CN112745978A - Amide auxiliary agent capable of being used as lubricant and preparation method thereof - Google Patents
Amide auxiliary agent capable of being used as lubricant and preparation method thereof Download PDFInfo
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- CN112745978A CN112745978A CN201911057339.4A CN201911057339A CN112745978A CN 112745978 A CN112745978 A CN 112745978A CN 201911057339 A CN201911057339 A CN 201911057339A CN 112745978 A CN112745978 A CN 112745978A
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- auxiliary agent
- citrate
- amide
- amide auxiliary
- aliphatic amine
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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
- 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
- C10M133/16—Amides; Imides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
Abstract
The invention provides an amide auxiliary agent capable of being used as a lubricant and a preparation method thereof, wherein the amide auxiliary agent comprises the following general structureA mixture of one or more of the formulae:
wherein X is NH; r1、R2、R3Each independently is one of alkyl groups having 8 to 20 carbon atoms. The amide auxiliary agent disclosed by the invention is almost smokeless, low in viscosity, wide in range of melt drop points, free of metal ions, lubricating and biodegradable.
Description
Technical Field
The invention particularly relates to an amide auxiliary agent capable of being used as a lubricant and a preparation method thereof.
Background
The lubricant is a lubricating medium for reducing frictional resistance. The lubricant also has cooling, dispersing, cleaning, and anti-fouling effects.
In the plastic processing and wood plastic processing industries, plastic particles (including wood plastic) usually have high viscosity after melting, and during the processing, when the molten high polymer passes through a narrow slit, a sprue and the like, the polymer melt must generate friction with the surface of a processing machine, and the friction is very unfavorable for the processing of the polymer, the melt fluidity is reduced due to the friction, and the surface of a product is rough, lack of gloss or generate flow marks due to the severe friction. Meanwhile, the service life of the die is shortened due to the severe friction between the material and the die, and the maintenance cost of the equipment is increased.
For this reason, it is necessary to add an auxiliary agent for the purpose of improving lubricity, reducing friction, and lowering interfacial adhesion, that is, an internal (external) lubricant. The external lubricant is mainly used for improving the friction condition of a polymer melt and a hot metal surface of equipment, so that a plastic part is easy to demould, has poor compatibility with a polymer and is easy to migrate outwards from the melt, and a thin isolating film can be formed between the melt and a mould in a forming process, so that the plastic does not stick to the surface of the mould. The internal lubricant has good compatibility with the polymer, and plays a role in reducing the cohesion force among polymer molecules in the polymer, thereby improving the internal friction heat of the plastic melt and the fluidity of the melt. The bonding between the internal lubricant and the long chain molecules of the polymer is not strong, and they may act similarly to a rolling bearing, and thus can align themselves in the melt flow direction to slide each other, so that the internal friction is reduced, which is the mechanism of internal lubrication.
Lubricants, in addition to improving flowability, may also function as melt accelerators, dispersants, antiblock and antistatic agents, slip agents, and the like.
At present, stearic acid, metal stearate, graphite, molybdenum disulfide, polytetrafluoroethylene, nylon, boron nitride, graphite fluoride and the like are frequently used as solid lubricants, inorganic mineral lubricants have the problems of difficult degradation and complex production process, organic metal salt lubricants have the problems of serious fuming, complex production process and the like, and stearic acid lubricants have the problems of complex production process, high-pressure reactor and the like.
During the operation of the machine, the lubricant is used for reducing the friction resistance of the friction pair and slowing down the wear of the friction pair. The lubricant can also play a role in cooling, cleaning, pollution prevention and the like on the friction pair. Suitable additives may be added to certain lubricants in order to improve the lubricating properties. When the lubricant is selected, various factors such as the motion condition, material, surface roughness, working environment and working condition of the friction pair, the performance of the lubricant and the like are generally considered. In mechanical systems, the lubricant is usually supplied to the respective parts to be lubricated by a lubrication system.
