CN111040179A - Preparation method and application of epoxy soybean oil-based hyperdispersant - Google Patents
Preparation method and application of epoxy soybean oil-based hyperdispersant Download PDFInfo
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
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- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
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- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
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Abstract
The invention discloses a preparation method and application of an epoxy soybean oil-based hyperdispersant. Preparing an amino-terminated hyperbranched polyamide intermediate product from triethylenetetramine and butyl acrylate; heating epoxidized soybean oil, trimethylaluminum and amino-terminated hyperbranched polyamide to 60 ℃ under the protection of nitrogen, stirring for 2h, then heating to 90 ℃, and continuing stirring for 2h to obtain the epoxidized soybean oil-based hyperdispersant (ESO-g-HBP). The invention has the advantages of simple preparation process, low production cost, small pollution, wide applicability and the like. The hyper-dispersant prepared by the invention not only can effectively improve the dispersibility of inorganic powder in polymers, but also can greatly improve the mechanical property and the processing rheological property of composite materials.
Description
Technical Field
The invention belongs to the technical field of a hyperdispersant for surface modification of inorganic powder, and particularly relates to a preparation method and application of an epoxy soybean oil-based hyperdispersant.
Background
Surface modification or surface treatment techniques have become one of the most important deep processing techniques for inorganic powders. The surface modification can endow the inorganic powder with new performances such as hydrophilicity, biocompatibility, antistatic performance and the like. There are many methods for surface modification, and methods capable of changing the physicochemical properties of the surface or interface of the powder, such as surface organic coating, liquid phase chemical precipitation coating, gas phase physical deposition, mechanochemistry, intercalation of powder with lamellar structure, etc., can be called surface modification methods. The surface organic coating modification is the most common inorganic powder surface modification method at present, which is a method for modifying the particle surface by utilizing the adsorption or chemical reaction of functional groups in organic surface modifier molecules on the particle surface. The surface modifier mainly comprises coupling agent (such as silane, titanate, aluminate, zirconium aluminate, organic complex, phosphate, etc.), higher fatty acid and its salt, higher amine salt, silicone oil or silicone resin, organic oligomer and unsaturated organic acid, water-soluble polymer, etc. But the coupling agent has high price, the modification process is complex, the titanate coupling agent generates pollution and the like, so the large-area popularization and application of the coupling agent are not always realized. However, the stearic acid lubricating dispersant which is most widely used in industry at present has only one carboxyl anchoring point, and the alkyl group is longer, so the modification effect is not ideal.
Epoxidized Soybean Oil (ESO) is obtained by epoxidizing edible soybean oil, is a non-toxic, harmless, low-cost and biodegradable environment-friendly raw material, can be used as a bio-based plasticizer for food and medicine packaging, and can also be used for improving the stability and toughness of a high polymer material. The molecular chain of the epoxidized soybean oil has rich epoxy groups, so that favorable modification conditions are provided for modifying the epoxidized soybean oil and improving the use value of the epoxidized soybean oil.
The ring-opening grafting reaction of ESO can be used for preparing environment-friendly hyper-dispersant, and the epoxy group on ESO can react with amino-terminated hyper-branched polyamide (HBP-NH)2) Ring-opening reaction is carried out to generate hyperbranched polyamide grafted soybean oil hyperdispersant (ESO-g-HBP), the molecular structure of the hyperdispersant contains a plurality of amino anchoring groups, and multi-point anchoring can be formed on the surface of inorganic powder particles, so that the adsorption fastness is improved, and desorption is not easy. Meanwhile, the hyperbranched polyamide is not easy to entangle macromolecular chains, has low viscosity, is beneficial to improving the fluidity of inorganic powder, improves the dispersibility of the powder in polymers and improves the mechanical property of the composite material.
Xudan et al reported the invention patent "Chitosan-based hyperdispersant and its preparation method" (CN 105949349B), firstly using the condensation reaction of cyanuric chloride and arylamine to prepare hydrophobic monochlorotriazine derivative, then grafting the hydrophobic monochlorotriazine derivative to chitosan, then making sulfomethylation reaction with hydroxymethyl sodium sulfonate to prepare the chitosan-based hyperdispersant. An invention patent of "a hyper-dispersant, a method for producing the same and a method for using the same" (CN 105778573B) reported by foal et al is that a silane coupling agent (KH-570), styrene, acrylic acid, azobisisobutyronitrile and isopropanol are mixed to obtain a solution A, and the solution A is placed in N2And (3) dropwise adding the mixture into a toluene solution in a protective environment and in a stirring state, and filtering, washing and drying the product to obtain the hyperdispersant. Welsh lotus reports an invention patent of 'a titanium dioxide hyper-dispersant and a preparation method and application thereof' (CN 108383938A), which synthesizes the polyacrylic acid-acrylamide copolymer hyper-dispersant by adopting an aqueous solution polymerization method, taking Acrylic Acid (AA) and Acrylamide (AM) as comonomers and ammonium persulfate and sodium hypophosphite as redox initiation systems.
In the research of the hyperdispersant, no document report is found at present for the hyperdispersant, wherein the biological epoxy soybean oil is used as a solvating chain segment of the hyperdispersant, the grafted amino-terminated hyperbranched polyamide is used as a multipoint anchoring end, and the hyperbranched polyamide grafted epoxy soybean oil hyperdispersant is synthesized.
Disclosure of Invention
The invention aims to overcome the defects in the prior art and provide a preparation method and application of an epoxy soybean oil-based hyperdispersant.
The purpose of the invention can be realized by the following technical scheme:
the hyperbranched polyamide grafted epoxy soybean oil hyperdispersant is prepared, and the molecular structure of the hyperdispersant contains a plurality of amino anchoring groups, so that multi-point anchoring can be formed on the surfaces of inorganic powder particles, the inorganic powder is anchored, the adsorption fastness is improved, and the uniform dispersion of the inorganic powder in a polymer matrix is facilitated. Meanwhile, the long chain of the epoxidized soybean oil on the dispersing agent can be entangled with the molecular chain of the polymer, so that the interface compatibility between the inorganic powder and the polymer is improved, and the mechanical property of the composite material is improved.
The preparation method of the epoxy soybean oil-based hyperdispersant comprises the following specific steps:
(1) amino-terminated hyperbranched polyamide (HBP-NH)2) Synthesis of (2)
Weighing 14.6g of triethylenetetramine, pouring the triethylenetetramine into a 250mL three-neck flask, weighing 12.8g of butyl acrylate, dissolving the butyl acrylate in 25mL of methanol, pouring the obtained solution into the three-neck flask, stirring and reacting at 25 ℃ for 5 hours under the protection of nitrogen, distilling under reduced pressure to remove the methanol, heating to 140 ℃, and continuously stirring and reacting for 5 hours to obtain a light yellow viscous product, namely the amino-terminated hyperbranched polyamide (HBP-NH)2）。
(2) Preparation of ESO-g-HBP hyperdispersant
Adding 6-12 g of epoxidized soybean oil, 0.1-0.4 g of trimethylaluminum and 15-25 g of amino-terminated hyperbranched polyamide into a 250mL three-neck flask, heating to 60 ℃ under the protection of nitrogen, stirring for reaction for 2h, heating to 90 ℃, continuing stirring for 2h, and cooling after the reaction is finished to obtain the epoxidized soybean oil-based hyper-dispersant (ESO-g-HBP).
The epoxy soybean oil-based hyperdispersant is applied to CaCO3Surface modification of the powder to increase CaCO3Interfacial compatibility between the powder and the aliphatic or aromatic hydrocarbon polymer.
The invention has the following advantages:
(1) wide raw material source, low industrial cost and little environmental pollution.
(2) The preparation process is simple and is suitable for industrial large-scale production.
(3) The prepared epoxy soybean oil-based hyperdispersant can form multi-point anchoring on the surface of inorganic powder, improve the adsorption fastness, reduce the viscosity of a composite system, improve the fluidity of the inorganic powder such as calcium carbonate, silicon dioxide, titanium dioxide, talcum powder and the like, and is beneficial to improving the mechanical property of the composite material.
Drawings
FIG. 1 is a molecular structural formula of the epoxidized soybean oil-based hyperdispersant prepared by the invention.
Detailed Description
The main raw materials used in the examples are as follows: epoxidized soybean oil (technical grade), triethylenetetramine, butyl acrylate, methanol, trimethylaluminum (chemical purity), ground calcium carbonate (1200 mesh, technical grade).
Example 1:
1. amino-terminated hyperbranched polyamide (HBP-NH)2) Synthesis of (2)
14.6g of triethylenetetramine was weighed into a 250mL three-necked flask, 12.8g of butyl acrylate was weighed into 25mL of methanol, and the mixed solution was poured into the three-necked flask. Stirring and reacting at 25 deg.C for 5h under nitrogen protection, distilling under reduced pressure to remove methanol, heating to 140 deg.C, and stirring and reacting for 5h to obtain yellowish viscous HBP-NH2And (5) producing the product.
