WO2022254910A1 - 塗料組成物、塗膜及び塗装物品 - Google Patents
塗料組成物、塗膜及び塗装物品 Download PDFInfo
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- WO2022254910A1 WO2022254910A1 PCT/JP2022/014609 JP2022014609W WO2022254910A1 WO 2022254910 A1 WO2022254910 A1 WO 2022254910A1 JP 2022014609 W JP2022014609 W JP 2022014609W WO 2022254910 A1 WO2022254910 A1 WO 2022254910A1
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- Prior art keywords
- coating composition
- coating
- resin
- coating film
- present disclosure
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- C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
- C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C09D179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- C09D127/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers
- C09D127/02—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
- C09D127/12—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
- C09D127/18—Homopolymers or copolymers of tetrafluoroethene
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/12—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
- C08L27/18—Homopolymers or copolymers or tetrafluoroethene
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
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- C09D181/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur, with or without nitrogen, oxygen, or carbon only; Coating compositions based on polysulfones; Coating compositions based on derivatives of such polymers
- C09D181/06—Polysulfones; Polyethersulfones
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- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/20—Diluents or solvents
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/61—Additives non-macromolecular inorganic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/65—Additives macromolecular
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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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
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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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/14—Polyamide-imides
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/16—Halogen-containing compounds
- C08K2003/162—Calcium, strontium or barium halides, e.g. calcium, strontium or barium chloride
Definitions
- the present disclosure relates to coating compositions, coatings and coated articles.
- Patent Document 1 discloses a composition containing a polyamideimide resin, polytetrafluoroethylene and an abrasion resistance imparting agent having a Mohs hardness of 2.0 to 5.0.
- US Pat. No. 5,300,003 discloses a composition containing polyamideimide resin, polytetrafluoroethylene and 3-methoxy-N,N-dimethylpropanamide.
- Patent Document 3 discloses the use of 3-methoxy-N,N-dimethylpropanamide as a solvent for dissolving polyamideimide.
- US Pat. No. 5,301,000 discloses a composition containing polyamideimide resin, polytetrafluoroethylene and 3-methoxy-N,N-dimethylpropanamide.
- JP 2008-261345 A Japanese Patent Publication No. 2018-524440 Japanese Patent Application Laid-Open No. 2020-15880 Japanese Patent Application Laid-Open No. 2020-203243
- An object of the present disclosure is to provide a coating composition that is superior in surface smoothness to conventional ones, and thereby can form a coating film that is excellent in sliding performance and sliding durability.
- This disclosure contains polytetrafluoroethylene, a binder resin, and a filler with a new Mohs hardness in the range of 1.0 to 6.0, and the content of N-methyl-2-pyrrolidone is less than 1% by weight of the composition.
- a coating composition characterized by
- the binder resin is preferably at least one selected from the group consisting of polyamideimide, polyethersulfone, polyetheretherketone, polyetherimide and polyimide.
- the coating composition preferably contains at least one solvent selected from the group consisting of N-ethyl-2-pyrrolidone, 3-methoxy-N,N-dimethylpropanamide and N-butylpyrrolidone.
- the filler is preferably at least one selected from the group consisting of graphite, calcium fluoride and iron oxide.
- the above coating composition is preferably for a sliding member of a compressor.
- the present disclosure is also a coating film formed from the coating composition described above.
- the present disclosure is also a coated article having the coating film.
- the coating composition of the present disclosure can form a coating film with excellent surface smoothness, it is possible to obtain a coating film with excellent sliding performance and sliding durability.
- polyamideimide resins containing N-methyl-2-pyrrolidone as a solvent have been used when used as binder resins in coating compositions. Since N-methyl-2-pyrrolidone is a resin with excellent dissolving ability, it was possible to obtain a suitable coating composition.
- the inventors of the present invention have investigated the improvement of surface smoothness and found that it is preferable not to use commonly used N-methyl-2-pyrrolidone as a solvent to be used. That is, since N-methyl-2-pyrrolidone has a high surface tension, it is not possible to sufficiently wet the polytetrafluoroethylene resin and the filler, and it is clear that this is one of the factors that impair the surface smoothness. became. That is, since the solid component cannot be sufficiently wetted, the gas is included in the coating film, which causes deterioration of the smoothness.
