CN113817532A

CN113817532A - Piezofluorescence color-changing lubricating oil and preparation process thereof

Info

Publication number: CN113817532A
Application number: CN202111270673.5A
Authority: CN
Inventors: 冀光亮; 詹志辉; 曹简雪生
Original assignee: Wuxi Quid Lubricating Oil Co ltd
Current assignee: Wuxi Quid Lubricating Oil Co ltd
Priority date: 2021-10-29
Filing date: 2021-10-29
Publication date: 2021-12-21

Abstract

The invention relates to the technical field of lubricating oil, in particular to a pressure-induced fluorescence color-changing lubricating oil and a preparation process thereof, aiming at solving the problem that bacteria or viruses in the air cannot be pre-warned or monitored, wherein the lubricating oil comprises, by mass, 200 parts of base oil, 1-6 parts of organic conjugated luminescent compound and 2-65 parts of surfactant; the organic conjugated luminescent compound is tetraphenylethylene, cyanophenyl ethylene and anthracenyl stilbene derivatives; the surfactant is one or a combination of more of octyl phenyl polyoxyethylene ether, hexadecyl trimethyl ammonium bromide, sodium bis (2-ethylhexyl) succinate sulfonate, alkyl glycoside and 1-hexadecyl-3-methylimidazole chloride salt; the base oil is a transparent liquid and is mutually soluble with THF solution at normal temperature. The lubricating oil has obvious pressure-induced fluorescence color change property, is easy to be monitored by maintenance personnel, and plays an important role under special working conditions such as darkness and the like.

Description

Piezofluorescence color-changing lubricating oil and preparation process thereof

Technical Field

The invention relates to the technical field of lubricating oil, in particular to piezofluorescence color-changing lubricating oil and a preparation process thereof.

Background

As the most widely used lubricating materials, the performance of lubricating oil directly affects the safety, reliability, operating efficiency and service life of mechanical equipment. Viscosity is one of the important indicators for the performance of a lubricating oil, and generally the performance of a lubricating oil deteriorates as the viscosity decreases. Temperature is the most important parameter affecting the viscosity of lubricating oils, and there is a specific viscosity-temperature relationship between the two. Therefore, the lubricating condition of mechanical equipment can be timely mastered by monitoring the temperature of lubricating oil in real time, and efficient and stable operation of the equipment is guaranteed.

In the application of lubricating oil, in addition to the traditional thermocouple temperature measurement technology, people also expect to develop some novel and convenient temperature sensing technologies or methods, so that the lubricating oil is more suitable for an automatic and intelligent lubricating system. Considering that the additive is a basic component of the lubricating oil, the novel lubricating oil additive with excellent tribological performance and intelligent oil temperature monitoring function is expected to be developed by combining the special physical and chemical properties of the additive.

The nano material has unique physical, chemical, mechanical and biological properties, and is widely used in the fields of energy, catalysis, materials, biomedicine and the like. Nano materials are also widely used as lubricating oil additives because they exhibit excellent properties of friction reduction, wear resistance, extreme pressure, thermal stability, and the like in lubricating oils. Nanoparticle-induced surface polishing, surface tribofilms, surface repair, and rolling bearing equivalents should significantly improve the lubricity of the lubricated product. More importantly, the functional nano material simultaneously shows special stimulus (chemical, optical, electric, magnetic, thermal and the like) response performance, which means that the functional nano material is used as a lubricating oil additive to endow the lubricating oil with specific sensing and monitoring functions, and is helpful for developing novel intelligent lubricating products.

Disclosure of Invention

Therefore, the invention aims to provide the piezofluorescence color-changing lubricating oil, which solves the problem that the lubricating oil monitoring is difficult in some special conditions.

The technical purpose of the invention is realized by the following technical scheme:

the pressure-induced fluorescence color-changing lubricating oil comprises, by mass, 150 parts of base oil, 1-6 parts of organic conjugated luminescent compound and 2-65 parts of surfactant;

the organic conjugated luminescent compound is tetraphenylethylene, cyanophenyl ethylene and anthracenyl stilbene derivatives;

the surfactant is one or a combination of more of octyl phenyl polyoxyethylene ether, hexadecyl trimethyl ammonium bromide, sodium bis (2-ethylhexyl) succinate sulfonate, alkyl glycoside and 1-hexadecyl-3-methylimidazole chloride salt;

the base oil is a transparent liquid and is mutually soluble with THF solution at normal temperature.

Optionally, the organic conjugated light-emitting compound is 9, 10-bis (N-phenylindole-3-vinyl) anthracene.

Alternatively, the 9, 10-bis (N-phenylindole-3-vinyl) anthracene is prepared from 9, 10-diphosphinolipoanthracene and a 1-phenyl-3-aldehydic indole by a ylide reaction.

Optionally, when the surfactant is octyl phenyl polyoxyethylene ether and/or 1-hexadecyl-3-methylimidazole chloride salt, the pressure-induced fluorescence color-changing lubricating oil further comprises 0-12 parts of cosurfactant;

when the surfactant is one or more of cetyl trimethyl ammonium bromide, sodium bis (2-ethylhexyl) succinate sulfonate and alkyl glycoside 1-hexadecyl-3-methylimidazole chloride salt; or when the surfactant is a mixture of octyl phenyl polyoxyethylene ether or 1-hexadecyl-3-methylimidazole chloride and one or more of hexadecyl trimethyl ammonium bromide, sodium bis (2-ethylhexyl) succinate sulfonate and alkyl glucoside, 1-12 parts of cosurfactant is further included in the pressure-induced fluorescence color-changing lubricating oil;

the cosurfactant is one or a combination of more of isopropanol, n-butanol, n-pentanol, n-hexanol, n-octanol and n-decanol.

The invention also aims to provide a preparation process of the lubricating oil.

A preparation process of a piezofluorescence color-changing lubricating oil comprises the following steps:

s1, uniformly mixing the surfactant and the cosurfactant at the temperature of 20-100 ℃ to obtain a clear and transparent mixture;

s2, uniformly mixing the mixture obtained in the step S1 and base oil at the temperature of 20-100 ℃ to obtain a clear and transparent oil-containing mixture;

s3, adding a THF solution containing the organic conjugated luminescent compound dropwise into the oil-containing mixture obtained in the step S2, uniformly mixing, and removing the THF solution through rotary evaporation to obtain the transparent isotropic piezofluorescence discoloration lubricating oil.

6. The process according to claim 5, wherein the step S1, S2 and S3 are performed by stirring at 300-1200 rpm for 5-10 minutes.

The invention has the beneficial effects that:

1. because the 9, 10-di (N-phenylindole-3-vinyl) anthracene has obvious pressure-induced fluorescence color change property under the stimulation of external grinding, when the friction and wear performance of the lubricating oil is weakened, the 9, 10-di (N-phenylindole-3-vinyl) anthracene can be changed from initial green fluorescence to orange red fluorescence, is easy to be monitored by maintenance personnel, and plays an important role under special working conditions such as darkness.

2. The addition of the surfactant and the cosurfactant ensures that the whole lubricating oil has excellent viscosity-temperature characteristics and thermal stability, and is convenient to be mutually soluble with various subsequent anti-wear additives, so that the lubricating effect of the base oil is effectively improved, and the combination of the organic conjugated compound and the base oil is promoted.

3. The preparation process of the invention has convenient operation, simple experimental equipment and low energy consumption.

Detailed Description

In order to make the technical solutions of the present application better understood by those skilled in the art, the technical solutions in the embodiments of the present application will be clearly and completely described below in conjunction with the embodiments of the present application, and it is obvious that the described embodiments are only some embodiments of the present application, but not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present application.

It is noted that the terms first, second and the like in the description and in the claims of the present application are used for distinguishing between similar elements and not necessarily for describing a particular sequential or chronological order. It should be understood that the data so used may be interchanged under appropriate circumstances such that embodiments of the application described herein may be used. Furthermore, the terms "comprises," "comprising," and "having," and any variations thereof, are intended to cover a non-exclusive inclusion, such that a process, method, system, article, or apparatus that comprises a list of steps or elements is not necessarily limited to those steps or elements expressly listed, but may include other steps or elements not expressly listed or inherent to such process, method, article, or apparatus.

Moreover, some of the above terms may be used to indicate other meanings besides the orientation or positional relationship, for example, the term "on" may also be used to indicate some kind of attachment or connection relationship in some cases. The specific meaning of these terms in this application will be understood by those of ordinary skill in the art as appropriate.

In addition, the term "plurality" shall mean two as well as more than two.

It should be noted that the embodiments and features of the embodiments in the present application may be combined with each other without conflict. The present application will be described in detail with reference to examples.

Example 1:

the pressure-induced fluorescence color-changing lubricating oil comprises 150 parts by mass of base oil, preferably PAO8 base oil, is transparent liquid and is mutually soluble with THF solution at normal temperature; 1 part of an organic conjugated compound, preferably 9, 10-bis (N-phenylindole-3-vinyl) anthracene; 2 parts of a surfactant, in this example octylphenyl polyoxyethylene ether; 1 part of a co-surfactant, in this example isopropanol. Because the 9, 10-di (N-phenylindole-3-vinyl) anthracene has obvious pressure-induced fluorescence color change property under the stimulation of external grinding, when the friction and wear performance of the lubricating oil is weakened, the 9, 10-di (N-phenylindole-3-vinyl) anthracene can be changed from initial green fluorescence to orange red fluorescence, is easy to be monitored by maintenance personnel, and plays an important role under special working conditions such as darkness. In addition, the addition of the surfactant and the cosurfactant ensures that the whole lubricating oil has excellent viscosity-temperature characteristics and thermal stability, and is convenient to be mutually soluble with various subsequent anti-wear additives, so that the lubricating effect of the base oil is effectively improved, and the combination of the organic conjugated compound and the base oil is promoted.