2. Preparation of ESO-g-HBP hyperdispersant
Adding 8g of epoxidized soybean oil, 0.2g of trimethylaluminum and 17g of amino-terminated hyperbranched polyamide into a 250mL three-neck flask, heating to 60 ℃ under the protection of nitrogen, stirring for reaction for 2 hours, heating to 90 ℃, and continuing stirring for 2 hours; after the reaction is finished, cooling to obtain the hyper-dispersant (ESO-g-HBP) of the hyper-branched polyamide grafted soybean oil.
3. Modified CaCO3Preparation of powder
Weighing 150g of ground calcium carbonate powder and 1g of ESO-g-HBP hyperdispersant, and stirring for 10min at 80 ℃ by using a high-speed stirrer to obtain modified CaCO3And (3) powder.
4. HDPE/ CaCO3Preparation of composite materials
Modified CaCO prepared in the step 33Extruding and granulating the powder and 100g of HDPE resin by a double screw, and performing injection molding on the granules by using a vertical injection machine to prepare the modified HDPE/CaCO3A composite material. HDPE/CaCO modified by ESO-g-HBP hyperdispersant3The tensile strength of the composite material is improved to 19.2MPa from 17.8MPa without adding ESO-g-HBP hyperdispersant, and the melt index is improved to 0.892g/10min from 0.871g/10 min.
Example 2:
1. amino-terminated hyperbranched polyamide (HBP-NH)2) Synthesis of (2)
14.6g of triethylenetetramine was weighed into a 250mL three-necked flask, 12.8g of butyl acrylate was weighed into 25mL of methanol, and the mixed solution was poured into the three-necked flask. Stirring and reacting at 25 deg.C for 5h under nitrogen protection, distilling under reduced pressure to remove methanol, heating to 140 deg.C, and stirring and reacting for 5h to obtain yellowish viscous HBP-NH2And (5) producing the product.
2. Preparation of ESO-g-HBP hyperdispersant
Adding 6g of epoxidized soybean oil, 0.1g of trimethylaluminum and 20g of amino-terminated hyperbranched polyamide into a 250mL three-neck flask, heating to 60 ℃ under the protection of nitrogen, stirring for reaction for 2 hours, heating to 90 ℃, and continuing stirring for 2 hours; after the reaction is finished, cooling to obtain the hyper-dispersant (ESO-g-HBP) of the hyper-branched polyamide grafted soybean oil.
3. Modified CaCO3Preparation of powder
Weighing 150g of ground calcium carbonate powder and 1.5g of ESO-g-HBP hyperdispersant, and stirring for 10min at 80 ℃ by using a high-speed stirrer to prepare modified CaCO3And (3) powder.
4. HDPE/ CaCO3Preparation of composite materials
Modified CaCO prepared in the step 33Extruding and granulating the powder and 100g of HDPE resin by a double screw, and performing injection molding on the granules by using a vertical injection machine to prepare the modified HDPE/CaCO3A composite material. HDPE/CaCO modified by ESO-g-HBP hyperdispersant3The tensile strength of the composite material is improved to 20.5MPa from 17.8MPa without adding ESO-g-HBP hyperdispersant, and the melt index is improved to 0.981g/10min from 0.871g/10 min.
Example 3:
1. amino-terminated hyperbranched polyamide (HBP-NH)2) Synthesis of (2)
14.6g of triethylenetetramine was weighed into a 250mL three-necked flask, 12.8g of butyl acrylate was weighed into 25mL of methanol, and the mixed solution was poured into the three-necked flask. Stirring and reacting at 25 deg.C for 5h under nitrogen protection, distilling under reduced pressure to remove methanol, heating to 140 deg.C, and stirring and reacting for 5h to obtain yellowish viscous HBP-NH2And (5) producing the product.
2. Preparation of ESO-g-HBP hyperdispersant
Adding 10g of epoxidized soybean oil, 0.3g of trimethylaluminum and 20g of amino-terminated hyperbranched polyamide into a 250mL three-neck flask, heating to 60 ℃ under the protection of nitrogen, stirring for reaction for 2 hours, heating to 90 ℃, and continuing stirring for 2 hours; after the reaction is finished, cooling to obtain the hyper-dispersant (ESO-g-HBP) of the hyper-branched polyamide grafted soybean oil.
3. Modified CaCO3Preparation of powder
Weighing 150g of ground calcium carbonate powder and 2g of ESO-g-HBP hyperdispersant, and stirring for 15min at 85 ℃ by using a high-speed stirrer to obtain modified CaCO3And (3) powder.
4. HDPE/ CaCO3Preparation of composite materials
Modified CaCO prepared in the step 33Extruding and granulating the powder and 100g of HDPE resin by a double screw, and performing injection molding on the granules by using a vertical injection machine to prepare the modified HDPE/CaCO3A composite material. HDPE/CaCO modified by ESO-g-HBP hyperdispersant3The tensile strength of the composite material is improved from 17.8MPa without adding ESO-g-HBP hyperdispersant to 21.3MPa, and the melt index is 0.871g/10min is increased to 1.38g/10 min.
Example 4:
1. amino-terminated hyperbranched polyamide (HBP-NH)2) Synthesis of (2)
14.6g of triethylenetetramine was weighed into a 250mL three-necked flask, 12.8g of butyl acrylate was weighed into 25mL of methanol, and the mixed solution was poured into the three-necked flask. Stirring and reacting at 25 deg.C for 5h under nitrogen protection, distilling under reduced pressure to remove methanol, heating to 140 deg.C, and stirring and reacting for 5h to obtain yellowish viscous HBP-NH2And (5) producing the product.
2. Preparation of ESO-g-HBP hyperdispersant
Adding 15g of epoxidized soybean oil, 0.4g of trimethylaluminum and 25 g of amino-terminated hyperbranched polyamide into a 250mL three-neck flask, heating to 60 ℃ under the protection of nitrogen, stirring for reaction for 2 hours, heating to 90 ℃, and continuing stirring for 2 hours; after the reaction is finished, cooling to obtain the hyper-dispersant (ESO-g-HBP) of the hyper-branched polyamide grafted soybean oil.
3. Modified CaCO3Preparation of powder
Weighing 150g of ground calcium carbonate powder and 3g of ESO-g-HBP hyperdispersant, and stirring for 20min at 90 ℃ by using a high-speed stirrer to obtain modified CaCO3And (3) powder.
4. HDPE/ CaCO3Preparation of composite materials
Modified CaCO prepared in the step 33Extruding and granulating the powder and 100g of HDPE resin by a double screw, and performing injection molding on the granules by using a vertical injection machine to prepare the modified HDPE/CaCO3A composite material. HDPE/CaCO modified by ESO-g-HBP hyperdispersant3The tensile strength of the composite material is improved to 20.8MPa from 17.8MPa without adding ESO-g-HBP hyperdispersant, and the melt index is improved to 0.118g/10min from 0.871g/10 min.
Claims (2)
1. The preparation method of the epoxy soybean oil-based hyperdispersant is characterized by comprising the following specific steps:
(1) synthesis of amino-terminated hyperbranched polyamide
Weighing 14.6g of triethylenetetramine, pouring the triethylenetetramine into a 250mL three-neck flask, weighing 12.8g of butyl acrylate, dissolving the butyl acrylate in 25mL of methanol, pouring the obtained solution into the three-neck flask, stirring and reacting at 25 ℃ for 5 hours under the protection of nitrogen, carrying out reduced pressure distillation to remove the methanol, heating to 140 ℃, and continuously stirring and reacting for 5 hours to obtain a light yellow viscous product, namely the amino-terminated hyperbranched polyamide;
(2) preparation of epoxy soybean oil-based hyperdispersant
Adding 6-12 g of epoxidized soybean oil, 0.1-0.4 g of trimethylaluminum and 15-25 g of amino-terminated hyperbranched polyamide into a 250mL three-neck flask, heating to 60 ℃ under the protection of nitrogen, stirring for reaction for 2h, heating to 90 ℃, continuing stirring for 2h, and cooling after the reaction is finished to obtain the epoxidized soybean oil-based hyperdispersant.
2. The use of the epoxidized soybean oil-based hyperdispersant prepared by the preparation method of claim 1, characterized in that the epoxidized soybean oil-based hyperdispersant is used as para-CaCO3Surface modification of the powder to increase CaCO3Interfacial compatibility between the powder and the aliphatic or aromatic hydrocarbon polymer.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112048070A (en) * | 2020-06-07 | 2020-12-08 | 桂林理工大学 | Preparation method of hydroxyl-terminated hyperbranched polyester grafted epoxy soybean oil hyperdispersant |
| CN115772362A (en) * | 2022-12-20 | 2023-03-10 | 上海甚龙新材料技术有限公司 | Laser ablation composition for flexographic printing plate and preparation method thereof |
| CN116333527A (en) * | 2023-04-24 | 2023-06-27 | 金华贝尔油墨有限公司 | Preparation method of renewable degradable ink |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112048070A (en) * | 2020-06-07 | 2020-12-08 | 桂林理工大学 | Preparation method of hydroxyl-terminated hyperbranched polyester grafted epoxy soybean oil hyperdispersant |
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| CN116333527A (en) * | 2023-04-24 | 2023-06-27 | 金华贝尔油墨有限公司 | Preparation method of renewable degradable ink |
| CN116333527B (en) * | 2023-04-24 | 2023-12-01 | 金华贝尔油墨有限公司 | Preparation method of renewable degradable ink |
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