At present, common mechanical lubricants are mainly derived from petroleum extracts and can be classified into mechanical oil (high-speed lubricating oil), loom oil, main shaft oil, rail oil, steel rolling oil, gas turbine oil, compressor oil, refrigerator oil, cylinder oil, marine oil, gear oil, machine pressure gear oil, axle oil, instrument oil and vacuum pump oil according to purposes. However, the lubricating oil from petroleum belongs to non-renewable resources, and the refining process is complex, and impurities are easily carried on the lubricating oil, so that the lubricating oil damages equipment.
Disclosure of Invention
The invention aims at the problems and provides an amide auxiliary agent which can be used as a lubricant, is easy to prepare, has no metal ions and is almost smokeless, and a preparation method thereof.
In order to solve the technical problems, the invention adopts the following technical scheme:
one aspect of the invention provides an amide auxiliary agent, wherein the amide auxiliary agent is a mixture of one or more of the following structural formulas:
In the present invention, the alkyl group means a straight-chain or branched alkyl group composed of hydrocarbon elements. For example, R1、R2、R3Independently selected from linear or branched alkyl groups having 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms. Preferably, R1、R2、R3Independently selected from one of linear chain or branched chain alkyl with 9-20 carbon atoms, and more preferably one of linear chain or branched chain alkyl with 10-18 carbon atoms. Wherein "independently selected" means R1、R2、R3The number of carbon atoms of the alkyl group(s) may be the same or different, e.g., R1May be an alkyl group having 10 carbon atoms, R2May be an alkyl group having 12 carbon atoms, R3An alkyl group having 18 carbon atoms, etc.
Preferably, R1、R2、R3Is in a straight chain or branched chain structure.
Further preferably, when the structure is a branched structure, the number of branches is not more than three, and the carbon atom of each branch is not more than three.
Preferably, the amide auxiliary agent is solid, liquid or paste at normal temperature. Wherein when R is1、R2、R3In the case of straight-chain alkyl, the auxiliaries of the invention are generally solid at ordinary temperature. When R is1、R2、R3When the auxiliary agent contains branched chains, the auxiliary agent is generally in a liquid state or a paste state at normal temperature.
The second aspect of the invention provides a preparation method of an amide auxiliary agent, wherein the amide auxiliary agent is generated by reacting a citric acid triester compound with fatty amine, and the fatty amine is one or more of saturated fatty amines with 8-20 carbon atoms.
Preferably, the aliphatic amine is a linear aliphatic amine, a branched aliphatic amine, or a mixture of a linear aliphatic amine and a branched aliphatic amine, and when the aliphatic amine has a branched structure, the number of branches is not more than three, and the carbon atom of each branch is not more than three.
Preferably, the number of carbon atoms of the aliphatic amine is 9-20.
Preferably, the molar ratio of the amino group to the ester group of the fatty amine to the citric acid triester compound is 2-5: 1, preferably 3-4: 1.
Preferably, the citric acid triester compound comprises one or more of, but not limited to, trimethyl citrate, triethyl citrate, tripropyl citrate, tributyl citrate, triisopropanol citrate, triolein citrate, trilauryl citrate, trioctyl citrate, triisooctyl citrate, triallyl citrate, and tripentyl citrate.
Preferably, the aliphatic amine includes, but is not limited to, one or more of octylamine, decylamine, undecylamine, laurylamine, tetradecylamine, hexadecylamine, octadecylamine, isooctylamine, isotridecylamine, and the like.
Preferably, the amide auxiliary agent is a mixture of one or more of the following structural formulas:
Preferably, the amide auxiliary agent is solid, liquid or paste at normal temperature.
Preferably, the reaction is carried out in the absence of a solvent or a liquid solvent, which may be a conventional low-toxicity organic solvent
Further preferably, the solvent includes but is not limited to one or more of ethanol, water, N-dimethylformamide, glycerol, ethylene glycol and methanol.
