JPH04124156A - Reagent for detecting fingerprint and its production - Google Patents
Reagent for detecting fingerprint and its productionInfo
- Publication number
- JPH04124156A JPH04124156A JP24589190A JP24589190A JPH04124156A JP H04124156 A JPH04124156 A JP H04124156A JP 24589190 A JP24589190 A JP 24589190A JP 24589190 A JP24589190 A JP 24589190A JP H04124156 A JPH04124156 A JP H04124156A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- ninhydrin
- formula
- fingerprints
- fingerprint
- 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
- 239000003153 chemical reaction reagent Substances 0.000 title claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 238000001514 detection method Methods 0.000 claims abstract description 24
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 239000000126 substance Substances 0.000 claims description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract description 48
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 abstract description 25
- 239000002798 polar solvent Substances 0.000 abstract description 10
- 239000002904 solvent Substances 0.000 abstract description 8
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract description 7
- 239000000463 material Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 description 19
- 239000007788 liquid Substances 0.000 description 10
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 6
- -1 1-heptyl Chemical group 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 4
- 238000002845 discoloration Methods 0.000 description 4
- WVZWEMOFSIEEMU-UHFFFAOYSA-N indene-1,2,3-trione Chemical compound C1=CC=C2C(=O)C(=O)C(=O)C2=C1 WVZWEMOFSIEEMU-UHFFFAOYSA-N 0.000 description 4
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000007605 air drying Methods 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- ACBMYYVZWKYLIP-UHFFFAOYSA-N 2-methylheptan-2-ol Chemical compound CCCCCC(C)(C)O ACBMYYVZWKYLIP-UHFFFAOYSA-N 0.000 description 1
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000000740 bleeding effect Effects 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
- 150000001721 carbon Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Landscapes
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野コ
本発明は、新規なニンヒドリンのＯ−アルキル誘導体、
その製法、及びそれらを用いた指紋検出試薬に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention provides novel O-alkyl derivatives of ninhydrin,
The present invention relates to a method for producing the same and a fingerprint detection reagent using the same.
［従来の技術ゴ
ニンヒドリンは、従来より紙類からの指紋検出試薬とし
て用いられてきたが、ケトン類、アルー−ル類等の極性
溶剤にしか溶解しないので、紙票から指紋検出を行う場
合には、この極性溶剤が紙上の記載文字を溶かし出した
り、感熱紙の場合は感熱紙自体を変色させてしまうため
、鮮明な指紋を検出できないばかりでなく、証拠価値を
も消滅させてしまう等の問題点を有することは一般に知
られていた。[Conventional technology Goninhydrin has traditionally been used as a reagent for detecting fingerprints from paper, but since it dissolves only in polar solvents such as ketones and alcohols, it is difficult to detect fingerprints from paper slips. This polar solvent dissolves the characters written on the paper, or in the case of thermal paper, discolors the thermal paper itself, which not only makes it impossible to detect clear fingerprints, but also destroys their evidentiary value. It was generally known that there were problems.
そこで、従来、感熱紙等からの指紋検出においては、感
熱紙等を変化させないヘキサン等の脂肪、原炭化水素系
溶剤に溶解させるために、エタノールなどの補助極性溶
剤を添加する方法（Ａ法と呼ぶ）が用いられてきた。し
かし、この方法においては、添加された極性溶剤が記載
文字や感熱紙等に与える変化を皆無にすることはできな
いものと考える。Therefore, conventionally, in the detection of fingerprints from thermal paper, etc., a method (method A) in which an auxiliary polar solvent such as ethanol is added to dissolve the thermal paper, etc. in a fat or raw hydrocarbon solvent such as hexane that does not change the thermal paper, etc. ) has been used. However, in this method, it is considered that it is not possible to completely eliminate changes caused by the added polar solvent to written characters, thermal paper, etc.
