Isocyanurate compound and preparation method and use thereof

Abstract

The present invention provides an isocyanurate compound and a preparation method and use thereof. The structural formula of the isocyanurate compound is shown in Formula III: wherein R1 and R3 are independently selected from ether groups and / or alkyl groups having 1 to 30 carbon atoms, and R2 is selected from ether groups having 1 to 30 carbon atoms. The present invention provides an isocyanurate compound and a preparation method and use thereof. The isocyanurate is used to prepare lubricating grease to improve the mechanical shear stability, colloidal stability, anti-friction performance, service life and water-spray resistance of the lubricating grease.

Description

Technical Field

[0001] The invention relates to the field of chemical industry, and in particular to an isocyanurate compound and a preparation method and application thereof. Background Art

[0002] Grease is used to reduce mechanical friction and wear and extend the service life of mechanical equipment. About 80% of rolling bearings on the market are lubricated with grease. The use conditions of modern precision bearings are becoming more and more demanding, and the requirements for grease are also getting higher and higher, mainly reflected in long life, adaptability to high / low temperature, high / low speed use, low noise, etc.

[0003] Common low-noise grease products at home and abroad are mostly lithium-based grease and polyurea grease. Ordinary lithium-based grease on the market has a good noise reduction effect at the beginning, but the noise becomes louder after running for a period of time. Polyurea grease has excellent low-noise performance, thermal stability, colloidal stability and oxidation stability, and has a long service life, especially at high temperatures. Although polyurea grease has many excellent properties, poor shear stability is one of its main disadvantages, which is usually reflected in severe softening at low shear rates. After 100,000 operations of the ASTM grease worker, the change in cone penetration is about 100 units. The obvious reduction in cone penetration will lead to the loss of grease in the bearing, causing it to lose its lubrication effect, thereby limiting the application of polyurea grease. Summary of the invention

[0004] In view of the above-mentioned shortcomings of the prior art, the object of the present invention is to provide an isocyanurate compound and a preparation method and use thereof, so as to solve the problems in the prior art.

[0005] To achieve the above objectives and other related objectives, the present invention is achieved through the following technical solutions.

[0006] The present invention provides an isocyanurate compound, the structural formula of the isocyanurate compound is shown in Formula III:

[0007]

[0008] Among them, R1 and R3 are independently selected from ether groups and / or alkyl groups having 1 to 30 carbon atoms, and R2 is selected from ether groups having 1 to 30 carbon atoms.

[0009] The number of carbon atoms in R1 and R3 may be 1 to 2, 2 to 3, 3 to 5, 5 to 7, 7 to 8, 8 to 12, 12 to 16, 16 to 25, or 25 to 30. Preferably, the number of carbon atoms in R1 and R3 is 1 to 12.

[0010] The number of carbon atoms in R2 may be 1 to 2, 2 to 3, 3 to 5, 5 to 7, 7 to 8, 8 to 10, 10 to 16, 16 to 25, or 25 to 30. Preferably, the number of carbon atoms in R2 is 1 to 12.

[0011] Preferably, R1 and R3 further contain alicyclic hydrocarbon groups and / or heterocyclic groups. More preferably, the alicyclic hydrocarbon groups are polycyclic monocyclic and / or polycyclic structures. More preferably, the heterocyclic groups are cyclic compounds containing heteroatoms (non-carbon atoms).

[0012] Preferably, R1 and R3 are branched or straight chains.

[0013] Preferably, R2 further contains an alicyclic hydrocarbon group and / or a heterocyclic group. More preferably, the alicyclic hydrocarbon group is a polycyclic and / or polycyclic structure. More preferably, the heterocyclic group is a cyclic compound containing heteroatoms (non-carbon atoms).

[0014] Preferably, the isocyanurate compound includes a compound of formula III-1, a compound of formula III-2, a compound of formula III-3, and a compound of formula III-4; the structural formulas of the compound of formula III-1, the compound of formula III-2, the compound of formula III-3, and the compound of formula III-4 are as follows:

[0015]

[0016] Wherein, R'1, R'2, and R'3 are independently selected from ether groups and / or alkyl groups having 1 to 10 carbon atoms, and R0 is selected from ether groups and / or alkyl groups having 1 to 20 carbon atoms.

[0017] Preferably, R'1, R'2, R'3 and R0 further contain alicyclic hydrocarbon groups and / or heterocyclic groups. More preferably, the alicyclic hydrocarbon groups are polycyclic and / or polycyclic structures. More preferably, the heterocyclic groups are cyclic compounds containing heteroatoms (non-carbon atoms).

[0018] Preferably, R'1, R'2, R'3 and R0 are branched or linear chains.

[0019] The number of carbon atoms in R'1, R'2 and R'3 may be 1 to 2, 2 to 3, 3 to 5, 5 to 7, or 7 to 10. Preferably, the number of carbon atoms in R'1, R'2 and R'3 is 1 to 4.

[0020] The number of carbon atoms in R0 may be 1 to 8, 8 to 15, or 15 to 20. Preferably, the number of carbon atoms in R0 is 1 to 8.