More preferably, the solvent is ethanol, wherein the ethanol can be absolute ethanol or ethanol water solution with any concentration, and ethanol water solution with the mass percentage of 5-90% is preferably adopted, and ethanol water solution with the mass percentage of 10-80% is further preferably adopted.
Preferably, the reaction temperature is controlled to be 20-150 ℃.
Further preferably, the reaction temperature is controlled to be 20-90 ℃.
Preferably, the reaction time is controlled to be 1-36 h, more preferably 5-30 h, even more preferably 5-20 h, and most preferably 5-15 h.
The third aspect of the invention provides the use of the amide auxiliary agent or the amide auxiliary agent prepared by the preparation method as a lubricant.
Preferably, when the amide auxiliary agent is in a solid state at normal temperature, the amide auxiliary agent is used as a lubricant to be added into the casting and molding process of wood plastic, plastic and high polymer material products, medicines and other products.
The plastic field comprises a general plastic field and a special purpose plastic field, the general plastic field comprises materials such as nylon (PA), Polyethylene (PE), polypropylene (PP), polyvinyl chloride (PVC), Polystyrene (PS), acrylonitrile-butadiene-styrene copolymer (ABS) and the like, and the general application comprises packaging, household use, toys, stationery and the like; the plastic with special application comprises the industries of food, medicine, toys for children and the like.
The wood-plastic industry is the industry of mixing and preparing plastic and wood powder, such as wood-plastic boards and the like.
Other polymer material fields include polymer filter membrane manufacturing industry and other industries relating to polymer material extrusion or calendering and demolding processes.
The field of medicine includes extrusion molding of pharmaceutical tablets, and the like.
Other areas are any where a lubricant is needed.
The amide auxiliary agent in the invention can replace the existing lubricant in the product formula in the corresponding field. The mass percentage of the amide auxiliary agent added in the invention is 0.1-5%.
For example, when the amide auxiliary agent of the present invention is used in the field of wood plastic, the addition mass of the amide auxiliary agent of the present invention is preferably 1.5 to 2%, and more preferably 1.6 to 1.8% of the total mass of the formula of the wood plastic product. Wherein, other components and the proportion of the formula of the wood-plastic product can be adjusted by adopting the conventional technology in the field, and the formula of the wood-plastic product can be adjusted if necessary.
When the amide auxiliary agent is used in the field of plastics, the addition mass of the amide auxiliary agent is 0.1-5.0% of the total mass of a plastic product formula. The plastic product formula can be adjusted by adopting conventional technology in the field, if necessary, the resin in the plastic product can be nylon (PA), Polyethylene (PE), polypropylene (PP), polyvinyl chloride (PVC), Polystyrene (PS) and acrylonitrile-butadiene-styrene copolymer (ABS), and also comprises other special plastic resin and the like.
When the amide auxiliary agent is used in the field of medicines, the addition mass of the amide auxiliary agent is 0.1-5.0% of the total mass of a medicine product formula. Wherein, other components and the proportion of the formula of the drug product can be adjusted by adopting the conventional technology in the field, if necessary, the formula of the drug product can also be adjusted, and the drug product can be tablets, granules and the like.
The amide auxiliary agent disclosed by the invention is almost smokeless, low in viscosity, wide in range of molten drop points, free of metal ions, good in internal and external lubricating performance, free of precipitation, beneficial to improvement of the glossiness of the surface of a product and capable of obviously reducing the energy consumption in the production process.
In the application process, the amide auxiliary agent also has the functions of a defoaming agent, a cleaning agent, a viscosity index improver, a dispersant, an anti-corrosion agent, an extreme pressure agent, a friction modifier, an anti-foaming agent and the like.
Preferably, when the amide-based auxiliary agent is in a liquid or paste state at normal temperature, the auxiliary agent is used for mechanical lubrication.
The mechanical lubrication includes, but is not limited to, lubrication of transmission gears, instruments, bearings, pump transmission shafts, guide rails, turbines, compressors, engines, reducers and other translation, transmission or rotation devices.
