CN116199880A - Amino acid-based ionic liquid, preparation method and application thereof, and water-based lubricant - Google Patents
Amino acid-based ionic liquid, preparation method and application thereof, and water-based lubricant Download PDFInfo
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- CN116199880A CN116199880A CN202310250620.XA CN202310250620A CN116199880A CN 116199880 A CN116199880 A CN 116199880A CN 202310250620 A CN202310250620 A CN 202310250620A CN 116199880 A CN116199880 A CN 116199880A
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- amino acid
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- 150000001413 amino acids Chemical class 0.000 title claims abstract description 81
- 239000002608 ionic liquid Substances 0.000 title claims abstract description 76
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 239000000314 lubricant Substances 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 235000001014 amino acid Nutrition 0.000 claims description 77
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 35
- 229920002643 polyglutamic acid Polymers 0.000 claims description 32
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 30
- 235000013922 glutamic acid Nutrition 0.000 claims description 30
- 239000004220 glutamic acid Substances 0.000 claims description 30
- 239000000178 monomer Substances 0.000 claims description 23
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 18
- 239000003960 organic solvent Substances 0.000 claims description 13
- 150000001768 cations Chemical class 0.000 claims description 12
- 239000003999 initiator Substances 0.000 claims description 12
- 238000005342 ion exchange Methods 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 10
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims description 9
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 238000007363 ring formation reaction Methods 0.000 claims description 7
- 238000007151 ring opening polymerisation reaction Methods 0.000 claims description 7
- 150000001450 anions Chemical class 0.000 claims description 6
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 6
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 claims description 6
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims description 6
- 239000003125 aqueous solvent Substances 0.000 claims description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 3
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 3
- 229940018564 m-phenylenediamine Drugs 0.000 claims description 3
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims 5
- 230000002209 hydrophobic effect Effects 0.000 abstract description 5
- 229920000642 polymer Polymers 0.000 abstract description 5
- 230000001050 lubricating effect Effects 0.000 abstract description 4
- 239000002184 metal Substances 0.000 abstract description 4
- 229910052751 metal Inorganic materials 0.000 abstract description 4
- 239000000758 substrate Substances 0.000 abstract description 4
- 241000894006 Bacteria Species 0.000 abstract description 2
- 239000002253 acid Substances 0.000 abstract description 2
- 239000000919 ceramic Substances 0.000 abstract description 2
- 238000013461 design Methods 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 150000002739 metals Chemical class 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 abstract description 2
- 229940024606 amino acid Drugs 0.000 description 66
- 229960002989 glutamic acid Drugs 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 230000000844 anti-bacterial effect Effects 0.000 description 11
- 238000004108 freeze drying Methods 0.000 description 8
- -1 quaternary ammonium salt cations Chemical class 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000000502 dialysis Methods 0.000 description 4
- 239000004205 dimethyl polysiloxane Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 230000005311 nuclear magnetism Effects 0.000 description 4
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000002390 rotary evaporation Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 241000588724 Escherichia coli Species 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- 238000005461 lubrication Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- LCBXSXVFOUKYDM-UHFFFAOYSA-O 2-hydroperoxyethyl(trimethyl)azanium Chemical compound C[N+](C)(C)CCOO LCBXSXVFOUKYDM-UHFFFAOYSA-O 0.000 description 1
- NXUKNNCMTMFSPF-UHFFFAOYSA-N 2-hydroxyethyl(methyl)azanium;bromide Chemical compound Br.CNCCO NXUKNNCMTMFSPF-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- UUOVEQAKKMIYCT-UHFFFAOYSA-N [N].[B].[P].[S] Chemical compound [N].[B].[P].[S] UUOVEQAKKMIYCT-UHFFFAOYSA-N 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- IDECBPHTOJUOLM-UHFFFAOYSA-M bis(2-hydroxyethyl)-methyl-octylazanium bromide Chemical compound [Br-].C(CCCCCCC)[N+](C)(CCO)CCO IDECBPHTOJUOLM-UHFFFAOYSA-M 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000009881 electrostatic interaction Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Images
Classifications
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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
- C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
- C10M149/12—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M149/14—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds a condensation reaction being involved
- C10M149/18—Polyamides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
- C08G69/10—Alpha-amino-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/48—Polymers modified by chemical after-treatment
-
- 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
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M133/08—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
-
- 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
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/044—Polyamides
-
- 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
-
- 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
- C10N2030/16—Antiseptic; (micro) biocidal or bactericidal
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyamides (AREA)
Abstract
The invention provides an amino acid-based ionic liquid, a preparation method and application thereof, and a water-based lubricant, and relates to the technical field of lubricating materials. The invention realizes the universality of the amino acid ionic liquid on different friction pairs by utilizing the molecular chain composition and the structural design of the polyamino acid, so that the amino acid ionic liquid has good lubricating performance on the surfaces of hydrophilic and hydrophobic substrates such as polymers, metals and ceramics, and the like, and simultaneously, the problem that water-based lubricants are easy to breed bacteria is effectively solved.