[0021] More preferably, in the compound of formula III-1, the structural formula of R'1 is:

[0022]

[0023] More preferably, in the compound of formula III-2, the structural formula of R'1 is:

[0024]

[0025] More preferably, in the compound of formula III-3, the structural formula of R'1 is:

[0026]

[0027] More preferably, in the compound of formula III-1, the structural formula of R'2 is:

[0028]

[0029] More preferably, in the compound of formula III-2, the structural formula of R'2 is:

[0030]

[0031] More preferably, in the compound of formula III-3, the structural formula of R'2 is:

[0032]

[0033] More preferably, in the compound of formula III-1, the structural formula of R'3 is:

[0034]

[0035] More preferably, in the compound of formula III-2, the structural formula of R'3 is:

[0036]

[0037] More preferably, in the compound of formula III-3, the structural formula of R'3 is:

[0038]

[0039] More preferably, in the compound of formula III-1, the structural formula of R'0 is:

[0040]

[0041] More preferably, in the compound of formula III-2, the structural formula of R'0 is:

[0042]

[0043] More preferably, in the compound of formula III-3, the structural formula of R'0 is:

[0044]

[0045] Preferably, the compound of formula III-1 comprises:

[0046]

[0047]

[0048] More preferably, the compound of formula III-2 comprises:

[0049]

[0050] More preferably, the compound of formula III-3 comprises:

[0051]

[0052]

[0053] The present invention also discloses a method for preparing the isocyanurate compound, which comprises the following steps: alcohol and halide undergo a substitution reaction to prepare the isocyanurate compound.

[0054] Preferably, the halide is selected from chloride, bromide or iodide.

[0055] Preferably, the reaction system includes a hydrogen-pulling agent, which is selected from one or more of lithium diisopropylamide, n-butyl lithium, tert-butyl lithium, sodium hydride, potassium carbonate, sodium methoxide, potassium methoxide, sodium ethoxide, potassium ethoxide, sodium tert-butoxide and potassium tert-butoxide. More preferably, it is sodium hydride. The function of the hydrogen-pulling agent is to promote the dehydrogenation of alcohol.

[0056] More preferably, the molar ratio of the hydrogen extraction agent to the hydroxyl group is (0.3-1.5):1, and further preferably (0.5-1.5):1.

[0057] More preferably, the addition temperature of the hydrogen extraction agent is 0-5°C.

[0058] Preferably, the reaction system comprises a reaction medium, and the reaction medium is selected from one or more of N,N-dimethylformamide, dimethyl sulfoxide, acetonitrile and acetone.

[0059] More preferably, the reaction medium is selected from one or both of acetonitrile and acetone.

[0060] Preferably, the reaction temperature is ≥ 40°C.

[0061] More preferably, the reaction temperature is 40 to 90°C, such as 50°C, 55°C, 60°C, 75°C, 78°C, or 80°C.

[0062] Preferably, the reaction time is (8-20) h.

[0063] Preferably, the reaction process further comprises a post-treatment step, and the post-treatment step comprises separation and impurity removal. More preferably, the separation is to quench the reaction and form layers at the same time, and then separate the liquids to obtain the organic phase. Further preferably, the aqueous phase is extracted with ethyl acetate and the organic phases are combined. More preferably, the impurity removal comprises one or more of water washing, drying, filtration and evaporation. Further preferably, the water washing is to wash the organic phase with water and / or saturated brine respectively. Further preferably, the drying is to dry the organic phase with anhydrous magnesium sulfate. Further preferably, the filtration is to perform solid-liquid separation on the organic phase to which the desiccant is added to extract the organic phase. Further preferably, the evaporation is to remove the solvent using a rotary evaporator, the evaporation temperature is 40 to 60°C, and the vacuum degree is 0.1 to 10KPa.

[0064] Preferably, when the isocyanurate compound has the structural formula III-1, its preparation method is as follows:

[0065] Alcohols and halides undergo substitution reaction to prepare isocyanurate compounds. The reaction route is as follows:

[0066]

[0067] More preferably, the molar ratio of the compound of formula I to the compound of formula II is (2.0-7.5):1. More preferably, it is (2.2-7.0):1.

[0068] Preferably, when the isocyanurate compound has the structural formula III-1, its preparation method is as follows:

[0069] Alcohols and halides undergo substitution reaction to prepare isocyanurate compounds. The reaction route is as follows:

[0070]

[0071] More preferably, the molar ratio of the compound of formula II'-1 to the compound of formula I' is (2.0-7.5):1. More preferably, it is (2.2-7.0):1.

[0072] More preferably, the compound of formula I-1 comprises

[0073] More preferably, the compound of formula II includes n-butyl bromide, n-hexyl bromide, isooctane bromide or 2-bromomethyltetrahydrofuran.

[0074] Preferably, when the structural formula of the isocyanurate compound is III-2, the preparation method thereof is as follows:

[0075] Alcohols and halides undergo substitution reaction to prepare isocyanurate compounds. The reaction route is as follows:

[0076]

[0077] More preferably, the molar ratio of the compound of formula I-2 to the compound of formula II is (2.0-7.5):1. More preferably, it is (2.2-7.0):1.

[0078] Preferably, when the structural formula of the isocyanurate compound is III-2, the preparation method thereof is as follows:

[0079] Alcohols and halides undergo substitution reaction to prepare isocyanurate compounds. The reaction route is as follows:

[0080]

[0081] More preferably, the molar ratio of the compound of formula II'-2 to the compound of formula I' is (2.0-7.5):1. More preferably, it is (2.2-7.0):1.

[0082] More preferably, the compound of formula II'-2 comprises

[0083]

[0084] More preferably, the compound of formula I' comprises

[0085]

[0086] Preferably, when the structural formula of the isocyanurate compound is III-3, the preparation method thereof is as follows:

[0087] Alcohols and halides undergo substitution reaction to prepare isocyanurate compounds. The reaction route is as follows:

[0088]

[0089] More preferably, the molar ratio of the compound of formula I-3 to the compound of formula II is (2.0-7.5):1. More preferably, it is (2.2-7.0):1.

[0090] Preferably, when the structural formula of the isocyanurate compound is III-3, the preparation method thereof is as follows:

[0091] Alcohols and halides undergo substitution reaction to prepare isocyanurate compounds. The reaction route is as follows:

[0092]

[0093] More preferably, the molar ratio of the compound of formula II'-3 to the compound of formula I' is (2.0-7.5):1. More preferably, it is (2.2-7.0):1.

[0094] More preferably, the compound of formula I-3 comprises

[0095]

[0096] Preferably, when the isocyanurate compound has the structural formula III-4, its preparation method is as follows:

[0097] Alcohols and halides undergo substitution reaction to prepare isocyanurate compounds. The reaction route is as follows:

[0098]

[0099] More preferably, the molar ratio of the compound of formula I-4 to the compound of formula II is (2.0-7.5):1. More preferably, it is (2.2-7.0):1.

[0100] Preferably, when the isocyanurate compound has the structural formula III-4, its preparation method is as follows:

[0101] Alcohols and halides undergo substitution reaction to prepare isocyanurate compounds. The reaction route is as follows:

[0102]

[0103] More preferably, the molar ratio of the compound of formula II'-4 to the compound of formula I' is (2.0-7.5):1. More preferably, it is (2.2-7.0):1.

[0104] More preferably, when the structural formula of the isocyanurate compound is III-1-1, the preparation method thereof is as follows:

[0105] Alcohols and halides undergo substitution reaction to prepare isocyanurate compounds. The reaction route is as follows:

[0106]

[0107] More preferably, when the isocyanurate compound has the structural formula III-1-2, the preparation method thereof is as follows: an alcohol and a halide undergo a substitution reaction to prepare an isocyanurate compound, and the reaction route is as follows:

[0108]

[0109] More preferably, when the isocyanurate compound has the structural formula III-2-1, the preparation method thereof is as follows: an alcohol is subjected to a substitution reaction with a halide to prepare the isocyanurate compound, and the reaction route is as follows:

[0110]

[0111] More preferably, when the isocyanurate compound has the structural formula III-2-2, the preparation method thereof is as follows: an alcohol is subjected to a substitution reaction with a halide to prepare the isocyanurate compound, and the reaction route is as follows:

[0112]

[0113] More preferably, when the isocyanurate compound has the structural formula III-3-1, the preparation method thereof is as follows: an alcohol and a halide undergo a substitution reaction to prepare an isocyanurate compound, and the reaction route is as follows:

[0114]

[0115] More preferably, when the structural formula of the isocyanurate compound is III-3-2, the preparation method thereof is as follows:

[0116] Alcohols and halides undergo substitution reaction to prepare isocyanurate compounds. The reaction route is as follows:

[0117]

[0118] The invention also discloses the use of the isocyanurate compound as a base oil in the field of lubricating grease.

[0119] The invention also discloses a base oil composition, which comprises an isocyanurate compound and a poly-alpha-olefin.

[0120] Preferably, the base oil composition comprises 60 to 90 parts by weight of the poly-alpha olefin and 2 to 20 parts by weight of the isocyanurate compound.

[0121] For example, the amount of polyalphaolefin used can be 60 parts by weight, 62 parts by weight, 63 parts by weight, 70 parts by weight, 71 parts by weight, 74 parts by weight, 76 parts by weight, 78 parts by weight, 80 parts by weight, or 90 parts by weight.

[0122] For example, the amount of the isocyanurate compound can be 2 parts by weight, 4 parts by weight, 5 parts by weight, 7 parts by weight, 8 parts by weight, 10 parts by weight, 15 parts by weight, 16 parts by weight, or 20 parts by weight.

[0123] Preferably, the amount of the isocyanurate compound is 2 to 20 parts by weight, more preferably 4 to 20 parts by weight, and further preferably 4 to 16 parts by weight.

[0124] Preferably, the kinematic viscosity of the polyalphaolefin at 100°C is 1 to 10 mm 2 / s. For example, it can be 1mm 2 / s, 2mm 2 / s、3mm 2 / s, 4mm2 / s, 5mm 2 / s, 6mm 2 / s、7mm 2 / s, 8mm 2 / s, 9mm 2 / s, 10mm 2 / s.

[0125] More preferably, the kinematic viscosity of the polyalphaolefin at 100°C is 2 to 8 mm 2 / s. For example, it can be 2mm 2 / s、3mm 2 / s, 4mm 2 / s, 5mm 2 / s, 6mm 2 / s、7mm 2 / s, 8mm 2 / s. Further preferably, the kinematic viscosity of the polyalphaolefin at 100°C is 2 to 6 mm 2 / s. Kinematic viscosity test method: GB / T265-1988 "Method for determination of kinematic viscosity and calculation of dynamic viscosity of petroleum products" was used to test the kinematic viscosity of the base oil composition at 100°C.

[0126] Preferably, the polyalphaolefin is selected from one or both of metallocene polyalphaolefin and non-metallocene polyalphaolefin. Metallocene polyalphaolefin is prepared using a metallocene catalyst, and the preparation process of non-metallocene polyalphaolefin uses a non-metallocene catalyst.

[0127] The non-metallocene catalyst includes a non-metallocene inorganic-organic complex, a homogeneous Lewis acid catalyst, a heterogeneous Lewis acid catalyst, a Ziegler-Natta catalyst, and a chromium-based catalyst.

[0128] Non-metallocene inorganic-organic complexes are formed by ligands without cyclopentadiene structures and metal elements, including transition metal elements and rare earth metal elements from Group IIIB to Group VIII, coordinated with ligands containing heteroatoms such as N, O, S, and P. Such as α-diimine metal organic compounds, β-diimine metal organic compounds, β-diketoimine metal organic compounds, amidine metal organic compounds, and P-containing metal organic compounds.

