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WO2015016259A1 - Composition d'ester polyamide composite, composition de lubrifiant et procédé de production de composition de lubrifiant et d'ester polyamide composite - Google Patents

Composition d'ester polyamide composite, composition de lubrifiant et procédé de production de composition de lubrifiant et d'ester polyamide composite Download PDF

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Publication number
WO2015016259A1
WO2015016259A1 PCT/JP2014/070057 JP2014070057W WO2015016259A1 WO 2015016259 A1 WO2015016259 A1 WO 2015016259A1 JP 2014070057 W JP2014070057 W JP 2014070057W WO 2015016259 A1 WO2015016259 A1 WO 2015016259A1
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WIPO (PCT)
Prior art keywords
substituent
group
oil
polyamide composition
lubricant
Prior art date
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Ceased
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PCT/JP2014/070057
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English (en)
Japanese (ja)
Inventor
祐二 寺田
鈴木　博幸
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Fujifilm Corp
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Fujifilm Corp
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Priority to JP2015529592A priority Critical patent/JPWO2015016259A1/ja
Publication of WO2015016259A1 publication Critical patent/WO2015016259A1/fr
Anticipated expiration legal-status Critical
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    • 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
    • C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • C08L77/06—Polyamides derived from polyamines and polycarboxylic acids
    • 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
    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/40—Lubricating compositions characterised by the base-material being a macromolecular compound containing nitrogen
    • C10M107/44—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • 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
    • 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
    • C10M2217/0443—Polyamides used as base material
    • 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
    • C10N2030/26—Waterproofing or water resistance
    • 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
    • C10N2030/66—Hydrolytic stability

Definitions

  • the present invention relates to a composite ester polyamide composition and a lubricant. Specifically, the present invention relates to a composite ester polyamide composition containing a specific ester polyamide and a lubricant containing the composite ester polyamide composition.
  • Lubricants generally contain base oil and various additives.
  • Base oils include mineral oils obtained from crude oils, chemically synthesized ester oils, fluorine oils, polyalphaolefin oils, and the like.
  • ester oils are suitably used for jet aircraft, automobile engine oils, greases and the like because of their low pour point, high viscosity index, high flash point, good lubricating performance, biodegradability, and the like.
  • ester oil monoester obtained from reaction of aliphatic monocarboxylic acid and monohydric alcohol; diester obtained from reaction of aliphatic dibasic acid and monohydric alcohol; polyhydric alcohol and aliphatic carboxylic acid;
  • Various esters are disclosed (Patent Documents 1 to 5), such as esters obtained from the above reaction; and complex esters obtained from reaction with polyols, polybasic acids, and aliphatic monocarboxylic acids.
  • Patent Documents 6 and 7 disclose ester polyamide compositions using polyvalent amines.
  • Patent Document 6 discloses an ester polyamide composition obtained from the reaction of an aliphatic dibasic acid such as dimer acid or trimer acid, diamine and methanol. Here, the obtained ester polyamide composition is used for an optical member such as a lens.
  • Patent Document 7 discloses an ester polyamide composition obtained from the reaction of a polyvalent amine, an aliphatic dibasic acid, and a polyhydric alcohol, and such a composition is used as a lubricant composition. ing.
  • the conventional ester composition may be hydrolyzed in the lubricant, there is a problem of promoting the deterioration of the lubricant.
  • Such a deteriorated lubricant has been a problem because it causes corrosion of metals and the like. That is, the conventional lubricant does not have excellent lubrication performance and hydrolysis resistance, and a lubricant having both of these performances is required.
  • the present inventors provide a lubricant capable of exhibiting excellent lubricating performance and having excellent hydrolysis resistance in order to solve such problems of the conventional technology.
  • the study was advanced for the purpose.
  • the present inventors have found that the lubricating performance can be improved by using a composite ester polyamide composition containing a specific ester polyamide as a lubricant.
  • the specific ester polyamide is a condensation product of a polyvalent amine containing at least two primary or secondary amino groups, a polyvalent carboxylic acid containing at least two carboxyl groups, and a monohydric alcohol having 4 or more carbon atoms. It is ester polyamide obtained by this.
  • the present inventors have found that a composite ester polyamide composition containing such an ester polyamide can exhibit excellent hydrolysis resistance, and have completed the present invention.
  • the present invention has the following configuration.
  • a composite ester polyamide composition comprising a polyamide.
  • the polyvalent amine is a divalent amine containing two primary or secondary amino groups
  • the polyvalent carboxylic acid is a polyvalent carboxylic acid containing three or more carboxyl groups.
  • the polyvalent amine is a polyvalent amine containing three or more primary or secondary amino groups
  • the polyvalent carboxylic acid is a divalent carboxylic acid containing two carboxyl groups.
  • At least one of the ester polyamides is a composite ester polyamide composition according to [1] or [2] represented by the following general formula (1);
  • R represents an aliphatic group having 2 to 60 carbon atoms
  • R 1 represents a hydrogen atom, an alkyl group which may have a substituent, a cycloalkyl group which may have a substituent
  • the aryl group which may have a substituent, the heteroaryl group which may have a substituent, or group represented by General formula (2) is represented.