- the present disclosure is a coating composition in which the content of N-methyl-2-pyrrolidone is less than 1% by weight of the composition. This makes it possible to achieve the objectives set forth above.
- Each component contained in the coating composition of the present disclosure will be described below.
- Polytetrafluoroethylene Polytetrafluoroethylene
- PTFE Polytetrafluoroethylene
- the PTFE may be homo-PTFE containing only TFE units, or modified PTFE containing TFE units and modified monomer units based on modified monomers copolymerizable with TFE.
- the PTFE is preferably a low-molecular-weight PTFE that has melt processability and does not have fibrillation properties. More specifically, it is preferable to use one having a number average molecular weight of 200,000 to 400,000.
- the modified monomer is not particularly limited as long as it can be copolymerized with TFE.
- examples include perfluoroolefins such as hexafluoropropylene [HFP]; chlorofluoroolefins such as chlorotrifluoroethylene [CTFE]; Hydrogen-containing fluoroolefins such as trifluoroethylene and vinylidene fluoride [VDF]; perfluorovinyl ether; perfluoroalkylethylene; ethylene; fluorine-containing vinyl ether having a nitrile group.
- one type of modifying monomer may be used, or a plurality of types thereof may be used.
- Rf 1 represents a perfluoro organic group.
- perfluoro organic group means an organic group in which all hydrogen atoms bonded to carbon atoms are substituted with fluorine atoms.
- the perfluoro organic group may have an ether oxygen.
- perfluorovinyl ether examples include perfluoro(alkyl vinyl ether) [PAVE] in which Rf 1 represents a perfluoroalkyl group having 1 to 10 carbon atoms in the general formula (1).
- the perfluoroalkyl group preferably has 1 to 5 carbon atoms.
- perfluoroalkyl group in PAVE examples include perfluoromethyl group, perfluoroethyl group, perfluoropropyl group, perfluorobutyl group, perfluoropentyl group, and perfluorohexyl group.
- the modified PTFE preferably contains modified monomer units in the range of 0.001 to 2 mol %, more preferably in the range of 0.001 to 1 mol %.
- the PTFE preferably has a melt viscosity (MV) of 1.0 ⁇ 10 Pa ⁇ s or more, more preferably 1.0 ⁇ 10 2 Pa ⁇ s or more, and more preferably 1.0 ⁇ 10 3 Pa ⁇ s. It is more preferable that it is above.
- the melt viscosity was determined according to ASTM D 1238 using a flow tester (manufactured by Shimadzu Corporation) and a 2 ⁇ -8L die. Measurement can be performed while maintaining the above temperature with a load of 7 MPa.
- the PTFE preferably has a standard specific gravity (SSG) of 2.130 to 2.230, more preferably 2.140 or more, and more preferably 2.190 or less.
- standard specific gravity (SSG) can be measured based on the water substitution method in accordance with ASTM D 4895-89.
- the PTFE preferably has a melting point of 324 to 360°C.
- the melting point of a fluororesin is a value determined as the temperature corresponding to the maximum value in the heat of fusion curve when the temperature is raised at a rate of 10° C./min using a differential scanning calorimetry (DSC) device. .
- the PTFE is not dissolved in the solvent and is present in the coating composition in the form of powder, it is preferable to use powder having a small particle size as the raw material. Specifically, it is preferable to use one having a primary particle size of 5 ⁇ m or less.
- the method for measuring the primary particle size is the same as the method for measuring the primary particle size of the filler described in detail below.
- the PTFE is preferably 20 to 60% by mass based on the total solid content of the coating composition.
- the above lower limit is more preferably 25% by mass, and even more preferably 30% by mass.
- the upper limit is more preferably 55% by mass, and even more preferably 50% by mass.
- the coating composition of the present disclosure contains a binder resin.
- the binder resin is not particularly limited, it is preferably a so-called super engineering plastic. Specifically, it is selected from the group consisting of polyamideimide, polyethersulfone, polyetheretherketone, polyetherimide and polyimide. is preferably at least one. These will be described below.
- a polyamide-imide resin is typically a resin obtained by reacting an acid component and a diisocyanate component, and has a structural site derived from the acid component and a structural site derived from the diisocyanate component.
- the acid component is not particularly limited and includes at least an aromatic tribasic acid anhydride and/or an aromatic tribasic acid halide.
