JPH03181453A - Phenolic compound - Google Patents
Phenolic compoundInfo
- Publication number
- JPH03181453A JPH03181453A JP1319599A JP31959989A JPH03181453A JP H03181453 A JPH03181453 A JP H03181453A JP 1319599 A JP1319599 A JP 1319599A JP 31959989 A JP31959989 A JP 31959989A JP H03181453 A JPH03181453 A JP H03181453A
- Authority
- JP
- Japan
- Prior art keywords
- bis
- difunctional
- oxapentane
- reacting
- color
- 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
- 150000002989 phenols Chemical class 0.000 title claims description 5
- 239000000126 substance Substances 0.000 claims description 4
- 239000000981 basic dye Substances 0.000 abstract description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract description 4
- 239000004014 plasticizer Substances 0.000 abstract description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 3
- 239000002253 acid Substances 0.000 abstract description 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 2
- -1 alkali metal salt Chemical class 0.000 abstract description 2
- 239000007800 oxidant agent Substances 0.000 abstract description 2
- 230000001590 oxidative effect Effects 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- NOMXFWAANLCUKA-UHFFFAOYSA-N 4-[2-[2-(4-hydroxyphenyl)sulfanylethoxy]ethylsulfanyl]phenol Chemical compound C1=CC(O)=CC=C1SCCOCCSC1=CC=C(O)C=C1 NOMXFWAANLCUKA-UHFFFAOYSA-N 0.000 abstract 1
- BXAVKNRWVKUTLY-UHFFFAOYSA-N 4-sulfanylphenol Chemical compound OC1=CC=C(S)C=C1 BXAVKNRWVKUTLY-UHFFFAOYSA-N 0.000 abstract 1
- ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 2
- 238000001454 recorded image Methods 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- OAIVIYSBZFEOIU-UHFFFAOYSA-N chloroform;propan-2-one Chemical compound CC(C)=O.ClC(Cl)Cl OAIVIYSBZFEOIU-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C317/22—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
「産業上の利用分野」
本発明は、無色ないしは淡色の塩基性染料に対する呈色
剤として有用なフェノール性化合物に関するものである
。DETAILED DESCRIPTION OF THE INVENTION "Industrial Application Field" The present invention relates to a phenolic compound useful as a coloring agent for colorless or light-colored basic dyes.
「従来の技術」
従来、無色ないしは淡色の塩基性染料と有機ないしは無
機呈色剤との呈色反応を利用した記録材料はよく知られ
ており、その−例として両発色戊分を熱により接触させ
て記録像を得るように構成した感熱記録体がある。"Prior Art" Conventionally, recording materials that utilize a color reaction between a colorless or light-colored basic dye and an organic or inorganic coloring agent are well known. There is a heat-sensitive recording medium that is configured to obtain a recorded image by
最近、感熱ファックスや感熱プリンター等の使用が急速
に普及し、それに伴って感熱記録体の使用形態も広範と
なり、プラスチックフィルムや油脂類、或いはアルコー
ル等の有機溶剤と接触するような状態で感熱記録体が使
用される機会が多くなっている。Recently, the use of thermal fax machines, thermal printers, etc. has rapidly spread, and with this the use of thermal recording media has become widespread. Opportunities for using the body are increasing.
ところが、一般に感熱記録体は、プラスチックフィルム
に含まれる可塑剤などの有機溶剤によって記録像が著し
く褪色したり、あるいは白紙部分の変色（カブリ現象）
が極めて起こり易い等の欠点を有している。かかる欠点
を改善し、耐溶剤性を高めるために、呈色剤としてビス
フェノールＳ誘導体（特開昭５７−２１０８８６号、特
開昭５８８２７８８号、特開昭５８−１６６０９８号、
特開昭６０−１３８５２号）を用いることが提案されて
いる。しかし、これらの化合物を用いた感熱記録体にお
いても、画像の保存性、特に油や可塑剤に対する安定性
の点で必ずしも充分であるとは言い難い。However, in general, with thermosensitive recording media, the recorded image may fade significantly due to organic solvents such as plasticizers contained in plastic films, or discoloration of blank areas (fogging phenomenon) may occur.
It has the disadvantage that it is extremely likely to occur. In order to improve such drawbacks and increase solvent resistance, bisphenol S derivatives (JP-A-57-210886, JP-A-5882788, JP-A-58-166098,
It has been proposed to use JP-A-60-13852). However, even in heat-sensitive recording materials using these compounds, it cannot be said that the images are always sufficient in terms of storage stability, especially stability against oils and plasticizers.