Due to the implementation of the technical scheme, compared with the prior art, the invention has the following advantages:
the amide auxiliary agent disclosed by the invention is almost smokeless, low in viscosity, wide in range of melt drop points, free of metal ions, and biodegradable, and has a lubricating effect.
The preparation method is simple, the post-treatment is easy, the reaction is easy to control, and the product has high yield and high purity.
Drawings
FIG. 1 is an FTIR spectrum of the solid product of examples 1 to 3;
Detailed Description
The following examples are intended to illustrate several embodiments of the present invention, but are not intended to limit the invention to these embodiments. It will be appreciated by those skilled in the art that the present invention encompasses all alternatives, modifications and equivalents as may be included within the scope of the claims.
Structures and the like not described in detail in the present invention are conventional technical means in the art.
Example 1
Triethyl citrate (100g, 0.36mol), octadecylamine (292g, 1.08mol), 10% ethanol (100mL) were added to a 1000mL round bottom flask equipped with a water condenser, and after 5 hours of isothermal reaction at 80 ℃, the reaction product was washed with water and dried to obtain a solid product.
The H-NMR results were as follows:1H NMR(500MHz，Chloroform-d)δ7.11(t，J＝5.9Hz，1H)，6.70(t, J ═ 5.7Hz, 2H), 3.19(m, J ═ 6.6, 5.7, 4.1Hz, 5H), 2.62(m, J ═ 75.8, 14.5Hz, 4H), 2.49(d, J ═ 10.8Hz, 0H), 1.47(m, J ═ 7.0Hz, 6H), 1.25(d, J ═ 3.3Hz, 89H), 0.87(t, J ═ 6.9Hz, 9H). The peak appearance of H-NMR shows that the substance structure contains the characteristic structure of citric acid (2.62ppm) and long-chain fat-CH2- (1.25ppm), with the occurrence of the characteristic hydrogens of the amide group (7.11ppm and 6.70 ppm).
FTIR results are shown in FIG. 1, example 1, at 2848.98cm-1-2955.10cm-1Strong alkane C-H stretching vibration occurs at 1467.35cm-1Strong C-H bending vibration appears, which indicates that the matter has long fat chains; at 1653.06cm-1The characteristic peak of C ═ O with strong amide bond appears, which indicates that a large number of amide bonds are formed in the reaction, and the peak is 1744.90cm-1The weak ester group C ═ O stretching vibration peak appears, which indicates that trace amount of triethyl citrate is remained.
The reaction was considered successful by a combined comparison of H-NMR and FTIR spectra.
The melting range of the solid product of this example is 92-104 ℃.
A viscosity of 77.5 mPas at 120 DEG C-1(ii) a Viscosity at 110 ℃ of 98.0 mPas-1。
Example 2
Triethyl citrate (100g, 0.36mol), dodecylamine (200g, 1.08mol) and 50% ethanol (100mL) were charged into a 1000mL round bottom flask equipped with a water condenser, and after a reaction at 80 ℃ for 8 hours, the reaction product was washed with water and dried to obtain a solid product.
The H-NMR results were as follows:1h NMR (400MHz, Chloroform-d)67.13(t, J ═ 5.9Hz, 1H), 6.87(t, J ═ 5.7Hz, 3H), 3.24-3.10(m, 7H), 2.71(d, J ═ 14.5Hz, 2H), 2.54(d, J ═ 14.5Hz, 2H), 1.46(t, J ═ 7.2Hz, 8H), 1.36-1.15(m, 66H), 0.87(t, J ═ 6.8Hz, 9H). The peak appearance of H-NMR indicates that the substance contains the characteristic structure of citric acid (2.71ppm and 2.54ppm) and long-chain fat-CH2- (1.15-1.36ppm) with the occurrence of the characteristic hydrogens of the amide group (7.13ppm and 6.87 ppm).
