JPH05247437A - Near-infrared-absorbing pigment - Google Patents
Near-infrared-absorbing pigmentInfo
- Publication number
- JPH05247437A JPH05247437A JP8034092A JP8034092A JPH05247437A JP H05247437 A JPH05247437 A JP H05247437A JP 8034092 A JP8034092 A JP 8034092A JP 8034092 A JP8034092 A JP 8034092A JP H05247437 A JPH05247437 A JP H05247437A
- Authority
- JP
- Japan
- Prior art keywords
- hexafluorophosphate
- formula
- infrared
- phenylenediamine
- tetrakis
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Optical Filters (AREA)
- 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、近赤外線吸収色素であ
るアニオン成分がヘキサフルオロリン酸イオンのアミニ
ウム塩に関する。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
ニレンジアミンのヘキサフルオロリン酸塩に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an aminium salt having a hexafluorophosphate ion as an anion component which is a near infrared absorbing dye. More specifically, it relates to the hexafluorophosphate 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
吸収色素として有用であり、また有機合成樹脂の光安定
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アニオン成分としては、過塩素
酸イオン、ヘキサフルオロアンチモン酸イオン等が知ら
れているが、アニオン成分がヘキサフルオロリン酸イオ
ンのアミニウム塩は知られていなかった。Aminium salts of N, N, N ', N'-tetrakis (P-dialkylaminophenyl) -P-phenylenediamine have strong absorption in the near infrared region and are useful as near infrared absorbing dyes. It is also used as a light stabilizer for organic synthetic resins. As the anion component of the aminium salt of N, N, N ′, N′-tetrakis (P-dialkylaminophenyl) -P-phenylenediamine, perchlorate ion, hexafluoroantimonate ion, etc. are known, An aminium salt having an anion component of hexafluorophosphate ion has not been known.
【０００３】アニオン成分が過塩素酸イオンのアミニウ
ム塩は、消防法危険物第１類（酸化性固体）に該当し、
貯蔵、運搬に際し法規制を受け、取り扱いに注意を要す
る。アニオン成分がヘキサフルオロアンチモン酸イオン
のアミニウム塩は、重金属を含有するため、大量に使用
した場合、環境が汚染されて人体に蓄積する危険性があ
る。そこで取り扱いが容易で、環境汚染の恐れのない、
安全性の高いアミニウム塩が望まれていた。The aminium salt whose anion component is perchlorate ion corresponds to Class 1 dangerous substances (oxidizing solid) under the Fire Service Act,
Be careful of handling due to legal regulations during storage and transportation. Since the aminium salt whose anion component is hexafluoroantimonate ion contains a heavy metal, when used in a large amount, there is a risk of polluting the environment and accumulating in the human body. Therefore, it is easy to handle and there is no risk of environmental pollution.
Aminium salt with high safety was desired.
【０００４】[0004]
【発明が解決しようとする課題】本発明の目的は、取り
扱いが容易で、かつ環境汚染の恐れもなく、安全性の高
い近赤外吸収色素として有用なアミニウム塩を提供する
ことである。SUMMARY OF THE INVENTION An object of the present invention is to provide an aminium salt which is easy to handle, has no fear of environmental pollution, and is useful as a near-infrared absorbing dye having high safety.
【０００５】[0005]
【課題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、上記のような問題点を解決した近赤外吸
収色素として有用なアミニウム塩を見いだし、本発明を
完成した。Means for Solving the Problems As a result of intensive studies, the present inventors have found an aminium salt useful as a near-infrared absorbing dye that has solved the above problems, and completed the present invention.
【０００６】本発明は、一般式＜Ａ＞（式中、Ｒ1、Ｒ2
は炭素数２〜６のアルキル基を示し、同じでも異なって
もよい。Ｘはアニオン成分を示し、mは１または２の整
数を示す。）で表される化合物において、アニオン成分
がヘキサフルオロリン酸イオンである近赤外線吸収色素
を提供するものである。The present invention has the general formula <A> (wherein R 1 , R 2
Represents an alkyl group having 2 to 6 carbon atoms and may be the same or different. X represents an anion component, and m represents an integer of 1 or 2. The present invention provides a near-infrared absorbing dye whose anion component is a hexafluorophosphate ion in the compound represented by (4).
【０００７】[0007]
【化１】[Chemical 1]
【０００８】本発明のアニオン成分がヘキサフルオロリ
ン酸イオンのアミニウム塩は、消防法危険物に該当しな
いので、貯蔵、運搬に際し法規制を受けず、取り扱いが
容易であり、また含まれているリンは、環境中に放出さ
れても、環境を汚染せず、人体にも無害である。加え
て、近赤外線吸収能力も従来の近赤外吸収色素と同等で
ある。The aminium salt of the hexafluorophosphate ion as the anion component of the present invention does not fall under the Fire Service Act as a dangerous substance, so it is not subject to legal regulations during storage and transportation, is easy to handle, and contains phosphorus. When released into the environment, it does not pollute the environment and is harmless to the human body. In addition, the near-infrared absorbing ability is also the same as that of the conventional near-infrared absorbing dye.
