JPH04352752A - Benzoic acid derivative - Google Patents
Benzoic acid derivativeInfo
- Publication number
- JPH04352752A JPH04352752A JP12722891A JP12722891A JPH04352752A JP H04352752 A JPH04352752 A JP H04352752A JP 12722891 A JP12722891 A JP 12722891A JP 12722891 A JP12722891 A JP 12722891A JP H04352752 A JPH04352752 A JP H04352752A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- benzoic acid
- acid derivative
- compound
- methylamino
- 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
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 239000000126 substance Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 abstract description 24
- 239000000463 material Substances 0.000 abstract description 9
- -1 fluoran compound Chemical class 0.000 abstract description 7
- 239000002994 raw material Substances 0.000 abstract description 7
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract description 5
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract description 5
- OMASSVVZMKZNBK-UHFFFAOYSA-N 3-[2-methylpropyl(propan-2-yl)amino]phenol Chemical compound CC(C)CN(C(C)C)C1=CC=CC(O)=C1 OMASSVVZMKZNBK-UHFFFAOYSA-N 0.000 abstract description 3
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical class NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 abstract description 3
- FSIUSWYIMPBSKX-UHFFFAOYSA-N 2-[4-[ethyl(methyl)amino]-2-hydroxybenzoyl]benzoic acid Chemical compound OC1=CC(N(C)CC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O FSIUSWYIMPBSKX-UHFFFAOYSA-N 0.000 abstract description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 2
- VESAVCMAQXXPGK-UHFFFAOYSA-N 3-[methyl(propan-2-yl)amino]phenol Chemical compound CC(C)N(C)C1=CC=CC(O)=C1 VESAVCMAQXXPGK-UHFFFAOYSA-N 0.000 abstract 1
- 238000004040 coloring Methods 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical class C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- PQTIRJGIJDODDP-UHFFFAOYSA-N 3-[ethyl(methyl)amino]phenol Chemical compound CCN(C)C1=CC=CC(O)=C1 PQTIRJGIJDODDP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- JHKKTXXMAQLGJB-UHFFFAOYSA-N 2-(methylamino)phenol Chemical compound CNC1=CC=CC=C1O JHKKTXXMAQLGJB-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- WPYMKLBDIGXBTP-VQEHIDDOSA-N benzoic acid Chemical compound OC(=O)C1=CC=C[13CH]=C1 WPYMKLBDIGXBTP-VQEHIDDOSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000003348 petrochemical agent Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は、新規な安息香酸誘導体
に関する。更に詳しくは、記録材料用の発色性化合物と
して有用なフルオラン化合物の重要な製造原料となる安
息香酸誘導体に関する。FIELD OF THE INVENTION This invention relates to novel benzoic acid derivatives. More specifically, the present invention relates to benzoic acid derivatives that are important raw materials for producing fluoran compounds useful as color-forming compounds for recording materials.
【０００２】0002
【従来の技術】従来、無色ないし淡色の電子供与性化合
物（発色性化合物）と有機もしくは無機の電子受容性物
質（顕色剤）との呈色反応を利用し、圧力、熱または電
気などの外部エネルギーの媒介により、伝達される情報
を記録する方法として、感圧記録、感熱記録および通電
感熱記録などがある。これらの記録方式には、発色性化
合物として、フルオラン化合物が広く用いられている。
フルオラン化合物の原料となる安息香酸誘導体としては
、従来、例えば、式〔ＩＩａ〕および式〔ＩＩｂ〕（化
２）の化合物が知られている。[Prior Art] Conventionally, a color reaction between a colorless or light-colored electron-donating compound (color-forming compound) and an organic or inorganic electron-accepting substance (color developer) is used. BACKGROUND ART Methods for recording information transmitted through the medium of external energy include pressure-sensitive recording, heat-sensitive recording, and energized heat-sensitive recording. In these recording methods, fluoran compounds are widely used as color-forming compounds. As benzoic acid derivatives serving as raw materials for fluoran compounds, for example, compounds of formula [IIa] and formula [IIb] (chemical formula 2) are known.
【０００３】0003
【化２】
これらの安息香酸誘導体を原料として、それぞれ式［Ｉ
ＩＩａ］ および式［ＩＩＩｂ］（化３）のフルオラン
化合物が製造されている。[I
IIa] and the fluoran compound of the formula [IIIb] (Chemical formula 3) have been produced.
