Aziridinyl compounds, polyolefin elastomer toughening agents, and methods of making and using the same

By reacting aziridine compounds with polyolefin elastomers to generate graft copolymers, the problems of low-temperature impact strength and poor compatibility of nylon materials were solved, and the low-temperature impact toughness and interfacial compatibility of nylon materials were improved.

CN117624007BActive Publication Date: 2026-08-25WANHUA CHEM GRP CO LTD
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Patent Information

Application Number
CN202210973387.3
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2022-08-15
Publication Date
2026-08-25
Estimated Expiration
2042-08-15

AI Technical Summary

Technical Problem

Nylon materials have low low-temperature impact strength, and existing elastomer toughening agents have poor compatibility with nylon, resulting in unsatisfactory toughening effects.

Method used

A graft copolymer was generated by melting and reacting an aziridine compound with a polyolefin elastomer. The interfacial compatibility was improved by reacting the aziridine group with the carboxyl group at the nylon end, thus preparing a polyolefin elastomer toughening agent.

Benefits of technology

It significantly improves the low-temperature impact toughness and interfacial compatibility of nylon materials, and enhances the mechanical properties of nylon.

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Abstract

The application discloses a kind of aziridinyl compounds, polyolefin elastomer toughening agent and preparation method and application.The aziridinyl compound has the following structural expression formula.The application first synthesizes a kind of compound containing double bond and aziridinyl group, then is bonded to the molecular chain of polyolefin elastomer by double bond addition reaction, finally by the reaction of aziridinyl group and nylon end carboxyl group generates a plurality of polyolefin elastomer toughening agent as side chain graft copolymer, can improve the interfacial compatibility of nylon and polyolefin elastomer, to effectively improve the low-temperature impact toughness and other mechanical properties of nylon material.
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Description

Technical Field

[0001] This invention relates to a compound and a toughening agent prepared therefrom, and more particularly to an aziridinyl compound, a polyolefin elastomer toughening agent, a preparation method therefrom, and its application. Background Technology

[0002] Nylon was one of the earliest polymer materials used as engineering plastics, and it is widely used in machinery, automotive, footwear, construction, and medical fields, ranking first among the five major engineering plastics. Nylon possesses excellent properties such as high strength, oil resistance, wear resistance, corrosion resistance, fatigue resistance, self-lubrication, and a low coefficient of friction. However, nylon also has significant drawbacks, primarily low low-temperature impact strength, high water absorption, and poor dimensional stability, especially in applications like the automotive and construction industries where high toughness is required. To expand the industrial applications of nylon, it is necessary to develop modification schemes that effectively improve its impact toughness.

[0003] Currently, nylon toughening methods mainly rely on the addition of toughening agents, which can be broadly classified into the following categories: elastomers, engineering plastics, polyolefins, and inorganic particles. Among these toughening agents, elastomers are the most effective and widely used. Due to their low hardness, good resilience, low modulus, and low glass transition temperature (Tg), elastomers can impart excellent low-temperature resistance to nylon and improve its low-temperature brittleness. Improving nylon toughness using toughening agents requires good interfacial compatibility between nylon and the toughening agent, and the toughening agent needs to achieve a certain degree of dispersion within the nylon matrix to effectively enhance nylon toughness. However, elastomer toughening agents are generally polyolefins, which are non-polar materials, while nylon contains highly polar amide groups, resulting in poor compatibility with polyolefin materials and significant phase separation, leading to unsatisfactory toughening effects.

[0004] To improve the compatibility of elastomers with nylon, maleic anhydride is often used to graft-modify the elastomer. The modified elastomer contains maleic anhydride side chains, which can react with the terminal amino groups of nylon molecules to generate elastomer-nylon graft copolymers, thus improving the compatibility between the elastomer and nylon. For example, invention patent CN103304989A discloses a method for preparing polyolefin elastomer-toughened nylon composite materials, which involves ultrasonically blending and extruding polyolefin elastomers and maleic anhydride to obtain maleic anhydride-grafted elastomers for toughening nylon. However, in nylon production, diacids or acyl chlorides are often used as end-capping agents to neutralize amino end groups. Therefore, the content of terminal amino groups in nylon materials is usually low, while the content of terminal carboxyl groups is high. Maleic anhydride is not reactive with terminal carboxyl groups, resulting in low reaction efficiency between maleic anhydride-grafted elastomers and nylon materials. A high addition amount is usually required to achieve the toughening effect, leading to low toughening agent utilization and material waste. Summary of the Invention

