WO2002094941A1 - Procede permettant la production d'un pigment noir - Google Patents

Procede permettant la production d'un pigment noir Download PDF

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Publication number
WO2002094941A1
WO2002094941A1 PCT/JP2001/004115 JP0104115W WO02094941A1 WO 2002094941 A1 WO2002094941 A1 WO 2002094941A1 JP 0104115 W JP0104115 W JP 0104115W WO 02094941 A1 WO02094941 A1 WO 02094941A1
Authority
WO
WIPO (PCT)
Prior art keywords
acid
black
aniline
persulfate
black pigment
Prior art date
Application number
PCT/JP2001/004115
Other languages
English (en)
Japanese (ja)
Inventor
Michichika Hikosaka
Original Assignee
Tokyo Shikizai Industry Co., Ltd.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to JP2000266731A priority Critical patent/JP4703826B2/ja
Application filed by Tokyo Shikizai Industry Co., Ltd. filed Critical Tokyo Shikizai Industry Co., Ltd.
Priority to PCT/JP2001/004115 priority patent/WO2002094941A1/fr
Publication of WO2002094941A1 publication Critical patent/WO2002094941A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
    • 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
    • C09B17/00—Azine dyes
    • C09B17/02—Azine dyes of the benzene series
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/41—Organic pigments; Organic dyes
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133509—Filters, e.g. light shielding masks
    • G02F1/133512—Light shielding layers, e.g. black matrix

