JPH0437101B2 - - Google Patents
Info
- Publication number
- JPH0437101B2 JPH0437101B2 JP15084183A JP15084183A JPH0437101B2 JP H0437101 B2 JPH0437101 B2 JP H0437101B2 JP 15084183 A JP15084183 A JP 15084183A JP 15084183 A JP15084183 A JP 15084183A JP H0437101 B2 JPH0437101 B2 JP H0437101B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- general formula
- compound
- formula
- present
- 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
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229930192627 Naphthoquinone Natural products 0.000 claims description 4
- 150000002791 naphthoquinones Chemical class 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000835 fiber 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
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004982 mineral liquid crystal Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Description
本発明は新規なナフトキノン誘導体に関するも
のである。
すなわち、本発明は、一般式
（式中、Ｒは水素原子、アルキル基、またはア
ルコキシ基を示し、Ｘはハロゲン原子を示し、Ｙ
はヒドロキシ基を示し、そしてＸおよびＹは
The present invention relates to novel naphthoquinone derivatives. That is, the present invention provides the general formula (In the formula, R represents a hydrogen atom, an alkyl group, or an alkoxy group, X represents a halogen atom, and Y
represents a hydroxy group, and X and Y are
【式】の基であつてもよく、こ
の場合Ｘは−Ｓ−に、Ｙは−NH−に対応しそし
てR′は水素原子、アルキル基またはアルコキシ
基を示す）で表わされるナフトキノン誘導体を要
旨とするものである。
本発明のナフトキノン誘導体は、染料、顔料あ
るいはそれらの中間体として価値ある新規な化合
物である。
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。すなわち一般式〔〕
（式中、Ｘは一般式〔Ｉ〕におけると同様の意
義を有する）で表わされる化合物と下記一般式
〔〕
（式中、Ｒは一般式〔Ｉ〕におけると同様の意
義を有する）で表わされる化合物とを反応させる
ことより、下記一般式〔〕
（式中、ＲおよびＸは一般式〔Ｉ〕におけると
同様の意義を有する）で表わされる化合物が製造
される。
その際、一般式〔〕で表わされる化合物を一
般式〔〕で表わされる化合物に対して多く使用
することにより、下記一般式〔Ｖ〕
（式中、Ｒは一般式〔Ｉ〕におけると同様の意
義を有する）で表わされる化合物が製造される。
又一般式〔〕で表わされる化合物に下記一般
式〔〕
（式中、R′は一般式〔Ｉ〕におけると同様の
意義を有する）で表わされる化合物を反応させる
ことにより下記一般式〔〕
（式中、ＲおよびR′は一般式〔Ｉ〕における
と同様の意義を有し、ＲおよびR′は同じであつ
ても異つていてもよい）で表わされる化合物が製
造される。
上記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、
ジクロロベンゼン、Ｎ−メチルピロリドンなどの
極性又は非極性溶媒の存在下に実施される。反応
温度は−50℃〜250℃の範囲で実施され、好まし
くは−10℃〜150℃で円滑に実施できる。
又、反応は苛性カリ、苛性ソーダ、炭酸ソーダ
等の酸結合剤の存在下で高収率で実施できる。
本発明の一般式〔Ｉ〕に於けるＲおよびR′の
具体例としては水素原子；メチル基、エチル基、
直鎖状乃至は分枝鎖状のプロピル基、ブチル基、
ペンチル基、ヘキシル基、ヘプチル基、オクチル
基、ノニル基、デシル基、ドデシル基などのアル
キル基；メトキシ基、エトキシ基、ｎ−ブトキシ
基等のアルコキシ基が挙げられる。Ｘの具体例と
しては塩素原子、臭素原子などのハロゲン原子が
挙げられる。
本発明の化合物は新規な化合物であり、また色
素として鉱油、液晶等の低分子物質の着色及びセ
ルロース、セルロース・アセテート、ポリエステ
ル、ポリスチレン等の天然〜合成高分子物質から
成るシート状、繊維状その他成型物の着色に有用
であり、着色法としては通常の染色法の外に昇
華、混練、転写等の方法が挙げられる。又本発明
化合物は種々の染料、顔料の中間体として価値あ
るものである。
次に本発明を実施例により更に具体的に説明す
るが、本発明は下記実施例に限定されるものでは
ない。
実施例 １
ｏ−アミノチオフエノール0.27ｇを、苛性カリ
0.125ｇおよびエタノール20mlから成る溶液に加
え、次いでこれに２，３−ジクロロナフタザリン
0.26ｇおよびエタノール65mlから成る溶液を加え
て室温で５時間攪拌し、反応させた。反応後塩酸
を加えて析出物を取したのち、得られたケーキ
をクロロホルムにより再結晶して、下記構造の化
合物（mp＞310℃、青黒色粉末）を得た。
本化合物のクロロホルム中での吸収スペクトル
は607nm、667nm、726nmに極大ピークを示し
た。
又、本化合物をポリスチレンに対して0.04重量
％添加して、常法により射出成型して青色に着色
されたポリスチレン板を得た。
実施例 ２
ｏ−アミノチオフエノール0.13ｇ、苛性カリ
0.06ｇを用い、他は実施例１と同様にして、下記
構造式の化合物を得た。
本化合物のクロロホルム中の吸収スペクトルは
570nmに極大ピークを示した。
又、本化合物を用いて実施例１と同様にポリス
チレンを成型して、紫色に着色された成型板を得
た。
実施例 ３
実施例１、２に準じた方法により、下記化合物
を得た。
A naphthoquinone derivative represented by [Formula], in which case X corresponds to -S-, Y corresponds to -NH-, and R' represents a hydrogen atom, an alkyl group, or an alkoxy group) That is. The naphthoquinone derivative of the present invention is a novel compound valuable as a dye, a pigment, or an intermediate thereof. The compound of the present invention can be produced, for example, as follows. In other words, the general formula [] (wherein, X has the same meaning as in general formula [I]) and the following general formula [] (wherein, R has the same meaning as in general formula [I]), the following general formula [] A compound represented by the formula (wherein R and X have the same meanings as in general formula [I]) is produced. At that time, by using more of the compound represented by the general formula [] than the compound represented by the general formula [], the following general formula [V] A compound represented by the formula (wherein R has the same meaning as in general formula [I]) is produced. In addition, the following general formula [] is added to the compound represented by the general formula [] (In the formula, R' has the same meaning as in general formula [I]) By reacting the compound represented by the following general formula [] A compound represented by the formula (wherein R and R' have the same meanings as in general formula [I], and R and R' may be the same or different) is produced. The above reaction is usually carried out using alcoholic solvents such as methanol, ethanol, propanol, butanol, etc.