また、ニンヒドリンをしみ込ませた和紙の間に指紋の控
着した紙類を挟み込み、圧力をかけることにより直接指
紋を検出する方法（Ｂ法と呼ぶ）も考えられているが、
この方法で検出した指紋は総体的に薄く、解析が困難で
あるばかりでなく。Another method has been considered (called method B) in which fingerprints are directly detected by sandwiching paper with fingerprints between Japanese paper impregnated with ninhydrin and applying pressure.
Fingerprints detected using this method are not only thin and difficult to analyze.
検出に長時閉を要する等の問題点を有するものと考える
。It is thought that there are problems such as the need to close the sensor for a long time for detection.
［発明が解決しようとする１１４８コ
ニンヒドリンがヘキサン等の脂肪族炭化水素系溶剤に溶
解しないのは、ニンヒドリンの分子ｗ道が極性基である
水酸基やカルボニル基を有しているからであり、これら
の極性基を残したままで脂肪族炭化水素系溶剤に溶かそ
うとした従来の方法は、おのずと限界があったと考える
。ニンヒドリンの水酸基が結合している炭素原子は、ｇ
接する２個のカルボニル基によって反応性が高められて
おり、指紋中のアミノ酸との反応に直接関与する部位で
あることは一般に知られていることである。[The reason why 1148 coninhydrin, which the invention seeks to solve, does not dissolve in aliphatic hydrocarbon solvents such as hexane is because the molecule of ninhydrin has polar groups such as hydroxyl and carbonyl groups. We believe that the conventional method of dissolving the compound in an aliphatic hydrocarbon solvent while leaving the polar group intact had its limitations. The carbon atom to which the hydroxyl group of ninhydrin is attached is g
It is generally known that the reactivity is enhanced by the two carbonyl groups in contact with each other, and that this is a site that directly participates in the reaction with the amino acid in the fingerprint.
したがって、この部位に置換基を導入すれば、アミノ酸
との反応性が低下し、指紋検出性能を有しなくなる恐れ
が多分にあった。この理由により、これまでニンヒドリ
ンのこの部位に置換基を導入しようとする試みがなされ
なかったものと思われる。Therefore, if a substituent is introduced into this site, the reactivity with amino acids will decrease, and there is a strong possibility that the fingerprint detection performance will be lost. It is believed that for this reason no attempt has been made to introduce substituents at this site of ninhydrin.
本発明は、指紋検出性能を有し、極性溶剤を添加するこ
となくヘキサン等の脂肪族炭化水素系溶剤に溶解するこ
とにより、記載文字をにじませることなく、また極性溶
剤で変化し易い物品からでも鮮明な指紋を検出すること
ができるニンヒドリン誘導体を提供することを目的とす
る。さらに、本発明は、その化合物を製造するための方
法を提供することも、目的とする。The present invention has the ability to detect fingerprints, and by dissolving in aliphatic hydrocarbon solvents such as hexane without adding polar solvents, the written characters do not smear and can be easily removed from articles that are easily changed by polar solvents. The purpose of the present invention is to provide a ninhydrin derivative that can detect even clear fingerprints. Furthermore, it is an object of the present invention to provide a method for producing the compound.
［課題を解決するための手段］
上記目的を達成するため、種々のニンヒドリンの○−ア
ルキル誘導体を合成し、そのヘキサンに対する溶解性と
指紋検出性能を試験した結果１式［式中、Ｒはアルキル
基を示す］
で表わされる新規なニンヒドリンの０−アルキル誘導体
、すなわちニンヒドリンの２１Ｉの水酸基の内のｉｌｌ
だけをアルキル化した誘導体が指紋検出性能を有し、か
つヘキサン等の脂肪族炭化水素系溶剤に溶解することを
見い出した。[Means for solving the problem] In order to achieve the above object, various O-alkyl derivatives of ninhydrin were synthesized and their solubility in hexane and fingerprint detection performance were tested. A novel 0-alkyl derivative of ninhydrin represented by
It has been found that a derivative obtained by alkylating only this has fingerprint detection performance and is soluble in aliphatic hydrocarbon solvents such as hexane.
