Amide compounds, processes for their preparation, and uses thereof

Abstract

This application relates to an amide compound, its preparation method, and its application. The amide compound has the following general structural formula: ; where R1 contains C5~C6. 10 The alicyclic group; n1 is an integer from 9 to 15, n2 ≥ 2. The above amide compounds can be added to polymers as plasticizers, improving the polymer's heat resistance and mechanical properties.

Description

Technical Field

[0001] This application relates to the field of polymer materials technology, and in particular to an amide compound, its preparation method, and its application. Background Technology

[0002] Introducing plasticizers into polymers during processing or use can improve their processing performance, promote material processing and molding, and enhance the gloss and texture of the material surface. However, while traditional plasticizers can improve the plasticizing effect, they can also reduce the heat resistance and mechanical properties of polymer materials to some extent. Summary of the Invention

[0003] Based on this, some embodiments of this application provide an amide compound that can be added to polymer materials as a plasticizer to improve the heat resistance and mechanical properties of the polymer materials.

[0004] In addition, some other embodiments of this application also provide a method for preparing an amide compound and its application.

[0005] An amide compound having the following general structural formula:

[0006] ;

[0007] In the formula, R1 contains C5~C 10 Alicyclic groups;

[0008] n1 is an integer between 9 and 15, and n2 ≥ 2.

[0009] In some of these embodiments, R1 contains a cyclohexyl group.

[0010] In some embodiments, n1 is an integer from 11 to 15.

[0011] In some of these embodiments, n2 is 2 or 3.

[0012] In some embodiments, n2 is 2, and R1 is selected from... , and One or more of them; or,

[0013] n2 is 3, and R1 is selected from... .

[0014] In some embodiments, the raw materials for preparing the amide compound include fatty acids and alicyclic amines, wherein the fatty acids have the structural formula CH3CH2(CH2). n1 COOH; the alicyclic amine contains C5~C6. 10The polyamine has an alicyclic group, wherein the molar ratio of the carboxyl group in the fatty acid to the amino group in the alicyclic amine is (1.02~1.2):1.

[0015] In some embodiments, the raw materials for preparing the amide compound also include a catalyst and an antioxidant;

[0016] The catalyst includes one or more of phosphoric acid, phosphorous acid, hypophosphite, sodium hypophosphite, and p-toluenesulfonic acid; the antioxidant includes one or more of hindered phenolic antioxidants and phosphite antioxidants.

[0017] In some embodiments, the alicyclic amine includes one or more of 4,4-diaminodicyclohexylmethane, polyamine polycyclohexylmethane, 1,3-cyclohexyldimethylamine, and isophorone diamine.

[0018] In some embodiments, the antioxidant comprises a hindered phenolic antioxidant and a phosphite antioxidant in a mass ratio of (1~5):1.

[0019] In some embodiments, the hindered phenolic antioxidant includes one or more of 2,6-di-tert-butyl-4-methylphenol, N,N′-bis-(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyl)hexamethylenediamine and pentaerythritol tetrakis[β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate];

[0020] The phosphite antioxidants include one or more of 2′-ethylbis(4,6-di-tert-butylphenyl)fluorophosphite and tris(2,4-di-tert-butylphenyl)phosphite.

[0021] In some embodiments, the mass ratio of the catalyst to the fatty acid is (0.2~1):100.

[0022] In some embodiments, the mass ratio of the antioxidant to the fatty acid is (1~6):100.

[0023] A method for preparing an amide compound, comprising the following steps:

[0024] Amide compounds are prepared by amidation reaction of fatty acids and alicyclic amines;

[0025] The fatty acid has the structural formula CH3CH2(CH2). n1 COOH; the alicyclic amine contains C5~C6. 10 The polyamine with alicyclic groups; the structural formula of the amide compound is: ;

[0026] In the formula, R1 contains C5~C 10Alicyclic groups;

[0027] n1 is an integer between 9 and 15, and n2 ≥ 2.

[0028] In some embodiments, the alicyclic amine is a polyamine containing a cyclohexyl group.

[0029] In some embodiments, the alicyclic amine includes one or more of 4,4-diaminodicyclohexylmethane, polyamine polycyclohexylmethane, 1,3-cyclohexyldimethylamine, and isophorone diamine.

[0030] In some embodiments, a catalyst and an antioxidant are also added in the step of amide reaction of fatty acids and alicyclic amines;

[0031] The catalyst includes one or more of phosphoric acid, phosphorous acid, hypophosphite, sodium hypophosphite, and p-toluenesulfonic acid.

[0032] The antioxidants include hindered phenolic antioxidants and phosphite antioxidants in a mass ratio of (1~5):1.

[0033] In some embodiments, the step of amidation of fatty acids and alicyclic amines includes:

[0034] Under a protective atmosphere, the fatty acid, catalyst, and antioxidant are mixed and heated to melt the fatty acid.

[0035] The alicyclic amine was added to the reaction system at a temperature of 70℃~90℃.

[0036] Heat the reaction system to 90℃~110℃ and hold for 0.5h~2h, then continue to heat to 190℃~220℃ and hold for 4h~6h. Stop the reaction when the acid value is less than 10mgKOH / g.

[0037] Applications of the amide compounds described above, or amide compounds prepared by the methods described above, in the preparation of powder coatings, aqueous dispersions, or polymer materials.

[0038] A polymer material comprising a polymer matrix and an additive, wherein the additive comprises the amide compound described above or an amide compound prepared by the preparation method described above.

[0039] In some embodiments, the polymer matrix includes one or more of polyamide resin, polycarbonate, polyurethane, polyvinyl chloride, polyolefin and polyacrylonitrile.

[0040] The aforementioned amide compounds contain polyamide polar groups and long carbon chain structures, enabling them to form covalent and / or hydrogen bonds with various plastic matrix materials, exhibiting good compatibility. Furthermore, their relatively soft alicyclic structure and long carbon chain structure have minimal impact on the mechanical properties of the plastic matrix, such as tensile strength, while significantly improving its fracture toughness. They also enhance the heat resistance and plasticizing effect of the plastic matrix. Therefore, these amide compounds can be added to polymers as plasticizers, improving both the polymer's heat resistance and its mechanical properties. Attached Figure Description

[0041] To more clearly illustrate the technical solutions in the embodiments of this application, the accompanying drawings used in the description of the embodiments will be briefly introduced below. Obviously, the accompanying drawings described below are only some embodiments of this application. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0042] Figure 1 This is a schematic diagram of a process flow for preparing amide compounds according to some embodiments of this application. Detailed Implementation

[0043] To facilitate understanding of this application, a more comprehensive description of the application will be provided below in conjunction with specific embodiments. Preferred embodiments of the application are given in the specific embodiments. However, this application can be implemented in many different forms and is not limited to the embodiments described herein. Rather, these embodiments are provided to provide a more thorough and complete understanding of the disclosure of this application.

[0044] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs. The terminology used herein in the specification of this application is for the purpose of describing particular embodiments only and is not intended to be limiting of the application. The term "and / or" as used herein includes any and all combinations of one or more of the associated listed items.

[0045] Unless otherwise stated or in case of conflict, the terms or phrases used in this application shall have the following meanings:

[0046] In this application, the terms "first" and "second" are used for descriptive purposes only and should not be construed as indicating or implying relative importance or implicitly specifying the number of technical features indicated. Therefore, a feature defined with "first" and "second" may explicitly or implicitly include at least one of those features.

[0047] In the description of this application, "multiple" means at least two, such as two, three, etc., unless otherwise expressly and specifically limited.

[0048] In this application, "one or more" refers to any one, any two, or any two or more of the listed items. "Several" refers to any two or more.

[0049] Unless otherwise specified, all percentage concentrations mentioned in this application refer to the final concentration. The final concentration refers to the proportion of the added component in the system after the addition of that component.

[0050] In this document, terms such as "further," "even further," "especially," "for example," "as," "example," and "exemplary" are used for descriptive purposes to indicate a connection in the coverage of different technical solutions presented earlier and later. However, they should not be construed as limitations on the preceding technical solution or on the scope of protection of this document. Unless otherwise specified, A (as in B) indicates that B is a non-limiting example of A, and it can be understood that A is not limited to B.

[0051] In this document, "optionally," "optionally," and "optional" mean that something is optional, that is, it is selected from either "present" or "absent." If multiple "options" appear in a technical solution, unless otherwise specified and there are no contradictions or mutual constraints, each "option" is independent. In this application, descriptions such as "optionally contains" and "optionally includes" indicate "contains or does not contain." "Optional component X" indicates whether component X exists or does not exist, or whether component X is contained or not.

[0052] When a numerical range is disclosed in this application, the range is considered continuous and includes the minimum and maximum values ​​of the range, as well as every value between the minimum and maximum values. Furthermore, when the range refers to an integer, it includes every integer between the minimum and maximum values ​​of the range. Additionally, when multiple ranges are provided to describe a feature or characteristic, the ranges may be merged. In other words, unless otherwise specified, all ranges disclosed in this application should be understood to include any and all subranges to which they are included.

[0053] In this application, the technical features described in an open-ended manner include both closed technical solutions consisting of the listed features and open technical solutions that include the listed features.

[0054] The terms "comprising" and "having," and any variations thereof, used in the embodiments of this application, are intended to cover non-exclusive inclusion. For example, a process, method, system, product, or device that includes a series of steps or units is not limited to the steps or units listed, but may optionally include steps or units not listed, or may optionally include other steps or components inherent to such processes, methods, products, or devices.

[0055] In this application, the reference to "embodiment" means that a specific feature, structure, or characteristic described in connection with an embodiment may be included in at least one embodiment of this application. The appearance of this phrase in various places throughout the specification does not necessarily refer to the same embodiment, nor is it a mutually exclusive, independent, or alternative embodiment. It will be explicitly and implicitly understood by those skilled in the art that the embodiments described in this application can be combined with other embodiments.

[0056] The term "alicyclic group" refers to a non-aromatic hydrocarbon containing a ring carbon atom, which can be a monocyclic alkyl, spirocyclic, or bridged alkyl group. Phrases containing this term include, for example, "C5~C...". 10 "Alicyclic group" refers to an alicyclic group containing 5 to 10 carbon atoms. Each time it appears, it can be independently a C5 alicyclic group, a C6 alicyclic group, a C7 alicyclic group, a C8 alicyclic group, a C9 alicyclic group, or a C10 alicyclic group. 10 Alicyclic groups. Suitable examples include, but are not limited to, cyclopentyl, cyclohexyl, cycloheptyl, or cyclooctyl. Additionally, an "alicyclic group" may contain one or more double bonds; representative examples of alicyclic groups containing double bonds include cyclopentenyl, cyclohexenyl, cyclohexadienyl, and cyclobutadienyl.

[0057] The first aspect of this application provides an amide compound having the following general structural formula:

[0058] ;

[0059] In the formula, R1 contains C5~C 10 Alicyclic groups;

[0060] n1 is an integer between 9 and 15, and n2 ≥ 2.

[0061] The aforementioned amide compounds contain polyamide polar groups and long carbon chain structures, enabling them to form covalent and / or hydrogen bonds with various plastic matrix materials, exhibiting good compatibility. Furthermore, their relatively soft alicyclic structure and long carbon chain structure have minimal impact on the mechanical properties of the plastic matrix, such as tensile strength, while significantly improving its fracture toughness. They also enhance the heat resistance and plasticizing effect of the plastic matrix. Therefore, these amide compounds can be added to polymers as plasticizers, improving both the polymer's heat resistance and its mechanical properties.

[0062] R1 in the above amide compounds contains C5~C6. 10Compared to alicyclic structures, the alicyclic groups in amide compounds, when used in polymer materials, are beneficial for improving their heat resistance and increasing elongation at break without reducing tensile strength. In contrast, the introduction of aromatic groups may reduce the mechanical strength, hardness, and elongation at break of polymer materials to some extent. Furthermore, the gloss and appearance of polymer materials may be affected, reducing the anti-aging properties and service life of plastic products. In some embodiments of this application, the amide compounds have the above-mentioned general structural formula and can be added to polymers as plasticizers, improving both the heat resistance and mechanical properties of the polymer while maintaining a good appearance and gloss.

[0063] Therefore, the amide compounds provided in some embodiments of this application have more regular structures, excellent heat resistance, high color and low acid value. They can be used as dispersants, plasticizers, release agents or lubricants for polymer materials, with good plasticizing effect and certain improvement on the mechanical properties of plastic matrix.

[0064] In some embodiments, R1 contains C5~C 10 The alicyclic group. For example, R1 contains cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc. In some embodiments, R1 contains cyclohexyl.

[0065] In some embodiments, R1 does not contain aromatic groups. The introduction of aromatic groups may reduce the mechanical strength, hardness, elongation at break, etc. of the polymer material to a certain extent. In addition, the gloss and appearance of the polymer material will also be affected. Therefore, in some embodiments of this application, R1 does not contain aromatic groups.

[0066] In some embodiments, n1 is an integer from 9 to 15. For example, n1 is 9, 10, 11, 12, 13, 14, 15, or a range of any two of these values. In some embodiments, n1 is an integer from 11 to 15.

[0067] In some embodiments, n2 ≥ 2. For example, n2 is 2, 3, 4, 5, or a range of any two of these values. In some embodiments, n2 is 2 or 3.

[0068] In some embodiments, n2 is 2, and R1 is selected from... , and One or more of them.

[0069] In other embodiments, n2 is 3, and R1 is selected from... .

[0070] In some embodiments, the amide compound has a melting point ≥140°C. Optionally, the amide compound has a melting point ≥145°C. The high melting point of the above-mentioned amide compounds is beneficial for improving the heat resistance of polymer materials.

[0071] In some embodiments, the acid value of the amide compound is less than 10 mg KOH / g. Optionally, the acid value of the amide compound is ≤6 mg KOH / g. The above-mentioned amide compounds have low acid values.

[0072] In some embodiments, the whiteness of the amide compound is ≤5. The high whiteness of the aforementioned amide compounds is beneficial for improving the appearance and color of polymer materials when used in them.