【０００４】0004
【化３】
しかし、式［ＩＩＩａ］ の化合物は、感圧記録材料と
して用いるには、カプセルオイルに対する溶解度が極め
て低いという欠点があり、また感熱記録材料として用い
るには、例えば、ビスフェノールＡ等の顕色剤と混合す
ると、それ自体灰色ないし黒灰色に発色し、これを紙に
塗布すると、灰色ないし黒灰色に着色（地汚れ）した紙
しか得られないという欠点があった。embedded image However, the compound of formula [IIIa] has the disadvantage of extremely low solubility in capsule oil when used as a pressure-sensitive recording material, and when used as a heat-sensitive recording material, for example, bisphenol A etc. When mixed with a color developer, it itself develops a gray or black-gray color, and when it is applied to paper, it has the disadvantage that only paper colored gray or black-gray (background stain) is obtained.
【０００５】また、［ＩＩＩｂ］ の化合物は、感熱記
録材料として用いるには、発色する温度が高すぎるため
、より高速かつ高密度に記録しようとする要望に適合し
た充分な性能とは言えず、より低温ですみやかに発色す
る発色性化合物およびこのような化合物を製造するため
の原料化合物が強く望まれている。[0005] Furthermore, the compound [IIIb] cannot be used as a heat-sensitive recording material because its color development temperature is too high, so it cannot be said to have sufficient performance to meet the demand for higher speed and higher density recording. There is a strong desire for color-forming compounds that quickly develop color at lower temperatures and raw material compounds for producing such compounds.
【０００６】[0006]
【発明が解決しようとする課題】本発明の課題は、上記
の欠点を解決した感圧および感熱等の記録材料に適した
フルオラン化合物の原料として有用な安息香酸誘導体を
提供することである。SUMMARY OF THE INVENTION An object of the present invention is to provide a benzoic acid derivative useful as a raw material for a fluoran compound suitable for pressure-sensitive and heat-sensitive recording materials, which solves the above-mentioned drawbacks.
【０００７】[0007]
【課題を解決するための手段】本発明者らは、上述の課
題を解消するために種々の化合物を探索し、本発明に到
達した。すなわち本発明は、一般式〔Ｉ〕（化４）で表
わされる安息香酸誘導体に関するものである。[Means for Solving the Problems] In order to solve the above-mentioned problems, the present inventors searched for various compounds and arrived at the present invention. That is, the present invention relates to a benzoic acid derivative represented by the general formula [I] (Chemical formula 4).
【０００８】[0008]
【化４】
本発明の化合物は前記一般式〔Ｉ〕で表わされる安息香
酸誘導体であり、具体的には下記式〔Ｉａ〕、式〔Ｉｂ
〕および式〔Ｉｃ〕（化５）で表わされる安息香酸誘導
体である。embedded image The compound of the present invention is a benzoic acid derivative represented by the general formula [I], specifically the following formula [Ia], the formula [Ib
] and a benzoic acid derivative represented by the formula [Ic] (Chemical formula 5).
【０００９】[0009]
【化５】
これらの化合物は、対応する３−アミノフェノール誘導
体、即ち、３−（Ｎ−エチル−Ｎ−メチルアミノ）フェ
ノール、３−（Ｎ−イソプロピル−Ｎ−メチルアミノ）
フェノールあるいは３−（Ｎ−イソプロピル−Ｎ−イソ
ブチルアミノ）フェノールと無水フタル酸とを反応させ
ることにより製造することができる。３−アミノフェノ
ール誘導体と無水フタル酸のモル比は１：１〜２である
。反応は無溶媒で行ってもよく、あるいはベンゼン、ト
ルエン、キシレンまたはテトラクロロエチレン等の溶媒
中で行ってもよい。反応温度は６０〜１４０℃の範囲が
好ましく、反応時間は反応温度により異なるが、数時間
から数十時間の間が好ましい。またこの反応の際、例え
ば、塩化亜鉛のようなルイス酸を添加してもよい。embedded image These compounds are derived from the corresponding 3-aminophenol derivatives, namely 3-(N-ethyl-N-methylamino)phenol, 3-(N-isopropyl-N-methylamino)
It can be produced by reacting phenol or 3-(N-isopropyl-N-isobutylamino)phenol with phthalic anhydride. The molar ratio of 3-aminophenol derivative to phthalic anhydride is 1:1-2. The reaction may be carried out without a solvent or in a solvent such as benzene, toluene, xylene or tetrachloroethylene. The reaction temperature is preferably in the range of 60 to 140°C, and the reaction time varies depending on the reaction temperature, but is preferably from several hours to several tens of hours. Further, during this reaction, a Lewis acid such as zinc chloride may be added.