- the acid component preferably comprises at least aromatic tribasic anhydride, more preferably trimellitic anhydride. Therefore, in one embodiment, the polyamide-imide resin preferably has a structure represented by general formula (I) below.
- R is an organic group (structural site) derived from a diisocyanate component.
- n is an integer of 1 or more.
- trimellitic anhydride is preferably 50 mol % or more based on the total amount of acid components constituting the polyamide-imide resin (100 mol %). In one embodiment, the trimellitic anhydride content may be 100 mol %.
- the content of trimellitic anhydride may be 50 mol% to 95 mol%, and other acids It may contain 5 mol % to 50 mol % of the component.
- dicarboxylic acids can be used as other acid components.
- succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, phthalic acid, isophthalic acid, terephthalic acid can be used.
- these compounds may be used individually or may be used in combination of 2 or more types.
- the diisocyanate component preferably contains at least an aromatic diisocyanate. Therefore, in one embodiment, in general formula (I) above, R is preferably an organic group derived from an aromatic diisocyanate.
- the content of the aromatic diisocyanate is preferably 30 mol% or more, more preferably 40 mol% or more, based on the total amount of diisocyanate components constituting the polyamide-imide resin (100 mol%). In one embodiment, the aromatic diisocyanate content may be 100 mol %.
- the aromatic diisocyanate is selected from the group consisting of 4,4'-diphenylmethane diisocyanate, 3,3'-dimethyl-4,4'-diisocyanatobiphenyl, 2,4-toluene diisocyanate, and 2,6-toluene diisocyanate. including one or more Among the above aromatic diisocyanates, 4,4'-diphenylmethane diisocyanate is preferred. Therefore, based on the total amount of diisocyanate components constituting the polyamide-imide resin, the content of the aromatic diisocyanate containing 4,4'-diphenylmethane diisocyanate is preferably 30 mol% or more, and is 40 mol% or more. is more preferable, and may be 100 mol %.
- the content of 4,4'-diphenylmethane diisocyanate may be 100 mol% based on the total amount of diisocyanate components constituting the polyamideimide resin. In another embodiment, the content of 4,4'-diphenylmethane diisocyanate may be 30 mol% to 95 mol% based on the total amount of diisocyanate components constituting the polyamideimide resin, and other aromatic diisocyanates may be from 5 mol % to 70 mol %.
- the polyamideimide resin preferably has a number average molecular weight of 5,000 to 50,000. That is, in order to obtain solubility in a solvent that does not substantially contain N-methyl-2-pyrrolidone, it is preferable to use such a relatively low molecular weight compound.
- the lower limit of the number average molecular weight is preferably 8,000, more preferably 10,000 or more.
- the upper limit of the number average molecular weight is preferably 40,000, more preferably 30,000.
- the number average molecular weight of a polyamideimide resin is a value measured by gel permeation chromatography (GPC).
- the polyamideimide resin is preferably 20 to 80% by mass with respect to the total solid content of the coating composition. More preferably, the above lower limit is 25% by mass. The upper limit is more preferably 77% by mass, and even more preferably 75% by mass.
- Polyethersulfone resin (polyether sulfone resin)
- PES Polyethersulfone resin
- PES is not particularly limited, and examples thereof include a resin made of a polymer obtained by polycondensation of dichlorodiphenylsulfone and bisphenol.
- Polyether ether ketone resin has the following general formula
- Polyetherimide resin Polyether ether ketone resin has the following general formula
- a polyimide resin is a resin composed of a polymer having an imide bond in its molecular structure.
- the polyimide resin is not particularly limited, and is composed of, for example, a high molecular weight polymer obtained by reaction of an aromatic tetravalent carboxylic acid anhydride such as pyromellitic anhydride and a polyamine compound such as 4,4'-diaminodiphenyl ether. Resin etc. are mentioned. From the viewpoint of excellent heat resistance, the polyimide resin is preferably composed of a polymer having an aromatic ring in the main chain.
- polyamide-imide resins are particularly preferable from the viewpoint of hardness and substrate adhesion.
- the coating composition of the present disclosure may use two or more of the binder resins described above in combination.
- the binder resin is preferably 20.0 to 80.0% by mass with respect to the total solid content of the coating composition.
- the above lower limit is more preferably 25.0% by mass, and even more preferably 30.0% by mass.
- the above upper limit is more preferably 77.0% by mass, even more preferably 75.0% by mass.