[0073] In some embodiments, the amide compound is a white powder or a white to pale yellow powder.

[0074] In some embodiments, the raw materials for preparing the amide compound include: fatty acids and alicyclic amines, wherein the fatty acids have the structural formula CH3CH2(CH2). n1 COOH; Alicyclic amines contain C5~C6 10 The polyamine has an alicyclic group, and the molar ratio of the carboxyl group in the fatty acid to the amino group in the alicyclic amine is (1.02~1.2):1. For example, the molar ratio of the carboxyl group in the fatty acid to the amino group in the alicyclic amine can be, but is not limited to, 1.02:1, 1.05:1, 1.08:1, 1.1:1, 1.12:1, 1.15:1, 1.18:1, 1.2:1, or any range of two of these values.

[0075] Specifically, the fatty acids include one or more of stearic acid, palmitic acid, lauric acid, and myristic acid. In one specific example, the fatty acid is stearic acid.

[0076] Specifically, the alicyclic amine is a polyamine containing a cyclohexyl group. Optionally, the alicyclic amine includes one or more of 4,4-diaminodicyclohexylmethane, polyaminopolycyclohexylmethane, 1,3-cyclohexyldimethylamine, and isophorone diamine.

[0077] In some embodiments, the raw materials for preparing the amide compound also include a catalyst and an antioxidant.

[0078] Specifically, the catalyst includes one or more of phosphoric acid, phosphorous acid, hypophosphite, sodium hypophosphite, and p-toluenesulfonic acid. In some embodiments, the mass ratio of the catalyst to the fatty acid is (0.2~1):100. Exemplarily, the mass ratio of the catalyst to the fatty acid may be, but is not limited to, 0.2:100, 0.3:100, 0.4:100, 0.5:100, 0.6:100, 0.7:100, 0.8:100, 0.9:100, 1:100, or any range of two of these values.

[0079] Specifically, the antioxidants include one or more of hindered phenolic antioxidants and phosphite antioxidants. Optionally, hindered phenolic antioxidants include one or more of 2,6-di-tert-butyl-4-methylphenol, N,N′-bis-(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyl)hexamethylenediamine, and pentaerythritol tetrakis[β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]. Phosphite antioxidants include one or more of 2′-ethylbis(4,6-di-tert-butylphenyl)fluorophosphite and tris(2,4-di-tert-butylphenyl)phosphite.

[0080] In some embodiments, the antioxidants include hindered phenolic antioxidants and phosphite antioxidants. Specifically, the antioxidants include hindered phenolic antioxidants and phosphite antioxidants in a mass ratio of (1~5):1. For example, the mass ratio of hindered phenolic antioxidants to phosphite antioxidants can be, but is not limited to, 1:1, 1.5:1, 2:1, 2.5:1, 3:1, 3.5:1, 4:1, 4.5:1, 5:1, or any combination of these values. Using the above-mentioned mass ratio of two types of antioxidants in combination is beneficial for further improving the appearance and whiteness of the amide compound and its plasticizing effect, while also improving the heat resistance and elongation at break of the prepared polymer material.

[0081] In some embodiments, the mass ratio of antioxidant to fatty acid is (1-6):100. For example, the mass ratio of antioxidant to fatty acid may be, but is not limited to, 1:100, 2:100, 3:100, 4:100, 5:100, 6:100, or any combination of these values.

[0082] In one specific example, the fatty acid is stearic acid, and the alicyclic amine includes one or more of 4,4-diaminodicyclohexylmethane, polyaminopolycyclohexylmethane, 1,3-cyclohexyldimethylamine, and isophorone diamine.

[0083] The aforementioned amide compounds have a more regular structure, excellent heat resistance, and high color due to the introduction of polyamine and amide polar groups. They can form covalent / hydrogen bonds with a variety of plastic matrix materials, exhibiting good compatibility. At the same time, the relatively soft alicyclic structure has little impact on the mechanical properties of the plastic matrix, resulting in stable plasticizing effect and excellent lubrication effect. This improves the processing performance of plastics and broadens their application range.

[0084] A second aspect of this application provides a method for preparing an amide compound, comprising the following steps:

[0085] Amide compounds are prepared by amidation reaction of fatty acids and alicyclic amines;

[0086] The structural formula of the fatty acid is CH3CH2(CH2). n1 COOH; Alicyclic amines contain C5~C6 10 Polyamines with alicyclic groups; the structural formula of the amide compound is ;

[0087] In the formula, R1 contains C5~C 10 Alicyclic groups;

[0088] n1 is an integer between 9 and 15, and n2 ≥ 2.

[0089] As is understandable, the specific fatty acids and alicyclic amines are as described in the first aspect above, and will not be repeated here.

