Agents for reworkable epoxy resins
Compounds of formula I, uses as crosslinking agents or curing agents thereof, and resins obtained by using the compounds as crosslinking agents.
1. An epoxy resin composition comprising:
an epoxy resin; and
a polyamine curing agent comprising a compound having Formula (I):
wherein:
m is 2, 1, or 0;
n is 2, 3, or 4;
the sum of m and n is 4;
each R 1 is independently hydrogen, alkyl, cycloalkyl, heterocycle, heterocycloalkyl, alkenyl, cycloalkenyl, aryl, heteroaryl, alkyloxyalkyl, or alkynyl;
each A is independently unsubstituted ethylene, propylene, isopropylene, butylene, iso-butylene, hexylene, ethylene-oxy-ethylene, ethylene-amino-ethylene,
each R 2 is independently —NHR 3 , wherein each R 3 is independently hydrogen, alkyl, aminoalkyl, alkylaminoalkyl, cycloalkyl, heterocycle, alkenyl, aryl, or heteroaryl;
or, every two —O-A-R 2 groups, together with the carbon atom to which they are attached to, can independently form an dioxanyl ring with no less than 4 ring members and one or more of the ring carbon atom(s), other than the carbon atom to which the two —O-A-R 2 groups are attached, are independently substituted with one or more independent amino group or aminoalkyl wherein each amino is independently a primary or secondary amino group.
2. An adhesive material comprising the epoxy resin composition of claim 1 .
3. A coating material comprising the epoxy resin composition of claim 1 .
4. A composite matrix material comprising the epoxy resin composition of claim 1 .
5. The composition of claim 1 , wherein R 1 is independently hydrogen, alkyl, or aryl.
6. The composition of claim 1 , wherein R 1 is independently hydrogen or methyl.
7. The composition of claim 1 , wherein the compound is:
8. The composition of claim 1 , wherein the compound is:
9. A composite comprising a cross-linked epoxy resin in contact with a substrate, wherein the cross-linked polymer comprises cleavable links derived from a cross-linking agent comprising a compound having Formula (I):
wherein:
m is 2, 1, or 0;
n is 2, 3, or 4;
the sum of m and n is 4;
each R 1 is independently hydrogen, alkyl, cycloalkyl, heterocycle, heterocycloalkyl, alkenyl, cycloalkenyl, aryl, heteroaryl, alkyloxyalkyl, or alkynyl;
each A is independently unsubstituted ethylene, propylene, isopropylene, butylene, iso-butylene, hexylene, ethylene-oxy-ethylene, ethylene-amino-ethylene,
each R 2 is independently —NHR 3 , wherein each R 3 is independently hydrogen, alkyl, aminoalkyl, alkylaminoalkyl, cycloalkyl, heterocycle, alkenyl, aryl, or heteroaryl;
or, every two —O-A-R 2 groups, together with the carbon atom to which they are attached to, can independently form an dioxanyl ring with no less than 4 ring members and one or more of the ring carbon atom(s), other than the carbon atom to which the two —O-A-R 2 groups are attached, are independently substituted with one or more independent amino group or aminoalkyl wherein each amino is independently a primary or secondary amino group.
10. The composite of claim 9 , wherein R 1 is independently hydrogen, alkyl, or aryl.
11. The composite of claim 9 , wherein R 1 is independently hydrogen or methyl.
12. The composite of claim 9 , wherein the compound is:
13. The composite of claim 9 , wherein the compound is:
14. A cross-linked epoxy matrix derived from an epoxy resin and cross-linking group derived from a polyamine curing agent having the structure of Formula (I):
wherein:
m is 2, 1, or 0;
n is 2, 3, or 4;
the sum of m and n is 4;
each R 1 is independently hydrogen, alkyl, cycloalkyl, heterocycle, heterocycloalkyl, alkenyl, cycloalkenyl, aryl, heteroaryl, alkyloxyalkyl, or alkynyl;
each A is independently unsubstituted ethylene, propylene, isopropylene, butylene, iso-butylene, hexylene, ethylene-oxy-ethylene, ethylene-amino-ethylene,
each R 2 is independently —NHR 3 , wherein each R 3 is independently hydrogen, alkyl, aminoalkyl, alkylaminoalkyl, cycloalkyl, heterocycle, alkenyl, aryl, or heteroaryl;
or, every two —O-A-R 2 groups, together with the carbon atom to which they are attached to, can independently form an dioxanyl ring with no less than 4 ring members and one or more of the ring carbon atom(s), other than the carbon atom to which the two —O-A-R 2 groups are attached, are independently substituted with one or more independent amino group or aminoalkyl wherein each amino is independently a primary or secondary amino group.
15. The epoxy matrix of claim 14 , wherein R 1 is independently hydrogen, alkyl, or aryl.
16. The epoxy matrix of claim 14 , wherein R 1 is independently hydrogen or methyl.
17. The epoxy matrix of claim 14 , wherein the compound is:
18. The epoxy matrix of claim 14 , wherein the compound is:
19. A method of recycling a cross-linked polymer, comprising:
(a) degrading the cross-linked polymer under an acidic condition into smaller, soluble molecules and/or polymers;
(b) and removing the degraded the cross-linked polymer,
wherein the cross-linked polymer comprises cleavable links derived from an acid-labile cross-linking agent comprising a compound selected from:
20. The method of claim 19 , wherein R 1 is independently hydrogen, alkyl, or aryl.
21. The method of claim 19 , wherein R 1 is independently hydrogen or methyl.
22. The method of claim 19 , wherein the compound is: