CN106609169B - Nano dendritic molecular fluorescent compound with good oil solubility and preparation method and application thereof - Google Patents
Nano dendritic molecular fluorescent compound with good oil solubility and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a nanoscale dendritic molecular fluorescent compound, which has the molecular formula as follows:
wherein Γ represents a nanoparticle, said
Is a group having a dendritic structure, said R2Is a lipophilic fluorescent group, and n is more than or equal to 0 and less than or equal to 100. The invention further discloses a lubricant containing the nanoscale dendrimer fluorescent compound. The nanoscale dendritic molecular fluorescent compound provided by the invention has fluorescence performance and good abrasion resistance due to the nanoscale structure. The compound is applied to lubricating oil, the lubricating oil is identified by fluorescence, and the addition amount is low, so that the performance of the lubricating oil cannot be adversely affected.
Description
Technical Field
The invention relates to the field of lubricating oil additives, in particular to a nanoscale dendritic molecular fluorescent compound with good oil solubility.
Background
In recent years, with the overall upgrade of industrial products, particularly automotive industrial products, the requirements on the performance of lubricating oils are becoming higher and higher. The emergence of new environmental regulations imposes strict limits on the amount of sulfur, phosphorus, and chlorine-containing lubricating oil additives used. For example, chlorine-based antiwear agents are banned for countries such as the united states and western europe where toxicity is an issue; lead naphthenate is also gradually eliminated due to ecological and toxicity problems; sulfur, phosphorus antiwear agents and ZnDDP have been used in limited amounts by international regulations due to their P and S content, which poison the three-way catalyst in the exhaust gas converter, affect the accuracy of oxygen sensor measurements and toxicity to the ecological environment. The conventional lubricating oil antiwear agents include sulfur antiwear agents (such as sulfurized olefin, sulfurized ester, sulfurized oil, and the like), phosphorus antiwear agents (such as phosphate, phosphite, alkyl phosphonate, and the like), halogen antiwear agents (such as chlorinated paraffin, chlorinated hydrocarbon, chlorinated fatty acid, and the like), organic metal (such as lead naphthenate, dialkyl dithiophosphate (ZnDDP), and the like). These conventional antiwear agents have become increasingly difficult to meet the demanding conditions and requirements for their development in the immediate future.
Just the great challenge faced by the traditional lubricating oil antiwear agent, the nanometer material becomes the lubricating oil antiwear agent and becomes the hot spot of research. The nanometer material is a novel material developed in the middle of the 80 th of the 20 th century, has extraordinary characteristics different from microscopic atoms, molecules and macroscopic substances, and is used as a lubricating oil additive, the novel lubricating material prepared on the basis of the nanometer material does not contribute to the tribology performance of the lubricating oil additive by utilizing the structural characteristics of the traditional lubricating oil additive to realize the functions of resisting wear and reducing a film, but is realized by utilizing the characteristics of the nanometer particles. The nano particles can more easily enter the friction surface due to small granularity, and a thicker surface film can be formed, so that the surfaces of the friction pair can be well separated, and the anti-wear and anti-friction effects are improved.
Dendritic molecules are three-dimensional macromolecules with high branching degree, have very regular and controllable structures, and have a large number of functional end groups. Since Vogtle et al first reported the concept of stepwise repetition to synthesize dendrimers in 1978, and subsequently the synthesis of true dendrimers by Tomalia group, they became a focus of attention by scientists. Because the molecule has nanometer size and molecular weight distribution can reach monodispersity, and the surface of the dendritic macromolecule has amino functional groups which are increased by geometric times and are easy to modify. The structural characteristics enable the dendritic macromolecules to have good dispersibility in the lubricating oil, and meet the most basic requirements of the lubricating oil nano additive. However, at present, the dendritic macromolecular fluorescent compound serving as the anti-wear additive of the lubricating oil is not reported.
Disclosure of Invention
The first purpose of the invention is to provide a novel nano dendrimer fluorescent compound.
The invention provides a nanoscale dendritic molecular fluorescent compound with good oil solubility, and the molecular formula of the compound is shown as formula I:
in the formula I, gamma represents nano-particles, and the formula I is characterized in that
Is a group having a dendritic structure, said R2Is a lipophilic fluorescent group, and n is more than or equal to 0 and less than or equal to 100.
The R is1Preferably a polyamidoamine dendrimer having a molecular structure represented by formula II:
-(CH2)2CONH(CH2)2NH- II。
the R is2Preferably having a molecular structure as shown in formula III:
as a preferable scheme, the nanoscale dendrimer fluorescent compound of the present invention is a nanoscale polyamidoamine dendrimer fluorescent compound, has a molecular structure shown in formula IV, and can be represented by PAMAM in the present invention:
in the molecular formula IV, gamma represents nano particles, n is more than or equal to 0 and less than or equal to 10, m is more than or equal to 1 and less than or equal to 18, and P is more than or equal to 1 and less than or equal to 18; namely, the nano polyamide-amine type dendritic polymer fluorescent compound (PAMAM) is specifically as follows: 0-generation nanoscale dendrimer fluorescent compound (0G, n ≤ 0, 1 ≤ m ≤ 18, 1 ≤ P ≤ 18), 1-generation nanoscale dendrimer fluorescent compound (1G, n ≤ 1, 1 ≤ m ≤ 18, 1 ≤ P ≤ 18), 2-generation nanoscale dendrimer fluorescent compound (2G, n ═ 2, 1 ≤ m ≤ 18, 1 ≤ P ≤ 18), 3-generation nanoscale dendrimer fluorescent compound (3G, n ≤ 3, 1 ≤ m ≤ 18, 1 ≤ P ≤ 18), 4-generation nanoscale dendrimer fluorescent compound (4G, n ≤ 4, 1 ≤ m ≤ 18, 1-generation nanoscale dendrimer fluorescent compound (5G, n ≤ 5, 1 ≤ m ≤ 18, 1 ≤ P ≤ 18), 6-generation nanoscale dendrimer fluorescent compound (6G, n ≤ 6, 1 ≤ m ≤ 18, 1 ≤ P18), 7-generation nanoscale dendrimer fluorescent compound (7G, n is 7, m is not less than 1 and not more than 18, P is not less than 1 and not more than 18), 8-generation nanoscale dendrimer fluorescent compounds (8G, n is 8, m is not less than 1 and not more than 18, P is not less than 1 and not more than 18), 9-generation nanoscale dendrimer fluorescent compounds (9G, n is 9, m is not less than 1 and not more than 18, P is not less than 1 and not more than 18) and 10-generation nanoscale dendrimer fluorescent compounds (10G, n is 10, m is not less than 1 and not more than 18, P is not less than 1 and not more than 18).
According to the invention, a large number of experiments show that in the molecular formula IV, the size of n determines the nano structure, when the value of n is smaller, the abrasion resistance of the compound is poorer, and when the value of n is larger, the compound is difficult to synthesize, and the cost is increased. The value of m influences the difficulty of combining the compound with the fluorescent structure FITC and the stability of the fluorescent compound, and when the value of m is larger or smaller, the property of the fluorescent compound is unstable, and the adding and using effect of the fluorescent compound in the lubricating oil is influenced. P determines the structure of the compound and the intersolubility of the compound and lubricating oil, when the P value is smaller, the solubility of the compound is poor, the compound is not suitable to be used as an additive, and when the P value is larger, the combination of the dendritic molecules and the fluorescent structure FITC is difficult, and the nano structure of the substance is influenced.
In the formula IV, n is an integer from 2 to 6, m is an integer from 1 to 4, and p is an integer from 8 to 12; more preferably, n is an integer of 4 to 6, m is 2, and p is 8 or 9.
The inner core of the nano-particle contains SiO2、Fe3O4Ni or gamma-Fe2O3At least one of (1).
The outer layer of the nano particles is coated with SiO2A housing.
The nanoparticles are preferably SiO-coated2Core-shell type Fe of shell3O4&SiO2Magnetic nanoparticles or core-shell SiO2&SiO2Magnetic nanoparticles.
As a preferable scheme of the invention, the nano particles are coated with SiO2Core-shell type Fe of shell3O4&SiO2Magnetic nanoparticles; in the molecular formula IV, n is an integer selected from 4-6, m is 2, and p is 8 or 9.
The nanoparticles are further preferably magnetic nanoparticles surface-modified with a silane coupling agent. The silane coupling agent is 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane or 3-aminopropyltrimethoxysilane.
The second purpose of the invention is to provide a preparation method of the novel nano dendritic molecular fluorescent compound.
The preparation method comprises the following steps:
i) providing a nanoparticle;
ii) modifying the surface of the nano-particles by using a silane coupling agent, and then reacting the modified product with dendritic molecules to obtain dendritic molecule bonded magnetic nano-particles;
iii) reacting the dendrimer bonded magnetic nanoparticles with a fluorescent compound to obtain a nanoscale dendrimer fluorescent compound;
iv) reacting the nanoscale dendritic molecular fluorescent compound with a compound with an oleophilic group to obtain the nanoscale dendritic molecular fluorescent compound with good oil solubility.
In the preparation method, the compound with lipophilic groups in the step iv) is preferably monohalogenated alkane or sodium alkane alkoxide; further preferred is monobromoalkane or sodium salt of linear paraffin alkoxide.
A third object of the invention is to protect the application of said nanotreemeric compounds.
The compound can be used as a magnetic nano anti-wear additive for lubricating oil or used for fluorescent recognition of the lubricating oil.
The fourth purpose of the invention is to protect the lubricant containing the said nanoscale dendrimer fluorescent compound. The mass content of the compound in the lubricant is preferably 100ppm to 2%.
The compound provided by the invention has the following beneficial effects:
(1) fluorescence: the nanoscale dendritic molecular fluorescent compound contains a Fluorescein Isothiocyanate (FITC) group, and the FITC group increases along with the algebraic increase of the dendritic molecular compound. The fluorescence intensity of different generations of dendritic molecular fluorescent compounds bonded on the inner wall of the capillary is directly measured by adopting a fluorescence microscope, the absorption wavelength is 495nm, and the excitation wavelength is 530 nm. The analysis result shows that the nanoscale dendrimer fluorescent compound presents bright yellow-green fluorescence, and the fluorescence intensity of the nanoscale dendrimer fluorescent compound increases along with algebraic increase of the dendrimer compound. Therefore, the prepared nanoscale dendritic molecular compound has strong fluorescence, and the correspondingly compatible lubricating oil also has yellow-green fluorescence, so that the nanoscale dendritic molecular compound has great potential application in the identification of lubricating oil products.
(2) Nano-scale particles: in the core-shell form of Fe3O4&SiO2Magnetic nanoparticles (or SiO)2Nano particles) surface modification, and preparing the nanoscale dendritic molecular fluorescent compound. Due to the nucleus (Fe)3O4&SiO2Or SiO2Nanoparticles) and surface modifications (dendrimer compounds) are of nanometer size, and the magnetic particle dendrimer compounds prepared should therefore also be of nanometer size. And (3) analyzing the particle size of the 5G magnetic nanoscale dendrimer fluorescent compound by adopting a transmission electron microscope, wherein the particle size of the nanoscale dendrimer fluorescent compound is about 30 nm.
(3) Good oil solubility: the nanoscale dendritic molecular fluorescent compound disclosed by the invention has good solubility in base oil, and can be dissolved in I, II, III, IV and V base oil. This is because the extreme end of the dendrimer fluorescent compound of the present invention is provided with a lipophilic group such as a long-chain alkyl group.
(4) Good wear resistance, excellent extreme pressure properties: the nanoscale magnetic dendrimer compound provided by the invention is added into a lubricant as an antiwear agent, and can achieve a good wear-resisting effect when added into engine lubricating oil, for example. For example, 5G magnetic nanoscale polyamide-amine compound is dissolved in 100N base oil, and the abrasion resistance is tested by using a multifunctional friction and wear tester (SRV). The friction coefficient is slightly reduced with the increase of the load, and the friction coefficient is stable around 0.119. The reason is that the oil film on the surface of the friction pair is gradually formed and stable, which shows that the 5G magnetic nano polyamide-amine compound has good abrasion resistance. In addition, the nanoscale magnetic dendrimer compound can form an oil film on the surface of an object, and the magnetic dendrimer compound is nanoscale particles and can be filled into pits or scratches on the surface of the object to fill the pits or scratches, so that the effect of repairing the surface of the object can be achieved. Meanwhile, the lubricant containing the nanoscale magnetic dendrimer compound also has the effects of cooling the surface of an object and sealing, and has excellent extreme pressure performance.
Drawings
FIG. 1 shows Fe3O4&SiO2A dendritic molecular fluorescent compound as a core nano-scale magnetic particle, and a nano-scale polyamide-amine dendritic fluorescent compound (0G, 1G, m is 3, and p is 9).
FIG. 2 shows fluorescence intensities of different generations under a fluorescence microscope when the polyamidoamine dendrimer of the present invention is bonded on the inner wall of a capillary; a is 0G polyamide-amine dendrimer; b is 1G polyamide-amine dendritic fluorescent compound; c is a 2G polyamide-amine dendritic fluorescent compound; d is a 3G polyamide-amine dendritic fluorescent compound.
Fig. 3 is a transmission electron microscope image of the 5G magnetic nanoscale polyamide-amine compound (m ═ 12) according to the present invention.
FIG. 4 shows Fe3O4&SiO2The core 5G magnetic nano polyamide-amine compound (m is 3, p is 9) multifunctional friction and wear test chart.
FIG. 5 shows Fe3O4&SiO2Comparison graph of extreme pressure performance of polyamide-amine antiwear agent (m 3, p 9) as core 5G and molybdenum dialkyl dithiophosphate.
Detailed Description
The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
In the invention, a fluorescence microscope is adopted to directly measure the nanoscale dendrimer fluorescent compound in the capillary, the absorption wavelength is 495nm, and the excitation wavelength is 530 nm. As can be seen from FIG. 2, the fluorescence intensity of the nanoscale dendrimer fluorescent compound increases as the generation number of the dendrimer compound increases. Therefore, the prepared nanoscale dendritic molecular compound has strong fluorescence, and the correspondingly compatible lubricating oil also has yellow-green fluorescence, so that the nanoscale dendritic molecular compound has great potential application in the identification of lubricating oil products.
The particle size analysis of the 5G magnetic nanoscale polyamide-amine compound was performed by transmission electron microscopy, and it can be seen from FIG. 3 that the particle size of the 5G magnetic nanoscale polyamide-amine compound was about 30 nm.
The lubricating oil containing the nanoscale polyamide-amine compound of the present invention was tested using a multifunctional frictional wear tester (SRV). The test conditions are as follows: friction pair mode: ball and dish, test conditions: 50hz, 50 ℃, gradient pressurization, initial 50N, pressure 100N after 2 minutes, sequential pressurization until 2000N (or coefficient of friction greater than 0.3) is terminated.
The distribution coefficient is a parameter accompanying measurement by gel chromatography, and the closer the parameter is to 1, the more uniform the molecular distribution is.
Example 1
The preparation of magnetic nanoscale polyamide-amine fluorescent compound (n is 0, m is 3, p is 9) with Fe3O4& SiO2 as core, the reaction process is shown in FIG. 1:
(1) adding FeC12 & 4H2O solution of 0.1mol/L and FeC13 & 6H2O solution of 0.2mol/L into a first container according to a volume ratio of 2: 1, placing the first container in an ultrasonic reactor at (30 +/-1) DEG C, performing ultrasonic treatment while dropwise adding NaOH solution of 0.1mol/L until the pH value of the solution is 12, and separating magnetic particles by using a magnetic field. Washing the magnetic particles with deionized water until the pH of the washing solution is 7 to obtain black Fe3O4 nanoparticles.
(2) Weighing 18.4g of Fe3O4 nanoparticles, dispersing in absolute ethyl alcohol (100mL), adding a few drops of oleic acid, and then carrying out ultrasonic dispersion for 10 minutes; transferring the dispersed solution into a second container, adding 20.8g of Tetraethoxysilane (TEOS) and 7g of NH 3. H2O, and stirring for 3 hours; after the reaction is finished, repeatedly washing the solution with distilled water under the condition of magnetic field attraction until the washed solution does not become turbid any more; and (3) carrying out vacuum drying on the obtained precipitate at the temperature of 80 ℃, and finally grinding to obtain the final core-shell Fe3O4& SiO2 magnetic nanoparticles.
(3) Weighing 5g of the core-shell type Fe3O4& SiO2 magnetic nanoparticles, placing the core-shell type Fe3O4& SiO2 magnetic nanoparticles into a flask, dropwise adding 20mL of 10% by volume silane coupling agent (KH 5503-aminopropyltriethoxysilane) toluene solution, reacting for 60min at the temperature of 50 ℃, reducing the temperature to room temperature, performing suction filtration under reduced pressure, washing with methanol, and drying in a vacuum drying oven at the temperature of 70 ℃ for 12 h.
(4) Placing 5g of silanized product in a flask, slowly dropwise adding 20mL of 30% (volume percentage) methyl acrylate methanol solution, stirring at 60 ℃ for 90min, cooling to room temperature, performing vacuum filtration, washing with methanol, and drying. And (3) putting 5.8 g of the mixture into a flask, adding 20mL of 30% (volume percentage) methanol solution of ethylenediamine, stirring for 180min at the temperature of 60 ℃, cooling to room temperature, performing vacuum filtration, washing with methanol, and drying to obtain the 0-generation PAMAM dendrimer modified magnetic nanoparticles.
(5) The resulting 1.8 g of 0 generation PAMAM dendrimer was added to 0.036g of FITC phosphate (pH 9.5) buffer, stirred at room temperature in the dark for 20min, filtered and rinsed to remove excess FITC. And adding the obtained product into 0.1mol/L propanol of sodium propoxide, reacting for 6H at 50 ℃ in a dark place, then dripping 1mol of LC9H19Br, continuing to react for 3H, filtering, leaching with ethanol for three times, and drying to obtain 2.1G of 0G magnetic nanoscale polyamide-amine fluorescent compound (0G, n is 0, m is 3, and p is 9).
Through detection and analysis, the molecular formula of the 0G PAMAM magnetic nano fluorescent compound is (Fe3O4& SiO2) Si (OCH3)3(CH2)3N [ (CH2)2CONH (CH2)2NH ]2[ (C21H9O4NS) (C12H26) ]2, and the molecular weight is 1733.
13CNMR, delta (ppm), 170 ═ O, 180 (bimodal, C ═ O),52-60 (pentamodal, C-Si), 45-51 (bimodal, CH3), 31-40 (bimodal, C-N), 10-20 (tetrameric, CH 2). FTIR (KBr) v (cm-1): 2980 (. nu CH3),2940, 2870, 1467(υCH2),1644(υC＝O)，1560(υ-N-H)，1350(υC-N),1275(υsi-C),1116
1080(υsi-O),1401.8(υsi-O-Fe),579((υFe-O-si)。
And (5) repeating the step 4 and the step 5 to sequentially obtain 1-10 generations of PAMAM dendrimer modified silica gel coated Fe3O4& SiO2 magnetic nanoparticles (m is 12). Repeating the steps to obtain 1-10 generation magnetic nanoscale polyamide-amine fluorescent compounds (1-10G, n is 1-10, m is 3, and p is 9).
The reaction process is shown in fig. 1, taking 0G, 1G, m ═ 3, and p ═ 9 as examples.
Analyzing the 1-10 generation PAMAM magnetic nano fluorescent compound by adopting gel permeation chromatography, wherein the result is as follows:
the molecular formula of the 1G PAMAM magnetic nano fluorescent compound (m is 3, p is 9) is (Fe)3O4&SiO2)Si(OCH3)3(CH2)3N3[(CH2)2CONH(CH2)2NH]6[(C21H9O4NS)(C12H26)]4The number average molecular weight was found to be 3209, and the distribution coefficient was 1.05.
The molecular formula of the 2G PAMAM magnetic nano fluorescent compound (m is 3, p is 9) is as follows: (Fe)3O4&SiO2)Si(OCH3)3(CH2)3N7[(CH2)2CONH(CH2)2NH]14[(C21H9O4NS)(C12H26)]8The number average molecular weight was found to be 6308 with a distribution coefficient of 1.09.
The molecular formula of the 3G PAMAM magnetic nano fluorescent compound (m is 3, p is 9) is as follows: (Fe)3O4&SiO2)Si(OCH3)3(CH2)3N15[(CH2)2CONH(CH2)2NH]30[(C21H9O4NS)(C12H26)]16The number average molecular weight was found to be 12193, and the distribution coefficient was 1.15.
The molecular formula of the 4G PAMAM magnetic nano fluorescent compound (m is 3, p is 9) is as follows: (Fe)3O4&SiO2)Si(OCH3)3(CH2)3N31[(CH2)2CONH(CH2)2NH]62[(C21H9O4NS)(C12H26)]32The number average molecular weight was found to be 24955 with a distribution coefficient of 1.18.
The molecular formula of the 5G PAMAM magnetic nano fluorescent compound (m is 3, p is 9) is as follows: (Fe)3O4&SiO2)Si(OCH3)3(CH2)3N63[(CH2)2CONH(CH2)2NH]126[(C21H9O4NS)(C12H26)]64The number average molecular weight was found to be 48932, with a distribution coefficient of 1.23.
The molecular formula of the 6G PAMAM magnetic nano fluorescent compound (m is 3, p is 9) is as follows: (Fe)3O4&SiO2)Si(OCH3)3(CH2)3N127[(CH2)2CONH(CH2)2NH]254[(C21H9O4NS)(C12H26)]128The number average molecular weight was found to be 93628 with a distribution coefficient of 1.29.
The molecular formula of the 7G PAMAM magnetic nano fluorescent compound (m is 3, p is 9) is as follows: (Fe)3O4&SiO2)Si(OCH3)3(CH2)3N255[(CH2)2CONH(CH2)2NH]510[(C21H9O4NS)(C12H26)]256The number average molecular weight was found to be 188477 with a distribution coefficient of 1.34.
The molecular formula of the 8G PAMAM magnetic nano fluorescent compound (m is 3, p is 9) is as follows: (Fe)3O4&SiO2)Si(OCH3)3(CH2)3N511[(CH2)2CONH(CH2)2NH]1022[(C21H9O4NS)(C12H26)]512The number average molecular weight was found to be 374523 with a distribution coefficient of 1.38.
The molecular formula of the 9G PAMAM magnetic nano fluorescent compound (m is 3, p is 9) is as follows: (Fe)3O4&SiO2)Si(OCH3)3(CH2)3N1023[(CH2)2CONH(CH2)2NH]204[(C21H9O4NS)(C12H26)]1024The number average molecular weight was found to be 751300 with a distribution coefficient of 1.41.
The molecular formula of the 10G PAMAM magnetic nano fluorescent compound (m is 3, p is 9) is as follows: (Fe)3O4&SiO2)Si(OCH3)3(CH2)3N2047[(CH2)2CONH(CH2)2NH]409[(C21H9O4NS)(C12H26)]2048The number average molecular weight was found to be 1490769 with a distribution coefficient of 1.49.
Wherein, Fe is used3O4&SiO2The core 5G magnetic nano polyamide-amine compound (m is 3, p is 9) is taken as an example, the multifunctional friction and wear test graph is shown in figure 4, and the extreme pressure performance of the compound compared with dialkyl molybdenum dithiophosphate is shown in figure 5.
Example 2
And (3) preparing a 0G PAMAM nano polyamide-amine fluorescent compound (m is 1, and P is 18) by taking SiO2 as a core.
(1) Weighing 5g of core-shell SiO2 nanoparticles, placing the core-shell SiO2 nanoparticles in a flask, dropwise adding 20mL of 10 vol% silane coupling agent (KH 5503-aminopropyltriethoxysilane) toluene solution, reacting at 50 ℃ for 60min, reducing the temperature to room temperature, performing vacuum filtration, washing with methanol, and drying in a vacuum drying oven at 70 ℃ for 12 h.
(3) Placing 5g of the silanized product in a second container, slowly dropwise adding 20mL of 30% (volume percentage) methyl acrylate methanol solution, stirring at 60 ℃ for 90min, cooling to room temperature, performing vacuum filtration, washing with methanol, and drying. And (3) putting 5.8 g of the mixture into a flask, adding 20mL of 30% (volume percentage) methanol solution of ethylenediamine, stirring for 180min at the temperature of 60 ℃, cooling to room temperature, performing vacuum filtration, washing with methanol, and drying to obtain the 0-generation PAMAM dendrimer modified magnetic nanoparticles.
(4) The resulting 1.8 g of 0 generation PAMAM dendrimer was added to 0.036g of FITC phosphate (pH 9.5) buffer, stirred at room temperature in the dark for 20min, filtered and rinsed to remove excess FITC. And adding the obtained product into 0.1mol/L sodium methoxide methanol, reacting for 6 hours at 50 ℃ in a dark place, then dripping 1mol of LC18H37Br, continuing to react for 3 hours, filtering, leaching with ethanol for three times, and drying to obtain 2.1G of 0G nanoscale polyamide-amine fluorescent compound (0G, n is 0, m is 1, and p is 18).
Through detection and analysis, the molecular formula of the 0G PAMAM nano fluorescent compound is (SiO2) Si (OCH3)3(CH2)3N (CH2)2CONH (CH2)2NH 2[ (C21H9O4NS) (C19H40) ]2, and the molecular weight is 1730.
13CNMR, delta (ppm), 170 ═ O, 180 (bimodal, C ═ O),52-60 (pentamodal, C-Si), 45-51 (bimodal, CH3), 31-40 (bimodal, C-N), 10-20 (tetrameric, CH 2). FTIR (KBr) v (cm-1): 2980 (upsilon CH3),2940, 2870, 1467 (upsilon CH2),1644 (upsilon C ═ O), 1560 (upsilon-N-H), 1350 (upsilon C-N),1275 (upsilon si-C),1116
1080(υsi-O)，403(υNi-O)
Repeating the step 3 and the step 4 to obtain the 1-to 10-generation nanoscale polyamide-amine fluorescent compound (1-10G, n is 1-10, m is 1, and p is 18).
Analyzing the 1-10 generation PAMAM nano fluorescent compound by adopting gel permeation chromatography, wherein the molecular formula of the 1G PAMAM nano fluorescent compound (m is 1, p is 18) is (SiO)2)Si(OCH3)3(CH2)3N3[(CH2)2CONH(CH2)2NH]6[(C21H9O4NS)(C19H40)]4The number average molecular weight was found to be 3371, with a distribution coefficient of 1.02.
The molecular formula of the 2G nanoscale polyamide-amine fluorescent compound (m is 1, p is 18) is as follows: (SiO)2)Si(OCH3)3(CH2)3N7[(CH2)2CONH(CH2)2NH]14[(C21H9O4NS)(C19H40)]8The number average molecular weight was found to be 6806 with a distribution coefficient of 1.05.
The molecular formula of the 3G nanoscale polyamide-amine fluorescent compound (m is 1, p is 18) is as follows: (SiO)2)Si(OCH3)3(CH2)3N15[(CH2)2CONH(CH2)2NH]30[(C21H9O4NS)(C19H40)]16The number average molecular weight was found to be 13363 with a distribution coefficient of 1.09.
The molecular formula of the 4G nanoscale polyamide-amine fluorescent compound (m is 1, p is 18) is as follows: (SiO)2)Si(OCH3)3(CH2)3N31[(CH2)2CONH(CH2)2NH]62[(C21H9O4NS)(C19H40)]32The number average molecular weight was found to be 27469 with a distribution coefficient of 1.15.
The molecular formula of the 5G nanoscale polyamide-amine fluorescent compound (m is 1, p is 18) is as follows: (SiO)2)Si(OCH3)3(CH2)3N63[(CH2)2CONH(CH2)2NH]126[(C21H9O4NS)(C19H40)]64The number average molecular weight was found to be 51074, and the distribution coefficient was 1.19.
The molecular formula of the 6G nanoscale polyamide-amine fluorescent compound (m is 1, p is 18) is as follows: (SiO)2)Si(OCH3)3(CH2)3N127[(CH2)2CONH(CH2)2NH]254[(C21H9O4NS)(C19H40)]128The number average molecular weight was found to be 104206 with a distribution coefficient of 1.22.
The molecular formula of the 7G nanoscale polyamide-amine fluorescent compound (m is 1, p is 18) is as follows: (SiO)2)Si(OCH3)3(CH2)3N255[(CH2)2CONH(CH2)2NH]510[(C21H9O4NS)(C19H40)]256The number average molecular weight was found to be 209807 with a distribution coefficient of 1.29.
The molecular formula of the 8G nanoscale polyamide-amine fluorescent compound (m is 1, p is 18) is as follows: (SiO)2)Si(OCH3)3(CH2)3N511[(CH2)2CONH(CH2)2NH]1022[(C21H9O4NS)(C19H40)]512The number average molecular weight was found to be 417359 with a distribution coefficient of 1.33.
The molecular formula of the 9G nanometer polyamide-amine fluorescent compound (m is 1, p is 18) is as follows: (SiO)2)Si(OCH3)3(CH2)3N1023[(CH2)2CONH(CH2)2NH]204[(C21H9O4NS)(C19H40)]1024The number average molecular weight was found to be 837142 with a distribution coefficient of 1.39.
The molecular formula of the 10G nanometer polyamide-amine fluorescent compound (m is 1, p is 18) is as follows: (SiO)2)Si(OCH3)3(CH2)3N2047[(CH2)2CONH(CH2)2NH]409[(C21H9O4NS)(C19H40)]2048The number average molecular weight was found to be 1662627 with a distribution coefficient of 1.45.
The present invention is illustrated by the synthesis of the fluorescent compounds in examples 1 and 2. According to the method, only relevant raw materials are adjusted, and other compounds with n being more than or equal to 0 and less than or equal to 10, m being more than or equal to 1 and less than or equal to 18 and P being more than or equal to 1 and less than or equal to 18 can be synthesized.
Example 3
The preparation method comprises the steps of using a 4G magnetic nanoscale polyamide-amine fluorescent compound (n is 4, m is 2, and P is 8) with Fe3O4& SiO2 as a core for gasoline engine lubricating oil, using the 4G magnetic nanoscale polyamide-amine fluorescent compound (n is 4, m is 2, and P is 8) as a 4G magnetic nanoscale antiwear agent A and an organic molybdenum salt antiwear agent (such as molybdenum dialkyl dithiophosphate) commonly used in the current market according to the formula shown in Table 1, and blending SM 5W-30 gasoline engine lubricating oil.
TABLE 1 SM 5W-30 gasoline engine lubricating oils
Note: a contains an anti-wear additive, which is zinc dialkyl dithiophosphate (ZnDDP).
The results of the SM 5W-30 gasoline engine lubricating oil analysis are shown in Table 2:
TABLE 2 SM 5W-30 gasoline engine lubricating oil analysis results
Note: m friction pair mode: ball and dish, test conditions: 50hz, 200g, 80 ℃; m is absorption wavelength 495nm, excitation wavelength 530 nm.
From the analysis data in table 2, it can be seen that the SM 5W-30 oil formulated with the 4G magnetic nano antiwear agent a of this example has a friction coefficient of 0.07, and the SM 5W-30 oil formulated with molybdenum dialkyl dithiophosphate as an antiwear agent has a friction coefficient of 0.11, thereby indicating that the 4G magnetic nano polyamide-amine fluorescent compound (n ═ 4, m ═ 2, P ═ 8) is a very excellent nano fluorescent antiwear agent.
Example 4
The 4G magnetic nano polyamide-amine fluorescent compound (n is 4, m is 3, and P is 12) taking gamma-Fe 2O3& SiO2 as a core is used in diesel engine lubricating oil as a magnetic nano antiwear agent.
CJ-45W-40 diesel engine lubricating oil was formulated according to the formulation in table 3 using 4G magnetic nano polyamide-amine compound (n ═ 4, m ═ 3, P ═ 12) as 4G magnetic nano antiwear agent B.
TABLE 3 CJ-45W-40 diesel engine lubricating oil formulations
Note: b is not containing antiwear additive.
The results of the analysis of CJ-45W-40 diesel engine oil are shown in Table 4:
TABLE 4 CJ-45W-40 Diesel Engine oil analysis results
Note: m friction pair mode: ball and dish, test conditions: 50hz, 200g, 80 ℃; m is absorption wavelength 495nm, excitation wavelength 530 nm.
As can be seen from the above table, the friction coefficient curve is unstable as shown by the test results of the anti-wear performance test of the formula I by using the SRV. After the 4G magnetic nano antiwear agent B of this example was added, the friction coefficient of CJ-45W-40 diesel engine lubricating oil was stable and was only 0.09, thus demonstrating that the 4G magnetic nano polyamide-amine fluorescent compound (n ═ 4, m ═ 3, and P ═ 12) had good antiwear performance and was a very excellent fluorescent antiwear additive.
Example 5
A4G nanometer polyamide-amine fluorescent compound (n is 4, m is 3 and P is 10) taking SiO2 as a core is used as a magnetic nanometer antiwear agent in diesel engine lubricating oil.
CJ-45W-40 diesel engine lubricating oil was formulated according to the formulation in table 5 using 4G of nano polyamide-amine fluorescent compound (n 4, m 3, P10) as 4G of nano antiwear agent C.
TABLE 5 CJ-45W-40 diesel engine lubricating oil formulations
Note: c is free of antiwear additives.
The results of the analysis of CJ-45W-40 diesel engine oil are shown in Table 6:
TABLE 6 CJ-45W-40 Diesel Engine oil analysis results
Note: m friction pair mode: ball and dish, test conditions: 50hz, 200g, 80 ℃.
M is absorption wavelength 495nm, excitation wavelength 530 nm.
As can be seen from the above table, the friction coefficient curve is unstable as shown by the test results of the anti-wear performance test of the formula I by using the SRV. After the 4G nano antiwear agent C of this example was added, the friction coefficient of CJ-45W-40 diesel engine lubricating oil was stable and was only 0.10, thus demonstrating that the 4G nano polyamide-amine fluorescent compound (n ═ 4, m ═ 3, and P ═ 10) had good antiwear performance and was a very excellent fluorescent antiwear additive.
Example 6
The Ni & SiO2 is used as a core 5G magnetic nano polyamide-amine fluorescent compound (n is 5, m is 4, and P is 11) which is used as a magnetic nano antiwear agent in diesel engine lubricating oil.
CF-45W-30 diesel engine lubricating oil was formulated according to the formulation in table 7 using 5G magnetic nanoscale polyamide-amine fluorescent compound (n ═ 5, m ═ 4, P ═ 11) as magnetic nano antiwear agent D.
TABLE 7 CF-45W-30 Diesel Engine lubricating oil formulation
Note: d is free of antiwear additives.
The results of the analysis of the CF-45W-30 diesel engine oil are shown in Table 8:
TABLE 8 analysis results of lubricating oil for CF-45W-30 Diesel engines
Note: m friction pair mode: ball and dish, test conditions: 50hz, 200g, 80 ℃.
M is absorption wavelength 495nm, excitation wavelength 530 nm.
As can be seen from the above table, the friction coefficient curve is unstable as shown by the test results of the anti-wear performance test of the formula I by using the SRV. After the 5G magnetic nano antiwear agent D of this example is added, the friction coefficient of the CF-45W-30 diesel engine lubricating oil is stable and is only 0.08, thus demonstrating that the 5G magnetic nano polyamide-amine compound (n is 5, m is 4, P is 11) has good antiwear performance and is a very excellent fluorescent antiwear additive.
Example 7
The magnetic nano polyamide-amine fluorescent compound (n is 5, m is 1, and P is 12) which takes Fe3O4& SiO2 as a core and is 5G is used as a magnetic nano antiwear agent for diesel engine lubricating oil.
CF-45W-30 diesel engine lubricating oils were formulated according to the formulation in table 9 using 5G magnetic nanoscale polyamide-amine fluorescent compounds (n ═ 5, m ═ 1, P ═ 12) as magnetic nano antiwear agents E.
TABLE 9 CF-45W-30 Diesel Engine lubricating oil formulation
Note: e is free of antiwear additives.
The results of the analysis of the CF-45W-30 diesel engine oil are shown in Table 10:
TABLE 10 analysis results of lubricating oil for CF-45W-30 Diesel engines
Note: m friction pair mode: ball and dish, test conditions: 50hz, 200g, 80 ℃.
M is absorption wavelength 495nm, excitation wavelength 530 nm.
As can be seen from the above table, the friction coefficient curve is unstable as shown by the test results of the anti-wear performance test of the formula I by using the SRV. After the 5G magnetic nanoscale polyamide-amine fluorescent compound E of the present example was added, the friction coefficient of the CF-45W-30 diesel engine lubricating oil was stable and was only 0.08, which indicates that the 5G magnetic nanoscale polyamide-amine fluorescent compound (n ═ 5, m ═ 1, and P ═ 12) had good antiwear performance and was a very excellent fluorescent antiwear additive.
Example 8
The 6G magnetic nano polyamide-amine fluorescent compound (n is 6, m is 2, and P is 9) taking Fe3O4& SiO2 as a core is used in diesel engine lubricating oil as a magnetic nano antiwear agent.
CF-45W-30 diesel engine lubricating oils were formulated according to the formulation in table 11 using 6G magnetic nanoscale polyamide-amine fluorescent compounds (n ═ 6, m ═ 2, P ═ 9) as magnetic nano antiwear agents F.
TABLE 11 CF-45W-30 Diesel Engine lubricating oil formulation
Note: f is free of antiwear additives.
The results of the analysis of the CF-45W-30 diesel engine oil are shown in Table 12:
TABLE 12 analysis results of CF-45W-30 Diesel Engine lubricating oil
Note: m friction pair mode: ball and dish, test conditions: 50hz, 200g, 80 ℃.
M is absorption wavelength 495nm, excitation wavelength 530 nm.
As can be seen from the above table, the friction coefficient curve is unstable as shown by the test results of the anti-wear performance test of the formula I by using the SRV. After the 6G magnetic nanoscale polyamide-amine fluorescent compound F of the present example was added, the friction coefficient of the CF-45W-30 diesel engine lubricating oil was stable and was only 0.07, which indicates that the 6G magnetic nanoscale polyamide-amine fluorescent compound (n ═ 6, m ═ 2, and P ═ 9) had good antiwear performance and was a very excellent fluorescent antiwear additive.
Example 9
The 6G magnetic nano polyamide-amine fluorescent compound (n is 6, m is 3, and P is 14) taking gamma-Fe 2O3& SiO2 as a core is used in diesel engine lubricating oil as a magnetic nano antiwear agent.
CF-45W-30 diesel engine lubricating oil was formulated according to the formulation in table 13 using 6G magnetic nanoscale polyamide-amine fluorescent compound (n ═ 6, m ═ 3, P ═ 14) as magnetic nano antiwear agent H.
TABLE 13 CF-45W-30 Diesel Engine lubricating oil formulation
Note: m is free of antiwear additives.
The results of the analysis of the CF-45W-30 diesel engine oil are shown in Table 14:
TABLE 14 CF-45W-30 Diesel Engine lubricating oil analysis results
Note: m friction pair mode: ball and dish, test conditions: 50hz, 200g, 80 ℃.
M is absorption wavelength 495nm, excitation wavelength 530 nm.
As can be seen from the above table, the friction coefficient curve is unstable as shown by the test results of the anti-wear performance test of the formula I by using the SRV. After the 6G magnetic nanoscale polyamide-amine fluorescent compound H of the present example was added, the friction coefficient of the CF-45W-30 diesel engine lubricating oil was stable and was only 0.08, which indicates that the 6G magnetic nanoscale polyamide-amine fluorescent compound (n ═ 6, m ═ 3, and P ═ 14) had good antiwear performance and was a very excellent antiwear additive.
Example 10
7G nano polyamide-amine fluorescent compound (n is 7, m is 1, P is 9) taking SiO2 as core and used as nano antiwear agent for diesel engine lubricating oil
CF-45W-40 diesel engine lubricating oils were formulated according to the formulation in table 15 using 7G of nano-polyamide-amine fluorescent compound (n-7, m-1, P-9) as magnetic nano antiwear agent J.
TABLE 15 CF-45W-40 Diesel Engine lubricating oil formulations
Note: n x does not contain an antiwear additive.
The results of the CF-45W-40 diesel engine lubricating oil analysis are shown in Table 16:
TABLE 16 analysis results of CF-45W-40 Diesel Engine lubricating oils
Note: m friction pair mode: ball and dish, test conditions: 50hz, 200g, 80 ℃.
M is absorption wavelength 495nm, excitation wavelength 530 nm.
As can be seen from the above table, the friction coefficient curve is unstable as shown by the test results of the anti-wear performance test of the formula I by using the SRV. After the 7G nanoscale polyamide-amine fluorescent compound J of this example was added, the friction coefficient of the CF-45W-40 diesel engine lubricating oil was stable and was only 0.06, which indicates that the 7G nanoscale polyamide-amine fluorescent compound (n-7, m-1, p-9) had good antiwear performance and was a very excellent antiwear additive.
Example 11
An 8G magnetic nano polyamide-amine fluorescent compound (n is 8, m is 8, and p is 10) taking Ni & SiO2 as a core is used in gasoline engine lubricating oil as a magnetic nano antiwear agent.
According to the formula shown in table 17, an SN/GF-50W-30 gasoline engine lubricating oil was formulated by using an 8G magnetic nanoscale polyamide-amine fluorescent compound (n ═ 8, m ═ 8, and p ═ 10) as a magnetic nano antiwear agent L and an organic molybdenum salt antiwear agent (e.g., molybdenum dialkyldithiophosphate) commonly used in the market at present, respectively.
TABLE 17 SN/GF-50W-20 gasoline engine lubricating oil
Note: q contains an antiwear additive, which is zinc dialkyldithiophosphate (ZDDP).
The results of the SN/GF-50W-30 gasoline engine lubricating oil analysis are shown in Table 18:
TABLE 18 SN/GF-50W-30 gasoline engine lubricating oil analysis results
Note: m friction pair mode: ball and dish, test conditions: 50hz, 200g, 80 ℃.
M is absorption wavelength 495nm, excitation wavelength 530 nm.
As can be seen from the analysis data in table 18, the SN/GF-50W-30 oil product formulated with the 8G magnetic nanoscale polyamidoamine fluorescent compound L of this example had a friction coefficient of 0.08, while the SN/GF-50W-20 oil product formulated with molybdenum dialkyldithiophosphate as an antiwear agent had a friction coefficient of 0.11, thereby indicating that the 8G magnetic nanoscale polyamidoamine fluorescent compound (n ═ 8, m ═ 8, p ═ 10) is a very excellent magnetic nano antiwear agent.
Example 12
The Ni & SiO2 is used as a core 9G magnetic nano polyamide-amine fluorescent compound (n is 9, m is 5, and p is 12) which is used as a magnetic nano antiwear agent in diesel engine lubricating oil.
According to the formula shown in table 19, a CI-410W-30 diesel engine lubricating oil was formulated by using a 9G magnetic nanoscale polyamide-amine fluorescent compound (n ═ 9, M ═ 5) as a magnetic nano antiwear agent M and an organic molybdenum salt antiwear agent (such as molybdenum dialkyldithiophosphate) commonly used in the market at present.
TABLE 19 CI-410W-30 Diesel Engine lubricating oils
Note: w is filled with an anti-wear additive, which is referred to as zinc dialkyldithiophosphate (ZDDP).
The results of the CI-410W-30 diesel engine lubricating oil analysis are shown in Table 20:
TABLE 20 CI-410W-30 Diesel Engine lubricating oil analysis results
Note: m friction pair mode: ball and dish, test conditions: 50hz, 200g, 80 ℃.