−数式［Ｉ］中のＲとしては、すべてのアルキル基が考
えられるが、特に炭素数１から９のアルキル基、例えば
、メチル、エチル、１−プロピル、１−ブチル、１−ペ
ンチル、１−ヘキシル、１−ヘプチル、１−オクチル、
３−メチル−１−ブチル、２−メチル−１−ペンチル、
２．２−ジエチルエチル、 ３． ５． ５−トリメ
チル−１−ヘキシル基等があげられる。- All alkyl groups are conceivable as R in formula [I], but in particular alkyl groups having 1 to 9 carbon atoms, such as methyl, ethyl, 1-propyl, 1-butyl, 1-pentyl, 1- hexyl, 1-heptyl, 1-octyl,
3-methyl-1-butyl, 2-methyl-1-pentyl,
2.2-diethylethyl, 3. 5. Examples include 5-trimethyl-1-hexyl group.
本発明の式［Ｉ］で表わされる化合物は、式 で表わされるニンヒドリンに。The compound represented by the formula [I] of the present invention has the formula to ninhydrin, which is expressed as
式
Ｒ−ＯＨ
［■］
で表わされる化合物を反応させることにより容易に製造
することができる。この反応は下記の反応式で示される
ように、トリケトインダン［ＩＶ］を中間体として可逆
的に進行し、ニンヒドリン［Ｉｌｌの１分子に対し化合
物Ｃｍ］が１分子結合しｋものと考えられる。すなわち
、トリケトインダン［ＩＶ］よりも、ニンヒドリン［■
コの方が分子構造的により安定であり、トリケトインダ
ン［■］に水分子が１（［だけ付加することによりニン
ヒドリン［Ｉｌｌが生成されるのと同様に、ニンヒドリ
ン［］Ｉ］から水分子が１個とれて生成したトリケトイ
ンダン［ＩＶ］に化合物［■コを１個付加させることに
より、化合物［Ｉ］を比較的容易に合成できることを見
い出した。It can be easily produced by reacting a compound represented by the formula R-OH [■]. As shown in the reaction formula below, this reaction proceeds reversibly using triketoindane [IV] as an intermediate, and it is thought that one molecule of ninhydrin [compound Cm] is bound to one molecule of ninhydrin [Ill]. That is, ninhydrin [■
This is more stable in terms of molecular structure, and in the same way that ninhydrin [Ill is produced by adding 1 water molecule to triketoindan [■], 1 water molecule is produced from ninhydrin [I] It has been found that compound [I] can be synthesized relatively easily by adding one compound [■] to triketoindan [IV] separately produced.
［式中、Ｒはアルキル基を表わすコ
本発明の方法によれば、化合物［■］と１．５〜５当量
の化合物Ｃ１［Ｉ］を、８０〜１３０℃の適宜な温度で
３０分から２時間反応させ、生成する４量の水と過剰の
化合物［ｍ］を留去させることにより化合物［１］が得
られる。[Wherein, R represents an alkyl group] According to the method of the present invention, compound [■] and 1.5 to 5 equivalents of compound C1 [I] are heated for 30 minutes at an appropriate temperature of 80 to 130°C. Compound [1] is obtained by reacting for a period of time and distilling off the produced 4 amounts of water and excess compound [m].
前記方法によって、化合物ＣＩ］は結晶もしくは油状で
得られるので、再結晶操作を行うことにより、さらに高
純度の精製品とすることができる。Compound CI] can be obtained in the form of crystals or oil by the above-mentioned method, and thus a purified product with even higher purity can be obtained by performing a recrystallization operation.