【００１０】本発明の一般式〔Ｉ〕で表される安息香酸
誘導体を単離する方法としては、通常、反応終了後、反
応溶液から安息香酸誘導体を結晶として析出させ、濾過
することによって単離する方法が用いられる。また、一
般式〔Ｉ〕で表される安息香酸誘導体をアルカリ水溶液
で抽出した後、酸により析出させる方法、あるいは安息
香酸誘導体のナトリウム塩として、一旦分離した後、酸
により析出させる方法等によっても単離することが出来
る。さらに、ベンゼン、トルエン、メタノール、イソプ
ロパノール等の有機溶媒、あるいはこれらとｎ−ヘキサ
ン等の他の有機溶媒との混合溶媒から再結晶することに
よっても結晶として単離することができる。本発明の一
般式〔Ｉ〕で表わされる安息香酸誘導体はフルオラン化
合物の製造における原料として非常に有用である。本発
明の一般式〔Ｉ〕で表わされる化合物を用いて製造され
るフルオラン化合物、例えば、下記の式〔ＩＶａ〕、式
〔ＩＶｂ〕および式〔ＩＶｃ〕（化６）の化合物は、[0010] As a method for isolating the benzoic acid derivative represented by the general formula [I] of the present invention, the benzoic acid derivative is usually precipitated as crystals from the reaction solution after the reaction is completed, and isolated by filtration. A method is used. Alternatively, the benzoic acid derivative represented by the general formula [I] may be extracted with an alkaline aqueous solution and then precipitated with an acid, or the sodium salt of the benzoic acid derivative may be separated and then precipitated with an acid. Can be isolated. Furthermore, it can be isolated as a crystal by recrystallization from an organic solvent such as benzene, toluene, methanol, isopropanol, or a mixed solvent of these and other organic solvents such as n-hexane. The benzoic acid derivative represented by the general formula [I] of the present invention is very useful as a raw material in the production of fluoran compounds. Fluoran compounds produced using the compound represented by the general formula [I] of the present invention, for example, the compounds of the following formula [IVa], formula [IVb] and formula [IVc] (chemical formula 6),
【
００１１】[
0011
【化６】
感圧記録材料に使用する際、カプセルオイル例えばＳＡ
Ｓ−２９６（日本石油化学製）に対して室温で１０重量
％以上溶解し、極めて溶解度が高く、実用上極めて優れ
た性能を有する発色性化合物である。また、感熱記録材
料に使用すると、地汚れのない、白色度の高い紙が得ら
れ、また式［ＩＩＩａ］ や式［ＩＩＩｂ］ の化合物
に比較して、より低温ですみやかに黒色に発色する優れ
た特徴を有している。[Chemical 6] When used in pressure-sensitive recording materials, capsule oils such as SA
It is a color-forming compound that dissolves 10% by weight or more in S-296 (manufactured by Nippon Petrochemicals) at room temperature, has extremely high solubility, and has extremely excellent performance in practical use. In addition, when used in heat-sensitive recording materials, paper with high whiteness without background staining can be obtained, and compared to the compounds of formula [IIIa] and formula [IIIb], it has the advantage of rapidly developing black color at a lower temperature. It has the following characteristics.