[0005] To address the above technical problems, this invention first proposes an aziridine-based compound and its preparation method. The aziridine-based compound is obtained by reacting a polyaziridine crosslinking agent SaC-100 containing three active aziridine groups with acrylic acid and a carboxyl compound, and its molecular structure contains at least one aziridine group and one double bond.

[0006] Based on a second aspect of the present invention, a polyolefin elastomer toughening agent is also provided, which is obtained by the melt reaction of the above-mentioned aziridine compound and a polyolefin elastomer, wherein the toughening agent molecular chain contains at least one aziridine group.

[0007] Based on a third aspect of the present invention, a nylon material comprising the above-mentioned polyolefin elastomer toughening agent is also provided. The nylon material and the polyolefin elastomer toughening agent are melt-blended and can form a graft copolymer through the reaction of the aziridine group with the nylon terminal carboxyl group, thereby enhancing the interfacial compatibility between nylon and polyolefin elastomer, and thus effectively improving the mechanical properties of the nylon material such as low-temperature impact toughness.

[0008] To achieve the above objectives, the technical solution adopted by the present invention is as follows:

[0009] This invention first provides an aziridinyl compound having the structural expression shown in Formula I:

[0010]

[0011] In Formula I, R1 is selected from the following groups, where the tilde has no specific meaning and only indicates the connection position of the group in Formula I:

[0012]

[0013] This invention also provides a method for preparing the aziridinyl compound as described above, comprising the following steps:

[0014] 1) Polyaziridine crosslinking agent SaC-100 and acrylic acid are mixed and reacted at a molar ratio of (0.9-1.1):1 to obtain intermediate of formula II;

[0015]

[0016] 2) The carboxyl compound and the reaction solution containing the intermediate of formula II are mixed at a molar ratio of 0-1 and reacted. After the reaction is completed, the solvent is removed to obtain the aziridinyl compound shown in formula I.

[0017] The carboxyl compound is selected from one or more of acrylic acid, methacrylic acid, 3-butenoic acid, 4-pentenoic acid, crotonic acid, 6-heptenoic acid, 7-octenic acid, 5-hexenoic acid, 9-decenoic acid, 10-undecenoic acid, 11-dodecenoic acid, 10-heptadecenoic acid, eicosenoic acid, oleic acid, and linoleic acid.

[0018] Preferably, the solvent is one or more of benzene, toluene, xylene, dichloromethane, and trichloromethane.

[0019] In the above preparation method, the reaction in step 1) introduces double bond groups into the compound structure, enabling it to react with polyolefin elastomers. The reaction in step 2) increases the content of double bond groups in the compound, thereby improving its crosslinking ability. Preferably, the introduction of long alkyl chains can reduce the polarity of the compound, making it more compatible with polyolefin elastomers and improving reaction efficiency. However, the reaction in step 2) is not mandatory. When the amount of carboxyl compound is 0, the aziridine group can be retained to improve the subsequent crosslinking ability of nylon materials.

[0020] It should be noted that the above preparation process is only to provide a feasible synthetic route. Based on the design purpose, other similar processes can also be used to prepare the aziridine compound, such as mixing and reacting acrylic acid and carboxyl compound with polyaziridine crosslinking agent SaC-100 in one step, or adjusting the order of addition of raw materials. Since the reaction principle is relatively simple and the reaction is relatively rapid, the above methods or their conventional adjustments can all obtain the aziridine compound with the desired structure. Therefore, the above preparation method is not intended to limit the present invention in any way.

[0021] The present invention also provides a polyolefin elastomer toughening agent, wherein the toughening agent is prepared by a melt grafting reaction of a polyolefin elastomer and an aziridine compound of Formula I, wherein the mass ratio of the polyolefin elastomer to the aziridine compound of Formula I is (93-99):(0.5-5).

[0022]

[0023] In Formula I, R1 is selected from the following groups, where the tilde has no specific meaning and only indicates the connection position of the group in Formula I:

[0024]

[0025] In a preferred embodiment of the present invention, the method for preparing the polyolefin elastomer toughening agent includes the following steps:

[0026] 1) Add 93-99% polyolefin elastomer, 0.5-5% aziridinyl compound of Formula I, 0-0.5% antioxidant, 0-0.5% crosslinking inhibitor and 0.1-1.5% initiator by mass percentage to a high-speed mixer and mix at 20-50℃ for 0.2-3h;

[0027] 2) The mixed material is fed into a twin-screw extruder for melt extrusion, pelletized, and dried to obtain the polyolefin elastomer toughening agent.

[0028] In a preferred embodiment of the present invention, the temperature of the twin-screw extruder is set as follows: Zone 1 70-90℃, Zone 2 170-180℃, Zone 3 180-190℃, Zone 4 190-200℃, Zone 5 190-200℃, Zone 6 190-200℃, Zone 7 180-190℃, and the extruder die temperature is 180-190℃; the residence time in each zone is 4-5 seconds, and the screw speed is set to 200-600 rpm.

[0029] In a preferred embodiment of the present invention, the polyolefin elastomer is a copolymer of ethylene and α-olefin or diene;

[0030] Preferably, the α-olefin is one or more selected from propylene, 1-butene, butadiene, 1-hexene, 4-methyl-1-pentene, and 1-octene; the diene is one or more selected from butadiene, pentadiene, hexadiene, and octadiene.

[0031] Preferably, the density of the polyolefin elastomer is 0.885-0.860 g / cm³. 3 The melt flow index (2.16 kg, 190℃) is 0.1-10 g / 10 min.

[0032] In a preferred embodiment of the present invention, the antioxidant is one or more of hindered phenols and hindered amine antioxidants; preferably, the antioxidant is one or more of tetrakis(β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate) pentaerythritol (antioxidant 1010), N,N'-bis-(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyl)hexamethylenediamine (antioxidant 1098), β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate n-octadecyl ester (antioxidant 1076), and N,N'-bis[β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyl]hydrazine (antioxidant 1024).

[0033] Preferably, the crosslinking inhibitor is one or more of dimethylformamide, triethylamine, and diphenylamine;

[0034] Preferably, the initiator is one or more of di(tert-butylperoxyisopropyl)benzene, diisopropylperoxy, benzoyl peroxide, and tert-butylperoxyhexane.

[0035] The present invention also provides a nylon material comprising the polyolefin elastomer toughening agent described above.

[0036] In a preferred embodiment of the invention, the nylon material is obtained by melt blending of components comprising the following mass percentages:

[0037] 80-95% nylon, 5-20% polyolefin elastomer toughening agent;

[0038] The nylon is selected from one or more of nylon 6, nylon 66, nylon 610, nylon 612, nylon 1010, nylon 11, and nylon 12, with a terminal carboxyl group content of 30-500 mmol / kg, preferably 45-300 mmol / kg.

[0039] During the melt blending process of the nylon material, the aziridine groups in the polyolefin elastomer toughening agent can react with the terminal carboxyl groups of nylon to generate a nylon-polyolefin elastomer comb-like graft copolymer. This graft copolymer can improve the interfacial compatibility between nylon and polyolefin elastomer, increase the dispersion of polyolefin elastomer in nylon, and effectively improve low-temperature impact toughness.

[0040] This invention first synthesizes a compound containing both double bonds and aziridine groups, then bonds it to the molecular chain of a polyolefin elastomer through a double bond addition reaction. Finally, a large number of graft copolymers with polyolefin elastomer toughening agents as side chains are generated through the reaction of the aziridine groups and the nylon terminal carboxyl groups. This can improve the interfacial compatibility between nylon and polyolefin elastomer, thereby effectively improving the mechanical properties of nylon materials such as low-temperature impact toughness. Detailed Implementation

[0041] The present invention will be further illustrated below with specific embodiments. These embodiments are merely illustrative and do not limit the scope of the invention.

[0042] Unless otherwise specified, the raw materials used in the following embodiments and comparative examples of this invention were obtained from commercial sources.

[0043] Among them, the polyaziridine crosslinking agent SaC-100 (CAS No.: 64265-57-2) was purchased from Shanghai Maclean;

[0044] Engage 8150, a polyolefin elastomer: an ethylene-octene copolymer, with a melt flow index (2.16 kg, 190℃) of 0.5 g / 10 min, a weight-average molecular weight of 14 kg / mol, and a density of 0.868 g / cm³. 3 Purchased from Dow Chemical;

[0045] Polyolefin elastomer LF575: ethylene-butene copolymer, melt flow index (2.16 kg, 190℃) 5 g / 10 min, weight-average molecular weight 6.5 kg / mol, density 0.877 g / cm³ 3 Purchased from LG Chem;

[0046] PA12: Purchased from Evonic, brand name VESTAMID L1940, weight average molecular weight 34.6 kg / mol, terminal carboxyl group content 96 mmol / kg.

[0047]

Example 1

[0048] (1) Preparation of aziridinyl compound G1

[0049] 100g of polyaziridine crosslinking agent SaC-100 was dissolved in 1200ml of toluene. Then, 16g of acrylic acid was slowly added to the mixture at a rate of 0.1ml / min while stirring. After the acrylic acid was added, the solvent was stirred at 25°C for 30 minutes. Next, 20g of methacrylic acid was dissolved in 100ml of toluene and slowly added to the above reaction solution. The mixture was stirred at 25°C for 30 minutes. The reaction solution was refluxed and stirred at 40°C for 1 hour. Finally, the solvent was removed by rotary evaporation to obtain aziridine compound G1.

[0050]

[0051] The resolved 1H NMR spectrum of aziridinyl compound G1 is as follows:

[0052] 1 H NMR (CDCl3, 400MHz): δ6.47(m,1H), δ6.4(m,1H), δ6.27(dd,1H), δ6.04(q,1H), δ5.6(dd,1H), δ4.36(m,4H), δ4.13(m,6H), δ3.39(m,2H), δ2.94(t ,4H),δ2.75(t,2H),δ2.36(t,6H),δ2.07(s,2H),δ2.01(s,3H),δ1.78(m ,1H),δ1.7(m,2H),1.25(m,2H),δ1.12(d,6H),δ1.07(d,3H),δ0.9(t,3H)

[0053] (2) Preparation of polyolefin elastomer toughening agent

[0054] 2 kg of polyolefin elastomer Engage 8150, 20 g of aziridine compound G1, 2 g of antioxidant 1010, 2 g of triethylamine, and 4 g of dicumyl peroxide were added to a high-speed mixer and mixed at 40°C for 1 hour. After the materials were evenly mixed in the high-speed mixer, they were fed into a twin-screw extruder for melt extrusion. The extruder temperatures were set as follows: Zone 1 70°C, Zone 2 170°C, Zone 3 180°C, Zone 4 190°C, Zone 5 190°C, Zone 6 190°C, and Zone 7 180°C; the extruder die temperature was 180°C; the residence time in each zone was 4–5 seconds, and the screw speed was set to 400 rpm. After extrusion from the extruder die, the materials were granulated by an underwater pelletizer and dried to obtain the polyolefin elastomer toughening agent.

[0055]

Example 2

[0056] (1) Preparation of aziridinyl compound G2

[0057] 100g of polyaziridine crosslinking agent SaC-100 was dissolved in 1200ml of toluene. Then, 15g of acrylic acid was slowly added to the mixture at a rate of 0.1ml / min while stirring. After the acrylic acid was added, the solvent was stirred at 25°C for 30 minutes. Then, 27g of 9-decenoic acid was dissolved in 500ml of toluene and slowly added to the above reaction solution. The mixture was stirred at 25°C for 40 minutes. The reaction solution was refluxed and stirred at 60°C for 1.5 hours. Finally, the solvent was removed by rotary evaporation to obtain aziridine compound G2.

[0058]

[0059] (2) Preparation of polyolefin elastomer toughening agent

[0060] 2 kg of polyolefin elastomer LF575, 77 g of aziridinyl compound G2, 0.5 g of antioxidant 1076, 0.1 g of triethylamine, and 1.2 g of tert-butylhexane were added to a high-speed mixer and mixed at 40°C for 1 hour. After the materials were evenly mixed in the high-speed mixer, they were fed into a twin-screw extruder for melt extrusion. The extruder temperatures were set as follows: Zone 1 90°C, Zone 2 180°C, Zone 3 190°C, Zone 4 200°C, Zone 5 200°C, Zone 6 200°C, and Zone 7 190°C; the extruder die temperature was 190°C; the residence time in each zone was 4–5 seconds, and the screw speed was set to 400 rpm. After extrusion from the extruder die, the materials were granulated by an underwater pelletizer and dried to obtain the polyolefin elastomer toughening agent.

[0061]

Example 3

[0062] (1) Preparation of aziridinyl compound G3

[0063] 150g of polyaziridine crosslinking agent SaC-100 was dissolved in 1200ml of toluene. Then, 25g of acrylic acid was slowly added to the mixture at a rate of 0.1ml / min while stirring. After the acrylic acid was added, the solvent was stirred at 25°C for 50 minutes. Then, 37.5g of 5-hexenoic acid was dissolved in 450ml of toluene and slowly added to the above reaction solution. The mixture was stirred at 25°C for 40 minutes. The reaction solution was refluxed and stirred at 50°C for 1 hour. Finally, the solvent was removed by rotary evaporation to obtain aziridine compound G3.

[0064]

[0065] (2) Preparation of polyolefin elastomer toughening agent

[0066] 2 kg of polyolefin elastomer LF575, 50 g of aziridine compound G3, 1 g of antioxidant 1010, 0.5 g of triethylamine, and 1.5 g of dicumyl peroxide were added to a high-speed mixer and mixed at 40°C for 1 hour. After the materials were evenly mixed in the high-speed mixer, they were fed into a twin-screw extruder for melt extrusion. The extruder temperatures were set as follows: Zone 1 70°C, Zone 2 170°C, Zone 3 180°C, Zone 4 200°C, Zone 5 200°C, Zone 6 200°C, and Zone 7 180°C; the extruder die temperature was 180°C; the residence time in each zone was 4–5 seconds, and the screw speed was set to 400 rpm. After extrusion from the extruder die, the materials were granulated by an underwater pelletizer and dried to obtain the polyolefin elastomer toughening agent.

[0067]

Example 4

[0068] (1) Preparation of aziridinyl compound G4

[0069] 50g of polyaziridine crosslinking agent SaC-100 was dissolved in 500ml of toluene. Then, 25g of acrylic acid was slowly added to the mixture at a rate of 0.1ml / min while stirring. After the acrylic acid was added, the solvent was stirred at 25°C for 40 minutes. Then, 33g of 5-oleic acid was dissolved in 1000ml of toluene and slowly added to the above reaction solution. The mixture was stirred at 25°C for 40 minutes. The reaction solution was refluxed and stirred at 50°C for 1 hour. Finally, the solvent was removed by rotary evaporation to obtain aziridine compound G4.

[0070]

[0071] (2) Preparation of polyolefin elastomer toughening agent

[0072] 2 kg of polyolefin elastomer Engage 8150, 63 g of aziridine compound G4, 2 g of antioxidant 1010, 1.5 g of triethylamine, and 3 g of dicumyl peroxide were added to a high-speed mixer and mixed at 40°C for 1 hour. After the materials were evenly mixed in the high-speed mixer, they were fed into a twin-screw extruder for melt extrusion. The extruder temperatures were set as follows: Zone 1 90°C, Zone 2 170°C, Zone 3 190°C, Zone 4 190°C, Zone 5 200°C, Zone 6 190°C, and Zone 7 190°C; the extruder die temperature was 180°C; the residence time in each zone was 4–5 seconds, and the screw speed was set to 400 rpm. After extrusion from the extruder die, the materials were granulated by an underwater pelletizer and dried to obtain the polyolefin elastomer toughening agent.

[0073]

Example 5

[0074] (1) Preparation of aziridinyl compound G5

[0075] 100g of polyaziridine crosslinking agent SaC-100 was dissolved in 1200ml of toluene. Then, 25g of acrylic acid was slowly added to the mixture at a rate of 0.1ml / min while stirring. After the acrylic acid was added, the solvent was stirred at 25℃ for 40 minutes, then refluxed at 50℃ for 1 hour. Finally, the solvent was removed by rotary evaporation to obtain aziridine compound G5.

[0076]

[0077] (2) Preparation of polyolefin elastomer toughening agent

[0078] 2 kg of polyolefin elastomer Engage 8150, 50 g of aziridine compound G5, 2 g of antioxidant 1010, 2 g of triethylamine, and 4 g of dicumyl peroxide were added to a high-speed mixer and mixed at 40°C for 1 hour. After the materials were evenly mixed in the high-speed mixer, they were fed into a twin-screw extruder for melt extrusion. The extruder temperatures were set as follows: Zone 1 90°C, Zone 2 170°C, Zone 3 190°C, Zone 4 190°C, Zone 5 200°C, Zone 6 190°C, and Zone 7 190°C; the extruder die temperature was 180°C; the residence time in each zone was 4–5 seconds, and the screw speed was set to 400 rpm. After extrusion from the extruder die, the materials were granulated by an underwater pelletizer and dried to obtain the polyolefin elastomer toughening agent.

[0079] Comparative Example 1

[0080] The polyolefin elastomer toughening agent was prepared using essentially the same method as in Example 1, except that the aziridine compound G1 was not added to the extrusion feedstock.

[0081] Comparative Example 2

[0082] The polyolefin elastomer toughening agent was prepared using essentially the same method as in Example 1, except that the aziridine compound G1 in the extrusion raw material was replaced with the polyaziridine crosslinking agent SaC-100.

[0083]

Application Example

[0084] Nylon alloys were prepared by melt blending the polyolefin elastomer toughening agents prepared in each example and comparative example with PA12, and nylon alloys prepared by melt blending commercially available polyolefin elastomer Engage 8150 and PA12 were used as blank controls.

[0085] Each nylon alloy was injection molded and then subjected to the performance tests shown in Table 1. The test results are shown in Table 1.

[0086] The specific preparation method of nylon alloy is as follows:

[0087] 0.6 kg of polyolefin elastomer toughening agent and 2.4 kg of PA12 were mixed evenly and then added to a twin-screw extruder. The extruder temperatures were set as follows: Zone 1 140℃, Zone 2 200℃, Zone 3 230℃, Zone 4 240℃, Zone 5 240℃, Zone 6 230℃, and Zone 7 230℃. The extruder die temperature was 230℃, and the screw speed was set to 600 rpm. After the material was extruded from the extruder die, it was pelletized by an underwater pelletizer and dried to obtain a nylon alloy.

[0088] Table 1. Performance Test Results

[0089]

[0090] As can be seen from Table 1, the nylon alloy toughened by polyolefin elastomer prepared in the embodiments of the present invention has improved in terms of room temperature impact and low temperature impact strength compared with the nylon alloy in the comparative example. In particular, the low temperature impact strength is significantly improved, indicating that the polyolefin elastomer toughening agent in the present invention has significant advantages when applied to the preparation of nylon materials.

[0091] The above description is only a preferred embodiment of the present invention. It should be noted that those skilled in the art can make several improvements and additions without departing from the method of the present invention, and these improvements and additions should also be considered within the scope of protection of the present invention.

Claims

1. An aziridinyl compound, characterized in that, It has the following formula The structural expression shown is: Mode , Mode In formula I, R1 is selected from the following groups, where the tilde has no specific meaning and only indicates the connection position of the group in formula I: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 。 2. A method for preparing the aziridinyl compound as described in claim 1, characterized in that, Includes the following steps: 1) Polyaziridine crosslinking agent SaC-100 and acrylic acid are mixed and reacted at a molar ratio of (0.9-1.1):1 to obtain the formula... intermediate; Mode , 2) The carboxyl compound and the reaction solution containing the intermediate of formula II are mixed at a molar ratio of 0-1 and reacted. After the reaction is completed, the solvent is removed to obtain the aziridinyl compound shown in formula I. The carboxyl compound is selected from one or more of acrylic acid, methacrylic acid, 3-butenoic acid, 4-pentenoic acid, crotonic acid, 6-heptenoic acid, 7-octenic acid, 5-hexenoic acid, 9-decenoic acid, 10-undecenoic acid, 11-dodecenoic acid, 10-heptadecenoic acid, eicosenoic acid, oleic acid, and linoleic acid.

3. A toughening agent for polyolefin elastomers, characterized in that, The toughening agent is prepared by melt grafting reaction of polyolefin elastomer and aziridine compound of Formula I, wherein the mass ratio of polyolefin elastomer to aziridine compound of Formula I is (93-99):(0.5-5). Mode , Mode In formula I, R1 is selected from the following groups, where the tilde has no specific meaning and only indicates the connection position of the group in formula I: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 。 4. The polyolefin elastomer toughening agent according to claim 3, characterized in that, Its preparation method includes the following steps: 1) Add 93-99% polyolefin elastomer, 0.5-5% aziridinyl compound as shown in Formula I, 0-0.5% antioxidant, 0-0.5% crosslinking inhibitor, and 0.1-1.5% initiator by mass percentage to a high-speed mixer and mix at 20-50℃ for 0.2-3 hours; 2) The mixed material is fed into a twin-screw extruder for melt extrusion, pelletized, and dried to obtain the polyolefin elastomer toughening agent.

5. The polyolefin elastomer toughening agent according to claim 4, characterized in that, The temperature settings of the twin-screw extruder are as follows: Zone 1 70-90℃, Zone 2 170-180℃, Zone 3 180-190℃, Zone 4 190-200℃, Zone 5 190-200℃, Zone 6 190-200℃, Zone 7 180-190℃, and extruder die temperature 180-190℃; the residence time in each zone is 4-5 seconds, and the screw speed is set to 200-600 rpm.

6. The polyolefin elastomer toughening agent according to claim 4, characterized in that, The polyolefin elastomer is a copolymer of ethylene and α-olefin or diene.

7. The polyolefin elastomer toughening agent according to claim 6, characterized in that, The α-olefin is one or more of propylene, 1-butene, butadiene, 1-hexene, 4-methyl-1-pentene, and 1-octene; the diene is one or more of butadiene, pentadiene, hexadiene, and octadiene.

8. The polyolefin elastomer toughening agent according to claim 6, characterized in that, The density of the polyolefin elastomer is 0.885-0.860 g / cm³. 3 Melt flow index 2.16 kg, 0.1-10 g / 10 min at 190℃.

9. The polyolefin elastomer toughening agent according to any one of claims 4-8, characterized in that, The antioxidant is one or more of hindered phenols and hindered amines.

10. The polyolefin elastomer toughening agent according to claim 9, characterized in that, The crosslinking inhibitor is one or more of dimethylformamide, triethylamine, and diphenylamine.

11. The polyolefin elastomer toughening agent according to claim 9, characterized in that, The initiator is one or more of di(tert-butylperoxyisopropyl)benzene, diisopropylbenzene peroxide, dibenzoyl peroxide, and tert-butylperoxyhexane.

12. A nylon material comprising the polyolefin elastomer toughening agent according to any one of claims 3-11.

13. The nylon material according to claim 12, characterized in that, The nylon material is prepared by melt blending of components comprising the following mass percentages: 80-95% nylon, 5-20% polyolefin elastomer toughening agent; The nylon is selected from one or more of nylon 6, nylon 66, nylon 610, nylon 612, nylon 1010, nylon 11, and nylon 12, with a terminal carboxyl group content of 30-500 mmol / kg.

14. The nylon material according to claim 13, characterized in that, The nylon is selected from one or more of nylon 6, nylon 66, nylon 610, nylon 612, nylon 1010, nylon 11, and nylon 12, with a terminal carboxyl group content of 45-300 mmol / kg.

Citation Information

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