- the present disclosure contains fillers.
- the filler one having a hardness of 1.0 to 6.0 on the new Mohs hardness scale is used.
- the Mohs hardness is the relative hardness of a substance evaluated in the range of 1 to 10, but the new Mohs hardness classifies the hardness evaluation into 15 stages, which is more detailed than the 10 stages of the Mohs hardness. is.
- the filler having a hardness of 1.0 to 6.0 in new Mohs hardness is not particularly limited, and examples include graphite (new Mohs hardness 2.0), calcium fluoride (new Mohs hardness 4.0), oxidation Iron (6.0 new Mohs hardness), boron nitride (2.0 new Mohs hardness), mica (3.0 new Mohs hardness), aluminum hydroxide (3.0 new Mohs hardness), calcium carbonate (3.0 new Mohs hardness) .0), zinc oxide (new Mohs hardness 4.0 to 5.0), tribasic calcium phosphate (new Mohs hardness 5.0), and the like.
- at least one selected from the group consisting of graphite, calcium fluoride, and iron oxide is preferable from the viewpoint of suppressing wear of the mating member during sliding. Two or more of these may be used in combination.
- the filler preferably has a primary particle size D50 of 0.1 to 30.0 ⁇ m.
- D50 primary particle size of the filler
- the average particle size of the primary particles is measured as follows. First, the particles within the field of view are photographed with a transmission electron microscope or scanning electron microscope. Then, the longest length (maximum length) of the inner diameter of each particle is determined for 300 primary particles that form the aggregate on the two-dimensional image. Let the average value of the maximum length of each particle be the average particle diameter of the primary particles.
- the coating composition of the present disclosure preferably contains a filler in a proportion of 0.1 to 50.0% by mass with respect to 100 parts by mass of the solid content of the binder resin in the coating composition. If the content is less than 0.1% by mass, there is a problem in that the wear resistance is lowered. If the content exceeds 50.0% by mass, there is a problem in that the slidability of the coating film surface is reduced.
- the above lower limit is more preferably 0.5% by mass, and even more preferably 1.0% by mass.
- the upper limit is more preferably 45.0% by mass, and even more preferably 40.0% by mass.
- the coating composition of the present disclosure has an N-methyl-2-pyrrolidone content of less than 1% by weight of the composition. That is, the above-mentioned effects are obtained due to the small content of N-methyl-2-pyrrolidone. Therefore, it may contain no N-methyl-2-pyrrolidone.
- the coating composition of the present disclosure preferably contains an organic solvent that dissolves the binder resin instead of N-methyl-2-pyrrolidone.
- a solvent that dissolves the resin may be selected according to the type of the binder resin. Specific examples of such solvents include N-ethyl-2-pyrrolidone (NEP), 3-methoxy-N,N-dimethylpropanamide, N-butyl-2-pyrrolidone (NBP), and the like. can. A mixed solvent of two or more of these may be used.
- the solvent containing the largest amount has a surface tension of 37.5 or less.
- the high surface tension of N-methyl-2-pyrrolidone has been a factor in impairing the surface smoothness. Therefore, it is presumed that using a solvent with a low surface tension will solve this problem.
- the surface tension is more preferably 37.0 or less, even more preferably 36.5 or less.
- the surface tension here is a value measured by the method described in Examples.
- the solvent having a surface tension of 37.0 or less is preferably 25.0% by weight or more, more preferably 30.0% by weight or more, of the total volatile components contained in the coating composition. preferable.
- the coating composition of the present disclosure uses solvents other than the above-described N-ethyl-2-pyrrolidone (NEP), 3-methoxy-N,N-dimethylpropanamide, and N-butyl-2-pyrrolidone (NBP) in combination.
- NEP N-ethyl-2-pyrrolidone
- NBP N-butyl-2-pyrrolidone
- Solvents that can be used in combination are not particularly limited, and general-purpose solvents such as toluene, xylene, methyl isopropyl ketone, methyl ethyl ketone, glycol solvents, and alcohol solvents can be mentioned.
- These general-purpose solvents are preferably blended at a ratio of 10.0 to 75.0% by weight with respect to the total amount of the solvent.
- the content of the solvent is not particularly limited, but generally can be 10.0 to 70.0% by mass with respect to the total amount of the coating composition.
