CN112592437A - Modified polyglycol ether water-soluble wetting dispersant and preparation method thereof - Google Patents
Modified polyglycol ether water-soluble wetting dispersant and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a modified polyethylene glycol monomethyl ether wetting dispersant, a preparation method and application thereof, wherein the method comprises the step of carrying out esterification reaction on a monomer of methacrylic acid or acrylic acid or maleic anhydride and a polyoxyethylene ether and polyoxypropylene ether block copolymer with the number average molecular weight of 600-2000 in the presence of a catalyst to obtain polyoxyethylene ether and polyoxypropylene ether block copolymer unsaturated ester. Then carrying out polymerization reaction with monomer sodium methyl propylene sulfonate or styrene or methyl methacrylate in a reaction solvent in the presence of an initiator under a certain temperature condition to obtain the high molecular polymer arranged in a comb-shaped structure. The modified polyethylene glycol monomethyl ether wetting dispersant is a water-soluble high polymer with a comb-shaped structure arrangement, and a propylene oxide monomer is creatively introduced, so that the HLB value of the original polyether is changed, the transparent temperature range value of the polyethylene glycol monomethyl ether is widened, the application range can be widened from the water reducing agent industry to the agrochemical industry, and the stability of the preparation is improved.
Description
Technical Field
The invention relates to the technical field of polymer additives, in particular to a modified polyethylene glycol monomethyl ether wetting dispersant, a preparation method and application thereof.
Background
Due to the unique performance of the ethylene oxide synthesized polyethylene glycol monomethyl ether, the ethylene oxide synthesized polyethylene glycol monomethyl ether is soluble in water, ethanol and most of high-polarity organic solvents, is difficult to volatilize, stable in chemical property, strong in hydrophilicity, difficult to hydrolyze and damage, low in steam pressure and good in thermal stability, and has wide application in the fields of building, coating, textile, electronics, rubber, medicine, packaging, food processing and the like. The MPEG acrylate is prepared by the synthetic reaction of polyethylene glycol monomethyl ether and acrylic acid, and the prepared polycarboxylate high-efficiency wetting dispersant can solve a plurality of industrial problems. For example, in 2017, the Weekun (acetaldehyde acetic acid chemical industry, 2017,11, 20-23) reports "modification application of methoxypolyethylene glycols in the aspect of water reducing agents", and in this document, modification research and application of methoxypolyethylene glycols in concrete water reducing agents are mainly introduced. However, the polycarboxylate high-efficiency wetting dispersant is directly used in the formulation of some pesticide water suspending agents, and a plurality of problems can not be effectively solved, such as the problems of creaming, water precipitation, particle size increase, poor fluidity and the like after hot storage after the wetting dispersant is used in the formulation of high-water-solubility raw pymetrozine. The main reasons for the existence are that the polyethylene glycol monomethyl ether has higher HLB value, good water solubility and smaller transparent temperature range value, can not bind the high water solubility of the raw pesticide particles when being directly used in the pesticide water suspending agent formula, and has great limited prospect when being used in the high water solubility of the raw pesticide, such as pymetrozine formula.
Disclosure of Invention
The invention aims to provide a modified polyethylene glycol monomethyl ether wetting dispersant and a preparation method thereof, which creatively introduces a propylene oxide monomer, reduces the HLB value of an auxiliary agent, makes the HLB value more suitable for pesticide raw materials, and widens the application range of the polyethylene glycol monomethyl ether efficient wetting dispersant.
The invention also aims to provide application of the modified polyethylene glycol monomethyl ether wetting dispersant, which has a proper HLB value, so that the application range of the modified polyethylene glycol monomethyl ether wetting dispersant can be widened to the agricultural chemical industry, and the stability of a preparation is improved.
The invention is realized by the following technical scheme:
the average relative molecular weight of the modified polyethylene glycol monomethyl ether wetting dispersant is 2000-10000, and the molecular weight distribution index PDI is less than 1.5; the modified polyethylene glycol monomethyl ether wetting dispersant is prepared by carrying out esterification reaction on 10-30 wt% of monomer methacrylic acid or acrylic acid or maleic anhydride and 40-80 wt% of polyoxyethylene ether and polyoxypropylene ether block copolymer with the number average molecular weight of 600-2000 in the presence of a catalyst to obtain polyoxyethylene ether and polyoxypropylene ether block copolymer unsaturated ester. And then carrying out polymerization reaction with 10-30% of monomer sodium methyl propylene sulfonate or styrene or methyl methacrylate in a reaction solvent in the presence of an initiator at a certain temperature to obtain a high molecular polymer arranged in a comb-shaped structure, wherein the average relative molecular weight of the polymer is 2000-10000, and the molecular weight distribution index PDI is less than 1.5.
The preparation method of the modified polyethylene glycol monomethyl ether wetting dispersant comprises the following steps: step 1, adding methanol as an initiator according to a ratio, adding a catalyst, spraying ethylene oxide and propylene oxide at a mass ratio of 1:0.3-0.5, and controlling reaction conditions to obtain a polyoxyethylene ether-polyoxypropylene ether block copolymer A with a number average molecular weight of 600-2000;
step 2, taking the block copolymer A as a raw material, adding a catalyst and a polymerization inhibitor, preparing a polyoxyethylene ether and polyoxypropylene ether block copolymer unsaturated ester macromonomer B by an esterification reaction with methacrylic acid or an acrylic acid monomer or maleic anhydride under the condition of introducing nitrogen to drive water, and taking a product as an intermediate for synthesizing the modified polyethylene glycol monomethyl ether wetting dispersant;
step 3, taking the macromonomer B and sodium methyl propylene sulfonate or styrene or methyl methacrylate as raw materials, and in the presence of an initiator, using an alcohol solvent to synthesize the modified polyethylene glycol monomethyl ether wetting dispersant with the average relative molecular weight of 2000-10000 and the molecular weight distribution index PDI of less than 1.5 by free radical polymerization.
In the preparation method of the modified polyethylene glycol monomethyl ether wetting dispersant, the catalyst in the step 1 is selected from sodium methoxide or potassium hydroxide; the catalyst in the step 2 is selected from p-toluenesulfonic acid or sulfuric acid; the polymerization inhibitor is selected from at least one of 4-methoxyphenol, hydroquinone or phenothiazine; the peroxy oxidizing agent in the step 3 is selected from ammonium persulfate, potassium persulfate or sodium persulfate.
The modified polyethylene glycol monomethyl ether wetting dispersant is applied to preparation of 25% pymetrozine SC. The 25% pymetrozine SC comprises the following components in percentage by weight:
25% of pymetrozine (95%) (book Bai);
6 percent of the modified polyethylene glycol monomethyl ether wetting dispersant;
1% of wetting agent (Morwet EFW);
propylene glycol: 4 percent;
magnesium aluminum silicate: 1 percent;
xanthan gum: 7 percent;
defoaming agent: 0.2 percent of
Citric acid: 1 percent of
Water: make up to 100%;
the product is ground to a particle size D90 ≦ 5um by sand grinding, and the product is examined after being stored at 54 ℃ for 14 days.
Compared with the prior art, the technical scheme of the invention has the following beneficial effects
The pymetrozine is a high-water-solubility compound, the stability of the preparation cannot be ensured for a long time by singly using the polyethylene glycol monomethyl ether wetting dispersant, and the preparation still keeps stable and has good fluidity after a sample is stored for 2 years by hot storage, cold storage and normal temperature storage by using the modified polyethylene glycol monomethyl ether wetting dispersant.
The propylene oxide monomer is creatively introduced, has a proper HLB value, widens the range value of the transparent temperature range of the polyethylene glycol monomethyl ether, widens the application range to the agricultural chemical industry, and improves the stability of the preparation. The epoxypropyl group changes the distribution of the binding points of the dispersing agent and the agricultural chemical particles, prevents the particles from being adsorbed together through thermal motion, and improves the dispersing performance of the dispersing agent on the agricultural chemicals. The raw material of the polyethylene glycol monomethyl ether is easy to obtain, and the modification of the propylene oxide monomer on the polyethylene glycol monomethyl ether is not reported.
Drawings
FIG. 1 is a diagram showing a synthesis equation of modified polyethylene glycol monomethyl ether;
FIG. 2 is a diagram showing a synthesis equation of an unsaturated ester of a block copolymer of polyoxyethylene ether and polyoxypropylene ether;
FIG. 3 is a diagram showing the synthesis equation of a block copolymer of polyoxyethylene ether and polyoxypropylene ether;
FIG. 4 is a structural schematic of comparative example 2;
FIG. 5 is a schematic configuration of example 2.
Detailed Description
The following examples are provided to further illustrate the technical solutions of the present invention, but the present invention is not limited by the following examples.
The raw materials used in the invention are as follows:
| numbering | Name of raw material | Suppliers of goods |
| 1 | Methacrylic acid | Shanghai and Hai industries Ltd |
| 2 | Acrylic acid | Shanghai and Hai industries Ltd |
| 3 | Maleic anhydride | Leping Xin shui vast chemical Co., Ltd |
| 4 | Sodium methallyl sulfonate | Shandong Songchuan New Material Co Ltd |
| 5 | Methacrylic acid methyl ester | Shanghai and Hai industries Ltd |
| 6 | Styrene (meth) acrylic acid ester | Shanghai Zhongwei Chemical Co., Ltd. |
| 7 | Ethylene oxide | ZHEJIANG HUANGMA TECHNOLOGY Co.,Ltd. |
| 8 | Propylene oxide | ZHEJIANG HUANGMA TECHNOLOGY Co.,Ltd. |
| 9 | Sodium methoxide | Yingde city Yiliang chemical Co Ltd |
| 10 | Potassium hydroxide | Yingde city Yiliang chemical Co Ltd |
| 11 | P-toluenesulfonic acid | Yingde city Yiliang chemical Co Ltd |
| 12 | Sulfuric acid | Yingde city Yiliang chemical Co Ltd |
| 13 | 4-methoxyphenol | Tianjin Xien Opp-Dr technology Ltd |
| 14 | Hydroquinone | Tianjin Xien Opp-Dr technology Ltd |
| 15 | Thiophenazine | Tianjin Xien Opp-Dr technology Ltd |
| 16 | Ammonium persulfate | GUANGDONG WENGJIANG CHEMICAL REAGENT Co.,Ltd. |
| 17 | Potassium persulfate | GUANGDONG WENGJIANG CHEMICAL REAGENT Co.,Ltd. |
| 18 | Sodium persulfate | GUANGDONG WENGJIANG CHEMICAL REAGENT Co.,Ltd. |
| 19 | Methanol | GUANGDONG WENGJIANG CHEMICAL REAGENT Co.,Ltd. |
According to the proportion, selecting methanol as a kettle washing liquid to ensure that the residual water in the reaction kettle is less than 0.05 percent, adding methanol as an initiator, adding a catalyst, spraying and introducing ethylene oxide and propylene oxide with a certain mass ratio, controlling the reaction conditions, wherein the reaction temperature is 120 ℃, and the pressure is 0.2-0.4 MPa, thus obtaining the polyoxyethylene ether-polyoxypropylene ether block copolymer A with the number average molecular weight of 600-2000. Taking the block copolymer A as a raw material, adding a catalyst and a polymerization inhibitor, preparing polyoxyethylene ether and polyoxypropylene ether block copolymer unsaturated ester by esterification reaction of methacrylic acid or acrylic acid or maleic anhydride at 100-120 ℃ under the condition of introducing nitrogen to drive water, and taking the product as an intermediate B for synthesizing the modified polyethylene glycol monomethyl ether wetting dispersant. The macromonomer B, sodium methyl acrylate or styrene or methyl methacrylate, an initiator and an alcohol solvent are subjected to free radical polymerization at 60-80 ℃ to synthesize the modified polyethylene glycol monomethyl ether wetting dispersant with the average relative molecular weight of 2000-10000 and the molecular weight distribution index PDI of less than 1.5.
