JP2009286832A - Coloring agent for petroleum product - Google Patents

Coloring agent for petroleum product Download PDF

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JP2009286832A
JP2009286832A JP2008138072A JP2008138072A JP2009286832A JP 2009286832 A JP2009286832 A JP 2009286832A JP 2008138072 A JP2008138072 A JP 2008138072A JP 2008138072 A JP2008138072 A JP 2008138072A JP 2009286832 A JP2009286832 A JP 2009286832A
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Japan
Prior art keywords
dyes
dye
solvent
petroleum product
coloring agent
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JP2008138072A
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Japanese (ja)
Inventor
Hiroaki Yamamoto
博明 山本
Sakae Matsumura
榮 松村
Kazuhiro Shirato
和弘 白土
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SHIRADO KAGAKU KK
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SHIRADO KAGAKU KK
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Abstract

<P>PROBLEM TO BE SOLVED: To provide a coloring agent for petroleum products that prevents generation of harmful substances based on an azo dye and is safe and friendly to the environment. <P>SOLUTION: The coloring agent for petroleum products has various color tones and are prepared by dissolving dyes comprising as the main components red and blue anthraquinone dyes and yellow methine and quinoline dyes in a mixed solvent of methylnaphthalene and styrenated phenol. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

本発明は、各種石油製品の成分内容を識別したり、または商品価値を高めるための石油製品着色剤に関するものである。   The present invention relates to a petroleum product colorant for identifying the component contents of various petroleum products or increasing the commercial value.

一般に、石油製品の着色剤は使用する際の容易性から、粉末染料を有機溶剤に溶解した液体染料、又は粉末化の工程を経ないで直接溶液タイプの染料に加工したものがある。   In general, because of the ease of use, petroleum product colorants include liquid dyes obtained by dissolving a powder dye in an organic solvent, or those processed directly into a solution type dye without passing through a powdering step.

しかも、これらの染料そのものは赤系及び黄系着色剤においてはアゾ系の染料を使用しており、この染料は価格が安く着色力も強いので、トリーティングコストが安く経済的な染料である(例えば非特許文献1、2参照)。
カラーケミカル事典 第67頁ないし第72頁 社団法人有機合成化学協会 境 鶴雄 株式会社シーエムシー発行 色素の化学と応用、第4頁ないし10頁 社団法人日本化学会、松岡 賢著 大日本図書株式会社発行
In addition, these dyes themselves use azo dyes in red and yellow colorants, and these dyes are inexpensive and have strong coloring power. Non-patent documents 1 and 2).
Color Chemical Encyclopedia Pages 67 to 72 Japan Synthetic Organic Chemistry Association Tsuruo Sakai Published by CMC Co., Ltd. Dye chemistry and application, pages 4 to 10 The Chemical Society of Japan, Ken Matsuoka Published by Dai Nippon Book Co., Ltd.

これらの非特許文献1、2に示す染料は、アゾ染料は出発原料にオルソアミノアゾトルエン又はオルソトルイジンなどを使用していることから、微量ではあるがその製品中にこれらの物質が含まれるか、又はその製品が分解した時にこれらの物質が発生する懸念があり、特定の有害アミンを放出する可能性のあるアゾ染料として懸念される。   In these dyes shown in Non-Patent Documents 1 and 2, since azo dyes use orthoaminoazotoluene or orthotoluidine as a starting material, are these substances contained in the product in a small amount? There is a concern that these substances may be generated when the product is decomposed, and there is a concern as an azo dye that may release a specific harmful amine.

本発明は如上の点に着目して成されたもので、特定の有害アミンの放出のない環境に適応した新規な石油製品着色剤を提供することを目的とするものである。   The present invention has been made in view of the above points, and an object of the present invention is to provide a novel petroleum product colorant adapted to an environment in which no specific harmful amine is released.

本発明は以下の構成を備えることにより、上記課題を解決するものである。   This invention solves the said subject by providing the following structures.

(1)赤色及び青色のアンソラキノン等染料及び黄色のメチン系染料及びキノリン系染料を主成分の染料とし、これをメチルナフタレン及びスチレン化フェノールの混合溶剤に溶解し、調整して、多種類の色調を得ることを特徴とする石油製品着色剤。   (1) Red and blue anthraquinone dyes and yellow methine dyes and quinoline dyes are the main dyes, which are dissolved and adjusted in a mixed solvent of methylnaphthalene and styrenated phenol to produce a variety of color tones A petroleum product colorant characterized in that it is obtained.

(2)主成分の染料の混合比5〜30%に対し、混合溶剤を70〜95%として成ることを特徴とする(1)記載の石油製品着色剤。   (2) The petroleum product colorant according to (1), wherein the mixed solvent is 70 to 95% with respect to the mixing ratio of the main component dye of 5 to 30%.

