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CN110016101B - Preparation method of soot dispersed polymethacrylate compound - Google Patents

Preparation method of soot dispersed polymethacrylate compound Download PDF

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Publication number
CN110016101B
CN110016101B CN201810015293.9A CN201810015293A CN110016101B CN 110016101 B CN110016101 B CN 110016101B CN 201810015293 A CN201810015293 A CN 201810015293A CN 110016101 B CN110016101 B CN 110016101B
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soot
dispersed polymethacrylate
monomer
reaction
preparing
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CN110016101A (en
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郭鹏
金鹏
徐小红
汤仲平
安文杰
杨蕾
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Petrochina Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00—Polymerisation catalysts
    • C08F4/28—Oxygen or compounds releasing free oxygen
    • C08F4/32—Organic compounds
    • C08F4/34—Per-compounds with one peroxy-radical
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
    • C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M145/10—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate
    • C10M145/12—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate monocarboxylic
    • C10M145/14—Acrylate; Methacrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1818—C13or longer chain (meth)acrylate, e.g. stearyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/04—Detergent property or dispersant property

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polymerisation Methods In General (AREA)

Abstract

The invention provides a preparation method of a soot dispersed polymethacrylate compound, which comprises the following steps: adding arylamine-containing monomer, solvent and initiator into a reaction kettle, dripping methacrylic acid alkyl ester monomer at 80-100 ℃, and reacting after dripping. The soot-dispersed polymethacrylate compound disclosed by the invention not only has good soot dispersing performance, but also has good pour point depressing performance.

Description

Preparation method of soot dispersed polymethacrylate compound
Technical Field
The invention relates to the field of lubricating oil additives, in particular to a soot dispersed polymethacrylate compound and a preparation method thereof.
Background
Polymethacrylates are polar polymeric compounds that are commonly used as viscosity index improvers and pour point depressants in lubricating oils, and can also exhibit excellent antiwear properties when used at higher concentrations. The introduction of functional groups or elements into the polymethacrylate polymer matrix can impart special properties to the polymers. Therefore, the development of the multifunctional additive by using the polymethacrylate as the carrier of the viscosity index improver is an effective way for developing the multifunctional additive.
In order to improve the soot dispersing properties of oils, researchers have developed soot dispersants of many structures that are characterized by aromatic amine groups in the structure. Patents US20030173251, US20080103074, US20100130393, US20100016192, US20120046206, EP2500406, EP2557144 report that dispersants containing aromatic amines have very good soot dispersing properties. Patents US20060025316, US20080139423, US2000128875, US7960320 and US20120323018 introduce arylamine into an ethylene-propylene copolymer structure to prepare a dispersion type with improved viscosity index, and the product has good soot dispersion performance.
CN1654453A discloses a polyolefin dispersant consisting of a low MW polyolefin having an average molecular weight of about 300 to 10,000 and an ethylenically unsaturated, aliphatic or aromatic, oxygen-and nitrogen-containing graftable monomer, and a method for preparing the same. The monomer can be formed by the reaction product formed by reacting an acylating agent with an amine having one or more primary or secondary amines. Grafted polyolefin dispersants containing such monomers can be formed by grafting the reaction product onto a polyolefin backbone. CN1654453A uses arylamine-containing monomer to polymerize with polyolefin, wherein, the preparation of arylamine-containing monomer (4-aminodiphenylamine) is similar to the present invention, and the polymerization reaction is completely different, CN1654453A uses arylamine-containing monomer to polymerize with olefin, and the obtained product is solid, which is obviously different from the present invention.
US5821313A uses N-heterocyclic (N-alkenyl pyrrolidone) -containing monomers to polymerize with methacrylate monomers.
CN103003400A relates to polyalkyl (meth) acrylates for improving lubricant properties comprising repeat units derived from (meth) acrylates having 6 to 22 carbon atoms in the alcohol residue and repeat units derived from amine derivatives of polar ethylenically unsaturated monomers. CN103003400A was polymerized with a methacrylate ester having 6 to 22 carbon atoms using an ethylenic bond-containing 4-aminodiphenylamine derivative, excluding methyl methacrylate. The methyl methacrylate, one of the monomers of the polymer of the invention, has obvious influence on the performance of the product, so the invention has obvious difference from CN103003400A, and the performance of the obtained polymer is also obviously different.
The monomer for polymerization of the invention uses polymerization raw materials comprising arylamine-containing monomer and methyl methacrylate, which is important for the performance of the obtained product. The polymerization solvent is selected from a mixture of two high boiling point solvents, which has a great influence on the result of the polymerization reaction. The polymerization reaction adopts the dropwise addition of methyl propionate monomers into a system containing arylamine monomers, and the process has great influence on the performance of the product. The ratio of the aromatic amine-containing monomer to methyl methacrylate has a crucial influence on the properties of the product. The initiator has obvious influence on the polymerization reaction, and the polymerization reaction can be smoothly carried out only by the tert-butyl peroxy-2-ethylhexanoate and tert-butyl peroxyacetate used in the invention. The invention adopts arylamine-containing monomer and methyl propionate for polymerization, and the obtained product has good soot dispersing performance.
Disclosure of Invention
The invention aims to provide a soot-dispersed polymethacrylate additive and a preparation method thereof.
The invention provides a preparation method of a soot dispersed polymethacrylate compound, which comprises the following steps: adding arylamine-containing monomer, solvent and initiator into a reaction kettle, dripping methacrylic acid alkyl ester monomer at 80-100 ℃, and reacting after dripping.
The preparation method of the soot-dispersed polymethacrylate compound disclosed by the invention is characterized in that the aromatic amine-containing monomer is preferably prepared by reacting aromatic amine containing primary amine and secondary amine with an acylation agent containing an olefinic bond.
The invention relates to a preparation method of a soot-dispersed polymethacrylate compound, wherein the structural formula of the arylamine of primary amine and secondary amine is preferably as follows:
Figure BDA0001541740020000031
wherein Ar is an aromatic ring, R1Is hydrogen, aryl, arylalkyl, alkenyl or alkoxy, R2is-NH2，CH2-(CH2)n-NH2Or Ar-NH2。
The preparation method of the soot-dispersed polymethacrylate compound provided by the invention is characterized in that the acylation reagent containing the ethylenic bond is preferably acrylic acid, crotonic acid, methacrylic acid, maleic acid or maleic anhydride.
The preparation method of the soot-dispersed polymethacrylate compound is characterized in that the solvent is preferably a mixed solution of petroleum ether, N-butanol, toluene, xylene and N, N-dimethylformamide and N-methylpyrrolidone.
The preparation method of the soot-dispersed polymethacrylate compound disclosed by the invention is characterized in that the initiator is preferably benzoyl peroxide, tert-butyl peroxybenzoate, tert-butyl peroxy-2-ethylhexanoate, tert-butyl peroxyacetate or di-tert-butyl peroxide.
The preparation method of the soot-dispersed polymethacrylate compound provided by the invention is characterized in that the alkyl methacrylate monomer is preferably methacrylic acid C1-C18One or more of alkyl esters.
The preparation method of the soot dispersed polymethacrylate compound is characterized in that the mass ratio of the arylamine-containing monomer to the alkyl methacrylate monomer is preferably 1: 10-100.
The preparation method of the soot-dispersed polymethacrylate compound provided by the invention is characterized in that the mass ratio of the initiator to the alkyl methacrylate monomer is preferably 1: 100-400.
The preparation method of the soot-dispersed polymethacrylate compound provided by the invention is characterized in that the mass ratio of the solvent to the alkyl methacrylate monomer is preferably 1:1 to 5.
The preparation method of the soot-dispersed polymethacrylate compound provided by the invention is characterized in that the reaction temperature of the reaction is preferably 100-160 ℃.
The preparation method of the soot dispersed polymethacrylate compound provided by the invention is characterized in that the reaction time of the reaction is preferably 4-12 hours.
In the preparation method of the soot-dispersed polymethacrylate compound, inert gas is preferably introduced into the reaction.
The invention can also be detailed as follows:
the preparation method of the soot dispersed polymethacrylate compound provided by the invention comprises the steps of adding an arylamine-containing monomer, a solvent and an initiator into a reaction kettle, dropwise adding an alkyl methacrylate monomer at 80-100 ℃, and continuously reacting for 4-12 hours at 100-160 ℃ after dropwise adding.
The invention relates to a preparation method of a soot dispersed polymethacrylate compound, wherein the aromatic amine-containing monomer is prepared by reacting aromatic amine containing primary amine and secondary amine with an acylation agent containing olefinic bond.
The invention relates to a preparation method of a soot dispersed polymethacrylate compound, wherein the structural formula of aromatic amine required by aromatic amine-containing monomer reaction is as follows:
Figure BDA0001541740020000041
wherein Ar is an aromatic ring, R1 is hydrogen, aryl, arylalkyl, alkenyl or alkoxy, R2is-NH2，CH2-(CH2)n-NH2Or Ar-NH2。
The preparation method of the soot-dispersed polymethacrylate compound is characterized in that the ethylenic acylation agent required for preparing the aromatic amine-containing monomer is preferably acrylic acid, methacrylic acid or maleic anhydride.
The preparation method of the soot dispersed polymethacrylate compound is characterized in that the reaction solvent is preferably a mixed solution of two of N-butanol, toluene, xylene, N-dimethylformamide and N-methylpyrrolidone.
In the preparation method of the soot-dispersed polymethacrylate compound, the initiator is preferably tert-butyl peroxybenzoate, tert-butyl peroxy-2-ethylhexanoate, tert-butyl peroxyacetate or di-tert-butyl peroxide.
The invention relates to a preparation method of a soot-dispersed polymethacrylate compound, wherein the alkyl methacrylate monomer is preferably one or more of C1-C16 alkyl methacrylate.
According to the preparation method of the soot dispersed polymethacrylate compound, the mass ratio of the arylamine-containing monomer to the alkyl methacrylate monomer is preferably 1: 10-80.
The preparation method of the soot-dispersed polymethacrylate compound provided by the invention is characterized in that the mass ratio of the initiator to the alkyl methacrylate monomer is preferably 1: 100-200.
In the method for preparing the soot-dispersed polymethacrylate compound, the mass ratio of the solvent to the alkyl methacrylate monomer is preferably 1: 2 to 5.
The preparation method of the soot dispersed polymethacrylate compound provided by the invention is characterized in that the reaction temperature is preferably 100-150 ℃.
The preparation method of the soot dispersed polymethacrylate compound provided by the invention has the advantage that the reaction time is preferably 4-10 hours.
The invention relates to a preparation method of a soot-dispersed polymethacrylate compound, wherein the inert gas is preferably nitrogen.
The invention has the beneficial effects that:
1: the polymerized monomer uses a polymerized raw material comprising arylamine-containing monomer and methyl methacrylate, which is important for the performance of the obtained product.
2: the polymerization solvent is selected from a mixture of two high boiling point solvents, which has a great influence on the result of the polymerization reaction.
3: the polymerization reaction adopts the dropwise addition of methyl propionate monomers into a system containing arylamine monomers, and the process has great influence on the performance of the product.
4: the ratio of the aromatic amine-containing monomer to methyl methacrylate has a crucial influence on the properties of the product.
5: the initiator has obvious influence on the polymerization reaction, and the polymerization reaction can be smoothly carried out only by using tert-butyl peroxy-2-ethylhexanoate and tert-butyl peroxyacetate.
6: the invention adopts arylamine-containing monomer and methyl propionate for polymerization, and the obtained product has good soot dispersing performance.
Detailed Description
FIG. 1: a block flow diagram of example 1;
FIG. 2: a block flow diagram of example 2;
FIG. 3: the flow diagram of example 3;
FIG. 4: a block flow diagram of example 4;
FIG. 5: example 5 flow block diagram.
Detailed Description
The following examples illustrate the invention in detail: the present example is carried out on the premise of the technical scheme of the present invention, and detailed embodiments and processes are given, but the scope of the present invention is not limited to the following examples, and the experimental methods without specific conditions noted in the following examples are generally performed according to conventional conditions.
Temperature at the time of dropping the alkyl methacrylate monomer:
in the present invention, the temperature when the alkyl methacrylate monomer is dropped is not particularly limited, and in general, the alkyl methacrylate monomer is dropped at 80 to 100 ℃ in the present invention, and if the temperature when the alkyl methacrylate monomer is dropped is less than 80 ℃, the reaction temperature is liable to be insufficient because the temperature when the alkyl methacrylate monomer is dropped is too low; the temperature when the alkyl methacrylate monomer is dripped is more than 100 ℃, and energy is wasted due to the overlarge temperature when the alkyl methacrylate monomer is dripped, and no other beneficial effects exist.
Aromatic amine-containing monomers:
in the present invention, the aromatic amine-containing monomer is not particularly limited, and is generally prepared by reacting an aromatic amine containing a primary amine and a secondary amine with an ethylenic bond-containing acylating agent.
Structural formula of arylamine of primary amine and secondary amine：
In the present invention, the aromatic amine-containing monomer is not particularly limited, and the aromatic amine of the primary amine and the secondary amine generally has the structural formula:
Figure BDA0001541740020000071
wherein Ar is an aromatic ring, R1Is hydrogen, aryl, arylalkyl, alkenyl or alkoxy, R2is-NH2，CH2-(CH2)n-NH2Or Ar-NH2。
Acylating agent containing an ethylenic bond:
in the present invention, the aromatic amine-containing monomer is not particularly limited, and the ethylenic bond-containing acylating agent is usually acrylic acid, crotonic acid, methacrylic acid, maleic acid, or maleic anhydride.
Solvent:
in the present invention, the aromatic amine-containing monomer is not particularly limited, and the solvent is usually a mixture of two components of petroleum ether, N-butanol, toluene, xylene, N-dimethylformamide and N-methylpyrrolidone.
Initiator:
in the present invention, the aromatic amine-containing monomer is not particularly limited, and the initiator is usually benzoyl peroxide, t-butyl peroxybenzoate, t-butyl peroxy-2-ethylhexanoate, t-butyl peroxyacetate, or di-t-butyl peroxide.
Alkyl methacrylate monomer:
in the present inventionIn the above description, the aromatic amine-containing monomer is not particularly limited, and usually the alkyl methacrylate monomer is methacrylic acid C1-C18One or more of alkyl esters.
The mass ratio of the aromatic amine-containing monomer to the alkyl methacrylate monomer is as follows:
in the invention, the mass ratio of the aromatic amine-containing monomer to the alkyl methacrylate monomer is not particularly limited, generally, the mass ratio of the aromatic amine-containing monomer to the alkyl methacrylate monomer is 1: 10-100, and if the mass ratio of the aromatic amine-containing monomer to the alkyl methacrylate monomer is less than 1:100, the effect of the prepared product is not ideal due to the small dosage of the aromatic amine-containing monomer; the mass ratio of the monomer containing the arylamine to the alkyl methacrylate monomer is more than 1:10, and the excessive dosage of the monomer containing the arylamine causes the waste of the dosage of the monomer containing the arylamine, and has no other beneficial effects.
Mass ratio of initiator to alkyl methacrylate monomer:
in the present invention, the mass ratio of the initiator to the alkyl methacrylate monomer is not particularly limited, and in general, the mass ratio of the initiator to the alkyl methacrylate monomer of the present invention is 1: 100-400, if the mass ratio of the initiator to the alkyl methacrylate monomer is less than 1:400, the effect of the prepared product is not ideal easily because the amount of the initiator is too small; the mass ratio of the initiator to the alkyl methacrylate monomer is more than 1:100, and the excessive initiator is wasted without other beneficial effects.
Mass ratio of solvent to alkyl methacrylate monomer:
in the present invention, the mass ratio of the solvent to the alkyl methacrylate monomer: the solvent of the present invention is not particularly limited, and the mass ratio of the solvent to the alkyl methacrylate monomer is usually 1: 1-5, if the mass ratio of the solvent to the alkyl methacrylate monomer is less than 1:5, the product prepared is not ideal enough due to too little solvent; the mass ratio of the solvent to the alkyl methacrylate monomer is more than 1:1, and the excessive solvent is excessive, so that the waste of the initiator is caused, and no other beneficial effects exist.
Reaction temperature of the reaction:
in the present invention, the reaction temperature of the reaction is not particularly limited, but the reaction temperature is usually 100 ℃ to 160 ℃, and if the reaction temperature is less than 100 ℃, the reaction temperature is too low, which causes insufficient temperature, and the reaction effect is not ideal; the reaction temperature of the reaction exceeds 160 ℃, and energy is wasted due to overhigh reaction temperature, and other beneficial effects are not achieved.
Reaction time of the reaction:
in the present invention, the reaction time of the reaction is not particularly limited, but the reaction time is usually 4 to 12 hours, and if the reaction time is less than 4 hours, the reaction time is insufficient due to too short reaction time; the reaction time of the reaction is longer than 12 hours, so that the reaction time is too long, the waste of time is caused, and no other beneficial effects exist.
Example 1
9.8g of maleic anhydride, 18.4g of tetraaminodiphenylamine, 30g of xylene and 20g N, N-dimethylformamide are added into a 250mL glass flask equipped with a stirrer, a thermometer, a heating jacket and a nitrogen pipeline, reaction is carried out for 5 hours at 142 ℃, the solvent is evaporated under reduced pressure, and the arylamine-containing monomer M is obtained after ethanol recrystallization.
Example 2
2.2g of arylamine-containing monomer M, 0.2g of tert-butyl peroxy-2-ethylhexanoate, 50g of xylene and 20g of N-methylpyrrolidone were placed in a 250mL glass flask equipped with a stirrer, a thermometer, a heating mantle and a nitrogen line, the temperature was raised to 80 ℃ and 40g of tetradecyl methacrylate was added dropwise, and after the addition was completed, the reaction was carried out at 145 ℃ for 6 hours. After the reaction was completed, the solvent was distilled off under reduced pressure.
Example 3
2.0g of arylamine-containing monomer M, 0.3g of di-tert-butyl peroxide, 50g of toluene and 10g N, N-dimethylformamide are added into a 250mL glass flask equipped with a stirrer, a thermometer, a heating jacket and a nitrogen pipeline, the temperature is raised to 90 ℃, a mixture of 40g of tetradecyl methacrylate and 30g of dodecyl methacrylate is dropwise added, the reaction is carried out at 120 ℃ for 8 hours after the dropwise addition is finished, and the solvent is evaporated under reduced pressure after the reaction is finished.
Example 4
1.8g of arylamine-containing monomer M, 0.2g of tert-butyl peroxy-2-ethylhexanoate, 40g of xylene and 10g N, N-dimethylformamide are added to a 250mL glass flask equipped with a stirrer, a thermometer, a heating mantle and a nitrogen gas line, the temperature is raised to 100 ℃, a mixture of 30g of tetradecyl methacrylate, 20g of dodecyl methacrylate and 10g of methyl methacrylate is added dropwise, the reaction is carried out for 4 hours at 150 ℃ after the dropwise addition is finished, and the solvent is evaporated under reduced pressure after the reaction is finished.
Example 5
This example is a soot dispersancy performance test of additives in oil.
A test agent was added to a test oil having a soot content of 4.6% in an equivalent amount of 1.0 wt%, and the soot dispersibility was examined by measuring the change in viscosity of the oil, and the results are shown in Table 1.
Table 1, soot dispersing property simulation evaluation of several soot-dispersed polymethacrylates.
Figure BDA0001541740020000111
As can be seen from Table 1, examples 2, 3 and 4 of the present invention all had very good soot dispersing properties.
Example 6
This example is a pour point depressant performance test experiment.
15g of soot-dispersed polymethacrylate compound is added into 85g of MVI150, heated and stirred at the constant temperature of 70 ℃ for 2 hours, and the pour point of the oil product is tested.
TABLE 2 evaluation of the pour point depressing properties of several soot-dispersed polymethacrylates.
Item Example 2 Example 3 Example 4 Test method
Pour point/. degree.C -27 -30 -36 GB/T 3535
As can be seen from Table 2, the soot-dispersed polymethacrylate compound of the invention has very good pour point depressing property.

Claims (10)

1. A preparation method of a soot dispersed polymethacrylate compound comprises the following steps: adding a monomer containing arylamine, a solvent and an initiator into a reaction kettle, dropwise adding an alkyl methacrylate monomer at 80-100 ℃, and reacting after dropwise adding;
the monomer containing the arylamine is prepared by the reaction of arylamine containing primary amine and secondary amine and an acylation reagent containing olefinic bond;
the structural formula of the arylamine of the primary amine and the secondary amine is as follows:
Figure FDA0003108863790000011
wherein Ar is an aromatic ring, R1Is aryl, arylalkylRadical, alkenyl or alkoxy, R2Is CH2-(CH2)n-NH2Or Ar-NH2；
The mass ratio of the aromatic amine-containing monomer to the methacrylic acid alkyl ester monomer is 1: 10-100.
2. The method of preparing a soot-dispersed polymethacrylate as claimed in claim 1, wherein the acylating agent containing an ethylenic bond is acrylic acid, crotonic acid, methacrylic acid, maleic acid or maleic anhydride.
3. The method of preparing a soot-dispersed polymethacrylate as claimed in claim 1, wherein the solvent is a mixture of petroleum ether, N-butanol, toluene, xylene, N-dimethylformamide and N-methylpyrrolidone.
4. The method of preparing a soot-dispersed polymethacrylate as claimed in claim 1, wherein the initiator is benzoyl peroxide, t-butyl peroxybenzoate, t-butyl peroxy-2-ethylhexanoate, t-butyl peroxyacetate or di-t-butyl peroxide.
5. The method of preparing a soot-dispersed polymethacrylate as claimed in claim 1, wherein the alkyl methacrylate monomer is methacrylic acid C1-C18One or more of alkyl esters.
6. The method of preparing a soot-dispersed polymethacrylate as claimed in claim 1, wherein the mass ratio of the initiator to the alkyl methacrylate monomer is 1: 100-400.
7. The method of preparing a soot-dispersed polymethacrylate as claimed in claim 1, wherein the mass ratio of the solvent to the alkyl methacrylate monomer is 1:1 to 5.
8. The method of preparing a soot-dispersed polymethacrylate as claimed in claim 1, wherein the reaction temperature of the reaction is 100 ℃ to 160 ℃.
9. The method of preparing a soot-dispersed polymethacrylate as claimed in claim 1, wherein the reaction time is 4-12 hours.
10. The method of preparing a soot-dispersed polymethacrylate as claimed in claim 1, wherein the reaction requires an inert gas.
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0274589A2 (en) * 1986-12-24 1988-07-20 Texaco Development Corporation Lubricating oil containing dispersant viscosity index improver
CN1286275A (en) * 1999-08-31 2001-03-07 中国石油化工集团公司 Process for preparing graft copolymerization type non-ash disperser
CN101130710A (en) * 2006-07-28 2008-02-27 雅富顿公司 Alkyl acrylate copolymer dispersants and uses thereof
CN103003400A (en) * 2010-07-29 2013-03-27 赢创油品添加剂有限公司 Polyalkyl (meth) acrylate for improving lubricating oil properties

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0274589A2 (en) * 1986-12-24 1988-07-20 Texaco Development Corporation Lubricating oil containing dispersant viscosity index improver
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