CN114524941B - Nitrogen/sulfur hybrid modified benzene Ma Shuzhi ceramic dispersant, and preparation method and application thereof - Google Patents

Nitrogen/sulfur hybrid modified benzene Ma Shuzhi ceramic dispersant, and preparation method and application thereof Download PDF

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CN114524941B
CN114524941B CN202210181035.4A CN202210181035A CN114524941B CN 114524941 B CN114524941 B CN 114524941B CN 202210181035 A CN202210181035 A CN 202210181035A CN 114524941 B CN114524941 B CN 114524941B
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shuzhi
copper phthalocyanine
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王斌
黄月文
宋斌
冯晓文
欧阳天生
钟春林
汪阳
林庆娜
年福伟
赵树录
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Zhaoqing Outao New Material Co ltd
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Abstract

The invention relates to the field of ceramic water-based pigment dispersants, and discloses a nitrogen/sulfur hybrid modified benzene Ma Shuzhi ceramic dispersant, a preparation method and application thereof, wherein the preparation method comprises the following steps: adding polyether monoamine under the condition of introducing protection gas, heating to 60-70 ℃, slowly adding styrene-maleic anhydride resin powder under the conditions of reflux and stirring, adding monothiocarboxylic acid after 0.5-1 hour, heating to 80-90 ℃, reacting for 1-2 hours, finally adding alkylbenzene sulfonic acid and triethanolamine, keeping the temperature at 80-90 ℃, reacting for 1-2 hours, adding water, stirring and adding alkali liquor, and adjusting the pH value of the mixed liquor to 5-8 to obtain the modified benzene Ma Shuzhi ceramic dispersant with the content of 10-50 wt%. The invention utilizes the ceramic reuse water, the prepared water-based color paste has good dispersion stability, and the application field of the ceramic reuse water is widened.

Description

Nitrogen/sulfur hybrid modified benzene Ma Shuzhi ceramic dispersant, and preparation method and application thereof
Technical Field
The invention relates to the field of ceramic water-based pigment dispersants, and in particular relates to application of a polyether monoamine/triethanolamine/mercaptocarboxylic acid ternary modified benzene Ma Shuzhi dispersant in ceramic water-based organic pigment color paste.
Background
With the development of national economy, the protection of people on the environment and water resources is increasingly improved, and the demands on the water-based color paste without organic volatile matters, the utilization of reuse water after wastewater treatment and the like are continuously increased. In the field of ceramics, the reduction of organic volatile matters of used materials, the comprehensive treatment, purification and recycling engineering of ceramic industrial wastewater become very urgent system engineering, and the application field of purified recycled water is continuously expanded.
At present, the common aqueous color paste is prepared together with a dispersant, a pigment, partial resin and other additives in a pure water medium, so that the interaction of the dispersant and impurities in water is reduced, and the effect is reduced or even the effect is ineffective. The dispersant can well wet, disperse and stabilize the pigment and filler in a system, and is widely applied to the fields of coatings, printing ink, ceramics and the like. In these fields, the dispersion of organic pigments is a difficult problem, and the existing high molecular dispersant has the disadvantages of large dosage, high viscosity of color paste, high cost, poor dispersion effect, poor stability and the like. Moreover, in the current ceramic industrial application, various water quality pollution factors including dust pollution, local waste water pollution and local recycled water pollution are difficult to avoid.
Copper phthalocyanine molecules are large conjugated systems containing benzene rings, show excellent chemical stability, thermal stability, flame retardance, light resistance and radiation resistance, can be used as a pigment, and are developed into multifunctional materials due to the conductivity, photoconductivity, gas sensitivity, electroluminescence, light storage property, catalytic activity and imitativeness. But the copper phthalocyanine particles have poor dispersibility in an aqueous medium, so that the application of the copper phthalocyanine particles is limited. Chinese patent CN201810524070.5 uses modified maleic anhydride acrylic acid copolymer as a dispersant to prepare aqueous phthalocyanine blue color paste; CN202110115027.5 phthalocyanine blue paste prepared by using a dispersing agent prepared from carboxylic acid extracted from natural plants, polyether modified polyfunctional amine and an active wetting agent has an anti-flooding function; CN201810565587.9 uses one of styrene-maleic anhydride copolymer, acrylic resin or amine alkyl hydroxyl adduct of styrene acrylic acid polymer as a dispersing agent to prepare phthalocyanine blue pigment emulsion with good dispersibility; CN03108739.6 uses sulfosuccinate anions, nonionic surfactants and polyether modified polycarboxylate as composite dispersants to prepare the hydrophobic phthalocyanine blue aqueous color paste. So far, no document reports that nitrogen/sulfur hybrid modified benzene Ma Shuzhi is used as a dispersant for organic pigment phthalocyanine colorant in an aqueous medium containing ceramic reuse water or mixed with reuse water impurities.
Disclosure of Invention
The invention aims to provide application of nitrogen/sulfur hybrid modified benzene Ma Shuzhi as a dispersing agent in organic pigment color paste in an aqueous medium containing ceramic reuse water.
The purpose of the invention is realized by the following technical scheme:
a preparation method of a nitrogen/sulfur hybrid modified benzene Ma Shuzhi ceramic dispersant comprises the following steps:
adding polyether monoamine under the condition of introducing protection gas, heating to 60-70 ℃, slowly adding styrene-maleic anhydride resin powder under the conditions of reflux and stirring, adding monothiocarboxylic acid after 0.5-1 hour, heating to 80-90 ℃, reacting for 1-2 hours, finally adding alkylbenzene sulfonic acid and triethanolamine, keeping the temperature at 80-90 ℃, reacting for 1-2 hours, adding water, stirring and adding alkali liquor, and adjusting the pH value of the mixed liquor to 5-8 to obtain the modified benzene Ma Shuzhi ceramic dispersant with the content of 10-50 wt%.
