Maleic anhydride functionalized long chain alkanes, methods of making and using the same

Abstract

The application belongs to the technical field of polymer material preparation, and particularly relates to maleic anhydride functionalized long-chain alkane shown in formula I and a preparation method and application thereof. The maleic anhydride functionalized long-chain alkane provided by the application has an extremely similar structure to ASA, and thus exhibits the same performance. The application adopts alkane as a raw material to prepare the maleic anhydride functionalized long-chain alkane, and the raw material is sufficient and low in price. In addition, conventional ASA needs to be subjected to double bond isomerization to transfer the reaction site of maleic anhydride from a terminal position to a non-terminal position. The application adopts a free radical path to synthesize the maleic anhydride functionalized long-chain alkane, and a non-terminal free radical (a double-substituted free radical) is more stable than a terminal substituent (a single-substituted free radical), so that the reaction site is preferentially on the non-terminal position. Therefore, the synthesis process provided by the application is simpler.

Description

Technical Field

[0001] This invention belongs to the field of polymer material preparation technology, specifically relating to a maleic anhydride-functionalized long-chain alkane, its preparation method, and its application. Background Technology

[0002] Alkenyl succinic anhydrides (ASA) are a general term for a class of organic chemical products, and their structural formulas are shown below.

[0003]

[0004] It contains two hydrophobic carbon chain groups (alkane and olefin segments) and one hydrophilic anhydride group. The anhydride group is highly reactive and can undergo reactions such as hydrolysis, alcoholysis, aminolysis, esterification, and acylation. This unique structure leads to the wide range of applications for ASA. Different carbon numbers in the carbon chain correspond to different uses: ASA with fewer than 10 carbons is typically used in food preparation and as a thickener in some foods such as juices and jellies, while ASA with 10–35 carbons is used as a sizing agent in papermaking, a preservative for wood, a waterproofing agent for leather and textiles, and an additive in varnishes, lubricants, and metalworking fluids, etc.

[0005] ASA is generally synthesized via an alpha-ene reaction between an inner olefin and maleic anhydride. The common industrial approach involves first isolating the α-olefin obtained through Fischer-Tropsch synthesis or ethylene oligomerization into an inner olefin via isomerization, followed by an alpha-ene reaction between the inner olefin and maleic anhydride. However, the supply of raw materials for this route is unreliable; therefore, finding alternatives to ASA and simple, efficient synthetic routes for these alternatives is of great significance. Summary of the Invention

[0006] In view of this, the present invention provides a maleic anhydride-functionalized long-chain alkane, its preparation method and application.

[0007] The technical solution provided by this invention is as follows:

[0008] A maleic anhydride-functionalized long-chain alkane having the following general structural formula I:

[0009]

[0010] Among them, R 1 and R 2 They may be the same or different, and are independently selected from hydrogen or C. 1-37 Alkyl, provided it is a long-chain alkane The carbon chain length is C5–40; R 3 Selected from hydrogen, fluorine, chlorine, bromine, iodine, and C 1-6 alkyl;

[0011] Among them, long-chain alkanes When the carbon chain length is less than C12, the side chain maleic anhydride functionalized groups Located on terminal or non-terminal carbons, but mainly on non-terminal carbons, where * indicates a connection site;

[0012] When the carbon chain length of a long-chain alkane is C13 or longer, the maleic anhydride functionalized group in the side chain is located on a non-terminal carbon.

[0013] According to an embodiment of the present invention, the maleic anhydride functionalized long-chain alkane The carbon chain length is C8–20, R 3 It is selected from fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl or isopropyl.

[0014] According to an embodiment of the present invention, the melting point of the maleic anhydride functionalized long-chain alkane is -80 to 20°C, preferably -70.5 to 10°C.

[0015] According to an embodiment of the present invention, the acid value of the maleic anhydride functionalized long-chain alkane is 50-600 mg KOH / g, preferably 100-500 mg KOH / g.

[0016] According to an embodiment of the present invention, the viscosity of the maleic anhydride functionalized long-chain alkane is 10-300 mPa*s, preferably 20-250 mPa*s.

[0017] According to an embodiment of the present invention, the density of the maleic anhydride functionalized long-chain alkane is 0.5 to 1.1 g / mL, preferably 0.7 to 1 g / mL.

[0018] According to an embodiment of the present invention, the maleic anhydride-functionalized long-chain alkane is selected from n-octane, n-dodecane, n-octadecaane, or n-tetracosane functionalized with the following functional monomers II-1 or II-2, i.e., substances formed by removing the halogen substituent of the functional monomers II-1 or II-2 and attaching them to n-octane, n-dodecane, n-octadecaane, or n-tetracosane.

[0019]

[0020] According to an embodiment of the present invention, the maleic anhydride-functionalized long-chain alkane is a mixture formed by grafting maleic anhydride onto different sites (carbons) of the long-chain alkane.

[0021] The present invention also provides a method for preparing maleic anhydride-functionalized long-chain alkanes as described above, comprising the following steps:

[0022] Add C to the reaction vessel 5-40 Long-chain alkanes Functionalized monomers The reactants and initiators are heated and reacted in an inert gas atmosphere.

[0023] Among them, long-chain alkanes Chinese R 1 and R 2 It has the definition as described above;

[0024] Functionalized monomers In this context, X is selected from fluorine, chlorine, bromine, and iodine, and R... 3 It has the definition described above.

[0025] According to an embodiment of the present invention, the molar ratio of the long-chain alkane to the functionalized monomer is 8:1 to 1000:1, preferably 9:1 to 100:1, and even more preferably 10:1 to 50:1.

[0026] According to an embodiment of the present invention, the molar ratio of the initiator to the functionalized monomer is 1:1 to 1:20, preferably 1:2 to 1:10, and even more preferably 1:3 to 1:8.

[0027] According to an embodiment of the present invention, the reaction temperature is 80–140°C and the reaction time is 1–48 hours.

[0028] According to an embodiment of the present invention, the method further includes a post-processing step after the reaction is completed, including: removing unreacted long-chain alkanes by vacuum distillation to obtain the target product, maleic anhydride-functionalized long-chain alkanes.

[0029] According to an embodiment of the present invention, the initiator is a free radical initiator, preferably at least one of benzoyl peroxide, dicumyl peroxide, and tert-butyl peroxide.

[0030] According to an embodiment of the present invention, the initiator can be added in a single application or in batches.

[0031] According to an embodiment of the present invention, the inert gas is selected from nitrogen and argon.

[0032] The present invention also provides the uses of maleic anhydride functionalized long-chain alkanes as described above, including for the preparation of food, sizing agents for papermaking, preservatives for wood, waterproofing agents for leather and textiles, and additives for varnishes, lubricants, and metalworking oils.

[0033] Beneficial effects:

[0034] (1) The maleic anhydride functionalized long-chain alkane provided by the present invention has a structure that is very similar to that of ASA, and thus exhibits the same properties.

[0035] (2) The present invention uses alkanes as raw materials to prepare maleic anhydride functionalized long-chain alkanes, and the raw materials are abundant and inexpensive.

[0036] (3) Conventional ASA requires double bond isomerization to shift the reaction site of maleic anhydride from the terminal to the non-terminal position. This invention uses a radical pathway to synthesize maleic anhydride-functionalized long-chain alkanes. Non-terminal radicals (disubstituted radicals) are more stable than terminal substituents (monosubstituted radicals), so the reaction site preferentially occurs at the non-terminal position. Therefore, the synthetic process provided by this invention is simpler. Attached Figure Description

[0037] Figure 1 The infrared spectrum of the maleic anhydride-functionalized long-chain alkane prepared in Example 1.

[0038] Terminology Definitions and Explanations

[0039] Unless otherwise stated, the definitions of groups and terms recorded in this application specification and claims, including their definitions as examples, exemplary definitions, preferred definitions, definitions recorded in tables, and definitions of specific compounds in the examples, can be arbitrarily combined and combined with each other. Such combinations and combinations of group definitions and compound structures shall fall within the scope of this application specification.

[0040] Term "C" 1-37 "Alkyl" should be understood to mean a straight-chain or branched saturated monovalent hydrocarbon group having 1 to 37 carbon atoms, such as a straight-chain or branched saturated monovalent hydrocarbon group having 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms. The alkyl group is, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, 2-methylbutyl, 1-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, neopentyl, 1,1-dimethylpropyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl, 2-ethylbutyl, 1-ethylbutyl, 3,3-dimethylbutyl, 2,2-dimethylbutyl, 1,1- Dimethylbutyl, 2,3-dimethylbutyl, 1,3-dimethylbutyl, or 1,2-dimethylbutyl, or their isomers. In particular, the group has 1, 2, 3, 4, 5, or 6 carbon atoms (“C…”). 1-6 Alkyl groups, such as methyl, ethyl, propyl, butyl, isopropyl, isobutyl, sec-butyl, tert-butyl, and more particularly, the groups having 1, 2, or 3 carbon atoms (“C”). 1-3 Alkyl), such as methyl, ethyl, n-propyl, or isopropyl. The same definition also includes "C". 1-6 alkyl".

[0041] The term "C5-40" refers to alkane having 5, 6, 7, 8, 9, 10...40 carbon atoms, and the alkane formed by these carbon atoms is a straight-chain or branched saturated alkane. The same definition also includes "C8-20". Detailed Implementation

[0042] The technical solution of the present invention will be further described in detail below with reference to specific embodiments. It should be understood that the following embodiments are merely illustrative and explanatory of the present invention, and should not be construed as limiting the scope of protection of the present invention. All technologies implemented based on the above content of the present invention are covered within the scope of protection intended by the present invention.

[0043] Unless otherwise stated, the raw materials and reagents used in the following examples are commercially available products or can be prepared by known methods.

[0044] 1. Product structure analysis

[0045] In the following examples, the ratio of end-grafted to non-end-grafted maleic anhydride-functionalized long-chain alkanes was calculated as follows:

[0046] R = A1 / A2

[0047] In the formula, A1 represents the integrated area of ​​chemical shifts σ2.53–2.29 in the 1H NMR spectrum of the compound; A2 represents the integrated area of ​​chemical shifts σ2.28–2.04 in the 1H NMR spectrum of the compound. Deuterated chloroform was used as the solvent for the 1H NMR spectra, and the measurements were performed on a Bruker Avance III 400HD liquid NMR spectrometer.

[0048] 2. Melting point analysis

[0049] The sample was characterized using a differential scanning calorimeter (DSC) under nitrogen protection. The temperature program was set from -120 °C to 50 °C, and the heating rate was 10 °C / min. The DSC curves were obtained, and the melting point of the product sample was calculated using the tangent method.

[0050] 3. Cobb 60s detection

[0051] ASA emulsifier (provided by Nalco Chemical Company, USA) was mixed with ASA or the samples prepared in Examples 1-8 at a ratio of 0.9:1 (mass ratio), and stirred for 2 minutes at 4000 rpm using a high-speed homogenizer to obtain a sizing solution. The sizing solution and additives (ASA dosage 2 kg / t paper, polymer sizing accelerator (provided by Guangdong Chengming Chemical Co., Ltd.) dosage 150 g / t paper) were added to the pulp and stirred. The sheet weight was 100 g / m³. 2After drying twice, paper samples were obtained. The obtained paper samples were placed in a desiccator to equilibrate the moisture for 10 minutes, and the water resistance of the paper was determined by the Cobb surface water absorption weight method. The Cobb 60s of the paper samples was tested (determined according to the national standard GB / T461.3-2005).

[0052] 4. Acid value test

[0053] Accurately weigh 3.00–5.00 g of the samples prepared in Examples 1–8 and Comparative Example 1, place them in a 250 ml Erlenmeyer flask, add 50 ml of neutral diethyl ether-ethanol mixture, shake to dissolve the sample, and if necessary, place it in hot water to warm and promote dissolution. Then cool to room temperature, add 2–3 drops of phenolphthalein indicator, and titrate with 0.1000 mol / L KOH standard solution until a faint pink color appears and does not fade within 30 seconds, which is the endpoint.

[0054] X = (cV * 56.1) / m

[0055] In the formula, c is the concentration of potassium hydroxide standard solution, which is 0.1000 mol / L; V is the volume of potassium hydroxide standard solution consumed; and m is the mass of the sample.

[0056] 5. Viscosity test

[0057] According to the national standard GB / T 265-1988 "Determination of kinematic viscosity and calculation of dynamic viscosity of petroleum products", the VISCO BALL viscometer was used for measurement, and the test temperature was 25℃.

[0058] 6. Density test

[0059] According to the national standard GB / T 6750-2007, the density test is conducted using the specific gravity cup method. This method involves filling a specific gravity cup of known volume with the product being tested, measuring the mass of the product using a balance, and dividing this mass by the volume of the specific gravity cup to obtain the density of the product. The test is conducted at (23.0±0.5)℃.

[0060] 7. Molecular weight HRMS (ESI) analysis

[0061] The molecular weight of the compounds was determined by HRMS (ESI) using a matrix-assisted laser desorption / ionization time-of-flight mass spectrometer according to the standard JY / T 003-1996 General Rules for Organic Mass Spectrometry.

[0062] Example 1

[0063] Functionalized monomer II-1

[0064] 200 g of n-octane (1.75 mol), 30 g of the functionalized monomer shown in structural formula II-1 (0.18 mol), and 9.7 g of benzoyl peroxide (0.04 mol) were added to a 500 mL reactor. The reactor was then purged with nitrogen five times and heated to 120 °C for 24 hours under a nitrogen atmosphere. The hydrogen chloride gas produced was absorbed with alkaline solution through a nitrogen line. Post-treatment: After cooling to room temperature, unreacted n-octane was removed by atmospheric distillation. Then, vacuum distillation was performed to obtain 38.4 g of the target product, maleic anhydride-functionalized n-octane. The theoretical yield, calculated based on complete reaction of the functionalized monomer, was 44.1 g, representing a yield of 87%. Theoretical calculation [M+H] + The value is 245.7720. A peak of 245.7715 was found on the HRMS (ESI) spectrum. The infrared spectrum is as follows. Figure 1 As shown in the figure. Based on the above characterization results, it can be confirmed that the functionalized monomer was successfully grafted onto n-octane. The properties of the product are shown in Table 1.

[0065] Example 2

[0066] 200 g of n-dodecane (1.18 mol), 20 g of the functionalized monomer shown in structural formula II-1 (0.12 mol), and 4.8 g of benzoyl peroxide (0.02 mol) were added to a 500 mL reactor. The reactor was then purged with nitrogen five times and heated to 120 °C for 24 hours under a nitrogen atmosphere. The hydrogen chloride gas produced was absorbed with alkaline solution through a nitrogen pipeline. Post-treatment: After cooling to room temperature, unreacted raw materials were removed by vacuum distillation to obtain 31.8 g of the target product, maleic anhydride-functionalized n-dodecane. The theoretical yield, calculated based on complete reaction of the functionalized monomer, is 36.1 g, representing a yield of 88%. Theoretical calculation [M+H] + The value was 301.8283, and a peak of 301.8273 was found on the HRMS (ESI) spectrum. Based on the above characterization results, it can be confirmed that the functionalized monomer was successfully grafted onto the long-chain alkane. The properties of the product are shown in Table 1.

[0067] Example 3

[0068] 200 g of n-tetane (1.09 mol), 20 g of the functionalized monomer shown in structural formula II-1 (0.12 mol), and 4.8 g of benzoyl peroxide (0.02 mol) were added to a 500 mL reactor. The reactor was then purged with nitrogen five times and heated to 120 °C for 24 hours under a nitrogen atmosphere. The hydrogen chloride gas produced was absorbed with alkaline solution through a nitrogen pipeline. Post-treatment: After cooling to room temperature, unreacted raw materials were removed by vacuum distillation to obtain 32.0 g of the target product, maleic anhydride-functionalized n-dodecane. The theoretical yield, calculated based on complete reaction of the functionalized monomer, is 42.5 g, representing a yield of 75%. Theoretical calculation [M+H] +The value was 315.8549, and a peak of 315.8565 was found on the HRMS (ESI) spectrum. Based on the above characterization results, it can be confirmed that the functionalized monomer was successfully grafted onto the long-chain alkane. The properties of the product are shown in Table 1.

[0069] Example 4

[0070] 200 g of n-octadecane (0.79 mol), 13.4 g of the functionalized monomer shown in structural formula II-1 (0.08 mol), and 4.8 g of benzoyl peroxide (0.02 mol) were added to a 500 mL reactor. The reactor was then purged with nitrogen five times and heated to 120 °C for 24 hours under a nitrogen atmosphere. The hydrogen chloride gas produced was absorbed with alkaline solution through a nitrogen pipeline. Post-treatment: After cooling to room temperature, unreacted raw materials were removed by vacuum distillation to obtain 27.7 g of the target product, maleic anhydride-functionalized n-octadecane. The theoretical yield, calculated based on complete reaction of the functionalized monomer, was 30.8 g, representing a yield of 90%. Theoretical calculation [M+H] + The value was 385.9878, and a peak of 385.9867 was found on the HRMS (ESI) spectrum. Based on the above characterization results, it can be confirmed that the functionalized monomer was successfully grafted onto the long-chain alkane. The properties of the product are shown in Table 1.

[0071] Example 5

[0072] 200 g of n-octadecane (0.79 mol), 13.4 g of the functionalized monomer shown in structural formula II-1 (0.08 mol), and 5.4 g of dicumyl peroxide (0.02 mol) were added to a 500 mL reactor. The reactor was then purged with nitrogen five times and heated to 120 °C for 40 hours under a nitrogen atmosphere. The hydrogen chloride gas produced was absorbed with alkaline solution through a nitrogen pipeline. Post-treatment: After cooling to room temperature, unreacted raw materials were removed by vacuum distillation to obtain 29.2 g of the target product, maleic anhydride-functionalized n-octadecane. The theoretical yield, calculated based on complete reaction of the functionalized monomer, was 30.8 g, representing a yield of 95%. Theoretical calculation [M+H] + The value was 385.9878, and a peak of 385.9867 was found on the HRMS (ESI) spectrum. Based on the above characterization results, it can be confirmed that the functionalized monomer was successfully grafted onto the long-chain alkane. The properties of the product are shown in Table 1.

[0073] Example 6

[0074] Functionalized monomer II-2

[0075] 200 g of n-octadecane (0.79 mol), 11.7 g of the functionalized monomer shown in structural formula II-2 (0.08 mol), and 3.9 g of tert-butyl peroxide (0.02 mol) were added to a 500 mL reactor. The reactor was then purged with nitrogen five times and heated to 120 °C for 40 hours under a nitrogen atmosphere. The hydrogen chloride gas produced was absorbed with alkaline solution through a nitrogen pipeline. Post-treatment: After cooling to room temperature, unreacted raw materials were removed by vacuum distillation to obtain 26.8 g of the target product, maleic anhydride-functionalized n-octadecane. The theoretical yield, calculated based on complete reaction of the functionalized monomer, was 29.1 g, representing a yield of 92%. Theoretical calculation [M+H] + The value was 365.5693, and a peak of 365.5685 was found on the HRMS (ESI) spectrum. Based on the above characterization results, it can be confirmed that the functionalized monomer was successfully grafted onto the long-chain alkane. The properties of the product are shown in Table 1.

[0076] Example 7

[0077] Add 200g of n-tetracosane (0.59mol), 10g of the functionalized monomer shown in structural formula II-1 (0.06mol), and 2.4g of benzoyl peroxide (0.01mol) to a 500mL reactor. Then, purge with nitrogen five times and heat to 120℃ for 24 hours under a nitrogen atmosphere. Add another 2.4g of benzoyl peroxide (0.01mol) and react at 120℃ for another 24 hours. The hydrogen chloride gas produced in the reaction is absorbed with alkaline solution through a nitrogen pipeline. Post-treatment: Cool to room temperature and remove unreacted raw materials by vacuum distillation to obtain 19.7g of the target product, maleic anhydride-functionalized n-tetracosane. The theoretical yield, calculated based on complete reaction of the functionalized monomer, is 28.1g, with a yield of 70%. Theoretical calculation [M+H] + The value was 421.6756, and a peak of 421.6764 was found on the HRMS (ESI) spectrum. Based on the above characterization results, it can be confirmed that the functionalized monomer was successfully grafted onto the long-chain alkane. The properties of the product are shown in Table 1.

[0078] Example 8

[0079] 200 g of liquid paraffin, 13.4 g of functionalized monomer (0.08 mol) as shown in structural formula II-1, and 4.8 g of benzoyl peroxide (0.02 mol) were added to a 500 mL reactor. The reactor was then purged with nitrogen five times and heated to 120 °C for 40 hours under a nitrogen atmosphere. The hydrogen chloride gas produced was absorbed with alkaline solution through a nitrogen pipeline. Post-treatment: After cooling to room temperature, unreacted raw materials were removed by vacuum distillation to obtain 32.2 g of the target product, maleic anhydride-functionalized liquid paraffin. The properties of the product are shown in Table 1.

[0080] Comparative Example 1

[0081] Commercially available ASA samples (prepared using octadecene), manufactured by NALCO. The properties of the ASA samples are shown in Table 1.

[0082] Table 1 Performance characterization results of the products

[0083]

[0084] Analysis of Examples 1-8 shows that as the number of carbon atoms in the functionalized alkane increases, the probability of maleic anhydride grafting to the terminal position gradually decreases. When the number of carbon atoms in the alkane is 13 or more, all grafting reactions occur on non-terminal carbons.

[0085] Comparing Examples 4-6 and Comparative Example 1, it can be seen that when the number of carbon atoms in the functionalized alkane is the same as the number of carbon atoms in the olefin used to synthesize ASA, the maleic anhydride functionalized alkane obtained by this invention has extremely similar properties to imported ASA (appearance, melting point, density, viscosity, acid value, and Cobb 60s value are almost identical). Furthermore, changing the reaction conditions—replacing other functionalized monomers or initiators provided by this invention—can yield maleic anhydride functionalized alkane with properties similar to ASA.

[0086] Comparing Examples 1 to 7, it can be seen that as the number of carbon atoms in the alkane undergoing the functionalization reaction increases, the obtained functionalized alkane exhibits a regular increase in melting point, a gradual decrease in Cobb 60s value, a gradual decrease in acid value, a gradual increase in viscosity, and a gradual decrease in density.

[0087] The liquid paraffin used in Example 8 is C 16 ~C 20 The mixed n-alkanes. Comparative Example 8 and Comparative Example 1 show that when mixed n-alkanes with 16 to 20 carbon atoms undergo functionalization reactions, the resulting maleic anhydride-functionalized liquid paraffin also possesses properties similar to the ASA sample.

[0088] In summary, through structural analysis of ASA, this invention proposes for the first time to replace it with maleic anhydride-functionalized long-chain alkanes, and achieves efficient synthesis of related products at extremely low cost and with a simple process route. Experimental results show that maleic anhydride-functionalized long-chain alkanes can exhibit properties and functions extremely similar to ASA, and are fully capable of replacing it to solve the predicament of insufficient domestic ASA production capacity.

[0089] The embodiments of the present invention have been described above. However, the present invention is not limited to the above embodiments. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. Maleic anhydride-functionalized long-chain alkanes, characterized in that, It was prepared by adding n-octadecane and a functionalized monomer to a reaction vessel. The reactants and initiators are heated and reacted in an inert gas atmosphere. The initiator is a free radical initiator; The maleic anhydride-functionalized long-chain alkane is a functionalized monomer. A mixture formed by grafting onto different sites of n-octadecane; The functionalized monomer is attached to the non-terminal carbon of n-octadecane.

2. The maleic anhydride-functionalized long-chain alkane according to claim 1, characterized in that, The density of the maleic anhydride-functionalized long-chain alkanes is 0.7~1 g / mL.

3. The method for preparing maleic anhydride-functionalized long-chain alkanes according to claim 1 or 2, characterized in that, Includes the following steps: Add the long-chain alkane n-octadecane and the functionalized monomer to the reaction vessel The reactants and initiators are heated and reacted in an inert gas atmosphere. The initiator is a free radical initiator.

4. The preparation method according to claim 3, characterized in that, The initiator is at least one of benzoyl peroxide, dicumyl peroxide, and tert-butyl peroxide.

5. The method according to claim 3, characterized in that, The molar ratio of the long-chain alkane to the functionalized monomer is 10:1 to 50:

1.

6. The method according to claim 3, characterized in that, The molar ratio of the initiator to the functionalized monomer is 1:1 to 1:

20.

7. The method according to claim 3, characterized in that, The reaction temperature is 80~140℃, and the reaction time is 1~48 hours.

8. The method according to claim 3, characterized in that, The method also includes a post-processing step after the reaction is completed, including: removing unreacted n-octadecane by vacuum distillation to obtain the target product, maleic anhydride-functionalized long-chain alkane.

9. The method according to any one of claims 3-8, characterized in that, The inert gas is selected from nitrogen and argon.

10. The use of the maleic anhydride functionalized long-chain alkane according to claim 1 or 2, characterized in that, Sizing agents used in the preparation of paper.

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