- the coating composition of the present disclosure preferably has a viscosity of 100-40,000 cps. By setting it within the above range, workability in the coating process can be improved. Furthermore, it is also preferable in terms of obtaining a predetermined film thickness.
- the above viscosity is a value measured at 25° C. using a Brookfield viscometer according to JIS Z8803.
- the lower limit of the paint used for spray coating or the like is more preferably 110 cps, and still more preferably 120 cps.
- the upper limit is preferably 3,000 cps, more preferably 2,500 cps.
- the lower limit of the paint used for dispensers and roll coating is more preferably 4,000 cps, and even more preferably 5,000 cps.
- the upper limit is more preferably 38,000 cps, even more preferably 35,000 cps.
- the viscosity can be set within the above-described range by appropriately adjusting the composition of the coating composition, the amount of the solvent, and the molecular weight of the component of the resin used that dissolves in the solvent.
- the coating composition of the present disclosure may contain other components in addition to the components described above within a range that does not impair the purpose of the present disclosure.
- the coating composition of the present disclosure may contain an epoxy resin.
- an epoxy resin By blending an epoxy resin, there is a possibility that the effect of being able to obtain a polyamide-imide and a cross-linking reaction product can be obtained.
- the epoxy resin is not particularly limited, and any known epoxy resin can be used.
- the blending amount is not particularly limited, and can be, for example, 10% by mass or less based on the solid mass of the polyamideimide.
- the coating composition of the present disclosure can be produced by mixing each component described above.
- Various known mills such as a bead mill, a ball mill, and a three-roll mill are used, and these are appropriately combined as necessary. Disintegration can be performed.
- a coating film formed by the coating composition of the present disclosure is also an object of the present disclosure. Formation of a coating film can be performed by a general method.
- the coating film of the present disclosure preferably has a surface roughness Ra of 1.0 or less. Such coatings can be formed by using the coating compositions of the present disclosure.
- the surface roughness Ra is more preferably 0.8 or less, even more preferably 0.7 or less.
- the coating film of the present disclosure preferably has a coefficient of friction of 0.09 or less as measured by the method described in the examples of this specification. By having such abrasion resistance, a coating film having excellent strength and durability can be obtained, and the coating film can be applied to applications where slidability is required.
- a friction coefficient means the value measured by the method described in the Example. The coefficient of friction is more preferably 0.08 or less, even more preferably 0.07 or less.
- the coating film of the present disclosure preferably has a sliding durability of 750 seconds or more as measured by the method described in the examples of this specification.
- the coating film of the present disclosure can be a coating film that can maintain slidability over a long period of time, and can be a coating film that can be applied to applications that require slidability.
- sliding durability means the value measured by the method described in the Examples. The sliding durability is more preferably 900 seconds or longer, and even more preferably 1000 seconds or longer.
- the coating film of this disclosure is limited by the manufacturing method.
- the coating composition of the present disclosure has excellent abrasion resistance and can be used as a coating material for sliding materials that can be used in high-temperature, high-heat environments. More specific products include air conditioner compressor pistons, swash plates, scroll compressor members, and the like. In particular, it is preferably used for car air conditioner compressor pistons. Substrates, coating methods, and the like in such applications can be carried out based on known methods.
- the present disclosure also provides a coating film obtained using the coating composition described above, and a coated article having the coating film.
- the surface roughness was measured using a contact-type surface roughness meter, Sartonic Duo manufactured by Shinto Kagaku Co., Ltd.
- sliding durability Sliding durability is measured by the ball-on-disk method. Specifically, Friction Player FPR2200 manufactured by Resca Co., Ltd. was used as a measuring device, a coating film prepared using the coating composition of the present invention was set in the measuring device, and a ⁇ 5 mm zirconia ball was used as a test piece mating material, and a load was applied. : 1.0 kgf, rotation speed: 14 mm/sec, moving distance: 7 mm, temperature: 150°C.
- solvent surface tension The surface tension was measured using a Dvol surface tension tester manufactured by Ito Seisakusho Co., Ltd.
- the coating composition of the present disclosure has a high surface smoothness, thereby forming a coating film excellent in sliding performance and sliding durability.
- the coating composition of the present disclosure can be suitably used for coating various sliding members, particularly members for air conditioner compressor pistons, swash plates, and scroll compressors.
