CN102863822A - Hyperbranched macromolecule dispersing agent for dispersing dyes and preparation method thereof - Google Patents
Hyperbranched macromolecule dispersing agent for dispersing dyes and preparation method thereof Download PDFInfo
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- CN102863822A CN102863822A CN2012103583741A CN201210358374A CN102863822A CN 102863822 A CN102863822 A CN 102863822A CN 2012103583741 A CN2012103583741 A CN 2012103583741A CN 201210358374 A CN201210358374 A CN 201210358374A CN 102863822 A CN102863822 A CN 102863822A
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Abstract
The invention provides a hyperbranched macromolecule dispersing agent used for a disperse dye. A constitutional formula of the hyperbranched macromolecule dispersing agent is as follows, wherein m is larger than or equal to 1, n is larger than or equal to 1, and relative molecular mass is 800-5000. With the adoption of the hyperbranched macromolecule dispersing agent, unique molecular structures and characters of a hyperbranched polymer are used and aromatic naphthoic acid and the like are adopted to modify the hyperbranched polymer to obtain the hyperbranched macromolecule dispersing agent for the dispersing dye. Compared with the existing dispersing agent for the dispersing dye, the hyperbranched macromolecule dispersing agent has excellent dissolving and dispersing effects.
Description
Technical field
The invention belongs to field of fine chemical, relate to a kind of dispersed dye hyper-branched polymer dispersion agent, also relate to the preparation method of this dispersion agent.
Background technology
Contain polar group in the dispersed dye molecule, but do not contain sulfonic group, the water soluble group such as carboxylic acid group, so the solvability of dispersed dye in water is very little.Dispersed dye in use need add a certain amount of dispersion agent, after adding dispersion agent dispersed dye with the particulate state dispersion suspension of small crystal in water.The dispersion agent that generally uses at present has nonionic, negatively charged ion, cats product and some low molecules or polymer substance (sulfonated lignin etc.).Adsorption by dispersion agent and dye molecule is wrapped up dispersion agent in the dye molecule periphery, because the repulsive interaction between the dispersion agent reaches the purpose of dispersed dye.But the difference of dye structure, requirement to dispersion agent also is different, and single tensio-active agent can change along with the change of ambient conditions the dissemination of dispersed dye, and dyestuff/dispersant system may be destroyed and can't be kept preferably dispersion stabilization.
Summary of the invention
The object of the present invention is to provide a kind of dispersed dye hyper-branched polymer dispersion agent, the problem that the dispersant of disperse dye kind is single and dispersion stabilization is poor that exists to solve prior art.
Another object of the present invention provides the preparation method of described hyper-dispersant.
The object of the present invention is achieved like this, a kind of dispersed dye hyper-branched polymer dispersion agent, and its structural formula is as follows:
Wherein, m 〉=1; N 〉=1; Relative molecular mass is 800～5000.
Above-mentioned dispersed dye are made by hyperbranched polymer solution and aromatic series naphthoic acid solution reaction with the preparation method of hyper-branched polymer dispersion agent.
Specifically comprise the steps:
Step 1. is got hyperbranched polymer and is dissolved in the solvent, makes hyperbranched polymer solution through fully dissolving, and gets the aromatic series naphthoic acid and is dissolved in the solvent, makes naphthoic acid solution through abundant dissolving;
Step 2, hyperbranched polymer solution is placed reaction vessel, add catalyzer, under agitation heating drips the naphthoic acid solution reaction again, cooling after reaction finishes, and the evaporation desolventizing gets crude product;
Step 3, will the gained crude product add in the solvent and dissolve, add precipitation agent, after filtration, washing, dry product.
In the above-mentioned steps 1, the mass ratio of hyperbranched polymer and solvent is 1 ︰ 1～5, and the mass ratio of aromatic series naphthoic acid and solvent is 1 ︰ 1～5.
In the above-mentioned steps 2, Heating temperature is 60～180 ℃, and cooling temperature is 20～50 ℃, and be 1～5h cooling time.