  • R 2 represents a linear or cyclic aliphatic linking group or aromatic linking group having a valence of (m + 1) or more
  • R 3 represents an alkyl group which may have a substituent or an cycloalkyl which may have a substituent.
  • n represents an integer of 2 to 4
  • m represents an integer of 1 to 3.
  • R 2 represents a chain or cyclic aliphatic linking group or aromatic linking group having a valence of (m + 1) or more
  • R 3 represents an alkyl group which may have a substituent, or a substituent.
  • the cycloalkyl group which may have, the aryl group which may have a substituent, and the heteroaryl group which may have a substituent are represented.
  • m represents an integer of 1 to 3.
  • R 6] The composite ester polyamide composition according to any one of [3] to [5], wherein in general formulas (1) and (2), R 2 is a dimer acid residue or a trimer acid residue.
  • X a1 and X a2 each independently represent a hydrogen atom, a halogen atom or an alkyl group.
  • Na1 represents an integer of 2 to 4
  • na2 represents an integer of 1 to 12.
  • R 2 represents a chain or cyclic aliphatic linking group or aromatic linking group having a valence of (m + 1) or more
  • R 3 represents an alkyl group which may have a substituent, or a substituent.
  • the cycloalkyl group which may have, the aryl group which may have a substituent, and the heteroaryl group which may have a substituent are represented.
  • m represents an integer of 1 to 3.
  • a lubricant composition containing one or more additives selected from a seal compatibilizer, an antifoaming agent, a rust inhibitor, a corrosion inhibitor, a friction modifier, and a thickener.
  • a seal compatibilizer an antifoaming agent
  • a rust inhibitor a corrosion inhibitor
  • a friction modifier a friction modifier
  • a thickener a thickener
  • a lubricant composition comprising at least one or two or more media selected from ether oils, diphenyl ether oils, aromatic ester oils, aliphatic monoester oils, aliphatic diester oils, and polyol ester lubricating oils.
  • a lubricant comprising the composite ester polyamide composition according to any one of [1] to [11], or the lubricant composition according to [12] or [13].
  • Grease lubricant, release agent engine oil for internal combustion engine, oil for metal processing (cutting), oil for bearing, fuel for combustion engine, vehicle engine oil, gear oil, hydraulic oil for automobile, Aircraft lubricant, machine oil, turbine oil, bearing oil, hydraulic fluid, compressor / vacuum pump oil, refrigeration oil, metalworking lubricant, magnetic recording medium lubricant, micromachine lubricant, artificial bone
  • the lubricant according to [14] which is used as a lubricant, shock absorber oil or rolling oil.
  • the manufacturing method of the composite ester polyamide composition including the process to do.
  • the step of obtaining a mixture is performed such that the equivalent ratio of mixing the polyvalent carboxylic acid with respect to the polyvalent amine is 1 to 3, and the equivalent ratio of mixing the monohydric alcohol is 0.5 to 3.
  • the manufacturing method of the composite ester polyamide composition as described in [16] which is a process to carry out.
  • the step of dehydrating condensation includes a step of adding 1 to 25% by mass of a hydrocarbon solvent having a boiling point of 110 to 160 ° C. with respect to the mixture, and allowing dehydration condensation to proceed while azeotropically distilling water. 16] or the method for producing a composite ester polyamide composition according to [17].
  • a composite ester polyamide composition capable of exhibiting high lubricating performance can be obtained. Furthermore, according to the present invention, a composite ester polyamide composition having excellent hydrolysis resistance can be obtained. For this reason, the composite ester polyamide composition of the present invention does not corrode metals even when used for a long period of time, and is preferably used as a lubricant for various applications.
  • a numerical range expressed using “to” means a range including numerical values described before and after “to” as a lower limit value and an upper limit value.
  • the present invention relates to a composite ester polyamide composition containing a predetermined ester polyamide.
  • the composite ester polyamide composition of the present invention comprises a polyvalent amine containing at least two primary or secondary amino groups, a polyvalent carboxylic acid containing at least two carboxyl groups, and a monohydric alcohol having 4 or more carbon atoms.
  • An ester polyamide obtained by condensation is included.
  • the composite ester polyamide composition which can exhibit high lubricating performance can be obtained by including such a specific ester polyamide.
  • the composite ester polyamide composition obtained in the present invention is also characterized by having excellent hydrolysis resistance.
  • the polyvalent amine used for the condensation of the ester polyamide is a compound containing at least two primary or secondary amino groups. Preferably, 2 to 4 amino groups are contained in one molecule, more preferably 2 or 3 amino groups.
  • polyvalent amine In one molecule of the polyvalent amine, 2 to 4 amino groups are preferably contained, and more preferably 2 or 3 amino groups are contained.
  • any one of divalent to tetravalent polyvalent amines may be used, or a plurality of types may be used.
  • a mixture of a divalent amine and a trivalent amine may be used, or a mixture of a divalent amine, a trivalent amine, and a tetravalent amine may be used.
  • a mixture of tetravalent amines may be used.
  • numerator either one of a primary amino group and a secondary amino group may be contained, and both may be contained.
  • the amino group in the molecule is linked by a chain or cyclic divalent or higher aliphatic hydrocarbon.
