JPH0598243A - Production of near-infrared absorber - Google Patents
Production of near-infrared absorberInfo
- Publication number
- JPH0598243A JPH0598243A JP3282020A JP28202091A JPH0598243A JP H0598243 A JPH0598243 A JP H0598243A JP 3282020 A JP3282020 A JP 3282020A JP 28202091 A JP28202091 A JP 28202091A JP H0598243 A JPH0598243 A JP H0598243A
- Authority
- JP
- Japan
- Prior art keywords
- tetrakis
- phenylenediamine
- solid catalyst
- salt
- formula
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、近赤外線吸収剤である
アミニウム塩の製造方法に関する。さらに詳しくは、
Ｎ,Ｎ,Ｎ',Ｎ'−テトラキス（p−ジアルキルアミノフェ
ニル）−p−フェニレンジアミンのアミニウム塩の製造
方法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing an aminium salt which is a near infrared absorber. For more details,
The present invention relates to a method for producing an aminium salt of N, N, N ', N'-tetrakis (p-dialkylaminophenyl) -p-phenylenediamine.
【０００２】[0002]
【従来の技術】Ｎ,Ｎ,Ｎ',Ｎ'−テトラキス（p−ジアル
キルアミノフェニル）−p−フェニレンジアミンのアミ
ニウム塩は、近赤外領域に強い吸収を持ち、近赤外線吸
収剤として有用であり、また有機合成樹脂の光吸収安定
化剤として用いられる。Ｎ,Ｎ,Ｎ',Ｎ'−テトラキス（p
−ジアルキルアミノフェニル）−p−フェニレンジアミ
ンのアミニウム塩の製造方法については、特公昭４３−
２５３３５号公報、特公昭４６−５８１０号公報、特開
昭６３−２９０２８８号公報で、Ｎ,Ｎ,Ｎ',Ｎ'−テト
ラキス（p−ジアルキルアミノフェニル）−p−フェニレ
ンジアミンに過塩素酸銀等の銀塩を用いてアミニウム塩
を得る方法、または電解法によって酸化する方法の記載
がある。また、特開平２−３１１４４７号公報には、第
２鉄塩を用いた方法が開示されている。BACKGROUND OF THE INVENTION N, N, N ', N'-tetrakis (p-dialkylaminophenyl) -p-phenylenediamine aminium salts have strong absorption in the near infrared region and are useful as near infrared absorbers. It is also used as a light absorption stabilizer for organic synthetic resins. N, N, N ', N'-tetrakis (p
The method for producing an aminium salt of -dialkylaminophenyl) -p-phenylenediamine is described in JP-B-43-
No. 25335, Japanese Patent Publication No. 46-5810, and Japanese Patent Laid-Open No. 63-290288, N, N, N ', N'-tetrakis (p-dialkylaminophenyl) -p-phenylenediamine and silver perchlorate. There is a description of a method of obtaining an aminium salt using a silver salt such as, or a method of oxidizing by an electrolytic method. Further, Japanese Patent Application Laid-Open No. 2-311447 discloses a method using a ferric salt.
【０００３】[0003]
【発明が解決しようとする課題】特公昭４３−２５３３
５号公報には、高価な銀塩を用いた化学的酸化法が記載
されているが、銀塩が反応して金属銀となるため生成物
からの除去が難しく、また銀塩は極めて鋭敏な爆発性を
有しているため取扱いが困難である。特公昭４６−５８
１０号公報には金属塩を用いた電解方法が記載されてい
るが、陰極に金属が析出するため長時間の電解が困難で
ある。特開昭６３−２９０２８８号公報に開示されてい
る電解による製造方法では、陰極に金属は析出しない
が、電解槽を用いているため製造コストが高いという欠
点がある。特開平１−３１１４４７号公報では、生成物
に微量の鉄が含有されることがあり、高純度を必要とす
る用途には不向きである。[Problems to be Solved by the Invention] Japanese Patent Publication No. 43-2533
Japanese Patent Laid-Open No. 5 (1993) describes a chemical oxidation method using an expensive silver salt, but it is difficult to remove from the product because the silver salt reacts to form metallic silver, and the silver salt is extremely sensitive. It is explosive and difficult to handle. Japanese Examined Japanese Patent Publication 46-58
No. 10 discloses an electrolysis method using a metal salt, but it is difficult to electrolyze for a long time because a metal is deposited on the cathode. The production method by electrolysis disclosed in JP-A-63-290288 does not deposit metal on the cathode, but has the drawback of high production cost because an electrolytic cell is used. In Japanese Patent Laid-Open No. 1-311447, the product may contain a trace amount of iron, and is not suitable for applications requiring high purity.
