CN113214442B - An anionic-nonionic dispersant and preparation method thereof - Google Patents

An anionic-nonionic dispersant and preparation method thereof Download PDF

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CN113214442B
CN113214442B CN202110541687.XA CN202110541687A CN113214442B CN 113214442 B CN113214442 B CN 113214442B CN 202110541687 A CN202110541687 A CN 202110541687A CN 113214442 B CN113214442 B CN 113214442B
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姜晔
周慧
惠紫嫣
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Guangzhou Bichi New Material Co ltd
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    • C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
    • C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
    • C08F299/026—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from the reaction products of polyepoxides and unsaturated monocarboxylic acids, their anhydrides, halogenides or esters with low molecular weight
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Abstract

The scheme relates to an anionic-nonionic dispersant and a preparation method thereof, which synthesizes amino-terminated polyethylene glycol NH with high selectivity by modifying hydroxyl groups at two ends of polyethylene glycol2And reacting the-PEG-OH with benzaldehyde-4-sodium sulfonate to smoothly introduce a sulfonic acid group and an imine group, performing esterification reaction on hydroxyl at the other end and carboxyl of acrylic acid to introduce a terminal double bond to obtain a reactive anionic-nonionic monomer, and synthesizing under an ATRP four-head initiator to obtain the macromolecular anionic-nonionic dispersing agent. The dispersant prepared by the invention has the anion-nonionic characteristic, is suitable for different solution systems, can be used for dispersing inorganic pigments or organic pigments, and has the advantages of good stability, low surface tension and critical micelle concentration and high dispersibility.

Description

Anionic-nonionic dispersant and preparation method thereof
Technical Field
The invention relates to the field of preparation of surfactants, in particular to an anionic-nonionic dispersant and a preparation method thereof.
Background
Surfactants can be classified into various additives such as emulsifiers, dispersants, thickeners and the like according to their functions, and almost cover all fine chemical industries, such as cosmetics industry, medicine industry, building material industry and the like. The traditional dispersing agent has small molecular weight, single and few anchoring groups combined with pigment particles, can not form firm adsorption, is easy to be influenced by factors such as temperature, impurity ions and the like, and has poor effect in practical use. The polymer dispersant has a longer molecular chain and a larger number of anchoring groups, so that the polymer dispersant can generate stronger adsorption and steric hindrance effects, and the performance of the polymer dispersant is far better than that of the traditional dispersant.
However, the dispersant with high molecular weight also has some defects, and chain entanglement can occur when the molecular chain is too long, so that the dispersing effect is influenced; the number of anchoring groups can be reduced while the molecular weight is reduced, firm adsorption can not be formed, and the influence of the environment is large.
Disclosure of Invention
Aiming at the defects in the prior art, the invention aims to provide a high-molecular-weight multi-arm anionic-nonionic polymer dispersant, which improves the steric hindrance effect by increasing polymer chains, avoids the dispersion effect influenced by the entanglement among the molecular chains, and provides more anchoring groups with higher molecular weight.
In order to achieve the purpose, the invention provides the following technical scheme:
an anionic-nonionic dispersant is a macromolecular anionic-nonionic dispersant shown in formula 2) which is obtained by modifying hydroxyl groups at two ends of polyethylene glycol to obtain a reactive anionic-nonionic monomer shown in formula 1) and then synthesizing under an ATRP four-head initiator;
Figure BDA0003071838370000021
wherein n is an integer of 5 to 20,
Figure BDA0003071838370000022
represents a polymer chain of the formula 1).
The present invention further provides a method for preparing the anionic-nonionic dispersant as described above, which comprises the steps of:
s1: adding polyethylene glycol and dichloromethane into a reaction bottle, stirring to uniformly mix, adding a catalytic amount of silver oxide/potassium iodide catalyst, adding paratoluensulfonyl chloride with the same molar amount as the polyethylene glycol, stirring to react for 2-3 h at room temperature, and filtering and washing to obtain TsO-PEG-OH;
s2: dissolving TsO-PEG-OH in 25% ammonia water, adding equimolar ammonium chloride, stirring at 30 deg.C for 3 days, extracting with dichloromethane, and purifying the collected organic layer by column chromatography to obtain NH2-PEG-OH；
S3: the obtained NH2-PEG-OH was dissolved in deionized water and addedAdjusting the pH value of equimolar benzaldehyde-4-sodium sulfonate to 6.5 to obtain a mixed solution, dropwise adding sodium amino borohydride into the mixed solution, stirring and reacting at room temperature for 12 hours, and dialyzing, freezing and drying the reaction solution to obtain a solid; dissolving the solid in toluene, adding a polymerization inhibitor hydroquinone, a catalyst p-toluenesulfonic acid and monomer acrylic acid, heating to 110-120 ℃, stirring and refluxing for 4 hours, washing with a saturated sodium carbonate solution, separating liquid, performing rotary evaporation on an organic layer to remove the solvent, and recrystallizing to obtain the reactive anionic-nonionic monomer shown in the formula 1);
s4: adding pentaerythritol, triethylamine and anhydrous dioxane into a reaction bottle, introducing nitrogen to replace air in the reaction bottle, placing the reaction bottle in an environment at-18 ℃, dropwise adding a tetrahydrofuran solution of 2-bromoisobutyryl bromide in a nitrogen atmosphere, and after dropwise adding, moving the reaction bottle to room temperature to react for 12 hours under stirring; extracting with dichloromethane, collecting an organic layer, washing, drying, rotary steaming and recrystallizing to obtain an ATRP four-head initiator;
s5: sequentially adding a catalyst, a coordination agent, the ATRP four-head initiator and a reactive anionic-nonionic monomer into a schlenk bottle, adding tetrahydrofuran, stirring to dissolve and mix the tetrahydrofuran uniformly, filling nitrogen into the schlenk bottle through three cycles of freezing, air extraction, thawing and inflation, and reacting for 2-5 hours at 60 ℃; after the reaction is finished, adding tetrahydrofuran for dissolving and diluting, and then precipitating and separating out a polymer in a large amount of n-hexane after passing through neutral alumina, thus obtaining the anionic-nonionic dispersing agent.
Further, the catalyst is cupric bromide, cuprous bromide or a mixture of the cupric bromide and the cuprous bromide; the complexing agent is bipyridine or N, N, N' -pentamethyldiethylenetriamine.
Furthermore, the feeding molar ratio of the catalyst, the complexing agent, the ATRP four-head initiator and the reactive anionic-nonionic monomer is 1:2:1: 50-100.
The invention has the beneficial effects that: the dispersant prepared by the invention has the characteristics of negative and non-ionic property, is suitable for different solution systems, can be used for dispersing inorganic pigments or organic pigments, and has the advantages of good stability, low surface tension and critical micelle concentration and high dispersibility.
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to the following embodiments, and it should be understood that the described embodiments are some, but not all, embodiments of the present invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
In addition, the technical features involved in the different embodiments of the present invention described below may be combined with each other as long as they do not conflict with each other.
The invention provides a preparation method of an anionic-nonionic dispersant, which comprises the following steps:
s1: adding polyethylene glycol (PEG) and dichloromethane into a reaction bottle, stirring to uniformly mix, adding a catalytic amount of silver oxide/potassium iodide catalyst, adding paratoluensulfonyl chloride with the same molar amount as the polyethylene glycol, stirring to react for 2-3 h at room temperature, and filtering and washing to obtain TsO-PEG-OH;
s2: dissolving TsO-PEG-OH in 25% ammonia water, adding equimolar ammonium chloride, stirring at 30 deg.C for 3 days, extracting with dichloromethane, and purifying the collected organic layer by column chromatography to obtain NH2-PEG-OH；