得られた化合物ＣＩ］は、空気中や有機溶剤中でゆっく
りともとのニンヒドリンとアルー−ルに分解する性質を
有している“が、指紋検出における実務上の支障はほと
んどない、また、ニンヒドリンが有しておらず、化合物
［Ｉ］が有している特徴には、ヘキサン等の脂肪族炭化
水素系溶剤に溶解する性質や、その赤外吸収スペクトル
や核磁気共鳴スペクトル中にアルキル基に出来するピー
クが存在することなどがあげられる。The obtained compound CI] has the property of slowly decomposing into the original ninhydrin and an allol in the air or in an organic solvent, but this poses almost no practical problem in fingerprint detection. Characteristics that Compound [I] does not possess include the property of being soluble in aliphatic hydrocarbon solvents such as hexane, and the presence of alkyl groups in its infrared absorption spectrum and nuclear magnetic resonance spectrum. For example, there is a peak that can occur.
［作泪コ
この化合物ＣＩ］を用いて、例えば１次のように指紋が
検出される。A fingerprint is detected, for example, as in the first order using [Compound CI].
化合物［Ｉ］ （Ｒ＝３．５．５−）リメチルー）１
−ヘキシル基）０．５．とヘキサンＬＯＯｍｌ弘
をヒーカーなどの容器に入れ、磁気式かくはん機などを
泪いて、室温で１５〜３０分間かくはんし、溶解させる
。この液をろ過することにより、指紋検出液である。化
合物ＣＩＩ （Ｒ＝３．５．５−トリメチル−１−ヘ
キシル基）のヘキサン溶液が得られる。この指紋検出液
の効力は９日間以上持続する。Compound [I] (R=3.5.5-)limethyl-)1
-hexyl group) 0.5. Pour 1 ml of hexane into a container such as a heater, use a magnetic stirrer, etc., and stir at room temperature for 15 to 30 minutes to dissolve. By filtering this liquid, it becomes a fingerprint detection liquid. A hexane solution of compound CII (R=3.5.5-trimethyl-1-hexyl group) is obtained. The effectiveness of this fingerprint detection liquid lasts for more than 9 days.
指紋を検出したい物品、例えば感熱紙、をこの検出液に
浸漬するか、またはこの検出液を指紋を検出したい物品
に塗布し、自然乾燥によりヘキサンを散逸させる。この
後、指紋を検出したい物品を室内に放置しておくだけで
青〜赤紫色系統の色に発色した鯉明な借款が検出される
。An article whose fingerprints are to be detected, such as thermal paper, is immersed in this detection liquid, or this detection liquid is applied to the article whose fingerprints are to be detected, and the hexane is dissipated by air drying. Thereafter, by simply leaving the item whose fingerprints are to be detected indoors, a bright color in the blue to reddish-purple range will be detected.
この指紋検出液は極性溶剤をまったく含んでいないので
、指紋を°検出したい物品やその記載文字を汚染しない
のが特徴である。＊た、得られる指紋自体は、従来のニ
ンヒドリン法で得られる指紋と同様に安定であり、かつ
過酸化水素水などにより容易に消去可能である。Since this fingerprint detection liquid does not contain any polar solvent, it is unique in that it does not contaminate the article whose fingerprints are to be detected or the characters written on it. *Furthermore, the obtained fingerprint itself is as stable as the fingerprint obtained by the conventional ninhydrin method, and can be easily erased with hydrogen peroxide solution or the like.
［実施例］
（実施例１）式［Ｉコの化合物（Ｒ＝１−ペンチル基）
の製造
ニンヒドリン５ｇと１−ペンタノール１０ｍ１を１００
℃で１時１ｆｆｉ加熱かくはんする。水と過剰の１−ペ
ンタノールが留去されれば、液が黄色から緑色に変化す
るので、この時点で加熱を終了する。室温まで冷却する
とニンヒドリンの０−ペンチル誘導体が油状の粗生成物
として得られる。この粗生成物をヘキサンから再結晶１
ｌＩＫすると、油状の１＃製品３ｇが得られる。[Example] (Example 1) Compound of formula [I (R = 1-pentyl group)
Production of 5 g of ninhydrin and 10 ml of 1-pentanol in 100
Heat and stir at ℃ for 1 hour and 1ffi. When water and excess 1-pentanol are distilled off, the liquid changes color from yellow to green, and heating is terminated at this point. Upon cooling to room temperature, the 0-pentyl derivative of ninhydrin is obtained as an oily crude product. This crude product was recrystallized from hexane.