Preferably, the mass ratio of the polyether monoamine to the styrene-maleic anhydride resin powder to the monothiocarboxylic acid to the alkylbenzene sulfonic acid to the triethanolamine is (100 to 200): 100: (5-15): (0.1-0.5): (5-15).
Preferably, the monothiocarboxylic acid is at least one of thioglycolic acid and mercaptopropionic acid; the alkylbenzene sulfonic acid is at least one of p-toluenesulfonic acid and dodecylbenzene sulfonic acid.
Preferably, the polyether monoamine is an amino group (-NH) having only one terminal amino group 2 ) At least one of methyl-terminated polyoxyethylene ether monoamine, methyl-terminated polyoxyethylene polyoxypropylene ether monoamine and methyl-terminated polyoxypropylene polyoxyethylene ether monoamine, wherein the molecular weight of the methyl-terminated polyoxyethylene ether monoamine, the methyl-terminated polyoxyethylene polyoxypropylene polyoxyethylene ether monoamine and the methyl-terminated polyoxypropylene polyoxyethylene ether monoamine are 500-2000, and the polyoxypropylene content is less than 30wt% of the total weight of the polyether monoamine.
Preferably, the polyether monoamine is CH 3 (OE) m NH 2 、CH 3 (OE) m (OP) n NH 2 、 CH 3 (OE) m1 [(OP) n (OE) m2 ]NH 2 At least one of m =7 to 46, n =0 to 11, m1=1 to 45, and m2=1 to 45, wherein oe is an oxyethylene group, and OP is an oxypropylene group.
Preferably, the styrene-maleic anhydride resin is a styrene-maleic anhydride copolymer having a molecular weight of 1000 to 3000, wherein the content of styrene monomer units is 50 to 65wt%.
Preferably, the alkali liquor is at least one of a sodium hydroxide solution and a potassium hydroxide solution, and the pH value of the mixed liquor is 6-7; the water is ceramic reuse water, tap water or a mixture of the ceramic reuse water and the tap water; the styrene-maleic anhydride resin powder is fine powder with the average mesh number of more than 80 meshes.
The modified benzene Ma Shuzhi ceramic dispersant prepared by the method is applied to water-based organic pigment color paste. Preferably, the dispersant is used for dispersing organic pigment in the ceramic-containing recycled water, and the organic pigment is phthalocyanine.
Preferably, the mass ratio of the organic pigment to the modified benzene Ma Shuzhi ceramic dispersant to the water is 100: (5-10): (≧ 100).
The macromolecular dispersant (see formula 1 below) comprises a group which has an anchoring effect on dispersed particles and a solvent chain which has an effect on a medium, wherein the size of the effect of the anchoring group is closely related to the interaction of the anchoring group and molecules of the particles, and the principle of similar intermiscibility is met, coordination atoms or groups in the macromolecular dispersant play a firmer interaction, and the particles tend to be stable due to the repulsion effect of the same charges after adsorbing the molecules of the dispersant; the solvating chain not only has the function of interacting with the solvent, thereby enabling the mutual space isolation among the particles and the dispersion in the medium, and having the function of stabilization.
Figure RE-GDA0003567272690000031
The copper phthalocyanine molecule forms a conjugated chromophoric system by 18 pi-electron cyclic annulene, 4 isoindolines are combined into a square polycyclic molecule, and a metal atom is positioned at the symmetrical center of a molecular plane. The side group of the molecular chain of the benzene Ma Shuzhi contains benzene ringAnd an acid anhydride group, wherein after the polyether monoamine, the mercapto carboxylic acid and the triethanolamine are modified in sequence, the polyether monoamine reacts with the acid anhydride to form a side-group amic acid group HOOC-CH-CH-CONH-, and the mercapto carboxylic acid reacts with the acid anhydride to form a thiol ester acid group HOOC-CH-CH-CO-S-R-COOH. Experimental results show that benzene Ma Shuzhi firstly undergoes a grafting reaction with monofunctional polyether monoamine and mercaptocarboxylic acid, the molecular weight is increased, the steric hindrance is increased, the whole molecular reactivity is reduced, and the benzene Ma Shuzhi is difficult to undergo an esterification reaction with triethanolamine in a short time without catalysis of alkylbenzene sulfonic acid, so that the molecule does not contain a tertiary amine N atom and a corresponding hydroxyl-N (CH) 2 CH 2 OH) 2 . The molecular weight of the benzene-maleic resin used in the invention is between 1000 and 3000, the mass ratio of the polyether monoamine to the benzene-maleic resin is 100 to 200:100, the molecular weight of the modified benzene horse resin of polyether monoamine is between 2000 and 9000. Then reacting with a proper amount of mercaptocarboxylic acid, and the molecular weight does not increase greatly. The used alkylbenzene sulfonic acid catalyst has good compatibility with the initially modified benzene maleic resin, and under the catalytic action of the alkylbenzene sulfonic acid catalyst, one hydroxyl in triethanolamine containing three hydroxyl is firstly reacted with an anhydride group to form an acid ester group HOOC-CH-CH-COO-CH 2 CH 2 N(CH 2 CH 2 OH) 2 These carboxyl groups COOH are neutralized with a base to form COO - The negative ions, the groups, the metal ions of the copper phthalocyanine and the metal ions in the ceramic reclaimed water form chelate bonds, even form a stable N, O, S atom (containing lone pair electrons or negative ions) multidentate coordination ring structure, and the ion stability of the pigment particles or the reclaimed water is obviously improved. Experiments also show that the reaction time of the triethanolamine and the modified benzene Ma Shuzhi obtained after the reaction of the monofunctional molecules is too long under the action of the catalyst can greatly increase the viscosity of the polymer, generate partial crosslinking, have too large molecular weight, generate an unstable phenomenon and sharply deteriorate the dispersibility of the polymer to pigment particles. In addition, a large number of benzene ring structures in the modified benzene-maleic resin have strong interaction with the aromatic ring structure of copper phthalocyanine molecules, which greatly contributes to the stability of pigment particles; the polyether structure in the polyether monoamine chain contributes to the formation of solvation chains and the steric stabilization. The experimental results also show that, compared with the prior art,the invention has the following remarkable characteristics and beneficial effects:
