JPH02311447A - Production of n,n,n',n'-tetrakis(p-dialkylaminophenyl)-p-phenylenediamine aminium salt - Google Patents
Production of n,n,n',n'-tetrakis(p-dialkylaminophenyl)-p-phenylenediamine aminium saltInfo
- Publication number
- JPH02311447A JPH02311447A JP12893889A JP12893889A JPH02311447A JP H02311447 A JPH02311447 A JP H02311447A JP 12893889 A JP12893889 A JP 12893889A JP 12893889 A JP12893889 A JP 12893889A JP H02311447 A JPH02311447 A JP H02311447A
- Authority
- JP
- Japan
- Prior art keywords
- ferric
- salt
- tetrakis
- formula
- phenylenediamine
- 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.)
- Granted
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 150000001450 anions Chemical group 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 abstract description 8
- 238000006243 chemical reaction Methods 0.000 abstract description 7
- -1 glycol ethers Chemical class 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 229910021578 Iron(III) chloride Inorganic materials 0.000 abstract description 3
- VEPSWGHMGZQCIN-UHFFFAOYSA-H ferric oxalate Chemical compound [Fe+3].[Fe+3].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O VEPSWGHMGZQCIN-UHFFFAOYSA-H 0.000 abstract description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical group Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 abstract description 3
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 abstract description 3
- 229910000360 iron(III) sulfate Inorganic materials 0.000 abstract description 3
- 239000006096 absorbing agent Substances 0.000 abstract description 2
- 150000001298 alcohols Chemical class 0.000 abstract description 2
- LHOWRPZTCLUDOI-UHFFFAOYSA-K iron(3+);triperchlorate Chemical compound [Fe+3].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O LHOWRPZTCLUDOI-UHFFFAOYSA-K 0.000 abstract description 2
- 150000002576 ketones Chemical class 0.000 abstract description 2
- 238000005406 washing Methods 0.000 abstract description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- RBWNDBNSJFCLBZ-UHFFFAOYSA-N 7-methyl-5,6,7,8-tetrahydro-3h-[1]benzothiolo[2,3-d]pyrimidine-4-thione Chemical compound N1=CNC(=S)C2=C1SC1=C2CCC(C)C1 RBWNDBNSJFCLBZ-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- FDOCOSUCHDHMCW-UHFFFAOYSA-K benzenesulfonate iron(3+) Chemical compound [Fe+3].[O-]S(=O)(=O)c1ccccc1.[O-]S(=O)(=O)c1ccccc1.[O-]S(=O)(=O)c1ccccc1 FDOCOSUCHDHMCW-UHFFFAOYSA-K 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
- 230000007423 decrease Effects 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-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
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- FEONEKOZSGPOFN-UHFFFAOYSA-K tribromoiron Chemical compound Br[Fe](Br)Br FEONEKOZSGPOFN-UHFFFAOYSA-K 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明はアミニウム塩の製造方法に関する。更に詳しく
はＮ、Ｎ、Ｎ’、Ｎ’−テトラキス（ｐ−ジアルキルア
ミノフェニル）−１）−７ｚニレンノアミン類のアミニ
ウム塩の製造方法に関する。DETAILED DESCRIPTION OF THE INVENTION (Industrial Field of Application) The present invention relates to a method for producing an aminium salt. More specifically, the present invention relates to a method for producing aminium salts of N,N,N',N'-tetrakis(p-dialkylaminophenyl)-1)-7z nylennoamines.
（従来の技術）
Ｎ、Ｎ、Ｎ’、Ｎ’−テトラキス（ｐ−ジアルキルアミ
／フェニル）−ｐ−フェニレンジアミンのアミニウム塩
は、赤外領域に強い吸収を持ち、赤外線吸収剤として有
用な物質である。(Prior art) Aminium salt of N,N,N',N'-tetrakis(p-dialkylami/phenyl)-p-phenylenediamine has strong absorption in the infrared region and is a useful substance as an infrared absorber. It is.