【０００９】本発明のアニオン成分がヘキサフルオロリ
ン酸イオンのアミニウム塩は、以下の方法により得られ
る。The aminium salt having hexafluorophosphate ion as the anion component of the present invention can be obtained by the following method.
【００１０】アセトン、アセトニトリル、ジメチルホル
ムアミド、酢酸エチルまたはその混合物等の親水性溶媒
に一般式＜Ｂ＞（式中、Ｒ1、Ｒ2は炭素数２〜６のアル
キル基を示し、同じでも異なってもよい。）で表される
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を溶解した後、ヘキ
サフルオロリン酸塩を溶解して白金等の触媒を加えて加
熱する。溶媒は、水または疎水性溶媒を少量含有しても
よい。反応後、水洗、減圧濃縮した後、ヘキサン等の疎
水性溶媒に投入し、ろ別、乾燥して本発明のアミニウム
塩を得る。In a hydrophilic solvent such as acetone, acetonitrile, dimethylformamide, ethyl acetate or a mixture thereof, the general formula <B> (in the formula, R 1 and R 2 represent an alkyl group having 2 to 6 carbon atoms, the same or different) N, N, N ′, N′-tetrakis (P-dialkylaminophenyl) -P-phenylenediamine represented by the formula (1) may be dissolved, and then hexafluorophosphate is dissolved to obtain a catalyst such as platinum. Add and heat. The solvent may contain a small amount of water or a hydrophobic solvent. After the reaction, the product is washed with water, concentrated under reduced pressure, added to a hydrophobic solvent such as hexane, filtered and dried to obtain the aminium salt of the present invention.
【００１１】[0011]
【化２】 [Chemical 2]
【００１２】反応時間が短い場合、一般式＜Ａ＞でm＝
１のアミニウム塩が得られ、反応時間が長くなるとm＝
２のアミニウム塩が得られる。したがって、反応時間の
制御によりmを制御することができる。When the reaction time is short, in the general formula <A>, m =
When the aminium salt of 1 is obtained and the reaction time becomes long, m =
An aminium salt of 2 is obtained. Therefore, m can be controlled by controlling the reaction time.
【００１３】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。Since the activity of the catalyst does not decrease due to the reaction, it can be used repeatedly.
【００１４】アミニウム塩を得る公知の技術である電解
法でも、本発明のアミニウム塩が得られるが、電極とし
て白金メッキチタン電極を用いた場合、電極がヘキサフ
ルオロリン酸イオンによって腐食されてしまう。また、
炭素電極を用いた場合は、電極は腐食されないが、徐々
に消耗してしまう。The aminium salt of the present invention can also be obtained by an electrolytic method, which is a known technique for obtaining an aminium salt, but when a platinum-plated titanium electrode is used as the electrode, the electrode is corroded by hexafluorophosphate ions. Also,
When a carbon electrode is used, the electrode is not corroded but is gradually consumed.
【００１５】本発明のアミニウム塩の用途としては、赤
外線用保護眼鏡、バーコード印刷用インク、電子写真用
トナー、熱線遮断用フィルム等がある。Applications of the aminium salt of the present invention include protective glasses for infrared rays, bar code printing inks, electrophotographic toners, heat ray blocking films and the like.
【００１６】[0016]
【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.
【００１７】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
ミンのモノヘキサフルオロリン酸塩］ アセトニトリル50ml、酢酸エチル100mlの混合溶媒に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を溶解し、ヘキサ
フルオロリン酸カリウム2.0ｇを加えアルミナ担体に白
金を被覆した固体触媒30ｇを加え、60℃で４時間攪はん
した。反応後、水洗、減圧濃縮した後、ｎ−ヘキサン45
0ml中に投入し、ろ別、乾燥して緑色の粉末9.0ｇ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147℃であった。Example 1 [N, N, N ', N'-tetrakis (P-dibutylaminophenyl) -P-phenylenediamine monohexafluorophosphate] N, N in a mixed solvent of 50 ml of acetonitrile and 100 ml of ethyl acetate.
9.2 g of N, N ', N'-tetrakis (P-dibutylaminophenyl) -P-phenylenediamine was dissolved, 2.0 g of potassium hexafluorophosphate was added, and 30 g of a solid catalyst coated with platinum on an alumina carrier was added, Stir at 4 ° C for 4 hours. After the reaction, washing with water and concentration under reduced pressure, n-hexane 45
It was put into 0 ml, filtered and dried to obtain 9.0 g of green powder. The product had a maximum absorption wavelength in acetone of 950 nm, a molar absorption coefficient of 2.0 × 10 4 , and a melting point of 147 ° C.