【０００４】本発明の目的は、前記のような問題点を解
決し、高純度のＮ,Ｎ,Ｎ',Ｎ'−テトラキス（p−ジアル
キルアミノフェニル）−p−フェニレンジアミンのアミ
ニウム塩を効率よく製造する方法を提供することであ
る。The object of the present invention is to solve the above-mentioned problems and to efficiently use a highly pure aminium salt of N, N, N ', N'-tetrakis (p-dialkylaminophenyl) -p-phenylenediamine. It is to provide a method of manufacturing well.
【０００５】[0005]
【問題点を解決するための手段】本発明者らは、鋭意検
討を重ねた結果、本発明を完成した。本発明は、化１
（式中、Ｒ1、Ｒ2は炭素数が２〜６のアルキル基を示
し、同じでも異なっていてもよい。）で表される化合物
を固体触媒の存在下で反応させることを特徴とする化２
（式中、Ｒ1、Ｒ2は炭素数が２〜６のアルキル基を示
し、同じでも異なっていてもよく、mは１または２の整
数を示し、Ｘはアニオン成分で表される）で表される近
赤外線吸収剤のアミニウム塩の製造方法である。アニオ
ン成分としては、塩素、臭素、過塩素酸、硝酸、６フッ
化アンチモン、４フッ化ホウ素、トルエンスルホン酸、
ベンゼンスルホン酸、チオシアンイオン等があげられ
る。The present inventors have completed the present invention as a result of intensive studies. The present invention is
(Wherein R 1 and R 2 represent an alkyl group having 2 to 6 carbon atoms and may be the same or different) and are reacted in the presence of a solid catalyst. Chemical 2
(In the formula, R 1 and R 2 each represent an alkyl group having 2 to 6 carbon atoms, which may be the same or different, m represents an integer of 1 or 2, and X represents an anion component). It is a method for producing an aminium salt of a near infrared absorber represented. As the anion component, chlorine, bromine, perchloric acid, nitric acid, antimony hexafluoride, boron tetrafluoride, toluenesulfonic acid,
Examples thereof include benzenesulfonic acid and thiocyanate.
【０００６】固体触媒としては、銀、チタン、バナジウ
ム、鉄、クロム、マンガン、コバルト、ニッケル、鉛の
酸化物、及び白金族金属及びその酸化物の少なくとも１
種以上を含有したものが使用できる。これらの固体触媒
は、粉末状、またはアルミナ等の担体に担持して使用さ
れる。酸化物としては、高次の酸化物が望ましい。As the solid catalyst, at least one of oxides of silver, titanium, vanadium, iron, chromium, manganese, cobalt, nickel, lead, and platinum group metals and their oxides is used.
Those containing more than one species can be used. These solid catalysts are used in the form of powder or supported on a carrier such as alumina. Higher order oxides are desirable.