Wherein, 9, 10-di (N-phenylindole-3-vinyl) anthracene is prepared by ylide reaction of 9, 10-diphospholityanthracene and 1-phenyl-3-aldehyde indole, cuprous iodide, DMF, indole and potassium carbonate are added into a single-neck flask, iodobenzene is added under magnetic stirring, a condensation reflux device is added, the temperature is increased to 90 ℃, the reaction is stirred for 10 hours, after the reaction is finished, the reaction liquid is cooled to room temperature, water and dichloromethane are used for extraction for 3 times, an organic phase is dried by anhydrous magnesium sulfate, filtered, a crude product is obtained by rotary evaporation of a solvent, the crude product is separated and purified by column chromatography, a lotion is N-hexane to obtain a 1-phenylindole solid product, then the anhydrous DMF is added into the single-neck flask, the flask is placed in an ice bath and stirred for 0.5 hour, phosphorus oxychloride is added for reaction for 0.5 hour, and 1 which is completely dissolved in 30mL is added, heating 1-phenylindole in a 2-dichloroethane solution to 35 ℃ for reaction for 1h, adding 3mL of ice distilled water and 5mL of NaOH solution with the mass fraction of 20%, adding a condensing reflux device, and heating to 100 ℃ for reaction for 6 h; after the reaction is finished, cooling the reaction solution to room temperature, extracting for 3 times by using water and dichloromethane, drying and filtering an organic phase by using anhydrous magnesium sulfate, and rotationally evaporating the solvent to obtain a crude product; separating and purifying by using column chromatography, wherein an eluent is n-hexane/ethyl acetate to obtain a 1-phenyl-3-aldehyde indole solid product, finally adding 9, 10-diphosphoranthracene, 1-phenyl-3-aldehyde indole and potassium tert-butoxide into a single-neck flask, pumping nitrogen for 3 times under magnetic stirring, adding 20mL of anhydrous tetrahydrofuran solution, stirring at room temperature for reacting for 6h, and adding 20mL of methanol to terminate the reaction; removing THF and methanol by rotary evaporation, washing with methanol, filtering, and separating by column chromatography to obtain 9, 10-di (N-phenylindole-3-vinyl) anthracene.

And (2) uniformly mixing the surfactant and the cosurfactant at the temperature of 20 ℃, stirring at the speed of 300 revolutions per minute for 5 minutes to obtain a clear and transparent mixture, adding the base oil into the mixture under the stirring condition at the rotating speed of 300 revolutions per minute, and stirring for 5 minutes to prepare the clear and transparent oil-containing mixture. Keeping the temperature and the stirring speed unchanged, dripping THF solution containing 9, 10-di (N-phenylindole-3-vinyl) anthracene into the oil-containing mixture, stirring for 5 minutes, removing the THF solution through rotary evaporation to obtain the transparent uniform pressure-induced fluorescence color-changing lubricating oil, and adding additives such as an antiwear agent and the like to improve the performance of the lubricating oil.

Example 2:

the pressure-induced fluorescence color-changing lubricating oil comprises, by mass, 200 parts of base oil, preferably PAO8 base oil, is transparent liquid, and is mutually soluble with THF solution at normal temperature; 6 parts of an organic conjugated compound, preferably 9, 10-bis (N-phenylindole-3-vinyl) anthracene; 65 parts of a surfactant, in this example cetyltrimethylammonium bromide; 12 parts of a cosurfactant, in this example n-butanol.

And (2) uniformly mixing the surfactant and the cosurfactant at the temperature of 100 ℃, stirring at the speed of 1200 revolutions per minute for 10 minutes to obtain a clear and transparent mixture, adding the base oil into the mixture under the stirring condition at the speed of 1200 revolutions per minute, and stirring for 10 minutes to prepare the clear and transparent oil-containing mixture. Keeping the temperature and the stirring speed unchanged, dripping THF solution containing 9, 10-di (N-phenylindole-3-vinyl) anthracene into the oil-containing mixture, stirring for 10 minutes, removing the THF solution through rotary evaporation to obtain the transparent uniform pressure-induced fluorescence color-changing lubricating oil, and adding additives such as an antiwear agent and the like to improve the performance of the lubricating oil.