In the above-mentioned steps 3, described precipitation agent is water, methyl alcohol, ethanol, acetone, ether and composition thereof; Described drying is vacuum-drying 24h, and vacuum tightness is 10～80KPa.
The present invention has following beneficial effect, the present invention utilizes molecular structure and the chemical property of hyperbranched polymer uniqueness, adopt the aromatic series naphthoic acid that hyperbranched polymer is carried out modification and obtain dispersed dye hyper-branched polymer dispersion agent, because the existence of vesicular structure in the product structure disperses to be packaged in to reach dissemination in the vesicular structure thereby be conducive to dispersed dye; In addition with respect to existing dispersed dye with dispersion agent such as Dispersant MF, dispersion agent NNO, sodium lignosulfonate etc., hyperbranched dispersion agent of the present invention has multiterminal hydrophilic and oleophilic group, and the naphthalene nucleus of its structure periphery can combine with the hydrophobic grouping on dispersed dye surface, hydrophilic oh group can make dispersion system stable in water, and therefore hyperbranched dispersion agent of the present invention has more excellent solubilization dispersion effect.
Description of drawings
Fig. 1 is the infrared spectrum that the embodiment of the invention 1 hyper-branched polymer dispersant structure is identified.
Fig. 2 is that the embodiment of the invention 1 hyper-branched polymer dispersant structure is identified
1H NMR spectrogram.
Embodiment
A kind of dispersed dye hyper-branched polymer dispersion agent, its structural formula is as follows:
Wherein, m 〉=1; N 〉=1; Relative molecular mass is 800～5000.
Its preparation method is: made by hyperbranched polymer solution and aromatic series naphthoic acid solution reaction, specifically comprise the steps:
Step 1. is got hyperbranched polymer and is dissolved in the solvent, makes hyperbranched polymer solution through fully dissolving, and gets the aromatic series naphthoic acid and is dissolved in the solvent, makes naphthoic acid solution through abundant dissolving; The mass ratio of hyperbranched polymer and solvent is 1 ︰ 1～5, and the mass ratio of aromatic series naphthoic acid and solvent is 1 ︰ 1～5.
Step 2, hyperbranched polymer solution is placed reaction vessel, add catalyzer, under agitation be heated to 60～180 ℃, drip again the naphthoic acid solution reaction, cooling after reaction finishes, the evaporation desolventizing gets crude product; Cooling temperature is 20～50 ℃, and be 1～5h cooling time.
Step 3, will the gained crude product add in the solvent and dissolve, add precipitation agent, after filtration, washing, dry product; Dry is vacuum-drying 12～24h, and vacuum tightness is 10～80KPa.
Hyperbranched polymer is terminal hydroxy group aliphatics hyper-branched polyester and terminal hydroxy group aliphatics hyperbranched poly (amide-ester).
Catalyzer is a kind of in tosic acid, butyl (tetra) titanate, the vitriol oil, the zinc chloride.
Catalyst levels is 0.1～10% of reactant total mass.
The aromatic series naphthoic acid is 2-naphthoic acid, 1-hydroxy-2-naphthoic acid, 1, a kind of in 8-naphthalic anhydride, 2-hydroxyl-3-naphthoic acid, Isosorbide-5-Nitrae-naphthalic acid, 3-amino-2-naphthoic acid, 5-amino-2-naphthoic acid and the 6-Hydroxy-2-naphthoic acid.
The mol ratio of hyperbranched polymer and aromatic series naphthoic acid is 1 ︰ 0.1～0.9.
Precipitation agent is water, methyl alcohol, ethanol, acetone, ether and composition thereof.
The mass ratio of precipitation agent and solvent is 1 ︰, 2～5 ︰ 1, and the mixing solutions quality of precipitation agent and solvent is 5～30 times of crude product quality.