After lIK, 3 g of oily 1# product is obtained.
（実施例２）式［エコの化合物（Ｒ＝３． ５． ５−
トリメチル−１−ヘキシル基）の製造ニンヒドリン５ｇ
と３．５．５−）ジメチル−１−ヘキサノール１５ｍ１
を１３０℃で１時間加熱かくはんする。水と過剰の３．
５． ５−）ジメチル−１−ヘキサノールが留去され
れば、液が黄色から緑色に変化するので、この時点で加
熱を終了する。＊温まで冷却するとニンヒドリンの〇−
３、５，５−）ジメチル−１−ヘキシル誘導体が粗結晶
として得られる。この粗結晶をヘキサンから再結晶精製
すると、ｗｍ＊晶５ｇが得られる。(Example 2) Compound of formula [Eco (R=3.5.5-
Production of trimethyl-1-hexyl group) 5g of ninhydrin
and 15 ml of 3.5.5-)dimethyl-1-hexanol
Heat and stir at 130°C for 1 hour. 3. Water and excess.
5. 5-) Once dimethyl-1-hexanol is distilled off, the liquid changes from yellow to green, and at this point the heating is terminated. *When cooled to warm temperature, ninhydrin 〇-
The 3,5,5-)dimethyl-1-hexyl derivative is obtained as crude crystals. When this crude crystal is purified by recrystallization from hexane, 5 g of wm* crystals are obtained.
（実施例３）式［１］の化合物（Ｒ＝３−メチル−１−
ブチル１＆）の製造
実施ｆ！４２． において３，５．５−）ジメチル−
１−ヘキサノールの代わりに３−メチル−１−ブタノー
ルを泪いる以外は実施例２．と同様にしてニンヒドリン
５ｇと３−メチル−１−ブタノール１０ｍｌより結晶状
の化合＊［エコ （Ｒ＝３−メチル−１−ブチル基）が
４１に得られる。(Example 3) Compound of formula [1] (R=3-methyl-1-
Production implementation of butyl 1 &) f! 42. 3,5.5-)dimethyl-
Example 2 except that 3-methyl-1-butanol is used instead of 1-hexanol. In the same manner as above, a crystalline compound *[Eco (R=3-methyl-1-butyl group) 41] was obtained from 5 g of ninhydrin and 10 ml of 3-methyl-1-butanol.
（実施例４）式〔エコの化合物（Ｒ＝１−オクチル基）
の製造
実施例１．において１−ペンタノールの代わりに１−オ
クタツールを泪いる以外は実施例１．と同様にしてニン
ヒドリン５ｇと１−オクタツール１０ｍ１より油状の化
合物［Ｉ］ （Ｒ＝１−オクチル＆）が５ｇ得られる
。(Example 4) Compound of formula [Eco (R=1-octyl group)
Manufacturing Example 1. Example 1 except that 1-octatool was used instead of 1-pentanol. In the same manner as above, 5 g of oily compound [I] (R=1-octyl&) was obtained from 5 g of ninhydrin and 10 ml of 1-octatool.
次に、ニンヒドリンと１２種のアルコールから裏道した
本発明化合物のヘキサンに対する溶解性試験を行い、そ
の比較結果をＩｌ１表に示す。Next, a solubility test in hexane of the compound of the present invention prepared from ninhydrin and 12 kinds of alcohols was conducted, and the comparative results are shown in Table I11.