[0090] In some embodiments, a catalyst and an antioxidant are also added during the amide reaction of fatty acids and alicyclic amines. The specific types and amounts of catalysts and antioxidants are as described in the first aspect above and will not be repeated here.

[0091] In some embodiments, the step of amidating fatty acids and alicyclic amines includes:

[0092] Under a protective atmosphere, fatty acids, catalysts, and antioxidants are mixed and heated to melt the fatty acids;

[0093] The alicyclic amine was added to the reaction system at a temperature of 70℃~90℃.

[0094] Heat the reaction system to 90℃~110℃ and hold for 0.5h~2h, then continue to heat to 190℃~220℃ and hold for 4h~6h. Stop the reaction when the acid value is less than 10mgKOH / g.

[0095] Specifically, in the step of adding alicyclic amines to the reaction system at 70℃~90℃, the addition time of the alicyclic amines is 40min~60min.

[0096] Specifically, the heating rate for each heating cycle is independently 0.5℃ / min to 1℃ / min.

[0097] Specifically, after stopping the reaction when the acid value is less than 10 mg KOH / g, the reaction system is further cooled to 160°C to 180°C to obtain the amide compound.

[0098] In one embodiment, please refer to Figure 1 The amidation reaction of fatty acids and alicyclic amines includes steps S110, S120, and S130:

[0099] Step S110: Under a protective atmosphere, fatty acids, catalyst and antioxidant are mixed and heated to melt the fatty acids. The mass ratio of the catalyst to the fatty acids is (0.2~1):100, and the mass ratio of the antioxidant to the fatty acids is (1~6):100.

[0100] Step S120: At 70℃~90℃, add alicyclic amine to the reaction system for 40min~60min. The molar ratio of the amine group in the alicyclic amine to the carboxyl group in the fatty acid is 1:(1.02~1.2).

[0101] Step S130: Heat the reaction system to 90℃~110℃ at a rate of 0.5℃ / min~1℃ / min and hold for 0.5h~2h. Continue to heat to 190℃~220℃ and hold for 4h~6h. Stop the reaction when the acid value is less than 10mgKOH / g. Cool to 160℃~180℃ to obtain the amide compound.

[0102] Figure 1 This is a schematic flowchart illustrating a method for preparing an amide compound according to an embodiment of this application. It should be understood that, although Figure 1 The steps in the flowchart shown are displayed sequentially according to the arrows. However, these steps are not necessarily performed in the order indicated by the arrows. Unless otherwise specified in this document, there is no strict order requirement for the execution of these steps; they can be executed in other orders. Figure 1 At least some of the steps in the process may include multiple sub-steps or multiple stages. These sub-steps or stages are not necessarily completed at the same time, but can be executed at different times. Their execution order is not necessarily sequential, but can be executed in turn or alternately with at least some of other steps or other sub-steps or stages.

[0103] Traditional techniques include transesterification to prepare amide compounds, such as reacting fatty acid esters with organic amines. However, this method leaves some fatty acid ester residues, which have poor antioxidant properties and are prone to oxidative deterioration during use, leading to decreased lubrication performance. In addition, fatty acid esters have low viscosity indices, and their viscosity varies greatly with temperature, which is not conducive to maintaining stable viscosity and / or lubrication effects under different temperature conditions. They also pose a certain risk of hydrolysis, affecting the performance of the product. In some embodiments of this application, amide compounds are prepared by amidation reaction of fatty acids and alicyclic amines. When applied to polymer materials, amide compounds have stable plasticizing and / or lubricating effects and do not pose a risk of hydrolysis. The prepared products have better performance, such as better surface gloss.

[0104] Furthermore, if the alicyclic amine is an aromatic amine, the preparation method of the amide compound in some embodiments of this application requires a higher reaction temperature for aromatic amines, which easily leads to oxidation of the amide compound, resulting in insufficient appearance and whiteness, thus affecting the appearance of the polymer material. In addition, the amide compound prepared from aromatic amines will cause a decrease in the mechanical properties of the polymer material, such as elongation at break. Therefore, in some embodiments of this application, the amide compound is prepared by amidation reaction of alicyclic amines with fatty acids. On the one hand, the prepared amide compound has stable plasticizing and / or lubricating effects and good high-temperature resistance. When used in polymer materials, it is beneficial to improve the elongation at break while ensuring high tensile strength. On the other hand, the prepared amide compound has a good appearance, appearing as a white powder or a white to pale yellow powder, with a whiteness of less than or equal to 5.

[0105] A third aspect of this application provides the use of an amide compound in the preparation of powder coatings, aqueous dispersions, or polymer materials.

[0106] Specifically, amide compounds can be used as one or more of the following: dispersants, plasticizers, release agents, and lubricants in powder coatings, aqueous dispersions, or polymer materials.

