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PERFLUOROPOLYETHER-CONTAINING COMPOUNDS WITH OXALYLAMINO GROUPS

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  • Publication Date:
    November 15, 2012
  • Additional Information
    • Document Number:
      20120289736
    • Appl. No:
      13/514322
    • Application Filed:
      December 22, 2010
    • Abstract:
      Compounds containing at least one perfluoropolyether segment and at least two oxalylamino groups as well as methods of making these compounds are described. The compounds can be polymeric materials or can be used in the preparation of various copolymeric materials by reaction with compounds having at least two primary or secondary amino groups.
    • Inventors:
      Yang, Yu (Eden Prairie, MN, US); Guerra, Miguel A. (Woodbury, MN, US); Hansen, Richard G. (Mahtomedi, MN, US); Hays, David S. (Woodbury, MN, US); Iyer, Suresh S. (Woodbury, MN, US); Kumar, Ramesh C. (Woodbury, MN, US); Moore, George G.I. (Afton, MN, US)
    • Assignees:
      3M INNOVATIVE PROPERTIES COMPANY (Saint Paul, MN, US)
    • Claim:
      1. A product of a reaction mixture comprising: a) a fluorinated amine having a perfluoropolyether segment and having at least two primary amino groups, at least two secondary amino groups, or at least one primary amino group plus at least one secondary amino group; and b) an oxalate compound of Formula (I) [chemical expression included] wherein each R1 is independently an alkyl, haloalkyl, aralkyl, substituted aralkyl, alkenyl, aryl, substituted aryl, or imino of formula —N═CR4R5; R4 is hydrogen, alkyl, aralkyl, substituted aralkyl, aryl, or substituted aryl; and R5 is an alkyl, aralkyl, substituted aralkyl, aryl, or substituted aryl.
    • Claim:
      2. The product of claim 1, wherein the fluorinated amine is a compound of Formula (V) RfY1—NHR2m  (V) wherein Rf is a perfluoropolyether group; each R2 is independently hydrogen, alkyl, aryl, or aralkyl; each Y1 is independently (a) a heteroalkylene, (b) alkylene, (c) a carbonylamino group linking a first group to a second group, wherein the first group and the second group are each a heteroalkylene or alkylene, or (d) a combination thereof; and n is an integer equal to at least 2.
    • Claim:
      3. The product of claim 1, wherein the fluorinated amine is of Formula (Vb). R2HN—Y1—Rf—Y1—NHR2  (Vb)
    • Claim:
      4. The reaction product of claim 1, wherein the fluorinated amine is Rf—(CH2CH2NH2)2, Rf—(CH2NH2)2, Rf—(CH2OC3H6NH2)2, Rf—(CH2OC2H4NH2)2, or a mixture thereof.
    • Claim:
      5. The product of claim 1, wherein the fluorinated amine is of Formula (VI) [chemical expression included] wherein Y1 in Formula (V) is equal to —Y2—(CO)—NR2—Y3— in Formula (VI); each Y2 is independently a single bond, heteroalkylene, alkylene, or combination thereof; and each Y3 is independently a heteroalkylene, alkylene, or combination thereof.
    • Claim:
      6. The product of claim 1, wherein Rf is of formula —CF(CF3)[OCF2CF(CF3)]bOCF2—R6—CF2O[CF(CF3)CF2O]dCF(CF3)— wherein R6 is a perfluoroalkylene group having 1 to 20 carbon atoms; and b and d are both integers with a sum in the range of 0 to 35.
    • Claim:
      7. The product of claim 5, wherein n is equal to 2 and the fluorinated amine is a compound of Formula (VIa). [chemical expression included]
    • Claim:
      8. A compound of Formula (II) [chemical expression included] wherein Rf is a perfluoropolyether group; each Y1 is independently (a) a heteroalkylene, (b) alkylene, or (c) a carbonylamino group linking a first group to a second group, wherein the first group and the second group are each a heteroalkylene or alkylene, or (d) a combination thereof; each R1 is independently an alkyl, haloalkyl, aralkyl, substituted aralkyl, alkenyl, aryl, substituted aryl, or imino of formula —N═CR4R5; each R2 is independently hydrogen, alkyl, aralkyl, or aryl; R4 is a hydrogen, alkyl, aralkyl, substituted aralkyl, aryl, or substituted aryl; and R5 is an alkyl, aralkyl, aryl, or substituted aryl; and n is an integer equal to at least 2.
