Recovery of monomeric and oligomeric building blocks from polymeric materials

A method, comprising:

• providing a polymer comprising a pendant group of Formula (I):
• wherein:
• X is O, S or NH;
• Y is N or CR3;
• R1 is independently H, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C1-6 heteroalkyl, substituted or unsubstituted C1-6 alkoxy, substituted or unsubstituted C1-6 thioalkoxy, substituted or unsubstituted C1-6 carbonyl, substituted or unsubstituted cyclo(C3-8) alkyl, substituted or unsubstituted cyclo(C3-8) heteroalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or R4 and R5 together form a 4-, 5-, 6-, 7-, or 8-membered ring selected from substituted or unsubstituted cyclo (C4-8) alkyl, substituted or unsubstituted cyclo (C4-8) heteroalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
• R2, R3, and R4 are each independently H, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C1-6 heteroalkyl, substituted or unsubstituted C1-6 alkoxy, substituted or unsubstituted C1-6 thioalkoxy, substituted or unsubstituted C1-6 carbonyl, substituted or unsubstituted C1-6 carboxyl, substituted or unsubstituted cyclo(C3-8) alkyl, substituted or unsubstituted cyclo(C3-8) heteroalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or R4 and R5 together form a 4-, 5-, 6-, 7-, or 8-membered ring selected from substituted or unsubstituted cyclo (C4-8) alkyl, substituted or unsubstituted cyclo (C4-8) heteroalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
• and
• R5 is substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C1-6 heteroalkyl, substituted or unsubstituted C1-6 alkoxy, substituted or unsubstituted C1-6 thioalkoxy, substituted or unsubstituted C1-6 carbonyl, substituted or unsubstituted C1-6 carboxyl, substituted or unsubstituted cyclo(C3-8) alkyl, substituted or unsubstituted cyclo(C3-8) heteroalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or R4 and R5 together form a 4-, 5-, 6-, 7-, or 8-membered ring selected from substituted or unsubstituted cyclo (C4-8) alkyl, substituted or unsubstituted cyclo (C4-8) heteroalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
• cleaving a bond coupling the pendant group to a backbone of the polymer to produce a mixture;
• and
• recovering the pendant group from the mixture.

A process, comprising:

• providing a curable composition;
• curing the curable composition to generate a polymer comprising a pendant group;
• subjecting the polymer to reaction conditions to cleave a bond coupling the pendant group to a backbone of the polymer;
• generating a mixture comprising the pendant group;
• and
• recovering at least 70% of the pendant group relative to an amount of the pendant group present in the polymer,
• wherein the recovered pendant group is a compound according to Formula (IX):
• wherein:
• R1 is independently H, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C1-6 heteroalkyl, substituted or unsubstituted C1-6 alkoxy, substituted or unsubstituted C1-6 thioalkoxy, substituted or unsubstituted C1-6 carbonyl, substituted or unsubstituted cyclo-(C3-8) alkyl, substituted or unsubstituted cyclo(C3-8) heteroalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
• R2, R3, and R4 are each independently H, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C1-6 heteroalkyl, substituted or unsubstituted C1-6 alkoxy, substituted or unsubstituted C1-6 thioalkoxy, substituted or unsubstituted C1-6 carbonyl, substituted or unsubstituted C1-6 carboxyl, substituted or unsubstituted cyclo-(C3-8) alkyl, substituted or unsubstituted cyclo(C3-8) heteroalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
• and
• R5 is substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C1-6 heteroalkyl, substituted or unsubstituted C1-6 alkoxy, substituted or unsubstituted C1-6 thioalkoxy, substituted or unsubstituted C1-6 carbonyl, substituted or unsubstituted C1-6 carboxyl, substituted or unsubstituted cyclo-(C3-8) alkyl, substituted or unsubstituted cyclo(C3-8) heteroalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.