S3: the obtained NH2Dissolving PEG-OH in deionized water, adding equimolar amount of benzaldehyde-4-sodium sulfonate, adjusting pH to 6.5 to obtain a mixed solution, dropwise adding sodium aminoborohydride into the mixed solution, stirring and reacting at room temperature for 12 hours, and dialyzing, freezing and drying the reaction solution to obtain a solid; dissolving the solid in toluene, adding a polymerization inhibitor hydroquinone, a catalyst p-toluenesulfonic acid and monomer acrylic acid, heating to 110-120 ℃, stirring and refluxing for 4 hours, washing with a saturated sodium carbonate solution, separating liquid, performing rotary evaporation on an organic layer to remove the solvent, and recrystallizing to obtain the reactive anionic-nonionic monomer shown in the formula 1);
s4: adding pentaerythritol, triethylamine and anhydrous dioxane into a reaction bottle, introducing nitrogen to replace air in the reaction bottle, placing the reaction bottle in an environment at-18 ℃, dropwise adding a tetrahydrofuran solution of 2-bromoisobutyryl bromide in a nitrogen atmosphere, and after dropwise adding, moving the reaction bottle to room temperature to react for 12 hours under stirring; extracting with dichloromethane, collecting an organic layer, washing, drying, rotary steaming and recrystallizing to obtain an ATRP four-head initiator;
s5: sequentially adding a catalyst (a mixture of copper bromide and cuprous bromide), a coordination agent (bipyridyl bby), the ATRP four-head initiator and a reactive anion-nonionic monomer into a schlenk bottle, adding tetrahydrofuran, stirring to dissolve and mix the ATRP four-head initiator and the reactive anion-nonionic monomer uniformly, filling nitrogen into the schlenk bottle through three cycles of freezing, air extraction, thawing and air inflation, and reacting for 2-5 hours at 60 ℃; after the reaction is finished, adding tetrahydrofuran for dissolving and diluting, and then precipitating and separating out a polymer in a large amount of n-hexane after passing through neutral alumina, thus obtaining the anionic-nonionic dispersing agent.
The above preparation process can be expressed by the following equation, wherein n is the functionality of polyethylene glycol, preferably 5-15, i.e. the molecular weight of PEG is preferably between 200 and 800g/mol,
Figure BDA0003071838370000041
represents a polymer chain composed of reactive anionic-nonionic monomers. In the scheme, hydroxyl groups at two ends of polyethylene glycol are modified respectively, and the modification is carried out according to the following formula: 549-551 can synthesize high-selectivity amino-terminated polyethylene glycol NH2PEG-OH reacts with benzaldehyde-4-sodium sulfonate to smoothly introduce sulfonic acid groups and imine groups, so that the anchoring effect is increased, and the compound has the anion-nonionic characteristic; at this time, the hydroxyl group at the other end is used to perform an esterification reaction with the carboxyl group of acrylic acid, and a terminal double bond is introduced to enable radical polymerization.
Pentaerythritol is used as a raw material to prepare a four-head ATRP initiator, the initiator is polymerized with the reactive anionic-nonionic monomer to obtain a multi-arm polymer, the steric hindrance between a molecular chain and the molecular chain is large, and the molecular weight of the polymer chain is not too large by regulating and controlling the polymerization degree, so that the possibility of molecular chain entanglement can be reduced, and the stability of the dispersing agent is improved; meanwhile, as the polymer has a plurality of molecular chains, the polymer can be ensured to have higher overall molecular weight and rich anchoring groups, thereby effectively improving the adsorption firmness and the dispersion performance. Meanwhile, the dispersing agent has nonionic characteristics of ether and anionic characteristics of sulfonate, and the application range of the dispersing medium is wide.
Figure BDA0003071838370000051
Example 1: PEG-200 is selected, and the feeding molar ratio of the catalyst, the coordination agent, the ATRP four-head initiator and the reactive anionic-nonionic monomer is 1:2:1: 100.
Example 2: PEG-400 is selected, and the feeding molar ratio of the catalyst, the coordination agent, the ATRP four-head initiator and the reactive anionic-nonionic monomer is 1:2:1: 80.
Example 3: PEG-800 is selected, and the feeding molar ratio of the catalyst, the coordination agent, the ATRP four-head initiator and the reactive anion-nonionic monomer is 1:2:1: 50.
Comparative example: the ATRP four-head initiator of example 1 was replaced directly with 2-bromoisobutyryl bromide as initiator, and the rest of the conditions were unchanged.
Measuring the critical micelle concentration CMC by using a surface tension meter; interfacial tensiometers measure surface tension. The test results are reported in table 1, with examples 1-3 having lower surface tensions and lower critical micelle concentrations.
