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US 11,370,889 B2Granted
Boroxine based dynamic thermosetting polymers
AssigneeThe Regents of the University of California
InventorsZhibin Guan, William Ogden
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Abstract
The disclosure provides for dynamic thermosetting polymers comprising boroxine crosslinks that exhibit unusual mechanical behavior by being strong, highly malleable, recyclable and fully reprocessable. The disclosure further provides methods of making the thermosetting polymers and applications thereof.
Claims18
A dynamic thermosetting polymer comprising:
- a plurality of boroxine crosslinks having the structure of:
- formed from monomers comprising the structure of Formula IV(a), Formula IV(b), Formula IV(c), Formula IV(d), Formula IV(e), Formula IV(f), Formula IV(g), Formula IV(h) and/or Formula IV(i):
- wherein,
- X1 is selected from optionally substituted (C3-C24)-alkylene, optionally substituted (C3-C24)-hetero-alkylene, optionally substituted (C3-C24)-alkenylene, optionally substituted (C3-12)-hetero-alkenylene, optionally substituted (C3-12)-alkynylene, optionally substituted (C3-C12)-hetero-alkynylene, optionally substituted (C5-C12)-cycloalkylene, optionally substituted (C5-C12)-cycloalkenylene, and optionally substituted heterocyclylidene;
- X7 is selected from optionally substituted (C3-C24)-alkylene, optionally substituted (C3-C24)-hetero-alkylene, optionally substituted (C3-C24)-alkenylene, optionally substituted (C3-12)-hetero-alkenylene, optionally substituted (C3-12)-alkynylene, optionally substituted (C3-C12)-hetero-alkynylene, optionally substituted (C5-C12)-cycloalkylene, optionally substituted (C5-C12)-cycloalkenylene, and optionally substituted heterocyclylidene;
- and
- R1-R15 are independently selected from the group consisting of H, D, aryl, heterocyclyl, (C1-C6)-alkyl, (C1-C6)-hetero-alkyl, (C2-C6)-alkenyl, (C2-6)-hetero-alkenyl, (C2-6)-alkynyl, (C2-C6)-hetero-alkynyl, ether, ester, halo, hydroxyl, boronic acid, boronic ester, carboxyl, carboxylate, aldehyde, ketone, haloformyl, carboxamide, amine, azide, isonitrile, nitroso, nitro, thiol, sulfinyl, and sulfo;
- optionally, the dynamic thermosetting polymer is also formed from one or more comonomers;
- optionally, the dynamic thermosetting polymer further comprises one or more plasticizers;
- wherein the dynamic thermosetting polymer is malleable, can be recycled back to monomers, and/or is capable of being reprocessed.
7 more elements
A dynamic thermosetting polymer comprising:
- a plurality of boroxine crosslinks having the structure of:
- formed from monomers comprising the structure of Formula III(c), Formula III(d) and/or Formula III(e):
- wherein,
- Ar is selected from optionally substituted arylene, or optionally substituted aromatic heterocyclylidene;
- Ar is selected from optionally substituted arylene, or optionally substituted aromatic heterocyclylidene;
- R is selected from optionally substituted (C1-C24)-alkylene, optionally substituted (C1-C24)-alkenylene, optionally substituted (C1-12)-hetero-alkenylene, optionally substituted (C2-12)-alkynylene, optionally substituted (C2-C12)-hetero-alkynylene, optionally substituted (C3-C12)-cycloalkylene, optionally substituted (C4-C12)-cycloalkenylene, or any combination of the foregoing groups;
- and
- X2 and X6 are each independently selected from optionally substituted aryl, optionally substituted (C1-C24)-alkyl, optionally substituted (C1-C24)-heteroalkyl, optionally substituted (C1-C24)-alkenyl, optionally substituted (C1-12)-heteroalkenyl, optionally substituted (C2-12)-alkynyl, optionally substituted (C2-C12)-heteroalkynyl, optionally substituted (C3-C12)-cycloalkyl, optionally substituted (C4-C12)-cycloalkenyl, and optionally substituted heterocyclyl;
- X3, X4, and X5 are each independently selected from optionally substituted arylene, optionally substituted (C1-C24)-alkylene, optionally substituted (C1-C24)-hetero-alkylene, optionally substituted (C1-C24)-alkenylene, optionally substituted (C1-12)-hetero-alkenylene, optionally substituted (C2-12)-alkynylene, optionally substituted (C2-C12)-hetero-alkynylene, optionally substituted (C3-C12)-cycloalkylene, optionally substituted (C4-C12)-cycloalkenylene, and optionally substituted heterocyclylidene;
- and
- n is an integer selected from 1 to 1000;
- optionally, the dynamic thermosetting polymer is also formed from one or more comonomers;
- optionally, the dynamic thermosetting polymer further comprises one or more plasticizers;
- wherein the dynamic thermosetting polymer is malleable, can be recycled back to monomers, and/or is capable of being reprocessed.
11 more elements
Dependencies are inferred from the claim text.