CN106609169A - Nanoscale dendritic molecular fluorescent compound with good oil solubility and preparation method and application thereof - Google Patents
Nanoscale 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. The molecular formula of the nanoscale dendritic molecular fluorescent compound is shown in the description, wherein gamma represents nanometer particles, (CH2)3N(2n+1-1)R1 is a group of a dendritic structure, R2 is a lipophilic fluorescent group, and n is larger than or equal to 0 and is smaller than or equal to 100. The invention further discloses a lubricating agent containing the nanoscale dendritic molecular fluorescent compound. The nanoscale dendritic molecular fluorescent compound has the fluorescence property and has the good wear resistance due to the nanoscale structure. The compound is applied in lubricating oil, the lubricating oil is recognized through fluorescence, the additive amount is small, and no adverse effect is produced to the property of the lubricating oil.
Description
Technical field
The present invention relates to lube oil additive field, specifically, is related to a kind of good oil-soluble nanoscale dendrimers fluorescent chemicalses.
Background technology
In recent years, with the complete upgrading of industrial products especially auto industry product so that the requirement more and more higher to lubricants performance.The appearance of new environmental regulation, to the usage amount of sulfur-bearing, phosphorus, chlorine lube oil additive strict restriction is proposed.As chlorine class antiwear additive is disabled to such as U.S. of country for having been had because of its toxicity problem and West Europe；Lead naphthenate is also because ecological and toxicity problem is gradually eliminated；The P and S that sulfur class, Phosphorus antiwear additive and ZnDDP contain because of it can make the three-way catalyst in tail gas converter be poisoned, affect oxygen sensor measurement accuracy and the toxicity to ecological environment, be used by international regulations limitation.Lubrication oil antiwear agent traditional at present has sulfur class antiwear additive (such as olefine sulfide, sulfurised ester, sulfurized oil), Phosphorus antiwear additive (such as phosphate ester, phosphite ester, phosphonate ester), halogen class antiwear additive (such as chlorinated paraffin, chlorohydrocarbon, chlorinated fatty acid), organic metal class (such as lead naphthenate, dialkyl dithiophosphate (ZnDDP)) etc..These traditional antiwear additives have been increasingly difficult to meet the requirement of harsh operating mode and era development to them.
The huge challenge that exactly conventional lubrication oil antiwear additive is faced, nano material becomes lubrication oil antiwear agent and becomes the focus of research.Nano material is 20th century new material that grows up of the mid-80, with different from microcosmic atom, molecule, also different from the extraordinary characteristic of macroscopic material, the novel lubricating material prepared using based on nano material is used as lube oil additive, the characteristics of its contribution to tribological property is not as conventional lubrication oil additive using in its structure is wear-resistant subtracting film effect to realize its, but realize by using nano-particle self character.Nanoparticle easily engaging friction surface because granularity is little, it is possible to create thicker skin covering of the surface, enables surface of friction pair to separate well, improves antiwear and antifriction effect.
Dendrimer is the three-dimensional macromolecular with Gao Zhiduization, with very regular and controllable structure, and has a large amount of functional end groups.Progressively repeat, to synthesize the concept of dendrimer, and since being subsequently combined into real dendritic macromole by Tomalia is little, progressively to have become the focus of scientists concern from reported firsts such as Vogtle in 1978.Because molecule itself has nano-scale, and molecular weight distribution is up to monodispersity, while dendritic macromole surface has the amido functional group easily modified increased with geometry multiple.These construction featuress make dendrimer be possibly realized with good dispersion in lubricating oil, meet the most basic requirement of Nanoparticles As Lubricating Oil Additives.But at present, there is not been reported as additive for wear resistance of lubricating oil for dendrimer fluorescent chemicalses.
The content of the invention
The first object of the present invention is to provide a kind of novel nano dendrimer fluorescent chemicalses.
The invention provides a kind of good oil-soluble nanoscale dendrimers fluorescent chemicalses, the molecular formula of the compound is shown in formula I：
In the molecule Formulas I, Γ represents nano-particle, describedIt is the group with dendritic structure, the R2For lipophile fluorophor, 0≤n≤100.
The R1Polyamidoamine dendrimer preferably containing molecular structure shown in Formula II：
-(CH2)2CONH(CH2)2NH- II。
The R2It is preferred that having the molecular structure as shown in formula III：
Used as a kind of preferred version, nanoscale dendrimers fluorescent chemicalses of the present invention are nanoscale polyamidoamine dendrimer fluorescent chemicalses, with the molecular structure as shown in formula IV, can be represented with PAMAM in the present invention：
In the molecule formula IV, Γ represents nano-particle, 0≤n≤10,1≤m≤18,1≤P≤18；I.e. described nanoscale polyamidoamine dendrimer fluorescent chemicalses (PAMAM) are specially：0 generation nanoscale dendrimers fluorescent chemicalses (0G，N=0，1≤m≤18，1≤P≤18)、1 generation nanoscale dendrimers fluorescent chemicalses (1G，N=1，1≤m≤18，1≤P≤18)、2 generation nanoscale dendrimers fluorescent chemicalses (2G，N=2，1≤m≤18，1≤P≤18)、3 generation nanoscale dendrimers fluorescent chemicalses (3G，N=3，1≤m≤18，1≤P≤18)、4 generation nanoscale dendrimers fluorescent chemicalses (4G，N=4，1≤m≤18，1≤P≤18)、5 generation nanoscale dendrimers fluorescent chemicalses (5G，N=5，1≤m≤18，1≤P≤18)、6 generation nanoscale dendrimers fluorescent chemicalses (6G，N=6，1≤m≤18，1≤P≤18)、7 generation nanoscale dendrimers fluorescent chemicalses (7G，N=7，1≤m≤18，1≤P≤18)、8 generation nanoscale dendrimers fluorescent chemicalses (8G，N=8，1≤m≤18，1≤P≤18)、9 generation nanoscale dendrimers fluorescent chemicalses (9G，N=9，1≤m≤18，1≤P≤18) and 10 generation nanoscale dendrimers fluorescent chemicalses (10G，N=10，1≤m≤18，1≤P≤18).
The present invention is had found by many experiments, and in the molecule formula IV, the size of n determines nanostructured, and when n values are less than normal, the wear resistence of compound is poor, and when n values are bigger than normal, compound synthesis are difficult, and cost increases.Complexity and the stability of fluorescent chemicalses that the value effect of m is combined to compound with fluorescence structure FITC, when m values are bigger than normal or less than normal, the property of fluorescent chemicalses is unstable, affects its addition using effect in lubricating oil.P determines the structure and compound of compound and the intersolubility of lubricating oil, and when P values are less than normal, compound dissolution is bad, should not use as additive, when P values are bigger than normal, the combination of dendrimer and fluorescence structure FITC is difficult, and affects the nanostructured of the material.
