CN103773078A

CN103773078A - Production method of nanometer anthraquinone organic pigment

Info

Publication number: CN103773078A
Application number: CN201410033622.4A
Authority: CN
Inventors: 陈文忠
Original assignee: CINIC CHEMICALS (SHANGHAI) Co Ltd
Current assignee: CINIC CHEMICALS (SHANGHAI) Co Ltd
Priority date: 2014-01-24
Filing date: 2014-01-24
Publication date: 2014-05-07

Abstract

The invention discloses a production method of nanometer anthraquinone organic pigment. The production method comprises the following steps: (1) mixing anthraquinone organic pigment dry powder and a good solvent, and then adding an obtained organic pigment good solvent solution to a poor solvent so as to dissolve out organic pigment, wherein the dissolving-out temperature is -30 DEG C to 30 DEG C, the good solvent is selected from a sulfuric acid solution, a benzenesulfonic acid solution or a p-toluenesulfonic acid solution, and the poor solvent is selected from one of water, alcohols or an inorganic salt aqueous solution; and (2) filtering, washing and drying the product in the step (1), thus obtaining the nanometer anthraquinone organic pigment. The production method disclosed by the invention has the advantages of simple process, low cost, convenience for industrial production and the like.

Description

The manufacture method of nanometer Anthraquinones pigment dyestuff

Technical field

The present invention relates to the manufacture method of Anthraquinones pigment dyestuff.

Background technology

Colored filter is liquid-crystal display important composition parts, liquid-crystal display can present chromatic image and mainly rely on colored filter to be irradiated to colored filter by the white light of light source through liquid crystal layer, form RGB light by " red " " green " " indigo plant " the three look pigment photoresistors on the corresponding each pixel of colored filter, finally in human eye, be mixed to form chromatic image.Pigment photoresistor is one of critical materials of colored filter, the crystalline size that wherein comprises pigment dyestuff and particle size make the precondition of high quality pigment photoresistor, and it directly affects the performances such as gloss, tinting strength, opacifying power, transparency and the tone of colored filter.

The crystalline size of the Anthraquinones pigment dyestuff that ordinary method obtains is at present generally more than 50nm, particle size (coacervate particle) is just larger, for obtaining the more pigment dyestuff of low particle size, the method adopting is mainly the method such as polishing and salt mill method, the method has good effect at the less micro-or nano size pigment dyestuff of preparation, further obtain the crystal of 10 ~ 30nm size during as thought, need very high energy and grind for a long time, crystalline size is reduced to and to a certain degree also may occurs afterwards to increase again simultaneously.

For addressing the above problem, Japanese fuji film Co., Ltd. [application number CN200680051777.4] has reported a kind of method, PR177 dry powder is dissolved in good solvent in (sulfoxide type solvent or amide solvent), and then in poor solvent, separate out the anthraquinone pigment that obtains nano-scale (5 ~ 80nm), but while using this method to prepare nano dye, PR177 solubleness in this kind solvent is very low, need to consume a large amount of high boiling organic solvents, difficult solvent recovery, meaningless in actual applications.

CN101376750A has also mentioned a kind of method of preparing nanometer pigment dyestuff, it is dissolved in two kinds of different pigment dyestuffs separately in good solvent, again this solution is separated out in poor solvent, but this method needs a kind of crystallizer of complexity, for the larger difficulty of implementing of suitability for industrialized production.

Summary of the invention

The object of the present invention is to provide a kind of manufacture method of nanometer Anthraquinones pigment dyestuff, the above-mentioned defect existing to overcome prior art.

Method of the present invention, comprises the steps:

(1) by Anthraquinones pigment dyestuff dry powder and good solvent at 50 ~ 160 ℃, preferably 90 ~ 160 ℃ of mixing, then, by the good solvent solution of the pigment dyestuff obtaining, add in poor solvent and separate out, Precipitation Temperature is-30 ℃ ~ 30 ℃, is preferably-20 ~ 5 ℃;

Preferably, adopt the good solvent solution of the pigment dyestuff obtaining, adopt the mode dripping, add in poor solvent, time for adding is 10 ~ 60min;

Described good solvent is selected from sulphuric acid soln, Phenylsulfonic acid solution or tosic acid solution etc.;

The weight concentration of sulphuric acid soln, Phenylsulfonic acid solution or tosic acid solution is 10% ~ 100%, is preferably 50% ~ 100%;

Described poor solvent is selected from more than one in water, alcohols or inorganic salt solution, and the alcoholic solvent that preferably carbonatoms is less than 10, as methyl alcohol, ethanol, ethylene glycol, NaCl, Na ₂sO ₄, NaNO ₃or CaCl ₂deng;

Described good solvent and the weight ratio of pigment are 100:1 ~ 1:1, are preferably 10:1 ~ 1:1;

Described poor solvent and the weight of pigment are 1000:1 ~ 1:1, are preferably 100:1 ~ 1:1;

(2) then the product of step (1) is filtered, washing, dry, obtain described nanometer Anthraquinones pigment dyestuff, its particle diameter is 10 ~ 30nm;

The preparation method of Anthraquinones pigment dyestuff nano particle of the present invention, has technique simple, and cost is low, is convenient to the advantages such as suitability for industrialized production.

Accompanying drawing explanation

Fig. 1 is the electromicroscopic photograph of the product of embodiment 2.

Embodiment

Embodiment 1

Sulfuric acid and 40gPR177 that the weight concentration that adds 90g in flask is 98%, be warming up to 140 ℃, stirs and make its dissolving;

In reactor, add 700g water, be cooled to 0 ℃, in 60min, the sulphuric acid soln of PR177 is dropped in water, separate out, separate out initial temperature and be-5 ℃, final temperature is 30 ℃, filters, and is washed to neutrality, is dried and obtains product, and product median size is 30nm.

Embodiment 2

In flask, adding the weight concentration of 120g is 80% sulfuric acid and 40gPR177, is warming up to 130 ℃, stirs and makes its dissolving.

In reactor, add the aqueous solution being formed by 1044g water and 240gNaCl, be cooled to-23 ℃, in 10min, the sulphuric acid soln of PR177 is dropped in water, separate out, separate out initial temperature and be-23 ℃, final temperature is 20 ℃, filter, be washed to neutrality, be dried and obtain product, product median size is that 20nm(is shown in accompanying drawing 1).

Embodiment 3

In flask, add 50% sulfuric acid and the 40gPR177 of 400g, be warming up to 120 ℃, stir and make its dissolving.

In reactor, add the aqueous solution being formed by 650g water and 280g methyl alcohol, be cooled to-30 ℃, in 10min, the sulphuric acid soln of PR177 is dropped in water, separate out, separate out initial temperature and be-30 ℃, final temperature is 10 ℃, filter, be washed to neutrality, be dried and obtain product, the median size of product is 20nm.

Embodiment 4

In flask, add Phenylsulfonic acid and the 40gPR177 of 500g, be warming up to 137 ℃, stir and make its dissolving.

In reactor, add the aqueous solution being formed by 1044g water and 240gNaCl, be cooled to-23 ℃, in 10min, the sulphuric acid soln of PR177 is dropped in water, separate out, separate out initial temperature and be-23 ℃, final temperature is 20 ℃, filter, be washed to neutrality, be dried and obtain product, product median size is 20nm.

Embodiment 5

In flask, add tosic acid and the 40gPR177 of 1000g, be warming up to 140 ℃, stir and make its dissolving.

Embodiment 6

In flask, add 98% sulfuric acid and the 40gPY199 of 300g, be warming up to 130 ℃, stir and make its dissolving.

Claims

1. the manufacture method of nanometer Anthraquinones pigment dyestuff, is characterized in that, comprises the steps:

(1) Anthraquinones pigment dyestuff dry powder is mixed with good solvent, then, by the good solvent solution of the pigment dyestuff obtaining, add in poor solvent and separate out, Precipitation Temperature is-30 ℃ ~ 30 ℃;

Described good solvent is selected from sulphuric acid soln, Phenylsulfonic acid solution or tosic acid solution;

Described poor solvent is selected from more than one in water, alcohols or inorganic salt solution;

(2) then the product of step (1) is filtered, washing, dry, obtain described nanometer Anthraquinones pigment dyestuff.

2. method according to claim 1, is characterized in that, Anthraquinones pigment dyestuff dry powder is mixed at 50 ~ 160 ℃ with good solvent.

3. method according to claim 1, is characterized in that, the weight concentration of sulphuric acid soln, Phenylsulfonic acid solution or tosic acid solution is 10% ~ 100%.

4. method according to claim 1, is characterized in that, described poor solvent is selected from alcoholic solvent, NaCl, the Na that carbonatoms is less than 10 ₂sO ₄, NaNO ₃or CaCl ₂.

5. method according to claim 4, is characterized in that, described good solvent and the weight ratio of pigment are 100:1 ~ 1:1; Described poor solvent and the weight of pigment are 1000:1 ~ 1:1.

6. method according to claim 5, is characterized in that, described good solvent and the weight ratio of pigment are 10:1 ~ 1:1, and described poor solvent and the weight of pigment are 100:1 ~ 1:1.

7. according to the method described in claim 4 ~ 6 any one, it is characterized in that, adopt the mode dripping, by the good solvent solution of the pigment dyestuff obtaining, adopt the mode dripping, add in poor solvent, time for adding is 10 ~ 60min.