【００１２】0012
【実施例】以下、実施例により本発明を更に具体的に説
明するが、本発明はこれらの実施例に限定されるもので
はない。
実施例１
（式〔Ｉａ〕の化合物の製造）３−（Ｎ−エチル−Ｎ−
メチルアミノ）フェノール１５０ｇと無水フタル酸１８
０ｇを３００ｍｌのトルエン中で９０〜１００℃で８時
間攪拌した。３００ｍｌの水を加えた後、６０℃で３０
分攪拌し、トルエン層を分離した。その後さらに温水（
３００ｍｌ）で２回洗浄した。トルエン層を分離し、ト
ルエンを減圧下留去後、析出した結晶を集め、少量のト
ルエンで洗浄した。さらに含水イソプロパノールで洗浄
後、乾燥を行い１５０ｇのクリーム色の結晶として２−
〔２’−ヒドロキシ−４’−（Ｎ−エチル−Ｎ−メチル
アミノ）ベンゾイル〕安息香酸を得た。収率は５１％で
、その融点は１７２〜１７５℃であった。EXAMPLES The present invention will be explained in more detail with reference to Examples below, but the present invention is not limited to these Examples. Example 1 (Production of compound of formula [Ia]) 3-(N-ethyl-N-
150g of (methylamino)phenol and 18g of phthalic anhydride
0g was stirred in 300ml of toluene at 90-100°C for 8 hours. After adding 300ml of water, heat at 60℃ for 30 minutes.
The mixture was stirred for several minutes and the toluene layer was separated. Then warm water (
300 ml) twice. The toluene layer was separated, the toluene was distilled off under reduced pressure, and the precipitated crystals were collected and washed with a small amount of toluene. Furthermore, after washing with aqueous isopropanol and drying, 2-
[2'-Hydroxy-4'-(N-ethyl-N-methylamino)benzoyl]benzoic acid was obtained. The yield was 51% and the melting point was 172-175°C.
【００１３】 １Ｈ−ＮＭＲ
δ（ＣＤＣｌ３ ）：１．０ 〜１．３ （ｔ，３Ｈ）
、２．８ （ｓ，３Ｈ）、３．３ 〜３．５ （ｍ，２
Ｈ）、６．０ 〜６．８ （ｍ，３Ｈ）、７．２ 〜８
．１ （ｍ，５Ｈ）、１２．５（ｓ，１Ｈ）1H-NMR δ(CDCl3): 1.0 to 1.3 (t, 3H)
, 2.8 (s, 3H), 3.3 ~ 3.5 (m, 2
H), 6.0 to 6.8 (m, 3H), 7.2 to 8
．． 1 (m, 5H), 12.5 (s, 1H)
【００１４】実施例２
（式〔Ｉｂ〕の化合物の製造）実施例１において、３−
（Ｎ−エチル−Ｎ−メチルアミノ）フェノール１５０ｇ
を使用する代わりに、３−（Ｎ−イソプロピル−Ｎ−メ
チルアミノ）フェノール１８０ｇを使用した他は、実施
例１に記載した方法に従い、目的とする２−〔２’−ヒ
ドロキシ−４’−（Ｎ−イソプロピル−Ｎ−メチルアミ
ノ）ベンゾイル〕安息香酸１８１ｇを製造した。収率は
５５％で、その融点は１７８〜１８０℃であった。Example 2 (Production of compound of formula [Ib]) In Example 1, 3-
(N-ethyl-N-methylamino)phenol 150g
The desired 2-[2'-hydroxy-4'-( 181 g of N-isopropyl-N-methylamino)benzoyl]benzoic acid were produced. The yield was 55% and the melting point was 178-180°C.