In the preferably molecule formula IV of the invention, integers of the n in 2～6, integers of the m in 1～4, integers of the p in 8～12；More preferably, integers of the n in 4～6, it is 8 or 9 that m is 2, p.
The kernel of nano-particle of the present invention contains SiO2、Fe3O4, Ni or γ-Fe2O3In at least one.
The external sheath of the nano-particle has SiO2Shell.
The nano-particle is preferably and is coated with SiO2The core-shell type Fe of shell3O4&SiO2Magnetic nanoparticle or core-shell type SiO2&SiO2Magnetic nanoparticle.
Used as the preferred version of the present invention, the nano-particle is to be coated with SiO2The core-shell type Fe of shell3O4&SiO2Magnetic nanoparticle；And in molecule formula IV, integers of the n in 4～6, it is 8 or 9 that m is 2, p.
The nano-particle more preferably carries out the magnetic nanoparticle of surface modification with silane coupler.The silane coupler is APTES, 3- glycydoxies trimethoxy silane or 3- TSL 8330s.
The second object of the present invention is to provide the preparation method of the novel nano dendrimer fluorescent chemicalses.
The preparation method comprises the steps：
I) nano-particle is provided；
Ii) surface of the nano-particle is modified using silane coupler, then reacts the product after modification and dendrimer, obtain dendrimers bonding magnetic nanoparticle；
Iii) dendrimers bonding magnetic nanoparticle and fluorescent chemicalses are reacted, nanoscale dendrimers fluorescent chemicalses are obtained；
Iv) the nanoscale dendrimers fluorescent chemicalses are reacted with the compound with lipophilic group, obtains that there are good oil-soluble nanoscale dendrimers fluorescent chemicalses.
In the preparation method, step iv) compound with lipophilic group is preferably a halogenated alkane or alkane sodium alkoxide；More preferably bromoalkanes hydrocarbon or linear paraffin sodium alkoxide.
The third object of the present invention is the application of the dendritic molecular compound of the protection nanotrees.
The compound can be as lubricating oil magnetic Nano antiwear additive, or as lubricating oil fluorescence identifying.
The fourth object of the present invention is lubricant of the protection containing the nanoscale dendrimers fluorescent chemicalses.Compound mass content in the lubricant is preferably 100ppm～2%.
The compound that the present invention is provided has the advantages that：
(1) fluorescence：Contain class fluorescein isothiocyanate (FITC) group in nanoscale dendrimers fluorescent chemicalses, and class FITC group increases as dendrimers compound algebraically increases.Different algebraically dendrimers fluorescent chemicalses fluorescence intensities using the direct para-linkage of fluorescence microscope on capillary tube inner wall are directly determined, absorbing wavelength 495nm, excitation wavelength 530nm.Analysis result shows that nanoscale dendrimers fluorescent chemicalses are presented bright yellow-green fluorescence, and increase as dendrimers compound algebraically increases its fluorescence intensity.It can thus be seen that the lubricating oil that the nanoscale dendrimers compound for preparing has very strong fluorescence, corresponding compatibility equally has yellow-green fluorescence, differentiate that there is great potential application in lube product.
(2) nanometer particle：In the Fe of core-shell type3O4&SiO2Magnetic nano-particle (or SiO2Nanoparticle) surface modification, prepare nanoscale dendrimers fluorescent chemicalses.Due to core (Fe3O4&SiO2Or SiO2Nanoparticle) and surface modification (dendrimers compound) all have nano-scale, therefore prepare magnetic-particle dendrimers compound also should be nano level.Granularmetric analyses are carried out to 5G magnetic Nano level dendrimers fluorescent chemicalses using transmission electron microscope, the particle diameter of the nanoscale dendrimers fluorescent chemicalses is about 30nm.
(3) good oil-soluble：Dissolubility of the nanoscale dendrimers fluorescent chemicalses of the present invention in base oil is fine, in can dissolving I, II, III, IV, V class base oil.This is because the least significant end of the dendrimers fluorescent chemicalses of the present invention is arranged just like lipophilic groups such as chain alkyls.
(4) good abrasion resistance, excellent extreme pressure property：It is when being for example added in engine lubricating oil, to play good abrasion resistant effect that the nano-scale magnetic dendrimers compound of the present invention is added in lubricant as antiwear additive.For example 5G magnetic Nano level polyamide-amide class compound dissolutions are carried out into abrasion resistance test using multifunction friction wear tester (SRV) in the base oil of 100N to it.As load increases, coefficient of friction is slightly reduced, and coefficient of friction tends towards stability 0.119 or so.This is because fastness sea surface oil slick is gradually formed and stable, illustrates that 5G magnetic Nano level polyamide-amide class compounds have good abrasion resistance.In addition, except forming oil film in body surface, because magnetic dendrimers compound is nano-scale particle, it can also be filled in the pit of the body surface or cut nano-scale magnetic dendrimers compound, the pit or cut are filled up, such that it is able to play a part of to repair body surface.Meanwhile, also there is the lubricant of the nano-scale magnetic dendrimers compound containing the present invention cooling body surface and sealing function to have excellent extreme pressure property simultaneously.
Description of the drawings
Fig. 1 is of the present invention with Fe3O4&SiO2For the dendrimers fluorescent chemicalses of core nanoparticles level magnetic-particle, nanoscale polyamide-amide class branch fluorescent chemicalses (0G, 1G, m=3, p=9) course of reaction.
Fig. 2 is bonded on capillary tube inner wall for polyamide-amide class dendrimers of the present invention, the fluorescence intensity of different algebraically under fluorescence microscope；A is 0G polyamide-amide class branch fluorescent chemicalses；B is 1G polyamide-amide class branch fluorescent chemicalses；C is 2G polyamide-amide class branch fluorescent chemicalses；D is 3G polyamide-amide class branch fluorescent chemicalses.
Fig. 3 is 5G magnetic Nanos level polyamide-amide class compound (m=12) transmission electron microscope picture of the present invention.
Fig. 4 is of the present invention with Fe3O4&SiO2For core 5G magnetic Nano level polyamide-aminated compoundss (m=3, p=9) multifunction friction wear Test Drawing.
Fig. 5 is of the present invention with Fe3O4&SiO2For core 5G polyamide-amide class antiwear additive (m=3, p=9) and molybdenum dialkyl-dithiophosphate extreme pressure property comparison diagram.
Specific embodiment
Following examples are used to illustrate the present invention, but are not limited to the scope of the present invention.
In the present invention, using fluorescence microscope directly to being placed on capillary tube in nanoscale dendrimers fluorescent chemicalses directly determined, absorbing wavelength 495nm, excitation wavelength 530nm.Figure it is seen that nanoscale dendrimers fluorescent chemicalses increase as dendrimers compound algebraically increases its fluorescence intensity.It can thus be seen that the lubricating oil that the nanoscale dendrimers compound for preparing has very strong fluorescence, corresponding compatibility equally has yellow-green fluorescence, differentiate that there is great potential application in lube product.
Granularmetric analyses are carried out to 5G magnetic Nano level polyamide-amide class compounds using transmission electron microscope, from figure 3, it can be seen that the particle diameter of 5G magnetic Nano level polyamide-amide class compounds is about 30nm.
The present invention is used the carrying out of the lubricating oil of the nanoscale polyamide-amide class compound containing the present invention is tested using multifunction friction wear tester (SRV).Experimental condition：Friction secondary mode：Ball and disk, experimental condition：50hz, 50 DEG C, gradient pressurization, initial 50N, pressure is 100N after 2 minutes, is pressurizeed successively, until 2000N (or coefficient of friction is more than 0.3) terminates.
Breadth coefficient is to determine incidental parameter using gel chromatography, and the parameter represents that the molecular distribution is more uniform closer to 1.
Embodiment 1
The preparation of magnetic Nano level polyamide-amide class fluorescent chemicalses (n=0, m=3, p=9) with Fe3O4＆SiO2 as core, the reaction mechanism mechanism of reaction is as shown in Figure 1：
(1) the FeC136H2O solution of the FeC124H2O solution of 0.1mol/L, 0.2mol/L is pressed into (volume ratio 2：1) in being added to the first container, (30 ± 1) DEG C ultrasonic reactor, the NaOH solution of ultrasonic Deca 0.1mol/L simultaneously, until pH value of solution=12, using magnetic field separation magnetic-particle is gone out are positioned over.Magnetic-particle is washed with deionized, to the pH=7 of cleaning mixture, you can obtain the Fe3O4 nanoparticles of black.
(2) the Fe3O4 nanoparticles for weighing 18.4g are scattered in dehydrated alcohol (100mL), add a few oil dripping acid, then ultrasonic disperse 10 minutes；Solution after dispersion is proceeded in second container, 20.8g tetraethyl orthosilicates (TEOS) and 7g NH3H2O is added, is stirred 3 hours；After the completion of reaction, under conditions of magnetic field suction, by solution distilled water cyclic washing, until the solution after cleaning no longer becomes cloudy；The precipitation for obtaining is carried out 80 DEG C of vacuum drying, the last finely ground Fe3O4＆SiO2 magnetic nano-particles for obtaining final core-shell type.
(3) the Fe3O4＆SiO2 magnetic nano-particles for weighing core-shell type described in 5g are placed in flask, Deca 20mL volumetric concentration is 10% silane coupler (KH550 APTESs) toluene solution, under the conditions of temperature 50 C, reaction 60min, reduce pressure sucking filtration after room temperature is down to, and washed with methanol, then it is dried 12h in 70 DEG C of vacuum drying ovens.
(4) product obtained after 5 grams of silanizations is placed in flask, the methanol solution 20mL of the acrylic acid methyl ester. of 30% (percentage by volume) is slowly added dropwise, after stirring 90min under conditions of temperature is for 60 DEG C, reduce pressure sucking filtration after room temperature is down to, washed with methanol, dried.Take 5.8 grams to be placed in flask, add the methanol solution of the ethylenediamine of 20mL 30% (percentage by volume), after stirring 180min under conditions of temperature is for 60 DEG C, reduce pressure sucking filtration after room temperature is down to, washed with methanol, dried, obtain the magnetic nanoparticle of 0 generation PAMAM dendrimers modification.
(5) 0.036g FITC phosphate (pH=9.5) buffer solution, lucifuge is added to be stirred at room temperature after 20min obtain 1.8 gram of 0 generation PAMAM dendrimers, filtration, drip washing remove unnecessary FITC.During then the product for obtaining to be added the propanol of sodium propoxide of 0.1mol/L, 50 DEG C of lucifuges react 6h, then instill 1moLC9H19Br, continue to react 3h, filter after doing, with ethanol rinse three times, drying, obtain 2.1 grams of 0G magnetic Nano level polyamide-amide class fluorescent chemicalses (0G, n=0, m=3, p=9).
Analyze after testing, the molecular formula of 0G PAMAM magnetic Nano fluorescent chemicalses is (Fe3O4＆SiO2) Si (OCH3) 3 (CH2) 3N [(CH2) 2CONH (CH2) 2NH] 2 [(C21H
9O4NS) (C12H26)] 2, molecular weight is 1733.
13CNMR, δ (ppm), 170-180 (bimodal, C=O), 52-60 (five peaks, C-Si), 45-51 (bimodal, CH3), 31-40 (bimodal, C-N), 10-20 (four peaks, CH2).FTIR(KBr)υ(cm-1)：2980 (υ CH3), 2940,2870,1467 (υ CH2), 1644 (υ C=O), 1560 (υ-N-H), 1350 (υ C-N), 1275 (υ si-C), 11161080(υsi-O),1401.8(υsi-O-Fe),579((υFe-O-si)。
Repeat step 4 and step 5 will successively obtain gel coated Fe3O4＆SiO2 magnetic nano-particles (m=12) of 1～10 generation PAMAM dendrimers modification.Repeat, will successively obtain for 1～10 generation magnetic Nano level polyamide-amide class fluorescent chemicalses (1～10G, n=1-10, m=3, p=9).
Wherein, with 0G, 1G, m=3, as a example by p=9, course of reaction is as shown in Figure 1.
1～10 generation PAMAM magnetic Nano fluorescent chemicalses are analyzed using gel permeation chromatography, as a result for：
The molecular formula of 1G PAMAM magnetic Nano fluorescent chemicalses (m=3, p=9) is (Fe3O4&SiO2)Si(OCH3)3(CH2)3N3[(CH2)2CONH(CH2)2NH]6[(C21H9O4NS)(C12H26)]4, number-average molecular weight actual measurement is 3209, and breadth coefficient is 1.05.
The molecular formula of 2G PAMAM magnetic Nano fluorescent chemicalses (m=3, p=9) is：(Fe3O4&SiO2)Si(OCH3)3(CH2)3N7[(CH2)2CONH(CH2)2NH]14[(C21H9O4NS)(C12H26)]8, number-average molecular weight actual measurement is 6308, and breadth coefficient is 1.09.