[0129] Homogeneous Lewis acid catalysts include AlCl3, AlBr3, TiCl3, SiCl3, BiCl3, FeCl3, BF3 or BF3-ROH.

[0130] The heterogeneous Lewis acid catalyst comprises the above-mentioned homogeneous Lewis acid catalyst and an inorganic porous substance, wherein the inorganic porous substance is selected from one or more of mesoporous carbon, carbon nanotubes, activated carbon fibers, acetylene black, carbon black, expanded graphite and graphene.

[0131] The Ziegler-Natta catalyst includes Et3Al and TiCl4.

[0132] The chromium-based catalyst includes chromium oxide, chromium halide, chromium phosphate, sulfate, nitrate or oxalate.

[0133] Preferably, the raw material components of the base oil composition further include alkylnaphthalene.

[0134] More preferably, the amount of the alkyl naphthalene is 2 to 20 parts, such as 2 parts, 5 parts, 10 parts, 15 parts, or 20 parts.

[0135] The present invention also discloses a lubricating grease, which comprises the base oil composition as described above and a thickener.

[0136] Preferably, the grease comprises the following raw material components in parts by weight:

[0137] Base oil composition 60-85 parts by weight

[0138] Thickener 5-25 parts by weight.

[0139] The base oil composition may be used in an amount of 60 parts by weight, 65 parts by weight, 70 parts by weight, 78 parts by weight, 80 parts by weight, or 85 parts by weight.

[0140] The thickener can be used in an amount of 5 parts by weight, 10 parts by weight, 13.5 parts by weight, 15 parts by weight, or 20 parts by weight.

[0141] Preferably, the thickener is selected from one or two of a compound or polymer with at least two urea bonds, and a hydroxy fatty acid lithium soap. The compound with at least two urea bonds includes a diurea compound, a compound obtained by reacting an organic amine with a diisocyanate compound. Further preferably, the diisocyanate compound is selected from one or more of diisocyanate phenylene, diisocyanate diphenyl, diisocyanate phenyl, diphenylmethane diisocyanate, cyclohexane diisocyanate, octadecane diisocyanate, decane diisocyanate and hexane diisocyanate. Further preferably, the organic amine is selected from one or two of aliphatic amines and aromatic amines. Further preferably, the organic amine has a carbon number of 6 to 20. Further preferably, the thickener does not contain a free isocyanate group (-NCO). Further preferably, the thickener is polyurea powder.

[0142] Preferably, other additives are also contained, and the other additives are selected from one or more of a tackifier, an anti-wear agent, an oiliness agent, an antioxidant and a rust inhibitor.

[0143] More preferably, in the grease, the amount of the other additives is 1.5 to 13 parts by weight.

[0144] More preferably, among the other additives, the amount of the tackifier is 1 to 10 parts by weight. The amount of the tackifier can be 1 part by weight, 3 parts by weight, 5 parts by weight, 7.3 parts by weight, 7.5 parts by weight, 9 parts by weight, or 10 parts by weight.

[0145] More preferably, among the other additives, the amount of the anti-wear agent is 0.1-1.0 parts by weight. For example, it can be 0.1 parts by weight, 0.2 parts by weight, 0.3 parts by weight, 0.4 parts by weight, 0.5 parts by weight, 0.6 parts by weight, 0.7 parts by weight, 0.8 parts by weight, 0.9 parts by weight, and 1.0 parts by weight. Too little anti-wear agent will affect the anti-wear performance of the grease. More preferably, the amount of the anti-wear agent is 0.5-1.0 parts by weight.

[0146] More preferably, in the additive, the amount of the oiliness agent is 0.1-0.5 parts by weight, such as 0.1 parts by weight, 0.2 parts by weight, 0.3 parts by weight, 0.4 parts by weight, or 0.5 parts by weight.

[0147] More preferably, in the additive, the amount of the antioxidant is 0.1-0.5 parts by weight. For example, it can be 0.1 parts by weight, 0.2 parts by weight, 0.3 parts by weight, 0.4 parts by weight, and 0.5 parts by weight. Too little antioxidant will affect the service life of the grease. More preferably, the amount of the antioxidant is 0.3-0.5 parts by weight.

[0148] More preferably, in the additive, the amount of the rust inhibitor is 0.05-0.2 parts by weight, such as 0.05 parts by weight, 0.1 parts by weight, 0.15 parts by weight, or 0.2 parts by weight.

[0149] More preferably, the tackifier is a high viscosity metallocene polyalphaolefin (mPAO).

[0150] Further preferably, the kinematic viscosity of the high viscosity metallocene poly-α-olefin at 100° C. is 100-1000 mm 2 / s, and the viscosity index is 200-350. For example, the kinematic viscosity of high-viscosity metallocene polyalphaolefin is 100 mm 2 / s, 150mm 2 / s、300mm 2 / s、500mm 2 / s、700mm 2 / s、1000mm 2 / s. For example, the viscosity index of high viscosity metallocene polyalphaolefin is 200, 250, 300, 350.

[0151] More preferably, the anti-wear agent is selected from an organic phosphide or a sulfur-containing organic phosphide. Further preferably, the organic phosphide is selected from one or more of tricresyl phosphate, triphenyl phosphate, triethyl phosphate, tributyl phosphate and dibutyl phosphite. Further preferably, the sulfur-containing organic phosphide is selected from triphenyl thiophosphate, trialkyl thiophosphate or amine thiophosphate. Further preferably, the anti-wear agent is triphenyl thiophosphate.

