Nova Patents
CA2309699C

Water compatible curing agents for epoxy resins

Abstract

A novel water compatible curing agent for epoxy resins is provided. The curing agent can be made by (a) reacting at least one polyamine having at least 3 active amine hydrogen atoms per molecule and at least one epoxy resin having a functionality of at least 1.5 in an epoxy functionality equivalents to polyamine mole ratio of 0.9:1 to 1:10 thereby producing an amine-terminated intermediate; (b) reacting the amine-terminated intermediate with 0.5 to 25 weight percent, based on the amine-terminated intermediate, of an acid-terminated polyalkyleneglycol-containing compound having formulae (I), (II) and (III) wherein R1 is an alkyl, aryl, or arylalkyl group having 1 to 15 carbon atoms, X and Y are independently a hydrogen, methyl, or ethyl group with the provision that if X is methyl or ethyl, Y is hydrogen or if Y is methyl or ethyl, X is hydrogen, and n + m + o is a real number from 100 to 200, and n + o is at least 70 percent of n + m + o, and in a ratio of (I) to (II) by weight in the range of 100:0 to 0:100, and in a ratio of (I) to (III) by weight in the range of 100:0 to 0:100, and in a ratio of (II) to (III) by weight in the range of 100:0 to 0:100, until essentially all of the acid group is consumed. Such amine-terminated curing agent can also be capped with a monoepoxy. The curing agent can also be made (a) reacting at least one polyamine described above and an epoxy resin thereby producing an amine- terminated intermediate; (b) reacting the amine-terminated intermediate with a monoepoxy to provide a capped amine-terminated intermediate; then (c) reacting the capped amine-terminated intermediate with an acid-terminated polyalkyleneglycol-containing compound described above.

CA2309699C, drawing sheet 1
Sheet 1 of 65

Term

Term ended

Expired 12 November 2018, 7.9 years ago.

  1. Priority
  2. Filed
  3. Granted
  4. Expired
  5. Today

9 claims: 6 independent, 3 dependent

  1. 1
    CLAIMS :1. A curing agent for epoxy resins comprising a reaction product prepared by the steps comprising: (a) reacting at least ore polyamine having at least 3 active amine hydrogen atoms per molecule and at least one epoxy resin having a functionality of . at least 1.5,in an epoxy functionality equivalents to polyamine mole ratio of 0.9:1 to 1:10, thereby producing an amine-terminated intermediate;(b) reacting the amine-terminated intermediate with 0.5 to 25 weight percent, based on the amineterminated intermediate, of an acid-terminated polyalkyleneglycol-containing compound having the formula : CA 02309699 2008-05-28 - 44 wherein R1 is an alkyl, aryl, or arylalkyl group, the alkyl group having 1 to 15 carbon atoms, the aryl group having 5 to 15 carbon atoms and the arylalkyl group having 6 to 15 carbon atoms, X and Y are independently a hydrogen, methyl or ethyl group with the provision that if X is methyl or ethyl, Y is hydrogen or if Y is methyl or ethyl, X is hydrogen, and n+m+o is a real number from 100 to 200, and n + o is at lest 70 percent of n + m + o, in a ratio of (I) to (II) by weight in the range of 100:0 to 0:100, a ratio of (I) to (III) by weight in the range of 100:0 to 0:100, and in a ratio of (II) to (III) by weight in the range of 100:0 to 0:100, until essentially all of the acid group is consumed, thereby producing the amine-terminated curing agent.
  2. 3
    The curing agent of claims 1 or 2, wherein the amine-terminated curing agent is prepared by reacting the acid-terminated polyalkyleneglycol-containing compound of structures (I) , (II) and (III) in an amount of 4 to 98 percent by weight of (I) , 1 to 95 percent by weight of (II) , 1 to 95 and percent by weight of (III) and the amineterminated intermediate.
  3. 5
    8. The curing agent of any one of claims 1 to 7, wherein the curing agent is prepared by reacting an acidterminated polyalkyleneglycol alkylether having the formula CH2-CH2-0 wherein R1 is an alkyl, aryl, or arylalkyl group, the alkyl group having 1 to 15 carbon atoms, the aryl group having 5 to 15 carbon atoms and the arylalkyl group having 6 to 15 carbon atoms, o is a positive real number from 100 to 200, and at least one diamine in an amine to acid equivalent ratio of 6:1 to 25:1. CA 02309699 2008-05-28
  4. 6
    9. The curing agent of any one of claims 1 to 8 wherein the acid-terminated polyalkyleneglycol alkylether is prepared by reacting can acid-terminated polyalkyleneglycol-containing compound having the formula wherein R1 is an alkyl or arylalkyl group, the alkyl group having 1 to 15 carbon atoms, the arylalkyl group having 6 to 15 carbon atoms, o is a positive real number from 100 to 200, and at least one amine-terminated intermediate in an amine to acid equivalent, ratio of 6:1 to 25:1.
  5. 7
    10. A composition comprising (a) water;and (b) curing agent of any one of claims 1 to 9.
  6. 8
    11. An aqueous curable epoxy resin system comprising:(a) water, (b) at least one epoxy resin;and (c) curing agent of anyone of claims 1 to 9.
Independent claims6