CN102532938B - Preparation method of pigment preparations containing superfine phthalocyanine pigment particles - Google Patents
Preparation method of pigment preparations containing superfine phthalocyanine pigment particles Download PDFInfo
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- CN102532938B CN102532938B CN 201110448719 CN201110448719A CN102532938B CN 102532938 B CN102532938 B CN 102532938B CN 201110448719 CN201110448719 CN 201110448719 CN 201110448719 A CN201110448719 A CN 201110448719A CN 102532938 B CN102532938 B CN 102532938B
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Abstract
The invention discloses a preparation method of pigment preparations containing superfine phthalocyanine pigment particles. According to the preparation method, auxiliary agents such as phthalocyanine pigments, phthalocyanine derivatives and dispersing agents are used as raw materials to be prepared into the pigment preparations containing the superfine phthalocyanine pigment particles through multiple-time dissolution, precipitation and filtering processes and then through tablet making and drying. The pigment preparations can be stably dispersed through simple stirring in a waterborne system, in addition, the problems that the particle size of the pigment particles is great, and the phenomena such as pigment precipitation and flocculation are generated in the use process can be avoided, and the pigment preparations can be used as coloring agents applied to various industries such as paint and ink.
Description
Technical field
The present invention relates to a kind of phthalocyanine pigment be carried out deep-processing method, relate in particular to a kind of pigment preparation matter that contains ultra-fine phthalocyanine pigment particle and preparation method thereof.
Background technology
Phthalocyanine pigment is a kind of important pigment dyestuff, particularly the color of the indigo plant made of copper phthalocyanine, veridian is very bright-coloured, tinting strength is high for phthalocyanine, because advantages such as that phthalocyanine pigment has is bright and lustrous, tinting strength good, anti-strong acid, alkali, solvent and weather resistance excellence, and the suitability for industrialized production manufacturing process is simple, therefore, be widely used in manufacturings such as printing-ink, coating, plastics, rubber, leather, textiles, papermaking, electric ink.
The primary particle particle diameter of phthalocyanine pigment is general all less than 100 nanometers, in the building-up process of phthalocyanine pigment, because by cohesion and agglomeration formation pigment aggregate, to cause commercial phthalocyanine pigment be particle diameter mostly at 200 microns to 1000 microns powdered granule between pigment particles.In use, the dust pollution that the phthalocyanine pigment of powder form disperses everywhere and causes, operator and production environment are tended to cause bigger harm, therefore, easily cause the powder pigment of dust pollution to carry out deep processing to phthalocyanine etc., its state with macrobead, liquid is used by the user, is an important directions in pigment deep processing field.Masterbatch is after pigment mixes with vector resin by a certain percentage, through grinding or the twin screw expressing technique is distributed to phthalocyanine pigment in the resin and the granules of pigments that makes equably, it is a kind of typical macrobead pigment preparation matter, have that coloring effect is good, stability is high, pigment content is high, be convenient to automatic gauge and transportation, advantages such as save energy, no dust pollution, be mainly used in the painted of industry such as plastic working; Aqueous color paste then is that raw materials such as pigment, dispersion agent, water are formed the liquid paint dispersion through the granules of pigments stable dispersion of prepared such as dispersion, grinding, froth breaking, filtration in water-based system, it is a kind of typical fluidization pigment preparation matter, have advantages such as coloring effect is good, no dust pollution, applied range, be widely used in industries such as coating, printing ink, fiber staining, papermaking and process hides.Yet industries such as coating, printing ink can't be used Masterbatch, and aqueous color paste exists defectives such as extended storage stability is poor, transportation cost height.
At water-borne coatings and ink area, the advantage of comprehensive Masterbatch and aqueous color paste, the lamellar pigment prepared product that manufacturing can disperse in water-based system, having use, transportation and convenient, the safe advantage of storage, is to avoid Masterbatch can't use in fields such as water-borne coatings and printing ink and aqueous color paste is poor because of the extended storage stability that the granules of pigments sedimentation causes, cross a very significant solution of the problems such as transportation cost height that low pigment content causes.