For example, in comparative example 2 and example 2, the main difference between the reactant monomers used is that in the first step of the reaction, only epoxy vinyl ether is used for copolymer A, and in the first step of the reaction, block copolymer A is formed by using epoxy vinyl ether and propylene oxide for copolymer A in example 2. Comparative example 2 and example 2 were synthesized by polymerizing methacrylic acid, the monomer predominantly used in the synthesis of intermediate B, with styrene monomer, and having the following structural formula:
comparative example 2:
1H NMR (600 MHz, Chloroform-d) δ 7.54 – 7.00 (m, 15H), 4.15 (t, J = 7.1 Hz, 2H), 4.11 – 4.00 (m, 2H), 3.61 (s, 56H), 3.49 (t, J = 7.1 Hz, 12H), 3.41 (t, J = 7.1 Hz, 4H), 2.78 (q, J = 6.9 Hz, 1H), 2.58 (p, J = 7.0 Hz, 2H), 2.40 – 2.30 (m, 2H), 2.19 – 2.00 (m, 2H), 1.98 – 1.86 (m, 4H), 1.85 – 1.74 (m, 9H), 1.69 – 1.50 (m, 9H), 1.38 – 1.23 (m, 7H), 1.22 – 1.05 (m, 1H), 0.90 (t, J = 8.0 Hz, 6H).
13C NMR (151 MHz, , Chloroform-d) δ 128.59 , 128.44 , 128.26 , 127.49 , 127.23 , 127.21 , 126.35 , 126.20 , 73.00 , 70.69 , 70.58 , 70.52 , 69.77 , 68.82 , 68.30 , 61.89 , 61.36 , 47.25 , 45.95 , 45.58 , 38.70 , 36.50 , 34.44 , 34.08 , 31.13 , 30.38 , 30.29 , 29.32 , 29.26 , 28.35 , 26.80 , 24.75 , 22.80 , 20.05 , 10.70 .
example 2:
1H NMR (600 MHz, Chloroform-d) δ 7.43 – 7.09 (m, 15H), 4.20 – 3.88 (m, 4H), 3.70 – 3.58 (m, 19H), 3.57 – 3.44 (m, 35H), 3.44 – 3.26 (m, 13H), 2.11 (dt, J = 25.4, 7.0 Hz, 2H), 1.85 – 1.65 (m, 12H), 1.66 – 1.49 (m, 4H), 1.39 – 1.28 (m, 23H), 1.29 – 1.14 (m, 11H).
13C NMR (151 MHz, Chloroform-d) δ 128.59 , 128.44 , 128.26 , 127.49 , 127.23 , 127.21 , 126.35 , 126.20 , 74.91 , 73.17 , 72.12 , 71.58 , 70.86 , 70.52 , 70.07 , 69.73 , 67.97 , 67.79 , 67.75 , 67.65 , 61.82 , 61.72 , 61.36 , 47.25 , 45.95 , 45.58 , 38.70 , 36.81 , 36.50 , 34.44 , 34.08 , 30.38 , 30.29 , 29.59 , 28.35 , 26.80 , 24.75 , 20.77 , 20.05 , 16.48 .