【０００７】[0007]
【化１】[Chemical 1]
【０００８】[0008]
【化２】[Chemical 2]
【０００９】反応に用いる溶媒は、親水性有機溶媒、例
えばメタノール、ブタノール、プロパノールなどのアル
コール類、アセトン、メチルイソブチルケトン、メチル
エチルケトンなどのケトン類、メチルセロソルブ、エチ
ルセロソルブ、ブチルセロソルフ、トリエチレングリコ
ールモノブチルエーテルなどのグリコールのエーテル
類、酢酸エチル等のエステル類、アセトニトリル、ジメ
チルホルムアミド、ジメチルスルホキシド、ジメチルア
セチルアミド、あるいはこれらの混合溶媒が使用でき
る。また、溶媒は、水あるいは疎水性有機溶媒を少量含
んでいてもよい。溶媒の使用量は、反応基質１重量部に
対して20〜80重量部である。反応温度は、室温から180
℃、好ましくは40〜120℃である。反応は数時間で終了
し、その後、固体触媒と溶媒を除去した後、未反応物を
除去し、化２のアミニウム塩を得ることができる。The solvent used in the reaction is a hydrophilic organic solvent such as alcohols such as methanol, butanol and propanol, ketones such as acetone, methyl isobutyl ketone and methyl ethyl ketone, methyl cellosolve, ethyl cellosolve, butyl cellosolve and triethylene glycol monobutyl ether. Ethers of glycol such as, esters such as ethyl acetate, acetonitrile, dimethylformamide, dimethylsulfoxide, dimethylacetylamide, or a mixed solvent thereof can be used. Further, the solvent may contain a small amount of water or a hydrophobic organic solvent. The amount of the solvent used is 20 to 80 parts by weight with respect to 1 part by weight of the reaction substrate. The reaction temperature ranges from room temperature to 180
℃, preferably 40-120 ℃. The reaction is completed in several hours, after which the solid catalyst and the solvent are removed, and then the unreacted substances are removed to obtain the aminium salt of Chemical formula 2.
【００１０】反応時間が短いと化２のm＝１の生成物が
得られ、反応時間が長くなるとm＝２の生成物が得られ
る。したがって反応時間を制御することによりmを制御
することができる。When the reaction time is short, the product of m = 1 in Chemical formula 2 is obtained, and when the reaction time is long, the product of m = 2 is obtained. Therefore, m can be controlled by controlling the reaction time.
【００１１】固体触媒は、反応によって活性が低下しな
いので繰り返して使用できる。触媒の種類によって多少
異なるが、どの触媒でも３回の使用では、生成物の収率
にほとんど差がなかった。Since the activity of the solid catalyst does not decrease due to the reaction, it can be used repeatedly. Although there were some differences depending on the type of the catalyst, there was almost no difference in the yield of the product when the catalysts were used three times with each catalyst.
【００１２】[0012]
【実施例】以下、実施例で本発明を説明する。The present invention will be described below with reference to examples.
【００１３】実施例１ Ｎ,Ｎ,Ｎ',Ｎ'−テトラキス（p−ジブチルアミノフェニ
ル−p−フェニレンジアミン9.2ｇをアセトニトリル100m
l、酢酸エチル180mlの混合溶媒に溶解し、過塩素酸ナト
リウム1.3ｇを含む水溶液５mlとアルミナ担体に白金を
被覆した固体触媒30ｇを加え、60℃で４時間攪拌した。
反応混合物を水洗、減圧濃縮した後、n−ヘキサン450ml
中に投入し、析出した固体をろ別した後、水洗、乾燥し
て緑色粉末9.8ｇを得た。生成物は、アセトン中の極大
吸収波長が950nm、モル吸光係数が2.0×104、融点が159
℃で、Ｎ,Ｎ,Ｎ',Ｎ'−テトラキス（p−ジブチルアミノ
フェニル）−p−フェニレンジアミンのモノパークロレ
ート塩であった。Example 1 N, N, N ', N'-tetrakis (p-dibutylaminophenyl-p-phenylenediamine) (9.2 g) was added to 100 m of acetonitrile.
1, dissolved in a mixed solvent of 180 ml of ethyl acetate, added with 5 ml of an aqueous solution containing 1.3 g of sodium perchlorate, and 30 g of a platinum-coated solid catalyst on an alumina carrier, and stirred at 60 ° C for 4 hours.
The reaction mixture was washed with water and concentrated under reduced pressure, then 450 ml of n-hexane.