  • the polyvalent amine preferably has 2 or more carbon atoms, more preferably 6 or more, still more preferably 7 or more, and still more preferably 8 or more. Further, the carbon number of the polyvalent amine is preferably 60 or less, more preferably 30 or less, further preferably 24 or less, and still more preferably 20 or less.
  • polyvalent amine examples include ethylenediamine, hexamethylenediamine, phenylenediamine, diaminonaphthalene, diaminocyclohexane, dimer diamine, piperazine, tris (2-aminoethylamine), and adamantane diamine.
  • polyvalent amine that can be used in the present invention are shown below, but the present invention is not limited thereto.
  • the polyvalent carboxylic acid used for the condensation of the ester polyamide is a compound containing at least two carboxyl groups. It is preferable that 2 to 4 carboxyl groups are contained in one molecule, and more preferably 2 or 3 carboxyl groups are contained in one molecule.
  • the polyvalent carboxylic acid is preferably dimer acid or trimer acid.
  • any one of divalent to tetravalent polyvalent carboxylic acids may be used, or a plurality of types may be used.
  • a mixture of a divalent carboxylic acid and a trivalent carboxylic acid may be used, or a mixture of a divalent carboxylic acid, a trivalent carboxylic acid, and a tetravalent carboxylic acid may be used, A mixture of a trivalent carboxylic acid and a tetravalent carboxylic acid may be used.
  • the valences of the polyvalent amine and the polyvalent carboxylic acid satisfy the following condition (i) or (ii).
  • the polyvalent amine is a divalent amine containing two primary or secondary amino groups
  • the polyvalent carboxylic acid is a polyvalent carboxylic acid containing three or more carboxyl groups.
  • the polyvalent amine is a polyvalent amine containing three or more primary or secondary amino groups
  • the polyvalent carboxylic acid is a divalent carboxylic acid containing two carboxyl groups.
  • the carboxyl group in the molecule is linked with a chain or cyclic divalent or higher valent aliphatic hydrocarbon or aromatic hydrocarbon.
  • One or more carbon atoms not adjacent to each other of the carbon atoms of the aliphatic hydrocarbon or aromatic hydrocarbon linking group may be substituted with oxygen atoms.
  • the number of carbon atoms of the polyvalent carboxylic acid is preferably 4 or more, preferably 10 or more, more preferably 18 or more, further preferably 22 or more, and particularly preferably 26 or more. preferable. Further, the carbon number of the polyvalent carboxylic acid is preferably 70 or less, more preferably 66 or less, and further preferably 59 or less. In the present invention, the carbon number of the polyvalent carboxylic acid represents the number of carbon atoms including the carbon atom constituting the carboxyl group. Thus, the lubrication performance of the composite ester polyamide composition can be further improved by setting the carbon number of the polyvalent carboxylic acid within the above range.
  • polyvalent carboxylic acid examples include terephthalic acid, phthalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, suberic acid, azelaic acid, sebacic acid, dodecanedioic acid, and trimellitic acid.
  • the group connecting the carboxyl groups in the molecule is preferably an aliphatic hydrocarbon having 22 to 66 carbon atoms.
  • a dimer acid or a trimer acid can be illustrated preferably.
  • polyvalent carboxylic acids that can be used in the present invention are shown below, but the present invention is not limited thereto.
  • polyhydric carboxylic acid anhydrides may be used in place of polycarboxylic acids.
  • the polyhydric carboxylic acid anhydride is a product obtained by intramolecular or intermolecular dehydration condensation of two COOHs of the above polycarboxylic acid.
  • the preferred form is the same as above.
  • the anhydrides include succinic anhydride, glutaric anhydride, adipic anhydride, maleic anhydride, phthalic anhydride, nadoic anhydride, methyl nadic anhydride, hexahydrophthalic anhydride and mixed polybasic anhydride Things are included.
  • the monohydric alcohol used for the condensation of the ester polyamide is a compound having one hydroxyl group in one molecule and having 4 or more carbon atoms.
  • a monohydric alcohol is represented by R (OH).
  • R is a monovalent aliphatic, alicyclic or aromatic ring group, and one or more carbon atoms which are not adjacent to each other in R may be substituted with an oxygen atom.
  • R preferably has 4 or more carbon atoms, more preferably 6 or more, and even more preferably 8 or more.
  • Examples of the monohydric alcohol suitable for the present invention include butanol, pentanol, propanol, hexanol, heptanol, octanol, decanol, dodecanol, hexadecanol, octadecanol, eicosadecanol, phytosterol, isostearol, stearol. Cetol, behenol, ethylene glycol monoether, polyethylene glycol monoether and the like.
  • the monohydric alcohol used in the present invention is preferably one represented by the following general formula (3).
  • Ra represents an alkyl group which may have a substituent, a cycloalkyl group which may have a substituent, an alkenyl group which may have a substituent, or a substituent.
  • the number of carbon atoms in the alkyl group part of the alkyl group which may have a substituent represented by R a is preferably 3 to 17, more preferably 4 to 13, and 5 to 9. Is more preferable.
  • the alkyl group represented by R a may be linear or branched.
