei Yoshida | Metal-containing indoaniline compound |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5218120A (en) * | 1990-10-04 | 1993-06-08 | Basf Aktiengesellschaft | Quinolinemethine dyes |
| CN103319404A (en) * | 2013-05-30 | 2013-09-25 | 苏州康润医药有限公司 | Nitroxoline derivatives and use of the nitroxoline derivatives as angiogenesis inhibitors |
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