The mixture was put into a container, the precipitated solid was separated by filtration, washed with water and dried to obtain 9.8 g of a green powder. The product has a maximum absorption wavelength in acetone of 950 nm, a molar absorption coefficient of 2.0 × 10 4 , and a melting point of 159.
At C, it was the monoperchlorate salt of N, N, N ', N'-tetrakis (p-dibutylaminophenyl) -p-phenylenediamine.
【００１４】実施例２ 実施例１において、過塩素酸ナトリウムが2.6ｇ、反応
時間が８時間であること以外は、実施例１と同様にし
て、青色粉末10.2ｇを得た。生成物は、アセトン中の極
大吸収波長が1078nm、モル吸光係数が9.2×104、融点が
175℃で、Ｎ,Ｎ,Ｎ',Ｎ'−テトラキス（p−ジブチルア
ミノフェニル）−p−フェニレンジアミンのジパークロ
レート塩であった。Example 2 Blue powder 10.2 g was obtained in the same manner as in Example 1 except that sodium perchlorate was 2.6 g and the reaction time was 8 hours. The product has a maximum absorption wavelength in acetone of 1078 nm, a molar extinction coefficient of 9.2 × 10 4 , and a melting point of
At 175 ° C. it was the diperchlorate salt of N, N, N ′, N′-tetrakis (p-dibutylaminophenyl) -p-phenylenediamine.
【００１５】実施例３ 実施例１において、過塩素酸ナトリウム1.3ｇの代わり
にチオシアン酸ナトリウム１ｇを用いる以外は、実施例
１と同様にして、緑色粉末9.7ｇを得た。生成物は、ア
セトン中の極大吸収波長が939nm、モル吸光係数が2.0×
104、融点が120℃で、Ｎ,Ｎ,Ｎ',Ｎ'−テトラキス（p−
ジブチルアミノフェニル）−p−フェニレンジアミンの
モノチオシアン酸塩であった。Example 3 Green powder 9.7 g was obtained in the same manner as in Example 1 except that 1 g of sodium thiocyanate was used instead of 1.3 g of sodium perchlorate. The product has a maximum absorption wavelength in acetone of 939 nm and a molar absorption coefficient of 2.0 ×.
10 4 , melting point 120 ° C., N, N, N ′, N′-tetrakis (p-
It was the monothiocyanate salt of dibutylaminophenyl) -p-phenylenediamine.
【００１６】実施例４ 実施例１において、過塩素酸ナトリウム1.3ｇの代わり
に４フッ化ホウ素酸リチウム１ｇを用いる以外は、実施
例１と同様にして、緑色粉末9.6ｇを得た。生成物は、
アセトン中の極大吸収波長が932nm、モル吸光係数が1.8
×104、融点が156℃で、Ｎ,Ｎ,Ｎ',Ｎ'−テトラキス（p
−ジブチルアミノフェニル）−p−フェニレンジアミン
のモノ４フッ化ホウ素酸塩であった。Example 4 In the same manner as in Example 1 except that 1 g of lithium tetrafluoroborate was used instead of 1.3 g of sodium perchlorate, 9.6 g of green powder was obtained. The product is
Maximum absorption wavelength in acetone is 932nm, molar absorption coefficient is 1.8
× 10 4 , melting point 156 ° C, N, N, N ', N'-tetrakis (p
-Dibutylaminophenyl) -p-phenylenediamine monotetrafluoroborate.
【００１７】実施例５ Ｎ,Ｎ,Ｎ',Ｎ'−テトラキス（p−ジブチルアミノフェニ
ル）−p−フェニレンジアミン9.2ｇをジメチルホルムア
ミド400mlに溶解し、６フッ化アンチモン酸ナトリウム
2.6ｇを含む水溶液40mlとアルミナ担体にパラジウムを
担持した固体触媒40ｇを加え、50℃で４時間攪拌した。
反応混合物を水500ml中に投入し、析出した固体をろ別
した後、水洗、乾燥して緑色粉末10.6ｇを得た。生成物
は、アセトン中の極大吸収波長が955nm、モル吸光係数
が2.1×104、融点が160℃で、Ｎ,Ｎ,Ｎ',Ｎ'−テトラキ
ス（p−ジブチルアミノフェニル）−p−フェニレンジア
ミンのモノ６フッ化アンチモン酸塩であった。Example 5 9.2 g of N, N, N ', N'-tetrakis (p-dibutylaminophenyl) -p-phenylenediamine was dissolved in 400 ml of dimethylformamide to give sodium hexafluoroantimonate.
