Classifications

• • 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
  • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
• • 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
  • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
  • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
  • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
  • C08G63/16—Dicarboxylic acids and dihydroxy compounds
  • C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
  • C08G63/19—Hydroxy compounds containing aromatic rings
  • C08G63/193—Hydroxy compounds containing aromatic rings containing two or more aromatic rings
• • 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
  • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
  • C08G63/66—Polyesters containing oxygen in the form of ether groups
  • C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
  • C08G63/672—Dicarboxylic acids and dihydroxy compounds
• • 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
  • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
  • C08G63/78—Preparation processes
• • 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
  • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
  • C08G63/78—Preparation processes
  • C08G63/79—Interfacial processes, i.e. processes involving a reaction at the interface of two non-miscible liquids
• • 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
  • C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers

Definitions

• the present invention relates to polyarylate, a method for producing polyarylate, a coating composition, a coating film, and a method for producing a coating film.
• Polyesters containing repeating units derived from an aromatic diol compound and repeating units derived from an aromatic dicarboxylic acid compound are widely used industrially because of their excellent heat resistance, mechanical strength, and the like.
• Patent Documents 1 and 2 disclose electrophotographic photoreceptors having a surface layer containing an electron transport material and a polyester resin (polyarylate) having a specific structure.
• an object of the present invention is to provide a polyarylate capable of forming a film having excellent heat resistance and abrasion resistance, and a method for producing the same.
• Another object of the present invention is to provide a coating composition, a coating film, and a method for producing a coating film.
• a polyarylate comprising a repeating unit I, a repeating unit II, and a repeating unit represented by formula (III) described below,
• the repeating unit I is at least one of the repeating units represented by formulae (IA) to (IC) described below
• the repeating unit II is at least one of the repeating units represented by formulae (II-A) to (II-E) described below, the content of the repeating unit II relative to the total content of the repeating unit I and the repeating unit II is 10 mol % or more;
• Requirement 1 The solubility in tetrahydrofuran is 5% by mass or more.
• Step 1 which comprises reacting compound i with a compound represented by formula (iii) described below; and step 2 of reacting the product obtained in step 1 with compound ii
• the compound i is at least one of the compounds represented by formulas (i-A) to (i-C) described below
• the compound ii is at least one of the compounds represented by formulas (ii-A) to (ii-E) described below
• a method for producing a polyarylate wherein the amount of the compound ii used is 10 mol % or more based on the total amount of the compound i used and the compound ii used.
• the method for producing a polyarylate according to [7] wherein the reactions in the steps 1 and 2 are interfacial polymerization reactions.
• the present invention it is possible to provide a polyarylate capable of forming a film having excellent heat resistance and abrasion resistance, and a method for producing the same. Furthermore, according to the present invention, it is possible to provide a coating composition, a coating film, and a method for producing a coating film.
• alkyl group includes not only alkyl groups that do not have a substituent (unsubstituted alkyl groups), but also alkyl groups that have a substituent (substituted alkyl groups).
• organic group in the present specification refers to a group that contains at least one carbon atom. Unless otherwise specified, the substituent is preferably a monovalent substituent.
• a numerical range expressed using “ ⁇ ” means a range that includes the numerical values written before and after " ⁇ " as the lower and upper limits.
• each repeat unit may be the same or different.
• the weight average molecular weight (Mw) of a polymer is a polystyrene-equivalent value measured by gel permeation chromatography (GPC). Tetrahydrofuran is a preferred eluent for GPC.
• the preferred embodiment of the weight average molecular weight is a polystyrene-equivalent value measured using tetrahydrofuran as the eluent.
• the bonding direction of the divalent groups described in this specification is not limited unless otherwise specified.
• Y when Y is -COO- in a compound represented by the formula "X-Y-Z", Y may be -CO-O- or -O-CO-.
• the above compound may be "X-CO-O-Z" or "X-O-CO-Z”.
• solids refers to components that form a film and does not include solvents.
• any component that forms a film is considered to be a solid even if it is in liquid form.
• the polyarylate of the present invention (hereinafter also referred to as “specific polyarylate”) is A repeating unit I (hereinafter also referred to as “repeating unit I”) which is at least one of repeating units represented by formulas (IA) to (IC) described later, A repeating unit II (hereinafter also referred to as “repeating unit II") which is at least one of repeating units represented by formulas (II-A) to (II-E) described later, A polyarylate comprising a repeating unit represented by the formula (III) described below (hereinafter also referred to as "repeating unit III”), the content of the repeating unit II relative to the total content of the repeating unit I and the repeating unit II is 10 mol % or more; Meet requirement 1.
• Requirement 1 The solubility in tetrahydrofuran (THF) is 5% by mass or more.
• the polylate of the present invention having such a constitution, a film having excellent heat resistance and abrasion resistance can be formed.
• the mechanism of the above-mentioned action and effect of the present invention is not necessarily clear, but the present inventors speculate as follows.
• the present inventors have recently synthesized and investigated polyarylates using the synthesis methods described in the examples of Patent Document 1 and Patent Document 2, and have found that when the amount of repeating unit II, which contains repeating units I to III and is a component that contributes to improving the abrasion resistance of the polyarylate, introduced is equal to or greater than a predetermined value (specifically, when the content of repeating unit II relative to the total content of repeating units I and II is equal to or greater than 10 mol %), the resulting polyarylate may be inferior in abrasion resistance and heat resistance.
• the present inventor further studied based on the above findings and found that when the solubility of polyarylate in THF is 5% by mass or more, the heat resistance of the film containing polyarylate and functional material is significantly improved.
• the reason for this is not necessarily clear, but it is speculated that the polyarylate having a solubility of 5% by mass or more in THF has a relatively high alternating copolymerization property of repeating unit I, repeating unit II, and repeating unit III (in other words, the occurrence of a structural portion in which a specific repeating unit is excessively unevenly distributed (for example, a structural portion in which repeating unit I and repeating unit III are continuous) is suppressed, and the repeating units I to III are relatively uniformly arranged).
• the film containing such polyarylate and functional material is unlikely to become cloudy or colored even when subjected to a heat treatment or the like at high temperatures, and the functional material contained in the film is unlikely to start to weep, due to the excellent uniformity of the arrangement of each repeating unit in the main chain of the polyarylate.
• the superior heat resistance of a film formed using the polyarylate of the present invention and/or the superior abrasion resistance of a film formed using the polyarylate of the present invention will also be referred to as "the effects of the present invention being superior.”
• the polyarylate of the present invention and the method for producing the same will be described in detail below.
• the polyarylate of the present invention contains repeating units I, II, and III.
• the repeating unit I is at least one of the repeating units represented by formulae (IA) to (IC).
• the repeating unit I in terms of obtaining better effects of the present invention, it is preferable that the repeating unit contains a repeating unit represented by formula (IA), and it is more preferable that the repeating unit contains a repeating unit represented by formula (IAa).
• the repeating units represented by formulae (IA) to (IC) will be described below.
• R 1 represents a branched alkyl group having 4 or more carbon atoms which may have a substituent.
• the number of carbon atoms in R 1 is preferably 4 to 20, more preferably 4 to 15, still more preferably 4 to 10, particularly preferably 4 to 8, and particularly preferably 4 to 6.
• R 1 examples include a 1-methylpropyl group, a 2-methylpropyl group, a 1,2-dimethylpropyl group, a 2,2-dimethylpropyl group, a 1-ethylpropyl group, a 1-methylbutyl group, a 2-methylbutyl group, a 3-methylbutyl group, a 1-ethylbutyl group, a 2-ethylbutyl group, a 1,1-dimethylbutyl group, a 1,2-dimethylbutyl group, a 1,3-dimethylbutyl group, a 2,2-dimethylbutyl group, a 3,3-dimethylbutyl group, a 4-methylpentyl group, a 1-ethylpentyl group, a 2-ethylpentyl group, a 3-ethylpentyl group, a 1,3-dimethylpentyl group, a 1,4-dimethylpentyl group, a 2,4,4
• R 1 is preferably a 1-methylpropyl group, a 2-methylpropyl group, a 1-methylbutyl group, a 3-methylbutyl group, a 1-ethylpropyl group, a 1-ethylbutyl group, a 1-ethylpentyl group, a 1-ethylhexyl group, a 1-ethylheptyl group, or a 2,4,4-trimethylpentyl group, more preferably a 2-methylpropyl group, a 1-ethylbutyl group, a 1-ethylpentyl group, a 2,4,4-trimethylpentyl group, or a 1-ethylheptyl group, and even more preferably a 2-methylpropyl group, a 1-ethylbutyl group, a 1-ethylpentyl group, or a 2,4,4-trimethylpentyl group.
• R2 represents a hydrogen atom, a linear alkyl group which may have a substituent, or an aryl group which may have a substituent.
• the linear alkyl group represented by R2 preferably has 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms, and even more preferably 1 to 4 carbon atoms.
• the substituent that the linear alkyl group represented by R2 may have is not particularly limited, and examples thereof include an alkoxy group, an acyl group, and an acyloxy group.
• the alkyl group moiety contained in the alkoxy group, the acyl group, and the acyloxy group may be linear, branched, or cyclic.
• the number of carbon atoms in the alkyl group and the alkyl group moiety contained in the alkoxy group, the acyl group, and the acyloxy group is preferably 1 to 20, more preferably 1 to 10, and even more preferably 1 to 6.
• the linear alkyl group represented by R2 above preferably has no substituent.
• the linear alkyl group represented by R2 is preferably a methyl group or an ethyl group, and more preferably a methyl group.
• the number of carbon atoms of the aryl group which may have a substituent and is represented by R2 is preferably 6 to 26, more preferably 6 to 20, still more preferably 6 to 15, particularly preferably 6 to 12, and most preferably 6 to 10.
• the substituent that the aryl group represented by R2 may have is not particularly limited, and examples thereof include an alkyl group, an alkoxy group, an acyl group, and an acyloxy group.
• the alkyl group moiety contained in the alkyl group, alkoxy group, acyl group, and acyloxy group may be any of linear, branched, and cyclic.
• the number of carbon atoms contained in the alkyl group moiety contained in the alkyl group, alkoxy group, acyl group, and acyloxy group is preferably 1 to 20, more preferably 1 to 10, and even more preferably 1 to 6.
• the optionally substituted aryl group represented by R2 is preferably a phenyl group, a 4-methoxyphenyl group, a 4-acetoxyphenyl group, a 1-naphthyl group, or a 2-naphthyl group.
• R2 is preferably a hydrogen atom or a methyl group, more preferably a methyl group.
• Each R3 independently represents a hydrogen atom, an alkyl group which may have a substituent, or an aryl group which may have a substituent.
• the alkyl group represented by R3 may be any of linear, branched and cyclic.
• the alkyl group represented by R3 preferably has 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms, and even more preferably 1 to 4 carbon atoms.
• the substituent that the alkyl group represented by R3 may have is not particularly limited, and examples thereof include an alkoxy group, an acyl group, and an acyloxy group.
• the alkyl group moiety contained in the alkoxy group, the acyl group, and the acyloxy group may be linear, branched, or cyclic.
• the number of carbon atoms in the alkyl group and the alkyl group moiety contained in the alkoxy group, the acyl group, and the acyloxy group is preferably 1 to 20, more preferably 1 to 10, and even more preferably 1 to 6.
• the alkyl group represented by R3 above preferably has no substituent.
• the alkyl group represented by R3 is preferably a methyl group or an ethyl group, and more preferably a methyl group.
• the aryl group which may have a substituent represented by R3 has the same meaning as the aryl group which may have a substituent represented by R2 in formula (IA), and the preferred embodiments are also the same.
• R3 is preferably a hydrogen atom or a methyl group.
• R 1 and R 2 do not bond to each other to form a ring structure.
• the repeating unit represented by formula (I-A) preferably contains a repeating unit represented by formula (I-Aa) in that the effect of the present invention is more excellent.
• R 4 represents a hydrogen atom, a linear alkyl group which may have a substituent, or an aryl group which may have a substituent.
• the linear alkyl group which may have a substituent represented by R4 has the same meaning as the linear alkyl group which may have a substituent represented by R2 in formula (IA), and the preferred embodiments are also the same.
• the aryl group which may have a substituent represented by R4 has the same meaning as the aryl group which may have a substituent represented by R2 in formula (IA), and the preferred embodiments are also the same.
• R4 is preferably a hydrogen atom or a methyl group.
• Each R5 independently represents a hydrogen atom, an alkyl group which may have a substituent, or an aryl group which may have a substituent.
• the alkyl group which may have a substituent represented by R5 has the same meaning as the alkyl group which may have a substituent represented by R3 in formula (IA), and the preferred embodiments are also the same.
• the aryl group which may have a substituent represented by R5 has the same meaning as the aryl group which may have a substituent represented by R2 in formula (IA), and the preferred embodiments are also the same.
• n represents an integer of 2 to 20.
• n is preferably an integer of 3 to 20, more preferably an integer of 4 to 20, still more preferably an integer of 4 to 15, particularly preferably an integer of 5 to 13, and most preferably an integer of 6 to 10.
• each R 6 independently represents a hydrogen atom, an optionally substituted alkyl group, or an optionally substituted aryl group.
• the optionally substituted alkyl group and the optionally substituted aryl group represented by R6 have the same meanings as the optionally substituted alkyl group and the optionally substituted aryl group represented by R3 in formula (IA), respectively, and the preferred embodiments are also the same.
• Each R 7 independently represents a hydrogen atom, an alkyl group which may have a substituent, or an aryl group which may have a substituent.
• the optionally substituted alkyl group and the optionally substituted aryl group represented by R7 have the same meanings as the optionally substituted alkyl group and the optionally substituted aryl group represented by R3 in formula (IA), respectively, and the preferred embodiments are also the same.
• repeating units represented by formula (IC) are shown below.
• the lower limit of the content of repeating unit I is preferably 5 mol% or more, more preferably 10 mol% or more, and even more preferably 15 mol% or more, based on the total repeating units of the specific polyarylate.
• the upper limit of the content of repeating unit I is preferably 45 mol% or less, more preferably 40 mol% or less, and even more preferably 35 mol% or less, based on the total repeating units of the specific polyarylate.
• the repeating unit I may be one kind or two or more kinds of the repeating units represented by formulae (IA) to (IC). When the repeating unit I contains two or more kinds of repeating units represented by formulae (IA) to (IC), the above content represents the total content.
• the repeating unit II is at least one of the repeating units represented by formulae (II-A) to (II-E).
• the repeating unit II preferably contains at least one of the repeating units represented by formula (II-A) and the repeating unit represented by formula (II-B), in that the effects of the present invention are more excellent.
• the lower limit of the content of repeating unit II is preferably 5 mol% or more, more preferably 9 mol% or more, and even more preferably 13 mol% or more, based on the total repeating units of the specific polyarylate.
• the upper limit of the content of repeating unit II is preferably 45 mol% or less, more preferably 35 mol% or less, and even more preferably 25 mol% or less, based on the total repeating units of the specific polyarylate.
• the repeating unit II may be one kind or two or more kinds of the repeating units represented by formulae (II-A) to (II-E). When the repeating unit II contains two or more kinds of repeating units represented by formulae (II-A) to (II-E), the above content represents the total content.
• the content of repeating unit II with respect to the total content of repeating unit I and repeating unit II is 10 mol% or more, and from the viewpoint that the wear resistance of the obtained film is more excellent, it is preferably 18 mol% or more, more preferably 26 mol% or more, and even more preferably 32 mol% or more.
• the upper limit is not particularly limited, but from the viewpoint that the film forming property is more excellent, it is preferably 50 mol% or less.
• the repeating unit III is a repeating unit represented by formula (III).
• L2 represents a divalent organic group.
• examples of the divalent organic group represented by L2 include a group represented by the following formula (IIIL), a naphthylene group, and an alkylene group.
• Ph 1 and Ph 2 each independently represent a phenylene group which may have a substituent.
• the substituent that the phenylene group may have is not particularly limited, and examples thereof include an alkyl group, an alkoxy group, an acyl group, an acyloxy group, an aryl group, and a halogen atom.
• the alkyl group moiety contained in the alkyl group, alkoxy group, acyl group, and acyloxy group may be linear, branched, or cyclic.
• the number of carbon atoms in the alkyl group, alkoxy group, acyl group, and acyloxy group is preferably 1 to 20, more preferably 1 to 10, and even more preferably 1 to 6.
• the number of carbon atoms in the aryl group is preferably 6 to 20, more preferably 6 to 15, even more preferably 6 to 12, and particularly preferably 6 to 10.
• the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
• L 21 represents a single bond or —O—.
• n1 represents 0 or 1.
• * represents the bonding position with the carbonyl group shown in formula (III).
• the alkylene group represented by L2 includes linear alkylene groups having 4 to 30 carbon atoms, and among these, linear alkylene groups having 4 to 20 carbon atoms are preferred.
• repeating unit III include repeating units represented by formulae (III-A) to (III-D) described below, as well as repeating units derived from dicarboxylic acids such as 1,4-cyclohexanedicarboxylic acid, orthophthalic acid, 1,4-naphthalenedicarboxylic acid, 2,3-naphthalenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, and eicosanediacid.
• dicarboxylic acids such as 1,4-cyclohexanedicarboxylic acid, orthophthalic acid, 1,4
• the repeating unit III preferably contains at least one of the repeating units represented by formulae (III-A) to (III-D), and more preferably contains a repeating unit represented by formula (III-A), in that the effects of the present invention are more excellent.
• the content of the repeating unit III is preferably 30 to 70 mol %, more preferably 40 to 60 mol %, and even more preferably 45 to 55 mol %, based on the total repeating units of the specific polyarylate.
• the repeating unit III may be of one type or of two or more types. When the repeating unit III is of two or more types, the above content represents the total content.
• the weight average molecular weight of the specific polyarylate is preferably 50,000 to 250,000, more preferably 80,000 to 180,000, and even more preferably 100,000 to 150,000.
• the specific polyarylate satisfies the following requirement 1.
• Requirement 1 The solubility in tetrahydrofuran (THF) is 5% by mass or more. Whether or not a specific polyarylate satisfies requirement 1 is determined by the following procedure. (Determination Procedure) 95 g of tetrahydrofuran (THF) is placed in a container, and 5 g of the polymer to be evaluated is added. After the addition, the mixture is stirred with a mix rotor for 1 hour and then allowed to stand. The above liquid preparation is carried out at room temperature (20 to 25° C.). Next, the polymer solution after standing is visually observed. If no precipitate or haze occurs, it is judged as passing, and if at least one of precipitate and haze occurs, it is judged as failing.
• the specific polyarylate preferably has a solubility in THF of 7% by mass or more, and more preferably 9% by mass or more. There is no particular upper limit to the solubility of the specific polyarylate in THF, but it is often 50% by mass or less.
• the specific polyarylate can be produced by the following production method: The production method of the specific polyarylate will be described below.
• the method for producing the specific polyarylate of the present invention (hereinafter also referred to as the "production method of the present invention”) is as follows: A step 1 of reacting at least one compound i represented by formula (i-A) to formula (i-C) (hereinafter also referred to as a “repeating unit I raw material”) with a compound represented by formula (iii) (hereinafter also referred to as a “repeating unit III raw material”); and step 2, in which the product obtained in step 1 is reacted with compound ii (hereinafter also referred to as “repeating unit II raw material"), which is at least one of the compounds represented by formulae (ii-A) to (ii-E),
• the amount of the compound ii used is 10 mol % or more based on the total amount of the compound i used and the compound ii used.
• step 2 in which the product obtained in step 1 is polymerized with the repeating unit II raw material is carried out.
• an ester compound (mono-adduct, di-adduct, and/or oligomer) is formed by dehydration condensation of the repeating unit I raw material and the repeating unit III raw material at the stage of step 1.
• step 2 By carrying out step 2 in which the product obtained in step 1 is reacted with the repeating unit II raw material, a polyarylate having a relatively high alternating copolymerizability of repeating units I to III (in other words, a structure in which the repeating units I to III are relatively uniformly arranged, with the occurrence of structural portions in which specific repeating units are excessively unevenly distributed (for example, a structural portion in which repeating units I and III are consecutive) is suppressed) can be produced.
• the polymerization reactions in steps 1 and 2 are preferably interfacial polymerization reactions (interfacial polycondensation reactions) in that a polymer having desired properties can be easily obtained.
• the raw material for repeating unit I is at least one of the compounds represented by formulae (iA) to (iC).
• R 1 , R 2 and R 3 have the same meanings as R 1 , R 2 and R 3 in formula (IA), and the preferred embodiments are also the same.
• each X independently represents a hydrogen atom, Na, Li, K, or Cs. However, R 1 and R 2 do not bond to each other to form a ring structure.
• the compound represented by formula (i-A) preferably includes a compound represented by formula (i-Aa), since this provides a more excellent effect of the present invention.
• each X independently represents a hydrogen atom, Na, Li, K, or Cs.
• R 4 , R 5 and n have the same meanings as R 4 , R 5 and n in formula (IB), and the preferred embodiments are also the same.
• Each X independently represents a hydrogen atom, Na, Li, K, or Cs.
• R 6 and R 7 have the same meanings as R 6 and R 7 in formula (IC), and the preferred embodiments are also the same.
• Each X independently represents a hydrogen atom, Na, Li, K, or Cs.
• Specific examples of the compounds represented by formulas (i-A) to (i-C) include compounds in which the oxygen atom at the position having the bond connecting the repeating units in the compounds exemplified as specific examples of the repeating units represented by formulas (i-A) to (i-C) is replaced with -OX (X represents a hydrogen atom, Na, Li, K, or Cs).
• the repeating unit II raw material is at least one of the compounds represented by formulae (ii-A) to (ii-E). (Compounds represented by formulas (ii-A) to (ii-E))
• each X independently represents a hydrogen atom, Na, Li, K, or Cs.
• the repeating unit II raw material preferably contains at least one of the compounds represented by formula (ii-A) and (ii-B), in that the effects of the present invention are more excellent.
• the repeating unit III raw material is a compound represented by formula (iii). (Compound represented by formula (iii))
• L2 has the same meaning as L2 in formula (III), and the preferred embodiments are also the same.
• each Y independently represents a hydroxyl group, F, Cl, Br, or I.
• repeating unit III raw material examples include, for example, compounds represented by formulas (iii-A) to (iii-D) described below, as well as dicarboxylic acids such as 1,4-cyclohexanedicarboxylic acid, orthophthalic acid, 1,4-naphthalenedicarboxylic acid, 2,3-naphthalenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, and eicosane diacid; acid halide compounds in which the hydroxyl groups of the above dicarboxylic acids are replaced with hal
• the repeating unit III raw material preferably contains at least one of the compounds represented by formulas (iii-A) to (iii-D), and more preferably contains a compound represented by formula (iii-A), in that the effects of the present invention are more excellent.