Embodiment 1: the 0.1mol superbrnaching end-hydroxy polyester is dissolved in the 30ml toluene, makes superbrnaching end-hydroxy polyester solution, the 0.02mol2-naphthoic acid is dissolved in the 20ml DMF, make 2-naphthoic acid solution; Superbrnaching end-hydroxy polyester solution is added in the four-hole boiling flask, add 2% tosic acid (quality with hyper-branched polyester is as the criterion), be heated to 120 ℃, drip 2-naphthoic acid solution, stir, reaction 4h, reaction finishes by cooling, cooling temperature is 35 ℃, cooling 3h, the rotary evaporation desolventizing obtains crude product behind the evaporate to dryness, then crude product is dissolved in the chloroform, solution being dropped in the water, the desolventizing of chloroform layer rotary evaporation is obtained faint yellow solid, is vacuum-drying 18h under the 20KPa in vacuum tightness, obtain the hyper-branched polymer dispersion agent, its structural formula is as follows:
Wherein, m=4; N=2; Relative molecular mass is 1000.
Embodiment 2-4, preparation process is referring to embodiment 1, and related data sees the following form 1.
Table 1 embodiment 2-4 related data
Embodiment 6, the end carboxyl super branched polymeric amide of 0.1mol is dissolved in the 50ml toluene makes solution, 0.01mol3-amino-2-naphthoic acid is dissolved in the 40ml pyridine makes solution, end carboxyl super branched polyamide solution is added in the four-hole bottle, add again the vitriol oil 1% (quality with ultrabranching polyamide is as the criterion), be heated to 140 ℃, drip 3-amino-2-naphthoic acid solution, stirring reaction 8h, reaction finishes by cooling, and cooling temperature is 45 ℃, cooling 2h, the rotary evaporation desolventizing obtains crude product behind the evaporate to dryness, then crude product is dissolved in the chloroform, solution dropped in the water precipitate, chloroform layer separation and rotary evaporation desolventizing are obtained faint yellow solid, and vacuum tightness is 30KPa, and vacuum-drying 20h obtains the hyper-branched polymer dispersion agent.
Embodiment 7,0.1mol superbrnaching end-hydroxy poly-(amine-ester) is dissolved in the 30ml toluene makes solution, with 0.02mol1, the 4-naphthalic acid is dissolved in N, make solution in the dinethylformamide, poly-(amine-ester) solution of superbrnaching end-hydroxy is added in the four-hole bottle, add again tosic acid 3% (quality with hyperbranched polyamine-ester is as the criterion), be heated to 120 ℃, drip Isosorbide-5-Nitrae-naphthalic acid solution, stirring reaction 4h, reaction finishes by cooling, cooling temperature is 25 ℃, cooling 1.5h, rotary evaporation desolventizing, obtain crude product behind the evaporate to dryness, then crude product is dissolved in the chloroform, solution is dropped in the water precipitate, separating chloroform layer also, the rotary evaporation desolventizing obtains faint yellow solid, vacuum tightness is 40KPa, and vacuum-drying 24h obtains the hyper-branched polymer dispersion agent.
Embodiment 8, poly-(amine-ester) solution of amine-terminated hyperbrancedization of 0.1mol is made solution in 30ml toluene, be placed in the reactor, stir also and progressively be heated to 100 ℃, add again tosic acid 1% (quality with hyperbranched polyamine-ester is as the criterion), 0.03mol1 has been dissolved in dropping, the pyridine solution of 4-naphthalic acid, continue to stir insulation reaction 4h, reaction finishes by cooling, and cooling temperature is 30 ℃, cooling 1h, the rotary evaporation desolventizing obtains crude product behind the evaporate to dryness, then crude product is dissolved in the methylene dichloride, solution dropped in the ether precipitate, dichloromethane layer separation and rotary evaporation desolventizing are obtained faint yellow solid, and vacuum tightness is 20KPa, and vacuum-drying 18h obtains the hyper-branched polymer dispersion agent.
Hyperbranched polymer is the macromole of the high degree of branching of a class, and its molecular structure is the 3 D stereo shape and has a large amount of many hollow structures and exists, and its molecule periphery exists a large amount of terminal functionality to make it have special chemical property in addition.