[0107] The fourth aspect of this application provides a polymer material comprising a polymer matrix and an additive, wherein the additive comprises the amide compound described in the first aspect or an amide compound prepared by the preparation method described in the second aspect.

[0108] Specifically, the polymer matrix includes one or more of polyamide resin, polycarbonate, polyurethane, polyvinyl chloride, polyolefin and polyacrylonitrile.

[0109] Specifically, the additives may be, but are not limited to, one or more of dispersants, plasticizers, mold release agents, and lubricants.

[0110] In one example, the mass ratio of the amide compound to the polymer matrix is ​​3:100. It is understood that the amide compounds in some embodiments of this application exhibit better plasticizing effects than conventional amide compounds, requiring less addition to the polymer matrix, or achieving effects comparable to conventional amide compounds with a smaller addition amount.

[0111] The aforementioned polymer materials possess good heat resistance, processing performance, mechanical properties, and a pleasant appearance.

[0112] To make the objectives and advantages of this application clearer, the amide compounds and their effects of this application are further described in detail below with reference to specific embodiments. It should be understood that the specific embodiments described herein are only for explaining this application and should not be used to limit this application. Unless otherwise specified, the following embodiments do not include components other than unavoidable impurities. Unless otherwise specified, the drugs and instruments used in the embodiments are conventional choices in the art. Experimental methods in the embodiments that do not specify specific conditions were implemented according to conventional conditions, such as those described in literature, books, or methods recommended by the manufacturer.

[0113] The main sources of raw materials used in the following examples and comparative examples are shown in Table 1 below.

[0114] Table 1 Sources of each raw material

[0115]

[0116] Example 1

[0117] This embodiment provides an amide compound, and the preparation steps are as follows:

[0118] Weigh out 100 parts by weight of stearic acid, 0.2 parts by weight of phosphorous acid, 5 parts by weight of antioxidant 501, and 1 part by weight of antioxidant 168 and add them to the reactor. After introducing a protective gas into the reactor, heat the reactor until the stearic acid is completely melted and start stirring. Continue heating to 90°C, and add 4,4-diaminodicyclohexylmethane to the reactor, making the molar ratio of the amino groups in 4,4-diaminodicyclohexylmethane to the carboxyl groups in stearic acid 1:1.02. After the addition is completed in about 40 minutes, heat the reactor to 100°C at a rate of 1.0°C / min and hold for 2 hours. Then heat the reactor to 200°C and hold for 5 hours for dehydration. The reaction is terminated when the acid value is less than 10 mg KOH / g. Cool the reactor to 170°C and discharge the product to obtain the amide compound of this embodiment.

[0119] This embodiment also provides a polymer material, the preparation steps of which are as follows:

[0120] By mass, 100 parts of polyurethane WH1185EC and 3 parts of the amide compound from Example 1 above were selected, thoroughly mixed, and then cast to prepare a sample for testing.

[0121] Example 2

[0122] This embodiment provides an amide compound, and the preparation steps are as follows:

[0123] Weigh out 100 parts by weight of stearic acid, 0.6 parts by weight of hypophosphite, 0.5 parts by weight of antioxidant 1098, and 0.5 parts by weight of antioxidant 168 and add them to the reactor. After introducing a protective gas into the reactor, heat the reactor until the stearic acid is completely melted and start stirring. Continue heating to 90°C, add wanamine 2300 to the reactor, ensuring a molar ratio of amine groups in wanamine 2300 to carboxyl groups in stearic acid of 1:1.1. After the addition is completed in about 50 minutes, heat the reactor to 110°C at a rate of 0.8°C / min and hold for 1.5 hours. Then heat the reactor to 220°C and hold for 4 hours for dehydration. The reaction is terminated when the acid value is less than 10 mg KOH / g. Cool the reactor to 180°C and discharge the product to obtain the amide compound of this embodiment.

[0124] This embodiment also provides a polymer material, the preparation steps of which are as follows:

[0125] By mass, 100 parts of polyurethane WH1185EC and 3 parts of the amide compound from Example 2 above were selected, thoroughly mixed, and then cast to prepare a sample for testing.

[0126] Example 3

[0127] This embodiment provides an amide compound, and the preparation steps are as follows:

[0128] Weigh out 100 parts by weight of decanoic acid, 1 part by weight of phosphorous acid, 3 parts by weight of antioxidant 1010, and 1 part by weight of antioxidant 168 and add them to the reactor. After introducing a protective gas into the reactor, heat the reactor until the stearic acid is completely melted and start stirring. Continue heating to 70°C, add isophorone diamine, making the molar ratio of the amino group in isophorone diamine to the carboxyl group in stearic acid 1:1.2. After the addition is completed in about 60 minutes, heat the reactor to 90°C at a rate of 0.5°C / min and hold for 0.5 hours. Then heat the reactor to 190°C and hold for 6 hours for dehydration. The reaction is terminated when the acid value is less than 10 mg KOH / g. Cool the reactor to 160°C and discharge the product to obtain the amide compound of this embodiment.