40 ml of an aqueous solution containing 2.6 g and 40 g of a solid catalyst supporting palladium on an alumina carrier were added, and the mixture was stirred at 50 ° C. for 4 hours.
The reaction mixture was poured into 500 ml of water, the precipitated solid was filtered off, washed with water and dried to obtain 10.6 g of a green powder. The product has a maximum absorption wavelength in acetone of 955 nm, a molar extinction coefficient of 2.1 × 10 4 , a melting point of 160 ° C., and is N, N, N ′, N′-tetrakis (p-dibutylaminophenyl) -p-phenylene. It was the monohexafluoroantimonate of diamine.
【００１８】実施例６ Ｎ,Ｎ,Ｎ',Ｎ'−テトラキス（p−ジイソプロピルアミノ
フェニル）−p−フェニレンジアミン8.6ｇをアセトニト
リル100ml、酢酸エチル180mlの混合溶媒に溶解し、過塩
素酸ナトリウム１ｇを含む水溶液５mlと固体触媒として
二酸化鉛10ｇを加え、60℃で４時間攪拌した。反応混合
物を水洗、減圧濃縮した後、n−ヘキサン450ml中に投入
し、析出した固体をろ別した後、水洗、乾燥して緑色粉
末9.3ｇを得た。生成物は、アセトン中の極大吸収波長
が957nm、モル吸光係数が2.1×104、融点が158℃で、
Ｎ,Ｎ,Ｎ',Ｎ'−テトラキス（p−ジイソプロピルアミノ
フェニル）−p−フェニレンジアミンのモノパークロレ
ート塩であった。Example 6 8.6 g of N, N, N ', N'-tetrakis (p-diisopropylaminophenyl) -p-phenylenediamine was dissolved in a mixed solvent of 100 ml of acetonitrile and 180 ml of ethyl acetate to give 1 g of sodium perchlorate. 5 ml of an aqueous solution containing the above and 10 g of lead dioxide as a solid catalyst were added, and the mixture was stirred at 60 ° C. for 4 hours. The reaction mixture was washed with water, concentrated under reduced pressure, put into 450 ml of n-hexane, the precipitated solid was filtered off, washed with water and dried to obtain 9.3 g of a green powder. The product has a maximum absorption wavelength in acetone of 957 nm, a molar extinction coefficient of 2.1 × 10 4 , and a melting point of 158 ° C.
It was a monoperchlorate salt of N, N, N ', N'-tetrakis (p-diisopropylaminophenyl) -p-phenylenediamine.
【００１９】実施例７ Ｎ,Ｎ,Ｎ',Ｎ'−テトラキス（p−ジエチルアミノフェニ
ル）−p−フェニレンジアミン8.1ｇをアセトニトリル10
0ml、酢酸エチル200mlの混合溶媒に溶解し、過塩素酸ナ
トリウム1.3ｇを含む水溶液５mlとアルミナ−シリカ担
体にパラジウムを被覆した固体触媒30ｇを加え、65℃で
４時間攪拌した。反応混合物を水洗、減圧濃縮した後、
n−ヘキサン450ml中に投入し、析出した固体をろ別した
後、水洗、乾燥して緑色粉末8.8ｇを得た。生成物は、
アセトン中の極大吸収波長が965nm、モル吸光係数が2.0
×104、融点が153℃で、Ｎ,Ｎ,Ｎ',Ｎ'−テトラキス（p
−ジエチルアミノフェニル）−p−フェニレンジアミン
のモノパークロレート塩であった。Example 7 8.1 g of N, N, N ', N'-tetrakis (p-diethylaminophenyl) -p-phenylenediamine was added to 10 g of acetonitrile.
The mixture was dissolved in a mixed solvent of 0 ml and 200 ml of ethyl acetate, 5 ml of an aqueous solution containing 1.3 g of sodium perchlorate and 30 g of a solid catalyst in which an alumina-silica carrier was coated with palladium were added, and the mixture was stirred at 65 ° C. for 4 hours. After washing the reaction mixture with water and concentrating under reduced pressure,
The mixture was poured into 450 ml of n-hexane, the precipitated solid was filtered off, washed with water and dried to obtain 8.8 g of a green powder. The product is
Maximum absorption wavelength in acetone is 965 nm, molar absorption coefficient is 2.0
× 10 4 , melting point 153 ° C., N, N, N ′, N′-tetrakis (p
-Diethylaminophenyl) -p-phenylenediamine monoperchlorate salt.
【００２０】実施例８ 実施例５において、６フッ化アンチモン酸ナトリウムが
6.0ｇ、反応時間が８時間であること以外は、実施例５
と同様にして、青色粉末15.1ｇを得た。生成物は、アセ
トン中の極大吸収波長が1078nm、モル吸光係数が9.1×1
04、融点が240℃で、Ｎ,Ｎ,Ｎ',Ｎ'−テトラキス（p−
ジブチルアミノフェニル）−p−フェニレンジアミンの
ジ６フッ化アンチモン酸塩であった。Example 8 In Example 5, sodium hexafluoroantimonate was
Example 5 except 6.0 g, reaction time 8 hours
In the same manner as in the above, 15.1 g of blue powder was obtained. The product has a maximum absorption wavelength in acetone of 1078 nm and a molar absorption coefficient of 9.1 x 1
0 4 , melting point 240 ° C., N, N, N ′, N′-tetrakis (p-
It was the dihexafluoroantimonate salt of dibutylaminophenyl) -p-phenylenediamine.
【００２１】実施例９ Ｎ,Ｎ,Ｎ',Ｎ'−テトラキス（p−ジブチルアミノフェニ
ル）−p−フェニレンジアミン9.2ｇをジメチルホルムア
ミド400mlに溶解し、臭化ナトリウム2.0ｇを含む水溶液
40mlと固体触媒として二酸化マンガン7ｇを加え、70℃
で３時間攪拌した。反応混合物を水洗、減圧濃縮した
後、n−ヘキサン450ml中に投入し、析出した固体をろ別
した後、水洗、乾燥して緑色粉末9.1ｇを得た。生成物
は、アセトン中の極大吸収波長が960nm、モル吸光係数
が2.1×104、融点が160℃で、Ｎ,Ｎ,Ｎ',Ｎ'−テトラキ
ス（p−ジブチルアミノフェニル）−p−フェニレンジア
ミンの臭化物であった。Example 9 An aqueous solution containing 9.2 g of N, N, N ', N'-tetrakis (p-dibutylaminophenyl) -p-phenylenediamine dissolved in 400 ml of dimethylformamide and containing 2.0 g of sodium bromide.
40 ml and 7 g of manganese dioxide as a solid catalyst were added, and the temperature was 70 ° C.
And stirred for 3 hours. The reaction mixture was washed with water, concentrated under reduced pressure, put into 450 ml of n-hexane, the precipitated solid was filtered off, washed with water and dried to obtain 9.1 g of a green powder. The product has a maximum absorption wavelength in acetone of 960 nm, a molar extinction coefficient of 2.1 × 10 4 , a melting point of 160 ° C., and is N, N, N ′, N′-tetrakis (p-dibutylaminophenyl) -p-phenylene. It was a bromide of a diamine.