The stronger resin of lipophilicity is different as solid support material with often selecting in the Masterbatch manufacturing processed, manufacturing can be in water-based system the dispersed solids pigment preparation matter, must select for use the stronger resin of wetting ability as carrier, and be applied to pigment dispersing agent in the water-based system in the granules of pigments surface adsorption.With regard to phthalocyanine pigment, because the phthalocyanine pigment surface polarity is low, pigment is carried out comparatively difficulty of surface treatment, the phthalocyanine pigment particle is relatively poor to the adsorptivity of hydrophilic resin and dispersion agent, causes making the generation that the macrobead pigment preparation matter that can disperse in water-based system tends to occur occur in the reunion, use of big and wide, the granules of pigments of distributing of the particle diameter of pigment particles phenomenons such as pigment sedimentation and flocculation.
The generation of problems such as the pigment sedimentation that occurs in the reunion of big and wide, the granules of pigments of distributing of the particle diameter of avoiding the phthalocyanine pigment particle and the use and flocculation is a crucial difficult problem of making the macrobead phthalocyanine pigment prepared product that can disperse in water-based system.
Summary of the invention
In order to overcome above-mentioned the deficiencies in the prior art, the invention provides a kind of preparation method of the pigment preparation matter that contains ultra-fine phthalocyanine pigment particle that can in water-based system, disperse.
The present invention for the technical scheme that solves its technical problem and adopt is:
A kind of preparation method who contains the pigment preparation matter of ultra-fine phthalocyanine pigment particle is characterized in that: may further comprise the steps:
A) phthalocyanine pigment is carried out stirring and dissolving with concentrated acid under 35～70 ℃ and handles, treat phthalocyanine pigment dissolve fully form homogeneous phase solution after, after filtration the homogeneous phase pigment solution;
B) the homogeneous phase pigment solution that step a) is obtained and with the phthalocyanine pigment mass ratio be that 0.2～2.0: 1 phthalocyanine derivates joins in the aqueous dispersant, heat under 70～95 ℃ and dispersed with stirring evenly after, be down to 45～55 ℃ and left standstill 0.5～8 hour, after treating that product is separated out fully, product is filtered, and use N, the aqueous solution of dinethylformamide and triethanolamine repeatedly washs filtration product, gets pigment filter cake;
C) will be distributed in the water soluble resin solution through the pigment filter cake of washing, form coloured material;
D) drip acid while disperseing in the coloured material that obtains to step c), treat that precipitation finishes after-filtration, throw out is repeatedly washed with deionized water and ethanol, when washings specific conductivity≤100 μ S/cm, finish to wash;
E) will push through the throw out of step d) washing and dehydrate after making sheet.
Concentrated acid described in the step a) of the present invention is that sulfuric acid content reaches the above vitriol oil of 90wt.%.
Phthalocyanine pigment described in the step a) be any can be by the phthalocyanine pigment of stable dispersion in water-based system, as pigment such as phthalocyanine blue 15:X (X=O, 1,2,3,4,6) and phthalocyanine greens.
Phthalocyanine derivates described in the step b) has following structure:
P-R
n
Wherein, n is 1,2 or 3; R is COOM
2Or SO
3M
2In a kind of, M
2A kind of in hydrogen, sodium or the potassium; P has following structure:
In this structure, M
1A kind of in iron, copper, cobalt or the nickel.Such phthalocyanine blue derivative has bigger bound energy, not only can with the surface bonding of phthalocyanine pigment, also can promote the interaction force between phthalocyanine pigment surface and hydrophilic resin, the dispersion agent, avoid the generation of the phenomenons such as reunion of granules of pigments.
Consisting of of the described aqueous dispersant of step b), dispersion agent account for 5.0～30.0wt.% of aqueous dispersant total mass, and surplus is deionized water, and dispersion agent has following structure:
Wherein, m is 6～12 integer.Bonding force with the dispersion agent of this structure and phthalocyanine surface is stronger, can effectively avoid the generation of phenomenons such as pigment sedimentation that the pigment preparation matter of this ultra-fine phthalocyanine pigment in use occurs and flocculation.
The described N of step b), dinethylformamide and the triethanolamine aqueous solution consist of, and N, dinethylformamide account for 3～8wt.% of described solution total mass, and triethanolamine accounts for 10～25wt.% of described solution total mass, and surplus is deionized water.