The hyperbranched polymer end has the active function groups that can further react in a large number, therefore can obtain a series of functional high molecule materials with property by end group is modified.Can obtain a kind of amphipathic hyperbranched polymer by hyperbranched polymer being carried out the modification of surface hydrophilic oleophylic, this polymkeric substance has excellent solvability in water and in a large amount of dissolving, and be different from general small molecules amphipathic molecule such as common small molecules tensio-active agent, amphipathy hyperbranched polymer can just have preferably surfactivity when its concentration is very little, can effectively reduce the surface tension of water, therefore this amphipathy hyperbranched polymer can be applied to make dispersed dye reach good dispersion in the dispersion application of dispersed dye.
Amphipathy hyperbranched polymer has than the more hydrophilic radical of general tensio-active agent and lipophilic group, thereby makes it have more excellent surfactivity.The unimolecular micelle that this amphipathic polymkeric substance forms in solution is more stable than the micella of traditional small molecules tensio-active agent or the formation of amphipathic linear copolymer, and there is a large amount of empty structures micella inside, make it can be used as the suitable guest molecule of host molecule parcel, can promote the solvability of hydrophobic material in water to strengthen, play the effect of solubilization.Therefore, the present invention utilizes the special molecular structure of amphipathy hyperbranched polymer and surfactivity preferably, is applied to dispersed dye, can make dispersed dye reach preferably dispersion effect in water.
As can be seen from Figure 1, at 3300cm
-1Near the absorption peak of hydroxyl has appearred produce each other hydrogen bond association between the hydroxyl owing to have numerous hydroxyls in the product, thereby cause near 3300cm-1, having occurred larger absorption peak; At 3030cm
-1Near the absorption peak of naphthalene nucleus has appearred, and at 2950.55cm
-1The place is the absorption peak of methyl, methylene radical.
As can be seen from Figure 2, wherein δ=0.65-3.0ppm place is the absorption peak of hyperbranched polymer; The unimodal of δ=3.89ppm place then is the absorption peak of OH proton in the product molecule, and δ=7.0-8.0ppm place belongs to the absorption peak of naphthalene nucleus.Contain naphthalene ring in the presentation of results product structure, substantially obtain expecting the object of experiment product.
Be different from as can be known traditional dispersion agent such as Dispersant MF, dispersion agent NNO from above analysis, the hyperbranched polymer dispersion agent that the present invention synthesizes, have numerous hydrophilic oh groups and hydrophobic naphthalene nucleus in the structure, thereby make it have good wetting effect, with synthetic hyperbranched polymer dispersion agent with after dispersed dye mix, the hydrophobic grouping on dispersion agent surface can interact with dispersed dye, make dispersant adsorption in the surface of dispersed dye, and the hydrophilic hydroxyl groups in the dispersion agent can make dispersion system stable for a long time in water.Vesicular structure in the hyperbranched polymer dispersant structure can be conducive in the molecule pore space structure that dispersed dye are scattered in dispersion agent in addition, thereby reaches the dispersion effect of more having a mind to.
Hyper-branched polymer dispersion agent service condition of the present invention contrasts with the service condition of existing dispersant of disperse dye commonly used:
Enchashment has common dispersants MF, dispersing agent NNO, sodium lignosulfonate, with hyper-branched polymer dispersion agent of the present invention Disperse Red E-3B is carried out dispersion experiment, concrete result such as following table 1.
The contrast of several dispersion agent service condition of table 1 situation
As can be seen from Table 1, compared to common in the market dispersion agent, hyperbranched polymer dispersant of disperse dye of the present invention has preferably dispersing property to dispersed dye, and the dispersion stabilization of the hyperbranched dispersion agent that forms/dispersed dye system is good.
Claims (10)
1. dispersed dye hyper-branched polymer dispersion agent is characterized in that its structural formula is as follows:
Wherein, m 〉=1; N 〉=1; Relative molecular mass is 800～5000.
2. dispersed dye as claimed in claim 1 is characterized in that: made by hyperbranched polymer solution and aromatic series naphthoic acid solution reaction with the preparation method of hyper-branched polymer dispersion agent.