Definitions

  • the present invention relates to a novel process for producing aniline black, a novel aniline black obtained thereby, and a printing ink composition, a coating composition and a black pigment for a liquid crystal display comprising the same.
  • Aniline black is a black dye and pigment obtained by the oxidative condensation of aromatic amines such as aniline, toluidine, and phenylenediamine.It has excellent features such as jet-blackness and certain suitability for use that are not found in Ripbon black. It is used for various purposes such as paints, printing inks, paints, posters, plastics, and thermal transfer inks.
  • Dichromates, chlorates, hydrogen peroxide, etc. have been used as oxidizing agents in the production of aniline black, and copper salts, vanadium oxides, etc. have been used and studied as catalysts. However, to date, the method using dichromate has been considered optimal. Disclosure of the invention
  • aniline black As described above, the method using dichromate has been considered the most suitable method for producing aniline black so far.
  • chromium ions are extremely harmful pollutants to the human body.
  • the chromium contained in aniline black coordinates with the dye and does not contain harmful hexavalent chromium, but its safety has been recognized.
  • copper ions derived from copper salts used as catalysts are also recognized. It is also a harmful substance. Therefore, aniline black, which does not use these harmful substances at the time of manufacture and has no danger of mixing these harmful substances into the product, and has properties not inferior to aniline black obtained by the chromium method It is an object of the present invention to provide a method for producing black. It is an issue. BEST MODE FOR CARRYING OUT THE INVENTION
  • the present invention provides a method for producing aniline black, which comprises oxidizing aniline with a persulfate in an aqueous acid solution.
  • the present invention also relates to aniline black obtained by the above production method. Furthermore, the present invention relates to a printing ink composition, a coating composition and a black pigment for a liquid crystal display, which comprise aniline black obtained by the above-mentioned production method. Furthermore, the present invention relates to a liquid crystal display using aniline black obtained by the above production method as a black matrix dye.
  • the persulfate used as an oxidizing agent is, for example, an ammonium salt, for example, an alkali metal salt such as sodium persulfate or potassium persulfate, or an alkaline earth metal salt such as barium persulfate. And the like, but ammonium persulfate is more inexpensive and more preferable.
  • the theoretical amount of persulfate used as an oxidizing agent is 14 moles per 11 moles of phosphorus, but is usually about the theoretical amount or about twice as much as the theoretical amount. Is about 1.2 to 1.7 times the theoretical amount.
  • the persulfate used as an oxidizing agent may be used alone or in combination with another oxidizing agent such as chlorate.
  • oxidizing agents When used in combination with other oxidizing agents, first oxidize with persulfate, then oxidize with chlorate, etc., or first oxidize with chlorate, etc., and then oxidize with persulfate. Alternatively, a persulfate and a chlorate may be used together from the beginning. However, a method of oxidizing with a persulfate first and then oxidizing with a chlorate or the like is more preferable.
  • persulfate and chlorate there is no particular limitation on the proportion of persulfate and chlorate used, but a higher proportion of persulfate is more desirable.
  • the total amount used as an oxidizing agent may be the same as when persulfate is used alone.
  • the aqueous solution of an acid used in the production method of the present invention includes, for example, aqueous solutions of mineral acids such as hydrochloric acid, sulfuric acid, nitric acid, tetrafluoroboric acid, perchloric acid, and periodic acid, for example, formic acid, acetic acid, and propionic acid.
  • Butyric acid and other carboxylic acid aqueous solution for example, benzene sulfo
  • examples thereof include aqueous solutions of sulfonic acids such as acid, p-toluenesulfonic acid, methanesulfonic acid, and ethanesulfonic acid.
  • aqueous solutions of mineral acids are preferable, and aqueous solutions of tetrafluoroboric acid are particularly preferable.
  • hydrochloric acid, sulfuric acid, nitric acid, or a mixture thereof, and the like also apply.
  • a mineral acid for example, tetrafluoroboric acid
  • an organic acid aqueous solution may be used in combination.
  • an aqueous solution of a diacid eg, tetrafluoroboric acid
  • an emulsion of a higher fatty acid insoluble in water eg, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, etc.
  • a mineral acid for example, tetrafluoroboric acid
  • an aqueous solution of a polymer having a carboxyl group such as polyacrylic acid or polymethacrylic acid or a water-soluble salt thereof
  • calcium chloride or the like is added to the reaction solution to convert the polymer into a water-insoluble salt, followed by ordinary post-treatment, since a black pigment with good dispersibility can be obtained.
  • the concentration of the aqueous acid solution depends on the type of the acid, but is usually 1 to 10%, and preferably about 2 to 8%.
  • a catalyst is not always required, but the use of an iron salt slightly increases the reaction rate.
  • iron salts include, for example, ferrous chloride, ferric chloride, ferrous bromide, ferric bromide, ferrous sulfate, and ferric sulfate.
  • inorganic water-soluble iron salts The amount of the iron salt to be used is usually about 0.1 to 5 mol, preferably about 1 to 2.5 mol, per 11 mol of aniline.
  • the reaction temperature and reaction time are not particularly limited, but are usually 10 to 60 ° C, preferably 20 to 50 ° C, and the dropping of the persulfate takes 10 to 60 minutes. Then, the reaction may be performed at 50 to 80 ° C. for 1 to 2 hours, and more preferably at 90 to 95 X: for 30 minutes to 1 hour. After the reaction, unnecessary substances are collected by filtration, washed with water, and if necessary, re-slurried with water and neutralized with an aqueous alkali solution such as an aqueous sodium hydroxide solution, and then, if necessary, 90 to 95 °.