The described water soluble resin solution of step c) is made up of water-soluble solid resin, deionized water and pH value conditioning agent, wherein the water-soluble solid resin accounts for 20～30wt.% of water soluble resin solution total mass, pH value conditioning agent consumption is 9.5～12 for the pH that be able to regulate water soluble resin solution, and surplus is deionized water.
Described water-soluble solid resin is at least a in polyvinyl alcohol, polyacrylamide, polyacrylic acid, polyoxyethylene glycol, polymaleic anhydride, polyvinylpyrrolidone, Resins, epoxy, resol, aminoresin, phenylethylene-maleic anhydride resin, Synolac and the urethane resin.
Among the present invention, described pH value conditioning agent can be selected the pH regulator agent commonly used of fields such as coating, printing ink, at least a as in the products such as AMP-95 of ammoniacal liquor, Monoethanolamine MEA BASF, trolamine and Angus company.
The acid that drips in the step d) of the present invention can be selected organic acid or the mineral acid of industrial adjusting pH value commonly used, at least a in example hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, oxalic acid, the Whitfield's ointment.
The pressure-controlling that sheet is made in extruding in the step e) of the present invention is at 10～30MPa, and the temperature control that dehydrates is at 60～80 ℃.
Use that the inventive method prepares contain the pigment preparation matter of ultra-fine phthalocyanine pigment particle the time, only needing that this phthalocyanine pigment prepared product is joined the AMP-95 or other industry that contain ammoniacal liquor, Angus company uses always in the aqueous solution of the alkaline matter of regulating the pH value, by simple stirring technique, pigment particles can be dispersed in the water-based system.
Useful technique effect of the present invention is: this preparation method is simple and easy to do, and the phthalocyanine pigment prepared product using method of preparing is simple, can also avoid the particle diameter of pigment particles in this phthalocyanine pigment prepared product big, occur the generation of phenomenons such as pigment sedimentation and flocculation in the use.
Embodiment
The present invention is described in further detail below in conjunction with specific embodiment, but the invention is not restricted to the following example.Except as otherwise noted, following percentage ratio is mass percent.
Embodiment
Among the embodiment 1～4, used dispersion agent DS-A is the compound with following structure:
Used dispersion agent DS-B is the compound with following structure:
Used dispersion agent DS-C is the compound with following structure:
Used phthalocyanine derivates A is the compound with following structure:
Used phthalocyanine derivates B is the compound with following structure:
Used phthalocyanine derivates C is the compound with following structure:
Embodiment 1
Follow these steps to prepare pigment preparation matter:
A). get the vitriol oil of 1000 gram 98.0wt.%, under the stirring velocity of 35 ℃ and 300r/min, dropping into 200 gram phthalocyanine blue (P.B.15:1) pigment disperses, after pigment dissolves the formation homogeneous phase solution fully, filter pigment solution with glass filter core pan, a homogeneous phase pigment solution, wherein phthalocyanine blue comes from Jiangsu two happy chemical color company limited;
B). step a) gained homogeneous phase pigment solution and 0.4 gram phthalocyanine derivates A joined (this aqueous dispersant contains 50 gram dispersion agent DS-A in the 1000 gram aqueous dispersants, surplus is deionized water), in disperseing 20 minutes under the stirring velocity of 70 ℃ and 300r/min after be uniformly dispersed, be down to 45 ℃, keep this temperature to leave standstill being beneficial to product in 3 hours separating out, treat product separate out finish after, filter this product with glass filter core pan, and use N, (this aqueous solution contains 3wt.%N to the aqueous solution of dinethylformamide and triethanolamine, dinethylformamide, 15wt.% triethanolamine, all the other are deionized water) repeatedly wash leaching product, get pigment filter cake;
C), step b) gained pigment filter cake is distributed to (this solution is with 100 gram water-soluble phenylethene-acrylic solid resins in the 500 gram water soluble resin solution, in deionized water, dissolve, and to utilize 2-amino-2-methyl-1-propanol to regulate pH value be 12 acquisitions), form coloured material, wherein water soluble resin is selected from water-soluble phenylethene-acrylic solid resin of BASF Aktiengesellschaft (BASF Corporation)
678;
D), drip the oxalic acid of 10w.% concentration in the coloured material of step c) gained while disperseing, treat that precipitation finishes after, filter with glass filter core pan, heavy t shallow lake thing is stopped until filtrate specific conductivity≤100 μ s/cm with deionized water and washing with alcohol;
E), be 10MPa with the coloured precipitation material of step d) gained pressure, make the sheet drying under 70 ℃ of the temperature, namely get the pigment preparation matter that contains ultra-fine phthalocyanine pigment particle.