Description
Technical Field
The invention relates to the technical field of lubricating materials, in particular to an amino acid-based ionic liquid, a preparation method and application thereof, and a water-based lubricant.
Background
Effective lubrication is an important way to reduce friction and wear. The use of the liquid lubricant not only can reduce friction and wear, but also has the function of cooling. With the rise of environmental awareness and the implementation of related environmental legislation, conventional petroleum-based lubricants have failed to meet the needs. Compared with the traditional oil-based lubricant, the water-based lubricant has become one of important branches in the technical field of lubrication by virtue of the advantages of greenness, low cost, flame retardance, good cooling performance and the like. The research of the high-performance water-based lubricant has important practical significance in the fields of machining, biological lubrication and the like.
The water-based lubricant currently existing mainly adopts fatty acid represented by carboxylic acid derivatives, high molecular polymer, heteroatom-containing nitrogen-sulfur-phosphorus-boron additive, water-soluble organic metal additive and the like. However, small molecule lubricant additives have low viscosity, high corrosiveness and risk of biotoxicity, which greatly limit their use in water-based lubricants.
Disclosure of Invention
The invention aims to provide an amino acid-based ionic liquid, a preparation method and application thereof.
In order to achieve the above object, the present invention provides the following technical solutions:
the invention provides an amino acid-based ionic liquid, wherein anions of the amino acid-based ionic liquid have a structure shown in a formula 1; the cation of the amino acid-based ionic liquid is quaternary ammonium salt type cation;
in the formula 1, m is more than or equal to 1, n is more than or equal to 0, and m+n=1 to 250.
Preferably, the quaternary ammonium salt type cation comprises one or more of structures shown in a formula 2-1, a formula 2-2, a formula 2-3 and a formula 2-4;
in the formula 2-1, the formula 2-2, the formula 2-3 and the formula 2-4, y is independently an integer of 1 to 20.
The invention provides a preparation method of the amino acid-based ionic liquid, which comprises the following steps:
mixing glutamic acid, triphosgene, epichlorohydrin and a first organic solvent, and performing cyclization reaction to obtain glutamic acid NCA monomer;
mixing the glutamic acid NCA monomer, an initiator and a second organic solvent, and carrying out ring-opening polymerization reaction to obtain alpha-polyglutamic acid;
mixing the alpha-polyglutamic acid, the quaternary ammonium salt and water, and performing ion exchange to obtain the amino acid-based ionic liquid.
Preferably, the molecular weight of the alpha-polyglutamic acid is 300-30000 g/mol.
Preferably, the molar ratio of the glutamic acid NCA monomer to the initiator is 10-300:1.
Preferably, the initiator comprises one or more of benzylamine, n-propylamine, aminopolyethylene glycol monomethyl ether, 1, 2-propylene diamine, 1, 3-propylene diamine, 1, 4-butylene diamine, p-phenylene diamine, and m-phenylene diamine.
Preferably, the molar ratio of carboxyl to quaternary ammonium salt in the alpha-polyglutamic acid is 1:0.5-1.5.
The invention provides an application of the amino acid-based ionic liquid prepared by the technical scheme or the preparation method of the amino acid-based ionic liquid in a water-based lubricant.
The invention provides a water-based lubricant, which comprises the amino acid-based ionic liquid prepared by the technical scheme or the amino acid-based ionic liquid prepared by the preparation method and an aqueous solvent.
Preferably, the mass fraction of the amino acid-based ionic liquid in the water-based lubricant is 0.1-5%.
The invention provides an amino acid-based ionic liquid, which realizes the universality of the amino acid-based ionic liquid on different friction pairs by utilizing the composition and structural design of a polyamino acid molecular chain, so that the amino acid-based ionic liquid has good lubricating performance on the surfaces of hydrophilic and hydrophobic substrates such as polymers, metals and ceramics, and the problem that water-based lubricants are easy to grow bacteria is solved. The carboxyl in the amino acid-based ionic liquid is favorable for being adsorbed on the surface of a metal substrate, and the hydrophobic unit is favorable for being adsorbed on the surface of a weak-polarity hydrophobic substrate, so that the water-based lubricant prepared by adopting the amino acid-based ionic liquid is suitable for various hydrophilic and hydrophobic friction pairs. Meanwhile, the quaternary ammonium salt cations in the amino acid-based ionic liquid not only can improve the water solubility of the amino acid-based ionic liquid, but also can endow the amino acid-based ionic liquid with antibacterial performance.
The invention also provides a preparation method of the amino acid based ionic liquid, which is characterized in that the glutamic acid NCA monomer is subjected to ring opening to obtain alpha-polyglutamic acid; and then pairing the-COOH of the alpha-polyglutamic acid with quaternary ammonium salt cations to obtain the amino acid-based ionic liquid.
Drawings
FIG. 1 shows the nuclear magnetism of an amino acid based ionic liquid prepared in example 1 1 HNMR spectrogram;
FIG. 2 is a graph showing the friction coefficient of the amino acid based ionic liquid prepared in example 1 when polydimethylsiloxane vs. glass is rubbed;
FIG. 3 is the results of the antibacterial properties of the amino acid based ionic liquid prepared in example 1;
FIG. 4 shows the nuclear magnetism of the amino acid based ionic liquid prepared in example 2 1 HNMR spectrogram;
FIG. 5 is a graph of the friction coefficient of the amino acid based ionic liquid prepared in example 2 when polydimethylsiloxane vs. glass is rubbed;
FIG. 6 is the results of the antibacterial properties of the amino acid based ionic liquid prepared in example 2;
FIG. 7 shows the nuclear magnetism of the amino acid based ionic liquid prepared in example 3 1 HNMR spectrogram;
FIG. 8 is a graph showing the friction coefficient of the amino acid based ionic liquid prepared in example 3 when polydimethylsiloxane vs. glass is rubbed;
FIG. 9 shows the results of the antibacterial properties of the amino acid based ionic liquid prepared in example 3.
Detailed Description
The invention provides an amino acid-based ionic liquid, wherein anions of the amino acid-based ionic liquid have a structure shown in a formula 1; the cation of the amino acid-based ionic liquid is quaternary ammonium salt type cation;
in the formula 1, m is more than or equal to 1, n is more than or equal to 0, and m+n=1 to 250. In the present invention, the m represents the number of repeating units; the m is preferably 1 to 200, more preferably 2 to 4. In the present invention, the n represents the number of repeating units; the n is preferably 1 to 200, more preferably 25 to 34. The m+n is preferably 2 to 250.