この表で示した溶解量は、ヘキサンｌｏｏｍｌに室温で
溶層した各化合物のグラム数およびモル数である。The dissolved amount shown in this table is the number of grams and number of moles of each compound dissolved in hexane room ml at room temperature.
寥
表
第１表から明らかなように、ニンヒドリンが全く溶解し
ないのに対し１本発明化合物はヘキサンに溶解し、特に
炭素数の大きいアルコール類から製造したちのは大きな
溶解性を示した。As is clear from Table 1, ninhydrin does not dissolve at all, whereas the compound of the present invention dissolves in hexane, and in particular, those prepared from alcohols with a large carbon number showed high solubility.
次に、本発明化合物の感熱紙からの指紋検出試験実施例
を示す。Next, an example of a fingerprint detection test using the compound of the present invention from thermal paper will be shown.
（指紋検出試験実施例１）本発明化合物［■］ （Ｒ：
３． ５． ５−）ツメチル−１−ヘキシル基）０．４
ｇをヘキサン１００ｍ１中でかくはん溶解させ、さらに
ろ過して得られたろ液を感熱紙からの指紋検出液とした
。この検出液を用いて、浸漬自然乾燥法により市販３種
の白色感熱紙に押捺した指紋の検出を試みた。なお、押
捺した指紋を３等分し、本法と従来から用いられている
２方法（前記のＡ法とＢ法）と比較した。検出結果をま
とめて第２表に示す。(Fingerprint detection test example 1) Compound of the present invention [■] (R:
3. 5. 5-) trimethyl-1-hexyl group) 0.4
g was stirred and dissolved in 100 ml of hexane, and the resulting filtrate was used as a fingerprint detection liquid from thermal paper. Using this detection liquid, an attempt was made to detect fingerprints printed on three types of commercially available white thermal paper using the immersion air-drying method. The imprinted fingerprint was divided into three equal parts, and the present method was compared with two conventionally used methods (method A and method B described above). The detection results are summarized in Table 2.
５１２表
１２表から明らかなように、従来から用いられているＡ
法では感熱紙の著しい変色が見られ、またＢ法では検出
した指紋が薄いのに対し、本発明化合物を泪いた本法で
は変色が全く見られず、しかも鮮明な指紋を検出するこ
とができた。512 Table 12 As is clear from Table 12, the conventionally used A
With method B, significant discoloration of the thermal paper was observed, and with method B, the detected fingerprints were faint, whereas with this method, which uses the compound of the present invention, no discoloration was observed at all and clear fingerprints could be detected. Ta.
（指紋検出試験実施例２）指紋検出試験実施例１と同機
に、本発明化合物［Ｉ］ （Ｒ＝３． ５． ５−ト
リメチル−１−ヘキシル基）から調製した検出液を月い
て、３種の感熱切符に押捺した指紋の検出を試みた。結
果を１１３表に示す。(Fingerprint Detection Test Example 2) A detection solution prepared from the compound [I] of the present invention (R = 3.5.5-trimethyl-1-hexyl group) was added to the same machine as in Fingerprint Detection Test Example 1, and An attempt was made to detect fingerprints stamped on seed heat-sensitive tickets. The results are shown in Table 113.
′１．３表
３１３表から明らかなように、従来から用いられている
へ方法では記載文字のにじみや変色が見られ、またＢ方
法ではほとんど指紋が検出されないのに対し１本発明化
合物を泪いた本法では記載文字のにじみや変色が全く見
られず、しかも鮮明な指紋を検出することができた。'1.3 Table 313 As is clear from Table 313, in the conventional method B, blurring and discoloration of the written characters were observed, and in method B, almost no fingerprints were detected, whereas in the case of the compound of the present invention, With this method, no bleeding or discoloration of written characters was observed, and clear fingerprints could be detected.