table 1: examples modified polyethylene glycol monomethyl ether wetting dispersant the amount of each monomer charged (weight percent)
| Comparison of Example 1 | Comparison of Example 2 | Comparison of Example 3 | Comparison of Example 4 | Practice of Example 1 | Practice of Example 2 | Practice of Example 3 | Practice of Example 4 | |
| Methacrylic acid | 15% | 15% | 15% | 15% | ||||
| Acrylic acid | 15% | 15% | ||||||
| Maleic anhydride | 15% | 15% | ||||||
| Styrene (meth) acrylic acid ester | 15% | 15% | ||||||
| Methacrylic acid methyl ester | 15% | 15% | ||||||
| Sodium methyl propenyl sulfonate | 15% | 15% | 15% | 15% | ||||
| Polyethylene glycol monomethyl ether with number average molecular weight of 600-2000- | 70% | 70% | 70% | 70% | ||||
| Polyoxyethylene ether and polyoxypropylene with number average molecular weight of 600-2000- Ether block copolymer (mass ratio 1: 0.3-0.7) | 70% | 70% | 70% | 70% | ||||
| Average relative molecular weight | 4381 | 5472 | 6584 | 6753 | 7034 | 7561 | 6420 | 6891 |
The preparation process and the formula of 25% pymetrozine SC are explained in detail by taking the modified polyethylene glycol monomethyl ether wetting dispersant used for 25% pymetrozine SC in the examples and the comparative examples. The formulation of the preparation is as follows:
TABLE 225% pymetrozine SC formulation
| Composition (I) | Mass fraction | Type (B) |
| Pymetrozine (book hundred) | 25 | Raw medicine |
| Self-grinding product | 6 | Dispersing agent |
| Morwet EFW | 1 | Wetting agent |
| Propylene glycol | 4 | Antifreezing agent |
| Magnesium aluminum silicate | 1 | Stabilizer |
| Xanthan gum | 7 | Stabilizer |
| Antifoaming agent AF1501 | 0.2 | Defoaming agent |
| Water (W) | Make up to 100% | Solvent(s) |
The production and feeding process comprises the following steps: adding water, propylene glycol, AF1501, a self-grinding product and Morwet EFW into a sanding cylinder, uniformly stirring, adding magnesium aluminum silicate and a raw pesticide, shearing and uniformly stirring, sanding for about 2 hours, wherein the particle size is less than or equal to 5um when D90. Weighing and adding xanthan gum mother liquor, shearing and stirring uniformly, and after the xanthan gum mother liquor is stored for 14 days, investigating the stability and the particle size growth condition of the preparation.
Table 3 stability of the examples and comparative examples on 25% pymetrozine SC formulation the results of the various performance tests
| Comparative example 1 | Comparative example 2 | Comparative example 3 | Comparative example 4 | Example 1 | Example 2 | Example 3 | Example 4 | |
| Number average molecular weight | 4381 | 5472 | 6584 | 6753 | 7034 | 7561 | 6420 | 6891 |
| The suspension rate is measured% | Fail to be qualified | Qualified | Qualified | Good effect | Is excellent in | Is excellent in | Is excellent in | Is excellent in |
| Stability in storage at ambient temperature | Fail to be qualified | Qualified | Qualified | Good effect | Is excellent in | Is excellent in | Is excellent in | Is excellent in |
| Low temperature storage stability | Fail to be qualified | Qualified | Qualified | Good effect | Is excellent in | Is excellent in | Is excellent in | Is excellent in |
| High temperature storage stability | Fail to be qualified | Fail to be qualified | Fail to be qualified | Fail to be qualified | Is excellent in | Is excellent in | Is excellent in | Is excellent in |
| Sanding for 1h particle size, D90, micron | 8.41 | 6.01 | 9.31 | 10.38 | 4.38 | 3.41 | 4.57 | 4.43 |
| Particle size D90, micron after heat storage for 14 days | 20.45 | 14.44 | 17.34 | 19.33 | 4.49 | 3.47 | 4.49 | 4.47 |
From examples 1-4, it can be seen that in the formulation of the present invention, the modified polyethylene glycol monomethyl ether wetting dispersant is used for 25% pymetrozine SC, so that the pymetrozine SC maintains properties during grinding, does not agglomerate, has high suspension rate, is stable during normal temperature, low temperature and high temperature heat storage, has high sanding efficiency, and has stable particle size for 14 days of preparation heat storage.
It can be seen from comparative examples 1 to 4 that the formulations not according to the invention are also not very stable and have poor dispersing properties.