(1) Under the condition that the addition amount is the same as that of other conditions, compared with the traditional dispersing agent sodium polyacrylate, polyether polycarboxylic acid dispersing agent and polyether modified benzene Ma Shuzhi, the dispersing agent has more remarkable dispersing effect. Under the action of a traditional dispersant sodium acrylate, the copper phthalocyanine begins to partially agglomerate and precipitate within 24 hours in a tap water medium with the copper phthalocyanine content of 1.2wt%, and under the action of a polyether polycarboxylic acid dispersant, the copper phthalocyanine also agglomerates and precipitates within 24 hours in a tap water medium with the copper phthalocyanine content of 2.3 wt%. Although the polyether modified benzene Ma Shuzhi dispersant is improved, the color difference phenomenon appears in a tap water medium with 5.4wt% of copper phthalocyanine within 24 hours, the sedimentation height is 5.5 ml, and partial sedimentation and agglomeration phenomena are found at the bottom after 2 days and 48 hours; whereas, when the content of copper phthalocyanine in the medium containing a part of the ceramic reuse water was 3.2wt%, the sedimentation height of the colored lower layer copper phthalocyanine was 7.9 ml in 24 hours, and partial precipitation and agglomeration were found at the bottom. The content of copper phthalocyanine in the medium containing ceramic reuse water can reach more than 30wt%, and the prepared water-based color paste is stable, and color difference and precipitation phenomena do not occur within 7 days after the water-based color paste is diluted by tap water by 10 times.
(2) The polyether monoamine/triethanolamine/mercaptocarboxylic acid modified benzene Ma Shuzhi dispersant uses ceramic reuse water, expands the utilization field of water after ceramic industrial water treatment, and has obvious social benefits in multiple aspects such as water saving, emission reduction and the like.
(3) The polyether monoamine/triethanolamine/mercaptocarboxylic acid modified benzene Ma Shuzhi dispersant disclosed by the invention is free from toxic waste gas and waste and VOC (volatile organic compounds) in the synthetic process, and is a green synthetic process.
Drawings
FIG. 1 is a graph of a copper phthalocyanine paste after the dispersant prepared in example 1 is diluted in different aqueous media and left at room temperature for 7 days; diluting tap water by 100 times (a), 1 ten thousand times (b) and 10 ten thousand times (c); tap water: ceramic reuse water =9:1 (mass ratio) dilution by 100 times (d), 1 ten thousand times (e), and 10 ten thousand times (f).
Detailed Description
The present invention will be described in further detail with reference to examples, but the embodiments of the present invention are not limited thereto.
The ceramic reuse water mentioned in the examples and comparative examples of the present application all uses ceramic reuse water provided by a Buddha ceramic manufacturer as a medium, and the main components are analyzed as follows:
Figure RE-GDA0003567272690000041
example 1
(1) 200 g of methyl-terminated polyoxyethylene polyoxypropylene ether monoamine M2070 (molecular weight 2000, CH) is added into a 1000 ml four-neck flask 3 (OE) m (OP) n NH 2 Wherein m =31, n =10, OP (i.e. PO, polyoxypropylene) total content<30 wt%), introducing nitrogen, heating to 65-70 ℃, and slowly adding 100g of styrene-maleic anhydride (SMA) powder (monomer unit mass ratio: styrene/maleic anhydride =65/35, molecular weight is 1000, all resin powder passes through a 100-mesh sieve), 15 g of mercaptopropionic acid is added after 1 hour, nitrogen is continuously introduced, and the temperature is raised to 85-90 ℃ for reaction for 2 hours;
(2) Adding 0.2g of p-toluenesulfonic acid and 10 g of triethanolamine, and reacting for 1.5 hours at the temperature of 80-85 ℃;
(3) 460 g of room temperature ceramic reuse water is added and stirred to form an aqueous solution, then 15.2 g of 50wt% NaOH aqueous solution is used for partial neutralization until the pH value of the solution is 6-7, thus obtaining Ma Shuzhi dispersant (noted as FS 1) 800.4 g of polyether monoamine/alcohol amine/mercapto carboxylic acid modified benzene, and the viscosity of the dispersant at 25 ℃ is measured to be 400mPa & s. The sample was dried, and the solid content was found to be 41.2% by weight. When the dispersant (FS 1) solution is placed and observed in a sealed manner at room temperature, no nonuniform phenomena such as layering and precipitation are found in 6 months, and the viscosity is almost unchanged after 6 months, which shows that the dispersant of the ceramic reuse water has good stability.
Test methods for dispersed organic pigments: taking the dispersed organic pigment copper phthalocyanine as an example, 10 g of the liquid dispersant FS1 is added into 90 g of tap water and 10 g of ceramic reuse water, after the mixture is uniformly stirred, the solid powder of the copper phthalocyanine is gradually added into the solution at 1000rpm until the viscosity of the aqueous dispersion is higher, the addition of the copper phthalocyanine is stopped, and the dispersion is ground for 1 time, so as to obtain the aqueous dispersion with the copper phthalocyanine content of 33.5 wt%. Pouring 10 ml of the dispersion into a 10 ml measuring cylinder, sealing and standing, observing the sedimentation height of the copper phthalocyanine in the measuring cylinder, and recording the sedimentation height and the chromatic aberration of the copper phthalocyanine corresponding to different standing times. The settlement height is 0 after 15 days, and no precipitation or uneven color difference phenomenon exists, which indicates that the copper phthalocyanine still keeps good dispersion in the water containing part of ceramic reuse water.
Then taking the copper phthalocyanine sample, diluting the copper phthalocyanine sample by 100, 1 ten thousand and 10 ten thousand times of tap water, and comparing and observing the color difference and sedimentation phenomenon before and after standing for 7 days to find that the color difference and sedimentation phenomenon do not exist within 7 days (see figure 1); then diluting the mixed solution by 100, 1 ten thousand and 10 ten thousand times (tap water: ceramic reuse water =9:1 (mass ratio)), and comparing and observing the color difference and sedimentation phenomenon before and after standing for 7 days, and finding that the color difference and sedimentation phenomenon do not exist within 7 days, which indicates that the copper phthalocyanine in the water quality containing partial ceramic reuse water still keeps good dispersion after being diluted.
Example 2
(1) 100g of methyl-terminated polyoxyethylene polyoxypropylene ether monoamine M600 (molecular weight 600, CH) is added into a four-mouth flask 3 (OE) m (OP) n NH 2 Wherein the total content of OP (namely PO) is 29wt%, m =8.98, n = 3), nitrogen is introduced, the temperature is raised to 65-60 ℃, and 100g of styrene-maleic anhydride SMA resin powder (mass ratio of monomer units: styrene/maleic anhydride =51.5/48.5, the molecular weight is 1000, all resin powder passes through a 100-mesh sieve), after 0.5 hour, 10 g of thioglycollic acid is added, nitrogen is continuously introduced, and the temperature is increased to 80-85 ℃ for reaction for 2 hours;
(2) Adding 0.5g of dodecyl benzene sulfonic acid and 10 g of triethanolamine, and reacting for 1 hour at the temperature of 90-85 ℃;
(3) 350 g of recycled water at room temperature is added and stirred to form an aqueous solution, and then 30.3 g of 50wt% NaOH aqueous solution is used for partial neutralization until the pH value of the solution is 6-7, so that 500.8 g of polyether monoamine/alkylol amine/mercapto carboxylic acid modified benzene Ma Shuzhi dispersant (recorded as FS 2) is obtained, and the viscosity of the dispersant at 25 ℃ is measured to be 340mPa & s. The sample was dried and the solid content was found to be 38.2wt%. When the dispersing agent (FS 2) solution is placed and observed in a sealed mode at room temperature, no nonuniform phenomena such as layering and precipitation are found in 6 months, the viscosity is almost unchanged after 6 months, and the stability of the dispersing agent in ceramic reuse water is good.
Test methods for dispersed organic pigments: taking dispersed organic pigment copper phthalocyanine as an example, 10 grams of the liquid dispersant FS2 is added into 90 grams of tap water and 10 grams of ceramic reuse water, after uniform stirring, the solid powder of copper phthalocyanine is gradually added into the solution at 1000rpm until the viscosity of the aqueous dispersion is higher, the addition of copper phthalocyanine is stopped, and the dispersion is ground for 1 time, so as to obtain the aqueous dispersion with the copper phthalocyanine content of 34.3 wt%. Pouring 10 ml of the dispersion into a 10 ml measuring cylinder, sealing and standing, observing the sedimentation height of the copper phthalocyanine in the measuring cylinder, recording that the sedimentation height of the copper phthalocyanine and the sedimentation height of the copper phthalocyanine are 0 after 15 days of the chromatism phenomenon corresponding to different standing times, and showing that the copper phthalocyanine still keeps good dispersion in water containing part of ceramic reuse water.
Then taking the copper phthalocyanine sample, diluting the copper phthalocyanine sample by 100, 1 ten thousand or 10 ten thousand times of tap water, and comparing and observing the color difference and sedimentation phenomena before and after standing for 7 days to find that the color difference and sedimentation phenomena do not exist within 7 days; then diluting the mixed solution by 100, 1 ten thousand and 10 ten thousand times (tap water: ceramic reuse water =9:1 (mass ratio)), and comparing and observing the color difference and sedimentation phenomenon before and after standing for 7 days, and finding that the color difference and sedimentation phenomenon do not exist within 7 days, which indicates that the copper phthalocyanine in the water quality containing partial ceramic reuse water still keeps good dispersion after being diluted.
Example 3
(1) 150 g of methyl-terminated polyoxypropylene polyoxyethylene ether monoamine L1000 (molecular weight is 1000, CH) is added into a four-neck flask 3 (OE) m1 [(OP) n (OE) m2 ]NH 2 Wherein the total content of OP (namely PO) is 28.3 weight percent, (m 1+ m 2) =15.59, n =4.88, and both m1 and m2 are more than or equal to 1), introducing nitrogen, heating to 65-60 ℃, and slowly adding 100g of styrene-maleic anhydride SMA resin powder under the conditions of reflux and rapid stirring(the mass ratio of monomer units is that styrene/maleic anhydride =51.5/48.5, the molecular weight is 2000, all resin powder passes through a 100-mesh sieve), after 0.5 hour, 15 g of thioglycollic acid is added, nitrogen is continuously introduced, and the temperature is raised to 85-90 ℃ for reaction for 2 hours;
(2) Adding 0.3g of dodecyl benzene sulfonic acid and 5g of triethanolamine, and reacting for 1.5 hours at the temperature of 90-85 ℃;
(3) 400 g of recycled ceramic water at room temperature is added and stirred to form an aqueous solution, and then 20.2 g of 50wt% NaOH aqueous solution is used for partial neutralization until the pH value of the solution is 6-7, thus obtaining 700.5 g of polyether monoamine/alcohol amine/mercapto carboxylic acid modified benzene Ma Shuzhi dispersant (marked as FS 3), and the viscosity of the dispersant at 25 ℃ is measured to be 450 mPas. A sample was taken and dried, and the solid content was found to be 39.8% by weight. When the dispersing agent (FS 3) solution is placed and observed in a sealed mode at room temperature, no nonuniform phenomena such as layering and precipitation are found in 6 months, the viscosity is almost unchanged after 6 months, and the stability of the dispersing agent in ceramic reuse water is good.