[0152] More preferably, the oiliness agent is selected from fatty amine salts of benzotriazole.

[0153] More preferably, the antioxidant is selected from one or both of phenolic antioxidants and amine antioxidants. More preferably, the antioxidant is an amine antioxidant, and the amine antioxidant is selected from one or more of diphenylamine, alkyl diphenylamine and phenyl-α-naphthylamine. Further preferably, the antioxidant is alkyl diphenylamine.

[0154] More preferably, the rust inhibitor is selected from one or more of benzotriazole, alkyltriazole, benzothiazole, benzimidazole, thiadiazole and derivatives thereof. Further preferably, the rust inhibitor is benzotriazole.

[0155] In the present application, the types of antiwear agent, oiliness agent, antioxidant and rust inhibitor are selected according to the conventional selection in the field, and those skilled in the art can select according to actual needs. Antiwear agent mainly plays a role in improving anti-friction performance and lubricity. Oiliness agent mainly plays a role in improving lubricity and preventing wear. The role of antioxidant is anti-oxidation. The role of rust inhibitor is to prevent metal corrosion.

[0156] The present invention also discloses a method for preparing the above-mentioned grease, and the specific method is as follows: after the raw material components of the grease are evenly mixed, the grease is heated to obtain the grease.

[0157] Preferably, the mixing temperature is 40-90°C.

[0158] Preferably, the heating temperature is 130-200° C., more preferably 150-180° C. If the heating temperature is too low, the formation of hydrogen bonds between the thickener and the polyurea compound will be affected, and the dropping point of the grease will be reduced; if the heating temperature is too high, the degree of oxidation will increase, the appearance color of the grease will darken, the dropping point will increase, and the shear stability will decrease.

[0159] Preferably, the heating time is 1-3 hours.

[0160] Preferably, the heating rate is ≤40°C / 10min.

[0161] Preferably, the heating treatment is followed by a grinding treatment.

[0162] More preferably, the grinding temperature is 100-120°C.

[0163] The present invention also discloses the use of the above-mentioned lubricating grease for lubricating bearings, sliding parts and joints of a device.

[0164] Preferably, the fields involved in the device include: automobile field, office equipment field, and working machinery field.

[0165] The fields of working machinery include construction, agricultural machinery, mining machinery, port machinery, road machinery, water conservancy machinery, oil and gas extraction machinery, electric machinery, industrial manufacturing machinery, and other special machinery fields (such as aerospace equipment, medical equipment, environmental protection equipment and other special field machinery and equipment).

[0166] The invention provides an isocyanurate compound and a preparation method and use thereof. The isocyanurate is used to prepare lubricating grease to improve the mechanical shear stability, colloid stability, anti-friction performance, service life and water-spray resistance of the lubricating grease. DETAILED DESCRIPTION

[0167] The following is a description of the implementation of the present invention by means of specific embodiments. Those skilled in the art can easily understand other advantages and effects of the present invention from the contents disclosed in this specification.

[0168] Before further describing the specific embodiments of the present invention, it should be understood that the scope of protection of the present invention is not limited to the specific embodiments described below; it should also be understood that the terms used in the examples of the present invention are intended to describe specific embodiments, rather than to limit the scope of protection of the present invention. The test methods in the following examples without specifying specific conditions are generally carried out under conventional conditions or under conditions recommended by the manufacturers.

[0169] When the embodiments give numerical ranges, it should be understood that, unless otherwise specified in the present invention, both endpoints of each numerical range and any numerical value between the two endpoints can be selected. Unless otherwise defined, all technical and scientific terms used in the present invention have the same meaning as those generally understood by those skilled in the art. In addition to the specific methods, equipment, and materials used in the embodiments, according to the grasp of the prior art by those skilled in the art and the record of the present invention, any methods, equipment, and materials of the prior art similar or equivalent to the methods, equipment, and materials described in the embodiments of the present invention can also be used to realize the present invention.

[0170] Example 1

[0171] This embodiment provides a specific isocyanurate compound III-1-1, the structural formula of the isocyanurate compound is

[0172]

[0173] The preparation method is as follows:

[0174] 130.5 g (0.5 mol) of tris (2-hydroxyethyl) isocyanurate was dissolved in 160 mL of acetonitrile, cooled to 0°C, 33.6 g (1.4 mol) of hydrogen extraction agent NaH was added, and the temperature naturally increased to room temperature with heat release. Then, 266 g (1.61 mol) of 1-bromohexane was slowly added dropwise at room temperature. After the addition was completed, the temperature was raised to 75°C and refluxed for 16 h. The reaction was confirmed to be complete by TLC spot plate (developing solvent was petroleum ether / ethyl acetate, v / v=1:1).

[0175] The reaction solution was poured into 300 mL of ice water, separated, the aqueous layer was extracted twice with ethyl acetate, the organic phases were combined, washed once with water and once with saturated brine, anhydrous magnesium sulfate was added for drying, and the filtrate was obtained by suction filtration. The solvent was removed from the filtrate by a rotary evaporator (45° C., vacuum degree 10 KPa) to obtain 210.3 g (0.423 mol) of the product with a yield of 84.6%.

[0176] The prepared isocyanurate compound III-1-1 was structurally characterized:

[0177] IR: 2965(ν C-H ), 2917(ν C-H ), 2854(ν C-H ), 1682(ν C＝O ), 1497(δ C-H ), 1423(δ C-H ), 1215(ν C-N ), 1181(ν C-O ), 1019(ν C-O ), 799(r -(CH2)n- ), 696(r -CH2-CH3 ). Where n ≥ 4, r represents the plane rocking vibration, and δ represents the deformation vibration.

