Silicon-containing compositions and their methods of use
Provided herein are silicon-containing recyclable polyamino compounds; epoxy resin compositions containing these silicon-containing reworkable or recyclable polyamino compounds; and methods of their use.
1. A compound of Formula (I-A-iv)
or a salt thereof, wherein:
z is an integer from 1 to 6;
t is an integer from 0 to 1;
q1 is an integer from 1 to 4;
q2 is an integer from 1 to 3;
each of R 4A , R 4B , R 4C , and R 4D is independently for each occurrence hydrogen or alkyl; and each occurrence of R 5A is independently alkyl, cycloalkyl, aryl, or —OR C , wherein R C is alkyl, cycloalkyl, heterocyclyl, alkenyl, alkynyl, cycloalkenyl, aryl or heteroaryl, provided that the sum of t, q1, and q2 is 4.
2. The compound of claim 1 , wherein the compound of Formula (I-A) is a compound of Formula (I-A-ii-1)
3. The compound of claim 1 , wherein the compound is:
4. The compound of claim 3 , wherein the compound is:
5. A composition comprising the reaction product of:
an epoxy resin; and
a compound of Formula (I-A-iv):
wherein:
z is an integer from 1 to 6;
t is an integer from 0 to 1;
q1 is an integer from 1 to 4;
q2 is an integer from 0 to 3;
each of R 4A , R 4B , R 4C , and R 4D is independently for each occurrence hydrogen or alkyl;
and each occurrence of R 5A is independently alkyl, cycloalkyl, aryl, or —OR C , wherein R C is alkyl, cycloalkyl, heterocyclyl, alkenyl, alkynyl, cycloalkenyl, aryl or heteroaryl, provided that the sum of t, q1, and q2 is 4.
6. The composition of claim 5 , wherein the compound of Formula (I-A) is a compound of Formula (I-A-ii-1):
7. The composition of claim 5 , wherein the compound of Formula (I-A) is:
8. The composition of claim 7 , wherein the compound of Formula (I-A) is:
9. The composition of claim 5 , wherein the epoxy resin comprises a diepoxide resin.
10. A composition comprising the reaction product of:
an epoxy resin;
a compound of Formula (I-A);
(R 5 ) t —Si O—W—NH 2 ) q Formula (I-A)
wherein:
q is 4, 3, 2, or 1;
t is 0, 1, 2, or 3;
the sum of q and t is 4;
each occurrence of W is independently alkylene, cycloalkylene, heterocyclylene, alkenylene, alkynylene, cycloalkenylene, arylene, or heteroarylene; and
each occurrence of R 5 is independently hydrogen, alkyl, cycloalkyl, heterocyclyl, alkenyl, alkynyl, cycloalkenyl, aryl, heteroaryl or —OR C , wherein R C is alkyl, cycloalkyl, heterocyclyl, alkenyl, alkynyl, cycloalkenyl, aryl or heteroaryl; and
a compound having the Formula (II-A-1):
wherein: each of R 6A and R 6B is independently hydrogen or alkyl;
each of R 7A , R 7B , R 8A , R 8B , R 8C and R 8D is independently for each occurrence hydrogen or alkyl; and
each of n1 and n2 is independently 1 or 2.
11. A method for recycling the composition of claim 10 , comprising contacting the composition with an acid.
12. The composition of claim 1 , wherein the compound of Formula (I-A) is a compound of Formula (I-A-iv)
wherein:
z is an integer from 1 to 6; t is an integer from 0 to 1;
q1 is an integer from 0 to 4; q2 is an integer from 0 to 4;
each of R 4A , R 4B , R 4C , and R 4D is independently for each occurrence hydrogen or alkyl; and
each occurrence of R 5A is independently alkyl, cycloalkyl, aryl, or —OR C , wherein R C is alkyl, cycloalkyl, heterocyclyl, alkenyl, alkynyl, cycloalkenyl, aryl or heteroaryl,
provided that the sum of t, q1, and q2 is 4, and the sum of q1 and q2 is not 0.
13. The composition of claim 10 , wherein the compound of Formula (I-A) is a compound of Formula (I-A-i-1) or (I-A-ii-1):
wherein:
z is an integer from 1 to 6; each of R 4A , R 4B , R 4C , and R 4D is independently for each occurrence hydrogen or alkyl; and
each occurrence of R 5A is independently alkyl, cycloalkyl, aryl, or —OR C , wherein R C is alkyl, cycloalkyl, heterocyclyl, alkenyl, alkynyl, cycloalkenyl, aryl or heteroaryl.
14. The composition of claim 10 , wherein the compound of Formula (I-A) is a compound of Formula (I-A-iii):
wherein:
each of X 1 , X 2 , X 3 , and X 4 is independently alkylene, cycloalkylene, heterocyclylene, alkenylene, alkynylene, cycloalkenylene, arylene, or heteroarylene.
15. The composition of claim 10 , wherein the compound of Formula (I-A) is:
16. The composition of claim 10 , wherein the compound of Formula (I-A) is:
17. The composition of claim 16 , wherein the compound of Formula (I-A) is:
18. The composition of claim 10 , wherein the compound of Formula (II-A-1) is:
19. The composition of claim 10 , wherein the composition comprises a chain extender.
20. The composition of claim 10 , wherein the epoxy resin comprises a diepoxide resin.