CN116144137B - Preparation method of hyperbranched polyurethane amide toughened ABS plastic - Google Patents
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- CN116144137B CN116144137B CN202310243487.5A CN202310243487A CN116144137B CN 116144137 B CN116144137 B CN 116144137B CN 202310243487 A CN202310243487 A CN 202310243487A CN 116144137 B CN116144137 B CN 116144137B
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- C—CHEMISTRY; METALLURGY
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L55/00—Compositions of homopolymers or copolymers, obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in groups C08L23/00 - C08L53/00
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- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
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- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
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Abstract
The invention relates to the technical field of plastics and discloses a preparation method of hyperbranched polyurethane amide toughened ABS plastics, which comprises the steps of reacting terephthalyl diisocyanate with 4-hydroxy phthalonitrile under the catalysis of dibutyl tin dilaurate to obtain terephthalyl (3, 4-dicyano) diphenyl carbamate, further hydrolyzing in a sodium hydroxide and sodium iodide system to obtain the terephthalyl (3, 4-dicarboxyl) diphenyl carbamate, and carrying out amidation polymerization reaction on the terephthalyl (3, 4-dicarboxyl) diphenyl carbamate and ethylenediamine under the catalysis of triphenyl phosphite and pyridine to obtain novel hyperbranched polyurethane amide, wherein the novel hyperbranched polyurethane amide is used as a toughening agent, and is subjected to melt granulation with ABS and a compatibilizer in a double-screw extruder to obtain the hyperbranched polyurethane amide toughened ABS plastics.
Description
Technical Field
The invention relates to the technical field of plastics, in particular to a preparation method of hyperbranched polyurethane amide toughened ABS plastics.
Background
ABS is a copolymer of three monomers, acrylonitrile, butadiene, and styrene. Has the advantages of acid resistance, corrosion resistance, innocuity, stable size, impact resistance and the like, and is commonly applied to manufacturing industries such as machinery, textile, automobiles and the like. But ABS has poor tensile properties and bending strength. Therefore, how to improve the mechanical properties of ABS plastic becomes a hot point of current research, and as reported in the literature PA6/ABS structure and mechanical properties research, the melt blending method for preparing the styrene-maleic anhydride copolymer compatibilized polyamide 6/acrylonitrile-butadiene-styrene copolymer blend shows that the particle size of a rubber phase in a blending system is continuously reduced along with the increase of the content of the styrene-maleic anhydride copolymer, the polydispersion coefficient is gradually increased, and the mechanical properties are enhanced.
The hyperbranched polymer is a highly branched quasi-three-dimensional spherical macromolecule, has a plurality of branching points, is not easy to tangle molecular chains, has rich active terminal functional groups, is easy to modify and modify, and is often applied to the fields of stabilizers, coatings, drug carriers, environmental repair and the like. For example, patent CN109251466 discloses a flame-retardant engineering plastic and a preparation method thereof, wherein ABS resin and a toughening agent are mixed uniformly, then a metal modified hyperbranched polymer is added, and the mixture is mixed uniformly again and then melted and granulated to obtain the flame-retardant engineering plastic, wherein the metal modified hyperbranched polymer is a network polymer formed by crosslinking a hyperbranched polymer with carboxyl groups at the end groups and metal ions, and the metal modified hyperbranched polymer is uniformly dispersed in the prepared engineering plastic, so that the prepared engineering plastic has good flame retardant property and excellent molding processability. The invention prepares the novel hyperbranched polyurethane amide, and enhances the tensile property, impact resistance and other properties of ABS plastic.
Disclosure of Invention
(one) solving the technical problems
Aiming at the defects of the prior art, the invention provides a preparation method of hyperbranched polyurethane amide toughened ABS plastic, and the obtained toughened modified ABS plastic has good performances of stretching, bending, shock resistance and the like.
(II) technical scheme
A preparation method of hyperbranched polyurethane amide toughened ABS plastic comprises the following steps:
(1) Preparation of hyperbranched polyurethane amides
At 120-150 ℃, ethylenediamine and (3, 4-dicarboxyl) diphenyl terephthalamide are put into a flask filled with N-methyl-2-pyrrolidone, triphenyl phosphite and pyridine catalyst are added into the flask, stirred and reacted for 3-5 hours, and cooled to room temperature, so that hyperbranched polyurethane amide is obtained.
(2) Preparation of hyperbranched polyurethane amide toughened ABS plastic
And (3) placing the ABS, the hyperbranched polyurethane amide and the compatibilizer into a double-screw extruder, uniformly mixing, melting, granulating for later use, drying the prepared granules, and preparing standard test sample bars through an injection molding machine to obtain the hyperbranched polyurethane amide toughened ABS plastic.
Preferably, the molar ratio of ethylenediamine to (3, 4-dicarboxy) diphenyl terephthalamide in step (1) is 1.8-2.5:1.
Preferably, the volume ratio of the triphenyl phosphite to the pyridine catalyst in the step (1) is 1:1.1-1.3.
Preferably, the hyperbranched polyurethane amide is used in an amount of 2-10% of the ABS.
Preferably, in the step (2), the screw rotating speed is 500-800r/min, and the temperature of the extruder is set to be 210-230 ℃.
Preferably, the preparation method of the (3, 4-dicarboxyl) diphenyl terephthalate comprises the following steps:
s1: preparation of (3, 4-dicyano) diphenyl terephthalamide
At 60-80 ℃, putting terephthal-diisocyanate into a flask filled with 4-hydroxy phthalonitrile, adding dibutyltin dilaurate into the flask, and stirring the mixture for reaction for 40-80min to obtain the (3, 4-dicyano) diphenyl terephthalamide.
S2: preparation of (3, 4-dicarboxyl) diphenyl terephthalamide
Sequentially adding the terephthalamide (3, 4-dicyano) diphenyl ester, sodium hydroxide and sodium iodide into a flask filled with N, N-dimethylformamide at 140-200 ℃, carrying out reflux reaction for 20-30min, cooling to room temperature, neutralizing with 5% dilute hydrochloric acid aqueous solution, and filtering to obtain the terephthalamide (3, 4-dicarboxyl) diphenyl ester.
Preferably, the molar ratio of the terephthalonitrile to the 4-hydroxyphthalonitrile in the step S1 is 1:2-2.5.
Preferably, the dibutyltin dilaurate (DBTD) in the step S1 is 0.2-0.8% of the total molar amount of the reactants.
Preferably, the method is characterized in that: in the step S2, the molar ratio of the terephthaloyl diphenyl (3, 4-dicyano) carbamate to the sodium hydroxide to the sodium iodide is 1:0.9-1.2:4-6.
(III) beneficial technical effects
Under the catalysis of dibutyl tin dilaurate, the terephthalyl diisocyanate reacts with 4-hydroxy phthalonitrile to obtain terephthalyl (3, 4-dicyano) diphenyl carbamate, and further in a sodium hydroxide and sodium iodide system, the terephthalyl (3, 4-dicarboxyl) diphenyl carbamate is obtained through hydrolysis, and the terephthalyl (3, 4-dicarboxyl) diphenyl carbamate and ethylenediamine undergo amidation polymerization reaction under the catalysis of the final triphenyl phosphite and pyridine to obtain the novel hyperbranched polyurethane amide, which is used as a toughening agent, and is subjected to melt granulation with ABS and a compatibilizer in a double-screw extruder to obtain the hyperbranched polyurethane amide toughened ABS plastic.
After hyperbranched polyurethane amide and ABS are melted, hyperbranched polyurethane amide particles are embedded in a continuous phase of the ABS, the compatibility and interaction between the ABS are stronger, when the ABS plastic is subjected to external force, the hyperbranched polyurethane amide is used as a stress concentrator to generate silver lines and a shearing band effect, and when the ABS plastic is subjected to impact, the development of the silver lines can be effectively controlled, a large amount of energy is consumed, the generation of cracks is effectively controlled, and the toughness and the strength of the ABS are greatly improved. The novel hyperbranched polyurethane amide synthesized by the method can enhance the tensile property, impact resistance and other properties of ABS plastic.
Drawings
FIG. 1 is a route to hyperbranched polyurethane amides.
Detailed Description
Example 1
(1) Preparation of (3, 4-dicyano) diphenyl terephthalamide
At 70℃0.3mol of terephthal-isocyanate was placed in a flask containing 0.7mol of 4-hydroxyphthalonitrile, and 6mmol of dibutyltin dilaurate (DBTD) was added thereto and reacted with stirring for 60 minutes to obtain 3, 4-dicyano-diphenyl terephthalamide.
(2) Preparation of (3, 4-dicarboxyl) diphenyl terephthalamide
0.3mol of (3, 4-dicyano) diphenyl terephthalamide, 0.3mol of sodium hydroxide and 1.5mol of sodium iodide are sequentially added into a flask filled with N, N-dimethylformamide at 140 ℃, reflux reaction is carried out for 40min, cooling is carried out to room temperature, a dilute hydrochloric acid aqueous solution with the concentration of 5% is used for neutralization, and filtration is carried out, thus obtaining (3, 4-dicarboxyl) diphenyl terephthalamide.
(3) Preparation of hyperbranched polyurethane amides
At 120℃4.5mmol of ethylenediamine and 2.5mmol of (3, 4-dicarboxy) diphenyl terephthalamide were placed in a flask containing N-methyl-2-pyrrolidone, 3.5mL of triphenyl phosphite and 3.8mL of pyridine catalyst were added thereto, stirred and reacted for 3 hours, and cooled to room temperature to obtain hyperbranched polyurethane amide.
(4) Preparation of hyperbranched polyurethane amide toughened ABS plastic
The preparation method comprises the steps of (1) placing 100% of ABS, 4% of hyperbranched polyurethane amide and 0.6% of styrene-N-phenylmaleimide-maleic anhydride terpolymer compatibilizer into a double-screw extruder, setting the temperature of the extruder to 220 ℃, setting the screw rotating speed to 700r/min, mixing, melting and granulating, and preparing standard test bars through an injection molding machine to obtain the hyperbranched polyurethane amide toughened ABS plastic.
Example 2
(1) Preparation of (3, 4-dicyano) diphenyl terephthalamide
At 80℃0.3mol of terephthal-isocyanate was placed in a flask containing 0.75mol of 4-hydroxyphthalonitrile, 1.8mmol of dibutyltin dilaurate was added thereto, and the reaction was stirred for 60 minutes to obtain (3, 4-dicyano) diphenyl terephthalamide.
(2) Preparation of (3, 4-dicarboxyl) diphenyl terephthalamide
0.3mol of (3, 4-dicyano) diphenyl terephthalamide, 0.27mol of sodium hydroxide and 1.2mol of sodium iodide are sequentially added into a flask filled with N, N-dimethylformamide at 140 ℃, reflux reaction is carried out for 40min, cooling is carried out to room temperature, a dilute hydrochloric acid aqueous solution with the concentration of 5% is used for neutralization, and filtration is carried out, thus obtaining (3, 4-dicarboxyl) diphenyl terephthalamide.
(3) Preparation of hyperbranched polyurethane amides
6mmol of ethylenediamine and 2.5mmol of (3, 4-dicarboxyl) diphenyl terephthalamide were placed in a flask containing N-methyl-2-pyrrolidone at 150 ℃, 3.5mL of triphenyl phosphite and 4.6mL of pyridine catalyst were added thereto, and the mixture was stirred and reacted for 4 hours, and cooled to room temperature to obtain hyperbranched polyurethane amide.
(4) Preparation of hyperbranched polyurethane amide toughened ABS plastic
The preparation method comprises the steps of (1) placing 100% of ABS, 2% of hyperbranched polyurethane amide and 0.8% of ABS grafted maleic anhydride compatibilizer into a double-screw extruder, setting the extruder at 220 ℃, mixing, melting and granulating, and preparing standard test bars through an injection molding machine to obtain the hyperbranched polyurethane amide toughened ABS plastic.
Example 3
(1) Preparation of (3, 4-dicyano) diphenyl terephthalamide
At 60℃0.3mol of terephthal-isocyanate was placed in a flask containing 0.65mol of 4-hydroxyphthalonitrile, and 5.4mmol of dibutyltin dilaurate was added thereto and reacted with stirring for 50 minutes to obtain (3, 4-dicyano) diphenyl terephthalamide.
(2) Preparation of (3, 4-dicarboxyl) diphenyl terephthalamide
0.3mol of (3, 4-dicyano) diphenyl terephthalamide, 0.36mol of sodium hydroxide and 1.8mol of sodium iodide are sequentially added into a flask filled with N, N-dimethylformamide at 130 ℃, reflux reaction is carried out for 60min, cooling is carried out to room temperature, a dilute hydrochloric acid aqueous solution with the concentration of 5% is used for neutralization, and filtration is carried out, thus obtaining (3, 4-dicarboxyl) diphenyl terephthalamide.
(3) Preparation of hyperbranched polyurethane amides
6mmol of ethylenediamine and 2.5mmol of (3, 4-dicarboxyl) diphenyl terephthalamide were placed in a flask containing N-methyl-2-pyrrolidone at 130 ℃, 3.5mL of triphenyl phosphite and 4mL of pyridine catalyst were added thereto, and the mixture was stirred and reacted for 4 hours, and cooled to room temperature to obtain hyperbranched polyurethane amide.
(4) Preparation of hyperbranched polyurethane amide toughened ABS plastic
The preparation method comprises the steps of (1) placing 100% of ABS, 10% of hyperbranched polyurethane amide and 1% of styrene grafted maleic anhydride compatibilizer into a double-screw extruder, setting the temperature of the extruder to 230 ℃, mixing, melting and granulating the materials, and preparing standard test bars through an injection molding machine to obtain the hyperbranched polyurethane amide toughened ABS plastic.
Example 4
(1) Preparation of (3, 4-dicyano) diphenyl terephthalamide
At 80℃0.3mol of terephthal-isocyanate was placed in a flask containing 0.75mol of 4-hydroxyphthalonitrile, 8.4mmol of dibutyltin dilaurate was added thereto, and the reaction was stirred for 80 minutes to obtain (3, 4-dicyano) diphenyl terephthalamide.
(2) Preparation of (3, 4-dicarboxyl) diphenyl terephthalamide
0.3mol of (3, 4-dicyano) diphenyl terephthalamide, 0.27mol of sodium hydroxide and 1.5mol of sodium iodide are sequentially added into a flask filled with N, N-dimethylformamide at 150 ℃, reflux reaction is carried out for 60min, cooling is carried out to room temperature, a dilute hydrochloric acid aqueous solution with the concentration of 5% is used for neutralization, and filtration is carried out, thus obtaining (3, 4-dicarboxyl) diphenyl terephthalamide.
(3) Preparation of hyperbranched polyurethane amides
6.3mmol of ethylenediamine and 2.5mmol of (3, 4-dicarboxyl) diphenyl terephthalamide were placed in a flask containing N-methyl-2-pyrrolidone at 150℃and 3.5mL of triphenyl phosphite and 4.6mL of pyridine catalyst were added thereto, and the reaction was stirred for 5 hours and cooled to room temperature to obtain hyperbranched polyurethane amide.
(4) Preparation of hyperbranched polyurethane amide toughened ABS plastic
The preparation method comprises the steps of (1) placing 100% of ABS, 8% of hyperbranched polyurethane amide and 0.4% of styrene-N-phenylmaleimide-maleic anhydride terpolymer compatibilizer into a double-screw extruder, setting the temperature of the extruder to be 210 ℃, setting the screw rotating speed to be 500r/min, mixing, melting and granulating, and preparing standard test bars through an injection molding machine to obtain the hyperbranched polyurethane amide toughened ABS plastic.
Example 5
(1) Preparation of (3, 4-dicyano) diphenyl terephthalamide
At 60℃0.3mol of terephthal-isocyanate was placed in a flask containing 0.6mol of 4-hydroxyphthalonitrile, 1.8mmol of dibutyltin dilaurate was added thereto, and the reaction was stirred for 40min to obtain (3, 4-dicyano) diphenyl terephthalamide.
(2) Preparation of (3, 4-dicarboxyl) diphenyl terephthalamide
0.3mol of (3, 4-dicyano) diphenyl terephthalamide, 0.3mol of sodium hydroxide and 1.6mol of sodium iodide are sequentially added into a flask filled with N, N-dimethylformamide at 150 ℃, reflux reaction is carried out for 30min, cooling is carried out to room temperature, a dilute hydrochloric acid aqueous solution with the concentration of 5% is used for neutralization, and filtration is carried out, thus obtaining (3, 4-dicarboxyl) diphenyl terephthalamide.
(3) Preparation of hyperbranched polyurethane amides
6.3mmol of ethylenediamine and 2.5mmol of (3, 4-dicarboxyl) diphenyl terephthalamide were placed in a flask containing N-methyl-2-pyrrolidone at 120℃and 3.5mL of triphenyl phosphite and 4mL of pyridine catalyst were added thereto, and the mixture was stirred and reacted for 4 hours, and cooled to room temperature to obtain hyperbranched polyurethane amide.
(4) Preparation of hyperbranched polyurethane amide toughened ABS plastic
The preparation method comprises the steps of (1) placing 100% of ABS, 6% of hyperbranched polyurethane amide and 0.6% of styrene grafted maleic anhydride compatibilizer into a double-screw extruder, setting the extruder at 220 ℃, mixing, melting and granulating, and preparing standard test bars through an injection molding machine to obtain the hyperbranched polyurethane amide toughened ABS plastic.
Comparative example 1
(1) Preparation of ABS Plastic
The preparation method comprises the steps of (1) placing 100% of ABS and 0.6% of styrene grafted maleic anhydride compatibilizer into a double-screw extruder, setting the extruder at 220 ℃ and the screw speed at 600r/min, mixing, melting, granulating, and preparing standard test bars through an injection molding machine to obtain the hyperbranched polyurethane amide toughened ABS plastic.
Tensile strength was measured according to GB/T1040 at a tensile speed of 50mm/min.
Impact strength was measured according to GB/T1843.
Flexural strength and flexural modulus were tested according to GB/T9341 at a speed of 2mm/min.
The tensile strength of example 5 was maximum, reaching 75.2MPa. The impact strength of example 3 was at a maximum of 7.8kJ/m 2 . The flexural strength and flexural modulus of example 1 were maximum, reaching 92.5MPa and 2.8GPa, far higher than those of the ABS plastic prepared in comparative example 1.
Claims (9)
1. A preparation method of hyperbranched polyurethane amide toughened ABS plastic is characterized by comprising the following steps: the preparation method comprises the following steps:
(1) Preparation of hyperbranched polyurethane amides
At 120-150 ℃, ethylenediamine and (3, 4-dicarboxyl) diphenyl terephthalamide are put into a flask filled with N-methyl-2-pyrrolidone, triphenyl phosphite and pyridine catalyst are added into the flask, stirred and reacted for 3-5 hours, and cooled to room temperature, so that hyperbranched polyurethane amide is obtained;
(2) Preparation of hyperbranched polyurethane amide toughened ABS plastic
And (3) placing the ABS, the hyperbranched polyurethane amide and the compatibilizer into a double-screw extruder, uniformly mixing, melting, granulating for later use, drying the prepared granules, and preparing standard test sample bars through an injection molding machine to obtain the hyperbranched polyurethane amide toughened ABS plastic.
2. The method for preparing hyperbranched polyurethane amide toughened ABS plastic according to claim 1, wherein the method comprises the following steps: the molar ratio of ethylenediamine to (3, 4-dicarboxyl) diphenyl terephthalamide in the step (1) is 1.8-2.5:1.
3. The method for preparing hyperbranched polyurethane amide toughened ABS plastic according to claim 1, wherein the method comprises the following steps: the volume ratio of the triphenyl phosphite to the pyridine catalyst in the step (1) is 1:1.1-1.3.
4. The method for preparing hyperbranched polyurethane amide toughened ABS plastic according to claim 1, wherein the method comprises the following steps: the rotating speed of the screw in the step (2) is 500-800r/min, and the temperature of the extruder is set to be 210-230 ℃.
5. The method for preparing hyperbranched polyurethane amide toughened ABS plastic according to claim 1, wherein the method comprises the following steps: the dosage of the hyperbranched polyurethane amide is 2-10% of that of ABS.
6. The method for preparing hyperbranched polyurethane amide toughened ABS plastic according to claim 1, wherein the method comprises the following steps: the preparation method of the (3, 4-dicarboxyl) diphenyl terephthalate comprises the following steps:
s1: preparation of (3, 4-dicyano) diphenyl terephthalamide
Placing terephthal-diisocyanate into a flask filled with 4-hydroxy phthalonitrile at 60-80 ℃, adding dibutyltin dilaurate into the flask, and stirring and reacting for 40-80min to obtain (3, 4-dicyano) diphenyl terephthalamide;
s2: preparation of (3, 4-dicarboxyl) diphenyl terephthalamide
Sequentially adding the terephthalamide (3, 4-dicyano) diphenyl ester, sodium hydroxide and sodium iodide into a flask filled with N, N-dimethylformamide at 140-200 ℃, carrying out reflux reaction for 20-30min, cooling to room temperature, neutralizing with 5% dilute hydrochloric acid aqueous solution, and filtering to obtain the terephthalamide (3, 4-dicarboxyl) diphenyl ester.
7. The method for preparing the hyperbranched polyurethane amide toughened ABS plastic according to claim 6, wherein the method is characterized by comprising the following steps: the molar ratio of the terephthalonitrile to the 4-hydroxyphthalonitrile in the step S1 is 1:2-2.5.
8. The method for preparing the hyperbranched polyurethane amide toughened ABS plastic according to claim 6, wherein the method is characterized by comprising the following steps: the dibutyltin dilaurate in the step S1 accounts for 0.2-0.8% of the total molar amount of the reactants.
9. The method for preparing the hyperbranched polyurethane amide toughened ABS plastic according to claim 6, wherein the method is characterized by comprising the following steps: in the step S2, the molar ratio of the terephthaloyl diphenyl (3, 4-dicyano) carbamate to the sodium hydroxide to the sodium iodide is 1:0.9-1.2:4-6.
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