Gel factor as well as preparation method and application thereof

By designing amino acid derivative-based gel factors with hydrophobic long alkyl tail chains, using bottom-up self-assembly strategy to form a three-dimensional network structure, the existing small molecule gel factor has been solved, and a high-strength and stable organic gel is achieved, with good oil absorption and mechanical properties.

CN119613295AActive Publication Date: 2025-03-14NANJING TECH UNIV

Patent Information

Application Number
CN202311194669.4
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2023-09-14
Publication Date
2025-03-14
Estimated Expiration
2043-09-14

AI Technical Summary

Technical Problem

The existing small molecule gel factor gel concentration is too high, and the mechanical strength of the organic gel is too low. It does not have the potential as an oil-absorbing material, making it difficult to effectively store and transport oil.

Method used

By structurally designing the amino acid molecules, an amino acid derivative-based gel factor with hydrophobic long alkyl tail chain is provided, and nanofibers are formed at a lower gel-forming concentration using a bottom-up self-assembly strategy, and assembled into a three-dimensional network structure to achieve gelation of the oil phase in an oil solvent or oil-water mixture.

Benefits of technology

It has achieved high-strength and stable organic gel at a low gel-forming concentration, with good oil absorption capacity and mechanical properties, and is suitable for oil-water separation and oil storage and transportation.

✦ Generated by Eureka AI based on patent content.

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Abstract

The invention discloses a gelator and a preparation method and application thereof, the structural formula of the gelator is # imgabs0 #, R1 is a side chain group connected to an amino acid central carbon atom except an amino group, a carboxyl group and a hydrogen atom; the amino acid is selected from one of glycine, alanine, valine, leucine, isoleucine, methionine, proline, tryptophan, serine, tyrosine, cysteine, phenylalanine, asparagine, glutamine, threonine, aspartic acid, glutamic acid, lysine, arginine, histidine, selenocysteine and pyrrole lysine; the amino acid is selected from one of glycine, alanine, valine, leucine, isoleucine, methionine, proline, tryptophan, serine, tyrosine, cysteine, phenylalanine, asparagine, glutamine, threonine, aspartic acid, glutamic acid, lysine, arginine, histidine, selenocysteine and pyrrole lysine; r2 is alkyl with the carbon atom number of 16 to 19; and R3 is 9-fluorenyl methoxy carbonyl group or t-butyloxycarbonyl group. The gelator has a hydrophobic long alkyl tail chain, can spontaneously gather and assemble into a three-dimensional network structure through hydrogen bonds, pi-pi interaction and hydrophobic force, and fixes an oil phase in an oil solvent or an oil-water mixture in an effective manner to form high-strength gel.
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Description

Technical Field

[0001] The present invention relates to the technical field of functional materials, and in particular to a gel factor and a preparation method and application thereof. Background Art

[0002] Oil spills during oil extraction and transportation are an important source of marine pollution, causing serious impacts on marine life and the environment. Therefore, obtaining efficient oil-water separation materials that meet production requirements has become a key issue that needs to be solved urgently. So far, conventional methods such as mechanical collection, combustion, the use of adsorbents and chemical dispersants, and biological removal have been developed in industrial production processes for oil spill treatment. However, these methods usually have disadvantages such as poor recyclability or complex synthesis and high cost, which limits their practical application.

[0003] In recent years, with the introduction of phase-selective organic gelling agents, gel materials that can be used for oil-water separation have emerged. However, existing small molecule gelling factors often have defects such as too high gelling concentration and too low mechanical strength of the formed organic gel, which is not conducive to the storage and transportation of oil, and is prone to oil leakage, diffusion and volatilization, and has no potential as an oil absorbing material.

[0004] Therefore, the prior art still needs to be improved and developed. Summary of the invention

[0005] In view of the above-mentioned deficiencies in the prior art, the purpose of the present invention is to provide a gelling factor and a preparation method and application thereof, aiming to solve the problems that the existing small molecule gelling factor has too high gelling concentration, the mechanical strength of the formed organic gel is too low, and it has no potential as an oil absorbing material.

[0006] The technical solution of the present invention is as follows:

[0007] The first aspect of the present invention provides a gel factor, wherein the structural formula of the gel factor is:

[0008]

[0009] Wherein, R1 is a side chain group other than an amino group, a carboxyl group and a hydrogen atom connected to the central carbon atom of an amino acid, and the amino acid is selected from one of glycine, alanine, valine, leucine, isoleucine, methionine, proline, tryptophan, serine, tyrosine, cysteine, phenylalanine, asparagine, glutamine, threonine, aspartic acid, glutamic acid, lysine, arginine, histidine, selenocysteine ​​and pyrrolysine;

[0010] R2 is an alkyl group having 16 to 19 carbon atoms;

[0011] R3 is 9-fluorenylmethoxycarbonyl or tert-butyloxycarbonyl.

[0012] The second aspect of the present invention provides a method for preparing the gel factor of the present invention as described above, wherein the method comprises the following steps:

[0013] supply R2-NH2;

[0014] Will R2-NH2, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloric acid, 1-hydroxybenzotriazole, and an organic solvent are mixed and stirred to react to obtain a crude product;

[0015] After purifying the crude product, the gel factor is obtained.

[0016] Optionally, the organic solvent includes at least one of dichloromethane, toluene, n-hexane and n-octane.

[0017] Optionally, the stirring reaction is carried out at room temperature for 3 to 7 days.

[0018] Optionally, after purifying the crude product, the step of obtaining the gel factor specifically comprises:

[0019] The crude product is washed with a mixed solution of ethanol and water, then recrystallized with ethyl acetate, and dried to obtain the gel factor.

[0020] The third aspect of the present invention provides a use of the gel factor of the present invention as described above and / or the gel factor prepared by the preparation method of the present invention as described above as an oil absorbing material.

[0021] A fourth aspect of the present invention provides an application of the gelling factor as described above in the present invention and / or the gelling factor prepared by the preparation method as described above in the field of oil-water separation.

[0022] Optionally, the gel factor realizes oil-water separation by forming a gel with the oil.

[0023] Optionally, the oil includes at least one of diesel, kerosene, gasoline and engine oil.

[0024] A fifth aspect of the present invention provides a gel, which includes a gel factor and an oil solvent, wherein the gel factor is the gel factor of the present invention as described above and / or a gel factor prepared by the preparation method of the present invention as described above.

[0025] Beneficial effects: The present invention provides a non-toxic, environmentally friendly amino acid derivative-based gel factor with excellent gelling properties by structural design of amino acid molecules. The gel factor has a long hydrophobic alkyl tail chain, and can spontaneously aggregate in an oil solvent or an oil-water mixture through hydrogen bonds, π-π interactions, and hydrophobic forces at a lower gelling concentration through a bottom-up self-assembly strategy, and form nanofibers through physical cross-linking, assemble into a three-dimensional network structure, gel the oil phase in the oil solvent or oil-water mixture, and form a gel. Therefore, the gel factor can be used as an oil-absorbing material to achieve oil-water separation. In addition, the cross-linked nanofibers can provide rigidity for the gel, so that the gel has sufficient mechanical strength and good mechanical properties, which is convenient for the storage and transportation of oil solvents or oil phases, and effectively reduces the leakage and diffusion of oil solvents or oil phases. BRIEF DESCRIPTION OF THE DRAWINGS

[0026] Figure 1 This is the hydrogen nuclear magnetic resonance spectrum of the gel factor prepared in Example 1 of the present invention.

[0027] Figure 2 This is a frequency scanning test result diagram of organogels of different concentrations in Example 2 of the present invention.

[0028] Figure 3 Graph showing the strain scanning test results of organogels of different concentrations in Example 2 of the present invention.

[0029] Figure 4 This is a physical picture of the organogel formed at the critical gelation concentration when the solvent is n-hexane in Example 3 of the present invention.

[0030] Figure 5 This is a diagram showing the oil absorption effect of the concentrated organogel in Example 4 of the present invention.

[0031] Figure 6 Detailed illustration of the organogel in Example 5 of the present invention, wherein (a) is a side view and (b) is a top view.

[0032] Figure 7 This is a physical picture of the gel beads with certain elasticity in Example 6 of the present invention.

[0033] Figure 8 This is a physical picture of the "gel fish" in Example 7 of the present invention.

[0034] Fig. 9 This is a physical picture of the "gel brain" in Example 7 of the present invention.

[0035] Fig.10 This is a physical picture of the "gel heart" in Example 7 of the present invention.

[0036] Fig.11This is an AFM image of the organogel in Example 7 of the present invention.

[0037] Fig.12 This is a physical picture of the reshaped organogel in Example 8 of the present invention.

[0038] Fig.13 This is a diagram showing the load-bearing effect of the reshaped organogel in Example 8 of the present invention. DETAILED DESCRIPTION

[0039] The present invention provides a gel factor and a preparation method and application thereof. To make the purpose, technical solution and effect of the present invention clearer and more specific, the present invention is further described in detail below. It should be understood that the specific embodiments described herein are only used to explain the present invention and are not used to limit the present invention.

[0040] Unless otherwise defined, all technical terms and scientific terms used herein have the same meanings as those commonly understood by those skilled in the art to which the present invention belongs. The terms used in the specification of the present invention herein are only for the purpose of describing specific embodiments and are not intended to limit the present invention. An embodiment of the present invention provides a gel factor, wherein the structural formula of the gel factor is:

[0041]

[0042] Wherein, R1 is a side chain group other than an amino group, a carboxyl group and a hydrogen atom connected to the central carbon atom of an amino acid, and the amino acid is selected from one of glycine, alanine, valine, leucine, isoleucine, methionine, proline, tryptophan, serine, tyrosine, cysteine, phenylalanine, asparagine, glutamine, threonine, aspartic acid, glutamic acid, lysine, arginine, histidine, selenocysteine ​​and pyrrolysine;

[0043] R2 is an alkyl group having 16 to 19 carbon atoms;

[0044] R3 is 9-fluorenylmethoxycarbonyl (Fmoc) or tert-butyloxycarbonyl (Boc).

[0045] It is understood that low molecular weight organic molecules can gel the solvent at a certain concentration, and such low molecular weight organic molecules are called gel factors.

[0046] In the embodiment of the present invention, by structurally designing the amino acid molecules, a series of amino acid derivative-based gel factors with biodegradability, non-toxicity, and environmental friendliness are provided, which enriches the types of gel factors to achieve the preparation of more functional materials, and can be specifically used for the preparation of supramolecular gels. At the same time, the gel factor has a long hydrophobic alkyl tail chain, which can spontaneously aggregate through hydrogen bonds, π-π interactions, and hydrophobic forces at a lower gel concentration through a bottom-up self-assembly strategy, and form nanofibers through physical cross-linking, assemble into a three-dimensional network structure, gel the oil phase in the oil solvent or oil-water mixture, and form a gel. Therefore, the gel factor can be used as an oil-absorbing material to achieve oil-water separation. In addition, the cross-linked nanofibers can provide rigidity for the gel, so that the gel has sufficient mechanical strength and good mechanical properties, which is convenient for the storage and transportation of oil solvents or oil phases, and effectively reduces the leakage and diffusion of oil solvents or oil phases.

[0047] Specifically, through molecular design, the molecular weight of the gel factor in this embodiment, i.e., the amino acid derivative small molecule, is less than 600, and the length is about 2-3nm. When it is dissolved in an oil solvent or an oil-water mixture, it is easy to form ultrafine fibers with a width of 2-3nm. The fibers will be spirally cross-linked to form a cross-linked three-dimensional network structure, which can capture a lot of oil phases in the oil solvent or oil-water mixture, and then form a high-strength and high-stability organic gel, which is still stable at room temperature for 2-3 months. The critical gel concentration of the gel factor provided by the embodiment of the present invention can be as low as 0.180wt%.

[0048] As we all know, the general structural formula of amino acids is R is a side chain group other than an amino group, a carboxyl group, and a hydrogen atom connected to the central carbon atom of the amino acid. Different side chain groups of R determine different types of amino acids. For example, in this embodiment, when the amino acid is glycine, R1 is -H; when the amino acid is alanine, R1 is -CH3; when the amino acid is valine, R1 is -CH(CH3)2; when the amino acid is methionine, R1 is When the amino acid is phenylalanine, R1 is When the amino acid is threonine, R1 is When the amino acid is aspartic acid, R1 is And so on. Indicates the connection site.

[0049] R2 is an alkyl group having 16 to 19 carbon atoms, and specifically, a straight-chain alkyl group having 16 to 19 carbon atoms, such as -C 16 H 33 , -C 17 H 35 , -C 18 H37 , -C 19 H 39 wait.

[0050] The present invention also provides a method for preparing the gel factor according to the present invention, which comprises the following steps:

[0051] supply R2-NH2;

[0052] Will R2-NH2, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloric acid (EDC·HCl), 1-hydroxybenzotriazole (HOBt), and an organic solvent are mixed and stirred to react to obtain a crude product;

[0053] After purifying the crude product, the gel factor is obtained, wherein the groups represented by R3 and R1 are the same as those described above and will not be described in detail herein.

[0054] In this embodiment, the amino acid with a protecting group R3 at the N-terminus is The fatty amine R2-NH2, the condensation agent EDC·HCl and HOBt react to obtain the gel factor. The use of EDC·HCl and HOBt together can effectively control side reactions, and HOBt can also prevent racemization during the synthesis process.

[0055] In some embodiments, the organic solvent includes at least one of dichloromethane, toluene, n-hexane, and n-octane, but is not limited thereto. Preferably, the organic solvent is dichloromethane, and the solubility of the reactants in dichloromethane is the highest.

[0056] In some embodiments, the stirring reaction is carried out at room temperature for 3 to 7 days, such as 3 days, 4 days, 5 days, 6 days or 7 days. Unless otherwise specified, 1 day in the present invention represents 24 hours.

[0057] In some embodiments, the step of purifying the crude product specifically comprises:

[0058] The crude product is washed with a mixed solution of ethanol and water (to remove unreacted condensing agent, amino acid with a protecting group R3 at the N-terminus, and fatty amine), then recrystallized with ethyl acetate, and dried to obtain the gel factor.

[0059] In this embodiment, since the gel factor having a hydrophobic long alkyl tail chain is insoluble in a mixed solution of ethanol and water, the target product can be obtained by filtering after the crude product is washed with a mixed solution of ethanol and water.

[0060] The embodiment of the present invention also provides an application of the gel factor described in the embodiment of the present invention as an oil absorbing material. Or, the embodiment of the present invention also provides an application of the gel factor prepared by the preparation method described in the embodiment of the present invention as an oil absorbing material. Or, the embodiment of the present invention also provides an application of the gel factor described in the embodiment of the present invention as an oil absorbing material and the gel factor prepared by the preparation method described in the embodiment of the present invention as an oil absorbing material.

[0061] The embodiment of the present invention also provides an application of the gelling factor described above in the embodiment of the present invention in the field of oil-water separation. Or, the embodiment of the present invention also provides an application of the gelling factor prepared by the preparation method described above in the embodiment of the present invention in the field of oil-water separation. Or, the embodiment of the present invention also provides an application of the gelling factor described above in the embodiment of the present invention and the gelling factor prepared by the preparation method described above in the embodiment of the present invention in the field of oil-water separation.

[0062] The gel factor provided by the present invention has special micro-nano structural characteristics, can efficiently and quickly form supramolecular gels in a variety of aliphatic hydrocarbons (such as hexane, heptane, octane, cyclohexane, etc.), and is relatively stable within 2-3 months, and can be used in harsh environments in the field of oil-water separation.

[0063] In this embodiment, the gel factor realizes oil-water separation by forming a gel with oil. Specifically, the oil includes at least one of diesel, kerosene, gasoline, and engine oil.