TABLE 1
CMC(mol/L) Surface tension (mN/m)
Example 1 1.1×10-3 27.5
Example 2 1.2×10-3 29.1
Example 3 1.1×10-3 28.3
Comparative example 3.2×10-3 36.8
Respectively taking inorganic matters and organic matters as dispersed particles, and preparing a dispersion liquid by using the prepared dispersing agent, wherein the dispersion liquid specifically comprises the following components:
application example 1: 0.2g of titanium dioxide is taken, 0.2g of the dispersing agent of the examples 1 to 3 and the comparative example of 10g of deionized water are respectively taken, mixed and stirred uniformly, and then ball-milled and dispersed for 40min to obtain titanium dioxide dispersion liquid which is respectively marked as products 1 to 4. After 30 days of standing, products 1-3 were observed to be homogeneous, with product 4 slightly agglomerated.
Application example 2: 1g of polyurethane emulsion is taken, 0.1g of the dispersant of the examples 1 to 3 and 10g of the deionized water of the comparative example are respectively taken to be mixed and stirred evenly by a machine, and the water-based polyurethane emulsion dispersion liquid is obtained and respectively marked as products 5 to 8. Products 5-8 are observed to be homogeneous after standing for 30 days, which shows that the dispersant has better dispersion stability for organic matters and inorganic fillers.
Application example 3: 1g of polyurethane emulsion is taken, 0.1g of the dispersant of the embodiment 1 and 10g of organic solvent (DMF or ethanol or ethyl acetate or diethanol amine) are mixed and stirred evenly by a machine, and aqueous polyurethane emulsion dispersion liquid is obtained and is respectively marked as products 9 to 12. After standing for 30 days, products 9-12 are observed to be homogeneous, namely the dispersant has a wide range of applicable solvent systems.
While embodiments of the invention have been disclosed above, it is not limited to the applications listed in the description and the embodiments, which are fully applicable in all kinds of fields of application of the invention, and further modifications may readily be effected by those skilled in the art, so that the invention is not limited to the specific details without departing from the general concept defined by the claims and the scope of equivalents.

Claims (4)

1.一种阴-非离子型分散剂，其特征在于，是通过对聚乙二醇两端羟基进行改性得到如式1)所示的反应型阴-非离子单体，随后在ATRP四头引发剂下合成得到如式2)所示的大分子阴-非离子型分散剂；1. an anion-nonionic dispersant, it is characterized in that, obtain the reactive anion-nonionic monomer shown in formula 1) by modifying the hydroxyl groups at both ends of polyethylene glycol, and then in ATRP four. Synthesize under the head initiator to obtain the macromolecular anion-nonionic dispersant shown in formula 2);
Figure FDA0003071838360000011
Figure FDA0003071838360000011
 其中，n是5～20的整数，
Figure FDA0003071838360000012
表示式1)构成的聚合物链。where n is an integer from 5 to 20,
Figure FDA0003071838360000012
The polymer chain constituted by the formula 1) is represented. 2.一种如权利要求1所述的阴-非离子型分散剂的制备方法，其特征在于，包括以下步骤：2. a preparation method of anionic-nonionic dispersant as claimed in claim 1, is characterized in that, comprises the following steps: S1：在反应瓶中加入聚乙二醇和二氯甲烷搅拌使其混合均匀，加入催化量的氧化银/碘化钾催化剂，再加入与聚乙二醇等摩尔量的对甲苯磺酰氯，室温下搅拌反应2～3h，随后过滤洗涤得到TsO-PEG-OH；S1: Add polyethylene glycol and dichloromethane to the reaction flask and stir to mix evenly, add a catalytic amount of silver oxide/potassium iodide catalyst, and then add p-toluenesulfonyl chloride in an equimolar amount with polyethylene glycol, and stir the reaction