3. dispersed dye as claimed in claim 2 is characterized in that with the preparation method of hyper-branched polymer dispersion agent, specifically comprise the steps:
Step 1. is got hyperbranched polymer and is dissolved in solvent, makes hyperbranched polymer solution through fully dissolving; Get the aromatic series naphthoic acid and be dissolved in solvent, make naphthoic acid solution through fully dissolving;
Step 2. places reaction vessel with hyperbranched polymer solution, adds catalyzer, and under agitation heating drips the modifier solution reaction again, cooling after reaction finishes, and the evaporation desolventizing gets crude product;
Step 3. will the gained crude product adds in the solvent dissolve, and add precipitation agent, after filtration, washing, dry product.
4. dispersed dye as claimed in claim 3 is characterized in that with the preparation method of hyper-branched polymer dispersion agent,
In the step 1, the mass ratio of hyperbranched polymer and solvent is 1 ︰ 5～10, and the mass ratio of naphthoic acid and solvent is 1 ︰ 5～10;
In the step 2, Heating temperature is 60～180 ℃, and cooling temperature is 20～50 ℃, and be 1～5h cooling time;
In the step 3, described drying is vacuum-drying 24h, and vacuum tightness is 10～80KPa.
5. such as the preparation method of each described dispersed dye of claim 2-4 with the hyper-branched polymer dispersion agent, it is characterized in that described hyperbranched polymer is terminal hydroxy group aliphatics hyper-branched polyester and terminal hydroxy group aliphatics hyperbranched poly (amide-ester).
6. such as the preparation method of each described dispersed dye of claim 2-4 with the hyper-branched polymer dispersion agent, it is characterized in that described catalyzer is tosic acid, butyl (tetra) titanate, the vitriol oil, zinc chloride; Described catalyst levels is 0.1～10% of reactant total mass.
7. such as the preparation method of each described dispersed dye of claim 2-4 with the hyper-branched polymer dispersion agent, it is characterized in that, described aromatic series naphthoic acid is 2-naphthoic acid, 1-hydroxy-2-naphthoic acid, 1, a kind of in 8-naphthalic anhydride, 2-hydroxyl-3-naphthoic acid, Isosorbide-5-Nitrae-naphthalic acid, 3-amino-2-naphthoic acid, 5-amino-2-naphthoic acid and the 6-Hydroxy-2-naphthoic acid.
8. such as the preparation method of each described dispersed dye of claim 2-4 with the hyper-branched polymer dispersion agent, it is characterized in that the mol ratio of described hyperbranched polymer and aromatic series naphthoic acid is 1 ︰ 0.1～0.9.
9. such as the preparation method of each described dispersed dye of claim 2-4 with the hyper-branched polymer dispersion agent, it is characterized in that: described precipitation agent is water, methyl alcohol, ethanol, acetone, ether and composition thereof.
10. such as the preparation method of each described dispersed dye of claim 2-4 with the hyper-branched polymer dispersion agent, it is characterized in that: the mass ratio of described precipitation agent and solvent is 1 ︰, 2～5 ︰ 1, and the mixing solutions quality of precipitation agent and solvent is 5～30 times of crude product quality.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103554462A (en) * | 2013-11-06 | 2014-02-05 | 桂林理工大学 | Preparation method of dispersing agent containing hyperbranched polyester |
| CN107216536A (en) * | 2017-08-03 | 2017-09-29 | 慈溪市赛斯特金属制品有限公司 | A kind of no-load body colour grains of sand and preparation method thereof |
| CN107245193A (en) * | 2017-08-03 | 2017-10-13 | 慈溪市赛斯特金属制品有限公司 | A kind of PP composite material and the method that faldstool is prepared using the material |