【００１８】生成物の赤外吸収特性値は、559cm-1のヘ
キサフルオロリン酸イオンの吸収を示した。The infrared absorption characteristic value of the product showed absorption of hexafluorophosphate ion at 559 cm -1 .
【００１９】生成物の元素分析結果を表１に示す。The results of elemental analysis of the product are shown in Table 1.
【００２０】[0020]
【表１】 [Table 1]
【００２１】実施例２［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
ミンのジヘキサフルオロリン酸塩］ 実施例１において、ヘキサフルオロリン酸カリウムを4.
6ｇ、反応時間を８時間とした以外は、実施例１と同様
にして、青色の粉末10.0ｇ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9.2×1
04、融点が175℃であった。Example 2 [N, N, N ', N'-tetrakis (P-dibutylaminophenyl) -P-phenylenediamine dihexafluorophosphate] In Example 1, potassium hexafluorophosphate was added to 4 parts. .
A blue powder of 10.0 g was obtained in the same manner as in Example 1 except that the reaction time was 6 g and the reaction time was 8 hours. The product has a maximum absorption wavelength in acetone of 1078 nm and a molar absorption coefficient of 9.2 × 1.
0 4 , the melting point was 175 ° C.
【００２２】生成物の赤外吸収特性値は、559cm-1のヘ
キサフルオロリン酸イオンの吸収を示した。The infrared absorption characteristic value of the product showed absorption of hexafluorophosphate ion at 559 cm -1 .
【００２３】生成物の元素分析の結果を表２に示す。The results of elemental analysis of the product are shown in Table 2.
【００２４】[0024]
【表２】 [Table 2]
【００２５】比較例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
ミンのモノ過塩素酸塩］ 実施例１において、ヘキサフルオロリン酸カリウムの代
りに過塩素酸ナトリウム1.3ｇの５ml水溶液を用いた以
外は、実施例１と同様にして、緑色の粉末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℃であった。Comparative Example 1 [N, N, N ', N'-Tetrakis (P-dibutylaminophenyl) -P-phenylenediamine monoperchlorate] In Example 1, instead of potassium hexafluorophosphate. 9.8 g of green powder was obtained in the same manner as in Example 1 except that a 5 ml aqueous solution of 1.3 g of sodium perchlorate was used. The product had a maximum absorption wavelength in acetone of 950 nm, a molar absorption coefficient of 2.0 × 10 4 , and a melting point of 159 ° C.
【００２６】[0026]
【発明の効果】本発明の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
アミンのヘキサフルオロリン酸塩は、消防法の危険物に
該当せず、取り扱いが容易で、また、重金属を含有しな
いので、環境を汚染せず、安全性が高く、近赤外吸収色
素として有用である。INDUSTRIAL APPLICABILITY The hexafluorophosphate salt of N, N, N ', N'-tetrakis (P-dialkylaminophenyl) -P-phenylenediamine of the present invention is not a dangerous substance under the Fire Defense Law and should be handled. Since it does not contain heavy metals, it does not pollute the environment, is highly safe, and is useful as a near-infrared absorbing dye.
─────────────────────────────────────────────────────
─────────────────────────────────────────────────── ───
【手続補正書】[Procedure amendment]
【提出日】平成５年３月２６日[Submission date] March 26, 1993
【手続補正１】[Procedure Amendment 1]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】０００４[Correction target item name] 0004
【補正方法】変更[Correction method] Change
【補正内容】[Correction content]
【０００４】[0004]
【発明が解決しようとする課題】 本発明の目的は、取
り扱いが容易で、かつ環境汚染の恐れもなく、安全性の
高い近赤外線吸収色素として有用なアミニウム塩を提供
することである。An object of the present invention is to provide an aminium salt which is easy to handle, has no fear of environmental pollution, and is useful as a highly safe near-infrared absorbing dye.
【手続補正２】[Procedure Amendment 2]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】０００５[Correction target item name] 0005
【補正方法】変更[Correction method] Change
【補正内容】[Correction content]
【０００５】[0005]
【課題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、上記のような問題点を解決した近赤外線
吸収色素として有用なアミニウム塩を見いだし、本発明
を完成した。As a result of intensive studies, the present inventors have found an aminium salt useful as a near-infrared absorbing dye that solves the above problems, and completed.
