Ultraviolet curable resin composition, sliding member, and method for producing sliding member

{
  "publication_number": "US9540584B2",
  "country": "US",
  "kind": "B2",
  "title": "Ultraviolet curable resin composition, sliding member, and method for producing sliding member",
  "abstract": "There is provided an ultraviolet curable resin composition for a self-lubricating liner. The composition includes a first (meth)acrylate compound having an isocyanuric acid ring represented by the following formula (1); a second (meth)acrylate compound different from the first (meth)acrylate compound; a first polytetrafluoroethylene resin with an average particle size in the range of 75 μm to 180 μm; and a second polytetrafluoroethylene resin with an average particle size in the range of 1 μm to 15 μm, wherein the total amount of the first polytetrafluoroethylene resin and the second polytetrafluoroethylene resin is in the range of 30% by weight to 50% by weight with respect to the entire amount of the ultraviolet curable resin composition; and the second polytetrafluoroethylene resin is contained in an amount of 20% by weight to 75% by weight with respect to the total amount of the first and second polytetrafluoroethylene resins.",
  "claims": [
    "1. An ultraviolet curable resin composition for a self-lubricating liner, the composition comprising: a first (meth)acrylate compound having an isocyanuric acid ring represented by the following formula (1): (wherein X is a group which contains an acryloyl group and is composed only of C, H, and O, and Y and Z are groups each composed only of C, H, and O); a second (meth)acrylate compound different from the first (meth)acrylate compound; a first polytetrafluoroethylene resin with an average particle size in the range of 75 μm to 180 μm; and a second polytetrafluoroethylene resin with an average particle size in the range of 1 μm to 15 μm, wherein a total amount of the first polytetrafluoroethylene resin and the second polytetrafluoroethylene resin is in the range of 30% by weight to 50% by weight with respect to an entire amount of the ultraviolet curable resin composition; and the second polytetrafluoroethylene resin is contained in an amount of 20% by weight to 75% by weight with respect to the total amount of the first and second polytetrafluoroethylene resins.",
    "2. The ultraviolet curable resin composition according to claim 1, wherein the first (meth)acrylate compound is contained in an amount of 15% by weight to 35% by weight with respect to the entire amount of the ultraviolet curable resin composition; and a total amount of the first (meth)acrylate compound and the second (meth)acrylate compound is in the range of 35% by weight to 65% by weight with respect to the entire amount of the ultraviolet curable resin composition.",
    "3. The ultraviolet curable resin composition according to claim 1, wherein a melting point of the first polytetrafluoroethylene resin is higher than a melting point of the second polytetrafluoroethylene resin.",
    "4. The ultraviolet curable resin composition according to claim 1, wherein the first (meth)acrylate compound having the isocyanuric acid ring represented by the formula (1) is one of di-(2-acryloxyethyl)isocyanurate, tris-(2-acryloxyethyl)isocyanurate, and ε-caprolactone modified tris-(2-acryloxyethyl)isocyanurate, or a mixture of the di-(2-acryloxyethyl)isocyanurate and the tris-(2-acryloxyethyl)isocyanurate.",
    "5. The ultraviolet curable resin composition according to claim 1, wherein the second (meth)acrylate compound includes at least one meth(acrylate) compound selected from the group consisting of: hydroxyethyl(meth)acrylate, hydroxypropyl (meth)acrylate and isobornyl (meth)acrylate; and the at least one meth(acrylate) compound is contained in an amount of 5% by weight to 20% by weight with respect to the entire amount of the ultraviolet curable resin composition.",
    "6. The ultraviolet curable resin composition according to claim 1, wherein the second (meth)acrylate compound includes at least one meth(acrylate) compound selected from the group consisting of: pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, and dipentaerythritol polyacrylate; and the at least one meth(acrylate) compound is contained in an amount of 8% by weight or less with respect to the entire amount of the ultraviolet curable resin composition.",
    "7. The ultraviolet curable resin composition according to claim 1, wherein the second (meth)acrylate compound includes bisphenol A-type epoxy modified acrylate; and the bisphenol A-type epoxy modified acrylate is contained in an amount of 10% by weight or less with respect to the entire amount of the ultraviolet curable resin composition.",
    "8. The ultraviolet curable resin composition according to claim 1, wherein the second (meth)acrylate compound includes at least one meth(acrylate) compound selected from the group consisting of: urethane acrylate, ethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, butylene glycol di(meth)acrylate, hexanediol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, and tripropylene glycol di(meth)acrylate; and the at least one meth(acrylate) compound is contained in an amount of 2% by weight or less with respect to the entire amount of the ultraviolet curable resin composition.",