In the present invention, the quaternary ammonium salt type cation preferably includes one or more of structures shown in formula 2-1, formula 2-2, formula 2-3 and formula 2-4;
in the formulae 2-1, 2-2, 2-3 and 2-4, y is independently preferably an integer of 1 to 20, more preferably 5 to 20.
The invention provides a preparation method of the amino acid-based ionic liquid, which comprises the following steps:
mixing glutamic acid, triphosgene, epichlorohydrin and a first organic solvent, and performing cyclization reaction to obtain glutamic acid NCA monomer;
mixing the glutamic acid NCA monomer, an initiator and a second organic solvent, and carrying out ring-opening polymerization reaction to obtain alpha-polyglutamic acid;
mixing the alpha-polyglutamic acid, the quaternary ammonium salt and water, and performing ion exchange to obtain the amino acid-based ionic liquid.
According to the invention, glutamic acid, triphosgene, epichlorohydrin and a first organic solvent are mixed for cyclization reaction, so that glutamic acid NCA monomer is obtained. In the invention, the molar ratio of the glutamic acid, the triphosgene and the epichlorohydrin is preferably 1:0.1-1: 2 to 5, more preferably 1:0.3 to 0.6:2 to 4. In the present invention, the mass ratio of the glutamic acid to the first organic solvent is preferably 1:8 to 20, more preferably 1:10 to 15. In the present invention, the glutamic acid is a reacted monomer, and triphosgene and epichlorohydrin are used to remove water and carbon dioxide generated in the reaction.
In the present invention, the glutamic acid is preferably L-glutamic acid.
In the present invention, the first organic solvent is preferably tetrahydrofuran.
In the present invention, the temperature of the cyclization reaction is preferably room temperature; the time for the cyclization reaction is preferably 6 to 96 hours, more preferably 18 hours.
Preferably, after the cyclization reaction, the obtained product is subjected to rotary evaporation to remove the organic solvent, and the obtained crude product is recrystallized to obtain the glutamic acid NCA monomer. In the present invention, the solvent used for the recrystallization preferably includes tetrahydrofuran and petroleum ether; the volume ratio of the tetrahydrofuran to the petroleum ether is preferably 1:1-4.
After obtaining the glutamic acid NCA monomer, the invention mixes the glutamic acid NCA monomer, an initiator and a second organic solvent, and carries out ring-opening polymerization reaction to obtain the alpha-polyglutamic acid. In the present invention, the molar ratio of the glutamic acid NCA monomer to the initiator is preferably 10 to 300:1, more preferably 20 to 250:1.
In the present invention, the initiator is preferably an amino initiator, more preferably comprises benzylamine, n-amineOne or more of propylamine, aminopolyethylene glycol monomethyl ether, 1, 2-propylene diamine, 1, 3-propylene diamine, 1, 4-butylene diamine, p-phenylenediamine and m-phenylenediamine. In the present invention, the molecular weight of the aminopolyethylene glycol is preferably 200 to 20000g/mol, more preferably 400g/mol. In the present invention, the aminopolyethylene glycol is preferably a double-ended polyethylene glycol (NH) 2 -PEG-NH 2 ). In the present invention, the molecular weight of the aminopolyethylene glycol monomethyl ether is preferably 200 to 20000g/mol.
In the present invention, the molar ratio of the amino group of the initiator to the glutamic acid NCA monomer is preferably 1:50 to 300.
In the present invention, the mass ratio of the glutamic acid NCA monomer to the second organic solvent is preferably 1:5 to 50, more preferably 1:10 to 30, still more preferably 1:12 to 25.
In the present invention, the second organic solvent is preferably N, N-dimethylformamide.
In the present invention, the temperature of the ring-opening polymerization reaction is preferably room temperature, particularly preferably 20 to 40 ℃, more preferably 23 to 35 ℃; the time for the ring-opening polymerization is preferably 12 to 100 hours, more preferably 72 hours.