FTIR results are shown in FIG. 1, example 2At 2848.98cm-1-2955.10cm-1Strong alkane C-H stretching vibration occurs at 1467.35cm-1Strong C-H bending vibration appears, which indicates that the matter has long fat chains; at 1653.06cm-1The characteristic peak of C ═ O with strong amide bond appears, which indicates that a large number of amide bonds are formed in the reaction, and the peak is 1744.90cm-1The weak ester group C ═ O stretching vibration peak appears, which indicates that trace amount of triethyl citrate is remained.
The reaction was considered successful by a combined comparison of H-NMR and FTIR spectra.
The melting range is 91.2-112 ℃.
Viscosity at 140 ℃ of 47.5 mPas-1(ii) a Viscosity of 56 mPas at 130 DEG C-1。
Example 3
A1000 mL round bottom flask equipped with a water condenser was charged with tributyl citrate (10g, 28mmol), octadecylamine (22.5g, 84mmol), 50% ethanol (100mL), reacted at 80 ℃ for 8 hours, and then the reaction product was washed with deionized water, filtered, and dried to obtain a solid product.
The H-NMR results were as follows:1h NMR (400MHz, Chloroform-d) δ 4.15-4.04(m, 12H), 2.80(t, J ═ 7.7Hz, 3H), 1.96(d, J ═ 5.4Hz, 3H), 1.63-1.45(m, 6H), 1.25(s, 81H), 0.98-0.81(m, 9H). The peak appearance of H-NMR shows that the substance structure contains the characteristic structure of citric acid (2.80ppm) and long-chain fat-CH2-(1.25ppm)。
FTIR results are shown in FIG. 1, example 3, at 2848.98cm-1-2955.10cm-1Strong alkane C-H stretching vibration occurs at 1467.35cm-1Strong C-H bending vibration appears, which indicates that the matter has long fat chains; at 1653.06cm-1The characteristic peak of C ═ O with strong amide bond appears, which indicates that a large number of amide bonds are formed in the reaction, and the peak is 1744.90cm-1A weak stretching vibration peak of the ester group C ═ O appears, indicating that a trace amount of tributyl citrate remains.
The reaction was considered successful by a combined comparison of H-NMR and FTIR spectra.
The melting range is 85-103 ℃.
At the temperature of 120 ℃, the temperature of the mixture is controlled,the viscosity was 80.2 mPas-1(ii) a A viscosity of 101.0 mPas at 110 DEG C-1。
The lubricant of example 1 replaces the domestic lubricant (HY8201A) in the formula of the wood-plastic raw material to carry out wood-plastic production experiments, and the specific method and the results are shown in Table 1.
TABLE 1
A comparison experiment shows that when the lubricant in the embodiment 1 is used for processing the hollow wood-plastic plate, compared with the lubricant in the original factory, the power consumption in the processing process is reduced under the same extrusion temperature and rotating speed, which shows that the lubricant in the embodiment 1 has good external lubricating effect and is beneficial to reducing the processing cost; in addition, the processed wood-plastic board pigment is uniformly dispersed, the hardness of the board reaches the standard, the surface gloss is good, and after the board is boiled for 24 hours, the lubricant is not separated out, which shows that the lubricant has good compatibility with the wood-plastic raw material and does not damage the internal structure.
The lubricant disclosed by the invention has a lubricating effect, and can promote the dispersion and uniform mixing of the pigment, the wood powder, the plastic particles and the filler in the material when being used for wood-plastic processing, so that the performance and the appearance of the wood-plastic board are improved to a certain extent. Meanwhile, the lubricant is used to reduce the friction between the material and the metal die, reduce the loss and maintenance cost of the equipment and effectively prolong the service life of the equipment.
In addition, it can be concluded from the structural properties of the materials that the lubricants of the present invention can achieve biodegradation, wherein the reaction products of example 1, after 20 or so days immersion in water, give off an odor, indicating that microorganisms can grow using the products of example 1.
The present invention includes but is not limited to the above embodiments, and those skilled in the art can convert more embodiments within the claims of the present invention.