  • an aqueous alkali solution such as an aqueous sodium hydroxide solution
  • the mixture is heated and stirred at C for 30 minutes to 1 hour, and then filtered, washed with water, and dried to obtain the desired black pigment.
  • the pH of the system is strongly acidic with 1 to 2, but even if it is filtered, washed, and dried without neutralization as it is, once filtered, it is re-slurried and neutralized. It may be filtered again, washed with water and dried.
  • the acid is reacted at 60 to 80 for 1 to 2 hours after dropping the persulfate. After that, for example, calcium chloride or the like is added, and the mixture is stirred at the same temperature for about 30 minutes to convert the polymer into a water-insoluble salt. If the above-mentioned post-treatment is performed, the dispersion is performed as described above. This is preferable since a black pigment having good properties can be obtained.
  • the aniline black of the present invention is not only chromium-free, but also has properties that are not inferior to those of the aniline black obtained by the conventional chromium method, and particularly has a jet-black color tone, and the coloring power of the former 2 Since it is twice as large, it can be used more effectively in any of the various applications conventionally known as uses of aniline black, including printing inks and paints. 'Furthermore, the aniline black of the present invention has an absorbance of 1.3 to 1.4 times higher than that of the conventional aniline black (by the chromium method).
  • the pigment concentration (pigment Z pigment + resin)
  • the absorbance at a wavelength of 400 to 800 nm at 0% shows a value of 2.5 to 3.0 (average), which is similar to that of Ripbon black when used as a black pigment for liquid crystal displays. Comparable.
  • the aniline black of the present invention exhibits a substantially flat value in all wavelength ranges, similarly to conventional aniline black, which is a great advantage. It is.
  • the printing ink composition of the present invention is characterized in that the aniline black of the present invention is used as a black pigment, and the other components may be exactly the same as those of the known printing ink composition.
  • Vegetable oils such as linseed oil; synthetic resin such as phenolic resin; varnishes for offset inks; natural resins such as rosins; semi-synthetic resins such as nitrocellulose and acetate cellulose; polyamide resins; An arbitrary combination with a varnish for gravure ink using a synthetic resin such as a resin, a polyurethane, or a polyester is exemplified.
  • the coating composition of the present invention is also characterized in that the aniline black of the present invention is used as a black pigment, and the other components may be exactly the same as those of the coating composition known per se.
  • examples of the resin component include any combination of alkyd resin, melamine resin, acrylic resin, urethane resin, polyester resin, and the like.
  • examples of the solvent include aromatic hydrocarbons such as toluene and xylene. And ketones such as methylethyl ketone, esters such as ethyl acetate, alcohols such as isopropanol, water alone and mixtures thereof.
  • the black pigment for a liquid crystal display of the present invention contains the aniline black of the present invention as a main component. If necessary, a resin component for improving dispersibility and other various additives are used as constituent components. May be included.
  • Example 1
  • Example 5 Dissolve 10 g of aniline in 200 ml of a 5.1% aqueous sulfuric acid solution, add 2.6 g of ferric chloride hexahydrate, and add 48 g of ammonium persulfate at 40 ° C with water 2 After the solution dissolved in 0 m1 was added dropwise over 15 minutes, the mixture was heated to 70 to 75 ° C and stirred for 1 hour. ⁇ After the reaction, the insolubles were collected by filtration, washed with water, and the obtained cake was collected. The slurry was reslurried in 300 ml of water, adjusted to pH 7 with a 10% aqueous sodium hydroxide solution, and then heated and stirred at 90 ° C. for 30 minutes. The insoluble material was collected by filtration, washed with water, and dried to obtain 8.9 g of a slightly bluish jet-black pigment (black pigment-5).
  • Example 6 Dissolve 10 g of aniline in 200 ml of a 5.1% aqueous
  • Dissolve 10 g of aniline in 22 ml of 8% tetrafluoroboric acid add 10 g of oleic acid, 10 g of xylene, and 0.7 g of polyoxyethylene lauryl ether (HLB14).
  • Emulsion was added to a solution composed of 100 g of water and 100 g of water, and a solution of 40 g of ammonium persulfate dissolved in 130 m of water was added dropwise at 30 to 55 over 30 minutes. Thereafter, the mixture was stirred at 50 to 55 ° C for 3 hours. After completion of the reaction, 10 ml of 10% calcium chloride was added to the reaction solution, and the mixture was stirred for 30 minutes.
  • black pigment-1 0.5 g was precisely weighed, 1.0 g of No. 4 varnish was added, and the mixture was kneaded with a Hoover muller to prepare black ink-1.
  • black pigments 1, 2, 1, 3, 4, and 5 were treated in the same manner to obtain black inks 1, 2, 3, 14, and 15.
  • No. 2 Super Black C. I. Pigment B lack 1 manufactured by Tokyo Color Materials Co., Ltd.
  • No. 2 SB is 1 0 g was precisely weighed and 1.0 g of No. 4 varnish was added, and the mixture was kneaded with a Hoover muller to obtain a dark standard ink.
  • the standard ink and the black ink 11 according to the present invention were placed on colored paper so as to be in contact with each other.
  • Developed samples of black inks 1, 2, 3, 4, and 5 were prepared in the same manner.
  • a light color sample was prepared by arranging the light-colored inks 1, 1, 2, 1, 3, 4 and 5 with the standard light-colored ink in the same manner as the dark-colored inks.
  • Table 1 shows the results of visually evaluating the hue, tinting strength, and jet-blackness of these test papers.
  • H represents a hue, and each represents a color in a range from B (blue one) representing blue to PB (purple blue one) representing purple blue.
  • B blue one