It should be finally noted that the above examples are only intended to illustrate the technical solutions of the present invention, and not to limit the scope of the present invention, and that other variations and modifications based on the above description and thought may be made by those skilled in the art, and that all embodiments need not be exhaustive. Any modification, equivalent replacement, and improvement made within the spirit and principle of the present invention should be included in the protection scope of the claims of the present invention.
Claims (11)
1. The modified polyethylene glycol monomethyl ether is characterized by being prepared by the following steps: polyoxyethylene ether and polyoxypropylene ether block copolymer unsaturated ester is used as a raw material, and the raw material and one of monomer sodium methyl propylene sulfonate or styrene or methyl methacrylate are subjected to polymerization reaction in the presence of an initiator to obtain a target product arranged in a comb-shaped structure.
The reaction equation of claim 1 is as follows:
r1 is methacrylic acid or acrylic acid or maleic anhydride, R2, R3 are monomer sodium methyl propylene sulfonate or styrene or methyl methacrylate.
2. The modified polyethylene glycol monomethyl ether according to claim 1, wherein the modified polyethylene glycol monomethyl ether has an average relative molecular weight of 2000 to 10000 and a molecular weight distribution index PDI of less than 1.5.
3. The modified polyethylene glycol monomethyl ether of claim 1, wherein the initiator is one of ammonium persulfate, potassium persulfate, or sodium persulfate.
4. The modified polyethylene glycol monomethyl ether according to claim 1, wherein the mass ratio of the polyoxyethylene ether and polyoxypropylene ether block copolymer unsaturated ester to the monomer of one of sodium methyl propylene sulfonate or styrene or methyl methacrylate is 70-80%: 20 to 30 percent.
5. The modified polyethylene glycol monomethyl ether of claim 1, wherein the polyoxyethylene ether-polyoxypropylene ether block copolymerThe unsaturated ester is prepared by the following process: from monomers R1One of methacrylic acid, acrylic acid or maleic anhydride and polyoxyethylene ether and polyoxypropylene ether block copolymer with the average molecular weight of 600-2000 are subjected to esterification reaction in the presence of a catalyst and a polymerization inhibitor to obtain polyoxyethylene ether and polyoxypropylene ether block copolymer unsaturated ester;
the reaction equation of claim 5 is as follows:
6. the modified polyethylene glycol monomethyl ether of claim 5, wherein the catalyst is p-toluenesulfonic acid, sulfuric acid, or tetrabutyl titanate.
7. The modified methoxypolyethylene glycol of claim 5, wherein the reaction is carried out in the presence of a polymerization inhibitor selected from the group consisting of 4-methoxyphenol, hydroquinone, and phenazine.
8. The modified polyethylene glycol monomethyl ether of claim 5, wherein the mass ratio of the monomer methacrylic acid or acrylic acid or maleic anhydride to the polyoxyethylene ether-polyoxypropylene ether block copolymer having an average molecular weight of 600-2000 is 10-30%: 70 to 90 percent.
9. The modified polyethylene glycol monomethyl ether of claim 5, wherein the polyoxyethylene ether-polyoxypropylene block copolymer having an average molecular weight of 600-2000 is prepared by: methanol is taken as an initiator, a catalyst 2 is added, and ethylene oxide and propylene oxide are added to react to obtain the polyoxyethylene ether and polyoxypropylene ether segmented copolymer with the number average molecular weight of 600-2000.
The reaction equation of claim 9 is as follows:
10. the modified polyethylene glycol monomethyl ether according to claim 9, wherein the catalyst 2 is sodium methoxide or potassium hydroxide.
11. The modified polyethylene glycol monomethyl ether according to claim 9, wherein the mass ratio of ethylene oxide to propylene oxide is 1: 0.3-0.5.
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| CN114292394A (en) * | 2021-12-29 | 2022-04-08 | 广东锦昱材料科技有限公司 | Method for producing polyethylene glycol methyl ether by using waste gas containing ethylene oxide |
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| CN114292394A (en) * | 2021-12-29 | 2022-04-08 | 广东锦昱材料科技有限公司 | Method for producing polyethylene glycol methyl ether by using waste gas containing ethylene oxide |
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