本発明によれば、色素としてアンソラキノン系染料及びメチン系染料,キノリン系染料を用いているので、有害物質の発生がなく安全に使用できると共に、溶剤としては、単一でなくメチルナフタレン及びスチレン化フェノールの混合溶剤を用いるので、溶解力を向上して色調の優れた着色剤を提供できる。   According to the present invention, anthoraquinone dyes, methine dyes, and quinoline dyes are used as pigments, so that no harmful substances are generated and they can be used safely, and the solvent is not single but methylnaphthalene and styrenation. Since a mixed solvent of phenol is used, it is possible to improve the dissolving power and provide a colorant having excellent color tone.

そして、赤色、青色、黄色、緑色、橙色、茶色及び黒色系の石油製品着色剤として、潤滑油用着色剤、グリース用着色剤、或は燃料油用着色剤などへ広く利用できる。   And as red, blue, yellow, green, orange, brown and black petroleum product colorants, they can be widely used as lubricant colorants, grease colorants, or fuel oil colorants.

本発明を実施するための最良の形態を実施例により詳しく説明する。   The best mode for carrying out the present invention will be described in detail by way of examples.

本発明者等は、数多くの染料の中から、毒性がなく、溶剤との溶解性に優れ、かつ油溶性のアンソラキノン系及びメチン系並びにキノリン系の染料を以下の通り選別した。   The present inventors selected from among a large number of dyes, non-toxic, excellent solubility in solvents and oil-soluble anthraquinone, methine, and quinoline dyes as follows.

本発明にあたって試験した染料
a.赤色系(アンソラキノン系)
染料A:C.I.ソルベントレッド111,C.I.60505
染料B:C.I.ソルベントレッド168,1−シクロヘキシルアミノア
ンソラキノン
染料C:C.I.ディスパーズレッド22,C.I.60510
染料D:C.I.ディスパーズレッド60,C.I.60756
染料E:C.I.ディスパーズバイオレット26,C.I.62025
染料F:1−アミノ、2−ブロム、4−ヒドロキシアンソラキノン
b.黄色系(キノリン系及びメチン系)
染料G:C.I.ソルベントイエロー33,C.I.47000
染料H:C.I.ソルベントイエロー93,C.I.48160
c.橙色系(アミノケトン系)
染料I:C.I.ソルベントオレンジ60,C.I.564100
d.青色系(アンソラキノン系)
染料J:ソルベントブルー35,C.I.61554
染料K:C.I.ソルベントブルー58,C.I.617043
e.緑色系(アンソラキノン系)
染料L:C.I.ソルベントグリーン3,C.I.61565
染料M:C.I.ソルベントグリーン28,C.I.625580
Dyes tested in the present invention a. Red (Ansolaquinone)
Dye A: C.I. I. Solvent Red 111, C.I. I. 60505
Dye B: C.I. I. Solvent Red 168,1-cyclohexylaminoa
Psoraquinone dye C: C.I. I. Disperse Red 22, C.I. I. 60510
Dye D: C.I. I. Disperse Red 60, C.I. I. 60756
Dye E: C.I. I. Dispers Violet 26, C.I. I. 62025
Dye F: 1-amino, 2-bromo, 4-hydroxyanthoraquinone b. Yellow (quinoline and methine)
Dye G: C.I. I. Solvent Yellow 33, C.I. I. 47000
Dye H: C.I. I. Solvent Yellow 93, C.I. I. 48160
c. Orange system (aminoketone system)
Dye I: C.I. I. Solvent Orange 60, C.I. I. 564100
d. Blue (Ansolaquinone)
Dye J: Solvent Blue 35, C.I. I. 61554
Dye K: C.I. I. Solvent Blue 58, C.I. I. 617043
e. Green (Ansolaquinone)
Dye L: C.I. I. Solvent Green 3, C.I. I. 61565
Dye M: C.I. I. Solvent Green 28, C.I. I. 625580

上記各染料は、それぞれのC.I.Constitution Numberによって特定した。   Each of the above dyes has its own C.I. I. Identified by Constitution Number.

つぎに、溶剤として知られる下記の2つの溶剤を抽出した。
溶剤1:スチレン化フェノール
溶剤2:メチルナフタレン
Next, the following two solvents known as solvents were extracted.
Solvent 1: Styrenated phenol solvent 2: Methylnaphthalene

その他の溶剤としてジノニルフェノール,N−メチル−2−ピロリドン,1−フェニル−1−キシリルエタンと1−フェニル−1−エチルフェニルエタンの混合物を選択したが、溶解性が不十分で実用に供し得なかった。   As other solvent, a mixture of dinonylphenol, N-methyl-2-pyrrolidone, 1-phenyl-1-xylylethane and 1-phenyl-1-ethylphenylethane was selected, but the solubility was insufficient and could not be put to practical use. It was.

上記各染料に対して、前記溶剤1と溶剤2との混合配合を異にして、実用性の有無を検討したところ、以下の表1の通りの結果が得られた。   For each of the above dyes, the presence or absence of practicality was examined by changing the mixing composition of the solvent 1 and the solvent 2, and the results shown in Table 1 below were obtained.

