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CN-122029212-A - Curable resin and method for producing same, curable resin composition, prepreg, metal-clad laminate, and method for producing same

CN122029212ACN 122029212 ACN122029212 ACN 122029212ACN-122029212-A

Abstract

The invention provides a curable resin excellent in adhesion to a metal foil and excellent in electrical characteristics and heat resistance, a method for producing the same, a curable resin composition containing the curable resin, a prepreg, a metal-clad laminate, and a method for producing the same. The curable resin has at least an alpha-olefin structure represented by the following formula (1), an iodine value of 70 or more, and a weight average molecular weight Mw of 2500 or more. In the formula (1), R 1 each independently represents a hydrocarbon group having 1 to 10 carbon atoms or a halogenated alkyl group, p1 represents a real number of 0 to 4, and each represents a bonding position.

Inventors

  • YAGISHITA MASASHI
  • HIRATA TAKUMA
  • IWAMOTO TADASHI
  • TAKEUCHI HIROSHI
  • LI MINGMIN
  • MAEDA HISAO

Assignees

  • ＡＧＣ株式会社

Dates

Publication Date
20260512
Application Date
20241016
Priority Date
20231016

Claims (20)

  1. 1. A curable resin having at least an alpha-olefin structure represented by the following formula (1), an iodine value of 70 or more and a weight average molecular weight Mw of 2500 or more, In the formula (1), R 1 each independently represents a hydrocarbon group having 1 to 10 carbon atoms or a halogenated alkyl group, p1 represents a real number of 0 to 4, and each represents a bonding position.
  2. 2. The curable resin according to claim 1, wherein the iodine value is 70 to 200.
  3. 3. The curable resin according to claim 1, wherein the content of the alpha olefin structure represented by the formula (1) is 1.0mmol/g or more.
  4. 4. The curable resin according to claim 3, wherein the content of the alpha olefin structure represented by the formula (1) is 1.0mmol/g to 6.3mmol/g.
  5. 5. The curable resin according to claim 1, wherein the following parameter FA represented by the content of the alpha-olefin structure represented by the formula (1), the content of the indane structure represented by the following formula (2) and the content of the internal olefin structure represented by the following formula (3) in the curable resin is 0.39 or more, Fa= [ content of alpha olefin structure ]/([ content of internal olefin structure ] + [ content of indan structure ] + [ content of alpha olefin structure ]) In the formula (2), R 2 independently represents a hydrocarbon group or a halogenated alkyl group having 1 to 10 carbon atoms, p2 represents a real number of 0 to 4, q1 represents a real number of 0 to 3, each represents a bonding position, In the formula (3), R 3 each independently represents a hydrocarbon group having 1 to 10 carbon atoms or a halogenated alkyl group, p3 represents a real number of 0 to 4, and each represents a bonding position.
  6. 6. The curable resin according to claim 1, wherein the following parameters FI represented by the content of the alpha-olefin structure represented by the formula (1), the content of the indane structure represented by the following formula (2), and the content of the internal olefin structure represented by the following formula (3) in the curable resin are less than 0.58, Fi= [ content of indane structure ]/([ content of internal olefin structure ] + [ content of indane structure ] + [ content of alpha olefin structure ]/2) In the formula (2), R 2 independently represents a hydrocarbon group or a halogenated alkyl group having 1 to 10 carbon atoms, p2 represents a real number of 0 to 4, q1 represents a real number of 0 to 3, each represents a bonding position, In the formula (3), R 3 each independently represents a hydrocarbon group having 1 to 10 carbon atoms or a halogenated alkyl group, p3 represents a real number of 0 to 4, and each represents a bonding position.
  7. 7. The curable resin according to claim 1, wherein the content of hetero atoms other than carbon atoms and hydrogen atoms is 3 mass% or less.
  8. 8. The curable resin according to claim 7, wherein the hetero atom is not contained.
  9. 9. The curable resin according to claim 1, wherein an olefin structure is present at a terminal of the molecular structure.
  10. 10. The curable resin according to claim 1, further comprising a side chain olefin structure having an olefin structure in a side chain portion.
  11. 11. The curable resin according to claim 1, wherein the total content of the alpha olefin structure, the olefin structure at the molecular structure terminal, and the side chain olefin structure having an olefin structure in the side chain portion is 1.8mmol/g or more.
  12. 12. The curable resin according to claim 1, wherein the indane structure represented by the following formula (2) is contained in an amount of 3.0mmol/g or less, In the formula (2), R 2 independently represents a hydrocarbon group or a halogenated alkyl group having 1 to 10 carbon atoms, p2 represents a real number of 0 to 4, q1 represents a real number of 0 to 3, and each represents a bonding position.
  13. 13. The curable resin according to claim 1, wherein the weight average molecular weight Mw is 5000 to 500000.
  14. 14. A process for producing a curable resin, comprising polymerizing a compound having a plurality of isopropenyl groups at a reaction temperature of 10-75 ℃ in the presence of an acid catalyst to obtain a curable resin having at least an alpha-olefin structure represented by the following formula (1), an iodine value of 70 or more and a weight average molecular weight Mw of 2500 or more, In the formula (1), R 1 each independently represents a hydrocarbon group having 1 to 10 carbon atoms or a halogenated alkyl group, p1 represents a real number of 0 to 4, and each represents a bonding position.
  15. 15. The method for producing a curable resin according to claim 14, wherein the acid catalyst is selected from a mixture of 1 or more of an ester compound, a ketone compound and an ether compound with 1 or more of a bronsted acid, a lewis acid, an organic sulfonic acid and an inorganic acid, and methanesulfonic acid, BF3 complex, stannic chloride and toluenesulfonic acid.
  16. 16. The method for producing a curable resin according to claim 14 or 15, wherein the curing temperature in the polymerization reaction of the compound having a plurality of isopropenyl groups is 10 to 75 ℃ and the curing time is 5 minutes to 72 hours.
  17. 17. A curable resin composition comprising the curable resin according to any one of claims 1 to 13.
  18. 18. A prepreg comprising the curable resin composition according to claim 17.
  19. 19. A metal-clad laminate comprising a cured product of the curable resin composition according to claim 17 and a metal foil.
  20. 20. The metal-clad laminate of claim 19 wherein the metal foil has a peel strength of 2.0N/cm or greater.

Description

Curable resin and method for producing same, curable resin composition, prepreg, metal-clad laminate, and method for producing same Technical Field The present disclosure relates to a curable resin and a method for producing the same, a curable resin composition, a prepreg, a metal-clad laminate, and a method for producing the same. Background A laminated board used for a printed circuit board for high-speed communication is required to have further higher performance. The curable resin used for the laminate is required to have practical performances such as heat resistance and adhesion to the metal foil, in addition to electrical insulation. Patent document 1 discloses an indane structure-containing polymer based on a specific diisoalkenyl aromatic hydrocarbon, which has sufficient thermal and electronic characteristics. Prior art literature Patent literature Patent document 1 Japanese patent application laid-open No. 2022-100270 Disclosure of Invention When a polymer containing many indane structures described in patent document 1 is used for a metal-clad laminate, adhesion to a metal foil may be poor. The present disclosure has been made in view of the above problems, and an object thereof is to provide a curable resin excellent in adhesion to a metal foil and excellent in electrical characteristics and heat resistance, a method for producing the curable resin, a curable resin composition containing the curable resin, a prepreg, a metal-clad laminate, and a method for producing the curable resin. The curable resin of the present disclosure has at least an alpha-olefin structure represented by the following formula (1), an iodine value of 70 or more, and a weight average molecular weight Mw of 2500 or more. (In the formula (1), R 1 each independently represents a hydrocarbon group having 1 to 10 carbon atoms or a haloalkyl group, p1 represents a real number of 0 to 4, and each represents a bonding position.) The iodine value of the curable resin may be 70 to 200. The content of the alpha-olefin structure represented by the formula (1) in any of the curable resins may be 1.0mmol/g or more. The content of the alpha-olefin structure represented by the formula (1) in any one of the curable resins may be 1.0 to 6.3mmol/g. In any of the curable resins, the following parameter FA represented by the content of the α -olefin structure represented by the above formula (1), the content of the indane structure represented by the following formula (2), and the content of the internal olefin structure represented by the following formula (3) in the curable resin may be 0.39 or more. Fa= [ content of alpha olefin structure ]/([ content of internal olefin structure ] + [ content of indan structure ] + [ content of alpha olefin structure ]) (In the formula (2), R 2 each independently represents a hydrocarbon group or a halogenated alkyl group having 1 to 10 carbon atoms, p2 represents a real number of 0 to 4, q1 represents a real number of 0 to 3, and each represents a bonding position.) (In the formula (3), R 3 each independently represents a hydrocarbon group having 1 to 10 carbon atoms or a haloalkyl group, p3 represents a real number of 0 to 4, and each represents a bonding position.) In any of the curable resins, the following parameter FI represented by the content of the α -olefin structure represented by the formula (1), the content of the indane structure represented by the formula (2), and the content of the internal olefin structure represented by the formula (3) in the curable resin may be less than 0.58. Fi= [ content of indane structure ]/([ content of internal olefin structure ] + [ content of indane structure ] + [ content of alpha olefin structure ]/2) The content of the hetero atoms other than the carbon atoms and the hydrogen atoms in any of the curable resins may be 3 mass% or less. Any of the curable resins may not contain the hetero atom. Any of the curable resins may have an olefin structure at the end of the molecular structure. Any of the curable resins may further have a side chain olefin structure having an olefin structure in a side chain portion. In any of the curable resins, the total content of the alpha olefin structure, the olefin structure at the terminal of the molecular structure, and the side chain olefin structure having an olefin structure in the side chain portion may be 1.8mmol/g or more. The content of the indane structure represented by the formula (2) in any of the curable resins may be 3.0mmol/g or less. The weight average molecular weight Mw of any of the curable resins may be 5000 to 500000. In the method for producing a curable resin, a compound having a plurality of isopropenyl groups is polymerized at a reaction temperature of 10-75 ℃ in the presence of an acid catalyst to obtain a curable resin having at least an alpha-olefin structure represented by formula (1), an iodine value of 70 or more, and a weight average molecular weight Mw of 2500 or more. In the method for pro