  • R a may be a cycloalkyl group.
  • the carbon number of the alkenyl group part of the alkenyl group which may have a substituent represented by Ra is preferably 3 to 17, more preferably 4 to 13, and 5 to 9. Is more preferable.
  • the alkyl group represented by R a may be linear, branched or cyclic.
  • the number of carbon atoms in the aryl group part of the aryl group or heteroaryl group which may have a substituent represented by R a is preferably 6-17, and more preferably 6-12.
  • Examples of the aryl group represented by Ra include a phenyl group and a naphthyl group, and among them, a phenyl group is particularly preferable.
  • Examples of the heteroaryl group represented by Ra include imidazolyl, pyridyl, quinolyl, furyl, thienyl, benzoxazolyl, indolyl, benzimidazolyl, benzthiazolyl, carbazolyl, azepinyl Can be illustrated.
  • the hetero atom contained in the heteroaryl group is preferably an oxygen atom, a sulfur atom, or a nitrogen atom, and more preferably an oxygen atom.
  • Ra is an alkyl group which may have a substituent.
  • the alkyl group may be a branched alkyl group.
  • X a1 and X a2 are each independently a hydrogen atom or an alkyl group.
  • na1 is more preferably an integer of 2 or 3, and more preferably 2.
  • Na2 is more preferably an integer of 1 to 8, more preferably an integer of 1 to 6, and particularly preferably an integer of 1 to 3.
  • the carbon number of the monohydric alcohol represented by the general formula (3) is preferably 4 or more, more preferably 6 or more, and further preferably 8 or more.
  • R a may have include a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms (for example, methyl, ethyl, which are both linear or branched, propyl, butyl, pentyl).
  • substituents include alkoxy groups, alkoxycarbonyl groups, halogen atoms, ether groups, alkylcarbonyl groups, cyano groups.
  • the composite ester polyamide composition of the present invention includes an ester polyamide obtained by mixing a polyvalent amine as described above, a polyvalent carboxylic acid, and a monohydric alcohol and condensing the mixture. At least one of the ester polyamides obtained by condensing the mixture is preferably represented by the following general formula (1).
  • R represents an aliphatic group having 2 to 60 carbon atoms
  • R 1 represents a hydrogen atom, an alkyl group which may have a substituent, a cycloalkyl group which may have a substituent
  • the aryl group which may have a substituent, the heteroaryl group which may have a substituent, or group represented by General formula (2) is represented.
  • R 2 represents a linear or cyclic aliphatic linking group or aromatic linking group having a valence of (m + 1) or more
  • R 3 represents an alkyl group which may have a substituent or an cycloalkyl which may have a substituent.
  • n represents an integer of 2 to 4
  • m represents an integer of 1 to 3.
  • R 2 represents a chain or cyclic aliphatic linking group or aromatic linking group having a valence of (m + 1) or more
  • R 3 represents an alkyl group which may have a substituent, or a substituent.
  • the cycloalkyl group which may have, the aryl group which may have a substituent, and the heteroaryl group which may have a substituent are represented.
  • m represents an integer of 1 to 3.
  • R represents an aliphatic group having 2 to 60 carbon atoms.
  • the number of carbon atoms in R is preferably 6 or more, more preferably 7 or more, and still more preferably 8 or more. Further, the carbon number of R is preferably 30 or less, more preferably 24 or less, and even more preferably 20 or less.
  • n represents an integer of 2 to 4, and in general formulas (1) and (2), m represents an integer of 1 to 3.
  • m is particularly preferably an integer of 1 or 2. Further, when m is 3, n is preferably 2, and when m is an integer of 1 or 2, n is preferably an integer of 3 or 4.
  • R 1 is a hydrogen atom, an alkyl group that may have a substituent, a cycloalkyl group that may have a substituent, an aryl group that may have a substituent, or a heteroaryl that may have a substituent.
  • the group represented by group or General formula (2) is represented. That is, when the polyvalent amine used in the present invention is a polyvalent amine containing a primary amino group, R 1 represents a hydrogen atom or a group represented by the general formula (2), and the polyvalent amine used in the present invention.
  • R 1 is an alkyl group that may have a substituent, a cycloalkyl group that may have a substituent, or an aryl that may have a substituent. It represents a heteroaryl group which may have a group or a substituent.
  • R 2 represents a residue of a polyvalent carboxylic acid.
  • the residue of the polyvalent carboxylic acid refers to a group constituting a portion obtained by removing two carboxyl groups from the polyvalent carboxylic acid.
  • R 2 represents a chain or cyclic aliphatic linking group or aromatic linking group having an (m + 1) valence or higher, and is preferably a chain or cyclic aliphatic linking group having an (m + 1) valence or higher.
  • One or more carbon atoms that are not adjacent to each other in the aliphatic linking group or the aromatic linking group may be substituted with an oxygen atom.
  • R 2 preferably has 22 to 66 carbon atoms, more preferably 26 to 60 carbon atoms, and still more preferably 30 to 50 carbon atoms.
  • R 2 is preferably a dimer acid residue or a trimer acid residue.