• each Y independently represents a hydroxyl group, F, Cl, Br, or I.
• Step 1 and Step 2 Next, the procedures of steps 1 and 2 will be described.
• the reactions in steps 1 and 2 can be carried out by a conventional polycondensation method or the like.
• the polymerization reactions in steps 1 and 2 include, for example, an interfacial polymerization method and a solution polymerization method, with the interfacial polymerization method being preferred.
• the interfacial polymerization method is a polymerization method for obtaining polyester (polyarylene) by mixing a divalent carboxylic acid halide dissolved in an organic solvent that is not compatible with water with a divalent phenol dissolved in an alkaline aqueous solution.
• Literature relating to the interfacial polymerization method includes W. M. EARECKSON, J. Poly. Sci., XL399, 1959, and JP-B-40-001959.
• the interfacial polymerization method Compared with the solution polymerization method, the interfacial polymerization method has a faster reaction rate, and therefore can suppress hydrolysis of the acid halide, and as a result, it is easy to obtain a high molecular weight resin.
• the dihydric phenol dissolved in an aqueous alkali solution is added in multiple stages (divided addition).
• step 1 it is preferable to carry out step 1 in which a divalent carboxylic acid halide (corresponding to the repeating unit III raw material) dissolved in an organic solvent that is not compatible with water is mixed with a dihydric phenol A (corresponding to the repeating unit I raw material) dissolved in an aqueous alkali solution and reacted, and then carry out step 2 in which the reaction liquid obtained in step 1 is mixed with a dihydric phenol B (corresponding to the repeating unit II raw material) dissolved in an aqueous alkali solution and reacted to obtain a polyester (polyarylene), as a polymerization method.
• a divalent carboxylic acid halide corresponding to the repeating unit III raw material
• step 2 the reaction liquid obtained in step 1 is mixed with a dihydric phenol B (corresponding to the repeating unit II raw material) dissolved in an aqueous alkali solution and reacted to obtain a polyester (polyarylene), as a polymerization method.
• an alkaline aqueous solution of dihydric phenol A (corresponding to the repeating unit I raw material) is prepared as the aqueous phase, followed by adding a polymerization catalyst.
• a divalent carboxylic acid halide (corresponding to the repeating unit III raw material) is dissolved in a solvent that is incompatible with water and dissolves the polymer, and this solution is mixed with the previous alkaline solution, and then the polymerization reaction is carried out while stirring at a temperature of preferably 50° C. or less for 10 minutes to 3 hours.
• a previously prepared alkaline aqueous solution of dihydric phenol B (corresponding to the repeating unit II raw material) is mixed with the resulting reaction liquid, and the polymerization reaction is carried out while stirring at a temperature of preferably 50° C. or less for 1 to 5 hours, thereby obtaining a desired polymer solution.
• the dicarboxylic acid halide (corresponding to the raw material of the repeating unit III) does not necessarily have to be entirely dissolved in the organic phase.
• the following method A may be used. This method is particularly effective when the dicarboxylic acid halide (corresponding to the raw material of the repeating unit III) is not soluble in the solvent of the organic layer or has low solubility.
• aqueous phase an alkaline aqueous solution of dihydric phenol A (corresponding to the raw material of repeating unit I) is prepared, and then a polymerization catalyst is added.
• the dihydric phenol A (corresponding to the raw material of repeating unit I) and/or its phenoxide may not be completely dissolved in the alkaline aqueous solution of dihydric phenol A (corresponding to the raw material of repeating unit I).
• an organic phase only an organic solvent that is incompatible with water and dissolves the polymer is mixed into the above-mentioned alkaline solution, and suspended by stirring.
• a solid divalent carboxylic acid halide such as powder (corresponding to the raw material for the repeating unit III) is added thereto, and a polymerization reaction is carried out.
• a previously prepared aqueous alkali solution of dihydric phenol B (corresponding to the raw material of repeating unit II) is added to the resulting reaction solution to carry out the polymerization reaction.
• This method has three advantages. The first point is that the dicarboxylic acid halide (corresponding to the repeating unit III raw material) is not previously made into a solution or solvent suspension, so that hydrolysis of the dihydric phenol A (corresponding to the repeating unit I raw material) can be suppressed until it is mixed with the alkaline aqueous solution. The second point is that the solvent suspension is not handled, so that the complicated operation of transferring the solvent suspension to mix with the alkaline aqueous solution can be avoided.
• the third advantage is that it is not necessary to completely dissolve the dicarboxylic acid halide (corresponding to the repeating unit III raw material) itself, so that the amount of organic solvent used can be reduced, and as a result, the production efficiency can be improved and the organic solvent can be saved.
• the polymerization catalyst may be added in advance to the aqueous layer or to the organic layer.
• Examples of the alkali used in preparing the aqueous solution of dihydric phenol A include sodium hydroxide, potassium hydroxide, lithium hydroxide, etc.
• the amount of the alkali used is generally 2 to 5 times the number of moles of dihydric phenol A (corresponding to the raw material of repeating unit I), that is, 1 to 2.5 equivalents relative to the hydroxyl group.
• Examples of the alkali used in preparing the aqueous solution of dihydric phenol B (corresponding to the raw material of repeating unit II) include sodium hydroxide, potassium hydroxide, lithium hydroxide, etc.
• the amount of the alkali used is generally 2 to 5 times the number of moles of dihydric phenol B (corresponding to the raw material of repeating unit II), that is, 1 to 2.5 equivalents relative to the hydroxyl group.
• the following method B may be used.
• an organic solvent that is incompatible with water and dissolves the polymer and a divalent carboxylic acid halide (corresponding to the repeating unit III raw material) are mixed and stirred to obtain a suspension.
• a aqueous phase an alkaline aqueous solution of dihydric phenol A (corresponding to the repeating unit I raw material) is prepared, followed by adding a polymerization catalyst. The obtained aqueous layer is added to the above suspension to carry out a polymerization reaction.