Embodiment 2
Follow these steps to prepare pigment preparation matter:
A). get the vitriol oil of 1000 gram 90wt.%, under the stirring velocity of 70 ℃ and 1000r/min, dropping into 400 gram phthalocyanine green (P.G.7) pigment disperses, after pigment dissolves the formation homogeneous phase solution fully, filter pigment solution with glass filter core pan, a homogeneous phase pigment solution, wherein phthalocyanine blue comes from Jiangsu two happy chemical color company limited;
B). step a) gained homogeneous phase pigment solution and 4 gram phthalocyanine derivates B are joined (this aqueous dispersant contains 100 gram dispersion agent DS-B in the 2000 gram aqueous dispersants, surplus is deionized water), in disperseing 20 minutes under the stirring velocity of 95 ℃ and 300r/min after be uniformly dispersed, be down to 55 ℃, keep this temperature to leave standstill being beneficial to product in 8 hours separating out, treat product separate out finish after, filter this product with glass filter core pan, and use N, (this solution contains 6wt.%N to the aqueous solution of dinethylformamide and triethanolamine, dinethylformamide, 10wt.% triethanolamine, all the other are deionized water) repeatedly wash leaching product, get pigment filter cake;
C). with step b) gained pigment filter cake be distributed to 1000 the gram resin solutions in (this solution be with 300 the gram water-soluble phenylethene-acrylic solid resins, in deionized water, dissolve, and to utilize ammoniacal liquor to regulate pH value be 10 acquisitions), form coloured material, wherein water soluble resin is selected from the DT-150 of Xi'an Great Sky Science ﹠ Technology Co., Ltd. water-soluble solid acrylic resin;
D). in the coloured material of step c) gained while disperseing the Whitfield's ointment of Dropwise 5 wt.% concentration, treat that precipitation finishes after, filter with glass filter core pan, throw out is stopped until filtrate specific conductivity≤100 μ s/cm with deionized water and washing with alcohol;
E). be 30MPa with the coloured precipitation material of step d) gained pressure, make the sheet drying under 60 ℃ of the temperature, namely get the pigment preparation matter that contains ultra-fine phthalocyanine pigment particle.
Embodiment 3
Follow these steps to prepare pigment preparation matter:
A). get the vitriol oil of 1000 gram 95.0wt.%, under the stirring velocity of 55 ℃ and 300r/min, dropping into 300 gram phthalocyanine blue (P.B.15:3) pigment disperses, after pigment dissolves the formation homogeneous phase solution fully, filter pigment solution with glass filter core pan, get a homogeneous phase pigment solution, wherein phthalocyanine blue comes from Shanghai prompt rainbow pigment chemical industry Group Co.,Ltd;
B). step a) gained homogeneous phase pigment solution and 6 gram phthalocyanine derivates C are joined (this aqueous dispersant contains 50 gram dispersion agent DS-B in the 2000 gram aqueous dispersants, surplus is deionized water), in disperseing 20 minutes under the stirring velocity of 80 ℃ and 300r/min after be uniformly dispersed, be down to 50 ℃, keep this temperature to leave standstill being beneficial to product in 3 hours separating out, treat product separate out finish after, filter this product with glass filter core pan, and use N, (this solution contains 8wt.%N to the aqueous solution of dinethylformamide and triethanolamine, dinethylformamide, 20wt.% triethanolamine, all the other are deionized water) repeatedly wash leaching product, get pigment filter cake;
C). step b) gained pigment filter cake is distributed to (this solution is with 100 gram water-soluble solid acrylic resins in the 500 gram resin solutions, in deionized water, dissolve, and to utilize ammoniacal liquor to regulate pH value be 9.5 acquisitions), form coloured material, wherein water soluble resin is selected from the DT-116 of Xi'an Great Sky Science ﹠ Technology Co., Ltd. water-soluble solid acrylic resin;
D). drip the phosphoric acid of 10wt.% concentration in the coloured material of step c) gained while disperseing, treat that precipitation finishes after, filter with glass filter core pan, throw out is stopped until filtrate specific conductivity≤100 μ s/cm with deionized water and washing with alcohol;
E). be 25MPa with the coloured precipitation material of step d) gained pressure, make the sheet drying under 70 ℃ of the temperature, namely get the pigment preparation matter that contains ultra-fine phthalocyanine pigment particle.
Embodiment 4
Follow these steps to prepare pigment preparation matter:
A). get the vitriol oil of 1000 gram 95.0wt.%, under the stirring velocity of 60 ℃ and 300r/min, dropping into 250 gram phthalocyanine green (P.G.36) pigment disperses, after pigment dissolves the formation homogeneous phase solution fully, filter pigment solution with glass filter core pan, a homogeneous phase pigment solution, wherein phthalocyanine green comes from Jiangsu two happy chemical color company limited;
B). step a) gained homogeneous phase pigment solution and 2 gram phthalocyanine derivates C are joined (this aqueous dispersant contains 300 gram dispersion agent DS-C in the 1000 gram aqueous dispersants, surplus is deionized water), in disperseing 20 minutes under the stirring velocity of 85 ℃ and 300r/min after be uniformly dispersed, be down to 45 ℃, keep this temperature to leave standstill being beneficial to product in 0.5 hour separating out, treat product separate out finish after, filter this product with glass filter core pan, and use N, (this solution contains 6wt.%N to the aqueous solution of dinethylformamide and triethanolamine, dinethylformamide, 25wt.% triethanolamine, all the other are deionized water) repeatedly wash leaching product, get pigment filter cake;
C). with step b) gained pigment filter cake be distributed to 500 the gram resin solutions in (this solution be with 100 the gram water-soluble maleic anhydride solid resin, in deionized water, dissolve, and to utilize trolamine to regulate pH value be 10 acquisitions), form coloured material, wherein water soluble resin is selected from the synthetic SM-181 maleic anhydride solid resin of Suzhou Sunmun Technology Co., Ltd.;
D). drip the hydrochloric acid of 10wt.% concentration in the coloured material of step c) gained while disperseing, treat that precipitation finishes after, filter with glass filter core pan, throw out is stopped until filtrate specific conductivity≤100 μ s/cm with deionized water and washing with alcohol;
E). be 15MPa with the coloured precipitation material of step d) gained pressure, make the sheet drying under 80 ℃ of the temperature, namely get the pigment preparation matter that contains ultra-fine phthalocyanine pigment particle.
Performance test
The pigment preparation matter that embodiment 1～4 gained is contained ultra-fine phthalocyanine pigment particle is got 100 grams respectively, putting into triethanolamine and 2-amino-2-methyl-1-propanol is in 12.0 the 400 gram aqueous solution by the pH value of 1: 2 mixing preparation of mass ratio, after disperseing 30 minutes with the stirring velocity of 800r/min, obtain dispersible pigment dispersion.
Respectively with above-mentioned dispersible pigment dispersion at 25 ℃ down when airtight placements 1 day and 30 days, the size distribution of testing this dispersible pigment dispersion with Zetasizer Nano Zs90 type nano particle size and the zeta potential instrument of Britain Ma Erwen Instr Ltd., in the test result, D50 represents that 50% passes through particle diameter, namely survey in the particle minimum grain size that 50% particle can both pass through, in like manner, D100 represents 100% by particle diameter, namely surveys the minimum grain size that particles all in the particle can both pass through; By range estimation, observe dispersion liquid at 25 ℃ down when airtight placement 1 day and 30 days, have or not obvious pigment precipitation, flocculation etc. to occur and have a strong impact on stable situation.
Table 1 is the test result of the pigment preparation matter institute pigment preparation dispersion liquid of above-described embodiment 1～4 preparation.