The molecular formula of 3G PAMAM magnetic Nano fluorescent chemicalses (m=3, p=9) is：(Fe3O4&SiO2)Si(OCH3)3(CH2)3N15[(CH2)2CONH(CH2)2NH]30[(C21H9O4NS)(C12H26)]16, number-average molecular weight actual measurement is 12193, and breadth coefficient is 1.15.
The molecular formula of 4G PAMAM magnetic Nano fluorescent chemicalses (m=3, p=9) is：(Fe3O4&SiO2)Si(OCH3)3(CH2)3N31[(CH2)2CONH(CH2)2NH]62[(C21H9O4NS)(C12H26)]32, number-average molecular weight actual measurement is 24955, and breadth coefficient is 1.18.
The molecular formula of 5G PAMAM magnetic Nano fluorescent chemicalses (m=3, p=9) is：(Fe3O4&SiO2)Si(OCH3)3(CH2)3N63[(CH2)2CONH(CH2)2NH]126[(C21H9O
4NS)(C12H26)]64, number-average molecular weight actual measurement is 48932, and breadth coefficient is 1.23.
The molecular formula of 6G PAMAM magnetic Nano fluorescent chemicalses (m=3, p=9) is：(Fe3O4&SiO2)Si(OCH3)3(CH2)3N127[(CH2)2CONH(CH2)2NH]254[(C21H9O4NS)(C12H26)]128, number-average molecular weight actual measurement is 93628, and breadth coefficient is 1.29.
The molecular formula of 7G PAMAM magnetic Nano fluorescent chemicalses (m=3, p=9) is：(Fe3O4&SiO2)Si(OCH3)3(CH2)3N255[(CH2)2CONH(CH2)2NH]510[(C21H9O4NS)(C12H26)]256, number-average molecular weight actual measurement is 188477, and breadth coefficient is 1.34.
The molecular formula of 8G PAMAM magnetic Nano fluorescent chemicalses (m=3, p=9) is：(Fe3O4&SiO2)Si(OCH3)3(CH2)3N511[(CH2)2CONH(CH2)2NH]1022[(C21H9O4NS)(C12H26)]512, number-average molecular weight actual measurement is 374523, and breadth coefficient is 1.38.
The molecular formula of 9G PAMAM magnetic Nano fluorescent chemicalses (m=3, p=9) is：(Fe3O4&SiO2)Si(OCH3)3(CH2)3N1023[(CH2)2CONH(CH2)2NH]204[(C21H9O4NS)(C12H26)]1024, number-average molecular weight actual measurement is 751300, and breadth coefficient is 1.41.
The molecular formula of 10G PAMAM magnetic Nano fluorescent chemicalses (m=3, p=9) is：(Fe3O4&SiO2)Si(OCH3)3(CH2)3N2047[(CH2)2CONH(CH2)2NH]409[(C21H9O4NS)(C12H26)]2048, number-average molecular weight actual measurement is 1490769, and breadth coefficient is 1.49.
Wherein, with Fe3O4&SiO2As a example by 5G magnetic Nanos level polyamide-amide class compound (m=3, p=9) of core, its multifunction friction wear Test Drawing is as shown in figure 4, it is as shown in Figure 5 with molybdenum dialkyl-dithiophosphate extreme pressure property comparison diagram.
Embodiment 2
With SiO2 as the preparation of core 0G PAMAM nanoscales polyamide-amide class fluorescent chemicalses (m=1, P=18).
(1) the SiO2 nanoparticles for weighing 5g core-shell types are placed in flask, Deca 20mL volumetric concentration is 10% silane coupler (KH550 APTESs) toluene solution, under the conditions of temperature 50 C, reaction 60min, reduce pressure sucking filtration after room temperature is down to, and washed with methanol, then it is dried 12h in 70 DEG C of vacuum drying ovens.
(3) product obtained after 5 grams of silanizations is placed in second container, the methanol solution 20mL of the acrylic acid methyl ester. of 30% (percentage by volume) is slowly added dropwise, after stirring 90min under conditions of temperature is for 60 DEG C, reduce pressure sucking filtration after room temperature is down to, washed with methanol, dried.Take 5.8 grams to be placed in flask, add the methanol solution of the ethylenediamine of 20mL 30% (percentage by volume), after stirring 180min under conditions of temperature is for 60 DEG C, reduce pressure sucking filtration after room temperature is down to, washed with methanol, dried, obtain the magnetic nanoparticle of 0 generation PAMAM dendrimers modification.
(4) 0.036g FITC phosphate (pH=9.5) buffer solution, lucifuge is added to be stirred at room temperature after 20min obtain 1.8 gram of 0 generation PAMAM dendrimers, filtration, drip washing remove unnecessary FITC.During then the product for obtaining to be added the methanol of Feldalat NM of 0.1mol/L, 50 DEG C of lucifuges react 6h, then instill 1moLC18H37Br, continue to react 3h, filter after doing, with ethanol rinse three times, drying, obtain 2.1 grams of 0G nanoscale polyamide-amide class fluorescent chemicalses (0G, n=0, m=1, p=18).
Analyze after testing, the molecular formula of 0G PAMAM nano fluorescent compounds is (SiO2) Si (OCH3) 3 (CH2) 3N (CH2) 2CONH (CH2) 2NH] 2 [(C21H9O4NS) (C19H40)] 2, molecular weight is 1730.
13CNMR, δ (ppm), 170-180 (bimodal, C=O), 52-60 (five peaks, C-Si), 45-51 (bimodal, CH3), 31-40 (bimodal, C-N), 10-20 (four peaks, CH2).FTIR(KBr)υ(cm-1)：2980 (υ CH3), 2940,2870,1467 (υ CH2), 1644 (υ C=O), 1560 (υ-N-H), 1350 (υ C-N), 1275 (υ si-C), 11161080 (υ si-O), 403 (υ Ni-O)
Repeat step 3 and step 4, will successively obtain for 1～10 generation nanoscale polyamide-amide class fluorescent chemicalses (1～10G, n=1-10, m=1, p=18).
1～10 generation PAMAM nano fluorescent compound is analyzed using gel permeation chromatography, wherein the molecular formula of 1G PAMAM nano fluorescents compound (m=1, p=18) is (SiO2)Si(OCH3)3(CH2)3N3[(CH2)2CONH(CH2)2NH]6[(C21H9O4NS)(C19H40)]4, number-average molecular weight actual measurement is 3371, and breadth coefficient is 1.02.
