JPH07242651A - Production of sulfonyl halide compound and substituted sulfonamide compound - Google Patents
Production of sulfonyl halide compound and substituted sulfonamide compoundInfo
- Publication number
- JPH07242651A JPH07242651A JP6034837A JP3483794A JPH07242651A JP H07242651 A JPH07242651 A JP H07242651A JP 6034837 A JP6034837 A JP 6034837A JP 3483794 A JP3483794 A JP 3483794A JP H07242651 A JPH07242651 A JP H07242651A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- halide
- represented
- thionyl
- 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
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
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- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyrane Compounds (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、カラーフィルター用色
素等の中間体として有用な一般式（ＩＩ）FIELD OF THE INVENTION The present invention relates to general formula (II) useful as an intermediate for dyes for color filters.
【０００２】[0002]
【化４】 [Chemical 4]
【０００３】（式中、Ｒ1 〜Ｒ7 は各々独立して水素原
子又は置換されていてもよいアルキル、アルケニル、シ
クロアルキル、アラルキルもしくはアリール基を表わ
し、Ｍは水素、アルカリ金属もしくはアルカリ土類金属
原子又は４級アンモニウム塩を表わし、Ｘはハロゲン原
子を表わし、ｋは０〜４の整数を表わし、ｎは１〜５の
整数を表わすが、ｋ及びｎの和は後述するｍに等しい。
ＳＯ3 Ｍ並びにＳＯ2 ＸはＳＯ3 - で置換されているベ
ンゼン環及びＲ1 〜Ｒ4 で表わされるアラルキルもしく
はアリール基の何れか或いは双方の置換基である。）で
示されるスルホニルハライド化合物、並びに、カラーフ
ィルター用色素等として有用な一般式（Ｉ）(In the formula, R 1 to R 7 each independently represent a hydrogen atom or an optionally substituted alkyl, alkenyl, cycloalkyl, aralkyl or aryl group, and M represents hydrogen, an alkali metal or an alkaline earth group. Represents a metal atom or a quaternary ammonium salt, X represents a halogen atom, k represents an integer of 0 to 4 and n represents an integer of 1 to 5, and the sum of k and n is equal to m described later.
SO 3 M and SO 2 X are substituents on either or both of the benzene ring substituted with SO 3 − and the aralkyl or aryl groups represented by R 1 to R 4 . ), A general formula (I) useful as a dye for color filters, etc.
【０００４】[0004]
【化５】 [Chemical 5]
【０００５】（式中、Ｒ1 〜Ｒ7 、Ｍ、Ｒ、ｋ及びｎは
上記と同じ意味を有する。）で示される置換スルホンア
ミド化合物の製造方法に関する。A method for producing a substituted sulfonamide compound represented by the formula (wherein R 1 to R 7 , M, R, k and n have the same meanings as described above).
【０００６】[0006]
【従来の技術】一般に色素の分野では、スルホンアミド
化合物は相当するスルホニルクロライド化合物と相当す
る１級アミンとの反応により得られ、上記スルホニルク
ロライド化合物はスルホン酸基を有する直接もしくは酸
性染料等をクロロスルホン酸、五塩化燐或いは酸塩化燐
等を用いてクロル化することにより製造されている。し
かしながら、これらの方法では、目的とするスルホン酸
基のクロル化ばかりでなく、色素骨格そのものに新たな
スルホン酸基を導入してしまう等、反応の制御が困難で
あった。特に、一般式（ＩＩＩ）2. Description of the Related Art Generally, in the field of dyes, sulfonamide compounds are obtained by reacting a corresponding sulfonyl chloride compound with a corresponding primary amine. It is produced by chlorination using sulfonic acid, phosphorus pentachloride, phosphorus acid chloride or the like. However, in these methods, it is difficult to control the reaction such as introducing a new sulfonic acid group into the dye skeleton itself as well as chlorinating the desired sulfonic acid group. In particular, the general formula (III)
【０００７】[0007]
【化６】 [Chemical 6]
【０００８】（式中、Ｒ1 〜Ｒ7 及びＭは上記と同じ意
味を有し、ｍは１〜５の整数を表わす。）で示されるキ
サンテン誘導体のような分子内塩では、クロロスルホン
酸、五塩化燐或いは酸塩化燐等を用いてクロル化する
と、骨格自体が開裂したり、反応が遅い等収率及び純度
の観点から工業的に満足できるものではない。(In the formula, R 1 to R 7 and M have the same meanings as described above, and m represents an integer of 1 to 5.) In the intramolecular salt such as the xanthene derivative, chlorosulfonic acid is used. Chlorination with phosphorus pentachloride or phosphorus oxychloride is not industrially satisfactory in terms of yield and purity such as cleavage of the skeleton itself and slow reaction.
【０００９】[0009]
【発明が解決しようとする課題】本発明は上記問題点を
解決して、上記一般式（ＩＩ）及び（Ｉ）で各々示され
るスルホニルハライド化合物及び置換スルホンアミド化
合物の工業的有利な製造方法を提供する。The present invention solves the above problems and provides an industrially advantageous method for producing a sulfonyl halide compound and a substituted sulfonamide compound represented by the general formulas (II) and (I), respectively. provide.
【００１０】[0010]
【課題を解決するための手段】本発明は、上記一般式
（ＩＩＩ）で示されるキサンテン誘導体とハロゲン化チ
オニルとを、Ｎ，Ｎ−ジメチルホルムアミド及びハロゲ
ン化脂肪族炭化水素溶媒の存在下に反応させることを特
徴とする一般式（ＩＩ）で示されるスルホニルハライド
化合物の製造方法、並びに、上記キサンテン誘導体とハ
ロゲン化チオニルとをＮ，Ｎ−ジメチルホルムアミド及
びハロゲン化脂肪族炭化水素溶媒の存在下に反応させて
上記スルホニルハライド化合物を得、次いで当該スルホ
ニルハライド化合物を下式 Ｒ−ＮＨ2 （式中、Ｒは置換されていてもよいアルキル、シクロヘ
キシルアルキル、アルキルカルボニルアミノアルキル、
アルコキシ、アルコキシアルキル、アリール、アラルキ
ルもしくはシクロアルキル基を表わす。）で示される１
級アミンと縮合反応させることを特徴とする一般式
（Ｉ）で示される置換スルホンアミド化合物の製造方法
である。According to the present invention, a xanthene derivative represented by the general formula (III) and a thionyl halide are reacted in the presence of N, N-dimethylformamide and a halogenated aliphatic hydrocarbon solvent. A method for producing a sulfonyl halide compound represented by the general formula (II), and the above xanthene derivative and thionyl halide in the presence of N, N-dimethylformamide and a halogenated aliphatic hydrocarbon solvent. The above sulfonyl halide compound is reacted to obtain the sulfonyl halide compound, and then the sulfonyl halide compound is represented by the following formula R-NH 2 (wherein R is an optionally substituted alkyl, cyclohexylalkyl, alkylcarbonylaminoalkyl,
Represents an alkoxy, alkoxyalkyl, aryl, aralkyl or cycloalkyl group. ) 1
A method for producing a substituted sulfonamide compound represented by the general formula (I), which comprises conducting a condensation reaction with a primary amine.
【００１１】キサンテン誘導体としては、例えば下式As the xanthene derivative, for example, the following formula
【００１２】[0012]
【化７】 [Chemical 7]
【００１３】[0013]
【化８】 [Chemical 8]
【００１４】（式中、Ｘ及びＹはこれらの中少なくとも
１つが−ＳＯ3 Ｍを表わすという条件付きで、各々水素
原子もしくは−ＳＯ3 Ｍを表わし、Ｍは上記と同じ意味
を有する。）等で示されるローダミン色素等が挙げられ
る。キサンテン誘導体は単独で又は２種以上混合して、
ハロゲン化チオニルとの反応に供される。ハロゲン化チ
オニルとしては塩化チオニルが好ましい。ハロゲン化脂
肪族炭化水素溶媒としては、例えばクロロホルム、塩化
メチレン、四塩化炭素、１，２−ジクロロエタン、ジク
ロロエチレン、トリクロロエチレン、パークロロエチレ
ン、ジクロロプロパン、塩化アミル、ジクロロペンタ
ン、テトラクロロエタン及び１，２−ジブロモエタン等
が挙げられるが、クロロホルムがより好ましい。キサン
テン誘導体とハロゲン化チオニルとの反応において、ハ
ロゲン化チオニルに対するＮ，Ｎ−ジメチルホルムアミ
ドの使用量は、好ましくはモル比で１：0.3 〜１：0.8
の範囲である。ハロゲン化チオニルの使用量はキサンテ
ン誘導体の種類及び純度により異なるが、通常はキサン
テン誘導体に対してモル比で１：１〜１：20の範囲であ
る。一般に、キサンテン誘導体の純度が高い場合にはハ
ロゲン化チオニルの使用量は化学当量或いは化学当量よ
りも若干多めでよく、一方、食塩又は芒硝等の不純物が
多くてキサンテン誘導体の純度が低い場合にはハロゲン
化チオニルの使用量は化学当量よりも相当過剰に用いる
ことが好ましい。反応は、通常はキサンテン誘導体、
Ｎ，Ｎ−ジメチルホルムアミド及びハロゲン化脂肪族炭
化水素溶媒の混合物中にハロゲン化チオニルを徐々に加
える方法で行なわれる。反応温度は通常は約０〜約70
℃、好ましくは約30〜約60℃で行なわれ、反応時間は通
常は30分〜６時間程度である。キサンテン誘導体に対す
るハロゲン化脂肪族炭化水素溶媒の使用量は適宜設定さ
れる。一般式（ＩＩ）で示されるスルホニルハライド化
合物の反応混合物からの取り出しは、通常は上記反応混
合物を必要なら冷却後、水又は氷水中に注いで残存する
ハロゲン化チオニルを分解した後、抽出、洗浄及び濃縮
等の慣用手段を用いて行なわれる。より好ましくは、得
られた上記反応混合物（上記スルホニルハライド化合物
及び残存するハロゲン化チオニルのハロゲン化脂肪族炭
化水素溶媒溶液）を、そのまま前記１級アミンとの縮合
反応に供する方法が挙げられる。[0014] (with the proviso that in the formula, X and Y are at least one of these represents a -SO 3 M, each represents a hydrogen atom or -SO 3 M, M has the same meaning as above.), Etc. And a rhodamine dye represented by The xanthene derivatives may be used alone or in combination of two or more,
Subjected to reaction with thionyl halide. The thionyl halide is preferably thionyl chloride. Examples of the halogenated aliphatic hydrocarbon solvent include chloroform, methylene chloride, carbon tetrachloride, 1,2-dichloroethane, dichloroethylene, trichloroethylene, perchloroethylene, dichloropropane, amyl chloride, dichloropentane, tetrachloroethane and 1,2-dichloroethane. Dibromoethane and the like can be mentioned, but chloroform is more preferable. In the reaction of the xanthene derivative and the thionyl halide, the amount of N, N-dimethylformamide used relative to the thionyl halide is preferably 1: 0.3 to 1: 0.8 in a molar ratio.
Is the range. Although the amount of thionyl halide used varies depending on the type and purity of the xanthene derivative, it is usually in the range of 1: 1 to 1:20 in molar ratio with respect to the xanthene derivative. In general, when the purity of the xanthene derivative is high, the amount of thionyl halide used may be a chemical equivalent or slightly higher than the chemical equivalent, while when the purity of the xanthene derivative is low due to many impurities such as salt or mirabilite. It is preferable that the amount of thionyl halide used is in excess of the chemical equivalent. The reaction is usually a xanthene derivative,
It is carried out by gradually adding thionyl halide into a mixture of N, N-dimethylformamide and a halogenated aliphatic hydrocarbon solvent. The reaction temperature is usually about 0 to about 70.
C., preferably about 30 to about 60.degree. C., and the reaction time is usually about 30 minutes to 6 hours. The amount of the halogenated aliphatic hydrocarbon solvent used with respect to the xanthene derivative is appropriately set. The sulfonyl halide compound represented by the general formula (II) is usually taken out from the reaction mixture by cooling the above reaction mixture, if necessary, and then pouring it into water or ice water to decompose the remaining thionyl halide, followed by extraction and washing. And conventional means such as concentration. More preferably, a method of subjecting the obtained reaction mixture (a solution of the sulfonyl halide compound and the remaining thionyl halide in a halogenated aliphatic hydrocarbon solvent) to the condensation reaction with the primary amine as it is can be mentioned.
【００１５】上記縮合反応は好ましくは塩基性触媒の存
在下に行なわれ、当該塩基性触媒として例えば、好まし
くはトリエチルアミン、ピリジン、ピペリジン、トリエ
タノールアミン等、脂肪族及び芳香族の２級もしくは３
級アミン等が挙げられ、より好ましくは３級アミンが挙
げられる。前記反応混合物をそのまま前記１級アミンと
の縮合反応に供し、且つ塩基性触媒を用いる場合に、前
記１級アミン及び上記塩基性触媒の合計使用量は、好ま
しくは、前記反応で使用したハロゲン化チオニルに対し
てモル比で１：2.2 〜１：2.5 の範囲である。又、塩基
性触媒を用いる場合には、当該触媒の使用量は１級アミ
ンに対してモル比で通常１：0.5 〜１：1.5 、好ましく
は１：0.8 〜１：1.2 の範囲である。ハロゲン化脂肪族
炭化水素溶媒等の縮合反応溶媒の使用量は適宜設定され
る。縮合反応温度は通常０〜60℃、好ましくは５〜40℃
であり、縮合反応時間は通常30分〜６時間である。一般
式（Ｉ）で示される置換スルホンアミド化合物の縮合反
応混合物からの取り出しは、通常は上記反応混合物を必
要なら冷却後、中和、結晶化、濾過等の慣用手段を用い
て行なわれる。結晶化はより好ましくは、中和後の縮合
反応混合物を30〜60％メタノール水溶液中に注ぐことに
より行なわれる。このようにして、水溶性を付与するス
ルホン酸基等の置換基を１〜５個有する一般式（ＩＩ
Ｉ）で示されるキサンテン誘導体から、当該置換基の少
なくとも１個がスルホニルハライド基に変換された一般
式（ＩＩ）で示されるスルホニルハライド化合物が得ら
れ、当該化合物を単離後、或いは当該化合物を単離する
ことなく１級アミンと縮合反応させることにより、上記
スルホニルハライド化合物のスルホニルハライド基と同
数の置換スルホンアミド基を有する一般式（Ｉ）で示さ
れる置換スルホンアミド化合物が得られる。The above-mentioned condensation reaction is preferably carried out in the presence of a basic catalyst, and the basic catalyst is, for example, preferably triethylamine, pyridine, piperidine, triethanolamine, etc., and an aliphatic or aromatic secondary or tertiary.
Examples thereof include tertiary amines, and more preferably tertiary amines. When the reaction mixture is directly subjected to a condensation reaction with the primary amine and a basic catalyst is used, the total amount of the primary amine and the basic catalyst used is preferably the halogenation used in the reaction. The molar ratio to thionyl is in the range of 1: 2.2 to 1: 2.5. When a basic catalyst is used, the amount of the catalyst used is usually in the range of 1: 0.5 to 1: 1.5, preferably 1: 0.8 to 1: 1.2 with respect to the primary amine in molar ratio. The amount of the condensation reaction solvent such as a halogenated aliphatic hydrocarbon solvent used is appropriately set. The condensation reaction temperature is usually 0 to 60 ° C, preferably 5 to 40 ° C
And the condensation reaction time is usually 30 minutes to 6 hours. Removal of the substituted sulfonamide compound represented by the general formula (I) from the condensation reaction mixture is usually carried out by using a conventional means such as neutralization, crystallization and filtration after cooling the reaction mixture, if necessary. Crystallization is more preferably performed by pouring the condensation reaction mixture after neutralization into a 30-60% methanol aqueous solution. In this way, the compound represented by the general formula (II) having 1 to 5 substituents such as a sulfonic acid group that imparts water solubility is used.
From the xanthene derivative represented by I), a sulfonyl halide compound represented by the general formula (II), in which at least one of the substituents is converted to a sulfonyl halide group, is obtained, and the compound is isolated or isolated. By carrying out a condensation reaction with a primary amine without isolation, a substituted sulfonamide compound represented by the general formula (I) having the same number of substituted sulfonamide groups as the sulfonyl halide group of the sulfonyl halide compound can be obtained.
【００１６】[0016]
【実施例】次に、実施例及び参考例により本発明を更に
具体的に説明する。尚、例中、部は重量部数を表わす。EXAMPLES Next, the present invention will be described more specifically by way of Examples and Reference Examples. In the examples, "part" means "part by weight".
【００１７】実施例１ 下式Example 1 The following formula
【００１８】[0018]
【化９】 [Chemical 9]
【００１９】で示されるスルホローダミンＢ〔関東化学
（株）製酸性染料、色素としての純度90.2％〕40ｇ、ク
ロロホルム300 ｇ及びジメチルホルムアミド12ｇの混合
物に、20℃以下で１時間かけて塩化チオニル42.2ｇを滴
下した。滴下終了後、直ちに40℃で２時間反応させた。
得られた反応混合物に20℃以下で１時間かけて、３−
（２−エチルヘキシルオキシ）プロピルアミン61ｇ及び
トリエチルアミン40.1ｇの混合物を滴下した。40℃で３
時間反応させた。縮合反応終了後、反応混合物を酢酸で
中和し、中和後の混合物を1800ｇの40％メタノール水溶
液中に注いで結晶化させた。得られた結晶を濾過後、60
℃で３日間乾燥して置換スルホンアミド化合物を得た。
スルホローダミンＢに対する収率は82.9％であり、置換
スルホンアミド化合物の純度（LC）は95.1％であった。A mixture of 40 g of sulforhodamine B (an acid dye manufactured by Kanto Kagaku Co., Ltd., a purity of 90.2% as a pigment), 300 g of chloroform and 12 g of dimethylformamide was added to thionyl chloride 42.2 at 20 ° C. or below for 1 hour. g was added dropwise. Immediately after completion of dropping, the reaction was carried out at 40 ° C. for 2 hours.
The resulting reaction mixture was heated at 20 ° C. or below for 1 hour to give 3-
A mixture of 61 g of (2-ethylhexyloxy) propylamine and 40.1 g of triethylamine was added dropwise. 3 at 40 ° C
Reacted for hours. After the completion of the condensation reaction, the reaction mixture was neutralized with acetic acid, and the neutralized mixture was poured into 1800 g of 40% aqueous methanol solution for crystallization. The obtained crystals were filtered and then 60
A substituted sulfonamide compound was obtained by drying at 3 ° C. for 3 days.
The yield based on sulforhodamine B was 82.9%, and the purity (LC) of the substituted sulfonamide compound was 95.1%.
【００２０】実施例２ ３−（２−エチルヘキシルオキシ）プロピルアミンに代
えて下式 ＣＨ3 ＣＨ2 Ｏ（ＣＨ2 ）3 ＮＨ2 で示されるアミン37.43 ｇを用いる以外は実施例１と同
様に操作して置換スルホンアミド化合物を得た。収率は
80.1％であり、純度は89.3％であった。Example 2 The same procedure as in Example 1 was repeated except that 37.43 g of an amine represented by the following formula CH 3 CH 2 O (CH 2 ) 3 NH 2 was used in place of 3- (2-ethylhexyloxy) propylamine. To obtain a substituted sulfonamide compound. The yield is
It was 80.1% and the purity was 89.3%.
【００２１】実施例３ ３−（２−エチルヘキシルオキシ）プロピルアミンに代
えて下式Example 3 The following formula was used in place of 3- (2-ethylhexyloxy) propylamine.
【００２２】[0022]
【化１０】 [Chemical 10]
【００２３】で示されるアミン40.2ｇを用い、且つトリ
エチルアミン量を45.3ｇに変える以外は実施例１と同様
に操作して置換スルホンアミド化合物を得た。収率は7
0.5％であり、純度は85.1％であった。A substituted sulfonamide compound was obtained in the same manner as in Example 1 except that 40.2 g of the amine represented by was used and the amount of triethylamine was changed to 45.3 g. Yield 7
It was 0.5% and the purity was 85.1%.
【００２４】実施例４ 下式Example 4 The following formula
【００２５】[0025]
【化１１】 [Chemical 11]
【００２６】で示される色素〔色素としての純度91.3
％〕47.7ｇ、クロロホルム400 ｇ及びジメチルホルムア
ミド16.7ｇの混合物に、20℃以下で１時間かけて塩化チ
オニル45ｇを滴下した。滴下終了後、直ちに40℃で１時
間30分反応させた。得られた反応混合物に20℃以下で１
時間かけて、３−（２−エチルヘキシルオキシ）プロピ
ルアミン79.6ｇ及びトリエチルアミン59.5ｇの混合物を
滴下した。40℃で３時間反応させた。縮合反応終了後、
反応混合物を酢酸で中和し、中和後の混合物を2500ｇの
45％メタノール水溶液中に注いで結晶化させた。得られ
た結晶を濾過後、60℃で３日間乾燥して置換スルホンア
ミド化合物を得た。上式で示される色素に対する収率は
85.3％であり、置換スルホンアミド化合物の純度（LC）
は94.9％であった。A dye represented by [purity as a dye 91.3
%] 47.7 g, chloroform 400 g, and dimethylformamide 16.7 g were added dropwise with thionyl chloride 45 g at 20 ° C. or lower over 1 hour. Immediately after completion of the dropping, reaction was carried out at 40 ° C. for 1 hour and 30 minutes. 1 at below 20 ° C for the resulting reaction mixture
A mixture of 79.6 g of 3- (2-ethylhexyloxy) propylamine and 59.5 g of triethylamine was added dropwise over time. The reaction was carried out at 40 ° C for 3 hours. After the condensation reaction,
The reaction mixture was neutralized with acetic acid, and the mixture after neutralization was treated with 2500 g of
Crystallization was performed by pouring into a 45% aqueous methanol solution. The obtained crystals were filtered and then dried at 60 ° C. for 3 days to obtain a substituted sulfonamide compound. The yield for the dye represented by the above formula is
85.3%, purity of the substituted sulfonamide compound (LC)
Was 94.9%.
【００２７】参考例１ ｍ−クレゾール、ｐ−クレゾール及びホルムアルデヒド
混合物（モル比＝５／５／7.5 ）から得られたクレゾー
ルノボラック樹脂（分子量2500）２ｇ、実施例１で得た
置換スルホンアミド化合物２ｇ、ヘキサメトキシメチロ
ール化メラミン１ｇ、下式Reference Example 1 2 g of cresol novolac resin (molecular weight 2500) obtained from a mixture of m-cresol, p-cresol and formaldehyde (molar ratio = 5/5 / 7.5), 2 g of substituted sulfonamide compound obtained in Example 1. , Hexamethoxymethylolated melamine 1 g, the following formula
【００２８】[0028]
【化１２】 [Chemical 12]
【００２９】で示されるフェノール化合物のｏ−ナフト
キノンジアジド−５−スルホン酸エステル（平均２個の
水酸基がエステル化されている）２ｇ、ジメチルホルム
アミド５ｇ並びに乳酸エチル12ｇを混合後、メンブラン
フィルターを用いて加圧濾過してポジ型レジスト組成物
を得た。上で得たポジ型レジスト組成物を、シリコンウ
エハーにスピンコートした後、100 ℃・１分加熱した。
このシリコンウエハーを露光後、アルカリ現像により露
光部を除去して0.8 μｍの解像度を有するマゼンタ色の
ポジ型パターンを得た。上で得たポジ型パターンを全面
露光後、150 ℃・15分加熱してカラーフィルターを得
た。このカラーフィルターは１μｍ以下の膜厚で優れた
性能を示した。After mixing 2 g of an o-naphthoquinonediazide-5-sulfonic acid ester of a phenol compound represented by the formula (on average two hydroxyl groups are esterified), 5 g of dimethylformamide and 12 g of ethyl lactate, a membrane filter was used. Pressure filtration was performed to obtain a positive resist composition. The positive resist composition obtained above was spin-coated on a silicon wafer and then heated at 100 ° C. for 1 minute.
After exposing this silicon wafer, the exposed portion was removed by alkali development to obtain a magenta-color positive type pattern having a resolution of 0.8 μm. The positive type pattern obtained above was exposed on the entire surface and then heated at 150 ° C. for 15 minutes to obtain a color filter. This color filter showed excellent performance at a film thickness of 1 μm or less.
【００３０】[0030]
【発明の効果】本発明によれば、スルホニルハライド化
合物及び置換スルホンアミド化合物を高純度且つ高収率
で製造することができる。According to the present invention, a sulfonyl halide compound and a substituted sulfonamide compound can be produced with high purity and high yield.
Claims (7)
れていてもよいアルキル、アルケニル、シクロアルキ
ル、アラルキルもしくはアリール基を表わし、Ｍは水
素、アルカリ金属もしくはアルカリ土類金属原子又は４
級アンモニウム塩を表わし、ｍは１〜５の整数を表わ
す。ＳＯ3 ＭはＳＯ3 - で置換されているベンゼン環及
びＲ1 〜Ｒ4 で表わされるアラルキルもしくはアリール
基の何れか或いは双方の置換基である。）で示されるキ
サンテン誘導体とハロゲン化チオニルとを、Ｎ，Ｎ−ジ
メチルホルムアミド及びハロゲン化脂肪族炭化水素溶媒
の存在下に反応させることを特徴とする一般式（ＩＩ） 【化２】 （式中、Ｒ1 〜Ｒ7 及びＭは上記と同じ意味を表わし、
Ｘはハロゲン原子を表わし、ｋは０〜４の整数を表わ
し、ｎは１〜５の整数を表わすが、ｋ＋ｎ＝ｍであ
る。）で示されるスルホニルハライド化合物の製造方
法。1. A compound represented by the general formula (III): (In the formula, R 1 to R 7 each independently represent a hydrogen atom or an optionally substituted alkyl, alkenyl, cycloalkyl, aralkyl or aryl group, and M represents a hydrogen atom, an alkali metal or alkaline earth metal atom, or Four
Represents a primary ammonium salt, and m represents an integer of 1 to 5. SO 3 M is a substituent of either or both of the benzene ring substituted with SO 3 − and the aralkyl or aryl group represented by R 1 to R 4 . ) And a thionyl halide represented by the formula (II) are reacted in the presence of N, N-dimethylformamide and a halogenated aliphatic hydrocarbon solvent. (In the formula, R 1 to R 7 and M have the same meanings as described above,
X represents a halogen atom, k represents an integer of 0 to 4, n represents an integer of 1 to 5, and k + n = m. ) The manufacturing method of the sulfonyl halide compound shown by these.
れるキサンテン誘導体とハロゲン化チオニルとを、Ｎ，
Ｎ−ジメチルホルムアミド及びハロゲン化脂肪族炭化水
素溶媒の存在下に反応させて請求項１に記載の一般式
（ＩＩ）で示されるスルホニルハライド化合物を得、次
いで、当該スルホニルハライド化合物を下式 Ｒ−ＮＨ2 （式中、Ｒは置換されていてもよいアルキル、シクロヘ
キシルアルキル、アルキルカルボニルアミノアルキル、
アルコキシ、アルコキシアルキル、アリール、アラルキ
ルもしくはシクロアルキル基を表わす。）で示される１
級アミンと縮合反応させることを特徴とする一般式
（Ｉ） 【化３】 （式中、Ｒ1 〜Ｒ7 、ｋ、ｎ、Ｍ及びＲは上記と同じ意
味を表わす。）で示される置換スルホンアミド化合物の
製造方法。2. A xanthene derivative represented by the general formula (III) according to claim 1 and a thionyl halide are mixed with N,
The reaction is carried out in the presence of N-dimethylformamide and a halogenated aliphatic hydrocarbon solvent to obtain a sulfonyl halide compound represented by the general formula (II) according to claim 1, and then the sulfonyl halide compound is converted to the following formula R- NH 2 (wherein R is an optionally substituted alkyl, cyclohexylalkyl, alkylcarbonylaminoalkyl,
Represents an alkoxy, alkoxyalkyl, aryl, aralkyl or cycloalkyl group. ) 1
A compound of the general formula (I), characterized in that it is subjected to a condensation reaction with a primary amine (In the formula, R 1 to R 7 , k, n, M and R have the same meanings as described above.) A method for producing a substituted sulfonamide compound.