• a previously prepared aqueous alkali solution of dihydric phenol B (corresponding to the raw material of repeating unit II) is added to the resulting reaction solution to carry out a polymerization reaction.
• the reproducibility of the polymerization step may be improved by preparing a dicarboxylic acid halide (corresponding to the repeating unit III raw material) as a suspension in an organic solvent in advance by the above-mentioned method B.
• the above-mentioned method B does not include a liquid transfer step of the solvent suspension, so that the complexity of the operation is reduced, and the concern of hydrolysis of the dicarboxylic acid halide (corresponding to the repeating unit III raw material) in the liquid transfer step is also reduced.
• an alkaline aqueous solution of dihydric phenol A (corresponding to the repeating unit I raw material) is prepared as an aqueous phase, followed by adding a polymerization catalyst, while a solution or solvent suspension of divalent carboxylic acid halide (corresponding to the repeating unit III raw material) is prepared as an organic phase, which is then added to the alkaline solution A to carry out a polymerization reaction.
• a previously prepared aqueous alkali solution of dihydric phenol B (corresponding to the raw material of repeating unit II) is added to the resulting reaction solution to carry out a polymerization reaction.
• a terminal blocking agent may be used during polymerization in order to control the molecular weight of the polymer. Also, in order to control the properties of the polymer, it is preferable that the terminals of the polymer are blocked with a monohydric phenol, a monohydric acid chloride, a monohydric alcohol, a monohydric carboxylic acid, or the like.
• Examples of monohydric phenols used as such end-capping agents include phenol, o-cresol, m-cresol, p-cresol, p-tert-butylphenol, o-phenylphenol, m-phenylphenol, p-phenylphenol, o-methoxyphenol, m-methoxyphenol, p-methoxyphenol, 2,3,5-trimethylphenol, 2,3,6-trimethylphenol, 2,3-xylenol, 2,4-xylenol, 2,5-xylenol, 2,6-xylenol, 3,4-xylenol, 3,5-xylenol, 2-phenyl-2-(4-hydroxyphenyl)propane (sometimes referred to as "p-( ⁇ -cumyl)phenol)").
• Examples of monovalent acid chlorides used as end-capping agents include benzoyl chloride, methanesulfonyl chloride, chlorocarbonic acid phenyl ester, acetyl chloride, and lauroyl chloride.
• Examples of monovalent alcohols used as end-capping agents include methanol, ethanol, n-propanol, isopropanol, n-butanol, 2-butanol, pentanol, hexanol, dodecyl alcohol, stearyl alcohol, benzyl alcohol, and phenethyl alcohol.
• Examples of monovalent carboxylic acids used as end-capping agents include acetic acid, propionic acid, octanoic acid, cyclohexanecarboxylic acid, benzoic acid, toluic acid, phenylacetic acid, p-tert-butylbenzoic acid, and p-methoxyphenylacetic acid.
• it is preferable to cap the ends with a monohydric phenol or a monoacid chloride it is more preferable to cap the ends with p-tert-butylphenol, 2,3,5-trimethylphenol, 2,3,6-trimethylphenol, benzoyl chloride, or acetyl chloride.
• polymerization catalysts for interfacial polymerization include quaternary ammonium salts such as tributylbenzylammonium halide, tetrabutylammonium halide, trimethylbenzylammonium halide, and triethylbenzylammonium halide; and quaternary phosphonium salts such as tributylbenzylphosphonium halide, tetrabutylphosphonium halide, trimethylbenzylphosphonium halide, and triethylbenzylphosphonium halide.
• tributylbenzylammonium halide tetrabutylammonium halide
• tributylbenzylphosphonium halide tributylbenzylphosphonium halide
• tetrabutylphosphonium halide tributylbenzylphosphonium halide
• Examples of the solvent for the organic phase in the interfacial polymerization include chlorine-based solvents such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, chlorobenzene, 1,1,2,2-tetrachloroethane, 1,1,1-trichloroethane, o-dichlorobenzene, m-dichlorobenzene, and p-dichlorobenzene; aromatic hydrocarbons such as toluene, benzene, xylene, and anisole; tetrahydrofuran; etc.
• dichloromethane and o-dichlorobenzene are preferred as the organic solvent for the organic layer.
• the dicarboxylic acid halide (corresponding to the repeating unit III raw material) is not dissolved in the organic solvent of the organic layer or has low solubility
• other organic solvents can also be used.
• the organic solvent of the organic layer is preferably one that is not soluble in water, but for the purpose of improving the solubility of the dicarboxylic acid halide (corresponding to the repeating unit III raw material) in the organic layer, or for the purpose of increasing the efficiency of the polymerization reaction, suppressing the hydrolysis of the dicarboxylic acid halide (corresponding to the repeating unit III raw material), and obtaining a polymer with a desired molecular weight, a part or all of the organic layer can also be replaced with an organic solvent that is also soluble in water.
• organic solvents that are effective for improving the solubility of the dicarboxylic acid halide (corresponding to the raw material of the repeating unit III) in the organic layer include tetrahydrofuran, N,N-dimethylacetamide (DMAc), N-methyl-2-pyrrolidone (NMP), dimethylsulfoxide (DMSO), 1,4-dioxane, and 1,3-dioxolane.
• DMAc N,N-dimethylacetamide
• NMP N-methyl-2-pyrrolidone
• DMSO dimethylsulfoxide
• 1,4-dioxane 1,3-dioxolane.
• the amount of polymer in the organic layer relative to the liquid amount is preferably 2% by mass or more, more preferably 6% by mass or more, and even more preferably 10% by mass or more.
• Acetic acid is added to the polymer solution obtained after polymerization, and after the polymerization is terminated, the polymer solution is repeatedly stirred and washed with water to remove ionic components contained in the polymer solution, such as sodium ions, potassium ions, lithium ions, chloride ions, and polymerization catalysts.
• the water used for washing can be either acidic or basic, and washing is repeated until the waste washing water becomes neutral.
• the obtained polymer solution is dropped into a poor solvent, whereby the polymer precipitates as a solid content.
• the solid content concentration of the polymer solution is preferably 7% by mass or less.
• the volume of the poor solvent is preferably at least three times the volume of the polymer solution. Examples of poor solvents include methanol, ethanol, isopropyl alcohol, acetone, acetonitrile, and hexane.
• the immersion time in the poor solvent after precipitation in the poor solvent is 1 minute or more.
• trimethylbenzylammonium halide or triethylbenzylammonium halide which has a relatively low polymerization activity, is used as the polymerization catalyst, it is preferable to set the immersion time to 3 minutes or more. If the polymer is removed in less than 3 minutes, the removal of residual monomers and impurities from the polymer may be insufficient. In order to reduce the amount of residual monomers and impurities, the above operation of dissolving the obtained polymer in a solvent again and adding it to a poor solvent for precipitation may be repeated.
• the amount of repeating unit II raw material (the amount of compound ii) used with respect to the total amount of repeating unit I raw material (the amount of compound i used) and the amount of repeating unit II raw material (the amount of compound ii used) is 10 mol% or more, and from the viewpoint that the wear resistance of the film formed by using the specific polyarylate obtained is more excellent, it is preferably 18 mol% or more, more preferably 26 mol% or more, and even more preferably 32 mol% or more.It should be noted that, although there is no particular limit as the upper limit, from the viewpoint that the film forming property of the specific polyarylate obtained is more excellent, it is preferably 50 mol% or less.
• the repeating unit I raw material is two or more kinds
• the above content represents the total content.
• the repeating unit II raw material is two or more kinds
• the above content represents the total content.
• the amount of the repeating unit I raw material used is preferably 5 to 45 mol %, more preferably 10 to 40 mol %, and even more preferably 15 to 35 mol %, based on the total content of the repeating unit I raw material, the repeating unit II raw material, and the repeating unit III raw material.
• the amount of the repeating unit II raw material used is preferably 5 to 45 mol %, more preferably 9 to 35 mol %, and even more preferably 13 to 25 mol %, based on the total content of the repeating unit I raw material, the repeating unit II raw material, and the repeating unit III raw material.
• the amount of the repeating unit III raw material used is preferably 30 to 70 mol %, more preferably 40 to 60 mol %, and even more preferably 45 to 55 mol %, based on the total content of the repeating unit I raw material, the repeating unit II raw material, and the repeating unit III raw material.
• the repeating unit I raw material may be one or more kinds, or two or more kinds may be used in combination.
• the above content represents the total content.
• the repeating unit II raw material may be one or more kinds, or two or more kinds may be used in combination.
• the repeating unit II raw material is two or more kinds
• the above content represents the total content.
• the repeating unit III raw material may be one or more kinds, or two or more kinds may be used in combination. When two or more kinds of repeating unit III raw materials are used, the above content represents the total content.
• the coating composition of the present invention contains a specific polyarylate.
• the coating composition of the present invention preferably contains the specific polyarylate and a solvent.
• the solvent include chlorine-based solvents such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, chlorobenzene, 1,1,2,2-tetrachloroethane, 1,1,1-trichloroethane, and o- and m-dichlorobenzene, aromatic hydrocarbons such as toluene, benzene, and xylene, N-methyl-2-pyrrolidone (NMP), N,N-dimethylacetamide (DMAc), 1,4-dioxane, and tetrahydrofuran. These solvents can be used alone or as a mixed solvent.
• the coating composition of the present invention may contain a functional material in order to impart desired functionality to the resulting coating film of the present invention.
• the function imparted to the coating film of the present invention is not limited to a specific function.
• the mass ratio of the specific polyarylene to the functional material is preferably, for example, 90:10 to 50:50, and more preferably 80:20 to 50:50.
• the functional material is not particularly limited, and from the viewpoint of further enhancing compatibility and interaction with the specific polyarylene, an aromatic ring-containing compound containing a benzene ring is preferred.
• the aromatic ring-containing compound containing a benzene ring is preferably a compound containing 2 to 15 benzene rings, more preferably a compound containing 3 to 12 benzene rings, and even more preferably a compound containing 4 to 10 benzene rings.
• the molecular weight of the aromatic ring-containing compound containing a benzene ring is preferably 200 to 2000, more preferably 250 to 1500, and even more preferably 300 to 1000.
• the aromatic ring-containing compound containing a benzene ring is preferably a compound represented by the following formula (V).
• X represents an oxygen atom, a sulfur atom, a hydrocarbon group which may have a substituent, or an imino group which may have a substituent
• n1 represents an integer of 0 to 4
• R represents a monovalent organic group or a hydroxyl group.
• the hydrocarbon group represented by X which may have a substituent is preferably a hydrocarbon group containing an aromatic ring and having 6 to 35 carbon atoms, more preferably a hydrocarbon group containing an aromatic ring and having 6 to 25 carbon atoms.
• n1 an integer of 0 to 2 is preferable, and 0 or 1 is more preferable.
• the monovalent organic group represented by R is preferably a linear alkyl group.
• the aromatic compound represented by the above formula (V) contains multiple benzene rings, contains heteroatoms such as oxygen atoms, sulfur atoms, and nitrogen atoms, and has a large mass ratio and rigidity of the benzene rings in the aromatic compound represented by the above formula (V), which can increase the compatibility and interaction between the specific polyarylene and the functional material, and can further improve the mechanical properties of the resulting coating film. It is also expected that the coating film will be densified, and the moisture permeability of the coating film will be reduced.
• the molecular weight of the aromatic compound represented by the above formula (V) is preferably 200 to 2,000, more preferably 250 to 1,500, and even more preferably 300 to 1,000.
• the number of benzene rings in the above formula (V) is preferably 2 to 15, more preferably 3 to 12, and even more preferably 4 to 10.
• the aromatic compound represented by the above formula (V) preferably contains at least one of an oxygen atom and a nitrogen atom.
• the coating film of the present invention may be composed of the specific polyarylene, or may contain other components in addition to the specific polyarylene. Examples of other components include the functional materials described above.
• the mass ratio of the specific polyarylene to the functional material is, for example, preferably 90:10 to 50:50, and more preferably 80:20 to 50:50.
• the coating film of the present invention has excellent film-forming properties when formed, and the coating film itself also has excellent heat resistance and abrasion resistance.