【００２２】[0022]
【発明の効果】固体触媒を用いる本発明によれば、高純
度のＮ,Ｎ,Ｎ',Ｎ'−テトラキス（p−ジアルキルアミノ
フェニル）−p−フェニレンジアミンのアミニウム塩
を、電解槽等の特殊な設備を用いることなく、容易にか
つ効率よく製造することができる。According to the present invention using a solid catalyst, a high-purity N, N, N ', N'-tetrakis (p-dialkylaminophenyl) -p-phenylenediamine aminium salt is used in an electrolytic cell or the like. It can be easily and efficiently manufactured without using special equipment.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｂ０１Ｊ 23/34 23/40 23/50 23/74 Ｃ０７Ｃ 209/00 6917−4Ｈ 211/54 6917−4Ｈ // Ｃ０７Ｂ 61/00 ３００ (72)発明者 平形 薫 群馬県渋川市半田2470番地 日本カーリツ ト株式会社中央研究所内─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification number Office reference number FI technical display location B01J 23/34 23/40 23/50 23/74 C07C 209/00 6917-4H 211/54 6917- 4H // C07B 61/00 300 (72) Inventor Kaoru Hirakata 2470 Handa, Shibukawa City, Gunma Japan Central Research Center, Japan Carlit Co., Ltd.
Claims (2)
のアルキル基を示し、同じでも異なっていてもよい。）
で表される化合物を固体触媒の存在下で反応させること
を特徴とする化２（式中、Ｒ1、Ｒ2は炭素数が２〜６の
アルキル基を示し、同じでも異なっていてもよく、mは
１または２の整数を示し、Ｘはアニオン成分で表され
る。）で表される近赤外線吸収剤の製造方法。 【化１】 【化２】 1. Chemical formula 1 (wherein R 1 and R 2 have 2 to 6 carbon atoms).
Represents an alkyl group and may be the same or different. )
Wherein the compound represented by the formula (2) is reacted in the presence of a solid catalyst (wherein R 1 and R 2 represent an alkyl group having 2 to 6 carbon atoms and may be the same or different). , M is an integer of 1 or 2, and X is represented by an anion component). [Chemical 1] [Chemical 2]
鉄、クロム、マンガン、コバルト、ニッケル、鉛の酸化
物、及び白金族金属及びその酸化物の少なくとも１種以
上を含有することを特徴とする請求項１記載の近赤外線
吸収剤の製造方法。2. The solid catalyst is silver, titanium, vanadium,
The method for producing a near-infrared absorber according to claim 1, further comprising at least one or more of oxides of iron, chromium, manganese, cobalt, nickel and lead, and platinum group metals and oxides thereof.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3282020A JPH0598243A (en) | 1991-10-03 | 1991-10-03 | Production of near-infrared absorber |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3282020A JPH0598243A (en) | 1991-10-03 | 1991-10-03 | Production of near-infrared absorber |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0598243A true JPH0598243A (en) | 1993-04-20 |
Family
ID=17647121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3282020A Pending JPH0598243A (en) | 1991-10-03 | 1991-10-03 | Production of near-infrared absorber |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0598243A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003055643A (en) * | 2001-08-10 | 2003-02-26 | Nagase Chemtex Corp | Method of producing near infrared ray absorber |
| JP2007092060A (en) * | 2005-09-05 | 2007-04-12 | Fujifilm Corp | Method for producing near-infrared-absorbing colorant compound |
| US7217839B2 (en) | 2005-09-07 | 2007-05-15 | Fujifilm Corporation | Method of producing near-infrared absorbing dye compound |
| US7473802B2 (en) | 2005-09-05 | 2009-01-06 | Fujifilm Corporation | Method of producing near-infrared absorbing dye compound |
-
1991
- 1991-10-03 JP JP3282020A patent/JPH0598243A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003055643A (en) * | 2001-08-10 | 2003-02-26 | Nagase Chemtex Corp | Method of producing near infrared ray absorber |
| JP2007092060A (en) * | 2005-09-05 | 2007-04-12 | Fujifilm Corp | Method for producing near-infrared-absorbing colorant compound |
| US7473802B2 (en) | 2005-09-05 | 2009-01-06 | Fujifilm Corporation | Method of producing near-infrared absorbing dye compound |
| US7217839B2 (en) | 2005-09-07 | 2007-05-15 | Fujifilm Corporation | Method of producing near-infrared absorbing dye compound |
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