【００１５】 １Ｈ−ＮＭＲ
δ（ＣＤＣｌ３ ）：１．１ 〜１．３ （ｄ，２Ｈ）
、２．８ （ｓ，３Ｈ）、３．８ 〜４．０ （ｍ，１
Ｈ）、６．０ 〜６．８ （ｍ，３Ｈ）、７．２ 〜８
．１ （ｍ，５Ｈ）、１２．５（ｓ，１Ｈ）1H-NMR δ(CDCl3): 1.1 to 1.3 (d, 2H)
, 2.8 (s, 3H), 3.8 ~ 4.0 (m, 1
H), 6.0 to 6.8 (m, 3H), 7.2 to 8
．． 1 (m, 5H), 12.5 (s, 1H)
【００１６】実施例３
（式〔Ｉｃ〕の化合物の製造）３−（Ｎ−イソプロピル
−Ｎ−イソブチルアミノ）フェノール２１０ｇと無水フ
タル酸１８０ｇを４００ｍｌのトルエン中で、９０〜１
００℃で１０時間攪拌した。４００ｍｌの水を加えた後
、６０℃で３０分攪拌し、トルエン層を分離した。その
後、さらに温水（４００ｍｌ）で２回洗浄した。トルエ
ン層を分離し、トルエンを減圧下留去した後、残渣にイ
ソプロパノール１０００ｍｌ、及び５０％ＮａＯＨ水３
２０ｍｌを加え、析出したナトリウム塩を濾過し、イソ
プロパノール４００ｍｌで洗浄した。このナトリウム塩
を水１０００ｍｌに分散後、濃塩酸を加えて、ｐＨを５
〜６とした。析出した結晶を濾過、水洗乾燥し、１７３
ｇのクリーム色の結晶として２−〔２’−ヒドロキシ−
４’−（Ｎ−イソプロピル−Ｎ−イソブチルアミノ）ベ
ンゾイル〕安息香酸を得た。収率は４８％で、その融点
は１８２〜１８５℃であった。Example 3 (Production of compound of formula [Ic]) In 400 ml of toluene, 210 g of 3-(N-isopropyl-N-isobutylamino)phenol and 180 g of phthalic anhydride were mixed with 90-1
The mixture was stirred at 00°C for 10 hours. After adding 400 ml of water, the mixture was stirred at 60°C for 30 minutes and the toluene layer was separated. Thereafter, it was further washed twice with warm water (400 ml). After separating the toluene layer and distilling off the toluene under reduced pressure, 1000 ml of isopropanol and 3 ml of 50% NaOH water were added to the residue.
20 ml was added, and the precipitated sodium salt was filtered and washed with 400 ml of isopropanol. After dispersing this sodium salt in 1000 ml of water, add concentrated hydrochloric acid to adjust the pH to 5.
~6. The precipitated crystals were filtered, washed with water, and dried.
2-[2'-hydroxy-
4'-(N-isopropyl-N-isobutylamino)benzoyl]benzoic acid was obtained. The yield was 48% and the melting point was 182-185°C.
【００１７】 １Ｈ−ＮＭＲ
δ（ＣＤＣｌ３ ）：０．８ 〜１．０ （ｄ，６Ｈ）
、１．１ 〜１．３ （ｄ，６Ｈ）、１．７ 〜２．０
（ｍ，１Ｈ）、２．８ 〜３．０ （ｄ，２Ｈ）、３
．８ 〜４．０ （ｍ，１Ｈ）、６．０ 〜６．８ （
ｍ，３Ｈ）、７．２ 〜８．１ （ｍ，５Ｈ）、１２．
５（ｓ，１Ｈ）1H-NMR δ(CDCl3): 0.8 to 1.0 (d, 6H)
, 1.1 ~ 1.3 (d, 6H), 1.7 ~ 2.0
(m, 1H), 2.8 to 3.0 (d, 2H), 3
．． 8 ~ 4.0 (m, 1H), 6.0 ~ 6.8 (
m, 3H), 7.2 to 8.1 (m, 5H), 12.
5 (s, 1H)
【００１８】[0018]
【発明の効果】本発明は、フルオラン化合物の製造にお
ける原料として非常に有用である一般式〔Ｉ〕で表わさ
れる安息香酸誘導体を提供するものであり、この安息香
酸誘導体を用いて製造されるフルオラン化合物は、感圧
、感熱記録材料の発色性化合物として優れた性能を有す
る化合物である。Effects of the Invention The present invention provides a benzoic acid derivative represented by the general formula [I] which is very useful as a raw material in the production of fluoran compounds, and a fluoran compound produced using this benzoic acid derivative. The compound has excellent performance as a color-forming compound for pressure-sensitive and heat-sensitive recording materials.
Claims (1)
息香酸誘導体。 【化１】Claim 1: A benzoic acid derivative represented by the general formula [I] (Chemical formula 1). [Chemical formula 1]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12722891A JPH04352752A (en) | 1991-05-30 | 1991-05-30 | Benzoic acid derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12722891A JPH04352752A (en) | 1991-05-30 | 1991-05-30 | Benzoic acid derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04352752A true JPH04352752A (en) | 1992-12-07 |
Family
ID=14954904
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12722891A Pending JPH04352752A (en) | 1991-05-30 | 1991-05-30 | Benzoic acid derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04352752A (en) |
-
1991
- 1991-05-30 JP JP12722891A patent/JPH04352752A/en active Pending
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