[0064] An embodiment of the present invention further provides an organic gel, comprising a gel factor and an oil solvent, wherein the gel factor is the gel factor described above in the embodiment of the present invention, or the gel factor is a gel factor prepared by the preparation method described above in the embodiment of the present invention, or the gel factor is the gel factor described above in the embodiment of the present invention and a gel factor prepared by the preparation method described above in the embodiment of the present invention.

[0065] In this embodiment, by selecting different solvents, supramolecular gels with different properties and functions can be obtained.

[0066] In some embodiments, the oil solvent includes a liquid hydrocarbon solvent, and the liquid hydrocarbon solvent includes at least one of pentane (e.g., n-pentane), hexane (e.g., n-hexane), cyclohexane, heptane (e.g., n-heptane), octane (e.g., n-octane), nonane (e.g., n-nonane), decane (e.g., n-decane), undecane (e.g., n-undecane), dodecane (e.g., n-dodecane), tridecane (e.g., n-tridecane), and tetradecane (e.g., n-tetradecane), but is not limited thereto.

[0067] The oil solvents may also include hydrocarbon mixtures such as petroleum ether, gasoline, diesel, kerosene, engine oil, lubricating oil, etc.; the oil solvents may also include liquid vegetable oils such as rapeseed oil, olive oil, palm oil, etc.; the oil solvents also include liquid ester solvents, and the liquid ester solvents include but are not limited to ethyl dichloroacetate.

[0068] The present invention also provides a method for preparing an organogel, which comprises the following steps:

[0069] The gel factor and the oil solvent are mixed, heated and stirred, and cooled at room temperature to obtain the organogel.

[0070] When the gel factor concentration is greater than 5 mg / mL, the organogel has good self-supporting properties; when the gel factor concentration is greater than 10 mg / mL, the organogel has good elasticity, and after being deformed under a certain pressure, it can return to its original shape when the pressure is removed; when the gel factor concentration is in the range of 10-20 mg / mL, the shape of the mold can be well replicated, and the obtained organogel will not deform after being placed for a long time.

[0071] The following describes it in detail through specific embodiments.

[0072] Example 1

[0073] Unless otherwise specified, the raw materials used in the following examples are all commercially available products, among which Fmoc-L-phenylalanine was purchased from Shanghai Aladdin Biochemical Technology Co., Ltd. with a brand number of F105472.

[0074] This embodiment provides a method for preparing a gel factor, comprising the following steps:

[0075] 2g Fmoc-L-phenylalanine 1.67 g of octadecylamine, 0.96 g of EDC·HCl, and 0.84 g of 1-hydroxybenzotriazole monohydrate were added to a round-bottom flask, and 125 mL of dichloromethane was added as a solvent. The mixture was stirred well at room temperature and reacted for 3 days.

[0076] The reaction product was subjected to rotary evaporation to remove the solvent, and 200 mL of a 1:1 ethanol / water mixed solvent was added, heated and stirred until boiling, filtered while hot, and the filter residue was taken. An ethanol / water mixed solvent (100 mL of ethanol and 234 mL of water) with a volume ratio of 3:7 was continued to be added, and the above operation was repeated 3 times to obtain a crude gel factor.

[0077] Add 400 mL of dichloromethane to the crude gel factor, heat to dissolve until the solution is clear, filter while hot, and take the filtrate. Cool the filtrate to room temperature and perform rotary evaporation.

[0078] The product obtained after rotary evaporation was recrystallized twice with ethyl acetate and finally vacuum dried to obtain the final product gel factor It is denoted as L-FPC18, which is a white solid powder. Its H NMR spectrum is as follows: Figure 1 shown.