    • Claim:
      9. The compound of claim 8, wherein n is equal to 2 and the compound is of Formula (IIa). [chemical expression included]
    • Claim:
      10. The compound of claim 8, wherein the compound is of Formula (IIb) [chemical expression included] wherein Y1 in Formula (II) is equal to —Y2—(CO)—NR2—Y3— in Formula (IIb); each Y2 is independently a single bond, heteroalkylene, alkylene, or combination thereof; and each Y3 is independently a heteroalkylene, alkylene, or combination thereof.
    • Claim:
      11. The compound of claim 10, wherein n is equal to 2 and the compound is of Formula (IIc). [chemical expression included]
    • Claim:
      12. The compound of claim 8, wherein Rf is of formula —CF(CF3)[OCF2CF(CF3)]bOCF2—R6—CF2O[CF(CF3)CF2O]dCF(CF3)— wherein R6 is a perfluoroalkylene group having 1 to 20 carbon atoms; and b and d are both integers with a sum in the range of 0 to 35.
    • Claim:
      13. A compound of Formula (III) [chemical expression included] wherein Rf is a perfluoropolyether group; each Y1 is independently (a) a heteroalkylene, (b) alkylene, (c) a carbonylamino group linking a first group to a second group, wherein the first group and the second group are each a heteroalkylene or alkylene, or (d) a combination thereof; each R1 is independently an alkyl, haloalkyl, aralkyl, substituted aralkyl, alkenyl, aryl, substituted aryl, or imino of formula —N═CR4R5; each R2 is independently hydrogen, alkyl, aralkyl, or aryl; R4 is hydrogen, alkyl, aralkyl, substituted aralkyl, aryl, or substituted aryl; R5 is alkyl, aralkyl, substituted aralkyl, aryl, or substituted aryl; and q is an integer equal to at least 1.
    • Claim:
      14. The compound of claim 13, wherein each Y1 is equal to a group of formula —Y2—(CO)—NR2—Y3— wherein each Y2 is independently a single bond, heteroalkylene, alkylene, or combination thereof; and each Y3 is independently a heteroalkylene, alkylene, or combination thereof.
    • Claim:
      15. The compound of claim 13, wherein Rf is of formula —CF(CF3)[OCF2CF(CF3)]bOCF2—R6—CF2O[CF(CF3)CF2O]dCF(CF3)— wherein R6 is a perfluoroalkylene group having 1 to 20 carbon atoms; and b and d are both integers with a sum in the range of 0 to 35.
    • Claim:
      16. A polymeric material comprising at least one group of Formula (IV) [chemical expression included] wherein Rf is a perfluoropolyether group; each Y1 is independently (a) a heteroalkylene, (b) alkylene, or (c) a carbonylamino group linking a first group to a second group, wherein the first group and the second group are each a heteroalkylene or alkylene, or (d) a combination thereof; each R2 is independently hydrogen, alkyl, aryl, or aralkyl; p is an integer equal to at least 1; and each asterisk denotes a site of attachment to another group of the polymeric material.
    • Claim:
      17. The polymeric material of claim 16, wherein each Y1 is equal to a group of formula —Y2—(CO)—NR2—Y3—, wherein each Y2 is independently a single bond, heteroalkylene, alkylene, or combination thereof; and each Y3 is independently a heteroalkylene, alkylene, or combination thereof.
    • Claim:
      18. The polymeric material of claim 16, wherein Rf is of formula —CF(CF3)[OCF2CF(CF3)]bOCF2—R6—CF2O[CF(CF3)CF2O]dCF(CF3)— wherein R6 is a perfluoroalkylene group having 1 to 20 carbon atoms; and b and d are both integers with a sum in the range of 0 to 35.
    • Current U.S. Class:
      560/168
    • Current International Class:
      07; 07
    • Accession Number:
      edspap.20120289736