| CN110511592A (en) * | 2019-07-19 | 2019-11-29 | 杭州红妍颜料化工有限公司 | A kind of preparation method of pigment yellow 83 |
| CN113666362A (en) * | 2021-08-06 | 2021-11-19 | 苏州汉纳材料科技有限公司 | Dispersing auxiliary agent, carbon nanotube dispersion liquid and conductive paste |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5749926A (en) * | 1996-09-12 | 1998-05-12 | Westvaco Corporation | Method of preparing high activity sulfonated lignin dye dispersants |
| CN1405205A (en) * | 2002-11-07 | 2003-03-26 | 上海交通大学 | Terminal group-adjustable superbranched polyamide and its preparation method |
| CN1405200A (en) * | 2002-11-07 | 2003-03-26 | 上海交通大学 | Terminal hydroxy superbranched polyester |
| DE10314203A1 (en) * | 2003-03-28 | 2004-10-21 | Stockhausen Gmbh & Co. Kg | Process for the separation / processing of (meth) acrylic acid-containing mixtures by using ionic liquids and hyperbranched polymers |
| CN101117450A (en) * | 2007-07-23 | 2008-02-06 | 江南大学 | Preparation method of non-ionic hyperbranched macromolecular dispersant for organic pigment |
| US20090270537A1 (en) * | 2006-10-11 | 2009-10-29 | Agfa Graphics Nv | Non-aqueous pigmented inkjet inks |
-
2012
- 2012-09-24 CN CN2012103583741A patent/CN102863822A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5749926A (en) * | 1996-09-12 | 1998-05-12 | Westvaco Corporation | Method of preparing high activity sulfonated lignin dye dispersants |
| CN1405205A (en) * | 2002-11-07 | 2003-03-26 | 上海交通大学 | Terminal group-adjustable superbranched polyamide and its preparation method |
| CN1405200A (en) * | 2002-11-07 | 2003-03-26 | 上海交通大学 | Terminal hydroxy superbranched polyester |
| DE10314203A1 (en) * | 2003-03-28 | 2004-10-21 | Stockhausen Gmbh & Co. Kg | Process for the separation / processing of (meth) acrylic acid-containing mixtures by using ionic liquids and hyperbranched polymers |
| US20090270537A1 (en) * | 2006-10-11 | 2009-10-29 | Agfa Graphics Nv | Non-aqueous pigmented inkjet inks |
| CN101117450A (en) * | 2007-07-23 | 2008-02-06 | 江南大学 | Preparation method of non-ionic hyperbranched macromolecular dispersant for organic pigment |
Non-Patent Citations (2)
| Title |
|---|
| BURKINSHAW S M等: "The effect of hyperbranched polymers on the dyeing of polypropylene fibres", 《DYES AND PIGMENTS》, vol. 53, no. 3, 30 June 2002 (2002-06-30) * |
| 王学川等: "端羟基超支化聚合物及其应用", 《皮革科学与工程》, vol. 17, no. 5, 28 October 2007 (2007-10-28) * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103554462A (en) * | 2013-11-06 | 2014-02-05 | 桂林理工大学 | Preparation method of dispersing agent containing hyperbranched polyester |
| CN103554462B (en) * | 2013-11-06 | 2016-02-24 | 桂林理工大学 | A kind of preparation method containing hyper-branched polyester dispersion agent |
| CN107216536A (en) * | 2017-08-03 | 2017-09-29 | 慈溪市赛斯特金属制品有限公司 | A kind of no-load body colour grains of sand and preparation method thereof |
| CN107245193A (en) * | 2017-08-03 | 2017-10-13 | 慈溪市赛斯特金属制品有限公司 | A kind of PP composite material and the method that faldstool is prepared using the material |
| CN107245193B (en) * | 2017-08-03 | 2019-12-10 | 慈溪市赛斯特金属制品有限公司 | polypropylene composite material and method for preparing folding stool by using same |
| CN110511592A (en) * | 2019-07-19 | 2019-11-29 | 杭州红妍颜料化工有限公司 | A kind of preparation method of pigment yellow 83 |
| CN113666362A (en) * | 2021-08-06 | 2021-11-19 | 苏州汉纳材料科技有限公司 | Dispersing auxiliary agent, carbon nanotube dispersion liquid and conductive paste |
| CN113666362B (en) * | 2021-08-06 | 2023-03-17 | 苏州汉纳材料科技有限公司 | Dispersing auxiliary agent, carbon nanotube dispersion liquid and conductive paste |
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Application publication date: 20130109 |