Organic small molecule compound as well as preparation method and application thereof

Abstract

The invention provides an organic small molecule compound as well as a preparation method and application thereof, and belongs to the field of fine chemical engineering. The organic small molecule compound has the following molecular structural formula: A-L-B, A is hydroxyl or a # imgabs 0 # group, B is a # imgabs 1 # group, and a Y element in the # imgabs 2 # group is selected from one of N and P; one end of L is connected with A, the other end of L is connected with B, L is an aliphatic chain or an aliphatic chain containing an aromatic substituent group, and the carbon atom number of the main chain of the aliphatic chain is 2-14. The organic small molecule compound provided by the invention is easy to form relatively strong intermolecular interaction through a non-covalent bond, has excellent bonding performance, shows good bonding performance in a relatively wide temperature range, and has excellent applicability to different use environments (such as solvents and bonding materials).

Description

Technical Field

[0001] The invention belongs to the technical field of fine chemical industry, and specifically relates to an organic small molecule compound and a preparation method and application thereof. Background Art

[0002] Adhesives, also known as adhesives, have the function of bonding the same or different types of substrates. They are an important industrial auxiliary material and are used in many fields of society. Existing adhesives are mainly divided into inorganic adhesives and organic adhesives. Organic adhesives include organic polymer adhesives and organic small molecule adhesives. Most of the organic adhesives reported so far belong to organic polymer adhesives, which have a high polymer structure. Adhesives of this type of structure show excellent adhesion properties and permeability to the target substrate, but the high adhesion and high permeability of organic polymer adhesives also lead to difficulties in debonding. At the same time, due to the participation of solvents in the preparation process, the adhesive performance decreases and environmental pollution occurs after the solvent evaporates. Compared with organic polymer adhesives, organic small molecule adhesives based on supramolecular interactions show their unique advantages, such as controllable synthesis, sufficient molecular-interface interaction, responsiveness and reversibility, etc. However, this type of adhesive is usually cumbersome to synthesize, the raw materials are expensive, the adhesion strength is insufficient, and in actual application, the adhesion performance is greatly affected by low temperature.

[0003] Therefore, although challenging, it is of great significance to develop a small-molecule-based supramolecular adhesive with simple synthesis, well-defined composition, broad temperature resistance, and low toxicity and environmental protection. Summary of the invention

[0004] In order to solve the problems in the prior art that organic small molecule adhesives based on supramolecular interactions are complicated to synthesize, have insufficient adhesion strength, do not have low-temperature applicability, and the adhesion performance is greatly affected by low temperature, the present invention provides an organic small molecule compound and a preparation method thereof and application in the preparation of adhesives and flame retardants.

[0005] The organic small molecule compound has the following molecular structure:

[0006] ALB, wherein A is hydroxyl or Group, B is Group, The Y element in the group is selected from one of N and P, and at least one of A and B is Group;

[0007] One end of L is connected to A and the other end is connected to B. It is a fatty chain or a fatty chain containing an aromatic substituent. The carbon number of the fatty chain main chain is 2-14.

[0008] Furthermore, the molecular structural formula of the organic small molecule compound is any one of the following molecular structural formulas:

[0009] Formula b Formula d n=1-13, and the Y element is selected from one of N and P. Further, the molecular structure of the organic small molecule compound is any one of the following molecular formulas:

[0010]

[0011]

[0012]

[0013]

[0014] Furthermore, the molecular structure of the organic small molecule compound is any one of the following molecular formulas:

[0015]

[0016]

[0017] The present invention also provides a method for preparing an organic small molecule compound. The method for preparing an organic small molecule compound comprises the following steps:

[0018] The diol reacts with hydrobromic acid in toluene to undergo a mono- or di-substitution reaction;

[0019] The substitution reaction product reacts with YPh3 in anhydrous acetonitrile for nucleophilic substitution reaction.

[0020] The diol includes a fat chain or a fat chain containing an aromatic substituent, the carbon number of the main chain of the fat chain is 2-14, and the Y element is one of N and P.

[0021] Further, the diol and hydrobromic acid are subjected to a monosubstituted reaction in toluene at a molar ratio of 1:(1-1.6), the monosubstituted reaction temperature is 80-100° C., and the reaction time is 20-26 hours;

[0022] The monosubstituted reaction product is reacted with YPh3 in anhydrous acetonitrile at a molar ratio of 1: (1-1.5) for nucleophilic substitution reaction at a reaction temperature of 80-100° C. for a reaction time of 22-26 h.