Abstract
Description
特許文献2は、ポリアミドイミド樹脂、ポリテトラフルオロエチレン及び3-メトキシ-N,N-ジメチルプロパンアミドを含有する組成物を開示している。
特許文献3は、ポリアミドイミドの溶解に使用する溶媒として、3-メトキシ-N,N-ジメチルプロパンアミドを使用することを開示している。
特許文献4は、ポリアミドイミド樹脂、ポリテトラフルオロエチレン及び3-メトキシ-N,N-ジメチルプロパンアミドを含有する組成物を開示している。
ポリテトラフルオロエチレン、バインダー樹脂、及び、新モース硬度が1.0~6.0の範囲にある充填剤を含み、N-メチル-2-ピロリドンの含有量が組成物の1重量%未満であることを特徴とする塗料組成物である。
上記塗料組成物は、N-エチル-2-ピロリドン、3-メトキシ-N,N-ジメチルプロパンアミド及びN-ブチルピロリドンからなる群から選択される少なくとも1種の溶剤を含むことが好ましい。
上記充填剤は、グラファイト、フッ化カルシウム及び酸化鉄からなる群から選択される少なくとも1種であることが好ましい。
本開示は、上述した塗料組成物から形成される塗膜でもある。
本開示は、上記塗膜を有する塗装物品でもある。
従来、ポリアミドイミド樹脂は、塗料組成物におけるバインダー樹脂として使用する場合は、N-メチル-2-ピロリドンを溶剤として含有するものが使用されてきた。N-メチル-2-ピロリドンは、優れた溶解能を有する樹脂であることから、これを使用することで好適な塗料組成物を得ることができた。
以下、本開示の塗料組成物に含まれる各成分について説明する。
ポリテトラフルオロエチレン(以下、これをPTFEと記すことがある)は、テトラフルオロエチレンの重合体である。上記PTFEは、TFE単位のみを含むホモPTFEであっても、TFE単位とTFEと共重合可能な変性モノマーに基づく変性モノマー単位とを含む変性PTFEであってもよい。
また、上記PTFEは溶融加工性を有し、フィブリル化性を有しない低分子量PTFEであることが好ましい。より具体的には、数平均分子量が200,000~400,000のものを使用することが好ましい。
CF2=CF-ORf1 (1)
(式中、Rf1は、パーフルオロ有機基を表す。)で表されるパーフルオロ不飽和化合物等が挙げられる。本明細書において、上記「パーフルオロ有機基」とは、炭素原子に結合する水素原子が全てフッ素原子に置換されてなる有機基を意味する。上記パーフルオロ有機基は、エーテル酸素を有していてもよい。
上記溶融粘度は、ASTM D 1238に準拠し、フローテスター(島津製作所社製)及び2φ-8Lのダイを用い、予め測定温度(380℃)で5分間加熱しておいた2gの試料を0.7MPaの荷重にて上記温度に保って測定することができる。
本明細書において、標準比重(SSG)は、ASTM D 4895-89に準拠して、水中置換法に基づき測定することができる。
本開示の塗料組成物は、バインダー樹脂を含有する。バインダー樹脂は特に限定されるものではないが、いわゆるスーパーエンプラであることが好ましく、具体的には、ポリアミドイミド、ポリエーテルサルフォン、ポリエーテルエーテルケトン、ポリエーテルイミド及びポリイミドからなる群から選択される少なくとも1種であることが好ましい。以下、これらについて説明する。
ポリアミドイミド樹脂は、代表的に、酸成分と、ジイソシアネート成分との反応によって得られる樹脂であり、酸成分に由来する構造部位と、ジイソシアネート成分に由来する構造部位とを有する。
上記酸成分は、特に限定されず、少なくとも、芳香族三塩基酸無水物及び/又は芳香族三塩基酸ハライドを含む。一実施形態において、酸成分は、少なくとも芳香族三塩基酸無水物を含むことが好ましく、なかでもトリメリット酸無水物を含むことがより好ましい。したがって、一実施形態において、ポリアミドイミド樹脂は、下記一般式(I)で表される構造を有することが好ましい。
その他の酸成分として、例えば、ジカルボン酸を使用することができる。ジカルボン酸として、例えば、コハク酸、グルタル酸、アジピン酸、ピメリン酸、スベリン酸、アゼライン酸、セバシン酸、フタル酸、イソフタル酸、テレフタル酸を使用することができる。
また、これらの化合物は、単独で使用しても、又は2種以上を組合せて使用してもよい。