Test methods for dispersed organic pigments: taking the dispersed organic pigment copper phthalocyanine as an example, 10 g of the liquid dispersant FS3 is added into 90 g of tap water and 10 g of ceramic reuse water, after the mixture is uniformly stirred, the solid powder of the copper phthalocyanine is gradually added into the solution at 1000rpm until the viscosity of the aqueous dispersion is higher, the addition of the copper phthalocyanine is stopped, and the dispersion is ground for 1 time, so as to obtain the aqueous dispersion with the copper phthalocyanine content of 32.1 wt%. Pouring 10 ml of the dispersion into a 10 ml measuring cylinder, sealing and standing, observing the sedimentation height of the copper phthalocyanine in the measuring cylinder, and recording the sedimentation height and the chromatic aberration of the copper phthalocyanine corresponding to different standing times. The settlement height is 0 after 15 days, and no precipitation or uneven color difference phenomenon exists, which indicates that the copper phthalocyanine still keeps good dispersion in the water containing part of ceramic reuse water.
Then taking the copper phthalocyanine sample, diluting the copper phthalocyanine sample by 100, 1 ten thousand and 10 ten thousand times of tap water, and comparing and observing the color difference and the sedimentation phenomenon before and after standing for 7 days, and finding that the color difference and the sedimentation phenomenon do not exist within 7 days; then diluting the mixed solution by 100, 1 ten thousand and 10 ten thousand times (tap water: ceramic reuse water =9:1 (mass ratio)), and comparing and observing the color difference and sedimentation phenomenon before and after standing for 7 days, and finding that the color difference and sedimentation phenomenon do not exist within 7 days, which indicates that the copper phthalocyanine in the water quality containing partial ceramic reuse water still keeps good dispersion after being diluted.
Example 4
(1) 200 g of methyl-terminated polyoxyethylene ether monoamine (molecular weight 1000, CH) is added into a four-mouth flask 3 (OE) m NH 2 And m = 22.02), introducing nitrogen, heating to 65-70 ℃, and slowly adding 100g of styrene-maleic anhydride SMA resin powder (monomer unit mass ratio: styrene/maleic anhydride =65/35, molecular weight is 3000, all resin powder passes through a 100-mesh sieve), 5g of thioglycollic acid is added after 1 hour, nitrogen is continuously introduced, and the temperature is raised to 85-90 ℃ for reaction for 2 hours;
(2) Adding 0.1g of p-toluenesulfonic acid and 8 g of triethanolamine, and reacting for 2 hours at the temperature of 85-90 ℃;
(3) 457 g of recycled ceramic water at room temperature is added and stirred to form an aqueous solution, and then 30.1 g of 50wt% NaOH aqueous solution is used for partial neutralization until the pH value of the solution is 6-7, so that Ma Shuzhi dispersant (noted as FS 4) 800.2 g of polyether monoamine/alcohol amine/mercapto carboxylic acid modified benzene is obtained, and the viscosity of the dispersant at 25 ℃ is measured to be 510mPa & s. The sample was dried, and the solid content was found to be 40.2% by weight. When the dispersant (FS 4) solution is placed and observed in a sealed manner at room temperature, no nonuniform phenomena such as layering and precipitation are found in 6 months, and the viscosity is almost unchanged after 6 months, which shows that the dispersant stability in the ceramic reuse water is good.
Test methods for dispersed organic pigments: taking the dispersed organic pigment copper phthalocyanine as an example, 10 g of the liquid dispersant FS4 is added into 90 g of tap water and 10 g of ceramic reuse water, after the mixture is uniformly stirred, the solid powder of the copper phthalocyanine is gradually added into the solution at 1000rpm until the viscosity of the aqueous dispersion is higher, the addition of the copper phthalocyanine is stopped, and the dispersion is ground for 1 time, so as to obtain the aqueous dispersion with the copper phthalocyanine content of 30.2 wt%. Pouring 10 ml of the dispersion into a 10 ml measuring cylinder, sealing and standing, observing the sedimentation height of the copper phthalocyanine in the measuring cylinder, and recording the sedimentation height and the chromatic aberration of the copper phthalocyanine corresponding to different standing times. The settlement height is 0 after 15 days, and no precipitation or uneven color difference phenomenon exists, which indicates that the copper phthalocyanine still keeps good dispersion in the water containing part of ceramic reuse water.
Then taking the copper phthalocyanine sample, diluting the copper phthalocyanine sample by 100, 1 ten thousand and 10 ten thousand times of tap water, and comparing and observing the color difference and the sedimentation phenomenon before and after standing for 7 days, and finding that the color difference and the sedimentation phenomenon do not exist within 7 days; then diluting the mixed solution by 100, 1 ten thousand and 10 ten thousand times (tap water: ceramic reuse water =9:1 (mass ratio)), and comparing and observing the color difference and sedimentation phenomenon before and after standing for 7 days, and finding that the color difference and sedimentation phenomenon do not exist within 7 days, which indicates that the copper phthalocyanine in the water quality containing partial ceramic reuse water still keeps good dispersion after being diluted.