【手続補正３】[Procedure 3]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】０００８[Correction target item name] 0008
【補正方法】変更[Correction method] Change
【補正内容】[Correction content]
【０００８】 本発明のアニオン成分がヘキサフルオロ
リン酸イオンのアミニウム塩は、消防法危険物に該当し
ないので、貯蔵、運搬に際し法規制を受けず、取り扱い
が容易であり、また含まれているリンは、環境中に放出
されても、環境を汚染せず、人体にも無害である。加え
て、近赤外線吸収能力も従来の近赤外線吸収色素と同等
である。The aminium salt of the hexafluorophosphate ion as the anion component of the present invention does not fall under the Fire Service Act as a dangerous substance, so it is not subject to legal restrictions during storage and transportation, is easy to handle, and contains phosphorus. When released into the environment, it does not pollute the environment and is harmless to the human body. In addition, the near-infrared absorbing ability is similar to that of conventional near-infrared absorbing dyes.
【手続補正４】[Procedure amendment 4]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】００１８[Correction target item name] 0018
【補正方法】変更[Correction method] Change
【補正内容】[Correction content]
【００１８】 生成物の赤外線吸収特性値は、５５９ｃ
ｍ−１のヘキサフルオロリン酸イオンの吸収を示した。The infrared absorption characteristic value of the product is 559c
It showed absorption of hexafluorophosphate ion of m −1 .
【手続補正５】[Procedure Amendment 5]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】００２２[Name of item to be corrected] 0022
【補正方法】変更[Correction method] Change
【補正内容】[Correction content]
【００２２】 生成物の赤外線吸収特性値は、５５９ｃ
ｍ−１のヘキサフルオロリン酸イオンの吸収を示した。The infrared absorption characteristic value of the product is 559c
It showed absorption of hexafluorophosphate ion of m −1 .
【手続補正６】[Procedure correction 6]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】００２６[Correction target item name] 0026
【補正方法】変更[Correction method] Change
【補正内容】[Correction content]
【００２６】[0026]
【発明の効果】本発明の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
ンジアミンのヘキサフルオロリン酸塩は、消防法の危険
物に該当せず、取り扱いが容易で、また、重金属を含有
しないので、環境を汚染せず、安全性が高く、近赤外線
吸収色素として有用である。INDUSTRIAL APPLICABILITY The hexafluorophosphate salt of N, N, N ′, N′-tetrakis (P-dialkylaminophenyl) -P-phenylenediamine of the present invention is not a dangerous substance under the Fire Defense Law and should be handled. Moreover, since it does not contain heavy metals, it does not pollute the environment, is highly safe, and is useful as a near-infrared absorbing dye.
Claims (1)
て、アニオン成分がヘキサフルオロリン酸イオンである
近赤外線吸収色素。 【化１】 （式中、Ｒ1、Ｒ2は炭素数２〜６のアルキル基を示し、
同じでも異なってもよい。Ｘはアニオン成分を示し、m
は１または２の整数を示す。）1. A near infrared absorbing dye in which the anion component is a hexafluorophosphate ion in the compound represented by formula <A>. [Chemical 1] (In the formula, R 1 and R 2 represent an alkyl group having 2 to 6 carbon atoms,
It may be the same or different. X represents an anion component, m
Represents an integer of 1 or 2. )
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8034092A JPH05247437A (en) | 1992-03-03 | 1992-03-03 | Near-infrared-absorbing pigment |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8034092A JPH05247437A (en) | 1992-03-03 | 1992-03-03 | Near-infrared-absorbing pigment |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH05247437A true JPH05247437A (en) | 1993-09-24 |
Family
ID=13715537
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8034092A Pending JPH05247437A (en) | 1992-03-03 | 1992-03-03 | Near-infrared-absorbing pigment |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH05247437A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998051661A1 (en) * | 1997-05-14 | 1998-11-19 | Nippon Kayaku Kabushiki Kaisha | Aminium compounds and optical recording media containing the same |
| JP2007092060A (en) * | 2005-09-05 | 2007-04-12 | Fujifilm Corp | Method for producing near-infrared-absorbing colorant compound |
| JP2012507058A (en) * | 2008-10-28 | 2012-03-22 | オプトドット コーポレイション | Crystalline infrared reflective film |
| US10858519B2 (en) | 2016-01-15 | 2020-12-08 | Toyo Ink Sc Holdings Co., Ltd. | Near-infrared absorbing composition for solid-state imaging device and filter |
-
1992
- 1992-03-03 JP JP8034092A patent/JPH05247437A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JP2007092060A (en) * | 2005-09-05 | 2007-04-12 | Fujifilm Corp | Method for producing near-infrared-absorbing colorant compound |
| JP2012507058A (en) * | 2008-10-28 | 2012-03-22 | オプトドット コーポレイション | Crystalline infrared reflective film |
| US10858519B2 (en) | 2016-01-15 | 2020-12-08 | Toyo Ink Sc Holdings Co., Ltd. | Near-infrared absorbing composition for solid-state imaging device and filter |
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