Ｎ、Ｎ、Ｎ’、Ｎ’−テトラキス（ｐ−ジアルキルアミ
７フエニル＞−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号公報に、Ｎ、Ｎ、Ｎ’、Ｎ’
−テトラキス（ｐ−ノアルキルアミ／フェニル）−ｐ−
７エニレンジアミン類を過塩素酸銀あるいはへキサフル
オロ砒酸銀なとの銀塩によって、又は電解法によって酸
化してアミニウム塩を製造する方法の記載がある。Regarding the production method of aminium salt of N,N,N',N'-tetrakis(p-dialkylami 7 phenyl>-p-phenylenediamine), see Japanese Patent Publication No. 43-25335 and Japanese Patent Publication No. 46-5810. N, N, N', N'
-tetrakis(p-noalkylami/phenyl)-p-
There is a description of a method for producing an aminium salt by oxidizing 7-enylenediamines with a silver salt such as silver perchlorate or silver hexafluoroarsenate, or by electrolysis.
（発明が解決しようとする問題点）
前記の従来の製造方法には問題点がある。特公昭４３−
２５３３５号に記述されている化学的酸化方法では高価
な銀塩を使用し、この銀塩は反応して金属状銀となり生
成物からの除去が困難である。また銀塩は感光性で、光
により銀が遊離し、取り扱いが困難である。特公昭４６
−５８１０号では電解酸化方法について記述がされてい
るが、金属塩を用いる電解法のｒこめ、陰極への金属の
析出が生じて電流値の低下により電解効率が低くなる。(Problems to be Solved by the Invention) The conventional manufacturing method described above has problems. Special Public Service 1977-
The chemical oxidation process described in No. 25335 uses expensive silver salts that react to form metallic silver that is difficult to remove from the product. Furthermore, silver salts are photosensitive, and silver is liberated by light, making them difficult to handle. Special Public Service (1977)
No. 5810 describes an electrolytic oxidation method, but due to the electrolytic method using a metal salt, metal is deposited on the cathode and the current value decreases, resulting in a lower electrolytic efficiency.
（問題点を解決するための手段）
本発明者らは前記のような問題点を解決すべく検討を重
ねた結果、本発明を完成した。(Means for Solving the Problems) The present inventors have completed the present invention as a result of repeated studies to solve the above problems.
即ち、本発明は一般式（Ｉ）
・ ・ ・（１）
（式中、Ｒ１、Ｒ２は炭素ａ１〜６のアルキル基を示し
、同じでも異なっていてもよい。）で表わされる化合物
に第２鉄塩を反応させることを特徴とする一般式（ＩＩ
）
・・・（ＩＩ）
（式中、Ｒ１は炭素数１〜６のアルキル基を示し、ｍは
１または２の整数を示し、Ｘは第２鉄塩のアニオン成分
を示す。）で表わされる化合物の製造方法を提供するも
のである。That is, the present invention provides a compound represented by the general formula (I) . General formula (II) characterized by reacting an iron salt
)...(II) (In the formula, R1 represents an alkyl group having 1 to 6 carbon atoms, m represents an integer of 1 or 2, and X represents an anion component of the ferric salt.) A method for producing a compound is provided.
反応に用いられる第２鉄塩には例えば塩化第２鉄、臭化
第２鉄、硫酸第２鉄、過塩素酸第２鉄、硝酸第２鉄、６
フ・／化アンチモン酸第２鉄、４７７化ホウ酸第２鉄、
トルエンスルホン酸第２鉄、ベンセンスルホン酸第２鉄
、シュウ酸第２鉄などがあげられる。使用する第２鉄塩
の量は反応させるＮ、Ｎ、Ｎ’、Ｎ’−テトラキス（１
）−ジアルキル７ミノ７エこル）−ｐ−フェニレンノア
ミノ類に対して１〜３当量である。Examples of ferric salts used in the reaction include ferric chloride, ferric bromide, ferric sulfate, ferric perchlorate, ferric nitrate, 6
ferric antimonate, ferric borate 477,
Examples include ferric toluenesulfonate, ferric benzenesulfonate, and ferric oxalate. The amount of ferric salt used is determined by the amount of N,N,N',N'-tetrakis(1
)-dialkyl7mino7ethyl)-p-phenylenenoamino.
