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US-20260125355-A1 - COMPOSITION CONTAINING FLUORINE-CONTAINING MONOMER AND FLUORIDE IONS, METHOD FOR PRODUCING FLUORINE-CONTAINING MONOMER HAVING REDUCED FLUORIDE ION CONTENT, AND METHOD FOR PURIFYING FLUORINE-CONTAINING MONOMER

US20260125355A1US 20260125355 A1US20260125355 A1US 20260125355A1US-20260125355-A1

Abstract

The present disclosure aims to provide a composition comprising a fluorine-containing monomer and fluoride ions wherein the amount of fluoride ions mixed in the fluorine-containing monomer is small, a method for producing a fluorine-containing monomer having a further reduced fluoride ion content from a fluorine-containing monomer contaminated with fluoride ions, a method for purifying a fluorine-containing monomer contaminated with fluoride ions, and the like. The present disclosure relates to a composition comprising a fluorine-containing monomer (M) and fluoride ions, wherein the fluoride ion content is 0.01 to 1000 ppm by mass based on the mass of the composition, and the fluorine-containing monomer (M) is at least one monomer selected from the group consisting of a compound represented by formula (M1), a compound represented by formula (M2), and a compound represented by formula (M3): wherein R 1 to R 10 each independently represent a fluorine atom, a perfluoroalkyl group, or a perfluoroalkoxy group.

Inventors

  • Daichi Mari
  • Noriyuki Shinoki
  • Tadashi Ino

Assignees

  • DAIKIN INDUSTRIES, LTD.

Dates

Publication Date
20260507
Application Date
20260105
Priority Date
20230711

Claims (20)

  1. 1 . A composition comprising a fluorine-containing monomer (M) and fluoride ions, wherein the fluoride ion content is 0.01 to 1000 ppm by mass based on the mass of the composition, and the fluorine-containing monomer (M) is at least one monomer selected from the group consisting of a compound represented by formula (M1): wherein R 1 and R 2 each independently represent a fluorine atom, a perfluoroalkyl group, or a perfluoroalkoxy group, a compound represented by formula (M2): wherein R 3 , R 4 , R 5 , and R 6 each independently represent a fluorine atom, a perfluoroalkyl group, or a perfluoroalkoxy group, and a compound represented by formula (M3): wherein R 7 , R 8 , R 9 , and R 10 each independently represent a fluorine atom, a perfluoroalkyl group, or a perfluoroalkoxy group.
  2. 2 . The composition according to claim 1 , wherein the fluorine-containing monomer (M) is at least one compound selected from the group consisting of a compound represented by the following formula (M1-1), a compound represented by the following formula (M2-1), a compound represented by the following formula (M2-2), a compound represented by the following formula (M3-1), and a compound represented by the following formula (M3-2):
  3. 3 . The composition according to claim 1 , wherein the fluorine-containing monomer (M) is a compound represented by the following formula (M3-1):
  4. 4 . The composition according to claim 3 , further comprising a compound represented by the following formula (C):
  5. 5 . The composition according to claim 4 , wherein the content of the compound represented by formula (C) is 0.01 to 10 mass % based on the mass of the composition.
  6. 6 . The composition according to claim 1 , wherein the fluoride ion content is 50 to 600 ppm by mass based on the mass of the composition.
  7. 7 . The composition according to claim 1 , wherein the fluorine-containing monomer (M) is a compound represented by the following formula (M3-1): and the fluoride ion content is 50 to 600 ppm by mass based on the mass of the composition.
  8. 8 . A method for producing a fluorine-containing monomer (M) having a further reduced fluoride ion content from a fluorine-containing monomer (M) contaminated with fluoride ions, the method comprising: subjecting the fluorine-containing monomer (M) contaminated with fluoride ions to at least one treatment selected from the group consisting of activated carbon adsorption and washing to reduce fluoride ions; wherein the fluoride ion content of the fluorine-containing monomer (M) produced is 0.01 to 1000 ppm by mass, and the fluorine-containing monomer (M) is at least one monomer selected from the group consisting of a compound represented by formula (M1): wherein R 1 and R 2 each independently represent a fluorine atom, a perfluoroalkyl group, or a perfluoroalkoxy group, a compound represented formula (M2): wherein R 3 , R 4 , R 5 , and R 6 each independently represent a fluorine atom, a perfluoroalkyl group, or a perfluoroalkoxy group, and a compound represented by formula (M3): wherein R 7 , R 1 , R 9 , and R 10 each independently represent a fluorine atom, a perfluoroalkyl group, or a perfluoroalkoxy group.
  9. 9 . The production method according to claim 8 , wherein the treatment of the fluorine-containing monomer (M) contaminated with fluoride ions is activated carbon adsorption.
  10. 10 . The production method according to claim 9 , wherein the activated carbon adsorption treatment comprises distilling the fluorine-containing monomer (M) contaminated with fluoride ions and subjecting the distilled fluorine-containing monomer (M) to activated carbon adsorption treatment.
  11. 11 . The production method according to claim 8 , wherein the washing is performed with water or an alkaline aqueous solution.
  12. 12 . The production method according to claim 8 , wherein the fluorine-containing monomer (M) is at least one compound selected from the group consisting of a compound represented by the following formula (M1-1), a compound represented by the following formula (M2-1), a compound represented by the following formula (M2-2), a compound represented by the following formula (M3-1), and a compound represented by the following formula (M3-2):
  13. 13 . The production method according to claim 8 , wherein the fluorine-containing monomer (M) is a compound represented by the following formula (M3-1):
  14. 14 . The production method according to claim 8 , wherein the fluoride ion content of the fluorine-containing monomer (M) produced is 50 to 600 ppm by mass.
  15. 15 . The production method according to claim 8 , wherein the fluorine-containing monomer (M) is a compound represented by the following formula (M3-1): the treatment of the fluorine-containing monomer (M) contaminated with fluoride ions comprises (1) subjecting the fluorine-containing monomer (M) contaminated with fluoride ions to activated carbon adsorption treatment, (2) distilling the fluorine-containing monomer (M) contaminated with fluoride ions and subjecting the distilled fluorine-containing monomer (M) to activated carbon adsorption treatment, or (3) washing the fluorine-containing monomer (M) contaminated with fluoride ions with water or an alkaline aqueous solution, and the fluoride ion content of the fluorine-containing monomer (M) produced is 50 to 600 ppm by mass.
  16. 16 . A method for purifying a fluorine-containing monomer (M) contaminated with fluoride ions, the method comprising: subjecting the fluorine-containing monomer (M) contaminated with fluoride ions to at least one treatment selected from the group consisting of activated carbon adsorption and washing to reduce fluoride ions; wherein the fluorine-containing monomer (M) is at least one monomer selected from the group consisting of a compound represented by formula (M1): wherein R 1 and R 2 each independently represent a fluorine atom, a perfluoroalkyl group, or a perfluoroalkoxy group, a compound represented by formula (M2): wherein R 3 , R 4 , R 5 , and R 6 each independently represent a fluorine atom, a perfluoroalkyl group, or a perfluoroalkoxy group, and a compound represented by formula (M3): wherein R 7 , R 1 , R 9 , and R 10 each independently represent a fluorine atom, a perfluoroalkyl group, or a perfluoroalkoxy group.
  17. 17 . The purification method according to claim 16 , wherein the fluoride ion content of a fluorine-containing monomer (M) purified is 0.01 to 1000 ppm by mass.
  18. 18 . The purification method according to claim 16 , wherein the fluoride ion content of a fluorine-containing monomer (M) purified is 50 to 600 ppm by mass.
  19. 19 . The purification method according to claim 16 , wherein the treatment of the fluorine-containing monomer (M) contaminated with fluoride ions is activated carbon adsorption.
  20. 20 . The purification method according to claim 19 , wherein the activated carbon adsorption treatment comprises distilling the fluorine-containing monomer (M) contaminated with fluoride ions and subjecting the distilled fluorine-containing monomer (M) to activated carbon adsorption treatment.

Description

TECHNICAL FIELD The present disclosure relates to a composition containing a fluorine-containing monomer and fluoride ions, a method for producing a fluorine-containing monomer having a reduced fluoride ion content, a method for purifying a fluorine-containing monomer, and the like. BACKGROUND ART Specific fluorine-containing monomers are used as starting materials for polymerization to obtain fluorine-containing polymers. For example, a fluorine-containing polymer obtained by polymerizing perfluoro(2-methylene-4-methyl-1,3-dioxolane), which is a fluorine-containing monomer with a ring structure, is useful for electronic components, optical materials, etc. Specific fluorine-containing monomers are prone to polymerization during storage. Thus, in order to stably store such monomers, techniques for inhibiting polymerization have been reported (PTL 1 and PTL 2). PTL 1 discloses a monomer composition containing a fluorine-containing monomer, 2,6-di-t-butyl-p-cresol, and the like. PTL 2 discloses a method for stabilizing perfluoro(2-methylene-4-methyl-1,3-dioxolane) by incorporating a hydroxy group-containing fluoroaromatic compound of a specific structure into a composition containing perfluoro(2-methylene-4-methyl-1,3-dioxolane). CITATION LIST Patent Literature PTL 1: WO2018/062193PTL 2: WO2020/130122 SUMMARY The present disclosure encompasses, for example, the following aspects. A composition comprising a fluorine-containing monomer (M) and fluoride ions, wherein the fluoride ion content is 0.01 to 1000 ppm by mass based on the mass of the composition, andthe fluorine-containing monomer (M) is at least one monomer selected from the group consisting ofa compound represented by formula (M1): wherein R1 and R2 each independently represent a fluorine atom, a perfluoroalkyl group, or a perfluoroalkoxy group, a compound represented by formula (M2): wherein R3, R4, R5, and R6 each independently represent a fluorine atom, a perfluoroalkyl group, or a perfluoroalkoxy group, and a compound represented by formula (M3): wherein R7, R8, R9, and R10 each independently represent a fluorine atom, a perfluoroalkyl group, or a perfluoroalkoxy group. Advantageous Effects The present disclosure provides a method for reducing fluoride ions mixed in a specific fluorine-containing monomer (i.e., a method for purifying a fluorine-containing monomer). The use of this method enables the provision of a composition comprising a fluorine-containing monomer and fluoride ions wherein the amount of fluoride ions mixed in the fluorine-containing monomer is small, and enables the production of a fluorine-containing monomer having a further reduced fluoride ion content from a fluorine-containing monomer contaminated with fluoride ions. DESCRIPTION OF EMBODIMENTS The above overview of the present disclosure is not intended to describe each of the disclosed embodiments or all of the implementations of the present disclosure. The following description of the present disclosure more specifically provides examples of illustrative embodiments. Guidance is provided through examples in several parts of the present disclosure, and these examples can be used in various combinations. In each case, the group of examples can function as a non-exclusive and representative group. All publications, patents, and patent applications cited herein are incorporated herein by reference in their entirety. Terms Unless otherwise specified, the symbols and abbreviations in the present specification can be understood in the context of the present specification in the meanings commonly used in the technical field to which the present disclosure belongs. In the present specification, the terms “comprise” and “contain” are used with the intention of including the phrases “consisting essentially of” and “consisting of.” Unless otherwise specified, the steps, treatments, or operations described in the present specification may be performed at room temperature. In the present specification, room temperature can refer to a temperature within the range of 10 to 40° C. In the present specification, the phrase “Cn-Cm” (n and m are each a number) indicates that the number of carbon atoms is n or more and m or less, as a person skilled in the art would generally understand. In the present specification, the description of compounds can include all stereoisomers (enantiomers, diastereomers, geometric isomers, etc.) unless otherwise specified by a person skilled in the art. In the present specification, unless otherwise specified, “alkyl” includes linear, branched, or cyclic alkyl groups. “Alkyl” may be linear or branched alkyl. The number of carbon atoms in “alkyl” may be, for example, 1 to 12, 1 to 6, 1 to 5, 1 to 4, 1 to 3, 6, 5, 4, 3, 2, or 1. Examples of alkyl include linear or branched alkyl groups, such as methyl, ethyl, propyl (e.g., n-propyl, isopropyl), butyl (e.g., n-butyl, isobutyl, sec-butyl, tert-butyl), pentyl (e.g., n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pe