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 method for recycling a composition, wherein the composition comprises the reaction product of:
an epoxy resin; and
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;
the method comprising contacting the composition with an acid.
2. The method 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 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; and
provided that the sum of t, q1, and q2 is 4.
3. The method of claim 1 , wherein the compound of Formula (I-A) is a compound of Formula (I-A-ii-1):
wherein:
q1 is an integer from 1 to 4; and
each occurrence of R 5A 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;
t is 0, 1, 2, or 3; and
each occurrence of R 4D is independently hydrogen or alkyl;
provided that the sum of t and q1, is 4.
4. The method of claim 1 , wherein the compound of Formula (I-A) is:
5. The method of claim 4 , wherein the compound of Formula (I-A) is:
6. The method of claim 5 , wherein the compound of Formula (I-A) is:
7. The method of claim 1 , wherein the composition comprises a chain extender.
8. The method of claim 1 , wherein the epoxy resin comprises a diepoxide resin.
9. The method of claim 1 , wherein the acid is selected from the group consisting of hydrochloric acid, acetic acid, chloroacetic acid, lactic acid, formic acid, propionic acid, citric acid, methane sulfonic acid, p-toluene sulfonic acid, sulfuric acid, benzoic acid, phthalic acid, and combinations thereof.
10. The method of claim 1 , comprising contacting the composition with the acid in the presence of a solvent.
11. The method of claim 1 , wherein the solvent is water.
12. The method of claim 1 , wherein the recycling is performed in the presence of heat.