The test result of table 1 pigment preparation matter institute pigment preparation dispersion liquid
Claims (4)
1. preparation method who contains the pigment preparation matter of ultra-fine phthalocyanine pigment particle is characterized in that: may further comprise the steps:
A) phthalocyanine pigment is carried out stirring and dissolving with concentrated acid under 35 ~ 70 ℃ and handles, treat phthalocyanine pigment dissolve fully form homogeneous phase solution after, after filtration the homogeneous phase pigment solution;
B) the homogeneous phase pigment solution that step a) is obtained and with the phthalocyanine pigment mass ratio be that 0.2～2.0: 1 phthalocyanine derivates joins in the aqueous dispersant, heat under 70 ~ 95 ℃ and dispersed with stirring evenly after, be down to 45 ~ 55 ℃ and left standstill 0.5 ~ 8 hour, after treating that product is separated out fully, product is filtered, and use N, the aqueous solution of dinethylformamide and triethanolamine repeatedly washs filtration product, gets pigment filter cake;
C) will be distributed in the water soluble resin solution through the pigment filter cake of washing, form coloured material;
D) drip acid while disperseing in the coloured material that obtains to step c), treat that precipitation finishes after-filtration, throw out is repeatedly washed with deionized water and ethanol, when washings specific conductivity≤100 μ S/cm, finish to wash;
E) will push through the throw out of step d) washing and dehydrate after making sheet;
Wherein the described concentrated acid of step a) is that sulfuric acid content reaches the above vitriol oil of 90wt.%,
Phthalocyanine derivates described in the step b) has following structure:
P—R
n
Wherein, n is 1,2 or 3; R is COOM
2Or SO
3M
2In a kind of,
M
2A kind of in hydrogen, sodium or the potassium; P has following structure:
In this structure, M
1A kind of in iron, copper, cobalt or the nickel,
Consisting of of the described aqueous dispersant of step b), dispersion agent account for 5.0 ~ 30.0wt.% of aqueous dispersant total mass, and surplus is deionized water, and dispersion agent has following structure:
Wherein, m is 6 ~ 12 integer.
2. the preparation method who contains the pigment preparation matter of ultra-fine phthalocyanine pigment particle according to claim 1, it is characterized in that: the described N of step b), dinethylformamide and the triethanolamine aqueous solution consist of, N, dinethylformamide accounts for 3～8wt.% of described solution total mass, triethanolamine accounts for 10～25wt. % of described solution total mass, and surplus is deionized water.
3. the preparation method who contains the pigment preparation matter of ultra-fine phthalocyanine pigment particle according to claim 1, it is characterized in that: the described water soluble resin solution of step c) is made up of water-soluble solid resin, deionized water and pH value conditioning agent, wherein the water-soluble solid resin accounts for 20 ~ 30wt.% of water soluble resin solution total mass, pH value conditioning agent consumption is 9.5 ~ 12 for the pH that be able to regulate water soluble resin solution, and surplus is deionized water.
4. the preparation method who contains the pigment preparation matter of ultra-fine phthalocyanine pigment particle according to claim 3 is characterized in that: described water-soluble solid resin is at least a in polyvinyl alcohol, polyacrylamide, polyacrylic acid, polyoxyethylene glycol, polymaleic anhydride, polyvinylpyrrolidone, Resins, epoxy, resol, aminoresin, phenylethylene-maleic anhydride resin, Synolac and the urethane resin.
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| CN110041730A (en) * | 2019-04-10 | 2019-07-23 | 镇江恒昌彩艺科技有限公司 | A kind of water-based ink of PVC coloured silk film easily disperses permanent yellow pigment and preparation method |
| CN110028806A (en) * | 2019-04-10 | 2019-07-19 | 镇江恒昌彩艺科技有限公司 | A kind of water-based ink of PVC coloured silk film easily disperses red pigment and preparation method |
| CN113736010B9 (en) * | 2021-09-22 | 2023-08-01 | 山东凯瑞尔光电科技有限公司 | Polymer dispersant and application thereof in surface treatment of halogenated phthalocyanine pigment |
| CN114479509B (en) * | 2021-12-20 | 2023-12-05 | 杭州红妍颜料化工有限公司 | Preparation method of uniformly dispersed pigment red |
| CN116970291B (en) * | 2023-07-31 | 2024-06-28 | 山东科莱福光电科技有限公司 | Preparation method and application of phthalocyanine nano pigment |
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