反応に用いる溶媒としては親水性育成）３媒、例えばメ
タノール、エタノール、ブタ／−ル、プロパ／−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、ブチルセロソルブ、ジエチレング
リコールモノブチルエーテル、トリエチレングリコール
モ／ブナルエーテルなどのグリフールのエーテル類、ア
セ）・二Ｙリル、ツメチルホルムアミド、ジメチルスル
ホキシド、ジメチルアセトアミドあるいはこれらの混合
溶媒が使用できる。又、これらの溶媒は少量の水あるい
は疎水性有機＠媒を含んでいてもよい、これらの溶媒の
使用量は反応基質に灯して１〜８０重量部である。The solvent used in the reaction is a hydrophilicity developing medium, such as alcohols such as methanol, ethanol, butyl, propyl, acetone, methyl isobutyl ketone,
Ketones such as methyl ethyl ketone, methyl cellosolve, ethyl cellosolve, butyl cellosolve, diethylene glycol monobutyl ether, glyfur ethers such as triethylene glycol mo/bunal ether, ace)-diYlyl, trimethylformamide, dimethyl sulfoxide, dimethyl acetamide, or these A mixed solvent of can be used. These solvents may also contain a small amount of water or a hydrophobic organic medium, and the amount of these solvents used is 1 to 80 parts by weight based on the reaction substrate.
反応温度は室温〜〕８０°Ｃであり、好しくは４０〜１
２０°Ｃである。反応は数時間で終了し、反応終了後、
溶媒を除去し未反応物を洗浄し式（Ｅｌ）のアミニウム
塩を高収率で得ることができる。The reaction temperature is room temperature to]80°C, preferably 40 to 1
It is 20°C. The reaction completes in a few hours, and after the reaction is complete,
By removing the solvent and washing unreacted substances, the aminium salt of formula (El) can be obtained in high yield.
以下、実施例で本発明の詳細な説明をするが重量部を部
と略して記載する。Hereinafter, the present invention will be described in detail with reference to Examples, where parts by weight are abbreviated as parts.
（実施例１）
Ｎ、Ｎ、Ｎ’、Ｎ’−テトラキス（ｐ−ジブチルアミ／
フェニル）−ｐ−７工ニレンノアミン９６２ｇをツメチ
ルホルムアミド４００ ＋ｏｌに溶解し、過塩素酸第２
鉄４．６ＦＫを含む水４０ｍ１の溶液を加え、室温で２
時間攪拌した。反応混合物を水５００ｍ１中へ投入し、
析出した固体をろ別し水洗、乾燥して緑色の粉末１０ｇ
を得た。このアミニウム塩（ビス（ｐ−ジブチルアミ／
フェニル）（Ｎ、Ｎ−ビス（１）−ノブチルアミノフェ
ニル゛）−ｐ−アミ／フェニル１アミニワム過塩素酸塩
）の元素分析の結果を下記に示す。(Example 1) N,N,N',N'-tetrakis(p-dibutylamide/
Dissolve 962 g of (phenyl)-p-7 engineered nylennoamine in 400 liters of trimethylformamide, and add
Add a solution of 40 ml of water containing 4.6 FK of iron and
Stir for hours. Pour the reaction mixture into 500 ml of water,
The precipitated solid was filtered, washed with water, and dried to give 10 g of green powder.
I got it. This aminium salt (bis(p-dibutylamine/
The results of elemental analysis of phenyl)(N,N-bis(1)-butylaminophenyl)-p-amino/phenyl 1-aminium perchlorate) are shown below.
元素分析値（Ｃ６２Ｈ，Ｎ６０４Ｃｆｆｉ）計算値 Ｃ
７２，９４、Ｈ９，０８、Ｎ ８．２３分析値 Ｃ７
２，７３、）（９，２４、Ｎ ８．１８（実施例２）
Ｎ、Ｎ、Ｎ”、Ｎｌ−テトラキス（ｐ−ジブチルアミ／
フェニル）−ｐ−フェニレンシアミン９．２ｇＦ酢酸エ
チル４００ｍ１とア七トン２００ｍ１の混合溶媒に溶解
し、塩化第２鉄２．７ｇを含む水５０ｍ１の溶液を加え
、５０°Ｃに加温して２時間攪拌した。溶媒を留去し、
残渣を水洗乾燥して緑色の粉末９．３ｇを得た。このア
ミニウム塩（ビス（ｐ−ジブチルアミ／フェニル）［Ｎ
、Ｎ−ビス（ｐ−ジブチルアミノフェニル）−ｐ−アミ
ノフェニル］アミニウム塩化物）の元素分析の結果を下
記に示す。Elemental analysis value (C62H, N604Cffi) calculated value C
72,94, H9,08, N 8.23 analysis value C7
2,73,)(9,24,N 8.18 (Example 2) N,N,N”,Nl-tetrakis(p-dibutylamide/
Phenyl)-p-phenylenecyamine (9.2 g) was dissolved in a mixed solvent of 400 ml of ethyl acetate and 200 ml of ethyl acetate, a solution of 50 ml of water containing 2.7 g of ferric chloride was added, and the mixture was heated to 50°C. Stirred for 2 hours. Distill the solvent,
The residue was washed with water and dried to obtain 9.3 g of green powder. This aminium salt (bis(p-dibutylamine/phenyl)[N
, N-bis(p-dibutylaminophenyl)-p-aminophenyl]aminium chloride) are shown below.