ジイソシアネート成分は、少なくとも、芳香族ジイソシアネートを含むことが好ましい。したがって、一実施形態では、上記一般式(I)において、Rは芳香族ジイソシアネートに由来する有機基であることが好ましい。ポリアミドイミド樹脂を構成するジイソシアネート成分の合計量を基準(100モル%)として、芳香族ジイソシアネートの含有量は30モル%以上であることが好ましく、40モル%以上であることがより好ましい。一実施形態において、芳香族ジイソシアネートの含有量は100モル%であってよい。
したがって、ポリアミドイミド樹脂を構成するジイソシアネート成分の合計量を基準として、4,4’-ジフェニルメタンジイソシアネートを含む芳香族ジイソシアネートの含有量は30モル%以上であることが好ましく、40モル%以上であることがより好ましく、100モル%であってもよい。
ポリエーテルスルホン樹脂(PES)は、下記一般式:
ポリエーテルエーテルケトン樹脂は、下記一般式
ポリエーテルエーテルケトン樹脂は、下記一般式
ポリイミド樹脂は、分子構造中にイミド結合を有する重合体からなる樹脂である。上記ポリイミド樹脂としては特に限定されず、例えば、無水ピロメリット酸等の芳香族四価カルボン酸無水物と4,4′-ジアミノジフェニルエーテル等のポリアミン化合物の反応等により得られる高分子量重合体からなる樹脂等が挙げられる。耐熱性に優れる点から、上記ポリイミド樹脂としては、主鎖中に芳香環を有する重合体からなるものが好ましい。
上記上限は、77.0質量%であることがより好ましく、75.0質量%であることが更に好ましい。
本開示は充填剤を含有するものである。充填剤としては、硬度が新モース硬度で1.0~6.0のものを使用する。
なお、モース硬度は物質の相対的な硬度を1~10の範囲で評価したものであるが、新モース硬度は、硬度の評価をモース硬度の10段階に対して15段階とさらに細かく分類したものである。
硬度が新モース硬度で1.0~6.0である充填剤としては、特に限定されず、例えば、グラファイト(新モース硬度2.0)、フッ化カルシウム(新モース硬度4.0)、酸化鉄(新モース硬度6.0)、窒化ホウ素(新モース硬度2.0)、マイカ(新モース硬度3.0)、水酸化アルミニウム(新モース硬度3.0)、炭酸カルシウム(新モース硬度3.0)、酸化亜鉛(新モース硬度4.0~5.0)、第三リン酸カルシウム(新モース硬度5.0)等を挙げることができる。なかでも、摺動時に相手部材の摩耗を抑制するという観点から、グラファイト、フッ化カルシウム及び酸化鉄からなる群から選択される
少なくとも1種であることが好ましい。
これらのうち、2種以上を併用して使用するものであってもよい。
上記上限は、45.0質量%であることがより好ましく、40.0質量%であることが更に好ましい。
本開示の塗料組成物は、N-メチル-2-ピロリドン含有量が組成物の1重量%未満である。すなわち、N-メチル-2-ピロリドン含有量が少ないことによって、上述した効果を有する。したがって、N-メチル-2-ピロリドンを全く含有しないものであってもよい。
このような溶媒として具体的には、例えば、N-エチル-2-ピロリドン(NEP)、3-メトキシ-N,N-ジメチルプロパンアミド、N-ブチル-2-ピロリドン(NBP)等を挙げることができる。これらの2種以上の混合溶媒であってもよい。
表面張力は、37.0以下であることがより好ましく、36.5以下であることが更に好ましい。なお、ここでの表面張力は実施例に記載した方法で測定した値である。
本開示の塗料組成物は、粘度が100~40,000cpsであることが好ましい。上記範囲内とすることで、塗装工程における作業性を良好なものとすることができる。更に、所定の膜厚を得るという点でも好ましい。
本開示の塗料組成物は、本開示の目的を損なわない範囲で上述した成分に加えてその他の成分を含有するものであってもよい。
本開示の塗料組成物は、上述した各成分を混合することによって製造することができる。
ビーズミル、ボールミル、三本ロール等の公知の各種ミルを用い、必要に応じてこれらを適宜組合せ、粉砕条件の調整、粉砕時間の調整、併用する樹脂成分の配合の調整等を行うことで適切な解砕を行うことができる。