Example 3:

a piezofluorescence color-changing lubricating oil comprises 175 parts of base oil by mass, preferably PAO8 base oil which is transparent liquid and mutually soluble with THF solution at normal temperature; 3 parts of an organic conjugated compound, preferably 9, 10-bis (N-phenylindole-3-vinyl) anthracene; 32 parts of a surfactant, in this example 1-hexadecyl-3-methylimidazolium chloride; 6 parts of a co-surfactant, in this example n-hexanol.

And (2) uniformly mixing the surfactant and the cosurfactant at the temperature of 60 ℃, stirring at the speed of 1000 revolutions per minute for 8 minutes to obtain a clear and transparent mixture, adding the base oil into the mixture under the stirring condition at the speed of 1000 revolutions per minute, and stirring for 8 minutes to prepare the clear and transparent oil-containing mixture. Keeping the temperature and the stirring speed unchanged, dripping THF solution containing 9, 10-di (N-phenylindole-3-vinyl) anthracene into the oil-containing mixture, stirring for 8 minutes, removing the THF solution through rotary evaporation to obtain the transparent uniform pressure-induced fluorescence color-changing lubricating oil, and adding additives such as an antiwear agent and the like to improve the performance of the lubricating oil.

Example 4:

the pressure-induced fluorescence color-changing lubricating oil comprises 160 parts by mass of base oil, preferably PAO8 base oil, is transparent liquid and is mutually soluble with THF solution at normal temperature; 4 parts of an organic conjugated compound, preferably 9, 10-bis (N-phenylindole-3-vinyl) anthracene; 40 parts of a surfactant, in this example sodium 1-hexadecyl-3-methylimidazolium bis (2-ethylhexyl) succinate sulfonate; 10 parts of a co-surfactant, in this example n-pentanol.

And (2) uniformly mixing the surfactant and the cosurfactant at 70 ℃, stirring at the speed of 800 revolutions per minute for 6 minutes to obtain a clear and transparent mixture, adding the base oil into the mixture under the stirring condition at the speed of 800 revolutions per minute, and stirring for 6 minutes to prepare the clear and transparent oil-containing mixture. Keeping the temperature and the stirring speed unchanged, dripping THF solution containing 9, 10-di (N-phenylindole-3-vinyl) anthracene into the oil-containing mixture, stirring for 8 minutes, removing the THF solution through rotary evaporation to obtain the transparent uniform pressure-induced fluorescence color-changing lubricating oil, and adding additives such as an antiwear agent and the like to improve the performance of the lubricating oil.

Example 5:

the pressure-induced fluorescence color-changing lubricating oil comprises 190 parts of base oil by mass, preferably PAO8 base oil which is transparent liquid and mutually soluble with THF solution at normal temperature; 5 parts of an organic conjugated compound, preferably 9, 10-bis (N-phenylindole-3-vinyl) anthracene; 32 parts of a surfactant, in this example an alkyl glycoside; 8 parts of a co-surfactant, in this example n-octanol.

Under the condition of 20 ℃, the surfactant and the cosurfactant are uniformly mixed, the mixture is stirred for 6 minutes at the stirring speed of 500 revolutions per minute to obtain a clear and transparent mixture, the base oil is added into the mixture under the stirring condition of the rotating speed of 500 revolutions per minute, and the mixture is stirred for 3 minutes to prepare the clear and transparent oil-containing mixture. Keeping the temperature and the stirring speed unchanged, dripping THF solution containing 9, 10-di (N-phenylindole-3-vinyl) anthracene into the oil-containing mixture, stirring for 3 minutes, removing the THF solution through rotary evaporation to obtain the transparent uniform pressure-induced fluorescence color-changing lubricating oil, and adding additives such as an antiwear agent and the like to improve the performance of the lubricating oil.

It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.

Claims

1. The pressure-induced fluorescence color-changing lubricating oil is characterized by comprising, by mass, 150-200 parts of base oil, 1-6 parts of organic conjugated luminescent compound and 2-65 parts of surfactant;

2. The piezochromic lubricant according to claim 1, wherein the organic conjugated luminescent compound is 9, 10-bis (N-phenylindole-3-vinyl) anthracene.

3. The piezochromic lubricant oil according to claim 2, wherein the 9, 10-bis (N-phenylindole-3-vinyl) anthracene is prepared from 9, 10-diphosphinoxanthene and 1-phenyl-3-aldehydic indole by ylide reaction.

4. The pressure-induced fluorescence color-changing lubricating oil according to claim 1, characterized in that when the surfactant is octyl phenyl polyoxyethylene ether and/or 1-hexadecyl-3-methylimidazolium chloride salt, the pressure-induced fluorescence color-changing lubricating oil further comprises 0-12 parts of cosurfactant;

5. A process for the preparation of a piezofluorescing lubricant, based on the piezofluorescing lubricant according to any one of claims 1 to 4, comprising the following steps: