An initiator and its use

Abstract

This application discloses an initiator and its application, wherein the initiator comprises a chalcone compound, metal A, and lithium chloride; the chalcone compound is selected from any compound having the structural formula shown in Formula I; and metal A is selected from at least one of magnesium, lithium, and sodium. The novel initiator disclosed in this application can initiate the polymerization of olefin monomers with high polymerization efficiency, broad substrate applicability, and mild reaction conditions.

Description

Technical Field

[0001] This application relates to an initiator and its application, belonging to the field of initiator technology. Background Technology

[0002] Free radical polymerization, as one of the earliest and most widely used polymerization processes developed by humankind, holds a crucial position in the field of polymer chemistry. Since its discovery, numerous scientists have made significant contributions to this field. After the 1990s, with the development of industrial technology, polymer technology has rapidly entered a new era. Free radical polymerization has advantages such as a wide range of monomers, diverse synthesis processes, simple operation, and low industrialization costs. Currently, approximately 70% of polymer products are obtained through free radical polymerization. Common examples include polystyrene, polypropylene, and rubber.

[0003] Because it is difficult to control the key parameters of macromolecular structure in free radical polymerization, such as molecular weight, molecular weight distribution, end-group functionality, chain segment structure, and composition, and because free radical polymerization involves chain termination reactions (including irreversible chain transfer reactions), it is generally difficult to control the size and structure of polymer molecules. This often results in simple linear homopolymers and random copolymers with wide molecular weight distributions, which negatively impacts the final polymer's performance and subsequent applications. However, living radical polymerization, by introducing free radical polymerization, can solve these problems. The advantages of living radical polymerization include the ability to control polymer molecular weight, achieve narrower molecular weight distributions (with the same chain length), end-group functionalization, stereopolymerization, block copolymers, graft copolymers, etc. Compared to traditional free radical polymerization, it offers better molecular design and is an important means of synthesizing polymers with specific structures and properties. Since its development in the 1990s, living radical polymerization has gradually evolved into three types of controlled radical polymerization: nitrile radical polymerization, reversible addition-fracture chain transfer polymerization, and atom transfer radical polymerization. Living controlled radical polymerization is applicable to a wide range of monomers, produces widely used products, and has lower industrialization costs. Therefore, the industrialization of living radical polymerization is considered to have extremely high commercial value. Consequently, the development of novel living radical initiation systems is of great significance in the field of living radical polymerization. Summary of the Invention

[0004] According to one aspect of this application, an initiator and its application are provided. The novel initiator disclosed in this application can initiate the polymerization of olefin monomers with high polymerization efficiency, wide substrate applicability, and mild reaction conditions.

[0005] According to a first aspect of this application, an initiator is provided, said initiator comprising a chalcone compound, metal A, and lithium chloride;

[0006] The chalcone compounds are selected from any one of the compounds having the structural formula shown in Formula I;

[0007]

[0008] In Formula I, R1 and R2 are independently selected from C1-C6 alkyl groups and C6-C6 alkyl groups. 16 aryl, substituted C6-C 16 Any one of aryl or substituted C2-C6 alkenyl groups;

[0009] The metal A is selected from at least one of magnesium, lithium, and sodium.

[0010] Optionally, R1 and R2 are independently selected from C1-C2 alkyl groups and C6-C4 alkyl groups. 10 aryl, substituted C6-C 10 Any of the aryl groups.

[0011] Optionally, in the initiator, the molar ratio of the chalcone compound, metal A, and lithium chloride is 1–10:1–5:1.

[0012] Specifically, a color change will occur during the reaction.

[0013] Optionally, the substituted C6-C 16 The substituents in the aryl group are selected from any one of the C1-C6 alkoxy groups;

[0014] The substituents in the substituted C2-C6 alkenyl group are selected from C6-C6. 16 Any of the aryl groups.

[0015] Optionally, the chalcone compound is selected from any one of the following compounds:

[0016]

[0017] According to a second aspect of this application, a method for preparing a polyolefin compound is provided, the method comprising:

[0018] The polyolefin compound can be obtained by reacting a mixture containing an initiator and an olefin compound.

[0019] The initiator is selected from the above-mentioned initiators.

[0020] This application describes a method for preparing polyolefins with narrow molecular weight distributions by mixing an initiator with an olefin compound and reacting them in a one-pot reaction at room temperature under anhydrous and oxygen-free conditions, followed by precipitation in a poor solvent. In this invention, polymerization is initiated by free radicals generated from the single-electron transfer between metal A and carbonyl groups. A simple one-pot mixing and stirring method is used to synthesize polymers with narrow molecular weight distributions. The method is simple to operate, has low operating costs, high polymerization efficiency, wide substrate applicability, and mild reaction conditions, opening up new methods for polymer synthesis and possessing high practical value.

[0021] Optionally, the reaction conditions are as follows: the reaction is carried out under anhydrous conditions; the reaction temperature is -20℃ to 100℃; and the reaction time is 20 min to 4 h.

[0022] Optionally, the molar ratio of the olefin compound to the chalcone compound in the initiator is 10-100:1-10.

[0023] Optionally, the molecular weight distribution of the polyolefin compound is 1.1 to 1.3.

[0024] Optionally, the olefin compound is selected from at least one of styrene compounds, acrylate compounds, and nitrogen-dimethylacrylamide.

[0025] Optionally, the styrene compound is selected from styrene;

[0026] The acrylate compound is selected from at least one of methyl acrylate and methyl methacrylate.

[0027] Optionally, the polystyrene has a molecular weight of 4,000 to 1,000,000; the polymethyl acrylate has a molecular weight of 2,000 to 12,000; and the polymethyl methacrylate has a molecular weight of 3,000 to 150,000.

[0028] Optionally, the reaction may involve color changes, and different chalcones may produce different color changes in the reaction solution.

[0029] Optionally, the olefin compound is styrene; the molecular weight of the styrene is 4,000 to 1,000,000.

[0030] Optionally, the mixture may also include a solvent.

[0031] Optionally, the solvent is selected from at least one of tetrahydrofuran and nitrogen-dimethylformamide.

[0032] Optionally, after the reaction, the following step is further included:

[0033] After removing metal A from the reacted material, extraction and precipitation in a poor solvent yield the polyolefin compound.

[0034] In this application, olefin compounds are polymerized into polymers efficiently. The method is simple to operate, has high polymerization efficiency, and can produce polymers with high molecular weight and excellent properties.

[0035] Preferably, the method includes: mixing an olefin compound with a chalcone compound, metal A and lithium chloride in a molar ratio of 5:1:1:1, then dissolving the mixture in a solvent, and stirring at room temperature or under heating conditions to carry out the reaction.

[0036] Optionally, the reaction process involves the magnesium reacting with chalcone to generate free radicals for polymerization via single-electron transfer.

[0037] Optionally, after the reaction, the following step is further included:

[0038] After removing metal A from the reaction, the product is extracted, concentrated, and then precipitated in a poor solvent to obtain a polyolefin compound.

[0039] Optionally, the reagent used to remove metal A is saturated ammonium chloride.

[0040] Optionally, the extractant used in the extraction is selected from dichloromethane.

[0041] Optionally, the method includes:

[0042] Step 1: Take molar equivalent amounts of metal A and lithium chloride and place them into the reactor;

[0043] Step 2: Dissolve chalcone compounds and olefin compounds in tetrahydrofuran according to the appropriate ratio and add them to the reactor;

[0044] Step 3: React under stirring conditions, and after 30 minutes, precipitate with a poor solvent to obtain polyolefin compounds.

[0045] This invention develops a highly efficient, simple, and easily operable living radical polymerization method using the reaction of chalcone compounds with metal A, providing an important reference for living radical polymerization systems. This method is a one-pot polymerization process, simple to operate, highly feasible, and highly efficient at initiating olefin monomers. Compared with existing polymerization methods, this invention has a series of advantages, including fast reaction speed, large polymer molecular weight, narrow polymer molecular weight distribution, and a novel initiation system. By mixing chalcone compounds with metal A in tetrahydrofuran and performing simple stirring at room temperature, a polymer with a narrow molecular weight distribution can be obtained.

[0046] Optionally, the reaction in this application is carried out in solution at room temperature, under heating conditions, or at zero degrees Celsius.

[0047] This invention provides a novel method for the living polymerization of olefin compounds initiated by a novel initiator. The industrialization of living radical polymerization has extremely high commercial value. Therefore, the development of novel living radical initiation systems is of great significance in the field of living radical polymerization. Current living radical polymerization methods suffer from a series of problems, such as long reaction times and low polymer molecular weights. This application develops a method for obtaining high molecular weight polymers by generating free radicals through single-electron transfer between metal A and chalcone. This method uses a mixture of chalcone compounds, metal A, lithium chloride, and olefin compounds, achieving a yield greater than 99% within 30 minutes. The advantages of this method include fast reaction speed, high polymer molecular weight, narrow polymer molecular weight distribution, novel initiation system, and the widespread availability and ease of preparation of chalcone, along with simple operation, making it highly advantageous for subsequent industrialization.

[0048] In this application, C1-C6 refers to the number of carbon atoms contained. The limitation on the carbon atoms in the term "substituted aryl" refers to the number of carbon atoms inherent in the aryl group itself, not the number of carbon atoms after substitution. For example, C6-C6... 16 A substituted aryl group refers to an aryl group with 6 to 16 carbon atoms in which at least one hydrogen atom is replaced by a substituent.

[0049] In this application, "alkyl" refers to a group formed by losing any one hydrogen atom from an alkane compound molecule. The alkane compound includes straight-chain alkanes, branched alkanes, cycloalkanes, and branched cycloalkanes.

[0050] In this application, "aryl" is a group formed by the loss of a hydrogen atom from the aromatic ring of an aromatic compound molecule; such as p-tolyl formed by the loss of a hydrogen atom at the para position of the methyl group on the benzene ring of toluene.

[0051] In this application, "alkenyl" is a group formed by losing a hydrogen atom from an alkenyl group on an olefin molecule.

[0052] The beneficial effects that this application can produce include:

[0053] First, the operation is simple and highly feasible. It only requires mixing metal A and substances such as chalcone with olefin monomers in a solvent in one pot and stirring to obtain polyolefin polymers.

[0054] Secondly, it has high polymerization efficiency. When the monomer is mixed with chalcone compounds, metal A and lithium chloride in a molar ratio of 5:1:1:1, the monomer conversion rate can reach 100% within 30 minutes.

[0055] Third, the initiation system is novel and can produce high molecular weight polymers with narrow molecular weight distribution. Attached Figure Description

[0056] Figure 1This is the 1H NMR spectrum of the polymer in Example 1 of this invention;

[0057] Figure 2 This is the gel permeation chromatogram of the polymer in Example 1 of the present invention;

[0058] Figure 3 This is the result of 1H NMR spectroscopy tracking during the polymerization reaction process in Example 1 of this invention. Detailed Implementation

[0059] The present application is described in detail below with reference to the embodiments, but the present application is not limited to these embodiments.

[0060] Unless otherwise specified, the raw materials and catalysts used in the embodiments of this application were all purchased commercially.

[0061] All pharmaceuticals used in the examples were commercially available, and the tetrahydrofuran used was of analytical grade. The polymers used in the examples were prepared in our laboratory.

[0062] The instruments used in the examples are: Bruker 400MHz nuclear magnetic resonance spectrometer and Agilent gel permeation chromatography system.

[0063] Example 1:

[0064] The chalcone monomers and olefins used in this embodiment are shown in the following formulas:

[0065]

[0066] This embodiment includes the following steps:

[0067] (1) Take 2 mol of magnesium filings (0.056 g) and 1 equivalent of lithium chloride (2 mol, 0.08 g) and put them into the reaction tube;

[0068] (2) Perform vacuum blowing and heat treatment to ensure a water-free and oxygen-free environment;

[0069] (3) Take 1g (i.e. 10mol) of the above styrene monomer and 2mol (i.e. 0.39g) of chalcone and dissolve them in 5ml of tetrahydrofuran solution. Mix and stir. At room temperature, as the reaction proceeds, the color of the reaction solution changes from colorless to green, and then gradually turns into dark reddish-brown.

[0070] (4) After 30 minutes, process the reaction.

[0071] (5) Magnesium shavings were removed by saturated ammonium chloride solution, followed by dichloromethane extraction, washing three times with deionized water, concentrated by rotary evaporation, and precipitated in methanol to obtain a polymer with a product mass of 0.99 g and a yield of 99%.

[0072] Figure 1The NMR spectrum of the polymer prepared in Example 1 of this invention is shown in the figure. The NMR spectrum shows that the polymer was successfully synthesized. Figure 2 This is a gel permeation chromatogram of the polymer prepared in Example 1. It can be seen from the gel permeation chromatogram that the synthesized polymer has a large molecular weight and a narrow molecular weight distribution, with a relative number-average molecular weight of 35,000 and a molecular weight distribution of 1.1. Figure 3 The figure shows the 1H NMR spectroscopy results during the polymerization reaction in Example 1 of this invention. The figure illustrates the disappearance of the characteristic peaks of the styrene monomer and the beginning of polymer formation. Therefore, based on... Figure 1-3 It can be seen that this novel initiation system can successfully generate high molecular weight polymers with narrow distribution.

[0073] Example 2:

[0074] The chalcone monomers and olefins used in this embodiment are shown in the following formulas:

[0075]

[0076] This embodiment includes the following steps:

[0077] (1) Take 2 mol of magnesium filings (0.056 g) and 1 equivalent of lithium chloride (2 mol, 0.08 g) and put them into the reaction tube;

[0078] (2) Perform vacuum blowing and heat treatment without water;

[0079] (3) Take 1g (i.e. 10mol) of the above styrene monomer and 2mol (i.e. 0.49g) of chalcone monomer and dissolve them in tetrahydrofuran solution. Mix and stir. React at room temperature for 30min. As the reaction proceeds, the color of the reaction solution changes from light yellow to dark reddish brown.

[0080] (4) After 30 minutes, process the reaction.

[0081] (5) Magnesium shavings were removed using a saturated ammonium chloride solution, followed by extraction with dichloromethane, washing three times with deionized water, and concentration by rotary evaporation. The polymer was then precipitated in methanol with a yield of 0.99 g and a yield of 99%. Gel permeation chromatography showed a relative number-average molecular weight of 68,000 and a molecular weight distribution of 1.2.

[0082] Example 3:

[0083] The chalcone monomers and olefins used in this embodiment are shown in the following formulas:

[0084]

[0085] This embodiment includes the following steps:

[0086] (1) Take 2 mol of magnesium filings (0.056 g) and 1 equivalent of lithium chloride (2 mol, 0.08 g) and put them into the reaction tube;

[0087] (2) Perform vacuum blowing and heat treatment without water;

[0088] (3) Take 1g (i.e. 10mol) of the above styrene monomer and 2mol (i.e. 0.49g) of chalcone monomer and dissolve them in tetrahydrofuran solution. Mix and stir. React at room temperature for 30min. As the reaction proceeds, the color of the reaction solution changes from colorless to light yellow.

[0089] (4) After 30 minutes, process the reaction.

[0090] (5) Magnesium shavings were removed using a saturated ammonium chloride solution, followed by extraction with dichloromethane, washing three times with deionized water, and concentration by rotary evaporation. The polymer was then precipitated in methanol with a yield of 0.98 g and a yield of 98%. Gel permeation chromatography yielded a relative number-average molecular weight of 81,000 and a molecular weight distribution of 1.1.

[0091] Example 4:

[0092] The chalcone monomers and olefins used in this embodiment are shown in the following formulas:

[0093]

[0094] This embodiment includes the following steps:

[0095] (1) Take 2 mol of magnesium filings (0.056 g) and 1 equivalent of lithium chloride (2 mol, 0.08 g) and put them into the reaction tube;

[0096] (2) Perform vacuum blowing and heat treatment without water;

[0097] (3) Take 1g (i.e. 10mol) of the above styrene monomer and 2mol (i.e. 0.44g) of chalcone monomer and dissolve them in tetrahydrofuran solution. Mix and stir. React at room temperature for 30min. As the reaction proceeds, the color of the reaction solution changes from yellow to reddish-brown.

[0098] (4) After 30 minutes, process the reaction.

[0099] (5) Magnesium shavings were removed using a saturated ammonium chloride solution, followed by extraction with dichloromethane, washing three times with deionized water, and concentration by rotary evaporation. The polymer was then precipitated in methanol with a yield of 0.99 g and a yield of 99%. Gel permeation chromatography showed a relative number-average molecular weight of 117,000 and a molecular weight distribution of 1.3.

[0100] Example 5:

[0101] The chalcone monomers and olefins used in this embodiment are shown in the following formulas:

[0102]

[0103] This embodiment includes the following steps:

[0104] (1) Take 2 mol of magnesium filings (0.056 g) and 1 equivalent of lithium chloride (2 mol, 0.08 g) and put them into the reaction tube;

[0105] (2) Perform vacuum blowing and heat treatment without water;

[0106] (3) Take 1g (i.e. 10mol) of the above styrene monomer and 2mol (i.e. 0.52g) of chalcone monomer and dissolve them in tetrahydrofuran solution. Mix and stir. React at room temperature for 30min. As the reaction proceeds, the color of the reaction solution changes from yellow to red.

[0107] (4) After 30 minutes, process the reaction.

[0108] (5) Magnesium shavings were removed using a saturated ammonium chloride solution, followed by extraction with dichloromethane, washing three times with deionized water, and concentration by rotary evaporation. The polymer was then precipitated in methanol with a yield of 0.99 g and a yield of 99%. Gel permeation chromatography showed a relative number-average molecular weight of 107,000 and a molecular weight distribution of 1.3.

[0109] Example 6:

[0110] The chalcone monomers and olefins used in this embodiment are shown in the following formulas:

[0111]

[0112] This embodiment includes the following steps:

[0113] (1) Take 2 mol of lithium (0.013 g) and 1 equivalent of lithium chloride (2 mol, 0.08 g) and put them into the reaction tube;

[0114] (2) Perform vacuum blowing and heat treatment without water;

[0115] (3) Take 1g (i.e. 10mol) of the above styrene monomer and 2mol (i.e. 0.39g) of chalcone monomer and dissolve them in tetrahydrofuran solution. Mix and stir. React at room temperature for 30min. As the reaction proceeds, the color of the reaction solution changes from colorless to reddish-brown.

[0116] (4) After 30 minutes, process the reaction.

[0117] (5) Magnesium shavings were removed using a saturated ammonium chloride solution, followed by extraction with dichloromethane, washing three times with deionized water, and concentration by rotary evaporation. The polymer was then precipitated in methanol with a yield of 0.95 g and a yield of 95%. Gel permeation chromatography yielded a relative number-average molecular weight of 99,000 and a molecular weight distribution of 1.2.

[0118] Example 7:

[0119] The chalcone monomers and olefins used in this embodiment are shown in the following formulas:

[0120]

[0121] This embodiment includes the following steps:

[0122] (1) Take 2 mol of sodium wire (0.046 g) and 1 equivalent of lithium chloride (2 mol, 0.08 g) and put them into the reaction tube;

[0123] (2) Perform vacuum blowing and heat treatment without water;

[0124] (3) Take 1g (i.e. 10mol) of the above styrene monomer and 2mol (i.e. 0.39g) of chalcone monomer and dissolve them in tetrahydrofuran solution. Mix and stir. React at room temperature for 30min. As the reaction proceeds, the color of the reaction solution changes from colorless to reddish-brown.

[0125] (4) After 30 minutes, process the reaction.

[0126] (5) Magnesium shavings were removed using a saturated ammonium chloride solution, followed by extraction with dichloromethane, washing three times with deionized water, and concentration by rotary evaporation. The polymer was then precipitated in methanol with a yield of 0.99 g and a yield of 99%. Gel permeation chromatography showed a relative number-average molecular weight of 61,000 and a molecular weight distribution of 1.1.

[0127] Example 8:

[0128] The chalcone monomers and olefins used in this embodiment are shown in the following formulas:

[0129]

[0130] This embodiment includes the following steps:

[0131] (1) Take 2 mol of magnesium filings (0.056 g) and 1 equivalent of lithium chloride (2 mol, 0.08 g) and put them into the reaction tube;

[0132] (2) Perform vacuum blowing and heat treatment without water;

[0133] (3) Take 0.2g (i.e. 2mol) of the above styrene monomer and 2mol (i.e. 0.39g) of chalcone monomer and dissolve them in tetrahydrofuran solution. Mix and stir. React at room temperature for 30min. As the reaction proceeds, the color of the reaction solution changes from colorless to reddish-brown.

[0134] (4) After 30 minutes, process the reaction.

[0135] (5) Magnesium shavings were removed using a saturated ammonium chloride solution, followed by extraction with dichloromethane, washing three times with deionized water, and concentration by rotary evaporation. The polymer was then precipitated in methanol with a yield of 0.99 g and a yield of 99%. Gel permeation chromatography showed a relative number-average molecular weight of 68,000 and a molecular weight distribution of 1.1.

[0136] Example 9:

[0137] The chalcone monomers and olefins used in this embodiment are shown in the following formulas:

[0138]

[0139] This embodiment includes the following steps:

[0140] (1) Take 2 mol of magnesium filings (0.056 g) and 1 equivalent of lithium chloride (2 mol, 0.08 g) and put them into the reaction tube;

[0141] (2) Perform vacuum blowing and heat treatment without water;

[0142] (3) Take 0.42g (i.e. 4mol) of the above styrene monomer and 2mol (i.e. 0.39g) of chalcone monomer and dissolve them in tetrahydrofuran solution. Mix and stir. React at room temperature for 30min. As the reaction proceeds, the color of the reaction solution changes from colorless to reddish-brown.

[0143] (4) After 30 minutes, process the reaction.

[0144] (5) Magnesium shavings were removed using a saturated ammonium chloride solution, followed by extraction with dichloromethane, washing three times with deionized water, and concentration by rotary evaporation. The polymer was then precipitated in methanol with a yield of 0.99 g and a yield of 99%. Gel permeation chromatography showed a relative number-average molecular weight of 67,000 and a molecular weight distribution of 1.2.

[0145] Example 10:

[0146] The chalcone monomers and olefins used in this embodiment are shown in the following formulas:

[0147]

[0148] This embodiment includes the following steps:

[0149] (1) Take 1 mol of magnesium shavings (0.028 g) and 1 equivalent of lithium chloride (0.04 g) and put them into the reaction tube;

[0150] (2) Perform vacuum blowing and heat treatment without water;

[0151] (3) Take 0.42g (i.e. 10mol) of the above styrene monomer and 2mol (i.e. 0.39g) of chalcone monomer and dissolve them in tetrahydrofuran solution. Mix and stir, and react at room temperature for 2h. As the reaction proceeds, the color of the reaction solution changes from colorless to reddish-brown.

[0152] (4) After 2 hours, process the reaction.

[0153] (5) Magnesium shavings were removed using a saturated ammonium chloride solution, followed by extraction with dichloromethane, washing three times with deionized water, and concentration by rotary evaporation. The polymer was then precipitated in methanol with a yield of 0.96 g and a yield of 96%. Gel permeation chromatography yielded a relative number-average molecular weight of 38,000 and a molecular weight distribution of 1.18.

[0154] Example 11:

[0155] The chalcone monomers and olefins used in this embodiment are shown in the following formulas:

[0156]

[0157] This embodiment includes the following steps:

[0158] (1) Take 2 mol of magnesium filings (0.056 g) and 1 equivalent of lithium chloride (2 mol, 0.08 g) and put them into the reaction tube;

[0159] (2) Perform vacuum blowing and heat treatment without water;

[0160] (3) Take 2g (i.e. 20mol) of the above styrene monomer and 2mol (i.e. 0.39g) of chalcone monomer and dissolve them in tetrahydrofuran solution. Mix and stir. React at room temperature for 30min. As the reaction proceeds, the color of the reaction solution changes from colorless to reddish-brown.

[0161] (4) After 30 minutes, process the reaction.

[0162] (5) Magnesium shavings were removed using a saturated ammonium chloride solution, followed by extraction with dichloromethane, washing three times with deionized water, and concentration by rotary evaporation. The polymer was then precipitated in methanol with a yield of 0.99 g and a yield of 99%. Gel permeation chromatography showed a relative number-average molecular weight of 38,000 and a molecular weight distribution of 1.3.

[0163] Example 12:

[0164] The chalcone monomers and olefins used in this embodiment are shown in the following formulas:

[0165]

[0166] This embodiment includes the following steps:

[0167] (1) Take 2 mol of magnesium filings (0.056 g) and 1 equivalent of lithium chloride (2 mol, 0.08 g) and put them into the reaction tube;

[0168] (2) Perform vacuum blowing and heat treatment without water;

[0169] (3) Take 1g (i.e. 10mol) of the above styrene monomer and 2mol (i.e. 0.39g) of chalcone monomer and dissolve them in tetrahydrofuran solution. Mix and stir, and react at 0℃ for 4h. As the reaction proceeds, the color of the reaction solution changes from colorless to reddish-brown.

[0170] (4) After 4 hours, process the reaction.

[0171] (5) Magnesium shavings were removed using a saturated ammonium chloride solution, followed by extraction with dichloromethane, washing three times with deionized water, and concentration by rotary evaporation. The polymer was then precipitated in methanol with a yield of 0.96 g and a yield of 96%. Gel permeation chromatography showed a relative number-average molecular weight of 50,000 and a molecular weight distribution of 1.2.

[0172] Example 13:

[0173] The chalcone monomers and olefins used in this embodiment are shown in the following formulas:

[0174]

[0175] This embodiment includes the following steps:

[0176] (1) Take 2 mol of magnesium filings (0.056 g) and 1 equivalent of lithium chloride (2 mol, 0.08 g) and put them into the reaction tube;

[0177] (2) Perform vacuum blowing and heat treatment without water;

[0178] (3) Take 1g (i.e. 10mol) of the above styrene monomer and 2mol (i.e. 0.39g) of chalcone monomer and dissolve them in tetrahydrofuran solution. Mix and stir, and react at 100℃ for 20min. As the reaction proceeds, the color of the reaction solution changes from colorless to reddish-brown.

[0179] (4) After 20 minutes, process the reaction.

[0180] (5) Magnesium shavings were removed using a saturated ammonium chloride solution, followed by extraction with dichloromethane, washing three times with deionized water, and concentration by rotary evaporation. The polymer was then precipitated in methanol with a yield of 0.90 g and a yield of 90%. Gel permeation chromatography showed a relative number-average molecular weight of 63,000 and a molecular weight distribution of 1.1.

[0181] Example 14:

[0182] The chalcone monomers and olefins used in this embodiment are shown in the following formulas:

[0183]

[0184] This embodiment includes the following steps:

[0185] (1) Take 2 mol of magnesium filings (0.056 g) and 1 equivalent of lithium chloride (2 mol, 0.08 g) and put them into the reaction tube;

[0186] (2) Perform vacuum blowing and heat treatment without water;

[0187] (3) Take 0.86g (i.e. 10mol) of the above methyl acrylate monomer and 2mol (i.e. 0.39g) of chalcone monomer and dissolve them in tetrahydrofuran solution. Mix and stir, and react at room temperature for 1h. As the reaction proceeds, the color of the reaction solution changes from colorless to light yellow.

[0188] (4) After 1 hour, process the reaction.

[0189] (5) Magnesium shavings were removed using a saturated ammonium chloride solution, followed by extraction with dichloromethane, washing three times with deionized water, and concentration by rotary evaporation. The polymer was then precipitated in methanol with a yield of 0.85 g and a yield of 98%. Gel permeation chromatography showed a relative number-average molecular weight of 104,000 and a molecular weight distribution of 1.3.

[0190] Example 15:

[0191] The chalcone monomers and olefins used in this embodiment are shown in the following formulas:

[0192]

[0193] This embodiment includes the following steps:

[0194] (1) Take 2 mol of magnesium filings (0.056 g) and 1 equivalent of lithium chloride (2 mol, 0.08 g) and put them into the reaction tube;

[0195] (2) Perform vacuum blowing and heat treatment without water;

[0196] (3) Take 1g (i.e. 10mol) of the above methyl methacrylate monomer and 2mol (i.e. 0.39g) of chalcone monomer and dissolve them in tetrahydrofuran solution. Mix and stir, and react at room temperature for 1h. As the reaction proceeds, the color of the reaction solution changes from colorless to light yellow.

[0197] (4) After 1 hour, process the reaction.

[0198] (5) Magnesium shavings were removed using a saturated ammonium chloride solution, followed by extraction with dichloromethane, washing three times with deionized water, and concentration by rotary evaporation. The polymer was then precipitated in methanol with a yield of 0.85 g and a yield of 98%. Gel permeation chromatography showed a relative number-average molecular weight of 95,000 and a molecular weight distribution of 1.3.

[0199] Example 16:

[0200] The chalcone monomers and olefins used in this embodiment are shown in the following formulas:

[0201]

[0202] This embodiment includes the following steps:

[0203] (1) Take 2 mol of magnesium filings (0.056 g) and 1 equivalent of lithium chloride (2 mol, 0.08 g) and put them into the reaction tube;

[0204] (2) Perform vacuum blowing and heat treatment without water;

[0205] (3) Take 1g (i.e. 10mol) of the above N,N-dimethylacrylamide monomer and 2mol (i.e. 0.39g) of chalcone monomer and dissolve them in tetrahydrofuran solution. Mix and stir, and react at room temperature for 1h. As the reaction proceeds, the color of the reaction solution changes from colorless to light yellow.

[0206] (4) After 1 hour, process the reaction.

[0207] (5) Magnesium shavings were removed using a saturated ammonium chloride solution, followed by extraction with dichloromethane, washing three times with deionized water, and concentration by rotary evaporation. The polymer was then precipitated in methanol with a yield of 0.85 g and a yield of 85%. Gel permeation chromatography showed a relative number-average molecular weight of 34,000 and a molecular weight distribution of 1.3.

[0208] The above description is merely a few embodiments of this application and is not intended to limit this application in any way. Although this application discloses preferred embodiments as described above, it is not intended to limit this application. Any changes or modifications made by those skilled in the art without departing from the scope of the technical solution of this application using the disclosed technical content are equivalent to equivalent implementation cases and fall within the scope of the technical solution.

Claims

1. A method for producing a polyolefin-based compound, characterized by, The preparation method includes: The polyolefin compound is obtained by reacting a mixture containing an initiator and an olefin compound; the initiator includes chalcone compounds, metal A, and lithium chloride. The chalcone compounds are selected from any one of the compounds having the structural formula shown in Formula I; Formula I In Formula I, R1 and R2 are independently selected from C1-C6 alkyl groups and C6-C6 alkyl groups. 16 aryl, substituted C6-C 16 Any one of aryl or substituted C2-C6 alkenyl groups; The metal A is selected from at least one of magnesium, lithium, and sodium; The substituted C6-C 16 The substituents in the aryl group are selected from any one of the C1-C6 alkoxy groups; The substituents in the substituted C2-C6 alkenyl group are selected from C6-C6. 16 Any of the aryl groups.

2. The production method according to claim 1, characterized by, In the initiator, the molar ratio of the chalcone compound, metal A, and lithium chloride is 1~10:1~5:

1.

3. The preparation method according to claim 1, characterized in that, The chalcone compounds are selected from any one of the following compounds: 。 4. The method of claim 1, wherein, The reaction conditions are as follows: the reaction is carried out under anhydrous conditions; the reaction temperature is -20℃ to 100℃; and the reaction time is 20 min to 4 h.

5. The preparation method according to claim 1, characterized in that, The molar ratio of the olefin compound to the chalcone compound in the initiator is 10~100:1~10.

6. The method of claim 1, wherein, The molecular weight distribution of the polyolefin compound is 1.1~1.

3.

7. The preparation method according to claim 1, characterized in that, The olefin compound is selected from at least one of styrene compounds, acrylate compounds, and nitrogen-dimethylacrylamide.

8. The preparation method according to claim 7, characterized in that, The styrene compounds are selected from styrene; The acrylate compound is selected from at least one of methyl acrylate and methyl methacrylate; The mixture also includes a solvent; The solvent is selected from at least one of tetrahydrofuran and nitrogen-dimethylformamide.

9. The production method according to claim 8, characterized by, Following the reaction, the following steps are also included: After removing metal A from the reacted material, extraction and precipitation in a poor solvent yield the polyolefin compound.

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