求項２に記載の置換スルホンアミド化合物の製造方法。3. The method for producing a substituted sulfonamide compound according to claim 2, wherein the condensation reaction is carried out in the presence of a basic catalyst.
記載の置換スルホンアミド化合物の製造方法。4. The method for producing a substituted sulfonamide compound according to claim 3, wherein the basic catalyst is a tertiary amine.
ルムである請求項１〜４のいずれかに記載の製造方法。5. The method according to claim 1, wherein the halogenated aliphatic hydrocarbon solvent is chloroform.
請求項１〜５のいずれかに記載の製造方法。6. The production method according to claim 1, wherein the thionyl halide is thionyl chloride.
チルホルムアミドの使用量がモル比で１：0.3 〜１：0.
8 である請求項１〜６のいずれかに記載の製造方法。7. A molar ratio of N, N-dimethylformamide to thionyl halide used is 1: 0.3 to 1: 0.
The method according to any one of claims 1 to 6, which is 8.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6034837A JPH07242651A (en) | 1994-03-04 | 1994-03-04 | Production of sulfonyl halide compound and substituted sulfonamide compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6034837A JPH07242651A (en) | 1994-03-04 | 1994-03-04 | Production of sulfonyl halide compound and substituted sulfonamide compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH07242651A true JPH07242651A (en) | 1995-09-19 |
Family
ID=12425317
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6034837A Pending JPH07242651A (en) | 1994-03-04 | 1994-03-04 | Production of sulfonyl halide compound and substituted sulfonamide compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07242651A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0947563A1 (en) * | 1998-03-31 | 1999-10-06 | Canon Kabushiki Kaisha | Ink, color filter, liquid crystal panel, and computer, and process for producing color filter |
| WO2006088171A1 (en) * | 2005-02-15 | 2006-08-24 | Canon Kabushiki Kaisha | Novel colorant compound and method of manufacturing the same as well as blue resist composition for use in color filter containing the same |
| JP2006257410A (en) * | 2005-02-15 | 2006-09-28 | Canon Inc | Coloring liquid, coloring liquid for inkjet recording method, ink tank, recording unit, recording device and recording method |
| JP2006257411A (en) * | 2005-02-15 | 2006-09-28 | Canon Inc | New pigment compound, manufacturing method thereof, and blue resist composition containing this pigment compound for use in color filter |
-
1994
- 1994-03-04 JP JP6034837A patent/JPH07242651A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0947563A1 (en) * | 1998-03-31 | 1999-10-06 | Canon Kabushiki Kaisha | Ink, color filter, liquid crystal panel, and computer, and process for producing color filter |
| US6203604B1 (en) | 1998-03-31 | 2001-03-20 | Canon Kabushiki Kaisha | Ink, color filter, liquid crystal panel, and computer, and process for producing color filter |
| WO2006088171A1 (en) * | 2005-02-15 | 2006-08-24 | Canon Kabushiki Kaisha | Novel colorant compound and method of manufacturing the same as well as blue resist composition for use in color filter containing the same |
| JP2006257410A (en) * | 2005-02-15 | 2006-09-28 | Canon Inc | Coloring liquid, coloring liquid for inkjet recording method, ink tank, recording unit, recording device and recording method |
| JP2006257411A (en) * | 2005-02-15 | 2006-09-28 | Canon Inc | New pigment compound, manufacturing method thereof, and blue resist composition containing this pigment compound for use in color filter |
| US7973197B2 (en) | 2005-02-15 | 2011-07-05 | Canon Kabushiki Kaisha | Colorant compound and blue resist composition for use in color filter containing the same |
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