[0079] Example 2

[0080] This embodiment provides a method for preparing an organogel, comprising the following steps:

[0081] The L-FPC18 and n-dodecane in Example 1 were heated and dissolved at 200°C until the solution was clear (the concentrations of L-FPC18 were 5 mg / mL, 10 mg / mL, and 20 mg / mL, respectively), and self-assembled at room temperature for 2 hours to obtain three organogels. The three organogels were tested for dynamic rheological behavior. The organogels were evenly dispersed on the sample stage of the MCR302 rheometer, and the dynamic frequency sweep and strain sweep were measured. Before each test, the height of the gel needs to be accurately measured with a ruler to control the gap distance between the parallel plate and the gel. During the test, a layer of glycerol needs to be applied around the parallel plate to alleviate the volatilization of the solvent in the gel. The results are as follows: Figure 2 As shown. Figure 2 It can be seen that in the dynamic frequency sweep (ω = 0.1 ~ 100rad·s -1 ) test, as the scanning frequency changes, the G′ of the organogel at the three concentrations is always greater than G″, indicating that it is not greatly affected by the frequency and can form stable gels. It is worth noting that when the concentration increases to 20 mg / mL, G′ / G″ is always at a constant value, which shows that it is not sensitive to changes in frequency at high concentrations.

[0082] In strain sweep testing, Figure 3 As shown, a small strain of 0.01% was applied, the gel concentration increased from 5 mg / mL to 20 mg / mL, and the elastic modulus G′ increased from 689 Pa to 4100 Pa. When the concentration increases, the elastic modulus and viscous modulus of the organic gel will also increase accordingly.

[0083] When the concentration is 5 mg / mL and the strain is in the range of 0.01% to 1.41%, it is the linear elastic region (LVE). The elastic modulus G′ and viscous modulus G″ of the gel remain almost unchanged within this range, and G′>G″, indicating that the organogel is a typical viscous soft material. When the strain value is 4.45%, G′ and G″ almost coincide, and it is at the critical point. When the strain value is greater than 4.45%, as the strain increases, the G′ value drops sharply, indicating that the three-dimensional network structure of the gel has been destroyed and causes flow.

[0084] Similarly, when the organogel concentration is 10 mg / mL, it is in the LVE region when the strain is in the range of 0.01 to 1%. When the applied strain exceeds 1%, a certain degree of damage occurs inside the gel and the modulus begins to decrease. When the strain increases to 21.36%, G′=G″.

[0085] For the gel with a concentration of 20 mg / mL, its linear viscoelastic region is relatively narrow, only the region with strain < 0.14%. The failure point is reached when the strain value is 1.06%. Since the wider the linear viscoelastic region, the more stable the gel, it can be seen that when the gel concentration is 10 mg / mL, it can withstand a large deformation without being destroyed.

[0086] Example 3

[0087] The L-FPC18 and n-hexane in Example 1 were heated and dissolved at 150°C until the solution was clear, wherein the concentration of L-FPC18 was as low as 0.531wt% (critical gelling concentration), and then cooled at room temperature for about 5 minutes. Figure 4 As shown, the sample bottle was inverted to form a stable organic gel. Therefore, L-FPC18 as an oil-absorbing material can fix the oil solvent n-hexane, and 3.57g of gel factor L-FPC18 can gel about 1L of n-hexane.

[0088] The L-FPC18 and n-octane in Example 1 were heated and dissolved at 180°C until the solution was clear, wherein the concentration of L-FPC18 was as low as 0.296wt% (critical gelling concentration), and then cooled at room temperature for about 5 minutes to form a stable organic gel. Therefore, L-FPC18 can fix the oil solvent n-octane as an oil absorbing material, and 2.08g of gel factor L-FPC18 can gel about 1L of n-octane.

[0089] The L-FPC18 and n-decane in Example 1 were heated and dissolved at 200°C until the solution was clear, wherein the concentration of L-FPC18 was as low as 0.189wt% (critical gelation concentration), and then cooled at room temperature for about 5 minutes to form a stable organic gel. Therefore, L-FPC18 can fix the oil solvent n-decane as an oil absorbing material, and 1.39g of gel factor L-FPC18 can gel about 1L of n-decane.

[0090] The L-FPC18 and dodecane in Example 1 were heated and dissolved at 220°C until the solution was clear, wherein the concentration of L-FPC18 was as low as 0.180wt% (critical gelling concentration), and then cooled at room temperature for about 5 minutes to form a stable organic gel. Therefore, L-FPC18 can fix the oil solvent dodecane as an oil absorbing material, and 1.35g of the gel factor L-FPC18 can gel about 1L of dodecane.

[0091] In addition, the L-FPC18 in Example 1 also has similar phenomena in gasoline, kerosene, diesel and engine oil, and can form a stable organic gel.

[0092] Therefore, the gel factor provided by the present invention has good oil absorption capacity.

[0093] Example 4

[0094] Weigh a certain amount of L-FPC18 and place it in a clean sample bottle, then add n-octane as a solvent and heat until it is clear. The concentration of L-FPC18 is 10 mg / mL. Then cool it at room temperature for 5 minutes and quickly transfer it to a mold. After a stable gel is formed at room temperature, place it in an 80°C oven to remove part of the solvent to form a gel with a higher concentration. Cut the concentrated organic gel after removing part of the solvent, place it in n-hexane solvent, and place it at room temperature for a period of time. The results are as follows: Figure 5 As shown in the figure, the concentrated organogel can gel n-hexane to form a new gel. This shows that the organogel with high concentration also has good oil absorption capacity.

[0095] Example 5

[0096] This embodiment provides a method for preparing an organogel, comprising the following steps:

[0097] The L-FPC18 and n-hexane in Example 1 were placed in a sample bottle and heated at 150°C to dissolve until the solution was clear, wherein the concentration of L-FPC18 was 5 mg / mL, and heated and stirred to dissolve until the solution was clear, and then cooled at room temperature for about 5 minutes, transferred to a mold, and assembled at room temperature to form an organogel. The actual figure is as shown in the figure. Figure 6 As shown, the prepared organogel has a certain strength and good self-supporting property.

[0098] Example 6

[0099] This embodiment provides a method for preparing an organogel, comprising the following steps:

[0100] The L-FPC18 and n-decane in Example 1 were heated and dissolved at 150°C until the solution was clear, wherein the concentration of L-FPC18 was 10 mg / mL, and cooled at room temperature for 5 minutes, and then transferred into a centrifuge tube and continued to assemble for about 30 minutes. The obtained gel product was as follows: Figure 7 As shown in the figure, the gel ball deflates after being stimulated, but the gel rebounds quickly after the pressure is removed, which shows that the gel has a certain elasticity.

[0101] Example 7

[0102] This embodiment provides a method for preparing an organogel, comprising the following steps:

[0103] The L-FPC18 and n-tetradecane in Example 1 were heated and dissolved at 200°C until the solution was clear, wherein the concentration of L-FPC18 was 20 mg / mL, and cooled at room temperature for 5 minutes, and then quickly moved into molds of different shapes and assembled at room temperature for about 2 hours to obtain organic gels of different shapes. During the gelation process, the L-FPC18 molecules can adhere to the molds for molding, be completely demolded, and not collapse after being placed for 7 days. The results are as follows Figure 8-10 As shown, the longest part of the "gel fish" can be up to 9.5cm, the size of the "gel brain" is roughly 4.5cm×3.5cm×1.5cm, and the thickness of the center of the "gel heart" can reach 2cm, with the longest dimension being 6cm. Gels of these shapes all have good mechanical strength and will not deform when placed at room temperature for 3 months.

[0104] The AFM image of the formed organogel is shown in Fig.11 As shown, it can be seen that the gel has an ultrafine, spirally cross-linked fiber network structure, which means that the gel factor provided by the present invention can capture more oil solvent molecules to form a high-strength gel.

[0105] Example 8

[0106] The organogel formed in Example 7, i.e., the "gel heart", was concentrated and reshaped by secondary heating. Specifically, the "gel heart" was heated at 200° C. for 15 minutes to obtain a hot solution. The hot solution was then quickly transferred to molds of different shapes, assembled for 10 minutes, and after demolding, reshaped organogels of different shapes (grape-shaped, strawberry-shaped, and apple-shaped) were obtained. Specifically, Fig.12 shown.