In the present invention, it is preferable that after the ring-opening polymerization reaction, the obtained polymer is dialyzed for 1 to 3 days and then freeze-dried for 3 to 7 days to obtain the α -polyglutamic acid. In the present invention, the dialysis bag used for the dialysis preferably has a molecular weight cut-off of 500kDa. The invention removes small molecular substances in the system by dialysis. In the present invention, the temperature of the freeze-drying is preferably-50 to-20 ℃. The invention removes water by freeze drying to obtain pure polymer.
In the present invention, the α -polyglutamic acid has a structure represented by formula 3:
in the formula 3, x is preferably an integer of 2 to 250, more preferably 50 to 250.
In the present invention, the molecular weight of the α -polyglutamic acid is preferably 300 to 30000g/mol, more preferably 2000 to 4000g/mol, and still more preferably 3500 to 4900g/mol.
After the alpha-polyglutamic acid is obtained, the alpha-polyglutamic acid, the quaternary ammonium salt and water are mixed, and ion exchange is carried out to obtain the amino acid-based ionic liquid. In the present invention, the molar ratio of the carboxyl group to the quaternary ammonium salt in the α -polyglutamic acid is preferably 1:0.5 to 1.5, more preferably 1:0.95 to 1.15. In the present invention, the mass ratio of the α -polyglutamic acid to water is preferably 1:4 to 15, more preferably 1:5 to 10.
In the present invention, the quaternary ammonium salt preferably includes hydroxycholine or octylbis (2-hydroxyethyl) methyl ammonium bromide.
In the present invention, the temperature of the ion exchange is preferably room temperature, particularly preferably 15 to 40 ℃, more preferably 20 to 35 ℃; the ion exchange time is preferably 24 to 72 hours, more preferably 48 hours.
Preferably, after the ion exchange, the obtained system is freeze-dried to obtain the amino acid-based ionic liquid.
The invention provides application of the amino acid-based ionic liquid in the technical scheme or the amino acid-based ionic liquid prepared by the preparation method in the technical scheme in water-based lubricants, and the application is preferably applied to the water-based lubricants in the biomedical or mechanical processing fields.
The invention provides a water-based lubricant, which comprises the amino acid-based ionic liquid prepared by the technical scheme or the amino acid-based ionic liquid prepared by the preparation method and an aqueous solvent. In the present invention, the aqueous solvent preferably includes water, physiological saline or PBS buffer solution having ph=7.2 to 7.4.
In the present invention, the mass fraction of the amino acid-based ionic liquid in the water-based lubricant is preferably 0.1 to 5%, more preferably 1 to 5%.
In the present invention, the method for producing the water-based lubricant preferably comprises: and mixing the amino acid-based ionic liquid with an aqueous solvent to obtain the water-based lubricant.
The technical solutions of the present invention will be clearly and completely described in the following in connection with the embodiments of the present invention. It will be apparent that the described embodiments are only some, but not all, embodiments of the invention. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1
(1) Adding 10.0. 10.0g L-glutamic acid, 16.0mL of epichlorohydrin, 10.0g of triphosgene and 150mL of tetrahydrofuran into a thick-wall pressure-resistant bottle, reacting for 18 hours at room temperature, removing a solvent through rotary evaporation, and recrystallizing the obtained crude product to obtain a glutamic acid NCA monomer;
(2) Dissolving 5.0g of glutamic acid NCA monomer and 0.08g of benzylamine in 20mL of anhydrous N, N-dimethylformamide, reacting at room temperature for 72h, and dialyzing and freeze-drying the obtained product to obtain alpha-polyglutamic acid; the molecular weight of the obtained alpha-polyglutamic acid is 3.5kg/mol;
(3) 1.0g of the alpha-polyglutamic acid and 0.8g of hydroxychol are dissolved in 5mL of water, ion exchange is carried out at room temperature for 48 hours, and then the amino acid-based ionic liquid is obtained through freeze drying.