Example 5
(1) 100g of methyl-terminated polyoxyethylene ether monoamine (molecular weight 1000, CH) is added into a four-mouth flask 3 (OE) m NH 2 M = 22.02), 50 g methyl capped polyoxyethylenepolyoxypropylene ether monoamine M600 (molecular weight 600,ch) 3 (OE) m (OP) n NH 2 Wherein the total content of OP (namely PO) is 29wt%, m =8.98, n = 3), nitrogen is introduced, the temperature is raised to 65-70 ℃, and 100g of styrene-maleic anhydride SMA resin powder (mass ratio of monomer units: styrene/maleic anhydride =60/40, molecular weight is 2000, all resin powder passes through a 100-mesh sieve), 5g of mercaptopropionic acid is added after 0.8 hour, nitrogen is continuously introduced, and the temperature is raised to 85-90 ℃ for reaction for 2 hours;
(2) Adding 0.3g of p-toluenesulfonic acid and 15 g of triethanolamine, and reacting for 1 hour at the temperature of 80-85 ℃;
(3) 390 g of recycled ceramic water at room temperature is added and stirred to form an aqueous solution, and then 40.3 g of 50wt% KOH aqueous solution is used for partial neutralization until the pH value of the solution is 6-7, thus obtaining Ma Shuzhi dispersant (noted as FS 5) 700.6 g of polyether monoamine/alcohol amine/mercapto carboxylic acid modified benzene, and the viscosity of the dispersant at 25 ℃ is 380mPa & s. The sample was dried, and the solid content was found to be 40.9% by weight. When the dispersing agent (FS 5) solution is placed and observed in a sealed mode at room temperature, no nonuniform phenomena such as layering and precipitation are found in 6 months, the viscosity is almost unchanged after 6 months, and the stability of the dispersing agent in ceramic reuse water is good.
Test methods for dispersed organic pigments: taking dispersed organic pigment copper phthalocyanine as an example, 10 grams of the liquid dispersant FS5 is added into 90 grams of tap water and 10 grams of ceramic reuse water, after uniform stirring, the solid powder of copper phthalocyanine is gradually added into the solution at 1000rpm until the viscosity of the aqueous dispersion is higher, the addition of the copper phthalocyanine is stopped, and the dispersion is ground for 1 time, so as to obtain the aqueous dispersion with the copper phthalocyanine content of 31.9 wt%. Pouring 10 ml of the dispersion into a 10 ml measuring cylinder, sealing and standing, observing the sedimentation height of the copper phthalocyanine in the measuring cylinder, and recording the sedimentation height and the chromatic aberration of the copper phthalocyanine corresponding to different standing times. The settlement height is 0 after 15 days, and no precipitation or uneven color difference phenomenon exists, which indicates that the copper phthalocyanine still keeps good dispersion in the water containing part of ceramic reuse water.
Then taking the copper phthalocyanine sample, diluting the copper phthalocyanine sample by 100, 1 ten thousand and 10 ten thousand times of tap water, and comparing and observing the color difference and the sedimentation phenomenon before and after standing for 7 days, and finding that the color difference and the sedimentation phenomenon do not exist within 7 days; then diluting the mixed solution by 100, 1 ten thousand and 10 ten thousand times (tap water: ceramic reuse water =9:1 (mass ratio)), and comparing and observing the color difference and sedimentation phenomenon before and after standing for 7 days, and finding that the color difference and sedimentation phenomenon do not exist within 7 days, which indicates that the copper phthalocyanine in the water quality containing partial ceramic reuse water still keeps good dispersion after being diluted.
Comparative example 1
Test method for the dispersion of organic pigments with sodium polyacrylate (molecular weight 3000, half carboxyl neutralized COONa): in the case of dispersing the organic pigment copper phthalocyanine, 10 g of the sodium polyacrylate solution (40 wt%) was added to 100g of tap water, and after stirring uniformly, a solid powder of copper phthalocyanine was gradually added to the solution at 1000rpm until the copper phthalocyanine of the aqueous dispersion started to partially agglomerate or precipitate, and the addition of copper phthalocyanine was stopped and ground 1 time. According to the method, the maximum amount of the copper phthalocyanine in the aqueous solution which can be dispersed stably for a short time is 1.2% (mass fraction of water), the amount of the copper phthalocyanine which can be dispersed stably for a short time is low, and the copper phthalocyanine is subjected to agglomeration and precipitation after standing for 1 night for 24 hours. Thus, simple carboxyl and carboxylate dispersants have limited dispersing effect on organic pigments.
Comparative example 2
A polyether polycarboxylic acid dispersant (polyethylene glycol ether or polyoxyethylene ether) TPEG monomer unit content of 30wt% and acrylic acid unit content of 70wt% is tested for dispersing organic pigments by adding 10 g of the polyether polycarboxylic acid dispersant (40 wt%, pH = 6-7) to 100g of tap water, stirring uniformly, adding copper phthalocyanine solid powder gradually to the solution at 1000rpm until the copper phthalocyanine of the aqueous dispersion starts to partially agglomerate or precipitate, stopping adding the copper phthalocyanine, and grinding 1 time.
Comparative example 3
(1) 150 g of monomethyl-terminated polyethylene glycol ether (or polyoxyethylene ether) MPEG (molecular weight 1000, CH) was placed in a four-neck flask 3 (OE) m OH), heating to 65-70 ℃, and slowly adding 100g of styrene-maleic anhydride SMA resin powder (monomer unit mass ratio: styrene/maleic anhydride =51.5/48.5, molecular weight is 2000, resin powder passes through a 100-mesh sieve completely), after heat preservation reaction is carried out for 2 hours, temperature is raised to 85-90 ℃ for reaction for 5 hours;
(2) 370 g of tap water at room temperature and 30 g of a 50wt% aqueous NaOH solution were added thereto and stirred to form an aqueous solution having a pH of 6 to 7, to give 650 g of a polyether-modified benzene Ma Shuzhi dispersant (designated as FS-01), and the mixture was sampled and dried to obtain a solid content of 39.7wt%.
