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JP-7857287-B2 - Coating resin composition, polymer, method for producing polymer, coating film, and method for producing the same.

JP7857287B2JP 7857287 B2JP7857287 B2JP 7857287B2JP-7857287-B2

Inventors

  • 弘中 幸治
  • 小川 泰輝
  • 上平 茂生

Assignees

  • 富士フイルム株式会社

Dates

Publication Date
20260512
Application Date
20220427
Priority Date
20210514

Claims (14)

  1. The polymer comprises a structural unit represented by the following formula (I-A), at least one of the structural units represented by the following formula (I-B), and a structural unit represented by the following formula (II). A coating resin composition in which the polymer contains, in total, 10% by mass or more of the structural unit represented by formula (I-A) and the structural unit represented by formula (I-B), and the content of the structural unit represented by formula (II) is 10% by mass or more. In the formula, R1 represents an unsubstituted chain-like branched alkyl group having four or more carbon atoms. R2 represents a hydrogen atom, a linear alkyl group, or an aryl group. R3 represents a hydrogen atom, an alkyl group, or an aryl group. R1 and R2 do not bond to form a ring structure. Also, the sum of the number of carbon atoms in R1 and the two R3 atoms is 6 or more. No substituents other than R3 exist on the two benzene rings shown in the formula. In the formula, R4 represents a hydrogen atom, a linear alkyl group, or an aryl group. n is an integer between 2 and 20. R5 represents a hydrogen atom, an alkyl group, or an aryl group. No substituents other than R 5 exist on the two benzene rings shown in the formula. In the formula, R c represents an alkyl group, an aryl group, or a halogen atom, and r is an integer from 0 to 4.
  2. The coating resin composition according to claim 1, wherein in formula (I-A), R2 is a hydrogen atom or an unsubstituted hydrocarbon group, and the content of the structural unit represented by formula (I-A) in the polymer is 10% by mass or more.
  3. The coating resin composition according to claim 2, wherein the polymer contains 20% by mass or more of the structural unit represented by formula (I-A).
  4. The coating resin composition according to claim 1 or 2, wherein at least a portion of the structural units represented by formula (II) are contained in the polymer as structural units represented by the following formula (II-1), and the content of the structural units represented by formula (II-1) in the polymer is 10% by mass or more. In the formula, R c and r are the same as R c and r in formula (II) above.
  5. The coating resin composition according to claim 4, wherein the polymer contains 20% by mass or more of the structural unit represented by formula (II-1).
  6. The coating resin composition according to claim 1 or 2, wherein in formula (I-A), R3 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and at least one of the two R3s is an alkyl group having 1 to 4 carbon atoms, and in formula (I-B), R5 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and at least one of the two R5s is an alkyl group having 1 to 4 carbon atoms.
  7. The coating resin composition according to claim 1 or 2, wherein the number of carbon atoms in R1 is 5 or more.
  8. The coating resin composition according to claim 1 or 2, wherein n is an integer from 4 to 20.
  9. A coating resin composition according to claim 1 or 2, comprising a solvent.
  10. A coating resin composition according to claim 1 or 2, comprising a functional material consisting of an aromatic ring compound containing a benzene ring, wherein the mass ratio of the polymer content to the functional material content is polymer/functional material = 90:10 to 50:50.
  11. It has a structural unit represented by the following formula (I-A), at least one of the structural units represented by the following formula (I-B), a structural unit represented by the following formula (II) , and a terminal structure represented by the following formula (IV-1) or (IV-2) , A polymer in which the total content of the structural unit represented by formula (I-A) and the structural unit represented by formula (I-B) is 10% by mass or more, and the content of the structural unit represented by formula (II) is 10% by mass or more. In the formula, R1 represents an unsubstituted chain-like branched alkyl group having four or more carbon atoms. R2 represents a hydrogen atom, a linear alkyl group, or an aryl group. R3 represents a hydrogen atom, an alkyl group, or an aryl group. R1 and R2 do not bond to form a ring structure. Also, the sum of the number of carbon atoms in R1 and the two R3 atoms is 6 or more. No substituents other than R3 exist on the two benzene rings shown in the formula. In the formula, R4 represents a hydrogen atom, a linear alkyl group, or an aryl group. n is an integer between 2 and 20. R5 represents a hydrogen atom, an alkyl group, or an aryl group. No substituents other than R 5 exist on the two benzene rings shown in the formula. In the formula, R c represents an alkyl group, an aryl group, or a halogen atom, and r is an integer from 0 to 4. In the formulas, Ra and Rb represent monovalent organic groups. In formula (IV-1), Ra is bonded to the oxygen atom shown in formula (IV-1) by the carbon atom in Ra , and in formula (IV-2), Rb is bonded to the carbonyl group shown in formula (IV-2) by the carbon atom in Rb . * indicates a bonding site.
  12. The process includes a step of mixing a mixture containing an alkaline aqueous solution of divalent phenol and an organic solvent with solid 4,4'-biphenyldicarbonyl chloride. A method for producing a polymer having at least one of the structural units represented by the following formula (I-A) and the structural unit represented by the following formula (I-B), and the structural unit represented by the following formula (II-2), wherein the total content of the structural unit represented by formula (I-A) and the structural unit represented by formula (I-B) is 10% by mass or more, and the content of the structural unit represented by formula (II-2) is 10% by mass or more. In the formula, R1 represents an unsubstituted chain-like branched alkyl group having four or more carbon atoms. R2 represents a hydrogen atom, a linear alkyl group, or an aryl group. R3 represents a hydrogen atom, an alkyl group, or an aryl group. R1 and R2 do not bond to form a ring structure. Also, the sum of the number of carbon atoms in R1 and the two R3 atoms is 6 or more. No substituents other than R3 exist on the two benzene rings shown in the formula. In the formula, R4 represents a hydrogen atom, a linear alkyl group, or an aryl group. n is an integer between 2 and 20. R5 represents a hydrogen atom, an alkyl group, or an aryl group. No substituents other than R 5 exist on the two benzene rings shown in the formula.
  13. A coating film comprising the polymer described in claim 11.
  14. A method for forming a coating film, comprising coating a substrate with the coating resin composition described in claim 1 or 2.