The structure of the anion of the amino acid based ionic liquid prepared in the embodiment is shown in a formula 1; in formula 1, m=2, n=25; the structure of the cation is shown as formula 4;
example 2
(1) Adding 10.0. 10.0g L-glutamic acid, 16.0mL of epichlorohydrin, 10.0g of triphosgene and 150mL of tetrahydrofuran into a thick-wall pressure-resistant bottle, reacting for 18 hours at room temperature, removing a solvent through rotary evaporation, and recrystallizing the obtained crude product to obtain a glutamic acid NCA monomer;
(2) 6.2g of the glutamic acid NCA monomer and 0.05. 0.05gNH 2 -PEG-NH 2 (M n =400 g/mol) was dissolved in 30mL of anhydrous N, N-dimethylformamide, and after 72 hours of reaction at room temperature, the obtained product was subjected to dialysis and freeze-drying treatment to obtain α -polyglutamic acid; the alpha-Polyglutamic acid having a molecular weight of 4.9kg/mol
(3) 1.0g of the alpha-polyglutamic acid and 0.5g of hydroxychol are dissolved in 7mL of water, ion exchange is carried out at room temperature for 48 hours, and then the amino acid-based ionic liquid is obtained through freeze drying.
The structure of the anion of the amino acid based ionic liquid prepared in the embodiment is shown as a formula 1; in formula 1, m=4, n=34; the structure of the cation is shown in formula 4 in example 1.
Example 3
(1) Adding 10.0. 10.0g L-glutamic acid, 16.0mL of epichlorohydrin, 10.0g of triphosgene and 150mL of tetrahydrofuran into a thick-wall pressure-resistant bottle, reacting for 18 hours at room temperature, removing a solvent through rotary evaporation, and recrystallizing the obtained crude product to obtain a glutamic acid NCA monomer;
(2) Dissolving 7.0g of glutamic acid NCA monomer and 0.02g of 1, 4-butanediamine in 30mL of anhydrous N, N-dimethylformamide, reacting at 30 ℃ for 72h, and then dialyzing and freeze-drying the obtained product to obtain alpha-polyglutamic acid; the molecular weight of the obtained alpha-polyglutamic acid is 3.7kg/mol;
(3) 1.2g of the alpha-polyglutamic acid and 2.23g of octyl bis (2-hydroxyethyl) methyl ammonium bromide are dissolved in 5mL of water, ion exchange is carried out at room temperature for 48 hours, and then the amino acid-based ionic liquid is obtained through freeze drying.
The structure of the anion of the amino acid based ionic liquid prepared in the embodiment is shown in a formula 1; in formula 1, m=3, n=25; the structure of the cation is shown in formula 5.
Test example 1
FIGS. 1,4 and 7 show the nuclear magnetism of amino acid based ionic liquids prepared in examples 1,2 and 3, respectively 1 As can be seen from the H NMR spectrum, the α -polyglutamic acid is bonded by electrostatic interaction between carboxyl groups and quaternary ammonium salts, and the molar ratio of carboxyl groups to quaternary ammonium salts in the α -polyglutamic acid in example 1 is 1:0.95, and the molar ratio of carboxyl groups to quaternary ammonium salts in the α -polyglutamic acid in example 2 is 1:1, example 3 carboxyl group in alpha-polyglutamic acidThe molar ratio of the base to the quaternary ammonium salt is 1:1.15.
test example 2
Fig. 2, fig. 5, and fig. 8 are the friction coefficients of the amino acid based ionic liquids prepared in examples 1,2, and 3, respectively, when the polydimethylsiloxane vs. glass is rubbed, the test method is as follows: the amino acid based ionic liquid prepared in example 1 was formulated with deionized water to 1wt% of an amino acid based lubricant; the amino acid based ionic liquid prepared in example 2 was formulated into 2wt% amino acid based lubricant with physiological saline; the amino acid based ionic liquid prepared in example 3 was formulated with deionized water to 4wt% amino acid based lubricant; the amino acid based lubricants were each subjected to a tribological test using a CSM frictional wear tester, wherein the test frequency was 1Hz and the frictional distance was 6mm.