The molecular formula of 2G nanoscales polyamide-amide class fluorescent chemicalses (m=1, p=18) is： (SiO2)Si(OCH3)3(CH2)3N7[(CH2)2CONH(CH2)2NH]14[(C21H9O4NS)(C19H40)]8, number-average molecular weight actual measurement is 6806, and breadth coefficient is 1.05.
The molecular formula of 3G nanoscales polyamide-amide class fluorescent chemicalses (m=1, p=18) is：(SiO2)Si(OCH3)3(CH2)3N15[(CH2)2CONH(CH2)2NH]30[(C21H9O4NS)(C19H40)]16, number-average molecular weight actual measurement is 13363, and breadth coefficient is 1.09.
The molecular formula of 4G nanoscales polyamide-amide class fluorescent chemicalses (m=1, p=18) is：(SiO2)Si(OCH3)3(CH2)3N31[(CH2)2CONH(CH2)2NH]62[(C21H9O4NS)(C19H40)]32, number-average molecular weight actual measurement is 27469, and breadth coefficient is 1.15.
The molecular formula of 5G nanoscales polyamide-amide class fluorescent chemicalses (m=1, p=18) is：(SiO2)Si(OCH3)3(CH2)3N63[(CH2)2CONH(CH2)2NH]126[(C21H9O4NS)(C19H40)]64, number-average molecular weight actual measurement is 51074, and breadth coefficient is 1.19.
The molecular formula of 6G nanoscales polyamide-amide class fluorescent chemicalses (m=1, p=18) is：(SiO2)Si(OCH3)3(CH2)3N127[(CH2)2CONH(CH2)2NH]254[(C21H9O4NS)(C19H40)]128, number-average molecular weight actual measurement is 104206, and breadth coefficient is 1.22.
The molecular formula of 7G nanoscales polyamide-amide class fluorescent chemicalses (m=1, p=18) is：(SiO2)Si(OCH3)3(CH2)3N255[(CH2)2CONH(CH2)2NH]510[(C21H9O4NS)(C19H40)]256, number-average molecular weight actual measurement is 209807, and breadth coefficient is 1.29.
The molecular formula of 8G nanoscales polyamide-amide class fluorescent chemicalses (m=1, p=18) is：(SiO2)Si(OCH3)3(CH2)3N511[(CH2)2CONH(CH2)2NH]1022[(C21H9O4NS)(C19H40)]512, number-average molecular weight actual measurement is 417359, and breadth coefficient is 1.33.
The molecular formula of 9G nanoscales polyamide-amide class fluorescent chemicalses (m=1, p=18) is：(SiO2)Si(OCH3)3(CH2)3N1023[(CH2)2CONH(CH2)2NH]204[(C21H9O4NS)(C19H40)]1024, number-average molecular weight actual measurement is 837142, and breadth coefficient is 1.39.
The molecular formula of 10G nanoscales polyamide-amide class fluorescent chemicalses (m=1, p=18) is：(SiO2)Si(OCH3)3(CH2)3N2047[(CH2)2CONH(CH2)2NH]409[(C21H9O4NS)(C19H40)]2048, number-average molecular weight actual measurement is 1662627, and breadth coefficient is 1.45.
The present invention enumerates the synthetic method of fluorescent chemicalses by embodiment 1 and 2.According to above method, only related raw material is adjusted, other compounds for obtaining 0≤n≤10 of the present invention, 1≤m≤18,1≤P≤18 can be synthesized.
Embodiment 3
4G magnetic Nano level polyamide-amide class fluorescent chemicalses (n=4 with Fe3O4＆SiO2 as core, m=2, P=8) it is used for formula of the petrol engine lubricating oil according to table 1 as magnetic Nano antiwear additive, 4G magnetic Nano level polyamide-amide class fluorescent chemicalses (n=4 are respectively adopted, m=2, P=8) as common are machine molybdenum salt antiwear additive (such as molybdenum dialkyl-dithiophosphate) in 4G magnetic Nano antiwear additive A, existing market, SM 5W-30 petrol engine lubricating oil is allocated.
The SM 5W-30 petrol engine lubricating oil of table 1
Note：A* contains antiwear additive in the inside, and antiwear additive refers to zinc dialkyl dithiophosphate (ZnDDP).
The analysis result of SM 5W-30 petrol engine lubricating oil is as shown in table 2：
The SM 5W-30 petrol engine lubricating oil analysis results of table 2
Note：M* friction secondary modes：Ball and disk, experimental condition：50hz, 200g, 80 DEG C；M** absorbing wavelength 495nm, excitation wavelength 530nm.
Can be seen that from the analytical data of table 2, the coefficient of friction of the SM 5W-30 oil products allocated using the use 4G magnetic Nano antiwear additive A of the present embodiment is 0.07, and the coefficient of friction of the SM 5W-30 oil products that molybdenum dialkyl-dithiophosphate is allocated as antiwear additive is 0.11, thus 4G magnetic Nano level polyamide-amide class fluorescent chemicalses (n=4 are illustrated, m=2, P=8) it is very outstanding nano fluorescent antiwear additive.
Embodiment 4
It is used in diesel engine lubricant as magnetic Nano antiwear additive by core 4G magnetic Nano level polyamide-amide class fluorescent chemicalses (n=4, m=3, P=12) of γ-Fe2O3＆SiO2.
According to the formula of table 3, CJ-4 5W-40 diesel engine lubricants are allocated as 4G magnetic Nano antiwear additives B with 4G magnetic Nanos level polyamide-amide class compound (n=4, m=3, P=12).
The CJ-4 5W-40 diesel engine lubricant formula of table 3
Note：B* the insides do not contain antiwear additive.
The analysis result of CJ-4 5W-40 diesel oil oil machine oil is as shown in table 4：
The CJ-4 5W-40 diesel engine lubricant analysis results of table 4
Note：M* friction secondary modes：Ball and disk, experimental condition：50hz, 200g, 80 DEG C；M** absorbing wavelength 495nm, excitation wavelength 530nm.
As can be seen from the above table, abrasion resistance test is carried out to formula I using SRV, result of the test shows that friction coefficient curve is unstable.And add after the 4G magnetic Nano antiwear additive B of the present embodiment, the stable friction factor of CJ-4 5W-40 diesel engine lubricants, only 0.09, thus 4G magnetic Nano level polyamide-amide class fluorescent chemicalses (n=4 are illustrated, m=3, P=12) there is good abrasion resistance, is very outstanding fluorescence antiwear additive.
Embodiment 5
It is used in diesel engine lubricant as magnetic Nano antiwear additive by core 4G nanoscale polyamide-amide class fluorescent chemicalses (n=4, m=3, P=10) of SiO2.