    "9. The ultraviolet curable resin composition according to claim 1, wherein the first (meth)acrylate compound is a mixture of di-(2-acryloxyethyl)isocyanurate and tris-(2-acryloxyethyl)isocyanurate; and the second (meth)acrylate compound is a mixture of bisphenol A-type epoxy modified acrylate, dipentaerythritol hexa(meth)acrylate, isobornyl (meth)acrylate, hydroxyethyl (meth)acrylate, and ethylene glycol di(meth)acrylate.",
    "10. The ultraviolet curable resin composition according to claim 1, further comprising a thermosetting agent.",
    "11. A sliding member comprising a self-lubricating liner which is formed on a sliding surface of the sliding member and is made of the ultraviolet curable resin composition according to claim 1.",
    "12. The sliding member according to claim 11, wherein the sliding member is a sliding bearing.",
    "13. The sliding member according to claim 12, wherein the sliding bearing is a spherical bearing.",
    "14. The sliding member according to claim 11, wherein the sliding member is a bolt comprising a head portion, a shaft portion, a thread portion, and the self-lubricating liner formed on an outer circumferential surface of the shaft portion.",
    "15. A manufacturing method for producing a sliding member, comprising: applying an ultraviolet curable resin composition on a sliding surface of the sliding member; and curing the ultraviolet curable resin composition by irradiation with ultraviolet rays to form a self-lubricating liner, wherein the ultraviolet curable resin composition comprises: a first (meth)acrylate compound having an isocyanuric acid ring represented by the following formula (1): (wherein X is a group which contains an acryloyl group and is composed only of C, H, and O and Y and Z are groups each composed only of C, H, and O); a second (meth)acrylate compound different from the first (meth)acrylate compound; a first polytetrafluoroethylene resin with an average particle size in the range of 75 μm to 180 μm; and a second polytetrafluoroethylene resin with an average particle size in the range of 1 μm to 15 μm, wherein a total amount of the first polytetrafluoroethylene resin and the second polytetrafluoroethylene resin is in the range of 30% by weight to 50% by weight with respect to an entire amount of the ultraviolet curable resin composition; and the second polytetrafluoroethylene resin is contained in an amount of 20% by weight to 75% by weight with respect to the total amount of the first and second polytetrafluoroethylene resins.",
    "16. The manufacturing method for producing the sliding member according to claim 15, wherein the first (meth)acrylate compound is contained in an amount of 15% by weight to 35% by weight with respect to the entire amount of the ultraviolet curable resin composition; and a total amount of the first (meth)acrylate compound and the second (meth)acrylate compound is in the range of 35% by weight to 65% by weight with respect to the entire amount of the ultraviolet curable resin composition.",
    "17. The manufacturing method for producing the sliding member according to claim 15, further comprising performing cutting or grinding of the self-lubricating liner to have a desired size.",
    "18. The manufacturing method for producing the sliding member according to claim 15, wherein the ultraviolet curable resin composition contains a thermosetting agent; the sliding member is a spherical bearing including an outer race member which has a concave first bearing surface and an inner race member which has a convex second bearing surface slidably movable on the first bearing surface; and the self-lubricating liner is formed by: applying the ultraviolet curable resin composition on the concave first bearing surface or the convex second bearing surface as a sliding surface; curing the ultraviolet curable resin composition applied on the concave first bearing surface or the convex second bearing surface until a semi-cured state by irradiation with the ultraviolet rays; inserting the inner race member into the outer race member after the ultraviolet curable resin composition is semi-cured; pressing the outer race member to cause plastic deformation so as to make the outer race member follow the convex second bearing surface of the inner race member; and curing the ultraviolet curable resin composition completely by heat after the plastic deformation."
  ],
  "cpc": [
    "C08F 2/48",
    "C08F 220/20",
    "C08F 220/34",
    "C08F 222/1006",
    "C08F 2220/1875",
    "C08F 2220/343",
    "C08F 2222/1013",
    "C08L 2312/00",
    "C09D 133/14",
    "C10M 107/00",
    "C10M 107/40",
    "C10M 145/16",
    "C10M 147/02",
    "C10M 2209/0845",
    "C10M 2213/0623",
    "C10M 2217/0245",
    "C10N 2020/06",
    "C10N 2030/06",
    "C10N 2220/082",
    "C10N 2230/06",
    "F16C 17/02",
    "F16C 2208/72",
    "F16C 23/045",
    "F16C 33/201",
    "F16C 33/208"
  ],
  "assignees": [
    "MINEBEA CO LTD"
  ],
  "filing_date": "2015-03-26",
  "publication_date": "2017-01-10",
  "grant_date": "2017-01-10",
  "priority_date": "2014-03-31",
  "application_number": "US-201514669950-A",
  "family_id": "54066911",
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  ]
}