As can be seen, with the addition of the amino acid based lubricant, the friction coefficient of example 1 was reduced from 0.741 to 0.325, the friction coefficient of example 2 was reduced from 0.144 to 0.127, and the friction coefficient of example 3 was reduced from 0.165 to 0.150. It is explained that the use of the amino acid based ionic liquids of the present invention allows for various degrees of reduction in the coefficient of friction.
Test example 3
Fig. 3, 6 and 9 show the results of the antibacterial properties of the amino acid based ionic liquids prepared in examples 1,2 and 3, respectively. As can be seen from the graph, compared with the control group, the antibacterial rate of the amino acid based ionic liquid prepared in example 1 to escherichia coli is 96.0%; the antibacterial rate to staphylococcus aureus is 99.9%; the antibacterial rate of the amino acid-based ionic liquid prepared in the example 2 to escherichia coli is 98.0%; the antibacterial rate to staphylococcus aureus is 99.9%; the antibacterial rate of the amino acid-based ionic liquid prepared in the example 3 on escherichia coli is 99.9%; the antibacterial rate to staphylococcus aureus is 99.99 percent.
The foregoing is merely a preferred embodiment of the present invention and it should be noted that modifications and adaptations to those skilled in the art may be made without departing from the principles of the present invention, which are intended to be comprehended within the scope of the present invention.
Claims (10)
1. An amino acid-based ionic liquid is characterized in that anions of the amino acid-based ionic liquid have a structure shown in a formula 1; the cation of the amino acid-based ionic liquid is quaternary ammonium salt type cation;
in the formula 1, m is more than or equal to 1, n is more than or equal to 0, and m+n=1 to 250.
2. The amino acid based ionic liquid according to claim 1, wherein the quaternary ammonium salt type cation comprises one or more of structures shown in formula 2-1, formula 2-2, formula 2-3 and formula 2-4;
in the formula 2-1, the formula 2-2, the formula 2-3 and the formula 2-4, y is independently an integer of 1 to 20.
3. The method for preparing the amino acid-based ionic liquid according to any one of claims 1 to 2, comprising the steps of:
mixing glutamic acid, triphosgene, epichlorohydrin and a first organic solvent, and performing cyclization reaction to obtain glutamic acid NCA monomer;
mixing the glutamic acid NCA monomer, an initiator and a second organic solvent, and carrying out ring-opening polymerization reaction to obtain alpha-polyglutamic acid;
mixing the alpha-polyglutamic acid, the quaternary ammonium salt and water, and performing ion exchange to obtain the amino acid-based ionic liquid.
4. The method according to claim 3, wherein the molecular weight of the α -polyglutamic acid is 300 to 30000g/mol.
5. The method of claim 3, wherein the molar ratio of glutamic acid NCA monomer to initiator is 10-300:1.
6. The method of preparation according to claim 3 or 5, wherein the initiator comprises one or more of benzylamine, n-propylamine, aminopolyethylene glycol monomethyl ether, 1, 2-propanediamine, 1, 3-propanediamine, 1, 4-butanediamine, p-phenylenediamine and m-phenylenediamine.
7. The method according to claim 3, wherein the molar ratio of the carboxyl group to the quaternary ammonium salt in the α -polyglutamic acid is 1:0.5-1.5.
8. Use of the amino acid based ionic liquid according to any one of claims 1 to 2 or the amino acid based ionic liquid prepared by the preparation method according to any one of claims 3 to 7 in a water-based lubricant.
9. A water-based lubricant comprising the amino acid-based ionic liquid according to any one of claims 1 to 2 or the amino acid-based ionic liquid prepared by the preparation method according to any one of claims 3 to 7 and an aqueous solvent.
10. The water-based lubricant according to claim 9, wherein the mass fraction of the amino acid-based ionic liquid in the water-based lubricant is 0.1 to 5%.
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