According to the formula of table 5, CJ-4 5W-40 diesel engine lubricants are allocated as 4G nano antiwear agents C with 4G nanoscales polyamide-amide class fluorescent chemicalses (n=4, m=3, P=10).
The CJ-4 5W-40 diesel engine lubricant formula of table 5
Note：C* the insides do not contain antiwear additive.
The analysis result of CJ-4 5W-40 diesel oil oil machine oil is as shown in table 6：
The CJ-4 5W-40 diesel engine lubricant analysis results of table 6
Note：M* friction secondary modes：Ball and disk, experimental condition：50hz, 200g, 80 DEG C.
M** absorbing wavelength 495nm, excitation wavelength 530nm.
As can be seen from the above table, abrasion resistance test is carried out to formula I using SRV, result of the test shows that friction coefficient curve is unstable.And add after the 4G nano antiwear agent C of the present embodiment, the stable friction factor of CJ-4 5W-40 diesel engine lubricants, only 0.10, thus 4G nanoscale polyamide-amide class fluorescent chemicalses (n=4 are illustrated, m=3, P=10) there is good abrasion resistance, is very outstanding fluorescence antiwear additive.
Embodiment 6
It is used in diesel engine lubricant as magnetic Nano antiwear additive by core 5G magnetic Nano level polyamide-amide class fluorescent chemicalses (n=5, m=4, P=11) of Ni＆SiO2.
According to the formula of table 7, CF-4 5W-30 diesel engine lubricants are allocated as magnetic Nano antiwear additive D with 5G magnetic Nanos level polyamide-amide class fluorescent chemicalses (n=5, m=4, P=11).
The CF-4 5W-30 diesel engine lubricant formula of table 7
Note：D* the insides do not contain antiwear additive.
The analysis result of CF-4 5W-30 diesel oil oil machine oil is as shown in table 8：
The CF-4 5W-30 diesel engine lubricant analysis results of table 8
Note：M* friction secondary modes：Ball and disk, experimental condition：50hz, 200g, 80 DEG C.
M** absorbing wavelength 495nm, excitation wavelength 530nm.
As can be seen from the above table, abrasion resistance test is carried out to formula I using SRV, result of the test shows that friction coefficient curve is unstable.And add after the 5G magnetic Nano antiwear additive D of the present embodiment, the stable friction factor of CF-4 5W-30 diesel engine lubricants, only 0.08, thus 5G magnetic Nano level polyamide-amide class compound (n=5 are illustrated, m=4, P=11) there is good abrasion resistance, is very outstanding fluorescence antiwear additive.
Embodiment 7
It is used in diesel engine lubricant as magnetic Nano antiwear additive by core 5G magnetic Nano level polyamide-amide class fluorescent chemicalses (n=5, m=1, P=12) of Fe3O4＆SiO2.
According to the formula of table 9, CF-4 5W-30 diesel engine lubricants are allocated as magnetic Nano antiwear additive E with 5G magnetic Nanos level polyamide-amide class fluorescent chemicalses (n=5, m=1, P=12).
The CF-4 5W-30 diesel engine lubricant formula of table 9
Note：E* the insides do not contain antiwear additive.
The analysis result of CF-4 5W-30 diesel oil oil machine oil is as shown in table 10：
The CF-4 5W-30 diesel engine lubricant analysis results of table 10
Note：M* friction secondary modes：Ball and disk, experimental condition：50hz, 200g, 80 DEG C.
M** absorbing wavelength 495nm, excitation wavelength 530nm.
As can be seen from the above table, abrasion resistance test is carried out to formula I using SRV, result of the test shows that friction coefficient curve is unstable.And add after the 5G magnetic Nano level polyamide-amide class fluorescent chemicalses E of the present embodiment, the stable friction factor of CF-4 5W-30 diesel engine lubricants, only 0.08, thus 5G magnetic Nano level polyamide-amide class fluorescent chemicalses (n=5 are illustrated, m=1, P=12) there is good abrasion resistance, is very outstanding fluorescence antiwear additive.
Embodiment 8
It is used in diesel engine lubricant as magnetic Nano antiwear additive by core 6G magnetic Nano level polyamide-amide class fluorescent chemicalses (n=6, m=2, P=9) of Fe3O4＆SiO2.
According to the formula of table 11, CF-4 5W-30 diesel engine lubricants are allocated as magnetic Nano antiwear additive F with 6G magnetic Nanos level polyamide-amide class fluorescent chemicalses (n=6, m=2, P=9).
The CF-4 5W-30 diesel engine lubricant formula of table 11
Note：F* the insides do not contain antiwear additive.
The analysis result of CF-4 5W-30 diesel oil oil machine oil is as shown in table 12：
The CF-4 5W-30 diesel engine lubricant analysis results of table 12
Note：M* friction secondary modes：Ball and disk, experimental condition：50hz, 200g, 80 DEG C.
M** absorbing wavelength 495nm, excitation wavelength 530nm.
As can be seen from the above table, abrasion resistance test is carried out to formula I using SRV, result of the test shows that friction coefficient curve is unstable.And add after the 6G magnetic Nano level polyamide-amide class fluorescent chemicalses F of the present embodiment, the stable friction factor of CF-4 5W-30 diesel engine lubricants, only 0.07, thus 6G magnetic Nano level polyamide-amide class fluorescent chemicalses (n=6 are illustrated, m=2, P=9) there is good abrasion resistance, is very outstanding fluorescence antiwear additive.
Embodiment 9
It is used in diesel engine lubricant as magnetic Nano antiwear additive by core 6G magnetic Nano level polyamide-amide class fluorescent chemicalses (n=6, m=3, P=14) of γ-Fe2O3＆SiO2.
According to the formula of table 13, CF-4 5W-30 diesel engine lubricants are allocated as magnetic Nano antiwear additive H with 6G magnetic Nanos level polyamide-amide class fluorescent chemicalses (n=6, m=3, P=14).
The CF-4 5W-30 diesel engine lubricant formula of table 13
Note：M* the insides do not contain antiwear additive.
The analysis result of CF-4 5W-30 diesel oil oil machine oil is as shown in table 14：
The CF-4 5W-30 diesel engine lubricant analysis results of table 14
Note：M* friction secondary modes：Ball and disk, experimental condition：50hz, 200g, 80 DEG C.
M** absorbing wavelength 495nm, excitation wavelength 530nm.
As can be seen from the above table, abrasion resistance test is carried out to formula I using SRV, result of the test shows that friction coefficient curve is unstable.And add after the 6G magnetic Nano level polyamide-amide class fluorescent chemicalses H of the present embodiment, the stable friction factor of CF-4 5W-30 diesel engine lubricants, only 0.08, thus 6G magnetic Nano level polyamide-amide class fluorescent chemicalses (n=6 are illustrated, m=3, P=14) there is good abrasion resistance, is very outstanding antiwear additive.
Embodiment 10
It is used for diesel engine lubricant as nano antiwear agent by core 7G nanoscale polyamide-amide class fluorescent chemicalses (n=7, m=1, P=9) of SiO2
According to the formula of table 15, CF-4 5W-40 diesel engine lubricants are allocated as magnetic Nano antiwear additive J with 7G nanoscales polyamide-amide class fluorescent chemicalses (n=7, m=1, P=9).
The CF-4 5W-40 diesel engine lubricant formula of table 15
Note：N* the insides do not contain antiwear additive.
The analysis result of CF-4 5W-40 diesel engine lubricants is as shown in table 16：
The CF-4 5W-40 diesel engine lubricant analysis results of table 16
Note：M* friction secondary modes：Ball and disk, experimental condition：50hz, 200g, 80 DEG C.
M** absorbing wavelength 495nm, excitation wavelength 530nm.
As can be seen from the above table, abrasion resistance test is carried out to formula I using SRV, result of the test shows that friction coefficient curve is unstable.And add after the 7G nanoscale polyamide-amide class fluorescent chemicalses J of the present embodiment, the stable friction factor of CF-4 5W-40 diesel engine lubricants, only 0.06, thus 7G nanoscale polyamide-amide class fluorescent chemicalses (n=7 are illustrated, m=1, p=9) there is good abrasion resistance, is very outstanding antiwear additive.
Embodiment 11
It is used in petrol engine lubricating oil as magnetic Nano antiwear additive by core 8G magnetic Nano level polyamide-amide class fluorescent chemicalses (n=8, m=8, p=10) of Ni＆SiO2.
According to the formula of table 17,8G magnetic Nano level polyamide-amide class fluorescent chemicalses (n=8 are respectively adopted, m=8, p=10) as common are machine molybdenum salt antiwear additive (such as molybdenum dialkyl-dithiophosphate) in magnetic Nano antiwear additive L and existing market, SN/GF-5 0W-30 petrol engine lubricating oil is allocated.
The SN/GF-5 0W-20 petrol engine lubricating oil of table 17
Note：Q contains antiwear additive in the inside, and antiwear additive refers to zinc dialkyl dithiophosphate (ZDDP).
The analysis result of SN/GF-5 0W-30 petrol engine lubricating oil is as shown in table 18：
The SN/GF-5 0W-30 petrol engine lubricating oil analysis results of table 18
Note：M* friction secondary modes：Ball and disk, experimental condition：50hz, 200g, 80 DEG C.
M** absorbing wavelength 495nm, excitation wavelength 530nm.
Can be seen that from the analytical data of table 18, the coefficient of friction of the SN/GF-5 0W-30 oil products allocated using the 8G magnetic Nano level polyamide-amide class fluorescent chemicalses L of the present embodiment is 0.08, and the coefficient of friction of the SN/GF-5 0W-20 oil products that molybdenum dialkyl-dithiophosphate is allocated as antiwear additive is 0.11, thus 8G magnetic Nano level polyamide-amide class fluorescent chemicalses (n=8 are illustrated, m=8, p=10) it is very outstanding magnetic Nano antiwear additive.
Embodiment 12
It is used in diesel engine lubricant as magnetic Nano antiwear additive by core 9G magnetic Nano level polyamide-amide class fluorescent chemicalses (n=9, m=5, p=12) of Ni＆SiO2.
According to the formula of table 19,9G magnetic Nano level polyamide-amide class fluorescent chemicalses (n=9 are respectively adopted, m=5) as common are machine molybdenum salt antiwear additive (such as molybdenum dialkyl-dithiophosphate) in magnetic Nano antiwear additive M and existing market, CI-4 10W-30 diesel engine lubricants are allocated.
The CI-4 10W-30 diesel engine lubricants of table 19
Note：W* contains antiwear additive in the inside, and antiwear additive refers to zinc dialkyl dithiophosphate (ZDDP).
The analysis result of CI-4 10W-30 diesel engine lubricants is as shown in table 20：
The CI-4 10W-30 diesel engine lubricant analysis results of table 20
Note：M* friction secondary modes：Ball and disk, experimental condition：50hz, 200g, 80 DEG C.
M** absorbing wavelength 495nm, excitation wavelength 530nm.
Can be seen that from the analytical data of table 20, the coefficient of friction of the CI-410W-30 oil products allocated using the 9G magnetic Nano level polyamide-amide classes fluorescent chemicalses of the present embodiment is 0.08, and the coefficient of friction of the CI-410W-30 oil products that molybdenum dialkyl-dithiophosphate is allocated as antiwear additive is 0.13, thus illustrate that 9G magnetics nanoscale polyamide-amide class fluorescent chemicalses (n=9, m=5) is very outstanding magnetic Nano antiwear additive.
Embodiment 13
It is used for diesel engine lubricant as magnetic Nano antiwear additive by core 10G magnetic Nano level polyamide-amide class fluorescent chemicalses (n=10, m=4, p=15) of γ-Fe2O3＆SiO2
According to the formula of table 21,10G magnetic Nano level polyamide-amide class fluorescent chemicalses (n=10 are respectively adopted, m=4, p=15) as common are machine molybdenum salt antiwear additive (such as molybdenum dialkyl-dithiophosphate) in magnetic Nano antiwear additive N and existing market, CF-4 15W-40 diesel engine lubricants are allocated.
The CF-4 15W-40 petrol engine lubricating oil of table 21
Note：Y* contains antiwear additive in the inside, and antiwear additive refers to zinc dialkyl dithiophosphate (ZDDP).
The analysis result of CF-4 15W-40 diesel engine lubricants is as shown in table 22：
The CF-4 15W-40 diesel engine lubricant analysis results of table 22
Note：M* friction secondary modes：Ball and disk, experimental condition：50hz, 200g, 80 DEG C.
M** absorbing wavelength 495nm, excitation wavelength 530nm.
Can be seen that from the analytical data of table 22, the coefficient of friction of the CF-4 15W-40 diesel engine lubricants allocated using the 10G magnetic Nano level polyamide-amide class fluorescent chemicalses N of the present embodiment is 0.09, and the coefficient of friction of the CF-415W-40 diesel engine lubricants that molybdenum dialkyl-dithiophosphate is allocated as antiwear additive is 0.13, thus 10G magnetic Nano level polyamide-amide class fluorescent chemicalses (n=10 are illustrated, m=4, p=15) it is very outstanding magnetic Nano antiwear additive.