  • R 3 represents an alkyl group which may have a substituent, a cycloalkyl group which may have a substituent, an alkenyl group which may have a substituent, an aryl group which may have a substituent, a substituent Represents a heteroaryl group which may have Specific examples of the group that R 3 can take include the group represented by R a in formula (3).
  • the substituent of each group that R 3 may have is not particularly limited. As the substituent, the above substituents can be exemplified similarly.
  • R 3 may have 4 or more carbon atoms, more preferably 6 or more, and still more preferably 8 or more.
  • R 3 is preferably a group having an oxyalkylene structure. That is, R 3 is preferably a branched alkyl group or an alkyl group containing an ether bond in the chain. By using R 3 as such a substituent, the lubricating performance of the composite ester polyamide composition can be further enhanced.
  • the equivalent ratio of mixing the polyvalent carboxylic acid with respect to the polyvalent amine is 1 to 3
  • the mixing ratio is more preferably 1: 1.2 to 2.8: 0.7 to 2.8, and more preferably 1: 1.5 to 2.5: 1 to 2.5. preferable.
  • the total equivalent of the polyvalent amine and the monohydric alcohol is preferably the same or larger than the equivalent of the polyvalent carboxylic acid.
  • the viscosity of the composite ester polyamide composition of the present invention at 40 ° C. is preferably 50 to 1650 mPas.
  • the viscosity of the composite ester polyamide composition at 40 ° C. is preferably 50 mPas or more, more preferably 70 mPas or more, and further preferably 100 mPas or more.
  • the viscosity at 40 ° C. of the composite ester polyamide composition is preferably 1650 mPas or less, more preferably 1200 mPas or less, and further preferably 1000 mPas or less.
  • the lubricant of the present invention has an excellent feature that the increase in the friction coefficient is small. Such an excellent effect is considered to be obtained when the ester polyamide obtained in the present invention has a three-dimensional structure in which side chains are arranged radially.
  • the ester polyamide obtained in the present invention is composed of a polyvalent amine capable of radially arranging side chains, a polyvalent carboxylic acid connected to the polyamine and extending radially, and a monohydric alcohol serving as a terminal linking group for the polyvalent carboxylic acid.
  • a compound composed of In the present invention a large free volume can be secured by the steric structure by having a side chain with a polyvalent amine as a central atomic group. Thereby, the raise of a friction coefficient can be suppressed.
  • the lubricant of the present invention is characterized by excellent hydrolysis resistance. Such an effect is considered to be obtained by forming a polyamine with a central atomic group and forming an amide bond between the polyamine and the polycarboxylic acid.
  • the change in the molecular weight of the ester polyamide can be kept small over a long period of time by forming an amide bond with a polyamine having a central atomic group. That is, in the present invention, it is possible to obtain a composite ester polyamide composition that is prevented from being decomposed over time and having a molecular weight that is not degraded, and is less likely to deteriorate over time. Thereby, the outstanding lubricating performance can be exhibited over a long period of time.
  • the lubricant having excellent hydrolysis resistance does not corrode metals, it can be applied to various materials such as metals.
  • a light component in addition to the predetermined ester polyamide, a light component may be further included.
  • the light component refers to a component having a low molecular weight, and examples thereof include an ester component represented by the general formula (4). That is, as a light part, the ester which polyhydric carboxylic acid and monohydric alcohol reacted can be illustrated.
  • R 2 represents a chain or cyclic aliphatic linking group or aromatic linking group having a valence of (m + 1) or more
  • R 3 represents an alkyl group which may have a substituent, or a substituent.
  • the cycloalkyl group which may have, the aryl group which may have a substituent, and the heteroaryl group which may have a substituent are represented.
  • m represents an integer of 1 to 3.
  • Specific groups that R 2 and R 3 can take are the same as the groups exemplified for R 2 and R 3 in the general formula (1).
  • the viscosity of the composite ester polyamide composition can be further reduced by the coexistence of a low-viscosity liquid containing the light components as described above.
  • lubrication performance can be improved, and high lubrication performance can be exhibited even under extreme pressure conditions.
  • the ratio between the predetermined ester polyamide and the light component is not particularly limited.
  • the content of light components is preferably 50% by mass or less, more preferably 45% by mass or less, and 40% by mass or less with respect to the predetermined ester polyamide. More preferably it is.
  • the ratio between the predetermined ester polyamide and the light component can be achieved by controlling the charging ratio of the three raw materials in the production method described later. Moreover, it can also adjust to a preferable range by isolate
  • the composition ratio between the predetermined ester polyamide and the light component containing dimer diol can be calculated by measuring gel permeation chromatography (GPC).
  • GPC gel permeation chromatography
  • unreacted COOH in the polyvalent carboxylic acid may remain in the side chain of the ester polyamide contained in the composite ester polyamide composition, and unreacted OH in the monohydric alcohol may remain.
  • OH and COOH remain, the hydroxyl value and the acid value increase, and depending on the use (for example, the use of a lubricant), it may not be preferable.
  • OH and COOH in the ester polyamide can be eliminated by separate acylation and / or esterification treatment, and the hydroxyl value and acid value can be reduced.
  • a treatment of acylating at least a part thereof can be performed.
  • monobasic acid R 1 COOH
  • monobasic acid anhydride ((R 1 CO) 2 O) is added to ester polyamide in which OH remains, and heated to convert the remaining OH to OCOR. This is a process of converting to 1 .
  • mixing with other oil-based media is preferable in terms of easy mixing.
  • the proportion of unreacted OH in the ester polyamide can be determined by measuring 13 C-NMR.
  • the residual ratio of OH in the ester polyamide is preferably 0 to 40%, more preferably 0 to 35%, and further preferably 0 to 30%.
  • the acid value of the ester polyamide is preferably 0 to 50, more preferably 0 to 40, and 0 to 30. More preferably. However, it is not limited to this range.
  • the composite ester polyamide composition of the present invention can be obtained by charging at least three raw materials of the above-described polyvalent amine, polyvalent carboxylic acid and monohydric alcohol, followed by dehydration condensation. That is, the method for producing a composite ester polyamide composition of the present invention comprises a polyvalent amine containing at least two primary or secondary amino groups, a polyvalent carboxylic acid containing at least two carboxyl groups, and a monohydric alcohol. A step of mixing to obtain a mixture and a step of dehydrating and condensing the mixture.
  • two raw materials for example, a polyvalent amine and a polyvalent carboxylic acid, or a polyvalent carboxylic acid and a monohydric alcohol
  • two raw materials for example, a polyvalent amine and a polyvalent carboxylic acid, or a polyvalent carboxylic acid and a monohydric alcohol
  • the charging ratio (mixing ratio) of the polyvalent amine, polyvalent carboxylic acid and monohydric alcohol is determined by the equivalent amount.
  • the equivalent here means the chemical equivalent of COOH, OH or NH in the reaction. If the number of NH in one molecule of the polyvalent amine is n and the number of moles is M1, the equivalent of the polyvalent amine is defined as n ⁇ M1. Similarly, when the number of COOH in one molecule of the polycarboxylic acid is m and the number of moles is M2, the equivalent of the polyvalent carboxylic acid is defined as m ⁇ M2. Since monohydric alcohol has one OH in one molecule, M3 is defined as M3. The above ratio is a ratio of these n ⁇ M1, m ⁇ M2, and M3.
  • the mixing ratio is more preferably 1: 1.2 to 2.8: 0.7 to 2.8, and more preferably 1: 1.5 to 2.5: 1 to 2.5. preferable.
  • the side chain of the ester polyamide is preferably end-capped, the total equivalent of the polyvalent amine and the monohydric alcohol is preferably the same or larger than the equivalent of the polyvalent carboxylic acid.
  • the composite ester polyamide composition of the present invention can be obtained by subjecting the mixture charged as described above to a dehydration condensation reaction in the presence or absence of a catalyst.
  • This solvent is preferably a hydrocarbon solvent having a boiling point of 100 to 200 ° C., more preferably a hydrocarbon solvent having a boiling point of 100 to 170 ° C., and most preferably a hydrocarbon solvent having a boiling point of 110 to 160 ° C.
  • these solvents include toluene, xylene, mesitylene and the like. If the amount to be added is too large, the liquid temperature will be in the vicinity of the solvent, and dehydration condensation will not proceed easily.
  • the addition amount is preferably 1 to 25% by mass, more preferably 2 to 20% by mass, particularly preferably 3 to 15% by mass, based on the total amount of polyvalent amine, polyvalent carboxylic acid and monohydric alcohol. ⁇ 12% by weight is also preferred.
  • the reaction is carried out at a liquid temperature of 120 to 250 ° C., preferably 130 to 230 ° C., more preferably 130 to 200 ° C., particularly preferably 140 to 200 ° C.
  • a solvent containing water is azeotroped, cooled at a cooling site such as Dean Stark, and becomes a liquid to separate water and the solvent. This water may be removed.
  • the reaction time since the theoretically generated water amount is calculated from the number of moles charged, it is preferable to carry out the reaction until the water amount is obtained, but it is difficult to complete the reaction completely. Even when the reaction is terminated when the theoretical water generation amount is 60 to 90%, the lubricity of the composite ester polyamide composition is good.
  • the reaction time is 1 to 24 hours, preferably 3 to 18 hours, more preferably 5 to 18 hours, and most preferably 6 to 15 hours.
  • the remaining OH may be acylated.
  • a suitable amount of monobasic acid (R 1 COOH) or monobasic acid anhydride ((R 1 CO) 2 O), preferably monobasic acid anhydride ((R 1 CO) 2 O) is added
  • at least a part, preferably almost all of the remaining OH can be converted to OCOR 1 by heating at 100 ° C. or higher, more preferably 120 ° C. or higher, particularly 150 ° C. or higher. It is preferable to remove the by-product volatile matter by distillation described later.
  • R 1 is an alkyl group or aryl group having 1 to 10 carbon atoms, preferably an alkyl group or aryl group having 1 to 6 carbon atoms, and is a methyl group, an ethyl group, a butyl group, or a phenyl group.
  • a methyl group or a phenyl group is preferable, and a methyl group is particularly preferable.
  • an esterification treatment may be performed in order to eliminate the remaining COOH.