It is carried out in the presence of a polar or non-polar solvent such as dichlorobenzene, N-methylpyrrolidone. The reaction temperature is carried out in the range of -50°C to 250°C, preferably -10°C to 150°C, so that the reaction can be carried out smoothly. Moreover, the reaction can be carried out in high yield in the presence of an acid binder such as caustic potash, caustic soda, or soda carbonate. Specific examples of R and R' in the general formula [I] of the present invention include a hydrogen atom; a methyl group, an ethyl group,
Straight chain or branched propyl group, butyl group,
Alkyl groups such as a pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, and dodecyl group; alkoxy groups such as a methoxy group, ethoxy group, and n-butoxy group. Specific examples of X include halogen atoms such as chlorine atoms and bromine atoms. The compound of the present invention is a new compound, and can be used as a pigment to color low-molecular substances such as mineral oil or liquid crystal, or in the form of sheets, fibers, etc. made of natural to synthetic polymer substances such as cellulose, cellulose acetate, polyester, and polystyrene. It is useful for coloring molded objects, and examples of coloring methods include sublimation, kneading, transfer, and other methods in addition to normal dyeing methods. The compounds of the present invention are also valuable as intermediates for various dyes and pigments. Next, the present invention will be explained in more detail with reference to examples, but the present invention is not limited to the following examples. Example 1 0.27 g of o-aminothiophenol was added to caustic potassium.
0.125 g and 20 ml of ethanol, then to this was added 2,3-dichloronaphthazarin
A solution consisting of 0.26 g and 65 ml of ethanol was added and stirred at room temperature for 5 hours to react. After the reaction, hydrochloric acid was added to remove the precipitate, and the resulting cake was recrystallized from chloroform to obtain a compound with the following structure (mp>310°C, blue-black powder). The absorption spectrum of this compound in chloroform showed maximum peaks at 607 nm, 667 nm, and 726 nm. Further, 0.04% by weight of this compound was added to polystyrene, and injection molding was performed by a conventional method to obtain a blue-colored polystyrene plate. Example 2 o-aminothiophenol 0.13g, caustic potash
A compound having the following structural formula was obtained in the same manner as in Example 1 except that 0.06 g was used. The absorption spectrum of this compound in chloroform is
It showed a maximum peak at 570nm. Further, polystyrene was molded using this compound in the same manner as in Example 1 to obtain a molded plate colored purple. Example 3 The following compound was obtained by a method similar to Examples 1 and 2.
Claims (1)
ルコキシ基を示し、Ｘはハロゲン原子を示し、Ｙ
はヒドロキシ基を示し、そしてＸおよびＹは
【式】の基であつてもよく、こ の場合Ｘは−Ｓ−に、Ｙは−NH−に対応しそし
てR′は水素原子、アルキル基またはアルコキシ
基を示す）で表わされるナフトキノン誘導体。[Claims] 1. General formula (In the formula, R represents a hydrogen atom, an alkyl group, or an alkoxy group, X represents a halogen atom, and Y
represents a hydroxy group, and X and Y may be a group of the formula, in which case X corresponds to -S-, Y corresponds to -NH-, and R' is a hydrogen atom, an alkyl group or an alkoxy group. A naphthoquinone derivative represented by (indicating a group).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15084183A JPS6042464A (en) | 1983-08-18 | 1983-08-18 | Naphthoquinone derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15084183A JPS6042464A (en) | 1983-08-18 | 1983-08-18 | Naphthoquinone derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6042464A JPS6042464A (en) | 1985-03-06 |
| JPH0437101B2 true JPH0437101B2 (en) | 1992-06-18 |
Family
ID=15505540
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15084183A Granted JPS6042464A (en) | 1983-08-18 | 1983-08-18 | Naphthoquinone derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6042464A (en) |
-
1983
- 1983-08-18 JP JP15084183A patent/JPS6042464A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6042464A (en) | 1985-03-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |