CN110003387A - A kind of copolymer and its preparation method and application of functional lubrication alkene - Google Patents
A kind of copolymer and its preparation method and application of functional lubrication alkene Download PDFInfo
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/14—Monomers containing five or more carbon atoms
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- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/12—Esters of phenols or saturated alcohols
- C08F222/14—Esters having no free carboxylic acid groups, e.g. dialkyl maleates or fumarates
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- 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
- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
- C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
- C10M107/22—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M107/28—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
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- 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
- C10M145/16—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 polycarboxylic
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- 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—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 type
- C10M2209/086—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 type polycarboxylic, e.g. maleic acid
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- 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—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 type
- C10M2209/086—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 type polycarboxylic, e.g. maleic acid
- C10M2209/0863—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 type polycarboxylic, e.g. maleic acid used as base material
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- 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
- C10N2030/02—Pour-point; Viscosity index
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- 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
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
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Abstract
The invention discloses a kind of copolymers and its preparation method and application of functional lubrication alkene.The copolymer of the functional lubrication alkene is the copolymer of alpha-olefin, olefin(e) acid ester and functional lubrication alkene, wherein the alpha-olefin is selected from C8‑C18One or more of alpha-olefin, the olefin(e) acid ester are selected from C10‑C15One or more of olefin(e) acid ester；Gained copolymer vi is 100~200, and weight average molecular weight is 1000~3500, and pour point is -9~-50 DEG C.Copolymer of the invention has ideal pour point and viscosity characteristics, can be used as lubricating oil, also can be used as additive, is added in mineral oil and high viscosity polymerization ester lubricant, adjusts viscosity and reduces pour point.
Description
Technical field
The present invention relates to technical field of high-molecular polymer, in particular to a kind of functional lubrication alkene, alpha-olefin and
Preparation and purposes of the carbon-carbon double bond in olefin(e) acid ester (hereinafter referred to as olefin(e) acid ester) copolymer of carbochain end.
Background technique
Researcher has carried out more research to lubrication technology at present, and general lubricating base oils are in not additive
In the case of show that high pour point, low-viscosity index obtain high viscosity index (HVI) and low pour point lubricating oil to solve the above-mentioned problems,
United States Patent (USP) 4045507 and 4282392 under the conditions of Louis acid catalysis, prepares low molecular weight poly alpha olefin using 1- decene
PAO, corresponding low temperature fluidity are improved；United States Patent (USP) US4827073 is using alpha-olefin in porous inert titanium dioxide
It is polymerize to obtain poly alpha olefin under the conditions of silicon carrier chrome catalysts, number average molecular weight is between 420 to 18000, pour point
At -15 DEG C or less.In order to further increase oil lubrication performance, maleic anhydride and alpha-olefin copolymer are generally used, so
Alpha-olefin-maleic anhydride-copolymer derivative is made with alkylol esterification afterwards, then mixes it with lubricating base oils
It closes, lubricating oil low temperature flow can be effectively improved；However, there is no clearly provide specific alpha-olefin and olefin(e) acid in the prior art
The copolymer of ester and functional maleic anhydride dialkyl ester, by research of the invention, which, which can provide, lower inclines
Point and high viscosity index (HVI).
Summary of the invention
The object of the invention provides a kind of copolymer of lubrication alkene with low pour point and desired viscosity properties, the present invention
Another purpose be to provide the preparation method and purposes of the copolymer.
The present invention provides a kind of copolymers of functional lubrication alkene, are alpha-olefin, olefin(e) acid ester and maleic anhydride
The copolymer of dialkyl ester, wherein the alpha-olefin is selected from C8-C18One or more of alpha-olefin, the olefin(e) acid ester are selected from
C10-C15One or more of olefin(e) acid ester.
For the copolymer of the functional lubrication alkene, maleic two in the maleic anhydride dialkyl ester
The esterification alcohol radical component of acid anhydrides is C2-C12Alcohol, the alcohol radical component are selected from butanol, isobutanol, amylalcohol, isoamyl alcohol, hexanol, diethyl
One or more of base hexanol, enanthol, octanol, preferably butanol, hexanol, 2-Ethyl Hexanol, octanol.
The alpha-olefin is linear alkene of the carbon-carbon double bond in last bit, is selected from 1- octene, 1- decene, 1- endecatylene, 1-
One or more of dodecylene, 1- tridecylene, tetradecene, 1- pentadecane alkene cetene, preferably the 1- last of the ten Heavenly stems
One or more of alkene, 1- dodecylene, tetradecene, cetene.
The olefin(e) acid ester is straight chain acid ester of the carbon-carbon double bond in last bit, is selected from 9- decenoate, 10 hendecenoic acid
Methyl esters, 10 hendecenoic acid ethyl ester, butyl 10-hendecenoate, 12- tridecylene methyl esters, one in 14- pentadecylenic acid methyl esters
Kind is several, preferably 9- decenoate, 10 hendecenoic acid methyl esters, 12- tridecylene methyl esters, 14- pentadecylenic acid methyl esters
One or more of.
The copolymer of the functional lubrication alkene is liquid copolymer, and viscosity index (VI) is 100~200, is divided equally again
Son amount is 1000~3500, and pour point is -9~-50 DEG C.
For the copolymer of the functional lubrication alkene, the alpha-olefin, olefin(e) acid ester and maleic anhydride dioxane
The molar ratio of base ester is 1~10:1:1~10, preferably 2~6:1:2~5, more preferably 3~5:1:2~4.
The preparation method of the copolymer of the functional lubrication alkene, comprising: alpha-olefin, olefin(e) acid ester and maleic acid
Acid anhydride dialkyl ester carries out copolyreaction, after reaction the isolated copolymer from system.
The preparation method of the copolymer of the functional lubrication alkene, copolyreaction are deposited in initiator and initiation promotor
In lower progress；The initiator is selected from di-tert-butyl peroxide, tert-butyl hydroperoxide, bis- (the tertiary fourths of 2,5- dimethyl -2,5-
Base peroxide) hexane, peroxidating -3,3,5- trimethylhexanoate, bis- (the t-butyl peroxy) -3,3,5- 3-methyl cyclohexanols of 1,1-
One or more of alkane；Preferably di-tert-butyl peroxide, tert-butyl hydroperoxide, peroxidating -3,3,5- trimethyl oneself
One or more of tert-butyl acrylate.
The initiation promotor is selected from imidazoles fluoboric acid salt ionic liquid, and the imidazoles borofluoride is 1- methyl -3-
Ethyl imidazol(e) tetrafluoroborate, 1,2- dimethyl -3- ethyl imidazol(e) tetrafluoroborate, 1- butyl -3- methylimidazole tetrafluoro boric acid
The one or more of salt, 1- ethyl-3-methylimidazole tetrafluoroborate.Preferably 1- ethyl-3-methylimidazole tetrafluoroborate,
One or more of 1,2- dimethyl -3- ethyl imidazol(e) tetrafluoroborate.
The molar ratio of the initiator usage amount and monomer is 0.005~0.05:1, and the initiator and initiation promote
It is 4:1~8:1 into agent molar ratio.
System is added portionwise in the initiator and promotor, and peroxide initiator is added batch-wise with time interval and draws
Hair promotor ionic liquid: being firstly added the peroxide initiator of integral molar quantity 1/3~2/3 and causes promotor ionic liquid
Body starts copolyreaction, then adds remaining peroxide initiator and the initiation promotor ionic liquid scale of construction with 8-12 parts
Enter.
The temperature of the copolyreaction is 180 DEG C~220 DEG C, and the time is 4~8h.
Copolymer of the invention has ideal pour point and viscosity characteristics, they are than long-chain alpha-olefin, maleic two
The high molecular weight copolymer of acid anhydrides has the pour point and viscosity characteristics for more significantly improving mineral oil and high viscosity polymerization ester lubricant.
Copolymer of the invention can be used as lubricating oil on the basis of its viscosity characteristics, lubricity and low pour point, also may be used
As additive, it is added in mineral oil and high viscosity polymerization ester lubricant, adjusts viscosity and reduce pour point.
Copolymer of the invention also is used as the high viscosity polymerization ester lubricant of thermoplastic forming processing.
Specific embodiment
Combined with specific embodiments below, the present invention is furture elucidated, it should be understood that these embodiments are merely to illustrate the present invention
Rather than limit the scope of the invention, after the present invention has been read, those skilled in the art are to various equivalences of the invention
The modification of form falls within the application range as defined in the appended claims.
Embodiment 1
By 0.8mol maleic anhydride di-n-octyl (CAS 2915-53-9) and 0.8mol 1- benzene (No. CAS
112-41-4), 0.2mol 12- tridecylene methyl esters (CAS 29780-00-5) is placed in reaction vessel, and uses vacuum
Negative pressure is carried out in -0.095mpa, high pure nitrogen is filled with to normal pressure, is repeated twice.160 DEG C are heated the mixture to, first
The initiation promotor 1- ethyl-3-methylimidazole tetrafluoroborate of 0.006mol tert-butyl hydroperoxide and 0.0012mol is added
(CAS 143314-16-3), then by 10 parts and every part di-tert-butyl peroxides and 0.0002mol containing 0.001mol
Cause promotor 1- ethyl-3-methylimidazole tetrafluoroborate, is added every 30min a.Di-t-butyl is added in last time
Peroxide and after causing accelerator mixture 30min, then heats to 180 DEG C and is kept for 4 hours, then be cooled to 160 DEG C of uses
Vacuum distillation carries out distillation processing to unpolymerized alkene and olefin(e) acid ester, removes the alkene and olefin(e) acid ester of final residual.
Viscosity is measured with Ubbelohde viscometer.
Weight average molecular weight is measured by gel permeation chromatography.
Pour point is determined according to GB/T 3535.
Viscosity index (VI) is measured according to GB/T2541 and GB/T1195.
Term " monomer ratio " is alpha-olefin used, the molar ratio of olefin(e) acid ester and maleic anhydride dialkyl ester.
The pour point of the copolymer obtained in this embodiment is -39 DEG C, molecular weight 2500, and viscosity index (VI) (VI) is 168.
Embodiment 2
Test group 1: by 5mol 1- decene (CAS 872-05-9), 1mol 9- decenoate (CAS 14436-32-
9) it is placed in reaction vessel with 2mol maleic anhydride bibutylester (CAS 105-76-0), and negative pressure is carried out using vacuum
Processing is filled with high pure nitrogen to normal pressure, is repeated twice in -0.095mpa.180 DEG C are heated the mixture to, is firstly added
The initiation promotor 1,2- dimethyl -3- ethyl imidazol(e) tetrafluoroborate of 0.03mol tert-butyl hydroperoxide and 0.0075mol
(CAS 307492-75-7), then by the initiation of 10 parts and every part tert-butyl hydroperoxide and 0.001mol containing 0.004mol
Promotor 1,2- dimethyl -3- ethyl imidazol(e) tetrafluoroborate are added a at interval of 30min.Peroxidating is added in last time
Object is warming up to 200 DEG C of holding 6h with after initiation accelerator mixture 30min, then is cooled to 180 DEG C using vacuum distillation to not anti-
The alkene answered, olefin(e) acid ester and maleic anhydride bibutylester carry out distillation processing, remove the alkene of final residual, olefin(e) acid ester and suitable
Anhydride maleique dibutyl ester.
Test group 2-8 is the type and maleic anhydride bibutylester monomer ratio for changing alpha-olefin, olefin(e) acid ester, other conditions
And method, with test group 1, olefin(e) acid ester is e pioic acid methyl ester
The molar ratio of other alpha-olefins, olefin(e) acid ester and maleic anhydride bibutylester is 3:1:4, when experiment specific additive amount
Respectively 3mol, 1mol, 4mol, test result are as shown in table 1.
1. embodiment of table, 2 test group feed molar when test result
Embodiment 3
Using alpha-olefin and olefin(e) acid ester (olefin(e) acid ester is e pioic acid methyl ester) and maleic anhydride dialkyl ester (esterifying alcohol C4-
C8 alcohol) it is copolymerized with the molar ratio of 3:1:4 and 5:1:2.Test result is as shown in table 2.To compare, under the same conditions, with
1- decene and 9- decenoate and maleic anhydride dimethyl ester (CAS 624-48-6) are total with the ratio of 3:1:4 and 5:1:2
It is poly-.Other conditions, method are the same as embodiment 2.
2. embodiment of table, 3 test group feed molar when test result
Test result shows the copolymer pour point of 1- decene and 9- decenoate and the preparation of maleic anhydride dimethyl ester
Height, and 1-tetradecylene hydrocarbon and 12- tridecylene acid esters and maleic anhydride dimethyl ester are inclined with the polymer that 4:3:1 is copolymerized
Point is -4 DEG C, and viscosity index (VI) is only 69.
Embodiment 4
Corresponding to the test method in embodiment 1, by alpha-olefin (1- decene, 1- dodecylene) and olefin(e) acid ester (9- decene
Sour methyl esters, 10 hendecenoic acid methyl esters) and maleic anhydride di-n-octyl (No. CAS be 2915-53-9) and maleic anhydride
Dihexyl (CAS 105-52-5) with monomer ratio 3:1:4 or 5:1:2 (additional amount be respectively 3mol, 1mol, 4mol or 5mol,
1mol, 2mol) copolymerization, other conditions, method are the same as embodiment 1.Test result is as shown in table 3.
3. embodiment of table, 4 test group feed molar when test result
Embodiment 5
By 30mol alpha-olefin the mixture of 2:1 (tetradecene and cetene in molar ratio), 6mol olefin(e) acid ester
The mixture of 1:1 (12- tridecylenic acid methyl esters and 14- pentadecylenic acid methyl esters in molar ratio) and 12mol maleic acid two
(2- ethylhexyl) ester (No. CAS be 1330-76-3) is placed in reaction vessel, and using vacuum carry out Negative pressure-
0.095mpa is filled with high pure nitrogen to normal pressure, is repeated twice.170 DEG C are heated the mixture to, 0.3mol tert-butyl is firstly added
Initiation promotor 1,2- dimethyl -3- ethyl imidazol(e) tetrafluoroborate (the CAS 307492- of hydrogen peroxide and 0.0375mol
75-7), 11 parts and every part di-tert-butyl peroxides and 0.005mol containing 0.04mol are then added with the interval of 30min
Cause promotor 1,2- dimethyl -3- ethyl imidazol(e) tetrafluoroborate.Peroxide is added in last time and causes promotor
30min after, be warming up to 200 DEG C of holding 8h, then be cooled to 170 DEG C using vacuum distillation to unpolymerized alkene and olefin(e) acid ester into
Row distillation processing, removes the alkene and olefin(e) acid ester of final residual.
Other copolymers are prepared according to this method, test result is as shown in table 4.
4. embodiment of table, 5 test group feed molar when test result
Claims (10)
1. a kind of copolymer of functional lubrication alkene, which is characterized in that be alpha-olefin, olefin(e) acid ester and maleic anhydride dioxane
The copolymer of base ester, wherein the alpha-olefin is selected from C8-C18One or more of alpha-olefin, the olefin(e) acid ester are selected from C10-
C15One or more of olefin(e) acid ester.
2. the copolymer of functional lubrication alkene according to claim 1, which is characterized in that the maleic anhydride
The esterification alcohol radical component of maleic anhydride is C in dialkyl ester2-C12Alcohol, the alcohol radical component are selected from butanol, isobutanol, penta
One or more of alcohol, isoamyl alcohol, hexanol, 2-Ethyl Hexanol, enanthol, octanol.
3. the copolymer of functional lubrication alkene according to claim 1, which is characterized in that the alpha-olefin is that carbon carbon is double
Key is selected from 1- octene, 1- decene, 1- endecatylene, 1- dodecylene, 1- tridecylene, 1- 14 in the linear alkene of last bit
One or more of carbene, 1- pentadecane alkene cetene.
4. the copolymer of functional lubrication alkene according to claim 1, which is characterized in that the olefin(e) acid ester is that carbon carbon is double
Key is selected from 9- decenoate, 10 hendecenoic acid methyl esters, 10 hendecenoic acid ethyl ester, 10- 11 in the straight chain acid ester of last bit
One or more of olefin(e) acid butyl ester, 12- tridecylenic acid methyl esters, 14- pentadecylenic acid methyl esters.
5. the copolymer of functional lubrication alkene according to claim 1, which is characterized in that viscosity index (VI) be 100~
200, weight average molecular weight is 1000~3500, and pour point is -9~-50 DEG C.
6. the copolymer of functional lubrication alkene according to claim 1, which is characterized in that the alpha-olefin, olefin(e) acid ester
Molar ratio with maleic anhydride dialkyl ester is 1~10:1:1~10.
7. the preparation method of the copolymer of described in any item functional lubrication alkene, feature exist according to claim 1~6
In, comprising: alpha-olefin, olefin(e) acid ester and maleic anhydride dialkyl ester carry out copolyreaction, divide from system after reaction
From obtaining the copolymer.
8. the preparation method of the copolymer of functional lubrication alkene according to claim 7, which is characterized in that copolyreaction
It is carried out in the presence of initiator and initiation promotor；The initiator be selected from di-tert-butyl peroxide, tert-butyl hydroperoxide,
Bis- (t-butyl peroxy) hexanes of 2,5- dimethyl -2,5-, peroxidating 3,3,5- trimethylhexanoate, the bis- (tert-butyls of 1,1-
One or more of peroxide) -3,3,5- trimethyl-cyclohexane；The initiation promotor is selected from 1- methyl -3- ethyl imidazol(e) four
Borofluoride, 1,2- dimethyl -3- ethyl imidazol(e) tetrafluoroborate, 1- butyl -3- methyl imidazolium tetrafluoroborate, 1- ethyl -
The one or more of 3- methyl imidazolium tetrafluoroborate.
9. the preparation method of the copolymer of functional lubrication alkene according to claim 8, the initiator usage amount
Molar ratio with monomer is 0.005~0.05:1, and the initiator and initiation promotor molar ratio are 4:1~8:1.
10. according to claim 1~6 the copolymer of described in any item functional lubrication alkene prepare lubricating oil or lubrication add
Add the application in agent.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111234082A (en) * | 2020-03-12 | 2020-06-05 | 广东巴德富新材料有限公司 | Amphoteric emulsion for permeation-sealed primer and preparation method thereof |
| CN118190728A (en) * | 2024-05-15 | 2024-06-14 | 营口星火化工有限公司 | Online detection analyzer for particles in lubricating oil |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111234082A (en) * | 2020-03-12 | 2020-06-05 | 广东巴德富新材料有限公司 | Amphoteric emulsion for permeation-sealed primer and preparation method thereof |
| CN118190728A (en) * | 2024-05-15 | 2024-06-14 | 营口星火化工有限公司 | Online detection analyzer for particles in lubricating oil |
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