本開示の塗料組成物によって形成された塗膜も本開示の対象である。塗膜の形成は一般的な方法によって行うことができる。
本開示の塗膜は、表面粗度Raが1.0以下であることが好ましい。本開示の塗料組成物を使用することによって、このような塗膜を形成することができる。上記表面粗度Raは、0.8以下であることがより好ましく、0.7以下であることが更に好ましい。
本開示の塗料組成物は優れた耐摩擦性能を有し、高温、高発熱環境下で使用可能な摺動材のコーティング材料として用いることができる。より具体的な製品としては、エアコンコンプレッサーピストン用、斜板用、スクロールコンプレッサー用部材、等を挙げることができる。特にカーエアコンコンプレッサーピストン用が好ましい。このような用途における基材、塗装方法等は公知の方法に基づいて行うことができる。
バインダー樹脂が3-メトキシ-N,N-ジメチルプロパンアミド、N-メチル-2-ピロリドン(NMP)、N-2-エチル-2-ピロリドン(NEP)のいずれかに溶解したポリアミドイミドワニス(固形分濃度 約34質量%、ポリアミドイミドの数平均分子量:13000~18000)の樹脂固形分に対し、ポリテトラフルオロエチレン(PTFE、数平均分子量:200000~400000、融点:300~330℃、比重:2.0~2.3、溶融粘度:1.0×103~1.0×107 Pa・s)、充填剤(D50:1~5μm)を所定量配合して撹拌ミルを用いて分散し、当該塗料を得た。塗料の粘度は20000~30000cpsであった。
上述の実施例1~9及び比較例1~7の塗料組成物を、アルミ板の基材試験片上にアプリケーターまたはスプレー塗装ガンを用いて、焼成時の膜厚が30~40μmとなるように塗装し、100℃で30分、230℃30分焼成させ、塗膜を作成し、試験片を得た。
ゲルパーミエーションクロマトグラフ(GPC)によって測定した値である。装置は東ソー(株)製 GEL PERMEATION CHROMATOGRAPH HLC-8020、カラムは昭和電工(株)製 shodex GPC KF-G(プレフィルターカラム)、溶剤はテトラヒドロフランを使用した。
ASTM D 1238に準拠しフローテスター(島津製作所社製)および2Φ-8Lのダイを用い、予め380℃で5分間加熱しておいた2gの試料を0.7MPaの荷重にて測定した溶融粘度の値から算出した。
表面粗度は接触式表面粗さ計である新東科学株式会社製のサートニック デュオを使用して測定した。
摩擦係数は接触式計測器であるアメテック株式会社製のトライボギア38を使用して測定した。
摺動持続性はボールオンディスク法により測定される。具体的には、測定装置として株式会社レスカ製フリクションプレーヤーFPR2200を用い、測定装置に本発明の塗料組成物を用いて作成された塗膜をセットし、試験片相手材としてφ5mmのジルコニアボール、荷重:1.0kgf、回転速度:14mm/sec、移動距離:7mm、温度:150℃の往復摺動試験の条件で測定される。
表面張力は株式会社伊藤製作所製のデュヌイ表面張力試験器を使用して測定した。
Claims (7)
- ポリテトラフルオロエチレン、バインダー樹脂、及び、新モース硬度が1.0~6.0の範囲にある充填剤を含み、N-メチル-2-ピロリドンの含有量が組成物の1重量%未満であることを特徴とする塗料組成物。
- バインダー樹脂が、ポリアミドイミド、ポリエーテルサルフォン、ポリエーテルエーテルケトン、ポリエーテルイミド及びポリイミドからなる群から選択される少なくとも1種である請求項1に記載の塗料組成物。
- N-エチル-2-ピロリドン、3-メトキシ-N,N-ジメチルプロパンアミド及びN-ブチルピロリドンからなる群から選択される少なくとも1種の溶剤を含む請求項1または2に記載の塗料組成物。
- 充填剤は、グラファイト、フッ化カルシウム及び酸化鉄からなる群から選択される少なくとも1種である、請求項1~3のいずれかに記載の塗料組成物。
- コンプレッサの摺動部材用である請求項1~4のいずれかに記載の塗料組成物。
- 請求項1~5のいずれかに記載の塗料組成物から形成される塗膜。
- 請求項6に記載の塗膜を有する塗装物品。
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