[0129] This embodiment also provides a polymer material, the preparation steps of which are as follows:

[0130] Weigh 100 parts by weight of polyurethane WH1185EC and 3 parts by weight of the amide compound of Example 3 above, mix them thoroughly and then pour them to prepare a sample for testing.

[0131] Example 4

[0132] This embodiment provides an amide compound, and the preparation steps are similar to those of the amide compound in Example 1, the difference being the alicyclic amine. In this embodiment, the alicyclic amine is aminomethylcyclopentylamine (structural formula: The other steps are the same as in Example 1, and will not be repeated here.

[0133] This embodiment also provides a polymer material, the preparation steps of which are as follows:

[0134] Weigh 100 parts by weight of polyurethane WH1185EC and 3 parts by weight of the amide compound of Example 4 above, mix them thoroughly and then pour them to prepare a sample for testing.

[0135] Comparative Example 1

[0136] Comparative Example 1 provides an amide compound, prepared by the following steps:

[0137] Weigh out 100 parts by weight of stearic acid, 0.2 parts by weight of phosphorous acid, 5 parts by weight of antioxidant 501, and 1 part by weight of antioxidant 168 and add them to the reactor. After introducing a protective gas into the reactor, heat the reactor until the stearic acid is completely melted and start stirring. Continue heating to 90°C, add ethylenediamine, with the molar ratio of the amino groups in ethylenediamine to the carboxyl groups in stearic acid being 1:1.02. After the addition is completed in about 40 minutes, heat the reactor to 100°C at a rate of 1.0°C / min and hold for 2 hours. Then heat the reactor to 200°C and hold for 5 hours for dehydration. The reaction is terminated when the acid value is less than 10 mg KOH / g. Cool the reactor to 170°C and discharge the product to obtain the amide compound of Comparative Example 1.

[0138] Comparative Example 1 also provides a polymer material, the preparation steps of which are as follows:

[0139] Weigh 100 parts by weight of polyurethane WH1185EC and 3 parts by weight of the amide compound of Comparative Example 1 above, mix thoroughly and then pour to prepare a sample for testing.

[0140] Comparative Example 2

[0141] Comparative Example 2 provides a plasticizer, dioctyl phthalate.

[0142] Comparative Example 2 also provides a polymer material, the preparation steps of which are as follows:

[0143] Weigh 100 parts by weight of polyurethane WH1185EC and 3 parts by weight of plasticizer dioctyl phthalate, mix thoroughly and then pour into a sample for testing.

[0144] Comparative Example 3

[0145] Comparative Example 3 provides a polymer material, the preparation steps of which are as follows:

[0146] Weigh 100 parts of polyurethane WH1185EC by weight, cast them to obtain a sample for testing.

[0147] Comparative Example 4

[0148] Comparative Example 4 provides an amide compound that differs from the amide compound of Example 1 in that cyclohexylamine is used instead of 4,4-diaminodicyclohexylmethane in Example 1. The other steps are the same as in Example 1 and will not be repeated here.

[0149] Comparative Example 4 also provides a polymer material, the preparation steps of which are as follows:

[0150] By mass, 100 parts of polyurethane WH1185EC and 3 parts of the amide compound of Comparative Example 4 were selected, thoroughly mixed, and then cast to prepare a sample for testing.

[0151] The amide compounds and polymer materials of the above embodiments and comparative examples were tested, and the main test methods are as follows:

[0152] 1. Melting point determination: The melting point of the amide compound shall be determined in accordance with ISO 11357-1:2023;

[0153] 2. Acid value determination: The acid value of the amide compound was determined according to ASTM D-1386-78;

[0154] 3. Whiteness test: The whiteness of the amide compound was determined according to ASTM E313-2015;

[0155] 4. Softening point and flow initiation temperature: The softening point and flow initiation temperature of the polymer material were tested using a constant pressure capillary rheometer with a test load of 10 N and a heating rate of 5 °C / min.

[0156] 5. Thermal stability test: The thermal decomposition temperature of the polymer material (at 5% weight loss) was determined according to the thermal decomposition method.

[0157] 6. Mechanical property testing: The tensile strength and elongation at break of the polymer material shall be determined in accordance with ISO 527-2:2012.

[0158] The test results of the amide compounds and polymer materials in each embodiment and comparative example are shown in Tables 2 and 3 below.

[0159] Table 2 Test results for each embodiment

[0160]

[0161] Table 3 Test results of each comparative example

[0162]

[0163] As can be seen from the table above, the amide compounds obtained in the embodiments of this application have low acid values ​​and high whiteness. Compared with Comparative Example 1, it can be seen that the amide compounds obtained by using alicyclic amines in the embodiments of this application have higher melting points and higher thermal decomposition temperatures of polyurethane. Furthermore, the amide compounds obtained in the embodiments have no adverse effect on the tensile strength of polyurethane materials and significantly improve their elongation at break. Compared with Comparative Examples 2 and 3, it can be seen that the processing window (the difference between the softening point and the flow initiation temperature) of the polymer materials prepared in the embodiments of this application is widened, and the plasticizing effect is significant. Compared with Comparative Example 4, the amide compounds prepared by using alicyclic amines containing at least two amino groups in the embodiments of this application are beneficial to improving the thermal decomposition temperature and elongation at break of polyurethane materials, while also exhibiting better plasticizing effects.

[0164] In addition, optimizing the structure of alicyclic amines can further improve the whiteness and plasticizing effect of amide compounds, as well as the thermal decomposition temperature and elongation at break of the prepared polyurethane materials.

[0165] The technical features of the above embodiments can be combined in any way. For the sake of brevity, not all possible combinations of the technical features in the above embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0166] The embodiments described above are merely illustrative of several implementation methods of this application, intended to facilitate a detailed understanding of the technical solutions of this application, but should not be construed as limiting the scope of protection of the invention patent. It should be noted that those skilled in the art can make various modifications and improvements without departing from the concept of this application, and these all fall within the scope of protection of this application. It should be understood that technical solutions obtained by those skilled in the art based on the technical solutions provided in this application through logical analysis, reasoning, or limited experimentation are all within the scope of protection of the appended claims. Therefore, the scope of protection of this patent application should be determined by the content of the appended claims, and the specification and drawings can be used to interpret the content of the claims.

Claims

1. A method for preparing an amide compound, characterized in that, Includes the following steps: Amide compounds are prepared by amidation reaction of fatty acids and alicyclic amines; The fatty acid has the structural formula CH3CH2(CH2). n1 COOH; the alicyclic amine is Wanamine 2300, derived from Wanhua Chemical; the structural formula of the amide compound is: ； In the formula, n2 is 3, and R1 is selected from... ; n1 is an integer between 9 and 15; In the step of amide reaction of fatty acids and alicyclic amines, a catalyst and an antioxidant are also added; The antioxidants include hindered phenolic antioxidants and phosphite antioxidants in a mass ratio of (1~5):1; The steps involved in the amidation reaction of fatty acids and alicyclic amines include: Under a protective atmosphere, the fatty acid, catalyst, and antioxidant are mixed and heated to melt the fatty acid. The alicyclic amine was added to the reaction system at a temperature of 70℃~90℃. Heat the reaction system to 90℃~110℃ and hold for 0.5h~2h, then continue to heat to 190℃~220℃ and hold for 4h~6h. Stop the reaction when the acid value is less than 10mgKOH / g.

2. The method for preparing the amide compound according to claim 1, characterized in that, n1 is an integer between 11 and 15.

3. The method for preparing the amide compound according to claim 1 or 2, characterized in that, The molar ratio of the carboxyl group in the fatty acid to the amino group in the alicyclic amine is (1.02~1.2):

1.

4. The method for preparing the amide compound according to claim 1 or 2, characterized in that, The catalyst includes one or more of phosphoric acid, phosphorous acid, hypophosphite, sodium hypophosphite, and p-toluenesulfonic acid.

5. The method for preparing the amide compound according to claim 1 or 2, characterized in that, One or more of the following conditions must be met: (1) The hindered phenolic antioxidants include one or more of 2,6-di-tert-butyl-4-methylphenol, N,N′-bis-(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyl)hexamethylenediamine and pentaerythritol tetrakis[β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]; The phosphite antioxidants include one or more of 2′-ethylbis(4,6-di-tert-butylphenyl)fluorophosphite and tris(2,4-di-tert-butylphenyl)phosphite; (2) The mass ratio of the catalyst to the fatty acid is (0.2~1):100; (3) The ratio of the mass of the antioxidant to the mass of the fatty acid is (1~6):

100.

6. The use of the amide compound prepared by the method of any one of claims 1 to 5 in the preparation of powder coatings, aqueous dispersions or polymer materials.

7. The application as described in claim 6, characterized in that, The amide compound is used as one or more of the following: dispersant, plasticizer, release agent, and lubricant in powder coatings, aqueous dispersions, or polymer materials.

8. A polymer material, characterized in that, It includes a polymer matrix and an additive, wherein the additive includes an amide compound prepared by the method for preparing an amide compound according to any one of claims 1 to 5.

9. The polymer material as claimed in claim 8, characterized in that, The polymer matrix includes one or more of polyamide resin, polycarbonate, polyurethane, polyvinyl chloride, polyolefin and polyacrylonitrile.

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