  • PB primary blue one
  • the coefficients of B and PB take values in the range of 1 to 10, and the larger the value, the more purple. Therefore, in Table 2, the black pigment 1-1 is more purple than the standard (No. 2 SB), and the black pigments 1-2, 1-3: One 4, — 5 is bluish (greenish).
  • this method is a colorimetric value for a gray developed material mixed with a white pigment, and does not make a noticeable difference in the dark black that is often used.
  • V is a value indicating the color density, and takes a value from 0 to 10; the larger the value, the closer to white.
  • the standard enamel and dark enamel 1 prepared in Example 9 were spread on art paper so as to be in contact with each other using a 6-mil applicator, allowed to stand for 20 minutes, and then left at 110 ° C. for 30 minutes. It was baked to make a dark colored sample.
  • a pale sample was prepared by the following procedure. 10 g of dark enamel-2 was weighed, and white enamel was added so as to have a pigment ratio of 1/10, and mixed with a homomixer to prepare light enamel-2.
  • the dark enamels 3, 4 and 15 as well as the standard dark enamel for comparison were prepared in the same manner as the light enamels 1-3,-,-5 and the standard light enamel.
  • the hue, tinting strength, and jet-blackness of the dark and light colored samples were visually evaluated.
  • light color samples were also evaluated by colorimetry.
  • Color measurement is Minolta The measurement was performed in a Munsell colorimetric system and an L * a * b * colorimetric measurement mode using a color difference meter CR-3331 manufactured by the company.
  • the Munsell color system is a color system that displays perceived color in three dimensions.
  • the hue is the rotation axis from the X axis
  • the brightness is the height of the center axis
  • the saturation (saturation) is the center axis. Expressed as the distance from.
  • the Munsell color solid has a total of 10 colors (red (R), yellow (Y), green (G), blue (B), purple (P) and their intermediate colors (YR, GY, BG, PB, RP)).
  • the colors of the same hue (having the same value of H) are arranged on the radius so that the saturation (C) increases. This color system is characterized by good correspondence with the senses.
  • the L * a * b * color system is also a color system that expresses colors in a three-dimensional space, and is configured so that intuitively the same color difference is the same distance in the color space It is one of the perceptual spaces.
  • the L axis corresponds directly to brightness.
  • the a and b axes are not values that directly represent color, but a small difference indicates that the hues are similar.
  • the difference ⁇ E between two colors is the distance between two colors located in this color space, and is expressed by the following equation.
  • black pigment 1-2 has a purple (reddish) color
  • black pigment 14 has a bluish color
  • black pigment— 3, 5 were almost the same hue as the standard.
  • the tinting strength of the black pigments 1, 2, 1-3, —4, and —5 was significantly higher than the standard.
  • the distance ⁇ E between two colors when the colors are represented in a three-dimensional space represents the overall hue difference. Both 14 and 15 show considerable differences. However, if you look at the content, you can see that many parts are due to the difference in L * value, in other words, due to the difference in coloring power.
  • Black pigment 17 was mixed with an alkyd melamine-based paint, applied to an acetate film, and the absorbance was measured.
  • anilin black (No. 2SB) obtained by the conventional chromium method was similarly measured.
  • Pigment concentration (pigment / pigment + resin): 10%
  • Measuring device Self-recording spectrophotometer UV-3 8 5 (Shimadzu Corporation)
  • Table 5 shows the results. Table 5 Black pigment wavelength (nm)
  • Example 10 With respect to the black pigment 18 obtained in Example 10, a paint test and evaluation of a coating film were performed in the same manner as in Test Example 2. Table 6 shows the results of the visual judgment of the dark and light colored coating films, and Table 7 shows the colorimetric results of the monochromatic coating films. Table 6 Color Light color
  • the present invention provides a method for producing aniline black which does not use harmful substances such as chromium and copper, and thus does not have a risk of mixing these harmful metals in the obtained black pigment.
  • the aniline black obtained by the production method of the present invention is chromium-free, and has properties comparable to those of the aniline black obtained by the chromium method, in particular, a jet-black color tone.
  • the aniline black of the present invention has an absorbance of 1.3 to 1.4 times higher than that of the conventional aniline black (by the chromium method).
  • the absorbance at a wavelength of 400 to 800 nm at 100% is remarkable in that it is comparable to that of carbon black when used as a black pigment for liquid crystal displays. Play an effect I do. Therefore, the present invention is a very large invention that contributes to the industry.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne un procédé permettant de produire du noir d'aniline sans utilisation de composants toxiques tels que chrome ou cuivre, et évitant ainsi tout risque de présence de ces composants dans le produit final, et un nouveau noir d'aniline préparé au moyen de ce procédé, dont les propriétés sont équivalentes à celles du noir d'aniline préparé au moyen d'un procédé au chrome. Le procédé décrit est caractérisé une oxydation de l'aniline à l'aide d'un persulfate, dans une solution acide aqueuse. L'invention concerne également une composition d'encre d'impression, une composition de revêtement et un pigment noir pour afficheurs à cristaux liquides, qui contiennent ou comprennent chacun le noir d'aniline préparé au moyen du procédé décrit.
PCT/JP2001/004115 2000-01-14 2001-05-17 Procede permettant la production d'un pigment noir WO2002094941A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2000266731A JP4703826B2 (ja) 2000-01-14 2000-09-04 黒色顔料の製造法
PCT/JP2001/004115 WO2002094941A1 (fr) 2000-01-14 2001-05-17 Procede permettant la production d'un pigment noir

