Thiol group-containing polymer and curable composition thereof

{
  "publication_number": "US9663619B2",
  "country": "US",
  "kind": "B2",
  "title": "Thiol group-containing polymer and curable composition thereof",
  "abstract": "A thiol group-containing polymer is represented by HS - (R - S r) n - R - SH, wherein R is an organic group including a - O - CH 2 - O - bond and/or a branched alkylene group, n is an integer of from 1 to 200, r is an integer of from 1 to 5, and the average value of r is 1.1 or more and 1.8 or less. A curable composition using the thiol group-containing polymer can be used in sealants, adhesives, paints and the like, which require properties such as a low specific gravity, a low viscosity and a low glass transition temperature.",
  "claims": [
    "1. A curable composition comprising a 1) thiol group-containing polymer represented by: HS - (R - S r) n - R - SH wherein R is an organic group including a - O - CH 2 - O - bond and/or a branched alkylene group, n is an integer of 1 to 200, r is an integer of 1 to 5, and an average value of r is 1.1 or more and lower than 1.8, and the thiol group-containing polymer is a liquid at room temperature, and 2) an oxidizing agent.",
    "2. The curable composition according to claim 1, wherein the organic group including a - O - CH 2 - O - bond is an organic group containing 50 mol % or more of - C 2 H 4 - O - CH 2 - O - C 2 H 4 -.",
    "3. The curable composition according to claim 1, wherein the branched alkylene group R is",
    "4. The curable composition according to claim 1, wherein the thiol group-containing polymer has a glass transition temperature of −85° C. or more and −50° C. or less.",
    "5. The curable composition according to claim 1, wherein the thiol group-containing polymer has a temperature at 50% weight loss of 300° C. or more and 350° C. or less.",
    "6. The curable composition according to claim 1, wherein the thiol group-containing polymer has a specific gravity at 23° C. of 1.18 to 1.28.",
    "7. A curable composition comprising a 1) thiol group-containing polymer represented by: HS - (R - S r) n - R - SH wherein R is an organic group including a - O - CH 2 - O - bond and/or a branched alkylene group, n is an integer of 1 to 200, r is an integer of 1 to 5, and an average value of r is 1.1 or more and lower than 1.8, and the thiol group-containing polymer is a liquid at room temperature, and 2) a compound containing two or more isocyanate groups in a molecule.",
    "8. The curable composition according to claim 7, wherein the organic group including a - O - CH 2 - O - bond is an organic group containing 50 mol % or more of - C 2 H 4 - O - CH 2 - O - C 2 H 4 -.",
    "9. The curable composition according to claim 7, wherein the branched alkylene group R is",
    "10. The curable composition according to claim 7, wherein the thiol group-containing polymer has a glass transition temperature of −85° C. or more and −50° C. or less.",
    "11. The curable composition according to claim 7, wherein the thiol group-containing polymer has a temperature at 50% weight loss of 300° C. or more and 350° C. or less.",
    "12. The curable composition according to claim 7, wherein the thiol group-containing polymer has a specific gravity at 23° C. of 1.18 to 1.28.",
    "13. A curable composition comprising a 1) thiol group-containing polymer represented by: HS - (R - S r) n - R - SH wherein R is an organic group including a - O - CH 2 - O - bond and/or a branched alkylene group, n is an integer of 1 to 200, r is an integer of 1 to 5, and an average value of r is 1.1 or more and lower than 1.8, and the thiol group-containing polymer is a liquid at room temperature, 2) an epoxy resin containing two or more glycidyl groups in a molecule, and 3) an amine.",
    "14. The curable composition according to claim 13, wherein the organic group including a - O - CH 2 - O - bond is an organic group containing 50 mol % or more of - C 2 H 4 - O - CH 2 - O - C 2 H 4 -.",
    "15. The curable composition according to claim 13, wherein the branched alkylene group R is",
    "16. The curable composition according to claim 13, wherein the thiol group-containing polymer has a glass transition temperature of −85° C. or more and −50° C. or less.",
    "17. The curable composition according to claim 13, wherein the thiol group-containing polymer has a temperature at 50% weight loss of 300° C. or more and 350° C. or less.",
    "18. The curable composition according to claim 13, wherein the thiol group-containing polymer has a specific gravity at 23° C. of 1.18 to 1.28."
  ],
  "description_excerpt": "This disclosure relates to a thiol group-containing polymer. In particular, the disclosure relates to a thiol group-containing polymer useful for polysulfide-based sealants, adhesives and paints having a low specific gravity, a low glass transition temperature, a high heat resistance and improved elastic recovery.\n\nLiquid polysulfide polymers have thiol groups at the terminals, and thus are easily oxidized and cured by an oxidizing agent such as lead dioxide and manganese dioxide. Rubber-like cured products obtained by curing polysulfide polymers contain sulfur in the main chain of the molecule, and do not contain double bonds, and thus have excellent features in oil resistance, weather resistance, water tightness and air tightness, and also have fine adhesibility, and thus are widely used as sealants, adhesives and paints.\n\nThe most common method of producing a polysulfide polymer is a method of obtaining a liquid polymer through a solid polysulfide described in U.S. Pat. No. 2,466,963. Furthermore, a production method using a phase transfer catalyst has been reported (see U.S. Pat. No. 6,939,941).\n\nThe thioether described in WO 2009/131796 is a thioether that does not substantially contain polysulfide bonds, and the reference describes that the thioether is formed into a sealant that is excellent in fuel resistance and the like.\n\nThe polythioether polymer described in WO 1998/039365 is a polythioether that does not contain polysulfide bonds and shows excellent low temperature flexibility and fuel oil resistance when it is cured, and thus is used as a sealant as in conventional polysulfide polymers.",
  "cpc": [
    "C08G 75/14",
    "C07C 323/14",
    "C08G 18/52",
    "C08G 18/73",
    "C08G 2190/00",
    "C08G 59/4028",
    "C08G 59/56",
    "C08G 59/66",
    "C08G 75/12",
    "C08L 63/00",
    "C08L 81/04",
    "C09D 181/02",
    "C09J 181/02",
    "C09K 3/1012"
  ],
  "ipc": [
    "C08G 75/12",
    "C08G 75/14",
    "C07C 323/14",
    "C08G 18/52",
    "C08G 18/73",
    "C08G 59/40",
    "C08G 59/56",
    "C08G 59/66",
    "C08L 63/00",
    "C09K 3/10"
  ],
  "assignees": [
    "Toray Fine Chemicals Co Ltd"
  ],
  "inventors": [
    "Koki Echigoya",
    "Yukiko Hamada",
    "Kazunori Matsumoto"
  ],
  "filing_date": "2013-07-10",
  "publication_date": "2017-05-30",
  "grant_date": "2017-05-30",
  "priority_date": "2012-08-01",
  "application_number": "US-201314416468-A",
  "family_id": "50027752",
  "cited_by_count": 46,
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}