Claims (20)
1. An amide auxiliary agent, which is characterized in that: the amide auxiliary agent is a mixture of one or more of the following structural formulas:
2. The amide auxiliary agent according to claim 1, wherein: r1、R2、R3Independently selected from alkyl with 9-20 carbon atoms.
3. The amide auxiliary agent according to claim 1 or 2, characterized in that: r1、R2、R3And a straight chain or branched structure, and when the structure is a branched structure, the number of branches is not more than three, and the carbon atom of each branch is not more than three.
4. The amide auxiliary agent according to claim 1, wherein: the amide auxiliary agent is solid, liquid or paste.
5. A preparation method of an amide auxiliary agent is characterized by comprising the following steps: the amide auxiliary agent is generated by reacting a citric acid triester compound with fatty amine, wherein the fatty amine is one or more of saturated fatty amines with 8-20 carbon atoms.
6. The method of claim 5, wherein: the aliphatic amine is linear chain aliphatic amine, branched chain aliphatic amine or a mixture of the linear chain aliphatic amine and the branched chain aliphatic amine, when the aliphatic amine is in a branched chain structure, the number of branched chains is not more than three, and the carbon atom of each branched chain is not more than three.
7. The method of claim 5, wherein: the number of carbon atoms of the aliphatic amine is 9-20.
8. The method of claim 5, wherein: the feeding ratio of the aliphatic amine to the citric acid triester compound is 2-5: 1, preferably 3-4: 1 according to the molar ratio of the amino group to the ester group.
9. The method of claim 5, wherein: the citric acid triester compound comprises one or more of, but not limited to, trimethyl citrate, triethyl citrate, tripropyl citrate, tributyl citrate, triisopropanol citrate, triolein citrate, trilauryl citrate, trioctyl citrate, triisooctyl citrate, triallyl citrate and tripentyl citrate.
10. The method of claim 5, wherein: the aliphatic amine includes, but is not limited to, one or more of octylamine, decylamine, undecylamine, laurylamine, tetradecylamine, hexadecylamine, octadecylamine, isooctylamine, isotridecylamine, and the like.
11. The method of claim 5, wherein: the amide auxiliary agent is a mixture of one or more of the following structural formulas:
12. The method of claim 5, wherein: the amide auxiliary agent is solid, liquid or paste.
13. The method of claim 5, wherein: the reaction is carried out in the absence of a solvent or a liquid solvent.
14. The method of manufacturing according to claim 13, wherein: the solvent is one or more of ethanol, water, N-dimethylformamide, glycerol, ethylene glycol and methanol.
15. The method of claim 5, wherein: the reaction temperature is controlled to be 20-150 ℃.
16. The method of claim 15, wherein: the reaction temperature is controlled to be 20-90 ℃.
17. The method of claim 5, wherein: the reaction time is controlled to be 1-36 h.
18. Use of the amide auxiliary according to any one of claims 1 to 4 or the amide auxiliary obtained by the production method according to any one of claims 5 to 17 as a lubricant.
19. Use according to claim 18, characterized in that: the amide auxiliary agent is used as a lubricant to be added into the casting and forming process of wood plastic, plastic and high polymer material products, medicines and other products, or used as mechanical lubrication.
20. Use according to claim 19, characterized in that: the mass percentage of the amide auxiliary agent added in the product formula is 0.1-5%.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09286768A (en) * | 1996-02-20 | 1997-11-04 | Fujisawa Pharmaceut Co Ltd | Hydroxycarboxylic amide derivative and its use |
| US20190241824A1 (en) * | 2016-07-20 | 2019-08-08 | The Lubrizol Corporation | Alkyl phosphate amine salts for use in lubricants |
-
2019
- 2019-10-31 CN CN201911057339.4A patent/CN112745978A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09286768A (en) * | 1996-02-20 | 1997-11-04 | Fujisawa Pharmaceut Co Ltd | Hydroxycarboxylic amide derivative and its use |
| US20190241824A1 (en) * | 2016-07-20 | 2019-08-08 | The Lubrizol Corporation | Alkyl phosphate amine salts for use in lubricants |
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