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2000006488 2000-01-14
JP2000266731A JP4703826B2 (ja) 2000-01-14 2000-09-04 黒色顔料の製造法
PCT/JP2001/004115 WO2002094941A1 (fr) 2000-01-14 2001-05-17 Procede permettant la production d'un pigment noir

Publications (1)

Publication Number Publication Date
WO2002094941A1 true WO2002094941A1 (fr) 2002-11-28

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108485306A (zh) * 2018-03-29 2018-09-04 江苏道博化工有限公司 一种苯胺黑染料的合成方法

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JP2003041127A (ja) * 2001-08-01 2003-02-13 Sakura Color Prod Corp 樹脂組成物
JP5712633B2 (ja) * 2011-01-21 2015-05-07 戸田工業株式会社 アニリンブラック及び該アニリンブラックを用いた樹脂組成物ならびに水系、溶剤系分散体
JP6018363B2 (ja) * 2011-01-21 2016-11-02 戸田工業株式会社 アニリンブラック及び該アニリンブラックを用いた樹脂組成物および水系、溶剤系分散体
KR20190040465A (ko) * 2017-10-10 2019-04-18 도다 고교 가부시끼가이샤 아닐린 블랙 그리고 해당 아닐린 블랙을 사용한 수지 조성물 및 분산체
JP7288579B2 (ja) 2017-12-25 2023-06-08 戸田工業株式会社 アニリンブラック粒子、並びに該アニリンブラック粒子を用いた樹脂組成物、水系分散体、及び非水系分散体

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JP3663807B2 (ja) * 1997-01-29 2005-06-22 ぺんてる株式会社 黒色顔料組成物

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JPH10245497A (ja) * 1997-02-28 1998-09-14 Kozo Horiuchi 黒色顔料
JP2000072974A (ja) * 1998-09-01 2000-03-07 Kozo Horiuchi アニリンブラックの製造方法

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Title
BEHRMAN E.J.: "The ortho-para ratio and the intermediate in the persulfate oxidation of aromatic amines (the boyland-sims oxidation)", J. ORG. CHEM., vol. 57, no. 8, 1992, pages 2266 - 2270, XP002945088 *
GVORKYAN M.G. ET AL.: "Kinetics of potassium peroxydisulfate reaction with aniline in water and water-ethanol mixtures", ARM. KHIM. ZH., vol. 22, no. 4, 1969, pages 288 - 292, XP002945087 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108485306A (zh) * 2018-03-29 2018-09-04 江苏道博化工有限公司 一种苯胺黑染料的合成方法

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JP2001261989A (ja) 2001-09-26

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