  • the esterification treatment can be performed, for example, by adding diazomethane, and at least a part, preferably almost all of COOH can be converted into a methyl ester.
  • a composite ester polyamide composition containing a predetermined ester polyamide and a soft component containing at least the ester produced as described above is obtained.
  • the resulting composite ester polyamide composition can be used as it is for various uses, for example, as a lubricant. Various processes may be performed depending on the application.
  • the composite ester polyamide After completion of the reaction and the treatment after the reaction, it is preferable to perform filtration to remove dust and the like.
  • the composite ester polyamide becomes solid, it can be melted out or taken out as a powder by reprecipitation.
  • the present invention may relate to a lubricant composition containing at least a composite ester polyamide composition.
  • the composite ester polyamide composition of the present invention and various additives and / or media can be added to the lubricant composition.
  • additives include antiwear agents, viscosity index improvers, antioxidants, detergents, dispersants, flow agents, curing agents, corrosion inhibitors, seal conformers, antifoaming agents, rust inhibitors, and corrosion inhibitors. , One or more selected from friction modifiers and thickeners. By adding such an additive, a preferable function as a lubricant such as wear suppression can be imparted.
  • the lubricant that can be used in the present invention reference can be made to the descriptions in paragraphs [0098] to [0165] of JP2011-89106A.
  • the “medium” means all the media generally called “fluid liquids”. However, it is not necessary to be liquid at room temperature or the temperature used, and any form of material such as solid and gel can be used in addition to liquid. There is no restriction
  • the description in paragraphs [0067] to [0096] of JP2011-89106A can be referred to.
  • the lubricant composition of the present invention preferably has a viscosity at 40 ° C. of 1650 mPa ⁇ s or less, more preferably 1200 mPa ⁇ s or less, and even more preferably 1000 mPa ⁇ s or less. Viscosity needs to be adjusted to an appropriate viscosity depending on the usage environment.
  • the constituent elements are preferably composed only of carbon, hydrogen, oxygen and nitrogen, and more preferably composed only of carbon, hydrogen and oxygen.
  • various materials that are composed only of carbon, hydrogen, and oxygen as oil used as the oily medium By combining these, it is possible to prepare a composition whose constituent elements consist only of carbon, hydrogen, oxygen and nitrogen.
  • the current lubricating oil usually contains phosphorus, sulfur and heavy metals.
  • Lubricating oil used in a two-stroke engine that also burns lubricating oil together with fuel does not include phosphorus and heavy metals in consideration of environmental impact, but sulfur is included in about half of the lubricating oil used in a four-stroke engine. Yes.
  • the lubricant composition of the present invention can be prepared by adding a complex ester polyamide composition in an oily medium or an aqueous medium, and dissolving and / or dispersing it. Dissolution and / or dispersion may be performed under heating.
  • the addition amount of the composite ester polyamide composition is preferably 10% by mass or more with respect to the mass of the oily medium. However, it is not limited to this range, and may be outside the above range as long as the compound is an amount sufficient to exhibit a friction reducing action.
  • the lubricant composition of the present invention is useful as a lubricant. That is, the present invention also relates to a lubricant including the above-described composite ester polyamide composition or a lubricant including the above-described lubricant composition.
  • the lubricant of the present invention is supplied, for example, between two sliding surfaces, and can be used to reduce friction.
  • the composition of the present invention can form a film on the sliding surface.
  • the material of the sliding surface in steel, specifically, carbon steel for machine structure, alloy steel for structural machinery such as nickel chrome steel, nickel chrome molybdenum steel, chrome steel, chrome molybdenum steel, aluminum chrome molybdenum steel, Examples include stainless steel and multi-aged steel.
  • various metals other than steel, or inorganic or organic materials other than metals are widely used.
  • inorganic or organic materials other than metals include various plastics, ceramics, carbon, etc., and mixtures thereof.
  • examples of the metal material other than steel include cast iron, copper / copper-lead / aluminum alloy, castings thereof, and white metal.
  • the lubricant of the present invention can be used for various applications.
  • Lubricant, machine oil, turbine oil, bearing oil, hydraulic fluid, compressor / vacuum pump oil, refrigerator oil, metalworking lubricant, magnetic recording medium lubricant, micromachine lubricant, artificial bone lubricant It can be used as an agent, shock absorber oil or rolling oil. It is also used for air conditioners and refrigerators with reciprocating and rotary hermetic compressors, automotive air conditioners and dehumidifiers, freezers, refrigerated warehouses, vending machines, showcases, chemical plant and other cooling devices. .
  • a lubricant for metal processing that does not contain chlorine compounds, for example, when hot rolling metal materials such as steel materials and Al alloys, or when performing processing such as cutting, cold rolling oil of aluminum, cutting oil
  • metal processing oil such as grinding oil, drawing oil, press processing oil and plastic processing oil of metal, especially as a deterrent for wear, breakage and surface roughness during high speed and high load processing, as well as broaching and gun drilling It is also useful as a metal working oil composition that can be applied to low speed and heavy cutting. Further, it can be used for various grease lubricants, magnetic recording medium lubricants, micromachine lubricants, artificial bone lubricants, and the like.
  • the elemental composition of the composition can be a carbohydrate, for example, polyoxyethylene ether widely used in cake mix, salad dressing, shortening oil, chocolate, etc. as an emulsifying, dispersing or solubilizing agent is used.
  • a high-performance lubricating oil that is completely harmless to the human body can be used for lubrication of food production line manufacturing equipment and medical equipment members.
  • the composition of the present invention can be used as cutting oil or rolling oil by emulsifying and dispersing it in an aqueous system or by dispersing it in a polar solvent or a resin medium.
  • the lubricant composition of the present invention can be used for various applications as a release agent.
  • a release agent for example, polycarbonate resin, flame retardant polycarbonate resin, crystalline polyester resin which is the main component of image forming toner used in electrophotographic apparatus and electrostatic recording apparatus, various molding thermoplastic resin compositions and semiconductor encapsulating Used as a mold release agent for epoxy resin compositions.
  • One embodiment of the release agent is an embodiment containing 0.01 to 10 parts by mass (preferably 0.1 to 5 parts by mass) of the composite ester polyamide composition with respect to 100 parts by mass of a resin such as a polycarbonate resin.
  • it can also be used as an antifouling agent that promotes the removal of dirt attached to the fiber product and prevents the fiber product from being soiled by being kneaded or applied in advance to a textile product such as clothing.
  • polyvalent amines used in the examples of the present invention are as follows.
  • polyvalent carboxylic acids used in the examples of the present invention are as follows.
  • the monohydric alcohol used in the examples of the present invention is as follows.
  • Example 1 Evaluation as Lubricating Oil for Internal Combustion Engine
  • a lubricant L1 containing 2.0% by mass of calcium sulfonate as a metallic detergent was prepared, and the coefficient of friction was measured.
  • Lubricants L2 to L24 were prepared in the same manner as in Example 1 except that the compositions PEA2 to 24 were used instead of the composition PEA-1 of the present invention, and the friction coefficients were measured. Evaluation was made according to the following evaluation criteria as an index for evaluating the coefficient of friction. The evaluation results are shown in Table 1 below.
  • the friction coefficient was determined using a vibration type friction and wear tester (manufactured by Optimol Instruments Prutechnik GmbH, trade name: SRV 4), with a vibration frequency of 100 Hz, an amplitude of 2.0 mm, a load of 30 N, a temperature of 65 ° C., and a test time of 30 minutes. Measured in In addition, the evaluation is C grade or higher.
  • Rank A Friction coefficient ⁇ 0.05 B rank: 0.05 ⁇ coefficient of friction ⁇ 0.06 C rank: 0.06 ⁇ friction coefficient ⁇ 0.07
  • D rank friction coefficient ⁇ 0.07
  • Test Example 2 Evaluation of Hydrolysis Stability
  • the hydrolysis stability of the composite ester polyamide compositions PEA-1 to PEA-1 to 24 of the present invention and the comparative example compounds were ranked according to the following evaluation criteria according to ASTM D2619.
  • the test conditions and evaluation items are as follows. In addition, the evaluation is C grade or higher.
  • Example 1 A lubricant was obtained in the same manner as in Example 1 except that the reaction product (PEA-25) described in Example of JP-A-9-12716 was used instead of the composite ester polyamide composition (PEA-1) of the present invention. L25 was prepared and evaluated in the same manner. The results are shown in Table 1.
  • the lubricant of the present invention can be suitably used as an automotive lubricating oil such as an internal combustion engine such as an automobile engine, a gear oil, an automatic transmission fluid, and a shock absorber oil. Moreover, it turns out that all the composite ester polyamide compositions of this invention are stable to hydrolysis and have the characteristic which does not change easily.
  • a composite ester polyamide composition capable of exhibiting high lubricating performance can be obtained. Furthermore, according to the present invention, a composite ester polyamide composition having excellent hydrolysis resistance can be obtained. For this reason, the composite ester polyamide composition of the present invention does not corrode metals, is preferably used as a lubricant in various applications, and has high industrial applicability.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)
  • Polyamides (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

　L'invention concerne un lubrifiant apte à présenter une excellente performance de lubrification et un lubrifiant ayant une excellente résistance à l'hydrolyse. L'invention concerne une composition d'ester polyamide composite contenant un ester polyamide obtenu par condensation d'une polyamine contenant au moins deux groupes amino primaires ou secondaires, d'un acide polycarboxylique comprenant au moins deux groupes carboxyle et d'un alcool monohydrique ayant au moins quatre carbones. L'invention concerne également une composition de lubrifiant contenant une composition de polyester composite et un procédé de production d'une composition de lubrifiant et d'ester polyamide composite.
PCT/JP2014/070057 2013-07-31 2014-07-30 Composition d'ester polyamide composite, composition de lubrifiant et procédé de production de composition de lubrifiant et d'ester polyamide composite Ceased WO2015016259A1 (fr)

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CN108456581A (zh) * 2018-05-08 2018-08-28 四会市格鲁森润滑技术有限公司 一种自消泡型聚醚共聚物润滑剂及其制造方法

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CN105925345A (zh) * 2016-05-10 2016-09-07 南京高崎电机有限公司 一种防腐蚀电机润滑油
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