M is absorption wavelength 495nm, excitation wavelength 530 nm.
As can be seen from the analysis data in table 20, the CI-410W-30 oil formulated with the 9G magnetic nanoscale polyamidoamine fluorescent compound of this example had a friction coefficient of 0.08, and the CI-410W-30 oil formulated with molybdenum dialkyldithiophosphate as an antiwear agent had a friction coefficient of 0.13, thereby indicating that the 9G magnetic nanoscale polyamidoamine fluorescent compound (n ═ 9, m ═ 5) is a very excellent magnetic nano antiwear agent.
Example 13
10G magnetic nano polyamide-amine fluorescent compound (n is 10, m is 4, p is 15) taking gamma-Fe 2O3& SiO2 as core and used for diesel engine lubricating oil as magnetic nano antiwear agent
According to the formulation in table 21, CF-415W-40 diesel engine lubricating oil was formulated by using 10G of magnetic nanoscale polyamide-amine fluorescent compound (N is 10, m is 4, and p is 15) as magnetic nano antiwear agent N and an organic molybdenum salt antiwear agent (such as molybdenum dialkyl dithiophosphate) commonly used in the market at present.
TABLE 21 CF-415W-40 gasoline engine lubricating oils
Note: y is filled with an anti-wear additive, which is zinc dialkyldithiophosphate (ZDDP).
The results of the analysis of the CF-415W-40 diesel engine lubricating oil are shown in Table 22:
TABLE 22 CF-415W-40 Diesel Engine oil analysis results
Note: m friction pair mode: ball and dish, test conditions: 50hz, 200g, 80 ℃.
M is absorption wavelength 495nm, excitation wavelength 530 nm.
As can be seen from the analysis data in table 22, the friction coefficient of the CF-415W-40 diesel engine lubricating oil formulated with the 10G magnetic nanoscale polyamide-amine fluorescent compound N of the present example was 0.09, and the friction coefficient of the CF-415W-40 diesel engine lubricating oil formulated with molybdenum dialkyldithiophosphate as an antiwear agent was 0.13, which indicated that the 10G magnetic nanoscale polyamide-amine fluorescent compound (N is 10, m is 4, and p is 15) was a very excellent magnetic nano antiwear agent.
Example 14
5G magnetic nano polyamide-amine fluorescent compounds taking gamma-Fe 2O3 and SiO2 as cores are dissolved in 100N base oil, and an SRV is used for carrying out an anti-wear performance test on the base oil. The results are shown in FIG. 4. As can be seen from fig. 4, as the load increases, the friction coefficient decreases slightly, and the friction coefficient becomes stable around 0.119. The reason is that the oil film on the surface of the friction pair is gradually formed and stable, which shows that the 5G magnetic nano polyamide-amine compound has good abrasion resistance. When the load is applied to 1100N, the coefficient of friction suddenly increases, because the oil film on the friction surface is broken and the lubrication is lost. Under the same conditions, when the load is added to 800N, the oil film on the surface of the friction pair is broken (as shown in figure 5), thereby demonstrating that the 5G magnetic nanoscale polyamide-amine fluorescent compound has excellent extreme pressure performance.
Comparing the above compounds together, the overall performance of the compounds provided in examples 3 and 8 is optimal.
Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that many modifications and improvements can be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.
Claims (9)
1. A nanoscale dendritic molecular fluorescent compound with good oil solubility is characterized in that the molecular formula of the compound is shown as formula I:
Γ(CH2)3N(2 n+1 -1)R1 (2 n+2 -2)R2 (2 n+1 )I；
in formula I, Γ represents nanoparticles, and the (CH)2)3N(2 n+1 -1)R1Is a group having a dendritic structure, said R2Is a lipophilic fluorescent group;
the R is1Is a polyamide-amine dendrimer with a molecular structure shown in a formula II;
-(CH2)2CONH(CH2)2NH- II；
the R is2The molecular structure of (A) is shown as formula III:
n is an integer from 2 to 6, m is an integer from 1 to 4, and p is an integer from 8 to 12.
2. The compound of claim 1, wherein n is an integer selected from 4 to 6, m is 2, and p is 8 or 9.
3. Compound according to claim 1 or 2, characterized in that the core of the nanoparticle contains SiO2、Fe3O4Ni or gamma-Fe2O3At least one of (1).
4. The compound of claim 3, wherein the nanoparticles are selected from the group consisting of outer layers coated with SiO2The core is Fe3O4Core-shell type Fe3O4&SiO2Magnetic nanoparticles, or coated with SiO2The inner core is SiO2Core-shell SiO2&SiO2Magnetic nanoparticles.
5. The compound of claim 4, wherein the nanoparticles are magnetic nanoparticles surface-modified with a silane coupling agent; the silane coupling agent is 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane or 3-aminopropyltrimethoxysilane.
6. The method for preparing the good oil-soluble nanoscale dendritic molecular fluorescent compound as claimed in any one of claims 1 to 5, characterized by comprising the following steps:
i) providing a nanoparticle;
ii) modifying the surface of the nano-particles by using a silane coupling agent, and then reacting the modified product with dendritic molecules to obtain dendritic molecule bonded magnetic nano-particles;
iii) reacting the dendrimer bonded magnetic nanoparticles with a fluorescent compound to obtain a nanoscale dendrimer fluorescent compound;
iv) reacting the nanoscale dendrimer fluorescent compound with a compound with an oleophilic group to obtain a nanoscale dendrimer fluorescent compound with good oil solubility;
the compound with lipophilic group is monohalogenated alkane or sodium alkane alcoholate.
7. The method according to claim 6, wherein the compound having lipophilic group is monobromoalkane or sodium salt of linear alkane alkoxide.
8. Use of the nanoscale dendritic molecular fluorescent compound of any one of claims 1 to 5 or the nanoscale dendritic molecular fluorescent compound prepared by the method of claim 6 or 7 in preparation of an anti-wear additive for lubricating oil and identification of lubricating oil products.
9. A lubricant containing the nanoscale dendrimer fluorescent compound according to any one of claims 1 to 5 or the nanoscale dendrimer fluorescent compound prepared by the method according to claim 6 or 7, wherein the nanoscale dendrimer fluorescent compound is contained in the lubricant in an amount of 100ppm to 2% by mass.
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