• An example of a coating film combined with a functional material is a low moisture permeable film as described in JP 2016-069468 A.
• a phenol compound as a functional material to a polymer, the polymer and the functional material exhibit high compatibility, and moisture permeability can be effectively suppressed.
• a composite coating film containing a functional material is an organic device, which contains a specific polyarylate as a binder and a functional material such as a charge transport material, and the binder is required to have high compatibility with the functional material.
• the coating film of the present invention can also be preferably used as, for example, a metal wire coating film and a polarizing plate protective film for a display device.
• the coating film of the present invention can also be used with other layers disposed on it.
• durability can be further increased by forming a protective layer in contact with the coating film of the present invention.
• the method for producing the coating film of the present invention is not particularly limited as long as it can form a film containing a specific polyarylene.
• the coating film can be formed by applying the coating composition of the present invention onto a substrate and drying the coating film.
• the coating method and drying method themselves can be appropriately applied to methods that can be normally adopted in applying and drying a coating liquid.
• the substrate is not particularly limited, and can be widely applied to materials, members, etc. that have a surface to be coated.
• aqueous solution B In a reaction vessel equipped with a stirrer, 4.78 g of 2,2'-dimethylbiphenol (synthesized by standard methods) and 80 mL of water were added to form a suspension. 2.16 g of sodium hydroxide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was added to this suspension at room temperature (20°C) while stirring, and the solution was stirred for 30 minutes under a nitrogen atmosphere to obtain a solution in which the solids were mostly dissolved. This is called aqueous solution B.
• Example 2 Synthesis of polymer (2) Polymer (2) was synthesized in the same manner as in the synthesis of polymer (1), except that the raw materials were changed as shown in the following scheme.
• Example 3 Synthesis of polymer (3) Polymer (3) was synthesized in the same manner as for polymer (1), except that the raw materials were changed as shown in the following scheme.
• Example 4 Synthesis of polymer (4) Polymer (4) was synthesized in the same manner as for polymer (1), except that the raw materials were changed as shown in the following scheme.
• Comparative Example 1 Synthesis of Polymer (R1) According to the procedure of Synthesis Example 1 of JP-A-2019-095642, the polyester resin of Synthesis Example 9 of JP-A-2019-095642 was synthesized as polymer (R1). Specifically, it is as follows.
• Comparative Example 2 Synthesis of Polymer (R2) According to the procedure of Synthesis Example 1 of JP-A-2017-215584, the polyester resin of Synthesis Example 15 of JP-A-2017-215584 was synthesized as polymer (R2). Specifically, the procedure is as follows.
• Comparative Example 3 Synthesis of Polymer (R3) According to the procedure of Synthesis Example 1 of JP-A-2017-215584, the polyester resin of Synthesis Example 7 of JP-A-2017-215584 was synthesized as polymer (R3). Specifically, the procedure is as follows.
• a coating solution was prepared by mixing 1.2 g of the polymer synthesized above with 18 g of tetrahydrofuran (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) as a solvent. The coating solution was then dropped into a petri dish and dried to prepare a cast film (coating film) with a thickness of 10 to 50 ⁇ m. This cast film was peeled off from the petri dish to prepare polymer film A for evaluation.
• a coating solution was prepared by mixing 800 mg of the polymer synthesized above, 400 mg of 4,4'-( ⁇ -methylbenzylidene)bisphenol (manufactured by Tokyo Chemical Industry Co., Ltd.) as an aromatic ring-containing compound (functional material), and 18 g of tetrahydrofuran (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) as a solvent.
• the coating solution was then dropped into a petri dish and dried to prepare a cast film (coating film) with a thickness of 10 to 50 ⁇ m. This cast film was peeled off from the petri dish to prepare polymer film B for evaluation.
• evaluation polymer film A (cast film) prepared in (1) was attached to a Taber "S-36" to prepare an evaluation sample for the abrasion resistance test.
• the prepared evaluation sample was set in a rotary abrasion tester (manufactured by Toyo Seiki Seisakusho Co., Ltd.), and an abrasion evaluation test was performed by rotating the sample 2000 times under the conditions of a load of 500 gf and a rotation speed of 60 rpm using an abrasion wheel CS-10 (manufactured by Taber Co., Ltd.).
• the abrasion loss (mg/2000 revolutions), which is the change in mass of the sample before and after the abrasion evaluation test, was measured. Based on the obtained abrasion loss, the abrasion resistance of the evaluation sample was evaluated according to the following criteria. The results are shown in Table 1 (column "Wear Resistance (1)”). ⁇ Evaluation Criteria for Abrasion Resistance> "A”: Abrasion loss is less than 7 mg. "B”: Abrasion loss is 7 mg or more but less than 8 mg. “C”: Abrasion loss is 8 mg or more but less than 10 mg. “D”: Abrasion loss is 10 mg or more but less than 13 mg. “E”: Abrasion loss is 13 mg or more.
• Abrasion loss is less than 7 mg.
• B Abrasion loss is 7 mg or more but less than 8 mg.
• C Abrasion loss is 8 mg or more but less than 10 mg.
• D Abrasion loss is 10 mg or more but less than 13 mg.
• E Abrasion loss is 13 mg or more.
• Table 1 is shown below.
• “Polymer synthesis method” “A” refers to synthesis by a method based on the polyarylate production method of the present invention (divided addition), and “B” refers to synthesis by a method in which the repeating unit I raw material, the repeating unit II raw material, and the repeating unit III raw material are added all at once without being added in portions.

Landscapes

• Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Organic Chemistry (AREA)
• Health & Medical Sciences (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)
• Wood Science & Technology (AREA)
• Polyesters Or Polycarbonates (AREA)

Priority Applications (1)

Applications Claiming Priority (2)

Publications (1)

Family

ID=92590534

Family Applications (1)

Country Status (2)

Citations (5)

• 2024
  • 2024-02-22 JP JP2025503846A patent/JPWO2024181315A1/ja active Pending
  • 2024-02-22 WO PCT/JP2024/006596 patent/WO2024181315A1/ja not_active Ceased

Patent Citations (5)

Also Published As

Similar Documents

Legal Events