［発明の効果］
本発明の目的化合物である式［１で表されるニンヒドリ
ンのＯ−アルキル誘導体化合物は、各種の紙をはじめと
した各種の物体などからでも今までの試薬より記載文字
をにじませることなく鮮明に指紋を検出できるし、今ま
で指紋検品が不可能、または、困難であると思われてい
た極性溶剤で変色したり、溶解したりする物品１例えば
感熱紙、Ｉ！！熱切符等の感熱物、に適用しても鮮明に
指紋検出ができる。[Effects of the Invention] The objective compound of the present invention, an O-alkyl derivative compound of ninhydrin represented by the formula Fingerprints can be clearly detected without any stains, and fingerprint inspection has been thought to be impossible or difficult until now for items that discolor or dissolve with polar solvents, such as thermal paper, I! ! Fingerprints can be clearly detected even when applied to heat-sensitive objects such as thermal tickets.
本発明により、指紋検出試薬として優れた性質を有する
新規化学物質を提供することができた。ADVANTAGE OF THE INVENTION According to the present invention, a new chemical substance having excellent properties as a fingerprint detection reagent could be provided.
また５式［■］で表されるニンヒドリンを出発物質とす
ることにより。Alternatively, by using ninhydrin represented by formula 5 [■] as a starting material.
式 ［ ］ で表される本発 明の目的化合物を容易にｍ造することができた。formula [ ] The origin expressed by The desired compound could be easily produced.
Claims (3)
１）記載の化合物（式［ I ］）の製法。(2) A claim consisting of reacting a compound represented by the formula ▲ Numerical formula, chemical formula, table, etc. ▼ [II] R-OH [III] [In the formula, R represents an alkyl group]
1) Method for producing the described compound (formula [I]).
る指紋検出試薬(3) A fingerprint detection reagent comprising the compound (formula [I]) according to claim (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24589190A JP2952609B2 (en) | 1990-09-14 | 1990-09-14 | Fingerprint detection reagent and its manufacturing method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24589190A JP2952609B2 (en) | 1990-09-14 | 1990-09-14 | Fingerprint detection reagent and its manufacturing method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04124156A true JPH04124156A (en) | 1992-04-24 |
| JP2952609B2 JP2952609B2 (en) | 1999-09-27 |
Family
ID=17140352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24589190A Expired - Fee Related JP2952609B2 (en) | 1990-09-14 | 1990-09-14 | Fingerprint detection reagent and its manufacturing method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2952609B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000186269A (en) * | 1998-10-13 | 2000-07-04 | Lintec Corp | Ninhydrin-containing pressure-sensitive adhesive composition and sheet for detecting amino compound |
| JP2006204398A (en) * | 2005-01-26 | 2006-08-10 | Asahi Glass Co Ltd | Liquid for detecting fingerprint, its manufacturing method, and method for detecting fingerprint by using it |
| JP2007269356A (en) * | 2006-03-31 | 2007-10-18 | Lintec Corp | Leakage detecting sheet and container carrying leakage detecting sheet |
-
1990
- 1990-09-14 JP JP24589190A patent/JP2952609B2/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000186269A (en) * | 1998-10-13 | 2000-07-04 | Lintec Corp | Ninhydrin-containing pressure-sensitive adhesive composition and sheet for detecting amino compound |
| JP2006204398A (en) * | 2005-01-26 | 2006-08-10 | Asahi Glass Co Ltd | Liquid for detecting fingerprint, its manufacturing method, and method for detecting fingerprint by using it |
| JP4609083B2 (en) * | 2005-01-26 | 2011-01-12 | 旭硝子株式会社 | Liquid for fingerprint detection, manufacturing method thereof, and fingerprint detection method using the same |
| JP2007269356A (en) * | 2006-03-31 | 2007-10-18 | Lintec Corp | Leakage detecting sheet and container carrying leakage detecting sheet |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2952609B2 (en) | 1999-09-27 |
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