Ceramic reuse water medium dispersant FS-02:
step (1) is the same as step (1) of FS-01;
(2) 370 g of recycled ceramic water at room temperature and 30 g of 50wt% NaOH aqueous solution are added and stirred to form an aqueous solution, the pH value of the aqueous solution is 6-7, 650 g of polyether modified benzene Ma Shuzhi dispersant (recorded as FS-02) is obtained, and the viscosity of the dispersant at 25 ℃ is 280 mPas. The sample was dried, and the solid content was found to be 39.8% by weight.
Test methods for dispersed organic pigments: taking the dispersed organic pigment copper phthalocyanine as an example, 10 g of liquid dispersant FS-01 is added into 100g of tap water, after stirring uniformly, the solid powder of copper phthalocyanine is gradually added into the solution at 1000rpm until the copper phthalocyanine of the aqueous dispersion starts to partially agglomerate or precipitate, the addition of copper phthalocyanine is stopped, and grinding is carried out for 1 time. Until the aqueous dispersion was highly viscous, the addition of copper phthalocyanine was stopped, and the dispersion was ground 1 time. According to this method, the maximum amount of copper phthalocyanine which can be dispersed in the aqueous solution with a short stabilization is 5.4% (mass fraction in water). Pouring 10 ml of the dispersion into a 10 ml measuring cylinder, sealing and standing, observing the sedimentation height of the copper phthalocyanine in the measuring cylinder, and recording the sedimentation height and the chromatic aberration of the copper phthalocyanine corresponding to different standing times. After standing for 24 hours over 1 night, the sedimentation height of the lower layer copper phthalocyanine with color is 5.5 ml, the upper layer is colorless liquid, and partial precipitation and agglomeration phenomena are found at the bottom after 2 days and 48 hours. It can be seen that only the polyether modified benzene Ma Shuzhi dispersant has a general dispersing ability.
After 10 g of a liquid dispersant FS-02 was added to 100g of tap water and stirred uniformly, solid copper phthalocyanine powder was gradually added to the solution at 1000rpm until the copper phthalocyanine in the aqueous dispersion started to partially agglomerate or precipitate, the addition of copper phthalocyanine was stopped, and the mixture was ground 1 time. Until the aqueous dispersion was highly viscous, the addition of copper phthalocyanine was stopped, and the dispersion was ground 1 time. According to this method, the maximum amount of copper phthalocyanine which can be dispersed in the aqueous solution with a short stabilization is 3.2% (mass fraction in water). Pouring 10 ml of the dispersion into a 10 ml measuring cylinder, sealing and standing, observing the sedimentation height of the copper phthalocyanine in the measuring cylinder, and recording the sedimentation height and the chromatic aberration of the copper phthalocyanine corresponding to different standing times. After standing for 24 hours over 1 night, the colored lower copper phthalocyanine had a settled height of 7.9 ml, the upper layer was a colorless liquid, and partial precipitation and agglomeration were found at the bottom. It can be seen that only the polyether modified benzene Ma Shuzhi dispersant has poorer dispersing ability in water containing part of ceramic reuse water.
Comparative example 4: without catalyst
(1) 200 g of methyl-terminated polyoxyethylene polyoxypropylene ether monoamine M2070 (molecular weight 2000, CH) is added into a 1000 ml four-neck flask 3 (OE) m1 [(OE) m2 (OP) n ]NH 2 Wherein (m 1+ m 2) =31, n =10, OP (i.e. PO, polyoxypropylene) total content<30 wt%), introducing nitrogen, heating to 65-70 ℃, and slowly adding 100g of styrene-maleic anhydride SMA resin powder (monomer unit mass ratio: styrene/maleic anhydride =65/35, molecular weight is 1000, all resin powder passes through a 100-mesh sieve), 15 g of mercaptopropionic acid is added after 1 hour, nitrogen is continuously introduced, and the temperature is raised to 85-90 ℃ for reaction for 2 hours;
(2) Adding 10 g of triethanolamine, and reacting for 1.5 hours at the temperature of 80-85 ℃;
(3) 460 g of room temperature ceramic reuse water was added thereto and stirred to form an aqueous solution, and the solution was partially neutralized with 15 g of a 50wt% aqueous NaOH solution until the pH value of the solution became 6 to 7 to obtain 800 g of a modified benzene Ma Shuzhi dispersant (designated as FS-04), which was found to have a viscosity of 560 mPas at 25 ℃. The sample was dried, and the solid content was found to be 40.0wt%.
Test methods for dispersed organic pigments: taking dispersed organic pigment copper phthalocyanine as an example, 10 g of the dispersing agent FS-04 is added into 100g of tap water, after stirring uniformly, the solid powder of copper phthalocyanine is gradually added into the solution at 1000rpm until the copper phthalocyanine of the aqueous dispersion starts to partially agglomerate or precipitate, the addition of copper phthalocyanine is stopped, and grinding is carried out for 1 time. According to the method, the maximum amount of the copper phthalocyanine in the aqueous solution which can be dispersed stably for a short time is 6.9% (mass fraction of water), the amount of the copper phthalocyanine which can be dispersed stably for a short time is low, and the copper phthalocyanine is subjected to agglomeration and precipitation after standing for 24 hours over 1 night. Therefore, the modified benzene Ma Shuzhi dispersant prepared by the catalysis of the alkylbenzene sulfonic acid catalyst is not used, the solid content is low, the triethanolamine molecules are rarely grafted on the molecules, and the obtained modified benzene Ma Shuzhi has limited dispersion effect on organic pigments.