元素分析値（Ｃ，□１−１，２Ｎ６ＣＮ）計算値 Ｃ７
７，８２、Ｈ９，６９、Ｎ ８．７８分析値 Ｃ７７，
６３、Ｈ９，６０、Ｎ ８．６９（実 施 例３）
Ｎ、Ｎ、Ｎ’、Ｎ’−テトラキス（ｐ−ジエチルアミノ
フェニル）−ｐ−フェニレンシアミン８．１ｇをジメチ
ルスルホキシド３００１ｆｉｌに溶解し、硫酸第２鉄１
０．２．を含む水５０ｍ１の溶液を加え５０°Ｃに加温
して３時間攪拌した。反応混合物を水５００ｍ１中へ投
入し、析出した固体をろ別し、水洗、乾燥して緑色の粉
末１０ｇを得た。このアミニウム塩（ビス（ｐ−ジエチ
ルアミノフェニル）（Ｎ、Ｎ−ビス（ｐ−ジエチルアミ
ノフェニル）−ｐ−アミ／７エ二ル］アミニウム硫酸塩
）の元素分析の結果を下記に示す。Elemental analysis value (C, □1-1,2N6CN) calculated value C7
7,82, H9,69, N 8.78 analysis value C77,
63, H9,60, N 8.69 (Example 3) 8.1 g of N, N, N', N'-tetrakis (p-diethylaminophenyl)-p-phenylenecyamine was dissolved in 3001 fil of dimethyl sulfoxide, Ferric sulfate 1
0.2. A solution containing 50 ml of water was added thereto, heated to 50°C, and stirred for 3 hours. The reaction mixture was poured into 500 ml of water, and the precipitated solid was filtered off, washed with water, and dried to obtain 10 g of green powder. The results of elemental analysis of this aminium salt (bis(p-diethylaminophenyl) (N,N-bis(p-diethylaminophenyl)-p-ami/7-enyl) aminium sulfate) are shown below.
元素分析値（Ｃ５，Ｈ，、Ｎ、Ｏ，Ｓ２）計算値Ｃ６４
，７８、Ｈ７，６５、Ｎ ８．３９分析値Ｃ６４，８
５、Ｈ７，６９、Ｎ ８．４８（実 施 例４）
Ｎ 、 Ｎ 、 Ｎ ’ 、 Ｎ ’−テトラアキス（
ρ−ツメチルアミ／フェニル）ｐ−７ｚニレンノアミン
７．０ｇをジメチルホルムアミド４００ｍ１に溶解し、
シュウ酸第２鉄４．７ｇを含む水４０＋ｎｌの溶液を加
え、室温で２時間攪拌しｔこ。反応混合物を水５００ｍ
１中へ投入し、析出した固体をろ別し、水洗、乾燥して
緑色の粉末７．８ｇを得た。このアミニウム塩（ビス（
ｐ−ツメチルアミノフェニル）（、Ｎ、Ｎ−ビス（ｐ−
ノメチルアミ／フェニル）−ｐ−アミ／フェニル１アミ
ニウムシユウ酸塩）の元素分析の結果を下記に示す。Elemental analysis value (C5, H,, N, O, S2) Calculated value C64
,78,H7,65,N 8.39 Analysis value C64,8
5, H7,69, N 8.48 (Example 4) N, N, N', N'-tetraakis (
Dissolve 7.0 g of p-7z nylennoamine (ρ-tmethylamine/phenyl) in 400 ml of dimethylformamide,
Add a solution of 40+nl of water containing 4.7g of ferric oxalate and stir at room temperature for 2 hours. Pour the reaction mixture into 500ml of water.
1, and the precipitated solid was filtered out, washed with water, and dried to obtain 7.8 g of green powder. This aminium salt (bis(
p-trimethylaminophenyl)(,N,N-bis(p-
The results of elemental analysis of p-aminium oxalate (p-aminium oxalate) are shown below.
元素分析値（Ｃ，、Ｈ６ｏＮ、０４）
計算値Ｃ７３，４４、Ｈ７，７０、Ｎ １０，７０分
析値Ｃ７２，０３、Ｉ−１７，５５、Ｎ １０．４９
（発明の効果）
本発明の方法によって、Ｎ、Ｎ、Ｎ’、Ｎ’−テトラキ
ス（ｐ−ンアルキルアミ７フェニル）−ｐ−フェニレン
シアミンの７ミニウム塩を効率良く製造できる。Elemental analysis value (C,, H6oN, 04) Calculated value C73,44, H7,70, N 10,70 Analysis value C72,03, I-17,55, N 10.49
(Effects of the Invention) According to the method of the present invention, the 7minium salt of N,N,N',N'-tetrakis(p-alkylami-7phenyl)-p-phenylenecyamine can be efficiently produced.
Claims (1)
示し、同じでも異なっていてもよい。）で表わされる化
合物に第２鉄塩を反応させることを特徴とする一般式（
II） ▲数式、化学式、表等があります▼・・・（II） （式中、Ｒ＾１、Ｒ＾２は炭素数１〜６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は第２鉄塩のアニオン成分を示す。）で表
わされるＮ，Ｎ，Ｎ’，Ｎ’−テトラキズ（ｐ−ジアル
キルアミノフエニル）−ｐ−フェニレンジアミンのアミ
ニウム塩の製造方法。[Claims] General formula (I) ▲ Numerical formulas, chemical formulas, tables, etc.▼... (I) (In the formula, R^1 and R^2 represent an alkyl group having 1 to 6 carbon atoms, The general formula (which may be the same or different) is reacted with a ferric salt.
II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(II) (In the formula, R^1 and R^2 represent an alkyl group having 1 to 6 carbon atoms, and may be the same or different, and m is an integer of 1 or 2, and X represents an anion component of the ferric salt. Method of manufacturing salt.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12893889A JP2715319B2 (en) | 1989-05-24 | 1989-05-24 | Method for producing an aminium salt of N, N, N ▲ ″, N ▲ ″ -tetrakis (p-dialkylaminophenyl) -p-phenylenediamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12893889A JP2715319B2 (en) | 1989-05-24 | 1989-05-24 | Method for producing an aminium salt of N, N, N ▲ ″, N ▲ ″ -tetrakis (p-dialkylaminophenyl) -p-phenylenediamine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02311447A true JPH02311447A (en) | 1990-12-27 |
| JP2715319B2 JP2715319B2 (en) | 1998-02-18 |
Family
ID=14997120
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12893889A Expired - Lifetime JP2715319B2 (en) | 1989-05-24 | 1989-05-24 | Method for producing an aminium salt of N, N, N ▲ ″, N ▲ ″ -tetrakis (p-dialkylaminophenyl) -p-phenylenediamine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2715319B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5705101A (en) * | 1994-12-21 | 1998-01-06 | Mitsui Toatsu Chemicals, Inc. | Near infrared absorber, preparation process therefor and use thereof |
| WO1998051661A1 (en) * | 1997-05-14 | 1998-11-19 | Nippon Kayaku Kabushiki Kaisha | Aminium compounds and optical recording media containing the same |
| 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 |
-
1989
- 1989-05-24 JP JP12893889A patent/JP2715319B2/en not_active Expired - Lifetime
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5705101A (en) * | 1994-12-21 | 1998-01-06 | Mitsui Toatsu Chemicals, Inc. | Near infrared absorber, preparation process therefor and use thereof |
| WO1998051661A1 (en) * | 1997-05-14 | 1998-11-19 | Nippon Kayaku Kabushiki Kaisha | Aminium compounds and optical recording media containing the same |
| GB2340833A (en) * | 1997-05-14 | 2000-03-01 | Nippon Kayaku Kk | Aminium compounds and optical recording media containing the same |
| US6214435B1 (en) | 1997-05-14 | 2001-04-10 | Nippon Kayaku Kabushiki Kaisha | Aminium compounds and optical information recording media containing the same |
| GB2340833B (en) * | 1997-05-14 | 2001-06-13 | Nippon Kayaku Kk | Aminium compounds and optical recording media containing the same |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2715319B2 (en) | 1998-02-18 |
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