[0023] Further, the diol and hydrobromic acid are subjected to a disubstituted reaction in toluene at a molar ratio of 1:(10-12), the temperature of the disubstituted reaction is 80-100° C., and the reaction time is 28-32 hours;

[0024] The binary substitution reaction product is reacted with YPh3 in a molar ratio of 1:(2-2.5) in N,N-dimethylacetamide for nucleophilic addition reaction, the reaction temperature is 80-100°C, and the reaction time is 16-20h.

[0025] The present invention also provides application of the above organic small molecule compound in preparing adhesives or flame retardants.

[0026] The present invention also provides an adhesive comprising at least one of the above-mentioned organic small molecule compounds.

[0027] Furthermore, the organic small molecule compound needs to be processed by a hot melt method or a solvent volatilization method before use.

[0028] Further, the adhesive further includes an additive;

[0029] Preferably, the additive is selected from one of hydroxyl-containing, amino-containing compounds or quaternary ammonium salt compounds;

[0030] Preferably, the additive is selected from one of ethylene glycol, acetamide and glycerol.

[0031] Beneficial effects:

[0032] The organic small molecule wide temperature range adhesive provided by the present invention belongs to an organic small molecule non-covalent action system, and can be easily synthesized in high yield in two simple steps using cheap and readily available raw materials; at the same time, its component structure contains more functional chemical sites, and is easy to form stronger intermolecular interactions; it has excellent bonding properties, and still exhibits good bonding properties within a wide temperature range (-80-80°C), and excellent adhesion is also observed in liquid nitrogen, and it has high tolerance to drastic temperature changes; it has excellent applicability to different use environments (such as solvents, adhesive materials); it has good reusability and long-term usability. BRIEF DESCRIPTION OF THE DRAWINGS

[0033] Figure 1 The bonding strength of the SA-17 adhesive provided in Example 1 of the present invention to glass, steel and PET at different temperatures;

[0034] Figure 2 The bonding strength of the SA-17 adhesive provided in Example 1 of the present invention after immersion treatment in different solvents using PET as the substrate;

[0035] Figure 3 The SA-17 provided in Example 1 of the present invention is subjected to a cyclic test at -18°C to 20°C (steel, 16 cm 2 );

[0036] Figure 4 SA-17 and (SA-17) provided in Example 1 of the present invention20 - Changes in adhesion strength of EG1 to PET over time;

[0037] Figure 5 The bonding strength of the structural adhesive represented by formula SA-41 to glass and steel at room temperature. DETAILED DESCRIPTION

[0038] In order to make the above-mentioned objects, features and advantages of the present invention more obvious and understandable, the specific implementation modes of the present invention are described in detail below with reference to the accompanying drawings, but they should not be construed as limiting the applicable scope of the present invention.

[0039] The supramolecular toolbox provides a promising solution to overcome the problems in the existing technology. Compared with traditional covalent polymer networks, supramolecular networks are more flexible and dynamic, and their smaller structural units are more conducive to overcoming the low-temperature failure problem. Organic small molecules provide an attractive option that can combine readily available raw materials, easy synthesis and integrated complex properties. In order to improve the bonding strength of adhesives, it is necessary to enhance adhesion and cohesion, introduce structural groups such as hydroxyl groups, positive and negative charges, and benzene rings, and covalently connect them through flexible carbon chains. These groups can produce non-covalent interactions such as hydrogen bonds, electrostatic forces, and π-π stacking, respectively, thereby forming strong cohesion and interfacial forces, so that the adhesive has excellent adhesion and low-temperature resistance.

[0040] The present invention provides an organic small molecule compound having the following molecular structure:

[0041] ALB, wherein A is hydroxyl or Group, B is Group, The Y element in the group is selected from one of N and P;

[0042] One end of L is connected to A and the other end is connected to B. It is a fatty chain or a fatty chain containing an aromatic substituent. The carbon number of the fatty chain main chain is 2-14.

[0043] There are a large number of hydrogen bond donors and acceptors and a variety of functional groups in the organic small molecule compound, which can provide non-covalent interactions such as hydrogen bonds, electrostatic effects and π-π stacking, giving the organic small molecule compound excellent responsiveness, reversibility, universality and adhesion properties in a wide temperature range.

[0044] Furthermore, the organic small molecule compound has many structural changes, and at least one molecular structural formula is one of the following molecular structural formulas:

[0045] Formula b Formula d n=1-13, and the Y element is selected from one of N and P.

[0046] When used to prepare an adhesive, the adhesive contains at least one of the above-mentioned small organic molecule compounds. In addition, the adhesive component may also contain a variety of additives. The molecular structural formula of the above-mentioned small organic molecule compound is one of formula b or formula d. Preferably, in the present invention, the molecular structure of the organic small molecule compound can be as shown in Formula 1, Formula 2, Formula 3, Formula 4, Formula 5, Formula 6, Formula 7, Formula 8, Formula 9, Formula 10, Formula 11, Formula 12, Formula 13, Formula 14, Formula 15, Formula 16, Formula 17, Formula 18, Formula 19, Formula 20, Formula 21, Formula 22, Formula 23, Formula 24, Formula 25, Formula 26, Formula 27, Formula 28, Formula 29, Formula 30, Formula 31, Formula 32, Formula 33, Formula 34, Formula 35, Formula 36, ​​Formula 37, Formula 38, Formula 39, Formula 40, Formula 41, Formula 42, Formula 43, Formula 44, Formula 45, Formula 46, Formula 47, Formula 48, Formula 49, Formula 50, Formula 51 or Formula 52. Name the organic small molecule compounds with the above molecular structural formulas in order SA-1, SA-2, SA-3, SA-4, SA-5, SA-6, SA-7, SA-8, SA-9, SA-10, SA-11, SA-12, SA-13, SA-14, SA-15, SA-16, SA-17, SA-18, SA-19, SA-20, SA-21, SA-22, SA-23, SA-24, SA-2 5. SA-26, SA-27, SA-28, SA-29, SA-30, SA-31, SA-32, SA-33, SA-34, SA-35, SA-36, SA-37, SA-38, SA -39, SA-40, SA-41, SA-42, SA-43, SA-44, SA-45, SA-46, SA-47, SA-48, SA-49, SA-50, SA-51, SA-52.

[0047]

[0048]

[0049]

[0050]

[0051] The present invention also provides a method for preparing the above-mentioned organic small molecule compound.

[0052] ①When A is hydroxyl group and B is When the group is present, the molecular structure of the organic small molecule compound has the formula b The structure shown (n=1-13), the synthesis route of the organic small molecule compound shown in formula b is shown in formula A-1:

[0053]

[0054] The method for preparing the organic small molecule compound represented by formula b comprises the following steps:

[0055] (1) Preparation of formula a Compounds shown:

[0056] Equation e-1 The diol shown is mixed with hydrobromic acid to undergo a substitution reaction to obtain formula a The monosubstituted product is shown.

[0057] S1: The diol represented by formula e-1 and hydrobromic acid are subjected to substitution reaction in toluene at a molar ratio of 1:(1-1.6). The temperature of the substitution reaction is 80-100°C and the reaction time is 20-26h.

[0058] S2: extract the organic phase of the reaction with ether, separate the liquids, dry and concentrate to obtain a crude product, and then separate the crude product by silica gel column chromatography. The eluent for column chromatography separation is preferably ethyl acetate and petroleum ether, and the volume ratio of ethyl acetate to petroleum ether is preferably 1: (4-5).

[0059] (2) Preparation of the compound shown in formula b:

[0060] Formula a prepared The compound shown in formula b undergoes a nucleophilic substitution reaction with YPh3 to obtain a compound shown in formula b.

[0061] S3: Formula a The compound is reacted with YPh3 in anhydrous acetonitrile at a molar ratio of 1:(1-1.5) for nucleophilic substitution reaction at a reaction temperature of 80-100°C for a reaction time of 22-26h.

[0062] S4: Cool the reaction product to room temperature, evaporate the acetonitrile, and then separate the crude product by silica gel column chromatography. The column chromatography eluent is preferably methanol and dichloromethane, and the volume ratio of methanol to dichloromethane is preferably (2-5): (95-98), and recrystallize.

[0063] ②When A and B are When the group is present, the molecular structure of the organic small molecule compound has the formula d The structure shown (n=1-13), the synthesis route of the organic small molecule compound shown in formula d is shown in formula A-2:

[0064]

[0065] The method for preparing the organic small molecule compound represented by formula d comprises the following steps:

[0066] (1) Preparation formula c Compounds shown:

[0067] The diol represented by formula e-1 is mixed with hydrobromic acid to carry out a substitution reaction to obtain formula c The disubstituted products are shown.

[0068] Sⅰ: The diol represented by formula e-1 is subjected to substitution reaction with hydrobromic acid in a molar ratio of 1:(10-12) in toluene. The temperature of the substitution reaction is 80-100°C and the reaction time is 28-32h.

[0069] Sⅱ: extracting the organic phase of the reaction with ether, separating the liquids, drying and concentrating to obtain a crude product, and then subjecting the crude product to silica gel column chromatography separation, wherein the column chromatography separation eluent is preferably petroleum ether.

[0070] (2) Preparation of the compound shown in formula d:

[0071] The prepared formula c The compound shown undergoes a nucleophilic substitution reaction with YPh3 to obtain a compound shown in formula d.

[0072] Sⅲ: Formula c The compound and YPh3 undergo nucleophilic addition reaction in N,N-dimethylacetamide at a molar ratio of 1:(2-2.5), the reaction temperature is 80-100°C, and the reaction time is 16-20h.

[0073] Sⅳ: Purify the obtained compound represented by formula d, and separate the crude product by silica gel column chromatography. The eluent for column chromatography separation is preferably methanol and dichloromethane. The volume ratio of methanol to dichloromethane is preferably (2-5): (95-98).

[0074] The present invention has no special requirements on the washing, extraction and purification methods, and the above operations well known to those skilled in the art can be used.

[0075] The organic small molecule compound provided by the present invention and its preparation method and application are described in detail below in conjunction with the embodiments, but they should not be construed as limiting the scope of protection of the present invention.

[0076] The present invention characterizes the organic small molecule compound obtained by the method for preparing the organic small molecule compound in the embodiment.

[0077] Example 1

[0078] A is hydroxyl group, B is group, n=5, Y is P, the molecular structure of the organic small molecule compound is as shown in Formula 17 shown.

[0079] (1) Formula a Preparation of the indicated compounds:

[0080] Formula a-1 The synthetic route of the compound is shown in Formula B:

[0081] Formula B

[0082] S1: Add 5g of 1,6-hexanediol and 100mL of toluene to a two-necked flask, and heat the mixture until it is completely dissolved. Then, drop 5.74ml of 48% hydrobromic acid, stir and reflux for 12h, and the TLC plate shows that there is still a lot of diol remaining. Therefore, further add 1.44mL of hydrobromic acid, and heat the mixture under reflux overnight, at which time the TLC plate shows that almost no diol remains.

[0083] S2: The reaction mixture was cooled to room temperature and phase separated. The organic phase was extracted with ether, neutralized with 1M NaOH to neutrality, and then dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain a yellow oily liquid. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate / petroleum ether = 1 / 4) and concentrated to obtain compound a-1, which was a colorless oil with a yield of 90%.

[0084] (2) Preparation of compound SA-17 represented by formula 17:

[0085] The synthetic route of compound SA-17 is shown in Formula C:

[0086] Formula C

[0087] S3: 9.15 g of the compound represented by formula a-1 and 14.58 g of triphenylphosphine were heated to reflux in 27 mL of anhydrous acetonitrile for 24 hours, and a white precipitate appeared.

[0088] S4: The reaction mixture was cooled to room temperature and concentrated. The crude product was purified by silica gel column chromatography (eluent: methanol / dichloromethane = 2 / 98), and recrystallized from dichloromethane / ethyl ether to obtain the organic small molecule compound SA-17 represented by Formula 17, which was a white powder with a yield of 87%.

[0089] LCMS (ESI+): Calculated [(M+H)+]: 363.2, found 363.1.

[0090] The hydrogen spectrum data are:

[0091] 1H NMR (400MHz, CDCl3) δ (ppm): 1.47 (apps, 4H), 1.65-1.66 (m, 4H), 3.57-3.67 (m, 5H), 7.70-7.75 (m, 6H), 7.79-7.84 (m, 9H)

[0092] Example 2

[0093] A is hydroxyl group, B is group, n=9, Y is P, the molecular structure of the organic small molecule compound is as shown in Formula 33 shown.

[0094] (1) Formula a Preparation of the indicated compounds:

[0095] Formula a-2 The synthetic route of the compound is shown in Formula D:

[0096] Formula D

[0097] Sⅰ: Add 1 g of 1,10-hexanediol and 60 mL of toluene to a two-necked flask, and heat the mixture until it is completely dissolved. Then, drop 0.72 mL of 48% hydrobromic acid, and heat the mixture to reflux. After 12 hours, drop 0.2 mL of 48% hydrobromic acid aqueous solution to the mixture again. After continuing to reflux for 12 hours, TLC shows that the reaction is basically completed.

[0098] Sⅱ: The temperature of the reaction product is lowered to room temperature, and the organic phase and the aqueous phase are separated. The aqueous phase is extracted with ethyl acetate, and the organic phase is finally collected and combined, and washed with 1M NaOH, deionized water and saturated brine in sequence, and finally dried with anhydrous sodium sulfate. The crude product is distilled under reduced pressure. The crude product is purified by silica gel column chromatography (eluent: ethyl acetate / petroleum ether = 1 / 4) to obtain the compound of pure formula a-2, which is a colorless oily liquid with a yield of 95%.

[0099] (3) Synthesis of compound SA-33 having the structure represented by formula 33

[0100] The synthetic route of compound SA-33 is shown in Formula E:

[0101] Formula E

[0102] Sⅲ: 1.00 g of the compound represented by formula a-2 and 1.22 g of triphenylphosphine were heated to reflux in 50 mL of anhydrous acetonitrile for 48 hours. TLC plate showed that no reactant remained.

[0103] Sⅳ: The temperature of the reaction product is lowered to room temperature, and the solvent is evaporated under reduced pressure to obtain a crude product. The crude product is recrystallized from anhydrous ether / dichloromethane to obtain the target product, that is, the organic small molecule compound SA-33 represented by formula 33, which is a white solid with a yield of 90%.

[0104] LCMS (ESI+): Calculated [(M+H)+]: 419.6, found 419.2.

[0105] The hydrogen spectrum data are:

[0106] 1H NMR (400MHz, CDCl3), δ (ppm): 7.85-7.80 (m, 9H), 7.76-7.71 (m, 6H), 3.67-3.56 (m, 4H), 1.62-1.48 (m, 6H), 1.26-1.20 (m, 10H).

[0107] Example 3

[0108] A and B are group, n=5, Y is P, the molecular structure of the organic small molecule compound is as shown in Formula 19 shown.

[0109] (1) Formula c Preparation of the indicated compounds:

[0110] Formula c-1 The synthetic route of the compound is shown in Formula F:

[0111] Formula F

[0112] S1: 2 g of 1,6-hexanediol and 24 mL of 48% hydrobromic acid aqueous solution were added to a two-necked flask, and the mixture was stirred and refluxed for 30 h in a dark environment. When the TLC plate showed that a small amount of reactants remained, the reaction was stopped.

[0113] S2: The reaction mixture was cooled to room temperature, phase separated, and the organic layer was collected. The crude product was purified by silica gel column chromatography (eluent: petroleum ether) and concentrated to obtain the compound of pure formula c-1 in the form of a colorless oil with a yield of 84%.

[0114] (2) Preparation of compound SA-19 ​​represented by formula 19:

[0115] The synthetic route of compound SA-19 ​​is shown in Formula G:

[0116] Formula G

[0117] S3: 500 mg of the compound represented by formula c-1 and 1.18 g of triphenylphosphine were heated in 5 mL of dimethylacetamide at 150° C. for 20 hours under nitrogen protection, and a white solid appeared.

[0118] S4: The solid is recrystallized from dichloromethane / ether to obtain an organic compound SA-19 ​​represented by formula 19, which is a white solid with a yield of 80%.

[0119] LCMS (ESI+): Calculated [(M+H)+]: 608.3, found 608.2.

[0120] The hydrogen spectrum data are:

[0121] 1H NMR (400MHz, CDCl3), δ (ppm): 7.86-7.69 (m, 30H), 3.78-3.71 (m, 4H), 1.83 (apps, 4H), 1.67 (apps, 4H).

[0122] The present invention also provides tests on material-related properties of the organic small molecule compound or the organic small molecule compound obtained by the preparation method, including lap shear tests at different temperatures, in different solvents, and on different substrates, temperature cycle tests, and long-term usability tests.

[0123] The organic small molecule compound provided by the present invention needs to be processed by a hot melt method or a solvent volatilization method before use to increase viscosity. Taking the hot melt method as an example, the organic small molecule undergoes a morphological change after heating and generates viscosity.

[0124] The organic small molecule compound provided by the present invention can also be used in combination with other additives (containing hydroxyl, amino compounds or quaternary ammonium salt compounds, such as ethylene glycol, acetamide, etc.) to further improve the properties of the adhesive, such as durability, elasticity and cyclic performance.

[0125] Take the SA-17 as an example

[0126] (I) Preparation method

[0127] ① Preparation of adhesive

[0128] SA-17 was prepared with reference to Example 1, SA-17 (or a mixture of SA-17 and ethylene glycol) was placed in a sealed bottle, and the sample was heated at 150° C. for 5 minutes. When cooled to room temperature, the resulting adhesive material was obtained.

[0129] SA-17 (or a mixture of SA-17 and ethylene glycol) has adhesive properties after being heated and melted at 150°C. Adhesives with added ethylene glycol have improved elasticity and durability compared to SA-17 adhesives. Adhesives have adhesive properties when the mass fraction of ethylene glycol is less than or equal to 30% of the total mass of SA-17 and ethylene glycol. The mass ratio of SA-17 to ethylene glycol is 20:1 (i.e., the mass fraction of ethylene glycol is approximately equal to 4.8% of the total mass of SA-17 and ethylene glycol, recorded as (SA-17) 20 -EG1), the comprehensive performance of the adhesive is the best.

[0130] ② Preparation of adhesive coating

[0131] The obtained SA-17 adhesive material was deposited on different substrates (thickness of 0.1-0.2 mm), then covered with another substrate and hot pressed, and finally cooled to room temperature. The substrate pair can be directly used for different tests or macro tests.

[0132] (II) Tensile mechanics test

[0133] ①Tensile strength test at different temperatures and on different substrates

[0134] The obtained SA-17 adhered substrate was kept at -40°C, 0°C, and 50°C for 8 hours, then stored at the specified temperature in a tensile machine incubator for 5 minutes, and then its tensile strength was quickly tested. The results are as follows: Figure 1 As shown. Figure 1 It can be seen that SA-17 has high bonding strength on the three substrates of glass, PET and steel, showing the wide temperature applicability of SA-17.

[0135] ②Tensile strength test in different solvents

[0136] PET was used as the test substrate and immersed in four solvents: 1,4-dioxane, ethyl acetate, petroleum ether, and toluene for 4 hours. Then its tensile strength was quickly tested. The results are as follows: Figure 2 As shown, from Figure 2 It can be seen that the bonding strength of SA-17 did not decrease significantly after being immersed in different solvents, and it still had a relatively high bonding strength, which demonstrated the good environmental applicability of SA-17 and ensured its application under different environmental conditions.

[0137] ③Temperature cycle test

[0138] First, the SA-17 adhesive test sample was prepared with a steel substrate and stored at -18°C for 24 hours, then heated to room temperature for a load test (load weight of 25 kg), and then stored again at -18°C for 24 hours. Figure 3 As shown in Figure 2, no displacement of the steel plate was observed within one week. Figure 3 It can be seen that SA-17 has high tolerance to drastic temperature changes, which proves the practical value of SA-17.

[0139] ④Long-term usability test

[0140] SA-17 and (SA-17) at -18°C 20 -EG1 was subjected to a time-dependent adhesion test, and the experimental results are shown in Figure 4 shown. Figure 4 It shows that the bonding strength of SA-17 adhesive began to decrease on the 4th day, while (SA-17) 20 -EG1 showed no attenuation during testing, indicating (SA-17)20 -EG1 has better durability at low temperatures.

[0141] ⑤ Adhesion performance test of carbon chain growth adhesive

[0142] Adhesion tests were conducted on glass and steel substrates using the adhesive structure shown in SA-41 at room temperature. The test results are shown in Figure 5 shown. Figure 5 The results show that the SA-41 adhesive has excellent bonding strength on the glass substrate, indicating that as the carbon chain grows, the structure still has excellent adhesion properties.

[0143] It can be seen from the above results that the organic small molecule compound provided by the present invention is SA-17 and the adhesive (SA-17) after adding ethylene glycol 20 -EG1, SA-41 as an example (of course, other n=1-13, etc.) have excellent bonding properties. They show good bonding properties on different substrates in a wide temperature range. They still show good bonding properties in a wide temperature range (-80-80°C). Excellent adhesion is also observed in liquid nitrogen. SA-17 can still achieve stable bonding in different solvents, and has good reusability and long-term usability, and has high practical value.

[0144] The organic small molecule adhesive provided by the present invention has good bonding properties within a wide temperature range, and has excellent applicability to different use environments (such as temperature, solvent, and bonding material) and high tolerance to drastic temperature changes. It can be reused multiple times and can maintain stable bonding over a long period of use, and has high practical value.

[0145] Those skilled in the art will readily appreciate other embodiments of the invention after considering the specification and practicing the invention herein. The invention is intended to cover any variations, uses or adaptations of the invention that follow the general principles of the invention and include common knowledge or customary techniques in the art of the invention. The specification and examples are to be considered exemplary only, and the true scope and spirit of the invention are indicated by the claims.

[0146] It should be understood that the present invention is not limited to what has been described above and shown in the accompanying drawings, and that various modifications and changes may be made without departing from the scope thereof. The scope of the present invention is limited only by the appended claims.

Claims

1. An organic small molecule compound, characterized in that: It has the following molecular structure: ALB, wherein A is hydroxyl or Group, B is group, the The Y element in the group is selected from one of N and P; One end of L is connected to A, and the other end is connected to B. L is a fatty chain or a fatty chain containing an aromatic substituent, and the carbon number of the fatty chain main chain is 2-14.

2. The organic small molecule compound according to claim 1, characterized in that: The molecular structural formula of the organic small molecule compound is any one of the following molecular structural formulas: Formula b Formula d n=1-13, and the Y element is selected from one of N and P.

3. The organic small molecule compound according to claim 1, characterized in that: The molecular structural formula of the organic small molecule compound is any one of the following molecular formulas:

4. The organic small molecule compound according to claim 1, characterized in that: The molecular structural formula of the organic small molecule compound is one of the following molecular formulas:

5. A method for preparing an organic small molecule compound according to any one of claims 1 to 4, characterized in that: The following steps are involved: A diol or an aliphatic diol containing an aromatic substituent reacts with hydrobromic acid in toluene to undergo a mono- or di-substitution reaction; The substitution reaction product reacts with YPh3 in anhydrous acetonitrile for nucleophilic substitution reaction. The diol comprises a fat chain or a fat chain containing an aromatic substituent, the carbon number of the main chain of the fat chain is 2-14, and the Y element is one of N and P.

6. The method for preparing an organic small molecule compound according to claim 5, characterized in that: The diol and the hydrobromic acid are subjected to a monosubstituted reaction in the toluene at a molar ratio of 1:(1-1.6), the temperature of the monosubstituted reaction is 80-100° C., and the reaction time is 20-26 hours; The monobasic substitution reaction product and the YPh3 are subjected to a nucleophilic substitution reaction in the anhydrous acetonitrile at a molar ratio of 1: (1 to 1.5), the reaction temperature is 80-100° C., and the reaction time is 22 to 26 hours; Preferably, the diol and the hydrobromic acid are subjected to a binary substitution reaction in the toluene at a molar ratio of 1:(10-12), the temperature of the binary substitution reaction is 80-100° C., and the reaction time is 28-32 hours; The binary substitution reaction product and the YPh3 are subjected to nucleophilic addition reaction in N, N-dimethylacetamide at a molar ratio of 1: (2-2.5), the reaction temperature is 80-100° C., and the reaction time is 16-20 hours.

7. Use of the organic small molecule compound according to any one of claims 1 to 4 in the preparation of adhesives or flame retardants.

8. An adhesive, characterized in that: It comprises at least one organic small molecule compound according to any one of claims 1 to 4.

9. An adhesive according to claim 8, characterized in that: The organic small molecule compound needs to be processed by a hot melt method or a solvent volatilization method before use.

10. An adhesive according to claim 9, characterized in that: The adhesive further comprises an additive; Preferably, the additive is selected from one of hydroxyl-containing, amino-containing compounds or quaternary ammonium salt compounds; Preferably, the additive is selected from one of ethylene glycol, acetamide and glycerol.

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