Embodiment 14
γ-Fe2O3＆SiO2 are dissolved in the base oil of 100N for the 5G magnetic Nano level polyamide-amide class fluorescent chemicalses of core, abrasion resistance test is carried out to it using SRV.Its result is as shown in Figure 4.From fig. 4, it can be seen that as load increases, coefficient of friction is slightly reduced, coefficient of friction tends towards stability 0.119 or so.This is because fastness sea surface oil slick is gradually formed and stable, illustrates that 5G magnetic Nano level polyamide-amide class compounds have good abrasion resistance.And when load is added to 1100N, coefficient of friction is raised suddenly, this is, due to the rupture of oil film on fastness surface, to lose lubrication.And conventional organic-molybdenum salt (such as molybdenum dialkyl-dithiophosphate) is under the same conditions, when load is added to 800N, the rupture of oil film (such as Fig. 5) on fastness surface, thus illustrates, 5G magnetic Nano level polyamide-amide class fluorescent chemicalses have excellent extreme pressure property.
Integrated comparative above-claimed cpd, the combination property of the compound that embodiment 3 and 8 is provided is optimum.
Although above having used general explanation, specific embodiment and test, the present invention is described in detail, on the basis of the present invention, it can be made some modifications or improvements, and this will be apparent to those skilled in the art.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, belong to the scope of protection of present invention.
Claims (10)
1. a kind of good oil-soluble nanoscale dendrimers fluorescent chemicalses, its feature exists
In the molecular formula of the compound is shown in formula I：
In Formulas I, Γ represents nano-particle, describedIt is with dendroid knot
The group of structure, the R2For lipophile fluorophor, 0≤n≤100；
The R1It is the polyamidoamine dendroid high score containing molecular structure shown in Formula II
Son；
-(CH2)2CONH(CH2)2NH- II；
The R2Molecular structure as shown in formula III：
2. compound according to claim 1, it is characterised in that the compound
Molecular formula is as shown in formula IV：
In formula IV, Γ represents nano-particle, 0≤n≤10,1≤m≤18,1≤P≤18.
3. compound according to claim 2, it is characterised in that the n is selected from
Integer in 2～6, integers of the m in 1～4, integers of the p in 8～12.
4. compound according to claim 3, it is characterised in that the n is selected from
Integer in 4～6, it is 8 or 9 that m is 2, p.
5. the compound according to any one of Claims 1 to 4, it is characterised in that institute
The kernel for stating nano-particle contains SiO2、Fe3O4, Ni or γ-Fe2O3In at least one.
6. compound according to claim 5, it is characterised in that the nano-particle
There is SiO selected from external sheath2, kernel be Fe3O4Core-shell type Fe3O4&SiO2Magnetic Nano
Granule, or external sheath has SiO2, kernel be SiO2Core-shell type SiO2&SiO2Magnetic is received
Rice grain.
7. compound according to claim 6, it is characterised in that the nano-particle
For the magnetic nanoparticle that silane coupler carries out surface modification；The silane coupler is 3-
Aminopropyltriethoxywerene werene, 3- glycydoxies trimethoxy silane or 3-
TSL 8330.
8. good oil-soluble nanoscale dendrimers are glimmering described in any one of claim 1～7
The preparation method of optical compounds, it is characterised in that comprise the steps：
I) nano-particle is provided；
Ii) surface of the nano-particle is modified using silane coupler, then will repaiies
Product after decorations reacts with dendrimer, obtains dendrimers bonding magnetic nanoparticle；
Iii) dendrimers bonding magnetic nanoparticle and fluorescent chemicalses are reacted, is obtained
To nanoscale dendrimers fluorescent chemicalses；
Iv) by the nanoscale dendrimers fluorescent chemicalses and the chemical combination with lipophilic group
Thing reacts, and obtains having good oil-soluble nanoscale dendrimers fluorescent chemicalses；
The compound with lipophilic group is a halogenated alkane or alkane sodium alkoxide；Preferably
Bromoalkanes hydrocarbon or linear paraffin sodium alkoxide.
9. nanoscale dendrimers fluorescent chemicalses described in any one of claim 1～7 or
It is prepared by the nanoscale dendrimers fluorescent chemicalses that claim 8 methods described is prepared from
Application in lubricating oil antiwear additive, lube product identification.
10. a kind of nanoscale dendrimers fluorescence containing described in any one of claim 1～7
The nanoscale dendrimers fluorescence chemical combination that compound or claim 8 methods described are prepared from
The lubricant of thing, it is characterised in that institute's nanoscale dendrimers fluorescent chemicalses are in the profit
Mass content in lubrication prescription is 100ppm～2%.
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|---|---|---|---|---|
| CN110669494A (en) * | 2019-09-10 | 2020-01-10 | 珠海量致科技有限公司 | Anti-counterfeiting oil product and preparation method thereof |
| CN112126490A (en) * | 2020-09-14 | 2020-12-25 | 南通盘天新材料有限公司 | Detectable shield tail sealing grease |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1172846A (en) * | 1996-07-12 | 1998-02-11 | Dsm共聚物公司 | Branched polyolefin polymers as additives in fuel and lubricating oil compositions |
| CN101694799A (en) * | 2009-09-29 | 2010-04-14 | 上海师范大学 | Preparation method of trimanganese tetroxide nanoparticles with magneto-optical double functions |
| CN104558628A (en) * | 2013-10-17 | 2015-04-29 | 中国石油化工股份有限公司 | Magnetic nanoscale resin compound as well as preparation method and application thereof |
-
2015
- 2015-10-21 CN CN201510686578.1A patent/CN106609169B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1172846A (en) * | 1996-07-12 | 1998-02-11 | Dsm共聚物公司 | Branched polyolefin polymers as additives in fuel and lubricating oil compositions |
| CN101694799A (en) * | 2009-09-29 | 2010-04-14 | 上海师范大学 | Preparation method of trimanganese tetroxide nanoparticles with magneto-optical double functions |
| CN104558628A (en) * | 2013-10-17 | 2015-04-29 | 中国石油化工股份有限公司 | Magnetic nanoscale resin compound as well as preparation method and application thereof |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110669494A (en) * | 2019-09-10 | 2020-01-10 | 珠海量致科技有限公司 | Anti-counterfeiting oil product and preparation method thereof |
| CN112126490A (en) * | 2020-09-14 | 2020-12-25 | 南通盘天新材料有限公司 | Detectable shield tail sealing grease |
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