Description

This invention relates to a resin composition for coating, a polymer, a method for producing a polymer, a coating film, and a method for producing the same. Polyesters containing structural units derived from aromatic diol compounds and aromatic dicarboxylic acid compounds, and polycarbonates containing structural units derived from aromatic diol compounds and phosgene, are excellent in terms of heat resistance and mechanical strength, and are widely used industrially. For example, Patent Document 1 describes a film-forming resin mainly composed of a polyester comprising residues of divalent carboxylic acids having biphenyl, diphenyl ether, and cyclohexane structures, and residues of divalent phenols. It states that by controlling the amount of free divalent carboxylic acids to 0.01 to 300 ppm, the electrical properties can be stabilized when applied to capacitors, electrophotographic photoreceptors, etc. Furthermore, Patent Document 2 describes a resin composition comprising 100 parts by mass of a polymer resin composition in which 95 to 5% by mass of a polyarylate component (A) and 5 to 95% by mass of a polycarbonate component (B) are combined to make 100% by mass, and 0.01 to 1 part by mass of a silicone compound (C) having a glycidyl group of a specific structure. According to Patent Document 2, molded articles using this composition possess both heat resistance and transparency, and are suitable for automotive lamp peripheral parts, lighting fixture reflectors, and the like. Japanese Patent Publication No. 2008-31347Japanese Patent Publication No. 2003-292756 In the description of this invention, the numerical range represented by "~" means a range that includes the numbers written before and after "~" as the lower limit and upper limit, respectively. In the description of this invention, substituents, linking groups, etc. (hereinafter referred to as "substituents, etc.") that are not explicitly stated as substituted or unsubstituted are considered to have appropriate substituents. Therefore, even when simply referred to as "~group" (e.g., "alkyl group") in this specification, this "~group" (e.g., "alkyl group") includes not only the unsubstituted form (e.g., "unsubstituted alkyl group") but also the form with a substituent (e.g., "substituted alkyl group"). The same applies to compounds that are not explicitly stated as substituted or unsubstituted. Preferred substituents include those selected from substituent T described below. In the description of the present invention, when there are multiple substituents, or when multiple substituents are specified simultaneously or alternatively, it means that each substituent may be the same as or different from the others. Furthermore, even if not specifically stated otherwise, when multiple substituents are adjacent to each other, they may be linked to each other or fused to form a ring. In this specification, if a polymer has multiple components of the same designation (designated by the same general formula), each component may be identical or different from the others. [Coating resin composition] The coating resin composition of the present invention comprises a polymer having at least one of the structural units represented by the following formula (I-A) and the following formula (I-B), and a structural unit represented by the following formula (II). This polymer may hereafter be simply referred to as "the above polymer." In the above formula (I-A), R1 represents an unsubstituted linear branched alkyl group having 4 or more carbon atoms (the linear branched alkyl group of R1 has no substituents). The number of carbon atoms in R1 is preferably 4 to 20, more preferably 4 to 15, even more preferably 4 to 10, and particularly preferably 4 to 8. It is also preferable that the number of carbon atoms in R1 be 5 or more. Therefore, it is also preferable that the number of carbon atoms in R1 be 5 to 20, 6 to 15, 6 to 10, and 7 to 8. Preferred specific examples of R1 include 1-methylpropyl group, 2-methylpropyl group, 1,2-dimethylpropyl group, 2,2-dimethylpropyl group, 1-ethylpropyl group, 1-methylbutyl group, 2-methylbutyl group, 3-methylbutyl group, 1-ethylbutyl group, 2-ethylbutyl group, 1,1-dimethylbutyl group, 1,2-dimethylbutyl group, 1,3-dimethylbutyl group, 2,2-dimethylbutyl group, 3,3-dimethylbutyl group, 4-methylpentyl group, 1-ethylpentyl group, 2-ethylpentyl group, 3-ethylpentyl group, 1,3-dimethylpentyl group, 1,4-dimethylpentyl group, 2,4,4-trimethylpentyl group, 1-ethylheptyl group, 2-ethylheptyl group, 3-methylhexyl group, 11-methyldodecyl group, and the like. In particular, R1 is preferably 1-methylpropyl group, 2-methylpropyl group, 1-methylbutyl group, 3-methylbutyl group, 1-ethylpropyl group, 1-ethylbutyl group, 1-ethylpentyl group, 1-ethylhexyl group, 1-ethylheptyl group, or 2,4,4-trimethylpentyl group, and more preferably 2-methylpropyl group, 1-ethylbutyl group, 1-ethylpentyl group, 2,4,4-trimethylpentyl group, or 1-ethylheptyl group. R2 repr