Comparative example 5: catalytic reaction time extension
(1) 200 g of methyl-terminated polyoxyethylene polyoxypropylene ether monoamine M2070 (molecular weight 2000, CH) is added into a 1000 ml four-neck flask 3 (OE) m1 [(OE) m2 (OP) n ]NH 2 Wherein (m 1+ m 2) =31, n =10, OP (i.e. PO, polyoxypropylene) total content<30wtPercent), introducing nitrogen, heating to 65-70 ℃, and slowly adding 100g of styrene-maleic anhydride SMA resin powder (monomer unit mass ratio: styrene/maleic anhydride =65/35, the molecular weight is 1000, all the resin powder passes through a 100-mesh sieve), 15 g of mercaptopropionic acid is added after 1 hour, nitrogen is continuously introduced, and the temperature is increased to 85-90 ℃ for reaction for 2 hours;
(2) Adding 0.2g of p-toluenesulfonic acid and 10 g of triethanolamine, and reacting for 3.5 hours at the temperature of 80-85 ℃;
(3) 460 g of room temperature ceramic reuse water was added thereto and stirred to form an aqueous solution, and then partially neutralized with 15.2 g of 50wt% aqueous NaOH solution until the pH value of the solution became 6 to 7, to obtain 800.4 g of a modified benzene Ma Shuzhi dispersant (designated as FS-05), even though the viscosity at 25 ℃ was found to be 7850 mPas. The sample was dried, and the solid content was found to be 41.2% by weight. The solution was left to stand under a sealed condition at room temperature, and after 6 months, the viscosity continued to increase, and the viscosity at 25 ℃ increased to 15600 mPas. Therefore, the catalytic reaction time is too long, the viscosity of the prepared modified dispersant is obviously increased, and the stability is greatly reduced. The partial cross-linking reaction is generated due to the fact that after the triethanolamine with three hydroxyl groups is primarily reacted with two monofunctional groups of polyether monoamine and hydroxycarboxylic acid, a plurality of anhydride groups remained in modified styrene-maleic resin molecules are too long in action time, and accordingly the molecular weight is greatly increased.
Test methods for dispersed organic pigments: taking the dispersed organic pigment copper phthalocyanine as an example, 10 g of the instantly prepared dispersant FS-05 is added into 100g of tap water, and after stirring uniformly, the solid powder of copper phthalocyanine is gradually added into the solution at 1000rpm until the copper phthalocyanine of the aqueous dispersion starts to partially agglomerate or precipitate, and the addition of copper phthalocyanine is stopped, and grinding is carried out for 1 time. According to the method, the maximum amount of the copper phthalocyanine in the aqueous solution which can be dispersed stably for a short time is 5.2% (mass fraction of water), the amount of the copper phthalocyanine which can be dispersed stably for a short time is low, and the copper phthalocyanine is subjected to agglomeration and precipitation after standing for 24 hours over 1 night. It can be seen that the modified benzene Ma Shuzhi dispersant prepared immediately after the catalytic action time of the alkylbenzene sulfonic acid is too long has too large molecular weight, and the dispersant action on the organic pigment is very limited.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such modifications are intended to be included in the scope of the present invention.

Claims (7)

1. A preparation method of a nitrogen/sulfur hybrid modified benzene Ma Shuzhi ceramic dispersant is characterized by comprising the following steps:
adding polyether monoamine under the condition of introducing protection gas, heating to 60-70 ℃, slowly adding styrene-maleic anhydride resin powder under the conditions of reflux and stirring, adding mercaptomonocarboxylic acid after 0.5-1 hour, heating to 80-90 ℃, reacting for 1~2 hours, finally adding alkylbenzene sulfonic acid and triethanolamine, keeping the temperature for 80-90 ℃, reacting for 1~2 hours, adding water, stirring, adding alkali liquor, adjusting the pH value of the mixed liquor to be 5~8, and obtaining a modified benzene Ma Shuzhi ceramic dispersing agent with the content of 10-50wt%;
the styrene-maleic anhydride resin is a styrene-maleic anhydride copolymer, the molecular weight is 1000 to 3000, and the content of styrene monomer units is 50 to 65wt%; the molecular weight of the modified styrene-maleic resin modified by polyether monoamine is between 2000 and 9000;
the mass ratio of the polyether monoamine to the styrene-maleic anhydride resin powder to the monothiocarboxylic acid to the alkylbenzene sulfonic acid to the triethanolamine is (100 to 200): 100: (5 to 15): (0.1 to 0.5): (5 to 15).
2. The method according to claim 1, wherein the monothiocarboxylic acid is at least one of thioglycolic acid and mercaptopropionic acid; the alkylbenzene sulfonic acid is at least one of p-toluenesulfonic acid and dodecylbenzene sulfonic acid; the polyether monoamine is CH 3 (OE) m NH 2 、CH 3 (OE) m (OP) n NH 2 、CH 3 (OE) m1 [(OP) n (OE) m2 ]NH 2 At least one of m =7 to 46, n =0 to 11, m1=1 to 45, m2=1 to 45, OE is an oxyethylene group, OP is an oxypropylene group, and the molecular weight is 500 to 2000, wherein polyoxypropylene is used as the active ingredientThe content is less than 30wt% of the total amount of polyether monoamine.
3. The preparation method according to claim 1 or 2, characterized in that the alkali liquor is at least one of sodium hydroxide solution and potassium hydroxide solution, and the pH value of the mixed liquor is 6~7; the water is ceramic reuse water, tap water or a mixture of the ceramic reuse water and the tap water; the styrene-maleic anhydride resin powder is fine powder with the average mesh number of more than 80 meshes.
4. A modified benzene Ma Shuzhi ceramic dispersant made by the process of any of claims 1~3.
5. The use of the modified benzene Ma Shuzhi ceramic dispersant of claim 4 in aqueous organic pigment mill base.
6. The use according to claim 5, wherein the dispersant is used for dispersing an organic pigment in ceramic-containing reuse water, wherein the organic pigment is phthalocyanine.
7. The use according to claim 6, wherein the mass ratio of the organic pigment to the modified benzene Ma Shuzhi ceramic dispersant and water is 100: (5 to 10): (≧ 100).
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