「発明が解決しようとする課題」
本発明の目的は、耐溶剤性、特に耐油性や耐可塑剤性に
優れた塩基性染料用の呈色剤として極めて有用な新規フ
ェノール性化合物を提供するところにある。``Problems to be Solved by the Invention'' The purpose of the present invention is to provide a novel phenolic compound that is extremely useful as a coloring agent for basic dyes and has excellent solvent resistance, particularly oil resistance and plasticizer resistance. It is in.
「課題を解決するための手段」 本発明は、化学構造式 で表されるフェノール性化合物である。"Means to solve problems" The present invention is based on the chemical structural formula It is a phenolic compound represented by
「作用」
上記化学構造式で表される１、５−ビス（４ヒドロキシ
フエニルスルホニル）−３−オキサペンクンは、■ｐ−
フェノールスルフィン酸のアルカリ金属塩とビス（２−
クロロエチル）エーテル等の二官能性ジエチルエーテル
誘導体との反応による方法、又は、■ｐ−ヒドロキシチ
オフェノールと上記の如き二官能性ジエチルエーテル誘
導体との反応で容易に合成できる１、５−ビス（４ヒド
ロキシフエニルチオ）−３−オキサペンクンを過酸化水
素水などの酸化剤で酸化する方法により、容易に高収率
、高純度でかつ比較的安価に製造することができる。"Action" 1,5-bis(4hydroxyphenylsulfonyl)-3-oxapencune represented by the above chemical structural formula is ■p-
Alkali metal salts of phenolsulfinic acid and bis(2-
1,5-bis(4), which can be easily synthesized by a reaction with a difunctional diethyl ether derivative such as By oxidizing hydroxyphenylthio)-3-oxapenkune with an oxidizing agent such as hydrogen peroxide, it can be easily produced in high yield, with high purity, and at a relatively low cost.
「実施例」 以下に実施例を挙げてより具体的に説明する。"Example" A more specific explanation will be given below with reference to Examples.
実施例
攪拌機および還流冷却器を備えた５００ｍ１容量のフラ
スコに、１．５−ビス（４−ヒドロキシフェニルチオ）
−３−オキサペンクン３２．３ｇ（０゜１０モル）と酢
酸２００ｍ１を秤取した。この系を約７０℃に加熱し、
攪拌下、３５％過酸化水素水４１ｇ（０，４２モル）を
約３０分かけて滴下した後、約７０℃で１０時間反応さ
せた。反応終了後、反応混合物を５００ｍ１の水中に注
ぎ、析出した結晶を、吸引濾過乾燥した。次いで、得ら
れた結晶をクロロホルム−アセトン混合溶媒にて再結晶
し、融点１３８〜１３９℃の１．５−ビス（４−ヒドロ
キシフェニルスルホニル）−３−オキサペンクンを白色
結晶として３５．５ ｇ得た。なお、収率は９２％であ
った。Example In a 500 ml flask equipped with a stirrer and a reflux condenser, 1,5-bis(4-hydroxyphenylthio)
32.3 g (0°10 mol) of -3-oxapencune and 200 ml of acetic acid were weighed out. This system was heated to about 70°C,
While stirring, 41 g (0.42 mol) of 35% hydrogen peroxide solution was added dropwise over about 30 minutes, and the mixture was reacted at about 70° C. for 10 hours. After the reaction was completed, the reaction mixture was poured into 500 ml of water, and the precipitated crystals were filtered and dried under suction. Next, the obtained crystals were recrystallized from a chloroform-acetone mixed solvent to obtain 35.5 g of 1.5-bis(4-hydroxyphenylsulfonyl)-3-oxapenkune as white crystals with a melting point of 138-139°C. . Note that the yield was 92%.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1319599A JPH03181453A (en) | 1989-12-09 | 1989-12-09 | Phenolic compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1319599A JPH03181453A (en) | 1989-12-09 | 1989-12-09 | Phenolic compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03181453A true JPH03181453A (en) | 1991-08-07 |
Family
ID=18112069
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1319599A Pending JPH03181453A (en) | 1989-12-09 | 1989-12-09 | Phenolic compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03181453A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102574784A (en) * | 2009-09-30 | 2012-07-11 | 日本曹达株式会社 | Phenolic compound and recording material |
-
1989
- 1989-12-09 JP JP1319599A patent/JPH03181453A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102574784A (en) * | 2009-09-30 | 2012-07-11 | 日本曹达株式会社 | Phenolic compound and recording material |
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