[0178] 1H-NMR (400MHz, CDCl3): 4.11 (6H,t,J=7.3Hz), 3.48 (6H,t,J=7.3Hz), 3.36 (6H,t,J=7.2Hz), 1.72 (6H,m,J=7.2 ,5.7Hz), 1.36(6H,m,J=7.0,5.7Hz), 1.28(6H,m,J=7.0Hz), 1.21(6H,quint,J=7.0Hz), 0.91(9H,t,J=7.0Hz).

[0179] 13 C-NMR (400MHz, CDCl3): 149.0, 71.5, 70.2, 48.7, 31.8, 29.3, 25.8, 22.6, 14.0.

[0180] Example 2

[0181] This embodiment provides a specific isocyanurate compound III-1-2, the structural formula of the isocyanurate compound is

[0182]

[0183] The preparation method is basically the same as that in Example 1, except that 1-bromobutane (223 g, 1.63 mol) is used as the reactant instead of 1-bromohexane, the reaction reflux temperature is 65° C., the reaction reflux time is 12 h, and 210.3 g (0.423 mol) of the product is obtained with a yield of 84.6%.

[0184] Compound characterization of isocyanurate compound III-1-2:

[0185] IR: 2963(ν C-H ), 2922(ν C-H ), 2859(ν C-H ), 1691(ν C＝O ), 1485(δ C-H ), 1406(δ C-H ), 1210(ν C-N ), 1182(ν C-O ), 1025(ν C-O ), 789(r -(CH2)n- ), 711(r -CH2-CH3 ).

[0186] 1H-NMR (400MHz, CDCl3): 4.06 (6H,t,J=7.3Hz), 3.43 (6H,t,J=7.3Hz), 3.29 (6H,m,J =6.9Hz), 1.69(6H,m,J=7.2,6.9Hz), 1.42(6H,m,J=7.1Hz), 0.94(9H,t,J=7.1Hz).

[0187] 13 C-NMR (400MHz, CDCl3): 149.1, 71.5, 70.2, 48.5, 31.1, 19.1, 14.0.

[0188] Example 3

[0189] This embodiment provides a specific isocyanurate compound III-3-1, the structural formula of the isocyanurate compound is

[0190]

[0191] The preparation method is as follows:

[0192] 108.5 g (0.5 mol) of 1-ethyl-3,5-bis(2-hydroxymethyl)-1,3,5-triazine-2,4,6-trione was dissolved in 140 mL of acetonitrile, cooled to 0°C, and 16.8 g (0.7 mol) of hydrogen extraction agent NaH was added. After the temperature naturally rose to room temperature as the heat was released, 220 g (1.14 mol) of isooctane bromide was slowly added dropwise at room temperature. After the addition was completed, the temperature was raised to 78°C and refluxed for 18 hours. The reaction was confirmed to be complete by TLC spot plate (developing solvent was petroleum ether / ethyl acetate, v / v=1:1).

[0193] The post-treatment method was the same as in Example 1. 183.4 g (0.415 mol) of product was obtained with a yield of 83.1%.

[0194] Compound characterization of isocyanurate compound III-3-1:

[0195] IR: 2958(ν C-H ), 2920(ν C-H ), 2861(ν C-H ), 1685(ν C＝O ), 1483(δ C-H ), 1464(δ C-H ), 1379(δ C-H ), 1223(ν C-N ), 1183(ν C-O ), 1022(ν C-O ), 794(r -(CH2)n- ), 710(r-CH2-CH3 ).

[0196] 1 H-NMR (400MHz, CDCl3): 5.38 (4H, s), 3.81 (2H, m, J = 7.1Hz), 3.66 (2H, tt, J = 6.4, 5.9Hz), 1.58 (4H, m, J = 7.5, 6.4Hz), 1.53 (4H, m, J = 7.5, 6.4Hz), 1.37 (4H, quint, J = 7.2Hz), 1.28 (4H, qt, J = 7.0, 6.9Hz), 1.25 (4H, tt, J = 7.1, 6.9Hz), 1.23 (3H, t, J = 7.1Hz), 0.95 (6H, t, J = 7.5Hz), 0.87 (6H, t, J = 7.0Hz).

[0197] 13 C-NMR (400MHz, CDCl3): 151.6, 78.1, 71.2, 44.3, 34.9, 31.8, 27.9, 25.4, 25.1, 22.6, 22.3, 14.0, 13.8, 12.9, 9.9, 9.7.

[0198] Example 4

[0199] This embodiment provides a specific isocyanurate compound III-3-2, the structural formula of the isocyanurate compound is

[0200]

[0201] The preparation method is basically the same as that of Example 3, except that 188 g (1.14 mol) of 2-bromomethyltetrahydrofuran is used as the reactant instead of isooctane bromide, and the reaction reflux temperature is 80° C. 154.5 g (0.401 mol) of the product is obtained, with a yield of 80.2%.

[0202] Compound characterization of isocyanurate compound III-3-2:

[0203] IR: 2959(ν C-H ), 2921(ν C-H ), 2858(ν C-H ), 1678(ν C＝O ), 1470(δ C-H ), 1373(δ C-H ), 1217(ν C-N ), 1120(ν C-O ).

[0204] 1H-NMR (400MHz, CDCl3): 5.39 (4H, s), 4.08 (2H, ddt, J = 7.7, 5.8, 5.0Hz), 3.92 ( 2H,d,J=5.0Hz), 3.70~3.88(8H,m), 1.76~2.12(8H,m), 1.21(3H,t,J=7.1Hz).

[0205] 13 C-NMR (400MHz, CDCl3): 151.9, 151.5, 78.1, 76.5, 68.7, 68.2, 65.7, 65.0, 44.5, 28.1, 27.4, 25.7, 12.9.

[0206] Example 5

[0207] This embodiment provides a specific isocyanurate compound III-2-2, the structural formula of the isocyanurate compound is

[0208]

[0209] The preparation method is as follows:

[0210] 315.4 g (3.5 mol) of ethylene glycol monoethyl ether was dissolved in 80 mL of acetone, cooled to 0°C, and 84 g (3.5 mol) of hydrogen extraction agent NaH was added. After the temperature naturally rose to room temperature as the heat was released, 360 mL of acetone solution containing 364.5 g (0.5 mol) of tris(2,3-dibromopropyl)isocyanurate was slowly added dropwise at room temperature. The solution was added dropwise over 3 h. After the addition was completed, the temperature was raised to 50°C and refluxed for 18 h. The reaction was confirmed to be complete by TLC spot plate (developing agent was petroleum ether / ethyl acetate, v / v=1:1).

[0211] The post-treatment method was the same as in Example 1. 311.2 g (0.397 mol) of product was obtained with a yield of 79.5%.

[0212] Compound characterization of isocyanurate compound III-2-2:

[0213] IR: 2960(ν C-H )、2922(ν C-H )、2858(ν C-H )、1689(ν C＝O )、1466(δ C-H )、1377(δ C-H )、1227(ν C-N )、1112(ν C-O ).

[0214] 1H-NMR (400MHz, CDCl3): 3.82~4.07(9H,m), 3.53~3.76(30H,m), 3.35~3.47(12H,m), 1.18~1.29(18H,m).

[0215] 13 C-NMR (400MHz, CDCl3): 149.6, 148.9, 75.5, 74.9, 70.6, 68.4, 66.7, 65.7, 57.9, 57.3, 14.2.

[0216] Example 6

[0217] This embodiment provides a specific isocyanurate compound III-2-1, the structural formula of the isocyanurate compound is

[0218]

[0219] The preparation method is basically the same as that in Example 5, except that tris(2,3-dibromopropyl)isocyanurate (364.5 g, 0.5 mol) is used instead of tris(2,3-dibromopropyl)isocyanurate, the amount of solvent acetone is 100 mL, and 299.5 g (0.382 mol) of the product is obtained with a yield of 76.4%.

[0220] Compound characterization of isocyanurate compound III-2-1:

[0221] IR: 2963(ν C-H )、2925(ν C-H )、2856(ν C-H )、1687(ν C＝O )、1465(δ C-H )、1376(δ C-H )、1219(ν C-N )、1126(ν C-O ).

[0222] 1 H-NMR (400MHz, CDCl3): 4.01 (6H, d, J = 10.1Hz), 3.90 (3H, tt, J = 10.1, 5.3Hz), 3.53~3.65 (6H,m), 3.15~3.44 (42H,m), 1.91~2.05 (12H,m).

[0223] 13 C-NMR (400MHz, CDCl3): 149.8, 149.0, 74.9, 68.7, 68.2, 66.4, 65.7, 59.4, 58.8, 57.9, 29.0.

[0224] Examples 7 to 22 and Comparative Example 1

[0225] Examples 7 to 22 provide specific base oil compositions and greases, and their formulations are shown in Tables 1 and 2.

[0226] The preparation method of the base oil composition is specifically as follows:

[0227] The isocyanurate compounds and poly-α-olefins prepared in Examples 1 to 6 were uniformly mixed and stirred until clear and transparent to obtain a base oil composition.

[0228] Polyalphaolefins used are mPAO10 and PAO6.

[0229] mPAO10: mPAO stands for metallocene polyalphaolefin, and the number behind it represents its kinematic viscosity at 100°C (in mm 2 / s).

[0230] PAO6: PAO stands for non-metallocene polyalphaolefin, and the number behind it represents its kinematic viscosity at 100°C (in mm 2 / s).

[0231] The preparation method of the grease is specifically as follows:

[0232] The base oil composition, thickener and other additives are fully stirred at 60°C, and the system temperature is gradually increased to 160°C at a heating rate of 25°C / 10min for expansion. The system temperature is kept unchanged during the expansion process. When the system temperature reaches the set expansion temperature, the timing is started. After 2 hours of expansion, the heating is stopped and the temperature is lowered. When the system is cooled to 110°C, it is transferred to a three-roll grinder and ground three times to obtain the corresponding grease.

[0233] The viscosity enhancer is mPAO150, mPAO stands for metallocene polyalphaolefin, and the number behind it represents its kinematic viscosity at 100°C (in mm 2 / s).

[0234] The thickener is polyurea powder, which is purchased from Hanguang New Materials (Dongguan) Co., Ltd. The polyurea powder has no free isocyanate group.

[0235] The anti-wear agent was T309 (triphenyl thiophosphate), purchased from Jinzhou Kangtai Lubricant Additive Co., Ltd.

[0236] The oiliness agent was T406 (benzotriazole fatty acid amine salt), purchased from Binzhou Kunhou Lubrication Technology Co., Ltd.

[0237] The antioxidant was T534 (alkyl diphenylamine), purchased from Jinzhou Shengda Chemicals Co., Ltd.

[0238] The rust inhibitor selected was T551 (benzotriazole derivative), purchased from Panhua Chemical (Shanghai) Co., Ltd.

[0239] Table 1: Units are parts by weight

[0240]

[0241] Table 2

[0242]

[0243] The following performance tests were conducted on the lubricating greases prepared in Examples 7 to 22 and Comparative Example 1 and commercially available lubricating greases: anti-friction performance, mechanical shear stability, dropping point, copper sheet corrosion, colloid stability, water-resistant performance and service life. The test results are shown in Tables 3 and 4.

[0244] The test methods or standards are as follows:

[0245] Anti-friction performance: The average wear spot diameter of the grease sample was measured using ASTM D2266 "Standard Test Method for Anti-wear Properties of Greases (Four-ball Test)"; the four-ball test conditions were: load: 392N (40kgf); spindle speed: 1200r / min; test time: 60min; test temperature: 75°C.

[0246] After the test, the wear spot diameter of the lower steel ball is measured. The smaller the wear spot diameter, the better the wear resistance of the sample. The average value of the wear spot diameters of the three lower steel balls is taken to evaluate the wear resistance of the grease sample.

[0247] Mechanical shear stability: GB / T 269-1991 "Determination of cone penetration of grease and petroleum grease" was used to measure the unworked cone penetration of the grease, the cone penetration after 60 reciprocating cycles, and the cone penetration after 100,000 reciprocating cycles at 25°C. The difference in cone penetration was obtained by subtracting the 60-cycle working cone penetration from the 100,000-cycle working cone penetration.

[0248] Dropping point: GB / T 4929-1985 "Determination of dropping point of grease" is used to determine the dropping point of grease.

[0249] Copper sheet corrosion: GB 7326-1987 "Lubricating grease copper sheet corrosion test method" is used to measure the corrosion of grease to copper sheets.

[0250] Colloid stability: NB / SH / T 0324-2010 "Determination of steel mesh oil separation of grease - cone mesh method" was used to test the steel mesh oil separation percentage (w / w, %) of the grease. The test conditions were: 100°C, 30h.

[0251] Water spray resistance: The water spray resistance of grease is determined by the standard SH / T0109-2004 "Test method for water spray resistance of grease". First, 4g of grease sample is filled in the ball bearing, and water is sprayed on the bearing filled with grease at a certain temperature (79°C) and flow rate (5mL / s) for 1 hour. The water spray loss of the grease is calculated to evaluate the water spray resistance of the grease.

[0252] Service life: The service life of grease is measured according to the method of ASTM D3336, with a test speed of 10,000 r / min and a test temperature of 300°F (148.9°C), and the time when the grease fails is recorded. Judgment of grease failure: The grease becomes thinner, dries out, hardens, cokes, or forms sticky carbon deposits, which makes it unable to perform its lubrication function normally.

[0253] Test cycle: 21 1 / 2 hours of operation at 149°C (300°F) and 22 hours of shutdown without heating.

[0254] Table 3

[0255]

[0256] Table 4

[0257]

[0258] From Tables 1 to 4, we can see that:

[0259] The higher the dosage of isocyanurate compounds, the higher the dropping point of the prepared grease, the lower the cone penetration difference, the lower the steel mesh oil separation rate and the lower the water spray weight loss ratio. This shows that the use of isocyanurate compounds in grease is beneficial to improving the dropping point, mechanical shear stability, colloidal stability and water spray resistance of the grease.

[0260] Adding an appropriate amount of isocyanurate compounds is beneficial to extending the service life, reducing the wear spot diameter and improving the anti-friction performance. However, when the amount of isocyanurate compounds is too high (>8 parts by weight), the anti-friction performance and service life of the grease will also decrease. This may be related to the fact that the isocyanurate ring compound itself has a high polarity and is easy to adsorb polar additives, thereby affecting its function and causing the overall performance to decline.

[0261] The above embodiments are merely illustrative of the principles and effects of the present invention, and are not intended to limit the present invention. Anyone familiar with the art may modify or alter the above embodiments without departing from the spirit and scope of the present invention. Therefore, all equivalent modifications or alterations made by a person of ordinary skill in the art without departing from the spirit and technical concept disclosed by the present invention shall still be covered by the claims of the present invention.

Claims

1. An isocyanurate compound, characterized in that Including the compound of formula III-1-1, the compound of formula III-2-1, the compound of formula III-2-2, the compound of formula III-3-1, and the compound of formula III-3-2, the structural formulas are shown below:

2. A base oil composition, characterized in that: The invention comprises the isocyanurate compound as claimed in claim 1 and a poly-alpha-olefin.

3. The base oil composition according to claim 2, characterized in that: The base oil composition includes 60 to 90 parts by weight of the poly-alpha olefin and 2 to 25 parts by weight of the isocyanurate compound.

4. A lubricating grease, characterized in that: The invention comprises the base oil composition as claimed in any one of claims 2 to 3 and a thickener.

5. The lubricating grease according to claim 4, characterized in that Includes one or more of the following features: a) the thickener is selected from one or two of a compound or polymer having at least two urea bonds and a hydroxy fatty acid lithium soap; b) further containing other additives, wherein the other additives are selected from one or more of a tackifier, an anti-wear agent, an oiliness agent, an antioxidant and a rust inhibitor; c) The lubricating grease comprises the following raw material components in parts by weight: Base oil composition 60-85 parts by weight Thickener 5-25 parts by weight.

6. The lubricating grease according to claim 5, characterized in that Includes one or both of the following features: a) the tackifier is a high viscosity metallocene poly α-olefin; b) In the grease, the amount of the other additives is 1.5 to 13 parts by weight.

7. The lubricating grease according to claim 6, characterized in that Among the other additives, the viscosity enhancer is used in an amount of 1 to 10 parts by weight.

8. Use of the lubricating grease according to any one of claims 4 to 6 for lubricating bearings, sliding parts and joints of a device.

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