[0107] Test: The hot solution obtained in Example 8 was poured into a mold and assembled for 10 minutes to obtain a reshaped organogel, which was then cut into four gel columns with a diameter of 18 mm, a height of 20 mm, and a weight of about 4.0 g. Fig.13 As shown, a glass plate is placed on it, and a heavy object is placed on the glass plate. Using these gel columns, a weight of more than 10 kg can be supported. The reshaped organogel has good mechanical properties and can support a weight about 600 times heavier than its own weight.

[0108] Example 9

[0109] A certain amount of water and gasoline are added to a beaker, the gasoline floats on the water surface, and the L-FPC18 in Example 1 is added thereto. After stirring, the gasoline forms a block gel, and the water remains in the beaker. The block gel can be taken out of the beaker. It can be seen that the gel factor provided by the present invention can be used for oil-water separation.

[0110] In summary, the present invention provides a gel factor and a preparation method and application thereof. The present invention provides a series of biodegradable, non-toxic, and environmentally friendly amino acid derivative-based gel factors through molecular structure design, enriching the types of gel factors, and can be used for the preparation of supramolecular gels. The gel factor has a hydrophobic long alkyl tail chain, which can spontaneously aggregate and assemble into a three-dimensional network structure through hydrogen bonds, π-π interactions, and hydrophobic forces. Specifically, through a bottom-up self-assembly strategy, the ultra-thin self-assembled nanofibers formed by physical cross-linking can fix the oil phase in an oil solvent or an oil-water mixture in a very effective way to form an organic gel with high strength.

[0111] It should be understood that the application of the present invention is not limited to the above examples. For ordinary technicians in this field, improvements or changes can be made based on the above description. All these improvements and changes should fall within the scope of protection of the claims attached to the present invention.

Claims

1. A gel factor, characterized in that: The structural formula of the gel factor is: Wherein, R1 is a side chain group other than an amino group, a carboxyl group and a hydrogen atom connected to the central carbon atom of an amino acid, and the amino acid is selected from one of glycine, alanine, valine, leucine, isoleucine, methionine, proline, tryptophan, serine, tyrosine, cysteine, phenylalanine, asparagine, glutamine, threonine, aspartic acid, glutamic acid, lysine, arginine, histidine, selenocysteine ​​and pyrrolysine; R2 is an alkyl group having 16 to 19 carbon atoms; R3 is 9-fluorenylmethoxycarbonyl or tert-butyloxycarbonyl.

2. A method for preparing the gel factor according to claim 1, characterized in that: The steps include: supply R2-NH2; Will R2-NH2, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloric acid, 1-hydroxybenzotriazole, and an organic solvent are mixed and stirred to react to obtain a crude product; After purifying the crude product, the gel factor is obtained.

3. The preparation method according to claim 2, characterized in that: The organic solvent includes at least one of dichloromethane, toluene, n-hexane and n-octane.

4. The preparation method according to claim 2, characterized in that: The stirring reaction is carried out at room temperature for 3 to 7 days.

5. The preparation method according to claim 2, characterized in that: After purifying the crude product, the step of obtaining the gel factor specifically comprises: The crude product is washed with a mixed solution of ethanol and water, then recrystallized with ethyl acetate, and dried to obtain the gel factor.

6. Use of the gel factor according to claim 1 and / or the gel factor prepared by the preparation method according to any one of claims 2 to 5 as an oil absorbing material.

7. Use of the gelling factor as claimed in claim 1 and / or the gelling factor prepared by the preparation method as claimed in any one of claims 2 to 5 in the field of oil-water separation.

8. The use according to claim 7, characterized in that: The gel factor realizes oil-water separation by forming a gel with the oil.

9. The use according to claim 7 or 8, wherein the oil comprises at least one of diesel, kerosene, gasoline and engine oil.

10. An organogel, characterized in that: The invention comprises a gelling factor and an oil solvent, wherein the gelling factor is the gelling factor according to claim 1 and / or a gelling factor prepared by the preparation method according to any one of claims 2 to 5.

Citation Information

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