Figure 2009286832
Figure 2009286832

上記の通り染料単品の混合溶剤に対する溶解性・安定性試験により下記染料は溶解性・安定性が良いことが判明した。
染料A(赤)、染料B(赤)、染料E(赤)、染料G(黄)、染料H(黄)、染料K(青)
As described above, the following dyes were found to have good solubility and stability by the solubility / stability test of the dye alone in the mixed solvent.
Dye A (red), Dye B (red), Dye E (red), Dye G (yellow), Dye H (yellow), Dye K (blue)

そして、更に検討した結果、溶剤の混合比は溶解性、価格及び取扱いやすさなどから判断し、溶剤1:溶剤2につき40%:40%が最良と結論した。   As a result of further investigation, the mixing ratio of the solvent was judged from solubility, cost, ease of handling, etc., and it was concluded that 40%: 40% per solvent 1: solvent 2 was the best.

次に、求められる各々の最終色調に合わせるため、上記染料より価格を加味した上で適当な数種類を選び下記の通り配合して染料(赤色系)、(橙色系)、(黄色系)、(茶色系)を調合し、この液体染料の溶解性・安定性試験を下記条件にて行い、表2の結果を得た。   Next, in order to match each required final color tone, several appropriate types are selected in consideration of the price from the above dyes and blended as follows, and dyes (red), (orange), (yellow), ( Brown) was prepared, and the solubility / stability test of this liquid dye was conducted under the following conditions to obtain the results shown in Table 2.

尚、本件における下記染料の配合比は、現在市販されている各色の一部の色調に合わせたものである。   In addition, the compounding ratio of the following dye in this case is adapted to a partial color tone of each color currently on the market.

Figure 2009286832
Figure 2009286832

この試験の結果、アンソラキノン系(赤色及び青色)及びメチン系,キノリン系(黄色系)染料5〜30%を主成分とし、スチレン化フェノール及びメチルナフタレンの混合溶剤70〜95%に溶解し調整した、赤色、青色、黄色、緑色、橙色、紫色、茶色及び黒色系の石油製品着色剤は、低温でも安定で沈殿の発生しないことが実証された。   As a result of this test, 5-30% of ansoraquinone (red and blue), methine, and quinoline (yellow) dyes are the main components, and dissolved and adjusted in 70-95% of a mixed solvent of styrenated phenol and methylnaphthalene. Red, blue, yellow, green, orange, purple, brown and black petroleum product colorants have been demonstrated to be stable and free of precipitation even at low temperatures.

Claims (2)

赤色及び青色のアンソラキノン系染料及び黄色のメチン系染料及びキノリン系染料を主成分の染料とし、これをメチルナフタレン及びスチレン化フェノールの混合溶剤に溶解し、調整して、多種類の色調を得ることを特徴とする石油製品着色剤。   Red and blue ansolaquinone dyes and yellow methine dyes and quinoline dyes are used as the main dyes, and they are dissolved in a mixed solvent of methylnaphthalene and styrenated phenol and adjusted to obtain a variety of colors. Petroleum product colorant characterized by. 主成分の染料の配合比5〜30%に対し、混合溶剤を70〜95%として成ることを特徴とする請求項1記載の石油製品着色剤。   The petroleum product colorant according to claim 1, wherein the mixed solvent is 70 to 95% with respect to the blending ratio of the main component dye of 5 to 30%.
JP2008138072A 2008-05-27 2008-05-27 Coloring agent for petroleum product Withdrawn JP2009286832A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011111710A1 (en) * 2010-03-09 2011-09-15 三菱化学株式会社 Ink containing anthraquinone pigment, pigment used in that ink and display
JP2012062349A (en) * 2010-09-14 2012-03-29 Adeka Corp Additive composition for lubricant and lubricant composition containing the same

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011111710A1 (en) * 2010-03-09 2011-09-15 三菱化学株式会社 Ink containing anthraquinone pigment, pigment used in that ink and display
CN102782052A (en) * 2010-03-09 2012-11-14 三菱化学株式会社 Ink containing anthraquinone pigment, pigment used in that ink and display
JPWO2011111710A1 (en) * 2010-03-09 2013-06-27 三菱化学株式会社 Ink containing anthraquinone dye, dye used in the ink, and display
CN102782052B (en) * 2010-03-09 2014-07-30 三菱化学株式会社 Ink containing anthraquinone pigment, pigment used in that ink and display
US8999050B2 (en) 2010-03-09 2015-04-07 Mitsubishi Chemical Corporation Ink containing anthraquinone based dye, dye used in the ink, and display
JP5747909B2 (en) * 2010-03-09 2015-07-15 三菱化学株式会社 Ink containing anthraquinone dye, dye used in the ink, and display
JP2012062349A (en) * 2010-09-14 2012-03-29 Adeka Corp Additive composition for lubricant and lubricant composition containing the same

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