at room temperature 2～3h, then filter and wash to obtain TsO-PEG-OH; S2：将TsO-PEG-OH溶于25％的氨水中，并加入等摩尔量的氯化铵，30℃下搅拌反应3天，用二氯甲烷萃取，收集到的有机层通过柱层析分离提纯得到NH2-PEG-OH；S2: Dissolve TsO-PEG-OH in 25% ammonia water, add equimolar amount of ammonium chloride, stir and react at 30°C for 3 days, extract with dichloromethane, and separate the collected organic layer by column chromatography Purified to obtain NH 2 -PEG-OH; S3：将得到的NH2-PEG-OH溶于去离子水中，加入等摩尔量的苯甲醛-4-磺酸钠，调节pH至6.5得混合溶液，取氨基硼氢化钠逐滴滴加入混合溶液中，室温下搅拌反应12h，随后将反应液透析冷冻干燥得到固体；将固体溶解于甲苯中加入阻聚剂对苯二酚、催化剂对甲苯磺酸和单体丙烯酸，升温至110～120℃，搅拌回流4h，用饱和碳酸钠溶液水洗后分液，将有机层旋蒸除去溶剂，重结晶得到式1)所示反应型阴-非离子单体；S3: Dissolve the obtained NH 2 -PEG-OH in deionized water, add an equimolar amount of sodium benzaldehyde-4-sulfonate, adjust the pH to 6.5 to obtain a mixed solution, and add sodium aminoborohydride to the mixed solution dropwise , the reaction was stirred at room temperature for 12 h, and then the reaction solution was dialyzed and freeze-dried to obtain a solid; the solid was dissolved in toluene, the polymerization inhibitor hydroquinone, catalyst p-toluenesulfonic acid and monomer acrylic acid were added, and the temperature was raised to 110-120 °C, Stir and reflux for 4h, wash with saturated sodium carbonate solution and separate liquids, spin the organic layer to remove the solvent, and recrystallize to obtain the reaction-type anion-nonionic monomer shown in formula 1); S4：在反应瓶中加入季戊四醇、三乙胺和无水二氧六环，通入氮气置换反应瓶中的空气，将反应瓶置于-18℃环境下，并在氮气氛围中逐滴滴加2-溴异丁酰溴的四氢呋喃溶液，滴加完毕后将反应瓶移至室温下搅拌反应12h；用二氯甲烷萃取，收集有机层经洗涤、干燥、旋蒸和重结晶得到ATRP四头引发剂；S4: Add pentaerythritol, triethylamine and anhydrous dioxane to the reaction flask, replace the air in the reaction flask with nitrogen, place the reaction flask at -18°C, and add dropwise in a nitrogen atmosphere The tetrahydrofuran solution of 2-bromoisobutyryl bromide was added dropwise, and then the reaction flask was moved to room temperature and stirred for 12 hours; extracted with dichloromethane, the organic layer was collected, washed, dried, rotary evaporated and recrystallized to obtain ATRP four-head initiator agent; S5：在舒伦克瓶中依次加入催化剂、配位剂、所述ATRP四头引发剂和反应型阴-非离子单体，加入四氢呋喃搅拌使其溶解混合均匀，舒伦克瓶经冷冻-抽气-解冻充气三次循环使瓶中充满氮气，在60℃下反应2-5h；反应完成后加四氢呋喃溶解稀释，随后经过中性氧化铝后在大量正己烷中沉淀析出聚合物，即得阴-非离子型分散剂。S5: Add the catalyst, the complexing agent, the ATRP four-head initiator and the reactive anion-nonionic monomer in sequence to the Schlenk bottle, add tetrahydrofuran and stir to dissolve and mix evenly, and the Schlenk bottle is frozen-pumped Gas-thaw and inflate three cycles to fill the bottle with nitrogen, and react at 60 °C for 2-5 hours; after the reaction is completed, add tetrahydrofuran to dissolve and dilute, and then pass through neutral alumina and then precipitate a polymer in a large amount of n-hexane, that is, an anion- Nonionic dispersant. 3.如权利要求2所述的阴-非离子型分散剂的制备方法，其特征在于，所述催化剂为溴化铜、溴化亚铜或二者的混合物；所述配位剂为联吡啶或N,N,N’,N”-五甲基二亚乙基三胺。3. the preparation method of anionic-nonionic dispersant as claimed in claim 2, is characterized in that, described catalyzer is cupric bromide, cuprous bromide or the mixture of the two; Described complexing agent is bipyridine Or N,N,N',N"-pentamethyldiethylenetriamine. 4.如权利要求2所述的阴-非离子型分散剂的制备方法，其特征在于，所述催化剂、配位剂、所述ATRP四头引发剂和反应型阴-非离子单体的投料摩尔比为1:2:1:50～100。4. the preparation method of anion-nonionic dispersant as claimed in claim 2, is characterized in that, the feed intake of described catalyzer, complexing agent, described ATRP four-head initiator and reactive anion-nonionic monomer The molar ratio is 1:2:1:50～100.
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